摘要
以松节油中的主要组分α-蒎烯和β-蒎烯为原料,合成17个具有六元环的萜类蚂蚁驱避剂。采用荞麦种子浸液选择性生测法测定了它们对小黄家蚁的驱避效果。结果表明,这些化合物都具有一定的驱避活性,其中8-羟基别二氢葛缕醇丙酸酯(4)、诺卜甲基醚(9)、乙酸诺卜酯(13)和内型1-异莰烷基-3-己醇乙酸酯(17)表现出良好的驱避活性。使用量子化学计算软件Gaussian 03W对这些化合物进行几何优化,并计算出驱避剂分子的最低能量,再通过半经验量子力学程序Ampac 8.16进行格式转变后导入程序Codessa 2.7.10,继而计算结构描述符,并通过启发式方法对这些驱蚁剂的定量构效关系进行计算,得到了对应于驱避率对数值(lgB)和R2值为0.926 5的最佳定量构效关系计算模型。该模型显示,对这些萜类驱蚁剂活性具有较大影响的4个结构描述符分别是分数原子正电荷加权部分表面积、碳原子的最小亲核反应指数、次高占用分子轨道能量、氧原子的最大单电子反应指数。
Seventeen terpenoid ant repellents with six-member-ring were synthesized from α-pinene and β-pinene, which are two main components of turpentine oil. Their repellency against Monomorium pharaonis Linn. was determined using the method of dual-choice bioassay with steeped grain. The result shows that all these compounds have repellency, in which 8-hydroxylcarveol propionate, nopyl methyl ether, nopyl acetate and endo-1-isocamphanyl-3-hexanol acetate have good repellency. Furthermore, the optimal conformer and lowest energy of these compounds were calculated using Gaussian 03W, then the results were changed into the format compatible with Codessa 2.7. 10 using Ampac 8. 16. Finally, the changed results were loaded and the structure descriptors were calculated in Codessa 2.7.10, and the quantitative structure-activity relationship was calculated by heuristic method in Codessa 2.7. I0. The quantitative structure-activity relationship model using lg B as activity was gained with the R^2 =0.926 5. The model suggests that the g structure descriptors influencing the repellency include ： fractional atomic charge weighted partial positive surface area（ ESP-FPSA-3 fractional PPSA）, minimum nucleophilic reactivity index of a carbon atom, secondhighest occupied molecular orbital（ HOMO-1 ）energy, maximum 1-electron reactivity index for an oxygen atom.
出处
《林产化学与工业》
EI
CAS
CSCD
北大核心
2009年第B10期47-53,共7页
Chemistry and Industry of Forest Products
基金
国家自然科学基金资助项目(30860223)
霍英东高等院校青年教师基金资助项目(101031)
江西省自然科学基金资助项目(2007GZN0262)
江西省教育厅资助项目([2007]148)
关键词
小黄家蚁
萜类蚂蚁驱避剂
驱避活性
定量构效关系
Monomorium pharaonis
terpenoid ant repellent
repellency
quantitative structure-activity relationship
