Fenpropathrin

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [Cyano-(3-phenoxyphenyl)methyl] 2,2,3,3-tetramethylcyclopropane-1-carboxylate

| image = Fenpropathrin.svg

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| CAS_number_Ref =

| CAS_number = 39515-41-8

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| ATC_prefix = None

| ATC_suffix =

| PubChem = 47326

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID_Ref =

| ChemSpiderID = 45352

| UNII = 87BH96P0MX

| KEGG = C18411

| C=22 | H=23 | N=1 | O=3

| smiles = CC1(C(C1(C)C)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = XQUXKZZNEFRCAW-UHFFFAOYSA-N

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}}

Fenpropathrin, or fenopropathrin, is a widely used pyrethroid insecticide in agriculture and household.{{cite book | vauthors = Aizawa H |title=Metabolic Maps of Pesticides|url=https://books.google.com/books?id=Cnv3hTkZyo0C&pg=PA185|date=2 December 2012|publisher=Elsevier Science|isbn=978-0-323-15753-7|pages=185–}}{{cite book | vauthors = Abou-Donia MB |title=Neurotoxicology|url=https://books.google.com/books?id=CBZ8An2koJkC&pg=PA462|date=15 July 1992|publisher=CRC Press|isbn=978-1-4398-0542-8|pages=462–}}{{cite book | vauthors = Johansen CA, Mayer DF |title=Pollinator Protection: A Bee & Pesticide Handbook|url=https://books.google.com/books?id=UutJAAAAYAAJ|year=1990|publisher=Wicwas Press|isbn=978-1-878075-00-0}}{{cite journal | vauthors = Xiong J, Zhang X, Huang J, Chen C, Chen Z, Liu L, Zhang G, Yang J, Zhang Z, Zhang Z, Lin Z, Xiong N, Wang T | display-authors = 6 | title = Fenpropathrin, a Widely Used Pesticide, Causes Dopaminergic Degeneration | journal = Molecular Neurobiology | volume = 53 | issue = 2 | pages = 995–1008 | date = March 2016 | pmid = 25575680 | pmc = 5333774 | doi = 10.1007/s12035-014-9057-2 }} 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.{{cite book | vauthors = Pfeil R | chapter =Pesticide Residues: Pyrethroids|date=2014 | title =Encyclopedia of Food Safety|pages=31–34|publisher=Elsevier|language=en|doi= 10.1016/B978-0-12-378612-8.00239-0|isbn=978-0-12-378613-5 }} Fenpropathrin was the first of the light-stable synthetic pyrethroids to be synthesized in 1971, but it was not commercialized until 1980.{{cite journal| vauthors = Holan G, Frelin C, Lazdunski M |date=1985|title=Selectivity of action between pyrethroids and combined DDT-pyrethroid insecticides on Na+ influx into mammalian neuroblastoma |journal=Experientia|volume=41|issue=4|pages=520–522|doi=10.1007/bf01966180|s2cid=11286824|issn=0014-4754}} 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).{{cite book|url=https://www.worldcat.org/oclc/31097583|title=Pesticide residues in food, 1993 : evaluations, 1993. Part II, Toxicology|date=1994|publisher=World Health Organization|others=World Health Organization, International Program on Chemical Safety|isbn=92-4-166509-2|location=Geneva, Switzerland|oclc=31097583}} Type II pyrethroids are a more potent toxicant than type I in depolarizing insect nerves.{{cite journal| vauthors = Salgado VL, Irving SN, Miller TA |date=1983|title=The importance of nerve terminal depolarization in pyrethroid poisoning of insects |journal=Pesticide Biochemistry and Physiology|language=en|volume=20|issue=2|pages=169–182|doi=10.1016/0048-3575(83)90021-4|bibcode=1983PBioP..20..169S }} 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/[https://www3.epa.gov/pesticides/chem_search/ppls/059639-00035-20170919.pdf acre].