RESUMEN
Ethyl cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure-activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chemistry (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined. The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the molecules, and the effects of the properties of the parent alcohol part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochemical descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were methyl 3-phenylpropanoates monosubstituted with chloro, fluoro, or methyl groups and the 3,4-dichlorinated methyl 3-phenylpropanoate.
Asunto(s)
Control de Plagas/métodos , Feromonas/química , Pinus/química , Propionatos/química , Gorgojos/efectos de los fármacos , Acrilatos/química , Acrilatos/farmacología , Animales , Conducta Alimentaria/efectos de los fármacos , Femenino , Masculino , Feromonas/farmacología , Propionatos/farmacología , Relación Estructura-Actividad , Gorgojos/fisiologíaRESUMEN
Feeding and oviposition in the pine weevil Hylobius abietis (Linnaeus) were monitored under laboratory conditions in two long-term experiments lasting over an extended breeding season. Data were also collected from weevils under semi-natural conditions outdoors. In addition, the effects of crowding and starvation were studied in separate experiments. During the main peak oviposition period, female H. abietis consumed 50% more bark tissue than males. When oviposition ceased, the feeding rate of the females declined to the same level as in the males. The rates and spatial distribution patterns of oviposition and feeding were clearly affected by climatic conditions and the degree of crowding. Females were estimated to lay on average 0.8 eggs per day during the season under outdoor conditions. The realized fecundity of a female weevil during the first season was estimated to be approximately 70 eggs. The estimated average rate of feeding was 23 mm2 of Scots pine bark per weevil per day. This implies that planted seedlings can only constitute a minor part of the food resources needed to sustain H. abietispopulations of the size that usually appear on fresh clear-cuttings in northern Europe.
Asunto(s)
Escarabajos/fisiología , Ingestión de Alimentos , Oviposición/fisiología , Alimentación Animal , Animales , Cruzamiento , Escarabajos/crecimiento & desarrollo , Escarabajos/metabolismo , Femenino , Masculino , Densidad de Población , Estaciones del Año , InaniciónRESUMEN
Pine weevils (Hylobius abietis) fed less on bark of lodgepole pine (Pinus contorta) than on bark of Scots pine (P. sylvestris). Two pine weevil antifeedants, ethyl trans-cinnamate and ethyl 2,3-dibromo-3-phenyl-propanoate, were isolated from bark of lodgepole pine. These two compounds significantly reduced pine weevil feeding in a laboratory bioassay. In field assays, the second compound significantly decreased pine weevil damage on planted seedlings. Ethyl 2,3-dibromo-3-phenylpropanoate has not previously been reported as a natural product.
Asunto(s)
Cinamatos/aislamiento & purificación , Escarabajos , Conducta Alimentaria , Fenilpropionatos/aislamiento & purificación , Pinus/química , Plantas Comestibles/química , Animales , Bioensayo , Cinamatos/química , Cinamatos/farmacología , Fenilpropionatos/química , Fenilpropionatos/farmacología , FeromonasRESUMEN
Responses of threeHylastes species,Dryocoetes autographus, and twoHylobius species to terpenes and ethanol were studied in field experiments on clear-cut forest sites in Sweden using baited ground traps.α-Pinene alone did not attract any of the six species. A terpene blend (spruce turpentine consisting mainly ofα-pinene,ß-pinene, and 3-carene) attractedHylastes cunicularius, H. brunneus, andHylobius abietis in some experiments, but not in others. The attractiveness of ethanol also varied; the only species consistently attracted wasH. abietis. Baits containing both terpenes and ethanol, particularly the combination of spruce turpentine and ethanol, were attractive to all species exceptHylobius pinastri. InH. abietis, the terpene plus ethanol/ ethanol catch ratios increased during early summer. Seasonal differences in catch levels were observed inH. cunicularius andH. abietis. The addition ofα-pinene reduced the attractiveness of the combination of spruce turpentine and ethanol toH. cunicularius, H. opacus, andD. autographus. The differences in response to the volatiles between species are probably related to differences in reproductive behavior and host preferences.