Resmethrin

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464381193 | Name = Resmethrin | ImageFile = Resmethrin v2.svg  | ImageName = | IUPACName = (5-benzylfuran-3-yl)methyl (2''R'')-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate; 5-benzyl-3-[({[(3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl) cyclopropyl]carbonyl}oxy)methyl]furan; (5-Benzyl-3-furyl)methyl-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropancarboxylate; 5-benzyl-3-furylmethyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; 5-benzyl-3-furylmethyl(1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; 5-benzyl-3-furylmethyl(±)-cis-trans-chrysanthemate | OtherNames = [5-(phenylmethyl)-3-furanyl]methyl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 19952179 | InChI = 1/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3/t19-,20?/m1/s1 | InChIKey = VEMKTZHHVJILDY-FIWHBWSRBD | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C22H26O3/c1-15(2)10-19-20(22(19,3)4)21(23)25-14-17-12-18(24-13-17)11-16-8-6-5-7-9-16/h5-10,12-13,19-20H,11,14H2,1-4H3/t19-,20?/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VEMKTZHHVJILDY-FIWHBWSRSA-N | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 2106605 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 10453-86-8 | CASNo1_Ref = {{cascite|correct|??}} | CASNo1 = 28434-01-7 | CASNo1_Comment = (Bioresmethrin) | ChEBI = 8811 | RTECS = GZ1310000 | UNNumber = 3082 3349 2902 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = Z6PN6KTG4K | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = YPP8YQZ13B | UNII1_Comment = (Bioresmethrin)

| PubChem = 5053 | EINECS = 233-940-7 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C10991 | SMILES = O=C(OCc2cc(Cc1ccccc1)oc2)C3[C@@H](/C=C(\C)C)C3(C)C }} | Section2 = {{Chembox Properties | Formula = C22H26O3 | MolarMass = 338.44 g/mol | Density = | MeltingPt = | BoilingPt = }} | Section6 = {{Chembox Pharmacology | Pharmacology_ref = | ATCCode_prefix = None | ATCCode_suffix = | ATC_Supplemental = | ATCvet = | Licence_EU = | INN = | INN_EMA = | Licence_US = | Legal_status = | Legal_AU = S6 | Legal_AU_comment = /{{nbsp}}Schedule 5<ref>{{cite web | title=Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025 | website=Therapeutic Goods Administration (TGA) | date=May 2025 | url=https://www.legislation.gov.au/F2025L00599/asmade/2025-05-28/text/original/pdf | format=pdf | access-date=31 August 2025}}</ref> | Legal_CA = | Legal_CA_comment = | Legal_NZ = | Legal_NZ_comment = | Legal_UK = | Legal_UK_comment = | Legal_US = | Legal_US_comment = | Legal_EU = | Legal_EU_comment = | Legal_UN = | Legal_UN_comment = | Pregnancy_category = | Pregnancy_AU = | Pregnancy_AU_comment = | Dependence_liability = | AdminRoutes = | Bioavail = | ProteinBound = | Metabolism = | Metabolites = | OnsetOfAction = | HalfLife = | DurationOfAction = | Excretion = }} |Section7={{Chembox Hazards | GHSPictograms = {{GHS07}}{{GHS09}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|302|410}} | PPhrases = {{P-phrases|264|270|273|301+312|330|391|501}} }} }}

'''Resmethrin''' is a pyrethroid insecticide with many uses, including control of the adult mosquito population.

The resmethrin molecule has four stereoisomers determined by cis-trans orientation around a carbon triangle and chirality. Technical resmethrin is a mixture of (1R,trans)-, (1R,cis)-, (1S,trans)-, and (1S,cis)- isomers, typically in a ratio of 4:1:4:1. The 1R isomers (both trans and cis) show strong insecticidal activity, while the 1S isomers do not. The (1R,trans)- isomer is also known as bioresmethrin,(+)-trans-resmethrin, or d-trans-resmethrin; although bioresmethrin has been used alone as a pesticide active ingredient, it is not now registered as a separate active ingredient (AI) by the U.S. EPA. The (1R,cis)- isomer is known as cismethrin, but this is also not registered in the U.S. for use alone as a pesticide AI.

Commercial trade names for products that contain resmethrin are: Chrysron, Crossfire, Lethalaire V-26, Pynosect, Raid Flying Insect Killer, Scourge, SPB-1382, Sun-Bugger #4, Synthrin, Syntox, Vectrin, and Whitmire PT-110.<ref>Pesticide Information Profiles, Extension Toxicology Network (EXTOXNET). [http://extoxnet.orst.edu/pips/resmethr.htm Resmethrin]</ref>

==References== {{reflist}}

==External links== *{{PPDB|585}} *[http://npic.orst.edu/factsheets/ResTech.pdf Resmethrin Technical Fact Sheet - National Pesticide Information Center] *[http://npic.orst.edu/factsheets/pyrethrins.pdf Pyrethrins and Pyrethroids Fact Sheet - National Pesticide Information Center] *[http://extoxnet.orst.edu/pips/resmethr.htm Resmethrin Pesticide Information Profile - Extension Toxicology Network] *[http://www.afpmb.org/pubs/standardlists/msds/6840-01-359-8533_msds.pdf MSDS] for Scourge Formula II *[http://www.inchem.org/documents/pds/pds/pest83_e.htm WHO/FAO DATA SHEETS ON PESTICIDES, No. 83, RESMETHRIN World Health Organization & Food and Agriculture Organization] {{Webarchive|url=https://web.archive.org/web/20110609010311/http://www.inchem.org/documents/pds/pds/pest83_e.htm |date=2011-06-09 }} *[https://web.archive.org/web/20061006094139/http://www.epa.gov/oppsrrd1/REDs/resmethrin_red.pdf Reregistration Eligibility Decision for Resmethrin (2006) - U.S. Environmental Protection Agency]

Category:Furans Category:Benzyl compounds Category:Chrysanthemate esters Category:Cyclopropanes