Absolute Configuration of the Invasive Mealybug Delottococcus aberiae (De Lotto) Sex Pheromone: Synthesis and Bioassay of Both Enantiomers
[EN] The mealybug Delottococcus aberiae (De Lotto) (Hemiptera: Pseudococcidae) is an invasive pest reported in Europe at the end of the first decade of the 2000s, causing severe damage to citrus production in eastern Spain. In a previous work, (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl)methyl a...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2024 |
| País: | España |
| Institución: | Universitat Politècnica de València (UPV) |
| Repositorio: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
| Idioma: | inglés |
| OAI Identifier: | oai:riunet.upv.es:10251/219872 |
| Acceso en línea: | https://riunet.upv.es/handle/10251/219872 |
| Access Level: | acceso abierto |
| Palabra clave: | D. aberiae Diastereomeric resolution Enantiomers Insect attractant Necrodol skeleton Pheromone |
| Sumario: | [EN] The mealybug Delottococcus aberiae (De Lotto) (Hemiptera: Pseudococcidae) is an invasive pest reported in Europe at the end of the first decade of the 2000s, causing severe damage to citrus production in eastern Spain. In a previous work, (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl)methyl acetate was identified as the sex pheromone emitted by females, a new compound with an unusual ß-necrodol skeleton possessing one stereocenter. This compound was assigned to the (-)-enantiomer but the absolute configuration was then not reported. In the present study, enantiomeric pure samples of both enantiomers were synthesized. X-ray diffraction analysis allowed the (-)-enantiomer, identical to the one emitted by virgin D. aberiae females, to be unequivocally identified as (-)-(R)-(4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl)methyl acetate. Bioassays carried out to test the activity of both enantiomers under field conditions suggest that the presence of the (+)-(S)-enantiomer has detrimental effects on the activity of the racemates. |
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