Preparation of Streochemically Pure Sex Pheromone Components of the Pine Sawfly (<i>Neodiprion sertifer</i>) and Field Tests of the Synthetic Compounds

Tai, Akira; Morimoto, Naotake; Yoshikawa, Masaharu; Uehara, K.; Sügimura, Takashi; Kdcukawa, Tadashi

doi:10.1080/00021369.1990.10870189

Cited by 6 publications

(6 citation statements)

References 4 publications

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“…First, a true synergism between the SSS-and other isomers was found only at the Siberian site (2), where addition of either the SRS-or the SRRisomer was necessary to catch significant numbers of N. sertifer males. Previous studies had reported considerable synergism in both Japan and North America, with catches increasing 5-8 times (Kikukawa et al, 1983;Tai et al, 1990). However, in the current study we did not find any combination of isomers to be significantly better than the pure SSS-isomer at these sites.…”

Section: Discussioncontrasting

confidence: 83%

“…(To improve readability, the numbers of the stereogenic carbons have been omitted from here on; thus the (2S,3S,7S)-isomer is abbreviated as SSS-isomer.) Both isomers have also been tested in Japan, where it was found that the SRR-isomer increased the catches even at high doses (Tai et al, 1990). Field tests in Europe, however, showed that the SRR-isomer was antagonistic even when added in amounts below 1% in relation to the SSS-isomer (Anderbrant et al, 1992a).…”

Section: Introductionmentioning

confidence: 99%

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Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer, to different pheromone stereoisomers and esters

Anderbrant

Löfqvist

Högberg

et al. 2000

Entomologia Exp Applicata

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The European pine sawfly, Neodiprion sertifer (Geoffroy) (Hymenoptera: Diprionidae), is a widespread and economically important forest insect. The sex pheromone communication system of this species has been previously investigated in North America, Japan and Europe, with the acetate or propionate of the alcohol (2S,3S,7S)‐3,7‐dimethyl‐2‐pentadecanol (diprionol) shown to be the main pheromone component. In some locations, male attraction either increased or decreased by the addition of the (2S,3R,7R)‐diprionyl acetate isomer. However, these studies were made with different batches of synthetic pheromones, with different types of traps and according to different procedures, so the observed differences might not reflect true geographic variation. Here we investigate the geographic pattern of male sawfly response by using identical chemicals, traps and experimental procedures at eight field sites ranging from Japan in the east to Canada in the west. We found an increased inhibitory effect of the (2S,3R,7R)‐isomer from Japan and Siberia to Europe. At the eastern sites, increasing amounts of the (2S,3R,7R)‐isomer up to and equal to the amount of the (2S,3S,7S )‐isomer, did not influence the trap catch, whereas at sites in Europe, as little as 1% of the (2S,3R,7R)‐isomer almost completely inhibited the attraction. The response of the North American population was intermediate. The only site in which the (2S,3R,7R)‐isomer was essential for the attraction of males was in Siberia. A similar pattern was found for the (2S,3R,7S)‐isomer. Both the acetate and the propionate form of the (2S,3S,7S)‐isomer were attractive by themselves in Japan, Europe and North America, and neither the (2S,3R,7S)‐isomer nor the (2S,3R,7R)‐isomer alone were attractive, in the acetate or propionate form. We discuss the significance of our findings for the development of more efficient monitoring schemes and for the causes of population divergence and speciation in the European pine sawfly.

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Section: Discussioncontrasting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer, to different pheromone stereoisomers and esters

Anderbrant

Löfqvist

Högberg

et al. 2000

Entomologia Exp Applicata

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“…The synergistic effect observed by Olaifa et al (1987), when the differently baited traps were rotated among positions, was not statistically significant. Like-wise, the results from Japan (Tai et al, 1990), indicating synergism of SRR over a large range of ratios, but only weak inhibitory effect, may partly be due to low captures and positional effects, and no statistical test was presented. When adding 2-20 ~o SRR-isomer to the SSS-isomer, Tai et al (1990) still caught as many sawflies as they did with SSS alone.…”

Section: Discussionmentioning

confidence: 99%

“…Like-wise, the results from Japan (Tai et al, 1990), indicating synergism of SRR over a large range of ratios, but only weak inhibitory effect, may partly be due to low captures and positional effects, and no statistical test was presented. When adding 2-20 ~o SRR-isomer to the SSS-isomer, Tai et al (1990) still caught as many sawflies as they did with SSS alone. However, large trap catches may be obtained with incorrect bait or even with no bait at all if the trap is too unspecific (Anderbrant et al, 1989, in litt.).…”

Section: Discussionmentioning

confidence: 99%

Field response of the pine sawfly Neodiprion sertifer to the pheromone (2S, 3S, 7S)‐diprionyl acetate and its stereoisomers

Anderbrant

Löfqvist

Högberg

et al. 1992

Entomologia Exp Applicata

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All eight optical isomers of 3,7‐dimethyl‐2‐pentadecanyl acetate (diprionyl acetate), of high optical purity (>97.4%), were tested for a behavioural activity on male pine sawflies, Neodiprion sertifer (Geoffr.) (Hymenoptera: Diprionidae), in northern Europe. Males were strongly attracted to (2S, 3S, 7S)‐diprionyl acetate. Addition of more than 0.1% of the (2S, 3R, 7R)‐isomer reduced the catch and above 2% the attraction was completely inhibited. Contrary to what has been reported for North American and Japanese populations, so significant synergistic effect of small amounts of the (2S, 3R, 7R)‐isomer could be demonstrated. The effects of addition of the other six optical isomers alone or in combinations, were also studied, but none was found to be a synergist. The (2S, 3R, 7S)‐isomer had a weak inhibitory effect, and completely inhibited the attraction to the (2S, 3S, 7S)‐isomer when applied in about equal amounts as the attractant. In some cases a reduction in catch was noted when other isomers were tested, but this could be attributed to the very small amounts of the inhibitory (2S, 3R, 7R)‐isomer present in these isomers.

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“…sertifer reacts differently to the (2S,3 R,7R)-isomer depending on where in the distribution range the test is conducted (ANDERBRANT, 1993). In Japan, for example, the effect of the (2S,3R,7R)-isomer seems to be mainly synergistic (TAI et al, 1990), whereas in Europe the addition of only 1 % to the attractive (2S,3S,7S)-isomer can reduce the catch completely (ANDERBRANT et al, 1992a).…”

Section: Discussionmentioning

confidence: 99%

Diprionyl esters attractive to males of the dailing pine sawfly Neodiprion dailingensis Xiao et Zhou (Hym., Diprionidae) in north‐eastern China

Anderbrant¹,

Zhang²,

Chen³

1997

J Applied Entomology

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The attraction of male Neodiprion duilingensis Xiao et Zhou to pheromone substances identified from other Neodiprion species was tested in plantations of Pinus tabulueformis Carr. in Liaoning Province in north-eastern China. Both the acetate and propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) were highly attractive. An addition of 10% of the (2S,3R,7R)-isomer did not significantly reduce the catch to the acetate. The (2S,3R,7R)-isomer was not attractive by itself. This is the first pheromone study of a species belonging to the recently described East Asian group of Neodiprion. The response of N. duilingensis males is similar to that of A'. sertifer males in eastern part of Asia.

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Preparation of Streochemically Pure Sex Pheromone Components of the Pine Sawfly (Neodiprion sertifer) and Field Tests of the Synthetic Compounds

Cited by 6 publications

References 4 publications

Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer, to different pheromone stereoisomers and esters

Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer, to different pheromone stereoisomers and esters

Field response of the pine sawfly Neodiprion sertifer to the pheromone (2S, 3S, 7S)‐diprionyl acetate and its stereoisomers

Diprionyl esters attractive to males of the dailing pine sawfly Neodiprion dailingensis Xiao et Zhou (Hym., Diprionidae) in north‐eastern China

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