Identification and Field Evaluation of a Sex Pheromone of the European Pine Moth

Abstract

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) ...

Identification of Components of the Female Sex Pheromone of the Simao Pine Caterpillar Moth, Dendrolimus kikuchii Matsumura

“…Furthermore, the minor components, Z5-12: OAc and (5Z,7E)-5,7-dodecadien-1-yl propionate, function to enhance the specificity of the signals, respectively. In addition, Z5,E7-12:OAc is known to serve as a strong inhibitor of European pine caterpillar moth D. pini whose major pheromone component is Z5,E7-12:Ald (Priesner et al, 1984). In the current research, Z5,E7-12:Ald at relatively high dose showed strong antagonistic effects on attraction of male D. kikuchii, although trace quantities of it have been found in the gland extracts.…”

“…So far, sex pheromones have been reported for the masson pine caterpillar moth, D. punctatus (Zhao et al, 1993), the pine moth, D. spectabilis (Ando et al, 1982;Kong et al, 2003), the larch caterpillar moth, D. superans (Klun et al, 2000;Kong et al, 2007a), the Yunnan pine caterpillar moth, D. houi (Kong et al, 2007b), and the European pine moth D. pini (Priesner et al, 1984;Kovalev et al, 1993). Sex pheromones components that have been identified from Dendrolimus species are all (5Z,7E)-5,7-dodecadienes with different terminal functional groups (alcohol, acetate, propionate, and aldehyde), except for the sex pheromone of D. houi, which was reported as a mixture of (5E,7Z)-5,7-dodecadien-1-yl acetate (E5,Z7-12:OAc), (5E,7Z)-5,7-dodecadien-1-ol (E5,Z7-12:OH), and (5E,7Z)-5,7-dodecadienal (E5,Z7-12:Ald) (Kong et al, 2007b).…”

Stimulation of sex pheromone production by PBAN‐like substance in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera: Lasiocampidae)

“…Z5,E7-12:Ald is a major pheromone component of a closely related species, D. pini (Prisner et al, 1984) and a likely inhibitor of the attractant pheromone blend in D. punctatus (Zhao, unpublished data). It may be hypothesized that decapitated females or gland incubations lose a factor or mechanism to control the specific pheromone blend produced by normal females.…”

Sex pheromone of the larch caterpillar moth, Dendrolimus superans, from northeastern China

“…All baits containing Z5,E7-12:Ald with or without other gland components trapped more male D. superans than controls. In D. pini, E5,Z7-12:Ald is a powerful antagonist to its sex pheromone, Z5,E7-12:Ald (Priesner et al, 1984). In D. pini, E5,Z7-12:Ald is a powerful antagonist to its sex pheromone, Z5,E7-12:Ald (Priesner et al, 1984).…”

“…The sex pheromone of Dendrolimus punctatus consists of ( Z,E )-5,7-dodecadienol ( Z 5, E 7-12:OH), ( Z,E )-5,7-dodecadienyl acetate ( Z 5, E 7-12:OAc), ( Z,E )-5,7-dodecadienyl propionate ( Z 5, E 7-12:OPr), ( Z )-5-dodecenol ( Z 5-12:OH), and ( Z )-5-dodecenyl acetate ( Z 5-12:OAc) in a ratio of 7.9:6.5:2.4:2.6:1.0 (Zhao et al, 1993), whereas the sex pheromones of Dendrolimus spectabilis and Dendrolimus pini consist of Z 5, E 7-12:OH (Ando et al, 1982) and ( Z,E )-5,7-dodecadienal ( Z 5, E 7-12:Ald), respectively (Priesner et al, 1984). The sex pheromone of Dendrolimus punctatus consists of ( Z,E )-5,7-dodecadienol ( Z 5, E 7-12:OH), ( Z,E )-5,7-dodecadienyl acetate ( Z 5, E 7-12:OAc), ( Z,E )-5,7-dodecadienyl propionate ( Z 5, E 7-12:OPr), ( Z )-5-dodecenol ( Z 5-12:OH), and ( Z )-5-dodecenyl acetate ( Z 5-12:OAc) in a ratio of 7.9:6.5:2.4:2.6:1.0 (Zhao et al, 1993), whereas the sex pheromones of Dendrolimus spectabilis and Dendrolimus pini consist of Z 5, E 7-12:OH (Ando et al, 1982) and ( Z,E )-5,7-dodecadienal ( Z 5, E 7-12:Ald), respectively (Priesner et al, 1984).…”