NOMENCLATURE

Common name acetamiprid (pa ISO)

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]  Development codes NI-25 (Nippon Soda) 

PHYSICAL CHEMISTRY

Mol. wt. 222.7  M.f. C₁₀H₁₁ClN₄  Form Colourless crystals.  M.p. 98.9 °C  V.p. <1 ´ 10^-3 mPa (25 ºC)  K_OW logP = 0.80 (25 ºC)  Henry <5.3 ´ 10^-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. 

ANALYSIS

Tech. product by hplc; residues by gc. 

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 (H. Saito et al., Proc. 9th IUPAC Int. Congr. Pestic. Chem., London, 1998, 2, 5A-010).  Soil/Environment DT₅₀ in clay loam 1 d; in light clay 1-2 d. DT₅₀ for total residues 15-30 d.