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Review Articles

Monoterpenes: chemistry, insecticidal activity against stored product insects and modes of action—a review

ORCID Icon, , , &
Pages 267-289 | Received 18 Dec 2020, Accepted 13 Sep 2021, Published online: 27 Sep 2021

References

  • Abdelgaleil SA, Mohamed MI, Badawy ME, El-Arami SA. 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(5):518–525.
  • Abdelgaleil SAM, Badawy MEI, Mahmoud NF, Marei AE. 2019. Acaricidal activity, biochemical effects and molecular docking of some monoterpenes against two-spotted spider mite (Tetranychus urticae Koch). Pestic Biochem Physiol. 156:105–115.
  • Aggarwal KK, Tripathi AK, Ahmad A, Prajapati V, Verma N, Kumar S. 2001. Toxicity of L-menthol and its derivatives against four storage insects. Int J Trop Insect Sci. 21(03):229–235.
  • Ajayi OE, Appel AG, Fadamiro HY. 2014. Fumigation toxicity of essential oil monoterpenes to Callosobruchus maculatus (Coleoptera: Chrysomelidae: Bruchinae). J Insects. 2014:1–7. http://dx.doi.org/10.1155/2014/917212.
  • Al-Nagar NMA, Abou-Taleb HK, Shawir MS, Abdelgaleil SAM. 2020. Comparative toxicity, growth inhibitory and biochemical effects of terpenes and phenylpropenes on Spodoptera littoralis (Boisd.). J Asia Pac Entomol. 23(1):67–75.
  • Anderson JA, Coats JR. 2012. Acetylcholinesterase inhibition by nootkatone and carvacrol in arthropods. Pestic Biochem Physiol. 102(2):124–128.
  • Bakkali F, Averbeck S, Averbeck D, Idaomar M. 2008. Biological effects of essential oils - a review. Food Chem Toxicol. 46(2):446–475.
  • Baldwin IT, Halitschke R, Paschold A, von Dahl CC, Preston CA. 2006. Volatile signaling in plant-plant interactions: “Talking trees” in the genomics era. Science. 311(5762):812–815.
  • Bedini S, Bougherra HH, Flamini G, Cosci F, Belhamel K, Ascrizzi R, Conti B. 2016. Repellency of anethole-and estragole-type fennel essential oils against stored grain pests: the different twins. Bull Insectol. 69:149–157.
  • Bhavaniramya S, Vishnupriya S, Al-Aboody MS, Vijayakumar R, Baskaran D. 2019. Role of essential oils in food safety: antimicrobial and antioxidant applications. Grain Oil Sci Technol. 2(2):49–55.
  • Brari J, Thakur DR. 2015. Fumigant toxicity and cytotoxicity evaluation of monoterpenes against four stored products pests. Int J Dev Res. 5:5661–5667.
  • Brari J, Thakur DR. 2016. Insecticidal potential properties of citronellol derived ionic liquid against two major stored grain insect pests. J Entomol Zool Stud. 4:365–370.
  • Cantrell CL, Dayan FE, Duke SO. 2012. Natural products as sources for new pesticides. J Nat Prod. 75(6):1231–1242.
  • Cao JQ, Guo SS, Wang Y, Pang X, Geng ZF, Du SS. 2018. Toxicity and repellency of essential oil from Evodia lenticellata Huang fruits and its major monoterpenes against three stored-product insects. Ecotoxicol Environ Saf. 160:342–348.
  • Caputi L, Aprea E. 2011. Use of terpenoids as natural flavouring compounds in food industry. Recent Pat Food Nutr Agric. 3(1):9–16.
  • Casida JE, Durkin KA. 2013. Neuroactive insecticides: targets, selectivity, resistance, and secondary effects. Annu Rev Entomol. 58:99–117.
  • Céspedes CL, Alarcón J, Aranda E, Becerra J, Silva M. 2001. Insect growth regulator and insecticidal activity of beta-dihydroagarofurans from Maytenus spp. (Celastraceae). Z Naturforsch C J Biosci. 56(7-8):603–613.
  • Chaubey MK. 2012. Responses of Tribolium castaneum (Coleoptera: Tenebrionidae) and Sitophilus oryzae (Coleoptera: Curculionidae) against essential oils and pure compounds. Herba Pol. 58:33–45.
  • Chaubey MK. 2015. Biological activities of terpenes against pulse beetle, Callosobruchus chinensis (Coleoptera: Bruchidae). Entomol Appl Sci Lett. 2:50–61.
  • Chen J, Lu M, Jing Y, Dong J. 2006. The synthesis of L-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells. Bioorg Med Chem. 14(19):6539–6547.
  • Chen Z-y, Guo S-s, Cao J-q, Pang X, Geng Z-f, Wang Y, Zhang Z, Du S-s. 2018. Insecticidal and repellent activity of essential oil from Amomum villosum Lour. and its main compounds against two stored-product insects. Int J Food Prop. 21(1):2265–2275.
  • Chu S, Wang CF, Du SS, Liu SL, Liu ZL. 2011. Toxicity of the essential oil of Illicium difengpi stem bark and its constituent compounds towards two grain storage insects. J Insect Sci. 11:152.
  • Crowell PL. 1999. Prevention and therapy of cancer by dietary monoterpenes. J Nutr. 129(3):775S–778S.
  • Czaja K, Góralczyk K, Struciński P, Hernik A, Korcz W, Minorczyk M, Łyczewska M, Ludwicki JK. 2015. Biopesticides-towards increased consumer safety in the European Union. Pest Manag Sci. 71(1):3–6.
  • Davoudi A, Shayesteh N, Shirdel D, Hosseinzadeh A. 2011. Effect of diethyl maleate on toxicity of linalool against two stored product insects in laboratory condition. Afr J Biotechnol. 10:9918–9921.
  • Dayan FE, Cantrell CL, Duke SO. 2009. Natural products in crop protection. Bioorg Med Chem. 17(12):4022–4034.
  • Dohi S, Terasaki M, Makino M. 2009. Acetylcholinesterase Inhibitory activity and chemical composition of commercial essential oils. J Agric Food Chem. 57(10):4313–4318.
  • Dudareva N, Klempien A, Muhlemann K, Kaplan I. 2013. Biosynthesis, function and metabolic engineering of plant volatile organic compounds. New Phytol. 198(1):16–32.
  • Elgizawy KKH, El-Shewy AM, Morsy AR. 2019. Evaluation of essential oil and its main active ingredients of Chinese Litsea cubeba against two stored-grain insects. Acad J Entomol. 12:29–39.
  • Enan E. 2001. Insecticidal activity of essential oils: octopaminergic sites of action. Comp Biochem Physiol C Toxicol Pharmacol. 130(3):325–337.
  • Enan E. 2005a. Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils. Arch Insect Biochem Physiol. 59(3):161–171.
  • Enan E. 2005b. Molecular response of Drosophila melanogaster tyramine receptor cascade to plant essential oils. Insect Biochem Mol Biol. 35(4):309–321.
  • Erler F. 2005. Fumigant activity of six monoterpenoids from aromatic plants in Turkey against the two stored-product pests confused flour beetle, Tribolium confusum, and Mediterranean flour moth, Ephestia kuehniella. J Plant Dis Prot. 112(6):602–611.
  • Gangwar P, Tiwari SN, 2017. Insecticidal activity of Curcuma longa essential oil and its fractions against Sitophilus oryzae L. and Rhyzopertha dominica F. (Coleoptera). Int J Pure App Biosci. 5(3):912–921.
  • Gonzalez AG, Jimenez IA, Ravelo AG, Coll J, Gonzalez JA, Lloria J. 1997. Antifeedant activity of sesquiterpene from celastraceae. Biochem Syst Ecol. 25(6):513–519.
  • Gross AD, Temeyer KB, Day TA, de León A, Kimber MJ, Coats JR. 2017. Interaction of plant essential oil terpenoids with the southern cattle tick tyramine receptor: a potential biopesticide target. Chem Biol Interact. 263:1–6.
  • Guo S, Zhang W, Liang J, You C, Geng Z, Wang C, Du S. 2016. Contact and repellent activities of the essential oil from Juniperus formosana against two stored product insects. Molecules. 21(4):504.
  • Hernández-Carlos B, Gamboa-Angulo M. 2019. Insecticidal and nematicidal contributions of Mexican flora in the search for safer biopesticides. Molecules. 24:897–940.
  • Houghton PJ, Ren Y, Howes MJ. 2006. Acetylcholinesterase inhibitors from plants and fungi. Nat Prod Rep. 23(2):181–199.
  • Hu D, Coats J. 2008. Evaluation of the environmental fate of thymol and phenethyl propionate in the laboratory. Pest Manag Sci. 64(7):775–779.
  • Isman MB, Miresmailli S, Machial C. 2011. Commercial opportunities for pesticides based on plant essential oils in agriculture, industry and consumer products. Phytochem Rev. 10(2):197–204.
  • Isman MB, Tak J-H. 2017. Inhibition of acetylcholinesterase by essential oils and monoterpenoids: a relevant mode of action for insecticidal essential oils? Biopestic Int. 13:71–78.
  • Isman MB. 2000. Plant essential oils for pest and disease management. Crop Prot. 19(8–10):603–608.
  • Isman MB. 2006. Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Annu Rev Entomol. 51(1):45–66.
  • Isman MB. 2008. Botanical insecticides: for richer, for poorer. Pest Manag Sci. 64(1):8–11.
  • Isman MB. 2015. A renaissance for botanical insecticides? Pest Manag Sci. 71(12):1587–1590.
  • Isman MB. 2016. Pesticides based on plant essential oils: phytochemical and practical considerations. In: Jeliazkov (Zheljazkov) VD, Cantrell CL, editors. Medicinal and aromatic crops: production, phytochemistry, and utilization. ACS Symposium Series. Washington: American Chemical Society.
  • Kamatou GPP, Vermaak I, Viljoen AM, Lawrence BM. 2013. Menthol: a simple monoterpene with remarkable biological properties. Phytochemistry. 96:15–25.
  • Kamatou GPP, Viljoen AM. 2008. Linalool - a review of a biologically active compound of commercial importance. Nat Prod Commun. 3:1183–1192.
  • 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(2):531–545.
  • Kang JS, Eunae K, Lee SH, Park K. 2013. Inhibition of acetylcholinesterases of the pinewood nematode, Bursaphelenchus xylophilus, by phytochemicals from plant essential oils. Pestic Biochem Physiol. 105(1):50–56.
  • Khanikor B, Parida P, Yadav RNS, Bora D. 2013. Comparative mode of action of some terpene compounds against octopamine receptor and acetyl cholinesterase of mosquito and human system by the help of homology modeling and Docking studies. J Appl Pharm Sci. 3:6–12.
  • Kim S-I, Lee D-W. 2014. Toxicity of basil and orange essential oils and their components against two coleopteran stored products insect pests. J Asia Pac Entomol. 17(1):13–17.
  • 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(4):443–447.
  • Kordali Ş, Usanmaz A, Bayrak N, Çakır A. 2017. Fumigation of volatile monoterpenes and aromatic compounds against adults of Sitophilus granarius (L.) (Coleoptera: Curculionidae). Rec Nat Prod. 11:362–373.
  • Koul O, Walia S, Dhaliwal GS. 2008. Essential oils as green pesticides: potential and constraints. Biopest Int. 4:63–84.
  • Kumrungsee N, Pluempanupat W, Koul O, Bullangpoti V. 2014. Toxicity of essential oil compounds against diamondback moth, Plutella xylostella, and their impact on detoxification enzyme activities. J Pest Sci. 87(4):721–729.
  • Lee S, Peterson CJ, Coats JR. 2003. Fumigation toxicity of monoterpenoids to several stored product insects. J Stored Prod Res. 39(1):77–85.
  • Lee SE, Lee BH, Choi WS, Park BS, Kim JG, Campbell BC. 2001. Fumigant toxicity of volatile natural products from Korean spices and medicinal plants towards the rice weevil, Sitophilus oryzae (L). Pest Manag Sci. 57(6):548–553.
  • Liang JY, Guo SS, Zhang WJ, Geng ZF, Deng ZW, Du SS, Zhang J. 2018. Fumigant and repellent activities of essential oil extracted from Artemisia dubia and its main compounds against two stored product pests. Nat Prod Res. 32(10):1234–1238.
  • Liao M, Xiao J-J, Zhou L-J, Liu Y, Wu X-W, Hua R-M, Wang G-R, Cao H-Q. 2016. Insecticidal activity of Melaleuca alternifolia essential oil and RNA-Seq analysis of Sitophilus zeamais transcriptome in response to oil fumigation. PLoS One. 11(12):e0167748.
  • Librowski T. 2005. Analgesic and anti-inflammatory activity of stereoisomers of carane derivatives in rodent test. Pharmacol Rep. 57(6):802–810.
  • Librowski T, Moniczewski A. 2010. Strong antioxidant activity of carane derivatives. Pharmacol Rep. 62(1):178–184.
  • Liška A, Rozman V, Kalinović I, Ivezić M, Baličević R. 2010. Contact and fumigant activity of 1,8-cineole, eugenol and camphor against Tribolium castaneum (Herbst). Proceedings of the 10th International Working Conference on Stored Product Protection, 27 June to 2 July 2010, Estoril, Portugal. Julius Kühn-Institut, Berlin, Germany, p. 716–720.
  • Liu ZL, Chu SS, Jiang GH. 2011. Toxicity of Schizonpeta multifida essential oil and its constituent compounds towards two grain storage insects. J Sci Food Agric. 91(5):905–909.
  • López M, Pascual-Villalobos M. 2010. Mode of inhibition of acetylcholinesterase by monoterpenoids and implications for pest control. Ind Crops Prod. 31(2):284–288.
  • López M, Pascual-Villalobos M. 2015. Are monoterpenoids and phenylpropanoids efficient inhibitors of acetylcholinesterase from stored product insect strains? Flavour Fragr J. 30(1):108–112.
  • López V, Cascella M, Benelli G, Maggi F, Gómez-Rincón C. 2018. Green drugs in the fight against Anisakis simplex-larvicidal activity and acetylcholinesterase inhibition of Origanum compactum essential oil. Parasitol Res. 117(3):861–867.
  • Naigre R, Kalck P, Roques C, Roux I, Michel G. 1996. Comparison of antimicrobial properties of monoterpenes and their carbonylated products. Planta Med. 62(3):275–277.
  • Obeng-Ofori D, Reichmuth CH. 1999. Plant oils as potentiation agents of monoterpenes for protection of stored grains against damage by stored product beetle pests. Int J Pest Manag. 45(2):155–159.
  • Pajaro-Castro N, Caballero-Gallardo K, Olivero-Verbel J. 2017. Neurotoxic Effects of Linalool and β-pinene on Tribolium castaneum Herbst. Molecules. 22:2052.
  • Park CG, Jang M, Yoon KA, Kim J. 2016. Insecticidal and acetylcholinesterase inhibitory activities of Lamiaceae plant essential oils and their major components against Drosophila suzukii (Diptera: Drosophilidae). Ind Crops Prod. 89:507–513.
  • Park JH, Lee HS. 2018. Toxicities of Eucalyptus dives oil, 3-carvomenthenone, and its analogues against stored-product insects. J Food Prot. 81(4):653–658.
  • Park YL, Tak JH. 2016. Essential oils for arthropod pest management in agricultural production systems, essential oils in food preservation. In Essential oils in food preservation, flavor and safety. Academic Press, UK. p. 61–70.
  • Pavela R, Benelli G. 2016. Essential oils as ecofriendly biopesticides? Challenges and constraints. Trends Plant Sci. 21(12):1000–1007.
  • Pavela R. 2016. History, presence and perspective of using plant extracts as commercial botanical insecticides and farm products for protection against insects–a review. Plant Prot Sci. 52:229–241.
  • Peixoto MG, Bacci L, Blank AF, Araújo APA, Alves PB, Silva JHS, Santos AA, Oliveira AP, da Costa AS, Arrigoni-Blank MF. 2015. Toxicity and repellency of essential oils of Lippia alba chemotypes and their major monoterpenes against stored grain insects. Ind Crops Prod. 71:31–36.
  • Picollo MI, Toloza AC, Mougabure CG, Zygadlo J, Zerba E. 2008. Anticholinesterase and pediculicidal activities of monoterpenoids. Fitoterapia. 79(4):271–278.
  • Pillmoor J, Wright K, Terry A. 1993. Natural products as a source of agrochemicals and leads for chemical synthesis. Pestic Sci. 39(2):131–140.
  • Priestley CM, Williamson EM, Wafford KA, Sattelle DB. 2003. Thymol, a constituent of thyme essential oil, is a positive allosteric modulator of human GABA(A) receptors and a homo-oligomeric GABA receptor from Drosophila melanogaster. Br J Pharmacol. 140(8):1363–1372.
  • Quan M, Liu QZ, Liu ZL. 2018. Identification of insecticidal constituents from the essential oil from the aerial parts Stachysriederi var. japonica. Molecules. 23:1200.
  • Raguso RA. 2008. Wake up and smell the roses: the ecology and evolution of floral scent. Annu Rev Ecol Evol Syst. 39(1):549–569. ‏
  • Rajendran S, Sriranjini V. 2008. Plant products as fumigant for stored product insect control. J Stored Prod Res. 44(2):126–135.
  • Rajkumar V, Gunasekaran C, Christy IK, Dharmaraj J, Chinnaraj P, Paul CA. 2019. Toxicity, antifeedant and biochemical efficacy of Mentha piperita L. essential oil and their major constituents against stored grain pest. Pestic Biochem Physiol. 156:138–144.
  • Ramadan GRM, Abdelgaleil SAM, Shawir MS, El-Bakary AS, Zhu KY, Phillips TW. 2020. Terpenoids, DEET and short chain fatty acids as toxicants and repellents for Rhyzopertha dominica (coleoptera: Bostrichidae) and Lasioderma serricorne (Coleoptera: Ptinidae). J Stored Prod Res. 87: 101610.
  • Reis SL, Mantello AG, Macedo JM, Gelfuso EA, da Silva CP, Fachin AL, Cardoso AM, Beleboni RO. 2016. Typical monoterpenes as insecticides and repellents against stored grain pests. Molecules. 21(3):258.
  • Rizvi SAH, Ling S, Tian F, Xie F, Zeng X. 2018. Toxicity and enzyme inhibition activities of the essential oil and dominant constituents derived from Artemisia absinthium L. against adult Asian citrus psyllid Diaphorinacitri kuwayama (Hemiptera: psyllidae). Ind Crops Prod. 121:468–475.
  • Rosa JS, Oliveira L, Sousa R, Escobar CB, Fernandes-Ferreira M. 2020. Bioactivity of some Apiaceae essential oils and their constituents against Sitophilus zeamais (Coleoptera: Curculionidae). Bull Entomol Res. 110(3):406–416.
  • 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(4):349–355.
  • Saad MMG, Abdelgaleil SAM. 2018. Effectiveness of monoterpenes and phenylpropenes on Sitophilus oryzae L.(Coleoptera: Curculionidae) in stored wheat. J Asia Pac Entomol. 21(4):1153–1158.
  • Saad MMG, Abou-Taleb HK, Abdelgaleil SAM. 2018. Insecticidal activities of monoterpenes and phenylpropenes against Sitophilus oryzae and their inhibitory effects on acetylcholinesterase and adenosine triphosphatases. Appl Entomol Zool. 53(2):173–181.
  • Saad MMG, El-Deeb DA, Abdelgaleil SAM. 2019. Insecticidal potential and repellent and biochemical effects of phenylpropenes and monoterpenes on the red flour beetle, Tribolium castaneum Herbst. Environ Sci Pollut Res Int. 26(7):6801–6810.
  • Seigler DS. 1998. Plant secondary metabolism. Boston: Kluwer Academic Publishers. p. 324–352.
  • Seo SM, Jung CS, Kang J, Lee HR, Kim SW, Hyun J, Park IK. 2015. Larvicidal and acetylcholinesterase inhibitory activities of apiaceae plant essential oils and their constituents against Aedes albopictus and formulation development. J Agric Food Chem. 63(45):9977–9986.
  • Shaaya E, Kostyukovysky M. 2006. Essential oils: potency against stored product insects and mode of action. Stewart Postharvest Rev. 4:1–6.
  • Shahriari M, Sahebzadeh N, Sarabandi M, Zibaee A. 2016. Oral toxicity of thymol, α-pinene, diallyl disulfide and trans-anethole, and their binary mixtures against Tribolium castaneum Herbst larvae (Coleoptera: Tenebrionidae). Jordan J Biol Sci. 9:213–219.
  • Shahriari M, Zibaee A, Sahebzadeh N, Shamakhi L. 2018. Effects of α-pinene, trans-anethole, and thymol as the essential oil constituents on antioxidant system and acetylcholine esterase of Ephestia kuehniella Zeller (Lepidoptera: Pyralidae). Pestic Biochem Physiol. 150:40–47.
  • Siegfried BD, Scott SC. 1992. Biochemical characterization of hydrolytic and oxidative enzymes in insecticide resistant and susceptible strains of the German cockroach (Dictyoptera: Blattellidae). J Econ Entomol. 85(4):1092–1098.
  • Singh B, Sharma RA. 2015. Plant terpenes: defense responses, phylogenetic analysis, regulation and clinical applications. 3 Biotech. 5(2):129–151.
  • Suthisut D, Fields PG, Chandrapatya A. 2011. Fumigant toxicity of essential oils from three Thai plants (Zingiberaceae) and their major compounds against Sitophilus zeamais, Tribolium castaneum and two parasitoids. J Stored Prod Res. 47(3):222–230.
  • Taktak NEM, Badawy MEI. 2019. Potential of hydrocarbon and oxygenated monoterpenes against Culex pipiens larvae: toxicity, biochemical, pharmacophore modeling and molecular docking studies. Pestic Biochem Physiol. 158:156–165.
  • Tayoub G, Alorfi M, Ismail H. 2016. Fumigant toxicities of essential oils and two monoterpenes against potato tuber moth (Phthorimaea operculella Zeller). Herba Pol. 62(4):82–96.
  • Tong F, Coats JR. 2010. Effects of monoterpenoid insecticides on [3H]-TBOB binding in house fly GABA receptor and 36Cl uptake in American cockroach ventral nerve cord. Pestic Biochem Physiol. 98(3):317–324.
  • Tong F, Gross AD, Dolan MC, Coats JR. 2013. The phenolic monoterpenoid carvacrol inhibits the binding of nicotine to the housefly nicotinic acetylcholine receptor. Pest Manag Sci. 69(7):775–780.
  • Tripathi AK, Prajapati V, Aggarwal KK, Kumar S. 2001. Toxicity, feeding deterrence, and effect of activity of 1, 8-cineole from Artemisia annua on progeny production of Tribolium castanaeum (Coleoptera: Tenebrionidae). J Econ Entomol. 94(4):979–983.
  • Tripathi AK, Prajapati V, Khanuja SPS, Kumar S. 2003. Effect of d-limonene on three stored-product beetles. J Econ Entomol. 96(3):990–995.
  • Unsicker SB, Kunert G, Gershenzon J. 2009. Protective perfumes: the role of vegetative volatiles in plant defense against herbivores. Curr Opin Plant Biol. 12(4):479–485.
  • Van Leeuwen T, Vontas J, Tsagkarakou A, Dermauw W, Tirry L. 2010. Acaricide resistance mechanisms in the two-spotted spider mite Tetranychus urticae and other important Acari: a review. Insect Biochem Mol Biol. 40(8):563–572.
  • Wahba TF, Mackled MI, Selim S, El-Zemity SR. 2018. Toxicity and reproduction inhibitory effects of some monoterpenes against the cowpea weevil Callosobruchus maculatus F. (Coleoptera: Chrysomelidae: Bruchinae). Middle East J Appl Sci. 8:1061–1070.
  • Wang JL, Li Y, Lei CL. 2009. Evaluation of monoterpenes for the control of Tribolium castaneum (Herbst) and Sitophilus zeamaise Motschulsky. Nat Prod Res. 23(12):1080–1088.
  • Wang Y, You C-X, Wang C-F, Yang K, Chen R, Zhang W-J, Du S-S, Geng Z-F, Deng Z-W. 2014. Chemical constituents and insecticidal activities of the essential oil from Amomum tsaoko against two stored-product insects. J Oleo Sci. 63(10):1019–1026.
  • Wang Y, Zhang L-T, Feng Y-X, Guo S-S, Pang X, Zhang D, Geng Z-F, Du S-S. 2019. Insecticidal and repellent efficacy against stored-product insects of oxygenated monoterpenes and 2-dodecanone of the essential oil from Zanthoxylum planispinum var. dintanensis. Environ Sci Pollut Res Int. 26(24):24988–24997. ‏
  • Watanabe Y, Mihara R, Mitsunaga T, Yoshimura T. 2005. Termite repellent sesquiterpenoids from Callitris glaucophylla heartwood. Forest Ecol Manag. 258:1918–1923.
  • Wei XM, Guo SS, Yan H, Cheng XL, Wei F, Du SS. 2018. Contact toxicity and repellency of the essential oil from Bupleurum bicaule helm against two stored product insects. J Chem. 2018:1–8.
  • Worth H, Schacher C, Dethlefsen U. 2009. Concomitant therapy with cineole (eucalyptole) reduces exacerbations in COPD: a placebo-controlled double-blind trial. Respir Res. 10:69.
  • Wu H-b, Wu H-b, Wang W-s, Liu T-t, Qi M-g, Feng J-c, Li X-y, Liu Y. 2016. Insecticidal activity of sesquiterpene lactones and monoterpenoid from the fruits of Carpesium abrotanoides. Ind Crops Prod. 92:77–83.
  • Yeom HJ, Kang JS, Kim GH, Park IK. 2012. Insecticidal and acetylcholine esterase inhibition activity of Apiaceae plant essential oils and their constituents against adults of German cockroach (Blattella germanica). J Agric Food Chem. 60(29):7194–7203.
  • Yildirim E, Emsen B, Kordali S. 2013. Insecticidal effects of monoterpenes on Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae). J Appl Bot Food Qual. 86:198–204.
  • You CX, Jiang HY, Zhang WJ, Guo SS, Yang K, Lei N, Ma P, Geng ZF, Du SS. 2015. Contact toxicity and repellency of the main components from the essential oil of Clausena anisum-olens against two stored product insects. J Insect Sci. 15:87.
  • Zahran HEH, Abdelgaleil SAM. 2011. Insecticidal and developmental inhibitory properties of monoterpenes on Culex pipiens L. (Diptera:Culicidae). J Asia Pac Entomol. 14(1):46–51.
  • Zarrad K, Hamouda AB, Chaieb I, Laarif AB, Jemâa JM. 2015. Chemical composition, fumigant and anti-acetylcholinesterase activity of the Tunisian Citrus aurantium L. essential oils. Ind Crops Prod. 76:121–127.

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