Exploring the growth inhibition potential of monoketone curcuminoids against Spodoptera frugiperda

Authors

  • Larissa Costa Oliveira Institute of Science, Technology, and Innovation, Federal University of Lavras, São Sebastião do Paraíso, MG – Brazil
  • Yan Ramalho Robles Department of Chemistry, Faculty of Philosophy, Sciences, and Letters at Ribeirão Preto, University of São Paulo (FFCLRP/USP), Ribeirão Preto, SP, Brazil
  • Murilo Norberto Pereira Department of Chemistry, Faculty of Philosophy, Sciences, and Letters at Ribeirão Preto, University of São Paulo (FFCLRP/USP), Ribeirão Preto, SP, Brazil
  • Michele Trombin Souza Research Center for Family Agriculture, Agricultural Research and Rural Extension Company of Santa Catarina (CEPAF/EPAGRI), Chapecó, SC – Brazil
  • Mireli Trombin Souza Research Center for Family Agriculture, Agricultural Research and Rural Extension Company of Santa Catarina (CEPAF/EPAGRI), Chapecó, SC – Brazil
  • Leandro Prado Ribeiro Research Center for Family Agriculture, Agricultural Research and Rural Extension Company of Santa Catarina (CEPAF/EPAGRI), Chapecó, SC – Brazil
  • Antônio Eduardo Miller Crotti Department of Chemistry, Faculty of Philosophy, Sciences, and Letters at Ribeirão Preto, University of São Paulo (FFCLRP/USP), Ribeirão Preto, SP, Brazil

DOI:

https://doi.org/10.33837/msj.v9i2.1822

Keywords:

Claisen-Schmidt condensation, fall armyworm, halogenated compounds, diarylpentanoids

Abstract

Spodoptera frugiperda, known as the fall armyworm (FAW), is a polyphagous pest that causes huge economic losses in different agricultural regions of the world. Its control is challenging due to its widespread resistance to conventional insecticides and Bt events. This study aimed to assess the lethal toxicity and growth-inhibitory effects of eight acetone-derived monoketone curcuminoids (MKCs) on S. frugiperda larvae. MKCs were synthesized by Claisen-Schmidt condensation between acetone and aromatic aldehydes in a basic medium and tested against FAW larvae at a concentration of 250 mg kg-1 (dietary exposure) over 7 days. None of the tested compounds showed a significant lethal toxicity to FAW. However, halogenated MKCs derivatives 4 ((1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one) and 5 ((1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one) exhibited sublethal effects, reducing larval weight by 59% and 55%, respectively, compared to the negative control. These results indicated that the halogenation of MKCs may be a promising strategy to be exploited in the search for novel bioactive compounds to manage FAW in agricultural food production systems.

Keywords: Claisen-Schmidt condensation; fall armyworm; halogenated compounds; monoketone curcuminoids

Author Biography

Larissa Costa Oliveira, Institute of Science, Technology, and Innovation, Federal University of Lavras, São Sebastião do Paraíso, MG – Brazil

Institute of Science, Technology, and Innovation, Federal University of Lavras, São Sebastião do Paraíso, MG – Brazil

References

Ajaiyeoba, E. O., Sama, W., Essien, E. E., Olayemi, J. O., Ekundayo, O., Walker, T. M. and Setzer, W. N. Larvicidal activity of turmerone-rich essential oils of Curcuma longa. Leaf and rhizome from Nigeria on Anopheles gambiae. Pharmaceutical Biology 2008, 46, 279-282. DOI: https://www.doi.org/10.1080/13880200701741138.

Ansante, T. F., do Prado Ribeiro, L., Bicalho, K. U., Fernandes, J. B., das Graças Fernandes da Silva, M. F., Vieira, P. C. and Vendramim, J. D. Secondary metabolites from Neotropical Annonaceae: screening, bioguided fractionation, and toxicity to Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae). Industrial Crops and Products 2015, 74, 969-976. DOI: https://www.doi.org/10.1016/j.indcrop.2015.05.058.

Chaudhary, M. N., Ayub, Q., Wee, W. Y., Lim, S. Y., Ling, F. Y., Tan, Y. E., Masilamany, D. and Song, B. K. From the Americas to Southeast Asia: navigating the genomic waves of fall armyworm (Spodoptera frugiperda) invasions. Evolutionary Applications 2025, 18, e70139. DOI: https://www.doi.org/10.1111/eva.70139.

Devi, A. P., Alsulimani, A., Hidalgo, J. R., Neske, A., Sayyed, R. Z., Hassan, M., Ameta, K. L. and Elshazly, H. Bis- and mono-substituted chalcones exert anti-feedant and toxic effects on fall armyworm Spodoptera frugiperda. Saudi Journal of Biological Sciences 2021, 28, 5754-5759. DOI: https://www.doi.org/10.1016/j.sjbs.2021.06.016.

Dohutia, C., Chetia, D., Gogoi, K. and Sarma, K. Design, in silico and in vitro evaluation of curcumin analogues against Plasmodium falciparum. Experimental Parasitology 2017, 175, 51-58. DOI: https://www.doi.org/10.1016/j.exppara.2017.02.006.

Gagandeep, Kumar, P., Kandi, S. K., Mukhopadhyay, K. and Rawat, D. S. Synthesis of novel monocarbonyl curcuminoids, evaluation of their efficacy against MRSA, including ex vivo infection model and their mechanistic studies. European Journal of Medicinal Chemistry 2020, 195, 112276. DOI: https://www.doi.org/10.1016/j.ejmech.2020.112276.

Gebissa, N., Tolossa, K., Gebresilassie, A., Aklilu, E., Bisrat, D., Kumsa, B. and Dugassa, S. Larvicidal effects of selected medicinal plant extracts against Anopheles arabiensis, Anopheles stephensi, and Aedes aegypti. Tropical Medicine and Health 2025, 53, 197. DOI: https://www.doi.org/10.1186/s41182-025-00879-2.

Greene, G. L., Leppla, N. C. and Dickerson, W. A. Velvetbean Caterpillar: A Rearing Procedure and Artificial Medium. Journal of Economic Entomology 1976, 69, 487-488. DOI: https://www.doi.org/10.1093/jee/69.4.487.

Hinde, J. and Demétrio, C. G. B. Overdispersion: models and estimation. Computational Statistics & Data Analysis 1998, 27, 151-170. DOI:https://www.doi.org/10.1016/s0167-9473(98)00007-3.

Ioannou, E., Stavrakaki, M., Alemany-Chavarria, M., Maréchal, J.-D., Pantiora, P., Georgakis, N., Tsakireli, D., Matiadis, D., Sagnou, M., Roditakis, E., Vontas, J. and Labrou, N. E. A novel monocarbonyl curcumin analog synergizes pesticide efficiency via cytochrome P450 inhibition in the whitefly Bemisia tabaci. Journal of Pest Science 2025, 99, 22. DOI: https://www.doi.org/10.1007/s10340-025-01974-3.

Jeon, J. H., Jeong, S. A., Park, D. S., Park, H. H., Shin, S. W. and Oh, H. W. Disruptive effects of two curcuminoids (demethoxycurcumin and bisdemethoxycurcumin) on the larval development of Drosophila melanogaster. Insects 2023, 14, DOI: https://www.doi.org/10.3390/insects14120959.

Jeschke, P. Latest generation of halogen-containing pesticides. Pest Management Science 2017, 73, 1053-1066. DOI: https://www.doi.org/10.1002/ps.4540.

Kartakis, S., Horrocks, K. J., Cingiz, K., Kriticos, D. J. and Wesseler, J. Migration extent and potential economic impact of the fall armyworm in Europe. Scientific Reports 2025, 15, 17405. DOI: https://www.doi.org/10.1038/s41598-025-02595-7.

Kausar, N., Shier, W. T., Ahmed, M., Maryam, Albekairi, N. A., Alshammari, A., Saleem, M., Imran, M. and Muddassar, M. Investigation of the insecticidal potential of curcumin derivatives that target the Helicoverpa armigera sterol carrier protein-2. Heliyon 2024, 10, e29695. DOI: https://www.doi.org/10.1016/j.heliyon.2024.e29695.

Li, Y., Li, S., Yin, X. and Liu, S. Design, synthesis and insecticidal activity of novel Isoxazoline Acylhydrazone compounds. Pest Management Science 2024, 80, 1654-1662. DOI: https://www.doi.org/10.1002/ps.7897.

Matiadis, D., Liggri, P. G. V., Kritsi, E., Tzioumaki, N., Zoumpoulakis, P., Papachristos, D. P., Balatsos, G., Sagnou, M. and Michaelakis, A. Curcumin derivatives as potential mosquito larvicidal agents against two mosquito vectors, Culex pipiens and Aedes albopictus. International Journal of Molecular Sciences 2021, 22, DOI: https://www.doi.org/10.3390/ijms22168915.

Mohd Faudzi, S. M., Leong, S. W., Abas, F., Mohd Aluwi, M. F. F., Rullah, K., Lam, K. W., Ahmad, S., Tham, C. L., Shaari, K. and Lajis, N. H. Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxide inhibitors. MedChemComm 2015, 6, 1069-1080. DOI: https://www.doi.org/10.1039/c4md00541d.

Montezano, D. G., Specht, A., Sosa-Gómez, D. R., Roque-Specht, V. F., Sousa-Silva, J. C., Paula-Moraes, S. V., Peterson, J. A. and Hunt, T. E. Host plants of Spodoptera frugiperda (Lepidoptera: Noctuidae) in the Americas. African Entomology 2018, 26, 286-300. DOI: https://www.doi.org/10.4001/003.026.0286.

Nelder, J. A. and Wedderburn, R. W. M. Generalized linear models. Journal of the Royal Statistical Society, Series A 1972, 135, DOI: https://www.doi.org/10.2307/2344614.

Nivedha, J., Kanimozhi, K., Olikkavi, S., Vidhyasagar, T., Vijayakumar, N., Uma, C., Rajeswari, K. and Vennila, L. In vitro screening for antioxidant and antimicrobial properties of 3,5-bis(E-thienylmethylene) piperidin-4-one, a curcumin analogue. Pharmacognosy Research 2022, 14, 276-283. DOI: https://www.doi.org/10.5530/pres.14.3.40.

Paredes-Sanchez, F. A., Rivera, G., Bocanegra-Garcia, V., Martinez-Padron, H. Y., Berrones-Morales, M., Nino-Garcia, N. and Herrera-Mayorga, V. Advances in control strategies against Spodoptera frugiperda: a review. Molecules 2021, 26, 5587. DOI: https://www.doi.org/10.3390/molecules26185587.

Prasad, S., Yadav, V. R., Ravindran, J. and Aggarwal, B. B. ROS and CHOP are critical for dibenzylideneacetone to sensitize tumor cells to TRAIL through induction of death receptors and downregulation of cell survival proteins. Cancer Research 2011, 71, 538-549. DOI: https://www.doi.org/10.1158/0008-5472.CAN-10-3121.

R Core Team. R: A language and environment for statistical computing, version 4.0.2. R Foundation for Statistical Computing. Vienna, Austria, 2020

Rashid, U., Panhwar, A., Farhan, A., Akhter, M., Jalbani, N. and Hashmi, D. R. Nematicidal effects of various fractions of Curcuma longa against Meloidogyne incognita (root knot nematodes). Turkish J. Agric. Engineer. Res. 2021, 2, 175-182. DOI: https://www.doi.org/10.46592/turkager.2021.v02i01.013.

Tay, W. T., Meagher, R. L., Jr., Czepak, C. and Groot, A. T. Spodoptera frugiperda: ecology, evolution, and management options of an invasive species. Annual Review of Entomology 2023, 68, 299-317. DOI: https://www.doi.org/10.1146/annurev-ento-120220-102548.

Verma, R. K., Kumari, P., Maurya, R. K., Kumar, V., Verma, R. B. and Singh, R. K. Medicinal properties of turmeric (Curcuma longa L.): A review. International Journal of Chemical Studies 2018, 6, 1354-1357.

Vieira, T. M., Dos Santos, I. A., Silva, T. S., Martins, C. H. G. and Crotti, A. E. M. Antimicrobial activity of monoketone curcuminoids against cariogenic bacteria. Chemistry & Biodiversity 2018, 15, e1800216. DOI: https://www.doi.org/10.1002/cbdv.201800216.

Vieira, T. M., Tanajura, L. S., Heleno, V. C. G., Magalhães, L. G. and Crotti, A. E. M. Monoketone curcuminoids: an updated review of their synthesis and biological activities. Future Pharmacology 2024, 4, 54-77. DOI: https://www.doi.org/10.3390/futurepharmacol4010006.

Xie, W., Li, P., Peng, J., Chen, Y., Liu, J., Wang, X., Yuchi, Z., He, L. and Li, Y. Novel boron-containing anthranilic diamide derivatives: design, synthesis, and exploration of the action mode against lepidopteran insects. Pest Management Science 2025, 81, 6385-6403. DOI: https://www.doi.org/10.1002/ps.8979.

Zhou, H., Guo, F., Luo, J., Zhang, Y., Liu, J., Zhang, Y., Zheng, X., Wan, F. and Ding, W. Functional analysis of an upregulated calmodulin gene related to the acaricidal activity of curcumin against Tetranychus cinnabarinus (Boisduval). Pest Management Science 2021, 77, 719-730. DOI: https://www.doi.org/10.1002/ps.6066.

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Published

2026-08-24

How to Cite

Oliveira, L. C., Robles, Y. R., Pereira, M. N., Souza, M. T., Souza, M. T., Ribeiro, L. P., & Crotti, A. E. M. (2026). Exploring the growth inhibition potential of monoketone curcuminoids against Spodoptera frugiperda. Multi-Science Journal, 9(2), 20–26. https://doi.org/10.33837/msj.v9i2.1822

Issue

Vol. 9 No. 2 (2026)

Section

Exact and Earth Sciences

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Copyright (c) 2026 Larissa Costa Oliveira, Yan Ramalho Robles, Murilo Norberto Pereira, Michele Trombin Souza, Mireli Trombin Souza, Leandro Prado Ribeiro, Antônio Eduardo Miller Crotti

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