Synthesis, characterization, and evaluation of derivatives from cardanol as repellents/pesticides agents of Liriomyza sativae (Diptera: Agromyzidae) and Bemisia tabaci (Hemiptera: Aleyrodidae) on melon plants

Authors

DOI:

https://doi.org/10.33448/rsd-v12i3.40454

Keywords:

Deterrent effect; Insecticidal effect; Repellence; White fly; Leafminer fly.

Abstract

Hydrogenated cardanol derivatives were evaluated as potentially active insecticides/repellent agents against insect pests such as Liriomyza sativae (Diptera: Agromyzidae) and Bemisia tabaci biotype B (Hemiptera: Aleyrodidae). Benzoylation, acetylation, and methylation were made on the hydrogenated cardanol aromatic ring to synthesize active ingredients with potential insecticide action. Nuclear magnetic resonance spectra (13C and 1H NMR) and infrared (IR) proposed the chemical elucidation of the products. The production of melon seedlings was made and each synthesized products, benzoylated 3-pentadecylphenol, acetylated 3-pentadecylphenol, and methylated 3-pentadecylphenol were applied to seedlings by glass sprayer. Phytotoxicity evaluations were carried out, noting that all the plants showed burnt leaves except for concentration of 1% which the leaves remained healthy look. The insecticidal efficacy as well as the repellent and dissuasive effects were evaluated by a completely randomized design (DIC) and a randomized complete block design (DBCA) with six treatments, five and four replicates respectively. The compounds derived from cardanol did not present insecticidal activity in DBCA for L. sativae; however, they had a noticeable effect on oviposition index (IPO). Ovicidal effect and nymphal mortality only were found for B. tabaci by methylated 3-pentadecylphenol and Mospilan® in terms of dissuasion and oviposition effects in the two bioassays evaluated and, methylated 3-pentadecyl showed a similar behavior as the effect of Abamectin® on the confinement test, with 53.5% - 65.4% repellence of adults, an important data to emphasize that the products synthesized from cardanol are promising in preventing the pests attack such as L. sativae and, B. tabaci.

Author Biography

Nádylla Régis Xavier de Oliveira, Universidade Federal do Ceará

 

 

References

Alcântara, D. B., Fernandes, T. S. M., Nascimento, H. O., Lopes, A. F., Menezes, M. G. G., Lima, A. C. A., Carvalho, T. v., Grinberg, P., Milhome, M. A. L., Oliveira, A. H. B., Becker, H., Zocolo, G. J., & Nascimento, R. F. (2019). Diagnostic detection systems and QuEChERS methods for multiclass pesticide analyses in different types of fruits: An overview from the last decade. Food Chemistry, 298, 124958. https://doi.org/10.1016/J.FOODCHEM.2019.124958

Arab, A., & Bento, J. M. S. (2006). Plant Volatiles: New Perspectives for Research in Brazil.

Araujo, E. L., Costa, E. M., Filho, E. R. M., Nogueira, C. H. F., & Santos, M. R. D. (2012). Efeito de inseticidas sobre a mosca minadora ( Diptera : Agromyzidae ), quando aplicados durante a fase de ovo Effect of insecticides on leafminer ( Diptera : Agromyzidae ) when applied during the phase of egg. 18–22.

Baldin, E. L., da Silva, J. P. G., & Pannuti, L. E. R. (2012). Resistance of melon cultivars to Bemisia tabaci biotype B. Horticultura Brasileira, 30(4), 600–606. https://doi.org/10.1590/S0102-05362012000400007

Birchfield, A. S., & McIntosh, C. A. (2020). Metabolic engineering and synthetic biology of plant natural products – A minireview. Current Plant Biology, 24, 100163. https://doi.org/10.1016/J.CPB.2020.100163

Capinera, J. L. (2020). Order Hemiptera—Bugs. Handbook of Vegetable Pests, 259–382. https://doi.org/10.1016/B978-0-12-814488-6.00008-X

Carrière, Y., & Onstad, D. W. (2023). The role of landscapes in insect resistance management. Insect Resistance Management, 329–379. https://doi.org/10.1016/B978-0-12-823787-8.00006-4

Celin, E. F., Oliveira, F. I. C., Dias-Pini, N. S., Nunes, G. H. S., & Aragão, F. A. S. (2017). New sources of resistance to leafminers (Liriomyza sativae) in melon (Cucumis melo L.) germplasm. Genetics and Molecular Research, 16(2). https://doi.org/10.4238/gmr16029561

Chang, Y. W., Wang, Y. C., Yan, Y. Q., Wu, C. D., Xie, H. F., Gong, W. R., & Du, Y. Z. (2022). Insect hormones affect the toxicity of the insecticidal growth regulator cyromazine in Liriomyza trifolii (Diptera: Agromyzidae). Pesticide Biochemistry and Physiology, 188, 105263. https://doi.org/10.1016/J.PESTBP.2022.105263

Cock, A. de, Ishaaya, I., van Veire, M. de, & DECHEELEl EconEntomol, D. J. (1995). Response of Buprofezin-Susceptible and-Resistant Strains of Trialeurodes vaporariorum (Homoptera: Aleyrodidae) to Pyriproxyfen and Diafenthiuron. Journal of Economy Entomology, 88(4), 763–767. http://jee.oxfordjournals.org/

Carvalho, G. H. F., de Andrade, M. A., de Araújo, C. N., Santos, M. L., de Castro, N. A., Charneau, S., Monnerat, R., de Santana, J. M., & Bastos, I. M. D. (2019). Larvicidal and pupicidal activities of eco-friendly phenolic lipid products from Anacardium occidentale nutshell against arbovirus vectors. Environmental Science and Pollution Research International, 26(6), 5514–5523. https://doi.org/10.1007/s11356-018-3905-y

Denholm, I., & Devine, G. (2013). Insecticide Resistance. Encyclopedia of Biodiversity: Second Edition, 298–307. https://doi.org/10.1016/B978-0-12-384719-5.00104-0

Devos, Y., Oberkofler, L., & Glandorf, D. C. M. (2022). Genetically modified plants and food/feed: Risk assessment considerations. Reference Module in Biomedical Sciences. https://doi.org/10.1016/B978-0-12-824315-2.00012-9

Fenemore, P. G. (1980). Oviposition of potato tuber moth, phthorimaea operculella zell. (lepidoptera: Gelechiidae); identification of host-plant factors influencing oviposition response. New Zealand Journal of Zoology, 7(3), 435–439. https://doi.org/10.1080/03014223.1980.10423798

Ferguson, J. S. (2004). Development and Stability of Insecticide Resistance in the Leafminer <I>Liriomyza trifolii</I> (Diptera: Agromyzidae) to Cyromazine, Abamectin, and Spinosad. Journal of Economic Entomology, 97(1), 112–119. https://doi.org/10.1603/0022-0493-97.1.112

Khursheed, A., Rather, M. A., Jain, V., Wani, A. R., Rasool, S., Nazir, R., Malik, N. A., & Majid, S. A. (2022). Plant based natural products as potential ecofriendly and safer biopesticides: A comprehensive overview of their advantages over conventional pesticides, limitations and regulatory aspects. Microbial Pathogenesis, 173, 105854. https://doi.org/10.1016/J.MICPATH.2022.105854

Klassen, D., Lennox, M. D., Dumont, M. J., Chouinard, G., & Tavares, J. R. (2023). Dispensers for pheromonal pest control. Journal of Environmental Management, 325, 116590. https://doi.org/10.1016/J.JENVMAN.2022.116590

Kubo, I., Nihei, K.-I., & Tsujimoto, K. (2003). Antibacterial action of anacardic acids against methicillin resistant Staphylococcus aureus (MRSA). Journal of Agricultural and Food Chemistry, 51(26), 7624–7628. https://doi.org/10.1021/jf034674f

Kubo, J., Lee, J. R., & Kubo, I. (1999). Anti-Helicobacter pylori agents from the cashew apple. Journal of Agricultural and Food Chemistry, 47(2), 533–537. https://doi.org/10.1021/jf9808980

Lacey, L. A., Grzywacz, D., Shapiro-Ilan, D. I., Frutos, R., Brownbridge, M., & Goettel, M. S. (2015). Insect pathogens as biological control agents: Back to the future. Journal of Invertebrate Pathology, 132, 1–41. https://doi.org/10.1016/J.JIP.2015.07.009

Lamichhane, J. R., Aubertot, J. N., Begg, G., Birch, A. N. E., Boonekamp, P., Dachbrodt-Saaydeh, S., Hansen, J. G., Hovmøller, M. S., Jensen, J. E., Jørgensen, L. N., Kiss, J., Kudsk, P., Moonen, A. C., Rasplus, J. Y., Sattin, M., Streito, J. C., & Messéan, A. (2016). Networking of integrated pest management: A powerful approach to address common challenges in agriculture. Crop Protection, 89, 139–151. https://doi.org/10.1016/J.CROPRO.2016.07.011

Lemos, L. J. U., Costa-Lima, T. C. da, Godoy, W. A. C., Barros, R. V., & Barros, R. (2021). Evidence for coabundance of leafminer flies and whiteflies in melon crops. Bragantia, 80. https://doi.org/10.1590/1678-4499.20190459

Lim, M.-Y., Choi, Y.-S., Shin, H., Kim, K., Myung Shin, D., & Lee, J.-C. (2018). Cross-Linked Graphene Oxide Membrane Functionalized with Self-Cross-Linkable and Bactericidal Cardanol for Oil/Water Separation. ACS Applied Nano Materials, 1(6), 2600–2608. https://doi.org/10.1021/acsanm.8b00241

Liu, Z., Chen, J., Knothe, G., Nie, X., & Jiang, J. (2016). Synthesis of Epoxidized Cardanol and Its Antioxidative Properties for Vegetable Oils and Biodiesel. ACS Sustainable Chemistry & Engineering, 4(3), 901–906. https://doi.org/10.1021/acssuschemeng.5b00991

Lomonaco, D., Pinheiro Santiago, G. M., Ferreira, Y. S., Campos Arriaga, Â. M., Mazzetto, S. E., Mele, G., & Vasapollo, G. (2009). Study of technical CNSL and its main components as new green larvicides. Green Chem., 11(1), 31–33. https://doi.org/10.1039/B811504D

Mendes Hacke, A. C., Lima, D., & Kuss, S. (2022). Green synthesis of electroactive nanomaterials by using plant-derived natural products. Journal of Electroanalytical Chemistry, 922, 116786. https://doi.org/10.1016/J.JELECHEM.2022.116786

Naegeli, H. (2023). Safety assessment of food and feed derived from genetically modified plants. Present Knowledge in Food Safety, 938–958. https://doi.org/10.1016/B978-0-12-819470-6.00033-0

Nagabhushana, K. S., Umamaheshwari, S., Tocoli, F. E., Prabhu, S. K., Green, I. R., & Ramadoss, C. S. (2002). Inhibition of soybean and potato lipoxygenases by bhilawanols from bhilawan (Semecarpus anacardium) nut shell liquid and some synthetic salicylic acid analogues. Journal of Enzyme Inhibition and Medicinal Chemistry, 17(4), 255–259. https://doi.org/10.1080/1475636021000006243

Nunes, G. H. de S., Medeiros, A. C., Araujo, E. L., Nogueira, C. H. F., & Sombra, K. D. da S. (2013). Resistência de acessos de meloeiro à mosca-minadora Liriomyza spp. (Diptera: Agromyzidae). Revista Brasileira de Fruticultura, 35(3), 746–754. https://doi.org/10.1590/S0100-29452013000300011

Oliveira, F. I. C. de, Fiege, L. B. C., Celin, E. F., Innecco, R., Nunes, G. H. S., & Aragão, F. A. S. (2017). Screening of melon genotypes for resistance to vegetable leafminer and your phenotypic correlations with colorimetry. Anais Da Academia Brasileira de Ciências, 89(2), 1155–1166. https://doi.org/10.1590/0001-3765201720150368

Padilha, A. C., Piovesan, B., Morais, M. C., Arioli, C. J., Zotti, M. J., Grützmacher, A. D., & Botton, M. (2019). Toxicity, attraction, and repellency of toxic baits to stingless bees Plebeia emerina (Friese) and Tetragonisca fiebrigi (Schwarz) (Hymenoptera: Apidae: Meliponini). Ecotoxicology and Environmental Safety, 183, 109490. https://doi.org/10.1016/J.ECOENV.2019.109490

Pirzada, T., de Farias, B. v., Mathew, R., Guenther, R. H., Byrd, M. v., Sit, T. L., Pal, L., Opperman, C. H., & Khan, S. A. (2020). Recent advances in biodegradable matrices for active ingredient release in crop protection: Towards attaining sustainability in agriculture. Current Opinion in Colloid & Interface Science, 48, 121–136. https://doi.org/10.1016/J.COCIS.2020.05.002

Santos, K. P. E. dos, Ferreira Silva, I., Mano-Sousa, B. J., Duarte-Almeida, J. M., Castro, W. V. de, Azambuja Ribeiro, R. I. M. de, Santos, H. B., & Thomé, R. G. (2023). Abamectin promotes behavior changes and liver injury in zebrafish. Chemosphere, 311, 136941. https://doi.org/10.1016/J.CHEMOSPHERE.2022.136941

Santos, S. R. L., Silva, V. B., Melo, M. A., Barbosa, J. D. F., Santos, R. L. C., de Sousa, D. P., & Cavalcanti, S. C. H. (2010). Toxic Effects on and Structure-Toxicity Relationships of Phenylpropanoids, Terpenes, and Related Compounds in Aedes aegypti Larvae. Vector-Borne and Zoonotic Diseases, 10(10), 1049–1054. https://doi.org/10.1089/vbz.2009.0158

Santos, T. de L., Nunes, A. B. A., Giongo, V., Barros, V. da S., & Figueirêdo, M. C. B. de. (2018). Cleaner fruit production with green manure: The case of Brazilian melons. Journal of Cleaner Production, 181, 260–270. https://doi.org/10.1016/J.JCLEPRO.2017.12.266

Silva, F. S., Lopes, M. C., Farias, E. S., Sarmento, R. A., Pereira, P. S., & Picanço, M. C. (2020). Standardized sampling plan for common blossom thrips management in melon fields from north Brazil. Crop Protection, 134, 105179. https://doi.org/10.1016/J.CROPRO.2020.105179

Silva, J. P. G. F., Zaché, R. R. C., Baldin, E. L. L., Oliveira, F. B., & Valtapeli, E. R. (2012). Repelência e deterrência na oviposição de Bemisia tabaci biótipo B pelo uso de extratos vegetais em Cucurbita pepo L. Revista Brasileira de Plantas Medicinais, 14(1), 76–83. https://doi.org/10.1590/S1516-05722012000100011

Singh, A., Dhiman, N., Kar, A. K., Singh, D., Purohit, M. P., Ghosh, D., & Patnaik, S. (2020). Advances in controlled release pesticide formulations: Prospects to safer integrated pest management and sustainable agriculture. Journal of Hazardous Materials, 385, 121525. https://doi.org/10.1016/J.JHAZMAT.2019.121525

Somers, J., Nguyen, J., Lumb, C., Batterham, P., & Perry, T. (2015). In vivo functional analysis of the Drosophila melanogaster nicotinic acetylcholine receptor Dα6 using the insecticide spinosad. Insect Biochemistry and Molecular Biology, 64, 116–127. https://doi.org/10.1016/J.IBMB.2015.01.018

Ware, G. W., & Whitacre, D. M. (2004). AN INTRODUCTION TO ( 3rd edition ). The Pesticide Book. Meister Pub. Willoughby, Ohio.

Wei, Q.-B., Lei, Z.-R., Nauen, R., Cai, D.-C., & Gao, Y.-L. (2015). Abamectin resistance in strains of vegetable leafminer, Liriomyza sativae (Diptera: Agromyzidae) is linked to elevated glutathione S-transferase activity. Insect Science, 22(2), 243–250. https://doi.org/10.1111/1744-7917.12080

Zhang, Y., Tian, T., Zhang, K., Zhang, Y., Wu, Q., Xie, W., Guo, Z., & Wang, S. (2022). Lack of fitness cost and inheritance of resistance to abamectin based on the establishment of a near-isogenic strain of Tetranychus urticae. Journal of Integrative Agriculture. https://doi.org/10.1016/J.JIA.2022.10.012

Zhu, X., Liu, X., Liu, T., Wang, Y., Ahmed, N., Li, Z., & Jiang, H. (2021). Synthetic biology of plant natural products: From pathway elucidation to engineered biosynthesis in plant cells. Plant Communications, 2(5), 100229. https://doi.org/10.1016/J.XPLC.2021.100229

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Published

28/02/2023

How to Cite

OLIVEIRA, M. R. F. .; DIAS-PINI, N. da S. .; CELIN, E. F.; ABREU, K. do V. .; OLIVEIRA, N. R. X. de .; MELO, A. M. A.; OLIVEIRA, M. de A. .; BISWAS, A.; CHENG, H. N.; ALVES, C. R. Synthesis, characterization, and evaluation of derivatives from cardanol as repellents/pesticides agents of Liriomyza sativae (Diptera: Agromyzidae) and Bemisia tabaci (Hemiptera: Aleyrodidae) on melon plants. Research, Society and Development, [S. l.], v. 12, n. 3, p. e11512340454, 2023. DOI: 10.33448/rsd-v12i3.40454. Disponível em: https://rsdjournal.org/index.php/rsd/article/view/40454. Acesso em: 14 nov. 2024.

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Agrarian and Biological Sciences