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Cis-Verbenol

SotF sexes will respond to a mixture of cis-verbenol, ipsdienol and methylbutenol. [Pg.49]

Practical use of pheromones started in 1978. That year we used 110.000 trap-trees sprayed with an insecticide (Lindane). The first year we used one dispenser with an initial loading of 70 mg cis-verbenol and 10 mg ipsdienol. A second dispenser was loaded with 100 mg methylbutenol. In 1979 we adjusted the loading and used only one dispenser containing all 3... [Pg.50]

Miller D. R. and Lafontaine J. R (1991) cis-Verbenol An aggregation pheromone for the mountain pine beetle Dendroctonus ponderosae Hopkins (Coleoptera Scolytidae), J. Entomol. Soc. Brit. Columbia 88, 34—38. [Pg.194]

Scolytidae. The worldwide ranges of bark beetles have made them ideal candidates for research directed toward the isolation and identification of pheromones that can be used for population monitoring and regulation. A decade ago, the aggregative pheromone liberated by males of Ips paraconfusus (=confusus) was identified as a mixture of (-)-2-methyl-6-methylene-7-octen-4-ol (ipsenol) (XVI), (+)-cis-verbenol (XVII), and (+)-2-methyl-6-methylene-2,7-octadien-4-ol (ipsdienol) (XVIII)... [Pg.213]

The major aggregation pheromone components of T. typographies are e-is-verbenol and 2-methyl-3-buten-ol (1). Cis-verbenol is common to several Ips species (2). Only the Ts)-(-) enantiomer evokes response in field experiments (3). Methylbutenol is specific to I. typographies. A different isomer is part of the pheromone of the related species Ips oembrae, which lives on larch in Europe C4). Ipsdienol (2-methyl-6-methylene-2, 7-octadiene-4-ol), which... [Pg.220]

The faecal pellets of the bark beetle Ips paraconfusus which had fed on the phloem of Pinus ponderosa contained large quantities of the aggregation pheromones cis-verbenol (24), ipsenol (25), and ipsdienol (26). The pheromones originate in the hindgut, but, although there is a precursor-product correlation between a-pinene or myrcene from the phloem and the pheromone terpenoids, the biosynthetic site is unclear. The demonstration68 of the conversion of a-pinene into cis- and trans-verbenol (27) by Bacillus cereus found in the gut of I. paraconfusus has led to the... [Pg.179]

Bark beetles are of great economic importance, which is one of the reasons more research has been done on the pheromones of the Scolytidae than on those of any other family of Coleoptera. Their pheromone systems also seem to be typical of the Coleoptera in that while there is considerable diversity in pheromone structure within this family, there also seems to be a pattern of structures, particularly within a genus. The first pheromone identified from a coleopterous species was from Ips paraconfusus Lanier (then I. confusus) by Silverstein et al. (13). Three compounds — ipsenol (I), ipsdienol (II), and cis-verbenol (III)... [Pg.369]

Isomeric cis-verbenol is an aggregation pheromone attractant for both the male and female insects of the species. The same author [105] published information concerning a defense secretion of the soldiers of the termites Nasutitermes nigriceps, N. Ephratae and Velocitermes velox from Peru). The enantiomeric compositions of a -pinene and limonene produced by three termite species are as follows ... [Pg.385]

Adult male and female bark beetles (Ipsparaconfusus) convert (—)-a-pinene into ( + )-cis-verbenol and (-)-myrtenol whereas (+)-rran5-verbenol and ( + )-myrtenol are produced from (+)-a-pinene. Since ( + )-cw-verbenol is the aggregation pheromone for this beetle it would appear that production of the pheromone is controlled by the host tree. [Pg.187]

As a contribution to a subproject of CMD of EUROTRAC-2, scientists from ICHF studied experimentally the effect of a-pinene and cis-verbenol on the rate of S(IV) oxidation catalyzed by Fe, as well as the ozone-affected autoxidation of aqueous SO2 in the presence of calcium. The investigations were aimed at clarifying the mechanism of the aqueous phase oxidation of SO(IV) simultaneously by O3 and O2, calcium acting as condensation nuclei. Inhibition of the S(IV) autoxidation in the atmosphere by secondary terpenic compounds was also studied... [Pg.321]

S)+ Ipsdienol (R)- Ipsdienol Ipsenol cis- Verbenol Methyl- ButenoP... [Pg.150]

The conformations of the verbanols have been discussed in relation to their n.m.r. spectra. The photochemical conversion of verbenone (347) into chry-santhenone (359) is discussed again, and it has been shown that the same reaction occurs with y-radiation. In the latter case the conversion is small, verbenone being surprisingly stable towards y-radiation. In these conditions, trans-verbenol is also stable, but cis-verbenol is converted into a mixture of the trans-isomer and verbenone. The known apoverbenone (360) has been made by a much improved route.The first stage, N-bromosuccinimide bromination of nopinone (361) leads initially to the a-bromoketone (362) (this is the kinetic... [Pg.75]

CioHi O, Mr 152.23. Unsaturated, bicyclic monoter-pene alcohols with the pinane structure. Pinocarveol and chrysanthenol occur in nature in the above shown configurations while all four possible stereoisomers of verbenol and the two possible enantiomers of myrte-nol are known. The table lists plants from which P. can be isolated from the essential oils. P. also occur as the acetates in nature. (,+)-trans- and (+)-cis -verbenol are components of the aggregation pheromone of the conifer bark beetle Ips typographus and the American Ips confusus, a pest of the yellow pine Firms ponderosa, Pinaceae). After a tree has been colonized by a sufficient number of individuals further beetles are diverted to other trees by means of verbenone (see pinenones). The other P. do not exhibit any particular biological activities. [Pg.495]

Bark beetles oxidise toxic monoterpenoid hydrocarbons in their respiratory air, which originate from the resin of the tree they colonise, and thereby circumvent this defense barrier of the tree. Converting these compounds into less toxic secondary metabolites serves another purpose, by providing pheromones to attract insects of the same species, of both sexes. Therefore, an oxygen function is often introduced species-specifically and stereoselectively. European spruce bark beetles oxidise (-)-a-pinene to (S)-cis-verbenol, whereas pine beetles produce (R)-trans-verheno. In the California fivespined engraver Ips paraconfu-sus), myrcene is converted into (S)-ipsdienol and (S)-ipsenol. But Ips pint and Ips paraconfusus are also able to synthesise their pheromones de novo via the classical mevalonate biosynthetic pathway. [Pg.760]

One of the most serious pest insects in old stciiids of spruce is the Europesn spruce bark beetle (Ips typographus) (Fig. 8.84). While colonising a tree, 2-methylbut-3-en-2-ol and (S)-cis-verbenol are secreted first. After establishing a mating chamber, the polygamous male attracts females with ipsenol and ips-dienol. [180]... [Pg.775]

The chiral GCxGC-TOFMS analyses of bark beetle samples showed clearly the advantage of the comprehensive two dimensional gas chromatography - all obtained data were easily interpreted and results showed the strong enantioselectivity in the pheromone component composition, especially in ipsenol (1) and cis-verbenol (3). We found practically only (S)-l and high excess (>1 10) of (lS)-3 in both species, in contrast to frfljjs-verbenol (4) which was in examined samples present mostly only in racemic form Racemic ipsdienol (2) we found in I, nitidus and predominantly as (R)-isomer in I. shangrila. [Pg.343]

The constitutional isomers a and p-pinene are both major constituents of pine resins and found in many essential oils, for example, Pinus species, Piper nigrum and Juniperus communis. Interestingly, a-pinene is more common in European pines, whereas P pinene is more common in North America (Bornscheuer et al., 2014 O Neil, 2006). As shown in Figure 9.22, metabolism of a- and p-pinene in humans leads to the formation of trans- and cis-verbenol and myrtenol,... [Pg.268]


See other pages where Cis-Verbenol is mentioned: [Pg.1050]    [Pg.240]    [Pg.266]    [Pg.277]    [Pg.1327]    [Pg.547]    [Pg.152]    [Pg.50]    [Pg.51]    [Pg.163]    [Pg.448]    [Pg.385]    [Pg.385]    [Pg.401]    [Pg.390]    [Pg.401]    [Pg.385]    [Pg.385]    [Pg.179]    [Pg.775]    [Pg.775]    [Pg.8]    [Pg.343]    [Pg.60]    [Pg.335]    [Pg.339]    [Pg.340]    [Pg.345]    [Pg.346]   
See also in sourсe #XX -- [ Pg.6 ]

See also in sourсe #XX -- [ Pg.6 , Pg.8 , Pg.90 ]




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