Abstract
Plant volatilomics such as essential oils (EOs) and volatile phytochemicals (PCs) are known as potential natural sources for the development of biofumigants as an alternative to conventional fumigant pesticides. This present work was aimed to evaluate the fumigant toxic effect of five selected EOs (cinnamon, garlic, lemon, orange, and peppermint) and PCs (citronellol, limonene, linalool, piperitone, and terpineol) against the Callosobruchus maculatus, Sitophilus oryzae, and Tribolium castaneum adults. Furthermore, for the estimation of the relationship between molecular descriptors and fumigant toxicity of plant volatiles, quantitative structural activity relationship (QSAR) models were developed using principal component analysis and multiple linear regression. Amongst the tested EOs, garlic EO was found to be the most toxic fumigant. The PCs toxicity analysis revealed that terpineol, limonene, linalool, and piperitone as potential fumigants to C. maculatus (< 20 µL/L air of LC50), limonene and piperitone as potential fumigants to T. castaneum (14.35 and 154.11 µL/L air of LC50, respectively), and linalool and piperitone as potential fumigants to S. oryzae (192.27 and 69.10 µL/L air of LC50, respectively). QSAR analysis demonstrated the role of various molecular descriptors of EOs and PCs on the fumigant toxicity in insect pest species. In specific, dipole and Randic index influence the toxicity in C. maculatus, molecular weight and maximal projection area influence the toxicity in S. oryzae, and boiling point and Dreiding energy influence the toxicity in T. castaneum. The present findings may provide insight of a new strategy to select effective EOs and/or PCs against stored product insect pests.
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Data availability
The datasets used in the current study are available upon reasonable request from the corresponding author.
References
Abbott WS (1925) The value of the dry substitutes for liquid lime. J Eco Entomol 18:265–267
Abdalla MI, Abdelbagi AO, Hammad AMA, Laing MD (2017) Use of volatile oils of garlic to control the cowpea weevil Callosobruchus maculatus (Bruchidae: Coleoptera). S Afr J Plant Soil 34(3):185–190. https://doi.org/10.1080/02571862.2016.1225232
Abdelgaleil SAM, Badawy MEI, Mohamed MIE, Mohamed S (2012) Chemical composition and fumigant toxicity of essential oils isolated from Egyptian plants against stored product insects Sitophilus oryzae (L.) and Tribolium castaneum (Herbst). In: Navarro S, Banks HJ, Jayas DS, Bell CH, Noyes RT, Ferizli AG, Emekci M, Isikber AA, Alagusundaram K (eds) Proceedings of 9th International Conference on Controlled Atmosphere and Fumigation in Stored Products, Antalya, Turkey. 15-19 October 2012. ARBER Professional Congress Services, Turkey, pp 50–57
Bincy K, Remesh AV, Prabhakar PR, Vivek Babu CS (2023) Chemical composition and insecticidal activity of Ocimum basilicum (Lamiaceae) essential oil and its major constituent, estragole against Sitophilus oryzae (Coleoptera: Curculionidae). J Plant Dis Prot 130(3):529–541. https://doi.org/10.1007/s41348-022-00695-4
Bond EJ, Monro HAU, Buckland CT (1967) The influence of oxygen on the toxicity of fumigants to Sitophilus granarius (L). J Stored Prod Res 3(4):289–294. https://doi.org/10.1016/0022-474X(67)90032-X
Bossou AD, Ahoussi E, Ruysbergh E, Adams A, Smagghe G, De Kimpe N, Avlessi F, Sohounhloue DCK, Mangelinckx S (2015) Characterization of volatile compounds from three Cymbopogon species and Eucalyptus citriodora from Benin and their insecticidal activities against Tribolium castaneum. Ind Crops Prod 76:306–317. https://doi.org/10.1016/j.indcrop.2015.06.031
Brari J, Kumar V (2020) Insecticidal potential of two monoterpenes against Tribolium Castaneum (Herbst.) and Sitophilus oryzae (L.) major stored product insect pests. Int J Pharm Biol Arch 11(4):175–181
Brari J, Thakur DR (2015) Insecticidal efficacy of essential oil from Cinnamomum zeylanicum Blume and its two major constituents against Callosobruchus maculatus (F.) and Sitophilus oryzae (L.). J Agric Technol 11(6):1323–1336
Central Insecticide Board and Registration Committee (CIBRC) (2022) Insecticides / Pesticides Registered under section 9(3) of the Insecticides Act, 1968 for use in the Country. http://ppqs.gov.in/sites/default/files/molecules_registered_under_section-93_as_on_01.07.2022.pdf. Accessed on 22 September 2022
Chaubey MK (2016) Fumigant and contact toxicity of Allium sativum (Alliaceae) essential oil against Sitophilus oryzae L. (Coleoptera: Dryophthoridae). Entomol Appl Sci Lett 3(2):43–48
Chen J, Jiang QD, Chai YP, Zhang H, Peng P, Yang XX (2016) Natural terpenes as penetration enhancers for transdermal drug delivery. Molecules 21(12):1709. https://doi.org/10.3390/molecules21121709
Chowdhury P (2021) In silico investigation of phytoconstituents from Indian medicinal herb ‘Tinospora cordifolia (giloy)’ against SARS-CoV-2 (COVID-19) by molecular dynamics approach. J Biomol Struct Dyn 39(17):6792–6809. https://doi.org/10.1080/07391102.2020.1803968
Comelli NC, Romero OE, Diez PA, Marinho CF, Schliserman P, Carrizo A, Ortiz EV, Duchowicz PR (2018) QSAR Study of biologically active essential oils against beetles infesting the walnut in Catamarca, Argentina. J Agric Food Chem 66(48):12855–12865. https://doi.org/10.1021/acs.jafc.8b04161
Davoudi A, Shayesteh N, Shirdel D, Hosseinzadeh A (2013) Effect of diethyl maleate on toxicity of linalool against two stored product insects in laboratory condition. Afr J Biotechnol 10(48):9918–9921. https://doi.org/10.5897/ajb11.1039
de Andrade Rodrigues RMB, da Silva Fontes L, de Carvalho Brito R, Barbosa DRES, das Graças Lopes Citó AM, do Carmo IS, de Jesus Sousa EM, Silva GN (2022) A sustainable approach in the management of Callosobruchus maculatus: essential oil of Protium heptaphyllum and its major compound d-limonene as biopesticides. J Plant Dis Prot 129(4):831–841. https://doi.org/10.1007/s41348-022-00617-4
Eddy NO (2020) Theoretical chemistry study on the toxicity of some polychlorobiphenyl (PCB) compounds using molecular descriptors. Sci Afr 10:e00587. https://doi.org/10.1016/j.sciaf.2020.e00587
El Nagar TFK, Fattah HMA, Khaled AS, Aly SA (2012) Efficiency of peppermint oil fumigant on controlling Callosobruchus maculatus F. infesting cowpea seeds. Life Sci J 9(2):337–383
Eljazi JS, Bachrouch O, Salem N, Msaada K, Aouini J, Hammami M, Boushih E, Abderraba M, Limam F, Jemaa JMB (2018) Chemical composition and insecticidal activity of essential oil from coriander fruit against Tribolium castaenum, Sitophilus oryzae, and Lasioderma serricorne. Int J Food Prop 20(3):S2833–S2845. https://doi.org/10.1080/10942912.2017.1381112
El-Sabrout AM, Salem MZ, Bin-Jumah M, Allam AA (2019) Toxicological activity of some plant essential oils against Tribolium castaneum and Culex pipiens larvae. Processes 7(12):933. https://doi.org/10.3390/pr7120933
Enan EE (2005) 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. https://doi.org/10.1002/arch.20076
Finney DJ (1971) Probit analysis. The University Press, Cambridge
Gallucci MN, Carezzano ME, Oliva MM, Demo MS, Pizzolitto RP, Zunino MP, Zygadlo JA, Dambolena JS (2014) In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure–activity relationship analysis. J Appl Microbiol 116(4):795–804. https://doi.org/10.1111/jam.12432
Gehring PJ, Nolan RJ, Watanabe PG, Schumann AM (1991) Solvents, fumigants and related compounds. In: Hayes WJ, Laws ER (eds) Handbook of Pesticide Toxicology, vol 2. Academic Press San Diego, California, pp 668–671
Ghasemi G, Arshadi S, Rashtehroodi AN, Nirouei M, Shariati S, Rastgoo Z (2013) QSAR investigation on quinolizidinyl derivatives in Alzheimer’s disease. J Computational Med 312728. https://doi.org/10.1155/2013/312728
Hammoudan I, Matchi S, Bakhouch M, Belaidi S, Chtita S (2021) QSAR modelling of peptidomimetic derivatives towards HKU4-CoV 3CLpro inhibitors against MERS-CoV. Chemistry 3(1):391–401. https://doi.org/10.3390/chemistry3010029
Hikal WM, Baeshen RS, Ahl HAHS (2017) Botanical insecticide as simple extractives for pest control. Cogent Biol 3:1404274. https://doi.org/10.1080/23312025.2017.1404274
Homayouni A, Azizi A, Keshtiban AK, Amini A, Eslami A (2015) Date canning: a new approach for the long time preservation of date. J Food Sci Technol 52(4):1872–1880. https://doi.org/10.1007/2Fs13197-014-1291-0
Ibrahim SS, Sahu U, Karthik P, Vendan SE (2023) Eugenol nanoemulsion as bio-fumigant: enhanced insecticidal activity against the rice weevil, Sitophilus oryzae adults. J Food Sci Technol 60(4):1435–1445. https://doi.org/10.1007/s13197-023-05690-7
Isman MB, Grieneisen ML (2014) Botanical insecticide research: many publications, limited useful data. Trends Plant Sci 19(3):140–145. https://doi.org/10.1016/j.tplants.2013.11.005
Jayaram CS, Chauhan N, Dolma SK, Reddy SE (2022) Chemical composition and insecticidal activities of essential oils against the pulse beetle. Molecules 27(2):568. https://doi.org/10.3390/2Fmolecules27020568
Jiang Z, Kempinski C, Chappell J (2016) Extraction and analysis of terpenes/terpenoids. Curr Protoc Plant Biol 1(2):345–358. https://doi.org/10.1002/cppb.20024
Karabörklü S, Ayvaz A (2023) A comprehensive review of effective essential oil components in stored-product pest management. J Plant Dis Prot 130:449–481
Kathirvelu C, Maline AS, Raja BAG, Kavitha T (2020) Effect of fumigation on Rhyzopertha dominica F. and Tribolium castaneum H. in stored products using essential oils. Ann Agri-Bio Res 25(2):258–262
Ketoh GK, Koumaglo HK, Glitho IA, Huignard J (2006) Comparative effects of Cymbopogon schoenanthus essential oil and piperitone on Callosobruchus maculatus development. Fitoterapia 77:506–510. https://doi.org/10.1016/j.fitote.2006.05.031
Lashgari A, Mashayekhi S, Javadzadeh M, Marzban R (2014) Effect of Mentha piperita and Cuminum cyminum essential oil on Tribolium castaneum and Sitophilus oryzae. Arch Phytopathol Plant Prot 47(3):324–329. https://doi.org/10.1080/03235408.2013.809230
Lee EJ, Kim JR, Choi DR, Ahn YJ (2008) Toxicity of cassia and cinnamon oil compounds and cinnamaldehyde-related compounds to Sitophilus oryzae (Coleoptera: Curculionidae). J Econ Entomol 101(6):1960–1966. https://doi.org/10.1603/0022-0493-101.6.1960
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. https://doi.org/10.1080/14786419.2017.1331227
Liang J, Ning A, Lu P, An Y, Wang Z, Zhang J, He C, Wang Y (2021) Biological activities and synergistic effects of Elsholtzia stauntoni essential oil from flowers and leaves and their major constituents against Tribolium castaneum. Eur Food Res Technol 247:2609–2619. https://doi.org/10.1007/s00217-021-03829-4
Lokesh M, Panneerselvam A, Gawali PP, Sreekrishnakumar AK, Sahu U, Vendan SE (2023) Profiling of semiochemicals from three stored product beetles by headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry. Nat Prod Res 1–7. https://doi.org/10.1080/14786419.2023.2200945
Lorestani FA, Khashaveh A, Lorestani RA (2013) Fumigant toxicity of essential oil from Tanacetum balsamita L. (Compositae) against adults and eggs of Callosobruchus maculatus F. (Coleoptera: Bruchidae). Arch Phytopathol Plant Prot 46(17):2080–2086. https://doi.org/10.1080/03235408.2013.785112
Mackled MI, El-Hefny M, Bin-Jumah M, Wahba TF (2019) Assessment of the toxicity of natural oils from from Mentha piperita, Pinus roxburghii, and Rosa spp. against three stored product insects. Processes 7(11):861. https://doi.org/10.3390/pr7110861
Manivannan S (2015) Toxicity of phosphine on the developmental stages of rust-red flour beetle, Tribolium castaneum Herbst over a range of concentrations and exposures. J Food Sci Technol 52:6810–6815. https://doi.org/10.1007/s13197-015-1799-y
Moravvej G, Abbar S (2008) Fumigant toxicity of Citrus oils against cowpea seed beetle Callosobruchus maculatus (F.) (Coleoptera: Bruchidae). Pak J Biol Sci 11(1):48–54. https://doi.org/10.3923/pjbs.2008.48.54
Nath NS, Bhattacharya I, Tuck AG, Schlipalius DI, Ebert PR (2011) Mechanisms of phosphine toxicity. J Toxicol: 494168.https://doi.org/10.1155/2F2011/2F494168
Navarro S, Navarro H (2016) Current global challenges to the use of fumigants. In: Navarro S, Jayas DS, Alagusundaram K (eds) Proceedings of the 10th International Conference on Controlled Atmosphere and Fumigation in Stored Products, New Delhi, India. 6-11 November 2016. CAF Permanent Committee Secretariat, Winnipeg, Canada, pp 126–133
Nayak MK, Daglish GJ, Phillips TW, Ebert PR (2020) Resistance to the fumigant phosphine and its management in insect pests of stored products: a global perspective. Annu Rev Entomol 65:333–350. https://doi.org/10.1146/annurev-ento-011019-025047
Oboh G, Ademosun AO, Olumuyiwa TA, Olasehinde TA, Ademiluyi AO, Adeyemo AC (2017) Insecticidal activity of essential oil from orange peels (Citrus sinensis) against Tribolium confusum, Callosobruchus maculatus and Sitophilus oryzae and its inhibitory effects on acetylcholinesterase and Na+/K+-ATPase activities. Phytoparasitica 45(4):501–508. https://doi.org/10.1007/s12600-017-0620-z
Oladipupo SO, Hu XP, Appel AG (2022) Essential oils in urban insect management - a review. J Econ Entomol 115(5):1375–1408. https://doi.org/10.1093/jee/toac083
Priestley CM, Burgess IF, Williamson EM (2006) Lethality of essential oil constituents towards the human louse, Pediculus humanus, and its eggs. Fitoterapia 77(4):303–309. https://doi.org/10.1016/j.fitote.2006.04.005
Pumnuan J, Insung A (2016) Fumigant toxicity of plant essential oils in controlling thrips, Frankliniella schultzei (Thysanoptera: Thripidae) and mealybug, Pseudococcus jackbeardsleyi (Hemiptera: Pseudococcidae). J Entomol Res 40(1):1–10. https://doi.org/10.5958/0974-4576.2016.00001.3
Rajendran S (2002) Postharvest pest losses. In: Pimentel D (ed) Encyclopedia of Pest Management. Marcel Dekker Inc, New York, pp 654–656
Rajendran S, Sriranjini V (2008) Plant products as fumigants for stored-product insect control. J Stored Prod Res 44(2):126–135. https://doi.org/10.1016/j.jspr.2007.08.003
Ramadan GRM, Maille JM, Phillips TW (2022) Sorption and desorption dynamics of ethyl formate and propylene oxide as fumigants in durable agricultural commodities. J Stored Prod Res 99:102007. https://doi.org/10.1016/j.jspr.2022.102007
Rees DP (2004) Insects of stored products. CSIRO Publishing, Collingwood, Victoria, Australia. https://doi.org/10.1071/9780643101128
Reyes EI, Farias ES, Silva EM, Filomeno CA, Plata MA, Picanço MC, Barbosa LC (2019) Eucalyptus resinifera essential oils have fumigant and repellent action against Hypothenemus hampei. Crop Prot 116:49–55. https://doi.org/10.1016/j.cropro.2018.09.018
Rodríguez A, Beato M, Usseglio VL, Camina J, Zygadlo JA, Dambolena JS, Zunino MP (2022) Phenolic compounds as controllers of Sitophilus zeamais: a look at the structure-activity relationship. J Stored Prod Res 99:102038. https://doi.org/10.1016/j.jspr.2022.102038
Sahu U, Ibrahim SS, Ezhil Vendan S (2021a) Persistence and ingestion characteristics of phytochemical volatiles as bio-fumigants in Sitophilus oryzae adults. Ecotoxicol Environ Saf 210:111877. https://doi.org/10.1016/j.ecoenv.2020.111877
Sahu U, Sreevathsan S, Mudliar SN, Vendan SE (2021b) Fumigant toxicity of garlic essential oil with the combined effect of ozone gas and determination of phytochemical residues from the treated rice weevil Sitophilus oryzae and wheat grains. In: Jayas DS, Jian F (eds) Proceedings of the 11th International Conference on Controlled Atmosphere and Fumigation in Stored Products (CAF2020), Winnipeg, Canada, 23-27 August 2021. CAF Permanent Committee Secretariat, Winnipeg, Canada, pp 261–268
Sayed S, Soliman MM, Al-Otaibi S, Hassan MM, Elarrnaouty SA, Abozeid SM, El-Shehawi AM (2022) Toxicity, deterrent and repellent activities of four essential oils on Aphis punicae (Hemiptera: Aphididae). Plants 11(3):463. https://doi.org/10.3390/plants11030463
Smissaert HR, Jansen AAM (1984) On the variation of toxic effects over species, its cause, and analysis by “structure-selectivity relations.” Ecotoxicol Environ Saf 8(3):294–302. https://doi.org/10.1016/0147-6513(84)90034-4
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. https://doi.org/10.1093/jee/96.3.990
Vendan SE, Manivannan S, Sunny AM, Murugesan R (2017) Phytochemical residue profiles in rice grains fumigated with essential oils for the control of rice weevil. PLoS One 12(10):1–17. https://doi.org/10.1371/journal.pone.0186020
Wang Y, Zhang LT, Feng YX, Zhang D, Guo SS, Pang X, Geng ZF, Xi C, Du SS (2019) Comparative evaluation of the chemical composition and bioactivities of essential oils from four spice plants (Lauraceae) against stored-product insects. Ind Crops Prod 140:111640. https://doi.org/10.1016/j.indcrop.2019.111640
Yang FL, Zhu F, Lei CL (2010) Garlic essential oil and its major component as fumigants for controlling Tribolium castaneum (Herbst) in chambers filled with stored grain. J Pest Sci 83(3):311–317. https://doi.org/10.1007/s10340-010-0300-y
Zaio YP, Gatti G, Ponce AA, Saavedra Larralde NA, Martinez MJ, Zunino MP, Zygadlo JA (2018) Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship. J Sci Food Agric 98(15):5822–5831. https://doi.org/10.1002/jsfa.9132
Zimmermann RC, de Carvalho Aragao CE, de Araújo PJP, Benatto A, Chaaban A, Martins CEN, do Amaral W, Cipriano RR, Zawadneak MA (2021) Insecticide activity and toxicity of essential oils against two stored-product insects. Crop Prot 144:105575. https://doi.org/10.1016/j.cropro.2021.105575
Acknowledgements
The authors are grateful to the Director, CSIR-Central Food Technological Research Institute, Mysuru, for providing support and facilities for the present study. First author greatly acknowledges the University Grants Commission, Government of India for the Senior Research Fellowship. The authors extend thanks to Mr. M. Bavani Eswaran, CIFS, CSIR-CFTRI for his technical support in GC-MS analysis.
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This research was supported by the Council of Scientific and Industrial Research (CSIR), Ministry of Science and Technology, Government of India, New Delhi, under the scheme CSIR-Fundamental and Innovative Research in Science of Tomorrow (CSIR-FIRST) (Grant Ref. No. MLP300).
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The study was conceptualized and supervised by Subramanian Ezhil Vendan. The experimentation and data analysis were performed by Madhurya Lokesh. The manuscript was written by Madhurya Lokesh, Urvashi Sahu, and Aswathi Kozhissery Sreekrishnakumar. Subramanian Ezhil Vendan reviewed and edited the manuscript as well as acquired fund.
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Lokesh, M., Sreekrishnakumar, A.K., Sahu, U. et al. Influence of molecular descriptors of plant volatilomics on fumigant action against the three major stored product beetle pests. Environ Sci Pollut Res (2024). https://doi.org/10.1007/s11356-024-33483-8
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DOI: https://doi.org/10.1007/s11356-024-33483-8