Skip to main content
SpringerLink
Log in

Insecticidal activities of monoterpenes and phenylpropenes against Sitophilus oryzae and their inhibitory effects on acetylcholinesterase and adenosine triphosphatases

  • Original Research Paper
  • Published:
Applied Entomology and Zoology Aims and scope Submit manuscript

Abstract

In the present study, six monoterpenes [(−)-citronellal, p-cymene, (−)-menthone, α-pinene, α-terpinene, and (−)-terpinen-4-ol] and two phenylpropenes [trans-cinnamaldehyde and eugenol] were evaluated for their contact and fumigant toxicities against Sitophilus oryzae adults. The effects of these compounds on the mortality of S. oryzae adults in stored wheat and their inhibitory effects on acetylcholinesterase (AChE) and adenosine triphosphatases (ATPases) were examined. The tested compounds showed varying degrees of contact toxicity, with trans-cinnamaldehyde (LC50 = 0.01 mg/cm2) being the most potent compound, followed by (−)-menthone (LC50 = 0.013 mg/cm2) and eugenol (LC50 = 0.015 mg/cm2). In a fumigant toxicity assay, the monoterpenes α-terpinene, p-cymene, and (−)-menthone showed the highest toxicities (LC50 = 50.79, 52.37, and 54.08 μl/L air, respectively). Trans-cinnamaldehyde, (−)-citronellal, and eugenol were the least toxic (LC50 > 100 μl/L air). In general, the oxygenated compounds exhibited high contact toxicities while the hydrocarbon compounds exhibited high fumigant toxicities. When tested for their insecticidal activities against S. oryzae in stored wheat, trans-cinnamaldehyde was found to be the most potent compound, with 73.9% mortality at an application rate of 0.5 g/kg and complete mortality (100%) at 1 and 5 g/kg after 1 week of treatment. All of the tested compounds showed AChE inhibition, although (−)-citronellal and trans-cinnamaldehyde presented the strongest enzyme inhibition, with IC50 values of 18.40 and 18.93 mM, respectively. On the other hand, (−)-terpinene-4-ol exhibited the highest inhibition of ATPases, followed by α-pinene and α-terpinene.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  • Abdelgaleil SAM, Mohamed MIE, Badawy MEI, El-arami SAA (2009) Fumigant and contact toxicities of monoterpenes to Sitophilus oryzae (L.) and Tribolium castaneum (Herbst) and their inhibitory effects on acetylcholinesterase activity. J Chem Ecol 35:225–232

    Google Scholar 

  • Abdelgaleil SAM, Mohamed MIE, Shawir MS, Abou-Taleb HK (2016) Insecticidal and biochemical effects of essential oils on the rice weevil, Sitophilus oryzae L. (Coleoptera: Curculionidae). J Pest Sci 89:219–229

    Google Scholar 

  • Abou-Taleb HK, Mohamed MIE, Shawir MS, Abdelgaleil SAM (2016) Insecticidal properties of essential oils against Tribolium castaneum (Herbst) and their inhibitory effects on acetylcholinesterase and adenosine triphosphatases. Nat Prod Res 30:710–714

    CAS  PubMed  Google Scholar 

  • Anderson JA, Coats JR (2012) Acetylcholinesterase inhibition by nootkatone and carvacrol in arthropods. Pestic Biochem Physiol 102:124–128

    CAS  Google Scholar 

  • Brari J, Thakur DR (2015) Fumigant toxicity and cytotoxicity evaluation of monoterpenes against four stored products pests. Int J Develop Res 5:5661–5667

    Google Scholar 

  • Broussalis AM, Ferraro GE, Martino VS, Pinzon R, Coussio JD, Alvarez JC (1999) Argentine plants as potential source of insecticidal compounds. J Ethnopharmacol 67:219–223

    CAS  PubMed  Google Scholar 

  • Busvine JR (1971) A critical review of the techniques for testing insecticides. Commonwealth Agricultural Bureau, London, p 345

  • Cantore PL, Shanmugaiah V, Iacobellis NS (2009) Antibacterial activity of essential oil components and their potential use in seed disinfection. J Agric Food Chem 57:9454–9461

    PubMed  Google Scholar 

  • Cärdenas-Ortega NC, Zavala-Sänchez MA, Aguirre-Rivera JR, Peärez-Gonzälez C, Peärez-Gutienärrez S (2005) Chemical composition and antifungal activity of essential oil of Chrysactinia mexicana Gray. J Agric Food Chem 53:4347–4349

    PubMed  Google Scholar 

  • Chaubey MK (2012) Responses of Tribolium castaneum (Coleoptera: Tenebrionidae) and Sitophilus oryzae (Coleoptera: Curculionidae) against essential oils and pure compounds. Herba Polonica 58:33–45

    CAS  Google Scholar 

  • Cristani M, D’arrigo M, Mandalari G, Castelli F, Sarpietro MG, Micieli D, Venuti V, Bisignano G, Saija A, Trombetta D (2007) Interaction of four monoterpenes contained in essential oils with model membranes: implications for their antibacterial activity. J Agric Food Chem 55:6300–6308

    CAS  PubMed  Google Scholar 

  • Duke SO, Romagni JG, Dayan FE (2000) Natural products as sources for new mechanisms of herbicidal action. Crop Protect 19:583–589

    CAS  Google Scholar 

  • El-arami SAA, Mohamed MIE, Abdelgaleil SAM (2009) Effectiveness of monoterpenes against Sitophilus oryzae (L.) and Tribolium castaneum (Herbst) in stored wheat. J Pest Cont Environ Sci 17:61–76

    Google Scholar 

  • Ellman GL, Courtney KD, Andres V, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–95

    CAS  Google Scholar 

  • Enan EE (2001) Insecticidal activity of essential oils: octopaminergic sites of action. Comp Biochem Physiol 130:325–337

    CAS  Google Scholar 

  • Finney DJ (1971) Probit analysis, 3rd edn. Cambridge University Press, London, p 318

    Google Scholar 

  • Garcia M, Donadel OJ, Ardanaz CE, Tonn CE, Sosa ME (2005) Toxic and repellent effects of Baccharis salicifolia essential oil on Tribulium castaneum. Pest Manag Sci 61:612–618

    CAS  PubMed  Google Scholar 

  • Grodnitzky JA, Coats JR (2002) QSAR evaluation of monoterpenoids’ insecticidal activity. J Agric Food Chem 50:4576–4580

    CAS  PubMed  Google Scholar 

  • Guo Z, Ma Z, Feng J, Zhang X (2009) Inhibition of Na+, K+-ATPase in housefly (Musca domestica L.) by terpinen-4-ol and its ester derivatives. Agric Sci China 8:1492–1497

    Google Scholar 

  • Gupta AK, Behal SR, Awasthi BK, Verma RA (1999) Screening of some maize genotypes against Sitophilus oryzae. Indian J Entomol 61:265–268

    Google Scholar 

  • Huang Y, Lam SL, Ho SH (2000) Bioactivities of essential oil from Elletaria cardamomum (L.) Maton to Sitophilus zeamais Motschulsky and Tribolium castaneum (Herbst). J Stored Prod Res 36:107–117

    CAS  Google Scholar 

  • Isman MB (2000) Plant essential oils for pest and disease management. Crop Protect 19:603–608

    CAS  Google Scholar 

  • Jukic M, Politeo O, Maksimovic M, Milos M, Milos M (2007) In vitro acetylcholinesterase inhibitory properties of thymol, carvacrol and their derivatives thymoquinone and thymohydroquinone. Phytotherapy Res 21:259–261

    CAS  Google Scholar 

  • Kanda D, Kaur S, Koul O (2017) A comparative study of monoterpenoids and phenylpropanoids from essential oils against stored grain insects: acute toxins or feeding deterrents. J Pest Sci 90:531–545. https://doi.org/10.1007/s10340-016-0800-5

    Google Scholar 

  • Kim DH, Ahn YJ (2001) Contact and fumigant activities of constituents of Foeniculum bulgare fruit against three coleopteran stored-product insects. Pest Manag Sci 57:301–306

    CAS  PubMed  Google Scholar 

  • Kim SW, Kang J, Park IK (2013) Fumigant toxicity of Apiaceae essential oils and their constituents against Sitophilus oryzae and their acetylcholinesterase inhibitory activity. J Asia Pac Entomol 16:443–447

    CAS  Google Scholar 

  • Kljajic P, Peric I (2006) Susceptibility to contact insecticides of granary weevil Sitophilus granarius (L.) (Coleoptera: Curculionidae) originating from different locations in the former Yugoslavia. J Stored Prod Res 42:149–161

    CAS  Google Scholar 

  • Koch BR, Laurence CP, Do FM (1969) Chlorinated hydrocarbon insecticide inhibition of cockroach and honey bee ATPase. Life Sci 8:289–297

    CAS  PubMed  Google Scholar 

  • Kohli RK, Batish D, Singh HP (1998) Allelopathy and its implications in agroecosystems. J Crop Prod 1:169–202

    Google Scholar 

  • Kostyukovsky M, Ravid U, Shaaya E (2002) The potential use of plant volatiles for the control of stored product insects and quarantine pests in cut flowers. In: Bernath J, ZamborineNemeth E, Crakerm L, and Kock O (eds) Proceedings of the International Conference on Medicinal and Aromatic Plant Protection in the 21st Century, 8–11 July 2001, Budapest, Hungary (Acta Hortic 576). International Society for Horticultural Science, The Hague, pp 347–358

  • Langenheim JH (1994) Higher plant terpenoids: a phytocentric overview of their ecological roles. J Chem Ecol 20:1223–1279

    CAS  PubMed  Google Scholar 

  • Lee SE, Lee BH, Choi WS, Park BS, Kim JG, Campbell BC (2001a) Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L). Pest Manag Sci 57:548–553

    CAS  PubMed  Google Scholar 

  • Lee BH, Choi WS, Lee SE, Park BS (2001b) Fumigant toxicity of essential oils and their constituent compounds towards the rice weevil, Sitophilus oryzae (L.). Crop Protect 20:317–320

    CAS  Google Scholar 

  • Lee SE, Peterson CJ, Coats JR (2003) Fumigation toxicity of monoterpenoids to several stored-product insects. J Stored Prod Res 39:77–85

    CAS  Google Scholar 

  • Lopez MD, Pascual-Villalobos MJ (2010) Mode of inhibition of acetylcholinesterase by monoterpenoids and implications for pest control. Ind Crops Prod 31:284–288

    CAS  Google Scholar 

  • Nayak MK, Collins PJ, Pavic H (2007) Developing fumigation protocols to manage strongly phosphine-resistant rice weevils, Sitophilus oryzae(L.). In: Donahaye EJ, Navarro S, Bell C, Jayas D, Noyes R, Phillips TW (eds) Proceedings of the International Conference on Controlled Atmosphere and Fumigation in Stored Products, Gold Coast, Australia, 8–13th August 2004. FTIC, Israel, pp 267–273

  • Okunola CO, Ofuya TI (2007) Effect of some essential plant oils on insect infestation of stored maize. Afr Crop Sci Proc 8:1003–1007

    Google Scholar 

  • Park I-K, Lee S-G, Choi D-H, Park J-D, Ahn Y-J (2003) Insecticidal activities of constituents identified in the essential oil from leaves of Chamaecyparis obtuse against Callosobruchus chinensis (L.) and Sitophilus oryzae (L.). J Stored Prod Res 39:375–384

    CAS  Google Scholar 

  • Pasay C, Mounsey K, Stevenson G, Davis R, Arlian L, Morgan M, Vyszenski-Moher D, Andrews K, McCarthy J (2010) Acaricidal activity of eugenol based compounds against scabies mites. PLoS ONE 5:e12079

    PubMed  PubMed Central  Google Scholar 

  • Raguso RA, Pichersky E (1995) Floral volatiles from Clarkia breweri and C. concinna (Onagraceae): recent evolution of floral scent and moth pollination. Plant Syst Evol 194:55–67

    CAS  Google Scholar 

  • Ren YL, Mahona D, Gravera JVS, Head M (2008) Fumigation trial on direct application of liquid carbonyl sulphide to wheat in a 2500 t concrete silo. J Stored Prod Res 44:115–125

    CAS  Google Scholar 

  • Rice PJ, Coats JR (2003) Insecticidal properties of several of several monoterpenoids to the house fly (Diptera: Muscidae), red flour beetle (Coleoptera: Tenebrionidae), and southern maize rootworm (Coleoptera: Chrysomelidae). J Econ Entomol 87:1172–1179

    Google Scholar 

  • Romagni JG, Allen SN, Dayan FE (2000) Allelopathic effects of volatile cineoles on two weedy plant species. J Chem Ecol 26:303–313

    CAS  Google Scholar 

  • Rozman V, Kalinovic I, Korunic Z (2007) Toxicity of naturally occurring compounds of Lamiaceae and Lauraceae to three stored product insects. J Stored Prod Res 43:349–355

    CAS  Google Scholar 

  • Schewe H, Mirata MA, Holtmann D, Schrader J (2011) Biooxidation of monoterpenes with bacterial monooxygenases. Process Biochem 46:1885–1899

    CAS  Google Scholar 

  • Sharma UK, Sood S, Sharma N, Rahi P, Kumar R, Sinha AK, Gulati A (2013) Synthesis and SAR investigation of natural phenylpropene derived methoxylated cinnamaldehydes and their novel Schiff bases as potent antimicrobial and antioxidant agents. Med Chem Res 22:5129–5140

    CAS  Google Scholar 

  • Singh HP, Batish DR, Kohli RK (2002) Allelopathic effect of two volatile monoterpenes against bill goat weed (Ageratum conyzoides L.). Crop Protect 21:347–350

    CAS  Google Scholar 

  • Stuurman J, Hoballah ME, Broger L, Moore J, Basten C, Kuhlemeier C (2004) Dissection of floral pollination syndromes in Petunia. Genetics 168:1585–1599

    CAS  PubMed  PubMed Central  Google Scholar 

  • Taussky HH, Shorr E (1953) A microcolorimetric method for the determination of inorganic phosphorus. J Biol Chem 202:675–685

    CAS  Google Scholar 

  • Templeton W (1969) An introduction to the chemistry of terpenoids and steroids. Butterworths, London

  • Windholz M, Budavari S, Blumetti RF, Otterbein ES (1983) The Merck index. Merck, Rahway

  • Wuryatmo E, Klieber A, Scott ES (2003) Inhibition of citrus postharvest pathogens by vapor of citral and related compounds in culture. J Agric Food Chem 51:2637–2640

    CAS  PubMed  Google Scholar 

  • Yoon C, Kang S-H, Jang S-A, Kim Y-J, Kim G-H (2007) Repellent efficacy of caraway and grapefruit oils for Sitophilus oryzae (Coleoptera: Curculionidae). J Asia Pac Entomol 10:263–267

    CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Alexandria University Research Fund (ALEX-REP, 2010–2013). We thank Eng. Entsar M.A. Sallama for her technical assistance.

Author information

Authors and Affiliations

  1. Department of Pesticide Chemistry and Technology, Faculty of Agriculture, Alexandria University, 21545, El-Shatby, Alexandria, Egypt

    Mona M. G. Saad & Samir A. M. Abdelgaleil

  2. Plant Protection Research Institute, Agricultural Research Center, Sabahia, Alexandria, Egypt

    Hamdy K. Abou-Taleb

Authors
  1. Mona M. G. Saad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hamdy K. Abou-Taleb
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Samir A. M. Abdelgaleil
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Samir A. M. Abdelgaleil.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Saad, M.M.G., Abou-Taleb, H.K. & Abdelgaleil, S.A.M. Insecticidal activities of monoterpenes and phenylpropenes against Sitophilus oryzae and their inhibitory effects on acetylcholinesterase and adenosine triphosphatases. Appl Entomol Zool 53, 173–181 (2018). https://doi.org/10.1007/s13355-017-0532-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13355-017-0532-x

Keywords

Search

Navigation