Estudio de potenciales insecticidas derivados de especies aromáticas con alto contenido de monoterpenoides para el control de Sitophilus Zeamais y Tribolium Castaneum

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dc.contributor.advisorPatiño Ladino, Oscar Javierspa
dc.contributor.advisorPrieto Rodríguez, Juliet Angélicaspa
dc.contributor.authorSierra Quitian, Andrés Germánspa
dc.contributor.orcidSierra Quitian, Andrés Germán [0000000319015133]spa
dc.date.accessioned2025-03-18T15:55:30Z
dc.date.available2025-03-18T15:55:30Z
dc.date.issued2025
dc.descriptionilustraciones, diagramas, fotografías a color, tablasspa
dc.description.abstractLos cereales desempeñan un papel importante en la seguridad alimentaria mundial ya que son una excelente fuente de nutrientes y pueden almacenarse durante largos períodos de tiempo. Sin embargo, durante la etapa de almacenamiento suelen presentarse los mayores problemas fitosanitarios que reducen la calidad de los cereales y que generalmente se asocian a diversos tipos de plagas, que incluyen insectos, roedores y microorganismos. Entre los insectos se destacan S. zeamais y T. castaneum por su distribución cosmopolita y por los daños que ocasionan en diversos cereales y productos de molienda. Para su control se suelen utilizar diversos productos sintéticos, muchos de los cuales suelen ser muy tóxicos para la salud humana y a nivel ambiental son poco selectivos, tienen problemas de acumulación y por su uso indiscriminado ha crecido la resistencia por parte de los insectos hacia los insecticidas. En la búsqueda de insecticidas eficaces y seguros para el control de este tipo de plagas de productos almacenados, los aceites esenciales (AEs) emergen como una alternativa prometedora de origen natural debido a sus propiedades fisicoquímicas, funciones ecológicas y propiedades biológicas reportadas. Entre los AEs con potencial productivo en este campo se destacan por sus altos rendimientos de extracción, composición química particular y sus propiedades insecticidas a Anethum graveolens L. (Apiaceae), Minthostachys mollis (Benth.) Griseb. (Lamiaceae), Satureja viminea L. (Lamiaceae) y Tagetes zypaquirensis Humb. & Bonpl. (Asteraceae). El presente estudio contribuye a la caracterización del potencial insecticida de estos cuatro AEs y de algunos de sus constituyentes químicos principales. En la primera etapa de la investigación se determinó el potencial insecticida frente a S. zeamais y T. castaneum de los AEs provenientes de A. graveolens, M. mollis, S. viminea y T. zypaquirensis. En este sentido los AEs fueron obtenidos mediante destilación por arrastre con vapor y se caracterizaron químicamente mediante CG-EM. Adicionalmente, se determinó la acción insecticida de algunos constituyentes químicos presentes en los AEs, algunos de los cuales fueron aislados por técnicas cromatográficas (éter de eneldo 1, oxido de piperitona 5, p-ment-3-en-8-ol 8, dihidrotagetona 9 y epóxido de mirceno 10) y otros fueron adquiridos comercialmente (R-carvona 2, D-limoneno 3, α-felandreno 4, R-pulegona 6, β-cariofileno 7 y β-mirceno 11). En una segunda etapa se establecieron algunas relaciones preliminares de estructura-actividad insecticida a partir de algunos de los monoterpenoides bioactivos presentes en los AEs. Para lo anterior fue necesario la adquisición de algunos monoterpenoides comerciales con estructura química relacionada (L-mentol 12, L-mentona 13, piperitona 14, carveol 15), la síntesis de algunos derivados (16 a 24) a partir de los constituyentes más activos (2, 5 y 6) y la determinación de la acción insecticida frente a S. zeamais y T. castaneum. Finalmente, en la tercera etapa del estudio se desarrolló una formulación de un insecticida encapsulado con los AEs de S. viminea y M. mollis, empleando el método de coprecipitación y usando β-ciclodextrina como matriz. Los complejos de inclusión (CI) obtenidos fueron caracterizados fisicoquímicamente y sus propiedades insecticidas determinadas sobre ambos insectos. Los resultados de composición química de los AEs permitieron establecer como componentes principales a éter de eneldo (28.56%), α-felandreno (25.78%) y R-carvona (23.67%) para A. graveolens, óxido de piperitona (30.40%) y pulegona (25.91%) en M. mollis, pulegona (37.40%) y p-ment-3-en-8-ol (11.83%) para S. viminea y dihidrotagetona (32.13%), epóxido de mirceno (19.64%) y β-mirceno (5.30%) en T. zypaquirensis. Los resultados destacan la acción fumigante (CL50) y la toxicidad por contacto (DL50) del AE de M. mollis contra T. castaneum (CL50 de 4.8 μL/L de aire y DL50 de 6.5 μg/insecto) y S. zeamais (CL50 de 7.0 μL/L de aire y DL50 de 5.81 μg/insecto). Este estudio describe el primer reporte sobre la actividad insecticida de los AEs de A. graveolens (contacto), M. mollis y S. viminea (de contacto y fumigante) contra T. castaneum, la toxicidad fumigante de M. mollis sobre S. zeamais y la acción insecticida del AE de T. zypaquirensis contra los dos insectos. Entre los constituyentes químicos evaluados, la R-carvona 2, el óxido de piperitona 5 y la R-pulegona 6 se destacan por su potencial insecticida contra S. zeamais (CL50 entre 3.0 y 42.4 μL/L, mientras que la DL50 está entre 14.9 y 24.6 μg/insecto) y T. castaneum (CL50 entre 2.2 y 4.8 μL/L, mientras que la DL50 está entre 4.8 y 13.1 μg/insecto). Este estudio proporciona por primera vez datos sobre la actividad insecticida, tanto fumigante como de contacto, de los compuestos 1, 5, 8, 9 y 11 frente a S. zeamais y T. castaneum. A partir de los compuestos 2, 5 y 6 se realizó la síntesis de nueve derivados (16 a 24) por modificaciones sobre sus grupos funcionales, encontrándose que los compuestos 20, 22 y 23 destacan por su potencial insecticida contra S. zeamais (CL50 entre 41.8 y 92.9 μL/L en el ensayo fumigante, y DL50 entre 24.5 y 45.1 μg/insecto en el ensayo tópico por contacto) y contra T. castaneum (CL50 entre 1.4 y 35.2 μL/L y DL50 entre 1.9 y 17.6 μg/insecto). El análisis preliminar de relación estructura-actividad permitió evidenciar: a) la halogenación y epoxidación de los monoterpenoides disminuyeron significativamente su actividad insecticida, excepto el compuesto 21, que presentó mayor toxicidad por contacto contra T. castaneum; b) la hidrogenación del doble enlace reduce la actividad fumigante sobre los dos insectos; c) la reducción del grupo carbonilo a alcohol disminuyó la actividad mediante la metodología fumigante, destacando la importancia del grupo carbonilo en la actividad insecticida; d) la isomerización del doble enlace afectó la actividad insecticida, resaltando la relevancia de los sistemas carbonilos α,β-insaturados exocíclicos para la actividad insecticida. Finalmente, se lograron obtener los CI con los AEs de S. viminea y M. mollis, partir del desarrollo de una formulación a base de β-ciclodextrina, lo cuales mostraron actividad insecticida frente a S. zeamais y T. castaneum después de 48 h de tratamiento, alcanzando el máximo efecto entre 96 y 148 h, resaltando el potencial que tiene el CI a base del mejor AE de S. viminea con una mortalidad superior al 80% a las 120 h. Finalmente, este estudio aporta de manera significativa al desarrollo de nuevos insecticidas basados en compuestos derivados de especies aromáticas, ofreciendo alternativas prometedoras para el control de plagas en granos almacenados. Los hallazgos abren nuevas perspectivas en la búsqueda de soluciones sostenibles y efectivas para la protección de productos agrícolas, destacando el potencial de estos compuestos naturales en el manejo integrado de plagas y la reducción de dependencia en pesticidas sintéticos (Texto tomado de la fuente).spa
dc.description.abstractCereals are crucial to global food security due to their rich nutrient content and long-term storage capability. However, during the storage phase, the greatest phytosanitary issues typically arise, which reduce cereal quality and are generally associated with various types of pests, including insects, rodents, and microorganisms. Among the insects, S. zeamais and T. castaneum stand out due to their cosmopolitan distribution and the damage they cause to various cereals and milling products. Various synthetic products are commonly used for their control, many of which are highly toxic to human health, environmentally non-selective, prone to accumulation issues, and have led to resistant insects due to indiscriminate use. In the search for effective and safe insecticides to control such pests in stored products, essential oils (EOs) emerge as a promising natural alternative due to their physicochemical properties, ecological functions and biological activities. Among the EOs with productive potential in this field, those from Anethum graveolens L. (Apiaceae), Minthostachys mollis (Benth.) Griseb. (Lamiaceae), Satureja viminea L. (Lamiaceae), and Tagetes zypaquirensis Humb. & Bonpl. (Asteraceae) stand out for their high extraction yields, unique chemical composition, and insecticidal properties. This study contributes to the characterization of the insecticidal potential of these four EOs and some of their main chemical constituents. In the first phase of the research, the insecticidal potential against S. zeamais and T. castaneum of the EOs from A. graveolens, M. mollis, S. viminea, and T. zypaquirensis was determined. The EOs were obtained by steam distillation and chemically characterized using GC-MS. Additionally, the insecticidal activity of some chemical constituents present in the EOs was determined, some of which were isolated by chromatographic techniques (dill ether 1, piperitone oxide 5, p-menth-3-en-8-ol 8, dihydrotagetone 9, and myrcene epoxide 10), while others were commercially acquired (R-carvone 2, D-limonene 3, α-phellandrene 4, R-pulegone 6, β-caryophyllene 7, and β-myrcene 11). In a second phase, preliminary structure-activity relationships of the insecticidal activity of some bioactive monoterpenoids present in the EOs were established. For this, several commercial monoterpenoids with related chemical structures were acquired (L-menthol 12, L-menthone 13, piperitone 14, carveol 15), and several derivatives (16 to 24) were synthesized from the most active constituents (2, 5, and 6). The insecticidal activity against S. zeamais and T. castaneum was then determined. Finally, in the third phase of the study, an encapsulated insecticide formulation was developed using the EOs of S. viminea and M. mollis, employing the co-precipitation method and using β-cyclodextrin as the matrix. The resulting inclusion complexes (ICs) were physicochemically characterized, and their insecticidal properties were assessed against both insects. The chemical composition results of the EOs identified dill ether (28.56%), α-phellandrene (25.78%), and carvone (23.67%) as the main components of A. graveolens; piperitone oxide (30.40%) and pulegone (25.91%) in M. mollis; pulegone (37.40%) and p-menth-3-en-8-ol (11.83%) for S. viminea; and dihydrotagetone (32.13%), myrcene epoxide (19.64%), and β-myrcene (5.30%) in T. zypaquirensis. The results highlight the fumigant action (LC50) and contact toxicity (LD50) of M. mollis EO against T. castaneum (LC50 of 4.8 μL/L of air and LD50 of 6.5 μg/insect) and S. zeamais (LC50 of 7.0 μL/L of air and LD50 of 5.81 μg/insect). This study reports for the first time the insecticidal activity of A. graveolens (contact), M. mollis, and S. viminea (contact and fumigant) EOs against T. castaneum, the fumigant toxicity of M. mollis against S. zeamais, and the insecticidal action of T. zypaquirensis EO against both insects. Among the evaluated chemical constituents, R-carvone 2, piperitone oxide 5, and R-pulegone 6 stood out for their insecticidal potential against S. zeamais (LC50 ranging from 3.0 to 42.4 μL/L, while the LD50 ranged from 14.9 to 24.6 μg/insect) and T. castaneum (LC50 ranging from 2.2 to 4.8 μL/L, while the LD50 ranged from 4.8 to 13.1 μg/insect). This study provides the first data on the fumigant and contact insecticidal activity of compounds 1, 5, 8, 9, and 11 against S. zeamais and T. castaneum. Nine derivatives (16 to 24) were synthesized from compounds 2, 5, and 6 through simple modifications of their functional groups, with compounds 20, 22, and 23 showing promising insecticidal potential against S. zeamais (LC50 ranging from 41.8 to 92.9 μL/L in the fumigant assay and LD50 from 24.5 to 45.1 μg/insect in the topical contact assay) and T. castaneum (LC50 ranging from 1.4 to 35.2 μL/L and LD50 from 1.9 to 17.6 μg/insect). Preliminary structure-activity relationship analysis revealed: a) halogenation and epoxidation of the monoterpenoids significantly decreased their insecticidal efficacy, except for compound 21, which exhibited greater contact toxicity against T. castaneum; b) hydrogenation of the double bond reduced fumigant activity on both insects; c) reduction of the carbonyl group to an alcohol diminished fumigant activity, highlighting the importance of the carbonyl group in insecticidal activity; d) double bond isomerization affected insecticidal activity, emphasizing the relevance of exocyclic α,β-unsaturated carbonyl systems for insecticidal activity. Finally, the ICs with the EOs of S. viminea and M. mollis were obtained, which showed insecticidal activity against S. zeamais and T. castaneum after 48 hours of treatment, with maximum effects observed between 96 and 148 hours. The IC based on S. viminea EO stood out with over 80% mortality at 120 hours. This study significantly contributes to the development of new insecticides based on compounds derived from aromatic species, offering promising alternatives for controlling pests in stored grains. The findings open new perspectives in the search for sustainable and effective solutions for agricultural product protection, highlighting the potential of these natural compounds in integrated pest management and reducing dependency on synthetic pesticides.eng
dc.description.degreelevelMaestríaspa
dc.description.degreenameMagíster en Ciencias - Químicaspa
dc.description.methodsEl análisis CG-EM se realizó en un cromatógrafo de gases Shimadzu GC 2010 Plus, el cual estaba acoplado a un detector selectivo de masas GCMS-TQ 8040 (Shimadzu© , Kioto, Japón) en modo de impacto electrónico (IE), operando a 70 eV con un analizador de cuadrupolo en modo de escaneo completo a 4.57 s⁻¹. Los espectros de masas se adquirieron en el rango de 40 a 400 m/z. Se realizaron dos análisis diferentes para los AEs utilizando dos columnas de polaridad ortogonal: columna DB-5MS ((5%)-fenilmetilpolisiloxano, 60 m × 0.25 mm × 0.25 μm) y columna HP-INNOWax (polietilenglicol (PEG), 60 m × 0.25 mm × 0.25 μm) adquiridas de Agilent Technologies (Santa Clara, CA, EE. UU.). Los índices de retención (IR) se calcularon usando una solución estándar de alcanos (C7–C40) a 1000 ppm adquirida en Sigma-Aldrich© (Saint Louis, MO, EE. UU.). El aislamiento y purificación de los compuestos químicos presentes en los AEs y de los compuestos obtenidos mediante modificaciones sintéticas se realizó mediante Cromatografía Flash (CF) en sílice gel SiliaFlash® P60 de tamaño 25–40 μm (SiliCycle® Inc., Quebec, QC, Canadá). Los estudios cromatográficos, el monitoreo de las CF y el control de pureza se realizaron por cromatografía en capa delgada (CCD) utilizando placas de aluminio SiliaPlateTM recubiertas con sílice gel P60 F254 de tamaño 5–20 μm (SiliCycle ® Inc., Quebec, QC, Canadá), utilizando luz UV (254 y 365 nm) vapores de yodo y una solución de 0.1% de vainillina en H2SO4. Se empleó un evaporador rotativo Heidolph HeiVAP (Heidolph Instruments GmbH & Co. KG, Schwabach, Alemania) en los procesos de eliminación y recuperación de solventes. Los solventes utilizados en las separaciones cromatográficas fueron adquiridos comercialmente en calidad técnica y fueron destilados y secados, antes de su uso. Los demás reactivos empleados en este estudio fueron adquiridos comercialmente y utilizados sin purificación previa. Los compuestos aislados y sintetizados se caracterizaron por sus propiedades físicas, espectros de RMN y por comparación con datos de la literatura. Las rotaciones ópticas fueron medidas en un polarímetro Atago® Polax-2L (Fukuya, Saitama, Japón) a 25 °C usando una lámpara de sodio a una longitud de onda de 589 nm. Las mediciones de RMN se realizaron en un equipo Bruker Advance AC-400 operado a 400 MHz para ¹H y a 100 MHz para APT a 25 °C (Bruker® , Hamburgo, Alemania), y utilizando cloroformo deuterado (CDCl3) como disolvente. Los desplazamientos químicos (δ) se expresan en partes por millón (ppm), y las constantes de acoplamiento (J) en Hertz (Hz). Se utilizaron las siguientes abreviaturas para indicar la multiplicidad de los desplazamientos químicos: s = singlete, d = doblete, dd = doble doblete, ddd = doble doble doblete, td = triple doblete, tdd = triple doble doblete, t = triplete, q = cuarteto, m = multiplete, brs = singlete ancho. Las eficiencias de encapsulación fueron medidas a través de un lector de microplacas Thermo Scientific Multiskan GO con la ayuda de un plato µDropTM (Thermo Scientific© , Waltham, MA, EE. UU.). La composición química de las sustancias encapsuladas se hizo mediante análisis de CG-EM, en el equipo previamente descrito. El análisis espectroscópico de los complejos de inclusión (CI) se realizó mediante análisis de RMN utilizando el quipo descrito anteriormente. El análisis de infrarrojo (IR) se realizó utilizando un espectrofotómetro Shimadzu modelo MIRACLE 10 ZnSe (Shimadzu© , Kyoto, Japón). Los análisis termogravimétricos se midieron utilizando una termobalanza. del sistema TGA/DSC de marca TA instrument SDT-Q600 (WatersTM, Lukens, New Castle. EE. UU.).spa
dc.description.researchareaQuímica de Productos Naturalesspa
dc.format.extent176 páginasspa
dc.format.mimetypeapplication/pdfspa
dc.identifier.instnameUniversidad Nacional de Colombiaspa
dc.identifier.reponameRepositorio Institucional Universidad Nacional de Colombiaspa
dc.identifier.repourlhttps://repositorio.unal.edu.co/spa
dc.identifier.urihttps://repositorio.unal.edu.co/handle/unal/87683
dc.language.isospaspa
dc.publisherUniversidad Nacional de Colombiaspa
dc.publisher.branchUniversidad Nacional de Colombia - Sede Bogotáspa
dc.publisher.facultyFacultad de Cienciasspa
dc.publisher.placeBogotá, Colombiaspa
dc.publisher.programBogotá - Ciencias - Maestría en Ciencias - Químicaspa
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dc.rights.accessrightsinfo:eu-repo/semantics/openAccessspa
dc.rights.licenseAtribución-NoComercial-SinDerivadas 4.0 Internacionalspa
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/spa
dc.subject.ddc620 - Ingeniería y operaciones afines::628 - Ingeniería sanitariaspa
dc.subject.ddc630 - Agricultura y tecnologías relacionadas::632 - Lesiones, enfermedades, plagas vegetalesspa
dc.subject.ddc660 - Ingeniería química::664 - Tecnología de alimentosspa
dc.subject.lembINSECTICIDAS DE ORIGEN VEGETALspa
dc.subject.lembBotanical insecticideseng
dc.subject.lembPLANTAS INSECTICIDASspa
dc.subject.lembPlants, insecticidaleng
dc.subject.lembALMACENAMIENTO DE ALIMENTOSspa
dc.subject.lembFood - Storageeng
dc.subject.lembPLAGAS DE ALIMENTOS ALMACENADOSspa
dc.subject.lembFood storage pestseng
dc.subject.lembALMACENAMIENTO DE PRODUCTOS AGRICOLAS-ENFERMEDADES Y DAÑOSspa
dc.subject.lembFarm produce - storage - diseases and injurieseng
dc.subject.proposalMinthostachys mollisspa
dc.subject.proposalTagetes zypaquirensisspa
dc.subject.proposalAnethum graveolensspa
dc.subject.proposalSatureja vimineaspa
dc.subject.proposalToxicidad fumigantespa
dc.subject.proposalToxicidad por contactospa
dc.subject.proposalMonoterpenoidesspa
dc.subject.proposalMinthostachys molliseng
dc.subject.proposalTagetes zypaquirensiseng
dc.subject.proposalAnethum graveolenseng
dc.subject.proposalSatureja vimineaeng
dc.subject.proposalFumigant toxicityeng
dc.subject.proposalContact toxicityeng
dc.subject.proposalMonoterpenoidseng
dc.titleEstudio de potenciales insecticidas derivados de especies aromáticas con alto contenido de monoterpenoides para el control de Sitophilus Zeamais y Tribolium Castaneumspa
dc.title.translatedStudy of insecticidal potentials derived from aromatic species with high monoterpenoid content for the control of Sitophilus Zeamais and Tribolium Castaneumeng
dc.typeTrabajo de grado - Maestríaspa
dc.type.coarhttp://purl.org/coar/resource_type/c_bdccspa
dc.type.coarversionhttp://purl.org/coar/version/c_ab4af688f83e57aaspa
dc.type.contentTextspa
dc.type.driverinfo:eu-repo/semantics/masterThesisspa
dc.type.redcolhttp://purl.org/redcol/resource_type/TMspa
dc.type.versioninfo:eu-repo/semantics/acceptedVersionspa
oaire.accessrightshttp://purl.org/coar/access_right/c_abf2spa

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