6568. Nitenpyram

Nomenclature

CAS number: 150824-47-8
(1E)-N-[(6-Chloro-3-pyridinyl)methyl]-N-ethyl-N′-methyl-2-nitro-1,1-ethenediamine; 1-[N-(6-chloro-3-pyridylmethyl)-N-ethyl]amino-1-methylamino-2-nitroethylene; TI-304; Bestguard (Takeda); Capstar (Novartis).
C11H15ClN4O2; mol wt 270.72.
C 48.80%, H 5.58%, Cl 13.10%, N 20.70%, O 11.82%.

Description and references

Chloronicotinyl insecticide; orally administered flea adulticide. Prepn: I. Minamida et al., EP 302389; eidem, US 5849768 (1989, 1998 both to Takeda); and insecticidal activity: eidem, J. Pestic. Sci. 18, 41 (1993). Physical and biological properties: Y. Kashiwada, Agrochem. Jpn. 68, 18 (1996). Effects on neuronal nicotinic acetylcholine receptor channel in rat cells: K. Nagata et al., J. Pestic. Sci. 24, 143 (1999). Efficacy study in flea infested dogs: M.-C. Cadiergues et al., Am. J. Vet. Res. 60, 1122 (1999). LC-MS determn in fruits and vegetables: D. Zywitz et al., Dtsch. Lebensm. Rundsch. 99, 188 (2003).

Chemical structure

Properties

White crystals, mp 83-84°; also reported as pale yellow solid. Vapor pressure: 8.3 × 10-12 mmHg. Soly at 25° (g/l): water 840; chloroform 700; acetone 290; methanol 670; ethanol 89. Log P (octanol/water): -0.64. LD50 in male, female rats, male, female mice (mg/kg): 1680, 1575, 867, 1281 orally; in male, female rats (mg/kg): >2000, >2000 dermally. LC50 (48 hr) in carp, water fleas (ppm): >1000, >10000 (Kashiwada).

Therapeutic Category (Veterinary)

Ectoparasiticide.