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Lepidopterous Sex Attractants with a Conjugated Diene System

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Lepidopterous Sex Attractants with a Conjugated Diene System Agric. Biol Chem., 51 (10), 2691 -2694, 1987 2691 Lepidopterous Sex Attractants with a Conjugated Diene System Tetsu Ando, Mizue Koike, Masaaki Uchiyama and Hiroshi Kuroko* Department of Plant Protection, Faculty of Agriculture, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183, Japan * Faculty of Agriculture, University of Osaka Prefecture, Sakai 591, Japan Received April 10, 1987 Each.of fifty-one conjugated dienes (alcohols, acetates and aldehydes) with a C12, C14 or C16 straight chain was applied to a rubber cap in a sticky-type trap as a single-component lure. Some diene compoundsweremixedwith their functional derivatives or structurally related monoenesto maketwo-componentlures. In field trials conducted from 1984 to 1986, the newattraction of malemothsof nineteen species wasobserved. Thesespecies wereclassified into nine families as follow: Gracillariidae, Yponomeutidae, Oecophoridae, Cosmopterigidae, Tortricidae (Olethreuti- nae and Tortricinae), Pyralidae, Pterophoridae, Drepanidae and Geometridae. This result indi- cates that the conjugated dienes are one of the maingroups of lepidopterous sex pheromones. Someinteresting information concerned with the taxonomyof the attracted moths and with the characteristics of the chemical structures of their attractants was obtained. Manyconjugated diene types of sex pher- metrical purity was applied to a rubber cap as a single- omones have been identified from female component lure. Three groups of two-component lures (alcohol+acetate, acetate+aldehyde, and aldehyde+ moths,1} and field screening tests with synthetic alcohol) were made up by combinations of two com- pheromonesand their analogues have success- pounds containing the same conjugated diene system, fully found newmale attraction for a number but with different functionalities. Thus, ten diene alcohols of lepidopterous species.2) These circumstances (seven dodecadien-1-ols: (7£,9Z)-, (8Z, 10Z)-, (8Z,10£>, (S^IOZ)-, (SE,10E)-, (Z)-9,l 1- and (E)-9,l 1-isomers; and encouraged us to conduct systematic field tests three tetradecadien-1-ols: (9Z,1 1£)-, (Z)-l l,13- and (E)- with the conjugated diene compoundsin order ll,13-isomers) and their derivatives (acetates and al- to get more information on the pheromones of dehydes) were chosen as components. Twocomponents species native to Japan. This paper deals with were mixed in three different ratios (9: 1, 5:5 and 1 :9), the preliminary result of a field test on about and thirty lures were then prepared. Furthermore, some conjugated dienes were mixed with structurally related fifty dienes. monoenespossessing same functionalities (also in ratios of 9:1, 5:5 and 1 :9) to make forty-five two-component MATERIALS AND METHODS lures as follow: (8£,10£)-8,10-dodecadiene and (£)-8- dodecene compounds, (Z)-9,l l-dodecadiene and (Z)-9- Using the methods reported previously,3) seventeen con- dodecene compounds, (.E)-9,l l-dodecadiene and (E)-9- jugated diene alcohols (nine dodecadien-1-ols: (6Z,8Z)-, dodecene compounds, (Z)-l l,1 3-tetradecadiene and (Z)- (6£,8Z)-, (1E,9Z)-, (8Z,10Z)-, (8Z,10£>, (8£,10Z)-, (8£, 1 1-tetradecene compounds, and (£>1 1, 1 3-tetradecadiene 10E)-, (Z)-9,l l- and (E)-9,1 1-isomers; five tetradecadien- and (^)-l l-tetradecene compounds. One mg of each two- 1-ols: (8£,10£)-, (9Z,1\E)-, (10£,12£)-, (Z)-l1,13- and (£)- componentmixture wasalso applied to a rubber cap for 1 1,13-isomers; and three hexadecadien-1-ols: (10£,12Z)-, evaluating its attractive activity. Each rubber cap was (\ \E,13Z)- and (l lis,13iT)-isomers) and their derivatives placed in a sticky-type trap,*1 the field test being con- (acetates and aldehydes) were synthesized. One mg of ducted from 1984 to 1986 in a forest located in the suburbs each of the fifty-one chemicals with more than 95%geo- of Tokyo*2 in the same manner as that used for the The traps were kindly supplied by Shin-etsu Chemical Co. AsakawaExperimental Forest, Forestry and Forest Products Research Institute. 2692 T. Ando et al. screening tests of monoenecompounds.4 monoene compounds was observed. These species had not been attracted to the lures RESULTS AND DISCUSSION consisting of only monoenecompounds. The scientific names of the attracted moths, their Wehave reported the sex attractants for attractants, time of their flight to the traps and about two hundred lepidopterous species the total numberof attracted males are sum- which had been discovered by random screen- marized in Table I. This result indicates that ing tests with monoenecompounds.4'5) In this the conjugated dienes are one of the main field trial, the newattraction of male moths of groups of sex pheromones,and that a random fifteen species to conjugated dienes and four screening test with synthetic dienes is useful for species to mixtures of conjugated diene and pheromone studies. The nineteen attracted Table I. Sex Attractants Discovered by Field Tests of Conjugated Diene Compounds in a Forest in Tokyo (Hachioji-shi) from 1984 to 1986 [L F_a m. il y ] A. ttractan tO.species Time of flight (Number of attracted moths) [G racillariid ae] Ac r oc er co ps s p . 1 E 8 ,E lO -1 4 : Ai d M ay (105) Ac ro ce rco ps s p. 2 E 8,E lO -1 4 : A id Ju ne (123) Phyllonorycter pulchrum Kumata E8,ElO-14 : OAc M ay ~ Ju ne (80) [Y p on om eu tid ae] Xyrosaris lichneuta Meyrick Z9,El 1-14 : OH Apr. -May (47) [O ecoph orid ae] Acr ia ceram itis Me yrick E8, ZlO-12 :Ald+E8 ,ZlO-12 : OAc July (158), Sept. -Oct. (337) (5 :5) [C o sm o pterigid ae] An at rac hyn tis s p. El l, 13- 14 : O Ac M ay - Ju ne (1173), A u g. (23 1) [T ortricidae] (O lethreutinae) A terp ia iss ikii Ka wabe Z 8,Z lO-1 2 : OH M ay (28), A ug . (22 ) He dya d imidi ana C lerck E8,E lO- 1 2 : O Ac M ay (23) Matsumuraeses (alcana Walsingham6)E8,ElO-12 : OAc+E8-12 : OAc (5 : 5) O ct. - D ec. (14 8) Proschistis marmaropa Meyrick Z8,ZlO- 12 : OH Apr. -May (41), Aug.-Sept. (14) Rhyacionia duplana simulata Z8,ElO- 12 : OAc A p r. (49) H ein rich (T o rtricin ae) Acleris affinitana Snellen E1 1,13-14 : Aid Apr. -May (55) Acleris hispidana Christoph Ell,13-14:Aid+Ell-14:A id (5 : 5) Apr. ~May (14) Acleris iaponica Walsi ngham Ell,13-14:Aid+Ell-14:Aid (9 : 1) A p r.- M ay (39), July - A u g. (58) Acleris nigrilineana Kawabe Ell,13-14:Aid+Ell-14: Aid (5 : 5) A p r.- M ay (2 1) [P yralid ael Tequlifera bicoloralis Leech El 1,13-14 : Aid+El 1-14 :Aid (9 : 1) Ju ly (37) fP teroph orid ae] Pselnophorus vilis Butler Z9,El 1-14 : Ald+Z9,El 1-14 : OAc June - Sept. (26) (9 :1) [D rep anid ae] Macra uzata maxima Inoue Z9.El 1-14 : Aid M ay - D ec. (65) [G eom etridae] Idaea biselata Hufnagel E7,Z9-12 : OAc+E7,Z9-12 : Aid (5 : 5) O ct. (12) Idaea tri setata Pr out E7,Z 9-12 : O H Ju ly (12), Sep t. (44) The chemical formulae are symbolized by Z =(Z)-isomer, E = (iT)-isomer, the number before the hyphen giving the position of unsaturation, the number after the hyphen giving the carbon atoms in the chain, OH=alcohol, OAc= acetate, and Aid = aldehyde. Lepidopterous Sex Attractants with a Conjugated Diene System 2693 species were divided into nine families as one of the key pheromone components for follow: Gracillariidae (three species), Tortricinae species, especially the genus Yponomeutidae (one species), Oecophoridae Acleris. The ll,13-dienes also attracted the (one species), Cosmopterigidae (one species), Cosmopterigidae and Pyralidae species (Ana- Tortricidae (Olethreutinae, four species; trachyntis sp. and Tequlifera bicoloralis) as Tortricinae, four species), Pyralidae (one spe- the 1 1-monoenes attracted some other species cies), Pterophoridae (onk species), Drepanidae in these two families in past field tests.4'5) (one species), and Geometridae (two species). Although (9Z,1 1£)-9,1 1-tetradecadienyl No species in the family Drepanidae have been acetate is known to be a pheromone com- attracted before in Japan, while monoeneat- ponent of Noctuidae females,1} no Noctuidae tractants for the eight other families were species but three species in other families were found in our previous tests.4'5) caught by the 9,ll-diene and its functional Compoundswith a 8, 10-dodecadiene system derivatives. Namely, Xyrosaris lichneuta in have been reported as pheromone components Yponomeutidae, Pselnophorus vilis in for some species in the sub-family Olethre- Pterophoridae and Macrauzata maxima in utinae of the family Tortricidae.1} In this field Drepanidae were attracted to the lures baited test, the newattraction to 8,10-dodecadienes with (9Z,11£)-9,ll-tetradecadien-l-ol, the of four Olethreutinae species (Aterpia issikii, mixture of its aldehyde and acetate derivatives, Hedyadimidiana, Proschistis marmaropaand and the aldehyde derivative, respectively. In Rhyacionia duplana Simulaid) was revealed, in Canada, the diene and (9Z,l lZ)-geometrical addition to Matsumuraeses Jalcana, the sex isomers have attracted male moths in two pheromone of which was recently found to families (Drepanidae and Geometridae).2) So be a mixture of (SE, 10£)-8,10-dodecadienyl the 9,1 1-diene system might be included in the acetate and (£)-8-dodecenyl acetate.6) It is pheromone components of several families supported by this result that 8,10-dodeca- without indicating the taxonomical character dienes are one of the characteristic compo- of the species. It is noteworthy that the nents in the pheromones of the Olethreuti- (9£,ll£)-geometrical isomer of the diene nae species, while Acria ceramitis in the fami- acetate has been isolated from one Tortrici- ly Oecophoridae, which taxonomically unre- dae species.7) lated to Olethreutinae, was interestingly at- Weobserved the attraction of three Gracil- tracted by the 8, 10-dodecadiene.
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