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Revision as of 14:41, 15 April 2014 editKathy.lewis180455 (talk | contribs)189 editsm External links← Previous edit Revision as of 12:29, 20 June 2014 edit undoLouisajb (talk | contribs)Extended confirmed users4,402 edits added chemblidNext edit →
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VEMKTZHHVJILDY-FIWHBWSRSA-N | StdInChIKey = VEMKTZHHVJILDY-FIWHBWSRSA-N
| ChEMBL = 2106605
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 10453-86-8 | CASNo = 10453-86-8

Revision as of 12:29, 20 June 2014

Resmethrin
Names
IUPAC name 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)cyclopropancarboxylat; 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 methyl 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.030.842 Edit this at Wikidata
KEGG
CompTox Dashboard (EPA)
InChI
  • InChI=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/s1Key: VEMKTZHHVJILDY-FIWHBWSRSA-N
  • 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/s1Key: VEMKTZHHVJILDY-FIWHBWSRBD
SMILES
  • O=C(OCc2cc(Cc1ccccc1)oc2)C3(/C=C(\C)C)C3(C)C
Properties
Chemical formula C22H26O3
Molar mass 338.44 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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)-, (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, Pynosect, Raid Flying Insect Killer, Scourge, Sun-Bugger #4, SPB-1382, Synthrin, Syntox, Vectrin and Whitmire PT-110.

References

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

External links

Pest control: Insecticides
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
Categories: