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Sex Pheromone of Tortrix Viridana: (Z)-Ll-Tetradecenyi Acetate As The

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Sex Pheromone of Tortrix Viridana: (Z)-Ll-Tetradecenyi Acetate As The Notizen 1281 Sex Pheromone of Tortrix viridana: chain alcohols, aldehydes and esters tested, acetates (Z)-ll-TetradecenyI Acetate as the Main Com­ of a 13 or 14 carbon chain with a double bond in po­ ponent sition 11 gave the highest responses. (£)-l 1-Tridecen- yl acetate (£ll-13A c) was the most effective test H. A m 1, E. Priesner2, H. Bogenschütz3, H. R. Buser1, chemical, followed by E\ 1-14 Ac (Table I). The D. L. Struble14, S. Rauscher1, and S. Voerman 5 findings were confirmed in gas chromatograms of 1 Eidg. Forschungsanstalt für Obst-, Wein- und Gartenbau, acetate standards with electroantennographic detec­ CH-8820 Wädenswil, Switzerland. tion [3] which showed the prominent signal obtained 2 Max-Planck-Institut für Verhaltensphysiologie, D-8131 with £11 -13 Ac at the expected retention time. In Seewiesen, German Federal Republic. 3 Forstliche Versuchs- und Forschungsanstalt Baden-Würt­ field tests in June 1977 at Freiburg/Br. 10 and lOOpg temberg, D-7801 Stegen-Wittental, German Federal Repu­ £11-13 Ac caught 7.0 and 44.3 T. viridana males blic. 4 permanent address: Canada Agriculture, Research Sta­ per trap, respectively, while E 11 -14 Ac at the same tion, Lethbridge, Alberta T1J 4B1, Canada. test amounts was not attractive. These re­ 5 Laboratory for Research on Insecticides, NL-6709 PG sults suggested that this unusual C 13 compound could Wageningen, The Netherlands. be a key substance in the sex pheromone of T. virida­ Z. Naturforsch. 34 c, 1281 - 1284 (1979); na. received June 5,1979 Extracts for chemical analysis were made by col­ Sex Pheromone, Sex Attractant, (Z)-ll-Tetradecenyl Ace­ lecting calling females in methylene chloride and re­ tate, Tortrix viridana moving the bodies within a few seconds to avoid ex­ In electroantennographic studies on Tortrix viridana ma­ tracting too much fatty material. A temperature les, (£)-l 1-tridecenyl acetate displayed the highest activity drop was found to be essential to induce calling in T. of all straight-chain alkenyl acetates. However, evidence obtained by gas chromatography coupled to an electroan­ viridana females. At the end of a 16 h light phase the tennographic detector or a mass spectrometer indicated temperature was lowered from 20 to 15 0 and a light that the ubiquitous pheromone compound (Z)-l 1-tetrade- cenyl acetate is the main component in the T. viridana fe­ of 4 lux was maintained for observation. During the male secretion. This compound and both (Z)- and (£)-ll- following 3 h, a substantial number of females was tridecenyl acetate were found to be attractants for T. viridana observed in calling position, and a wash of 76 fema­ males in the field. (Z)-9- and (£)-l 1-tetradecenyl acetate were not attractive and reduced male catches when added les could be obtained in one session. to either (Z)-l 1-tetradecenyl acetate or (£)-l 1-tridecenyl Gas chromatography of the female wash was car­ acetate. No evidence for synergistic effects was obtained. ried out on a Silar 10 C glass capillary column; the effluent gas was split in a 1 0 : 1 ratio between the flame ionization (FID) and the electroantennograph- (Z)-l 1-Tetradecenyl acetate (Z 11-14 Ac) has been identified in the sex pheromone secretion of many species of Lepidoptera, notably of the tortricid Table I. Electroantennogram response values of male Tor­ family, and is an important component of many sex trix viridana to (Z)- ana (£)-alkenyl acetates. Values indi­ attractants discovered by field screening [1]. We cate equipotent stimulus amounts in a half log scale ( 0.01 represents a range from 0.0056 to 0.018 fxg; 0.03, from 0.018 have now obtained evidence that the chemical is also to 0.056 jxg; etc.). the main component of the sex pheromone of the Z 8 - 12Ac 1 E 8 - 12 Ac 0.3 European oak leaf roller or green tortrix moth, Tor­ Z9 - 12 Ac 0.3 E 9 - 12Ac 0.3 trix viridana L. (Lepidoptera: Tortricidae), and a Z 10- 12 Ac 0.1 £ 10- 12 Ac 0.1 strong attractant for males of the species. Z 9 - 13 Ac 0.3 £9-13 Ac 0.3 Outbreaks of the leaf roller moth near Freiburg/ Z 10- 13 Ac 0.1 E 10- 13 Ac 0.1 Z 11 - 13 Ac 0.03 £ 11-13 Ac 0.003 Br. permitted field collection of substantial numbers of insects in the pupal stage for electrophysiological Z 9 - 14 Ac 0.3 £9-14 Ac 0.3 Z 10- 14 Ac 0.1 £ 10- 14Ac 0.1 and chemical investigation. Electroantennogram Z l l - 14Ac 0.03 £11 - 14Ac 0.01 (EAG) and single receptor responses were recorded Z 12 - 14 Ac 0.1 £ 12- 14Ac 0.03 as reported in earlier studies with tortricid species Z 10- 15 Ac 0.3 £ 10- 15 Ac 0.1 [2], Of the series of monounsaturated straight- Z l l - 15 Ac 0.1 £ 11- 15 Ac 0.03 Z 12 - 15 Ac 0.1 £ 12- 15 Ac 0.1 Reprint requests to Dr. H. Arn. Z l l - 16Ac 1 £11 - 16Ac 0.3 Z 12- 16Ac 1 £ 12- 16Ac 1 0341-0382/79/1200-1281 $01.00/0 1282 Notizen the spectra were searched for tri- and tetradecenyl acetates. The mass chromatogram at m /e 255 contain­ ed a major peak whose retention time and mass spectrum (M + 1 = 255, M + 1 — C H 3CO O H = 195) were as expected for a tetradecenyl acetate. The amount was estimated at 4 ng per female. No iso­ mers were found at neighbouring retention times; if present, their amount would have been less than 5% of the main peak. No tridecenyl acetate was detect- To allow an isomer assignment, mass fragmento- grams were carried out at a slower temperature pro­ gram (2°/min), using the fragment of m /e 194 (M +- C H 3COOH) obtained in electron impact ioni­ zation. Its main peak coincided with that of synthetic I I----------------------------- 1-----------------------------1---------------------- Z11-14 Ac on two different columns. The Silar 100 120 140 160° 10C column separated Z ll-14A c from all other Fig. 1. Gas chromatogram of a Tortrix viridana female wash, recorded with flame ionization (FID)and electroan- tetradecenyl acetates except from £12-14Ac and tennographic detection (EAD). Arrows point at EAD peaks 13-14 Ac; separation of these isomers from reproducible in multiple runs. Elution ranges of straight- Z 11-14Ac was achieved on OV-lOl. The above chain acetates are indicated. Conditions: Silar IOC, 22 m x 0.3 mm glass capillary column. Injection of 1 female evidence indicated that Z11-14 Ac is the main equivalent at 70 °, after 2 min heated to 90 ° at 30 °/min, component of the T. viridana sex pheromone. then heated at 6 °/min to end. The dip in the EAD trace following the main peak is caused by the electronic filter Extensive attraction studies were conducted in used to compensate for baseline drift. June 1978 near Freiburg/Br. in the same test area as in 1977. Since the middle of the 19th century the ri­ ic detector (EAD) [3]. The filtered extract was in­ parian woodland in the Upper Rhine Valley be­ troduced by splitless injection without prior cleanup. tween Basel and Freiburg has changed into incom­ EAD recordings consistently showed a main peak at plete brushwood by ground water subsidence. Only a retention time of Z11-14 Ac which coincided a few solitary oaks (Quercus robur L.) overtop the with a small but sharp peak in the FID trace corre­ xerophilous shrubs; their crowns often extend to the sponding to an amount of a few nanograms per fe­ ground and are periodically infested with T. viridana. male (Fig. 1). The relative heights of the peaks ob­ The field tests included Z 11 — 14 Ac as the identi­ tained with the two detectors was approximately the fied component, E\ 1 — 13Ac as an attractant discov­ same for the female wash and synthetic Z 11 -14 Ac. ered in 1977, Z9- and E 11 — 14 Ac as candidate sec­ Some chromatograms also showed a small EAD ondary components, and the analogues Z 11 - 13 Ac peak eluting just before Z ll-14A c, at a retention and Z ll - 140H. Test compounds were at least time similar to Zsll-M Ac or Z9-14Ac (Fig. 1). 99% pure and contained less than 0.1% of the opposite This peak appeared with the front slope of a major geometric isomer. The chemicals were applied to the peak on the FID trace. Two other small EAD peaks cavity of serum bottle caps (Tellergummikappen No. were observed during elution of the solvent. These 90142, Auer Bittmann Soulie AG, Zürich) from hex­ results indicate that other, unidentified compounds ane solutions. Tetra Traps with flaps [4] were hung beside Z 11 -14 Ac may be involved in the sex phe- from oak tree branches at eye level. Each test includ­ rom one o f T. viridana. No other EAD activity was ed a comparison of 6 treatments per tree in 6 repli­ observed within the retention range of 10 to 18 car­ cates. Distances between treatments were 2 — 3 m, bon acetates. between replicates 20 — 200 m. Trap positions were Further information on the main component was systematically changed for each replicate. Catches obtained by gas chromatography/mass spectrometry were recorded weekly and the figures subjected to on a Finnigan 4000 GC-MS instrument equipped log (-V + 1) transformation followed by two-way with a data system. Complete mass spectra ( m /e analysis of variance.
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