Chemical Composition and Insecticidal Activity of Myrtle (Myrtus communis L.) Essential Oil against Two Stored-Product Pests

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1 Journl of Mediinl Plnts nd By-produts (2012) 2: Originl Artile Chemil Composition nd Insetiidl Ativity of Myrtle (Myrtus ommunis L.) Essentil Oil ginst Two Stored-Produt Pests Abbs Khni* nd Frzneh Bsvnd Deprtment of Plnt Protetion, Fulty of Agriulture, University of Zbol, P.O. Box , Zbol, Irn Artile History: Reeived: 7 Deember 2012/Aepted in revised form: 26 Jnury Irnin Soiety of Mediinl Plnts. All rights reserved. Abstrt Essentil oil extrted from the leves of Myrtle, Myrtus ommunis L. (Myrtee) ws tested in vitro for voltile toxiity ginst two stored-produt insets (Tribolium onfusum nd Cllosobruhus multus). The hemil omposition of the plnt oil ws exmined by gs hromtogrphy-mss spetrometry (GC-MS). The mjor oil omponents were α-pinene (10.4%), α- Terpineol (10.1%), linlool (9.0%), 1, 8-ineole (7.6%), Gernyl butyrte (6.3%), Gerniol (6.2%), Cryophyllene oxide (5.3%) nd Neryl ette (5.0%). In the fumignt toxiity test, signifint differenes in mortlity of insets to essentil oil vpor were observed in different onentrtions fter n exposure time of 24 hours. C. multus (LC 50 =9.5 µl/l ir) ws more suseptible to the plnt oil thn T. onfusum (LC 50 =260.7 µl/l ir). The results suggested tht essentil oil of M. ommunis L. ould be used s potentil bioontrol gent for stored-produt insets. Key words: Fumignt toxiity, GC-MS, Myrtus ommunis L., Stored-produts, Essentil oil. Introdution Confused flour beetle, Tribolium onfusum (Jquelin du Vl) ttks stored grins nd foods. Adults nd lrve feed on broken kernels nd finely ground mterils in grin storges, flour mills, wrehouses nd wherever grin or grin produts re stored. This speies is probbly the most serious pest of the genus Tribolium nd one of the most eonomilly importnt beetles [1]. A key pest of owpe is the owpe weevil, C. multus (Fb.), bruhid tht infests both pods in the field nd seeds in storge. Tnzubil [2] found tht this inset n dmge 100% of stored seeds using weight losses of up to 60%. Control of storge pest insets is dependent on the use of hemil methods suh s fumigtion tretments. At present, phosphine nd methyl bromide re the prinipl fumignts vilble for pest ontrol in durbles, perishbles nd in qurntine tretments [3]. However, the extended use of brod-spetrum insetiides hs resulted in the development of inset resistne, environmentl pollution, workers dnger nd destrution of non-trget orgnisms. In reent yers, interest in sreening mediinl plnts for inset ontrol hs inresed signifintly nd interest in the oils ws renewed with emerging demonstrtion of their fumignt nd ontt insetiidl tivities to wide rnge of pests in the 1990s [4]. The insetiidl tivity of essentil oils nd plnt extrts ginst different oleoptern stored produt insets hs been evluted [5]. In ft, pestiides derived from plnt essentil oils do hve severl importnt benefits. Due to their voltile nture, there is muh lower level of risk to the environment thn with urrent syntheti pestiides. Predtor, prsitoid nd pollintor inset popultions will be less impted beuse of the miniml residul tivity, mking essentil-oil-bsed pestiides omptible with integrted pest mngement progrms [6]. *Corresponding uthor: Deprtment of Plnt Protetion, Fulty of Agriulture, University of Zbol, P.O. Box , Zbol, Irn. Tel. nd Fx: E-mil Address: bbkhni@yhoo.om & bbkhni@uoz..ir

2 Journl of Mediinl Plnts nd By-produts (2012) 2: Myrtus ommunis L. (Myrtee), mediinl nd romti speies, is n romti evergreen perennil shrub or smll tree, m in height with smll folige nd deep fissured brk. It is ntive to Southern Europe, North Afri nd West Asi. It is distributed in south, north, nd entrl prts of Irn [7]. Vrious biologil tivities hve been reported for M. ommunis L., suh s ntibteril [8], ntifungl [9, 10] nd insetiidl properties [11-14]. In the present study, the hemil onstituent of essentil oil from M. ommunis L. leves ws determined, nd the insetiidl tivity of these essentil oils ws tested ginst the dult stges of the stored-produts pests, Tribolium onfusum nd Cllosobruhus multus. Mterils nd Methods Insets Cllosobruhus multus nd Tribolium onfusum were rered ording to method of khni nd Asghri [15]. Essentil oil extrtion The leves of M. ommunis L. olleted from Irnshhr (27 15' N, 60 40' E; lt. 590 m), loted in Sistn nd Bluhestn provine, Irn, from June to July, Essentil oil extrtion ws done following the method desribed by Khni et l. [16]. The extrted oil ws dehydrted with nhydrous sodium sulphte (10 min) nd immeditely stored in irtight glsswre in refrigertor t 4 C. Gs hromtogrphy-mss spetrometry The essentil oils ws nlyzed on gs hromtogrph mss spetrometer (GC MS) (Shimdzu 17A QP5050, Jpn). The GC olumn ws DB-5 (30 m 0.25 mm i.d, 0.25 µm film thikness). The olumn oven temperture ws set t 60 C for 3 min, nd then inresed to 260 C t rte of 5 C/min. Injetor nd detetor tempertures were 230 nd 245 C, respetively. The GC mss nlysis ws rried out with the sme hrteristis s used in GC. The ioniztion energy ws 70 ev with sn time of 1s nd mss rnge of mu. Unknown essentil oil ws identified by ompring its GC retention time to tht of known ompounds nd by omprison of its mss spetr, either with known ompounds or published spetr. Fumignt toxiity To determine the fumignt toxiity of the oil, filter pper (2.0 m dimeter) ws impregnted with 3, 5, 10, 15 nd 20 µl of oils without using ny solvent for T. onfusum nd impregnted with 0.3, 0.4, 0.5, 0.75, 1, 1.25 nd 1.5 µl of oils for C. multus. Then the filter pper ws tthed to the under surfe of the srew p of glss vil volume (60 ml) to generte onentrtions of 50, 83.33, , 250 nd µl/l ir for T. onfusum nd onentrtions of 5, 6.66, 8.33, 12.5, 16.66, nd 25 µl/l ir for C. multus. The p ws srewed tightly on the vil ontining ten dults (1-7 dys old with undefined sex) of eh speies of inset seprtely. Eh onentrtion nd ontrol ws replited four times. All experiments were rried out in the drk in growth hmber set t 27±1 C nd 65±5% reltive humidity. Mortlity ws determined 24 h fter exposure to essentil oil from M. ommunis L. leves. When no sign of leg or ntennl movement were observed, inset were onsidered s ded. Mortlity (%) Mortlity (%) T. onfusum C. multus Conentrtion (µl/l ir) b Fig 1 Lethl effet of essentil oil from Myrtus ommunis L. leves on Tribolium onfusum nd Cllosobruhus multus fter 24 hours. To ssessment 50% lethl doses (LC 50 ) fter n exposure time of 24 hours, the onentrtions of the essentil oils using 10 to 90% mortlity were used. Five different onentrtions (83.33, , 250 nd b Conentrtion (µl/l ir) b b

3 85 Khni nd Bsvnd nd µl/l ir for T. onfusum nd 5, 6.66, 8.33, 12.5 nd µl/l ir for C. multus), eh with four replites nd ten individuls per eh replite, were used. The mortlity ws determined s desribed in previous experiment. The tretment bottles were monitored for 48 h fter reording the dt nd no ffeted inset reovered. Dt obtined from eh dose response biossy were subjeted to probit nlysis. LC 50 vlues were determined by logprobit regression using SPSS 16.0 for Windows [17]. Sttistil nlysis Sttistil nlysis of the mortlity dt ws performed by one-wy nlysis of vrine (ANOVA) with post-ho Tukey test using SPSS version Normlity of dt ws tested using, Kolmogorov- Smirnov test, non-prmetri test. The results were expressed s men ± SE, nd onsidered signifintly different t P< Results nd Disussion Chemil omposition of essentil oils The hemil omposition of essentil oils of M. ommunis L. leves is presented in the Tble 1. The mjor omponents were α-pinene (10.4%), α-terpineol (10.1%), linlool (9.0%), 1,8-ineole (7.6%), gernyl butyrte (6.3%), gerniol (6.2%), ryophyllene oxide (5.3%) nd neryl ette (5.0%). Furthermore, lesser mounts of the other importnt insetiidl omponents inlude ryophyllene (2.9%), methyl eugenol (2.8%), β-pinene (2.4%), α-dinol (1.5%) nd Trns rveol (1.7%) were existed in essentil oil of this plnt. Literture reveled the qulittive nd quntittive nlysis of different hemotypes of M. ommunis L. essentil oils from different ountries. The oil in leves of M. ommunis L. growing in Turkey ontined 1,8 ineole, linlool, myrtenyl ette nd myrtenol s mjor omponents [18]. α- pinene (29.4%), limonene (21.2%), 1,8 ineole (18%), linlool (10.6%), linlyl ette (4.6%) nd α-terpineole (3.1%) were reported to be the mjor omponents of myrtle leves [19]. The essentil oil of M. ommunis L. in Frne ontined 14 ompounds, α-pinene nd 1,8-ineol (Eulyptol) together representing round 86% [9]. The oil in leves of nturl popultions of M. ommunis L. growing in Tunisi ontins α-pinene (19.2%), 1,8- ineole (16%), linlool (7.7%), α-terpineol (7.5%) nd limonene (5.7%) [20]. The oil obtined from leves of M. ommunis L. in Itly (Srdinin) were hrterized by high ontents of α-pinene, limonene nd 1,8-ineole [21]. Fig 2 Mortlity probit line for Tribolium onfusum nd Cllosobruhus multus 24 hours fter exposure to essentil oil from Myrtus ommunis L. leves. LC 50 point is shown by the red str. The mjor ompounds in the essentil oils of M. ommunis L. leves were α pinene (30.0%), 1,8 ineole (28.8%), nd limonene (17.5%) in Itly [21]. In other study, the mjor ompounds reported were α- pinene (19.2%), 1,8-ineole (16.0%), linlool (7.7%), α-terpineol (7.5%) nd limonene (5.7%) [22]. Mhboubi nd Ghzin [23] reported the presene of 1,8-ineole (36.1%), α-pinene (22.5%), linlool (8.4%), bornyl ette (5.2%), α-terpineol (4.4%), linlyl ette (4.2%) nd limonene (3.8%) s mjor omponents of leves of M. ommunis L. in Irn. The essentil oil of M. ommunis L. in Elb Islnd ontined α-pinene (51.8%), 1,8-ineol (24.6%) nd limonene (7.6%) s mjor omponents [12]. The min omponents found in M. ommunis L. in Southern Turkey were linlool (31.3%), linlyl ette (17.8%), 1,8-ineol (14.7%), gernyl ette (9.1%), α pinene (8.4%) nd α-terpineol (6.5%) [14]. Twenty one different omponents were identified in the essentil oils of M. ommunis leves olleted from Chm Moord re in Lorestn provine, Irn, tht the min

4 Journl of Mediinl Plnts nd By-produts (2012) 2: omponents were limonene (18.5%), α pinene (13.3%) nd 1,8 ineole (10.6%) [24]. In our study the omposition of essentil oils of M. ommunis L ws reltively similr to the previous reports of other prts of world, whih the mjor omponents were α-pinene, linlool nd 1,8 ineole. Compred to other reserhes, in our study, limonene, linlyl ette, bornyl ette, gernyl ette nd myrtenyl ette were bsent nd myrtenol (1.36%) ws t low mount. On the other hnd, gernyl butyrte (6.3%), gerniol (6.2%), ryophyllene oxide (5.3%) nd neryl ette (5.0%), α- terpinyl ette (4.1%) were t reltively high mounts. Fumignt toxiity In ll ses, onsiderble differenes in mortlity of inset to essentil oil vpor were observed in different onentrtions. The mortlity inresed signifintly with rising onentrtions (Fig 1, 2) (F 5,18 = 64.6; P=0 for T. onfusum nd F 6,21 = 45.7; P=0 for C. multus). Results indited tht the oil of tested plnt ws signifintly more toxi ginst C. multus thn T. onfusum, s inferred by the onfidene intervls of LC 50 (Tble 2). Bsed on LC 50, the oil of M. ommunis displyed strong insetiidl tivity ginst C. multus (LC 50 =9.50 µl/l ir), but reveled fewer tivity ginst T. onfusum (LC 50 =260.7 µl/l ir) (Tble 2). Similrly, differene response of the inset speies to the essentil oils hs previously been reported for these stored produt insets [15,16]. The differene of sensitivity my be ttributed minly to the phenotypi resistne (modifitions in the trget site), metboli resistne (bility to detoxify insetiides) or behviorl modifition. Behviorl hnges tht minimize ontt between inset nd insetiide my use severe impt in the insetiide pplition effiy, espeilly if resistne is seleted by physiologil fetures [25]. T. onfusum hd tendeny to be less tive (behviorl resistne mehnism) nd hd limited movement (our observtions) ompred to C. multus tht my redue brething nd insetiide penetrtion vi the inset spirle. Bsed on our knowledge, no study hs been previously reported on the insetiidl tivity of M. ommunis oil ginst C. multus nd T. onfusum. However, the insetiidl effiy of M. ommunis oil hs been reported ginst other insets. The LC 50 vlues of essentil oils of M. ommunis L. ginst Tetrnyhus urtie Koh (Ari: Tetrnyhide) ws 53.2 µl /l ir [26]. At 24 h- exposure period, LC 50 for M. ommunis L. leves essentil oil on eggs, lrve, pupe nd dults of khpr beetle, Trogoderm grnrium Everts (Coleopter: Dermestide), were 54.7, 307.4, nd 68.4 µl/l ir, respetively [27]. Toxiity of M. ommunis L. essentil oil on some mosquito ws reported. M. ommunis L. essentil oil indued only 36.7% lrvl mortlity on the mosquito, Aedes lbopitus (Dipter: Culiide) t dosge of 300 ppm [12]. Amer nd Mehlhorn [13] tested the lrviidl effet of essentil oils extrted from 41 plnts ginst third instr lrve of three different mosquitoes nd showed tht M. ommunis L. essentil oil used 100% lrvl mortlity t low dosge (50 ppm) ginst A. egypti. Probit nlysis showed tht LC 50 vlues of M. ommunis L. essentil oil ginst Ephesti kuehniell (Lepidopter: Pyrlide), Plodi interpuntell (Lepidopter: Pyrlide) nd Anthoselides obtetus (Coleopter: Bruhide) were 12.7, 22.6 nd 49.6 µl/l ir, respetively [14]. Methnol extrts of M. ommunis L. reveled insetiidl tivity on Cllosobruhus hinensis [28]. The extrts from leves nd flowers of M. ommunis L. were found to be toxi ginst fourth-instr lrve of Culex pipiens molestus, nd thymol, rvrol, nd α-pinene were the most toxi pure omponents [11]. Tble 1 Chemil omposition of essentil oil from Myrtus ommunis L. leves Compounds Conentrtion (%) Kovts index Propnoi id α- pinene β-pinene β-myrene ,8-ineole Linlool Terpinen-4-ol α- Terpineol Myrtenol Trns rveol Gerniol Isobornyl_ette α- Terpinyl Aette Neryl ette β- Elemene Methyl eugenol Cryophyllene, (E) Curumol α- Bergmoten Alloromdendrene Germrene D Nerolidol, (E) Gernyl butyrte Cryophyllene oxide α- Humulene oxide α- Cdinol Cedrn-diol Phthli id Isopropyl plmitte Other ompounds

5 87 Khni nd Bsvnd Tble 2 Effiieny of essentil oil extrted from Myrtus ommunis L. leves ginst Tribolium onfusum nd Cllosobruhus multus dults Insets LC 50 95% CL χ 2 (df) Probbility Slope ± SE T. onfusum ( ) 6.17 (3) ±0.51 C. multus 9.50 ( ) 4.03 (3) ±0.55 * Ten individuls per replite, four replites per onentrtion, five onentrtions per ssy; LC: lethl onentrtion (µl/l ir), CL: onfidene limits (µl/l ir) In our study, both thymol nd rvrol were bsent in M. ommunis L. essentil oil, while α- pinene ws the most bundnt omponent. Monoterpenes in generl hve been well doumented to be tive s fumignts, repellents or insetiides towrd stored produts insets [29]. The insetiidl tivity of the essentil oils investigted in the present study my be ttributed to their mjor onstituents of monoterpenes. Insetiidl tivity of mjor onstitutes of the tested oil were before reported. 1,8-ineole, terpineol, nd linlool hve been evluted s fumignts ginst Tribolium stneum. [30]. Essentil oils rih in 1,8-ineole nd rveol were effetive ginst dults of Germn okroh, Blttell germni [31]. 1,8-ineole isolted from Artemisi nnu ws lso potentil insetiidl llelohemil tht ould redue the growth rte, food onsumption nd food utiliztion in some post hrvest pests nd house hold insets [32]. 1,8-ineole exhibited both ontt nd fumignt toxiity when tested ginst T. stneum [33]. IC 50 vlues (inhibitor onentrtion yielding 50% inhibition) of α-pinene ginst femle etylholine esterse of Blttell germni ws 0.28 mg/ml [31]. Topil pplition of gerniol on femle Pediulus humnus pitis De Geer (Phthirpter: Pediulide) demonstrted its insetiidl tivity with LD 50 vlue of 12.7 µg/inset [34]. The LC 50 vlues of linlool ginst Cllosobruhus multus nd Rhyzoperth domini were 23.6 nd 31 µl/l ir, respetively [35]. Linlool nd α-terpineol signifintly inresed the nymphl durtion in Germn okroh, Blttell germni (Linneus) when fed through rtifiil diet [36]. Similr effets ginst Ostrini nubillis (rered from 1st instrs on diet) hve been reorded with rveol, gerniol, linlool, α-pinene, α-terpineol, in the onentrtion rnge of mg/g diet [37]. Cryophyllene oxide, isolted from Uvri sp., turned out to be insetiidl nd ntifeednt [38]. Monzote et t. [39] observed tht ryophyllene oxide inhibited the mitohondril eletron trnsport hin in rt liver. Substituted phenol, methyl eugenol, showed ontt toxiity to Sitophilus zemis nd T. stneum [40]. The essentil oil from M. ommunis L. ould beome n interesting lterntive to onventionl hemil ontrol strtegies. However further studies need to be onduted to evlute the sfety of these oils before prtil use in stored produt inset ontrol. Aknowledgments This reserh ws supported finnilly by the University of Zbol, whih is gretly ppreited. Referenes 1. Rees DP. Coleopter. In: Subrmnym Bh, Hgstrum DW (eds.). Integrted mngement of insets in stored produts, Mrel Dekker, New York, 1995; Tnzubil PB. Control of some inset pests of owpe (Vign unguiult) with neem (Azdirht indi A. Juss.) in Northern Ghn. Trop Pest Mng. 1991;37: Shy E, Kostyukovsky M. Essentil oils: poteny ginst stored produt insets nd mode of tion. Stewrt Posthrvest Rev. 2006;2(4):(pper no. 5)./ ugust_2006/shy.pdfs. 4. Ismn MB. Plnt essentil oils for pest nd disese mngement. Crop Prot. 2000;19: Pérez SG, Rmos-López MA, Zvl-Sánhez MA, Cárdens-Orteg NC. Ativity of essentil oils s biortionl lterntive to ontrol oleoptern insets in stored grins. J Med Plnts Res. 2010;4(25): Koul O, Wli1 S, Dhliwl GS. Essentil Oils s Green Pestiides: Potentil nd Constrints. Biopesti Int. 2008;4: Zrgr A. Mediinl plnts. 6th ed. Tehrn University Press, Tehrn, Pourmnd MR, Yzdi MH, Byt M, Shhinjfri A. In vitro ntimirobil effets of Ztri multiflor Boiss, Myrtus ommunis L, Eulyptus offiinlis ginst Streptoous pneumonie, Morxell trrhlis nd Hemophilus influenze. Irnin J Med Arom Plnts. 2008;23: (In Persin, English bstr.) 9. Curini M, Binhi A, Epifno F, Bruni R, Tort L, Zmbonelli A. Composition nd invitro ntifungl tivity of essentil oils of Erigeron ndensis nd

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