Field and Electroantennogram Responses of the Pine Sawfly, Diprion nipponica, to Chiral Synthetic Pheromone Candidates.

Tai, Akira; Higashiura, Yasutomo; Kakizaki, Masashi; Naito, Tikahiko; Tanaka, Kazuki; Fujita, Morifumi; Sügimura, Takashi; Hara, Hideho; Hayashi, Naoaki

doi:10.1271/bbb.62.607

Cited by 21 publications

(8 citation statements)

References 7 publications

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“…Most of these pheromones have been reported in the Diprionidae and are made up of various methyl branched acetate or propionate products of diprionol (Jewett et al 1976;Ahlgren et al 1979;Anderbrant et al 1992Anderbrant et al , 2000Anderbrant et al , 2005Bergström et al 1995Bergström et al , 1998Chen et al 1997;Tai et al 1998Tai et al , 2002Wassgren et al 2000;Ostrand et al 2003;Hedenström et al 2006). Acantholyda erythrocephala differs from diprionids in that its pheromone, (Z)-6,14-pentadecadienal, and likely pheromone precursor, (Z,Z)-1,9,15-pentacosatriene, are both simple unbranched straight chain hydrocarbons.…”

Section: Discussionmentioning

confidence: 99%

Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala

et al. 2009

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Females of the pine false webworm Acantholyda erythrocephala (L) produce the sex pheromone (Z)-6, 14-pentadecadienal, which attracts flying males in the field. By using gas chromatography coupled with electroantennographic detection (GC-EAD) and mass spectrometry (GC-MS), we detected (Z)-6,14-pentadecadienal in volatile collections and in whole body extracts of female A. erythrocephala. Females, but not males, also exhibited a 25-carbon cuticular hydrocarbon, (Z,Z)-1,9,15-pentacosatriene, which can oxidize to (Z)-6,14-pentadecadienal upon exposure to air and sunlight. (Z,Z)-1,9,15-Pentacosatriene and (Z)-6,14-pentadecadienal identifications were corroborated by comparison with synthetic standards. (Z)-6, 14-Pentadecadienal is the second pheromone identified for pamphilliid sawflies, and the first to elicit strong field attraction, and thus offer potential as a pheromone lure to aid in control of this forest pest.

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Section: Discussionmentioning

confidence: 99%

Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala

et al. 2009

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“…All known sex pheromones in non-apocrita Hymenoptera have been reported to be female emitted. Sex pheromones in Diprionidae species possess acetate and/or propanoate of di-and tri-methyl-branched 2-alkanol of 11-20 carbon long backbones with different chiral centres [40][41][42][43][44][45][46][47][48][49][50]. In Cephidae, 9-acetyloxynonanal in Cephus cinctus [51] and (9Z)-octadec-9-en-4-olide in Janus integer [52] were described as sex pheromones.…”

Section: Discussionmentioning

confidence: 99%

Biology of a putative male aggregation-sex pheromone in Sirex noctilio (Hymenoptera: Siricidae)

et al. 2020

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A putative male-produced pheromone has recently been described for the global pest of pines, Sirex noctilio, but field-activity has not been demonstrated. This study aimed to investigate the pheromone biology of S. noctilio in more detail. Specifically, we i) analysed effluvia and extracts for additional compounds by gas chromatography coupled with electro-antennographic detection (GC-EAD), mass spectrometry (GC-MS) and two dimensional time of flight mass spectrometry (GC X GC TOF MS), ii) conducted dose-response experiments for putative pheromone components, iii) determined the site of synthesis/ storage of the putative pheromone and iv) determined the release rate of the putative pheromone from males and three types of lures. A blend of four compounds was identified, including the previously described (Z)-3-decenol and (Z)-4-decenol, and two new compounds (Z)-3-octenol and (Z)-3-dodecenol. All compounds elicited a response from both male and female antennae, but the strength of the response varied according to sex, compound and dose tested. (Z)-3-Decenol and (Z)-3-octenol at lower and higher doses, respectively, elicited larger responses in males and females than the other two compounds. (Z)-3-Octenol and (Z)-4-decenol generally elicited larger female than male antennal responses. The site of synthesis and/or storage in males was determined to be the hind legs, likely in the leg-tendon gland. The relative release rate of the major compound by male wasps was shown to be 90 ± 12.4 ng/min, which is between 4 and 15 times greater than that observed from typical lures used previously. These observations are consistent with the hypothesis that these compounds may mediate lek formation in S. noctilio males and lek location in females.

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“…Phenoxyl-radicals possess a wide fi eld of possible applications, e.g., as antioxidants in plants, [ 1 ] integral parts in metal complexes, [ 2,3 ] in single-molecule magnetic materials, [ 4 ] or as active materials for organic radical batteries (ORBs). [ 5,6 ] In plants, phenoxyl-radicals are generated from phenols like resveratrol, [ 1,7,8 ] α -tocopherol, [ 9 ] or vanillin [ 10 ] by oxidation with hydroxyl-and peroxyl-radicals, which are usually generated by ionizing radiation. [ 11 ] Most of these radicals are only stable for a very short time and rapidly form dimers; [ 12 ] however, there are also some stable radicals (up to several months).…”

Section: Introductionmentioning

confidence: 99%

Assorted Phenoxyl-Radical Polymers and Their Application in Lithium-Organic Batteries

Jähnert

Hager

Schubert

2016

Macromol. Rapid Commun.

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The synthesis and electrochemical characterization of novel polymers bearing phenoxyl-radicals as redox-active side chains is described. The monomers are synthesized from the corresponding phenols and quinones, respectively. These compounds are subsequently poly-merized via ring-opening metathesis polymerization. The electrochemical properties of the phenoxyl-radical polymers are characterized using cyclic voltammetry and the most promising polymer is investigated as active material in a lithium coin-cell, creating the first phenoxyl-lithium battery. These phenoxyl-containing polymers represent interesting anode materials for organic radical and lithium batteries due to their suitable redox-potentials and possibility to create batteries with higher potentials as well as straightforward synthesis procedures.

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Field and Electroantennogram Responses of the Pine Sawfly, Diprion nipponica, to Chiral Synthetic Pheromone Candidates.

Abstract: (1S, 2R, 6RS)-1,2,6-Trimethyldecyl propionate, a lower homolog of the sex pheromone of known sawflies, strongly attracted Diprion nipponica, a popular species in Japan.

Cited by 21 publications

References 7 publications

Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala

Sex Pheromone of the Pine False Webworm Acantholyda erythrocephala

Biology of a putative male aggregation-sex pheromone in Sirex noctilio (Hymenoptera: Siricidae)

Assorted Phenoxyl-Radical Polymers and Their Application in Lithium-Organic Batteries

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