Mitsubishi-Kasei Institute of Life Sciences, 11 Minamiooya, Machida-shi, 194, Tokyo, Japan.
J Chem Ecol. 1983 Mar;9(3):433-48. doi: 10.1007/BF00988460.
Many compounds related to (+)-bornyl acetate (a sex phero-mone mimic of the American cockroach) were synthesized and tested for sex pheromonal activity. All compounds except for esters of (+)- and (-)-borneol were inactive, whereas (+)-bornyl acetate (Ib) and propionate (Ic) showed the activity at 0.05 mg. Although (-)-bornyl propionate (IVc) is the enantiomer of Ic, it exhibited weak activity at 0.5 mg dose. On the basis of the behavioral assay results, important chemical factors in Ib for pheromonal activity were elucidated and are discussed in connection with another mimic, (+)-trans-verbenyl acetate. The M/ F ratio index in EAG was evaluated for both active and inactive compounds. The index demonstrated a good correlation with the behavioral activity.
许多与(+)-莰烯乙酸酯(美洲大蠊性信息素类似物)相关的化合物被合成并测试了其性信息素活性。除了(+)-和(-)-龙脑醇的酯之外,所有化合物均没有活性,而(+)-莰烯乙酸酯(Ib)和丙酸酯(Ic)在 0.05mg 时表现出活性。尽管(-)-莰烯丙酸酯(IVc)是 Ic 的对映异构体,但在 0.5mg 剂量时表现出较弱的活性。基于行为测定结果,阐明了 Ib 中对信息素活性很重要的化学因素,并与另一种类似物(+)-反式马鞭烯醇乙酸酯进行了讨论。EAG 中对活性和非活性化合物进行了 M/F 比值指数评估。该指数与行为活性有很好的相关性。