Electrophysiological and behavioral activity of (E)-2-hexenal in the granary weevil and its application in food packaging.

The purpose of this work was to develop a biodegradable carrier material to control insect pests in cereal products. To this aim, (E)-2-hexenal was used, being a natural compound with antimicrobial activity that is also commonly adopted as a flavoring agent. Three coating layers of polycaprolactone (PCL) were spread onto the internal side of a paperboard carton, the first being the active coating containing (E)-2-hexenal. The antennal sensitivity of Sitophilus granarius to a broad range of doses of (E)-2-hexenal was first demonstrated. Next, the ability of different concentrations of this compound to disrupt the orientation of adult S. granarius beetles to odors of intact wheat kernels was established in a two-choice pitfall bioassay. In addition, invasion tests were carried out over an 8-week period to highlight the effects of the biobased repellent packaging and their potential persistence. The results demonstrated that during the entire monitoring period, the percentage of S. granarius adults found in cartons coated with (E)-2-hexenal-loaded multilayer PCL was about 10 % of the total number of insects used in the bioassay, very low compared with the respective control samples, thus assessing both the effectiveness and persistence of the repellent system developed. Although the infestation level of treated packages was reduced relative to the infestation levels in the controls, any infestation of food packages is unacceptable to consumers, so further tests are required to determine whether infestation can be completely prevented using (E)-2-hexenal.

Control of Lobesia botrana (Lepidoptera: Tortricidae) by biodegradable ecodian sex pheromone dispensers.

Mating disruption with a high density of sex pheromone dispensers is a new strategy recently developed for the control of the moth Lobesia botrana (Denis & Schiffermüller) (Lepidoptera: Tortricidae). Ecodian LB dispensers, made of low-cost biodegradable material, were formulated with 10 mg of (E,Z) -7,9-dodecadienyl acetate and placed at a rate of 1,600 dispensers per ha. Seasonal dispenser performances were studied using different methods. The female attractiveness disruption and the efficacy of the method were evaluated in the field. The release rates of field-aged Ecodian LB dispensers, measured directly by solid phase microextraction, was comparable with that of the standard monitoring lure after 50-60 d of field exposure and significantly lower beyond 60 d; however, at the end of the season, it was approximately 46 times higher than that of a calling L. botrana female. Electroantennographic recordings showed that dispensers of different field age strongly stimulated male antennae. In a wind tunnel test, dispensers elicited close-range approaches and direct source contacts irrespective of their age. In fields treated with Ecodian dispensers the attractiveness of traps lured with calling females and monitoring baits was significantly reduced. Our data suggest that Ecodian dispensers are active sources of pheromone throughout the season. The efficacy of Ecodian strategy for L. botrana control was comparable with standard mating disruption and curative insecticides.

Stereoselective synthesis of trifluoro- and monofluoro-analogues of frontalin and evaluation of their biological activity.

The stereoselective synthesis of both enantiomers of trifluoro frontalin (-)-(1S,5R)- and (+)-(1R,5S)-8, as well as of diastereomeric monofluoro frontalines (-)-(1R,2R,5R)-18 and (-)-(1R,2S,5R)-20, analogues of the bioactive component of the aggregation pheromone of the Scolytidae insect family, has been accomplished starting from (-)-(1R)- and (+)-(1S)-menthyl (S)-toluene-4-sulfinate as a source of chirality and methyl trifluoroacetate or fluoroacetate, respectively, as sources of fluorine. The C-1 stereocenters were installed via stereoselective epoxidation of beta-sulfinyl ketones 2 and 13 with diazomethane. The bicyclic core was obtained by totally stereocontrolled and chemoselective tandem Wacker oxidation/intramolecular ketalization of the intermediate unsatured sulfinyl diols 5, 15, and 19. Axially fluorinated (-)-20 elicited a strong electroantennographic response in laboratory tests on females of Dendroctonus micans, whereas equatorially fluorinated (-)-18 and the trifluoroanalogue (-)-8 showed modest responses. Field trials using (-)-20 were not indicative owing to the locally scarce population of D. micans, but it showed some attractiveness for other Coleoptera families.