Chemical composition and antibacterial effects of Etlingera elatior (Jack) R.M. Smith against Staphylococcus aureus efflux pumps.

Multidrug resistance is a significant health problem worldwide, with increasing mortality rates, especially in the last few years. In this context, a consistent effort has been made to discover new antibacterial agents, and evidence points to natural products as the most promising source of bioactive compounds. This research aimed to characterize the antibacterial effect of the essential oil of Etlingera elatior (EOEE) and its major constituents against efflux pump-carrying Staphylococcus aureus strains. The essential oil was extracted from fresh inflorescences by hydrodistillation. Chemical analysis was performed using gas chromatography coupled to mass spectrometry (GC-MS) and gas chromatography equipped with a flame ionization detector (GC-FID). The strains RN-4220, 1199B, IS-58, and 1199 of S. aureus were used to evaluate the antibacterial activity and the inhibition of efflux pumps. A total of 23 compounds were identified, including dodecanal and 1-dodecanol as major compounds. EOEE and dodecanal showed weak activity against the strains, while 1-dodecanol inhibited bacterial growth at low concentrations, indicating strong antibacterial activity. In addition, this compound potentiated the activity of norfloxacin against S. aureus 1199. In conclusion, 1-dodecanol was identified as the most effective compound of EOEE, showing significant potential to be used in antibacterial drug development.

Dodecanol, metabolite of entomopathogenic fungus Conidiobolus coronatus, affects fatty acid composition and cellular immunity of Galleria mellonella and Calliphora vicina.

One group of promising pest control agents are the entomopathogenic fungi; one such example is Conidiobolus coronatus, which produces a range of metabolites. Our present findings reveal for the first time that C. coronatus also produces dodecanol, a compound widely used to make surfactants and pharmaceuticals, and enhance flavors in food. The main aim of the study was to determine the influence of dodecanol on insect defense systems, i.e. cuticular lipid composition and the condition of insect immunocompetent cells; hence, its effect was examined in detail on two species differing in susceptibility to fungal infection: Galleria mellonella and Calliphora vicina. Dodecanol treatment elicited significant quantitative and qualitative differences in cuticular free fatty acid (FFA) profiles between the species, based on gas chromatography analysis with mass spectrometry (GC/MS), and had a negative effect on G. mellonella and C. vicina hemocytes and a Sf9 cell line in vitro: after 48 h, almost all the cells were completely disintegrated. The metabolite had a negative effect on the insect defense system, suggesting that it could play an important role during C. coronatus infection. Its high insecticidal activity and lack of toxicity towards vertebrates suggest it could be an effective insecticide.

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.

Deletion of the Golgi Ca2+-ATPase PMR1 gene potentiates antifungal effects of dodecanol that depend on intracellular Ca2+ accumulation in budding yeast.

One strategy for overcoming infectious diseases caused by drug-resistant fungi involves combining drugs rendered inactive by resistance with agents targeting the drug resistance mechanism. The antifungal activity of n-dodecanol disappears as incubation time passes. In Saccharomyces cerevisiae, anethole, a principal component of anise oil, prolongs the transient antifungal effect of dodecanol by downregulating genes of multidrug efflux pumps, mainly PDR5. However, the detailed mechanisms of dodecanol's antifungal action and the anethole-induced prolonged antifungal action of dodecanol are unknown. Screening of S. cerevisiae strains lacking genes related to Ca2+ homeostasis and signaling identified a pmr1Δ strain lacking Golgi Ca2+-ATPase as more sensitive to dodecanol than the parental strain. Dodecanol and the dodecanol + anethole combination significantly increased intracellular Ca2+ levels in both strains, but the mutant failed to clear intracellular Ca2+ accumulation. Further, dodecanol and the drug combination reduced PMR1 expression and did not lead to specific localization of Pmr1p in the parental strain after 4-h treatment. By contrast with the parental strain, dodecanol did not stimulate PDR5 expression in pmr1Δ. Based on these observations, we propose that the antifungal activity of dodecanol is related to intracellular Ca2+ accumulation, possibly dependent on PMR1 function, with anethole enabling Ca2+ accumulation by restricting dodecanol efflux.

The use of micelles to deliver potential hedgehog pathway inhibitor for the treatment of liver fibrosis.

Rationale: Hedgehog (Hh) pathway plays an essential role in liver fibrosis by promoting the proliferation of hepatic stellate cells (HSCs) by enhancing their metabolism via yes-associated protein 1 (YAP1). Despite the presence of several inhibitors, Hh signaling cannot be controlled exclusively due to their poor efficacy and the lack of a suitable delivery system to the injury site. Therefore, it is rationale to develop new potent Hh inhibitors and suitable delivery carriers. Methods: Based on the structure and activity of Hh inhibitor GDC-0449, we replaced its sulfonamide group with two methylpyridine-2yl at amide nitrogen to synthesize MDB5. We compared the Hh pathway inhibition and anti-fibrotic effect of MDB5 with GDC-0449 in vitro. Next, we developed MDB5 loaded micelles using our methoxy poly(ethylene glycol)-blockpoly(2-methyl-2-carboxyl-propylene carbonate-graft-dodecanol (PEG-PCC-g-DC) copolymer and characterized for physicochemical properties. We evaluated the therapeutic efficacy of MDB5 loaded micelles in common bile duct ligation (CBDL) induced liver fibrosis, mouse model. We also determined the intrahepatic distribution of fluorescently labeled micelles after MDB5 treatment. Results: Our results show that MDB5 was more potent in inhibiting Hh pathway components and HSC proliferation in vitro. We successfully developed MDB5 loaded micelles with particle size of 40 ± 10 nm and drug loading up to 10% w/w. MDB5 loaded micelles at the dose of 10 mg/kg were well tolerated by mice, without visible sign of toxicity. The serum enzyme activities elevated by CBDL was significantly decreased by MDB5 loaded micelles compared to GDC-0449 loaded micelles. MDB5 loaded micelles further decreased collagen deposition, HSC activation, and Hh activity and its target genes in the liver. MDB5 loaded micelles also prevented liver sinusoidal endothelial capillarization (LSEC) and therefore restored perfusion between blood and liver cells. Conclusions: Our study provides evidence that MDB5 was more potent in inhibiting Hh pathway in HSC-T6 cells and showed better hepatoprotection in CBDL mice compared to GDC-0449.

Curcumin potentiates the fungicidal effect of dodecanol by inhibiting drug efflux in wild-type budding yeast.

Drug resistance commonly occurs when treating immunocompromised patients who have fungal infections. Curcumin, is a compound isolated from Curcuma longa, has been reported to inhibit drug efflux in several human cell lines and nonpathogenic budding yeast Saccharomyces cerevisiae cells that overexpresses the ATP-binding cassette (ABC) transporters S. cerevisiae Pdr5p and pathogenic Candida albicans Cdr1p and Cdr2p. The aim of this study was to examine the effects of curcumin on multidrug resistance in a wild-type strain of the budding yeast with an intrinsic expression system of multidrug efflux-related genes. The antifungal activity of dodecanol alone was temporary against S. cerevisiae; however, restoration of cell viability was completely inhibited when the cells were co-treated with dodecanol and curcumin. Furthermore, restriction of rhodamine 6G (R6G) efflux from the cells and intracellular accumulation of R6G were observed with curcumin treatment. Reverse transcription-polymerase chain reaction analysis revealed that curcumin reduced the dodecanol-induced overexpression of the ABC transporter-related genes PDR1, PDR3 and PDR5 to their control levels in untreated cells. Curcumin can directly restrict the glucose-induced drug efflux and inhibits the expression of the ABC transporter gene PDR5, and can thereby inhibit the efflux of dodecanol from S. cerevisiae cells. Curcumin is effective in potentiating the efficacy of antifungal drugs via its effects on ABC transporters. SIGNIFICANCE AND IMPACT OF THE STUDY: Drug resistance is common in immunocompromised patients with fungal infections. Curcumin, isolated from Curcuma longa, inhibits drug efflux in nonpathogenic budding yeast Saccharomyces cerevisiae cells overexpressing ABC transporters S. cerevisiae Pdr5p and pathogenic Candida albicans Cdr1p and Cdr2p. We examined the effects of curcumin on multidrug resistance in a wild-type strain of the budding yeast with an intrinsic expression system of multidrug efflux-related genes. Curcumin directly inhibited drug efflux and also suppressed the PDR5 expression, thereby enhancing the antifungal effects. Thus, curcumin potentially promotes the efficacy of antifungals via its effects on ABC transporters in wild-type fungal strains.

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.

Bioactive phenylpropanoid analogues from Piper betle L. var. birkoli leaves.

Phytochemical analyses of the chloroform extract of Piper betle L. var. birkoli, Piperaceae, leaves led to the isolation of two new phenylpropanoid analogues: bis-chavicol dodecanoyl ester (2) and bis-hydroxychavicol dodecanoyl ester (3), along with one known compound: allyl-3-methoxy-4-hydroxybenzene (1) on the basis of spectroscopic data 1D (1H and 13C) and 2D (1H-1H COSY and HMBC) NMR, as well as ESI-MS, FT-IR, HR-ESI-MS and LC-ESI-MS. Compound 2 and 3 exhibited excellent antioxidant DPPH radical scavenging activity with IC50 values of 12.67 µg/mL and 1.08 µg/mL compared to ascorbic acid as a standard antioxidant drug with IC50 value of 6.60 µg/mL. Evaluation of cytotoxic activity against two human oral cancer cell lines (AW13516 and AW8507) showed significant effect with GI50 values of 19.61 and 23.01 µg/mL for compound 2 and 10.25 and 13.12 µg/mL for compound 3, compared to Doxorubicin® as a standard cytotoxic drug with GI50 value of < 10 µg/mL.

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.

Anethole potentiates dodecanol's fungicidal activity by reducing PDR5 expression in budding yeast.

BACKGROUND: trans-Anethole (anethole), a major component of anise oil, has a broad antimicrobial spectrum and a weaker antimicrobial potency than other available antibiotics. When combined with polygodial, nagilactone E, and n-dodecanol, anethole has been shown to exhibit synergistic antifungal activity against a budding yeast, Saccharomyces cerevisiae, and a human opportunistic pathogenic yeast, Candida albicans. However, the mechanism underlying this synergistic effect of anethole has not been characterized. METHODS: We studied this mechanism using dodecanol-treated S. cerevisiae cells and focusing on genes related to multidrug efflux. RESULTS: Although dodecanol transiently reduced the number of colony forming units, this recovered to levels similar to those of untreated cells with continued incubation beyond 24h. Reverse transcription polymerase chain reaction analysis revealed overexpression of an ATP-binding cassette (ABC) transporter gene, PDR5, in addition to a slight increase in PDR11, PDR12, and PDR15 transcriptions in dodecanol-treated cells. In the presence of anethole, these effects were attenuated and the fungicidal activity of dodecanol was extended. Dodecanol showed longer lasting fungicidal activity against a Δpdr5. In addition, Δpdr3 and Δlge1, lack transcription factors of PDR5 and PDR3, were partly and completely susceptible to dodecanol, respectively. Furthermore, combination of anethole with fluconazole was also found to exhibit synergy on C. albicans. CONCLUSIONS: These results indicated that although anethole reduced the transcription of several transporters, PDR5 expression was particularly relevant to dodecanol efflux. GENERAL SIGNIFICANCE: Anethole is expected to be a promising candidate drug for the inhibition of efflux by reducing the transcription of several ABC transporters.

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.

Labware additives identified to be selective monoamine oxidase-B inhibitors.

Plastic labware is used in all processes of modern pharmaceutical research, including compound storage and biological assays. The use of these plastics has created vast increases in productivity and cost savings as experiments moved from glass test tubes and capillary pipettes to plastic microplates and multichannel liquid handlers. One consequence of the use of plastic labware, however, is the potential release of contaminants and their resultant effects on biological assays. We report herein the identification of biologically active substances released from a commonly used plastic microplate. The active contaminants were identified by gas chromatography-mass spectroscopy as dodecan-1-ol, dodecyl 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoate, and dodecanoic acid, and they were found to be selective monoamine oxidase-B inhibitors.

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.

Sensory adaptation of antennae and sex pheromone-mediated flight behavior in male oriental fruit moths (Leptidoptera: Tortricidae) after prolonged exposure to single and tertiary blends of synthetic sex pheromone.

Sensory adaptation has been measured in the antennae of male Grapholita molesta (Busck) after 15 min of exposure to its main pheromone compound (Z)-8-dodecen-1-yl acetate (Z8-12:OAc) at the aerial concentration of 1 ng/m(3) measured in orchards treated with pheromone for mating disruption. Exposing males to this aerial concentration of Z8-12:OAc for 15 min, however, had only a small effect on their ability to orientate by flight to virgin calling females in a flight tunnel. Experiments were undertaken to determine if exposure to the main pheromone compound in combination with the two biologically active minor compounds of this species, (E)-8-dodecen-1-yl acetate (E8-12:OAc) and (Z)-8-dodecen-1-ol (Z8-12:OH) would induce greater levels of sensory adaptation and have a greater effect on male sexual behavior. The exposure of male antennae to 0.5 g/m(3) air of one of the three pheromone compounds induced sensory adaptation to this compound and to the other two pheromone compounds demonstrating cross adaptation. Average percentage sensory adaptation to a pheromone compound was similar after 15 min of exposure to 1 ng/m(3) air of Z8-12:OAc, or to 1 ng/m(3) air of a 1:1:1 or 93:6:1 blend of Z8-12:OAc, E8-12:OAc, and Z8-12:OH. The exposure of males to 1 ng/m(3) air of Z8-12:OAc or the two ratios of Z8-12:OAc, E8-12:OAc, and Z8-12:OH for 15 min had no effect on their ability to orientate to a virgin calling female. The implications of these results for the operative mechanisms of sex pheromone-mediated mating disruption of this species are discussed.

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.

Membrane-assisted extractive butanol fermentation by Clostridium saccharoperbutylacetonicum N1-4 with 1-dodecanol as the extractant.

A polytetrafluoroethylene (PTFE) membrane was used in membrane-assisted extractive (MAE) fermentation of acetone-butanol-ethanol (ABE) by Clostridium saccharoperbutylacetonicum N1-4. The growth inhibition effects of 1-dodecanol, which has a high partition coefficient for butanol, can be prevented by employing 1-dodecanol as an extractant when using a PTFE membrane. Compared to conventional fermentation, MAE-ABE fermentation with 1-dodecanol decreased butanol inhibition and increased glucose consumption from 59.4 to 86.0 g/L, and total butanol production increased from 16.0 to 20.1g/L. The maximum butanol production rate increased from 0.817 to 0.979 g/L/h. The butanol productivity per membrane area was remarkably high with this system, i.e., 78.6g/L/h/m(2). Therefore, it is expected that this MAE fermentation system can achieve footprint downsizing.

Synthesis and field test of three candidates for soybean pod borer's sex pheromone.

Three candidates for the soybean pod borer's sex pheromone, dodec-10-en-1-yl acetate (E:Z = 95:5) (9a), (E, E)-dodeca-8, 10-dien-1-yl acetate (9b) and (E)-dodec-8-en-1-yl acetate (9c), were synthesized through the coupling reaction between Grignard reagents and acetates catalyzed by Li2CuCl4. Furthermore, the compounds 9a, 9b, and 9c, when tested in the field, showed that dodec-10-en-1-yl acetate (E:Z = 95:5) (9a) has promise as a lure for male soybean pod borer.