Processionary Moth Thaumetopoea Pityocampa Research Articles

Pine processionary caterpillar Thaumetopoea pityocampa as a new threat for relict Mediterranean Scots pine forests under climatic warming

The wide distribution of Scots pine ( Pinus sylvestris L.) in Europe includes two relict populations in southern Spain (Sierra Nevada and Sierra de Baza), belonging to the subspecies nevadensis. These populations are isolated in high mountains, which tends to protect them from the attack of a severe defoliating Mediterranean pest, the pine processionary moth Thaumetopoea pityocampa. However, as a consequence of climate change, the pine processionary caterpillar has increasingly attacked populations of this pine in recent years. This work describes the detrimental effects of defoliation by the pine processionary caterpillar in P. sylvestris subsp. nevadensis in Sierra Nevada. Defoliation strongly reduced pine growth as well as all the reproductive parameters measured (female and male cone production, mature cone size, seed production and seed weight), in addition to some deaths. If winter temperatures continue to increase, the pine processionary caterpillar will have a dangerous impact in these relict pine populations, by further reducing the pine's weak regeneration capacity. We suggest some mitigation actions based on managing habitat structure, in order to reduce or avoid such negative impacts.

Host utilisation by moth and larval survival of pine processionary caterpillar Thaumetopoea pityocampa in relation to food quality in three Pinus species

Abstract 1. The work reported here analysed host utilisation by the pine processionary moth Thaumetopoea pityocampa (Lepidoptera: Thaumetopoeidae), the relationship between moth oviposition patterns and larval performance, the chemical characteristics of the plant in relation to the performance of different larval instars, and the role of these factors in the outbreak capacity of the species. In order to do this, a combination of field and laboratory techniques was used to study three pine species differing in nutritional characteristics.2. Moths oviposited in the three pine species analysed, although cluster pine received a lower number of batches. Late‐instar larvae were able to feed on all three pine species, however first‐instar larvae developed on Scots and black pine but died on cluster pine. Consequently, oviposition in cluster pine can be considered an oviposition mistake, and indicates that moths are rather unselective when ovipositing on different pine species.3. Chemical analysis of needles suggested that the quantity of nitrogen was the main factor responsible for the difference in survival of larvae.4. The oviposition pattern of the moth and the larval susceptibility to food quality in Thaumetopoea pityocampa agree with the theory that unselective oviposition of the moth is a precondition for eruptive dynamics in phytophagous insects.5. The success of the larvae depends mainly on the probability of the moth finding a suitable host. This probability is determined strongly by the changes of structure and coverage in Mediterranean pine woodlands, due to human management.

Female calling behaviour and male response to the sex pheromone in Thaumetopoea pityocampa (Den. & Schiff.) (Lep., Thaumetopoeidae)

Abstract: Female calling behaviour and male response to natural and synthetic pheromone sources were used for a Portuguese population of the winter pine processionary moth Thaumetopoea pityocampa (Den. & Schiff.). Virgin females 1–5 days old were studied, the mean calling longevity being 3.3 ± 0.7 days. Calling started ≅ 3 h after the onset of scotophase, and 7 h after emergence, lasting, nightly, for 6.4 ± 0.7 h, and was not affected by female age. A drop in air temperatures during the first half of scotophase and an increase in light intensity at dawn apparently determined the onset and termination of calling. Male flight activity began, on average, 3 h before the females started emitting pheromone, and was similarly affected by air temperatures and light intensity. The attractivity of traps baited with synthetic pheromone (TP056A; Yne 11, Z13–16AC) was compared with that of virgin females. Male flight activity was monitored in central and southern Portugal, using pheromone traps, and seen to last between 6 and 10 weeks, with a major peak occurring, in all sites, at the beginning of September.

Reinvestigation of Female Sex Pheromone of Processionary Moth (Thaumetopoea pityocampa): No Evidence for Minor Components

The female sex pheromone of the processionary moth Thaumetopoea pityocampa has been reinvestigated to look for possible minor components. Examination by GC-MS and GC-EAD of the contents of virgin female glands, after stimulation with PBAN (pheromone-biosynthesis-activating neuropeptide), showed that the major component, (Z)-13-hexadecen-11-ynyl acetate (1), appears to be the only pheromone compound present in the gland. Comparison of female attractivity with that of the natural extract and synthetic (Z)-13-hexadecen-11-ynyl acetate showed that this chemical is able to elicit a similar activity to that displayed by virgin females in a wind tunnel. In single cell recording experiments, two specialist receptor cell types were found in the trichoid sensilla. One cell type was tuned to enyne acetate 1. The other one was tuned to (Z,Z)-11,13- hexadecadienal and (Z)-13-hexadecen-11-ynal, the major components of the pheromone blend of other Thaumetopoea spp., and constitutes a further example of interspecific inhibitor receptor cells. Our results show that the processionary moth may not need minor components for successful mate recognition.

Synthesis of tritiated sex pheromones of the processionary moth Thaumetopoea pityocampa and the Egyptian armyworm Spodoptera littoralis

Synthesis of tritiated sex pheromones of the processionary moth Thaumetopoea pityocampa and the Egyptian armyworm Spodoptera littoralis

Synthesis of tritiated sex pheromones of the processionary moth Thaumetopoea pityocampa and the Egyptian armyworm Spodoptera littoralis

Synthesis of tritiated sex pheromones of the processionary moth Thaumetopoea pityocampa and the Epyptian armyworm Spodoptera littoralis has been accomplished by a simple route involving tritiated sodium borohydride reduction of the corresponding aldehyde followed by acetylation of the resulting radiolabelled alcohol. The process occurs with high chemical and radiochemical yields and the compounds have been used in pheromone catabolism studies.

Ligand Specificity of Pheromone‐Binding Proteins of the Processionary Moth

Photoaffinity labeling of proteins extracted from sensory hairs and antennal branches of the processionary moth Thaumetopoea pityocampa with a tritium-labeled diazoacetate analogue of the sex pheromone (Z)-13-hexadecen-11-ynyl acetate revealed a 15-kDa pheromone-binding protein in male moth sensory hairs (SH-15). A different 15-kDa protein in male antennal branches (B-15) was not photolabeled. All extracts except male sensory hairs showed a photolabeled 20-kDa protein; a photolabeled male 30-kDa protein in the branches (B-30) was also observed. The 20-kDa proteins in the sensory hairs (SH-20) and branches (B-20) showed differing affinities for the photoaffinity analogues; moreover, SH-15 exhibits higher affinity for the natural pheromone, (Z)-13-hexadecen-11-ynyl acetate, than for its alcohol metabolite and other analogues in competitive displacement experiments. The affinity shown by the pheromone-binding protein for the metabolic product suggests that the alcohol may be also transported by the binding protein. Interestingly, a shift in labeling from SH-15 to SH-20 was produced in the presence of an excess of the natural pheromone, its alcohol and other analogues. The binding showed little discrimination among structurally similar analogues of the pheromone, while saturated and aromatic molecules showed little affinity for the proteins of either sensory hairs or antennal branches.

Synthesis of trifluoromethyl ketones as inhibitors of antennal esterases of insects

A variety of long chain aliphatic and aromatic trifluoromethyl ketones I-XIV has been conveniently prepared, many of them for the first time, from the corresponding Grignard or organolithium derivatives. Two of them, ( Z)-1,1, 1-trifluoro-15-octadecen-13-yn-2-one ( XV) and ( Z)-1,1,1-trifluoro-16-nonadecen-14-yn-2-one ( XVI), structurally-closed analogues of (Z)-13-hexadecen-11-ynylacetate, the sex pheromone of the processionary moth Thaumetopoea pityocampa, have been stereospecifically synthesized in excellent yield by a convenient new method. The procedure involves lithiation ot the corresponding iododerivative XXIX and XXX with one equivalent of tert-BuLi to obviate addition of the reagent to the enyne system. Some of the compounds have already been tested and found to be good inhibitors of antennal esterases in the Egyptian armyworm Spodoptera littoralis and the pheromone action in the processionary moth Thaumetopoea pityocampa. β-Thiotrifluoromethylketones XVII-XX, which are expected to enhance the inhibition activity of the parent ketones due to their higher hydration constants, have also been prepared in good yields,

Trifluoromethyl ketones as inhibitors of the processionary moth sex pheromone.

Aliphatic and aromatic trifluoromethyl ketones have been evaluated in the laboratory and in the field as inhibitors of the pheromone response of the processionary moth Thaumetopoea pityocampa males. Among them, two compounds, (Z)-1,1,1-trifluoro-15-octadecen-13-yn-2-one and (Z)-1,1,1-trifluoro-16-nonadecen-14-yn-2-one, are closely related analogs of the natural pheromone (Z)-13-hexadecen-11-ynyl acetate. In the laboratory experiments, carried out by pre-exposure of males to vapors of the chemicals, alpha-naphthyl trifluoromethyl ketone, beta-naphthyl trifluoromethyl ketone, 1,1,1-trifluorotetradecan-2-one and (Z)-16-nonadecen-14-yn-2-one displayed notable blockage of the pheromone detection on EAG. The activity of 1,1,1-trifluorotetradecan-2-one is postulated to be due to the inhibition of the pheromone-degrading esterase. In general, the compounds have shown low specificity for the substrate and exhibited only a modest or null EAG intrinsic activity. In the field, benzyl trifluoromethyl ketone, trifluoroacetophenone, (Z)-1,1,1-trifluoro-15-octadecen-13-yn-2-one, (Z)-1,1,1-trifluoro-16-nonadecen-14-yn-2-one and beta-naphthyl trifluoroacetate showed a remarkable disruptant effect when mixed with the pheromone in 1:0.1, 1:1 and 1:10 ratio. (Z)-16-Nonadecen-14-yn-2-one has been found to be a modest agonist of the natural pheromone, exhibiting an attractant activity threefold lower than the parent molecule.

Inhibitory pheromonal activity promoted by sulfur analogs of the sex pheromone of the female processionary mothThaumetopoea pityocampa (Denis and schiff)

New sulfur analogs of the sex pheromone of the female processionary mothThaumetopoea pityocampa have been found to be effective inhibitors of the natural pheromone activity both in EAG bioassays and field tests. The structures of these analogs have been derived from replacement of the oxygen atom(s) of the acetate group by sulfur (compounds 3-5) and the olefinic moiety of the enyne function by the isosteric SCH2 group (compounds 6 and 7). The synthesis and biological activity of 3-[(Z)-12-pentadecen-10-ynylthio]-1,1,1-trifluoropropan-2-one (8), a closely related structure to the pheromone is also described.

Sila-pheromones: Silicon analogues of the female sex pheromone of the processionary moth thaumetopoea pityocampa

The 15- and 10-dimethylsila-analogues of (Z)-13-hexadecen-11-ynyl acetate, the main component of the female sex pheromone of the processionary moth Thaumetopoea pityocampa, were synthesized to evaluate the influence of the silicon atom on the biological activity.

Inhibition of the processionary moth sex pheromone by some haloacetate analogues

AbstractSeveral haloacetate analogues of (Z)‐13‐hexadecen‐ll ‐ynyl acetate, the main component of the sex pheromone of the pine processionary moth Thaumetopoea pityocampa, have been found to be good inhibitors of the natural pheromone. In field tests, the fluorinated compounds exhibited higher antipheromone activity than the corresponding chlorinated analogues, the order of activity being monofluoro > difluoro > trifluoro > monochloro > dichloro > trichloroacetate. In EAG bioassays the trifluoroacetate analogue showed the highest inhibition effect among all the compounds tested. These results agree with others previously reported, and show the primary role played by the steric size of the halogen in these analogues in order to achieve a notable inhibition of the pheromone action.

Field studies on the behaviour of two egg parasitoids of the pine processionary mothThaumetopoea pityocampa

An investigation on the behaviour ofTetrastichus servadeii Domenichini (Hym.: Eulophidae) andOoencyrtus pityocampae Mercet (Hym.: Encyrtidae) was carried out in 2 stands ofPinus nigra Arnold in the Venitian Prealps (NE Italy) by quantitative observations in the field and by trapping with different baits. The results indicate that: 1)O.pityocampae is caught by traps baited with pityolure, the synthetic sex pheromone of the host, whileT. servadeii was never caught. 2) The host selection process ofT. servadeii seems to be associated with the host plant ofThaumetopoea pityocampa (Denis & Schiffermuller) and with the aggregative behaviour of the parasitoid females. 3) The frequency distribution ofT. servadeii on the egg masses follows the negative binomial distribution; the degree of aggregation decreases with the egg mass age. These results may be taken into account in the utilization of egg parasitoids for the biological control ofTh. pityocampa.

Analogs of sex pheromone of processionary moth,Thaumetopoea pityocampa: Synthesis and biological activity

The synthesis and biological activity of some analogs of (Z)-13-hexadecen-11-ynyl acetate1, the major component of the sex pheromone of the processionary mothThaumetopoea pityocampa is described. The analogs have been formally derived by structural modification of the enyne and acetate functions of the parent compound1. In field tests, trifluoroacetate ester16 and the analog,11, with fluorine substitution at the olefin site, decreased the pheromone action, whereas epoxy derivative,10, from epoxidation of the olefin moiety in1, and propionate ester15 gave synergistic activity. The formate14 had a variable effect according to the composition of the lure. Formal reduction of the enyne to give the acetylene2 was found to retain activity. Alcohols12 and13, resulting from hydrolysis of the enyne1 and acetylene2, respectively, inhibited the action of their parent compounds.

ChemInform Abstract: Synthesis of a Fluorinated Analog of the Sex Pheromone of the Processionary Moth Thaumetopoea pityocampa (Denis and Schiff).

AbstractThe four‐step synthesis of the title compound, i.e. the fluoro compound (V), is described, the key‐step being the regioselective ring opening of the oxirane (II) by Olah′s reagent to afford the fluoro‐ hydrin (III) as a 1:1 mixture of the erythro and the threo isomers.

Synthesis of a fluorinated analog of the sex pheromone of the processionary moth thaumetopoea. pityocampa(denis and schiff.)

The synthesis of ( E )-13-fluorohexadec-13-en-11-ynyl acetate 1 , a fluorinated analog of the sex pheromone of the processionary moth Thaumetopoea pityocampa is described. The synthetic scheme involves epoxidation of the double bond, regioselective opening of the oxirane ring with Olah's reagent, tosylation of the resulting fluorohydrin and dehydrotosylation. Structural features of the intermediate diastereomeric fluorohydrins 4a and 4b and tosylates 5a and 5b are also discussed on the basis of their 1H and 19F NMR spectra.

Simple and stereoselective synthesis of sex pheromone of processionary mothThaumetopoea pityocampa (Denis and Schiff.)

A simple and stereoselective synthesis of (Z)-13-hexadecen-11-yn-1-yl acetate, the major component of the sex pheromone ofThaumetopoea pityocampa (Denis and Schiff.) is described. The procedure essentially involves formylation of a terminal acetylene to the corresponding aldehyde followed by a stereochemically controlled Wittig reaction, which has been studied under a variety of conditions.

Synthesis of (Z)-13-hexadecen-11-yn-1-yl acetate Major component of sex pheromone of the processionary moth

The synthesis of the major component of the sex pheromone of the processionary mothThaumetopoea pityocampa is described. The synthesis uses the carbocupration of acetylene, followed by the coupling with the appropriate 1-iodoalkyne. This synthetic pheromone was shown to be of 98.8%Z purity.

Initial field trials with the synthetic sex pheromone of the processionary mothThaumetopoea pityocampa (Denis and Schiff.)

Synthetic (Z)-13-hexadecen-11-ynyl acetate has been shown to be highly active in catchingThaumetopoea pityocampa (Denis and Schiff.) males in field trials carried out in different parts of Spain. A variety of formulations containing antioxidants or solid paraffin were tested. Formulations containing 3 and 10% ofE isomer showed a decrease of activity compared with those prepared with pureZ isomer. Dodecyl acetate, also found in the virgin female gland, did not show any synergistic effect when tested in a 9∶1 mixture with the synthetic pheromone. The product exhibited a remarkable persistence of activity under the field conditions even in the absence of stabilizer.