neonicotinoid

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]

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) KOW 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

COMMERCIALISATION

History Reported by H. Takahashi et al., Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 89. Registered in Japan in 1995 and introduced by Nippon Soda Co., Ltd. Patents US 5304566

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. Selected tradenames: 'Mospilan' (Nippon Soda)

OTHER TRADENAMES

'Assail' (Aventis); 'Rescate' (Nippon Soda, Aventis); 'Saurus' (Nippon Soda, Aventis)

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.