Development of pyrethroids for household use and recent advances in the syntheses of (1R)-trans-chrysanthemic acid, the acid moiety of most of the household pyrethroids, are reviewed. As another important acid moiety, we discovered norchrysanthemic acid to have a significant vapor action at room temperature when esterified with fluorobenzyl alcohols. In particular, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R)-trans-norchrysanthemate (metofluthrin) exhibits the highest potency in mosquito coil formulations as well as the vapor action at room temperature against various mosquitoes. Structure-activity relationships of norchrysanthemic acid esters and synthetic studies of norchrysanthemic acid are discussed.
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http://dx.doi.org/10.1007/128_2011_253 | DOI Listing |
Top Curr Chem
March 2012
Sumitomo Chemical Co., Ltd, Takarazuka, Hyogo, Japan.
Development of pyrethroids for household use and recent advances in the syntheses of (1R)-trans-chrysanthemic acid, the acid moiety of most of the household pyrethroids, are reviewed. As another important acid moiety, we discovered norchrysanthemic acid to have a significant vapor action at room temperature when esterified with fluorobenzyl alcohols. In particular, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R)-trans-norchrysanthemate (metofluthrin) exhibits the highest potency in mosquito coil formulations as well as the vapor action at room temperature against various mosquitoes.
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January 2004
Agricultural Chemicals Research Laboratory, Sumitomo Chemical Co., Ltd, Hyogo, Japan.
(1R)-trans-Norchrysanthemic acid fluorobenzyl esters are synthesized and their structure-activity relationships are discussed. These esters show outstanding insecticidal activity against mosquitoes. In particular, the 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl analog (metofluthrin) exhibits the highest potency, being approximately forty times as potent as d-allethrin in a mosquito coil formulation when tested against southern house mosquitoes (Culex quinquefasciatus).
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