7394. Picaridin

Nomenclature

CAS number: 119515-38-7
2-(2-Hydroxyethyl)-1-piperidinecarboxylic acid 1-methylpropyl ester; 1-methylpropyl 2-(2-hydroxyethyl)piperidine-1-carboxylate; hydroxyethyl isobutyl piperidine carboxylate; icaridin; KBR 3023; Bayrepel (Bayer); Saltidin (Saltigo).
C12H23NO3; mol wt 229.32.
C 62.85%, H 10.11%, N 6.11%, O 20.93%.

Description and references

Acts on certain olfactory receptor cell types to reduce the activating or attracting effect of odor sources. Prepn: B.-W. Krüger et al., EP 289842; eidem, US 4900834 (1988, 1990 both to Bayer). Synthesis and mode of action: J. Boeckh et al., Pestic. Sci. 48, 359 (1996) DOI. Field trials in mosquito repellency: H. H. Yap et al., J. Vector Ecol. 23, 62 (1998) PubMed; A. Badolo et al., Trop. Med. Int. Health 9, 330 (2004) DOI PubMed. Physical, chemical and toxicological properties: WHO Interim Specification for Icaridin (WHO/IS/TC/ 668/2001) 16 pp. MS characterization: T. P. Knepper, J. Chromatogr. A 1046, 159 (2004) DOI PubMed.

Chemical structure

Properties

Colorless, nearly odorless liquid. mp <-170°. bp1013 hPa 280°. d20 1.07. nD20 1.4717. Flash pt: 142°C. Log P (octanol/water) at 20°: 2.11 (unbuffered), 2.23 (pH 4-9). Vapor pressure (hPa): 3.4×10-4 at 20°; 5.9×10-4 at 25°; 7.1×10-3 at 50°. Soly at 20° (g/l): water 8.2 (pH 4-9), 8.6 (unbuffered); acetone 7250. Viscosity at 20°: 135.5 mPa s. LD50 in rats (mg/kg): 4743 orally; >2000 dermally (Yap). LC50 in rainbow trout (96 hr): 173 mg/l; in bobwhite quail (5 day diet): >5000 ppm a.i. in diet (WHO).

Use

Insect repellent.