1-(6-Chlor-3-pyridiylmethyl)-N-ni-troimidazolidin-2-ylidenamin

log Kow = 0.57 at 21 °C

0.570

0.57

In water, 6.1X10+2 mg/L at 20 °C

At 20 °C: dichloromethane 6.7X10+4 mg/L, isopropanol 2.3X10+4 mg/L, toluene 6.9X10+2 mg/L

610 mg/L @ 20 °C (exp)

Solubility in water, g/100ml at 20 °C: 0.061

On combustion, forms toxic gases. Decomposes on heating.

When heated to decomposition it emits toxic vapors of /nitrogen oxides/ and /chloride/.

144 °C

143 - 144 °C

144 °C

4X10-7 mPa (3X10-12 mm Hg) at 20 °C; 9X10-7 mPa (7X10-12 mm Hg) at 25 °C

Vapor pressure at 20 °C: negligible

Colorless or beige solid; [ICSC]

Solid

COLOURLESS CRYSTALS OR BEIGE POWDER.

Stable under recommended storage conditions.

Stable to hydrolysis at pH 5-11.

Positive

1.94

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]；H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

Regulation (EC) No 1107/2009 (amended)

Imidacloprid is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/116/EC, 2010/21/EU, Reg. (EU) 2017/195, Reg. (EU) 2020/1643, Reg. (EU) 2022/801, Reg. (EU) No 485/2013, Reg. (EU) No 540/2011, Reg.(EU) No 2018/783

Status: Active Update: 04-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/33173；Status: Cease Manufacture Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/5039

Imidacloprid: HSNO Approval: HSR003302 Approved with controls

Indications for use: Kills adult fleas and is indicated for the treatment of flea infestations on dogs and puppies 10 weeks of age and older and weighing 4 lb or greater. ... Limitations. Do not give to puppies younger than 10 weeks of age or to dogs weighing less than 4 lb. Do not give more than one tablet a day.

Tolerances are established for residues of the insecticide imidacloprid, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of imidacloprid (1-[6-chloro-3-pyridinyl) methyl]-N-nitro-2-imidazolidinimine) and its metabolites containing the 6-chloropyridinyl moiety, calculated as the stoichiometric equivalent of imidacloprid, in or on the following commodities:[Table#6947]

Time-limited tolerances are established for residues of the insecticide imidacloprid, including its metabolites and degradates in connection with use of the pesticide under a Section 18 emergency exemption granted by EPA. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of imidacloprid (1-[6-chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine) and its metabolites containing the 6-chloropyridinyl moiety, calculated as the stoichiometric equivalent of imidacloprid. These tolerances will expire and are revoked on the dates specified in the following table:[Table#6948]

Tolerances are established for indirect or inadvertent residues of the insecticide imidacloprid, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of imidacloprid (1-[6-chloro-3-pyridinyl) methyl]-N-nitro-2-imidazolidinimine) and its metabolites containing the 6-chloropyridinyl moiety, calculated as the stoichiometric equivalent of imidacloprid, in or on the following commodities, when present therein as a result of the application of the pesticide to growing crops listed in this section and other non-food crops as follows:[Table#6949]

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 129099; Type of Pesticide: conventional - insecticide/termiticide; Use Site: domestic, food, ornamental use; Year: 1994.

Acute Tox. 3 (43.6%)；Acute Tox. 4 (56.4%)；Aquatic Acute 1 (96.4%)；Aquatic Chronic 1 (100%)

Acute toxicity (Oral) - Category 4；Specific target organ toxicity - Single exposure - Category 1 (nervous system)；Specific target organ toxicity - Repeated exposure - Category 2 (nervous system)；Hazardous to the aquatic environment (Acute) - Category 1；Hazardous to the aquatic environment (Long-term) - Category 1

Acute Tox. 3；Aquatic Acute 1；Aquatic Chronic 1

... Technical imidacloprid (94.2% pure) is a ... Category III dermal toxicant (dermal LD50 between 2000 to 20,000 mg/kg), Category IV inhalation toxicant (greater than 20 mg/liter or 0.02 mg/cu m), Category IV eye irritant (no irritation) and a category IV dermal irritant (caused erythema in rabbits that was cleared by 48 hours).

... Clinical signs of ... workers included eye irritation ... .

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Induce vomiting (ONLY IN CONSCIOUS PERSONS!).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray, powder, foam, carbon dioxide.

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids

Suitable materials: HDPE (high density polyethylene). ... Only use containers that are approved specifically for the product.

Separated from food and feedstuffs.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

Pesticide storage: Keep pesticide in original container. Do not put concentrate or dilute into food or drink containers. Store in cool, dry place. Do not store diluted spray.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided; Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

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.

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.

Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. 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.

For more Disposal Methods (Complete) data for IMIDACLOPRID (8 total), please visit the HSDB record page.

Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment.

Precautions for safe handling: Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

/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 refer for medical attention. /If ingested/: Induce vomiting (ONLY IN CONSCIOUS PERSONS!).

For more Preventive Measures (Complete) data for IMIDACLOPRID (16 total), please visit the HSDB record page.

Imidacloprid was detected in 21 of 32 samples (65.6%) of human air from residents of a rural area in Crete Island, Greece. The median and maximum concentrations reported were 0.03 and 0.27 ng/mg, respectively. The compound was not detected in hair samples from residents of an urban center, Heraklion (Crete, Greece)(1).

There is no known antidote for neonicotinoid insecticide exposures. The treatment is supportive and symptomatic. Administer charcoal as a slurry. In case of inhalation, move patient to fresh air, monitor for respiratory distress. If the exposure occurred via eye contact, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Remove contaminated clothing and wash exposed area thoroughly with soap and water if the exposure occurred via dermal contact. (T36)

Standard ecotoxicological risk assessments are conducted on individual substances, however monitoring of streams in agricultural areas has shown that pesticides are rarely present alone. In fact, brief but intense pulse events such as storm water runoff and spray drift during application subject freshwater environments to complex mixtures of pesticides at high concentrations. This study investigates the potential risks to non-target aquatic organisms exposed to a brief but intense mixture of the neonicotinoid pesticides imidacloprid and thiacloprid and the pyrethroid pesticides deltamethrin and esfenvalerate, compared to single substance exposure. All four of these pesticides have been detected in surface waters at concentrations higher than benchmark values and both classes of pesticides are known to exert adverse effects on non-target aquatic organisms under single substance exposure scenarios. First instar midge larvae of the non-target aquatic organism, Chironomus riparius, were exposed to combinations of these four pesticides at 50% of their LC50 (96 hr) values in a 1 hr pulse. They were then reared to adulthood in uncontaminated conditions and assessed for survival, development time and fecundity. Our results show that the risk of disruption to survival and development of non-target aquatic organisms under this scenario is not negligible on account of the significant increases in mortality of C. riparius found in the majority of the pesticide exposures and the delays in development after pyrethroid exposure. While none of the deleterious effects appear to be amplified by combination of the pesticides, there is some evidence for antagonism. No effects on fecundity by any of the pesticide treatments were observed.

Earlier research has evidenced the oxidative and neurotoxic potential of imidacloprid, a neonicotinoid insecticide, in different animal species. The primary aim of this study was to determine how metabolic modulators piperonyl butoxide and menadione affect imidacloprid's adverse action in the liver and kidney of Sprague-Dawley rats of both sexes. The animals were exposed to imidacloprid alone (170 mg/kg) or in combination with piperonyl butoxide (100 mg/kg) or menadione (25 mg/kg) for 12 and 24 hr. Their liver and kidney homogenates were analyzed spectrophotometrically for glutathione peroxidase, glutathione S-transferase, catalase, total cholinesterase specific activities, total glutathione, total protein content, and lipid peroxidation levels. Imidacloprid displayed its prooxidative and neurotoxic effects predominantly in the kidney of male rats after 24 hr of exposure. Our findings suggest that the observed differences in prooxidative and neurotoxic potential of imidacloprid could be related to differences in its metabolism between the sexes. Co-exposure (90-min pre-treatment) with piperonyl butoxide or menadione revealed tissue-specific effect of imidacloprid on total cholinesterase activity. Increased cholinesterase activity in the kidney could be an adaptive response to imidacloprid-induced oxidative stress. In the male rat liver, co-exposure with piperonyl butoxide or menadione exacerbated imidacloprid toxicity. In female rats, imidacloprid+menadione co-exposure caused prooxidative effects, while no such effects were observed with imidacloprid alone or menadione alone. In conclusion, sex-, tissue-, and duration-specific effects of imidacloprid are remarkable points in its toxicity.

The combined toxicity of five insecticides (chlorpyrifos, avermectin, imidacloprid, lambda-cyhalothrin, and phoxim), two herbicides (atrazine and butachlor) and a heavy metal (cadmium) has been examined with the earthworm acute toxicity test. Toxicological interactions of these chemicals in four, five, six, seven, and eight-component mixtures were studied using the combination-index (CI) equation method. In four-component and five-component mixtures, the synergistic effects predominated at lower effect levels, while the patterns of interactions found in six, seven, and eight-component mixtures displayed synergism. The lambda-CY+IMI+BUT+ATR+CPF+PHO combination displayed the most strongly synergistic interaction, with CI values ranging from 0.09 to 0.15. The nature of the interaction changes with the effect level and the relevance of synergistic effects increase with the complexity of the mixture. The CI method was compared with the classical models of concentration addition (CA) and independent action (IA) and we found that the CI method could accurately predict the combined toxicity. The predicted synergism resulted from co-existence of the pesticides and the heavy metal especially at low effect levels may have important implications in risk assessment for the real terrestrial environment.

Metabolic modifiers and other pharmaceutical drugs have been shown to modify the toxicity of imidacloprid. The CYP450-inhibiting piperonyl butoxide synergized the toxicity of imidacloprid. In subchronic and chronic feeding studies, mice developed hypersensitivity to ether, which was used as anesthesia during procedures such as blood withdrawal and tattooing. These animals exhibited dyspnea, respiratory failure and spasms and died shortly after administration of ether. The specific mechanism of the imidacloprid-induced hypersensitivity to ether is presently unknown.

For more Interactions (Complete) data for IMIDACLOPRID (6 total), please visit the HSDB record page.

LD50; Species: Scaptotrigona postica (Bee) oral 24.5-25.2 ng a.i./bee

LC50; Species: Scaptotrigona postica (Bee) diet 42.5 ng a.i./uL for 24 hr

LC50; Species: Scaptotrigona postica (Bee) diet 14.3 ng a.i./uL for 48 hr

LD50; Species: Apis mellifera (Honeybee) oral 60 ng/bee at 48 hr

For more Ecotoxicity Values (Complete) data for IMIDACLOPRID (42 total), please visit the HSDB record page.

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 imidacloprid is 11.12(5), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Imidacloprid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.0X10-12 mm Hg at 25 °C(7). Photodegradation of imidacloprid in soil occurs with a half-life on the order of months(8). 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(9). 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). Half-lives of 2.35 and 2.97 days were calculated for imidacloprid applied at 400 and 800 mL/ha, respectively, to a vineyard in India(11).

FIELD STUDY: Imidacloprid persistence on vegetables was investigated. The compound was below detectable levels 5-7 days after final application. The difference in persistence was attributed to the involvement of non-enzymatic oxidation in plants(1).[Table#6944]

FIELD STUDY: The degradation of imidacloprid in chrysanthemum flowers (Chrysanthemum morifolium) and soil was studied. Samples were collected from Tongxinag, Zhejiang Province, China. The soil was a loamy clay soil (pH 7.41; organic matter 1.09% ; clay 42.8%). Chrysanthemum flower extracts are used in foods, beverages and medicines(1).[Table#6945]

FIELD STUDY: Half-lives of imidacloprid on mustard seeds and leaves(1).；Table: Residues (mg/kg) [Table#6946]

For more Environmental Fate (Complete) data for IMIDACLOPRID (6 total), please visit the HSDB record page.

Oranges, tangerines, watermelons and date plums from Valencia, Spain were analyzed for the presence of imidacloprid. The compound was detected in 1 of 56 orange samples; 0.02 mg/kg, 1 of 24 date plums samples; 0.04 mg/kg, and 7 of 134 tangerine samples; 0.2-0.7 mg/kg. It was not detected in 13 watermelons samples (detection limit = 0.2 mg/kg). The average levels of imidacloprid were 0.35, 1.67, 1.65 and 0 ug/kg for oranges, date plums, tangerines and watermelons, respectively. Sampling was conducted in 2001(1). Imidacloprid was measured at a concentration range of 15-31 ug/kg in 8 samples of fresh potatoes sold in 34 farmer's markets in Alberta, Canada; the maximum residue limit is 300 ug/kg(2).

The substance can be absorbed into the body by ingestion.

Inhalation (L1130) ; dermal (L1130) ; oral (L1130)

IDENTIFICATION AND USE: Imidacloprid (IM) forms colorless crystals. It is registered for pesticide use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. IM is used to control insect pests on agricultural and nursery crops, structural pests and parasites on companion animals. HUMAN EXPOSURE AND TOXICITY: The most common clinical signs included: rash, breathing difficulty, headache, tearing eyes, nausea, itching, dizziness, increased salivation, vomiting, numbness and dry mouth. One case was reported for a worker who had imidacloprid splashed into the eyes. The clinical signs were burning and corneal abrasion in the eye. IM blood concentrations found in two fatal cases were 12.5 and 2.05 ug/mL. The damage induced by imidacloprid in the HepG2 cells resulted from a clastogenic action of this insecticide (76.6% of the MN /micronucleus test/ did not present a centromeric signal). ANIMAL STUDIES: IM (purity, 94.2%) did not irritate the eyes or skin of rabbits and did not sensitize the skin of guinea-pigs. IM given orally as a single dose was moderately toxic to rats and mice. Behavioral and respiratory signs, disturbances of motility, narrowed palpebral fissures, transient trembling and spasms were seen in rats and mice treated orally at doses /greater than or equal/ to 200 mg/kg bw and /greater than or equal to/ 71 mg/kg bw, respectively. The clinical signs were reversed within 6 days. In chronic experiments conducted in rats, the liver was the principal target organ, with hypertrophy of hepatocytes and sporadic cell necrosis in high-dose males only. Liver pathology was mild at termination of the study and was fully reversible within the recovery period. IM-treated male rats showed histopathological alterations in testis and epididymis. In developmental studies in rats, there was a high percentage of male fetuses and an increased incidence of wavy ribs was observed. In

Imidacloprid acts on the nicotinic acetylcholine receptor; the chlorination inhibits degradation by acetylcholine-esterase (L1130).

Regulation (EC) No 1107/2009 (amended)

Imidacloprid is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/116/EC, 2010/21/EU, Reg. (EU) 2017/195, Reg. (EU) 2020/1643, Reg. (EU) 2022/801, Reg. (EU) No 485/2013, Reg. (EU) No 540/2011, Reg.(EU) No 2018/783

Status: Active Update: 04-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/33173；Status: Cease Manufacture Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/5039

Imidacloprid: HSNO Approval: HSR003302 Approved with controls

Indications for use: Kills adult fleas and is indicated for the treatment of flea infestations on dogs and puppies 10 weeks of age and older and weighing 4 lb or greater. ... Limitations. Do not give to puppies younger than 10 weeks of age or to dogs weighing less than 4 lb. Do not give more than one tablet a day.

Tolerances are established for residues of the insecticide imidacloprid, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of imidacloprid (1-[6-chloro-3-pyridinyl) methyl]-N-nitro-2-imidazolidinimine) and its metabolites containing the 6-chloropyridinyl moiety, calculated as the stoichiometric equivalent of imidacloprid, in or on the following commodities:[Table#6947]

Time-limited tolerances are established for residues of the insecticide imidacloprid, including its metabolites and degradates in connection with use of the pesticide under a Section 18 emergency exemption granted by EPA. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of imidacloprid (1-[6-chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine) and its metabolites containing the 6-chloropyridinyl moiety, calculated as the stoichiometric equivalent of imidacloprid. These tolerances will expire and are revoked on the dates specified in the following table:[Table#6948]

Tolerances are established for indirect or inadvertent residues of the insecticide imidacloprid, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of imidacloprid (1-[6-chloro-3-pyridinyl) methyl]-N-nitro-2-imidazolidinimine) and its metabolites containing the 6-chloropyridinyl moiety, calculated as the stoichiometric equivalent of imidacloprid, in or on the following commodities, when present therein as a result of the application of the pesticide to growing crops listed in this section and other non-food crops as follows:[Table#6949]

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 129099; Type of Pesticide: conventional - insecticide/termiticide; Use Site: domestic, food, ornamental use; Year: 1994.

QP - Antiparasitic products, insecticides and repellents；QP53 - Ectoparasiticides, insecticides and repellents；QP53A - Ectoparasiticides for topical use, incl. insecticides；QP53AX - Other ectoparasiticides for topical use；QP53AX17 - Imidacloprid

The half-lives for excretion of the radiolabeled imidacloprid were calculated in rats after a single i.v. dose of 1 mg/kg, after single oral doses of 1 and 20 mg/kg or after multiple doses of 1 mg/kg. The excretion half-life values varied greatly (from 26 hr to 118 hr), but the variation was not dose-, sex-, or route-dependent. ...

methylene-[(14)C] imidacloprid (86.4 - 123 uCi/mg, 98.4 - 99% purity): single [1 mg/kg (5 males), 150 mg/kg (7 males)] and chronic treatment with the unlabeled imidacloprid for 1 year in diet prior to receiving radiolabeled imidacloprid (80 mg/kg, 10 males); methylene-[(14)C] WAK 3839 (40 uCi/mg, 99% purity): 1 mg/kg 5 males); both compound absorbed rapidly after single oral dosing; terminal half-lives for imidacloprid and WAK 3839 are 35.7 and 46.9 hrs, respectively ... .

... Honeybees were treated orally with imidacloprid at 20 and 50 ug/kg per bee. ... Imidacloprid had a half-life ranging between 4.5 and 5 hr and was rapidly metabolized into 5-hydroxyimidacloprid and olefin. ...

A: NTN 33893, 99.9% purity), B: 1-[(6-chloro-3pyridinyl)(14)C-methyl]-4,5-dihydro-N-nitro-(1)H-imidazol-2-amine] (150.7 uCi/mg, >99% purity); oral: single (1 mg/kg B, 20 mg/kg B), multiple (1 mg/kg A qd @ 14 days followed by 24 hrs after final dose by a single dose of B); IV: single (1 mg/kg B); 5 rats/sex/dose; >90% of administered radioactivity eliminated 48 hours after dosing with less than 1% remaining in the carcass in all dose groups; no sex differences in excretion pattern and metabolic profiles of the excreta were evident following low dose administration; however, at the high dose, females showed a slightly higher renal elimination rate than males; males showed a higher capacity to metabolize the test compound and the amount of parent compound was lower as compared to females; oxidation cleavage of the parent compound yields 6-chloronicotinic acid which then reacts with glycine to form a conjugate (WAK 3583); second major route of metabolism involves hydroxylation and elimination of water from the imidazolidine ring in the 4- or 5-position to produce the metabolite NTN 35884; these metabolites are excreted in urine and feces; no evidence of bioaccumulation following multiple dosing was reported.

methylene-[(14)C] imidacloprid (86.4 - 123 uCi/mg, 98.4 - 99% purity): single [1 mg/kg (5 males), 150 mg/kg (7 males)] and chronic treatment with the unlabeled imidacloprid for 1 year in diet prior to receiving radiolabeled imidacloprid (80 mg/kg, 10 males); methylene-[(14)C] WAK 3839 (40 uCi/mg, 99% purity): 1 mg/kg 5 males); both compound absorbed rapidly after single oral dosing; terminal half-lives for imidacloprid and WAK 3839 are 35.7 and 46.9 hrs, respectively; 75% of the given dose of both compounds are eliminated primarily via urine within 48 hrs; fecal elimination plays a minor role, since 21% and 16% of the recovered radioactivity are excreted by this route, respectively; glycine conjugate of 6-Cl-nicotinic acid (WAK 3583), two monohydroxylated metabolites (WAK 4103) and the unsaturated metabolite (NTN 35884) were identified in the urine and accounted for 82% of the total radioactivity; same metabolites were also identified in feces; besides unchanged WAK 3839, one other metabolite NTN 33823 was identified in urine and feces obtained from rats treated with WAK 3839; WAK 3839 and other metabolites identified after a single low dose were detected in urine from rats and mice treated chronically with imidacloprid in their diet; this finding suggests that WAK 3839 is formed during chronic exposure to imidacloprid.

WAK 3839, a metabolite of NTN 33893; 98.9% purity; /V79-HGPRT assay with/ doses (based on solubility limit and cytotoxicity test): 500, 1000, 1500, 1750, & 2000 ug/mL for both -S9 trials and 1 of 2 +S9 trials; for the other +S9 trial the doses were 500, 750, 1000, 1250, 1500, & 1750 ug/mL; after plating 4 x 106 cells/250 mL flask, the cells were exposed to test article (-/+ S9 microsomes) for 5 hr followed by an "expression period" of exponential growth and subsequent replating under selective conditions (10 ug/mL 6thioguanine) at 3 x 105 cells/100 mm dish; after 7 days the colonies were fixed and counted; duplicate exposure dishes were run, each dish generating 8 replicate dishes in the selection condition; test article did not induce 6-thioguanine resistance at any dose despite success of positive controls (-S9, ethyl methane sulfonate; +S9, DMBA); it is not mutagenic in this system under these conditions.

WAK 3839, a metabolite of NTN 33893; 94.3% purity; /CHO-HGPRT assay with/ doses (based on solubility limit and cytotoxicity test), -S9: 62.5, 125, 250, 500, 1000, & 2000 ug/mL; +S9: 500, 750, 1000, 1250, 1500, & 2000; after plating 4 x 106 cells/250 mL flask, the cells were exposed to test article (-/+ S9 microsomes) for 5 hr followed by an "expression period" of exponential growth and subsequent replating under selective conditions (10 ug/mL 6-thioguanine) at 3 x 105 cells/100 mm dish; after 7 days the colonies were fixed and counted; duplicate exposure dishes were run, each dish generating 8 replicate dishes in the selection condition; test article did not consistently induce 6-thioguanine resistance at any dose despite success of positive controls (-S9, ethyl methane sulfonate; +S9, DMBA); it is not mutagenic in this system under these conditions.

For more Metabolism/Metabolites (Complete) data for IMIDACLOPRID (14 total), please visit the HSDB record page.

Imidacloprid has known human metabolites that include 1H-Imidazol-2-amine, 1-[(6-chloro-3-pyridinyl)methyl]-4,5-dihydro-N-nitroso-, olefin, and 5-hydroxy-imidacloprid.

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.

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.

/MILK/ [(14)C-methylene]Imidacloprid was administered to one 41 kg lactating goat by intubation in three consecutive daily doses of 10 mg/kg. The goat was sacrificed 2 hr after the last dose. The highest plasma concentration of 3.98 mg/mL was measured after 2 hr of last dosing. The highest radioactivity of 3.16-3.65 ug/g in the milk was determined 8 hr after the first dose and 2 hours after the third dose; the concentration in the milk prior to second dosing was 2.77 ug/g. Assuming a daily milk production of about 2 liters, the radioactivity in the milk was about 0.4% of the total administered radioactivity. The total residue in the edible tissues and organs measured two hours after the third dose was about 5% of the administered radioactivity. The respective residual radioactivity in the edible tissues was 1.3% (liver), (0.1%) kidney, (3%) muscles and 0.4% (fat). The main compounds in the milk and the edible tissues were imidacloprid, olefinic imidacloprid (NTN 35884) and 4- and 5-OH-imidacloprid.

Five laying hens were intubated with 10 mg/kg methylene-labeled- (14)C-imidacloprid for 3 days. The highest radioactivity of 0.34 ug/mL in the plasma was measured at 0.5 hr after the third dosing. At that time, the total residue in the edible tissues and organs was about 3% of the total dose. The highest radioactivity of 1.347 ug/g in eggs was found 2 hr after the last dose. This level was less than 0.2% of the total administered radioactivity. The main metabolite in the eggs was the olefine-imidacloprid. Olefine- and desnitro-imidacloprid were detected in muscle and kidney tissues.

A: NTN 33893, 99.9% purity), B: 1-[(6-chloro-3-pyridinyl) (14)C-methyl]-4,5dihydro- N-nitro-1H-imidazol-2-amine] (150.7 uCi/mg, >99% purity); oral: single (1 mg/kg B, 20 mg/kg B), multiple (1 mg/kg daily for 14 days followed by 24 hr after final dose by a single dose of B); IV: single (1 mg/kg B); 5 rats/sex/dose; following oral and intravenous administration 94 - 100% of the administered radioactivity is absorbed and readily distributed to the body from the central compartment as indicated by a short mean absorption half-life (35 minutes) and an apparent volume of distribution accounting for about 84% of the total body volume; the small mean residence time which vary between 9 and 17 hours suggests that the total radioactivity is rapidly eliminated from the body; after oral or intravenous administration, 91.4 to 96% of the given dose was excreted via urine and feces by 48 hours; no significant amount of radioactivity was found in expired air; high concentrations of total radioactivity were observed in the kidney, liver, lung and skin; no signs of bioaccumulation were evident.

[Imidazolidine-4,5-(14)C] Imidacloprid (0.827 uCi/mg, 99.8% purity, ... and 124 uCi/mg, >99% purity ... ); oral; 1 mg/kg (10 male /rats/, 5 female /rats/) and 150 mg/kg (5 male /rats/); absorption after oral dosing is rapid and maximal plasma concentration is achieved between 1 and 1.5 hr at the low dose and 4 hr at the high dose; after oral administration of the imidazolidine labeled compound, the renal-excreted portion of the given dose is higher (91%) as compared to methylene labeled Imidacloprid (75%); fecal elimination plays a minor role and 1% of the administered radioactivity remains in the body at 48 hr; highest radioactivity concentrations were reported in liver irrespective of dose level; 5 metabolites were identified in urine which represent 77% of radioactivity recovered in urine.

For more Absorption, Distribution and Excretion (Complete) data for IMIDACLOPRID (10 total), please visit the HSDB record page.

Used as insecticide for soil, seed, or foliar treatment in cereal, cotton, fruit, maize, potatoes, rice, sugar beets, turf, and vegetables; to control fleas in dogs and cats; [HSDB] Other examples of neonicotinoids (derived from guanidine compounds) are Thiamethoxam and Clothianidine; Effective against termites; [Ullmann]

Farming (Pesticides) [Category: Industry]

Cholinergic Agents; Insecticides

For imidacloprid (USEPA/OPP Pesticide Code: 129099) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Imidacloprid is registered to control insect pests on agricultural and nursery crops, structural pests and parasites on companion animals.

For control of aphids, Colorado potato beetle, ricehoppers, thrips, whiteflies, and turf and soil insects in cereal, corn, cotton, sorghum, fruit, maize, potatoes, rice, soybeans, sugarbeets, turf, and vegetables. Acceleron seed treatment for use on soybeans. CropStar seed treatment for use on maize. Genesis XT seed treatment for use on potatoes. Aeris seed treatment for use on cotton (delinted seed only).

The National Pesticide Information Retrieval System (NPIRS) identifies 66 companies with active labels for products containing the chemical imidacloprid. To view the complete list of companies, product names and percent imidacloprid in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.

Nuprid 2F Insecticide (Nufarm Americas, Inc.): Active ingredient: imidacloprid 21.4%.

Imidacloprid Technical Insecticide (Bayer Cropscience LP): Active ingredient: imidacloprid 98.0%.

Triple Crown Golf Insecticide (FMC Corp.): Active ingredient: imidacloprid 13.83%; bifenthrin 7.87%; and zeta-cypermethrin 2.7%..

For more Formulations/Preparations (Complete) data for IMIDACLOPRID (33 total), please visit the HSDB record page.

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes