以蚜虫报警信息素[(E)-β-farnesene,EBF]为先导,通过活性亚结构拼接和生物电子等排原理,设计合成了一系列结构新颖的异烟酸类EBF类似物.以香叶醇为原料,经4步反应制得20个目标化合物(19个未见文献报道),其结构经1H NMR,13C NMR,IR及HRMS确证.初步生物活性测定结果表明,所有化合物对桃蚜有驱避活性和杀死活性,其中化合物7d,8f和8n表现出较好的桃蚜驱避活性,对桃蚜的驱避率分别为62.6%,62.0%和61.0%;化合物8a,8b和8d对桃蚜的致死率分别为73.6%,81.1%和70.2%.初步构效关系分析发现,酯基的引入对桃蚜的驱避活性有利;酰胺基的引入对杀蚜活性有利;N烷基取代的链长及支链数量影响驱避活性.
A series of new aphid alarm pheromone[( E)-β-farnesene,EBF]analogues containing isonicotinic acid was designed based on the principles of connecting sub-structure and bioisosterism. With EBF as a lead compound,20 EBF analogues were prepared via four steps starting from geraniol. Their structures were confirmed by 1 H NMR,(3C NMR,IR and HRMS. The preliminary bioassay suggested that all the analogues showed repellent and aphicidal activities against Myzus persicae( Sulzer). Among them,compounds 7d,8f and8 n showed good repellent activity with the repellent rate of 62. 6%,62. 0% and 61. 0% respectively; and the analogues 8a,8b and 8d exhibited better aphicidal mortality of 73. 6%,81. 1% and 70. 2% than lead EBF.The primary structure-activity relationship( SAR) analysis indicated that introducing of ester group was favorable to repellent activity while introducing amide was conducive to aphicidal activity. Moreover,N-substituted carbon chain length,number of branched chain as well as aromaticity played roles in repellent activity. This study provides useful clues for further development of novel aphid control agent.