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Synthetic pheromones have been used for pest control over several decades. The conventional synthesis of di-unsaturated pheromone compounds is usually complex and costly. Camelina (Camelina sativa) has emerged as an ideal, non-food biotech oilseed platform for production of oils with modified fatty acid compositions. We used Camelina as a plant factory to produce mono- and di-unsaturated C 12 chain length moth sex pheromone precursors, (E)-9-dodecenoic acid and (E,E)-8,10-dodecadienoic acid, by introducing a fatty acyl-ACP thioesterase FatB gene UcTE from California bay laurel (Umbellularia californica) and a bifunctional ∆9 desaturase gene Cpo_CPRQ from the codling moth, Cydia pomonella. Different transgene combinations were investigated for increasing pheromone precursor yield. The most productive Camelina line was engineered with a vector that contained one copy of UcTE and the viral suppressor protein encoding P19 transgenes and three copies of Cpo_CPRQ transgene. The T 2 generation of this line produced 9.4% of (E)-9-dodecenoic acid and 5.5% of (E,E)-8,10-dodecadienoic acid of the total fatty acids, and seeds were selected to advance top-performing lines to homozygosity. In the T 4 generation, production levels of (E)-9-dodecenoic acid and (E,E)-8,10-dodecadienoic acid remained stable. The diene acid together with other seed fatty acids were converted into corresponding alcohols, and the bioactivity of the plant-derived codlemone was confirmed by GC-EAD and a flight tunnel assay. Trapping in orchards and home gardens confirmed significant and specific attraction of C. pomonella males to the plant-derived codlemone., (© 2021. The Author(s).)

Research to discover and develop attractants for the codling moth, Cydia pomonella L., has involved identification of the chemicals eliciting moth orientation to conspecific female moths, host fruits, fermented baits, and species of microbes. Pear ester, acetic acid, and N-butyl sulfide are among those chemicals reported to attract or enhance attractiveness to codling moth. We evaluated the trapping of codling moth with N-butyl sulfide alone and in combination with acetic acid and pear ester in apple orchards. Acetic acid was attractive in two tests and N-butyl sulfide was attractive in one of two tests. N-Butyl sulfide increased catches of codling moth when used with acetic acid to bait traps. N-Butyl sulfide also increased catches of codling moth when added to traps baited with the combination of acetic acid and pear ester. Male and female codling moth both responded to these chemicals and chemical combinations. These results provide a new three-component lure comprising N-butyl sulfide, acetic acid, and pear ester that is stronger for luring codling moth females than other attractants tested.

Background: Pheromone antagonists are good disruptants of the pheromone communication in insects and, as such, have been used in mating disruption experiments. In this study, new non-fluorinated electrophilic keto derivatives structurally related to the pheromone of Cydia pomonella (codlemone) have been synthesised and tested as putative pheromone antagonists., Results: Codlemone (1) was prepared in excellent stereoselectivity in a new, iterative approach involving two Horner-Wadsworth-Emmons reactions. Methyl ketone (2), keto ester (3) and diketone (4) were obtained from codlemone in straightforward approaches in good overall yields and excellent stereochemical purity (≥98% E,E). In electrophysiology, only compound 2 displayed inhibition of the antennal response to the pheromone after presaturation of the antennal receptors. Compounds 2 to 4 did not inhibit the pheromone-degrading enzyme responsible for codlemone metabolism, but mixtures of ketone 2 and diketone 4 with codlemone elicited erratic flights on males in a wind tunnel. In the field, blends of either compound (2 or 4) with the pheromone caught significantly fewer males than codlemone alone., Conclusion: Codlemone and the potential antagonists 2 to 4 have been synthesised in good yields and excellent stereoselectivity. These chemicals behave as pheromone antagonists of the codling moth both in the laboratory and in the field., (© 2013 Society of Chemical Industry.)

Modern insect pest management is faced with an increasingly sophisticated set of requirements. Control agent/dispenser combinations must be at the same time safe, nontoxic, inexpensive, reproducibly efficacious, environmentally compatible, biodegradable, and sustainable, and should be based on renewable resources. The methods employed preferably should be suitable for the growing and tightly controlled organic growing sector as well. All this calls for a level of sophistication and reproducibility previously unknown. Only very few systems can offer this kind of performance, but fortunately can be found in the area of suitable pheromone/dispenser combinations. This report is an attempt to adapt electrospun Ecoflex polyester micro fibers of the Greiner-Wendorff type to the very specific needs of the grape growing industry. Specifically required are "semi-intelligent" dispenser materials. On a weight basis, the electrospun product should achieve as high a proportion as possible of "retainable" sex pheromone (E,Z)-7,9-dodecadienyl acetate of Lobesia botrana (Lep.: Tortricidae) and should release it as uniformly as possible into the surrounding airspace. Using the Doye bioassay, some progress indeed has recently been achieved with electrospun Ecoflex microfibers of 0.5-3.5 microm diameter. They were employed as dispensers for programmed sex pheromone release with an effective mating disruption duration of up to seven weeks. With one microfiber/pheromone treatment, this covers one entire flight period of the trivoltine L. botrana. Mechanical application of this microfiber/pheromone preparation (with the option of automation) is possible. Disruption effects are comparable with those of commercially available dispensers of the Isonet type. Exposed under vineyard conditions, Ecoflex polyester fibers are a spider silk like material which is biodegradable within half a year. Thus, after releasing its pheromone load, it does not need removal, which saves one cultivation step. The fibers are under rigorous quantitative pretesting by analytical lab methods such as scanning EM, CLSA, timed weight loss curves in isothermal wind tunnels, and by thermogravimetry. Grapes produced under protection with these pheromone-charged biodegradable and mechanically deployable Ecoflex microfibers are completely free of pesticide residues.

Pheromone eluting oligolactide (OLA) microcapsules immobilized in electrospun biodegradable polyester nanofibers were obtained by electrospinning of aqueous dispersions of the microcapsules. OLA was prepared by conventional melt polycondensation of lactic acid. Following the protocol of the solvent displacement method, OLA was dissolved in acetone and mixed with Brij S20 and the pheromone of the European grape vine moth, Lobesia Botrana, (E,Z)-7,9-dodecadien-l-yl acetate (DA). Up to 32 wt % of this mixture could be dispersed in water with colloidal stability of several weeks without any sedimentation. Without DA as well as OLA, no stable dispersions of OLA in water were obtained. Replacement of DA by classical hydrophobes typically used for miniemulsions did not yield stable dispersions, but the addition of octyl acetate, which shows structural similarity to DA, yielded stable dispersions in water up to 10 wt %. Dispersions of OLA/DA were successfully electrospun in combination with an aqueous dispersion of a biodegradable block copolyester resulting in water-stable nanofibers containing OLA/DA microcapsules. Release of DA from microcapsules and fibers was retarded in comparison with non-encapsulated DA, as shown by model studies.

A new pheromone antagonist of the codling moth Cydia pomonella is reported. Presaturation of the antennae of the insects with vapors of the antagonist (E,E)-8,10-dodecadienyl trifluoromethyl ketone, analogue of the main component of the pheromone (codlemone), resulted in lower electrophysiological responses to the pheromone relative to untreated insects. In the wind tunnel, the compound elicited a remarkable disruptive effect on all types of behavior of males flying toward a source baited with a pheromone/antagonist blend in 1:1, 1:5, and 1:10 ratios. The insects displayed erratic flights in the presence of the antagonist, as shown by their flight parameters in comparison to insects attracted to the pheromone alone. In the field, traps baited with mixtures of 1:10 codlemone/antagonist attracted considerably lower numbers of males than the natural attractant. The antagonist, however, did not inhibit the pheromone-degrading enzymes present in male antennae, suggesting that trifluoromethyl ketones are not sufficiently electrophilic to produce a stable intermediate adduct with a cysteine residue of the enzyme, a mechanism previously proposed for oxidase inhibition in insects. Overall and taking into account our previous reports and, particularly, the reduction in damage induced in maize fields by a trifluoromethyl ketone analogue of the pheromone of Sesamia nonagrioides (Sole, J.; Sans, A.; Riba, M.; Rosa, E.; Bosch, M. P.; Barrot, M.; Palencia, J.; Castella, J.; Guerrero, A. Reduction of damage by the Mediterranean corn borer, Sesamia nonagrioides , and the European corn borer, Ostrinia nubilalis , in maize fields by a trifluoromethyl ketone pheromone analog . Entomol. Exp. Appl. 2008, 126, 28-39), the antagonist might be a new candidate to consider in future strategies to control the codling moth.

Factors affecting the efficacy of an attracticide strategy for the control of the codling moth Cydia pomonella L (Lepidoptera: Tortricidae) were investigated using laboratory and field experiments. The sex-pheromone-based insect-control strategy utilises 100-microliters droplets of a sticky, paste-like formulation containing 1 mg g-1 (E,E)-8,10-dodecadien-1-ol (codlemone) as an attractant for male moths and 40 mg g-1 cyfluthrin, a contact insecticide, applied to branches in the upper parts of the tree crown. The longevity of the treatment under field conditions was assessed in the laboratory by biological testing of variously aged samples of the attracticide formulation which had been applied to the bark of apple trees growing in commercial orchards. Electroantennogram responses of male moth antennae were used to compare codlemone release from the attracticide after different lengths of environmental exposure. Changes in insecticidal efficacy of the same samples were assessed with reference to the speed of knockdown (KT50) and the mortalities after 48 h among populations of male moths confined in cages containing samples of fresh and field-aged formulations. Gradual declines in both the amount of pheromone released and insecticidal activity were observed over the 10-week period of the experiments. Various factors associated with the behaviour of codling moths in the field which might influence the attracticide strategy were also investigated. Although the vertical position of attracticide sources within apple trees had a strong influence on their attractiveness, their horizontal position had none. Results of field trials showed that efficacy of the attracticide depends on the population density of the pest. Under the conditions of the current study a density of three or more sources per tree (= 4500 sources per ha) was required to attain satisfactory levels of codling moth control.

In a previous study we have reported that both (E,Z)-8,10-dodecadienol (E,Z) and (Z,Z)-8,10-dodecadienol (Z,Z) isomers inhibit the attraction of male codling moth, Cydia pomonella L. when added to (E,E)-8,10-dodecadienol (E,E) while the (Z,E)-8,10-dodecadienol (Z,E) isomer induces slight increase in the number of males attracted to the pheromone source. In the present study, we have tested the behavioral activity of the individual geometrical isomers E,Z; Z,E and Z,Z. A few number of codling moth males flew to the Z,E-isomer while the other two isomers (i.e. E,Z and Z,Z) did not elicit any upwind orientation. Analysis of the flight behavior to the E,E- and Z,E-isomer showed significant differences in most of the flight parameters evaluated. Based on the biological observations and molecular modeling, we suggest that the behavioral activity of the Z,E-isomer is due to presence of specific receptors for this isomer on male antennae and not to its structural resemblance to the E,E-isomer. These results underline the importance of the Z,E-isomer in sex attraction of male codling moth.