Chlorfenapyr Knowpia

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 ;
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

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.

History and Applications edit

Chlorfenapyr was developed by American Cyanamid from the natural product dioxapyrrolomycin, which was isolated from Streptomyces fumanus.^[1]

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.^[2] However, it was registered by the EPA in January, 2001 for use on non-food crops in greenhouses.^[3] 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.^[4]

In April 2016, in Pakistan, 31 people died when their food was spiked with chlorfenapyr.^[5]

Mode of Action edit

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."

Notes edit

^ Black, B.C.; Hollingworth, R.M.; Ahammadsahib, K.I.; Kukel, C.D.; Donovan, S. (October 1994). "Insecticidal Action and Mitochondrial Uncoupling Activity of AC-303,630 and Related Halogenated Pyrroles". Pesticide Biochemistry and Physiology. 50 (2): 115–128. doi:10.1006/pest.1994.1064.
^ US EPA (2000). "Decision Memorandum: Denial of Registration of Chlorfenapyr for Use on Cotton" (PDF). Retrieved 2006-07-28.
^ US EPA (2001). "Pesticide Fact Sheet: Chlorfenapyr" (PDF). Retrieved 2014-09-09.
^ Ingham, P. E.; McNeil, S. J.; Sunderland, M. R. (2012). "Functional finishes for wool – Eco considerations". Advanced Materials Research. 441: 33–43. doi:10.4028/www.scientific.net/AMR.441.33.
^ Fred Barbash (May 6, 2016). "31 people suddenly dropped dead in a Pakistani village. Now police claim to know the horrible reason why". Washington Post.