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<span class="vector-toc-numb">4.3</span> <span>2012 Class action lawsuit</span> </div> </a> <ul id="toc-2012_Class_action_lawsuit-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-2015_Canadian_regulatory_review" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#2015_Canadian_regulatory_review"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>2015 Canadian regulatory review</span> </div> </a> <ul id="toc-2015_Canadian_regulatory_review-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" 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Available in 27 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-27" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">27 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%AA%D8%B1%D8%A7%D8%B2%D9%8A%D9%86" title="أترازين – Arabic" lang="ar" hreflang="ar" data-title="أترازين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D8%AA%D8%B1%D8%A7%D8%B2%DB%8C%D9%86" title="آترازین – South Azerbaijani" lang="azb" hreflang="azb" data-title="آترازین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Atrazina" title="Atrazina – Catalan" lang="ca" hreflang="ca" data-title="Atrazina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Atrazin" title="Atrazin – Czech" lang="cs" hreflang="cs" data-title="Atrazin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Atrazin" title="Atrazin – German" lang="de" hreflang="de" data-title="Atrazin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Atrazina" title="Atrazina – Spanish" lang="es" hreflang="es" data-title="Atrazina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D8%AA%D8%B1%D8%A7%D8%B2%DB%8C%D9%86" title="آترازین – Persian" lang="fa" hreflang="fa" data-title="آترازین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Atrazine" title="Atrazine – French" lang="fr" hreflang="fr" data-title="Atrazine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Atrazina" title="Atrazina – Galician" lang="gl" hreflang="gl" data-title="Atrazina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%ED%8A%B8%EB%9D%BC%EC%A7%84" title="아트라진 – Korean" lang="ko" hreflang="ko" data-title="아트라진" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Atrazina" title="Atrazina – Italian" lang="it" hreflang="it" data-title="Atrazina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%90%D1%82%D1%80%D0%B0%D0%B7%D0%B8%D0%BD" title="Атразин – Kyrgyz" lang="ky" hreflang="ky" data-title="Атразин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D1%82%D1%80%D0%B0%D0%B7%D0%B8%D0%BD" title="Атразин – Macedonian" lang="mk" hreflang="mk" data-title="Атразин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Atrazine" title="Atrazine – Dutch" lang="nl" hreflang="nl" data-title="Atrazine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%88%E3%83%A9%E3%82%B8%E3%83%B3" title="アトラジン – Japanese" lang="ja" hreflang="ja" data-title="アトラジン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Atrazin" title="Atrazin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Atrazin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Atrazyna" title="Atrazyna – Polish" lang="pl" hreflang="pl" data-title="Atrazyna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Atrazina" title="Atrazina – Portuguese" lang="pt" hreflang="pt" data-title="Atrazina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D1%82%D1%80%D0%B0%D0%B7%D0%B8%D0%BD" title="Атразин – Russian" lang="ru" hreflang="ru" data-title="Атразин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Atraz%C3%ADn" title="Atrazín – Slovak" lang="sk" hreflang="sk" data-title="Atrazín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Atrazin" title="Atrazin – Serbian" lang="sr" hreflang="sr" data-title="Atrazin" 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/Atrazin" title="Atrazin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Atrazin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Atratsiini" title="Atratsiini – Finnish" lang="fi" hreflang="fi" data-title="Atratsiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Atrazin" title="Atrazin – Swedish" lang="sv" hreflang="sv" data-title="Atrazin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%86%E0%AE%9F%E0%AF%8D%E0%AE%B0%E0%AE%BE%E0%AE%9A%E0%AF%88%E0%AE%A9%E0%AF%8D" title="ஆட்ராசைன் – Tamil" lang="ta" hreflang="ta" data-title="ஆட்ராசைன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%90%D1%82%D1%80%D0%B0%D0%B7%D0%B8%D0%BD" title="Атразин – Tajik" lang="tg" hreflang="tg" data-title="Атразин" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8D%89%E8%84%AB%E6%B7%A8" title="草脫淨 – Chinese" lang="zh" hreflang="zh" data-title="草脫淨" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q408652#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" 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">Herbicide</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Atrazine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:AtrazineVector.svg" class="mw-file-description" title="Atrazine"><img alt="Atrazine" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/AtrazineVector.svg/220px-AtrazineVector.svg.png" decoding="async" width="220" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/AtrazineVector.svg/330px-AtrazineVector.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/AtrazineVector.svg/440px-AtrazineVector.svg.png 2x" data-file-width="417" data-file-height="264" /></a><figcaption>Atrazine</figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Atrazine-3D-balls.png" class="mw-file-description" title="Atrazine"><img alt="Atrazine" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Atrazine-3D-balls.png/250px-Atrazine-3D-balls.png" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Atrazine-3D-balls.png/330px-Atrazine-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/Atrazine-3D-balls.png/500px-Atrazine-3D-balls.png 2x" data-file-width="1100" data-file-height="767" /></a><figcaption>Atrazine</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;">6-Chloro-<i>N</i><sup>2</sup>-ethyl-<i>N</i><sup>4</sup>-(propan-2-yl)-1,3,5-triazine-2,4-diamine</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;">Atrazine<br />1-Chloro-3-ethylamino-5-isopropylamino-2,4,6-triazine<br />2-Chloro-4-ethylamino-6-isopropylamino-<i>s</i>-triazine<br />6-Chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine</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=1912-24-9">1912-24-9</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=Clc1nc%28nc%28n1%29NC%28C%29C%29NCC">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15930">CHEBI:15930</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL15063">ChEMBL15063</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/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.2169.html">2169</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB07392">DB07392</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.016.017">100.016.017</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408652#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C06551">C06551</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/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/2256">2256</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/QJA9M5H4IM">QJA9M5H4IM</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/DTXSID9020112">DTXSID9020112</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408652#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/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MXWJVTOOROXGIU-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MXWJVTOOROXGIU-UHFFFAOYAJ</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%;">Clc1nc(nc(n1)NC(C)C)NCC</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>8</sub><span title="Hydrogen">H</span><sub>14</sub><span title="Chlorine">Cl</span><span title="Nitrogen">N</span><sub>5</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="7002215690000000000♠"></span>215.69</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless solid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.187 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>175 °C (347 °F; 448 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>200 °C (392 °F; 473 K) decomposes<sup id="cite_ref-PGCH_1-0" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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>7 mg/100 mL </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>Noncombustible<sup id="cite_ref-PGCH_1-4" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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>None<sup id="cite_ref-PGCH_1-1" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<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>TWA 5 mg/m<sup>3</sup><sup id="cite_ref-PGCH_1-2" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<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/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>N.D.<sup id="cite_ref-PGCH_1-3" class="reference"><a href="#cite_note-PGCH-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443663905&page2=Atrazine">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Atrazine</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'t' in 'tie'">t</span><span title="'r' in 'rye'">r</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'z' in 'zoom'">z</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling"><span style="font-size:90%">A</span>-trə-zeen</i></a>) is a <a href="/wiki/Organochlorine_compound" class="mw-redirect" title="Organochlorine compound">chlorinated</a> <a href="/wiki/Herbicide" title="Herbicide">herbicide</a> of the <a href="/wiki/Triazine" title="Triazine">triazine</a> class.<sup id="cite_ref-EPAatrazine_2-0" class="reference"><a href="#cite_note-EPAatrazine-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is used to prevent pre-emergence broadleaf <a href="/wiki/Weed" title="Weed">weeds</a> in crops such as <a href="/wiki/Maize" title="Maize">maize</a> (corn),<sup id="cite_ref-DrinkTap.org_3-0" class="reference"><a href="#cite_note-DrinkTap.org-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Soybean" title="Soybean">soybean</a><sup id="cite_ref-DrinkTap.org_3-1" class="reference"><a href="#cite_note-DrinkTap.org-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Sugarcane" title="Sugarcane">sugarcane</a> and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is <a href="/wiki/Syngenta" title="Syngenta">Syngenta</a> and it is one of the most widely used herbicides in the United States,<sup id="cite_ref-EPAatrazine_2-1" class="reference"><a href="#cite_note-EPAatrazine-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Canadian,<sup id="cite_ref-:can_4-0" class="reference"><a href="#cite_note-:can-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and Australian agriculture.<sup id="cite_ref-APVMAmain_5-0" class="reference"><a href="#cite_note-APVMAmain-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Its use was banned in the <a href="/wiki/European_Union" title="European Union">European Union</a> in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe.<sup id="cite_ref-EUban_6-0" class="reference"><a href="#cite_note-EUban-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NYT2004_7-0" class="reference"><a href="#cite_note-NYT2004-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>At least two significant Canadian farm well studies showed that atrazine was the most common contaminant found.<sup id="cite_ref-:can_4-1" class="reference"><a href="#cite_note-:can-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> As of 2001<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Atrazine&action=edit">[update]</a></sup>, atrazine was the most commonly detected pesticide contaminating drinking water in the U.S.<sup id="cite_ref-USGS_8-0" class="reference"><a href="#cite_note-USGS-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 44">: 44 </span></sup> Studies suggest it is an <a href="/wiki/Endocrine_disruptor" title="Endocrine disruptor">endocrine disruptor</a>, an agent that can alter the natural hormonal system.<sup id="cite_ref-AtrazineChemSummEPA_9-0" class="reference"><a href="#cite_note-AtrazineChemSummEPA-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> However, in 2006 the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">U.S. Environmental Protection Agency</a> (EPA) had stated that under the <a href="/wiki/Food_Quality_Protection_Act" title="Food Quality Protection Act">Food Quality Protection Act</a> "the risks associated with the pesticide residues pose a reasonable certainty of no harm",<sup id="cite_ref-EPATriazine_10-0" class="reference"><a href="#cite_note-EPATriazine-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> and in 2007, the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted.<sup id="cite_ref-EPAUpdateAmphib_11-0" class="reference"><a href="#cite_note-EPAUpdateAmphib-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The EPA's 2009 review<sup id="cite_ref-EPAPress_12-0" class="reference"><a href="#cite_note-EPAPress-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> concluded that "the agency's scientific bases for its regulation of atrazine are robust and ensure prevention of exposure levels that could lead to reproductive effects in humans".<sup id="cite_ref-AtraUpdateHealth_13-0" class="reference"><a href="#cite_note-AtraUpdateHealth-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> However, in their 2016 Refined Ecological Risk Assessment for Atrazine, it was stated that "it is difficult to make definitive conclusions about the impact of atrazine at a given concentration but multiple studies have reported effects to various endpoints at environmentally-relevant concentrations."<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> EPA started a registration review in 2013.<sup id="cite_ref-AtraUpdateHealthB_15-0" class="reference"><a href="#cite_note-AtraUpdateHealthB-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The EPA's review has been criticized, and the safety of atrazine remains controversial.<sup id="cite_ref-yorker_16-0" class="reference"><a href="#cite_note-yorker-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NYT_17-0" class="reference"><a href="#cite_note-NYT-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TillittFish_18-0" class="reference"><a href="#cite_note-TillittFish-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> EPA has however stated that "If at any time EPA determines there are urgent human or environmental risks from atrazine exposure that require prompt attention, we will take appropriate regulatory action, regardless of the status of the registration review process."<sup id="cite_ref-EPAatrazine_2-2" class="reference"><a href="#cite_note-EPAatrazine-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=1" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Atrazine is an <a href="/wiki/Herbicide" title="Herbicide">herbicide</a> that is used to stop pre- and post-emergence broadleaf and grassy <a href="/wiki/Weed" title="Weed">weeds</a> in crops such as <a href="/wiki/Sorghum" title="Sorghum">sorghum</a>, <a href="/wiki/Maize" title="Maize">maize</a>, <a href="/wiki/Sugarcane" title="Sugarcane">sugarcane</a>, <a href="/wiki/Lupins" class="mw-redirect" title="Lupins">lupins</a>, <a href="/wiki/Pine" title="Pine">pine</a>, and <a href="/wiki/Eucalypt" title="Eucalypt">eucalypt</a> plantations, and triazine-tolerant <a href="/wiki/Canola" class="mw-redirect" title="Canola">canola</a>.<sup id="cite_ref-APVMAmain_5-1" class="reference"><a href="#cite_note-APVMAmain-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In the <a href="/wiki/United_States" title="United States">United States</a> as of 2014, atrazine was the second-most widely used herbicide after <a href="/wiki/Glyphosate" title="Glyphosate">glyphosate</a>,<sup id="cite_ref-yorker_16-1" class="reference"><a href="#cite_note-yorker-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> with 76 million pounds (34 thousand metric tons) of it applied each year,<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><sup id="cite_ref-rupr_20-0" class="reference"><a href="#cite_note-rupr-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> nearly identical to its usage in 1974, of 76.8 million pounds.<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> Atrazine continues to be one of the most widely used herbicides in Australian agriculture.<sup id="cite_ref-APVMAmain_5-2" class="reference"><a href="#cite_note-APVMAmain-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Its effect on corn yields has been estimated from 1% to 8%, with 3–4% being the conclusion of one economics review.<sup id="cite_ref-Ackerman2007_22-0" class="reference"><a href="#cite_note-Ackerman2007-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><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> In another study looking at combined data from 236 university corn field trials from 1986 to 2005, atrazine treatments showed an average increase of 5.7 US bushels per acre (0.50 m<sup>3</sup>/ha) (~400 kilograms per hectare (360 lb/acre)) than alternative herbicide treatments.<sup id="cite_ref-NCWSS_24-0" class="reference"><a href="#cite_note-NCWSS-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Effects on sorghum yields have been estimated to be as high as 20%, owing in part to the absence of alternative weed control products that can be used on sorghum.<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-heading2"><h2 id="Chemistry_and_biochemistry">Chemistry and biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=2" title="Edit section: Chemistry and biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Atrazine was invented in 1958 in the <a href="/wiki/Geigy" class="mw-redirect" title="Geigy">Geigy</a> laboratories as the second of a series of <a href="/wiki/1,3,5-triazine" class="mw-redirect" title="1,3,5-triazine">1,3,5-triazines</a>.<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>Atrazine is prepared from <a href="/wiki/Cyanuric_chloride" title="Cyanuric chloride">cyanuric chloride</a>, which is treated sequentially with <a href="/wiki/Ethylamine" title="Ethylamine">ethylamine</a> and <a href="/wiki/Isopropylamine" title="Isopropylamine">isopropylamine</a>. Like other triazine herbicides, atrazine functions by binding to the <a href="/wiki/Plastoquinone" title="Plastoquinone">plastoquinone</a>-binding <a href="/wiki/Protein" title="Protein">protein</a> in <a href="/wiki/Photosystem_II" title="Photosystem II">photosystem II</a>, which animals lack. Plant death results from starvation and oxidative damage caused by breakdown in the <a href="/wiki/Electron_transport" class="mw-redirect" title="Electron transport">electron transport</a> process. Oxidative damage is accelerated at high light intensity.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Atrazine's effects in humans and animals primarily involve the <a href="/wiki/Endocrine_system" title="Endocrine system">endocrine system</a>. Studies suggest that atrazine is an <a href="/wiki/Endocrine_disruptor" title="Endocrine disruptor">endocrine disruptor</a> that can cause <a href="/wiki/Hormone_imbalance" class="mw-redirect" title="Hormone imbalance">hormone imbalance</a>.<sup id="cite_ref-AtrazineChemSummEPA_9-1" class="reference"><a href="#cite_note-AtrazineChemSummEPA-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Atrazine has been found to act as an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/G_protein-coupled_estrogen_receptor_1" class="mw-redirect" title="G protein-coupled estrogen receptor 1">G protein-coupled estrogen receptor 1</a>.<sup id="cite_ref-ProssnitzBarton2014_28-0" class="reference"><a href="#cite_note-ProssnitzBarton2014-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Atrazine has been shown to bind covalently to (chemically react with) a large number of mammalian proteins.<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="Environment">Environment</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=3" title="Edit section: Environment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Levels">Levels</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=4" title="Edit section: Levels"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Atrazine contamination of surface water (lakes, rivers, and streams) in the U.S. has been monitored by the EPA and has consistently exceeded levels of concern in two Missouri watersheds and one in Nebraska.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Monitoring of atrazine levels in community water systems in 31 high-use states found that levels exceeded levels of concern for infant exposure during at least one year between 1993 and 2001 in 34 of 3670 community water systems using surface water, and in none of 14,500 community water systems using groundwater.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Surface water monitoring data from 20 high atrazine use watersheds found peak atrazine levels up to 147 parts per billion, with daily averages in all cases below 10 parts per billion.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biodegradation">Biodegradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=5" title="Edit section: Biodegradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Pathway_Atrazine_degradation.svg" class="mw-file-description"><img alt="Biodegradation - atrazine chlorohydrolase pathway" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Pathway_Atrazine_degradation.svg/330px-Pathway_Atrazine_degradation.svg.png" decoding="async" width="300" height="249" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Pathway_Atrazine_degradation.svg/500px-Pathway_Atrazine_degradation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a9/Pathway_Atrazine_degradation.svg/600px-Pathway_Atrazine_degradation.svg.png 2x" data-file-width="622" data-file-height="516" /></a><figcaption><a href="/wiki/Atrazine_chlorohydrolase" title="Atrazine chlorohydrolase">Atrazine chlorohydrolase</a> pathway</figcaption></figure> <p>Atrazine remains in soil for a matter of months (although in some soils can persist to at least four years)<sup id="cite_ref-AtrazineChemSummEPA_9-2" class="reference"><a href="#cite_note-AtrazineChemSummEPA-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and can migrate from soil to <a href="/wiki/Groundwater" title="Groundwater">groundwater</a>; once in groundwater, it degrades slowly. It has been detected in groundwater at high levels in some regions of the U.S. where it is used on some crops and turf. The U.S. Environmental Protection Agency expresses concern regarding contamination of surface waters (lakes, rivers, and streams).<sup id="cite_ref-AtrazineChemSummEPA_9-3" class="reference"><a href="#cite_note-AtrazineChemSummEPA-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Atrazine degrades in <a href="/wiki/Soil" title="Soil">soil</a> primarily by the action of <a href="/wiki/Microbe" class="mw-redirect" title="Microbe">microbes</a>. The <a href="/wiki/Half-life" title="Half-life">half-life</a> of atrazine in soil ranges from 13 to 261 days.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Atrazine <a href="/wiki/Biodegradation" title="Biodegradation">biodegradation</a> can occur by two known pathways: </p> <ol><li><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> of the C-Cl bond is followed by the <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> and <a href="/wiki/Isopropyl" class="mw-redirect" title="Isopropyl">isopropyl</a> groups, catalyzed by the <a href="/wiki/Hydrolase" title="Hydrolase">hydrolase</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> called AtzA, AtzB, and AtzC. The end product of this process is <a href="/wiki/Cyanuric_acid" title="Cyanuric acid">cyanuric acid</a>, itself unstable with respect to ammonia and carbon dioxide. The best characterized organisms that use this pathway are of <i><a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a></i> sp. strain ADP.</li> <li>Dealkylation of the <a href="/wiki/Amino_group" class="mw-redirect" title="Amino group">amino groups</a> gives 2-chloro-4-hydroxy-6-amino-1,3,5-triazine, the degradation of which is unknown. This path also occurs in <i>Pseudomonas</i> species, as well as a number of bacteria.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-wackett_34-0" class="reference"><a href="#cite_note-wackett-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup></li></ol> <p>Rates of biodegradation are affected by atrazine's low solubility; thus <a href="/wiki/Surfactant" title="Surfactant">surfactants</a> may increase the degradation rate. Though the two alkyl moieties readily support growth of certain microorganisms, the atrazine ring is a poor energy source due to the oxidized state of ring carbon. In fact, the most common pathway for atrazine degradation involves the intermediate, cyanuric acid, in which carbon is fully oxidized, thus the ring is primarily a nitrogen source for aerobic microorganisms. Atrazine may be <a href="/wiki/Catabolism" title="Catabolism">catabolized</a> as a carbon and nitrogen source in reducing environments, and some aerobic atrazine degraders have been shown to use the compound for growth under anoxia in the presence of nitrate as an electron acceptor,<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> a process referred to as a <a href="/wiki/Denitrification" title="Denitrification">denitrification</a>. When atrazine is used as a nitrogen source for bacterial growth, degradation may be regulated by the presence of alternative sources of nitrogen. In pure cultures of atrazine-degrading bacteria, as well as active soil communities, atrazine ring nitrogen, but not carbon are assimilated into microbial biomass.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Low concentrations of <a href="/wiki/Glucose" title="Glucose">glucose</a> can decrease the bioavailability, whereas higher concentrations promote the catabolism of atrazine.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Gene" title="Gene">genes</a> for enzymes <a href="/wiki/AtzA" class="mw-redirect" title="AtzA">AtzA</a>-C have been found to be highly conserved in atrazine-degrading organisms worldwide. In <i><a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a></i> sp. ADP<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="Is ADP a provisional name? (October 2023)">clarification needed</span></a></i>]</sup>, the Atz genes are located noncontiguously on a <a href="/wiki/Plasmid" title="Plasmid">plasmid</a> with the genes for <a href="/wiki/Mercury_(element)" title="Mercury (element)">mercury</a> catabolism. AtzA-C genes have also been found in a <a href="/wiki/Gram-positive_bacteria" title="Gram-positive bacteria">Gram-positive bacterium</a>, but are chromosomally located.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> The insertion elements flanking each gene suggest that they are involved in the assembly of this specialized catabolic pathway.<sup id="cite_ref-wackett_34-1" class="reference"><a href="#cite_note-wackett-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Two options exist for degradation of atrazine using microbes, <a href="/wiki/Bioaugmentation" title="Bioaugmentation">bioaugmentation</a> or <a href="/wiki/Biostimulation" title="Biostimulation">biostimulation</a>.<sup id="cite_ref-wackett_34-2" class="reference"><a href="#cite_note-wackett-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Like the herbicides <a href="/wiki/Trifluralin" title="Trifluralin">trifluralin</a> and <a href="/wiki/Alachlor" title="Alachlor">alachlor</a>, atrazine is susceptible to rapid transformation in the presence of reduced iron-bearing soil clays, such as ferruginous <a href="/wiki/Smectite" title="Smectite">smectites</a>. In natural environments, some iron-bearing minerals are reduced by specific bacteria in the absence of oxygen, thus the abiotic transformation of herbicides by reduced minerals is viewed as "microbially induced".<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Photolysis">Photolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=6" title="Edit section: Photolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2016, photolytic degradation with 254 nm <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> was seen by the authors of a particular study as an efficient process, which could be used in pilot plants to reduce or eliminate compounds of the atrazine class or similar emerging contaminants, in effluents.<sup id="cite_ref-fdel_40-0" class="reference"><a href="#cite_note-fdel-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicology">Toxicology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=7" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to Extension Toxicology Network in the U.S., "The oral median Lethal Dose or <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> for atrazine is 3090 mg/kg in <a href="/wiki/Rat" title="Rat">rats</a>, 1750 mg/kg in <a href="/wiki/Mouse" title="Mouse">mice</a>, 750 mg/kg in <a href="/wiki/Rabbit" title="Rabbit">rabbits</a>, and 1000 mg/kg in hamsters. The dermal LD<sub>50</sub> in rabbits is 7500 mg/kg and greater than 3000 mg/kg in rats. The 1-hour inhalation LC<sub>50</sub> is greater than 0.7 mg/L in rats. The 4-hour inhalation LC<sub>50</sub> is 5.2 mg/L in rats." The <a href="/wiki/Maximum_contaminant_level" title="Maximum contaminant level">maximum contaminant level</a> is 0.003 mg/L and the <a href="/wiki/Reference_dose" title="Reference dose">reference dose</a> is 0.035 mg/kg/day.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Atrazine_USA_2019.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Atrazine_USA_2019.png/220px-Atrazine_USA_2019.png" decoding="async" width="220" height="288" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Atrazine_USA_2019.png/330px-Atrazine_USA_2019.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Atrazine_USA_2019.png/440px-Atrazine_USA_2019.png 2x" data-file-width="1162" data-file-height="1520" /></a><figcaption>Atrazine use in the U.S. in 2019</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Mammals">Mammals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=8" title="Edit section: Mammals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A September 2003 review by the <a href="/wiki/Agency_for_Toxic_Substances_and_Disease_Registry" title="Agency for Toxic Substances and Disease Registry">Agency for Toxic Substances and Disease Registry</a> (ATSDR) stated that atrazine is "currently under review for pesticide re-registration by the EPA because of concerns that atrazine may cause cancer", but not enough information was available to "definitely state whether it causes cancer in humans." According to the ATSDR, one of the primary ways that atrazine can affect a person's health is "by altering the way that the reproductive system works. Studies of couples living on farms that use atrazine for weed control found an increase in the risk of preterm delivery, but these studies are difficult to interpret because most of the farmers were men who may have been exposed to several types of pesticides. Little information is available regarding the risks to children, however "[m]aternal exposure to atrazine in drinking water has been associated with low fetal weight and heart, urinary, and limb defects in humans".<sup id="cite_ref-ATSDR_42-0" class="reference"><a href="#cite_note-ATSDR-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Incidence of a birth defect known as <a href="/wiki/Gastroschisis" title="Gastroschisis">gastroschisis</a> appears to be higher in areas where surface water atrazine levels are elevated especially when conception occurs in the spring, the time when atrazine is commonly applied.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a>'s <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> has classified atrazine as "not classifiable as to its carcinogenicity to humans" (<a href="/wiki/List_of_IARC_Group_3_Agents_-_Not_classifiable_as_to_its_carcinogenicity_to_humans" class="mw-redirect" title="List of IARC Group 3 Agents - Not classifiable as to its carcinogenicity to humans">Group 3</a>).<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>The EPA determined in 2003 "that atrazine is not likely to cause cancer in humans".<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>In 2006, the EPA stated, "the risks associated with the pesticide residues pose a reasonable certainty of no harm".<sup id="cite_ref-EPATriazine_10-1" class="reference"><a href="#cite_note-EPATriazine-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EPAUpdateAmphib_11-1" class="reference"><a href="#cite_note-EPAUpdateAmphib-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In 2007, the EPA said, "studies thus far suggest that atrazine is an <a href="/wiki/Endocrine_disruptor" title="Endocrine disruptor">endocrine disruptor</a>". The implications for children's health are related to effects during pregnancy and during sexual development, though few studies are available. In people, risks for preterm delivery and intrauterine growth retardation have been associated with exposure. Atrazine exposure has been shown to result in delays or changes in <a href="/wiki/Pubertal" class="mw-redirect" title="Pubertal">pubertal</a> development in female rats; conflicting results have been observed in males. Male rats exposed via milk from orally exposed mothers exhibited higher levels of prostate inflammation as adults; immune effects have also been seen in male rats exposed in utero or while nursing.<sup id="cite_ref-AtrazineChemSummEPA_9-4" class="reference"><a href="#cite_note-AtrazineChemSummEPA-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> EPA opened a new review in 2009<sup id="cite_ref-EPAPress_12-1" class="reference"><a href="#cite_note-EPAPress-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> that concluded that "the agency's scientific bases for its regulation of atrazine are robust and ensure prevention of exposure levels that could lead to reproductive effects in humans."<sup id="cite_ref-AtraUpdateHealth_13-1" class="reference"><a href="#cite_note-AtraUpdateHealth-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Deborah A. Cory-Slechta, a professor at the University of Rochester in New York has said in 2014, "The way the E.P.A. tests chemicals can vastly underestimate risks." She has studied atrazine's effects on the brain and serves on the E.P.A.'s science advisory board. She further stated, "There's still a huge amount we don't know about atrazine."<sup id="cite_ref-yorker_16-2" class="reference"><a href="#cite_note-yorker-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>A <a href="/wiki/Natural_Resources_Defense_Council" title="Natural Resources Defense Council">Natural Resources Defense Council</a> report from 2009 said that the EPA is ignoring atrazine contamination in surface and drinking water in the central United States.<sup id="cite_ref-NRDC,_Poisoning_the_Well_46-0" class="reference"><a href="#cite_note-NRDC,_Poisoning_the_Well-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>"There was no consistent evidence of an association between atrazine use and any cancer site". The study tracked 57,310 licensed pesticide applicators over 13 years.<sup id="cite_ref-EHP2011_47-0" class="reference"><a href="#cite_note-EHP2011-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>A 2011 review of the mammalian reproductive toxicology of atrazine jointly conducted by the <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> and the <a href="/wiki/Food_and_Agriculture_Organization" title="Food and Agriculture Organization">Food and Agriculture Organization</a> of the United Nations concluded that atrazine was not <a href="/wiki/Teratogenic" class="mw-redirect" title="Teratogenic">teratogenic</a>. Reproductive effects in rats and rabbits were only seen at doses that were toxic to the mother. Observed adverse effects in rats included <a href="/wiki/Fetal_resorption" title="Fetal resorption">fetal resorption</a> in rates (at doses ≥50 mg/kg per day), delays in sexual development in female rats (at doses ≥30 mg/kg per day), and decreased birth weight (at doses ≥3.6 mg/kg per day).<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>A 2014 systematic review, funded by atrazine manufacturer Syngenta, assessed its relation to reproductive health problems. The authors concluded that the quality of most studies was poor and without good quality data, the results were difficult to assess, though it was noted that no single category of negative pregnancy outcome was found consistently across studies. The authors concluded that a causal link between atrazine and adverse pregnancy outcomes was not warranted due to the poor quality of the data and the lack of robust findings across studies. Syngenta was not involved in the design, collection, management, analysis, or interpretation of the data and did not participate in the preparation of the manuscript.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Amphibians">Amphibians</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=9" title="Edit section: Amphibians"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Atrazine has been a suspected <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogen</a>, with some studies reporting causing demasculinization in male <a href="/wiki/Northern_leopard_frog" title="Northern leopard frog">northern leopard frogs</a> even at low concentrations.<sup id="cite_ref-EU_50-0" class="reference"><a href="#cite_note-EU-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> A 2002 study by <a href="/wiki/Tyrone_Hayes" title="Tyrone Hayes">Tyrone Hayes</a>, of the University of California, Berkeley, found that exposure caused male <a href="/wiki/Tadpole" title="Tadpole">tadpoles</a> to turn into <a href="/wiki/Hermaphrodites" class="mw-redirect" title="Hermaphrodites">hermaphrodites</a> – frogs with both male and female sexual characteristics.<sup id="cite_ref-Briggs_51-0" class="reference"><a href="#cite_note-Briggs-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> However, this study has not been able to be <a href="/wiki/Reproducibility" title="Reproducibility">replicated</a>,<sup id="cite_ref-eparesp_53-0" class="reference"><a href="#cite_note-eparesp-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> and a 2003 EPA review of this study concluded that overcrowding, questionable sample handling techniques, and the failure of the authors to disclose key details including sample sizes, dose-response effects, and the variability of observed effects made it difficult to assess the study's credibility and ecological relevance.<sup id="cite_ref-eparesp_53-1" class="reference"><a href="#cite_note-eparesp-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> A 2005 study, requested by EPA and conducted under EPA guidance and inspection, was unable to reproduce Hayes' results.<sup id="cite_ref-Jooste-et-al-2005_55-0" class="reference"><a href="#cite_note-Jooste-et-al-2005-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>In 2010, the <a href="/wiki/Australian_Pesticides_and_Veterinary_Medicines_Authority" title="Australian Pesticides and Veterinary Medicines Authority">Australian Pesticides and Veterinary Medicines Authority</a> (APVMA) tentatively concluded that environmental atrazine "at existing levels of exposure" was not affecting amphibian populations in Australia consistent with the 2007 EPA findings.<sup id="cite_ref-apvma2010_56-0" class="reference"><a href="#cite_note-apvma2010-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> APVMA responded to Hayes' 2010 published paper,<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> that his findings "do not provide sufficient evidence to justify a reconsideration of current regulations which are based on a very extensive dataset."<sup id="cite_ref-apvma2010_56-1" class="reference"><a href="#cite_note-apvma2010-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> The EPA's Scientific Advisory Panel examined relevant studies and concluded in 2010, "atrazine does not adversely affect amphibian gonadal development based on a review of laboratory and field studies".<sup id="cite_ref-EPAUpdateAmphib_11-2" class="reference"><a href="#cite_note-EPAUpdateAmphib-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It recommended proper study design for further investigation. As required by the EPA, two experiments were conducted under Good Laboratory Practices (GLP) and were inspected by EPA and German regulatory authorities, concluding 2009 that "long-term exposure of larval <i>X. laevis</i> to atrazine at concentrations ranging from 0.01 to 100 μg/L does not affect growth, larval development, or sexual differentiation".<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> A 2008 report cited the independent work of researchers in Japan, who were unable to replicate Hayes' work. "The scientists found no hermaphrodite frogs; no increase in aromatase as measured by aromatase mRNA induction; and no increase in <a href="/wiki/Vitellogenin" title="Vitellogenin">vitellogenin</a>, another marker of feminization."<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> The Atrazine Saga has been chronicled.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="2012_Class_action_lawsuit">2012 Class action lawsuit</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=10" title="Edit section: 2012 Class action lawsuit"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2012, Syngenta, an atrazine manufacturer, was the defendant in a class-action lawsuit concerning the levels of atrazine in human water supplies. Syngenta agreed to pay $105 million to reimburse more than one thousand water systems for "the cost of filtering atrazine from drinking water". The company denied all wrongdoing.<sup id="cite_ref-yorker_16-3" class="reference"><a href="#cite_note-yorker-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="2015_Canadian_regulatory_review">2015 Canadian regulatory review</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=11" title="Edit section: 2015 Canadian regulatory review"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Prompted by the EU's 2004 ban, a regulatory review of the product in Canada by the <a href="/wiki/PMRA" class="mw-redirect" title="PMRA">PMRA</a> was begun in 2015. On 31 March 2017 the review result was published and the PMRA decided to leave the product's registration unchanged. This was done because while the EU's ban was based on a legislated pollutant level of 0.1 μg/L, the Canadian regulations call for a home-grown "<a href="/wiki/Pest_Management_Regulatory_Agency#Risk_Assessment_Process" title="Pest Management Regulatory Agency">risk-based scientific approach</a> in determining the risk to human health from pesticides in drinking water." The U.S. drinking water standard of 3 μg/L is approximately the same to the Canadian standard of 5 μg/L. Both maximum pollutant levels in North America were not exceeded by the maximum pollutant level in Canadian data of 2.32 μg/L.<sup id="cite_ref-PMRA17_63-0" class="reference"><a href="#cite_note-PMRA17-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atrazine&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Pesticides_in_the_United_States#Atrazine" title="Pesticides in the United States">Pesticides in the United States – Atrazine</a></li> <li><a href="/wiki/Endocrine_disruptor" title="Endocrine disruptor">Endocrine disruptor</a></li> <li><a href="/wiki/Simazine" title="Simazine">Simazine</a></li></ul> <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=Atrazine&action=edit&section=13" 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 reflist-columns references-column-width" style="column-width: 35em;"> <ol class="references"> <li id="cite_note-PGCH-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PGCH_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-PGCH_1-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0043.html">"#0043"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230043&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0043.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-EPAatrazine-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-EPAatrazine_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EPAatrazine_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-EPAatrazine_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.epa.gov/ingredients-used-pesticide-products/atrazine">"Ingredients Used in Pesticide Products-Atrazine"</a>. <i>US Environmental Protection Agency</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220506084754/https://www.epa.gov/ingredients-used-pesticide-products/atrazine">Archived</a> from the original on 2022-05-06<span class="reference-accessdate">. Retrieved <span class="nowrap">2021-08-08</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=US+Environmental+Protection+Agency&rft.atitle=Ingredients+Used+in+Pesticide+Products-Atrazine&rft_id=https%3A%2F%2Fwww.epa.gov%2Fingredients-used-pesticide-products%2Fatrazine&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-DrinkTap.org-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-DrinkTap.org_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-DrinkTap.org_3-1"><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 news cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20180101024239/https://drinktap.org/Water-Info/Whats-in-My-Water/Atrazine">"Water Info : What's In My Water?: Atrazine"</a>. DrinkTap.org. Archived from <a rel="nofollow" class="external text" href="https://drinktap.org/Water-Info/Whats-in-My-Water/Atrazine">the original</a> on 1 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Water+Info+%3A+What%27s+In+My+Water%3F%3A+Atrazine&rft_id=https%3A%2F%2Fdrinktap.org%2FWater-Info%2FWhats-in-My-Water%2FAtrazine&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-:can-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-:can_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:can_4-1"><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 news cs1"><a rel="nofollow" class="external text" href="https://www.canada.ca/en/health-canada/services/publications/healthy-living/guidelines-canadian-drinking-water-quality-guideline-technical-document-atrazine.html">"Guidelines for Canadian Drinking Water Quality: Guideline Technical Document – Atrazine"</a>. Health Canada. 1 November 2011. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221105184514/https://www.canada.ca/en/health-canada/services/publications/healthy-living/guidelines-canadian-drinking-water-quality-guideline-technical-document-atrazine.html">Archived</a> from the original on 5 November 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">5 November</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Guidelines+for+Canadian+Drinking+Water+Quality%3A+Guideline+Technical+Document+%E2%80%93+Atrazine&rft.date=2011-11-01&rft_id=https%3A%2F%2Fwww.canada.ca%2Fen%2Fhealth-canada%2Fservices%2Fpublications%2Fhealthy-living%2Fguidelines-canadian-drinking-water-quality-guideline-technical-document-atrazine.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-APVMAmain-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-APVMAmain_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-APVMAmain_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-APVMAmain_5-2"><sup><i><b>c</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="http://apvma.gov.au/node/12371">"Chemical Review: Atrazine"</a>. Australian Pesticides and Veterinary Medicines Authority. 2014-05-28. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150211172609/http://apvma.gov.au/node/12371">Archived</a> from the original on 2015-02-11<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-02-11</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Chemical+Review%3A+Atrazine&rft.pub=Australian+Pesticides+and+Veterinary+Medicines+Authority&rft.date=2014-05-28&rft_id=http%3A%2F%2Fapvma.gov.au%2Fnode%2F12371&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-EUban-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-EUban_6-0">^</a></b></span> <span class="reference-text">European Commission. <a rel="nofollow" class="external text" href="http://eur-lex.europa.eu/legal-content/EN/TXT/?uri=uriserv:OJ.L_.2004.078.01.0053.01.ENG">2004/248/EC: Commission Decision of 10 March 2004 concerning the non-inclusion of atrazine in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing this active substance (Text with EEA relevance) (notified under document number C(2004) 731)</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220315165754/https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=uriserv:OJ.L_.2004.078.01.0053.01.ENG">Archived</a> 15 March 2022 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> Decision 2004/248/EC - Official Journal L 078, Decision 2004/248/EC. March 16, 2004: Quote: "(9) Assessments made on the basis of the information submitted have not demonstrated that it may be expected that, under the proposed conditions of use, plant protection products containing atrazine satisfy in general the requirements laid down in Article 5(1)(a) and (b) of Directive 91/414/EEC. In particular, available monitoring data were insufficient to demonstrate that in large areas concentrations of the active substance and its breakdown products will not exceed 0,1 μg/L in groundwater. Moreover, it cannot be assured that continued use in other areas will permit a satisfactory recovery of groundwater quality where concentrations already exceed 0,1 μg/L in groundwater. These levels of the active substance exceed the limits in Annex VI to Directive 91/414/EEC and would have an unacceptable effect on groundwater." (10) Atrazine should therefore not be included in Annex I to Directive 91/414/EEC. (11) Measures should be taken to ensure that existing authorisations for plant protection products containing atrazine are withdrawn within a prescribed period and are not renewed and that no new authorisations for such products are granted."</span> </li> <li id="cite_note-NYT2004-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-NYT2004_7-0">^</a></b></span> <span class="reference-text">Danny Hakimfeb for the New York Times. February 23, 2015. <a rel="nofollow" class="external text" href="https://www.nytimes.com/2015/02/24/business/international/a-pesticide-banned-or-not-underscores-trans-atlantic-trade-sensitivities.html?_r=0">A Pesticide Banned, or Not, Underscores Trans-Atlantic Trade Sensitivities</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161223091121/http://www.nytimes.com/2015/02/24/business/international/a-pesticide-banned-or-not-underscores-trans-atlantic-trade-sensitivities.html?_r=0">Archived</a> 2016-12-23 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-USGS-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-USGS_8-0">^</a></b></span> <span class="reference-text">Gilliom RJ et al. US Geological Survey <a rel="nofollow" class="external text" href="https://pubs.usgs.gov/circ/2005/1291/pdf/circ1291_chapter4.pdf">The Quality of Our Nation's Waters: Pesticides in the Nation's Streams and Ground Water, 1992–2001</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20131126164946/http://pubs.usgs.gov/circ/2005/1291/pdf/circ1291_chapter4.pdf">Archived</a> 2013-11-26 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> March 2006, Revised February 15, 2007</span> </li> <li id="cite_note-AtrazineChemSummEPA-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-AtrazineChemSummEPA_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AtrazineChemSummEPA_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AtrazineChemSummEPA_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-AtrazineChemSummEPA_9-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-AtrazineChemSummEPA_9-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation report cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20120316130312/http://www.epa.gov/teach/chem_summ/Atrazine_summary.pdf">Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children's Health</a> <span class="cs1-format">(PDF)</span> (Report). U.S. Environmental Protection Agency. 2007-04-24. Archived from <a rel="nofollow" class="external text" href="http://www.epa.gov/teach/chem_summ/Atrazine_summary.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 2012-03-16.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Atrazine%3A+Chemical+Summary.+Toxicity+and+Exposure+Assessment+for+Children%27s+Health&rft.pub=U.S.+Environmental+Protection+Agency&rft.date=2007-04-24&rft_id=http%3A%2F%2Fwww.epa.gov%2Fteach%2Fchem_summ%2FAtrazine_summary.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-EPATriazine-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-EPATriazine_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EPATriazine_10-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.epa.gov/oppsrrd1/cumulative/triazine_fs.htm">Triazine Cumulative Risk Assessment and Atrazine, Simazine, and Propazine Decisions</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130601222524/http://www.epa.gov/oppsrrd1/cumulative/triazine_fs.htm">Archived</a> June 1, 2013, at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, June 22, 2006, EPA.</span> </li> <li id="cite_note-EPAUpdateAmphib-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-EPAUpdateAmphib_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EPAUpdateAmphib_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-EPAUpdateAmphib_11-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#amphibian">Atrazine Updates: Amphibians</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150930062846/http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#amphibian">Archived</a> 2015-09-30 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, April 2010, EPA.</span> </li> <li id="cite_note-EPAPress-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-EPAPress_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EPAPress_12-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://yosemite.epa.gov/opa/admpress.nsf/d0cf6618525a9efb85257359003fb69d/554b6abea9d0672f85257648004a88c1!OpenDocument">EPA Begins New Scientific Evaluation of Atrazine</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160304110232/http://yosemite.epa.gov/opa/admpress.nsf/d0cf6618525a9efb85257359003fb69d/554b6abea9d0672f85257648004a88c1!OpenDocument">Archived</a> 2016-03-04 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, October 7, 2009, EPA.</span> </li> <li id="cite_note-AtraUpdateHealth-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-AtraUpdateHealth_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AtraUpdateHealth_13-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">EPA <a rel="nofollow" class="external text" href="http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#atrazine">Atrazine Updates: Scientific Peer Review—Human Health</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150930062846/http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#atrazine">Archived</a> 2015-09-30 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> Current as of January 2013. Accessed March 15, 2014</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</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.regulations.gov/document?D=EPA-HQ-OPP-2013-0266-0315">"Refined Ecological Risk Assessment for Atrazine"</a>. EPA. p. 184. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200911135522/https://www.regulations.gov/document?D=EPA-HQ-OPP-2013-0266-0315">Archived</a> from the original on 11 September 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">12 October</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Refined+Ecological+Risk+Assessment+for+Atrazine&rft.pages=184&rft.pub=EPA&rft_id=https%3A%2F%2Fwww.regulations.gov%2Fdocument%3FD%3DEPA-HQ-OPP-2013-0266-0315&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-AtraUpdateHealthB-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-AtraUpdateHealthB_15-0">^</a></b></span> <span class="reference-text">EPA [ww.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#amphibian Atrazine Updates: Scientific Peer Review—Amphibians] Current as of January 2013. 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(2021). <a rel="nofollow" class="external text" href="https://setac.onlinelibrary.wiley.com/doi/full/10.1002/etc.5037">"The Atrazine Saga and its Importance to the Future of Toxicology, Science, and Environmental and Human Health"</a>. <i>Environmental Toxicology and Chemistry</i>. <b>40</b> (6): <span class="nowrap">1544–</span>1558. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fetc.5037">10.1002/etc.5037</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Toxicology+and+Chemistry&rft.atitle=The+Atrazine+Saga+and+its+Importance+to+the+Future+of+Toxicology%2C+Science%2C+and+Environmental+and+Human+Health&rft.volume=40&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1544-%3C%2Fspan%3E1558&rft.date=2021&rft_id=info%3Adoi%2F10.1002%2Fetc.5037&rft.aulast=Rohr&rft.aufirst=Jason+R.&rft_id=https%3A%2F%2Fsetac.onlinelibrary.wiley.com%2Fdoi%2Ffull%2F10.1002%2Fetc.5037&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.atrazinesettlement.com/">City of Greenville v. Syngenta Crop Protection, Inc., and Syngenta AG Case No. 3:10-cv-00188-JPG-PMF</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210506104414/http://atrazinesettlement.com/">Archived</a> 2021-05-06 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, accessed August 23, 2013</span> </li> <li id="cite_note-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-62">^</a></b></span> <span class="reference-text">Clare Howard for Environmental Health News. June 17, 2013 <a rel="nofollow" class="external text" href="http://www.environmentalhealthnews.org/ehs/news/2013/atrazine">Special Report: Syngenta's campaign to protect atrazine, discredit critics.</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140330221647/http://www.environmentalhealthnews.org/ehs/news/2013/atrazine">Archived</a> 2014-03-30 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-PMRA17-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-PMRA17_63-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.canada.ca/en/health-canada/services/consumer-product-safety/reports-publications/pesticides-pest-management/decisions-updates/reevaluation-note/2017/atrazine-rev-2017-09.html">"Re-evaluation Note REV2017-09, Special Review Decision: Atrazine"</a>. Pest Management Regulatory Agency. 31 March 2017. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221105192643/https://www.canada.ca/en/health-canada/services/consumer-product-safety/reports-publications/pesticides-pest-management/decisions-updates/reevaluation-note/2017/atrazine-rev-2017-09.html">Archived</a> from the original on 5 November 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">5 November</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Re-evaluation+Note+REV2017-09%2C+Special+Review+Decision%3A+Atrazine&rft.date=2017-03-31&rft_id=https%3A%2F%2Fwww.canada.ca%2Fen%2Fhealth-canada%2Fservices%2Fconsumer-product-safety%2Freports-publications%2Fpesticides-pest-management%2Fdecisions-updates%2Freevaluation-note%2F2017%2Fatrazine-rev-2017-09.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtrazine" class="Z3988"></span></span> </li> </ol></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=Atrazine&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/Atrazine">Atrazine</a>- PubChem(National library of medicine) - atrazine</li> <li><a rel="nofollow" class="external text" href="http://npic.orst.edu/factsheets/atrazine.html">Atrazine Fact Sheet</a> - National Pesticide Information Center - Atrazine Fact Sheet</li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0043.html">Atrazine</a> - CDC - NIOSH Pocket Guide to Chemical Hazards</li> <li><i><a rel="nofollow" class="external text" href="http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/43.htm">Atrazine</a></i> in the Pesticide Properties DataBase (PPDB)</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output 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href="/wiki/Template:Herbicides" title="Template:Herbicides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Herbicides" title="Template talk:Herbicides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Herbicides" title="Special:EditPage/Template:Herbicides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Pest_control:_herbicides438" style="font-size:114%;margin:0 4em"><a href="/wiki/Pest_control" title="Pest control">Pest control</a>: <a href="/wiki/Herbicide" title="Herbicide">herbicides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aniline#Acylation" title="Aniline">Anilides</a>/<a href="/wiki/Aniline" title="Aniline">anilines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetochlor" title="Acetochlor">acetochlor</a></li> <li><a href="/wiki/Alachlor" title="Alachlor">alachlor</a></li> <li><a href="/wiki/Asulam" title="Asulam">asulam</a></li> <li><a href="/wiki/Benfluralin" title="Benfluralin">benfluralin</a></li> <li><a href="/wiki/Butachlor" title="Butachlor">butachlor</a></li> <li><a href="/w/index.php?title=Diethatyl&action=edit&redlink=1" class="new" title="Diethatyl (page does not exist)">diethatyl</a></li> <li><a href="/wiki/Diflufenican" title="Diflufenican">diflufenican</a></li> <li><a href="/wiki/Dimethenamid" title="Dimethenamid">dimethenamid</a></li> <li><a href="/wiki/Flamprop" title="Flamprop">flamprop</a></li> <li><a href="/w/index.php?title=Metazachlor&action=edit&redlink=1" class="new" title="Metazachlor (page does not exist)">metazachlor</a></li> <li><a href="/wiki/Metolachlor" title="Metolachlor">metolachlor</a></li> <li><a href="/wiki/Oryzalin" title="Oryzalin">oryzalin</a></li> <li><a href="/wiki/Pendimethalin" title="Pendimethalin">pendimethalin</a></li> <li><a href="/w/index.php?title=Pretilachlor&action=edit&redlink=1" class="new" title="Pretilachlor (page does not exist)">pretilachlor</a></li> <li><a href="/wiki/Propachlor" title="Propachlor">propachlor</a></li> <li><a href="/wiki/Propanil" title="Propanil">propanil</a></li> <li><a href="/wiki/Trifluralin" title="Trifluralin">trifluralin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromaticity" title="Aromaticity">Aromatic</a> <a href="/wiki/Organic_acid" title="Organic acid">acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopyralid" title="Aminopyralid">aminopyralid</a></li> <li><a href="/wiki/Chloramben" title="Chloramben">chloramben</a></li> <li><a href="/wiki/Clopyralid" title="Clopyralid">clopyralid</a></li> <li><a href="/wiki/Dicamba" title="Dicamba">dicamba</a></li> <li><a href="/wiki/Picloram" title="Picloram">picloram</a></li> <li><a href="/w/index.php?title=Pyrithiobac&action=edit&redlink=1" class="new" title="Pyrithiobac (page does not exist)">pyrithiobac</a></li> <li><a href="/wiki/Quinclorac" title="Quinclorac">quinclorac</a></li> <li><a href="/wiki/Quinmerac" title="Quinmerac">quinmerac</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsenic" title="Arsenic">Arsenicals</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cacodylic_acid" title="Cacodylic acid">cacodylic acid</a></li> <li><a href="/wiki/Copper(II)_arsenate" title="Copper(II) arsenate">copper arsenate</a></li> <li><a href="/wiki/Disodium_methyl_arsonate" title="Disodium methyl arsonate">DSMA</a></li> <li><a href="/wiki/Monosodium_methyl_arsonate" title="Monosodium methyl arsonate">MSMA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/4-hydroxyphenylpyruvate_dioxygenase_inhibitor" class="mw-redirect" title="4-hydroxyphenylpyruvate dioxygenase inhibitor">HPPD inhbitors</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Flurochloridone&action=edit&redlink=1" class="new" title="Flurochloridone (page does not exist)">flurochloridone</a></li> <li><a href="/wiki/Isoxaflutole" title="Isoxaflutole">isoxaflutole</a></li> <li><a href="/wiki/Leptospermone" title="Leptospermone">leptospermone</a></li> <li><a href="/wiki/Mesotrione" title="Mesotrione">mesotrione</a></li> <li><a href="/wiki/Nitisinone" title="Nitisinone">nitisinone</a></li> <li><a href="/wiki/Sethoxydim" title="Sethoxydim">sethoxydim</a></li> <li><a href="/w/index.php?title=Sulcotrione&action=edit&redlink=1" class="new" title="Sulcotrione (page does not exist)">sulcotrione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrile" title="Nitrile">Nitriles</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,6-Dichlorobenzonitrile" title="2,6-Dichlorobenzonitrile">DCBN</a></li> <li><a href="/wiki/Bromoxynil" title="Bromoxynil">bromoxynil</a></li> <li><a href="/wiki/Ioxynil" title="Ioxynil">ioxynil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organophosphorus_compound" class="mw-redirect" title="Organophosphorus compound">Organophosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bensulide" title="Bensulide">bensulide</a></li> <li><a href="/wiki/Bialaphos" title="Bialaphos">bialaphos</a></li> <li><a href="/wiki/Ethephon" title="Ethephon">ethephon</a></li> <li><a href="/w/index.php?title=Fosamine&action=edit&redlink=1" class="new" title="Fosamine (page does not exist)">fosamine</a></li> <li><a href="/wiki/Glufosinate" title="Glufosinate">glufosinate</a></li> <li><a href="/wiki/Glyphosate" title="Glyphosate">glyphosate</a></li> <li><a href="/w/index.php?title=Piperophos&action=edit&redlink=1" class="new" title="Piperophos (page does not exist)">piperophos</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenoxy_herbicide" title="Phenoxy herbicide">Phenoxy</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" 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:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Auxin#Synthetic_auxins" title="Auxin">Auxins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,4-Dichlorophenoxyacetic_acid" title="2,4-Dichlorophenoxyacetic acid">2,4-D</a></li> <li><a href="/wiki/2,4-DB" title="2,4-DB">2,4-DB</a></li> <li><a href="/wiki/Dichlorprop" title="Dichlorprop">dichlorprop</a></li> <li><a href="/wiki/Fenoprop" title="Fenoprop">fenoprop</a></li> <li><a href="/wiki/MCPA" title="MCPA">MCPA</a></li> <li><a href="/wiki/MCPB" title="MCPB">MCPB</a></li> <li><a href="/wiki/Mecoprop" title="Mecoprop">mecoprop</a></li> <li><a href="/wiki/2,4,5-Trichlorophenoxyacetic_acid" title="2,4,5-Trichlorophenoxyacetic acid">2,4,5-T</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Phenoxy_herbicide#ACCase_inhibitors" title="Phenoxy herbicide">ACCase inhibitors</a></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:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/FOP_herbicide" class="mw-redirect" title="FOP herbicide">FOP herbicides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorazifop" class="mw-redirect" title="Chlorazifop">chlorazifop</a></li> <li><a href="/wiki/Cyhalofop" class="mw-redirect" title="Cyhalofop">cyhalofop</a></li> <li><a href="/wiki/Diclofop" class="mw-redirect" title="Diclofop">diclofop</a></li> <li><a href="/wiki/Fenoxaprop" class="mw-redirect" title="Fenoxaprop">fenoxaprop</a></li> <li><a href="/wiki/Fluazifop" title="Fluazifop">fluazifop</a></li> <li><a href="/wiki/Haloxyfop" class="mw-redirect" title="Haloxyfop">haloxyfop</a></li> <li><a href="/wiki/Quizalofop" title="Quizalofop">quizalofop</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/DIM_herbicide" class="mw-redirect" title="DIM herbicide">DIM herbicides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sethoxydim" title="Sethoxydim">sethoxydim</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/PPO_herbicide" class="mw-redirect" title="PPO herbicide">Protox inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" 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:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Nitrophenol" title="Nitrophenol">Nitrophenyl ethers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acifluorfen" title="Acifluorfen">acifluorfen</a></li> <li><a href="/wiki/Aclonifen" title="Aclonifen">aclonifen</a></li> <li><a href="/wiki/Bifenox" title="Bifenox">bifenox</a></li> <li><a href="/wiki/Fluorodifen" title="Fluorodifen">fluorodifen</a></li> <li><a href="/wiki/Fomesafen" title="Fomesafen">fomesafen</a></li> <li><a href="/wiki/Lactofen" title="Lactofen">lactofen</a></li> <li><a href="/wiki/Nitrofen" title="Nitrofen">nitrofen</a></li> <li><a href="/wiki/Oxyfluorfen" title="Oxyfluorfen">oxyfluorfen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Pyrimidinedione" title="Pyrimidinedione">Pyrimidinediones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butafenacil" title="Butafenacil">butafenacil</a></li> <li><a href="/wiki/Saflufenacil" title="Saflufenacil">saflufenacil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;">Triazolinones</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carfentrazone" title="Carfentrazone">carfentrazone</a></li> <li><a href="/wiki/Sulfentrazone" title="Sulfentrazone">sulfentrazone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyridine" title="Pyridine">Pyridines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dithiopyr" title="Dithiopyr">dithiopyr</a></li> <li><a href="/wiki/Fluroxypyr" title="Fluroxypyr">fluroxypyr</a></li> <li><a href="/wiki/Imazapyr" title="Imazapyr">imazapyr</a></li> <li><a href="/w/index.php?title=Thiazopyr&action=edit&redlink=1" class="new" title="Thiazopyr (page does not exist)">thiazopyr</a></li> <li><a href="/wiki/Triclopyr" title="Triclopyr">triclopyr</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Quaternary</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Photosystem_I_inhibitors42" scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Photosystem_I" title="Photosystem I">Photosystem I inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/MPP%2B" title="MPP+">cyperquat</a></li> <li><a href="/wiki/Diquat" title="Diquat">diquat</a></li> <li><a href="/wiki/Paraquat" title="Paraquat">paraquat</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiocarbamate" title="Thiocarbamate">Thiocarbamates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benthiocarb" title="Benthiocarb">Benthiocarb</a></li> <li><a href="/wiki/Butylate_(herbicide)" title="Butylate (herbicide)">Butylate</a></li> <li><a href="/wiki/S-Ethyl_dipropylthiocarbamate" title="S-Ethyl dipropylthiocarbamate">S-Ethyl dipropylthiocarbamate</a></li> <li><a href="/wiki/Prosulfocarb" title="Prosulfocarb">prosulfocarb</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triazine" title="Triazine">Triazines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" 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:1%;line-height:1.2em;font-weight:normal;">cellulose biosynthesis inhibitors</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Indaziflam" title="Indaziflam">indaziflam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Photosystem_II" title="Photosystem II">Photosystem II inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Ametryn&action=edit&redlink=1" class="new" title="Ametryn (page does not exist)">ametryn</a></li> <li><a class="mw-selflink selflink">atrazine</a></li> <li><a href="/wiki/Cyanazine" title="Cyanazine">cyanazine</a></li> <li><a href="/wiki/Hexazinone" title="Hexazinone">hexazinone</a></li> <li><a href="/wiki/Metamitron" title="Metamitron">metamitron</a></li> <li><a href="/wiki/Metribuzin" title="Metribuzin">metribuzin</a></li> <li><a href="/wiki/Prometon" title="Prometon">prometon</a></li> <li><a href="/w/index.php?title=Prometryn&action=edit&redlink=1" class="new" title="Prometryn (page does not exist)">prometryn</a></li> <li><a href="/w/index.php?title=Propazine&action=edit&redlink=1" class="new" title="Propazine (page does not exist)">propazine</a></li> <li><a href="/wiki/Simazine" title="Simazine">simazine</a></li> <li><a href="/w/index.php?title=Simetryn&action=edit&redlink=1" class="new" title="Simetryn (page does not exist)">simetryn</a></li> <li><a href="/wiki/Terbuthylazine" title="Terbuthylazine">terbuthylazine</a></li> <li><a href="/w/index.php?title=Terbutryn&action=edit&redlink=1" class="new" title="Terbutryn (page does not exist)">terbutryn</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Urea" title="Urea">Ureas</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" 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:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Photosystem_II" title="Photosystem II">Photosystem II inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlortoluron" title="Chlortoluron">chlortoluron</a></li> <li><a href="/wiki/DCMU" title="DCMU">DCMU</a></li> <li><a href="/wiki/Difenoxuron" title="Difenoxuron">difenoxuron</a></li> <li><a href="/wiki/Isoproturon" title="Isoproturon">isoproturon</a></li> <li><a href="/wiki/Linuron" title="Linuron">linuron</a></li> <li><a href="/w/index.php?title=Monuron&action=edit&redlink=1" class="new" title="Monuron (page does not exist)">monuron</a></li> <li><a href="/wiki/Monolinuron" title="Monolinuron">monolinuron</a></li> <li><a href="/wiki/Tebuthiuron" title="Tebuthiuron">tebuthiuron</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Acetolactate_synthase" title="Acetolactate synthase">ALS inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorsulfuron" title="Chlorsulfuron">chlorsulfuron</a></li> <li><a href="/wiki/Flazasulfuron" title="Flazasulfuron">flazasulfuron</a></li> <li><a href="/wiki/Metsulfuron-methyl" title="Metsulfuron-methyl">metsulfuron-methyl</a></li> <li><a href="/wiki/Sulfometuron_methyl" title="Sulfometuron methyl">sulfometuron methyl</a></li> <li><a href="/wiki/Tribenuron" title="Tribenuron">tribenuron</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Amino-1,2,4-triazole" title="3-Amino-1,2,4-triazole">3-AT</a></li> <li><a href="/wiki/Aminocyclopyrachlor" title="Aminocyclopyrachlor">aminocyclopyrachlor</a></li> <li><a href="/wiki/Bentazon" title="Bentazon">Bentazon</a></li> <li><a href="/wiki/Clomazone" title="Clomazone">clomazone</a></li> <li><a href="/wiki/Dinoseb" title="Dinoseb">dinoseb</a></li> <li><a href="/wiki/Dinoterb" title="Dinoterb">dinoterb</a></li> <li><a href="/wiki/Juglone" title="Juglone">juglone</a></li> <li><a href="/wiki/Methazole" title="Methazole">methazole</a></li> <li><a href="/wiki/Metam_sodium" title="Metam sodium">metam sodium</a></li> <li><a href="/wiki/Pyribenzoxim" title="Pyribenzoxim">pyribenzoxim</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators1222" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</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/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</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 Estrogen receptor</span></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">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</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 Selective estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</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/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</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 G protein-coupled estrogen receptor</span></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">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a class="mw-selflink selflink">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/G-1_(drug)" class="mw-redirect" title="G-1 (drug)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</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:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a 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data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>27 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> 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