bonagota feromonio

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Behavioural effects of minor sex pheromone components inBrazilian apple leafroller Bonagota cranaodes (Lep., Tortricidae)

M. D. A. Coracini1, M. Bengtsson1, A. Reckziegel2, A. E. Eiras3, E. F. Vilela4, P. Anderson1, W. Francke2,J. Lo fqvist1 and P. Witzgall11Department of Crop Science, Swedish University of Agricultural Sciences, Alnarp, Sweden; 2Department ofOrganic Chemistry and Biochemistry, University of Hamburg, Germany; 3Department of Parasitology, FederalUniversity of Minas Gerais, Belo Horizonte, Brazil; 4Department of Animal Biology, Federal University ofVicosa, Brazil

Ms. received: March 3, 2002; accepted: August 26, 2002

Abstract: The behavioural response of Brazilian apple leafroller males, Bonagota cranaodes (Meyrick), to natural andsynthetic sex pheromone was studied in a wind tunnel. Calling females elicited upwind flights followed by landing and

wingfanning at the source in 72% of the males tested. Female gland extracts, with the main compound

(E, Z)3,5dodecadienyl acetate released at 100 pg/min, attracted 57% of the males to the source. Few males (1%)

were attracted to the main compound alone, released at the same rate. Even a synthetic blend of all five gland

compounds eliciting an antennal response, formulated according to their proportion in female gland extracts, was

barely attractive (7%). Comparison of this synthetic blend and female gland extracts indicates a behavioural role of

other gland compounds. Male attraction was significantly increased (34%) in response to a 100 : 5 : 5 : 5-blend of the

main compound and three minor gland compounds, (Z)-5-dodecenyl acetate, (E, Z)-3,5-tetradecadienyl acetate, and

(Z)-9-hexadecenyl acetate.

Key words: antennal response, redundancy, sex pheromone blend, synergism, synthesis, upwind flight behaviour

1 Introduction

The Brazilian apple leafroller, Bonagota cranaodes(Meyrick) (Lep., Tortricidae), is an economicallyimportant insect of apple in Brazil and Uruguay. Themoths are on the wing throughout the year (Lorenzato,1984), necessitating multiple sprays for populationcontrol. New methods for controlling B. cranaodesneed to be developed as insecticide treatments are notefficient enough, and as insecticide residues are notonly a health hazard, but are also serious obstacles for

exportation of fruit.Orchard pests introduced to Brazil from the Old

World, such as the Oriental fruit moth Grapholitamolesta and codling moth Cydia pomonella can becontrolled with pheromones, either by mating disrup-tion (Rice and Kirsch, 1990; Waldner, 1997; Gut andBrunner, 1998; Thomson et al., 1998; Brunner et al.,2002) or the attract-and-kill technique (Charmillotet al., 2000). The first step towards the deploymentof pheromone-based control techniques againstB. cranaodes is the study of the behavioural effect offemale-produced pheromone-related compounds. Themain pheromone compound of B. cranaodes, (E,Z)-

3,5-dodecadienyl acetate (E3,Z512Ac), and a numberof additional compounds have been identified from thefemale gland (Unelius et al., 1996; Eiras et al., 1999;

Coracini et al., 2001). The male antennal response tominor gland compounds and their behavioural effect inthe wind tunnel has been studied.

2 Materials and methods

2.1 Insects

Larvae were collected in apple orchards near Vacaria (Rio

Grande do Sul, Brazil), and reared on a semiartificial agar-based diet. Field-collected insects were interbred with thelaboratory population each year. The insects were held at2224C, under a 14 : 10 hours L : D photoperiod, and 55%relative humidity. The insects were sexed in the pupal stageand adults were maintained in different rooms. Males weretested on the day after eclosion, 14 h after the onset of the

scotophase.

2.2 Pheromone gland extraction

Single glands of 23-day-old calling females were extracted1 h before, and 1, 3, and 5 h after onset of scotophase(n 10). Glands were extracted in 1 min in 5 ll of redistilledhexane (Labscan, Malmo , Sweden), and the extracts were

immediately analysed on a Hewlett Packard 5890 gaschromatograph (GC) (Hewlett Packard, Wilmington,

JEN 127 (2003)

J. Appl. Ent. 127, 427434 (2003) 2003 Blackwell Verlag, BerlinISSN 0931-2048

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USA), with flame ionization detection (FID) on a DB-Waxcolumn (30 m 0.25 mm; J & W Scientific, Folsom, CA,USA).

For behavioural tests in the wind tunnel, 75 pheromoneglands of 2- to 3-day-old calling females were extracted in

7 ll of redistilled hexane, during the first 3 h of scotophase.The amount of the main compound E3,Z5-12Ac in these

extracts was quantified by GC, and the extracts were thendiluted in redistilled ethanol to obtain E3,Z5-12Ac at 0.1and 10 pg/ll. The diluted extracts were stored at 18C. Forelectrophysiological recordings, gland extracts were pre-pared from the glands of five female insects (n 9).

2.3 Chemicals

The four stereoisomers of 3,5-dodecadienyl acetate weresynthesized as shown in fig. 1.

Synthesis of the (E,Z)3,5-isomer (1) started with 2-bromo-ethanol (5), which was chain-elongated with propargylalcohol (Brandsma, 1988). The resulting product was conver-ted to the corresponding 2-alkenol by (E)-selective reductionwith LiAlH4 (Raphael, 1955) and oxidized by Swern-oxida-

tion (Mancuso and Swern, 1981) to yield the aldehyde (6).Wittig reaction (Bestmann et al., 1976) of (6) with n-heptyltriphenylphosphonium bromide, followed by deprotection of

the alcohol moiety and subsequent acetylation yielded (1).

The (E,E)-3,5-isomer (2) was synthesized in a short but lessstereospecific way: 3-bromopropan-1-ol (7) was converted to3-hydroxypropyl triphenylphosphonium bromide (8) and

made to react with commercially available (E)2-nonenal(10) (Aldrich, Steinheim, Germany). Addition of two equiv-

alents ofn-butyllithium to (8) yielded a 3 : 1-mixture of (E,E)and (Z,E)3,5-dodecadien-1-ol, which was subsequently acet-

ylated to yield (2).Both the (Z,E)-3,5-isomer (3) and the (Z,Z)-3,5-isomer (4)were prepared from the protected Wittig salt (9) of3-bromopropan-1-ol (7) (Schow and McMorris, 1979). Con-trary to the synthesis of (2), addition of one equivalent ofsodium bis(trimethylsilyl)amide to (9) and Wittig reactionwith (E)2-nonenal (10), followed by deprotection and acety-lation of the resulting tetrahydropyranyl ether (11), yielded

(3) in 92% isomeric purity.The same type of (Z)-selective Wittig reaction (Bestmann

et al., 1976) was used to obtain 2-[(3Z)-dodecen-5-ynyloxy]-tetrahydro-2H-pyran (14) from the reaction of (9) with2-nonynal (13). The latter was generated by chain elongationof 1-bromohexane (12) with propargyl alcohol (Brandsma,1988) and subsequent Swern oxidation (Mancuso and Swern,

1981) of the resulting 2-nonynol. The triple bond of (14) was(Z)-selectively reduced by addition of dicyclohexylborane(Wong et al., 1984). Finally, deprotection and acetylationyielded (4) in good amounts.

Fig. 1. Synthesis of E,E-,

E,Z-, Z,E-, and Z3,Z5-12Ac

428 M. D. A. Coracini et al.


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(E,Z)-3,5-tetradecadienyl acetate (E3,Z5-14Ac) was syn-thesized the same way as described for (1) using n-nonyltriphenylphosphonium bromide instead of n-heptyl triphe-

nylphosphonium bromide.Due to the synthetic route, crude compounds (1) and (3)

were both contaminated with 8% of E3,E5-12Ac (2).Complete removal of this byproduct was achieved by Diels-

Alder reaction with tetracyanoethylene in tetrahydrofurane(Paquette, 1964). Crude (2) represented a 3 : 1-mixture withZ3,E5-12Ac (3), while crude (4) contained 12% of E3,Z5-12Ac (1). Both compounds could be purified to >99% byflash chromatography on AgNO3/SiO2 (Unelius et al., 1996)(230400 mesh; 15% v/v; 400 g impregnated silica gel/0.5 gof dodecadienyl acetate), using hexane/ethyl acetate 20/1 v/vas the eluent.

Isomeric and chemical purity of E3,Z5-12Ac and itsisomers was 99.4% and >99%, respectively. The other test

compounds were >99% pure.

2.4 Gas chromatographyelectroantennographic

detection

Freshly prepared extracts of five female glands were analysedby coupled GC and electroantennographic detection (GC

EAD), using a Hewlett Packard 6890 GC (Hewlett Packard,Wilmington, USA) with a HP-INNOWax capillary column(30 m, 0.25 mm ID) (Hewlett Packard, Wilmington, USA),interfaced with an electroantennogram apparatus (Syntech,Hilversum, The Netherlands). A split column allows simul-taneous recordings from the flame ionization (FID) and theelectroantennographic detector (EAD) (Arn et al., 1975).

One arm of the split column led to a glass tube (diameter8 mm), with a charcoal-filtered and humidified air stream

(0.5 l/min). Male antennae of B. cranaodes were 0.5 cm fromthe end of this glass tube and 30 cm from the EAD-outlet ofthe GC. The antennae were mounted between two glass

pipette electrodes containing Ringer solution; one electrodewas connected to the ground and the other to an amplifier(Syntech). The GC was operated in splitless injection modeand the oven programmed from 50C (2-min hold), at 10C/min to 230C. Injector and EAD-outlet temperature was220C and the split ratio between FID and EAD was 1 : 1.Recordings (n 9) were averaged according to Hillbur et al.(2003).

2.5 Wind tunnel tests

The tunnel was the one described by Witzgall and Arn

(1991). It has a flight section of 63 90 200 cm, and was litdiffusely from behind and above at 6 lx, the wind speed was

30 cm/s, and air temperature ranged from 22 to 24C.Batches of 15 males were transferred to glass tubes

(2.5 15 cm) stoppered with gauze on both ends, 5 min

before the tests. Single males were given 2 min to respondand were scored for the following behaviours: taking flight,upwind flight over 50, 100 and 150 cm, and landing atsource, 180 cm from the release point. Males were used once.Each test session comprised three batches of 15 males,starting after scotophase, and lasted 34 h. For each phero-mone source, four or eight batches of 15 males (n 60

and n 120, respectively) were tested on four or eightdifferent days.

Males were flown to single calling females, a pheromonegland extract or synthetic compounds. Calling females wereplaced individually in small glass tubes. Quantified phero-mone gland extracts (see above) and blends of syntheticcompounds were diluted in redistilled ethanol to obtain the

main pheromone compound E3,Z5-12Ac at 0.1 and 10 pg/ll.Pheromone solutions were dispensed from a sprayingapparatus (El-Sayed et al., 1998, 1999a) at a rate of 10 ll/min.

2.6 Statistical analysis

The percentage of males, within one test batch of 15 males,showing a specific behaviour was transformed to log(x + 1).The four or eight batches of 15 males flown to the variousblends were compared by an analysis of variance, followedby a Tukey test (P < 0.05).

3 Results and discussion

3.1 Diel periodicity of pheromone production

The gland titre of the main compound E3,Z5-12Acpeaked approximately 2 h after onset of female calling,3 h into the scotophase at 0.8 0.6 ng/female

Table 1. Diel periodicity ofpheromone titre in Bonagotacranaodes female glandextracts as analysed by GC

Individual glandsa 75 glandsb

Compound 1 hc 1 hc,d 3 hc,d 5 hc,d (13 h)c,d

12Ac e 32 32 34 9 18

Z5-12Ac 137 44 3

E3,Z5-12Ac 100 32 100 100 100 32 100

(0.4 0.3 ng)f (0.5 0.2 ng)f (0.8 0.6 ng)f (0.6 0.3 ng)f

Z3,Z5-12Ac 38 6 34 11 33 9 13

E3,Z5-12OH 190 61 173 92 97 48 121 50 100

14Ac 173 77 181 149 149 137 213 130 200

Z7-14Ac 24 11 7

E3,Z5-14Ac 273 88 71 22 12

16Ac 85 36 83 50 77 29 102

Z9-16Ac 190 101 217 134 237 122 245 107 224

18Ac 758 641 974 739 935 717 1126 838 1296

Z11-18Ac 33 14 42 18 41 38 49 37 16

18OH 60 23 71 52 40 37 80 48 87

a Proportion of pheromonal compounds in extracts of single female glands (n 10).b Batch extract of 75 glands of calling females used in wind tunnel tests (fig. 1).c Time before and after onset of scotophase.d

Calling females.e Trace amounts (


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(table 1). A correlation between female calling andpheromone production has been reported for variousother lepidopteran species (Delisle and Royer, 1994).No significant changes were found in the proportions ofthe female blend, as in codling moth (Backman et al.,1997). A release of behaviourally active pheromonecomponents in rather constant ratios has been

observed in several moths, such as Heliothis virescens(Pope et al., 1982), Pectinophora gossypiella (Hayneset al., 1984), Yponomeuta padellus and Y. rorellus (Duet al., 1987), and Cacoecimorpha pronubana (Witzgalland Frerot, 1989). Compounds previously identi-fied in B. cranaodes (Coracini et al., 2001) were allpresent in individual gland extracts, although several ofthe minor compounds were found only in traceamounts.

3.2 Gas chromatographyelectroantennographic

detection

Subsequent GCEAD analysis of B. cranaodes femalegland extracts (n 9) showed five compounds whichconsistently elicited a male antennal response (fig. 2).The antennae responded in addition to Z3,Z5-12Ac, as

shown by subsequent tests with synthetic compound.The antennal response to the Z,Z isomer cannot bedistinguished when using gland extracts, as it elutesshortly after the main compound E3,Z5-12Ac.

3.3 Wind tunnel bioassay

Calling females attracted 72% of the males tested, andthese males wing-fanned after landing at the female

Fig. 2. Wind tunnel attrac-tion of Bonagota cranaodesmales (n 120) to naturaland synthetic sex pheromone

(ae), and averaged maleantennal response (n 9)

to female gland extracts

(GC-EAD). Female glandextracts (b), a syntheticblend of the GC-EAD-activecompounds at the proportion

found in the female glandextract (c), the best syn-

thetic blend (d), and themain component alone (e)were released from a sprayer

at 1 and 100 pg E3,Z5-12-

Ac/min, respectively. Barswith the same letter are notdifferent (P < 0.05; Tukey

test), each step in thebehavioural sequence is

treated separately



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cage (fig. 2a). All males taking flight (75%) flewupwind over 150 cm, 30 cm downwind from the callingfemale. Males which did not arrive at the female (3%)landed several centimetres below, on the rod holdingthe female cage. The activation behaviour of B.cranaodes (data not shown in fig. 2) is different fromother tortricids, inasmuch as only 22% of the maleswere wing-fanning while walking before taking flight.In codling moth, for example, all males start wing-fanning before taking off (El-Sayed et al., 1998).

Female extracts released from a sprayer attractedonly 2% of the males at a release rate of 1 pg E3,Z5-12Ac per minute, but 57% were attracted at a 100-foldhigher release rate, 45% wing-fanned after landing atthe source (fig. 2b). The composition of the extractused for wind tunnel tests is shown in table 1.

A release of 100 pg/min of E3,Z5-12Ac (fig. 2b)may be slightly higher than the female emission: glandsof calling B. cranaodes females contained up to0.8 0.6 ng of E3,Z5-12Ac (table 1). Codling moth

female glands contained 9 ng of the main compoundcodlemone at peak calling, and calling females released7 ng/h (Backman et al., 1997). A dual choice testshowed equivalent male codling moth attraction tosingle calling females and sprayed extracts, whenextracts were released at 100 pg/min or 6 ng/h(El-Sayed et al., 1999b). In two other tortricids,females released their gland content approximatelyonce an hour (Witzgall and Frerot, 1989; Witzgallet al., 1991).

The male response to sprayed extracts stronglyincreased with release rate (fig. 2b), but this was notthe case with the main compound E3,Z5-12Ac alone

(fig. 1e). Therefore, the four compounds were addedto the main compound eliciting an antennalresponse (12Ac, Z5-12Ac, E3,Z5-14Ac, Z9-16Ac), at

the proportion found in the female gland extract usedin the wind tunnel (fig. 2; table 1). Surprisingly, thisblend was hardly attractive, with only 7% of the maleslanding at the source of the higher release rate (fig. 2c).

Therefore, the behavioural activity of these fourcompounds, and two other compounds, Z3,Z5-12Acand Z7-14Ac, in two-component blends with the maincompound were screened (table 2). Addition of 5%and 20% Z5-12Ac seemed to have a synergistic effecton male behaviour, but differences in the maincompound alone were not significant. The saturated12Ac had an antagonistic effect on activation andupwind flight; and blends including Z3,Z5-12Ac, Z7-14Ac (5%), or Z9-16Ac (20%), were less attractivethan blends of the main compound and Z5-12Ac.

Best attraction to synthetics was obtained with a100 : 5 : 5 : 5-blend of E3,Z5-12Ac, Z5-12Ac, E3,Z5-14Ac, and Z9-16Ac (table 2, fig. 2d). Omission of Z9-16Ac from this blend, as well as addition of 12Acdiminished male attraction compared with the main

compound alone. On the contrary, a blend of thesecompounds, formulated according to the gland pro-portions 100 : 3 : 10 : 200 was not attractive andaddition of 12Ac seemed to further decrease the maleresponse (table 2).

4 Conclusion

Males of the Brazilian apple leafroller B. cranaodeswere strongly attracted to calling females and femalegland extracts. Significantly fewer males were attractedto the best synthetic four-component blend than to

calling females, and the wing-fanning response afterlanding at the source was strongly diminished (fig. 1).A discrepancy in male attraction to natural and

Table 2. Wind tunnel response ofBonagota cranaodes males to the main pheromone compound blended with furthergland compounds

Compound (pg/min) Male response (% SD)

E3,Z5-12Ac 12Ac Z5-12Ac Z3,Z5-12Ac Z7-14Ac E3,Z5-14Ac Z9 -1 6Ac Takeoff Upwind flig ht* La nding

1 57 20ab 25 17ab 6 10bc

1 0.05 15 15c 0d 0c

1 0.2 18 13c 2 6d 0c

1 0.05 85 12a 58 18a 17 19ab

1 0.2 67 21ab 48 25ab 15 19ab

1 0.05 67 18ab 28 18ab 0c

1 0.2 63 17ab 13 13bcd 0c

1 0.05 71 26a 35 28ab 0c

1 0.2 58 25ab 20 21bc 3 11bc

1 0.05 87 16a 50 35ab 7 16bc

1 0.2 85 15a 38 16ab 3 8bc

1 0.05 90 16a 37 7ab 2 6bc

1 0.2 80 17a 27 26ab 0c

1 0.05 0.05 58 31ab 42 32ab 18 28ab

1 0.05 0.05 0.05 70 22a 52 26a 32 21a

1 0.2 0.05 0.05 0.05 62 18ab 48 26ab 12 10ab

1 0.03 0.1 2 33 23bc 7 9cd 0c

1 0.2 0.03 0.1 2 16 16c 2 9d 0c

Percentages followed by the same letter within each behavioural category are not significantly different (n 60: four batches of 15 males;

P < 0.05, Tukey test).

* Upwind flight over 150 cm, 30 cm downwind from source.

Behavioural effects of minor sex pheromone components in Bonagota cranaodes 431


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synthetic pheromone in the wind tunnel is known fromvarious other moths (Vetter and Baker, 1983; Sanders,1984; Baker et al., 1991).

Multicomponent blends would have to be tested forthe identification of further behaviourally active com-pounds in B. cranaodes, as even addition of twosynergists, Z5-12Ac and E3,Z5-14Ac, did not signifi-

cantly augment male attraction over the main com-pound alone (table 2). In addition, a more stringentbioassay, such as flight track analysis (El-Sayed et al.,1999c) may help to overcome the individual variationof male attraction in the wind tunnel, and to reveal therole of further pheromone synergists.

The most attractive synthetic blend, containingE3,Z5-12Ac, Z5-12Ac, E3,Z5-14Ac and Z9-16Ac ina 100 : 5 : 5 : 5-proportion, was derived from flighttunnel tests with two-component blends (fig. 2d,table 2) and previous field trapping tests (Coraciniet al., 2001). Weak attraction to a blend of thesecompounds plus 12Ac, in a proportion designed to

mimic the composition of female gland extracts(table 1, fig. 2c) is probably because of the presenceof 12Ac, as well as large amounts ofZ9-16Ac (table 2).The saturated 12Ac had an antagonistic effect;Z9-16Ac is approximately 256 times less volatile thanthe main compound (a factor of 4 for each methylenegroup), and the proportion of this compound in thefemale effluvia is thus likely to be much lower than ingland extracts.

Unlike passive dispensers, the pheromone sprayer(El-Sayed et al., 1998, 1999a) evaporates compoundblends at the proportions formulated in the solutionapplied. Sprayed gland extracts and female effluvium

are thus different with respect to blend proportion,because of differences in the volatility of the blendcomponents. They may also be different in blendcomposition, as gland extracts contain biosyntheticprecursors which may not be released by callingfemales.

It is therefore noteworthy that the best four-component blend (fig. 2d) was more attractive thanthe five-component mimic (fig. 2c); sprayed glandextracts (fig. 2b) did contain the same amounts of12Ac and Z9-16Ac as the five-component mimic. Thisshows that there are further, behaviourally activegland compounds which compensate for a suboptimalblend composition of sprayed gland extracts. An

increase of male behavioural response with dosefurther corroborates this (fig. 2b). However, these yetunidentified compounds did not elicit a male antennalresponse (fig. 1), and two candidate compounds,Z3,Z5-12Ac and Z7-14Ac (table 1; Coracini et al.,2001), did not have a synergistic effect on malebehaviours when tested in two-component blends withthe main compound (table 2).

Most lepidopteran pheromones are blends of a maincompound and pheromone synergists. Females usuallyproduce further compounds in the gland, which do notplay an overt behavioural role (Arn et al., 1992, 2000).In some multicomponent pheromone blends, beha-

vioural synergists can be substituted with other glandcompounds, to produce the same behavioural effect.This phenomenon has been termed pheromone

redundancy (Linn et al., 1984; King et al., 1995; Toddet al., 1995; Mayer and Mitchell, 1999).

However, this concept of redundant pheromonecompounds may merely reflect the use of imperfectbehavioural assays. Wind tunnels do not reflect thenatural stimulus milieu. Differences between subopti-mal and optimal pheromone blends may become

obvious during long-range upwind flights in the field.Furthermore, some pheromone components show aneffect only in rather complete blends (e.g. Arn et al.,1986; Wu et al., 1995; El-Sayed et al., 1999c). InB. cranaodes, the difference between the main com-pound alone and the four-component blend is clear(fig. 1d,e), but none of the minor compounds signifi-cantly increased male attraction in two-componentblends (table 2). The blend ratio of these and yetunknown synergists can thus only be optimized whentesting multi-component blends.

Considerable resources are needed for such work,and it is therefore important to keep the goal of a

pheromone identification in B. cranaodes in mind,which is the development of an environmentally safecontrol strategy. Any pheromone blend will have tobe adapted to the dispenser used in the field and itis thus meaningful to first identify the most prom-ising technique and the corresponding dispensermaterial.

An advantage of the mating disruption technique isthat control of codling moth C. pomonella and Orientalfruit moth G. molesta is well-established (Rice andKirsch, 1990; Waldner, 1997; Gut and Brunner, 1998;Thomson et al., 1998; Brunner et al., 2002), both speciesare important in Brazilian apple orchards. In view of

technical synthesis needed for mating disruption andthe field life of dispenser formulations, it is encouragingthat the isomers of the main compound E3,Z5-12Acdid not have a strong antagonistic effect in B. cranaodes.The Z,Zisomer is present in female gland extracts, butdid not modify male behaviours in a two-componentblend (table 2). The other isomers E,Eand Z,Ehad noeffect on male attraction in the field (Coracini et al.,2001). Synthesis of rather pure E3,Z5-12Ac and pro-tection of this compound against isomerization indispenser formulations would be costly.

The attract-and-kill technique, which has beensuccessfully used against codling moth C. pomonella(Charmillot et al., 2000), has considerable potential for

control of B. cranaodes. Trap lures baited with thefour-component blend remained attractive in the fieldover several months (Coracini et al., 2001). In addition,B. cranaodes does not diapause, as this is the case withorchard insects from temperate climate zones. Whileapple trees are devoid of leaves, B. cranaodes larvaefeed at greatly reduced population densities on nativeplants and this period is thus ideal for populationcontrol. However, mating disruption in orchardswithout leaves is expected to be difficult. In grapevinetortricids, mating disruption is known to be lessefficient during spring, as the absence of vine foliageprevents aerial pheromone concentrations from build-

ing up (Arn and Louis, 1996). An attracticide aiming atmale insects that can be combined with femaleattractants, is are currently under development.



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Acknowledgements

We wish to thank John A. Byers for helpful assistance. This

study was supported by the International Foundation forScience (IFS) and the Foundation for Strategic Environmen-

tal Research (MISTRA).

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Authors addresses: Miryan D. A. Coracini (correspondingauthor), Marie Bengtsson, Jan Lofqvist, Peter Anderson, Peter

Witzgall, SLU, Box 44, 23053 Alnarp, Sweden; AureliaReckziegel, Wittko Francke, Department of OrganicChemistry and Biochemistry, University of Hamburg,Martin-Luther-King-Platz 6, 20146 Hamburg, Germany;

Alvaro E. Eiras, Department of Parasitology, FederalUniversity of Minas Gerais, Box 486, 31270-901 BeloHorizonte-MG, Brazil; Evaldo F. Vilela, Department of

Animal Biology, Federal University of Vicosa, 36571-000Vicosa-MG, Brazil. E-mail: [email protected]


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