Chlorfenapyr

Chlorfenapyr is an insecticide, and specifically a pro-insecticide (meaning it is metabolized into an active insecticide after entering the host).^[1] It is derived from a class of microbially produced compounds known as halogenated pyrroles.

Chlorfenapyr

Names
Preferred IUPAC name 4-Bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
Identifiers
CAS Number	122453-73-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:39347
ChEMBL	ChEMBL1869551
ChemSpider	82875
ECHA InfoCard	100.116.332
EC Number	602-782-4
KEGG	C18455 Y
PubChem CID	91778
UNII	NWI20P05EB
CompTox Dashboard (EPA)	DTXSID9032533
InChI InChI=1/C15H11BrClF3N2O/c1-2-23-8-22-13(9-3-5-10(17)6-4-9)11(7-21)12(16)14(22)15(18,19)20/h3-6H,2,8H2,1H3 Key: CWFOCCVIPCEQCK-UHFFFAOYAO
SMILES Clc2ccc(c1c(C#N)c(Br)c(n1COCC)C(F)(F)F)cc2
Properties
Chemical formula	C15H11BrClF3N2O
Molar mass	407.62 g·mol−1
Density	0.543 g/ml tapped bulk density
Melting point	100 to 101 °C (212 to 214 °F; 373 to 374 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H320, H331, H371, H373, H410
Precautionary statements	P260, P261, P264, P270, P271, P273, P301+P312, P304+P340, P305+P351+P338, P309+P311, P311, P314, P321, P330, P337+P313, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

History and Applications

Chlorfenapyr was developed by American Cyanamid from the natural product dioxapyrrolomycin, which was isolated from Streptomyces fumanus.^[2]

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.^[3] However, it was registered by the EPA in January, 2001 for use on non-food crops in greenhouses.^[4] In 2005, the EPA established a tolerance for residues of chlorfenapyr in or on all food commodities.

Chlorfenapyr is also used as a wool insect-proofing agent, and was introduced as an alternative to synthetic pyrethroids due to a lower toxicity to mammalian and aquatic life.^[5]

In April 2016, in Pakistan, 31 people died when their food was spiked with chlorfenapyr.^[6]

Mode of Action

See also: Uncoupler

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."^[1] It is in IRAC group 13.