Resmethrin

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title: "Resmethrin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["furans", "benzyl-compounds", "chrysanthemate-esters", "cyclopropanes"] topic_path: "general/furans" source: "https://en.wikipedia.org/wiki/Resmethrin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464381193 | Name = Resmethrin | ImageFile = Resmethrin v2.svg | ImageName = | IUPACName = (5-benzylfuran-3-yl)methyl (2R)-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 = | 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 = | 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 = | StdInChIKey = VEMKTZHHVJILDY-FIWHBWSRSA-N | ChEMBL_Ref = | ChEMBL = 2106605 | CASNo_Ref = | CASNo = 10453-86-8 | CASNo1_Ref = | CASNo1 = 28434-01-7 | CASNo1_Comment = (Bioresmethrin) | ChEBI = 8811 | RTECS = GZ1310000 | UNNumber = 3082 3349 2902 | UNII_Ref = | UNII = Z6PN6KTG4K | UNII1_Ref = | UNII1 = YPP8YQZ13B | UNII1_Comment = (Bioresmethrin)

| PubChem = 5053 | EINECS = 233-940-7 | KEGG_Ref = | KEGG = C10991 | SMILES = O=C(OCc2cc(Cc1ccccc1)oc2)C3C@@HC3(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 = /Schedule 5 | 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 = | GHSSignalWord = Warning | HPhrases = | PPhrases =

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.

References

References

  1. (May 2025). "Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025".
  2. Pesticide Information Profiles, Extension Toxicology Network (EXTOXNET). [http://extoxnet.orst.edu/pips/resmethr.htm Resmethrin]

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furansbenzyl-compoundschrysanthemate-esterscyclopropanes