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Azadirachtin

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Azadirachtin Basic information

Product Name:
Azadirachtin
Synonyms:
  • AZADIRACHTIN B
  • AZATIN
  • AZATIN(R)
  • KAYNEEM
  • 3-TIGLOYL-AZADIRACHTOL
  • AZADIRACHTIN, 10MG, NEAT
  • 1H,7H-Naphtho1,8-bc:4,4a-cdifuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(2E)-2-methyl-1-oxo-2-butenyloxy-4-(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro2,3-boxirenoeoxepin-1a(2H)
  • AZADIRACHTIN pure
CAS:
11141-17-6
MF:
C35H44O16
MW:
720.71
Product Categories:
  • Chiral Reagents
  • Heterocycles
  • Tri-Terpenoids
  • A
  • A-BAlphabetic
  • Intermediates & Fine Chemicals
  • Botanicals
  • Insecticides
  • Pesticides
  • Alpha sort
  • AR to AZPesticides
  • Pesticides&Metabolites
  • Pharmaceuticals
Mol File:
11141-17-6.mol
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Azadirachtin Chemical Properties

Melting point:
159°C
alpha 
D -53° (c = 0.5 in CHCl3)
Boiling point:
792.4±60.0 °C(Predicted)
Density 
1.51
storage temp. 
−20°C
solubility 
DMSO (Sparingly), Methanol (Slightly)
form 
Solid
pka
9.78±0.70(Predicted)
color 
White to Pale Yellow
Merck 
13,896
Stability:
Light Sensitive
InChIKey
TWGPOIQWWGNBKW-POEZYEDVSA-N
CAS DataBase Reference
11141-17-6
EPA Substance Registry System
Azadirachtin A (11141-17-6)
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Safety Information

Risk Statements 
22
Safety Statements 
22-45
RIDADR 
3077
WGK Germany 
3
HazardClass 
9
PackingGroup 
III
HS Code 
13021920
Hazardous Substances Data
11141-17-6(Hazardous Substances Data)

MSDS

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Azadirachtin Usage And Synthesis

Description

Kernel extracts from the Indian neem tree (Azadirachta indica) have insecticidal and insect-repellent properties. The key active ingredient is azadirachtin, a nortriterpenoid that exhibits insect growth regulator effects but no adulticidal activity.

Chemical Properties

Off-white, yellowish powder or dark brown emulsifiable concentrate.

Uses

Azadirachtin is a tetranortriterpinoid isolated from the seeds of the neem tree. Highly active insect feeding deterrent and growth regulator.It is used experimentally as insect control agent.

Uses

Azadiractin is extracted from the neem tree (Azadirachta indica). It is the principal active ingredient of extracts of neem. Neem extracts and pure azadirachtin are used to control whitefly, leaf miners and other pests including pear psylla.

Definition

ChEBI: A member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica).

Agricultural Uses

Insecticides, Nematicide: Azadirachtin is an extract of fruit from the Neem tree, which is largely grown in India. It is used as a commercial insect growth regulator that controls the metamorphosis process as the insect passes from the larva stage to the pupa stage. The Neem tree also yields extracts from its bark, leaves and wood that are used in medicine and cosmetics.

Trade name

ALIGN®; AZATIN EC®; AZATIN®-XL PLUS; AZATROL EC®; AMAZIN® ECOZIN® EI- 783®; MARGOSAN-O®; NEEM®; NEEMAZAL®; ORNAZIN® SALANNIN®; SUPERNEEM®; TURPLEX®

Biochem/physiol Actions

Triterpenoid found in need tree seeds, azadiractin suppresses feeding by many insect species and disrupts growth of most insect and other arthropod species, while having very low mammalian toxicity. Promising as a natural pesticide.

Potential Exposure

Biological tetranortriterpinoid insecticide; insect growth regulator. A natural product extracted from seeds of the Neem tree (Azadirachta indica).

Metabolic pathway

The natural insecticide azadirachtin is most stable in mildly acidic solutions between pH 4 and 6 at room temperature and unstable in alkaline and strong acidic conditions. While azadirachtin is relatively stable to heating in the seeds or as a pure solid, it is rapidly destroyed or altered by heating in aqueous solution and methanol. In methanol at 90°C, it is quantitatively converted to 3-acetyl-1-tigloylazadirachtinin.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Degradation

After 90 hours exposure to UV radiation, very little azadirachtin (l)its 3- acetyl derivative and 22,23-dihydroazadirachtin remained intact. However, these compounds retained biological activity, and at least 200 hours irradiation was necessary to reduce the biological activity of 1. It is suggested that the effect of ultraviolet radiation is confined to the tigloyl residue which is common to these three compounds and which may undergo cis-trans isomerisation, rearrangement, etc. without significant effect on the biological activity of the molecule, because reduction or removal of the tigloyl residue causes only limited reduction in biological activity of the parent (Barnby ef al., 1989).
Azadirachtin was hydrolysed readily in several buffers (pH 4.1-8.1) and natural waters (pH 6.2,7.3,8.0 and 8.1) at 35 °C and its disappearance followed pseudo-first-order kinetics (Szeto and Wan, 1996). Rates of disappearance of the parent were faster in basic than in acidic solution (DT50 was 12 hours at pH 8 and 206 hours at pH 6) and the compound is not expected to be persistent in water.

Mode of action

Azadirachtin acts on insect gustatory receptors to inhibit feeding, and also interferes with development by inhibiting synthesis of the neuropeptide that triggers ecdysone release. The molecular targets mediating these effects are not known.

Toxicity evaluation

Azadirachtin is practically non-toxic to mammals, birds and plants. It is moderately toxic to aquatic invertebrates, but exposure is negligible due to low application rates and rapid degradation. Since it is only active by ingestion of treated foliage, exposure of non-target insects and honeybees is minimal.

Incompatibilities

Powder or liquid may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, reducing agents and metals, acid chlorides, alkalis, alkali metals, high heat, including sunlight.

Waste Disposal

Waste product may be disposed of onsite (open dumping may be prohibited) or at an approved waste disposal facility. All federal, state, and local environmental regulations must be observed.

AzadirachtinSupplier

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