acetamiprid
Insecticide
IRAC 4A; 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]; [160430-64-8] unspecified stereochemistry Development codes NI-25 (Nippon Soda); EXP60707B
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 Manufacturers Nippon Soda; Sharda
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 products: 'Mospilan' (Nippon Soda); 'Vapcomore' (Vapco)
OTHER PRODUCTS
'Assail' (Nippon Soda); 'Gazel' (Nippon Soda); 'Gazelle' (Nippon Soda); 'Intruder' (Nippon Soda); 'Profil' (Nippon Soda); 'Rescate' (Nippon Soda); 'Saurus' (Nippon Soda); 'Supreme' (Nippon Soda); 'Tristar' (Nippon Soda); 'Adjust' (Bayer CropScience); 'Epik' (Sipcam Inagra) Discontinued products: 'Pristine' * (Aventis)
ANALYSIS
Tech. product by hplc; residues by glc.
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. ADI 0.066 mg/kg (Japan) 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.
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