for LC with LC oil leaf the from significantly differed and toxicity same LC T. urticae (Neoseiulus californicus McGregor).Based on with regard to the susceptibility of the natural enemy of eugenol asapositivecontrol. The oilswerealsoevaluated spider mite(T. urticae)andtheresultswerecomparedwith regarding their acaricidal potential against the two-spotted marginatum Jacq. were evaluated in the laboratory properties. Essential oils from stems, flowers, and leaves of and repellent effects, antifeedant, ovicidal, and other been broadlystudiedforpest-control,includingtoxic with synthetic chemicals. The essential oils ofplants have -based pesticideshavefewersideeffects compared crops worldwide.Ithasbeenshownthatmanyofnatural economically important pest of agricultural and ornamental Tetranychus urticaeKoch(Acari: Tetranychidae) is an ABSTRACT sesquiterpenes were more toxic with an LC oviposition. Among the chemical constituents tested, for lower significantly to that of thepositive control. The oilmortality rate was of theoilstestedexhibitedtoxicitygreaterthanorequal L , predatormite,two-spottedspidermite. Key words: Acaricidal activity, chemical constituents, in aplant-basedacaricidalagent. these oilsstrongcandidates for useastheactive ingredient properties, oviposition deterrence and selectivity make doi:10.4067/S0718-58392016000100010 Accepted: 7September2015. Received: 11 March2015. Irmãos, 52171-900Recife,Pernambuco, Brasil. Ciências Moleculares, Rua DomManoeldeMedeiros s/n,Dois 2 * 900 Recife,Pernambuco,Brasil. Agronomia, Rua DomManoel de Medeiross/n,DoisIrmãos,52171- 1 (McGregor) Nicolle Ribeiro Toxicity ofessentialoils marginatum urticae Universidade FederalRuraldePernambuco, Departamento de Corresponding author([email protected]). Universidade FederalRuraldePernambuco,Departamento de -1 than phenylpropanoids 50 50 T. urticae CHILEAN JOURNAL OF AGRICULTURALCHILEAN JOURNAL OF AGRICULTURAL RESEARCH 76(1) JANUARY RESEARCH 76(1)JANUARY estimates, oils from stems and flowers exhibited the exhibited flowers and stems from oils estimates, .4 n 85 μ L μL 8.51 and 6.64 50 0.37, 0.56, and 3.77 μL L μL 3.77 and 0.56, 0.37, (>95%). The Koch and 1 , ClaudioCamara N. californicus P. marginatum oils also deterred -1 CHILEAN JOURNAL OF AGRICULTURAL RESEARCH 76(1)JANUARY Z-asarone and , respectively. The acaricidal Jacq.against -1 , respectively. None (50% to70%)than 1* , andClecioRamos E-asarone with Neoseiulus californicus Neoseiulus 50 of 2.89 μL 2.89 of - - MARCH 2016 MARCH 2016 Tetranychus Tetranychus 2 demonstrate potent insecticidal activity on 4 sesquiterpenes asthepredominant chemical classes. These oils research grouprevealed the presenceofphenylpropanoids and of leaves and flowers, stems, al., 2011). A preliminary chemical investigation of oilsfrom of Pernambuco, Paraíba, and Rio Grande do Norte) (Chahal et forest andisknownas‘‘malvaisco” innortheastern Brazil (states shrub that grows abundantly around the borders ofthe Atlantic occur inPernambuco,Pipermarginatum Jacq.isanaromatic herbivory (Scottetal.,2008). Among thespeciesofPiperthat amides, andalkaloids,whichareusedinthedefense against of secondarymetabolites, such asphenylpropanoids, lignans, known forthe production of essential oils and the accumulation potential for thecontrolofagricultural pests. These plantsare Forest inthestateofPernambuco(northeastern Brazil), and have throughout South America, includingfragmentsofthe Atlantic al., 2013). et insect, causingphysiologicalandbehavioralresponses(Mossi pests, asthesesubstancesactonthenervoussystemoftarget Essential oils are promising agents forthe control of agricultural including the use of essential oils (Motazedian et al., 2012). alternative methods forthecontrolofT. urticae insects (Motazedian etal.,2012). To reduce these negative effects, well astheelimination ofN.californicus caused serious damage due to environmental contamination as 2007). However, the continual use of conventional acaricides has of mite pesticides, together with biological control involving the generalist economic returnsforfarmers. and grapecrops,exerting a negative impact on productivity and pest hascaused considerable harm to tomato, melon, strawberry, of Pernambuco, Brazil, date back to the 1980s. Since then, this of records the two-spotted spider mite in agricultural systems in the state first The 2012). Weintraub, and (Gerson fruit citrus cucumber, melon,strawberry, corn,soybean,apple,grape,and pest feeds on several plant species, including crops suchastomato, Tetranychidae) is considered the most important. This cosmopolitan the two-spottedspidermite(Tetranychus urticaeKoch; Acari: Among the different species of mites of the family Tetranychidae, INTRODUCTION Piper Piper T. urticaefoundindifferent regionsofBrazil(FrauloandLiburd, Species of the genus Piper (Piperaceae) are widely distributed The main form of control for T. urticae Neoseiulus californicus McGregor, which is a natural predator - MARCH 2016 P. marginatum conductedbyour

andvariouspollinating isthe use ofsynthetic th instarlarvae of arebeingtested,

71 RESEARCH CHILEAN JOURNAL OF AGRICULTURALCHILEAN JOURNAL OF AGRICULTURAL RESEARCH 76(1) JANUARY RESEARCH 76(1)JANUARY Constituents listed inorderofelutiononanon-polarDB-5 column. Patchoulol E-Asarone Z-Asarone β-Caryophyllene from essentialoilsofPipermarginatum Table 1.Percentageselected for ofcompounds investigation the mosquito group (Autranetal.,2009)(Table 1)andtheircommercial of identification chemical marginatum oilsdetermined previously byourresearch the on based selected were kept underrefrigerationat5°Cuntiltheacaricidalassays. sulfate, storedinhermetically sealed glasscontainersand modified a using oil layerswereseparatedanddriedoveranhydroussodium of isolated leaves were and Clevenger-type apparatus and hydrodistillation for 2 h. The g) flowers, (100 stems, marginatum from oils Essential Isolation ofessentialoils University ofPernambuco(accessionnumber:48210). Vasconcelos SobrinhoHerbariumoftheFederalRural samples andavoucherspecimen was depositedatthe identified previously with comparisons through (UFRPE) Department of theRuralFederalUniversityPernambuco Biology the of Sales de Margareth F. Dr. by identified was 34°52’30” (8°7’30” S, W), Pernambuco,Brazil. The plant from a fragment of the Atlantic forest in the city of Recife of leaves and flowers, Stems, Collection ofplantmaterial MATERIALS ANDMETHODS marginatum previous study has evaluated the acaricidal action of and al., 2006; Coitinho et al., 2011), molitor such asSolenopsissaevissima(Soutoetal.,2012),Tenebrio P. marginatum oilhasbeenreportedforotherarthropods, oviposition (Autranetal.,2009). The insecticidal activity of urticae on leaves) and flowers, parts ofP. (stems, marginatum acaricidal properties ofessentialoilvaporsfromdifferent of thepresentstudywastoconductalaboratorytest Atlantic ForestinthestateofPernambuco,Brazil,aim of essential oils from aromatic that occur inthe californicus Z-asarone and phenylpropanoids the and patchoulol and β-caryophyllene, positive control. The relative toxicity ofthesesquiterpenes Compounds The compoundsforinvestigation ofacaricidal potential As part of ourinvestigation into the acaricidal properties udsa pontifica Suidasia andN.californicus (Fazolin et al., 2007), Sitophilus (Estrela zeamais et . oil onT. urticae E-asarone isalsodiscussed. Stem 6.8 32.6 8.5 25.7 (Assis et al.,2011)(Assis . However, no , comparingwitheugenol,usedas andalso serve as a deterrent to P. marginatum werecollected anditsnatural enemy, N. Tyrophagus putrescentiae Inflorescence . 13.1 22.1 4.5 23.4 - - MARCH 2016 MARCH 2016 Leaf 7.5 6.4 30.4 16.0 P. P. P. T. T. P. oils, 0.2 to 14 μL L μL 14 to 0.2 oils, the positivecontrol. together witheugenol,whichwasusedas Missouri, USA), to 99%)wereacquired commercially from Sigma(St.Louis, availability. Compoundswith a high degree of purity (97% communis L.;Euphorbiaceae)wereoffered every2d. urticae on thejack bean leaf to stimulate oviposition. placed were fibers Cotton mites. the of escape the prevent filter paper with the margin surround by moistened cotton to thepolyethylene on foam and a jack bean (C. ensiformis) leaf was placed on the was placed disc paper filter A water. was made of apolyethylene foam disc soakedin distilled temperature of 27°Canda12:12hphotoperiod. Each arena reared in plastic arena maintained in BOD with a mean was usedto rear this predatory mite. The specimens were The method described by Monteiro (2002) with modifications Acarology Laboratorywithnoexposuretoacaricidal agents. Pernambuco) andmaintained at theUFRPE Agricultural was collected from the municipality of Bonito (State of ± 5%RHanda12:12hphotoperiod. Department. All bioassayswereperformedat25±1°C,65 exposure toacaricidal agents at the UFRPE Agronomy on jack bean (Canavalia ensiformis [L.] DC.) without any Specimens of T. urticae Insect rearing marginatum oilsvaporsagainst The fumigant method used toassess toxicity of P. Fumigant toxicity andfecunditytest L mortality rate in thetestswithT. urticae marginatum essential oils testedwerethosethatledto a95% offered as food on each leaf disc. The concentrations of specimens of T. urticae of modifications. Each leaf disc was infested with 10 specimens californicus assay method used to measure the toxicity of the oils to concentrations ofessentialoilsandcompounds that chamber withtheaidofan automatic pipette. The lowest attached totheinnersurface ofthelidfumigation compounds were applied to strips of filter paper (10 × 2 cm) females per Petri dish. The essential oils and chemical was infested with anadult disc leaf Each water. with saturated paper filter containing (1.5 cm)wereplaced equidistant inaPetridish(10cm) adapted from Pontesetal.(2007a).Fivejack bean leaves from The to 1.2 μL L of oils and compounds ranged from 0.005 to 8 μL8 to 0.005 from ranged L compounds and oils of that employed by Araújo etal.(2012). The concentrations -1 The population ofN.californicus usedinthebioassays airforoilfromstems,flowers,andleaves,respectively. N. californicus P. marginatum oilswasdetermined using amethod andpollenfromthecastoroilplant(Ricinus T. urticae -1 wasthat described by Araújo et al. (2012) with air for eugenol (positive control). The fumigant ovipositiondeterrenteffect ofthevapors , totaling30mitesperPetridish.Fifteen -1 airfortheconstituents and 6.4×10 usedforthebioassayswerereared andcastoroil plant pollen were eae ttln five totaling female, T. urticae T. urticae : 0.8,1.0,and8.0µL werethesameas Tetranychus -1 air for N. P. P. -5

72 CHILEAN JOURNAL OF AGRICULTURALCHILEAN JOURNAL OF AGRICULTURAL RESEARCH 76(1) JANUARY RESEARCH 76(1)JANUARY urticae. respectively; 6.4×10 for theoilsfromP. treatments andcontrolswasrecordedafter24h. fivereplicates, totaling10replicates. The numberofeggsin with employed, was design randomized entirely An chamber wasclosedandcoveredwithPVCplasticwrap. after theapplicationofoil/compound,fumigation substances wereusedinthenegativecontrol.Immediately patchoulol, that causedgreater than95%ofspecimensT. urticae inthefumigationbioassay(stem=0.8,flower =1.0,andleaf8.0µL L Figure 1.Meanmortality rateofTetranychusto Piper marginatumoilsatconcentrations and Neoseiuluscalifornicussubmitted urticae E-Asarone Z-Asarone Patchoulol β-Caryophyllene Leaf Inflorescence Table 2. Toxicity by fumigation (LC concentration necessary for50%mortality (LC (LeOra Software, 1987)forthe determination of the lethal the ProbitmodelusingPOLO-PCsoftwareprogram and flowers, stems, from leaves of P. oils marginatum andeugenol were analyzed with the for data mortality The Statistical analysis tests were usedinthefecunditytests:0.005,0.2,and1.0µL L the fumigation in oviposition reduced significantly Stem EU Preisler, 1992). In the fecundity bioassays, the method describedbyRobertsonandPreisler(Robertson confidence 95% levels. Toxicity of ratios weredetermined based onthe calculation the with population, mite 5.0, and8.0µL L EU: Eugenol used as positive control, N: number of mites, DF: degrees of freedom, SD: standard deviation, CI: confidence interval; χ interval; confidence CI: deviation, standard SD: freedom, of degrees DF: mites, of number N: control, positive as used Eugenol EU: * toxicity ratiocalculatedbyRobertson&Preislermethod. Oil/Compound Significant whenconfidenceintervaldoesnotinclude1. Z -asarone, andE -1 air for the compounds β-caryophyllene,

marginatum stems,flowers,andleaves, -5 630 540 630 540 540 540 540 640 µL L µL N -1 airforeugenol;and0.2,2.5, -asarone, respectively. No 50 DF , µL L 4 3 4 3 3 3 3 3 -1 air)ofthePipermarginatumessentialoilsandmajor constituentsagainstTetranychus 5.39 ±0.54 6.93 ±0.75 2.31 ±0.20 2.44 ±0.28 3.85 ±0.49 6.46 ±0.74 5.64 ±0.58 0.85 ±0.076 Slope ±SD 50 t-test was - - ) ofthe MARCH 2016 MARCH 2016 -1 air N. californicus comparison tothepositivecontrol. compounds exhibited greater orequalacaricidal activity in with itsisomerE-asarone(6.4%).Noneoftheisolated (30.4%), showedlesstoxicity than theoilandsimilar toxicity phenylpropanoid leaf oilintheconcentration of 16.0%(Tables 1and2). The the in found β-caryophyllene, sesquiterpene to susceptible fold moretoxicthanthestemoil(Table 2). was morepotentthanthepositivecontrol,which92.5- more 10-fold toxic in comparison to theleaf oil. However, noneoftheoils approximately were which oils, flower and LC chemical constituents were toxic to The vaporsfromtheP. marginatum oilsandselected RESULTS N. californicus treatments and controls. The used to compare data on the number of eggsper female in 8.51 (7.14-9.61) 6.64 (5.05-7.70) 4.00 (2.79-5.24) 2.89 (1.51-4.30) 3.77 (2.12-4.12) 0.56 (0.42-0.65) 0.37 (0.27-0.46) 0.004 (0.002-0.005) Figure 1displaysthesusceptibilityofpredatorymite Among thecompoundstested,T. urticae LC 50 values demonstrate the same degree of toxicity for stem 50 (CIat95%) andT. urticae totheP. marginatum oilsatconcentrations Z-asarone, major compound of leaf oil 8.80 6.84 8.96 6.81 6.94 6.28 7.61 1.52 χ 2 t-test wasalsousedtocompare mortality data T. urticae 2413.3 1883.9 1070.6 1134.9 820.78 159.2 105.84 - * * * * * . (333.3-17471.9) 258.2-13744.5) (164.2-7840.9) (145.7-7866.1) (25.4-995.4) * * 2 (57.56-11702.94) (16.9-659.3) : Chi-squared, TR: : . The estimated . The TR wasmost 50 -1 air).

73 CHILEAN JOURNAL OF AGRICULTURALCHILEAN JOURNAL OF AGRICULTURAL RESEARCH 76(1) JANUARY RESEARCH 76(1)JANUARY was significantly higher than mean this test were selected based on the fumigation bioassay in which the number of eggs differed significantly from the negative control. constituents (β-caryophyllene,patchoulol,Z-asarone, and Figure 2. Mean number ofeggsper Tetranychus urticae female when submittedtovaporsfrom Piper marginatum essential oils, major 95% ≥ to led that et al.,2012). (Araújo-Júnior et al., 2010), andPiper aduncum (Araújo (Pontes et al., 2007b), heptaphyllum investigated previously, suchProtium bahianum, activity of otherplantspeciesagainstT. hasbeen urticae californicus marginatum oilsonT. urticaeanditsnaturalenemyN. oviposition deterrence. in separately causedphysiological andbehaviorresponses and leaves and their major components either together or In the present study, oilsfromP. marginatum stems, flowers, DISCUSSION eggs inthenegativecontrol. of the number than smaller significantly was constituents) number ofeggsonthediscsintreatments (oils andmajor female when exposedtothe different substances. The Figure 2displaysthemeannumberofeggslaidperT. urticae the sublethal concentration of each oil and major constituent. the death of mites, further experiments were performed with in the number of eggs was due to exposure to the oils or specimens ofT. urticae. To determine whetherthisreduction in theconcentration oftheoilsandconsequentdeath urticae suggesting thattheP. marginatum oilswereselective to T. = 1.0, and leaves = 8.0 µL L This is the first report of the fumigating action of action the fumigating of report first the is This The number of eggslaid was reduced with the increase T. urticae, as demonstrated by fumigant toxicity and . . However, theevaluation of theacaricidal (Pontes et al., 2007a; 2010), Xylopia sericea T. urticae Citrus sinensis, -1 mortality (stems = 0.8, flowers 0.8, = (stems mortality

air). Mean N. californicus T. urticae mortality Citrus aurantium mortality, - - Protium MARCH 2016 MARCH 2016 E-asarone)positive control and (eugenol). The concentrationsemployedin P. P. been confirmed in previous reports involving thelarvae involving of reports previous in confirmed been acaricidal activity. The biological properties of itdemonstrated and oils, leaf and flower, stem, patchoulol, which werefoundindifferent proportionsin and β-caryophyllene only components, major the Among were moretoxictoT. oils urticae flower and stem constituents, chemical in differences oils islikelyduetoqualitative and/or quantitative LC using thefumigantmethod β-caryophyllene against mites (Oh et al., 2013). In this of study, action the involving reports previous in confirmed been and previousreportrevealedtheLD eugenol, isassignedtotheallylicchain(Borchertetal.,1973), safrole, anaturalinsecticideandchemicallysimilarto eugenol has an allylic chain. The toxicity of phenylpropanoid phenylpropanoids havesimilarchemicalstructures,but about 1750timesmoretoxicthanthetwoisomers. The three E (Trouessart), respectively. Dermatophagoides farinae high toxicityofthesecompoundsagainstthemiteT. urticae. group in the phenylpropanoids can contribute significantly to against more active against themitewithLC in smalleramounts(Moraesetal.,2012). likely that these compounds act in synergy withthosefound the fumigating action observed inthe experiments and it is constituents are not the only components responsible for and -azarone andZ The difference intoxicity among different P. marginatum Eugenol (positive control) is a phenylpropanoid, with Eugenol (positivecontrol)isaphenylpropanoid,with Among the major components, the β-caryophyllene was β-caryophyllene the components, major the Among Aedes aegypti 50 T. urticae(Araújoet al., 2012). Moreover, the major f .3 n 35 μ cm μg 3.58 and 3.13 of T. urticaefemales. These dataindicatethattheallylic -azarone isomers, however eugenol was -azarone isomers,howevereugenolwas (Diptera: Culicidae) (Dória et al., 2010) (Hughes) andD.pteronyssinus thantheleafoil(Table 1). -2 againsthousedustmites -aypyln exhibited β-caryophyllene 50 50 0.36µL L β-caryophyllene have β-caryophyllene 2.89µL L -1 -1 for safrole forsafrole thathave

74 CHILEAN JOURNAL OF AGRICULTURALCHILEAN JOURNAL OF AGRICULTURAL RESEARCH 76(1) JANUARY RESEARCH 76(1)JANUARY (Lamiaceae), Eucalyptus citriodora (Myrtaceae), the toxicity of oils from in differences significant no found authors cited However, (Lamiaceae) on the same predator (Han et al., 2010). Eugenia caryophyllata reported for essential oils fromCarumcarvi(Apiaceae), oil astheactive ingredient. Similar resultshavebeen use ofaplant-based acaricide with of N. californicus. susceptible toP. marginatum essentialoilsthanitspredator et al.,2004). officinalis susceptible to conventional acaricides than effective due tothefactthatpredatormite is more control ofT. urticae greenhouse in intensified operations and hasbecome a keymeasure in the integral has enemies natural of use the developed resistance to suchacaricides in recent years. Thus, of Petrolina,Pernambuco,Brazil.However, thispesthas groves and greenhouses in agricultural systems in the city widely employed methodsforthecontrol of T. urticae drastically reduced. constituents did notimpede oviposition, fecundity was concentrations of theP. marginatum oilsandtheirmajor to theessential oil vapors. While exposure tosublethal that study, theresultsof fecundity experiments demonstrated properties oftheoilsordeathmites.Inpresent as towhetherthisreduction in fecundity was duetothe (Pontes et al., 2007a; 2007b; 2010),butwithnoindication reported inpreviousstudiesanalyzing fumigant toxicity of essential oils toreducefecundity in T. urticae urticae affected fecundity in T. urticaeindicating an action on T. californicus Thymus vulgaris(Lamiaceae) between T. urticaeandN. as theactiveingredientinaplant-based acaricide. Neoseiulus californicus, make these oils astrongcandidate and the less toxic effect on the natural enemy of this mite, properties oftheseoils,alongwithovipositiondeterrence for thecontrolofTetranychus urticae from promising oils are oils, flower and stem essential especially marginatum, findings, present the on Based CONCLUSION In the present study, The use ofconventional acaricides is one ofthemost Piper marginatum oilsandtheirmajor compounds also T. urticaewithN.californicus iscompatible with the T. urticaefemales exhibited a behavioral response fecundity at sublethal concentrations. The ability (Lamiaceae), . This finding suggests that the management the that suggests finding This Mentha ×piperita . Nonetheless,thispractice is notalways (Myrtaceae) andOcimumbasilicum Mentha spicata (Lamiaceae) or Cymbopogon nardus (Poaceae), T. urticae P. marginatum proved to be more (Lamiaceae), Mentha pulegium . The acaricidal . The T. urticae hasbeen - - essential MARCH 2016 MARCH 2016 Salvia (Choi Piper in Araújo-Junior, C.P.,da Câmara,I.A.Neves,N.C.Ribeiro, C.A.G. Araújo, M.J.C.,C.A.G.daCâmara, F.S. Born,M.M.Moraes,and REFERENCES Project (nr477778/2013-5). e Científico Carvalho Ribeiro and funding through the CNPq Universal Desenvolvimento de Tecnológico (CNPq) forthegrantawardedtoNicolle de Nacional Conselho The authors are grateful to theBrazilian Forest Agency ACKNOWLEDGEMENTS Autran, E.S., I.A. Neves, C.S.B. Da Silva, G.K.N. Santos, Autran, E.S.,I.A.Neves,C.S.B.DaSilva,G.K.N. Assis, C.P.O., M.G.C.Gondim,H.A.A.Siqueira, and C.A.G.da Estrela, J.L.V., M.Fazolin, V. Catani, M.R. Alécio, eM.S.Lima. Dória, G.A., W.J. Silva,G.A.Carvalho, P.B. Alves, and Coitinho, R.L.B.C., J.V. Oliveira, M.G.C. Gondim Junior, e C.A.G. Choi, W.,Park, and S.Lee,H. Y. 2004. Ahn. Toxicity ofplant Chahal, J., R.Ohlyan, A. Kandale, A. Walia, and S.Puri.2011. Borchert, P., P.G. Wislocki, J.A. Miller, andE.C. 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(Coleoptera: Curculionidae). Ciência e Agrotecnologia 35:172- de óleosessenciais paraSitophilus zeamais Motschulsky, 1885 da Câmara. 2011. Toxicidade por fumigação, contato e ingestão org/10.1093/jee/97.2.553. of Economic Entomology 97:553-558. doi:http://dx.doi. and essential oilstoTetranychus urticae Pharmaceutical ReviewandResearch2:130-144. activity of genus Piper: A review. International Journal of Current Introduction, phytochemistry, traditional uses and biological 1’-acetoxysafrole. Cancerresearch33:575-589. safrole to 1’-hydroxysafrole and the electronphilic reactivity of The metabolism of itnaturally occurring hepatocarcinogen doi:10.1016/j.biortech.2008.10.055. Jacq. (Piperaceae). Bioresource Technology 100:2284-2288. Phytoseiulus persimilis (Acari: Phytoseiidae). Journal . Experimental and Applied Acarology 57:139-155. Aedes aegypti Tetranychus urticae . Pharmaceutical Biology 48:615-20. . 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