Chlorfenapyr

Title: Chlorfenapyr
CAS Registry Number: 122453-73-0
CAS Name: 4-Bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
Manufacturers' Codes: AC-303630; CL-303630
Trademarks: Pirate (BASF); Stalker
Molecular Formula: C15H11BrClF3N2O
Molecular Weight: 407.61
Percent Composition: C 44.20%, H 2.72%, Br 19.60%, Cl 8.70%, F 13.98%, N 6.87%, O 3.93%
Literature References: Halogenated pyrrole mitochondrial uncoupler. Prepn: D. G. Brown et al., BR 8803788; eidem, US 5010098 (1988, 1991 both to Am. Cyanamid). Chemical and biological properties: J. B. Lovell et al., Brighton Crop Prot. Conf. - Pests Dis. 1990, 37. Summary of field trials: T. P. Miller et al., ibid., 43. Field trials on apples: Y.-J. Ahn et al., Appl. Entomol. Zool. 31, 67 (1996). Mechanism of action: B. C. Black et al., Pestic. Biochem. Physiol. 50, 115 (1994).
Properties: White solid, mp 91-92°. Sol in acetone, diethyl ether, DMSO, THF, acetonitrile, alcohols. Insol in water. Log P ~5. LD50 (single dose) in male, female rats (mg/kg): 223, 459 orally; in rabbits: >2000 dermally (Lovell). LC50 in Japanese carp: 0.5 ppm (Lovell).
Melting point: mp 91-92°
Toxicity data: LD50 (single dose) in male, female rats (mg/kg): 223, 459 orally; in rabbits: >2000 dermally (Lovell); LC50 in Japanese carp: 0.5 ppm (Lovell)
Use: Insecticide. Acaricide.
Chlorfenethol Chlorfenson Chlorfenvinphos Chlorhexadol Chlorhexidine

Chlorfenapyr
Skeletal formula
Space-filling model
Identifiers
CAS number 122453-73-0
ChemSpider 82875
UNII NWI20P05EB
KEGG C18455 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H11BrClF3N2O
Molar mass 407.6 g/mol
Density 0.543 g/ml tapped bulk density
Melting point 100-101 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chlorfenapyr is a pesticide, and specifically a pro-insecticide (meaning it is metabolized into an active insecticide after entering the host), derived from a class of microbially produced compounds known as halogenated pyrroles. The United States Environmental Protection Agency initially denied registration in 2000 for use on cotton primarily because of concerns that the insecticide was toxic to birds and because effective alternatives were available. However, it was registered by EPA in January, 2001 for use on non-food crops in greenhouses. In 2005, EPA established a tolerance for residues of chlorfenapyr in or on all food commodities. Chlorfenapyr works by disrupting the production of Adenosine triphosphate, specifically, "Oxidative removal of the N-ethoxymethyl group of chlorfenapyr by mixed function oxidases forms the compound CL 303268. CL 303268 uncouples oxidative phosphorylation at the mitochondria, resulting in disruption of production of ATP, cellular death, and ultimately organism mortality."