Imidacloprid (CHEM000710)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (12)XML
Record Information
Version1.0
Creation Date2009-06-01 19:33:01 UTC
Update Date2026-03-26 18:29:04 UTC
Accession NumberCHEM000710
Identification
Common NameImidacloprid
ClassSmall Molecule
DescriptionImidacloprid is a neonicotinoid insecticide, which is a class of neuro-active insecticides modeled after nicotine. Nicotine was identified and used as an insecticide and rat poison as early as the 1600’s. Its effectiveness as an insecticide spurred a search for insecticidal compounds that have selectively less effect on mammals, which led to the discovery of neonicotinoids. Neonicotinoids, like nicotine, bind to nicotinic acetylcholine receptors of a cell. In mammals, nicotinic acetylcholine receptors are located in cells of both the central and peripheral nervous systems. In insects these receptors are limited to the CNS. While low to moderate activation of these receptors causes nervous stimulation, high levels overstimulate and block the receptors causing paralysis and death. Nicotinic acetylcholine receptors are activated by the neurotransmitter acetylcholine. Acetylcholine is broken down by acetylcholinesterase to terminate signals from these receptors. However, acetylcholinesterase cannot break down neonicotinoids and the binding is irreversible. Because most neonicotinoids bind much more strongly to insect neuron receptors than to mammal neuron receptors, these insecticides are selectively more toxic to insects than mammals. The low mammalian toxicity of neonicotinoids can be explained in large part by their lack of a charged nitrogen atom at physiological pH. The uncharged molecule can penetrate the insect blood–brain barrier, while the mammalian blood–brain barrier filters it. However, Some neonicotinoid breakdown products are toxic to humans, especially if they have become charged. Because of their low toxicity and other favorable features, neonicotinoids are among the most widely used insecticides in the world. Most neonicotinoids are water-soluble and break down slowly in the environment, so they can be taken up by the plant and provide protection from insects as the plant grows. Neonicotinoids are currently used on corn, canola, cotton, sorghum, sugar beets and soybeans. They are also used on the vast majority of fruit and vegetable crops, including apples, cherries, peaches, oranges, berries, leafy greens, tomatoes, and potatoes. The use of neonicotinoids has been linked in a range of studies to adverse ecological effects, including honey-bee colony collapse disorder (CCD) and loss of birds due to a reduction in insect populations. This has led to moratoriums and bans on their use in Europe.
Contaminant Sources
  • EPA Endocrine Screening
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • Suspected Compounds - Waste Water
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Aromatic Hydrocarbon
  • Food Toxin
  • Household Toxin
  • Insecticide
  • Metabolite
  • Neonicotinoid
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-((6-Chloro-3-pyridinyl)methyl)-N-nitro-2-imidazolidinimineChEBI
1-((6-Chloro-3-pyridyl)methyl)-N-nitro-2-imidazolidinimineChEBI
IMDChEBI
(e)-ImidaclopridHMDB
(Z)-ImidaclopridHMDB
1-(2-chloro-5-Pyridylmethyl)-2-(nitroimino)imidazolidineHMDB
1-[(6-chloro-3-Pyridinyl)methyl]-4,5-dihydro-N-nitro-1H-imidazol-2-amine, 9ciHMDB
AdmireHMDB
AdvantageHMDB
Advantage flea adulticideHMDB
Bayer brand OF imidaclopridHMDB
ConfidorHMDB
Confidor 200 SLHMDB
Confidor SLHMDB
GauchoHMDB
Imidacloprid (old RN)HMDB
MeritHMDB
Merit (insecticide)HMDB
Premise 75HMDB
ProvadoHMDB
Chemical FormulaC9H10ClN5O2
Average Molecular Mass255.660 g/mol
Monoisotopic Mass255.052 g/mol
CAS Registry Number105827-78-9
IUPAC Name2-chloro-5-{[2-(nitroamino)-4,5-dihydro-1H-imidazol-1-yl]methyl}pyridine
Traditional Nameimidacloprid
SMILES[O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1
InChI IdentifierInChI=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)
InChI KeyYWTYJOPNNQFBPC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitroguanidines. These are organonitrogen compounds containing a nitro group, which is N-linked to a guanidine.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentNitroguanidines
Alternative Parents
Substituents
  • Nitroguanidine
  • 2-halopyridine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • 2-imidazoline
  • Nitramine
  • Heteroaromatic compound
  • Organic nitro compound
  • Azacycle
  • Carboximidamide
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organochloride
  • Organic oxygen compound
  • Organic zwitterion
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless crystals (2).
Experimental Properties
PropertyValue
Melting Point143 - 144°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP0.65ALOGPS
logP1.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)5.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.34 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.75 m³·mol⁻¹ChemAxon
Polarizability23.17 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2910000000-16207f958c3941d24901Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05di-2920000000-c29270e5a1a153c5bef7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0290000000-0812870c582a68d58f9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0930000000-343db00f5be70f0fe78cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-719eaaca2c7a38c90d68Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-942ea462298844bafdc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-56328a93fd1e38aa2242Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-9000000000-cad2f4a13e5493517e85Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-9000000000-5f6d2d344bf6659eca47Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-68418a137b14a769367cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-47ad82be374a283a9dbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0920000000-46ef972fc42dceee7393Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0090000000-fc3fa48055c83ff1de5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0190000000-0cd6e54fe940f97ccb1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-0980000000-e48625fbd18b2d626cc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-0960000000-89d9de4658faefa962b1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a6r-0940000000-16fe6279a6031f08bb67Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0aba-0910000000-2859fa22e79d10470b94Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-08fr-0390000000-ab06f369da2af69be924Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0190000000-af26c2abec118b42cc59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-3250c0b819f9c6714e58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0090000000-e8976c6ed0aab7cb6f36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-7910000000-216222493c38e9ac9d30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3090000000-b3146d60a6f2b5d2900cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2190000000-54519332ebe8fd4cbef0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-b63d477ace752edc00a8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureInhalation (2) ; dermal (2) ; oral (2)
Mechanism of ToxicityImidacloprid acts on the nicotinic acetylcholine receptor; the chlorination inhibits degradation by acetylcholine-esterase (2).
MetabolismTwo main routes of metabolism responsible for the degradation of imidacloprid were identified. The first is oxidative cleavage, yielding 6-chloronicotinic acid, which is conjugated with glycine to form a hippuric acid-type conjugate. These two metabolites together represented most of the identified metabolites, or about 30% of the recovered radiolabel. Of minor importance in terms of quantity is dechlorination of the pyridinyl moiety, producing the 6-hydroxy nicotinic acid and its methylmercapturic acid derivative, probably as a degradation product of a glutathione conjugate. The 6-methylmercapto nicotinic acid conjugated with glycine, and the glycine conjugate constituted 5.6% of the recovered radiolabel. The second important biodegradation step starts with hydroxylation of the imidazolidine ring at the 4 or 5 position, and about 16% of the recovered radiolabel was identified as the sum of 4- and 5-hydroxy imidacloprid. The loss of water yields the olefinic compound. These biotransformation products and the unchanged parent compound were excreted in urine and feces, while the guanidine compound was a less important metabolite and was eliminated only in feces (1).
Toxicity ValuesLD50: 450 mg/kg (Oral, Rat) (2) LD50: 131 mg/kg (Oral, Mouse) (2) LD50: >5000 mg/kg (Dermal, Rat) (2) LD50: 69 mg/m3 (Inhalation (aerosol), Rat) (2) LD50: 5 323 mg/m3 (Inhalation (dust), Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThe most widely used applications for Imidacloprid in California are pest control in structures, turf pest control, grape growing, and head and leaf lettuce growing. Other widespread crop uses are rice, grains/cereals (2).
Minimum Risk LevelChronic Oral: 72 mg/kg/day (Rabbit) (2)
Health EffectsHypotension, fatal ventricular dysrhythmias, tremors, impaired pupillary function, and hypothermia may result from Imidacloprid poisoning (3).
SymptomsFatigue, twitching, cramps, and weakness leading to asphyxia (2).
TreatmentThere 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. (3)
Concentrations
Not Available
DrugBank IDDB11421
HMDB IDHMDB0040292
FooDB IDFDB020013
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDIM4
Wikipedia LinkImidacloprid
Chemspider ID77934
ChEBI ID5870
PubChem Compound ID86418
Kegg Compound IDC11110
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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