1.Recent advances of pyrethroids for household use.
Ujihara K1, Mori T, Matsuo N. Top Curr Chem. 2012;314:31-48. doi: 10.1007/128_2011_253.
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.
2.Stereoselective Production of (+)-trans-Chrysanthemic Acid by a Microbial Esterase: Cloning, Nucleotide Sequence, and Overexpression of the E
Nishizawa M, Shimizu M, Ohkawa H, Kanaoka M. Appl Environ Microbiol. 1996 Apr;62(4):1491.
Volume 61, no. 9, p. 3209, column 2, line 23: "L22165" should read "L22516." [This corrects the article on p. 3208 in vol. 61.].
3.The effectiveness of mosquito coils containing esbiothrin under laboratory and field conditions.
Birley MH1, Mutero CM, Turner IF, Chadwick PR. Ann Trop Med Parasitol. 1987 Apr;81(2):163-71.
Tests were made to correlate the chemical content of mosquito coils with the knockdown and bite-inhibitory action of the smoke in the laboratory and with the protective effect in field use. Smoke from a blank coil, containing no pyrethroid, gave no knockdown, 10% inhibition of biting in the laboratory using Aedes aegypti, and 39% protection in field tests in village huts on the Kenyan coast with a mixed population of mosquitoes including 71% Anopheles gambiae. Coils containing low experimental contents of 0.044% and 0.099% Esbiothrin, an isomer blend rich in the D-allethrolone ester of D-trans-chrysanthemic acid, gave rapid knockdown in both small chamber and 25 m3 room tests, and 71% and 94% inhibition of biting respectively in the laboratory. In the field they gave 74% and 84% protection from mosquitoes alighting. Chemical content was therefore a good guide to knockdown and bite inhibition in the laboratory and also to the considerable protection found in the field.
4.Characteristics and function of Alcaligenes sp. NBRC 14130 esterase catalysing the stereo-selective hydrolysis of ethyl chrysanthemate.
Mitsukura K1, Shimizu M, Matsushita K, Yoshida T, Nagasawa T. J Appl Microbiol. 2010 Apr;108(4):1263-70. doi: 10.1111/j.1365-2672.2009.04522.x. Epub 2009 Sep 13.
AIMS: Alcaligenes sp. NBRC 14130 was found as a strain hydrolysing a mixture of (+/-)-trans- and (+/-)-cis ethyl chrysanthemates to (1R,3R)-(+)-trans-chrysanthemic acid. The Alcaligenes cells also have hydrolytic activity for 6-aminohexanoate-cyclic dimer (6-AHCD, 1,8-diazacyclotetradecane-2,9-dione). The correlation of function on the enzyme from the Alcaligenes strain with hydrolysis activities for both ethyl chrysanthemate and 6-AHCD was demonstrated.