SEX-PHEROMONE OF THE PINE SAWFLY DIPRION PINI (HYMENOPTERA, DIPRIONIDAE) - CHEMICAL-IDENTIFICATION, SYNTHESIS AND BIOLOGICAL-ACTIVITY

被引:50
作者
BERGSTROM, G
WASSGREN, AB
ANDERBRANT, O
FAGERHAG, J
EDLUND, H
HEDENSTROM, E
HOGBERG, HE
GERI, C
AUGER, MA
VARAMA, M
HANSSON, BS
LOFQVIST, J
机构
[1] LUND UNIV,DEPT ECOL,S-22362 LUND,SWEDEN
[2] MID SWEDEN UNIV,DEPT SCI & ENGN,S-85170 SUNDSVALL,SWEDEN
[3] CTR RECH ORLEANS,INRA,F-45160 OLIVET,FRANCE
[4] FINNISH FOREST RES INST,SF-01301 VANTAA,FINLAND
[5] SWEDISH UNIV AGR SCI,DEPT PLANT PROTECT SCI,S-23053 ALNARP,SWEDEN
来源
EXPERIENTIA | 1995年 / 51卷 / 04期
关键词
DIPRION PINI; SEMIOCHEMICALS; SEX ATTRACTANT; 3,7-DIMETHYL-7-TRIDECANOL; CHIRAL SYNTHESIS; LIPASE; CHIRAL ANALYSIS;
D O I
10.1007/BF01928898
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (> 99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R) -3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a nonchiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 mu g of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 mu g in France and 50 mu g in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.
引用
收藏
页码:370 / 380
页数:11
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