10399. Chlorantraniliprole

Nomenclature

CAS number: 500008-45-7
3-Bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; DPX-E2Y45; Altacor (DuPont); Coragen (DuPont); Dermacor (DuPont); Rynaxypyr (DuPont).
C18H14BrCl2N5O2; mol wt 483.15.
C 44.75%, H 2.92%, Br 16.54%, Cl 14.68%, N 14.50%, O 6.62%.

Description and references

Anthranilic diamide pesticide; insect-specific ryanodine receptor activator. Prepn: G. P. Lahm et al., WO 03015519; eidem, US 7232836 (2003, 2007 both to DuPont); and ryanodine receptor activity: idem et al., Bioorg. Med. Chem. Lett. 17, 6274 (2007) DOI PubMed. Physical properties and activity: A. Bassi et al., Proc. 16th Int. Plant Prot. Congr. 1, 52 (2007). HPLC-MS/MS determn in fruits and vegetables: P. Caboni et al., J. Agric. Food Chem. 56, 7696 (2008) DOI PubMed. Field trials vs white grubs: A. M. Koppenhfer, E. M. Fuzy, Biol. Control 45, 93 (2008) DOI; vs fruit flies: L. A. F. Teixeira et al., Pest Manag. Sci. 65, 137 (2009) DOI PubMed.

Chemical structure

Properties

Fine crystalline off-white powder, mp 208-210°. Log P (octanol/water): 2.76 (pH 7). Vapor pressure (20°): 6.3 × 1012 Pa. pKa (20°): 10.88. Soly (mg/l) at 20°: acetone 3446, methanol 1714, ethyl acetate 1144, water 1.0. LD50 in rats (mg/kg): >5000 orally; >5000 dermally. LC50 (4 hr) in rats (mg/l): >5.1 by inhalation. LC50 in rainbow trout, bluegill sunfish (mg/l): >13.8, >15.7 (Bassi).

Use

Insecticide.