Synthesis and Field Test of a Pheromone Mimic of the Pine Sawfly<i>(Neodiprion sertifer)</i>

Tai, Akira; Sügimura, Takashi; Kikukawa, T.; Naito, Chikahiko; Nishimoto, Yutaka; Morimoto, Naotake

doi:10.1271/bbb.56.1711

Cited by 6 publications

(9 citation statements)

References 5 publications

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“…Chemicals used were of high chemical and stereogenic purities, and were synthesized according to Högberg et al (1990), Hedenström et al (1992), Tai et al (1990Tai et al ( , 1992, and Hedenström et al (2002). Purity details and abbreviations of compounds used below are given in Table 1.…”

Section: Methodsmentioning

confidence: 99%

“…In test 1, each compound was tested alone, while in test 2 the analogs were combined with (SSS)Ac to evaluate possible synergistic or antagonistic effects. In 1993 (test 3), three different doses of each analog were used to make a comparison with the results in Japan of Tai et al (1992) possible. In 1995, the effects of addition of (SR-)Ac, (SRR)Ac, or (SRS)Ac analogs to (SSS)Ac were tested (tests 4 and 5].…”

Section: Methodsmentioning

confidence: 99%

“…c a The hyphen in acronyms indicates a missing methyl group relative to compound 1 b Chemical purity % ð Þ : 100 Â Amount of the stereoisomers of the indicated compound=Amount of all compounds ð Þ. Stereochemical purity % ð Þ : 100 Â Amount of the indicated stereoisomer=Sum of amounts of all stereoisomers ð Þ c 1) Högberg et al (1990), Anderbrant et al (1992b), and Hedenström et al (2006), 2) Tai et al (1990), 3) Tai et al (1992), 4) Hedenström et al (1992) main attractant Anderbrant et al, 1995;Bergström et al, 1995), suggesting that the length of the carbon chain is an essential characteristic of the pheromone for a given species. On the other hand, these two, and several other Neodiprion species, also are attracted to two or more compounds in which the acetate group of the main pheromone compound has been replaced with other acyl moieties (Anderbrant et al, 1992a(Anderbrant et al, , 1997Anderbrant, 1999).…”

Section: Introductionmentioning

confidence: 99%

“…To evaluate whether simpler molecules could mimic pheromonal activity, Tai et al (1992) synthesized the diprionol acetate analogs, (2S,3S)-3-methyl-2-pentadecanol acetate [(SS-)Ac] and (2S,3S)-3-methyl-2-pentadecanol acetate [(SR-)Ac] (Table 1). These analogs lacked the methyl group in the 7-position (the hyphen in our compound acronyms indicates a missing methyl group relative to diprionol, see Table 1).…”

Section: Introductionmentioning

confidence: 99%

“…In order to get a more complete picture of what molecular elements are important for pheromonal activity in this species, we investigated the effect of the two analogs tested by Tai et al (1992), as well as of analogs lacking the methyl group at the 3-position, (2S,7S)-7-methyl-2-pentadecanol acetate [(S-S)Ac], or the first methyl group of the carbon chain, (2S,6S)-2,6-dimethyl-1-tetradecanol acetate [(-SS)Ac, Table 1]. Field trials were performed both in Sweden and in Japan.…”

Section: Introductionmentioning

confidence: 99%

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Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden

et al. 2010

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The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2S,3R,7R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2S,7S)-7-methyl-2-pentadecanol, (2S,6S)-2,6-dimethyl-1-tetradecanol, and (2S,3S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2S,3S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10-20 times higher than the acetate pheromone component. The acetate esters of the (2S,3R)-analog and the (2S,3R,7R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden

et al. 2010

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Asymmetric Syntheses of the Sex Pheromones of Pine Sawflies, Their Homologs and Stereoisomers

Zheng

Lan

Yang

et al. 2012

Helvetica Chimica Acta

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We describe efficient and flexible enantioselective syntheses of the active enantiomers of the pheromones of pine sawflies, including the species Diprion jingyuanensis, their homologs and, stereoisomers, as well as those identified from the Chinese species Diprion jingyuanensis, i.e., 126. A total of 48 compounds, including acetates 78101 and propanoates 102125, have been synthesized. Our general approach towards these compounds originated from the commercially available chirons diethyl (S)- and (R)-malates, as well as ethyl (R)-3-hydroxybutanoate. The Seebach asymmetric methylation was employed in a key step to control additional configuration.National Basic Research Program (973 Program) of China [2010CB833200]; NSF of China [20832005, 21072160]; Natural Science Foundation of Fujian Province of China [2011J01054

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Enantiopure building blocks for the synthesis of 3-methyl-2-alkanols. Diastereoselective methylmetal addition to a chiral 2-methylaldehyde followed by lipase catalysed esterification

Larsson

Andersson

Liu

et al. 2004

Tetrahedron: Asymmetry

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Synthesis and Field Test of a Pheromone Mimic of the Pine Sawfly(Neodiprion sertifer)

Cited by 6 publications

References 5 publications

Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden

Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden

Asymmetric Syntheses of the Sex Pheromones of Pine Sawflies, Their Homologs and Stereoisomers

Enantiopure building blocks for the synthesis of 3-methyl-2-alkanols. Diastereoselective methylmetal addition to a chiral 2-methylaldehyde followed by lipase catalysed esterification

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