Bark of ten woody species, known to be rejected as a food source by the pine weevil, Hylobius abietis, were sequentially extracted by a Soxhlet apparatus with pentane followed by methanol. Species were alder (Alnus glutinosa), aspen (Populus tremula), beech (Fagus sylvatica), guelder rose (Viburnum opulus), holly (Ilex aquifolium), horse chestnut (Aesculus hippocastanum), lilac (Syringa vulgaris), spindle tree (Evonymus europaeus), walnut (Juglans regia), and yew (Taxus baccata). Bark of each species was collected in southern Scandinavia during the summer. Resulting extracts were tested for antifeedant activity against the pine weevil by a micro-feeding choice assay. At a dose corresponding to that in the bark, methanol extracts from Aesculus, Taxus, Ilex, and Populus were antifeedant active, while pentane extracts of Aesculus, Fagus, Syringa, and Viburnum were stimulatory. Four known antifeedants against H. abietis, the straight-chained carboxylic acids, hexanoic and nonanoic acid (C6 and C9), carvone, and carvacrol were identified by gas chromatography (GC)-mass spectrometry (MS) in several extracts. The major constituents were identified and tested for feeding deterrence. The aromatic compounds benzyl alcohol and 2-phenylethanol are new non-host plant-derived feeding deterrents for the pine weevil. Additionally, two feeding stimulants, β-sitosterol and 5-(hydroxymethyl)-2-furaldehyde, were identified. One active methanol extract of Aesculus bark was sequentially fractionated by liquid chromatography, and major compounds were tentatively identified as branched alcohols and esters of hexanoic acid. Five commercially available hexanoate esters and two commercially available branched alcohols were identified as new active antifeedants. Both stimulatory and inhibiting compounds were found in the same extracts and co-eluted in the same or adjacent fractions. The mix of semiochemicals of opposite activity in each extract or fraction could explain the stimulatory-, inhibitory-, or sometimes neutral activity. Generally, such co-occurrence confounds the isolation of antifeedants.

Linden (Tilia cordata) bark was shown to contain an antifeedant effective against the large pine weevil, Hylobius abietis. Soxhlet extraction of inner and outer bark resulted in an extract that showed antifeedant activity in a microfeeding assay. The extract was fractionated by chromatography on silica gel using gradient elution with solvents of increasing polarity. The content of the fractions obtained was monitored by thin layer- and gas chromatography. Fractions of similar chemical composition were merged. Two of the 17 fractions showed antifeedant activity in the microfeeding assay. Nonanoic acid was identified in both of these fractions. Subsequent testing in the microfeeding assay showed that nonanoic acid possessed strong antifeedant activity against H. abietis adults.

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Mercury(II) perchlorates effect the rapid and efficient concomitant deprotection/cyclization of 3,6-substituted-(silyloxypropyl)(pyridylthio)piperazinediones 6 to afford the corresponding bridged bicyclic piperazinediones 3. The pyridyl thioethers 6 are synthesized from the corresponding N-protected piperazinediones by sequential enolate alkylation followed by regio-and stereoselective enolate sulfenylation. This sequence provides an efficient "three-pot" synthesis of the bridged

A medium‐length, straight‐chain alkanoic acid, nonanoic acid, is known from laboratory microassays to be an antifeedant in adults of the large pine weevil, Hylobius abietis (L.) (Coleoptera: Curculionidae). Our hypothesis was that we could find new, less volatile alkanoic acids or related compounds suitable for field application and with improved long‐term duration. Alkanoic acids of varying chain lengths (C6–C13) were tested for antifeedant activity in H. abietis adults. Microassay choice tests showed that straight‐chain (C6–C11) alkanoic acids were active. However, high activities were restricted to the (C6–C10) acids, with the C9 (nonanoic acid) at 4 µmol cm−2 being the most active one. In a no‐choice test on pine twigs, the antifeedant effect of C10 acid was lower than that of the C8 and C9 acids. In microassays, less volatile methyl‐branched alkanoic acids exhibited lower antifeedant activities than did the corresponding straight‐chain ones. However, the most active of the methyl‐branched acids, 2‐methyldecanoic acid, had an activity similar to that of nonanoic acid. Compounds related to nonanoic acid were either active (1‐nonanol), weakly active (nonanoic anhydride), or inactive (nonanal, sodium nonanoate). The anhydride was highly active in the microassay, but less active on twigs. The antifeedant effects of the straight chain (C8–C10) alkanoic acids against pine weevil feeding were tested in the field. In contrast to the results from the twig tests, the less volatile C10 acid was more active in the field for the protection of transplants on fresh clear cuts over a 3‐month period than both the C8 and C9 acids. Phytotoxic effects of the alkanoic acids were observed both in the field and in laboratory studies. If a protective layer of paraffin was applied to the stem prior to application of the alkanoic acids, these undesired side effects were reduced.