CA1306263C - (z)-3-dodecen-1-o1 (e)-2-butenoate and its use in monitoring and controlling the sweetpotato weevil - Google Patents

Abstract

ABSTRACT
A pheromonal compound produced by the sweetpotato weevil has been identified as (Z)-3-dodecen-1-ol (E)-2-butenoate. The synthetically-prepared compound demonstrates activity toward the sweetpotato weevil comparable to or greater than that of the natural female and comparable to that of its natural counterpart under field conditions. The novel compound provides a sensitive tool for detection of the sweetpotato weevil. By attracting adult weevils to field traps, this compound provides a means for monitoring and controlling this major agricultural pest.

Description

130fi~63 ..
., PC ~-1021 ` Robert R. Heath James A Coffelt Fredrlck I. Proshold Phlllp E. Sonnet James H. Tumllnson III
Serial No. 06/879,~96 Filed: June 27, 1986 ~ 3-DODECEN-l-OL (E)-2-BUTENOATE AND ITS USE IN
M~NITORING AND CONTR~LLING THE S~EETPOTATO ~EEVIL

BACKGROUND OF THE INVENTION

l. Fleld of the Inventlon Thts 1nvent10n relates to a novel compound ~nd use thereof to mon1tor and control the sweetpotato weevll. More partlcularly, the lnvent10n relates to (Z)-3-dodecen-l-ol (E)-2-butenoate and lts use ~s an attractant, dlsruptant, and monltorlng agent for the sweetpotato weev11.

2. Descrlpt10n of the Art Sweet pot~to 1s consldered the s1xth most tmportant human food crop 1n the world ~nd 1s surpassed 1n 1mportance ~s ~ root crop only by the potato. The sweetpotato weevll, Cylas fon~lcarlus elegantulus (Summers), 1s the most devastat1ng pest of sweet potatoes worldwlde.
r' Even very low level pre- and postharvest 1nfestat10ns reduce both - quallty and marketable y1eld and c~n render the sweet potato unf1t for , lS consumpt10n. Th1s 1s due to the presence of extremely b1tter tast1ng and tox1c sesqulterpenes that are produced by the sweet potato tlssue -~ ln response to 1nsect feedlng and th~t lmpart ~ b1tter taste to the sweet potato. Losses due to such lnfestat10ns and d1seases that often follow weevll attack are est1mated at 35 to 95S.
Presently, there 1s no sultable method av~tlable for the detect10n of low level lnfestatlons; by the t1me 1nsects are seen on the crop, conslderable damage h~s already been done. The underground feedtng hab1ts of the sweetpotato weevll larvae and the nocturn~l actlvlty of ' I_ ~

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13~fiZ2~3 the adu1ts m~ke 1t d1ff1cult for f~rmers to m~ke effect1ve use of pest1c1des Thus, there ts ~ need for ~ sens1t1ve detectlon tool to sld the grower ln mon1tor1ng ~nd controlllng 1nfestatlons of th1s ma~or ~gr1cul tural pest.
The use of 1nsect sex ~ttr~ctants ~s potent1~1 control ~gents ln 1ntegr~ted pest m~n~gement progr~ms h~s been reported A number of econom1c~11y 1mport~nt 1nsects ~re currently mon1tored. pdrtlally controlled, or completely controlled by use of the1r own speclfic sex pheromone The use of pheromones h~s ~tso been reported for loc~t1ng, IO survey1ng, or monttor1ng pest popul~tlons ~t levels not otherwlse detectable In the c-se of the sweetpot~to weevll, the lack of 1denti-f1c~t10n and ~n11~b111ty of ~ sweetpot~to weev11 pheromone h~s precluded appl1c~t10n of th1s technology to the treatnent of th1s pest SUMMARY OF THE INVENTION
We h~ve now for the flrst t1me obt~1ned 1n pure or substont1ally pure fonn the ~or fem~le-produced sex sttr~ct~nt of the sweetpot~to wcev11, Cyl~s form1csr1u~ eleg~n us ~Summers). Th1s ncw compound, 1dent1f1ed ~s (Z)-3-dodecen-I-ol (E)-2-butenoAte, h~s bcen 1sol~ted from fcm~les of the sweetpot~to weev11 (SPW) end hss ~lso been success-fully synthes1zd The novel ccmpound of the 1ment10n 1s the f1rst croton~te ester ~dent1f1d ~s ~n 1nsect sex ~ttr~ct nt. The synthet1c ~ter1sl demon-str~tes b1010g1c~1 ~ct1v1ty tow~rd SP~I n~les c~nparable to or grester th~n th~t of the nstur~l SPl~l female ~nd comp~r~ble to that of the pur1-f1ed natural sttr ctont. ~Z)-3-~odecen-I-ol (E)-2-butcno~te 1s h1ghly effect1ve ln ~ttr~ct1ng SP~I ~ales to tr~ps b~1ted wlth the campound.
The novel c~mpound prov1des ~ #ns1t1ve tool for detect10n of the SP~ ~nd prov1des ~ mesns for popul~t10n control snd popul~t10n dens1ty est1m~t10n of th1s pest Its usefulness 1n el1c1t1ng ~ beh~v10r~1 response when ~ppl1ed to ~ locus of SPW m~les suggests the follow1ng fi~63 econom1c app11cat10ns: (I) the detectton of lnfest~tlon outbre~ks;
~2) the monltorlng of exlstlng adult populatlons tn order to predlct future tnfestatlon levels for schedullng tre~tment w1th conventlonal pest1c1des; and ~3) the control of reproductlon ln adult popul~tlons elther by d1rect dtsruptlon of matlng through tonfus1ng or lnh1bltory propert1es, or by attract1ng ~ demographlcally s1gnlflcant portlon of the male populat10n for subsequent destructlon or sterlllzDtton.
In accordance w1th thls dlscovery lt ls ~n ob~ect of the lnvention to tdent1fy for the f1rst t1me a un1que sex attractant for the sweetpotato IO weevll.
It ls also an ob~ect of the 1nventlon to prov1de a Ineans for the productlon of synthetlc (Z)-3-dodecen-I-ol (E)-2-butenoate.
Another ob~ect of the lnventlon 1s to utlllze (Z)-3-dodecen-I-ol (E)-2-butenoate as a detect10n, nlon1tor1ng, or control agent for this IS ~ or agr1cultural pest.
A further ob~ect ls to provlde a SPW sex attractant for use w1th 1nsect1c1des, b1010g1cal control agents and the 11ke to attr~ct and combat the pest.
Other ob~ects and advantages of the lnvent10n wlll become reDdlly ~pparent from the ensu1 ng descr1pt10n .

BRIEF DESCRIP~ION OF ~HE DRAWIN6S
FlG. I shows the synthes1s of (Z)-3-dodecen-I-ol tE)-2-butenoate.
FIGS. 2A and 2B show the laboratory (A) and f1eld (B) response of the SPW to varlous 1solates contaln1ng (Z)-3-dodecen-I-ol (E)-2-buteno~te.
FIGS. 3A and 3B show the 1sobutane (A) ~nd methane (B) lonlzatton mass spectr~ of the act1~e fractton from SPW female volattles.
EIG. 4 shows the PMR spectrum of the pur1f1d natural sex attractant.
FIGS. SA and SB show the f1eld response of SPW Inales to the pur1-fled natural sex attract~nt ~nd synthetlc se)~ ~ttractant on glass ~A) and rubber sept~ (B).

1 3 ~6X63 FlG. 6 shows the field response of SP~ males to ~Z~-3-dodecen-I-ol (E)-2-buteno~te tn rubber septa.

DE~AILED DESCRIPTION OF THE INVENTION
The novel sex attractant compound of the 1nventlon, IZ)-3-dodecen-I-ol (E)-2-butenoate ls char~cter1zed by the follow1ng structural formula:

- C8HI7 ~ ~

The novel compound was 1solated from volat11es of SPW fe~ales follow1ng a sequence of four chromatogr~phlc separ~tlons: (I) s111ca (grav1ty n ow), (2) hlgh perform~nce llqu1d chrom~togr~phy (HPLC), (3) IO gas-11qu1d chromatography (GLC) us1ng a nonpol~r ~methyl s111cone statlonary phase) column, and (4) GLC us1ng ~ polar (polyethylene glycol st~t10nary phase) column. The novel sex ~ttr~ct~nt compound also c~n be prep~red synthet1cally 4s descr1bed 1n Examp~e 2 below and shown ln FIG. I. As used 1n the spec1f1cat10n ana the clalms, the phrase ~pure or subst~ntlally pure~ ~eans that the novel compound of the 1nventlon ls subst4ntl~11y free of undeslrable m~sklng or lnh1bltory èffects w1th regsrd to the 1ntended act1v1ty, and 1n cases ~here lt 1s obtalned from SPW volat11es, 1t has been purlflea follow1ng the sequence of four chromatographlc procedures descrlbed above or by procedures prov1d1ng equlvalcnt pur1ty.
The blologlcal and chemlc~l d~ta ~how th~t (Z)-3-dodecen-I-ol (E)-2-butenoate 1s the ~a~or component of thè female produced sex pheromone of the SP~ (C. f. eleg~ntulus). Unl1ke pheromone components that h~ve been descrlbed for m~ny Coleoptera spec1es, the mater1al funct10ns as a sex pheromone 1n that 1t 1s produced by one sex, and el1c1ts ~n overt ser1es of behavlDrs l~ctlvat10n, orlent~tlon, etc.) only by the opposlte sex.
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~3C~ 3 ISOLATION OF THE ATTRACTANT
To obta1n the act1ve compound 1n pure or substant1ally pure form from the 1nsect volat11es, a lengthy sequence of complex chromatograph~c procedures was carr1ed out. The complete deta11s of the tsolat10n procedure are descrlbed 1n Example I below. Brlefly, the tnsect vola-t~les were obta~ned by draw~ng alr over SPW females and collect1ng the volatlles on an adsorbent cont1nuously over a 30-day per10d for a glven batch of 1nsects. The concentrated volat11e fract~on wh1ch contalned 1n excess of several thousand compounds, was then chromato-IO graphed on s111ca (grav1ty flow). The act1ve fractlons from the grav1ty flow column were concentrated and chromatographed by HPLC. The act1ve fractlons eluted from the HPLC column were comblned, concentrated, and further pur1fied by GLC on a nonpolar methyl sil1cone (OV-101) column.
The actlve fract10n obta1ned from the OY-101 GLC column conta1ned 1n I5 excess of 400 compounds. The mater1al requ1red still further pur1f1-cat10n by GLC us1ng a polar polyethylene glycol (Carbowax) column.
8eg1nn1ng w1th the unpur~f1ed volat11es (crude extract) and cont1nu1ng through the pur1f1cat10n, all mater1al (comb1ned, act1ve, and 1nact1ve fract10ns) were b10assayed 1n ser~al d11utlon (6-IO repl1cates per dose) 1n the laboratory (FIG. 2A~ to ensure that no loss 1n act1v1ty had occurred. In add1t10n, f1eld b10assays of the crude extract, the HPLC pur1f1ed ~ater1al, and the Carbowax GLC pur1f1ed mater~al were conducted to ensure that no loss of act1v1ty 1n the f1eld occurred as a result of the separat10n performed. Results of these f1eld b10assays at equal dose are summar1zed ln FIG. 2B. The d11ut10n ser1es obtalned for the grav1 b flow s111ca column and for the m1cropreparat1ve GLC
samples from the nonpolar column and the 1nactlve fract10ns are om1tted from FIG. 2 for s1mpl1c1ty. For all compar1sons, there was no 1nd1cat10n of loss of b101091cal act1v1ty 1n e1ther f1eld or laboratory b10assays.
All b1010g1cal act1v1ty of the act1ve mater1al that was obta~ned from the HPLC column followed by further pur1f1cat10n by GLC on a packed ~etnyl s11tcone ~OV-101) eolumn was cont~1ned ~thln ~ 2-mln fractlon ~th ~ Kov~t's Index (KI) of 17~0-1800 (Kov~ts, 1965). No lncre~se or decre~se tn btologtcal actlvtty ~as observed when the ~ctlve fractton w~s recomb1ned wlth other 6LC fr~cttons and subsequently bto~ss~yed over ~ r~nge of 1 X lO-4 to 1 X 10-1 fem~le equlvalent d~ys (FED) 1n the l~bor~tory.
Further pur1flc~t10n on a polar (C~rbowax 20M) column ytelded a s1ngle peak wlth KI ~ 2200 that produced full act1v1ty tn l~boratory and f1eld b10~ssoys (FIGS. 2A and 2B). Quant1tatlve analys1s of thls m~ter1al 1ndlcated th~t a FED w~s equ1valent to ca. 4 pg 14 pg ~
4 X 1o-l2 9 ~ 1.4 X 10-13 02). The actlve peak from the Cbrbowax 20M
column was found to be ~99.8S pure when ~n~lyzed on the cyanopropyl methyl s111cone, nethyl s11~cone, polyethylene glycol, and cholesteryl-p-chloroclnnam~te cap111~ry columns ~s described 1n Ex~mple 1.

IDENTIFICATION OF TH~ ATTRACTANT
Identlflc~t10n of (Z)-3-dodecen-I-ol-(El-2-buteno~te w~s p~rtl-cul~rly dlff1cult bec~use no precedent for th1s structure ex1sted.
Pr10r to the 1nvent10n, th1s compound was not known. In ~dd1t10n. pr10r to the 1nvent10n, no 1nsect sex attractant compound w~s known ~h1ch h~d ~ crotonate ester port10n ~s part of the chemlcal structure, thus, there w~s no suggest10n of ~ structur~l/funct10nal relat10nsh1p of the novel compound ~s ~n 1nsect pheromone, 1n general, or spec1f1c~11y for the SPW. Structural eluc1d~t10n of unknown chemlcals ls except10nally d1ff1cult because 11mlted theoretlc~l bas1s ex1sts for pred1ct1ng chemlcal structure from spectroscop1c dat~. The relat10nsh1ps between spectr~l pattern and structure ~re not well understood theoretlcally 1n en~ugh c~ses to penm1t structure Dss1gn~ent by theory ~lone.
In addltlon to lack of precedent of structure ~ss1gnment, another dlfflculty 1n the 1dent1f1catlon of the compDund was that only 11m1ted * Trade mark .. . , . . . ... , . _.. .. . . . . . . .. .

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amounts ka. 4 X lO-6 ~ obt~lned after collect1ng 850,000 v1rgln female SP~ hours) of the lsolated compound ~ere av~11able, thus llmlt~ng 1nvestlgatlons to use of g~s chrom~tography/mass spectrometry tGC/MS) and nucle~r m~gnetlc reson~nce (NMR) spectroscopy whkh employed m1cro-~n~lyt1c~1 techn1ques developed by us.
Another d1ff1culty 1n 1dent1f1cat10n of (Z)-3-dodecen-1-ol (E)-2-butenoate was thot ~ computer comp~r1son of the ~ass spectrum or HMR spectrum og~1nst a f11e of reference spectra could not be c~rr1ed out because there w~s no spectrum on f11e for the (E)-2-butenoate molety. ~dd1t10n~11y, 1n th1s case because of the novel structure of the compound, prevlously descr1bed methods of m1cro-analyt1cal techntques usçd to determlne the double bond pos1tlon of the pheromone were amb1guous. To obta1n f1n~1 eluctdat10n of the SPW
sex attr~ct~nt compound, 12 compounds, In idd1t10n to (Z)-3-dodecen-1-ol (E)-2-butenoate, wh1ch were all closely related tn structure, were synthes1zed and tested. Of these compounds, f1ve showed poss1ble attract~ncy ln the l~bor~tor~ ~100ss~y. These ~re (Z)-3-dodecen-1-ol ~E)-2-buteno~te, ~E)-3-dodecen-1-ol ~E)-2-buteno~te, (Z)-2-dodecen-1-ol ~E)-2-butenoate, (Z)-3-dodecen-1-ol (Z)-2-buteno~te, and lZ)-4-dodecen-1-ol ~E)-2-butenoate. The only compound wh1ch showed s1gn1f1c~nt f1eld response w~s ~Z)-3-dodecen-1-ol (E)-2-butenoote.
~he follow1ng structural 1nformat10n was eluc1d~ted from the mass ~pectr~l d~t~. ~he 1sobutane chem1c~1 10ntzat10n (Cl) mBSS spectrum (FIG. 3A) est~bl1shed that the moleculcr ~e1ght of the sex attr~ct~nt was 252 w1th d1~gnostlc pe~ks at m/e 251 (M-l), 253 (M~l), 254 (M~2), and 291 (M~39). The fragment 10n at m/e 167 (M~1-86) suggested the loss of buteno1c ac1d ~C4H602) from the p~rent molecule. ~he m*thane Cl m~ss spectrum tFl6. 3B) 1n ~dd1t10n to show1ng a pe~k ~t (M~-86) prov1ded a base pedk ~t m/e 87 tC4H7O2~ cons1stent wlth proton~ted buteno1c ac1d. B~sed on the m~ss spectr~1 data the structure n s ~3~i263 .
proposed ~s ~ butenoate of ~ 12-c~rbon ~lcohol whlch cont~lned one degree of uns~turatton Ozonolysls of the sex ~ttr~ct~nt (c~ 50 ng/o7onolyslsl produced t~o m~or protucts th~t ~ere tdentlfled ~s nonan~t ~nd dec~nal (1 0 8, respectlvely) by comparlson of thelr reten-t10n tlmes on ~ 50 m C~-20M caplll~ry column ~nd thelr mass spectr~
wlth synthetlc st~ndards.
Hlgh-fleld 300 ~Hz PMR w1th decoupllng experlments provlded the followlng spectral 1nform~tlon. Results obt~lned ln PMR coupling experlments of the purlfled n~tur~l m~terl~l ~re shown ln Table 1.
The spectrum (FIG. 4) 1ndlc~ted four oleflnlc protons. The proton glvlng rlse to the slyn~l t 6 ~ 7.03 (lH sextet) was coupled to the oleflnlc prcton ~t 6 ~ 5.95 (lH, d) ~nd the ~ethyl protons of 6 ~ 1.43 (3H, t). Thus the croton~te molety, O~C-CH~CH-CH3, WAS
est~bllshed The oleflnlc proton 6 ~ 5.41 (lH, m) was coupled to the ~ethylene protons at 6 ~ 2.44 (2H, q), ~hlch also ~ere coupled to the methylene protons ~t ~ ~ 4.22 (2H, t), CH~CH-CH~-CH2-0. Thus the posltlon of the olef1n1c bond 1n the ~lcohol ch~1n w~s unequlvoc~lly est~bllshed 4s belng 1n the three~pos1t10n. The oleflnlc proton 6 ~ 5.60 (lH, ~ s coupled to the methylene protons ~t 6 ~ 2 12 (2H, m) ~nd the olefln1c proton et 5.41 (lH, q) . The ~ethylene envelope 6 ~ 1.40 (12H, w) end the ~ethyl protons 6 ~ 1.05 (3H, t) ~re con-slstent wlth ~ heptyl molety. Examln~tlon of PM~ spectra of synthetlc s~mples of (Z)- end lE)-3-dodecen-1-ol ~nd the ~ethyl esters of (Z)-~nd (E)-2-buteno~te 1ndlc~ted th~t the geometry of the olefln1c bonds ~ere (Z)-3-dodecen-1-ol (E)-2-butenoate.

-- B --13~6~3 ' ~ABLE 1 . . . _ . .
Decoupler settlngs PPM of ~ proton(s) ln PPM
_ 7.03 5.95 (d `S)b ~ 1.43 ld ~s) 5.93 7.03 (m-~q) 5.60 2.12 (~-~t) ~ ~.41 t-) 5.41 2.44 (q >t) ~ 5.6 (-) -4.22 2.44 (q ~d) 2.44 5.41 (m-~d) ~ 4.22 (t ~s) 2.12 5.60 (m ~d) ~300 0Hz bs ~ S1nglet, d ~ toublet, t ~ tr1plet, ~ ~ mult1plet, q ~ quartet, ~nd (-) ~ not d1scernable due to decoupler spl~sh.

~n cdd1t10n to (Z)-3-dodecen-l~ol (E)-2-buteno~t¢, the other three poss1ble geometr~c lsomers were synthes1zed. ~11 four 1somer1c fon~s were ~dequ~tely resolved on ~ cy~nopropyl methyl s111cone c~plll~ry column. ~he 1soleted n~tur~l sex ottr~ct~nt h~d ~ retent10n t1me 1dent1c~1 to th~t of the synthet1c (Z)-3-dodecen-1-ol (E)-2-buteno~te.
- 20 ~he synthet1c ~Z)-3-dodecen-1-ol ~E)-2-buteno~te was 99~S pure ~nd 1dent1c~1 to the pur1f1ed nitur~l m~ter1el by ~ll en~lyt1cal procedures.
PMR ~nd c~p111~ry 6C d~t~ est~bl1shed th~t only one compound 1dent1c~1 to the synthet1c IZ)-3-dodecen-1-ol (E)-2-buteno~te h~d been 1sol~ted es the n~tural sex ~ttr~ct~nt. Ozonolysls of the synthetlc sex ~ttr~ct~nt ~lso produced the s-me two ~ldehyde products (non~n~l ~nd dec~n~l) th~t were produced by ozonolys1s of the n~tural sex ettract~nt m~ter1~1.

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- : . .- ~ 1, - ;

~3t~`6;~3 .' ..
USES OF THE A~TRACTANT
As prev10usly dlscussed, the pure or subst~ntlally pure sex ~ttract~nt compound nay be used as a detectlng ~gent, monltorlng ~gent, or control agent for edult weev11s. In pr~ctlce, (Z)-3-dodecen-1-ol 1~)-2-butenoate ts used as a trap bo1t or 1s otherw1se appl1ed to ~
locus of the adults ln ~n amount effectlve to 1ntuce the deslred response.
In the c~se of ~n attractant response, for example, an effectlve ~m3unt 1s def1ned as that qu~nt1ty of compound wh1ch attracts weev11 males to the locat10n of a b~1t at a rate slgn1f1cantly hlgher than males are attracted to a nonb~tted locatlon. Under typlc~l fleld cond1t10ns, ~mounts ln excess of about 5.7 X 10-12 9 wlll be effectlve. F~ctors such as populat10n dens1ty, temperature, w1nd veloGlty, and release r~te wlll 1nfluence the actual number of weev11s tr~pped.
In the c~se where the des1red response 1s dlsrupt10n of m~tlng by confus1ng or Inh1blt1ng the weev11, ~n effect1ve amount 1s def1ned ~s th~t qu~ntlty of compound wh1ch permeates the atmosphere such that m~les ~re prevented from orlent1ng to ~nd 1nsemlnat1ng the fem~les, 1.e., d1sruptlon of matlng, at ~ rate slgn1flc~ntly hlgher thdn dlsruptton o- m~t1ng of m~les at a nontreated loc~t10n. As wlth the ~ttr~ct~nt response, ~ctors such as populatlon dens1ty, temper~ture, wlnd vcloc1ty, and release rate w111 1nfluence the actual number of weevl1s dlsrupted.
It ls enY1sloned th~t IZ)-3-dodecen-1-ol (~)-2-buteno~te ~ould be effectlve ln detectlng, mon1torlng, or controll1ng SP~ popul~t10ns when used 1n con~unct10n wlth any b pe of trap or pheromone dlssem1n~tor known 1n the art. lllustrat1ve of the wlde v~rlety of tr~ps or pheromone dlsem1n~tors wh1ch mdy be used are the followlng: st1cky tr~p, funnel trAp, and p~nk bollworm tr~p. Typ1c~11y, the compound would be appl1ed to the rele~se substrate 1n solut10n w1th a su1t~ble carrler such ~s ~n 3G organ1c solvent or und11uted. Yolat111z~t10n can be ret~rded by 1nclu-s10n of ~ hlgher nolecul~r we1ght m~ter1al to the (Z)-3-dodecen-1-ol - 10 _ ~3~ 63 (E)-2-butenoate solutlon. Slow release may also be effected by encapsu-lat10n or absorpt10n tnto ~ porous substrate.
~Ihen used as a detectlon or ~onltorlng agent, traps are balted with the novel compound of the lnvent10n and the catch tabulated to determ1ne slze and loc~t10n of tnfestat10n. Economlc use of approprlate pest m~nagement systems cm then be determ1ned.
Use of the sex attract~nt of the 1nventlon ~s ~ control ~gent c~n be c~rrled out 1n several ~ays. One method ls to use the compound to attract the 1nsects to su1table substrates and subsequently or s1mult~neously expose the lnsects to 1nsectlcldes ~hlch control the - weev11. An effect1ve amount of the 1nsect1c1de ts used, that ts, an amount that ls lethol for an exposed tnsect or at least sublethal but sufflclent to tncapacltate the tnsect tn regard to mat1ng actlv1ty.
Illustrat1ve of the ~1de var1ety of tnsectlcldes ~htch may be used wlth the compound of the 1nventlon ls endosulfan. Insectlctdes cAn be used 1n traps h1ted ~1th the novet sex attr~ctant of the 1nventlon. Thls ellmlnates the need to spread the 1nsectlc1des unnecess~r11y and helps prcvent k1111ng useful tnsects and other an1mals.
A second method to control weev11s us1ng the novel compound 1s to detect the locot10n and boundar1es of local1zed weev11 1nfest~-t10ns and employ 1n the area blologtcal control agents, e.g., par~s1tes such as M1crobr~con, predators such as Argenttne ants, and pathogens such as Beauvar1a globultfera. As w1th the use of tnsecttctdes, th1s method el1m1n~tes the need to spread the control agents unnecesssr11y and m1nlmlzes ~dverse 1mpact to useful 1nsects and the envlronment.
~Z)-3-dodecen-1-ol (E)-2-buteno~te may also be used to control weevlls by confuslon of SPW ~les, thus preventlng mat1ng. For ex~mple, one technlque ls to perme~te the atmosphere w1th suff1c1ent compound to prevent the ~ales from or1ent1ng to and 1nsem1n~t1ng the females.
~ther uses of the novel sex attractant w111 be obv10us to those ln the ~rt.

i3`~6~263 EXAMPLES
The followlng examples are lntended only to further lllustrate the 1nvent10n and are not lntended to llmlt the scope of the lnvent~on wh1ch ls def1ned by the cl~1ms.

EXAMPLE I
Isol~t10n of the Natural Sex Attractant Sweetpotato ~eev11 Rearlng and Handl1ng. Insects were reared 1n the laboratory on commercl~ obtalned sweet potatoes ~t 26~1C
60~52 RKH under a 14:10 (L:D) photoper10d uslng the procedures descrlbed by Coffelt et al., Envlronment~l Entomology ~: ~56-758 (1978). Vlrg1n lnsects were obta~ned (females for sex ~ttractant collect10n and male for use 1n b10ass~ys) by separatlng male and fem~le weev11s w1th1n 24 hours of eclos10n. Adults were ~1nt~1ned, pr10r to test1ng, for 5-7 days ln groups of 50 to 75 1n lO0 X 15 mm gl~ss Petrl dlshes w1th bottoms llned w1th ~h~tman ~1 f11ter paper. Dur~ng th1s per10d, males and fem~les were kept ln gep~rate growth chambers w1th envlronment~l paromenters ldent1c~1 to those used for 1nsect re~rlng. Adults were prov1ded ~ sm~ll sl1ce of sweet pot~to every 48 hours.
Collectlon of SP~ Yol~t11es. Collect~ons of SP~ volat11es were made by draw1ng a1r over vlrg1n female weev11s that were conf1ned ln a 10.5-11ter (24.5 cm X 22.2 cm d1~meter) glass ~r. E~ch ,7sr cont~lned 1500-2000 fem~les ~nd one sweet potato. The ,7ars were kept 1n a laboratory hood w1th1n ~ room m~1nto1ned at 26~1-C and 65l5S RH and a 1~:10 (L:D) photoperlod. Vacuum was used to pull amb1ent a1r through the un1t at ~ rate of 2 llters/m1n. Volat11es emanat~ng from the un1t were entra1ned us1ng two glass adsorptlon traps (1.5 X 8 cm) each cont~1n1ng 2.0 9 of d1atomaceous earth (60/80) mesh sold under the tradename Chromosorb 102 by Johns Mbnv117e. Pr10r to use the adsorbent was eluted w1th 100 ml of reagent gr~de d1ethyl ether.

*Trade Mark ~ i ~3~ i3 ,. ..
Volat11es were collected cont1nuously over a 30-day per1Od for a glven batch of lnsects. Sex attractant was collected at 48-hour 1ntervals by elutlng the entra1ned volattles wtth 5-7 ml of pentane:ether (90:lO).
A fresh sweet potato was placed 1n the un1t at th1s t1me. Approx1mately 850,000 female equ1valent days (FED) were collected.
Isolat10n of Sex Attractant. Excess solvent was removed from the collected volat11es us1n~ heat (25C) and N2. ~ext, the concentrate was chromatographed on a grav1ty-flow glass column (15 cm X l cm 1.d.) prepared by slurry pack1ng 5.0 9 of 60-I00 mesh stl1ca (J. T.
Baker Chem1cal Co., Ph1111psburg, NJ). Solvents used for the gravlty flow column 1ncluded 5S ether-hexane ~80 ml) and lO~ and 20~ ether-hexane (80 ml each). The act1ve fract1Ons from the grav1ty flow column were concentrated and 1n~ected onto a HPLC column 1250 mm X 4.4 mm l.d.) packed w1th 5 pm stltca (sold under the tradename Llchrosorb St-60 by E. M. Laborator1es, Inc.). The HPLC column was eluted w1th 2~ ether 1n hexane at a flow rate of 2.0 ml/m1n, Ten fract10ns (2 ml each) were collected. An add1t10nal 20 ml of 5~ ether-hexane was used to remove the (1nact1ve) polar mater1al from the column. The actlve fract10ns from the HPLC column were combfned, concentrated, and further pur1fled by GLC.
All m1croprep~rat1ve GLC was performed w1th a Var1an Model 1400 gas chromatograph equ1pped w1th a flame-1Onlzat1On detector. The effluent from the packed columns was spl1t w1th 2S of the effluent routed to the detector, and 98~ collected 1n a cooled, 30-cm glass cap111ary tube as descr1bed by Brownlee and 511versteln, Analytlcal Chem1stry 40: 2077-2079 (1968).
The 1n1t1al column used for further pur1f1cat1On of the act1ve mater1al from HPLC was a 2 m X 2.3 mm 1.d. glass column packed ~1th 5 methyl stl1cone (sold under the tradename W-101 by Altech Assoc.) on 80-I00 mesh d1atomaceous earth (sold under the tradename Chromosorb G-HP by Johns Manv111e). Heltum was used as the carr~er gas at 20 ml/m1n i~3~6;2~3 and the column temperature was programmed from 120 to 220-C at lO-/m1n.
The actlve fractton coltected from the OV-101 column was subsequent1y chromatographed on a 1.8 m X 2.0 ~m 1.d. glass column p~cked wfth 4.4S
polyethylene glycol Isold under the tradename Carbowax 20M by Altech Assoc.) on 120-140 mesh d1at~maceous earth (sold under the tradename Chromosorb ~ b~ Johns Manvflle). Hel1um was used as the carrler gas at 20 ml/m1n and the column was operated lsothennally at 180-C.
All analyt1cal GLC was performed wlth a Hewlett-Packard Model 5790 gas chromatograph equlpped wfth a flame 1Onlzatlon detector and a splltless caplllary tn~ector. Output from the detector was 1nterf~ced to a Nelson 4416 data system. The act1ve fractlon from the Carbowax packed column was ~nalyzed on the follow1ng fused slllca caplllary columns: S0 m X 0.25 mm 1.d. ~ethyl sfllcone sold under the tradename BP-l by Sc1ent1f1c Glass Eng1neer1ng; 50 ~ X 0.25 nm 1.d.
Carbowsx 20M; 50 m X 0.25 mm 1.d. cyanopropyl methyl sll1cone sold under the tradename CPS-l by Quadrex Corp.; and a 35 m X 0.25 nm 1.d.
soft glass column co~ted w1th tholesteryl-p-chloroc1nn~mate as descr1bed by Heath ~nd Dooltttle, Journ~l of H1gh Resolutlon Chromatosra~y 6: 16-19 (1983). Hel1um ~as used as the carrk r gas for ~ll columns st a 11near flow of 18 cm/sec.
Ident1f1cat1On. The act1ve component was 1dentlf~ed by chem1cal 1On1z~t1On mass spectrometry ICI-MS) and by Four1er transform proton nuclear Dagnetlc resonance ~FT-PMR). Addft1Onal structural 1nfon~at1On on the ~ct1Ye compound was der1ved from the mass spectra of the pro-ducts from m1croozonolys1s.
M~ss spectra were obta1ned w1th an upgraded F1nnlgan 1015/3200 chemlc~l 10n12at10n mass spectrometer coupled w1th a Var1an 1400 g~s chromatograph and a user-des1gned spl1tless 1n~ector. Fused sll1ca cap111ary columns used 1n the gas chromatograph1c 1nlet s~stem 1ncluded a S0 m X 0.25 nm 1.~. setb~l s111tone (BP-l) and a 50 ~ X 0.25 I.d.
Carbow~x 20M (~uadrex) column. Hel1um was used as the carr1er gas :13~ 63 , , at a 11near flow of 18 cm/sec. Re~gent gas, elther meth~ne or lsobut~ne, was lntroduced as ~ake up gas. The PMR spectra were obtatned wlth a ~lcolet 300 ~H, Fourler transform spectrometer. Approx1mately 4 ~4 of the purlf1ed compound was placed ln a ~0 ~l extern~l captll~ry extenslon tube (~11mad, Buen~, NJ) contalnlng 15 ~ of deuterated benzene. Two thousand translents were collected over a l-hour per10d uslng a 6 ~sec pulse t90 tlp angle). Proton decoupl1ng was accompllshed by us1ng standard decoupllng technlques (decoupler power c~. 1/2 watt) and 400Q translents spectra were obtalned over a 2~hw r perlod.
I0 Mlcroo20nolys1s of the sex attract~nt IS0 ng each experlment) was carrled out ln carbon dlsulflde or hexane at -70-C and the ozonlde was reduced wlth tr1phenylphosphlne accordlng to the method descrlbed by Beroza and Blerl, Analytlcal Chemlstry 38: 1131-1135 11967). ~he ozonolys1s products were analy2ed by CI-M5. Synthet1c st~ndards were used to conflrm the 020nolysls products and also to verlfy the spectral data.
Beglnnlng w1th the crude m~ter1al, and cont1nulng through the pur1f1c~tlon, ~ll n~tert~ls were b10assayed 1n the laboratory to ensure no loss of act1v1ty occurred. In add1t10n, f1eld b10assays of the crude, HPLC, and GLC t~rbowax samples were conducted to ensure that no loss of act1v1ty 1f the fleld occurred as 8 result of the separat10n performed.
~he bloassay procedures are descr1bed ln Example 3. As shown ln ~I65.
2A and 2B, no loss of blolog1cal ~ct1v1 b relat1ve to the crude mater1al was noted elther 1n the laboratory of the fleld bloassay. The regress10n data are s1gn1f1cant at the IS or 5S level.
Laboratory b10ass~ys lndlcated a~l of the act1vlty of the lnltlal collections was recovered ln the 5S ether-hexane eluant ~80 ~l) from the grbv1ty f10w s111ca column. No lncrease ln actlv1ty was observed by the addit10n of the ~ore polar components that were obta1ned by ~urther elut10n w1th lOS and 20S ether-hexane. ~he act1ve fract10ns from sever~1 gr~vlty n ow runs were eomb1ned and subsequently pur1fled ~3~ i3 .', .
by HPLC. The blologlc~lly ~ctlve fractlon from HPLC eluted between column c~p~clty r~tlo Ik ) of 3.67 ~nd 4.33.

Synthes1s Df (Z)-3-Dodecen-l-ol (E)-2-Butenoate The synthes1s of (Z)-3-dodecen-I-ol (E)-2-butenoate, I, shown ln FIG. I, was ln1t~ted wlth the prepar~tlon of 3-dodecyn-l-ol from I decyne.
For the synthesls of 3-dodecyn-I-ol, Il, n-butylllthlum (9.3 ml of 2.7 M ln hex~ne) was tn~ected lnto ~ cooled solutlon 1~ O-C) of I-decyne (4.5 ml, 25 mmote) 1n dry tetrahydrofurdn (THF, 36 ml) under nltrogen.
Ethylene oxlde 1I.5 ml, 30 rmole) was 1n~ected from ~ precooled syrlnge, ~nd then hex~methylphosphorlc tr1~m1de (9 ml, ca. 2 equlv.) was ln~ected.
The resultlng m1xture was st1rred overn1ght ~t ~mb1ent temperature and then worked up by d11ut10n wlth w~ter ~nd extr~ct10n w1th hexane. The product ~lcohol w~s d1stllled under reduced pressure to g1ve 3.45 9 177.5S): b.p. 74-79-C/0.05 mm; lR (CC14) 3640 cm~l; UMR b O.B8 (3H, t, CH3), I.27 (CH2 envelope), 2.18 (2H, ~, CH2CHC~C), 2.41 (2H, ~, HOCH2CH2C~C), 3.67 (ZH, m, CH20H) ppm.
To synthes1ze (Z)-3-Dodecen-I-ol, III, ~lkynol II (3.25 9, 17.9 mmole) w~s hydrogen~ted over 30 mg of L1ndl~r c~t~lyst prepared ~ccord1ng to Moz1ngo, Org~n1c Syntheses 3: 685-690 ~I955). ~he reduct10n w~s c~rr1ed out 1n pent~ne (35 ml) ~t ~b~ospher1c pressure end emblent temper~ture. The reduct10n w~s mon1tored by g~s chromatogr~phy uslng 25-m 10.25 mm 1.d.) fused s111c~ c~p11t~ry column co~ted w1th CPS-I
tQuadrex Corpor~t10n). After f11tr~t10n ~nd concentrat10n, the ~lkenol lII w~s d1st111ed under reduced pressure to g1ve 2.87 9 (88.3S): b.p. 67-70-C/0.05 mm, IR (CC14) 3300 bro~d, 1050 cm~l;
NMR ~ 0.88 (3H, t, CH3) I.27 (CH2 envelope), 2.05 12H, m, CH~C-C), 2.33 (2H, m, HOCH2CH~C~C), 3.64 12H, ~, CH20H), 5.38, 5.55 (2H, m s, cls olef1n1c H).
3G To synthes1ze ~Z)-3-Dodecen-I-ol (E)-2-buteno~te, I, crotonyl chlorlde (5.7 mt of 90S techn1c~1 gr~de, 59.4 ~mole) ~nd ~lkenol III

~3~r~&~

.
(8.75 9, 47.5 ~mole) were dlssolved ln ~ethylene chlorlde (CH2Cl2, 90 ~ nd cooled 1n an lce both. Pyrldlne (3.8 ml, 47.5 mmole) w~s ~dded 1n CH2Cl2 (10 ml) dropwlse. The result1ng m1xture was st1rred cold for l hour ond then worked up wlth w~ter ~nd CH2Cl2. The organlc ph~se wos drled ~MgS04~ ond concentrotet. The yleld of crude ester 112.0 9) w~s nearly quont1t~tlve. Dlst111Rtlon of 6.0 9 of crude product under reduced pressure g~ve 5.1 9 (84S) of I contolnlng less than 10S of the 1somer1c 3-butenoate ester: b.p. 105-lO9~C/0.1 ~m; IR
(CCl4) 1729 (C~0), 1660 (C~C) ond 970 cm~l (trans HC~CH).
The d1st111ed synthet1c mater101 ~as pur1fled on o 5 ~m s111c~
gel HPLC column (25 cm X 4.4 mm l.d.) us1ng 2S ether:988 hex~ne.
Thls HPLC purlf1ed mDter1~1 wos then further pur1fled uslng ~ 20S
AgN03 slllco gel HPLC column, 25 cm X 1.25 cm o.d., ~nd w~s eluted wlth toluene. Th1s mater1~1 was ~nalyzed by cap1110ry 6C on the some columns descr1bet obove.

Sex ~ttr~ctancy of the N~tur~l ~nd Synthet1c Mbter1al Quont1tot~ve b100ssoys compor1ng the ottr~ct1ve propert1es toword the SP~ of v~r10us prepar~t10ns of notural ond synthet1c sex ~ttr~ctont were conducted 1n the l~bor~tory cnd the f1eld on SP~ ~les re~red by the procedure descr1bed 1n ~xomple 1.
L~borotory B10ass~y. Somples were b100ssoyed us1ng the proce-dure descr1bed by Coffelt et ~l., supra. Br1efly, 3-5 ~1 of test extr~ct were p1petted onto the fl~ttened end of ~ gloss rod ~nd then exposed to ~ ser1es of ten ~oles th~t were held lnd1v1duolly 1n 1.6 X 5-cm Teflon cooted shell v101s. The treated rod wos suspended w1th1n 1 cm of the test 1nsect for o per10d not greater than 15 ~econds. ~ pos1t1ve response, def1net ~s ontenn~l elevDt1on ond locomot10n, was taken os ev1dence of the presence of sex ~ttroctont. Rods tre~ted w1th solvent only served ~s controls ona exposure of ~ s1ngle rod to ten males 13~ ~3 const1tuted one repl1c~t10n. ~h1s blo~ss~y was emplo~ed only ~fter 1n1t1al stud1es revealed that only those fr~ct~ons th~t ellc1ted the ~bove responses were ~ttr~ct1ve to males ~n the f1eld. All l~bor~tory b1o~ssays were conducted under Cool-~h1te fluorescent room llghtlng ~t 26~2DC dur1ng the l~tter I/2 of the photoph~se us1ng m~les th~t were between 7 ond 30 d~ys of oge. Sex ~ttract~nt un1ts are expressed 1n tenms of FED; one FED be1ng the est1mated qu~nt1ty of sex ~ttractant obta1ned from one female per 24-hour per10d. ~he cpllected volat11e m~ter1al ~nd ~11 fractlons obta1ned tn the pur1f1c~t10n of the sex I0 ~ttr~ct~nt were b10~ss~yed ot I0-I, I0-2, 10-3, ond 10-4 FED.
~1eld tests. F1eld b10~ss~ys were conducted ln February-August 1n 0.2-ha plots of sweet pot~to ~t the Feder~l Exper1ment Staff on, St. Cro1x, U.S. V1rg1n Isl~nds.
In the f1rst ser1es of tests ~February), unpur1fied volat~les that conta1ned sex ~ttr~ct~nt, p~rt1ally pur1f1ed m~ter1~ ct1ve froct10ns from HPLC) ond purlf1ed moter101 (from the Corbowax 20M GC
column) were comp~red to det-rm1ne whether ony loss of ottr~ct1veness to feral ~les occurred os o consequence of the 1nd1c~ted fract10n~t10ns.
Doses of 0.0, 0.2, 2.0, and 20 FED ln 50 ~l hexone were oppl1ed to 22 X 22-mm gl~ss cover sl1des. After solvent evoporat10n, the cover sl1des were pl~ced 1n the center of ~ I00 X I5-mm Teflon-11ned Petr1 d1sh (cover sl1des elev~ted 16 mm ~bDve floor of d1sh). lHshes were placed at the center of 1nd1v1du~1 50 X 50-cm wooden plotforms ~th the he19ht of the platform be1ng ~pprox1m~tely equ~l to the pl~nt c~nopy he19ht (15-20 om). ~he number of m~les on the pl~tform and 1n the d1sh (<15 mm from source) w1th1n 5 0~nutes of deployment of the s~mple were recorded and t~ken as ev1dence of response. All tests were conducted bet~een 1930 ~nd 2145 h Atl~nt1c ST ~t temper~tures rong~ng frcm 20.5-22.2C.
Plotforms were deployed ot 2-m 1nterv~1s 1n o 11ne ~pprox1~ately perpend1cul~r to the prev~111ng e~sterly w~nd d1rect10n. ~re~tment *Trade Mark ., ~

~3(~6'~i3 locat10ns were randomlzed wlth1n plots, and a total of n1ne repl1catlons were made 1n three d~fferent plots over several nlghts wlth no plot be1ng used for more than one repl1catlon per nlght. Cover slldes treated wlth hexane only served as controls.
The second serles of fleld bloassays was conducted ln March and September to compare the relat1ve attract1veness of the pur1fled natural product wlth synthet1c pheromone l>99~purlty). Doses tested were 0.0, 0.08, 0.8, 8.0, and 80 ngl50 ~l; the materlal was formulated on glass slldes. Addltlonally, the purlf1ed natural materlal was compared wlth synthet1c pheromone when formulated on rubber septa ~A. H. Thomas 08753-D22). The materlal was dlssolved ln 100 mt of hexane and plpetted 1nto the large reservolr of the septum cap. Septa were loaded w1th 10, 30. lOO, and 300 ng of materlal and bged a mlnlmum of 2 days prlor to use. Septa treated w1th hexane served as controls.
Septa were posltloned about 3 cm aboYe the floor of the Petrl dlsh wlth a paper c11p. Test duratlon was 20 mlnutes. There were four repllca-tlons at e~ch dose 1n two t1fferent plots on dlfferent days. ~lth1n plots, treatment locat10ns were random1zed between repl1cat10ns. Treat-ments were random1zed w1th1n plots and two plots were used. Other parameters were as 1n the prev10usly descr1bed f1eld b10assay.
The th1rd ser1es of f1eld b10assays was conducted ln August to 1dentlfy the nature of the relatlonsh1p between the applled dose of synthet1c sex attractant (>99~ purlty) and the number of feral males attrtcted. Bloassays were carrled out as descr1bed above. The sex attractant was formulated on rubber septa ln doses of 0, l, lO, lOO, and 1000 ng ~elght repl1cat10ns).
The results of the laboratory study comparlng the relat1ve actlvlty of the pur1f1ed natural product and the synthet1c ~ater1al ~slx to ten repl1cAt10ns at four dlfferent dosages for each mater1al) 1nd~cated that there was no measurable d1fference between the two mater1als.
The relatlve actlvlty, 1n terms of male attractlon ln the f1eld, 1s 13~`3 .. , ~
shown ln FIG. 5. Two rele~se substr~tes, gl~ss (FIG. 5A) and rubber (FIG. 5B), were used and the sim11ar~ty 1n response 1s shown 1n the f19ures. The dose-response of SPW males to (Z)-3-dodecen-1-ol (E)-2-butenoate formulated 1n rubber septa (e19ht repl1cates/polnt) 1s shown 1n FIG. 6. Controls d1d not c~pture a s19n1flcant number of sweetpotato weev11s ln any test.

Field Tests The attr~ct1ve propert1es tow~rd the SP~ of the synthet1c compound prep~red as descr1bed 1n Ex~mple 2 under fleld cond1tlons was tested 1n St. Cro1x, U.S.V.I. The numbers of sweetpotato weev11s caught uslng a 11ght trap, one sweetpotato weev11 female, three females, and septa lo~ded w1th 100 ng or lO ~9 of the synthetlc sex attract~nt compound were comp~red. ~hen females served as ba1t, they ~ere held 1n ~
tetrahedral cage ~ade from f1berglass. ~he synthet1c compound w~s d1~solved 1n hexane pr10r to appl1cat10n to the rubber sept~. ~n a 24-hour test, tr~ps b~1ted w1th lO0 ng or lO ~9 of synthet1c compound captured 75 and 275 ~ales, respect1vely. For comp~r1son the 11ght trdp captured two males Iplus one female) and traps b~lted w1th one or three females captured two and f1ve ~ales, respect1vely.
The effect1veness of n1ne d1fferent types of traps balted wlth the synthet1c compound prepared as descr1be~ 1n Example 2 was evaluated under f1eld eond1t10ns 1n St. Cro1x, U.S.Y.I. The trDp types used were 11ght trap; st1cky trap; w~ter trap; PFT~ plast1c funnel 11ve trap used for mon1torlng the p1nk bollworm, set wlth1n a truncated cone m~de from standard hardw~re cloth); PFT-2 Itrap s1m11ar to PFT-l but w1th larger entrance holes); black trdp Islmllar to PFT-l except truncated cone w~s pa1nted black); yellow trap Is1mll~r to PFT-l but w1th a yellow base~; orange trap ts~m11ar to PF~-I but wlth an orange base);
and AFT Islmllar to ~FT-l but wlth an alum1num funnel).

13~

. .
Table 2 shows the number of males tr~pped per n~ght (b~ck transformat10n of~ Y~O.~ nd tr~p rank1ng w~th A n trap equ~ll1ng 1 .00.

.
Trap Tr~p Comparisona Tr~pb r~nk L19ht 21~ 2a 0.06 Sticky 94 0-14 Orange 210 46 0.28 Yellow 196 45 0.29 Black 40 0.24 ~ter 46 0.27 PFT-1 81 l07ab 4Bb 0.43 PFT-2 347b 137c 0.94 A~T 141c 1.00 P for F test<0.1 <0.1 ~0.025 <0.001 Me~ns followed by the s~me letter were not s1gn1f1cantly dlfferent (P~0.05).
bR~nk1ng from non-tr~nsfonmed ~eans.

It 1s understood that the foregolng dkta11ed descr1pt10n 1s g1ven ~erely by ~ay of 111ustrat10ns end th~t mod1flcat10n and var1at10ns m~y be m~de there1n w1thout depart1ng from the sp1r1t and scope of the 1nvent10n.

Claims (10)

1. The substantially pure compound (Z)-3-dodecen-1-ol(E)-2-butenoate.

2. A sex attractant composition for the sweetpotato weevil, which comprises an effective attractant amount of the substantially pure compound (Z)-

3-dodecen-1-ol (E)-2-butenoate and a carrier.
3. The attractant composition of claim 2 in combination with an effective amount of a control agent for the sweetpotato weevil.

4. The attractant composition of claim 3 wherein said control agent is an insecticide for the sweetpotato weevil.

5. The attractant composition of claim 3 wherein said control agent is a predator, parasite, or pathogen of the sweetpotato weevil.

6. A method of eliciting a behavioral response in an adult male sweetpotato weevil, comprising applying to the locus thereof an effective amount of (Z)-3-dodecen-1-ol (E)-2-butenoate.

7. The method of claim 6 wherein said (Z)-3-dodecen-1-ol (E)-2-butenoate is synthetically prepared.

8. The method of claim 6 wherein said (Z)-3-dodecen-l-ol (E)-2-butenoate is in combination with a suitable carrier therefore.

9. The method of claim 6 wherein (Z)-3-dodecen-l-ol (E)-2-butenoate is in combination with an effective amount of a control agent for the sweetpotato weevil.

10. The method of claim 9 wherein said control agent is an insecticide for the sweetpotato weevil.