Resmethrin

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

Resmethrin
Names
IUPAC names
(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
Other names
[5-(phenylmethyl)-3-furanyl]methyl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.030.842
EC Number
  • 233-940-7
KEGG
RTECS number
  • GZ1310000
UNII
UN number 3082 3349 2902
Properties
C22H26O3
Molar mass 338.44 g/mol
Hazards
GHS pictograms
GHS Signal word Warning
H302, H400, H410
P264, P270, P273, P301+312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1]

References
  1. Pesticide Information Profiles, Extension Toxicology Network (EXTOXNET). Resmethrin
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