Fenpropathrin

Fenpropathrin
Clinical data
ATC code
  • None
Identifiers
  • [Cyano-(3-phenoxyphenyl)methyl] 2,2,3,3-tetramethylcyclopropane-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.049.514 Edit this at Wikidata
Chemical and physical data
FormulaC22H23NO3
Molar mass349.430 g·mol−1
3D model (JSmol)
  • CC1(C(C1(C)C)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C
  • InChI=InChI=1S/C22H23NO3/c1-21(2)19(22(21,3)4)20(24)26-18(14-23)15-9-8-12-17(13-15)25-16-10-6-5-7-11-16/h5-13,18-19H,1-4H3
  • Key:XQUXKZZNEFRCAW-UHFFFAOYSA-N

Fenpropathrin, or fenopropathrin, is a widely used pyrethroid insecticide in agriculture and household.[1][2][3][4] Fenpropathrin is an ingestion and contact synthetic pyrethroid. Its mode of action is similar to other natural (pyrethrum) and synthetic pyrethroids where in they interfere with the kinetics of voltage gated sodium channels causing paralysis and death of the pest.[5] Fenpropathrin was the first of the light-stable synthetic pyrethroids to be synthesized in 1971, but it was not commercialized until 1980.[6] Like other pyrethroids with an α-cyano group, fenpropathrin also belongs to the termed type II pyrethroids (e.g. cyfluthrin, cyhalothrin, cypermethrin, deltamethrin and esfenvalerate).[7] Type II pyrethroids are a more potent toxicant than type I in depolarizing insect nerves.[8] Application rates of fenpropathrin in agriculture according to US environmental protection agency (EPA) varies by crop but is not to exceed 0.4 lb ai/acre.

  1. ^ Aizawa H (2 December 2012). Metabolic Maps of Pesticides. Elsevier Science. pp. 185–. ISBN 978-0-323-15753-7.
  2. ^ Abou-Donia MB (15 July 1992). Neurotoxicology. CRC Press. pp. 462–. ISBN 978-1-4398-0542-8.
  3. ^ Johansen CA, Mayer DF (1990). Pollinator Protection: A Bee & Pesticide Handbook. Wicwas Press. ISBN 978-1-878075-00-0.
  4. ^ Xiong J, Zhang X, Huang J, Chen C, Chen Z, Liu L, et al. (March 2016). "Fenpropathrin, a Widely Used Pesticide, Causes Dopaminergic Degeneration". Molecular Neurobiology. 53 (2): 995–1008. doi:10.1007/s12035-014-9057-2. PMC 5333774. PMID 25575680.
  5. ^ Pfeil R (2014). "Pesticide Residues: Pyrethroids". Encyclopedia of Food Safety. Elsevier. pp. 31–34. doi:10.1016/B978-0-12-378612-8.00239-0. ISBN 978-0-12-378613-5.
  6. ^ Holan G, Frelin C, Lazdunski M (1985). "Selectivity of action between pyrethroids and combined DDT-pyrethroid insecticides on Na+ influx into mammalian neuroblastoma". Experientia. 41 (4): 520–522. doi:10.1007/bf01966180. ISSN 0014-4754. S2CID 11286824.
  7. ^ Pesticide residues in food, 1993 : evaluations, 1993. Part II, Toxicology. World Health Organization, International Program on Chemical Safety. Geneva, Switzerland: World Health Organization. 1994. ISBN 92-4-166509-2. OCLC 31097583.{{cite book}}: CS1 maint: others (link)
  8. ^ Salgado VL, Irving SN, Miller TA (1983). "The importance of nerve terminal depolarization in pyrethroid poisoning of insects". Pesticide Biochemistry and Physiology. 20 (2): 169–182. Bibcode:1983PBioP..20..169S. doi:10.1016/0048-3575(83)90021-4.