Chlorfenapyr

Chlorfenapyr
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
4-Bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.116.332 Edit this at Wikidata
EC Number
  • 602-782-4
KEGG
UNII
  • 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
  • Clc2ccc(c1c(C#N)c(Br)c(n1COCC)C(F)(F)F)cc2
Properties
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:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H320, H331, H371, H373, H410
P260, 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).

Chlorfenapyr is an insecticide, and specifically a pro-insecticide (meaning it is metabolized into an active insecticide after entering the host).

History, applications and toxicity

Chlorfenapyr was developed by American Cyanamid from the natural bacterial toxin dioxapyrrolomycin, which was first isolated from Streptomyces fumanus.

The United States Environmental Protection Agency initially denied registration in 2000 for use on cotton primarily because of concerns that the insecticide was very toxic to birds and because effective alternatives were available. However, it was registered by the EPA in January, 2001 for use on non-food crops in greenhouses. 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.

In April 2016, in Pakistan, 33 people died following the deliberate contamination of a batch of laddu with chlorfenapyr.

Mode of Action

Oxidative removal of the N-ethoxymethyl group of chlorfenapyr by mixed function oxidases forms a compound known as Tralopyril or CL 303268. This active metabolite uncouples oxidative phosphorylation at the mitochondria, resulting in disruption of production of ATP, cellular death, and ultimately organism mortality.


Chlorfenapyr is in IRAC group 13.

Notes

  1. 1 2 Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "32.2 Inhibitors of Oxidative Phosphorylation via Disruption of the Proton Gradient". Modern Crop Protection Compounds (3rd ed.). Wiley-VCH. pp. 1149–1155. doi:10.1002/9783527699261. ISBN 9783527699261.
  2. ↑ 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. Bibcode:1994PBioP..50..115B. doi:10.1006/pest.1994.1064.
  3. ↑ US EPA (2000). "Decision Memorandum: Denial of Registration of Chlorfenapyr for Use on Cotton" (PDF). Retrieved 2006-07-28.[dead link]
  4. ↑ US EPA (2001). "Pesticide Fact Sheet: Chlorfenapyr" (PDF). Retrieved 2014-09-09.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Agence France-Presse (1 May 2016). "Mass Food Poisoning Kills 33 Including 5 Children In Pakistan's Multan". NDTV. Archived from the original on 21 September 2019. Retrieved 2 May 2016.