Wimmer Zdenek, Kuldová Jelena, Hrdý Ivan, Bennettová Blanka
Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo námestí 2, CZ-16610 Prague 6, Czech Republic.
Insect Biochem Mol Biol. 2006 Jun;36(6):442-53. doi: 10.1016/j.ibmb.2006.03.006. Epub 2006 Mar 30.
Two different types of juvenogens, biochemically targeted hormonogen compounds were tested for their potency to act as insect pest management agents. In the performed biological screening, wax-like esteric juvenogens (3-10) proved to be convenient agents for controlling blowfly and termites, and displayed species selectivity: cis-N-{2-[4-(2-butanoyloxycyclohexyl)methyl]phenoxy}ethyl carbamate (3) was highly active on blowfly (Neobellieria bullata), while trans-N-{2-[4-(2-hexadecanoyloxycyclohexyl)methyl]-phenoxy}ethyl carbamate (6) showed high activity on termite (Prorhinotermes simplex). Glycosidic juvenogens, isomeric N-{2-{4-{[2-(beta-D-galactopyranosyloxy)cyclohexyl]methyl}phenoxy}ethyl carbamates (13 and 14), were proved to act as systemic agents, suitable for protecting plants against phytophagous insects (e.g. aphids). Due to the prolonged action of juvenogens, which is connected with the sequential liberating of the biologically active molecule of the insect juvenile hormone bioanalog from the juvenogen molecule by means of enzymic systems of target insects and/or their host plants, more insect individuals can be treated by juvenogens, which are species-targeted structures due to their different physicochemical properties. The results achieved with both types of juvenogens were promising, concerning their final effect on the tested insect species, and the compounds 3-6, 9 (cis-(9Z)-N-{2-[4-(2-(octadec-9-enoyl)oxycyclohexyl)methyl]phenoxy}ethyl carbamate), 13 and 14 proved to represent convenient insect pest management agents for potential practical applications against different insect pests.
对两种不同类型的保幼激素,即生化靶向激素原化合物,进行了作为害虫治理剂的效能测试。在进行的生物筛选中,蜡状酯类保幼激素(3 - 10)被证明是控制绿头苍蝇和白蚁的便捷药剂,并表现出物种选择性:顺式 - N - {2 - [4 - (2 - 丁酰氧基环己基)甲基]苯氧基}乙基氨基甲酸酯(3)对绿头苍蝇(新钟蝇)具有高活性,而反式 - N - {2 - [4 - (2 - 十六酰氧基环己基)甲基]苯氧基}乙基氨基甲酸酯(6)对白蚁(简单原鼻白蚁)表现出高活性。糖苷类保幼激素,即异构的N - {2 - {4 - {[2 - (β - D - 吡喃半乳糖氧基)环己基]甲基}苯氧基}乙基氨基甲酸酯(13和14),被证明可作为内吸性药剂,适用于保护植物免受植食性昆虫(如蚜虫)侵害。由于保幼激素的作用持久,这与通过目标昆虫和/或其寄主植物的酶系统从保幼激素分子中依次释放昆虫保幼激素类似物的生物活性分子有关,保幼激素作为具有不同物理化学性质的物种靶向结构,可以处理更多的昆虫个体。就这两种类型的保幼激素对测试昆虫物种的最终效果而言,所取得的结果很有前景,化合物3 - 6、9(顺式 - (9Z) - N - {2 - [4 - (2 - (十八碳 - 9 - 烯酰)氧基环己基)甲基]苯氧基}乙基氨基甲酸酯)、13和14被证明是针对不同害虫的潜在实际应用的便捷害虫治理剂。