49. Acetamiprid

Nomenclature

CAS number: 160430-64-8
(1E)-N-[(6-Chloro-3-pyridinyl)methyl]-N′-cyano-N-methylethanimidamide; (E)-N-cyano-N′-(2-chloro-5-pyridylmethyl)-N′-methylacetamidine; NI-25; Assail (Nippon Soda); Intruder (Nippon Soda); Mospilan (Nippon Soda); Profil (Nippon Soda); Tri-Star (Nippon Soda).
C10H11ClN4; mol wt 222.67.
C 53.94%, H 4.98%, Cl 15.92%, N 25.16%.

Description and references

Neonicotinoid insecticide for use in food crops and ornamental plants. Prepn: K. Ishimitsu et al., WO 9104965; eidem, US 5304566 (1991, 1994 both to Nippon Soda); of tritiated form: B. Latli et al., J. Labelled Compd. Radiopharm. 38, 971 (1996). Physical properties, biological activity and field trials: H. Takahashi et al., Proc. Br. Crop Prot. Conf. - Pests Dis. 1992, 89. HPLC determn in soil: M. Tokieda et al., J. Pestic. Sci. 23, 296 (1998). LC-MS/MS determn in urine: A. Marín et al., J. Chromatogr. B 804, 269 (2004) DOI PubMed. Stereochemistry and active conformation: A. Nakayama et al., Pestic. Sci. 51, 157 (1997) DOI. Efficacy against diamondback moth: H. Takahashi et al., J. Pestic. Sci. 24, 23 (1999); against green peach aphid: eidem, ibid. 270.

Chemical structure

Properties

White crystals, mp 101.0-103.3°. Soly in water at 25°: 4200 mg/l. Sol in acetone, methanol, ethanol, dichloromethane, chloroform, acetonitrile, tetrahydrofuran. Vapor pressure at 25°: < 1 × 108 mmHg. LD50 in male, female rats, male, female mice (mg/kg): 217, 146, 198, 184 orally (Takahashi).

Use

Insecticide.