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</div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Azadirachtin</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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href="https://cs.wikipedia.org/wiki/Azadirachtin" title="Azadirachtin – Czech" lang="cs" hreflang="cs" data-title="Azadirachtin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Azadirachtin" title="Azadirachtin – German" lang="de" hreflang="de" data-title="Azadirachtin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Azadiractina" title="Azadiractina – Spanish" lang="es" hreflang="es" data-title="Azadiractina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Azadirachtine" title="Azadirachtine – French" lang="fr" hreflang="fr" data-title="Azadirachtine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Azadiractina" title="Azadiractina – Galician" lang="gl" hreflang="gl" data-title="Azadiractina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Azadiractina" title="Azadiractina – Italian" lang="it" hreflang="it" data-title="Azadiractina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%96%D7%93%D7%A8%D7%9B%D7%98%D7%99%D7%9F" title="אזדרכטין – Hebrew" lang="he" hreflang="he" data-title="אזדרכטין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%82%B6%E3%82%B8%E3%83%A9%E3%82%AF%E3%83%81%E3%83%B3" title="アザジラクチン – Japanese" lang="ja" hreflang="ja" data-title="アザジラクチン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Azadiraktin" title="Azadiraktin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Azadiraktin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Azadirahtin" title="Azadirahtin – Serbian" lang="sr" hreflang="sr" data-title="Azadirahtin" 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/Azadirahtin" title="Azadirahtin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Azadirahtin" 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-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%AD%E0%B8%B2%E0%B8%8B%E0%B8%B2%E0%B8%94%E0%B8%B4%E0%B9%80%E0%B8%A3%E0%B8%8B%E0%B8%95%E0%B8%B4%E0%B8%99" title="อาซาดิเรซติน – Thai" lang="th" hreflang="th" data-title="อาซาดิเรซติน" 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href="/wiki/File:Azadirachtin.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Azadirachtin.png/200px-Azadirachtin.png" decoding="async" width="200" height="185" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Azadirachtin.png/300px-Azadirachtin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Azadirachtin.png/400px-Azadirachtin.png 2x" data-file-width="789" data-file-height="731" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Azadirachtin_model.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Azadirachtin_model.png/200px-Azadirachtin_model.png" decoding="async" width="200" height="224" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Azadirachtin_model.png/300px-Azadirachtin_model.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Azadirachtin_model.png/400px-Azadirachtin_model.png 2x" data-file-width="634" data-file-height="711" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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;">Dimethyl (2a<i>R</i>,2a<sup>1</sup><i>R</i>,3<i>S</i>,4<i>S</i>,4a<i>R</i>,5<i>S</i>,7a<i>S</i>,8<i>S</i>,10<i>R</i>,10a<i>S</i>)-10-(acetyloxy)-3,5-dihydroxy-4-[(1a<i>R</i>,2<i>S</i>,3a<i>S</i>,6a<i>S</i>,7<i>S</i>,7a<i>S</i>)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-<i>b</i>]oxireno[2,3-<i>e</i>]oxepin-1a(2<i>H</i>)-yl]-4-methyl-8-{[(2<i>E</i>)-2-methylbut-2-enoyl]oxy}octahydro-1<i>H</i>,7<i>H</i>-naphtho[1,8-<i>bc</i>:4,4a-<i>c</i>′]difuran-5,10a(8<i>H</i>)-dicarboxylate</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=11141-17-6">11141-17-6</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=O%3DC%28OC%29%5BC%40%40%5D1%28O%29OC%5BC%40%5D82%5BC%40%40H%5D%28OC%28%3DO%29%2FC%28%3DC%2FC%29C%29C%5BC%40%40H%5D%28OC%28%3DO%29C%29%5BC%40%40%5D7%28C%28%3DO%29OC%29CO%5BC%40%40H%5D%28%5BC%40%40H%5D%28O%29%5BC%40%5D%28C%29%28%5BC%40H%5D12%29%5BC%40%5D64O%5BC%40%5D6%28%5BC%40%40H%5D3%5BC%40%40%5D5%28O%29%2FC%3DC%5CO%5BC%40H%5D5O%5BC%40H%5D4C3%29C%29%5BC%40%40H%5D78">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=2942">CHEBI:2942</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4444685.html">4444685</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/100.115.924">100.115.924</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q793471#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C08748">C08748</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5281303">5281303</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/O4U1SAF85H">O4U1SAF85H</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID0037497">DTXSID0037497</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q793471#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; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1<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: FTNJWQUOZFUQQJ-NDAWSKJSSA-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; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(OC)[C@@]1(O)OC[C@]82[C@@H](OC(=O)/C(=C/C)C)C[C@@H](OC(=O)C)[C@@]7(C(=O)OC)CO[C@@H]([C@@H](O)[C@](C)([C@H]12)[C@]64O[C@]6([C@@H]3[C@@]5(O)/C=C\O[C@H]5O[C@H]4C3)C)[C@@H]78</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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>35</sub><span title="Hydrogen">H</span><sub>44</sub><span title="Oxygen">O</span><sub>16</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002720721000000000♠"></span>720.721</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443410207&page2=Azadirachtin">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Azadirachtin</b>, a <a href="/wiki/Chemical" class="mw-redirect" title="Chemical">chemical</a> compound belonging to the <a href="/wiki/Limonoid" title="Limonoid">limonoid</a> group, is a <a href="/wiki/Secondary_metabolite" title="Secondary metabolite">secondary metabolite</a> present in <a href="/wiki/Neem" class="mw-redirect" title="Neem">neem</a> seeds. It is a highly oxidized <a href="/wiki/Tetranortriterpenoid" title="Tetranortriterpenoid">tetranortriterpenoid</a> which boasts a plethora of oxygen-bearing functional groups, including an <a href="/wiki/Enol_ether" title="Enol ether">enol ether</a>, acetal, <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a>, tetra-substituted <a href="/wiki/Epoxide" title="Epoxide">epoxide</a> and a variety of <a href="/wiki/Carboxylic_ester" class="mw-redirect" title="Carboxylic ester">carboxylic esters</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemical_synthesis">Chemical synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azadirachtin&action=edit&section=1" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Azadirachtin has a complex molecular structure; it presents both secondary and tertiary hydroxyl groups and a <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> ether in its <a href="/wiki/Molecular_structure" class="mw-redirect" title="Molecular structure">molecular structure</a>, alongside 16 stereogenic centres, 7 of which are tetrasubstituted. These characteristics explain the great difficulty encountered when trying to prepare this compound from simple precursors, using methods of <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthetic organic chemistry</a>. </p><p>Hence, the first total synthesis was published over 22 years after the compound's discovery: this first synthesis was completed by the research group of <a href="/wiki/Steven_Ley" class="mw-redirect" title="Steven Ley">Steven Ley</a> at the <a href="/wiki/University_of_Cambridge" title="University of Cambridge">University of Cambridge</a> in 2007.<sup id="cite_ref-pmid17665403_1-0" class="reference"><a href="#cite_note-pmid17665403-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17687288_2-0" class="reference"><a href="#cite_note-pmid17687288-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The described synthesis was a <a href="/w/index.php?title=Relay_approach&action=edit&redlink=1" class="new" title="Relay approach (page does not exist)">relay approach</a>, with the required, heavily functionalized <a href="/wiki/Decalin" title="Decalin">decalin</a> intermediate being made by total synthesis on a small scale, but being derived from the natural product itself for the gram-scale operations required to complete the synthesis. </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence_and_use">Occurrence and use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azadirachtin&action=edit&section=2" title="Edit section: Occurrence and use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Initially found to be active as a feeding inhibitor towards the <a href="/wiki/Desert_locust" title="Desert locust">desert locust</a> (<i>Schistocerca gregaria</i>),<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> it is now known to affect over 200 species of <a href="/wiki/Insects" class="mw-redirect" title="Insects">insects</a>, by acting mainly as an antifeedant and growth disruptor. Azadirachtin exhibits considerable toxicity towards <a href="/wiki/Spodoptera_littoralis" title="Spodoptera littoralis">African cotton leafworm</a> (<i>Spodoptera littoralis</i>), which are resistant to a commonly used biological pesticide, <i><a href="/wiki/Bacillus_thuringiensis" title="Bacillus thuringiensis">Bacillus thuringiensis</a></i>. Azadirachtin fulfills many of the criteria needed for a good <a href="/wiki/Insecticide" title="Insecticide">insecticide</a>. Azadirachtin is <a href="/wiki/Biodegradable" class="mw-redirect" title="Biodegradable">biodegradable</a> (it degrades within 100 hours when exposed to light and water) and shows very low <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> to <a href="/wiki/Mammals" class="mw-redirect" title="Mammals">mammals</a> (the <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> in rats is > 3,540 mg/kg making it practically non-toxic). </p><p>This compound is found in the seeds (0.2 to 0.8 percent by weight) of the <a href="/wiki/Neem" class="mw-redirect" title="Neem">neem</a> tree, <i><a href="/wiki/Azadirachta_indica" title="Azadirachta indica">Azadirachta indica</a></i> (hence the prefix aza does not imply an <a href="/wiki/Aza-" title="Aza-">aza compound</a>, but refers to the <a href="/wiki/Binomial_nomenclature" title="Binomial nomenclature">scientific species name</a>). Many more compounds, related to azadirachtin, are present in the seeds as well as in the leaves and the bark of the neem tree which also show strong biological activities among various pest insects <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><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> Effects of these preparations on beneficial arthropods are generally considered to be minimal <sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2020)">citation needed</span></a></i>]</sup>. Some laboratory and field studies have found neem extracts to be compatible with biological control. Because pure neem oil contains other insecticidal and fungicidal compounds in addition to azadirachtin, it is generally mixed at a rate of 1 US fluid ounce per US gallon (7.8 mL/L) of water when used as a pesticide. </p><p>Azadirachtin is the active ingredient in many pesticides including TreeAzin,<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> AzaMax,<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> BioNEEM,<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> AzaGuard,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and AzaSol,<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Terramera Proof <sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> and Terramera Cirkil.<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>Azadirachtin has a synergistic effect with the <a href="/wiki/Biocontrol" class="mw-redirect" title="Biocontrol">biocontrol</a> agent <i><a href="/wiki/Beauveria" title="Beauveria">Beauveria</a></i>.<sup id="cite_ref-Vyas-et-al-1992_13-0" class="reference"><a href="#cite_note-Vyas-et-al-1992-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Nimbecidine" class="mw-redirect" title="Nimbecidine">Nimbecidine</a> is a natural product insecticide mix which is mostly azadirachtin, with some other <a href="/wiki/Limonoid" title="Limonoid">limonoids</a>.<sup id="cite_ref-Fountain-Hopkin-2005_14-0" class="reference"><a href="#cite_note-Fountain-Hopkin-2005-14"><span class="cite-bracket">[</span>14<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=Azadirachtin&action=edit&section=3" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Azadirachtin interferes with a wide variety of insect pathways.<sup id="cite_ref-KM_15-0" class="reference"><a href="#cite_note-KM-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <ul><li>The substance acts as an <a href="/wiki/Insect_growth_regulator" title="Insect growth regulator">insect growth regulator</a>. It antagonizes both <a href="/wiki/Ecdysteroid" title="Ecdysteroid">ecdysteroid</a> (mainly 20E) and <a href="/wiki/Juvenile_hormone" title="Juvenile hormone">juvenile hormone</a> activities by reducing secretion of <a href="/wiki/Prothoracicotropic_hormone" title="Prothoracicotropic hormone">prothoracicotropic hormone</a> (PTTH) and <a href="/w/index.php?title=Allatotropin&action=edit&redlink=1" class="new" title="Allatotropin (page does not exist)">allatotropins</a> from the <a href="/wiki/Corpus_cardiacum" class="mw-redirect" title="Corpus cardiacum">corpus cardiacum</a> complex. This neuroendocrine disruption reduces <a href="/wiki/Pupation" class="mw-redirect" title="Pupation">pupation</a>. It also causes degeneration of other neuroendocrine glands.<sup id="cite_ref-KM_15-1" class="reference"><a href="#cite_note-KM-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li> <li>The substance disrupts reproductive functions, going as far as sterility in some insects. This is partially due to the aforementioned neuroendocrine disruption surrounding 20E and JH. It could also affect yolk protein and vitallogenin synthesis. It also reduces mating success by deterrence.<sup id="cite_ref-KM_15-2" class="reference"><a href="#cite_note-KM-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li> <li>The substance also deters feeding, making it an <a href="/wiki/Antifeedant" title="Antifeedant">antifeedant</a>. It disrupts the sense of smell to the point that some insects would rather starve than eat azadirachtin-laced food. If the insect ingests the compound, the substance further inhibits digestive enzymes and could leave an aversive taste memory by activating dopaminergic neurons.<sup id="cite_ref-KM_15-3" class="reference"><a href="#cite_note-KM-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li> <li>Azadirachtin additionally has a long list of cellular and molecular targets. It upregulates p53, disrupts protein synthesis possibly through binding to Hsp60, and changes the expression of many other pathways.<sup id="cite_ref-KM_15-4" class="reference"><a href="#cite_note-KM-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azadirachtin&action=edit&section=4" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Azadirachtin is formed via an elaborate biosynthetic pathway, but is believed that the steroid <a href="/w/index.php?title=Tirucallol&action=edit&redlink=1" class="new" title="Tirucallol (page does not exist)">tirucallol</a> is the precursor to the neem <a href="/wiki/Triterpenoid" class="mw-redirect" title="Triterpenoid">triterpenoid</a> secondary metabolites. Tirucallol is formed from two units of <a href="/wiki/Farnesyl_diphosphate" class="mw-redirect" title="Farnesyl diphosphate">farnesyl diphosphate</a> (FPP) to form a C<sub>30</sub> triterpene, but then loses three methyl groups to become a C<sub>27</sub> steroid. Tirucallol undergoes an allylic isomerization to form <a href="/w/index.php?title=Butyrospermol&action=edit&redlink=1" class="new" title="Butyrospermol (page does not exist)">butyrospermol</a>, which is then oxidized. The oxidized butyrospermol subsequently rearranges via a <a href="/wiki/Wagner-Meerwein_rearrangement" class="mw-redirect" title="Wagner-Meerwein rearrangement">Wagner-Meerwein 1,2-methyl shift</a> to form <a href="/w/index.php?title=Apotirucallol&action=edit&redlink=1" class="new" title="Apotirucallol (page does not exist)">apotirucallol</a>. </p><p>Apotirucallol becomes a tetranortriterpenoid when the four terminal carbons from the side chain are cleaved off. The remaining carbons on the side chain cyclize to form a <a href="/wiki/Furan" title="Furan">furan</a> ring and the molecule is oxidized further to form azadirone and <a href="/wiki/Azadiradione" title="Azadiradione">azadiradione</a>. The third ring is then opened and oxidized to form the C-seco-limonoids such as <a href="/wiki/Nimbin_(chemical)" title="Nimbin (chemical)">nimbin</a>, <a href="/w/index.php?title=Nimbidinin&action=edit&redlink=1" class="new" title="Nimbidinin (page does not exist)">nimbidinin</a> and <a href="/w/index.php?title=Salannin&action=edit&redlink=1" class="new" title="Salannin (page does not exist)">salannin</a>, which has been <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterified</a> with a molecule of <a href="/wiki/Tiglic_acid" title="Tiglic acid">tiglic acid</a>, which is derived from <a href="/wiki/Isoleucine" title="Isoleucine">L-isoleucine</a>. It is currently proposed that the target molecule is arrived at by biosynthetically converting azadirone into salanin, which is then heavily oxidized and cyclized to reach azadirachtin. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azadirachtin&action=edit&section=5" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Arid_Forest_Research_Institute" title="Arid Forest Research Institute">Arid Forest Research Institute</a> (AFRI)</li> <li><a href="/wiki/Neem" class="mw-redirect" title="Neem">Neem</a></li> <li><a href="/wiki/Neem_cake" title="Neem cake">Neem cake</a></li> <li><a href="/wiki/Neem_oil" title="Neem oil">Neem oil</a></li> <li><a href="/wiki/Nimbin_(chemical)" title="Nimbin (chemical)">Nimbin</a>, another chemical isolated from <i>Azadirachta indica</i> also thought to contribute to the biological activity of neem</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azadirachtin&action=edit&section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-pmid17665403-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17665403_1-0">^</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 id="CITEREFVeitchBeckmannBurkeBoyer2007" class="citation journal cs1">Veitch GE, Beckmann E, Burke BJ, Boyer A, Maslen SL, Ley SV (2007). 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"<i>Folsomia candida</i> (Collembola): A "Standard" Soil Arthropod". <i><a href="/wiki/Annual_Review_of_Entomology" title="Annual Review of Entomology">Annual Review of Entomology</a></i>. <b>50</b> (1). <a href="/wiki/Annual_Reviews_(publisher)" title="Annual Reviews (publisher)">Annual Reviews</a>: 201–222. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1146%2Fannurev.ento.50.071803.130331">10.1146/annurev.ento.50.071803.130331</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/0066-4170">0066-4170</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/15355236">15355236</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annual+Review+of+Entomology&rft.atitle=Folsomia+candida+%28Collembola%29%3A+A+%22Standard%22+Soil+Arthropod&rft.volume=50&rft.issue=1&rft.pages=201-222&rft.date=2005&rft.issn=0066-4170&rft_id=info%3Apmid%2F15355236&rft_id=info%3Adoi%2F10.1146%2Fannurev.ento.50.071803.130331&rft.aulast=Fountain&rft.aufirst=Michelle+T.&rft.au=Hopkin%2C+Steve+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAzadirachtin" class="Z3988"></span></span> </li> <li id="cite_note-KM-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-KM_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-KM_15-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-KM_15-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-KM_15-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-KM_15-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKilani-MorakchiMorakchi-GoudjilSifi2021" class="citation journal cs1">Kilani-Morakchi, Samira; Morakchi-Goudjil, Houda; Sifi, Karima (20 July 2021). <a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffagro.2021.676208">"Azadirachtin-Based Insecticide: Overview, Risk Assessments, and Future Directions"</a>. <i>Frontiers in Agronomy</i>. <b>3</b>: 676208. <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%2Ffagro.2021.676208">10.3389/fagro.2021.676208</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Agronomy&rft.atitle=Azadirachtin-Based+Insecticide%3A+Overview%2C+Risk+Assessments%2C+and+Future+Directions&rft.volume=3&rft.pages=676208&rft.date=2021-07-20&rft_id=info%3Adoi%2F10.3389%2Ffagro.2021.676208&rft.aulast=Kilani-Morakchi&rft.aufirst=Samira&rft.au=Morakchi-Goudjil%2C+Houda&rft.au=Sifi%2C+Karima&rft_id=https%3A%2F%2Fdoi.org%2F10.3389%252Ffagro.2021.676208&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAzadirachtin" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Azadirachtin&action=edit&section=7" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://doi.org/10.17226/1924"><i>Neem: A Tree For Solving Global Problems</i></a>. National Research Council (US) Panel on Neem. 1992. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.17226%2F1924">10.17226/1924</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-309-04686-2" title="Special:BookSources/978-0-309-04686-2"><bdi>978-0-309-04686-2</bdi></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/25121266">25121266</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Neem%3A+A+Tree+For+Solving+Global+Problems&rft.pub=National+Research+Council+%28US%29+Panel+on+Neem&rft.date=1992&rft_id=info%3Apmid%2F25121266&rft_id=info%3Adoi%2F10.17226%2F1924&rft.isbn=978-0-309-04686-2&rft_id=https%3A%2F%2Fdoi.org%2F10.17226%2F1924&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAzadirachtin" class="Z3988"></span> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK234646/pdf/Bookshelf_NBK234646.pdf">PDF Copy</a></li> <li><a rel="nofollow" class="external text" href="http://extoxnet.orst.edu/pips/azadirac.htm">Extoxnet</a></li> <li><a rel="nofollow" class="external text" href="http://www.pakissan.com/english/allabout/horticulture/neem.wonder.tree.shtml">Neem: The wonder tree</a></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; 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