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Azadirachtin information


Azadirachtin
Names
Preferred IUPAC name
Dimethyl (2aR,2a1R,3S,4S,4aR,5S,7aS,8S,10R,10aS)-10-(acetyloxy)-3,5-dihydroxy-4-[(1aR,2S,3aS,6aS,7S,7aS)-6a-hydroxy-7a-methyl-3a,6a,7,7a-tetrahydro-2,7-methanofuro[2,3-b]oxireno[2,3-e]oxepin-1a(2H)-yl]-4-methyl-8-{[(2E)-2-methylbut-2-enoyl]oxy}octahydro-1H,7H-naphtho[1,8-bc:4,4a-c′]difuran-5,10a(8H)-dicarboxylate
Identifiers
CAS Number
  • 11141-17-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:2942 checkY
ChemSpider
  • 4444685 checkY
ECHA InfoCard 100.115.924 Edit this at Wikidata
KEGG
  • C08748 checkY
PubChem CID
  • 5281303
UNII
  • O4U1SAF85H checkY
CompTox Dashboard (EPA)
  • DTXSID0037497 Edit this at Wikidata
InChI
  • 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 checkY
    Key: FTNJWQUOZFUQQJ-NDAWSKJSSA-N checkY
SMILES
  • 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
Properties
Chemical formula
C35H44O16
Molar mass 720.721 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Azadirachtin, a chemical compound belonging to the limonoid group, is a secondary metabolite present in neem seeds. It is a highly oxidized tetranortriterpenoid which boasts a plethora of oxygen-bearing functional groups, including an enol ether, acetal, hemiacetal, tetra-substituted epoxide and a variety of carboxylic esters.

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Azadirachtin

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Azadirachtin, a chemical compound belonging to the limonoid group, is a secondary metabolite present in neem seeds. It is a highly oxidized tetranortriterpenoid...

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Azadirachta indica

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extracts, such as azadirachtin established in the 1960s as an insect antifeedant, growth disruptor, and insecticide. The yield of azadirachtin from crushing...

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Neem oil

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properties have found widespread use as a pesticide in organic farming. Azadirachtin is the most well known and studied triterpenoid in neem oil. Nimbin is...

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Limonoid

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Rutaceae, and Meliaceae. Certain limonoids are antifeedants such as azadirachtin from the neem tree. Chemically, the limonoids consist of variations of...

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Azadirachta

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components of this resin has been found to be an effective insecticide; see azadirachtin. Another component is an effective anti-fungal; see Azadirachta indica...

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Tetranortriterpenoid

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noted compound is azadirachtin, extracted from the neem tree (Azadirachta indica) that displays insecticidal properties. Azadirachtin mimics insect hormones...

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Neem cake

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cake contains salannin, nimbin, azadirachtin, meliantriol and azadiradione as the major components. Of these, azadirachtin and meliantriol are used as locust...

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Exoskeleton

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reproducing. This is the mechanism behind some insect pesticides, such as Azadirachtin. Exoskeletons, as hard parts of organisms, are greatly useful in assisting...

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Melia azedarach

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constitute an important toxic principle. These are chemically related to azadirachtin, the primary insecticidal compound in the commercially important neem...

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Insecticide

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Anethole (mosquito larvae) Annonin Asimina (pawpaw tree seeds) for lice Azadirachtin Caffeine Carapa Cinnamaldehyde (very effective for killing mosquito larvae)...

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EID Parry

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Beemax. The company is now expanding its range of products away from Azadirachtin, its core product extracted from neem seed kernel. Acquired from GMR...

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DDT

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Insect growth regulator

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chemicals (phytoecdysteroids) which use this mode of action to kill insects. Azadirachtin (AzaGuard), a natural product found in extracts from the neem tree, shows...

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List of insecticides

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amidithion [Wikidata] aminocarb amiton amitraz anabasine athidathion [Wikidata] azadirachtin azamethiphos azinphos-ethyl azinphos-methyl azothoate [Wikidata] barium...

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Pesticide poisoning

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Tuta absoluta

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chlorantraniliprole, and metaflumizone, but not azadirachtin - while the Urla, İzmir population was only resistant to azadirachtin, and even then only weakly so. Many...

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Organic farming

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Neem oil is used as an insect repellant in India; since it contains azadirachtin its use is restricted in the UK and Europe. Pyrethrin comes from chemicals...

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Permethrin

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Cyfluthrin

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Cockchafer

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collecting feeding adults can reduce population, though it is time consuming. Azadirachtin is a chemical that inhibits maturation feeding and egg development, but...

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Emerald ash borer

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sourwood, and bald cypress. Insecticides with active ingredients such as azadirachtin, imidacloprid, emamectin benzoate, and dinotefuran are currently used...

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Plant secondary metabolism

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Nitrogen-containing 2000 Concanavalin A Terpenes Without nitrogen >15,000 Azadirachtin, Artemisinin, Tetrahydrocannabinol Steroids and saponins Without nitrogen...

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Fipronil

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Boric acid

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Chlorpyrifos

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Secondary metabolite

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Examples of terpenoids built from hemiterpene oligomerization are: Azadirachtin, present in Azadirachta indica, the (Neem tree) Artemisinin, present...

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Carbaryl

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Pest control

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Flubendiamide Ryanodine Ryanodol Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin...

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Aluminium phosphide

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