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id="toc-Uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> 5 Uses </div> </a> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Uses subsection </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Genetically_modified_crops" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Genetically_modified_crops"> <div class="vector-toc-text"> 5.1 Genetically modified crops </div> </a> <ul id="toc-Genetically_modified_crops-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Environmental_fate" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Environmental_fate"> <div class="vector-toc-text"> 6 Environmental fate </div> </a> <button aria-controls="toc-Environmental_fate-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Environmental fate subsection </button> <ul id="toc-Environmental_fate-sublist" class="vector-toc-list"> <li id="toc-Residues_in_food_products" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Residues_in_food_products"> <div class="vector-toc-text"> 6.1 Residues in food products </div> </a> <ul id="toc-Residues_in_food_products-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> 7 Toxicity </div> </a> <button aria-controls="toc-Toxicity-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Toxicity subsection </button> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> <li id="toc-Glyphosate_alone" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Glyphosate_alone"> <div class="vector-toc-text"> 7.1 Glyphosate alone </div> </a> <ul id="toc-Glyphosate_alone-sublist" class="vector-toc-list"> <li id="toc-Humans" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Humans"> <div class="vector-toc-text"> 7.1.1 Humans </div> </a> <ul id="toc-Humans-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cancer" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cancer"> <div class="vector-toc-text"> 7.1.2 Cancer </div> </a> <ul id="toc-Cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_mammals" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_mammals"> <div class="vector-toc-text"> 7.1.3 Other mammals </div> </a> <ul id="toc-Other_mammals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aquatic_fauna" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Aquatic_fauna"> <div class="vector-toc-text"> 7.1.4 Aquatic fauna </div> </a> <ul id="toc-Aquatic_fauna-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antimicrobial_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antimicrobial_activity"> <div class="vector-toc-text"> 7.1.5 Antimicrobial activity </div> </a> <ul id="toc-Antimicrobial_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Soil_biota" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Soil_biota"> <div class="vector-toc-text"> 7.1.6 Soil biota </div> </a> <ul id="toc-Soil_biota-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Endocrine_disruption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Endocrine_disruption"> <div class="vector-toc-text"> 7.1.7 Endocrine disruption </div> </a> <ul id="toc-Endocrine_disruption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effect_on_plant_health" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Effect_on_plant_health"> <div class="vector-toc-text"> 7.1.8 Effect on plant health </div> </a> <ul id="toc-Effect_on_plant_health-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Glyphosate-based_formulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Glyphosate-based_formulations"> <div class="vector-toc-text"> 7.2 Glyphosate-based formulations </div> </a> <ul id="toc-Glyphosate-based_formulations-sublist" class="vector-toc-list"> <li id="toc-Human" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Human"> <div class="vector-toc-text"> 7.2.1 Human </div> </a> <ul id="toc-Human-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aquatic_fauna_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Aquatic_fauna_2"> <div class="vector-toc-text"> 7.2.2 Aquatic fauna </div> </a> <ul id="toc-Aquatic_fauna_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Genetic_damage" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Genetic_damage"> <div class="vector-toc-text"> 7.2.3 Genetic damage </div> </a> <ul id="toc-Genetic_damage-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Government_and_organization_positions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Government_and_organization_positions"> <div class="vector-toc-text"> 7.3 Government and organization positions </div> </a> <ul id="toc-Government_and_organization_positions-sublist" class="vector-toc-list"> <li id="toc-European_Food_Safety_Authority" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#European_Food_Safety_Authority"> <div class="vector-toc-text"> 7.3.1 European Food Safety Authority </div> </a> <ul id="toc-European_Food_Safety_Authority-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-International_Agency_for_Research_on_Cancer" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#International_Agency_for_Research_on_Cancer"> <div class="vector-toc-text"> 7.3.2 International Agency for Research on Cancer </div> </a> <ul id="toc-International_Agency_for_Research_on_Cancer-sublist" class="vector-toc-list"> <li id="toc-Reviews_of_the_EFSA_and_IARC_reports" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Reviews_of_the_EFSA_and_IARC_reports"> <div class="vector-toc-text"> 7.3.2.1 Reviews of the EFSA and IARC reports </div> </a> <ul id="toc-Reviews_of_the_EFSA_and_IARC_reports-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-US_Environmental_Protection_Agency" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#US_Environmental_Protection_Agency"> <div class="vector-toc-text"> 7.3.3 US Environmental Protection Agency </div> </a> <ul id="toc-US_Environmental_Protection_Agency-sublist" class="vector-toc-list"> <li id="toc-Monsanto_response_and_campaign" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Monsanto_response_and_campaign"> <div class="vector-toc-text"> 7.3.3.1 Monsanto response and campaign </div> </a> <ul id="toc-Monsanto_response_and_campaign-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-California_Office_of_Environmental_Health_Hazard_Assessment" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#California_Office_of_Environmental_Health_Hazard_Assessment"> <div class="vector-toc-text"> 7.3.4 California Office of Environmental Health Hazard Assessment </div> </a> <ul id="toc-California_Office_of_Environmental_Health_Hazard_Assessment-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-European_Chemicals_Agency" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#European_Chemicals_Agency"> <div class="vector-toc-text"> 7.3.5 European Chemicals Agency </div> </a> <ul id="toc-European_Chemicals_Agency-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Effects_of_use" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Effects_of_use"> <div class="vector-toc-text"> 8 Effects of use </div> </a> <button aria-controls="toc-Effects_of_use-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Effects of use subsection </button> <ul id="toc-Effects_of_use-sublist" class="vector-toc-list"> <li id="toc-Emergence_of_resistant_weeds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Emergence_of_resistant_weeds"> <div class="vector-toc-text"> 8.1 Emergence of resistant weeds </div> </a> <ul id="toc-Emergence_of_resistant_weeds-sublist" class="vector-toc-list"> <li id="toc-Palmer_amaranth" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Palmer_amaranth"> <div class="vector-toc-text"> 8.1.1 Palmer amaranth </div> </a> <ul id="toc-Palmer_amaranth-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conyza_species" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Conyza_species"> <div class="vector-toc-text"> 8.1.2 Conyza species </div> </a> <ul id="toc-Conyza_species-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ryegrass" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Ryegrass"> <div class="vector-toc-text"> 8.1.3 Ryegrass </div> </a> <ul id="toc-Ryegrass-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Johnson_grass" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Johnson_grass"> <div class="vector-toc-text"> 8.1.4 Johnson grass </div> </a> <ul id="toc-Johnson_grass-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Monarch_butterfly_populations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Monarch_butterfly_populations"> <div class="vector-toc-text"> 8.2 Monarch butterfly populations </div> </a> <ul id="toc-Monarch_butterfly_populations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> 9 Legal status </div> </a> <button aria-controls="toc-Legal_status-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Legal status subsection </button> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> <li id="toc-Europe" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Europe"> <div class="vector-toc-text"> 9.1 Europe </div> </a> <ul id="toc-Europe-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_countries" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_countries"> <div class="vector-toc-text"> 9.2 Other countries </div> </a> <ul id="toc-Other_countries-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Legal_cases" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Legal_cases"> <div class="vector-toc-text"> 10 Legal cases </div> </a> <button aria-controls="toc-Legal_cases-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Legal cases subsection </button> <ul id="toc-Legal_cases-sublist" class="vector-toc-list"> <li id="toc-Lawsuits_claiming_liability_for_cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lawsuits_claiming_liability_for_cancer"> <div class="vector-toc-text"> 10.1 Lawsuits claiming liability for cancer </div> </a> <ul id="toc-Lawsuits_claiming_liability_for_cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Advertising_controversies" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Advertising_controversies"> <div class="vector-toc-text"> 10.2 Advertising controversies </div> </a> <ul id="toc-Advertising_controversies-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Trade_dumping_allegations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Trade_dumping_allegations"> <div class="vector-toc-text"> 10.3 Trade dumping allegations </div> </a> <ul id="toc-Trade_dumping_allegations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Misinformation_campaigns" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Misinformation_campaigns"> <div class="vector-toc-text"> 11 Misinformation campaigns </div> </a> <ul id="toc-Misinformation_campaigns-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> 12 See also </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"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 13 References </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"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 14 External links </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" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Glyphosate</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 48 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-48" aria-hidden="true" > 48 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Glifosaat" title="Glifosaat – Afrikaans" lang="af" hreflang="af" data-title="Glifosaat" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%BA%D9%84%D9%8A%D9%81%D9%88%D8%B3%D8%A7%D8%AA" title="غليفوسات – Arabic" lang="ar" hreflang="ar" data-title="غليفوسات" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Glifosatu" title="Glifosatu – Asturian" lang="ast" hreflang="ast" data-title="Glifosatu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target">Asturianu</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%82%D9%84%DB%8C%D9%81%D8%B3%D8%A7%D8%AA" title="قلیفسات – South Azerbaijani" lang="azb" hreflang="azb" data-title="قلیفسات" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%84%D0%BE%D0%B7%D0%B0%D1%82" title="Глифозат – Bulgarian" lang="bg" hreflang="bg" data-title="Глифозат" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Glifosat" title="Glifosat – Bosnian" lang="bs" hreflang="bs" data-title="Glifosat" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Glifosat" title="Glifosat – Catalan" lang="ca" hreflang="ca" data-title="Glifosat" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Glyfos%C3%A1t" title="Glyfosát – Czech" lang="cs" hreflang="cs" data-title="Glyfosát" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Glyfosat" title="Glyfosat – Danish" lang="da" hreflang="da" data-title="Glyfosat" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Glyphosat" title="Glyphosat – German" lang="de" hreflang="de" data-title="Glyphosat" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Gl%C3%BCfosaat" title="Glüfosaat – Estonian" lang="et" hreflang="et" data-title="Glüfosaat" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%93%CE%BB%CF%85%CF%86%CE%BF%CF%83%CE%AC%CF%84%CE%B7" title="Γλυφοσάτη – Greek" lang="el" hreflang="el" data-title="Γλυφοσάτη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Glifosato" title="Glifosato – Spanish" lang="es" hreflang="es" data-title="Glifosato" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Glifosato" title="Glifosato – Esperanto" lang="eo" hreflang="eo" data-title="Glifosato" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Glifosato" title="Glifosato – Basque" lang="eu" hreflang="eu" data-title="Glifosato" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%AF%D9%84%DB%8C%D9%81%D9%88%D8%B3%D8%A7%D8%AA" title="گلیفوسات – Persian" lang="fa" hreflang="fa" data-title="گلیفوسات" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Glyphosate" title="Glyphosate – French" lang="fr" hreflang="fr" data-title="Glyphosate" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Glifosato" title="Glifosato – Galician" lang="gl" hreflang="gl" data-title="Glifosato" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B8%80%EB%A6%AC%ED%8F%AC%EC%84%B8%EC%9D%B4%ED%8A%B8" title="글리포세이트 – Korean" lang="ko" hreflang="ko" data-title="글리포세이트" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Glifosat" title="Glifosat – Croatian" lang="hr" hreflang="hr" data-title="Glifosat" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Glifosato" title="Glifosato – Ido" lang="io" hreflang="io" data-title="Glifosato" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target">Ido</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Glifosat" title="Glifosat – Indonesian" lang="id" hreflang="id" data-title="Glifosat" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Glifosato" title="Glifosato – Italian" lang="it" hreflang="it" data-title="Glifosato" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%92%D7%9C%D7%99%D7%99%D7%A4%D7%95%D7%A1%D7%98" title="גלייפוסט – Hebrew" lang="he" hreflang="he" data-title="גלייפוסט" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Glyphosatum" title="Glyphosatum – Latin" lang="la" hreflang="la" data-title="Glyphosatum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target">Latina</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Glifoz%C3%A1t" title="Glifozát – Hungarian" lang="hu" hreflang="hu" data-title="Glifozát" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%84%D0%BE%D1%81%D0%B0%D1%82" title="Глифосат – Mongolian" lang="mn" hreflang="mn" data-title="Глифосат" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target">Монгол</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Glyfosaat" title="Glyfosaat – Dutch" lang="nl" hreflang="nl" data-title="Glyfosaat" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Glyfosat" title="Glyfosat – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Glyfosat" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Glifosat" title="Glifosat – Occitan" lang="oc" hreflang="oc" data-title="Glifosat" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Glifosat" title="Glifosat – Polish" lang="pl" hreflang="pl" data-title="Glifosat" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Glifosato" title="Glifosato – Portuguese" lang="pt" hreflang="pt" data-title="Glifosato" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D1%84%D0%BE%D1%81%D0%B0%D1%82" title="Глифосат – Russian" lang="ru" hreflang="ru" data-title="Глифосат" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%9C%E0%B7%8A%E0%B6%BD%E0%B6%BA%E0%B7%92%E0%B7%86%E0%B7%9C%E0%B7%83%E0%B7%99%E0%B6%A7%E0%B7%8A" title="ග්ලයිෆොසෙට් – Sinhala" lang="si" hreflang="si" data-title="ග්ලයිෆොසෙට්" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target">සිංහල</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Glyphosate" title="Glyphosate – Simple English" lang="en-simple" hreflang="en-simple" data-title="Glyphosate" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Glyfos%C3%A1t" title="Glyfosát – Slovak" lang="sk" hreflang="sk" data-title="Glyfosát" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Glifosat" title="Glifosat – Slovenian" lang="sl" hreflang="sl" data-title="Glifosat" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Glifosat" title="Glifosat – Serbian" lang="sr" hreflang="sr" data-title="Glifosat" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Glifosat" title="Glifosat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Glifosat" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Glyfosaatti" title="Glyfosaatti – Finnish" lang="fi" hreflang="fi" data-title="Glyfosaatti" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Glyfosat" title="Glyfosat – Swedish" lang="sv" hreflang="sv" data-title="Glyfosat" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%BF%E0%AE%B3%E0%AF%88%E0%AE%AA%E0%AF%8B%E0%AE%9A%E0%AF%87%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%81" title="கிளைபோசேட்டு – Tamil" lang="ta" hreflang="ta" data-title="கிளைபோசேட்டு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target">தமிழ்</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%81%E0%B8%A5%E0%B9%82%E0%B8%9F%E0%B9%80%E0%B8%AA%E0%B8%95" title="ไกลโฟเสต – Thai" lang="th" hreflang="th" data-title="ไกลโฟเสต" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Glifosat" title="Glifosat – Turkish" lang="tr" hreflang="tr" data-title="Glifosat" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%BB%D1%96%D1%84%D0%BE%D1%81%D0%B0%D1%82" title="Гліфосат – Ukrainian" lang="uk" hreflang="uk" data-title="Гліфосат" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Glyphosat" title="Glyphosat – Vietnamese" lang="vi" hreflang="vi" data-title="Glyphosat" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-wa mw-list-item"><a href="https://wa.wikipedia.org/wiki/Glifozate" title="Glifozate – Walloon" lang="wa" hreflang="wa" data-title="Glifozate" data-language-autonym="Walon" data-language-local-name="Walloon" class="interlanguage-link-target">Walon</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8D%89%E7%94%98%E8%86%A6" title="草甘膦 – Chinese" lang="zh" hreflang="zh" data-title="草甘膦" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li> </ul> <div class="after-portlet after-portlet-lang"><a 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<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">Systemic herbicide and crop desiccant</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Glufosinate" title="Glufosinate">Glufosinate</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">This article is about the chemical alone. For herbicides based on it, see <a href="/wiki/Glyphosate-based_herbicides" title="Glyphosate-based herbicides">Glyphosate-based herbicides</a>. For the brand-name formulation developed by Monsanto, see <a href="/wiki/Roundup_(herbicide)" title="Roundup (herbicide)">Roundup (herbicide)</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.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%}</style> <table class="infobox ib-chembox"> <caption>Glyphosate </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Glyphosate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Glyphosate.svg/220px-Glyphosate.svg.png" decoding="async" width="220" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Glyphosate.svg/330px-Glyphosate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/04/Glyphosate.svg/440px-Glyphosate.svg.png 2x" data-file-width="620" data-file-height="247" /></a> <div style="text-align:center;">Idealised <a href="/wiki/Skeletal_formula" title="Skeletal formula">skeletal formula</a> of the uncharged molecule</div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Glyphosate-from-xtal-view-2-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Glyphosate-from-xtal-view-2-3D-bs-17.png/220px-Glyphosate-from-xtal-view-2-3D-bs-17.png" decoding="async" width="220" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Glyphosate-from-xtal-view-2-3D-bs-17.png/330px-Glyphosate-from-xtal-view-2-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Glyphosate-from-xtal-view-2-3D-bs-17.png/440px-Glyphosate-from-xtal-view-2-3D-bs-17.png 2x" data-file-width="3000" data-file-height="1939" /></a> <div style="text-align:center;"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of the <a href="/wiki/Zwitterion" title="Zwitterion">zwitterion</a> (charged form), based on the <a href="/wiki/Crystal_structure" title="Crystal structure">crystal structure</a><a href="#cite_note-PHOGLY05-1">[1]</a><a href="#cite_note-2">[2]</a></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td>Pronunciation </td> <td><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˈɡlɪfəseɪt, ˈɡlaɪfə-/</a>,<a href="#cite_note-3">[3]</a> <a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ɡlaɪˈfɒseɪt/</a><a href="#cite_note-4">[4]</a><a href="#cite_note-5">[5]</a> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">N-(Phosphonomethyl)glycine</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic 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;">[(Phosphonomethyl)amino]acetic acid</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1071-83-6">1071-83-6</a> (free acid) <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" />Y</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=38641-94-0">38641-94-0</a> (isopropylammonium salt) <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" />N</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=70393-85-0">70393-85-0</a> (sesquisodium salt) <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" />N</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=81591-81-3">81591-81-3</a> (<a href="/wiki/Trimethylsulfonium" title="Trimethylsulfonium">trimethylsulfonium</a> salt) <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" />N</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><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29CNCP%28%3DO%29%28O%29O">Interactive image</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>2045054 </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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=27744">CHEBI:27744</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL95764">ChEMBL95764</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3376.html">3376</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04539">DB04539</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.012.726">100.012.726</a> <a href="https://www.wikidata.org/wiki/Q407232#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> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number">EC Number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>213-997-4</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>279222 </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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01705">C01705</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3496">3496</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>MC1075000</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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/4632WW1X5A">4632WW1X5A</a> <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" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>3077 2783 </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> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID1024122">DTXSID1024122</a> <a href="https://www.wikidata.org/wiki/Q407232#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></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; background:transparent;"><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/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9) <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" />Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XDDAORKBJWWYJS-UHFFFAOYSA-N <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" />Y</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/C3H8NO5P/c5-3(6)1-4-2-10(7,8)9/h4H,1-2H2,(H,5,6)(H2,7,8,9)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XDDAORKBJWWYJS-UHFFFAOYAE</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)CNCP(=O)(O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties<a href="#cite_note-EHC-6">[6]</a> </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>C3H8NO5P </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>169.073 g·mol−1 </td></tr> <tr> <td>Appearance </td> <td>white crystalline powder </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.704 (20 °C) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>184.5 °C (364.1 °F; 457.6 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>187 °C (369 °F; 460 K) decomposes </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>1.01 g/100 mL (20 °C) </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> </td> <td>−2.8 </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (pKa) </td> <td><2, 2.6, 5.6, 10.6 </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards<a href="#cite_note-EHC-6">[6]</a><a href="#cite_note-7">[7]</a> </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals">GHS labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="Eye Dam. 1"><img alt="Eye Dam. 1" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="Aquatic Chronic 2"><img alt="Aquatic Chronic 2" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td>Danger </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H318: Causes serious eye damage">H318</abbr>, <abbr class="abbr" title="H411: Toxic to aquatic life with long lasting effects">H411</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>Non-flammable </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0160.htm">InChem MSDS</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; 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;"><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443847907&page2=Glyphosate">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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" />Y<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" />N ?) </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> Glyphosate (<a href="/wiki/IUPAC_name" class="mw-redirect" title="IUPAC name">IUPAC name</a>: N-(phosphonomethyl)glycine) is a broad-spectrum <a href="/wiki/Systemic_herbicide" class="mw-redirect" title="Systemic herbicide">systemic herbicide</a> and <a href="/wiki/Crop_desiccant" class="mw-redirect" title="Crop desiccant">crop desiccant</a>. It is an organophosphorus compound, specifically a <a href="/wiki/Phosphonate" title="Phosphonate">phosphonate</a>, which acts by <a href="/wiki/EPSP_inhibitor" class="mw-redirect" title="EPSP inhibitor">inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase</a> (EPSP). <a href="/wiki/Glyphosate-based_herbicides" title="Glyphosate-based herbicides">Glyphosate-based herbicides</a> are used to kill <a href="/wiki/Weed" title="Weed">weeds</a>, especially annual <a href="/wiki/Forbs" class="mw-redirect" title="Forbs">broadleaf weeds</a> and grasses that compete with <a href="/wiki/Crop" title="Crop">crops</a>. Its herbicidal effectiveness was discovered by <a href="/wiki/Monsanto" title="Monsanto">Monsanto</a> chemist <a href="/wiki/John_E._Franz" title="John E. Franz">John E. Franz</a> in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name <a href="/wiki/Roundup_(herbicide)" title="Roundup (herbicide)">Roundup</a>. Monsanto's last commercially relevant United States <a href="/wiki/Patent" title="Patent">patent</a> expired in 2000. Farmers quickly adopted glyphosate for agricultural weed control, especially after Monsanto introduced glyphosate-resistant <a href="/wiki/Roundup_Ready_crops" class="mw-redirect" title="Roundup Ready crops">Roundup Ready crops</a>, enabling farmers to kill weeds without killing their crops. In 2007, glyphosate was the most used herbicide in the United States' agricultural sector and the second-most used (after <a href="/wiki/2,4-Dichlorophenoxyacetic_acid" title="2,4-Dichlorophenoxyacetic acid">2,4-D</a>) in home and garden, government and industry, and commercial applications.<a href="#cite_note-EPAusage-8">[8]</a> From the late 1970s to 2016, there was a 100-fold increase in the frequency and volume of application of <a href="/wiki/Glyphosate-based_herbicides" title="Glyphosate-based herbicides">glyphosate-based herbicides</a> (GBHs) worldwide, with further increases expected in the future. Glyphosate is absorbed through foliage, and minimally through roots, and from there translocated to growing points. It inhibits <a href="/wiki/EPSP_synthase" title="EPSP synthase">EPSP synthase</a>, a plant enzyme involved in the synthesis of three <a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">aromatic amino acids</a>: <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>, <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>, and <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>. It is therefore effective only on actively growing plants and is not effective as a <a href="/wiki/Preemergent_herbicides" class="mw-redirect" title="Preemergent herbicides">pre-emergence herbicide</a>. Crops have been <a href="/wiki/Genetic_engineering" title="Genetic engineering">genetically engineered</a> to be tolerant of glyphosate (e.g. <a href="/wiki/Roundup_Ready_soybean" class="mw-redirect" title="Roundup Ready soybean">Roundup Ready soybean</a>, the first Roundup Ready crop, also created by Monsanto), which allows farmers to use glyphosate as a post-emergence herbicide against weeds. While glyphosate and formulations such as Roundup have been approved by regulatory bodies worldwide, concerns about their effects on humans and the environment have persisted.<a href="#cite_note-biomedcentral_2016-9">[9]</a><a href="#cite_note-NatureonWHO2015-10">[10]</a> A number of regulatory and scholarly reviews have evaluated the relative toxicity of glyphosate as an herbicide. The WHO and <a href="/wiki/Food_and_Agriculture_Organization" title="Food and Agriculture Organization">FAO</a> Joint committee on pesticide residues issued a report in 2016 stating the use of glyphosate formulations does not necessarily constitute a health risk, and giving an <a href="/wiki/Acceptable_daily_intake" title="Acceptable daily intake">acceptable daily intake</a> limit of 1 milligram per kilogram of body weight per day for chronic toxicity.<a href="#cite_note-11">[11]</a> The <a href="/wiki/Scientific_consensus" title="Scientific consensus">consensus</a> among national pesticide regulatory agencies and scientific organizations is that labeled uses of glyphosate have demonstrated no evidence of human carcinogenicity.<a href="#cite_note-Tarazona-12">[12]</a> In March 2015, 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> (IARC) classified glyphosate as "probably carcinogenic in humans" (<a href="/wiki/List_of_IARC_Group_2A_carcinogens" class="mw-redirect" title="List of IARC Group 2A carcinogens">category 2A</a>) based on epidemiological studies, animal studies, and <a href="/wiki/In_vitro" title="In vitro">in vitro</a> studies.<a href="#cite_note-NatureonWHO2015-10">[10]</a><a href="#cite_note-Lancet20March2015-13">[13]</a><a href="#cite_note-IARC20March2015-14">[14]</a><a href="#cite_note-iarcmono-15">[15]</a> In contrast, the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> concluded in November 2015 that "the substance is unlikely to be <a href="/wiki/Genotoxicity" title="Genotoxicity">genotoxic</a> (i.e. damaging to <a href="/wiki/DNA" title="DNA">DNA</a>) or to pose a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogenic</a> threat to humans", later clarifying that while carcinogenic glyphosate-containing formulations may exist, studies that "look solely at the active substance glyphosate do not show this effect".<a href="#cite_note-16">[16]</a><a href="#cite_note-17">[17]</a> In 2017, the <a href="/wiki/European_Chemicals_Agency" title="European Chemicals Agency">European Chemicals Agency</a> (ECHA) classified glyphosate as causing serious eye damage and as toxic to aquatic life but did not find evidence implicating it as a carcinogen, a mutagen, toxic to reproduction, nor toxic to specific organs.<a href="#cite_note-18">[18]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Discovery">Discovery</h2></div> Glyphosate was first synthesized in 1950 by Swiss chemist Henry Martin, who worked for the Swiss company <a href="/wiki/Cilag" title="Cilag">Cilag</a>. The work was never published.<a href="#cite_note-Dill-19">[19]</a>: 1  Early studies found it to be a weak chemical <a href="/wiki/Chelation" title="Chelation">chelating agent</a>.<a href="#cite_note-Casida-2017-20">[20]</a><a href="#cite_note-21">[21]</a> Somewhat later, glyphosate was independently discovered in the <a href="/wiki/United_States" title="United States">United States</a> at Monsanto in 1970. <a href="/wiki/Monsanto" title="Monsanto">Monsanto</a> chemists had synthesized about 100 <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> of <a href="/wiki/Aminomethylphosphonic_acid" title="Aminomethylphosphonic acid">aminomethylphosphonic acid</a> as potential <a href="/wiki/Water_softening" title="Water softening">water-softening</a> agents. Two were found to have weak herbicidal activity, and <a href="/wiki/John_E._Franz" title="John E. Franz">John E. Franz</a>, a chemist at Monsanto, was asked to try to make analogs with stronger herbicidal activity. Glyphosate was the third analog he made.<a href="#cite_note-Dill-19">[19]</a>: 1–2 <a href="#cite_note-pmid11248008-22">[22]</a><a href="#cite_note-23">[23]</a> Franz received the <a href="/wiki/National_Medal_of_Technology" class="mw-redirect" title="National Medal of Technology">National Medal of Technology</a> of the United States in 1987 and the <a href="/wiki/Perkin_Medal" title="Perkin Medal">Perkin Medal</a> for Applied Chemistry in 1990 for his discoveries.<a href="#cite_note-urlThe_National_Medal_of_Technology_and_Innovation_Recipients_–_1987-24">[24]</a><a href="#cite_note-25">[25]</a><a href="#cite_note-SCI_Perkin_Medal-26">[26]</a> Monsanto developed and patented the use of glyphosate to kill weeds in the early 1970s and first brought it to market in 1974, under the Roundup brandname.<a href="#cite_note-Duke-27">[27]</a><a href="#cite_note-monsantofaq-28">[28]</a> While its initial patent<a href="#cite_note-29">[29]</a> expired in 1991, Monsanto retained exclusive rights in the United States until its patent<a href="#cite_note-30">[30]</a> on the isopropylamine salt expired in September 2000.<a href="#cite_note-31">[31]</a> In 2008, United States Department of Agriculture <a href="/wiki/Agricultural_Research_Service" title="Agricultural Research Service">Agricultural Research Service</a> (USDA ARS) scientist Stephen O. Duke and Stephen B. Powles – an Australian weed expert – described glyphosate as a "virtually ideal" herbicide.<a href="#cite_note-Duke-27">[27]</a> In 2010 Powles stated: "glyphosate is a one in a 100-year discovery that is as important for reliable global food production as penicillin is for battling disease."<a href="#cite_note-PNAS_2010_Powles-32">[32]</a> As of April 2017, the Canadian government stated that glyphosate was "the most widely used herbicide in Canada",<a href="#cite_note-pmrare-33">[33]</a> at which date the product labels were revised to ensure a limit of 20% <a href="/wiki/Polyethoxylated_tallow_amine" title="Polyethoxylated tallow amine">POEA</a> by weight.<a href="#cite_note-pmrare-33">[33]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] <a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a>'s <a href="/wiki/Pest_Management_Regulatory_Agency" title="Pest Management Regulatory Agency">Pest Management Regulatory Agency</a> found no risk to humans or the environment at that 20% limit, and that all products registered in <a href="/wiki/Canada" title="Canada">Canada</a> at that time were at or below that limit. <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glyphosate_Dissociation_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Glyphosate_Dissociation_V.1.svg/170px-Glyphosate_Dissociation_V.1.svg.png" decoding="async" width="170" height="352" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Glyphosate_Dissociation_V.1.svg/255px-Glyphosate_Dissociation_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Glyphosate_Dissociation_V.1.svg/340px-Glyphosate_Dissociation_V.1.svg.png 2x" data-file-width="505" data-file-height="1045" /></a><figcaption>Ionic states</figcaption></figure> Glyphosate is an aminophosphonic analogue of the natural amino acid <a href="/wiki/Glycine" title="Glycine">glycine</a> and, like all amino acids, exists in different ionic states depending on <a href="/wiki/PH" title="PH">pH</a>. Both the <a href="/wiki/Phosphonic_acid" class="mw-redirect" title="Phosphonic acid">phosphonic acid</a> and <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> moieties can be ionised and the <a href="/wiki/Amine" title="Amine">amine</a> group can be protonated and the substance exists as a series of <a href="/wiki/Zwitterion" title="Zwitterion">zwitterions</a>. Glyphosate is soluble in water to 12 g/L at room temperature. The original synthetic approach to glyphosate involved the reaction of <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a> with <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> followed by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> to yield a <a href="/wiki/Phosphonate" title="Phosphonate">phosphonate</a>. Glycine is then reacted with this phosphonate to yield glyphosate, and its name is taken as a contraction of the compounds used in this synthesis step, namely glycine and a phosphonate.<a href="#cite_note-Chenier-34">[34]</a> <ul><li>PCl3 + H2CO → Cl2P(=O)−CH2Cl</li> <li>Cl2P(=O)−CH2Cl + 2 H2O → (HO)2P(=O)−CH2Cl + 2 HCl</li> <li>(HO)2P(=O)−CH2Cl + H2N−CH2−COOH → (HO)2P(=O)−CH2−NH−CH2−COOH + HCl</li></ul> The main deactivation path for glyphosate is hydrolysis to <a href="/wiki/Aminomethylphosphonic_acid" title="Aminomethylphosphonic acid">aminomethylphosphonic acid</a>.<a href="#cite_note-urlwww.cdpr.ca.gov-35">[35]</a> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3></div> Two main approaches are used to synthesize glyphosate industrially, both of which proceed via the <a href="/wiki/Kabachnik%E2%80%93Fields_reaction" title="Kabachnik–Fields reaction">Kabachnik–Fields reaction</a>. The first is to react <a href="/wiki/Iminodiacetic_acid" title="Iminodiacetic acid">iminodiacetic acid</a> and <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> with <a href="/wiki/Phosphorous_acid" title="Phosphorous acid">phosphorous acid</a> (sometimes formed in situ from <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a> using the water generated by the <a href="/wiki/Mannich_reaction" title="Mannich reaction">Mannich reaction</a> of the first two reagents). <a href="/wiki/Decarboxylation" title="Decarboxylation">Decarboxylation</a> of the <a href="/wiki/Hydrophosphonylation" title="Hydrophosphonylation">hydrophosphonylation</a> product gives the desired glyphosate product. Iminodiacetic acid is usually prepared on-site by various methods depending on reagent availability.<a href="#cite_note-Dill-19">[19]</a> <a href="/wiki/File:Glyphosate_synthesis_from_iminodiacetic_acid.svg" class="mw-file-description" title="Iminodiacetic acid approach to glyphosate synthesis"><img alt="Iminodiacetic acid approach to glyphosate synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Glyphosate_synthesis_from_iminodiacetic_acid.svg/660px-Glyphosate_synthesis_from_iminodiacetic_acid.svg.png" decoding="async" width="660" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Glyphosate_synthesis_from_iminodiacetic_acid.svg/990px-Glyphosate_synthesis_from_iminodiacetic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Glyphosate_synthesis_from_iminodiacetic_acid.svg/1320px-Glyphosate_synthesis_from_iminodiacetic_acid.svg.png 2x" data-file-width="538" data-file-height="70" /></a> The second uses <a href="/wiki/Glycine" title="Glycine">glycine</a> in place of iminodiacetic acid. This avoids the need for decarboxylation but requires more careful control of <a href="/wiki/Stoichiometry" title="Stoichiometry">stoichiometry</a>, as the primary amine can react with any excess formaldehyde to form bishydroxymethylglycine, which must be hydrolysed during the <a href="/wiki/Work-up_(chemistry)" class="mw-redirect" title="Work-up (chemistry)">work-up</a> to give the desired product.<a href="#cite_note-Dill-19">[19]</a> <a href="/wiki/File:Glyphosate_synthesis_from_dimethyl_phosphite.svg" class="mw-file-description" title="Glyphosate synthesis from dimethyl phosphite"><img alt="Glyphosate synthesis from dimethyl phosphite" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Glyphosate_synthesis_from_dimethyl_phosphite.svg/440px-Glyphosate_synthesis_from_dimethyl_phosphite.svg.png" decoding="async" width="440" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Glyphosate_synthesis_from_dimethyl_phosphite.svg/660px-Glyphosate_synthesis_from_dimethyl_phosphite.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Glyphosate_synthesis_from_dimethyl_phosphite.svg/880px-Glyphosate_synthesis_from_dimethyl_phosphite.svg.png 2x" data-file-width="365" data-file-height="156" /></a> This synthetic approach is responsible for a substantial portion of the production of glyphosate in China, with considerable work having gone into recycling the triethylamine and methanol solvents.<a href="#cite_note-Dill-19">[19]</a> Progress has also been made in attempting to eliminate the need for triethylamine altogether.<a href="#cite_note-36">[36]</a> <div class="mw-heading mw-heading3"><h3 id="Impurities">Impurities</h3></div> Technical grade glyphosate is a white powder which, according to <a href="/wiki/FAO" class="mw-redirect" title="FAO">FAO</a> specification, should contain not less than 95% glyphosate. <a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a>, classified as a known human carcinogen, <a href="#cite_note-IARC2006-37">[37]</a> <a href="#cite_note-NTP2011-38">[38]</a> and <a href="/wiki/N-Nitrosoglyphosate" title="N-Nitrosoglyphosate">N-nitrosoglyphosate</a>, have been identified as toxicologically relevant impurities.<a href="#cite_note-ImpuritiesFAO2014-39">[39]</a> The FAO specification limits the formaldehyde concentration to a maximum of 1.3 g/kg glyphosate. N-Nitrosoglyphosate, "belonging to a group of impurities of particular concern as they can be activated to genotoxic carcinogens",<a href="#cite_note-ESFApeerRev2015-40">[40]</a> should not exceed 1 ppm.<a href="#cite_note-ImpuritiesFAO2014-39">[39]</a> <div class="mw-heading mw-heading2"><h2 id="Formulations">Formulations</h2></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Glyphosate-based_herbicides" title="Glyphosate-based herbicides">Glyphosate-based herbicides</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Roundup_herbicide_logo.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/2/2c/Roundup_herbicide_logo.jpg" decoding="async" width="150" height="180" class="mw-file-element" data-file-width="150" data-file-height="180" /></a><figcaption>Monsanto's <a href="/wiki/Roundup_(herbicide)" title="Roundup (herbicide)">Roundup</a> is the earliest formulation</figcaption></figure> Glyphosate is marketed in the United States and worldwide by many <a href="/wiki/Agrochemical" title="Agrochemical">agrochemical</a> companies, in different solution strengths and with various <a href="/wiki/Agricultural_spray_adjuvant" title="Agricultural spray adjuvant">adjuvants</a>, under dozens of tradenames.<a href="#cite_note-41">[41]</a><a href="#cite_note-AlbertaQuick2015-42">[42]</a><a href="#cite_note-urlISU_Weed_Science_Online_–_Glyphosate_–_A_Review-43">[43]</a><a href="#cite_note-Weed_Handbook_Glyphosate-44">[44]</a> As of 2010, more than 750 glyphosate products were on the market.<a href="#cite_note-45">[45]</a> In 2012, about half of the total global consumption of glyphosate by volume was for agricultural crops,<a href="#cite_note-ReuterMarkets2014-46">[46]</a> with <a href="/wiki/Forestry" title="Forestry">forestry</a> comprising another important market.<a href="#cite_note-47">[47]</a> Asia and the Pacific was the largest and fastest growing regional market.<a href="#cite_note-ReuterMarkets2014-46">[46]</a> As of 2014, Chinese manufacturers collectively are the world's largest producers of glyphosate and its precursors<a href="#cite_note-48">[48]</a> and account for about 30% of global exports.<a href="#cite_note-ReuterMarkets2014-46">[46]</a> Key manufacturers include Anhui Huaxing Chemical Industry Company, <a href="/wiki/BASF" title="BASF">BASF</a>, <a href="/wiki/Bayer_CropScience" class="mw-redirect" title="Bayer CropScience">Bayer CropScience</a> (which also acquired the maker of glyphosate, <a href="/wiki/Monsanto" title="Monsanto">Monsanto</a>), <a href="/wiki/Dow_AgroSciences" title="Dow AgroSciences">Dow AgroSciences</a>, <a href="/wiki/DuPont" title="DuPont">DuPont</a>, Jiangsu Good Harvest-Weien Agrochemical Company, Nantong Jiangshan Agrochemical & Chemicals Co., <a href="/wiki/Nufarm" title="Nufarm">Nufarm</a>, SinoHarvest, <a href="/wiki/Syngenta" title="Syngenta">Syngenta</a>, and Zhejiang Xinan Chemical Industrial Group Company.<a href="#cite_note-ReuterMarkets2014-46">[46]</a> Glyphosate is an acid molecule, so it is formulated as a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> for packaging and handling. Various salt formulations include isopropylamine, diammonium, monoammonium, or potassium as the <a href="/wiki/Counterion" title="Counterion">counterion</a>. The <a href="/wiki/Active_ingredient" title="Active ingredient">active ingredient</a> of the Monsanto herbicides is the <a href="/wiki/Isopropylamine" title="Isopropylamine">isopropylamine</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> of glyphosate. Another important ingredient in some formulations is the <a href="/wiki/Surfactant" title="Surfactant">surfactant</a> <a href="/wiki/Polyethoxylated_tallow_amine" title="Polyethoxylated tallow amine">polyethoxylated tallow amine (POEA)</a>. Some brands include more than one salt. Some companies report their product as acid equivalent (ae) of glyphosate acid, or some report it as active ingredient (ai) of glyphosate plus the salt, and others report both. To compare performance of different formulations, knowledge of how the products were formulated is needed. Given that different salts have different weights, the acid equivalent is a more accurate method of expressing and comparing concentrations. Adjuvant loading refers to the amount of adjuvant<a href="#cite_note-Tu_Randall_2003-49">[49]</a><a href="#cite_note-urlCrops_and_Soils_–_Penn_State_Extension-50">[50]</a> already added to the glyphosate product. Fully loaded products contain all the necessary adjuvants, including <a href="/wiki/Surfactant" title="Surfactant">surfactant</a>; some contain no adjuvant system, while other products contain only a limited amount of adjuvant (minimal or partial loading) and additional surfactants must be added to the spray tank before application.<a href="#cite_note-UDelFormulations-51">[51]</a> Products are supplied most commonly in formulations of 120, 240, 360, 480, and 680 g/L of active ingredient. The most common formulation in agriculture is 360 g/L, either alone or with added <a href="/wiki/Cationic_surfactant" class="mw-redirect" title="Cationic surfactant">cationic surfactants</a>.<a href="#cite_note-AlbertaQuick2015-42">[42]</a> For 360 grams per litre (0.013 lb/cu in) formulations, European regulations allow applications of up to 12 litres per hectare (1.1 imp gal/acre) for control of perennial weeds such as <a href="/wiki/Elytrigia_repens" class="mw-redirect" title="Elytrigia repens">couch grass</a>. More commonly, rates of 3 litres per hectare (0.27 imp gal/acre) are practiced for control of annual weeds between crops.<a href="#cite_note-52">[52]</a> <div class="mw-heading mw-heading2"><h2 id="Mode_of_action">Mode of action</h2></div> Glyphosate interferes with the <a href="/wiki/Shikimate_pathway" title="Shikimate pathway">shikimate pathway</a>, which produces the <a href="/wiki/Aromatic_amino_acids" class="mw-redirect" title="Aromatic amino acids">aromatic amino acids</a> <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>, <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> and <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> in plants and microorganisms<a href="#cite_note-Funke_2006-53">[53]</a> – but does not exist in the genome of animals, including humans.<a href="#cite_note-pmid22554242-54">[54]</a><a href="#cite_note-Casida-2017-20">[20]</a> It blocks this pathway by inhibiting the enzyme <a href="/wiki/EPSP_synthase" title="EPSP synthase">5-enolpyruvylshikimate-3-phosphate synthase</a> (EPSPS), which <a href="/wiki/Catalysis" title="Catalysis">catalyzes</a> the reaction of <a href="/wiki/Shikimate" class="mw-redirect" title="Shikimate">shikimate</a>-3-phosphate (S3P) and <a href="/wiki/Phosphoenolpyruvate" class="mw-redirect" title="Phosphoenolpyruvate">phosphoenolpyruvate</a> to form 5-enolpyruvyl-shikimate-3-phosphate (EPSP).<a href="#cite_note-pmid7396959-55">[55]</a> Glyphosate is absorbed through foliage and minimally through roots, meaning that it is only effective on actively growing plants and cannot prevent seeds from germinating.<a href="#cite_note-NPIC_Data_Sheet-56">[56]</a><a href="#cite_note-moneuro-57">[57]</a> After application, glyphosate is readily transported around the plant to growing roots and leaves and this <a href="/wiki/Herbicide#Mechanism_of_action" title="Herbicide">systemic</a> activity is important for its effectiveness.<a href="#cite_note-Duke-27">[27]</a><a href="#cite_note-Dill-19">[19]</a> Inhibiting the enzyme causes shikimate to accumulate in plant tissues and diverts energy and resources away from other processes, eventually killing the plant. While growth stops within hours of application, it takes several days for the leaves to begin <a href="/wiki/Chlorosis" title="Chlorosis">turning yellow</a>.<a href="#cite_note-hock04-58">[58]</a> Glyphosate may chelate <a href="/wiki/Co2%2B" class="mw-redirect" title="Co2+">Co2+</a> which contributes to its mode of action.<a href="#cite_note-Shick-Dunlap-2002-59">[59]</a><a href="#cite_note-Kishore-Shah-1988-60">[60]</a><a href="#cite_note-Bentley-Haslam-1990-61">[61]</a> <a href="/wiki/File:EPSPreactionII.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/EPSPreactionII.svg/660px-EPSPreactionII.svg.png" decoding="async" width="660" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/EPSPreactionII.svg/990px-EPSPreactionII.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/EPSPreactionII.svg/1320px-EPSPreactionII.svg.png 2x" data-file-width="1483" data-file-height="325" /></a> Under normal circumstances, EPSP is <a href="/wiki/Dephosphorylation" title="Dephosphorylation">dephosphorylated</a> to <a href="/wiki/Chorismate" class="mw-redirect" title="Chorismate">chorismate</a>, an essential precursor for the amino acids mentioned above.<a href="#cite_note-62">[62]</a> These amino acids are used in protein synthesis and to produce secondary metabolites such as <a href="/wiki/Folate" title="Folate">folates</a>, <a href="/wiki/Ubiquinone" class="mw-redirect" title="Ubiquinone">ubiquinones</a>, and <a href="/wiki/Naphthoquinones" class="mw-redirect" title="Naphthoquinones">naphthoquinone</a>. <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallographic</a> studies of glyphosate and EPSPS show that glyphosate functions by occupying the binding site of the phosphoenolpyruvate, mimicking an intermediate state of the ternary enzyme–substrate complex.<a href="#cite_note-pmid11171958-63">[63]</a><a href="#cite_note-64">[64]</a> Glyphosate inhibits the EPSPS enzymes of different species of plants and microbes at different rates.<a href="#cite_note-65">[65]</a><a href="#cite_note-Pollegioni_2011-66">[66]</a> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glyphosate_USA_2019.png" class="mw-file-description"><img alt="Estimated use in the US in 2019 and estimated total use from 1992 to 2019" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Glyphosate_USA_2019.png/330px-Glyphosate_USA_2019.png" decoding="async" width="330" height="428" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Glyphosate_USA_2019.png/495px-Glyphosate_USA_2019.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Glyphosate_USA_2019.png/660px-Glyphosate_USA_2019.png 2x" data-file-width="1166" data-file-height="1514" /></a><figcaption>Second graph is global</figcaption></figure> Glyphosate is effective in killing a wide variety of plants, including <a href="/wiki/Grass" class="mw-redirect" title="Grass">grasses</a> and <a href="/wiki/Broadleaf_weeds" title="Broadleaf weeds">broadleaf</a> and <a href="/wiki/Woody_plant" title="Woody plant">woody plants</a>. By volume, it is one of the most widely used herbicides.<a href="#cite_note-NPIC_Data_Sheet-56">[56]</a> In 2007, glyphosate was the most used herbicide in the United States agricultural sector, with 180 to 185 million pounds (82,000 to 84,000 tonnes) applied, the second-most used in home and garden with 5 to 8 million pounds (2,300 to 3,600 tonnes) and 13 to 15 million pounds (5,900 to 6,800 tonnes) in non-agricultural settings.<a href="#cite_note-EPAusage-8">[8]</a> It is commonly used for <a href="/wiki/Agriculture" title="Agriculture">agriculture</a>, <a href="/wiki/Horticulture" title="Horticulture">horticulture</a>, <a href="/wiki/Viticulture" title="Viticulture">viticulture</a>, and <a href="/wiki/Silviculture" title="Silviculture">silviculture</a> purposes, as well as garden maintenance (including home use). It has a relatively small effect on some clover species and <a href="/wiki/Morning_glory" title="Morning glory">morning glory</a>.<a href="#cite_note-67">[67]</a> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Roundup-in-apple-orchard.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Roundup-in-apple-orchard.jpg/170px-Roundup-in-apple-orchard.jpg" decoding="async" width="170" height="227" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Roundup-in-apple-orchard.jpg/255px-Roundup-in-apple-orchard.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Roundup-in-apple-orchard.jpg/340px-Roundup-in-apple-orchard.jpg 2x" data-file-width="600" data-file-height="800" /></a><figcaption>Glyphosate used as an alternative to mowing in an apple orchard in Ciardes, Italy</figcaption></figure> Glyphosate and related herbicides are often used in <a href="/wiki/Invasive_species" title="Invasive species">invasive species</a> eradication and <a href="/wiki/Habitat_restoration" class="mw-redirect" title="Habitat restoration">habitat restoration</a>, especially to enhance <a href="/wiki/Native_plant" class="mw-redirect" title="Native plant">native plant</a> establishment in <a href="/wiki/Prairie" title="Prairie">prairie</a> ecosystems. The controlled application is usually combined with a selective herbicide and traditional methods of weed eradication such as <a href="/wiki/Mulch" title="Mulch">mulching</a> to achieve an optimal effect.<a href="#cite_note-68">[68]</a> In many cities, glyphosate is sprayed along the sidewalks and streets, as well as crevices in between pavement where weeds often grow. However, up to 24% of glyphosate applied to hard surfaces can be run off by water.<a href="#cite_note-69">[69]</a> Glyphosate contamination of surface water is attributed to urban and agricultural use.<a href="#cite_note-pmid19482331-70">[70]</a> Glyphosate is used to clear <a href="/wiki/Railroad_track" class="mw-redirect" title="Railroad track">railroad tracks</a> and get rid of unwanted aquatic vegetation.<a href="#cite_note-moneuro-57">[57]</a> Since 1994, glyphosate has been used in aerial spraying in Colombia in <a href="/wiki/Coca_eradication" title="Coca eradication">coca eradication</a> programs; Colombia announced in May 2015 that by October, it would cease using glyphosate in these programs due to concerns about human toxicity of the chemical.<a href="#cite_note-BBCColumbia-71">[71]</a> Glyphosate is also used for <a href="/wiki/Crop_desiccation" title="Crop desiccation">crop desiccation</a> to increase harvest yield and uniformity.<a href="#cite_note-moneuro-57">[57]</a> Glyphosate itself is not a chemical <a href="/wiki/Desiccant" title="Desiccant">desiccant</a>; rather crop desiccants are so named because application just before harvest kills the crop plants so that the food crop dries from normal environmental conditions ("dry-down") more quickly and evenly.<a href="#cite_note-72">[72]</a><a href="#cite_note-74">[74]</a> Because glyphosate is systemic, excess residue levels can persist in plants due to incorrect application and this may render the crop unfit for sale.<a href="#cite_note-75">[75]</a> When applied appropriately, it can promote useful effects. In sugarcane, for example, glyphosate application increases sucrose concentration before harvest.<a href="#cite_note-LSUAgExt-76">[76]</a> In grain crops (wheat, barley, oats), uniformly dried crops do not have to be <a href="/wiki/Windrow" title="Windrow">windrowed</a> (swathed and dried) prior to harvest, but can easily be straight-cut and harvested. This saves the farmer time and money, which is important in northern regions where the growing season is short, and it enhances grain storage when the grain has a lower and more uniform moisture content.<a href="#cite_note-moneuro-57">[57]</a><a href="#cite_note-77">[77]</a><a href="#cite_note-78">[78]</a> <div class="mw-heading mw-heading3"><h3 id="Genetically_modified_crops">Genetically modified crops</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Genetically_modified_crops" title="Genetically modified crops">Genetically modified crops</a>, <a href="/wiki/Genetically_modified_organism" title="Genetically modified organism">Genetically modified organism</a>, <a href="/wiki/Genetically_modified_food" title="Genetically modified food">Genetically modified food</a>, and <a href="/wiki/Genetically_modified_food_controversies" title="Genetically modified food controversies">Genetically modified food controversies</a></div> Some micro-organisms have a version of <a href="/w/index.php?title=5-enolpyruvoyl-shikimate-3-phosphate_synthetase&action=edit&redlink=1" class="new" title="5-enolpyruvoyl-shikimate-3-phosphate synthetase (page does not exist)">5-enolpyruvoyl-shikimate-3-phosphate synthetase</a> (EPSPS) resistant to glyphosate inhibition. A version of the enzyme that was both resistant to glyphosate and that was still efficient enough to drive adequate plant growth was identified by Monsanto scientists after much trial and error in an <a href="/wiki/Agrobacterium" title="Agrobacterium">Agrobacterium</a> strain called CP4, which was found surviving in a waste-fed column at a glyphosate production facility.<a href="#cite_note-Pollegioni_2011-66">[66]</a><a href="#cite_note-Green_2011-79">[79]</a><a href="#cite_note-80">[80]</a>: 56  This CP4 EPSPS gene was <a href="/wiki/Molecular_cloning" title="Molecular cloning">cloned</a> and <a href="/wiki/Transfection" title="Transfection">transfected</a> into soybeans. In 1996, genetically modified soybeans were made commercially available.<a href="#cite_note-urlMonsanto_|_Company_History-81">[81]</a> Current glyphosate-resistant crops include soy, <a href="/wiki/Maize" title="Maize">maize</a> (corn), <a href="/wiki/Canola" class="mw-redirect" title="Canola">canola</a>, <a href="/wiki/Alfalfa" title="Alfalfa">alfalfa</a>, <a href="/wiki/Sugar_beets" class="mw-redirect" title="Sugar beets">sugar beets</a>, and <a href="/wiki/Cotton" title="Cotton">cotton</a>, with <a href="/wiki/Wheat" title="Wheat">wheat</a> still under development. In 2023, 91% of corn, 95% of soybeans, and 94% of cotton produced in the United States were from strains that were genetically modified to be tolerant to multiple herbicides, including <a href="/wiki/Dicamba" title="Dicamba">dicamba</a>, <a href="/wiki/Glufosinate" title="Glufosinate">glufosinate</a>, and glyphosate.<a href="#cite_note-USDA1-82">[82]</a> <div class="mw-heading mw-heading2"><h2 id="Environmental_fate">Environmental fate</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Landscape_company_Oklahoma.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Landscape_company_Oklahoma.jpg/220px-Landscape_company_Oklahoma.jpg" decoding="async" width="220" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Landscape_company_Oklahoma.jpg/330px-Landscape_company_Oklahoma.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Landscape_company_Oklahoma.jpg/440px-Landscape_company_Oklahoma.jpg 2x" data-file-width="1532" data-file-height="1099" /></a><figcaption><a href="/wiki/Landscaping" title="Landscaping">Landscaping</a> company in <a href="/wiki/Oklahoma" title="Oklahoma">Oklahoma</a> applying a weed control product that contains glyphosate</figcaption></figure> Glyphosate has four ionizable sites, with <a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a> values of 2.0, 2.6, 5.6 and 10.6.<a href="#cite_note-83">[83]</a> Therefore, it is a zwitterion in aqueous solutions and is expected to exist almost entirely in zwitterionic forms in the environment. Zwitterions generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts.<a href="#cite_note-84">[84]</a> Glyphosate strongly <a href="/wiki/Sorption" title="Sorption">sorbs</a> onto <a href="/wiki/Soil" title="Soil">soil</a> minerals, and, with the exception of <a href="/wiki/Colloid-facilitated_transport" title="Colloid-facilitated transport">colloid-facilitated transport</a>, its soluble residues are expected to be poorly mobile in the free porewater of soils. The spatial extent of <a href="/wiki/Groundwater" title="Groundwater">ground</a> and <a href="/wiki/Surface_water" title="Surface water">surface water</a> pollution is therefore considered to be relatively limited.<a href="#cite_note-Borggaard_2008-85">[85]</a> Glyphosate is readily degraded by soil microbes to <a href="/wiki/Aminomethylphosphonic_acid" title="Aminomethylphosphonic acid">aminomethylphosphonic acid</a> (AMPA, which like glyphosate strongly adsorbs to soil solids and is thus unlikely to leach to groundwater). Though both glyphosate and AMPA are commonly detected in water bodies, a portion of the AMPA detected may actually be the result of degradation of detergents and other <a href="/wiki/Aminophosphonate" title="Aminophosphonate">aminophosphonates</a> rather than degradation of glyphosate.<a href="#cite_note-86">[86]</a> The proportion of AMPA from non-glyphosate sources is claimed to be higher in Europe compared to USA.<a href="#cite_note-u859-87">[87]</a> Glyphosate does have the potential to contaminate surface waters due to its aquatic use patterns and through erosion, as it adsorbs to <a href="/wiki/Colloid" title="Colloid">colloidal</a> soil particles suspended in <a href="/wiki/Surface_runoff" title="Surface runoff">runoff</a>. Detection in surface waters (particularly downstream from agricultural uses) has been reported as both broad and frequent by the <a href="/wiki/United_States_Geological_Survey" title="United States Geological Survey">United States Geological Survey</a> (USGS) researchers,<a href="#cite_note-88">[88]</a> although other similar research found equal frequencies of detection in urban-dominated small streams.<a href="#cite_note-89">[89]</a> Rain events can trigger dissolved glyphosate loss in transport-prone soils.<a href="#cite_note-90">[90]</a> The mechanism of glyphosate sorption to soil is similar to that of <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> fertilizers, the presence of which can reduce glyphosate sorption.<a href="#cite_note-91">[91]</a> Phosphate fertilizers are subject to release from sediments into water bodies under <a href="https://en.wiktionary.org/wiki/anaerobic" class="extiw" title="wikt:anaerobic">anaerobic</a> conditions, and similar release can also occur with glyphosate, though significant impact of glyphosate release from sediments has not been established.<a href="#cite_note-92">[92]</a> Limited leaching can occur after high rainfall after application. If glyphosate reaches surface water, it is not broken down readily by water or sunlight.<a href="#cite_note-epa_reds-93">[93]</a><a href="#cite_note-Borggaard_2008-85">[85]</a> The <a href="/wiki/Half-life" title="Half-life">half-life</a> of glyphosate in soil ranges between 2 and 197 days; a typical field half-life of 47 days has been suggested. Soil and climate conditions affect glyphosate's persistence in soil. The median half-life of glyphosate in water varies from a few to 91 days.<a href="#cite_note-NPIC_Data_Sheet-56">[56]</a> At a site in Texas, half-life was as little as three days. A site in Iowa had a half-life of 141.9 days.<a href="#cite_note-Giesy2000-94">[94]</a> The glyphosate metabolite AMPA has been found in Swedish forest soils up to two years after a glyphosate application. In this case, the persistence of AMPA was attributed to the soil being frozen for most of the year.<a href="#cite_note-pmid2806176-95">[95]</a> Glyphosate adsorption to soil, and later release from soil, varies depending on the kind of soil.<a href="#cite_note-pmid19447533-96">[96]</a><a href="#cite_note-97">[97]</a> Glyphosate is generally less persistent in water than in soil, with 12- to 60-day persistence observed in Canadian ponds, although persistence of over a year has been recorded in the sediments of American ponds.<a href="#cite_note-epa_reds-93">[93]</a> The half-life of glyphosate in water is between 12 days and 10 weeks.<a href="#cite_note-Sparling-98">[98]</a> <div class="mw-heading mw-heading3"><h3 id="Residues_in_food_products">Residues in food products</h3></div> According to the <a href="/wiki/National_Pesticide_Information_Center" title="National Pesticide Information Center">National Pesticide Information Center</a> fact sheet, glyphosate is not included in compounds tested for by the Food and Drug Administration's Pesticide Residue Monitoring Program, nor in the United States Department of Agriculture's Pesticide Data Program.<a href="#cite_note-NPIC_Data_Sheet-56">[56]</a> The U.S. has determined the <a href="/wiki/Acceptable_daily_intake" title="Acceptable daily intake">acceptable daily intake</a> of glyphosate at 1.75 milligrams per kilogram of body weight per day (mg/kg/bw/day) while the European Union has set it at 0.5.<a href="#cite_note-99">[99]</a> Pesticide residue controls carried out by EU Member States in 2016 analysed 6,761 samples of food products for glyphosate residues. 3.6% of the samples contained <a href="/wiki/Limit_of_quantification" class="mw-redirect" title="Limit of quantification">quantifiable</a> glyphosate residue levels with 19 samples (0.28%) exceeding the European <a href="/wiki/Maximum_residue_limit" title="Maximum residue limit">maximum residue levels</a> (MRLs), which included six samples of honey and other apicultural products (MRL = 0.05 mg/kg) and eleven samples of buckwheat and other pseudo‐cereals (MRL = 0.1 mg/kg). Glyphosate residues below the European MRLs were most frequently found in dry lentils, linseeds, soya beans, dry peas, tea, buckwheat, barley, wheat and rye.<a href="#cite_note-ESFA2018residues-100">[100]</a> In Canada, a survey of 7,955 samples of food found that 42.3% contained detectable quantities of glyphosate and only 0.6% contained a level higher than the Canadian MRL of 0.1 mg/kg for most foods and 4 mg/kg for beans and chickpeas. Of the products that exceeded MRLs, one third were organic products. <a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a> concluded based on the analysis "that there was no long-term health risk to Canadian consumers from exposure to the levels of glyphosate".<a href="#cite_note-101">[101]</a> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2></div> Glyphosate is the active ingredient in herbicide formulations containing it. However, in addition to glyphosate salts, commercial formulations of glyphosate contain additives (known as adjuvants) such as <a href="/wiki/Surfactant" title="Surfactant">surfactants</a>, which vary in nature and concentration. Surfactants such as <a href="/wiki/Polyethoxylated_tallow_amine" title="Polyethoxylated tallow amine">polyethoxylated tallow amine</a> (POEA) are added to glyphosate to enable it to wet the leaves and penetrate the <a href="/wiki/Plant_cuticle" title="Plant cuticle">cuticle</a> of the plants. <div class="mw-heading mw-heading3"><h3 id="Glyphosate_alone">Glyphosate alone</h3></div> <div class="mw-heading mw-heading4"><h4 id="Humans">Humans</h4></div> The acute oral toxicity for mammals is low,<a href="#cite_note-pmid29117584-102">[102]</a> but death has been reported after deliberate overdose of <a href="/wiki/Dose%E2%80%93response_relationship" title="Dose–response relationship">concentrated</a> formulations.<a href="#cite_note-pmid22835958-103">[103]</a> The surfactants in glyphosate formulations can increase the relative acute toxicity of the formulation.<a href="#cite_note-Bradberry_2004-104">[104]</a><a href="#cite_note-SERA2003-105">[105]</a> Glyphosate is less toxic than 94% of herbicides, and is also less toxic than household chemicals such as <a href="/wiki/Table_salt" class="mw-redirect" title="Table salt">table salt</a> or <a href="/wiki/Vinegar" title="Vinegar">vinegar</a>.<a href="#cite_note-PennStateExt-106">[106]</a> In a 2017 risk assessment, the European Chemicals Agency (ECHA) wrote: "There is very limited information on skin irritation in humans. Where skin irritation has been reported, it is unclear whether it is related to glyphosate or co-formulants in glyphosate-containing herbicide formulations." The ECHA concluded that available human data was insufficient to support classification for skin corrosion or irritation.<a href="#cite_note-107">[107]</a> Inhalation is a minor route of exposure, but spray mist may cause oral or nasal discomfort, an unpleasant taste in the mouth, or tingling and irritation in the throat. Eye exposure may lead to mild conjunctivitis. Superficial corneal injury is possible if irrigation is delayed or inadequate.<a href="#cite_note-Bradberry_2004-104">[104]</a> <div class="mw-heading mw-heading4"><h4 id="Cancer">Cancer</h4></div> The <a href="/wiki/Scientific_consensus" title="Scientific consensus">consensus</a> among national pesticide regulatory agencies and scientific organizations is that labeled uses of glyphosate have demonstrated no evidence of human carcinogenicity.<a href="#cite_note-Tarazona-12">[12]</a> The Joint FAO/WHO Meeting on Pesticide Residues (JMPR),<a href="#cite_note-JMPR2016-108">[108]</a> the <a href="/wiki/European_Commission" title="European Commission">European Commission</a>, the Canadian <a href="/wiki/Pest_Management_Regulatory_Agency" title="Pest Management Regulatory Agency">Pest Management Regulatory Agency</a>, the <a href="/wiki/Australian_Pesticides_and_Veterinary_Medicines_Authority" title="Australian Pesticides and Veterinary Medicines Authority">Australian Pesticides and Veterinary Medicines Authority</a><a href="#cite_note-109">[109]</a> and the German <a href="/wiki/Federal_Institute_for_Risk_Assessment" title="Federal Institute for Risk Assessment">Federal Institute for Risk Assessment</a><a href="#cite_note-110">[110]</a> have concluded that there is no evidence that glyphosate poses a carcinogenic or <a href="/wiki/Genotoxic" class="mw-redirect" title="Genotoxic">genotoxic</a> risk to humans. The <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> (EPA) has classified glyphosate as "not likely to be carcinogenic to humans."<a href="#cite_note-111">[111]</a><a href="#cite_note-CARC2015-112">[112]</a> One international scientific organization, the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a>, classified glyphosate in <a href="/wiki/List_of_IARC_Group_2A_carcinogens" class="mw-redirect" title="List of IARC Group 2A carcinogens">Group 2A</a>, "probably carcinogenic to humans" in 2015.<a href="#cite_note-iarcmono-15">[15]</a><a href="#cite_note-Lancet20March2015-13">[13]</a> As of 2020<a class="external text" href="https://en.wikipedia.org/w/index.php?title=Glyphosate&action=edit">[update]</a>, the evidence for long-term exposure to glyphosate increasing the risk of human cancer remains inconclusive.<a href="#cite_note-113">[113]</a> There is weak evidence human cancer risk might increase as a result of occupational exposure to large amounts of glyphosate, such as in agricultural work, but no good evidence of such a risk from home use, such as in domestic gardening.<a href="#cite_note-cruk-114">[114]</a><a href="#cite_note-115">[115]</a> Although some small studies have suggested an association between glyphosate and <a href="/wiki/Non-hodgkin_lymphoma" class="mw-redirect" title="Non-hodgkin lymphoma">non-hodgkin lymphoma</a>, subsequent work confirmed the likelihood this work suffered from bias, and the association could not be demonstrated in more robust studies.<a href="#cite_note-boff-116">[116]</a><a href="#cite_note-EFSA2023-117">[117]</a><a href="#cite_note-118">[118]</a> <div class="mw-heading mw-heading4"><h4 id="Other_mammals">Other mammals</h4></div> Amongst mammals, glyphosate is considered to have "low to very low toxicity". The <a href="/wiki/LD50" class="mw-redirect" title="LD50">LD50</a> of glyphosate is 5,000 mg/kg for rats, 10,000 mg/kg in mice and 3,530 mg/kg in goats. The acute dermal LD50 in rabbits is greater than 2,000 mg/kg. Indications of glyphosate toxicity in animals typically appear within 30 to 120 minutes following ingestion of a large enough dose, and include initial excitability and <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a>, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>, depression, and <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a>, although severe toxicity can develop into collapse and convulsions.<a href="#cite_note-NPIC_Data_Sheet-56">[56]</a> A review of unpublished short-term rabbit-feeding studies reported severe toxicity effects at 150 mg/kg/day and "<a href="/wiki/NOAEL" class="mw-redirect" title="NOAEL">no observed adverse effect level</a>" doses ranging from 50 to 200 mg/kg/day.<a href="#cite_note-pmid23286529-119">[119]</a> Glyphosate can have carcinogenic effects in nonhuman mammals. These include the induction of positive trends in the incidence of <a href="/wiki/Kidney_cancer" title="Kidney cancer">renal tubule carcinoma</a> and <a href="/wiki/Haemangiosarcoma" class="mw-redirect" title="Haemangiosarcoma">haemangiosarcoma</a> in male mice, and increased <a href="/wiki/Pancreatic_cancer" title="Pancreatic cancer">pancreatic islet-cell adenoma</a> in male rats.<a href="#cite_note-Lancet20March2015-13">[13]</a> In reproductive toxicity studies performed in rats and rabbits, no adverse maternal or offspring effects were seen at doses below 175–293 mg/kg/day.<a href="#cite_note-NPIC_Data_Sheet-56">[56]</a> Large quantities of glyphosate-based herbicides may cause life-threatening <a href="/wiki/Arrhythmia" title="Arrhythmia">arrhythmias</a> in mammals. Evidence also shows that such herbicides cause direct electrophysiological changes in the cardiovascular systems of rats and rabbits.<a href="#cite_note-120">[120]</a> <div class="mw-heading mw-heading4"><h4 id="Aquatic_fauna">Aquatic fauna</h4></div> In many freshwater invertebrates, glyphosate has a 48-hour <a href="/wiki/LC50" class="mw-redirect" title="LC50">LC50</a> ranging from 55 to 780 ppm. The 96-hour LC50 is 281 ppm for <a href="/wiki/Grass_shrimp" class="mw-redirect" title="Grass shrimp">grass shrimp</a> (Palaemonetas vulgaris) and 934 ppm for <a href="/wiki/Fiddler_crabs" class="mw-redirect" title="Fiddler crabs">fiddler crabs</a> (Uca pagilator). These values make glyphosate "slightly toxic to practically non-toxic".<a href="#cite_note-NPIC_Data_Sheet-56">[56]</a> <div class="mw-heading mw-heading4"><h4 id="Antimicrobial_activity">Antimicrobial activity</h4></div> The <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> activity of glyphosate has been described in the microbiology literature since its discovery in 1970 and the description of glyphosate's mechanism of action in 1972. Efficacy was described for numerous bacteria and fungi.<a href="#cite_note-121">[121]</a> Glyphosate can control the growth of <a href="/wiki/Apicomplexa" title="Apicomplexa">apicomplexan</a> parasites, such as <a href="/wiki/Toxoplasma_gondii" title="Toxoplasma gondii">Toxoplasma gondii</a>, <a href="/wiki/Plasmodium_falciparum" title="Plasmodium falciparum">Plasmodium falciparum</a> (malaria), and <a href="/wiki/Cryptosporidium_parvum" title="Cryptosporidium parvum">Cryptosporidium parvum</a>, and has been considered an antimicrobial agent in mammals.<a href="#cite_note-pmid11865437-122">[122]</a> Inhibition can occur with some <a href="/wiki/Rhizobium" title="Rhizobium">Rhizobium</a> species important for soybean nitrogen fixation, especially under moisture stress.<a href="#cite_note-pmid15224916-123">[123]</a> <div class="mw-heading mw-heading4"><h4 id="Soil_biota">Soil biota</h4></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glyphosate_degradation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Glyphosate_degradation.svg/330px-Glyphosate_degradation.svg.png" decoding="async" width="330" height="226" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Glyphosate_degradation.svg/495px-Glyphosate_degradation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Glyphosate_degradation.svg/660px-Glyphosate_degradation.svg.png 2x" data-file-width="820" data-file-height="562" /></a><figcaption>Degradation pathway of glyphosate in the ground<a href="#cite_note-Giesy2000-94">[94]</a></figcaption></figure> When glyphosate comes into contact with the soil, it can be bound to <a href="/wiki/Soil_texture" title="Soil texture">soil particles</a>, thereby slowing its degradation.<a href="#cite_note-epa_reds-93">[93]</a><a href="#cite_note-Andrea-124">[124]</a> Glyphosate and its degradation product, <a href="/wiki/Aminomethylphosphonic_acid" title="Aminomethylphosphonic acid">aminomethylphosphonic acid</a> are considered to be much more benign toxicologically and environmentally than most of the herbicides replaced by glyphosate.<a href="#cite_note-125">[125]</a> A 2016 meta-analysis concluded that at typical application rates glyphosate had no effect on soil microbial biomass or respiration.<a href="#cite_note-NguyenRose2016-126">[126]</a> A 2016 review noted that contrasting effects of glyphosate on earthworms have been found in different experiments with some species unaffected, but others losing weight or avoiding treated soil. Further research is required to determine the impact of glyphosate on earthworms in complex ecosystems.<a href="#cite_note-RoseCavagnaro2016-127">[127]</a> <div class="mw-heading mw-heading4"><h4 id="Endocrine_disruption">Endocrine disruption</h4></div> In 2007, the EPA selected glyphosate for further screening through its Endocrine Disruptor Screening Program (EDSP). Selection for this program is based on a compound's prevalence of use and does not imply particular suspicion of <a href="/wiki/Endocrine" class="mw-redirect" title="Endocrine">endocrine</a> activity.<a href="#cite_note-128">[128]</a> On June 29, 2015, the EPA released the Weight of Evidence Conclusions of the EDSP Tier 1 screening for glyphosate, recommending that glyphosate not be considered for Tier 2 testing. The Weight of Evidence conclusion stated "...there was no convincing evidence of potential interaction with the <a href="/wiki/Estrogen" title="Estrogen">estrogen</a>, <a href="/wiki/Androgen" title="Androgen">androgen</a> or <a href="/wiki/Thyroid" title="Thyroid">thyroid</a> pathways."<a href="#cite_note-129">[129]</a> A review of the evidence by the European Food Safety Authority published in September 2017 showed conclusions similar to those of the EPA report.<a href="#cite_note-130">[130]</a> <div class="mw-heading mw-heading4"><h4 id="Effect_on_plant_health">Effect on plant health</h4></div> Some studies have found causal relationships between glyphosate and increased or decreased disease resistance.<a href="#cite_note-131">[131]</a> Exposure to glyphosate has been shown to change the species composition of <a href="/wiki/Endophyte" title="Endophyte">endophytic bacteria</a> in plant hosts, which is highly variable.<a href="#cite_note-132">[132]</a> <div class="mw-heading mw-heading3"><h3 id="Glyphosate-based_formulations">Glyphosate-based formulations</h3></div> Glyphosate-based formulations may contain a number of <a href="/wiki/Agricultural_spray_adjuvant" title="Agricultural spray adjuvant">adjuvants</a>, the identities of which may be proprietary.<a href="#cite_note-www2.epa.gov-133">[133]</a> Surfactants are used in herbicide formulations as <a href="/wiki/Wetting" title="Wetting">wetting</a> agents, to maximize coverage and aid penetration of the herbicide(s) through plant leaves. As agricultural spray adjuvants, surfactants may be pre-mixed into commercial formulations or they may be purchased separately and mixed on-site.<a href="#cite_note-134">[134]</a> <a href="/wiki/Polyethoxylated_tallow_amine" title="Polyethoxylated tallow amine">Polyethoxylated tallow amine</a> (POEA) is a surfactant used in the original Roundup formulation and was commonly used in 2015.<a href="#cite_note-usgs.glyphosate.poea-135">[135]</a> Different versions of Roundup have included different percentages of POEA. A 1997 US government report said that Roundup is 15% POEA while Roundup Pro is 14.5%.<a href="#cite_note-fs.fed.us-136">[136]</a> Since POEA is more toxic to fish and amphibians than glyphosate alone, POEA is not allowed in aquatic formulations.<a href="#cite_note-Langeland-137">[137]</a><a href="#cite_note-fs.fed.us-136">[136]</a><a href="#cite_note-Mann-138">[138]</a> A 2000 review of the ecotoxicological data on Roundup shows at least 58 studies exist on the effects of Roundup on a range of organisms.<a href="#cite_note-Giesy2000-94">[94]</a> This review concluded that "...for terrestrial uses of Roundup minimal acute and chronic risk was predicted for potentially exposed non-target organisms".<a href="#cite_note-139">[139]</a> <div class="mw-heading mw-heading4"><h4 id="Human">Human</h4></div> Overall, there is no conclusive evidence on glyphosate's effect on human health.<a href="#cite_note-140">[140]</a><a href="#cite_note-141">[141]</a> <a href="/wiki/Acute_toxicity" title="Acute toxicity">Acute toxicity</a> and <a href="/wiki/Chronic_toxicity" title="Chronic toxicity">chronic toxicity</a> are dose-related. Skin exposure to ready-to-use concentrated glyphosate formulations can cause irritation, and <a href="/wiki/Contact_dermatitis#Photocontact_dermatitis" title="Contact dermatitis">photocontact dermatitis</a> has been occasionally reported. These effects are probably due to the preservative <a href="/wiki/Benzisothiazolin-3-one" class="mw-redirect" title="Benzisothiazolin-3-one">benzisothiazolin-3-one</a>. Severe skin burns are very rare.<a href="#cite_note-Bradberry_2004-104">[104]</a> Inhalation is a minor route of exposure, but spray mist may cause oral or nasal discomfort, an unpleasant taste in the mouth, or tingling and irritation in the throat. Eye exposure may lead to mild conjunctivitis. Superficial corneal injury is possible if irrigation is delayed or inadequate.<a href="#cite_note-Bradberry_2004-104">[104]</a> Death has been reported after deliberate overdose.<a href="#cite_note-Bradberry_2004-104">[104]</a><a href="#cite_note-pmid22835958-103">[103]</a> Ingestion of Roundup ranging from 85 to 200 ml (of 41% solution) has resulted in death within hours of ingestion, although it has also been ingested in quantities as large as 500 ml with only mild or moderate symptoms.<a href="#cite_note-pmid1673618-142">[142]</a> Adult consumption of more than 85 ml of concentrated product can lead to corrosive esophageal burns and kidney or liver damage. More severe cases cause "respiratory distress, impaired consciousness, <a href="/wiki/Pulmonary_edema" title="Pulmonary edema">pulmonary edema</a>, <a href="/wiki/Pulmonary_infiltrate" title="Pulmonary infiltrate">infiltration</a> on chest X-ray, shock, arrhythmias, renal failure requiring haemodialysis, metabolic acidosis, and hyperkalaemia" and death is often preceded by <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a> and <a href="/wiki/Ventricular_arrhythmia" class="mw-redirect" title="Ventricular arrhythmia">ventricular arrhythmias</a>.<a href="#cite_note-Bradberry_2004-104">[104]</a> While the surfactants in formulations generally do not increase the toxicity of glyphosate itself, it is likely that they contribute to its acute toxicity.<a href="#cite_note-Bradberry_2004-104">[104]</a> <div class="mw-heading mw-heading4"><h4 id="Aquatic_fauna_2">Aquatic fauna</h4></div> Glyphosate products for aquatic use generally do not use surfactants, and aquatic formulations do not use POEA due to aquatic organism toxicity.<a href="#cite_note-Langeland-137">[137]</a> Due to the presence of POEA, such glyphosate formulations only allowed for terrestrial use are more toxic for amphibians and fish than glyphosate alone.<a href="#cite_note-Langeland-137">[137]</a><a href="#cite_note-fs.fed.us-136">[136]</a><a href="#cite_note-Mann-138">[138]</a> The half-life of POEA (21–42 days) is longer than that for glyphosate (7–14 days) in aquatic environments.<a href="#cite_note-Mesnage-143">[143]</a> Aquatic organism exposure risk to terrestrial formulations with POEA is limited to drift or temporary water pockets where concentrations would be much lower than label rates.<a href="#cite_note-Langeland-137">[137]</a> Some researchers have suggested the toxicity effects of pesticides on amphibians may be different from those of other aquatic fauna because of their lifestyle; amphibians may be more susceptible to the toxic effects of pesticides because they often prefer to breed in shallow, <a href="/wiki/Lentic" class="mw-redirect" title="Lentic">lentic</a>, or ephemeral pools. These habitats do not necessarily constitute formal water-bodies and can contain higher concentrations of pesticide compared to larger water-bodies.<a href="#cite_note-Mann-138">[138]</a><a href="#cite_note-Govindarajulu-144">[144]</a> Studies in a variety of amphibians have shown the toxicity of GBFs containing POEA to amphibian larvae. These effects include interference with gill morphology and mortality from either the loss of osmotic stability or <a href="/wiki/Asphyxiation" class="mw-redirect" title="Asphyxiation">asphyxiation</a>. At sub-lethal concentrations, exposure to POEA or glyphosate/POEA formulations have been associated with delayed development, accelerated development, reduced size at <a href="/wiki/Metamorphosis" title="Metamorphosis">metamorphosis</a>, developmental malformations of the tail, mouth, eye and head, histological indications of intersex and symptoms of oxidative stress.<a href="#cite_note-Mann-138">[138]</a> Glyphosate-based formulations can cause <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a> in bullfrog tadpoles.<a href="#cite_note-iarcmono-15">[15]</a> A 2003 study of various formulations of glyphosate found, "[the] risk assessments based on estimated and measured concentrations of glyphosate that would result from its use for the control of undesirable plants in wetlands and over-water situations showed that the risk to aquatic organisms is negligible or small at application rates less than 4 kg/ha and only slightly greater at application rates of 8 kg/ha."<a href="#cite_note-Solomon-145">[145]</a> A 2013 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> reviewed the available data related to potential impacts of glyphosate-based herbicides on amphibians. According to the authors, the use of glyphosate-based pesticides cannot be considered the major cause of amphibian decline, the bulk of which occurred prior to the widespread use of glyphosate or in pristine tropical areas with minimal glyphosate exposure. The authors recommended further study of per-species and per-development-stage chronic toxicity, of environmental glyphosate levels, and ongoing analysis of data relevant to determining what if any role glyphosate might be playing in worldwide amphibian decline, and suggest including amphibians in standardized test batteries.<a href="#cite_note-ReferenceA-146">[146]</a> <div class="mw-heading mw-heading4"><h4 id="Genetic_damage">Genetic damage</h4></div> Several studies have not found <a href="/wiki/Mutagen" title="Mutagen">mutagenic effects</a>,<a href="#cite_note-147">[147]</a> so glyphosate has not been listed in the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> or the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> databases.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Various other studies suggest glyphosate may be mutagenic.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] The IARC monograph noted that glyphosate-based formulations can cause DNA strand breaks in various <a href="/wiki/Class_(biology)" title="Class (biology)">taxa</a> of animals in vitro.<a href="#cite_note-iarcmono-15">[15]</a> <div class="mw-heading mw-heading3"><h3 id="Government_and_organization_positions">Government and organization positions</h3></div> <div class="mw-heading mw-heading4"><h4 id="European_Food_Safety_Authority">European Food Safety Authority</h4></div> A 2013 systematic review by the <a href="/wiki/Federal_Institute_for_Risk_Assessment" title="Federal Institute for Risk Assessment">German Institute for Risk Assessment</a> (BfR) examined more than 1000<a href="#cite_note-148">[148]</a> <a href="/wiki/Epidemiological" class="mw-redirect" title="Epidemiological">epidemiological</a> studies, animal studies, and <a href="/wiki/In_vitro" title="In vitro">in vitro</a> studies. It found that "no classification and labelling for carcinogenicity is warranted" and did not recommend a carcinogen classification of either 1A or 1B.<a href="#cite_note-BFR2014-149">[149]</a>: 34–37, 139  It provided the review to <a href="/wiki/EFSA" class="mw-redirect" title="EFSA">EFSA</a> in January 2014 which published it in December 2014.<a href="#cite_note-BFR2014-149">[149]</a><a href="#cite_note-Renewal_Assessment_Report-150">[150]</a><a href="#cite_note-151">[151]</a> In November 2015, EFSA published its conclusion in the Renewal Assessment Report (RAR), stating it was "unlikely to pose a carcinogenic hazard to humans".<a href="#cite_note-152">[152]</a> The <a href="/wiki/EU" class="mw-redirect" title="EU">EU</a> was largely informed by this report when it made its decision on the use of glyphosate in November 2017.<a href="#cite_note-theguardian.com-153">[153]</a> EFSA's decision and the BfR report were criticized in an <a href="/wiki/Open_letter" title="Open letter">open letter</a> published by 96 scientists in November 2015 saying that the BfR report failed to adhere to accepted scientific principles of open and transparent procedures.<a href="#cite_note-154">[154]</a><a href="#cite_note-portier-155">[155]</a> The BfR report included unpublished data, lacked authorship, omitted references, and did not disclose conflict-of-interest information.<a href="#cite_note-portier-155">[155]</a> In July 2023, EFSA re-evaluated after three years of assessment the putative impact of glyphosate on the health of humans, animals and the environment. As a result, no critical areas of concern were identified that would otherwise prevent glyphosate's registration renewal in the <a href="/wiki/EU" class="mw-redirect" title="EU">EU</a>.<a href="#cite_note-156">[156]</a><a href="#cite_note-157">[157]</a><a href="#cite_note-Open_EFSA_m798-158">[158]</a> <div class="mw-heading mw-heading4"><h4 id="International_Agency_for_Research_on_Cancer">International Agency for Research on Cancer</h4></div> In March 2015, the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC), an intergovernmental agency forming part of the <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> of the <a href="/wiki/United_Nations" title="United Nations">United Nations</a>, published a summary of their forthcoming monograph on glyphosate, and classified glyphosate as "probably carcinogenic in humans" (category 2A) based on epidemiological studies, animal studies, and in vitro studies. It noted that there was "limited evidence" of carcinogenicity in humans for <a href="/wiki/Non-Hodgkin_lymphoma" title="Non-Hodgkin lymphoma">non-Hodgkin lymphoma</a>.<a href="#cite_note-NatureonWHO2015-10">[10]</a><a href="#cite_note-Lancet20March2015-13">[13]</a><a href="#cite_note-IARC20March2015-14">[14]</a><a href="#cite_note-iarcmono-15">[15]</a><a href="#cite_note-159">[159]</a> The IARC classifies substances for their carcinogenic potential, and "a few positive findings can be enough to declare a hazard, even if there are negative studies, as well." Unlike the BfR, it does not conduct a <a href="/wiki/Risk_assessment" title="Risk assessment">risk assessment</a>, weighing benefits against risk.<a href="#cite_note-160">[160]</a> The BfR responded that IARC reviewed only a selection of what they[<a href="/wiki/Wikipedia:Manual_of_Style/Words_to_watch#Unsupported_attributions" title="Wikipedia:Manual of Style/Words to watch">who?</a>] had reviewed earlier, and argued that other studies, including a cohort study called Agricultural Health Study, do not support the classification.<a href="#cite_note-161">[161]</a> The IARC report did not include unpublished studies, including one completed by the IARC panel leader.<a href="#cite_note-162">[162]</a> The agency's international protocol dictates that only published studies be used in classifications of carcinogenicity,<a href="#cite_note-163">[163]</a> since national regulatory agencies including the EPA have allowed agrochemical corporations to conduct their own unpublished research, which may be biased in support of their profit motives.<a href="#cite_note-164">[164]</a> <div class="mw-heading mw-heading5"><h5 id="Reviews_of_the_EFSA_and_IARC_reports">Reviews of the EFSA and IARC reports</h5></div> A 2017 review done by personnel from EFSA and BfR argued that the differences between the IARC's and EFSA's conclusions regarding glyphosate and cancer were due to differences in their evaluation of the available evidence. The review concluded that "Two complementary exposure assessments ... suggests that actual exposure levels are below" the reference values identified by the EFSA "and do not represent a public concern."<a href="#cite_note-Tarazona-12">[12]</a> In contrast, a 2016 analysis by Christopher Portier, a scientist advising the IARC in the assessment of glyphosate and advocate for its classification as possibly carcinogenic, concluded that in the EFSA's Renewal Assessment Report, "almost no weight is given to studies from the published literature and there is an over-reliance on non-publicly available industry-provided studies using a limited set of assays that define the minimum data necessary for the marketing of a pesticide", arguing that the IARC's evaluation of probably carcinogenic to humans "accurately reflects the results of published scientific literature on glyphosate".<a href="#cite_note-165">[165]</a> In October 2017, an article in The Times revealed that Portier had received consulting contracts with two law firm associations representing alleged glyphosate cancer victims that included a payment of US$160,000 to Portier.<a href="#cite_note-166">[166]</a><a href="#cite_note-167">[167]</a> The IARC final report was also found to have changed compared to an interim report, through the removal of text saying certain studies had found glyphosate was not carcinogenic in that study's context, and through strengthening a conclusion of "limited evidence of animal carcinogenicity," to "sufficient evidence of animal carcinogenicity".<a href="#cite_note-168">[168]</a> <div class="mw-heading mw-heading4"><h4 id="US_Environmental_Protection_Agency">US Environmental Protection Agency</h4></div> In a 1993 review, the <a href="/wiki/EPA" class="mw-redirect" title="EPA">EPA</a>, considered glyphosate to be <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">noncarcinogenic</a> and relatively low in <a href="/wiki/Dermal" class="mw-redirect" title="Dermal">dermal</a> and oral acute toxicity.<a href="#cite_note-epa_reds-93">[93]</a> The EPA considered a "worst case" dietary risk model of an individual eating a lifetime of food derived entirely from glyphosate-sprayed fields with residues at their maximum levels. This model indicated that no adverse health effects would be expected under such conditions.<a href="#cite_note-epa_reds-93">[93]</a> In 2015, the EPA initiated a review of glyphosate's toxicity and in 2016 reported that glyphosate is likely not carcinogenic.<a href="#cite_note-NatureonWHO2015-10">[10]</a><a href="#cite_note-169">[169]</a> In August 2019, the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">EPA</a> announced that it no longer allowed labels claiming glyphosate is a carcinogen, as those claims would "not meet the labeling requirements of the <a href="/wiki/Federal_Insecticide,_Fungicide,_and_Rodenticide_Act" title="Federal Insecticide, Fungicide, and Rodenticide Act">Federal Insecticide, Fungicide, and Rodenticide Act</a>" and misinform the public.<a href="#cite_note-auto-170">[170]</a> In 2017, evidence collected in a lawsuit brought against Monsanto by cancer patients revealed company emails which appeared to show a friendly relationship with a senior EPA official.<a href="#cite_note-171">[171]</a> <div class="mw-heading mw-heading5"><h5 id="Monsanto_response_and_campaign">Monsanto response and campaign</h5></div> Monsanto called the IARC report biased and said it wanted the report to be retracted.<a href="#cite_note-172">[172]</a> In 2017, internal documents from Monsanto were made public by lawyers pursuing litigation against the company,<a href="#cite_note-173">[173]</a> who used the term "Monsanto papers" to describe the documents.<a href="#cite_note-174">[174]</a> This term was later used also by <a href="/wiki/Leemon_McHenry" title="Leemon McHenry">Leemon McHenry</a><a href="#cite_note-175">[175]</a> and others.<a href="#cite_note-176">[176]</a> The documents indicated Monsanto had planned a public relations effort to discredit the IARC report, and had engaged <a href="/wiki/Henry_I._Miller" title="Henry I. Miller">Henry Miller</a> to write a 2015 opinion piece in <a href="/wiki/Forbes_Magazine" class="mw-redirect" title="Forbes Magazine">Forbes Magazine</a> challenging the report. Miller did not reveal the connection to Forbes, and according to the <a href="/wiki/New_York_Times" class="mw-redirect" title="New York Times">New York Times</a>, when Monsanto asked him if he was interested in writing such an article, he replied "I would be if I could start from a high-quality draft" provided by the company.<a href="#cite_note-177">[177]</a> Once this became public, Forbes removed his blog from their site. Two journalists from <a href="/wiki/Le_Monde" title="Le Monde">Le Monde</a> won the 2018 <a href="/wiki/European_Press_Prize" title="European Press Prize">European Press Prize</a> for a series of articles on the documents, also titled Monsanto Papers. Their reporting described, among other things, Monsanto's lawyers' letters demanding that IARC scientists turn over documents relating to Monograph 112, which contained the IARC finding that glyphosate was a "probable carcinogen"; several of the scientists condemned these letters as intimidating.<a href="#cite_note-EPP-178">[178]</a> <div class="mw-heading mw-heading4"><h4 id="California_Office_of_Environmental_Health_Hazard_Assessment">California Office of Environmental Health Hazard Assessment</h4></div> In March 2015, the <a href="/wiki/California_Office_of_Environmental_Health_Hazard_Assessment" title="California Office of Environmental Health Hazard Assessment">California Office of Environmental Health Hazard Assessment</a> (OEHHA) announced plans to have glyphosate listed as a known carcinogen based on the IARC assessment. In 2016, Monsanto started a case against OEHHA and its acting director, Lauren Zeise,<a href="#cite_note-179">[179]</a> but lost the suit in March 2017.<a href="#cite_note-180">[180]</a> Glyphosate was listed as "known to the State of California to cause cancer" in 2017, requiring warning labels under <a href="/wiki/Proposition_65" class="mw-redirect" title="Proposition 65">Proposition 65</a>.<a href="#cite_note-181">[181]</a> In February 2018, as part of an ongoing case, an injunction was issued prohibiting California from enforcing carcinogenicity labeling requirements for glyphosate until the case was resolved. The injunction stated that arguments by a <a href="/wiki/US_District_Court_Judge" class="mw-redirect" title="US District Court Judge">US District Court Judge</a> for the <a href="/wiki/Eastern_District_of_California" class="mw-redirect" title="Eastern District of California">Eastern District of California</a> "[do] not change the fact that the overwhelming majority of agencies that that have examined glyphosate have determined it is not a cancer risk."<a href="#cite_note-182">[182]</a> In August 2019, the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">EPA</a> also said it no longer allowed labels claiming glyphosate is a carcinogen, as those claims would "not meet the labeling requirements of the <a href="/wiki/Federal_Insecticide,_Fungicide,_and_Rodenticide_Act" title="Federal Insecticide, Fungicide, and Rodenticide Act">Federal Insecticide, Fungicide, and Rodenticide Act</a>" and misinform the public.<a href="#cite_note-auto-170">[170]</a> <div class="mw-heading mw-heading4"><h4 id="European_Chemicals_Agency">European Chemicals Agency</h4></div> On March 15, 2017 the <a href="/wiki/European_Chemicals_Agency" title="European Chemicals Agency">European Chemicals Agency</a> (ECHA) announced recommendations proceeding from a risk assessment of glyphosate performed by ECHA's Committee for Risk Assessment (RAC). Their recommendations maintained the current classification of glyphosate as a substance causing serious eye damage and as a substance toxic to aquatic life. However, the RAC did not find evidence implicating glyphosate to be a carcinogen, a mutagen, toxic to reproduction, nor toxic to specific organs.<a href="#cite_note-183">[183]</a> In 2022, the agency reiterated these findings in a later review and stated on cancer risk that, "Based on a wide-ranging review of scientific evidence, the committee again concludes that classifying glyphosate as a carcinogen is not justified."<a href="#cite_note-184">[184]</a> <div class="mw-heading mw-heading2"><h2 id="Effects_of_use">Effects of use</h2></div> <div class="mw-heading mw-heading3"><h3 id="Emergence_of_resistant_weeds">Emergence of resistant weeds</h3></div> In the 1990s, no <a href="/wiki/Glyphosate_resistance" class="mw-redirect" title="Glyphosate resistance">glyphosate-resistant</a> weeds were known to exist.<a href="#cite_note-NYT_2010-185">[185]</a> In 2005 a slow upward trend began, resistant weeds appearing rarely around the world.<a href="#cite_note-Trends-186">[186]</a> Another <a href="/wiki/Inflection_point" title="Inflection point">inflection point</a> occurred in 2011 and resistance accelerated globally.<a href="#cite_note-Trends-186">[186]</a> By 2014, glyphosate-resistant weeds dominated herbicide-resistance research. At that time, 23 glyphosate-resistant species were found in 18 countries.<a href="#cite_note-springer_2016_heap_2014-187">[187]</a> "Resistance evolves after a weed population has been subjected to intense selection pressure in the form of repeated use of a single herbicide."<a href="#cite_note-NYT_2010-185">[185]</a><a href="#cite_note-canada-188">[188]</a> According to Ian Heap, a weed specialist, who completed his PhD on resistance to multiple herbicides in annual ryegrass (<a href="/wiki/Lolium_rigidum" title="Lolium rigidum">Lolium rigidum</a>) in 1988<a href="#cite_note-Heap_PhD_1988-189">[189]</a> – the first case of an herbicide-resistant weed in Australia<a href="#cite_note-agannex_2015-190">[190]</a> – by 2014 Lolium rigidum was the "world’s worst herbicide-resistant weed" with instances in "12 countries, 11 sites of action, 9 cropping regimens" and affecting "over 2 million hectares."<a href="#cite_note-springer_2016_heap_2014-187">[187]</a> Annual ryegrass has been known to be resistant to herbicides since 1982. The first documented case of glyphosate-resistant L. rigidum was reported in Australia in 1996 near <a href="/wiki/Orange,_New_South_Wales" title="Orange, New South Wales">Orange, New South Wales</a>.<a href="#cite_note-weeds_iastate_1998-191">[191]</a><a href="#cite_note-192">[192]</a><a href="#cite_note-ResistanceBook2010-193">[193]</a> In 2006, farmers associations were reporting 107 biotypes of weeds within 63 weed species with herbicide resistance.<a href="#cite_note-SEFarmPressResistance-194">[194]</a> In 2009, Canada identified its first resistant weed, <a href="/wiki/Giant_ragweed" class="mw-redirect" title="Giant ragweed">giant ragweed</a>, and at that time 15 weed species had been confirmed as resistant to glyphosate.<a href="#cite_note-canada-188">[188]</a><a href="#cite_note-WeedScience-resistance-195">[195]</a> As of 2010, in the United States 7 to 10 million acres (2.8 to 4.0 million hectares) of soil were afflicted by herbicide-resistant weeds, or about 5% of the 170 million acres planted with corn, soybeans, and cotton, the crops most affected, in 22 states.<a href="#cite_note-nytimes-196">[196]</a> In 2012, Charles Benbrook reported that the <a href="/wiki/Weed_Science_Society_of_America" title="Weed Science Society of America">Weed Science Society of America</a> listed 22 herbicide-resistant species in the U.S., with over 5.7×10<s style="display:none">^</s>6 ha (14×10<s style="display:none">^</s>6 acres) infested by GR weeds and that <a href="/wiki/Dow_AgroSciences" title="Dow AgroSciences">Dow AgroSciences</a> had carried out a survey and reported a figure of around 40×10<s style="display:none">^</s>6 ha (100×10<s style="display:none">^</s>6 acres).<a href="#cite_note-Benbrook2012-197">[197]</a> The International Survey of Herbicide Resistant Weeds database lists species that are resistant to glyphosate.<a href="#cite_note-WeedScience-resistance-195">[195]</a> In response to resistant weeds, farmers are hand-weeding, using tractors to turn over soil between crops, and using other herbicides in addition to glyphosate. Monsanto scientists have found that some resistant weeds have as many as 160 extra copies of a gene called <a href="/wiki/EPSP_synthase" title="EPSP synthase">EPSPS</a>, the enzyme glyphosate disrupts.<a href="#cite_note-198">[198]</a> <div class="mw-heading mw-heading4"><h4 id="Palmer_amaranth">Palmer amaranth</h4></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Amaranthus_palmeri.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Amaranthus_palmeri.jpg/170px-Amaranthus_palmeri.jpg" decoding="async" width="170" height="227" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Amaranthus_palmeri.jpg/255px-Amaranthus_palmeri.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Amaranthus_palmeri.jpg/340px-Amaranthus_palmeri.jpg 2x" data-file-width="400" data-file-height="533" /></a><figcaption><a href="/wiki/Palmer_amaranth" class="mw-redirect" title="Palmer amaranth">Palmer amaranth</a> (Amaranthus palmeri)</figcaption></figure> In 2004, a glyphosate-resistant variation of <a href="/wiki/Amaranthus_palmeri" title="Amaranthus palmeri">Palmer amaranth</a> was found in the U.S. state of Georgia.<a href="#cite_note-Culpepper-199">[199]</a> In 2005, resistance was also found in North Carolina.<a href="#cite_note-Hampton-200">[200]</a> The species can quickly become resistant to multiple herbicides and has developed multiple mechanisms for glyphosate resistance due to <a href="/wiki/Selection_pressure" class="mw-redirect" title="Selection pressure">selection pressure</a>.<a href="#cite_note-201">[201]</a><a href="#cite_note-Hampton-200">[200]</a> The glyphosate-resistant weed variant is now widespread in the southeastern United States.<a href="#cite_note-Culpepper-199">[199]</a><a href="#cite_note-FS03Mar09-202">[202]</a> Cases have also been reported in Texas<a href="#cite_note-FS03Mar09-202">[202]</a> and Virginia.<a href="#cite_note-203">[203]</a> <div class="mw-heading mw-heading4"><h4 id="Conyza_species">Conyza species</h4></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Canadese_fijnstraal_plant_Conyza_canadensis.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Canadese_fijnstraal_plant_Conyza_canadensis.jpg/170px-Canadese_fijnstraal_plant_Conyza_canadensis.jpg" decoding="async" width="170" height="227" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Canadese_fijnstraal_plant_Conyza_canadensis.jpg/255px-Canadese_fijnstraal_plant_Conyza_canadensis.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Canadese_fijnstraal_plant_Conyza_canadensis.jpg/340px-Canadese_fijnstraal_plant_Conyza_canadensis.jpg 2x" data-file-width="1278" data-file-height="1704" /></a><figcaption><a href="/wiki/Conyza_canadensis" class="mw-redirect" title="Conyza canadensis">Horseweed</a></figcaption></figure> <a href="/wiki/Conyza_bonariensis" class="mw-redirect" title="Conyza bonariensis">Conyza bonariensis</a> (also known as hairy fleabane and buva) and <a href="/wiki/Conyza_canadensis" class="mw-redirect" title="Conyza canadensis">C. canadensis</a> (known as horseweed or marestail) are other weed species that have lately developed glyphosate resistance.<a href="#cite_note-204">[204]</a><a href="#cite_note-205">[205]</a><a href="#cite_note-pmid20063320-206">[206]</a> A 2008 study on the current situation of glyphosate resistance in South America concluded "resistance evolution followed intense glyphosate use" and the use of glyphosate-resistant soybean crops is a factor encouraging increases in glyphosate use.<a href="#cite_note-pmid18161884-207">[207]</a> In the 2015 growing season, glyphosate-resistant marestail proved to be especially problematic to control in Nebraska production fields.<a href="#cite_note-cw-marestail-208">[208]</a> <div class="mw-heading mw-heading4"><h4 id="Ryegrass">Ryegrass</h4></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Lolium_perenne_Engels_raaigras_doorgeschoten_plant.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Lolium_perenne_Engels_raaigras_doorgeschoten_plant.jpg/170px-Lolium_perenne_Engels_raaigras_doorgeschoten_plant.jpg" decoding="async" width="170" height="227" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Lolium_perenne_Engels_raaigras_doorgeschoten_plant.jpg/255px-Lolium_perenne_Engels_raaigras_doorgeschoten_plant.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Lolium_perenne_Engels_raaigras_doorgeschoten_plant.jpg/340px-Lolium_perenne_Engels_raaigras_doorgeschoten_plant.jpg 2x" data-file-width="1248" data-file-height="1664" /></a><figcaption><a href="/wiki/Ryegrass" class="mw-redirect" title="Ryegrass">Ryegrass</a></figcaption></figure> Glyphosate-resistant <a href="/wiki/Ryegrass" class="mw-redirect" title="Ryegrass">ryegrass</a> (Lolium) has occurred in most of the Australian agricultural areas and other areas of the world. All cases of evolution of resistance to glyphosate in Australia were characterized by intensive use of the herbicide while no other effective weed control practices were used. Studies indicate resistant ryegrass does not compete well against nonresistant plants and their numbers decrease when not grown under conditions of glyphosate application.<a href="#cite_note-209">[209]</a> <div class="mw-heading mw-heading4"><h4 id="Johnson_grass">Johnson grass</h4></div> Glyphosate-resistant <a href="/wiki/Johnson_grass" title="Johnson grass">Johnson grass</a> (Sorghum halepense) has been found in Argentina as well as Arkansas, Louisiana, and Mississippi.<a href="#cite_note-210">[210]</a> <div class="mw-heading mw-heading3"><h3 id="Monarch_butterfly_populations">Monarch butterfly populations</h3></div> Use of glyphosate and other herbicides like <a href="/wiki/2,4-D" class="mw-redirect" title="2,4-D">2,4-D</a> to clear <a href="/wiki/Asclepias" title="Asclepias">milkweed</a> along roads and fields may have contributed to a decline in <a href="/wiki/Monarch_butterfly" title="Monarch butterfly">monarch butterfly</a> populations in the Midwestern United States.<a href="#cite_note-211">[211]</a> Along with deforestation and adverse weather conditions,<a href="#cite_note-212">[212]</a> the decrease in milkweed contributed to an 81% decline in monarchs.<a href="#cite_note-213">[213]</a><a href="#cite_note-214">[214]</a> The <a href="/wiki/Natural_Resources_Defense_Council" title="Natural Resources Defense Council">Natural Resources Defense Council</a> (NRDC) filed a suit against the <a href="/wiki/EPA" class="mw-redirect" title="EPA">EPA</a> in 2015, in which it argued that the agency ignored warnings about the potentially dangerous impacts of glyphosate usage on monarchs.<a href="#cite_note-215">[215]</a> <div class="mw-heading mw-heading2"><h2 id="Legal_status">Legal status</h2></div> Glyphosate was first approved for use in the 1970s, and as of 2010 was labelled for use in 130 countries.<a href="#cite_note-Dill-19">[19]</a>: 2  In 2017 Vandenberg et al. cited a 100-fold increase in the use of glyphosate-based herbicides from 1974 to 2014, the possibility that herbicide mixtures likely have effects that are not predicted by studying glyphosate alone, and reliance of current safety assessments on studies done over 30 years ago. They recommended that current safety standards be updated, writing that the current standards "may fail to protect public health or the environment."<a href="#cite_note-216">[216]</a> <div class="mw-heading mw-heading3"><h3 id="Europe">Europe</h3></div> In April 2014, the legislature of the <a href="/wiki/Netherlands" title="Netherlands">Netherlands</a> passed legislation prohibiting sale of glyphosate to individuals for use at home; commercial sales were not affected.<a href="#cite_note-217">[217]</a> In June 2015, the <a href="/wiki/Ministry_of_the_Ecological_Transition_(France)" class="mw-redirect" title="Ministry of the Ecological Transition (France)">French Ecology Minister</a> asked nurseries and garden centers to halt over-the-counter sales of glyphosate in the form of Monsanto's Roundup. This was a nonbinding request and all sales of glyphosate remain legal in France until 2022, when it was planned to ban the substance for home gardening.<a href="#cite_note-url_Reuters_France-218">[218]</a> However, more recently the French parliament decided to not to impose a definitive date for such a ban.<a href="#cite_note-219">[219]</a> In January 2019, "the sale, distribution, and use of Roundup 360 [wa]s banned" in France. Exemptions for many farmers were later implemented, and a curb of its use by 80% for 2021 is projected.<a href="#cite_note-220">[220]</a><a href="#cite_note-FrenchBan-221">[221]</a> A vote on the relicensing of glyphosate in the EU stalled in March 2016. Member states France, Sweden, and the Netherlands objected to the renewal.<a href="#cite_note-222">[222]</a> A vote to reauthorize on a temporary basis failed in June 2016<a href="#cite_note-223">[223]</a> but at the last minute the license was extended for 18 months until the end of 2017.<a href="#cite_note-224">[224]</a> On 27 November 2017, in the <a href="/wiki/Council_of_the_European_Union" title="Council of the European Union">EU Council</a> a majority of eighteen member states voted in favor of permitting the use of glyphosate for five more years. A <a href="/wiki/Voting_in_the_Council_of_the_European_Union" title="Voting in the Council of the European Union">qualified majority</a> of sixteen states representing 65% of EU citizens was required to pass the law.<a href="#cite_note-225">[225]</a> The German Minister of Agriculture, <a href="/wiki/Christian_Schmidt_(politician)" title="Christian Schmidt (politician)">Christian Schmidt</a>, unexpectedly voted in favor while the German coalition government was internally divided on the issue which usually results in Germany abstaining.<a href="#cite_note-226">[226]</a> In December 2018, attempts were made to reopen the decision to license the weed-killer. These were condemned by Conservative MEPs, who said the proposal was politically motivated and flew in the face of scientific evidence.<a href="#cite_note-227">[227]</a> In March 2019, the <a href="/wiki/European_Court_of_Justice" title="European Court of Justice">European Court of Justice</a> (ECJ) ordered the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) to release all carcinogenicity and toxicity pesticide industry studies on glyphosate to the general public.<a href="#cite_note-228">[228]</a> In March 2019, the <a href="/wiki/States_of_Austria" class="mw-redirect" title="States of Austria">Austrian state</a> of <a href="/wiki/Carinthia" title="Carinthia">Carinthia</a> outlawed the private use of glyphosate in residential areas while the commercial application of the herbicide is still permitted for farmers. The use of glyphosate by public authorities and road maintenance crews was already halted a number of years prior to the current ban by local authorities.<a href="#cite_note-229">[229]</a> In June 2019, <a href="/wiki/Deutsche_Bahn" title="Deutsche Bahn">Deutsche Bahn</a> and <a href="/wiki/Swiss_Federal_Railways" title="Swiss Federal Railways">Swiss Federal Railways</a> announced that glyphosate and other commonly used herbicides for weed eradication along railway tracks will be phased out by 2025, while more environmentally sound methods for vegetation control are implemented.<a href="#cite_note-230">[230]</a><a href="#cite_note-231">[231]</a> In July 2019, the <a href="/wiki/Austria" title="Austria">Austrian</a> parliament voted to ban glyphosate in Austria.<a href="#cite_note-a-report-constitution-water-public-232">[232]</a> In September 2019, the German Environment Ministry announced that the use of glyphosate will be banned from the end of 2023. The use of glyphosate-based herbicides will be reduced starting from 2020.<a href="#cite_note-233">[233]</a> The assessment process for an approval of glyphosate in the European Union will begin in December 2019. France, Hungary, the Netherlands and Sweden will jointly assess the application dossiers of the producers. The draft report of the assessment group will then be peer-reviewed by the EFSA before the current approval expires in December 2022.<a href="#cite_note-234">[234]</a> The date has since been pushed back, partially due to very high interest and input in the participation process, with the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) even calling it an “unprecedented number”.<a href="#cite_note-235">[235]</a> Because the EFSA has to review all these 2400 comments and almost 400 responses, the process is expected to take longer. The created document is under extra review by the specially formed Glyphosate Renewal Group (GRG) and the Assessment Group on Glyphosate (AGG), the panel consisting of the four mentioned member states. With their responses now being scheduled for September 2022, the consultations with member states are supposed to be held by the very end of 2022.<a href="#cite_note-236">[236]</a><a href="#cite_note-237">[237]</a> This would allow to finish the final assessment by mid-2023 and pass it on to further legislature to decide. In November 2023, glyphosate received 10 year renewed authorization for use in the EU.<a href="#cite_note-238">[238]</a> <div class="mw-heading mw-heading3"><h3 id="Other_countries">Other countries</h3></div> In September 2013, the <a href="/wiki/Legislative_Assembly_of_El_Salvador" title="Legislative Assembly of El Salvador">Legislative Assembly of El Salvador</a> approved legislation to ban 53 agrochemicals, including glyphosate; the ban on glyphosate was set to begin in 2015.<a href="#cite_note-239">[239]</a><a href="#cite_note-240">[240]</a><a href="#cite_note-241">[241]</a> In the <a href="/wiki/United_States" title="United States">United States</a>, the state of <a href="/wiki/Minnesota" title="Minnesota">Minnesota</a> preempts local laws that attempt to ban glyphosate. In 2015 there was an attempt to pass legislation at the state level that would repeal that preemption.<a href="#cite_note-Minnea-StPaul-glyph-res-242">[242]</a> In May 2015, the <a href="/wiki/President_of_Sri_Lanka" title="President of Sri Lanka">President of Sri Lanka</a> banned the use and import of glyphosate, effective immediately.<a href="#cite_note-243">[243]</a><a href="#cite_note-244">[244]</a> However, in May 2018 the Sri Lankan government decided to re-authorize its use in the plantation sector.<a href="#cite_note-245">[245]</a> In May 2015, <a href="/wiki/Bermuda" title="Bermuda">Bermuda</a> blocked importation on all new orders of glyphosate-based herbicides for a temporary suspension awaiting outcomes of research.<a href="#cite_note-Bermuda1-246">[246]</a> In May 2015, <a href="/wiki/Colombia" title="Colombia">Colombia</a> announced that it would stop using glyphosate by October 2015 in the destruction of illegal plantations of <a href="/wiki/Coca" title="Coca">coca</a>, the raw ingredient for <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>. Farmers have complained that the aerial fumigation has destroyed entire fields of <a href="/wiki/Coffee" title="Coffee">coffee</a> and other legal produce.<a href="#cite_note-BBCColumbia-71">[71]</a> In April 2019, <a href="/wiki/Vietnam" title="Vietnam">Vietnam</a>'s Ministry of Agriculture and Rural Development banned the use of glyphosate throughout the country.<a href="#cite_note-Vietnam-247">[247]</a> In August 2020, <a href="/wiki/Mexico" title="Mexico">Mexican</a> President <a href="/wiki/Andr%C3%A9s_Manuel_L%C3%B3pez_Obrador" title="Andrés Manuel López Obrador">Andrés Manuel López Obrador</a> announced that glyphosate will be gradually phased out of use in Mexico by late 2024.<a href="#cite_note-248">[248]</a> Thailand's National Hazardous Substances Committee decided to ban the use of glyphosate in October 2019<a href="#cite_note-249">[249]</a> but reversed the decision in November 2019.<a href="#cite_note-250">[250]</a> After a court-ruling in 2018, glyphosate was temporarily banned in <a href="/wiki/Brazil" title="Brazil">Brazil</a>. This decision was later overturned, causing major criticism by the federal agency of health (<a href="/wiki/Brazilian_Health_Regulatory_Agency" title="Brazilian Health Regulatory Agency">Anvisa</a>). This comes, as the latest evaluations declared glyphosate as noncarcinogenic. Since all carcinogenic agrichemicals are automatically banned in the country, this allowed the continuous use.<a href="#cite_note-251">[251]</a> In New Zealand, glyphosate is an approved herbicide for killing weeds,<a href="#cite_note-mpi-nz-252">[252]</a> with the most popular brand being <a href="/wiki/Roundup_(herbicide)" title="Roundup (herbicide)">Roundup</a>.<a href="#cite_note-mpi-nz-252">[252]</a><a href="#cite_note-epa-nz-253">[253]</a> Genetically modified crops designed to resist glyphosate are absent in New Zealand.<a href="#cite_note-mpi-nz-252">[252]</a> Crops applied with glyphosate must be regulated under the HSNO Act 1996 and ACVM Act 1997.<a href="#cite_note-mpi-nz-252">[252]</a><a href="#cite_note-govtepa-pdf-nz-254">[254]</a> Legal status for glyphosate use in New Zealand is approved for commercial and personal use.<a href="#cite_note-epa-nz-253">[253]</a> In 2021, exports of New Zealand honey were found to contain traces of glyphosate, causing some concern to Japanese importers.<a href="#cite_note-honey-nz-shun-255">[255]</a><a href="#cite_note-honey-nz-shun2-256">[256]</a> <div class="mw-heading mw-heading2"><h2 id="Legal_cases">Legal cases</h2></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Monsanto_legal_cases#Roundup" title="Monsanto legal cases">Monsanto legal cases § Roundup</a></div> <div class="mw-heading mw-heading3"><h3 id="Lawsuits_claiming_liability_for_cancer">Lawsuits claiming liability for cancer</h3></div> Since 2018, in a number of court cases in the United States, plaintiffs have argued that their cancer was caused by exposure to glyphosate in glyphosate-based herbicides produced by Monsanto/Bayer. Defendant Bayer has paid out over $9.6 billion in judgements and settlements in these cases. Bayer has also won at least 10 cases, successfully arguing that their glyphosate-based herbicides were not responsible for the plaintiff's cancer.<a href="#cite_note-bayer-wins-257">[257]</a> <div class="mw-heading mw-heading3"><h3 id="Advertising_controversies">Advertising controversies</h3></div> In 2016, a lawsuit was filed against <a href="/wiki/Quaker_Oats" class="mw-redirect" title="Quaker Oats">Quaker Oats</a> in the <a href="/wiki/United_States_district_court" title="United States district court">Federal district courts</a> of both <a href="/wiki/New_York_(state)" title="New York (state)">New York</a> and <a href="/wiki/California" title="California">California</a> after trace amounts of glyphosate were found in <a href="/wiki/Oatmeal" title="Oatmeal">oatmeal</a>. The lawsuit alleged that the claim of "100% natural" was <a href="/wiki/False_advertising" title="False advertising">false advertising</a>.<a href="#cite_note-258">[258]</a> That same year <a href="/wiki/General_Mills" title="General Mills">General Mills</a> dropped the label "Made with 100% Natural Whole Grain Oats" from their <a href="/wiki/Nature_Valley" title="Nature Valley">Nature Valley</a> <a href="/wiki/Granola_bars" class="mw-redirect" title="Granola bars">granola bars</a> after a lawsuit was filed that claimed the <a href="/wiki/Oat" title="Oat">oats</a> contained trace amounts of glyphosate.<a href="#cite_note-259">[259]</a> <div class="mw-heading mw-heading3"><h3 id="Trade_dumping_allegations">Trade dumping allegations</h3></div> United States companies have cited trade issues with glyphosate being <a href="/wiki/Dumping_(pricing_policy)" title="Dumping (pricing policy)">dumped</a> into western world market areas by Chinese companies, and a formal dispute was filed in 2010.<a href="#cite_note-urlwww.usitc.gov-260">[260]</a><a href="#cite_note-261">[261]</a> <div class="mw-heading mw-heading2"><h2 id="Misinformation_campaigns">Misinformation campaigns</h2></div> Glyphosate has become a locus of campaigning and misinformation by anti-GMO activists because of its association with genetically-modified glyphosate-resistant crops.<a href="#cite_note-bogey-262">[262]</a> The US politician <a href="/wiki/Robert_F._Kennedy_Jr." title="Robert F. Kennedy Jr.">Robert F. Kennedy Jr.</a> has incorporated glyphosate into his <a href="/wiki/Anti-vaccination" class="mw-redirect" title="Anti-vaccination">anti-vaccination</a> rhetoric, falsely claiming that both glyphosate and vaccines may be contributing to the American <a href="/wiki/Obesity_epidemic" class="mw-redirect" title="Obesity epidemic">obesity epidemic</a>.<a href="#cite_note-bogey-262">[262]</a> <a href="/wiki/Stephanie_Seneff" title="Stephanie Seneff">Stephanie Seneff</a> has also falsely claimed that it may have a role in <a href="/wiki/Autism" title="Autism">autism</a> and in worsening <a href="/wiki/Concussion" title="Concussion">concussion</a>.<a href="#cite_note-ss-263">[263]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col div-col-small" style="column-width: 20em;"> <ul><li><a href="/wiki/2,4-Dichlorophenoxyacetic_acid" title="2,4-Dichlorophenoxyacetic acid">2,4-Dichlorophenoxyacetic acid</a></li> <li><a href="/wiki/Ammonium_sulfamate" title="Ammonium sulfamate">Ammonium sulfamate</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Environmental_impact_of_pesticides" title="Environmental impact of pesticides">Environmental impact of pesticides</a></li> <li><a href="/wiki/Health_effects_of_pesticides" title="Health effects of pesticides">Health effects of pesticides</a></li> <li><a href="/wiki/Integrated_pest_management" title="Integrated pest management">Integrated pest management</a></li> <li><a href="/wiki/Monsanto_legal_cases" title="Monsanto legal cases">Monsanto legal cases</a></li> <li><a href="/wiki/Pesticide_regulation_in_the_United_States" title="Pesticide regulation in the United States">Pesticide regulation in the United States</a></li> <li><a href="/wiki/Regulation_of_pesticides_in_the_European_Union" title="Regulation of pesticides in the European Union">Regulation of pesticides in the European Union</a></li> <li><a href="/wiki/S%C3%A9ralini_affair" title="Séralini affair">Séralini affair</a></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-PHOGLY05-1"><a href="#cite_ref-PHOGLY05_1-0">^</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output 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title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2190-4707">2190-4707</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5044953">5044953</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27752438">27752438</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:1660085">1660085</a>.</cite><span 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href="https://commons.wikimedia.org/wiki/Category:Glyphosate" class="extiw" title="commons:Category:Glyphosate">Glyphosate</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/373.htm">Glyphosate</a> in the Pesticide Properties DataBase (PPDB)</li> <li><a rel="nofollow" class="external text" href="http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1062.htm">Glyphosate trimesium</a> in the Pesticide Properties DataBase (PPDB)</li> <li><a rel="nofollow" class="external text" href="http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/2395.htm">Glyphosate, isopropylamine salt</a> in the Pesticide Properties DataBase (PPDB)</li> <li><a rel="nofollow" class="external text" href="http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/2396.htm">Glyphosate, potassium salt</a> in the Pesticide Properties DataBase (PPDB)</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist 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.navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a 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:_herbicides" 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="/w/index.php?title=Flamprop&action=edit&redlink=1" class="new" title="Flamprop (page does not exist)">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" 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 class="mw-selflink selflink">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/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="/w/index.php?title=Carfentrazone&action=edit&redlink=1" class="new" title="Carfentrazone (page does not exist)">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_inhibitors" 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/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 id="Photosystem_II_inhibitors" 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 href="/wiki/Atrazine" title="Atrazine">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/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> <li><a href="/wiki/Metamitron" title="Metamitron">metamitron</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/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 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