Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay
The banana-spotting bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae), is one of the principal pests of tree fruits and nuts across northern and eastern Australia. Apart from visual damage assessment, there are currently no reliable methods for monitoring bug activity to aid manage...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2012-01-01
|
| Series: | Psyche: A Journal of Entomology |
| Online Access: | http://dx.doi.org/10.1155/2012/536149 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849402125946191872 |
|---|---|
| author | Ashot Khrimian Harry A. C. Fay Filadelfo Guzman Kamlesh Chauhan Chris Moore Jeffrey R. Aldrich |
| author_facet | Ashot Khrimian Harry A. C. Fay Filadelfo Guzman Kamlesh Chauhan Chris Moore Jeffrey R. Aldrich |
| author_sort | Ashot Khrimian |
| collection | DOAJ |
| description | The banana-spotting bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae), is one of the principal pests of tree fruits and nuts across northern and eastern Australia. Apart from visual damage assessment, there are currently no reliable methods for monitoring bug activity to aid management decisions. An attractant pheromone for this species that could be used as a trap lure could potentially fill this void. Earlier, two male-specific compounds were identified in airborne extracts from A. lutescens lutescens, (E,E)-α-farnesene and (R,E)-nerolidol; an unknown compound with a molecular weight 220 was also detected. We now report the identification of this hitherto unknown compound as (R,E,E)-α-farnesene-10,11-oxide. Synthesis of this epoxide was conducted using a regioselective asymmetric dihydroxylation of a sulfolene. A blend mimicking the natural proportions of (E,E)-α-farnesene, (R,E)-nerolidol, and (R,E,E)-α-farnesene-10,11-oxide attracted male and female A. lutescens lutescens as well as nymphs in the field, verifying that the aggregation pheromone comprises or is contained within this group of compounds. |
| format | Article |
| id | doaj-art-8aa8032977dd464c8bd3d0e4877c2463 |
| institution | Kabale University |
| issn | 0033-2615 1687-7438 |
| language | English |
| publishDate | 2012-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Psyche: A Journal of Entomology |
| spelling | doaj-art-8aa8032977dd464c8bd3d0e4877c24632025-08-20T03:37:37ZengWileyPsyche: A Journal of Entomology0033-26151687-74382012-01-01201210.1155/2012/536149536149Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field BioassayAshot Khrimian0Harry A. C. Fay1Filadelfo Guzman2Kamlesh Chauhan3Chris Moore4Jeffrey R. Aldrich5Beltsville Agricultural Research Center, Agricultural Research Service, USDA, Building 007, Room 326, BARC-West, 10300 Baltimore Avenue, Beltsville, MD 20705, USADepartment of Employment, Economic Development and Innovation, Horticulture and Forestry Science, 28 Peters Street, P.O. Box 1054, Mareeba, QLD 4880, AustraliaBeltsville Agricultural Research Center, Agricultural Research Service, USDA, Building 007, Room 326, BARC-West, 10300 Baltimore Avenue, Beltsville, MD 20705, USABeltsville Agricultural Research Center, Agricultural Research Service, USDA, Building 007, Room 326, BARC-West, 10300 Baltimore Avenue, Beltsville, MD 20705, USASchool of Biological Sciences, The University of Queensland, Brisbane, QLD 4072, AustraliaBeltsville Agricultural Research Center, Agricultural Research Service, USDA, Building 007, Room 326, BARC-West, 10300 Baltimore Avenue, Beltsville, MD 20705, USAThe banana-spotting bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae), is one of the principal pests of tree fruits and nuts across northern and eastern Australia. Apart from visual damage assessment, there are currently no reliable methods for monitoring bug activity to aid management decisions. An attractant pheromone for this species that could be used as a trap lure could potentially fill this void. Earlier, two male-specific compounds were identified in airborne extracts from A. lutescens lutescens, (E,E)-α-farnesene and (R,E)-nerolidol; an unknown compound with a molecular weight 220 was also detected. We now report the identification of this hitherto unknown compound as (R,E,E)-α-farnesene-10,11-oxide. Synthesis of this epoxide was conducted using a regioselective asymmetric dihydroxylation of a sulfolene. A blend mimicking the natural proportions of (E,E)-α-farnesene, (R,E)-nerolidol, and (R,E,E)-α-farnesene-10,11-oxide attracted male and female A. lutescens lutescens as well as nymphs in the field, verifying that the aggregation pheromone comprises or is contained within this group of compounds.http://dx.doi.org/10.1155/2012/536149 |
| spellingShingle | Ashot Khrimian Harry A. C. Fay Filadelfo Guzman Kamlesh Chauhan Chris Moore Jeffrey R. Aldrich Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay Psyche: A Journal of Entomology |
| title | Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay |
| title_full | Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay |
| title_fullStr | Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay |
| title_full_unstemmed | Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay |
| title_short | Pheromone of the Banana-Spotting Bug, Amblypelta lutescens lutescens Distant (Heteroptera: Coreidae): Identification, Synthesis, and Field Bioassay |
| title_sort | pheromone of the banana spotting bug amblypelta lutescens lutescens distant heteroptera coreidae identification synthesis and field bioassay |
| url | http://dx.doi.org/10.1155/2012/536149 |
| work_keys_str_mv | AT ashotkhrimian pheromoneofthebananaspottingbugamblypeltalutescenslutescensdistantheteropteracoreidaeidentificationsynthesisandfieldbioassay AT harryacfay pheromoneofthebananaspottingbugamblypeltalutescenslutescensdistantheteropteracoreidaeidentificationsynthesisandfieldbioassay AT filadelfoguzman pheromoneofthebananaspottingbugamblypeltalutescenslutescensdistantheteropteracoreidaeidentificationsynthesisandfieldbioassay AT kamleshchauhan pheromoneofthebananaspottingbugamblypeltalutescenslutescensdistantheteropteracoreidaeidentificationsynthesisandfieldbioassay AT chrismoore pheromoneofthebananaspottingbugamblypeltalutescenslutescensdistantheteropteracoreidaeidentificationsynthesisandfieldbioassay AT jeffreyraldrich pheromoneofthebananaspottingbugamblypeltalutescenslutescensdistantheteropteracoreidaeidentificationsynthesisandfieldbioassay |