| Identification | Back Directory | [Name]
AZADIRACHTIN A | [CAS]
11141-17-6 | [Synonyms]
AZAD
Oikos
Ecozin
Gronim
NEEMIX
AZATIN
Suneem
Ornazin
Nimurin
KAYNEEM
NEEMOLIN
NEEMAZAD
NEEMAZAL
Neemazol
Neemgold
Azatin XL
Azatin EC
Nsc368675
PHEROTECH
AZATIN(R)
Superneem
NeemAzal F
NeemAzal T
NeemAzal W
Nimbicidine
AZADIRACTIN
AZADIRACHTIN
Azatin Magnum
Oikos 25 plus
Oikos 323 Bio
Azaditrachtin
Safer BioNEEM
AZADIRACHTIN B
AZADIRACHTIN A
AZADIRACCHTIN A
AZADIRACHTIN pure
AZADIRACHTIN A(P)
3-TIGLOYL-AZADIRACHTOL
Azadirachtin(Technical)
AZADIRACHTIN, 10MG, NEAT
Azadirachtin Solution, 100ppm
Azadirachtin 10mg [11141-17-6]
Azadirachtin @100 μg/mL in Methanol
(2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-(Acetyloxy)octahydro-3,5-dihydroxy-4-Methyl-8-[[(2E)-2-Methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-Methyl-2,7-Methanofuro[2,3-b]oxireno[e]oxepin-1a(2
1H,7H-Naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylicacid,10-(acetyloxy)octahydro-3,5-dihydroxy-4-Methyl-8-[[(2E)-2-Methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-Methyl-2,7-Methanofuro[2,3-b]oxireno[e]
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)
1H,7H-Naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-, 5,10a-dimethyl ester, (...
(2aR,3S,4S,4aR,5S,7aS,8S,10R,10aS,10bR)-10-(Acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-buten-1-yl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-1H,7H-naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylic acid 5,10a-dimethyl ester | [Molecular Formula]
C35H44O16 | [MDL Number]
MFCD00210582 | [MOL File]
11141-17-6.mol | [Molecular Weight]
720.71 |
| Chemical Properties | Back Directory | [Appearance]
Off-white, yellowish powder or dark brown
emulsifiable concentrate. | [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 | [LogP]
1.090 | [CAS DataBase Reference]
11141-17-6 | [EPA Substance Registry System]
Azadirachtin A (11141-17-6) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white, yellowish powder or dark brown
emulsifiable concentrate. | [Uses]
A tetranortriterpinoid isolated from the seeds of the neem tree. Highly active insect feeding deterrent and growth regulator.
Isolation from A. indica and identification as feeding inhibitor in locus
ts. Used experimentally as insect control agent. | [Definition]
ChEBI: A member of the family of azadirachtins that is isolated from the neem tree (Azadirachta indica). | [Uses]
Experimentally as insect control agent. | [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® | [Potential Exposure]
Biological tetranortriterpinoid insecticide;
insect growth regulator. A natural product extracted
from seeds of the Neem tree (Azadirachta indica). | [First aid]
Eyes: First check the victim for contact lenses
and remove if present. Flush victim’s eyes with water or
normal saline solution for 20 to 30 minutes while simultaneously
calling a hospital or poison control center. Do not
put any ointments, oils, or medication in the victim’s eyes
without specific instructions from a physician. Immediately
transport the victim after flushing eyes to a hospital even if
no symptoms (such as redness or irritation) develop. Skin:
Immediately flood affected skin with water while removing
and isolating all contaminated clothing. Gently wash all
affected skin areas thoroughly with soap and water. If
symptoms such as redness or irritation develop, immediately
call a physician and be prepared to transport the victim
to a hospital for treatment. Inhalation: Immediately
leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of
Azadirachtin 327
breath, or burning in the mouth, throat, or chest) develop,
call a physician and be prepared to transport the victim to a
hospital. Provide proper respiratory protection to rescuers
entering an unknown atmosphere. Whenever possible,
SCBA (SCBA) should be used; if not available, use a level
of protection greater than or equal to that advised under
Protective Clothing. Ingestion: Do Not induce vomiting.
If the victim is conscious and not convulsing, give 1 or 2
glasses of water to dilute the chemical and immediately
call a hospital or poison control center. Be prepared to
transport the victim to a hospital if advised by a physician.
If the victim is convulsing or unconscious, do not give anything
by mouth, ensure that the victim’s airway is open and
lay the victim on his/her side with the head lower than the
body. Do Not induce vomiting. Immediately transport the
victim to a hospital. | [Shipping]
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required. | [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. | [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. | [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. | [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. | [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. | [storage]
Store at -20°C | [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. |
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