In addition to three known sex lure components [(Z)-11-hexadecenyl acetate, (Z)-11-hexadecenal, and (Z)-11-hexadecenol], (Z)-9-tetradecenyl acetate was field-proven as a trace coattractant for malePlutella xylostella, with an optimal content below 0.01% in blends. This potent four-component lure for diamondback males also attractedCrymodes devastator males, and in this respect is not different in its attractancy from virgin diamondback females. Replacement of (Z)-9-tetradecenyl acetate in the four component lure with (Z)-9-tetradecen-1-ol, at the level of 10% of the total lure mixture, did not alter its attractancy for diamondback males, but it did inhibit attraction ofCrymodes devastator. The status of biologically active components as possible sex pheromones or para-pheromones is discussed.

Forstliche Versuchs-und Forschungsanstalt B a d en -W ü rt tem berg, D-7801 Stegen-W ittental Sex Pherom one, (Z ,£ )-5 ,7 -D o d ec ad ie n al, P h ero m o n e In hibitors, Olfactory Receptors, D endrolim us pini, L asiocam pidae The principal com ponent o f the fem ale sex p h e ro m o n e of the E uropean pine m oth Dendrolimus p in i L. (L asiocam pidae) was identified as (Z ,E )-5 ,7 -dodecadienal by capillary gas chrom atography, m ass spectrom etry, single receptor analyses, and field trap p in g tests. T rap s initially baited with 1000 ng o f (Z ,£ )-5 ,7 -d o d e c ad ien a l (> 9 9 % Z E ) effectively m onitored low D. p in i p o p u latio n s over 6 weeks w ithout rebaiting. C aptures d isa p p ea red upon addition o f ^ 1% o f either (£ ,Z )-5 ,7 -d o d e c ad ien a l or (Z ,£)-5,7-dodecadienyl acetate, the key stim u la n ts for additional receptor cell types located in m ale an ten n al h a ir sensilla. The Forest Services o f central E uropean coun tries w ith stands o f Scots pine (Pinus sylvestris L.) en dangered by the feeding o f Panolis flam m ea Schiff. (Noctuidae), Lymantria monacha L. (L ym antriidae), Dendrolimus pini L. (L asiocam pidae) and Bupalus piniarius L. (G eom etridae), are req u ired by law to survey for population densities o f these lepidopterous pests. Bogenschütz [1,2] has em phasized th e p o te n tial o f traps baited w ith sex-attractant chem icals for early detection o f population increases am ong low (non-dam aging) populations o f P. flam m ea and L. monacha. We report here the id en tificatio n o f the prim ary sex pherom one com ponent p ro d u ced by the female European pine m oth, Dendrolimus pin i L. We also describe a synthetic chem ical fo rm u latio n suitable for use in population m onitoring o f this species by survey traps. Fem ale sex pherom one com ponents are c h e m i cally known for four species o f the fam ily L asioReprint requests to E. Priesner or M. D. C hisholm . 0341-0382/84/1100-1192 $ 0 1 .3 0 /0 cam pidae. The tent caterpillars Malacosoma disstria Hbn. and M. californicum Pack, produce sex p heromones whose principal com ponents are (Z ,£ )-5 ,7 -dodecadienal ( Z 5 ,£ 7 -1 2 ;A id) and (£ ,Z )-5 ,7 -d o d e cadienal (£ 5 ,Z 7 -1 2 : Aid) [3, 4], T he sex p h ero m o n e o f the Japanese pine m oth Dendrolimus spectabilis Butl. was reported as (Z ,£ )-5 ,7 -d o d e c a d ie n -l-o l (Z 5 ,£ 7 -1 2 : O H ) [5, 6], and th at o f the M asson pine m oth D. punctatus Wlk., as a co m b in atio n o f this alcohol with the corresponding acetate and p ro p io n ate [7, 8].All four geom etrical isom ers o f the 5,7-dodecadien-l-ols and their acetate and ald ehyde a n a logues were included in o u r study o f the D. pini pherom one. The 5,7-dodecadienes were synthesized and purified by W ittig condensation reactions previously described [9,10]. T he purity o f all final products was b etter th an 98%; the Z 5 ,£ 7 -1 2 :A ld had a purity o f b etter th an 99%.N erve im pulse responses o f single recep to r cells located in h air sensilla (S. trichodea) ...

L-Methionine-35S and DL-cysteine-35S were good sources of sulfur for the biosynthesis of sinigrin in Armoracia lapathifolia Gilib. and were incorporated with approximately the same efficiency. Homomethionine-35S was a slightly poorer source of sulfur than methionine, while taurine-35S was a very poor source. When homomethionine, methionine, and cysteine were employed as sources of sulfur, the distribution of radioactivity between the two sulfur atoms in sinigrin was approximately 80% in the isothiocyanate moiety and 10–15% in the sulfate moiety. When taurine was employed, the distribution was reversed. 1-Thio-β-D-glucose (1-thioglucose) also was a poor source of sulfur for sinigrin. The carbon skeleton of 1-thioglucose was only slightly incorporated into this thioglucoside. The experiments indicated that 1-thioglucose was not a direct precursor of the 1-thioglucosyl residue of sinigrin.The administration of doubly labeled methionine-2-14C-35S clearly demonstrated that this amino acid was not incorporated intact into sinigrin. The carbon-2 and sulfur atoms were metabolized by two different routes.Preliminary studies related to sulfur incorporation into the thioglucosides of Nasturtium officinale R.Br., Tropaeolum majus L., and Reseda luteola L. indicated that there were some differences depending on the source of sulfur; DL-cysteine was a better source of sulfur than either methionine or 1-thioglucose. Tropaeolum majus L. appeared to utilize the sulfur of cysteine for the production of thioglucoside as efficiently as Armoracia lapathifolia Gilib.; however, the other two species utilized the sulfur from the amino acids very poorly.

An abdominal tip extract of female bertha armyworm moths, Mamestra configurata (Walker), was found to contain two sex pheromone components. One corresponded to (Z)-11-hexadecen-1-ol acetate, previously identified from this source, and the other to a tetradecen-1-ol acetate, identified by gas chromatography – mass spectrometry. Data obtained from the EAG profile of isomeric tetradecen-1-ol acetates indicated the active component to be (Z)-9-tetradecen-1-ol acetate. Neither of these two acetates was by itself attractive to males in field tests; however, mixtures were attractive, with the best attraction occurring with a C16:C14 acetate ratio of about 19:1.

Selected primary (Z)-alkenals and (Z)-alkenyl acetates (odd-numbered unsaturation positions, even-numbered carbon chains C10–C16) were field tested in three groups for ability to attract male moths into traps. Within each group all possible combinations (1:1:1) of components were examined. From 441 combinations, consistent attractants for 47 species were found. In one case three components were required for attractancy, while in others two or one were minimally sufficient. Possible trapping inhibitors were revealed for most of the species taken. Of the captured species 44 were noctuids, two were tortricids, and one was a gelechiid.

A potent sex pheromone produced by female bertha army worm moths was isolated. A 16 carbon, unsaturated, alkenol acetate was indicated from chemical degradative and GLC retention data. The location and configuration of the double bond was determined from the antennal responses (EAG) of male moths to a series of cis and trans mono-unsaturated alken-1-ol acetates; cis-11-hexadecen-1-ol acetate elicited the greatest EAG response. GLC retention times of the purified insect sex pheromone corresponded exactly with those of authentic cis-11-hexadecen-1-ol acetate on several analytical columns. Maximum biological response in laboratory bioassays of synthetic materials was obtained from a mixture of approximately 85% cis- and 15% trans-11-hexadecen-1-ol acetates.

The administration of C14-labelled compounds to horseradish (Armoracia lapathifolia Gilib.) demonstrated that both methionine and acetate were efficiently incorporated into the aglycone (allyl isothiocyanate) of sinigrin. Chemical degradation of the aglycone showed that the methyl group of acetate appeared in the "isothiocyanate carbon" and that carbons 2, 3, and 4 of methionine were incorporated into carbons 2, 3, and 4 respectively of the aglycone with very little randomization. Homocysteine was the only other compound that was incorporated into the aglycone. Other degradation products of methionine did not appear to be incorporated into allyl isothiocyanate.

(Z,Z,Z)-3,6,9-Eicosatriene and (Z,Z,Z)-3,6,9-heneicosatriene have been identified as components of the sex pheromone of the noctuid,Caenurgina erechtea (Cramer), the forage looper. Structural assignments were made on the basis of spectroscopic and chromatographic data and were confirmed by comparison with synthetic material. Flight tunnel behavioral studies demonstrated that either component, when tested individually, would elicit wing fanning responses in males; however, mixtures of the two components increased this response and were essential for initiation of upwind flight and landing. In field experiments, traps baited with either component alone captured few or no adult forage looper males while those baited with both components captured several target males.