IMIDACLOPRID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10ClN5O2
Molecular Weight	255.661
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)NC1=NCCN1CC2=CN=C(Cl)C=C2

InChI

InChIKey=YWTYJOPNNQFBPC-UHFFFAOYSA-N

InChI=1S/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)

HIDE SMILES / InChI

Molecular Formula	C9H10ClN5O2
Molecular Weight	255.661
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://npic.orst.edu/factsheets/archive/imidacloprid.html
Curator's Comment: description was created based on several sources, including: http://npic.orst.edu/factsheets/archive/imidacloprid.html | https://www.ncbi.nlm.nih.gov/pubmed/10936213

Imidacloprid is a systemic, chloro-nicotinyl insecticide used for the control of sucking insects such as fleas, aphids, whiteflies, termites, turf insects, soil insects, and some beetles. It is used on co on and vegetable crops as foliar and seed treatments, soil, structures, indoor and outdoor insect control, home gardening and pet products. It is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species, Whipworms. Adverse events in animals included: malaise, vomiting, diarrhea, shaking, mydriasis, hypersalivation with abnormal neurologic signs, seizures, death, generalized hematoma of the body, and alopecia at the treatment site. Adverse reactions in humans included: burning, tingling, numbness, bad taste in the mouth, dizziness, and headache.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nicotinic acetylcholine receptor (insects) 1 Target ID: Nicotinic acetylcholine receptor (insects) Sources: https://www.drugs.com/dict/imidacloprid.html	Blocker 555		5.14 null [pIC50]

Conditions

Condition	Modality	Highest Phase	Product
Heartworm disease 3 Sources: https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051438.pdf	Curative	Approved 8583	Advantage® DUO Approved Use Drug is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species. Launch Date 2002
Flea infestations 12 Sources: https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051438.pdf	Curative	Approved 8583	Advantage® DUO Approved Use Drug is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species. Launch Date 2002
Hookworm infection 2 Sources: https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051438.pdf	Curative	Approved 8583	Advantage® DUO Approved Use Drug is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species. Launch Date 2002
Toxascariasis 1 Sources: https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051438.pdf	Curative	Approved 8583	Advantage® DUO Approved Use Drug is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species (Toxocara canis, Toxascaris leonine). Launch Date 2002
Toxocariasis 2 Sources: https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051438.pdf	Curative	Approved 8583	Advantage® DUO Approved Use Drug is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species (Toxocara canis, Toxascaris leonine). Launch Date 2002
Trichuriasis infection 6 Sources: https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051438.pdf	Curative	Approved 8583	Advantage® DUO Approved Use Drug is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species (Toxocara canis, Toxascaris leonine), Whipworm (Trichuris vulpis). Launch Date 2002
Mite infestation 3 Sources: https://animaldrugsatfda.fda.gov/adafda/app/search/public/document/downloadFoi/804	Curative	Approved 8583	Advantage® DUO Approved Use Drug is indicated for the prevention of heartworm disease caused by Dirofilaria immitis. It kills adult fleas and is indicated for the treatment of flea infestations (Ctenocephalides felis). It is also indicated for the treatment and control of the following intestinal parasites Hookworm species, Roundworm species (Toxocara canis, Toxascaris leonine), Whipworm (Trichuris vulpis). It is indicated for the treatment and control of sarcoptic mange caused by Sarcoptes scabiei var. canis. Launch Date 2002

PubMed

Title	Date	PubMed
Comparative speed of kill between nitenpyram, fipronil, imidacloprid, selamectin and cythioate against adult Ctenocephalides felis (Bouché) on cats and dogs.	2003-03-10	12591200
Learning performances of honeybees (Apis mellifera L) are differentially affected by imidacloprid according to the season.	2003-03	12639043
In vitro and in vivo studies on the effect of a combination containing 10% imidacloprid and 50% permethrin against Ixodes ricinus ticks.	2003-03	12632172
5-Azidoepibatidine: an exceptionally potent photoaffinity ligand for neuronal alpha 4 beta 2 and alpha 7 nicotinic acetylcholine receptors.	2003-02-10	12565964
European monitoring of resistance to insecticides in Myzus persicae and Aphis gossypii (Hemiptera: Aphididae) with special reference to imidacloprid.	2003-02	12593682
Variation in response to neonicotinoid insecticides in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae).	2003-02	12587870
Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors.	2003	12208819
Modeling of single-step and multistep adsorption isotherms of organic pesticides on soil.	2002-12-04	12452653
Competitive sorption between imidacloprid and imidacloprid-urea on soil clay minerals and humic acids.	2002-11-06	12405782
Desnitro-imidacloprid activates the extracellular signal-regulated kinase cascade via the nicotinic receptor and intracellular calcium mobilization in N1E-115 cells.	2002-11-01	12460746
Comparison of microextraction procedures to determine pesticides in oranges by liquid chromatography-mass spectrometry.	2002-09-13	12350094
Toxicological and mechanistic studies on neonicotinoid cross resistance in Q-type Bemisia tabaci (Hemiptera: Aleyrodidae).	2002-09	12233176
Neonicotinoid insecticides: reduction and cleavage of imidacloprid nitroimine substituent by liver microsomal and cytosolic enzymes.	2002-09	12230409
Effects of mutations of a glutamine residue in loop D of the alpha7 nicotinic acetylcholine receptor on agonist profiles for neonicotinoid insecticides and related ligands.	2002-09	12208772
Nerve membrane ion channels as the target site of insecticides.	2002-08	12370061
Fecundity in twospotted spider mite (Acari: Tetranychidae) is increased by direct and systemic exposure to imidacloprid.	2002-08	12216813
Hazards of insecticides to the bumble bees Bombus impatiens (Hymenoptera: Apidae) foraging on flowering white clover in turf.	2002-08	12216812
Bioassay and field-simulator studies of the efficacy of pymetrozine against peach-potato aphids, Myzus persicae (Hemiptera: Aphididae), possessing different mechanisms of insecticide resistance.	2002-08	12192905
Sorption behaviour of acetochlor, atrazine, carbendazim, diazinon, imidacloprid and isoproturon on Hungarian agricultural soil.	2002-08	12146633
Determination of acetamiprid, imidacloprid, and nitenpyram residues in vegetables and fruits by high-performance liquid chromatography with diode-array detection.	2002-07-31	12137461
Imidacloprid residues in Willapa Bay (Washington State) water and sediment following application for control of burrowing shrimp.	2002-07-17	12105979
[Investigation and case study of Imidacloprid insecticide caused poisoning].	2002-07	12415875
Effects of formulation on the run-off of imidacloprid from turf.	2002-07	12146171
Structural effects of dinotefuran and analogues in insecticidal and neural activities.	2002-07	12146167
Development of a larval bioassay for susceptibility of cat fleas (Siphonaptera: Pulicidae) to imidacloprid.	2002-07	12144302
Therapy and prevention of parasitic insects in veterinary medicine using imidacloprid.	2002-07	12052186
Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian alpha4beta2 and Drosophila nicotinic receptors.	2002-06-20	12061885
Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction.	2002-06-07	12084621
Comparison of two bioassay techniques for assessing the acute toxicity of pesticides to chironomid larvae (Diptera: Chironomidae).	2002-06	12083354
Effects of dissolved organic carbon on sorption and mobility of imidacloprid in soil.	2002-05-25	12026091
Nicotinic acetylcholine receptor binding of imidacloprid-related diaza compounds with various ring sizes and their insecticidal activity against Musca domestica.	2002-05	11997976
The relative toxicities of insecticides to earthworms of the Pheretima group (Oligochaeta).	2002-05	11997970
Subcritical water extraction to evaluate desorption behavior of organic pesticides in soil.	2002-04-10	11929294
Leaching behavior of imidacloprid formulations in soil.	2002-04	12069054
Safety evaluation and persistence of imidacloprid on acid lime (Citrus aurantiifolia Swingle).	2002-04	12069053
Resistance of aphis gossypii (Homoptera: Aphididae) to fenvalerate and imidacloprid and activities of detoxification enzymes on cotton and cucumber.	2002-04	12020021
Action threshold for applying insect growth regulators to tomato for management of irregular ripening caused by Bemisia argentifolii (Homoptera: Aleyrodidae).	2002-04	12020016
Managing Brachycaudis persicae (Homoptera: Aphididae) during peach orchard establishment.	2002-04	12020015
The insecticide imidacloprid is a partial agonist of the nicotinic receptor of honeybee Kenyon cells.	2002-03-15	11872245
Toxicology of newer pesticides for use in dogs and cats.	2002-03	12012747
Behaviour of beta-cyfluthrin and imidacloprid in mustard crop: alternative insecticide for aphid control.	2002-03	11993817
New developments in insecticide resistance in the glasshouse whitefly (Trialeurodes vaporariorum) and the two-spotted spider mite (Tetranychus urticae) in the UK.	2002-02	11852636
Laboratory evaluation of fipronil and imidacloprid topical insecticides for control of the plague vector Oropsylla montana (Siphonaptera: Ceratophyllidae) on california ground squirrels (Rodentia: Sciuridae).	2002-01	11931250
Translocation and translaminar bioavailability of two neonicotinoid insecticides after foliar application to cabbage and cotton.	2002-01	11838278
Evaluation of differential gene expression during behavioral development in the honeybee using microarrays and northern blots.	2002	11864369
Comparison of the activity of selamectin, imidacloprid and fipronil for the treatment of dogs infested experimentally with Ctenocephalides canis and Ctenocephalides felis felis.	2001-12-08	11787782
DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid.	2001-12	11810226
Effect of insecticides used in corn, sorghum, and alfalfa on the predator Orius insidiosus (Hemiptera: Anthocoridae).	2001-12	11777036
First steps to improve cotton crop management in Thailand.	2001	12425063
Biorational agents--mechanism and importance in IPM and IRM programs for controlling agricultural pests.	2001	12425057

Patents

Sample Use Guides

In Vivo Use Guide

The recommended minimum dose is 4.5 mg/lb (10 mg/kg) imidacloprid and 1.1 mg/lb (2.5 mg/kg) moxidectin, once a month.

Route of Administration: Topical

In Vitro Use Guide

The highest sister chromatid exchange (SCE) per cell in rabbit peripheral blood lymphocytes was observed after exposure to 0.6 mg/L of Imidacloprid - 8.69±3.17 SCE per cell.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:31:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:04 GMT 2025`
Record UNII	3BN7M937V8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BAY NTN 33893

Preferred Name

English

IMIDACLOPRID

Common Name

English

IMIDACLOPRID [HSDB]

Common Name

English

1-((6-CHLORO-3-PYRIDINYL)METHYL)-N-NITRO-2-IMIDAZOLIDINIMINE

Systematic Name

English

1-(2-CHLORO-5-PYRIDYLMETHYL)-2-(NITROIMINO)IMIDAZOLIDINE

Systematic Name

English

1-((6-CHLORO-3-PYRIDINYL)METHYL)-4,5-DIHYDRO-N-NITRO-1H-IMIDAZOL-2-AMINE

Systematic Name

English

IMIDACLOPRID [MART.]

Common Name

English

ADVOCATE COMPONENT IMIDACLOPRID

Brand Name

English

IMIDACLOPRID [ISO]

Common Name

English

IMIDACLOPRID [EMA EPAR VETERINARY]

Common Name

English

IMIDACLOPRID [GREEN BOOK]

Common Name

English

IMIDACLOPRID [MI]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 524.1140