(1 R ,6 R )-2,2,6-Trimethyl-3-oxabicyclo[4.2.0]octan-4-one, a new monoterpene lactone produced by males of the cocoa borer Conotrachelus humeropictus (Col.: Curculionidae)

Grandisol as an attractant for the sugar beet pest Bothynoderes affinis and data on other Lixinae species

“…To the best of our knowledge, this is the first report about an attractant for this species. The racemic grandisol or its (1 R ,2 S )‐enantiomer is an aggregation pheromone component of the boll weevil A. grandis (Tumlinson et al, ) and other curculionid species including several pine weevils of genus Pissodes (Booth et al, ; Phillips et al, ; Hibbard & Webster, ; Ze et al, ; Marques et al, ), the soybean stalk weevil, Sternechus subsignatus Boheman (Ambrogi et al, ), the cocoa borer, Conotrachelus humeropictus Fiedler (Szczerbowski et al, ), Homalinotus validus (Olivier) (Vidal et al, ), the avocado seed weevil, Heilipus lauri Boheman (Romero‐Frías et al, ), the pecan weevil, Curculio caryae (Horn) (Hedin et al, ), the strawberry blossom weevil, Anthonomus rubi (Herbst) (Innocenzi et al, ), Pseudopiazurus obesus (Boheman) (Zarbin et al, , ), and four bark beetles species – Pityophthorus pityographus (Ratzeburg) (Francke et al, ), Pityogenes bidentatus (Herbst) (Francke et al, ; Byers et al, ), Pityogenes calcaratus (Eichhoff) (Francke et al, ), and Polygraphus punctifrons Thomson (Rahmani et al, ). The current study demonstrated that grandisol also attracted A. punctiventris .…”

Pheromones as management tools for non-Scolytinae Curculionidae: development and implementation considerations

“…Mass spectra associated with those chromatographic fractions that are active in electrophysiological assays can be compared to known mass spectra on the NIST, WILEY or other databases (Hedin et al 1997;Romero-Frías et al 2016). Comparison of retention indexes on different polarity columns together with matching mass spectra from standard reference compounds can be used to assign tentative identities to putative pheromone compounds (Hedin et al 1997;Perez et al 1997;Giblin-Davis et al 2000;Szendrei et al 2011;Palacio-Cortés et al 2015;Szczerbowski et al 2016;Branco et al 2019). Specialized chiral columns are often used to separate chiral pheromone constituents from one another.…”

“…This requires that the molecular ion is detected with sufficient accuracy to establish the unique combination of elements that make up of the unknown compound (Tumlinson et al 1969;Collins 1996;Zarbin et al 2003). A match of the retention indexes and mass spectra of reference standards to components in extracts can serve as compound identification (Hedin et al 1997;Perez et al 1997;Giblin-Davis et al 2000;Szendrei et al 2011;Palacio-Cortés et al 2015;Szczerbowski et al 2016;Branco et al 2019) (Supplementary Table 4). Other methods can be used in conjunction with mass spectrometry for novel compound structure determination.…”

“…Electrophysiological assays with synthetic standards can be used to validate or invalidate putative pheromone structures (Ruiz-Montiel et al 2008;Azuara-Domínguez et al 2013;Branco et al 2019). After these electrophysiologically-based screening procedures, the compound identity can be confirmed based on the same retention index values and mass spectral profiles as was determined from experimental samples (Phillips et al 1989;Szczerbowski et al 2016;Branco et al 2019) (Supplementary Table 4). The Kovats retention index is often used as a standardized parameter to compare the elution time of compounds from GC columns of polar, semi-nonpolar and non-polar polarities.…”