Rothamsted Research, Harpenden, Hertfordshire AL5 2JQ, United Kingdom.
J Agric Food Chem. 2011 Apr 13;59(7):2770-2. doi: 10.1021/jf102256s. Epub 2010 Sep 14.
Replacement of the pyrethronyl alcohol portion of the natural pyrethrins with the 5-benzyl-3-furylmethyl moiety gave bioresmethrin, a synthetic pyrethroid of high potency and safety but with limited photostability. Introduction of novel substituents at the 3-position of the cyclopropane ring then led to the discovery of insecticidally active compounds with greatly improved potency. Systematic changes of both the alcohol and acid components gave second-generation pyrethroids (permethrin, cypermethrin, and deltamethrin) with improved potency and photostability suitable for agricultural use. Metabolic studies showed that the photostabilized compounds remained biodegradable. Deltamethrin, discovered in 1974, was the cream of the crop and remains 36 years later as one of the most important synthetic pyrethroid insecticides.
用 5-苄基-3-呋喃甲基取代天然除虫菊酯中的醇部分得到生物丙烯菊酯，这是一种高效、安全但光稳定性有限的合成拟除虫菊酯。然后在环丙烷环的 3-位引入新型取代基，发现了具有大大提高杀虫活性的化合物。对醇和酸部分进行系统的改变，得到了具有更高杀虫活性和光稳定性的第二代拟除虫菊酯（氯菊酯、氯氰菊酯和溴氰菊酯），适合农业使用。代谢研究表明，光稳定化合物仍可生物降解。1974 年发现的溴氰菊酯是其中的佼佼者，36 年后仍然是最重要的合成拟除虫菊酯杀虫剂之一。
