Use of Starch Granules Enriched with Carvacrol for the Lesser Mealworm, Alphitobius diaperinus Control in Chicken House: Effects on Insects and Poultry.

The aim of this study was to investigate the effect of starch granules enriched with carvacrol and mixed with straw pellets (as poultry litter) on the mortality of larvae and adults of the lesser mealworm, Alphitobius diaperinus Panzer, a cosmopolitan pest inhabiting chicken houses in vast numbers worldwide. Additionally, the effect of starch granules on the growth parameters and survival of broiler chickens exposed to treated litter was examined. In this study, granules containing 3, 5, and 10% carvacrol was used. In a simulated chicken house bioassay, this material was mixed with pellets in three different proportions: 30/70%, 40/60%, and 50/50% (granules/pellets, respectively). On this medium, young larvae (approximately 10 days old), older larvae (last stage before pupa), and unsexed 7-10 days old adults of the lesser mealworm, with access to food, were colonized. Experiments were performed at 29°C in the dark. The study shows that poultry litter with the addition of starch granules enriched with 10% of carvacrol in the proportion of 40:60% (granules:pellets) appears to be the optimal medium applicable to broiler houses for A. diaperinus control. In this environment, all larvae and adults died within 3-4 days and the overall development of the experimental chickens was similar to that of the control. However, the feed conversion rate was slightly higher in the treated group (1.72) than in the control group (1.56). The average final body weight in the treated group was 100 g lower than that in the control group (the differences were not statistically significant).

Synthesis and biological activity of new derivatives with the preserved carane system.

Terpenoid derivatives, which contain a preserved carane system in their structure, exhibit a broad spectrum of biological activities. Among them, we can distinguish insecticides, structures with pharmacological application etc. In the presented paper, the substrate - (-)-cis-caran-trans-4-ol was transformed using the reactions of typical organic synthesis to obtain novel derivatives. Most importantly, bromolactone ((-)-(1R,4R,6S)-2'-(bromomethyl)-4,7,7-trimethylspiro[bicyclo[4.1.0]heptan-3,3'-furan]-5'(4'H)-one) with the preserved carane system was synthesized. This bromolactone was tested for antifeedant activity against the lesser mealworm, Alphitobius diaperinus Panzer, and peach potato aphid (Myzus persicae). In addition, its moderate antibacterial activity was observed against the Bacillus subtilis strain (with Minimal Inhibitory Concentration of 200 µg/mL).

Synthesis and Biological Activity of New 4-tert-Butylcyclohexanone Derivatives.

In the synthesis performed in this study, derivatives of 4-tert-butylcyclohexanone 1 were obtained using typical reactions of organic synthesis. The bioactivity of the selected compounds was evaluated. 1-(Bromomethyl)-8-tert-butyl-2-oxaspiro[4.5]decan-3-one (5) was characterized by attractant properties against larvae and a weak feeding deterrent activity against adults of Alphitobius diaperinus Panzer. This bromolactone was a moderate antifeedant towards Myzus persicae Sulzer. In addition, ethyl (4-tert-butylcyclohexylidene)acetate (2) and bromolactone 5 displayed antibacterial activity. The strongest bacteriostatic effect was observed against Gram-positive strains: Bacillus subtilis and Staphylococcus aureus. The bromolactone 5 also limited the growth of Escherichia coli strain.

Microbial Hydrolysis of Racemic ß-Aryl-γ-ethylidene-γ-lactones and Antifeedant Activity of the Products against Alphitobius diaperinus Panzer.

Hydrolysis of (±)-ß-aryl-γ-ethylidene-γ-lactones by fungal strain Aspergillus ochraceus AM370 afforded (−)-(S)-γ-ethylidene-γ-lactones 2a⁻d and (+)-(R)-γ-ketoacids 3a⁻d. Enantiomeric purity of the unreacted lactones was strictly related to a size of an aryl substituent at C-4 of γ-lactone ring, with the highest ee (77%) obtained for the (−)-(S)-γ-ethylidene-γ-lactone possessing unsubstituted benzene ring (2a) and the lowest one (15%) determined for the (−)-(S)-γ-ethylidene-γ-lactone with bulky 1,3-benzodioxole system (2d). Lactones 2a⁻d, both racemic and enantiomerically enriched, as well as products of their hydrolysis showed varying degrees of feeding deterrent activity against lesser mealworm, Alphitobius diaperinus Panzer, which depended on the structure of the compound and the developmental stage of the lesser mealworm. In the case of adults, more active were γ-lactones 2a⁻d, compared with ketoacids 3a⁻d. Only in the case of lactone 2a was the effect of configuration of stereogenic center on the activity found. Particularly strong deterrents against this stage (T > 180) were racemic and (−)-(S)-γ-ethylidene-γ-lactone with p-methoxysubstituted phenyl ring (2c).

Chemical composition, antimicromicrobial activity and insecticidal activity against the lesser mealworm Alphitobius diaperinus (Panzer) (Coleoptera: Tenebrionidae) of Origanum vulgare L. ssp. hirtum (Link) and Artemisia dracunculus L. essential oils.

BACKGROUND: Essential oils (EOs) from Artemisia dracunculus L. and Origanum vulgare L. ssp. hirtum were obtained and the qualitative and quantitative chemical composition of the extracts was investigated. The insecticidal activity of EOs against the larval stages of Alphitobius diaperinus (Panzer) was studied. Moreover, the antimicrobial activity of these oils against pathogens transmitted by this pest was also investigated. RESULTS: The obtained results indicate the possibility of using Greek oregano EO with a high content of carvacrol as a feed additive in poultry nutrition. The use of the Greek oregano oil at 1% (w/w) dose showed stronger reduction of body weight gain of stage IV larvae. Their body mass was only 10.92% of the control. Moreover, EOs from O. vulgare strongly inhibited the growth of tested bacterial strains as well as Candida albicans. CONCLUSION: Greek oregano EO may be a good alternative to antibiotic growth promoters and coccidiostats whose use in feeding farm animals has been prohibited since January 2006 under European Union directives. The introduction of O. vulgare L. ssp. hirtum EO into the premises of farm and poultry houses may help to improve sanitary conditions and control of the lesser mealworm inhabiting these buildings. © 2017 Society of Chemical Industry.

Alkyl-Substituted δ-Lactones Derived from Dihydrojasmone and Their Stereoselective Fungi-Mediated Conversion: Production of New Antifeedant Agents.

A chemoenzymatic method was applied to obtain optically pure alkyl-substituted δ-lactones. First, chemical Baeyer-Villiger oxidation of dihydrojasmone (1) was carried out, affording two new alkyl-substituted δ-lactones: 3,4-dihydro-5-methyl-6-pentyl-2H-pyran-2-one (2) and 5-methyl-6-pentyl-1,13-dioxabicyclo[4.1.0]heptan-2-one (3). In the next step, fungal strains were investigated as biocatalysts to enantioselective conversion of δ-lactones (2) and (3). The fungal cultures: Fusarium culmorum AM10, Fusarium equiseti AM15 and Beauveria bassiana AM278 catalyzed the stereoselective hydration of the double bond of lactone (2) (ee = 20%-99%) while Didymosphaeria igniaria KCh6670 proved to be the best biocatalyst for the reduction of carbonyl group in the epoxylactone (3) (ee = 99%). In both cases, chiral oxyderivatives were obtained in low to high yields (7%-91%). The synthetic lactones (2), (3) and its derivatives (4), (5) were tested for their antifeedant activity towards larvae and adults of lesser mealworm (Alphitobius diaperinus Panzer) and peach potato aphid (Myzus persicae [Sulzer]) and some of them were active towards studied insects.

Effects of halolactones with strong feeding-deterrent activity on the growth and development of larvae of the lesser mealworm, Alphitobius diaperinus (Coleoptera: Tenebrionidae).

The effects of dietary applied of ß-damascone and its synthetic derivatives γ- and δ-halolactones, which show strong antifeedant activity, on the growth and development of larvae of the lesser mealworm, Alphitobius diaperinus Panzer (Coleoptera: Tenebrionidae), were studied. Bioassays were performed in a dose-dependent manner. In the bioassays, oat flakes treated with 1.0, 0.5, and 0.1 % (w/v) acetone solutions of the tested compound or acetone alone as control were served as food. The experiments were conducted using 2-week-old larvae with an average body weight of 4.35-4.88 mg. High correlations between antifeedant activity and larvicidal and growth-inhibitory effects were observed. Larvae reared on diets containing the compounds (at a concentration of 1 %) with high deterrent activity were characterized by a prolonged period of development, lower body weight gain, and strong tendency for cannibalism as a result of starvation. The control larvae ended their development after 24 days with a mean body weight of 22.9 mg. At the same developmental time, the mean body weights of larvae treated with the δ-halolactones γ-chloro- and γ-bromo-δ-lactone were only 60.3 % and 43.2 % of that of the control larvae. The larval periods for larvae on the diets containing γ-chloro- and γ-bromo-δ-lactone were 33 and 41 days, respectively. The larval developmental time and body weight gain were not significantly influenced by lower doses of the compounds, with the exception of γ-bromo-δ-lactone. This compound, when applied at a concentration of 0.5 %, significantly prolonged larval development as compared to the control larvae, and caused high mortality of larvae and pupae. The adult emergence percentage was 37.51 % when this treatment was applied, as compared to 90.0 % in the control. Thus, ß-damascone derivatives with a lactone ring exhibit both dose-dependent behavioral effects and post-ingestion toxicity against A. diaperinus larvae, and may have the potential to control this pest.

Synthesis and Antifeedant Activity of Racemic and Optically Active Hydroxy Lactones with the p-Menthane System.

Two racemic and two enantiomeric pairs of new δ-hydroxy-γ-lactones based on the p-menthane system were prepared from racemic and optically active cis- and trans-piperitols. The Johnson-Claisen rearrangement of the piperitols, epoxidation of the γδ-unsaturated esters, and acidic lactonization of the epoxy esters were described. The structures of the compounds were confirmed spectroscopically. The antifeedant activities of the hydroxy lactones and racemic piperitone were evaluated against three insect pests: lesser mealworm, Alphitobius diaperinus (Panzer); Colorado potato beetle, Leptinotarsa decemlineata (Say); and peach-potato aphid, Myzus persicae (Sulz.). The chemical transformation of piperitone by the introduction of a lactone moiety and a hydroxy group changed its antifeedant properties. Behavioral bioassays showed that the feeding deterrent activity depended on the insect species and the structure of the compounds. All hydroxy lactones deterred the settling of M. persicae. Among chewing insects, the highest sensitivity showed A. diaperinus adults.

Structure-related antifeedant activity of halolactones with a p-menthane system against the lesser mealworm, Alphitobius diaperinus Panzer.

BACKGROUND: Feeding deterrent activity of synthetic halogen lactones against larvae and adults of the lesser mealworm, Alphitobius diaperinus Panzer, in laboratory choice and no-choice tests was studied. The compounds were synthesised from racemic and enantiomerically enriched (ee = 91-98%) cis- and trans-piperitols, which were obtained from (±)-piperitone. RESULTS: Structure-activity relationship studies identified several synthetic halolactones with a very strong feeding deterrent activity. The most active were the enantiomeric chlorolactones with chiral centre configurations (1S,4S,5R,6R) and (1R,4R,5S,6S) and their racemic mixture. The racemic bromo- and iodolactones obtained from cis-piperitol and saturated lactones with a chiral centre configuration (1R,4S,6R) were also very good antifeedants in comparison with piperitone. Most of the studied compounds were better antifeedants against adults than against larvae-among the 21 compounds, only one bromolactone with a chiral centre configuration (1S,4R,5R,6R) was a weaker deterrent for adults. CONCLUSION: Chemical transformation of the piperitone molecule by the introduction of a lactone function and a halogen atom strongly changed its antifeedant properties against the lesser mealworm. Optimum activity is dependent on the presence of a chlorine atom at C-5 of the cyclohexane ring. The activity of bromo- and iodolactones depended strongly on the chiral centre configuration and the halogen substituent.

An anomaly within the genital system in a female Ascaris suum Goeze.

The authors describe an individual of the female Ascaris suum Goeze with a unique genital system. A female with such an anomaly was found during laboratory classes of Invertebrate Zoology at the Faculty of Biology and Environmental Protection, NCU. The specimen was about 200 mm long, and the total length of the reproductive system was 1970 mm. Further comparative analysis between unchanged and changed individuals revealed differences in the length of individual sections of the studied system, as well as in the diameter of the uterus. The described case is extremely interesting because of the phenomenon of eutely occurring in nematodes. The exact cause and mechanism of abnormalities described in Ascaris suum are not known and difficult to explain experimentally because of the extremely small number of these anomalies. Moreover, the interpretation of the anomaly is difficult because of the specific behavior and complex morphogenesis of this endoparasite.

Synthesis and insect antifeedant activity of precocene derivatives with lactone moiety.

Starting from precocenes I and II, four of their derivatives with a lactone moiety were obtained. The compounds have been assessed as antifeedants against several diverse insect species including the storage pests the confused flour beetle (Tribolium confusum Duv., larvae and adults), the granary weevil beetle (Sitophilus granarius L., adults), and the khapra beetle (Trogoderma granarium Ev., larvae) and against the herbivorous pest insects Colorado potato beetle (Leptinotarsa decemlineata Say, adults and larvae) and aphids (Myzus persicae Sulz.). Precocenes, especially precocene II, showed a very strong antifeedant effect against all storage pests and aphids. The introduction of a lactone moiety caused a decrease in antifeedant activity against these species. Both precocenes were moderately active against L. decemlineata adults. The best antifeedants to this species were precocene derivatives, especially iodolactones. The introduction of iodine into a molecule had a great effect on the antifeedant activity of those compounds.