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class="vector-toc-numb">2</span> <span>Structure and reactivity</span> </div> </a> <ul id="toc-Structure_and_reactivity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Hydrolysis</span> </div> </a> <ul id="toc-Hydrolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleophilic_Substitution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_Substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Nucleophilic Substitution</span> </div> </a> <ul id="toc-Nucleophilic_Substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reductive_Debromination" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reductive_Debromination"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Reductive Debromination</span> </div> </a> <ul id="toc-Reductive_Debromination-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Photodegradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Photodegradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Photodegradation</span> </div> </a> <ul id="toc-Photodegradation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Available forms</span> </div> </a> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> 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id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">DBNPA</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/2,2-Dibrom-2-cyanacetamid" title="2,2-Dibrom-2-cyanacetamid – German" lang="de" hreflang="de" data-title="2,2-Dibrom-2-cyanacetamid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%DB%8C%E2%80%8C%D8%A8%DB%8C%E2%80%8C%D8%A7%D9%86%E2%80%8C%D9%BE%DB%8C%E2%80%8C%D8%A7%DB%8C" title="دی‌بی‌ان‌پی‌ای – Persian" lang="fa" hreflang="fa" data-title="دی‌بی‌ان‌پی‌ای" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/2,2-Dibromo-3-nitrilopropionamide" title="2,2-Dibromo-3-nitrilopropionamide – French" lang="fr" hreflang="fr" data-title="2,2-Dibromo-3-nitrilopropionamide" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/2,2-dibromo-2-cianoacetammide" title="2,2-dibromo-2-cianoacetammide – Italian" lang="it" hreflang="it" data-title="2,2-dibromo-2-cianoacetammide" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/DBNPA" title="DBNPA – Japanese" lang="ja" hreflang="ja" data-title="DBNPA" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/DBNPA" title="DBNPA – Serbian" lang="sr" hreflang="sr" data-title="DBNPA" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/DBNPA" title="DBNPA – Serbo-Croatian" lang="sh" hreflang="sh" data-title="DBNPA" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/2,2-dibromi-2-syanoasetamidi" title="2,2-dibromi-2-syanoasetamidi – Finnish" lang="fi" hreflang="fi" data-title="2,2-dibromi-2-syanoasetamidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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<caption>DBNPA </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:2,2-Dibromo-2-cyanacetamide_Structural_Formula_V1.svg" class="mw-file-description" title="Skeletal formula of DBNPA"><img alt="Skeletal formula of DBNPA" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/2%2C2-Dibromo-2-cyanacetamide_Structural_Formula_V1.svg/160px-2%2C2-Dibromo-2-cyanacetamide_Structural_Formula_V1.svg.png" decoding="async" width="160" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/2%2C2-Dibromo-2-cyanacetamide_Structural_Formula_V1.svg/240px-2%2C2-Dibromo-2-cyanacetamide_Structural_Formula_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/2%2C2-Dibromo-2-cyanacetamide_Structural_Formula_V1.svg/320px-2%2C2-Dibromo-2-cyanacetamide_Structural_Formula_V1.svg.png 2x" data-file-width="234" data-file-height="151" /></a><figcaption>Skeletal formula of DBNPA</figcaption></figure> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:DBNPA-3D-balls.png" class="mw-file-description" title="Ball and stick model of DBNPA"><img alt="Ball and stick model of DBNPA" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/DBNPA-3D-balls.png/120px-DBNPA-3D-balls.png" decoding="async" width="110" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/DBNPA-3D-balls.png/250px-DBNPA-3D-balls.png 1.5x" data-file-width="2000" data-file-height="1474" /></a><figcaption>Ball and stick model of DBNPA</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:DBNPA-3D-spacefill.png" class="mw-file-description" title="Spacefill model of DBNPA"><img alt="Spacefill model of DBNPA" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/DBNPA-3D-spacefill.png/120px-DBNPA-3D-spacefill.png" decoding="async" width="110" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/DBNPA-3D-spacefill.png/250px-DBNPA-3D-spacefill.png 1.5x" data-file-width="2000" data-file-height="1734" /></a><figcaption>Spacefill model of DBNPA</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2,2-Dibromo-2-cyanoacetamide<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><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>Dibromocyano acetic acid amide</li><li>2,2-Dibromo-3-nitrilopropionamide</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=10222-01-2">10222-01-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=NC%28%3DO%29C%28Br%29%28Br%29C%23N">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.23422.html">23422</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.030.477">100.030.477</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q5204411#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>233-539-7</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=2,2-dibromo-3-nitrilopropionamide">2,2-dibromo-3-nitrilopropionamide</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/25059">25059</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>AB5956000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/7N51QGL6MJ">7N51QGL6MJ</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>1759 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5032361">DTXSID5032361</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q5204411#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3H2Br2N2O/c4-3(5,1-6)2(7)8/h(H2,7,8)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: UUIVKBHZENILKB-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">NC(=O)C(Br)(Br)C#N</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>2</sub><span title="Bromine">Br</span><sub>2</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002241870000000000♠"></span>241.870</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>White, translucent crystals </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>122 to 125 °C (252 to 257 °F; 395 to 398 K) </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" 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></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H400: Very toxic to aquatic life">H400</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> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>10 mg kg<sup>−1</sup> <small>(intravenous, mouse)</small> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Cyanoacetamide" title="Cyanoacetamide">Cyanoacetamide</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>2-2 dibromo-3-nitrilopropionamide (DBNPA)</b> is a <a href="/wiki/Halogenation" title="Halogenation">brominated</a> <a href="/wiki/Acetamide" title="Acetamide">acetamide</a>. Its synonym is 2,2-Dibromo-2-carbamoylacetonitrile Alpha, alpha-Dibromo-alpha-cyanoacetamide Dibromocyanoacetamide. The physical appearance of DBNPA is an off-white solid at ambient temperatures with a mild antiseptic odor and is often sold in powder form. DBNPA is often used as an algicide, bactericide and fungicide in industrial water treatment systems and as a preservative used in the manufacture of paper, glues, coatings, enhanced oil recovery systems and metalworking.<sup id="cite_ref-:11_2-0" class="reference"><a href="#cite_note-:11-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:10_3-0" class="reference"><a href="#cite_note-:10-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first documented synthesis of 2,2-dibromo-3-nitrilopropionamide (DBNPA) was carried out by Bernhard Conrad Hesse in 1896.<sup id="cite_ref-:11_2-1" class="reference"><a href="#cite_note-:11-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> DBNPA's practical applications were not explored until 1947,when it started being used as a seed and plant fungicide.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Despite this early use, its complete potential as an antibacterial agent was not yet understood. </p><p>By the early 1970s, DBNPA had gained attention for its effectiveness in controlling microbial contaminations in industrial settings. It started being widely used as a slimicide in papermaking systems, cooling water treatment, and other industries vulnerable to biofouling.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> DBNPA's demonstrated biocidal efficacy led to its official registration as a pesticide in the US in 1972. </p><p>Beyond its typical use as a biocide, DBNPA has been investigated for other uses in recent years. Research has investigated its potential as an alternative to antibiotics in bacterial control during ethanol fermentation.<sup id="cite_ref-:5_6-0" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> DBNPA is often used today as a fast-acting antimicrobial agent to eliminate microbial contamination in manufacturing and industrial processes. Applications needing efficient microbial control with little environmental persistence favour the use of DBNPA due to its quick disintegration in water.<sup id="cite_ref-:5_6-1" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Its effectiveness and safety in a variety of industries are still being explored. </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_reactivity">Structure and reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=2" title="Edit section: Structure and reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA is a halogenated cyanoacetamide compound, characterized by the presence of two bromine atoms at the 2,2-position of the carbon backbone. DBNPA contains a cyano (-CN) group and an amide (-CONH₂) group attached to a three-carbon chain. The molecular formula is <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">2</sub>Br<sub class="template-chem2-sub">2</sub>N<sub class="template-chem2-sub">2</sub>O</span>, with a molecular weight of 241.87 g/mol.<sup id="cite_ref-:0_7-0" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>DBNPA is highly reactive due to the two electron-withdrawing bromine atoms and a cyano (-CN) group attached to the central carbon backbone. These substituents form a very electron-deficient core, making it highly vulnerable to nucleophilic attacks. The cyano group increases the reactivity of the compound by stabilizing the electron deficiency while the amide (−CONH₂) group affects its water solubility. The electron-deficient carbon adjacent to the bromine atoms plays a critical role in DBNPA’s biocidal properties, leading to the disruption of microbial cellular functions.<sup id="cite_ref-:3_8-0" class="reference"><a href="#cite_note-:3-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Since DBNPA is a highly reactive molecule, it is prone to pH-dependent hydrolysis at neutral and alkaline conditions because of the weak carbon-bromide bonds.<sup id="cite_ref-:7_9-0" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> DBNPA is also susceptible to be broken down in reducing environments by stepwise debromination. Additionally, DBNPA is highly sensitive to ultraviolet (UV) exposure, which accelerates its degradation in aqueous environments.<sup id="cite_ref-:5_6-2" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Due to its reactive nature, DBNPA must be stabilized in products to prevent premature degradation before application. The rapid breakdown of DBNPA in water and light-exposed environments reduces concerns about long-term contamination but raises considerations regarding the toxicity of its degradation byproducts, such as DBAA and DBAN.<sup id="cite_ref-:6_10-0" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=3" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The process used to create DBNPA is acid-catalyzed bromination of 3-cyanoacetamide.<sup id="cite_ref-:11_2-2" class="reference"><a href="#cite_note-:11-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Polyethylene glycol is often used as the solvent due to its ability to dissolve both reactants and products effectively.<sup id="cite_ref-:1_11-0" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Next, the bromination step is initiated by introducing bromine (Br₂) or an alternative brominating agent, such as sodium bromide (NaBr) with an oxidant. DBNPA (C₃H₂Br₂N₂O) is formed as a result of an electrophilic bromination reaction at the α-carbon of 3-cyanoacetamide. Isolation and purification of DBNPA are carried out after bromination.  The reaction mixture is neutralized, and the product is extracted and purified. The next step is drying, which yields DBNPA in its stable crystalline form. Usually, the reaction temperature is kept between 10°C and 20°C to minimize unintended side reactions. The concentration of bromine is carefully controlled, because an excess can lead to the formation of undesired byproducts that reduces the overall yield.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>The stability of DBNPA depends on the storage conditions. Due to its incompatibility with metals, DBNPA should be stored in non-metal containers.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It must also be stored away from UV exposure, as this can degrade DBNPA.<sup id="cite_ref-:7_9-1" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=4" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA decomposition is dominated by two reaction pathways: pH-dependent hydrolysis and light-catalyzed reactions with reducing nucleophiles.<sup id="cite_ref-:7_9-2" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> DBNPA's electrophilic bromine atoms and electron-withdrawing cyano (-CN) group play a major role in determining its reactivity. A number of variables, including temperature, pH, light exposure, and reducing agents, have a substantial impact on the rate and mechanism of DBNPA breakdown. Different organic and inorganic byproducts could therefore develop, which could have an impact on DBNPA's toxicity and biocidal effectiveness.<sup id="cite_ref-:8_14-0" class="reference"><a href="#cite_note-:8-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hydrolysis">Hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=5" title="Edit section: Hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA undergoes rapid pH-dependent hydrolysis in aqueous environments, leading to the formation of different degradation products. The C-Br bonds break down rapidly into smaller organic and inorganic byproducts when exposed to neutral to alkaline environments due to nucleophilic substitution.<sup id="cite_ref-:7_9-3" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> DBNPA can endure longer in acidic settings since the hydrolysis rate is lower. </p><p>The pH has a significant impact on DBNPA's breakdown. The main degradation product at pH 5 is dibromoacetic acid (DBAA), which makes up 30.6% of all DBNPA breakdown products. The breakdown mechanism changes as the pH rises, favouring the synthesis of dibromoacetonitrile (DBAN), which dominates at pH 7 (54.5%) and pH 9 (38.6%). Ammonia, carbon dioxide, bromide ions, and cyanoacetic acid are produced by further hydrolysis in neutral or slightly alkaline conditions.<sup id="cite_ref-:6_10-1" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>   </p> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_Substitution">Nucleophilic Substitution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=6" title="Edit section: Nucleophilic Substitution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA reacts with nucleophiles due to its electrophilic bromine atoms.<sup id="cite_ref-:9_15-0" class="reference"><a href="#cite_note-:9-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> One of the most important reactions is the formation of thioether derivatives with thiol groups (R-SH). </p><p>R-SH+DBNPA→R-S-CH2C(Br)(NO2)NH2 </p><p>Similarly, DBNPA reacts with amines (R-NH₂) to form substituted amide compounds. </p><p>R-NH2+DBNPA→R-NH-C(Br)(NO2)NH2 </p><p>In basic environments, DBNPA undergoes nucleophilic substitution by hydroxide ions, which initiates hydrolysis. This reaction reduces the environmental persistence of DBNPA by breaking it down into smaller degradation products.<sup id="cite_ref-:7_9-4" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>DBNPA+OH−→Hydrolysis products </p> <div class="mw-heading mw-heading3"><h3 id="Reductive_Debromination">Reductive Debromination</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=7" title="Edit section: Reductive Debromination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the presence of reducing agents, DBNPA undergoes stepwise debromination, leading to less brominated derivatives or complete dehalogenation. </p><p>DBNPA + Reducing Agent → Mono- or Debrominated Products </p> <div class="mw-heading mw-heading3"><h3 id="Photodegradation">Photodegradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=8" title="Edit section: Photodegradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Additionally, DBNPA is prone to light-induced degradation, especially when exposed to ultraviolet (UV) radiation. Photocatalytic breakdown leads to debromination and the formation of less reactive intermediates, further accelerating its degradation in aqueous systems.<sup id="cite_ref-:5_6-3" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Available_forms">Available forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=9" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA’s available form is dependent on its intended industrial use. Its pure state is a crystalline solid, with a melting point of 123-126°C. It is slightly soluble in water (1.5 g per 100 g at 25°C) but dissolves readily in certain organic solvents like acetone and ethanol.<sup id="cite_ref-:0_7-1" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> For practical applications, DBPNA is most commonly used in the form of a mixture of 20% active solution combined with water and polyethylene glycol, which enhances its stability and handling in aqueous systems.<sup id="cite_ref-:1_11-1" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Its solid forms are also available but are mainly used for packaging and storage; it is often packaged in containers within 25 kg woven bags in order to prevent moisture exposure in storage mechanisms.<sup id="cite_ref-:2_16-0" class="reference"><a href="#cite_note-:2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=10" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA is a moderate electrophile.<sup id="cite_ref-:1_11-2" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It acts as a broad-spectrum, non-oxidizing biocide by very quickly disrupting important cellular processes in microorganisms like bacteria, fungi and algae, ultimately causing cell death.<sup id="cite_ref-:3_8-1" class="reference"><a href="#cite_note-:3-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Its primary mechanism involves penetrating the cell membrane and targeting nucleophilic sites, and relies on bromine interacting with sulfur containing groups on proteins critical for cellular metabolism.<sup id="cite_ref-:4_17-0" class="reference"><a href="#cite_note-:4-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Once inside the cell, DBNPA reacts with these sulfur-containing groups, forming covalent bonds that inactivate enzymes involved in redox equations.<sup id="cite_ref-:3_8-2" class="reference"><a href="#cite_note-:3-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> This disruption is irreversible and stops energy production, leading to cell death within 5-10 minutes of exposure.<sup id="cite_ref-:1_11-3" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_16-1" class="reference"><a href="#cite_note-:2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> To summarize, DBNPA stops biofouling in water systems, which is the undesirable accumulation of microorganisms, very quickly, by permanently attacking microbiological cell walls.<sup id="cite_ref-:1_11-4" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>The non-oxidative mechanism distinguishes DBNPA from other oxidizing agents like bleach; instead of oxidizing cellular components broadly, DBNPA selectively targets functional protein groups, making it effective against pathogens like gram-negative bacteria and fungi.<sup id="cite_ref-:4_17-1" class="reference"><a href="#cite_note-:4-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> For example, in cooling water systems, DBNPA has been shown to reduce gram-negative bacteria <i>Legionella pneumophila</i> counts by 99.9% within 10 minutes, at low concentrations of 5 mg/L.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>There may also be a secondary mechanism, through which DBNPA’s nitrile group contributes towards its biocidal activity by a potential interaction with other nucleophilic sites like amino groups on proteins or amino acids, however, this mechanism is not widely studied, so not much is known about it.<sup id="cite_ref-:4_17-2" class="reference"><a href="#cite_note-:4-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Unlike other similar biocides which require prolonged exposure in order to be effective, like isothiazolinone, DBNPA’s fast reaction is attributed towards its chemical instability in aqueous environments, where it is able to degrade within hours.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_11-5" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> This instability ensures that microorganisms are exposed to a high initial dose but the likelihood of resistance development is small, since surviving cells are not exposed to sublethal concentrations over extended periods of time.<sup id="cite_ref-:2_16-2" class="reference"><a href="#cite_note-:2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> This rapid degradation also means that DBNPA is only well-suited for short-term microbial control, but not long-term preservation, making it serve a different purpose to more stable biocides.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Indications">Indications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=11" title="Edit section: Indications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA is used as a disinfectant, bactericide, algicide, slime remover, and mildew inhibitor in several industrial applications. It is frequently used to regulate the growth of bacteria, algae, and slime in oilfield water injection systems and circulating cooling water systems. DBNPA is used in the paper industry as a slime remover, bactericide, and algicide to keep machinery free of microorganisms and maintain product quality. Additionally, it is utilized as a preservative to prevent microbiological deterioration in paints, waxes, inks, detergents, surfactants, slurries, and resins. DBNPA also serves as a fungicide and algaecide in municipal water landscapes, guaranteeing water safety and clarity, and as a biocide in process water and air purifier systems in the machinery manufacturing sector.<sup id="cite_ref-:0_7-2" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:2_16-3" class="reference"><a href="#cite_note-:2-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> The concentration used when it is being used as a water treatment slime stripper is 30~50 mg/L. When it is being used for water treatment, as a bactericide, it is used at a concentration of 10~20 mg/L.<sup id="cite_ref-:0_7-3" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>In terms of analytical detection in industrial and environmental samples, high-performance liquid chromatography with UV detection, measuring absorption at 230 nm, detects DBNPA at extremely low concentrations (>0.1 mg/L) in water samples.<sup id="cite_ref-:5_6-4" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Gas chromatography-mass spectrometry can also identify and quantify DBNPA and the associated degradation products, (detection limit is 0.05 mg/L) in environmental samples.<sup id="cite_ref-:5_6-5" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Efficacy_and_side_effects">Efficacy and side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=12" title="Edit section: Efficacy and side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA was used to limit bacterial growth in different water applications, such as cooling water and paper processing.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> In these applications, positive application of DBNPA were instantaneous antimicrobial activity and rapid chemical breakdown into relatively non-toxic by-products.<sup id="cite_ref-:8_14-1" class="reference"><a href="#cite_note-:8-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:9_15-1" class="reference"><a href="#cite_note-:9-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> These applications could be beneficial in the ethanol industry <sup id="cite_ref-:5_6-6" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Medical_efficacy">Medical efficacy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=13" title="Edit section: Medical efficacy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The microbiological efficacy of DBNPA against bacteria coupled with the degradation results found early in the corn-to-ethanol process, could allow this biocide to replace antibiotics in the corn-to-ethanol biofuel industry.<sup id="cite_ref-:9_15-2" class="reference"><a href="#cite_note-:9-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:8_14-2" class="reference"><a href="#cite_note-:8-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> DBNPA can be used to protect against bacterial infection of the corn-to-ethanol process, saving on costs of raw materials, finished products, and post bacterial infection clean-outs, but it is also suggested that use of this biocide can help prevent antibiotic resistance.<sup id="cite_ref-:5_6-7" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p><b>Adverse effects</b> </p><p>Exposure to DBNPA can lead to several health concerns like acute toxicity, skin and eye irritation and respiratory effects. Potential for occupational exposure to DBNPA exists during manufacture, at bulk unloading, storage and staging areas, but also during sampling and maintenance operations in facilities while using the chemical as an additive in the manufacture of other products. A much lower potential for exposure exists in facilities using DBNPA in closed manufacturing processes by trained personnel. A positive pressure air-supplied respirator is required when airborne concentrations of DBNPA exceeds the recommended exposure limit. In addition, LANXESS recommends the use of safety glasses with side shields or safety goggles, chemical-resistant gloves, a chemical-resistant protective suit and suitable protective footwear be worn when handling DBNPA. Regarding short-term health effects, DBNPA is very toxic by inhalation and toxic by ingestion. Prolonged exposure may cause severe nose, throat and lung irritation. DBNPA dust may cause mechanical (abrasive) irritation to the skin, eyes and respiratory system and is severely irritating to the eyes and may cause permanent corneal damage. Skin contact may cause an allergic skin reaction. Pre-existing skin disorders may even be aggravated by over-exposure to this product. Regarding long-term health effects, DBNPA contains material that may cause target organ damage, based on animal data. Repeated or prolonged inhalation of DBPNA dust can lead to chronic respiratory problems. Once sensitized, an allergic skin reaction may occur when subsequently exposed to very low levels of DBNPA.<sup id="cite_ref-:10_3-1" class="reference"><a href="#cite_note-:10-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=14" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA exhibits various degrees of toxicity like acute oral toxicity, dermal toxicity and inhalation toxicity while it is stable under normal conditions of use. Contact with strong amines should however be avoided including bases, oxidizing agents and reducing agents. DBNPA is corrosive to mild steel, iron and aluminum. The creation of dust when handling DBNPA should be avoided and precautionary measures against electrostatic discharges should be taken. Avoid heat, open flames and other potential sources of ignition when handling DBNPA.<sup id="cite_ref-:10_3-2" class="reference"><a href="#cite_note-:10-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Additionally, DBNPA is corrosive to the eyes. It is moderately  toxic by oral or inhalation routes and slightly toxic by the dermal route. DBNPA can kill skin tissue in rabbits when administered at high doses for a prolonged period of time. DBNPA is also a skin sensitizer. In a toxicity study using rats, DBNPA caused breathing difficulty associated with lung or heart disease, as well as weight loss and several deaths at higher doses. When applied to the skin of rats in another study, DBNPA caused changes in body chemistry and dermal irritation at the higher doses. DBNPA is a developmental toxicant in rabbits. It was shown to cause structural alterations (retarded ossification of several fetal skeleton elements) at a maternally non-toxic dose level. DBNPA is not mutagenic. The US Environmental protection agency (EPA) has received several human incident reports in which eye, throat and respiratory irritation, runny nose and headache resulted from spills or misuse of DBNPA.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Acute Toxicity Values for DBNPA. The lower the toxicity category, the higher the toxicity.<sup id="cite_ref-:6_10-2" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <td>Test (species) </td> <td>Result </td> <td>Toxicity Category </td></tr> <tr> <td>81-1 Oral Toxicity (rat) </td> <td>LD50 - 235 mg/kg (M); 178 mg/kg (F) </td> <td>2 </td></tr> <tr> <td>81-2 Dermal Toxicity (rabbit) </td> <td>LD50 - >2 g/kg </td> <td>3 </td></tr> <tr> <td>81-3 Inhalation Toxicity (rat) </td> <td>LC50 - 0.32 mg/L </td> <td>2 </td></tr> <tr> <td>81-4 Eye Irritation (rabbit) </td> <td>Corrosive </td> <td>1 </td></tr> <tr> <td>81-5 Skin Irritation (rabbit) </td> <td>Moderate dermal irritant </td> <td>3 </td></tr> <tr> <td>81-6 Dermal sensitization (guinea pig) </td> <td>Dermal sensitizer </td> <td>n/a </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Effects_on_animals">Effects on animals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=15" title="Edit section: Effects on animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ecological exposure in water has severe toxic effects on wildlife. When adult and larval zebrafish were exposed to various concentrations of DBNPA, significant morphological changes and mortality rates were observed. Even relatively low concentrations of DBNPA can have detrimental effects on zebrafish embryonic development, and high concentrations resulted in rapid mortality in adult zebrafish and larvae.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> DBNPA is highly toxic to mammals and birds concerning acute oral inhalation, but has low toxicity to birds concerning consummation of food. The pesticide is moderately toxic to freshwater fish, estuarine fish and shrimp; moderately to highly toxic to freshwater crustaceans; and highly to very highly toxic to estuarine shellfish and larvae. Many effects to aquatic organisms occur within 24 hours of exposure.<sup id="cite_ref-:6_10-3" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Residual antibiotics in meat were previously found to disrupt its fermentation, increase the risk of infection, and make pathogens less susceptible medically to treatment with antibiotics.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Apparently, antibiotics found at low concentrations at the end of the ethanol process can cause high levels of antimicrobial resistance.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> These problems can be avoided by the application of DBNPA instead of an antibiotic to control bacteria in the ethanol process. This represents a significant advance in the field because DBNPA breaks down prior to the end of the process and thus cannot enter DDGS used for animal foods.<sup id="cite_ref-:5_6-8" class="reference"><a href="#cite_note-:5-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This means that the application of DBNPA can circumvent the bacterial antibiotic resistance problem of FDA concern, making it a successful alternative to antibiotics.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Then agricultural use of DDGS in feed would represent a safer practice because DBNPA would be degraded, would make the use of antibiotics oblivious and reduce antibiotic resistance in bacteria in bovine, swine, and poultry applications in the food chain. </p> <div class="mw-heading mw-heading2"><h2 id="Environmental_Implications">Environmental Implications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=16" title="Edit section: Environmental Implications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DBNPA breaks down chemically in systems rather than biologically, like pharmaceuticals do in living organisms. Both biotic and abiotic processes can cause degradation in soil and water.<sup id="cite_ref-:6_10-4" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Half-lives in soil range from 4 to 25 hours, with pH values between 4.8 and 7.5.<sup id="cite_ref-:7_9-5" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> DBNPA is prone to photodegradation in regions exposed to sunlight and aqueous hydrolysis in moist soil.<sup id="cite_ref-:6_10-5" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>DBNPA is not expected to adsorb to sediment and suspended solids in water. In water, the primary product of degradation at pH 5 is dibromoacetic acid, while at pH 7 and 9, the primary product of degradation is dibromoacetonitrile.<sup id="cite_ref-:6_10-6" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Additionally, it can break down into bromoacetamide, bromoacetic acid, 2-cyanoacetamide, and oxalic acid. About 4 hours is the half-life.<sup id="cite_ref-:6_10-7" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> DBNPA is prone to photodegradation.<sup id="cite_ref-:7_9-6" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Its atmospheric fate is that the vapour-phase DBNPA is degraded in the atmosphere by photochemically-produced hydroxyl radicals, and the half-life of this process is approximately 8 days.<sup id="cite_ref-:6_10-8" class="reference"><a href="#cite_note-:6-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> DBNPA is also susceptible to photolysis in the atmosphere, directly.<sup id="cite_ref-:7_9-7" class="reference"><a href="#cite_note-:7-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=DBNPA&action=edit&section=17" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=25059">"2,2-dibromo-3-nitrilopropionamide - Compound Summary"</a>. <i>PubChem Compound</i>. USA: National Center for Biotechnology Information. 26 March 2005. Identification<span class="reference-accessdate">. Retrieved <span class="nowrap">9 June</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem+Compound&rft.atitle=2%2C2-dibromo-3-nitrilopropionamide+-+Compound+Summary&rft.pages=Identification&rft.date=2005-03-26&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fsummary%2Fsummary.cgi%3Fcid%3D25059&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:11-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:11_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:11_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:11_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHesse1896" class="citation book cs1">Hesse, Bernhard Conrad (1896). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=-plPAAAAYAAJ&dq=Hesse+BC+acetamide&pg=PA1"><i>Hesse, B. C. (1896). On malonic nitrile and some of its derivatives... Chemical Publishing Company</i></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hesse%2C+B.+C.+%281896%29.+On+malonic+nitrile+and+some+of+its+derivatives...+Chemical+Publishing+Company.&rft.date=1896&rft.aulast=Hesse&rft.aufirst=Bernhard+Conrad&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D-plPAAAAYAAJ%26dq%3DHesse%2BBC%2Bacetamide%26pg%3DPA1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:10-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-:10_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:10_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:10_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://lanxess.com/-/media/project/lanxess/corporate-internet/07_us-media/product-safety-assessments/dbnpa.pdf">"Lanxess product safety assessment"</a> <span class="cs1-format">(PDF)</span>. 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Lanxess+product+safety+assessment&rft.date=2015&rft_id=https%3A%2F%2Flanxess.com%2F-%2Fmedia%2Fproject%2Flanxess%2Fcorporate-internet%2F07_us-media%2Fproduct-safety-assessments%2Fdbnpa.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://scholar.google.com/scholar_lookup?journal=U%20S%20Patent&title=Seed%20and%20Plant%20Disinfectants&author=HK%20Nolan&author=I%20Hechenbleikner&volume=2&publication_year=1947&pages=419888&">"Google Scholar"</a>. <i>scholar.google.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2025-03-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=scholar.google.com&rft.atitle=Google+Scholar&rft_id=https%3A%2F%2Fscholar.google.com%2Fscholar_lookup%3Fjournal%3DU%2520S%2520Patent%26title%3DSeed%2520and%2520Plant%2520Disinfectants%26author%3DHK%2520Nolan%26author%3DI%2520Hechenbleikner%26volume%3D2%26publication_year%3D1947%26pages%3D419888%26&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWolfSterner1972" class="citation journal cs1">Wolf, Paul A.; Sterner, P. W. (October 1972). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC380617">"2,2-Dibromo-3-Nitrilopropionamide, a Compound with Slimicidal Activity"</a>. <i>Applied Microbiology</i>. <b>24</b> (4): <span class="nowrap">581–</span>584. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2Fam.24.4.581-584.1972">10.1128/am.24.4.581-584.1972</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0003-6919">0003-6919</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC380617">380617</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16349941">16349941</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Applied+Microbiology&rft.atitle=2%2C2-Dibromo-3-Nitrilopropionamide%2C+a+Compound+with+Slimicidal+Activity&rft.volume=24&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E581-%3C%2Fspan%3E584&rft.date=1972-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC380617%23id-name%3DPMC&rft.issn=0003-6919&rft_id=info%3Apmid%2F16349941&rft_id=info%3Adoi%2F10.1128%2Fam.24.4.581-584.1972&rft.aulast=Wolf&rft.aufirst=Paul+A.&rft.au=Sterner%2C+P.+W.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC380617&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:5-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-:5_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:5_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:5_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:5_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:5_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-:5_6-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-:5_6-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-:5_6-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-:5_6-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSimpsonWiatr2022" class="citation journal cs1">Simpson, J. V.; Wiatr, C. L. (May 2022). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8964648">"Quantification and Degradation of 2,2-Dibromo-3-Nitrilopropionamide (DBNPA) in Bioethanol Fermentation Coproducts"</a>. <i>World Journal of Microbiology and Biotechnology</i>. <b>38</b> (5): 82. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11274-022-03253-0">10.1007/s11274-022-03253-0</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0959-3993">0959-3993</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8964648">8964648</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35348889">35348889</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=World+Journal+of+Microbiology+and+Biotechnology&rft.atitle=Quantification+and+Degradation+of+2%2C2-Dibromo-3-Nitrilopropionamide+%28DBNPA%29+in+Bioethanol+Fermentation+Coproducts&rft.volume=38&rft.issue=5&rft.pages=82&rft.date=2022-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8964648%23id-name%3DPMC&rft.issn=0959-3993&rft_id=info%3Apmid%2F35348889&rft_id=info%3Adoi%2F10.1007%2Fs11274-022-03253-0&rft.aulast=Simpson&rft.aufirst=J.+V.&rft.au=Wiatr%2C+C.+L.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8964648&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:0-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:0_7-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:0_7-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPubChem" class="citation web cs1">PubChem. <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2_2-Dibromo-3-nitrilopropionamide">"2,2-Dibromo-3-nitrilopropionamide"</a>. <i>pubchem.ncbi.nlm.nih.gov</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2025-03-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=2%2C2-Dibromo-3-nitrilopropionamide&rft.au=PubChem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F2_2-Dibromo-3-nitrilopropionamide&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:3-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-:3_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:3_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:3_8-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBarrosMeloPereira2022" class="citation journal cs1">Barros, Ana C.; Melo, Luis F.; Pereira, Ana (2022-02-18). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8894764">"A Multi-Purpose Approach to the Mechanisms of Action of Two Biocides (Benzalkonium Chloride and Dibromonitrilopropionamide): Discussion of Pseudomonas fluorescens' Viability and Death"</a>. <i>Frontiers in Microbiology</i>. <b>13</b>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffmicb.2022.842414">10.3389/fmicb.2022.842414</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1664-302X">1664-302X</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8894764">8894764</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35250955">35250955</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Microbiology&rft.atitle=A+Multi-Purpose+Approach+to+the+Mechanisms+of+Action+of+Two+Biocides+%28Benzalkonium+Chloride+and+Dibromonitrilopropionamide%29%3A+Discussion+of+Pseudomonas+fluorescens%27+Viability+and+Death&rft.volume=13&rft.date=2022-02-18&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8894764%23id-name%3DPMC&rft.issn=1664-302X&rft_id=info%3Apmid%2F35250955&rft_id=info%3Adoi%2F10.3389%2Ffmicb.2022.842414&rft.aulast=Barros&rft.aufirst=Ana+C.&rft.au=Melo%2C+Luis+F.&rft.au=Pereira%2C+Ana&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8894764&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:7-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-:7_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:7_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:7_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:7_9-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:7_9-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-:7_9-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-:7_9-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-:7_9-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFExnerBurkKyriacou1973" class="citation journal cs1">Exner, Jurgen H.; Burk, George A.; Kyriacou, Demetrios (May 1973). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/abs/10.1021/jf60189a012">"Rates and products of decomposition of 2,2-dibromo-3-nitrilopropionamide"</a>. <i>Journal of Agricultural and Food Chemistry</i>. <b>21</b> (5): <span class="nowrap">838–</span>842. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1973JAFC...21..838E">1973JAFC...21..838E</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf60189a012">10.1021/jf60189a012</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0021-8561">0021-8561</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/4733375">4733375</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Agricultural+and+Food+Chemistry&rft.atitle=Rates+and+products+of+decomposition+of+2%2C2-dibromo-3-nitrilopropionamide&rft.volume=21&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E838-%3C%2Fspan%3E842&rft.date=1973-05&rft_id=info%3Adoi%2F10.1021%2Fjf60189a012&rft.issn=0021-8561&rft_id=info%3Apmid%2F4733375&rft_id=info%3Abibcode%2F1973JAFC...21..838E&rft.aulast=Exner&rft.aufirst=Jurgen+H.&rft.au=Burk%2C+George+A.&rft.au=Kyriacou%2C+Demetrios&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fjf60189a012&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:6-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-:6_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:6_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:6_10-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:6_10-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:6_10-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-:6_10-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-:6_10-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-:6_10-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-:6_10-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUS_Environmental_protection_agency1994" class="citation web cs1">US Environmental protection agency (1994). <a rel="nofollow" class="external text" href="https://archive.epa.gov/pesticides/reregistration/web/pdf/3056.pdf">"prevention, pesticides and Toxic substances"</a> <span class="cs1-format">(PDF)</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=prevention%2C+pesticides+and+Toxic+substances&rft.date=1994&rft.au=US+Environmental+protection+agency&rft_id=https%3A%2F%2Farchive.epa.gov%2Fpesticides%2Freregistration%2Fweb%2Fpdf%2F3056.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:1-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:1_11-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:1_11-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:1_11-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-:1_11-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDa-Silva-CorreaSmithThibodeauWelsh2022" class="citation journal cs1">Da-Silva-Correa, Luiz H.; Smith, Hayley; Thibodeau, Matthew C.; Welsh, Bethany; Buckley, Heather L. (2022-01-22). <a rel="nofollow" class="external text" href="https://iwaponline.com/aqua/article/71/2/261/86389/The-application-of-non-oxidizing-biocides-to">"The application of non-oxidizing biocides to prevent biofouling in reverse osmosis polyamide membrane systems: a review"</a>. <i>AQUA - Water Infrastructure, Ecosystems and Society</i>. <b>71</b> (2): <span class="nowrap">261–</span>292. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.2166%2Faqua.2022.118">10.2166/aqua.2022.118</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2709-8028">2709-8028</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=AQUA+-+Water+Infrastructure%2C+Ecosystems+and+Society&rft.atitle=The+application+of+non-oxidizing+biocides+to+prevent+biofouling+in+reverse+osmosis+polyamide+membrane+systems%3A+a+review&rft.volume=71&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E261-%3C%2Fspan%3E292&rft.date=2022-01-22&rft_id=info%3Adoi%2F10.2166%2Faqua.2022.118&rft.issn=2709-8028&rft.aulast=Da-Silva-Correa&rft.aufirst=Luiz+H.&rft.au=Smith%2C+Hayley&rft.au=Thibodeau%2C+Matthew+C.&rft.au=Welsh%2C+Bethany&rft.au=Buckley%2C+Heather+L.&rft_id=https%3A%2F%2Fiwaponline.com%2Faqua%2Farticle%2F71%2F2%2F261%2F86389%2FThe-application-of-non-oxidizing-biocides-to&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent" id="CITEREF李建生刘炳光苏超翟梦雅2012"><a rel="nofollow" class="external text" href="https://patents.google.com/patent/CN102432500A/en">CN102432500A</a>, 李建生; 刘炳光 & 苏超 et al., "A kind of 2,2-dibromo-3-nitrilopropionamide preparation method", issued 2012-05-02</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=CN102432500A&rft.cc=&rft.title=A+kind+of+2%2C2-dibromo-3-nitrilopropionamide+preparation+method&rft.inventor=%E6%9D%8E%E5%BB%BA%E7%94%9F&rft.date=2012-05-02"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKucera2019" class="citation journal cs1">Kucera, Jane (2019-08-30). <a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fmembranes9090111">"Biofouling of Polyamide Membranes: Fouling Mechanisms, Current Mitigation and Cleaning Strategies, and Future Prospects"</a>. <i>Membranes</i>. <b>9</b> (9): 111. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fmembranes9090111">10.3390/membranes9090111</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2077-0375">2077-0375</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/31480327">31480327</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Membranes&rft.atitle=Biofouling+of+Polyamide+Membranes%3A+Fouling+Mechanisms%2C+Current+Mitigation+and+Cleaning+Strategies%2C+and+Future+Prospects&rft.volume=9&rft.issue=9&rft.pages=111&rft.date=2019-08-30&rft.issn=2077-0375&rft_id=info%3Apmid%2F31480327&rft_id=info%3Adoi%2F10.3390%2Fmembranes9090111&rft.aulast=Kucera&rft.aufirst=Jane&rft_id=https%3A%2F%2Fdoi.org%2F10.3390%252Fmembranes9090111&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:8-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-:8_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:8_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:8_14-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWiatr" class="citation web cs1">Wiatr, Christopher L. <a rel="nofollow" class="external text" href="https://patentimages.storage.googleapis.com/cb/de/86/3e3b7a59ac13c1/EP2955231B1.pdf">"Patent 2018: Processes Using Antibiotic Alternatives in Bioethanol Production"</a> <span class="cs1-format">(PDF)</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Patent+2018%3A+Processes+Using+Antibiotic+Alternatives+in+Bioethanol+Production&rft.aulast=Wiatr&rft.aufirst=Christopher+L&rft_id=https%3A%2F%2Fpatentimages.storage.googleapis.com%2Fcb%2Fde%2F86%2F3e3b7a59ac13c1%2FEP2955231B1.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:9-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-:9_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:9_15-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:9_15-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWiatrCorcoran" class="citation web cs1">Wiatr, Christopher, L.; Corcoran, Michael. <a rel="nofollow" class="external text" href="https://patentimages.storage.googleapis.com/a5/5c/68/3b76a0c8b4919d/EP2955231A2.pdf">"Patent 2011: Processes Using Antibiotic Alternatives in Bioethanol Production"</a> <span class="cs1-format">(PDF)</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Patent+2011%3A+Processes+Using+Antibiotic+Alternatives+in+Bioethanol+Production&rft.aulast=Wiatr&rft.aufirst=Christopher%2C+L.&rft.au=Corcoran%2C+Michael&rft_id=https%3A%2F%2Fpatentimages.storage.googleapis.com%2Fa5%2F5c%2F68%2F3b76a0c8b4919d%2FEP2955231A2.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_web" title="Template:Cite web">cite web</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-:2-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-:2_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:2_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:2_16-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:2_16-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWater2019" class="citation web cs1">Water, I. R. O. (2019-06-27). <a rel="nofollow" class="external text" href="https://www.irowater.com/2-2-dibromo-3-nitrilopropionamide-dbnpa-guide-part-1/">"2,2-Dibromo-3-Nitrilopropionamide (DBNPA) Guide Part 1"</a>. <i>IRO Water Treatment</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2025-03-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=IRO+Water+Treatment&rft.atitle=2%2C2-Dibromo-3-Nitrilopropionamide+%28DBNPA%29+Guide+Part+1&rft.date=2019-06-27&rft.aulast=Water&rft.aufirst=I.+R.+O.&rft_id=https%3A%2F%2Fwww.irowater.com%2F2-2-dibromo-3-nitrilopropionamide-dbnpa-guide-part-1%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-:4-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-:4_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:4_17-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:4_17-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIshikawaMuraguchiAzumaNawata2016" class="citation journal cs1">Ishikawa, Mizuki; Muraguchi, Ryosuke; Azuma, Ayako; Nawata, Shogo; Miya, Mutsumi; Katsuura, Tetsuya; Naito, Tohru; Oyama, Yasuo (2016-09-01). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6062308">"Cytotoxic actions of 2,2-dibromo-3-nitrilopropionamide, a biocide in hydraulic fracturing fluids, on rat thymocytes"</a>. <i>Toxicology Research</i>. <b>5</b> (5): <span class="nowrap">1329–</span>1334. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fc6tx00027d">10.1039/c6tx00027d</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2045-4538">2045-4538</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6062308">6062308</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30090437">30090437</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicology+Research&rft.atitle=Cytotoxic+actions+of+2%2C2-dibromo-3-nitrilopropionamide%2C+a+biocide+in+hydraulic+fracturing+fluids%2C+on+rat+thymocytes&rft.volume=5&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1329-%3C%2Fspan%3E1334&rft.date=2016-09-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6062308%23id-name%3DPMC&rft.issn=2045-4538&rft_id=info%3Apmid%2F30090437&rft_id=info%3Adoi%2F10.1039%2Fc6tx00027d&rft.aulast=Ishikawa&rft.aufirst=Mizuki&rft.au=Muraguchi%2C+Ryosuke&rft.au=Azuma%2C+Ayako&rft.au=Nawata%2C+Shogo&rft.au=Miya%2C+Mutsumi&rft.au=Katsuura%2C+Tetsuya&rft.au=Naito%2C+Tohru&rft.au=Oyama%2C+Yasuo&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6062308&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKimAndersonMuellerGaines2002" class="citation journal cs1">Kim, B. R.; Anderson, J. E.; Mueller, S. A.; Gaines, W. A.; Kendall, A. M. (2002-11-01). <a rel="nofollow" class="external text" href="https://linkinghub.elsevier.com/retrieve/pii/S0043135402001884">"Literature review—efficacy of various disinfectants against Legionella in water systems"</a>. <i>Water Research</i>. <b>36</b> (18): <span class="nowrap">4433–</span>4444. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2002WatRe..36.4433K">2002WatRe..36.4433K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0043-1354%2802%2900188-4">10.1016/S0043-1354(02)00188-4</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0043-1354">0043-1354</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/12418646">12418646</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Water+Research&rft.atitle=Literature+review%E2%80%94efficacy+of+various+disinfectants+against+Legionella+in+water+systems&rft.volume=36&rft.issue=18&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4433-%3C%2Fspan%3E4444&rft.date=2002-11-01&rft_id=info%3Adoi%2F10.1016%2FS0043-1354%2802%2900188-4&rft.issn=0043-1354&rft_id=info%3Apmid%2F12418646&rft_id=info%3Abibcode%2F2002WatRe..36.4433K&rft.aulast=Kim&rft.aufirst=B.+R.&rft.au=Anderson%2C+J.+E.&rft.au=Mueller%2C+S.+A.&rft.au=Gaines%2C+W.+A.&rft.au=Kendall%2C+A.+M.&rft_id=https%3A%2F%2Flinkinghub.elsevier.com%2Fretrieve%2Fpii%2FS0043135402001884&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation cs2"><a class="external text" href="https://en.wikipedia.org/wiki/Isothiazolinone">"Isothiazolinone"</a>, <i>Wikipedia</i>, 2025-02-06<span class="reference-accessdate">, retrieved <span class="nowrap">2025-03-13</span></span></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Wikipedia&rft.atitle=Isothiazolinone&rft.date=2025-02-06&rft_id=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FIsothiazolinone&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEachusPohlman2004" class="citation web cs1">Eachus, A. C.; Pohlman, J. L. (2004). <a rel="nofollow" class="external text" href="https://www.researchgate.net/publication/289837237">"Applications of 2,2-dibromo-3-nitrilopropionamide (DBNPA), a non-traditional antimicrobial agent, in metalworking-fluid production and use. Lubrication Engineering"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Applications+of+2%2C2-dibromo-3-nitrilopropionamide+%28DBNPA%29%2C+a+non-traditional+antimicrobial+agent%2C+in+metalworking-fluid+production+and+use.+Lubrication+Engineering&rft.date=2004&rft.aulast=Eachus&rft.aufirst=A.+C.&rft.au=Pohlman%2C+J.+L.&rft_id=https%3A%2F%2Fwww.researchgate.net%2Fpublication%2F289837237&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSkinnerLeathers2004" class="citation journal cs1">Skinner, Kelly A.; Leathers, Timothy D. (2004). <a rel="nofollow" class="external text" href="https://academic.oup.com/jimb/article/31/9/401/5992257">"Bacterial contaminants of fuel ethanol production"</a>. <i>Journal of Industrial Microbiology & Biotechnology</i>. <b>31</b> (9): <span class="nowrap">401–</span>408. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10295-004-0159-0">10.1007/s10295-004-0159-0</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1367-5435">1367-5435</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/15338420">15338420</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Industrial+Microbiology+%26+Biotechnology&rft.atitle=Bacterial+contaminants+of+fuel+ethanol+production&rft.volume=31&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E401-%3C%2Fspan%3E408&rft.date=2004&rft.issn=1367-5435&rft_id=info%3Apmid%2F15338420&rft_id=info%3Adoi%2F10.1007%2Fs10295-004-0159-0&rft.aulast=Skinner&rft.aufirst=Kelly+A.&rft.au=Leathers%2C+Timothy+D.&rft_id=https%3A%2F%2Facademic.oup.com%2Fjimb%2Farticle%2F31%2F9%2F401%2F5992257&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShiromaMarquesJesus2015" class="citation journal cs1">Shiroma, Letícia S.; Marques, Thaís T.; Jesus, Dosil P. (2015-01-03). <a rel="nofollow" class="external text" href="https://doi.org/10.2166/wst.2015.009">"A rapid and simple capillary electrophoresis method for indirect determination of the biocide 2,2-dibromo-3-nitrilo-propionamide (DBNPA) in cooling waters"</a>. <i>Water Science and Technology</i>. <b>71</b> (3): <span class="nowrap">434–</span>439. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2015WSTec..71..434S">2015WSTec..71..434S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2166%2Fwst.2015.009">10.2166/wst.2015.009</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0273-1223">0273-1223</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/25714644">25714644</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Water+Science+and+Technology&rft.atitle=A+rapid+and+simple+capillary+electrophoresis+method+for+indirect+determination+of+the+biocide+2%2C2-dibromo-3-nitrilo-propionamide+%28DBNPA%29+in+cooling+waters&rft.volume=71&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E434-%3C%2Fspan%3E439&rft.date=2015-01-03&rft_id=info%3Adoi%2F10.2166%2Fwst.2015.009&rft.issn=0273-1223&rft_id=info%3Apmid%2F25714644&rft_id=info%3Abibcode%2F2015WSTec..71..434S&rft.aulast=Shiroma&rft.aufirst=Let%C3%ADcia+S.&rft.au=Marques%2C+Tha%C3%ADs+T.&rft.au=Jesus%2C+Dosil+P.&rft_id=https%3A%2F%2Fdoi.org%2F10.2166%2Fwst.2015.009&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKiuruTsitkoSievänenWathén2010" class="citation journal cs1">Kiuru, Jani; Tsitko, Irina; Sievänen, Jenni; Wathén, Rolf (2010-01-28). <a rel="nofollow" class="external text" href="https://doi.org/10.15376/biores.5.2.514-524">"Optimization of biocide strategies on fine paper machines"</a>. <i>BioResources</i>. <b>5</b> (2): <span class="nowrap">514–</span>524. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.15376%2Fbiores.5.2.514-524">10.15376/biores.5.2.514-524</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1930-2126">1930-2126</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BioResources&rft.atitle=Optimization+of+biocide+strategies+on+fine+paper+machines&rft.volume=5&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E514-%3C%2Fspan%3E524&rft.date=2010-01-28&rft_id=info%3Adoi%2F10.15376%2Fbiores.5.2.514-524&rft.issn=1930-2126&rft.aulast=Kiuru&rft.aufirst=Jani&rft.au=Tsitko%2C+Irina&rft.au=Siev%C3%A4nen%2C+Jenni&rft.au=Wath%C3%A9n%2C+Rolf&rft_id=https%3A%2F%2Fdoi.org%2F10.15376%2Fbiores.5.2.514-524&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFExnerBurkKyriacou1973" class="citation journal cs1">Exner, Jurgen H.; Burk, George A.; Kyriacou, Demetrios (1973). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/abs/10.1021/jf60189a012">"Rates and products of decomposition of 2,2-dibromo-3-nitrilopropionamide"</a>. <i>Journal of Agricultural and Food Chemistry</i>. <b>21</b> (5): <span class="nowrap">838–</span>842. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1973JAFC...21..838E">1973JAFC...21..838E</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf60189a012">10.1021/jf60189a012</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0021-8561">0021-8561</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/4733375">4733375</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Agricultural+and+Food+Chemistry&rft.atitle=Rates+and+products+of+decomposition+of+2%2C2-dibromo-3-nitrilopropionamide&rft.volume=21&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E838-%3C%2Fspan%3E842&rft.date=1973&rft_id=info%3Adoi%2F10.1021%2Fjf60189a012&rft.issn=0021-8561&rft_id=info%3Apmid%2F4733375&rft_id=info%3Abibcode%2F1973JAFC...21..838E&rft.aulast=Exner&rft.aufirst=Jurgen+H.&rft.au=Burk%2C+George+A.&rft.au=Kyriacou%2C+Demetrios&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fjf60189a012&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://archive.epa.gov/pesticides/reregistration/web/pdf/3056.pdf">"Reregistration Eligibility Decision (RED) DBNPA of US Environmental protection agency"</a> <span class="cs1-format">(PDF)</span>. 1994.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Reregistration+Eligibility+Decision+%28RED%29+DBNPA+of+US+Environmental+protection+agency&rft.date=1994&rft_id=https%3A%2F%2Farchive.epa.gov%2Fpesticides%2Freregistration%2Fweb%2Fpdf%2F3056.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span><span class="noviewer" typeof="mw:File"><span><img alt="Public Domain" src="//upload.wikimedia.org/wikipedia/en/thumb/6/62/PD-icon.svg/12px-PD-icon.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/62/PD-icon.svg/18px-PD-icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/62/PD-icon.svg/24px-PD-icon.svg.png 2x" data-file-width="196" data-file-height="196" /></span></span> This article incorporates text from this source, which is in the <a href="/wiki/Public_domain" title="Public domain">public domain</a>.</span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPourshaban-ShahrestaniHassanKoohi2023" class="citation journal cs1">Pourshaban-Shahrestani, Ali; Hassan, Jalal; Koohi, Mohammad Kazem (2023-11-28). <a rel="nofollow" class="external text" href="https://doi.org/10.1007/s00128-023-03824-3">"In Vivo Toxicity of Industrial Biocide Containing 2,2-Dibromo-3-nitrilopropionamide in Adult and Zebrafish Larvae"</a>. <i>Bulletin of Environmental Contamination and Toxicology</i>. <b>112</b> (1): 2. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00128-023-03824-3">10.1007/s00128-023-03824-3</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0007-4861">0007-4861</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/38017139">38017139</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+of+Environmental+Contamination+and+Toxicology&rft.atitle=In+Vivo+Toxicity+of+Industrial+Biocide+Containing+2%2C2-Dibromo-3-nitrilopropionamide+in+Adult+and+Zebrafish+Larvae&rft.volume=112&rft.issue=1&rft.pages=2&rft.date=2023-11-28&rft.issn=0007-4861&rft_id=info%3Apmid%2F38017139&rft_id=info%3Adoi%2F10.1007%2Fs00128-023-03824-3&rft.aulast=Pourshaban-Shahrestani&rft.aufirst=Ali&rft.au=Hassan%2C+Jalal&rft.au=Koohi%2C+Mohammad+Kazem&rft_id=https%3A%2F%2Fdoi.org%2F10.1007%2Fs00128-023-03824-3&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKjeldgaardCohnCaseyHill2012" class="citation journal cs1">Kjeldgaard, Jette; Cohn, Marianne T.; Casey, Pat G.; Hill, Colin; Ingmer, Hanne (2012). Casadevall, Arturo (ed.). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3445968">"Residual Antibiotics Disrupt Meat Fermentation and Increase Risk of Infection"</a>. <i>mBio</i>. <b>3</b> (5): e00190-12. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FmBio.00190-12">10.1128/mBio.00190-12</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2161-2129">2161-2129</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3445968">3445968</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22930338">22930338</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=mBio&rft.atitle=Residual+Antibiotics+Disrupt+Meat+Fermentation+and+Increase+Risk+of+Infection&rft.volume=3&rft.issue=5&rft.pages=e00190-12&rft.date=2012&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3445968%23id-name%3DPMC&rft.issn=2161-2129&rft_id=info%3Apmid%2F22930338&rft_id=info%3Adoi%2F10.1128%2FmBio.00190-12&rft.aulast=Kjeldgaard&rft.aufirst=Jette&rft.au=Cohn%2C+Marianne+T.&rft.au=Casey%2C+Pat+G.&rft.au=Hill%2C+Colin&rft.au=Ingmer%2C+Hanne&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3445968&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWistrand-YuenKnoppHjortKoskiniemi2018" class="citation journal cs1">Wistrand-Yuen, Erik; Knopp, Michael; Hjort, Karin; Koskiniemi, Sanna; Berg, Otto G.; Andersson, Dan I. (2018-04-23). <a rel="nofollow" class="external text" href="https://doi.org/10.1038/s41467-018-04059-1">"Evolution of high-level resistance during low-level antibiotic exposure"</a>. <i>Nature Communications</i>. <b>9</b> (1): 1599. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2018NatCo...9.1599W">2018NatCo...9.1599W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fs41467-018-04059-1">10.1038/s41467-018-04059-1</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2041-1723">2041-1723</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5913237">5913237</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Communications&rft.atitle=Evolution+of+high-level+resistance+during+low-level+antibiotic+exposure&rft.volume=9&rft.issue=1&rft.pages=1599&rft.date=2018-04-23&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5913237%23id-name%3DPMC&rft.issn=2041-1723&rft_id=info%3Adoi%2F10.1038%2Fs41467-018-04059-1&rft_id=info%3Abibcode%2F2018NatCo...9.1599W&rft.aulast=Wistrand-Yuen&rft.aufirst=Erik&rft.au=Knopp%2C+Michael&rft.au=Hjort%2C+Karin&rft.au=Koskiniemi%2C+Sanna&rft.au=Berg%2C+Otto+G.&rft.au=Andersson%2C+Dan+I.&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%2Fs41467-018-04059-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChingZaman2020" class="citation journal cs1">Ching, Carly; Zaman, Muhammad H. (2020-05-29). <a rel="nofollow" class="external text" href="https://www.nature.com/articles/s41598-020-65602-z">"Development and selection of low-level multi-drug resistance over an extended range of sub-inhibitory ciprofloxacin concentrations in Escherichia coli"</a>. <i>Scientific Reports</i>. <b>10</b> (1): 8754. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2020NatSR..10.8754C">2020NatSR..10.8754C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fs41598-020-65602-z">10.1038/s41598-020-65602-z</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2045-2322">2045-2322</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7260183">7260183</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scientific+Reports&rft.atitle=Development+and+selection+of+low-level+multi-drug+resistance+over+an+extended+range+of+sub-inhibitory+ciprofloxacin+concentrations+in+Escherichia+coli&rft.volume=10&rft.issue=1&rft.pages=8754&rft.date=2020-05-29&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7260183%23id-name%3DPMC&rft.issn=2045-2322&rft_id=info%3Adoi%2F10.1038%2Fs41598-020-65602-z&rft_id=info%3Abibcode%2F2020NatSR..10.8754C&rft.aulast=Ching&rft.aufirst=Carly&rft.au=Zaman%2C+Muhammad+H.&rft_id=https%3A%2F%2Fwww.nature.com%2Farticles%2Fs41598-020-65602-z&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADBNPA" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBischoffZhangRich2016" class="citation journal cs1">Bischoff, Kenneth M.; Zhang, Yanhong; Rich, Joseph O. 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