11141-17-6 Usage
Uses
Used in Agricultural Industry:
AZADIRACHTIN A is used as an insect control agent for controlling various pests, including whitefly, leaf miners, and pear psylla. It acts as a highly active insect feeding deterrent and growth regulator, particularly effective in managing the metamorphosis process as insects transition from the larva stage to the pupa stage.
AZADIRACHTIN A is also used as an insect growth regulator in the commercial agricultural sector, where it is derived from the neem tree's fruit extract. This application helps control the insect's development and metamorphosis, providing an alternative to traditional chemical insecticides.
Used in Environmental and Biological Research:
AZADIRACHTIN A is used experimentally as an insect control agent in various research and development programs. Its unique properties as an insect growth regulator and feeding deterrent make it a valuable tool for studying insect behavior, ecology, and the development of sustainable pest management strategies.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 11141-17-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,1,1,4 and 1 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 11141-17:
(7*1)+(6*1)+(5*1)+(4*4)+(3*1)+(2*1)+(1*7)=46
46 % 10 = 6
So 11141-17-6 is a valid CAS Registry Number.
InChI:InChI=1/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
11141-17-6Relevant articles and documents
Synthesis of natural products from the Indian neem tree Azadirachta indica
Veitch, Gemma E.,Pinto, Andrea,Boyer, Alistair,Beckmann, Edith,Anderson, James C.,Ley, Steven V.
, p. 569 - 572 (2008/04/12)
The synthesis of five natural products (3, 6, 7, 10, and 14), isolated from the Indian neem tree Azadirachta indica, is reported from a common intermediate (2). The judicious choice of transacetalization conditions allows efficient access to both the azadirachtinin (9 and 10) and the azadirachtin (3, 6, 7, and 14) skeletons
The synthesis of azadirachtin: A potent insect antifeedant
Ley, Steven V.,Abad-Somovilla, Antonio,Anderson, James C.,Ayats, Carles,Baenteli, Rolf,Beckmann, Edith,Boyer, Alistair,Brasca, Maria G.,Brice, Abigail,Broughton, Howard B.,Burke, Brenda J.,Cleator, Ed,Craig, Donald,Denholm, Alastair A.,Denton, Ross M.,Durand-Reville, Thomas,Gobbi, Luca B.,Goebel, Michael,Gray, Brian Lawrence,Grossmann, Robert B.,Gutteridge, Claire E.,Hahn, Norbert,Harding, Sarah L.,Jennens, David C.,Jennens, Lynn,Lovell, Peter J.,Lovell, Helen J.,De La Puente, Mary L.,Kolb, Hartmuth C.,Koot, Win-Jan,Maslen, Sarah L.,McCusker, Catherine F.,Mattes, Amos,Pape, Andrew R.,Pinto, Andrea,Santafianos, Dinos,Scott, James S.,Smith, Stephen C.,Somers, Andrew Q.,Spilling, Christopher D.,Stelzer, Frank,Toogood, Peter L.,Turner, Richard M.,Veitch, Gemma E.,Wood, Anthony,Zumbrunn, Cornelia
experimental part, p. 10683 - 10704 (2009/12/31)
We describe in full the first synthesis of the potent insect antifeedant azadirachtin through a highly convergent approach. An O-alkylation reaction is used to unite decalin ketone and propargylic mesylate fragments, after which a Claisen rearrangement constructs the central C8-C14 bond in a stereoselective fashion. The allene which results from this sequence then enables a second critical carboncarbon bond forming event whereby the [3.2.1] bicyclic system, present in the natural product, is generated via a 5-exo-radical cyclisation process. Finally, using knowledge gained through our early studies into the reactivity of the natural product, a series of carefully designed steps completes the synthesis of this challenging molecule.
A relay route for the synthesis of azadirachtin
Veitch, Gemma E.,Beckmann, Edith,Burke, Brenda J.,Boyer, Alistair,Ayats, Carles,Ley, Steven V.
, p. 7633 - 7635 (2008/09/19)
(Chemical Equation Presented) 22 Years in the making: Azadirachtin (1) was synthesized for the first time by a highly convergent approach, utilizing a Claisen rearrangement and a radical cyclization as key steps. End-game strategies relied on intermediate 2, which could be obtained by synthetic methods as well as by degradation of 1. Bn = benzyl, TBS = tert- butyldimethylsilyl.
Stable extracts from neem seeds
-
, (2008/06/13)
A neem seed extract containing azadirachtin with improved stability has been developed using a process involving dissolution of the crude neem seed extract in a polar solvent and removal of impurities by precipitation and/or treatment of the extract with an oxidizing agent. The resulting extract, optionally formulated as a wettable powder, is a useful insecticide for the control of foliar pests.
Chemistry of Insect Antifeedants from Azadirachta Indica (Part 19): A Potential Relay Route for the Synthesis of Azadirachtin.
Denholm, Alastair A.,Jennens, Lyn,Ley, Steven V.,Wood, Anthony
, p. 6591 - 6604 (2007/10/02)
A potential relay route for the synthesis of azadirachtin (1) has been established.An advanced intermediate 4 has been prepared and methods to convert this back to the natural product has been developed, in particular, the reintroduction of the enol double bond using an acetal exchange process.
CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA INDICA (PART 11) : CHARACTERISATION AND STRUCTURE ACTIVITY RELATIONSHIPS OF SOME NOVEL REARRANGED AZADIRACHTINS.
Ley, Steven V.,Anderson, James C.,Blaney, Wally M.,Morgan, E. David,Sheppard, Richard N.,et al.
, p. 9231 - 9246 (2007/10/02)
Several novel rearrangement reactions of the natural product azadirachtin and related derivatives have been characterised using a combination of x-ray crystallographic and high field nmr techniques.The insect antifeedant properties of these and a number of C7 modified compounds have been investigated.
CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA INDICA (Part 3) REACTIONS ON THE C-22,23 ENOL ETHER DOUBLE BOND OF AZADIRACHTIN AND CONVERSION TO 22,23-DIHYDRO-23-&β-METHOXYAZADIRACHTIN.
Ley, Steven V.,Anderson, James C.,Blaney, Wally M.,Lidert, Zev,Morgan, E. David,et al.
, p. 5433 - 5436 (2007/10/02)
Azadirachtin (1) can be converted to the natural product 22,23-dihydro-23β-methoxyazadirachtin (2) via selective bromomethoxylation of the C-22,23 enol ether double bond and tri-n-butyltin hydride reduction; the corresponding acetic acid adduct on pyrolysis affords (1) in high yield.The antifeedant effects of the addition compounds were assessed.
