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Name:	Imidacloprid
CAS No:	105827-78-9
CAS No:	138261-41-3

PRODUCT DESCRIPTION

【Name】: Imidacloprid

【CAS Registry number】: 105827-78-9;; 138261-41-3

【Synonyms】: 1-((6-Chloro-3-pyridinyl)methyl)-N-nitro-imidazolidinimine
((6-Chloro-3-pyridinyl)methyl)-N-nitro-2-imidazolidinimine,96% imidacloprid TC
1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine
1-[(6-chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine
(EZ)-1-(6-Chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine

1-((6-chloro-3-pyridinyl)methyl)-4,5-dihydro-N-nitro-1H-imidazol-2-amine
1-((6-Chloro-3-pyridinyl)methyl)-4,5-dihydro-N-nitro-imidazol-2-amine
Admire
Confidor
Gaucho
Merit
NTN33823
NTN 33893
NTN-33893
1-(6-chloro-3-pyridymethyl)-N-nitromidazolidin-2-ylideneamine

【Molecular Formula】: C9H10ClN5O2 (Products with the same molecular formula)

【Molecular Weight】: 255.66

【Inchi】: InChI=1/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13)

【Canonical SMILES】: C1CN(C(=N1)N[N+](=O)[O-])CC2=CN=C(C=C2)Cl

【MOL File】
138261-41-3;105827-78-9.mol

Chemical and Physical Properties

【Density】: 1.54

【Melting Point】: 144℃

【Boiling Point】: 411.7°C at 760 mmHg

【Vapour】: 5.47E-07mmHg at 25°C

【Refractive Index】: 1.713

【Flash Point】: 202.8°C

【Water】: 0.061 g/100mL at 20℃

【Solubilities】: At 20 deg C: dichloromethane 6.7X10+4 mg/L, isopropanol 2.3X10+4 mg/L, toluene 6.9X10+2 mg/L
In water, 6.1X10+2 mg/L at 20 deg C

【Color/Form】: Colorless crystals

【Computed Properties】: Molecular Weight:255.661 [g/mol]
Molecular Formula:C₉H₁₀ClN₅O₂
XLogP3-AA:0.8
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:255.052302
MonoIsotopic Mass:255.052302
Topological Polar Surface Area:86.3
Heavy Atom Count:17
Formal Charge:0
Complexity:319
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:4.6
Conformer Sampling RMSD:0.6
CID Conformer Count:66

Safety and Handling

【Hazard Codes】: N:Dangerousfortheenvironment;

【Cleanup Methods】: 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.

【Fire Fighting Procedures】: Powder, water spray, foam, carbon dioxide.

【Fire Potential】: Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

【Formulations/Preparations】: Dustable powder, granules, seed dressing (flowable concentrate, slurry), soluble concentrate, suspension concentrate, wettable powder.
Discontinued products: Amidor, Commet, Gaucho MZ, and Storm
Selected products: Admire; Confidor; Conidor; Gaucho; Midas; Mogambo; Picador; Suncloprid; Tiddo; Winner; ...Advantage; Agrofidor; Bilogic; Commando; Hachidusan; Intercapt; Lizetan; Merit; Premise; Provado; Trimax; Vaplex. Mixtures: Amister Admire (+azoxystrobin); Baytan C (+fuberidazole, +triadimenol); Baytan Secur (+fuberidazole, +triadimenol); Carrena (+carpropamid); Chinook (+beta-cyfluthrin); Conidan (+tebufenozide); Gaucho Ble'; (+anthraquinone, +bitertanol); Gaucho M; (+pencycuron, +thiram); Gaucho T (+thiram); Imprimo (+tefluthrin); Leverage (+cyfluthrin); Monceren G (+pencycuron); Prestige (+pencycuron); Traffic (+tefluthrin); Win Admire (+carpropamid); ...Beam Admire (+tricyclazole); Cereline Secur (+fuberidazole+triadimenol); Confidor Supra (+cyfluthrin); Confidor Ultra (+beta-cyfluthrin); Gaucho Orge (+tebuconazole+triazoxide); Gaucho Rx 246 FS (+tebuconazole); Gaucho XT (+metalaxyl+tebuconazole); Legend (+cyfluthrin); Manta Plus (+fuberidazole+imazalil+triadimenol; Monceren Admire (+pencycuron); Monceren Star (+pencycuron); Montur (+tefluthrin); Raxil Secur (+tebuconazole+triazoxide); Sibutol Secur (+bitertanol+fuberidazole); Vget Admire (+tiadinil).

【Other Preventative Measures】: /If inhaled/: /Get/ fresh air, rest. /If contacted with skin/: Rinse and then wash skin with water and soap. /If contacted with eyes/: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. /If ingested/: Induce vomiting (ONLY IN CONSCIOUS PERSONS!).
Avoid inhalation of dust. /Wear/ protective gloves and safety spectacles. Do not eat, drink, or smoke during work. Wash hands before eating.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
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.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
/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.

【Octanol/Water Partition Coefficient】: log Kow = 0.57 at 21 deg C

【Disposal Methods】: Sweep spilled substance into containers. Carefully collect remainder, then remove to safe place. Personal protection: P2 filter respirator for harmful particles. Do NOT let this chemical enter the environment.
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.

Biomedical Effects and Toxicity

【Pharmacological Action】: - Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of ACETYLCHOLINE, and drugs that affect the survival of cholinergic neurons. The term cholinergic agents is sometimes still used in the narrower sense of MUSCARINIC AGONISTS, although most modern texts discourage that usage.
- 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.

【Therapeutic Uses】: (VET): Ectoparasiticide.

【Biomedical Effects and Toxicity】: After oral administration of methylene-14C and 4,5-imidazolidine-14C-labelled imidacloprid to rats, the radioactivity was quickly and almost completely absorbed from the gastrointestinal tract and quickly eliminated (96% within 48 hours, mainly via the urine). Only about 15% was eliminated as unchanged parent compound; the most important metabolic steps were hydroxylation at the imidazolidine ring, hydrolysis to 6-chloronicotinic acid with glycine. All metabolites found in the edible organs and tissues of farm animals contained the 6-chloronicotinic acid moiety. Imidacloprid is also quickly largely eliminated from hens and goats.
After oral administration of 1 or 20 mg/kg bw of [pyridinyl-14C-methylene]imidacloprid, the radiolabel was extensively absorbed from the intestinal lumen and readily distributed from the plasma into the body. The radiolabel was also readily eliminated. After intravenous administration of 1 mg/kg bw, about 92% of the recovered radiolabel was excreted in urine and feces within 48 hr. Most of the radiolabel was excreted via the kidneys, with an average ratio in urine:feces of 4:1. After oral administration, about 96% of the dose was excreted in urine and feces within 48 hr. No difference was found between female and male rats. More than 90% of the renal radiolabel was excreted during 24 hr after dosage. The average residual radiolabel in the body, excluding the gastrointestinal tract, at sacrifice was about 0.5%, and that in the gastrointestinal tract was about 0.06% of the administered dose. The rats with bile-duct fistulas excreted only 4.7% of the administered dose with feces, 56% in urine and about 36% with bile. These findings indicate the existence of enterohepatic circulation of the radiolabel. Significant amounts of radiolabel were not excreted in expired air (CO2).
The distribution of [pyridinyl-14C-methylene]imidacloprid was investigated in male rats by conventional whole-body autoradiography on X-ray film in a study conducted according to GLP. The rats were given a single oral dose of 20 mg/ kg bw, and the distribution of radiolabel was visualized at 1, 2, 4, 24 and 48 hr after treatment. The radiolabel was readily absorbed and rapidly distributed to the tissues and organs. The pattern of distribution showed that the radiolabel could readily permeate tissues: With the exception of fatty tissues, the central nervous system and the mineral part of bone, blackening on the autoradiogram was seen on all other parts of the body 5 min after intravenous injection and 1 hr after oral dosage. Higher concentrations were seen later in the thyroid and adrenals, but, after 24 hr, all other organs and tissues showed only small amounts of radiolabel. The high degree of blackening over the kidney during the first 24 hr is a reflection of the high rate of renal excretion of the administered compound. The concentration of radiolabel decreased in organs and tissues with time after administration. The concentrations in the fatty tissues and in the central nervous system were very low throughout the study.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】: TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 156 to 800(2-4), indicate that imidacloprid is expected to have moderate to low mobility in soil(SRC). The pKa of the amino group of imidacloprid is 11.12(5), indicating that this compound will primarily exist in the cation form in the environment and cations do not volatilize from moist soil surfaces. Imidacloprid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(7). Imidacloprid is reported to be metabolized slowly in standard laboratory tests in soil under aerobic conditions(8). Photodegradation of imidacloprid in soil occurs with a half-life on the order of months(9). Imidacloprid was found to degrade more rapidly in soil under vegetation; half-lives of 48 and 190 days were determined in experiments with and without vegetation, respectively(8). A half-life of 34 days was reported for imidacloprid in a field experiment using soil (pH = 7.9, 0.52% organic carbon, 16.6% clay, 31.3% silt, 52.1% sand) where citrus products are grown extensively(10).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 156 to 800(2-4), indicate that imidacloprid is not expected to adsorb to suspended solids and sediment(SRC). The pka of the amino group of imidacloprid is 11.12(5), indicating that this compound will primarily exist in the cation form in the environment and cations generally adsorb more strongly to suspended solids and sediment than their neutral counterparts and are not expected to volatilize from water surfaces(6). According to a classification scheme(9), an estimated BCF of 3.2(SRC), from its log Kow of 0.57(8) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Imidacloprid is reported to be stable to hydrolysis at pH 5-11(8,11). Imidacloprid is photodegraded in water with a half-life on the order of hours(11). Imidacloprid is degraded under anaerobic aquatic conditions more rapidly than under aerobic soil conditions(11).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), imidacloprid, which has a vapor pressure of 3X10-12 mm Hg at 20 deg C(2) is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase imidacloprid may be removed from the air by wet or dry deposition(SRC).

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PRODUCT DESCRIPTION

Chemical and Physical Properties

Safety and Handling

Biomedical Effects and Toxicity

Environmental Fate and Exposure Potential

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