Imidacloprid
General product information
IMIDACLOPRID 95% TC, 200G/LT SL, 350G/LT SC, 700G/KG WSNOMENCLATURE
Common name: Imidacloprid
Other name: Imidacloprid (BSI, djaft E-ISO); imidaclopride ((m) F-ISO)
Iupac name: q-(6-chloro-3-pyridylmethyl)-N-nitr~imidaz~lidin-2-ylideneamine
Chemical abstracts name: 1-[(6-chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine
Type: Insecticide for Agriculture
CAS RN: [138261-41-3]
PHYSICAL CHEMISTRY
M.F: C9H10ClN5O2
Mol.wt.: 255.7
Style/Appearance: Colourless crystals, with a weak characteristic odour
M.p.: 144℃
V.p.: 4 10-7 mPa (20℃); 9 10-7 mPa (25℃)
S.g./density: 1.54 (23℃)
Solubility: In water 0.61 g/l (20℃). In dichloromethane 55, isopropanol 1.2, toluene 0.68, n-hexane 0.1 (all in g/l, 20℃).
Stability: Stable to hydrolysis at pH 5-11.
Henry: 2 10-10 Pa m3 mol-1 (20℃, calc.)
KowlogP: 0.57 (21℃)
APPLICATION
Formulation type(s): DP; FS; GR; SC; SL; WG; WP; WS.
Biochemistry: Acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system.
Mode of action: Systemic insecticide with translaminar activity and with contact and stomach action. Readily taken up by the plant and further distributed acropetally, with good root-systemic action.
Uses: Control of sucking insects, including rice-, leaf-and planthoppers, aphids, thrips and whitefly. Also effective against soil insects, termites and some species of biting insects, such as rice water weevil and Colorado beetle. Has no effect on nematodes and spider mites. Used as a seed dressing, as soil treatment and as foliar treatment in different crops, e.g. rice, cotton, cereals, maize, sugar beet, potatoes, vegetables, citrus fruit, pome fruit and stone fruit.
MAMALIAN TOXICOLOGY
Oral: Acute oral LD50 for male and female rats c. 450 mg/kg.
Skin & Eye: Acute percutaneous LD50 (24 h) for rats 5000 mg/kg. Non-irritating to eyes and skin (rabbits). Not a skin sensitiser.
Inhalation: LC50 (4 h) for rats 5323 mg/m3 dust, 69 mg/m3 air (aerosol).
Noel: (2 y) for male rats 100, female rats 300, mice 330 mg/kg diet; (52 w) for dogs 500 mg/kg diet.
ADI: 0.057 mg/kg b.w. /Other Not mutagenic or city class: WHO (a.i.) II; EPA (formulation) II
ENVIRONMENTAL FATE
Animals: 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 gastro-intestina[ tract and quickly eliminated (96% within 48 hours, mainly via the urine). Only c. 15% was eliminated as unchanged parent compound: the most important metabolic steps were hydroxylatJon at the Jmidazolidine ring, hydrolysis to 6chloronicotinic acid, loss of the nitro group with formation of the guanidine and conjugation of the 6-chtoronicotinic 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 ts Metabolism was investigated on rice (after soil treatment), maize (seed treatment), potatoes (granule or spray application), aubergines (granules) and tomatoes (spray all cases, imidacloprid is metabolised by loss of the nitro group, hydroxylation at the imidazolidine ring, hydrolysis to 6-chloronicotinic acid and formation of conjugates; all metabolites contained the 6-chloropyridinylmethylene moiety.
Soil / environment: In lab. studies, the most important metabolic steps were oxidation at the imidazolidine ring, reduction or loss of the nitro group, hydrolysis to 6-chtoronicotinic acid and mineralisation; these processes were strongly accelerated by vegetation, tmidacloprid shows a medium adsorption to soil. Column leaching tests (with prior ageing) with a.i. and various formulations showed that imidacloprid and soil metabolites are to be classified as immobile; leaching into deeper soil layers is not to be expected if imidacioprid is used as recommended. Stable to hydrolysis under sterile conditions (under exclusion of light). Environmental DT50 c. 4 h (calc., based on tests of direct photolysis in aqueous solutions). Besides sunlight, the microbial activity of a water/sediment system is an important factor for the degradation of imidactoprid.
Analysis: Residues by hplc (F-J. Placke & E. Weber, Pfianzenschutz-Nachrich. Bayer, 93/2, 46, 109-182 (1993)). A method has been developed based on the presence of the 6-chloropyridinylmethylene moiety in all known plant and animal metabolites.