Studies towards the identification of the sex pheromone of Thyrinteina arnobia

Journal of the Brazilian Chemical Society

Deobald, Anna M.¹  Neppe, Tiago¹  Paiva, Marcelo M. de¹  Universidade Federal de São Carlos, São Carlos, Brazil¹  Corrêa, Arlene G.¹  Paixão, Marcio W.¹  Moreira, Jardel A.¹  Batista-Pereira, Luciane G.¹ 

关键词: electroantennography;    Thyrinteina arnobia;    sex pheromone;    3;    4-epoxy-Z6;    Z9-heneicosadiene;    asymmetric synthesis;   

DOI  :  10.5935/0103-5053.20130241

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

The eucalyptus brown-looper Thyrinteina arnobia (Lepidoptera: Geometridae) is considered an important pest in Brazilian native plants, e.g. Psidium guajava, and exotic plants, such as Eucalyptus species. In this work we describe the isolation of the pheromone components of T. arnobia, using glands extract and solid phase micro extraction (SPME) of virgin females. The samples were analyzed by gas chromatography with an electroantennographic detector (GC-EAD), and mass spectrometry (GC-MS). Two reproducible electroantennographic responses were elicited in the male antenna of T. arnobia and one of them was identified as 3,4-epoxy-6,9-heneicosadiene by CG-MS. The racemic synthesis of this epoxydiene was carried out in 10 steps and 28% overall yield. The four stereoisomers of the epoxydiene were also synthesized employing the corresponding enantiomeric enriched epoxyalcohols.

【 授权许可】

Unknown