Common name: acetamiprid
IUPAC name: (E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamidine
Chemical Abstracts name: (E)-N-[(6-chloro-3-pyridinyl)methyl]-N'-cyano-N-methylethanimidamide
CAS RN: [135410-20-7]
PHYSICAL CHEMISTRY
Mol. wt.: 222.7; M.f.: C10H11ClN4; Form: Colourless crystals; M.p.: 98.9 °C; V.p. <1x10-3 mPa (25 ºC); KOW: logP = 0.80 (25 ºC); Henry: <5.3x10-8 Pa m3 mol-1 (calc.); S.g./density: 1.330 (20 °C); Solubility: In water 4250 mg/l (25 ºC). Soluble in acetone, methanol, ethanol, dichloromethane, chloroform, acetonitrile and tetrahydrofuran; Stability: Stable in buffered solutions at pH 4, 5, 7. Degraded slowly at pH 9 and 45 ºC. Stable under sunlight; pKa: 0.7, v. weak base.
APPLICATIONS
Biochemistry: Agonist of the nicotinic acetylcholine receptor, affecting the synapses in the insect central nervous system.
Mode of action: Systemic insecticide with translaminar activity and with contact and stomach action.
Uses: Control of Hemiptera, especially aphids, Thysanoptera and Lepidoptera, by soil and foliar application, on a wide range of crops, especially vegetables, fruit and tea. Applied at 75-300 g/ha on vegetables, 100-700 g/ha in orchards.
Formulation types: FU; GR; EC; WP.
MAMMALIAN TOXICOLOGY
Oral: Acute oral LD50 for male rats 217, female rats 146, male mice 198, female mice 184 mg/kg.
Skin and eye: Acute percutaneous LD50 for male and female rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits); not a skin sensitiser (guinea pigs).
Inhalation: LC50 (4 h) for male and female rats >0.29 mg/l.
NOEL: (2 y) for rats 7.1 mg/kg b.w.; (18 mo) for mice 20.3 mg/kg b.w.; (1 y) for dogs 20 mg/kg b.w.
Other: Negative in the Ames test.
ECOTOXICOLOGY
Birds: LD50 for bobwhite quail 180 mg/kg. LC50 for bobwhite quail >5000 ppm.
Fish: LC50 (24-96 h) for carp >100 mg/l.
Daphnia: LC50 (24 h) >200 mg/l.
Algae: EC50 (72 h) >98.3 mg/l; NOEC (72 h) 98.3 mg/l.
ENVIRONMENTAL FATE
Plants: Slowly degraded on or in plants, forming five identified metabolites.
Soil/Environment: DT50 in clay loam 1 d; in light clay 1-2 d. DT50 for total residues 15-30 d.
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