Molecular and Functional Characterization of Three General Odorant-Binding Protein 2 Genes in Cydia pomonella (Lepidoptera: Tortricidae).

General odorant-binding proteins (GOBPs) play a crucial role in the detection of host plant volatiles and pheromones by lepidopterans. Previous studies identified two duplications in the GOBP2 gene in Cydia pomonella. In this study, we employed qRT-PCR, protein purification, and fluorescence competitive binding assays to investigate the functions of three GOBP2 genes in C. pomonella. Our findings reveal that CpomGOBP2a and CpomGOBP2b are specifically highly expressed in antennae, while CpomGOBP2c exhibits high specific expression in wings, suggesting a potential divergence in their functions. Recombinant proteins of CpomGOBP2a, CpomGOBP2b, and CpomGOBP2c were successfully expressed and purified, enabling an in-depth exploration of their functions. Competitive binding assays with 20 host plant volatiles and the sex pheromone (codlemone) demonstrated that CpomGOBP2a exhibits strong binding to four compounds, namely butyl octanoate, ethyl (2E,4Z)-deca-2,4-dienoate (pear ester), codlemone, and geranylacetone, with corresponding dissolution constants (Ki) of 8.59993 µM, 9.14704 µM, 22.66298 µM, and 22.86923 µM, respectively. CpomGOBP2b showed specific binding to pear ester (Ki = 17.37481 µM), while CpomGOBP2c did not exhibit binding to any tested compounds. In conclusion, our results indicate a functional divergence among CpomGOBP2a, CpomGOBP2b, and CpomGOBP2c. These findings contribute valuable insights for the development of novel prevention and control technologies and enhance our understanding of the evolutionary mechanisms of olfactory genes in C. pomonella.

Structural insights into the discrepant synergistic activity of Codlemone and (Z)-8-dodecenol towards Grapholita molesta pheromones.

BACKGROUND: Insect pheromone synergists have been widely used to produce potent pheromone products for environment-friendly pest control. Codlemone (Cod) and (Z)-8-dodecenol (Dod) are two major Grapholita molesta pheromone synergists, with Cod having greater synergism and affinity for G. molesta pheromone binding protein 2 (GmolPBP2). Uncovering structural information key to the different binding affinity of Cod and Dod to GmolPBP2 would gain insights into what causes their synergy activity discrepancy. RESULTS: Binding modes of the two synergists in the binding pocket of GmolPBP2 were analyzed and compared by molecular dynamics-based approaches. Although Cod and Dod were stabilized in a similar hydrophobic pocket, their interaction details with GmolPBP2 were divergent due to the extra double bond (C10═C11) in Cod. The C10═C11 improved the hydrophobic interactions of Cod with around residues. Such hydrophobic interaction improvement was also reflected in the raised importance of Phe11 in the GmolPBP2-Cod interaction. Not only that, the increased hydrophobic forces introduced by the C10═C11 changed the CH2-OH orientation in the GmolPBP2-Cod complex, which improved the H-bond interaction. Electrostatic complementarity analysis further indicated the positive role of C10═C11 in optimizing GmolPBP2-Cod interaction. CONCLUSION: The C10═C11 is thought to contribute greatly to Cod's stronger synergy as a group key to the higher GmolPBP2-affinity, based on which the improvement directions for Cod and Dod were addressed as well. Our findings will aid in the development and optimization of more effective pheromone synergists, resulting in more effective pheromone-based pest management.

Green Chemistry Production of Codlemone, the Sex Pheromone of the Codling Moth (Cydia pomonella), by Metabolic Engineering of the Oilseed Crop Camelina (Camelina sativa).

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 C12 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 T2 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 T4 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.

Biosynthesis of the Sex Pheromone Component (E,Z)-7,9-Dodecadienyl Acetate in the European Grapevine Moth, Lobesia botrana, Involving ∆11 Desaturation and an Elusive ∆7 Desaturase.

The European grapevine moth, Lobesia botrana, uses (E,Z)-7,9-dodecadienyl acetate as its major sex pheromone component. Through in vivo labeling experiments we demonstrated that the doubly unsaturated pheromone component is produced by ∆11 desaturation of tetradecanoic acid, followed by chain shortening of (Z)-11-tetradecenoic acid to (Z)-9-dodecenoic acid, and subsequently introduction of the second double bond by an unknown ∆7 desaturase, before final reduction and acetylation. By sequencing and analyzing the transcriptome of female pheromone glands of L. botrana, we obtained 41 candidate genes that may be involved in sex pheromone production, including the genes encoding 17 fatty acyl desaturases, 13 fatty acyl reductases, 1 fatty acid synthase, 3 acyl-CoA oxidases, 1 acetyl-CoA carboxylase, 4 fatty acid transport proteins and 2 acyl-CoA binding proteins. A functional assay of desaturase and acyl-CoA oxidase gene candidates in yeast and insect cell (Sf9) heterologous expression systems revealed that Lbo_PPTQ encodes a ∆11 desaturase producing (Z)-11-tetradecenoic acid from tetradecanoic acid. Further, Lbo_31670 and Lbo_49602 encode two acyl-CoA oxidases that may produce (Z)-9-dodecenoic acid by chain shortening (Z)-11-tetradecenoic acid. The gene encoding the enzyme introducing the E7 double bond into (Z)-9-dodecenoic acid remains elusive even though we assayed 17 candidate desaturases in the two heterologous systems.

Sexual communication of Spodoptera frugiperda from West Africa: Adaptation of an invasive species and implications for pest management.

The pest species Spodoptera frugiperda, which is native to North and South America, has invaded Africa in 2016. The species consists of two strains, the corn-strain and rice-strain, which differ in their sexual communication. When we investigated populations from Benin and Nigeria, consisting of corn-strain and rice-corn-hybrid descendants, we found no strain-specific sexual communication differences. Both genotypes exhibited the same pheromone composition, consisting of around 97% (Z)-9-tetradecenyl acetate (Z9-14:Ac), 2% (Z)-7-dodecenyl acetate (Z7-12:Ac), and 1% (Z)-9-dodecenyl acetate (Z9-12:Ac), they had similar electrophysiological responses, and all mated around three hours into scotophase. However, we found geographic variation between African and American populations. The sex pheromone of African corn-strain and hybrid descendant females was similar to American rice-strain females and showed higher percentages of the male-attracting minor component Z7-12:Ac. In addition, African males exhibited the highest antennal sensitivity towards Z7-12:Ac, while American males showed highest sensitivity towards the major pheromone component Z9-14:Ac. Increasing the production of and response to the critical minor component Z7-12:Ac may reduce communication interference with other African Spodoptera species that share the same major pheromone component. The implications of our results on pheromone-based pest management strategies are discussed.

Molecular and Functional Characterization of pheromone binding protein 1 from the Oriental Fruit Moth, Grapholita molesta (Busck).

Pheromone binding protein (PBP) is thought primarily to bind and transport the sex pheromone in moths. The accumulated studies suggest that three PBPs were identified in moth species. In Grapholita molesta, the functions of GmolPBP2 and GmolPBP3 have been previously studied. However, the function of GmolPBP1 is still unclear. Furthermore, the Cydia pomonella sex pheromone Codlemone can act as a sex pheromone synergist of G. molesta. In C. pomonella, CpomPBP1 specifically bind the Codlemone. CpomPBP1 displays high identity with GmolPBP1 (70%), indicating that the two PBPs may share a similar 3D structure thus can bind the similar or same ligands. In this study, we explored the molecular and functional characterization of GmolPBP1. GmolPBP1, bearing the typical characteristics of Lepidopteran odorant binding proteins, was closest phylogenetically to CpomPBP1. Binding studies demonstrated that GmolPBP1 exhibited strong binding affinities with (Z)-8-dodecenyl alcohol, 1-dodecanol and Codlemone. Molecular docking showed that GmolPBP1 has different ligand recognition mechanism for the three ligands. Our results suggest that GmolPBP1 functions as recognizer of (Z)-8-dodecenyl alcohol and 1-dodecanol of the female sex pheromone blend, and may be the potential transporter of Codlemone, which contributes to the synergism of the pheromone response of G. molesta by Codlemone.

Line-Trapping of Codling Moth (Lepidoptera: Tortricidae): A Novel Approach to Improving the Precision of Capture Numbers in Traps Monitoring Pest Density.

This field study of codling moth, Cydia pomonella (L.), response to single versus multiple monitoring traps baited with codlemone demonstrates that precision of a given capture number is alarmingly poor when the population is held constant by releasing moths. Captures as low as zero and as high as 12 males per single trap are to be expected where the catch mode is three. Here, we demonstrate that the frequency of false negatives and overestimated positives for codling moth trapping can be substantially reduced by employing the tactic of line-trapping, where five traps were deployed 4 m apart along a row of apple trees. Codling moth traps spaced closely competed only slightly. Therefore, deploying five traps closely in a line is a sampling technique nearly as good as deploying five traps spaced widely. But line trapping offers a substantial savings in time and therefore cost when servicing aggregated versus distributed traps. As the science of pest management matures by mastering the ability to translate capture numbers into estimates of absolute pest density, it will be important to employ a tactic like line-trapping so as to shrink the troublesome variability associated with capture numbers in single traps that thwarts accurate decisions about if and when to spray. Line-trapping might similarly increase the reliability and utility of density estimates derived from capture numbers in monitoring traps for various pest and beneficial insects.

Addition of Pear Ester With Sex Pheromone Enhances Disruption of Mating by Female Codling Moth (Lepidoptera: Tortricidae) in Walnut Orchards Treated with Meso Dispensers.

We evaluated the low-density application of 50 dispensers per hectare, in contrast to the traditional >800 dispensers per hectare in apple orchards, to achieve disruption of communication of adult codling moth, Cydia pomonella (L.), in walnuts, Juglans regia (L.), using several methods. These methods included cumulative catches of male moths in traps baited with sex pheromone (Ph) or codlemone, (E,E)-8,10-dodecadien-1-ol, or a combination of codlemone, pear ester (PE), ethyl (E,Z)-2,4-decadienoate, and acetic acid, and by examining the mating status of females. These data were collected from 2011-2014 in nontreated plots and in similar plots treated with Meso dispensers loaded with codlemone (Ph Meso) or codlemone and PE (Ph + PE Meso). Male moth captures in both the Ph and combination lure traps reduced by 88-96% and 72 to 77%, respectively, compared with traps in the nontreated plots. A significantly higher proportion of female moths were nonmated in plots treated with Ph + PE Meso dispensers (33%) than in plots treated with Ph Meso (18-26%), or left nontreated (13%). In addition, significantly fewer multiple-mated females were trapped in the Ph + PE Meso-treated plots (6%) than in either Ph Meso-treated (13-18%) or nontreated plots (23%). These data suggest that the addition of PE can effectively improve Ph-based disruption of C. pomonella in walnut orchards. In addition, these data suggest that the use of low-density hand-applied dispensers can be an effective and lower-cost approach to manage this pest in the large canopy presented by walnut orchards.

Candidate pheromone receptors of codling moth Cydia pomonella respond to pheromones and kairomones.

Olfaction plays a dominant role in the mate-finding and host selection behaviours of the codling moth (Cydia pomonella), an important pest of apple, pear and walnut orchards worldwide. Antennal transcriptome analysis revealed a number of abundantly expressed genes related to the moth olfactory system, including those encoding the olfactory receptors (ORs) CpomOR1, CpomOR3 and CpomOR6a, which belong to the pheromone receptor (PR) lineage, and the co-receptor (CpomOrco). Using heterologous expression, in both Drosophila olfactory sensory neurones and in human embryonic kidney cells, together with electrophysiological recordings and calcium imaging, we characterize the basic physiological and pharmacological properties of these receptors and demonstrate that they form functional ionotropic receptor channels. Both the homomeric CpomOrco and heteromeric CpomOrco + OR complexes can be activated by the common Orco agonists VUAA1 and VUAA3, as well as inhibited by the common Orco antagonists amiloride derivatives. CpomOR3 responds to the plant volatile compound pear ester ethyl-(E,Z)-2,4-decadienoate, while CpomOR6a responds to the strong pheromone antagonist codlemone acetate (E,E)-8,10-dodecadien-1-yl acetate. These findings represent important breakthroughs in the deorphanization of codling moth pheromone receptors, as well as more broadly into insect ecology and evolution and, consequently, for the development of sustainable pest control strategies based on manipulating chemosensory communication.

A Binary Host Plant Volatile Lure Combined With Acetic Acid to Monitor Codling Moth (Lepidoptera: Tortricidae).

Field studies were conducted in the United States, Hungary, and New Zealand to evaluate the effectiveness of septa lures loaded with ethyl (E,Z)-2,4-decadienoate (pear ester) and (E)-4,8-dimethyl-1,3,7-nonatriene (nonatriene) alone and in combination with an acetic acid co-lure for both sexes of codling moth, Cydia pomonella (L.). Additional studies were conducted to evaluate these host plant volatiles and acetic acid in combination with the sex pheromone, (E,E)-8,10-dodecadien-1-ol (codlemone). Traps baited with pear ester/nonatriene + acetic acid placed within orchards treated either with codlemone dispensers or left untreated caught significantly more males, females, and total moths than similar traps baited with pear ester + acetic acid in some assays. Similarly, traps baited with codlemone/pear ester/nonatriene + acetic acid caught significantly greater numbers of moths than traps with codlemone/pear ester + acetic acid lures in some assays in orchards treated with combinational dispensers (dispensers loaded with codlemone/pear ester). These data suggest that monitoring of codling moth can be marginally improved in orchards under variable management plans using a binary host plant volatile lure in combination with codlemone and acetic acid. These results are likely to be most significant in orchards treated with combinational dispensers. Significant increases in the catch of female codling moths in traps with the binary host plant volatile blend plus acetic acid should be useful in developing more effective mass trapping strategies.

N-Butyl sulfide as an attractant and coattractant for male and female codling moth (Lepidoptera: Tortricidae).

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.

Aerosol emitters disrupt codling moth, Cydia pomonella, competitively.

BACKGROUND: Isomate(®) CM MIST aerosol emitters (Pacific BioControl Corp, Vancouver, WA) containing 36 g of codlemone, (E,E)-8,10-dodecadien-1-ol, were deployed at various densities in a commercial apple orchard to generate dosage-response profiles in order to elucidate the behavioral mechanism of disruption. RESULTS: Moth captures decreased asymptotically as Isomate(®) CM MIST densities increased. Data fitting to Miller-Gut and Miller-de Lame plots yielded straight lines, with positive and negative slopes respectively. Catch of male moths decreased from 28 trap(-1) in the control to 0.9 trap(-1) at the highest emitter density. Disruption of >90% was realized at emitter densities greater than 5 units ha(-1) . CONCLUSION: The resulting set of profiles explicitly matched the predictions for competitive rather than non-competitive disruption. Thus, these devices probably disrupt by inducing false-plume following rather than by camouflaging traps and females. The use of 5 MIST units ha(-1) would be necessary to achieve the same level of codling moth control provided by a standard pheromone treatment with passive reservoir dispensers. The need for only a few aerosol emitters, 2.5-5 units ha(-1) , mitigates the cost of labor required to hand-apply hundreds of passive reservoir dispensers; however, a potential weakness in using this technology is that the low deployment density may leave areas of little or no pheromone coverage, where mate finding may occur. This technology is likely to benefit substantially from treatment of large contiguous blocks of crop.

Separating the attractant from the toxicant improves attract-and-kill of codling moth (Lepidoptera: Tortricidae).

The behavior of codling moth, Cydia pomonella (L.), responding to three attract-and-kill devices was compared in flight tunnel experiments measuring attraction and duration of target contact. Placing a 7.6 by 12.6 cm card immediately upwind of a rubber septum releasing pheromone, dramatically increased the duration on the target to > 60 s. In this setting, nearly all the males flew upwind, landed on the card first, and spent the majority of time searching the card. In contrast, male codling moths spent < 15 s at the source if given the lure only. In a forced contact bioassay, knockdown rate or mortality of male codling moths increased in direct proportion to duration of contact on a lambda-cyhalothrin-loaded filter paper. When this insecticide-treated paper was placed immediately upwind of the lure in the flight tunnel, > 90% of males contacting the paper were knocked down 2 h after voluntary exposure. These findings suggest that past attempts to combine insecticide directly with sex pheromones into a small paste, gel, or other forms of dollops are ill-advised because moths are likely over-exposed to pheromone and vacate the target before obtaining a lethal dose of insecticide. It is better to minimize direct contact with the concentrated pheromone while enticing males to extensively search insecticide-treated surface nearby the lure.

A portable gas chromatograph with simultaneous detection by mass spectrometry and electroantennography for the highly sensitive in situ measurement of volatiles.

Mating disruption is a sustainable method for the control of insect pests, involving the release of synthetic sex pheromones that disrupt the olfactory localization of females by males. However, the development and refinement of this strategy is hampered because current instruments lack the sensitivity to detect volatile organic chemicals in the field, and portable electroantennograms produce non-comparable relative units and distorted results in the presence of plant volatiles. To address the demand for more sensitive instruments that are suitable for the rapid in situ detection of airborne pheromones, we have developed a portable, automated needle trap device connected to a gas chromatograph, mass spectrometer, and electroantennographic detector (NTD-GC-MS/EAD) suitable for field applications. We tested the instrument by measuring the concentration of the sex pheromone (E,Z)-7,9-dodecadienyl acetate, which is used to disrupt the mating of the European grapevine moth Lobesia botrana (Lepidoptera: Tortricidae). Our data confirm that the instrument generates highly reproducible results and is highly sensitive, with a detection threshold of 3 ng/m(3) (E,Z)-7,9-dodecadienyl acetate in outside air.

Blend chemistry and field attraction of commercial sex pheromone lures to grape berry moth (Lepidoptera: Tortricidae), and a nontarget tortricid in vineyards.

Anecdotal reports by scientists and growers suggested commercial sex pheromone lures were ineffective with monitoring field populations of grape berry moth, Paralobesia viteana (Clemens), in vineyards. This study addressed the need to evaluate commercial sex pheromone lures for chemical purity and efficacy of attracting grape berry moth and a nontarget tortricid, the sumac moth, Episumus argutanus (Clemens). The percentage of chemical components from a set of eight lures from each manufacturer was found using gas chromatography-mass spectrometry and confirmed by chemical standards. No lures adhered to the 9:1 blend of (Z)-9-dodecenyl acetate (Z9-12:Ac) to (Z)-11-tetradecenyl acetate (Z11-14:Ac), though Suterra (9.1:1), ISCA (5.7:1), and Trécé (5.4:1) lures were closest. The Trécé lures contained ≍98 µg Z9-12:Ac, which is 3-51 times more than the other lures. The Suterra and ISCA lures were loaded with ≍29 and 33 µg Z9-12:Ac, and the Alpha Scents lures only contained ≍2 µg Z9-12:Ac. An antagonistic impurity, (E)-9-tetradecenyl acetate (E9-12:Ac), was found in all manufacturer lures at concentrations from 3.2 to 4.8%. Field attraction studies were done in summer 2010, and again in 2011, to evaluate commercial lures for their potential to attract P. viteana and E. argutanus in the presence of lures from other manufacturers. Separate experiments were established in two vineyards in Augusta County, VA, one with open and the other with wooded surroundings. In field experiments, Suterra lures detected P. viteana most often, Trécé lures detected more E. argutanus, and ISCA lures detected P. viteana in the open vineyard the least, while Alpha Scents lures were least attractive to E. argutanus in both environments. Fewer P. viteana were captured in the wooded versus open vineyard, which may limit the potential for sex pheromone monitoring of P. viteana in wooded vineyards.

Electrophilic derivatives antagonise pheromone attraction in Cydia pomonella.

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.

Lobesia botrana IPM: electrospun polyester microfibers serve as biodegradable sex pheromone dispensers.

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.

Total synthesis and antifungal activity of (2S,3R)-2-aminododecan-3-ol.

We report the total synthesis of (2S,3R)-2-aminododecan-3-ol has been achieved starting from commercially available 10-undecenoic acid. The key steps involved are Sharpless asymmetric epoxidation, Miyashita's boron-directed C-2 regioselective azidolysis, generated the asymmetric centers and in situ detosylation and reduction of azido tosylate. The antifungal activity of the synthesized (2S,3R)-2-aminododecan-3-ol was evaluated on several Candida strains and was comparable to miconazole, a standard drug.

Evaluating dispensers loaded with codlemone and pear ester for disruption of codling moth (Lepidoptera: Tortricidae).

Polyvinyl chloride polymer (PVC) dispensers loaded with ethyl (E,Z)-2,4-decadienoate (pear ester) plus the sex pheromone, (E,E)-8,10-dodecadien-1-ol (codlemone) of codling moth, Cydia pomonella (L.), were compared with PVC dispensers and a commercial dispenser (Isomate-C Plus) loaded with codlemone. Evaluations were conducted in replicated plots (0.1-0.2 ha) in apple, Malus domestica (Borkhausen) during both generations of codling moth from 2007 to 2009. Dispensers were applied at 1,000 ha(-1). Male captures in traps baited with virgin female moths and codlemone lures were recorded. Residual analysis of field-aged dispensers over both moth generations was conducted. Dispensers exhibited linear declines in release rates of both attractants, and pear ester was released at a significantly higher rate than codlemone during both time periods. The proportion of virgin female-baited traps catching males was significantly lower with combo dispenser TRE24 (45/110, mg codlemone/mg pear ester) during the second generation in 2007 and the combo dispensers TRE144 (45/75) and TRE145 (75/45) during the first generation in 2008 compared with Isomate-C Plus. Similarly, male catches in female-baited traps in plots treated with the combo dispensers TRE144 during the first generation in 2008 and TRE23 (75/110) during the second generation, in 2007 were significantly lower than in plots treated with Isomate-C Plus. No significant differences were found for male catches in codlemone-baited traps in plots treated with Isomate-C Plus and any of the combo dispensers. However, male catches were significantly lower in plots treated with Cidetrak CM (codlemone-only dispenser) than the combo TRE144 dispenser during both generations in 2009.

Water-stable all-biodegradable microparticles in nanofibers by electrospinning of aqueous dispersions for biotechnical plant protection.

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.