ISOLATION, IDENTIFICATION, AND SYNTHESIS OF THE SEX PHEROMONE OF THE TOBACCO BUDWORM

被引:132
作者
Tumlinson, J. H. [1 ]
Hendricks, D. E. [2 ]
Mitchell, E. R. [1 ]
Doolittle, R. E. [1 ]
Brennan, M. M. [1 ]
机构
[1] USDA ARS, Insect Attractants Behav & Basic Biol Res Lab, Gainesville, FL 32604 USA
[2] USDA ARS, Cotton Insects Res Lab, Brownsville, TX 78520 USA
关键词
sex pheromone; Heliothis virescens (F.); (Z)-11-hexadecenal; (Z)-9-tetradecenal;
D O I
10.1007/BF00987869
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The sex attractant of adult tobacco budworms, Heliothis virescens (F.) was isolated from ether washes of "calling" females and verified as active by field cage bioassays. The components of the pheromone were identified as (Z)-11-hexadecenal and (Z)-9-tetradecenal by spectroscopic and microdegradative methods. The two components are inactive when tested separately, but when they are mixed in the ratio in which they occur in female washes (16: 1, respectively), the synthesized mixture is equivalent to the natural one in attracting males in large cages. In field tests, 53 mu g of synthesized mixture was competitive with four live females.
引用
收藏
页码:203 / 214
页数:12
相关论文
共 19 条
[1]   A SYNTHESIS OF CIS-11-OCTADECENOIC AND TRANS-11-OCTADECENOIC (VACCENIC) ACIDS [J].
AHMAD, K ;
BUMPUS, FM ;
STRONG, FM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (10) :3391-3394
[2]   SEX ATTRACTANTS OF HELIOTHIS ZEA AND H VIRESCENS [J].
BERGER, RS ;
MCGOUGH, JM ;
MARTIN, DF .
JOURNAL OF ECONOMIC ENTOMOLOGY, 1965, 58 (05) :1023-&
[3]   RAPID DETERMINATION OF OLEFIN POSITION IN ORGANIC COMPOUNDS IN MICROGRAM RANGE BY OZONOLYSIS AND GAS CHROMATOGRAPHY [J].
BEROZA, M ;
BIERL, BA .
ANALYTICAL CHEMISTRY, 1967, 39 (10) :1131-&
[4]   APPARATUS FOR OZONOLYSIS OF MICROGRAM TO MILLIGRAM AMOUNTS OF COMPOUND [J].
BEROZA, M ;
BIERL, BA .
ANALYTICAL CHEMISTRY, 1966, 38 (13) :1976-&
[5]  
BEROZA M., 1966, ANAL CHEM, V38, P1042
[6]  
GASTON LYLE K., 1964, ANN ENTOMOL SOC AMER, V57, P779, DOI 10.1093/aesa/57.6.779
[7]   SEX ATTRACTANT IN TOBACCO BUDWORM [J].
GENTRY, CR ;
LAWSON, FR ;
HOFFMAN, JD .
JOURNAL OF ECONOMIC ENTOMOLOGY, 1964, 57 (06) :819-&
[8]   FIELD CAGE BIOASSAY SYSTEM FOR TESTING CANDIDATE SEX-PHEROMONES OF TOBACCO BUDWORM [J].
HENDRICK.DE ;
TUMLINSO.JH .
ANNALS OF THE ENTOMOLOGICAL SOCIETY OF AMERICA, 1974, 67 (04) :547-552
[9]  
HENDRICKS D E, 1973, Environmental Entomology, V2, P911, DOI 10.1093/ee/2.5.911
[10]   THE OXIDATION OF UNSATURATED ACETALS AND ACYLALS WITH PERACETIC ACID [J].
HEYWOOD, DL ;
PHILLIPS, B .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (10) :1699-1703