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Aggregation Pheromones

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Robert J. Bartelt – One of the best experts on this subject based on the ideXlab platform.

  • male specific sesquiterpenes from phyllotreta flea beetles
    Journal of Natural Products, 2011
    Co-Authors: Robert J. Bartelt, Bruce W. Zilkowski, Allard A. Cossé, Udo Schnupf, Karl E Vermillion, Frank A. Momany
    Abstract:

    Flea beetles in several genera are known to possess male-specific sesquiterpenes, at least some of which serve as Aggregation Pheromones that attract both sexes. In continuing research on the chemical ecology of Phyllotreta flea beetles, six new male-specific sesquiterpenes were identified, one from P. striolata (hydroxyketone 9) and five from P. pusilla (aldehydes 10−12 and 14 and alcohol 13); both species are crop pests. The minute amounts from beetles provided mass spectra and chromatographic data but were insufficient for complete structure determination. However, it was discovered that the new compounds could all be produced by applying organic reactions to previously identified flea beetle sesquiterpenes, and the resulting, larger amounts of material permitted definitive structure analysis by NMR. Molecular modeling was used in conjunction with NMR to define relative configurations of several newly created stereogenic centers. The absolute configurations of natural 9−14 were established by chiral ga…

  • Aggregation Pheromones of drosophila immigrans d phalerata and d subobscura
    Journal of Chemical Ecology, 1996
    Co-Authors: Katarina Hedlund, Robert J. Bartelt, Marcel Dicke, L E M Vet
    Abstract:

    Aggregation Pheromones ofDrosophila immigrans, D. phalerata andD. subobscura were demonstrated by testing attraction of adult flies to hexane extracts of the flies in a windtunnel bioassay. Extracts of adult males of all species attracted conspecific males and females. However,D. subobscura flies were attracted only when the extract (cVA) in the extracts of adult maleD. immigrans andD. phalerata. Both species were attracted to synthetic cVA. Male and femaleD. phalerata. Both species were attracted to synthetic cVA. Male and femaleD. subobscura produced 5,9-pentacosadiene, 5-pentacosene, 2-methylhexacosene and 5,9-heptacosadiene, while only maleD. subobscura produced (Z)-5-tricosene and minor amounts of cVA.

  • Mass-trapping ofCarpophilus spp. (Coleoptera: Nitidulidae) in stone fruit orchards using synthetic Aggregation Pheromones and a coattractant: Development of a strategy for population suppression
    Journal of Chemical Ecology, 1996
    Co-Authors: David G. James, Robert J. Bartelt, Christopher J Moore
    Abstract:

    Experiments were conducted in southern New South Wales to evaluate the potential of mass-trapping using synthetic Aggregation Pheromones and a coattractant as a control option for Carpophilus spp. in stone fruit orchards. A cordon of 54 pipe and 54 funnel traps (one trap of each type per perimeter tree) baited with Pheromones of C. mutilatus and C. davidsoni and coattractant (fermenting bread dough) was maintained around an apricot orchard for three weeks prior to harvest. The incidence of Carpophilus spp. in ripe fruit in the center of the orchard was significantly reduced compared to a nearby orchard or the perimeter trees containing traps. A cordon of 16 water-filled Magnet funnel traps baited with Pheromones of C. mutilatus and C. davidsoni and coattractant was placed around a 9 × 9 block of trees in a peach orchard (single traps on alternate perimeter trees). This trapping regime significantly reduced infestation of fruit baits by Carpophilus spp. in the center tree over a period of six weeks compared to fruit baits in trap trees and distant (100 m) control trees. However, cordons of eight pheromone traps within 1 m of single trees or a single trap adjacent to a tree increased Carpophilus spp. infestation of fruit baits by up to 7.5 × compared to trees without pheromone traps. Mass-trapping based on perimeter positioning of pheromone traps (at a yet to be determined distance from protected trees) appears to show potential as a control strategy for Carpophilus spp. in stone fruit orchards during fruit ripening and harvest but traps too close to trees must be avoided. Development of a strategy for population suppression is discussed with respect to trap type, efficacy, positioning, and density; pheromone and coattractant delivery systems; and orchard sanitation.

David G. James – One of the best experts on this subject based on the ideXlab platform.

  • Mass-trapping ofCarpophilus spp. (Coleoptera: Nitidulidae) in stone fruit orchards using synthetic Aggregation Pheromones and a coattractant: Development of a strategy for population suppression
    Journal of Chemical Ecology, 1996
    Co-Authors: David G. James, Robert J. Bartelt, Christopher J Moore
    Abstract:

    Experiments were conducted in southern New South Wales to evaluate the potential of mass-trapping using synthetic Aggregation Pheromones and a coattractant as a control option for Carpophilus spp. in stone fruit orchards. A cordon of 54 pipe and 54 funnel traps (one trap of each type per perimeter tree) baited with Pheromones of C. mutilatus and C. davidsoni and coattractant (fermenting bread dough) was maintained around an apricot orchard for three weeks prior to harvest. The incidence of Carpophilus spp. in ripe fruit in the center of the orchard was significantly reduced compared to a nearby orchard or the perimeter trees containing traps. A cordon of 16 water-filled Magnet funnel traps baited with Pheromones of C. mutilatus and C. davidsoni and coattractant was placed around a 9 × 9 block of trees in a peach orchard (single traps on alternate perimeter trees). This trapping regime significantly reduced infestation of fruit baits by Carpophilus spp. in the center tree over a period of six weeks compared to fruit baits in trap trees and distant (100 m) control trees. However, cordons of eight pheromone traps within 1 m of single trees or a single trap adjacent to a tree increased Carpophilus spp. infestation of fruit baits by up to 7.5 × compared to trees without pheromone traps. Mass-trapping based on perimeter positioning of pheromone traps (at a yet to be determined distance from protected trees) appears to show potential as a control strategy for Carpophilus spp. in stone fruit orchards during fruit ripening and harvest but traps too close to trees must be avoided. Development of a strategy for population suppression is discussed with respect to trap type, efficacy, positioning, and density; pheromone and coattractant delivery systems; and orchard sanitation.

  • Trap Design Effect on Capture of Carpophilus spp. (Coleoptera: Nitidulidae) Using Synthetic Aggregation Pheromones and a Coattractant
    Journal of Economic Entomology, 1996
    Co-Authors: David G. James, Robert J. Bartelt, Christopher J Moore
    Abstract:

    In a series of experiments conducted in stone fruit orchards in southern Australia, water-based funnel-type traps baited with synthetic Aggregation pheromone and fermenting bread dough, trapped 3- to 7-fold as many Carpophihus beetles (primarily C. dauidsoni) than wind-oriented pipe traps or dry funnel traps. The efficacy of dry funnel traps but not pipe traps, appeared to be improved by using water-filled collecting bottles. The potential for using water-based funnel traps in population suppression of Carpophilus spp. in stone fruit orchards through mass trapping is discussed.

  • Attraction ofCarpophilus spp. (Coleoptera: Nitidulidae) to synthetic Aggregation Pheromones and host-related coattractants in Australian stone fruit orchards: Beetle phenology and pheromone dose studies
    Journal of Chemical Ecology, 1994
    Co-Authors: David G. James, Robert J. Bartelt, Richard J. Faulder
    Abstract:

    Synthetic Aggregation Pheromones of Carpophilus hemipterus (L.) and Carpophilus mutilatus Erichson were field tested during a 10-month period in southern New South Wales stone fruit orchards to determine Carpophilus spp. phenology and the effect of two pheromone doses on attraction. Aggregation Pheromones synergize the attraction of host volatiles to Carpophilus spp. Four major species, C. hemipterus, C. mutilatus, C. davidsoni Dobson and C. (Urophorus) humeralis (F.), were trapped, with greater numbers of each species in C. hemipterus pheromone/fermenting whole-wheat breaddough-baited traps, than in dough-only-traps. In C. mutilatus pheromone/ fermenting-dough-baited traps, only C. mutilatus and C. davidsoni responded in greater numbers than to dough-only traps. Beetles first appeared in traps in late September (early spring) when daily maximum temperatures averaged 17.5‡C. Trappings reached a peak during October and declined to very low levels in November–December (late spring-early summer). Numbers trapped of all species increased during February–March (late summer–early autumn), presumably due to the presence of abundant host resources (ripening and fallen fruit), and continued at high levels until May (late autumn). An 18-week study demonstrated significantly greater responses by Carpophilus spp. to 5000- Μ g than to 500- Μ g doses of C. hemipterus and C. mutilatus Pheromones. Greatest responses to 5000 Μ g were recorded for C. hemipterus and C. mutilatus responding to their own Pheromones (increased attraction over dough alone of 259x and 21.2x respectively). Implications of the study and the potential for using synthetic Aggregation Pheromones for managing Carpophilus spp. populations in Australian stone fruit are discussed.

Anja Nühring – One of the best experts on this subject based on the ideXlab platform.

  • First asymmetric synthesis of (+)-sordidin and (-)-7-epi-sordidin, Aggregation Pheromones of the banana weevil Cosmopolites sordidus
    European Journal of Organic Chemistry, 2005
    Co-Authors: Dieter Enders, Irene Breuer, Anja Nühring
    Abstract:

    The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(–)-sordidin, both components of the natural male-produced Aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza-enolate of 3-pentanone SAEP-hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C-7 epimers in good overall yield (39 %) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97 %, ee ≥ 98 %). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  • first asymmetric synthesis of sordidin and 7 epi sordidin Aggregation Pheromones of the banana weevil cosmopolites sordidus
    European Journal of Organic Chemistry, 2005
    Co-Authors: Dieter Enders, Irene Breuer, Anja Nühring
    Abstract:

    The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(–)-sordidin, both components of the natural male-produced Aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza-enolate of 3-pentanone SAEP-hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C-7 epimers in good overall yield (39 %) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97 %, ee ≥ 98 %). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  • Cover Picture: First Asymmetric Synthesis of (+)-Sordidin and (−)-7-epi-Sordidin, Aggregation Pheromones of the Banana Weevil Cosmopolites sordidus (Eur. J. Org. Chem. 12/2005)
    European Journal of Organic Chemistry, 2005
    Co-Authors: Dieter Enders, Irene Breuer, Anja Nühring
    Abstract:

    The cover picture shows the most important worldwide insect pest of banana plants, the banana weevil Cosmopolites sordidus (Germar). These long-lived weevils lay their eggs in the rhizome of the plant. The larvae hatch and then feed and tunnel in the rhizome of the plant, weakening it and leading to the snapping of the rhizome at the ground level before the bunch is ripe. The first evidence for the depicted volatile male-produced Aggregation Pheromones, sordidin and 7-epi-sordidin was supplied by Budenberg et al. in 1993. Details of the first asymmetric synthesis of the major pheromone compound, sordidin, and its C-7-epimer based on the SAMP/RAMP-hydrazone methodology are described in the article by D. Enders et al. on p. 2677 ff.

Richard J. Faulder – One of the best experts on this subject based on the ideXlab platform.

  • Attraction ofCarpophilus spp. (Coleoptera: Nitidulidae) to synthetic Aggregation Pheromones and host-related coattractants in Australian stone fruit orchards: Beetle phenology and pheromone dose studies
    Journal of Chemical Ecology, 1994
    Co-Authors: David G. James, Robert J. Bartelt, Richard J. Faulder
    Abstract:

    Synthetic Aggregation Pheromones of Carpophilus hemipterus (L.) and Carpophilus mutilatus Erichson were field tested during a 10-month period in southern New South Wales stone fruit orchards to determine Carpophilus spp. phenology and the effect of two pheromone doses on attraction. Aggregation Pheromones synergize the attraction of host volatiles to Carpophilus spp. Four major species, C. hemipterus, C. mutilatus, C. davidsoni Dobson and C. (Urophorus) humeralis (F.), were trapped, with greater numbers of each species in C. hemipterus pheromone/fermenting whole-wheat breaddough-baited traps, than in dough-only-traps. In C. mutilatus pheromone/ fermenting-dough-baited traps, only C. mutilatus and C. davidsoni responded in greater numbers than to dough-only traps. Beetles first appeared in traps in late September (early spring) when daily maximum temperatures averaged 17.5‡C. Trappings reached a peak during October and declined to very low levels in November–December (late spring-early summer). Numbers trapped of all species increased during February–March (late summer–early autumn), presumably due to the presence of abundant host resources (ripening and fallen fruit), and continued at high levels until May (late autumn). An 18-week study demonstrated significantly greater responses by Carpophilus spp. to 5000- Μ g than to 500- Μ g doses of C. hemipterus and C. mutilatus Pheromones. Greatest responses to 5000 Μ g were recorded for C. hemipterus and C. mutilatus responding to their own Pheromones (increased attraction over dough alone of 259x and 21.2x respectively). Implications of the study and the potential for using synthetic Aggregation Pheromones for managing Carpophilus spp. populations in Australian stone fruit are discussed.

  • attraction of carpophilus spp coleoptera nitidulidae to synthetic Aggregation Pheromones and host related coattractants in australian stone fruit orchards beetle phenology and pheromone dose studies
    Journal of Chemical Ecology, 1994
    Co-Authors: David G. James, Robert J. Bartelt, Richard J. Faulder
    Abstract:

    Synthetic Aggregation Pheromones ofCarpophilus hemipterus (L.) andCarpophilus mutilatus Erichson were field tested during a 10-month period in southern New South Wales stone fruit orchards to determineCarpophilus spp. phenology and the effect of two pheromone doses on attraction. Aggregation Pheromones synergize the attraction of host volatiles toCarpophilus spp. Four major species,C. hemipterus, C. mutilatus, C. davidsoni Dobson andC. (Urophorus) humeralis (F.), were trapped, with greater numbers of each species inC. hemipterus pheromone/fermenting whole-wheat breaddough-baited traps, than in dough-only-traps. InC. mutilatus pheromone/ fermenting-dough-baited traps, onlyC. mutilatus andC. davidsoni responded in greater numbers than to dough-only traps. Beetles first appeared in traps in late September (early spring) when daily maximum temperatures averaged 17.5‡C. Trappings reached a peak during October and declined to very low levels in November–December (late spring-early summer). Numbers trapped of all species increased during February–March (late summer–early autumn), presumably due to the presence of abundant host resources (ripening and fallen fruit), and continued at high levels until May (late autumn). An 18-week study demonstrated significantly greater responses byCarpophilus spp. to 5000-Μg than to 500-Μg doses of C.hemipterus andC. mutilatus Pheromones. Greatest responses to 5000Μg were recorded forC. hemipterus andC. mutilatus responding to their own Pheromones (increased attraction over dough alone of 259x and 21.2x respectively). Implications of the study and the potential for using synthetic Aggregation Pheromones for managingCarpophilus spp. populations in Australian stone fruit are discussed.

Dieter Enders – One of the best experts on this subject based on the ideXlab platform.

  • First asymmetric synthesis of (+)-sordidin and (-)-7-epi-sordidin, Aggregation Pheromones of the banana weevil Cosmopolites sordidus
    European Journal of Organic Chemistry, 2005
    Co-Authors: Dieter Enders, Irene Breuer, Anja Nühring
    Abstract:

    The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(–)-sordidin, both components of the natural male-produced Aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza-enolate of 3-pentanone SAEP-hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C-7 epimers in good overall yield (39 %) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97 %, ee ≥ 98 %). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  • first asymmetric synthesis of sordidin and 7 epi sordidin Aggregation Pheromones of the banana weevil cosmopolites sordidus
    European Journal of Organic Chemistry, 2005
    Co-Authors: Dieter Enders, Irene Breuer, Anja Nühring
    Abstract:

    The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(–)-sordidin, both components of the natural male-produced Aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza-enolate of 3-pentanone SAEP-hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C-7 epimers in good overall yield (39 %) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97 %, ee ≥ 98 %). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  • Cover Picture: First Asymmetric Synthesis of (+)-Sordidin and (−)-7-epi-Sordidin, Aggregation Pheromones of the Banana Weevil Cosmopolites sordidus (Eur. J. Org. Chem. 12/2005)
    European Journal of Organic Chemistry, 2005
    Co-Authors: Dieter Enders, Irene Breuer, Anja Nühring
    Abstract:

    The cover picture shows the most important worldwide insect pest of banana plants, the banana weevil Cosmopolites sordidus (Germar). These long-lived weevils lay their eggs in the rhizome of the plant. The larvae hatch and then feed and tunnel in the rhizome of the plant, weakening it and leading to the snapping of the rhizome at the ground level before the bunch is ripe. The first evidence for the depicted volatile male-produced Aggregation Pheromones, sordidin and 7-epi-sordidin was supplied by Budenberg et al. in 1993. Details of the first asymmetric synthesis of the major pheromone compound, sordidin, and its C-7-epimer based on the SAMP/RAMP-hydrazone methodology are described in the article by D. Enders et al. on p. 2677 ff.