Major sex pheromone components of the

Gries, G., Gries, R., Underhill, E. W. and Humble, L. (1993). (6Z,9Z-3R,45)-Epoxy-heptadecadiene major sex pheromone component of the larch looper, Semiothisa sexmaculata (Packard) (Lepidoptera Geometridae). J. Chem. Ecol., 19, 843-850. 

The occurrence of hydrocarbons (usually mono- and di-alkenes) with an epoxide function group have been reported usually as sex attractants. The sex attractant of the female gypsy moth, Lymantria dispar, was identified as the C18 2-methyl alkane derivative cis-7,S-epoxy-2-methyloctadecane (Bierl et al 1972). For the housefly, M. domestica, a major sex pheromone component is the C23 -alkane epoxide d.v-9,1O-cpoxytricosane (Uebel et al 1978) with a lesser quantity of 9,10-epoxyheptacosane (Mpuru et al., 2001). 

Becker, D., Cyjon, R., Cosse, A., Moore, I., Kimmel, T. and Wysoki, M. (1990). Identification and enantioselective synthesis of (Z,Z),6,9-cis-3S,4R-epoxynonadecadiene, the major sex pheromone component of Boarmia selenaria. Tetrahedron Lett., 31,4923 4926. 

M., Toshova, T., Pickett, J.A., Wadhams, L. J. and Woodcock, C.M. (2000). Major sex pheromone component of female herald moth Scoliopteryx libatrix is the novel branched alkene (6Z)-13-methylheneicoscne../. Chem. Ecol., 26, 1135-1149. 

Males of the scarab beede Amphimatton solstitialis are attracted to the pheromone (/ )-3-hydro.xy-2-butanone (A62), released by both males and females.368 Although the ( -enantiomer and 2,3-butanediol (A4) are also produced, they were not active in the field. 3-Hydroxy-2-butanone of unknown enantiomeric composition is the major sex pheromone component of male cockroach Leucophaea mademe2m The rhinoceros beetle Scapanes australis uses a 84 12 4 mixture of 2-butanol (A61) (R/S 67 33), 3-hydroxy-2-butanone (A62), and 2,3-butanediol (A4, RJl/S,S/meso 43 17 40), whereas the pheromone of another rhinoceros beetle Strategus aloeus is a 95.5 4.0 0.5 mixture of2-butanone (A63), 3-pentanone (A66), and 1-methylpropyl acetate (A64). As mixtures of all components of the natural secretion were used in this study, it is not clear whether all compounds really possess pheromonal activity.369... 

Decane is an alarm pheromone of the ant C. obscuripes866 Decanal (A95) is a pheromone component of larvae of C. pomonella (see Section 4.04.5.3.7),382 and is used by the red bug C. lectularius as an aggregation pheromone component.193 Males of a long-horned beetle, the coffee white stem borer Xylotrechus quadripes, a serious coffee pest in India, produce (S)-2-hydroxy-3-decanone (A96) as sex pheromone to attract female beetles.393 9-Oxo- (A97) and 9-hydroxydecanoic acid (A98) are the major sex pheromone components of females of the scoliid wasp Campsoscolia ciliata. Interestingly, the orchid Ophrys speculum also produces these compounds to attract males of Campsoscolia for pollination.394 ( )-4-Decanolide (A99)... 

The major sex pheromone component of Drosophila ananassae and D. pallidosa, (Z,Z)-5,25-hentriacondiene 16 and (Z,Z)-5,27-tritriacontadiene 17, respectively, have been synthesized by applying sulfone alkylation and subsequent Sml2-induced reductive removal of the benzenesulfonyl moiety (Scheme 22.5). ... 

Morita A, Matsuyama S, Oguma Y, Kuwahara S. Simple synthesis of the major sex pheromone components of Drosophila ananassae and D-paUidosa. Biosci. Biotechnol. Biochem. 2005 69(8) 1620-1623. 

Gemeno, C., Yeargan, . V. and Haynes, K. F. (2000). Aggressive chemical mimicry by the bolas spider Mastophora hutchinsoni identification and quantification of a major prey s sex pheromone components in the spider s volatile emissions. Journal of Chemical Ecology 26 1235-1243. 

Grapholitha molesta (22). Females of this species emit (Zj-8-dodecenyl acetate as a major sex pheromone component, along with a synercjist, dodecyl alcohol (23). Addition of the (E)-isomer of 8-dodecenyl acetate increased male catches about 25-fold maximum attractiveness occurred with about 8% of this isomer. 

Drugstore beetle (Stegobium paniceum) is a serious pest of a wide variety of commodities and stored products. In 1978 Y. Kuwahara et al. proposed the structure of stegobinone, the major and crystalline component of the female-produced sex pheromone of 5. paniceum, as 114 (Figure 4.69). Nothing was... 

Ac [34010-21-4]. Major component of the sex pheromone of the bertha armyworm (Mamestra configure at a) female sex pheromone of the purple stem borer moth (Sesamia inferens) and rice green caterpillar (Natanga aenescens) sex pheromone component of diamond back moth and cabbage armyworm moth (Ma-mestra brassicae).Bpo.i 108°. 

Axons of male-specific antennal ORCs specialized to detect components of the sex pheromone project exclusively to the MGC (64, 89), and all AL neurons that respond to antennal stimulation with sex pheromone components have arborizations in the MGC (65, 72, 73). The MGC in M. sexta has two major, easily distinguishable divisions a donut-shaped neuropil structure (the "toroid") and a globular structure (the "cumulus") adjacent to the toroid and closer to the entrance of the antennal nerve into the AL (74). AL PNs that respond to antennal stimulation with sex pheromone component A have arborizations in the toroid and PNs responsive to component B, in the cumulus (74). Thus first-order synaptic processing of sensory information about these key components of the sex pheromone apparently is confined to different, distinctive neuropil regions of the MGC. 

In females of the genus Agriotes, several esters of acyclic terpenes have been identified as pheromone components. Typical examples are geranyl 3-methyl-butyrate 95, the first pheromone identified from an Agriotis species [193] or ( , )-farnesyl butyrate 96, which together with geranyl butyrate is the major component of the sex pheromone of A. brevis [194]. In A. lineatus, the activity... 

The female produced sex pheromone of the black carpet beetle, Attagenus unicolor (formerly called A. megatoma or A. piceus) has been identified as early as 1967 to be (3 ,5Z)-3,5-tetradecadienoic acid, megatomoic acid 106 [204,205] (Scheme 12). The (3Z)-isomer of megatomoic acid was found to be the major male attracting component in the female produced pheromone of A. brunneus (formerly A. elongatulus) [206]. 

A component of the vaginal secretion, dimethyl disulfide, was found to be the major sex attractant of the golden hamster [ 59 ]. Volatile alcohols, fatty acids and, interestingly, dimethyl trisulfide in the secretion do not appear to enhance the attractancy of the secretion [60]. However, proteins in the mass range of 15-16 kDa that are present in the vaginal secretion act as a mounting pheromone [61]. No comprehensive chemical characterization of the semiochemical secretions of golden hamsters has yet been undertaken. 

Male Megacyllene caryae Gahan (Coleoptera Cerambycidae) respond to females only after touching them with their antennae, indicating the presence of a contact sex pheromone. The hydrocarbon, (Z )-9-nonacosene, was identified as the major component of the contact sex pheromone of the beetle. ... 

The major component of the female sex pheromone produced by the herald moth, Scoliopteryx libatrix (L.) (Lepidoptera Noctuidae), has been identified as (6Z)-13-methylheneicosene. This is the first example of a branched chain alkene as a sex pheromone in the Noctuidae family and is markedly different from the pheromones of the other members in the group. The authors have not conclusively stated, but they suggest that it is probably the (Id-Sj-isomer. ... 

Enantioselective syntheses of four different stereoisomers of the major component of the sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, maconelliyl... 

Marko et al. used this approach during the total synthesis of one of the major components of the Dacus oleae sex pheromone mixture (Scheme 13.90) [59, 60], The desired spiro-ketal 246 was obtained in three steps and 51% overall yield starting from allylsilyl ether 106a. 

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