Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females.

The rice stalk stink bug, Tibraca limbativentris, is an important rice pest in Brazil with a high invasive potential for Mexico and the USA. The sex pheromone of this species was previously identified as a combination of two stereoisomers of 1,10-bisaboladien-3-ol (zingiberenol), but the absolute configurations of these sesquiterpenes were not determined, neither were their effect(s) on T. limbativentris behavior evaluated. In this study, using two chiral columns, we compared retention times of the two natural 1,10-bisaboladien-3-ol stereoisomers from air-entrainment samples of male T. limbativentris with those of synthetic stereoisomers of 1,10-bisaboladien-3-ol. The results showed that T. limbativentris males produce (3S,6S,7R)-1,10-bisaboladien-3-ol (1) and (3R,6S,7R)-1,10-bisaboladien-3-ol (5) as their sex pheromone. Two new minor, male-specific components were also identified as cis and trans isomers of 2,10-bisaboladien-1-ol (sesquipiperitol). Y-tube olfactometer bioassays showed that the major (3S,6S,7R) isomer 1 was essential for attraction of T. limbativentris females, but the minor (3R,6S,7R) isomer 2 was not, nor did it show synergistic/antagonistic effects when added to the major isomer. The (1S,6S,7R) and (1R,6S,7R) stereoisomers of sesquipepiritol also attracted T. limbativentris females.

Kairomones from Euschistus heros egg masses and their potential use for Telenomus podisi parasitism improvement.

Telenomus podisi Ashmead (Hymenoptera: Scelionidae) is the most important egg parasitoid of Euschistus heros (Fabricius) (Hemiptera: Pentatomidae), and its successful parasitism is related to their searching ability to find suitable hosts under a complex chemical environment using host-reliable cues. Thus, the objective of this study was to elucidate chemical substances on the external layer of E. heros eggs and report its potential kairomonal activity on T. podisi. We tested female wasps in olfactometer system to synthetic compounds obtained from a chemical identification of E. heros egg masses. The synthetic blend was also evaluated in parasitism tests under laboratory and semi-field conditions. We identified 31 substances from egg surface extracts, including monoterpenes, aldehydes and alkanes. Among those compounds, a synthetic solution including camphene, ß-pinene, limonene and benzaldehyde-induced chemotaxic behaviour on the wasps and increased the parasitism on E. heros eggs, either in laboratory or semi-field test, suggesting its potential use to T. podisi manipulation and parasitism improvement.

The influence of volatile semiochemicals from stink bug eggs and oviposition-damaged plants on the foraging behaviour of the egg parasitoid Telenomus podisi.

During host selection, physical and chemical stimuli provide important cues that modify search behaviours of natural enemies. We evaluated the influence of volatiles released by eggs and egg extracts of the stink bug Euschistus heros and by soybean plants treated with the eggs and egg extracts on Telenomus podisi foraging behaviour. Responses to volatiles were evaluated in Y-tube olfactometers after exposure to (1) one egg cluster for 24 h; (2) plants with eggs laid by the stink bug, tested at 24, 48, and 72 h after treatment; (3) plants with eggs laid artificially, tested at 24, 48, and 72 h after treatment; and (4) plants treated with acetone or hexane extracts of eggs. Telenomus podisi was attracted to volatiles emitted by one egg cluster and to acetone extracts of one egg cluster, but not to air or acetone controls. There were no responses to odours of plants treated with eggs or egg extracts. Analysis of acetone extracts of egg clusters by gas chromatography revealed the major components were saturated and unsaturated fatty acids, including hexadecanoic acid, linoleic acid, and (Z)-9-octadecenoic acid. Our results suggest that one egg cluster and the acetone extract of one egg cluster contain volatile compounds that can modify T. podisi foraging behaviour, and that the amounts of these compounds, probably together with some minor compounds, are important for host recognition by T. podisi. Also, the oviposition damage or egg extracts on the plant did not elicit indirect defences that attracted Telenomus podisi.