Azadirachtin

720.71

720.71

O4U1SAF85H

DTXSID0037497

Microcrystalline powder|Yellow green powder

13021920

212.04000

1.75

1.5±0.1 g/cm3

155-158 °C @ Solvent: Carbon tetrachloride

792.4±60.0 °C at 760 mmHg

244.8±26.4 °C

1.623

3.61e-04 M|Readily soluble in ethanol, diethyl ether, acetone, and chloroform. Insoluble in hexane.|In water, 0.26 g/L at 25 °C

−20°C

0mmHg at 25°C

D -53° (c = 0.5 in CHCl3)

Strong garlic/sulfur odor

Henry's Law constant = 2.8X10-25 atm-cu m/mole at 25 °C (est)

241.4 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Hydroxyl radical reaction rate constant = 2.3X10-10 cu cm/molec-sec at 25 °C (est)

III

9

3077

3

22

22-45

Stable in the dark. DT50 50 days (pH 5, room temperature); rapidly decomposed at higher temperatures, in alkaline and strongly acidic media.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.|SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 5 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical-resistant gloves. Long-sleeved shirt and long pants. Protective eyewear. Shoes plus socks.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

/For applying the product/ wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.|Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.|Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.|Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

LD50 Rat oral >5000 mg/kg|LD50 Rabbit oral >2000 mg/kg|LD50 Rabbit dermal >2000 mg/kg|LD50 Mouse oral 13 mg/kg /Neem extract/

/AQUATIC SPECIES/ ...Exposure to concentrations of 0.40 and 0.50 mg/L /azadirachtin/ resulted in a significant decrease in percent fertilization success of B. quercicus eggs, and a marked reduction in swimming speed of stage 24 tadpoles. At a concentration of 0.50 mg/L, food consumption by stage 24 tadpoles was significantly reduced.|/AQUATIC SPECIES/ ... . Chlorophyll and protein contents of the algae, and the concentrations of the insecticides in water and algae were monitored at intervals of time up to 20 days. Chlorophyll and protein contents in algae were inhibited at treatment levels of 3.0 and 4.5 ug AZ-A/mL, whereas at 1.5 ug/mL, the chemical stimulated the chlorophyll production. The partition of AZ-A between water and algae was reversible, and the bioconcentration factor (BCF) was low. In contrast, TF dosed at 0.25 to 0.75 ug/mL stimulated algal growth.|/FIELD STUDIES/ Outdoor stream channels were treated with a commercial neem formulation, Neemix 4.5, and a neem extract (no formulation ingredients) to determine the effects on aquatic insect communities. An exposure period of 5 hr was chosen to simulate the transient nature of pesticide residues in streams and rivers after aerial applications. Multivariate analytic procedures based on Bray-Curtis similarity matrices were used to compare community structure among the replicate channels 9 days after treatment. No significant differences in community structure were found among controls and channels treated with Neemix at an azadirachtin concentration of 0.28 mg/L, but a multivariate measure of community stress indicated an increase in variability among treated channels. Significant differences in community structure were found among controls and channels treated with Neemix at 0.84 and 2.54 mg/L. The formulation ingredients of Neemix were at least partially responsible for the significant effects on community structure at 0.84 mg/L azadirachtin. No significant differences were found among controls and channels treated with the extract at 0.9 mg/L, whereas the community structure of aquatic insects in channels treated at 3.0 mg/L differed significantly from controls.

Azadirachtin oil is the main component of neem seed extract(1,2).

Azadirachtin's production may result in its release to the environment through various waste streams; it's use as an insecticide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 93(SRC), determined from a log Kow of 1.07(2) and a regression-derived equation(3), indicates that azadirachtin is expected to have high mobility in soil(SRC). Volatilization of azadirachtin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.9X10-14 atm-cu m/mole(SRC), derived from a vapor pressure of 2.7X10-11 mm Hg(4) and a water solubility of 260 mg/L(4). Azadirachtin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). The half-life range of azadirachtin in soil at 18 °C, pH 6.0 and exposed to natural light was 26-29 days(5). Soil half-lives in non-autoclaved soils ranging from 19.9 to 43.9 days(6,7) as opposed to half-lives of 37.6 to 91.2 days in autoclaved soils(6,7) suggesting that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 93(SRC), determined from a log Kow of 1.07(2) and a regression-derived equation(3), indicates that azadirachtin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.9X10-14 atm-cu m/mole(SRC), derived from a vapor pressure of 2.7X10-11 mm Hg(4) and a water solubility of 260 mg/L(4). According to a classification scheme(5), an estimated BCF of 1.3(SRC), from its log Kow(2)and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A measured half-life of 282 hours was observed at 25 °C when azadirachtin was placed in a phosphate buffer at pH 7(7). Soil half-lives in non-autoclaved soils ranging from 19.9 to 43.9 days(8,9) as opposed to half-lives of 37.6 to 91.2 days in autoclaved soils(8,9) suggest that biodegradation may be an important environmental fate process in water(SRC).|AQUATIC FATE: In-situ enclosures treated with azadirachtin concentrations ranging from 0.035 to 1.75 mg/L were deployed in a lake in Ontario Canada(1). Thirteen different samples from these enclosures were taken over a 50 day period. A dissipation half-life of azadirachtin with natural sun light, pH6, and 18 °C is 24.7 days which is similar to the half-life of 30.5 days from an experiment done in the dark at 20 °C and pH 7(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), azadirachtin, which has a vapor pressure of 2.7X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase azadirachtin may be removed from the air by wet and dry deposition(SRC). The half-life for photolysis of azadirachtin is 50 days(2). Azadirachtin has a reported half-life of 3.9 days when exposed to UV light(3).

The rate constant for the vapor-phase reaction of azadirachtin with ozone has been estimated as 8.3X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 0.14 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2).|A measured half-life of 282 hours was observed at 25 °C when azadirachtin was placed in a phosphate buffer at pH 7(1). Solutions of azadirachtin with or without UV absorbing chemicals dihydroxybenzophenone, para-amino benzoic acid or florescent brightener 28, were placed on a glass slides and placed in a chamber where they were exposed to 2 halide and one sodium lamp with wavelenghts ranging from 300-1000 nm and an intensity that corresponded to about 26.3 % of natural sunlight on glass surfaces during that time period(2). Azadirachtin had a reported half-life of 3.9 days when exposed to UV light. Addition of dihydroxybenzophenone, para-amino benzoic acid increased the half-life to 22.54 and 7.37 days(2).|Azadirachtin was sprayed on both oak and balsam at rates of 7 g in 2.8 L/hour, 15 g in 5.9 L/hour and 40 g in 15.8 L/hour (1). Despite the fact that the initial concentrations ranged from 4-96 ug/g, azadirachtin had a half life of 17-22 hours on all of the plants(1).

An estimated BCF of 1.3 was calculated for azadirachtin(SRC), using a log Kow of 1.09(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of azadirachtin is estimated as 93(SRC), using a log Kow of 1.09(1)and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that azadirachtin is expected to have high mobility in soil.

The Henry's Law constant for azadirachtin is estimated as 2.8X10-25 atm-cu m/mole(SRC)derived from a vapor pressure of 2.7X10-11 mm Hg(1) and a water solubility of 260 mg/L(1). This Henry's Law constant indicates that azadirachtin is expected to be essentially nonvolatile from moist soil and water surfaces(2). Azadirachtin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to azadirachtin may occur through inhalation and dermal contact with this compound at workplaces where azadirachtin is produced or used. The greatest potential for dermal and inhalation exposure to azadirachtin is expected when the material is being applied to fields and crops for use in insect control. (SRC)

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

Injection of a tritiated azadirachtin derivative, (22,23-(3)H)dihydroazadirachtin into locusts indicated fast clearing of radiolabeled material from the blood. Ninety percent of the applied radioactivity was excreted during the first 7 hr with the feces, whereas the remaining (22,23-(3)H)dihydroazadirachtin accumulated in the Malpighian tubules where it could be detected even 24 days after treatment. After the first 24 hr, feces contained at least three polar, unidentified metabolites but no (22,23-(3)H)dihydroazadirachtin.

Skin decontamination: If skin contamination occurs, the skin should be thoroughly washed with soap and water.|Gastrointestinal decontamination: Due to the severe gastrointestinal irritation, gastric emptying and catharsis are not indicated. Consideration should be given to administration of activated charcoal...|Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/SIGNS AND SYMPTOMS/ Neem seed oil produced occasional diarrhea, nausea, and general discomfort when given orally as an anthelmintic. /Neem seed oil/|/SIGNS AND SYMPTOMS/ ... 13, including 2 fatal, poisoning cases due to neem seed (margosa) oil, a traditional remedy in India and Malaysia, /were reported/. Five to ten milliliters of the oil given orally to children against minor ailments caused vomiting, drowsiness, tachypnea with acidotic respiration, and polymorphonuclear leukocytosis, and encephalopathy developed within hours of ingestion. Seizures, associated with coma, developed in some cases. Autopsy demonstrated pronounced fatty acid infiltration of the liver and proximal renal tubules, with mitochondrial damage, and cerebral edema, changes consistent with Reye's syndrome.

azadirachtin

Discontinued products: Blokade, Bollwhip, Margosan-O, Neemazad, Turplex, SureFire, and Neemachtin|Trade Names: Azatin EC, Azatin Technical and Azatin-Plus EC.

Analysis by hplc.

Agrochemicals -> Insecticides|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]|Insecticides, Acaricides, Fungicides|Environmental transformation -> Pesticides (parent, predecessor)

Azadirachtin has known environmental transformation products that include 3-Deacetyl-azadirachtinA and 3-Deacetyl-azadirachtinin.