11 results on '"Felipe Barrera‐Méndez."'
Search Results
2. Synthesis and Insecticidal Evaluation of Chiral Neonicotinoids Analogs: The Laurel Wilt Case
- Author
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Saúl A. Luna-Hernández, Israel Bonilla-Landa, Alfonso Reyes-Luna, Alfredo Rodríguez-Hernández, Ulises Cuapio-Muñoz, Luis A. Ibarra-Juárez, Gabriel Suarez-Mendez, Felipe Barrera-Méndez, Irving D. Pérez-Landa, Francisco J. Enríquez-Medrano, Ramón E. Díaz de León-Gómez, and José L. Olivares-Romero more...
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neonicotinoids ,nitroguanidines ,chiral ,enantiopure compound ,insecticidal activity ,Organic chemistry ,QD241-441 - Abstract
Xyleborus sp beetles are types of ambrosia beetles invasive to the United States and recently also to Mexico. The beetle can carry a fungus responsible for the Laurel Wilt, a vascular lethal disease that can host over 300 tree species, including redbay and avocado. This problem has a great economic and environmental impact. Indeed, synthetic chemists have recently attempted to develop new neonicotinoids. This is also due to severe drug resistance to “classic” insecticides. In this research, a series of neonicotinoids analogs were synthesized, characterized, and evaluated against Xyleborus sp. Most of the target compounds showed good to excellent insecticidal activity. Generally, the cyclic compounds also showed better activity in comparison with open-chain compounds. Compounds R-13, 23, S-29, and 43 showed a mortality percent of up to 73% after 12 h of exposure. These results highlight the enantioenriched compounds with absolute R configuration. The docking results correlated with experimental data which showed both cation-π interactions in relation to the aromatic ring and hydrogen bonds between the search cavity 3C79 and the novel molecules. The results suggest that these sorts of interactions are responsible for high insecticidal activity. more...
- Published
- 2021
- Full Text
- View/download PDF
Catalog
3. Chiral Hydroxamic Acid Ligands in Asymmetric Synthesis: The Evolution of Metal‐Catalyzed Oxidation Reactions
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Tushar Janardan Pawar, Israel Bonilla‐Landa, Alfonso Reyes‐Luna, Felipe Barrera‐Méndez., Francisco Javier Enríquez‐Medrano, Ramón Enrique Díaz‐de‐León‐Gómez, and José Luis Olivares‐Romero
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General Chemistry - Published
- 2023
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4. Nanoencapsulation of Permethrin in Polylactic Acid to Enhance Insecticide Persistence for Scolytinae Pest Control
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Irving David Pérez-Landa, Guadalupe Hernández-Cervantes, Mónica Vázquez, Israel Bonilla-Landa, Siuly Xenia Ramos Cruz, José Luis Olivares-Romero, Luis Arturo Ibarra-Juárez, and Felipe Barrera-Méndez
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0106 biological sciences ,Materials science ,business.industry ,Pest control ,food and beverages ,02 engineering and technology ,021001 nanoscience & nanotechnology ,01 natural sciences ,Persistence (computer science) ,Toxicology ,010602 entomology ,chemistry.chemical_compound ,Polylactic acid ,chemistry ,medicine ,0210 nano-technology ,business ,Permethrin ,medicine.drug - Abstract
Nanotechnology can be used to protect plants against Fusarium Dieback and the Laurel Wilt, that are new and lethal insect-vectored diseases that can host over 300 tree species, including avocado trees. The vectors of these diseases are beetles members of the Scolytinae subfamily, notoriously difficult to control because they spend most of their lives hidden within galleries. Nevertheless, when tested on avocado bolts, some insecticides (including permethrin) provided a reduction in the number of entrance holes or beetle emergence, but the persistence of pesticide residues might have been influenced by factors like rainfall and sunlight. The present study aims to encapsulate permethrin in polylactic acid nanospheres, conferring protection against losses by physic and chemical factors, ultimately increasing its persistence. The particle size, zeta potential, and encapsulation efficiency obtained were 393nm, -32mV, and 27%, respectively. After 96 h of exposure to UV-A light, the insecticidal activity of unencapsulated permethrin was severely diminished, having a reduction in mortality in scolytinae beetles from 80% to 40%, while the nanoencapsulated permethrin retained a 70%. The study has concluded the potential advantage of formulating permethrin into nanometric biodegradable spheres, enhancing the persistence of the insecticide while removing the use of toxic organic solvents as vehicle for the active ingredient, reducing the environmental impact.) more...
- Published
- 2021
- Full Text
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5. Photoprotection and release study of spinosad biopolymeric microparticles obtained by spray drying
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Juan L. Monribot-Villanueva, W. Ramos-Torres, I.D. Pérez-Landa, Felipe Barrera-Méndez, Mónica Ramírez-Vázquez, José Luis Olivares-Romero, Israel Bonilla-Landa, and R. Lasa
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Materials science ,Carrier system ,Scanning electron microscope ,Sodium lignosulfonate ,General Chemical Engineering ,Spinosad ,02 engineering and technology ,021001 nanoscience & nanotechnology ,Chitosan ,chemistry.chemical_compound ,020401 chemical engineering ,chemistry ,Chemical engineering ,Spray drying ,medicine ,Particle size ,0204 chemical engineering ,0210 nano-technology ,Photodegradation ,medicine.drug - Abstract
Microparticles containing the photosensitive spinosad (SP) were obtained using a combination of chitosan (CH) and sodium lignosulfonate (SL) as encapsulating materials to develop a photoprotective system for intake administration. The microparticles were obtained by a spray drying technique and were characterized in terms of morphology (scanning electron microscopy - SEM) and particle size. In vitro release studies showed an initial burst effect that fits very well with the zero order kinetic model and then a slow release of the bioinsecticide, which fits best with the first order model. The results of this work demonstrate that the bioinsecticide carrier system developed with natural polymeric materials presents high stability to photodegradation and adequate insecticide release for use as a strategy to reduce negative impacts on the environment in agronomic practices. more...
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- 2021
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6. Synthesis and Insecticidal Evaluation of Chiral Neonicotinoids Analogs: The Laurel Wilt Case
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Alfredo Rodríguez-Hernández, Saúl A. Luna-Hernández, Felipe Barrera-Méndez, Irving David Pérez-Landa, Gabriel Suarez-Mendez, Israel Bonilla-Landa, Ramón Díaz de León-Gómez, Alfonso Reyes-Luna, Ulises Cuapio-Muñoz, José Luis Olivares-Romero, Luis Arturo Ibarra-Juárez, and Francisco Javier Enríquez-Medrano more...
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0106 biological sciences ,Insecticides ,enantiopure compound ,Stereochemistry ,Pharmaceutical Science ,Fungus ,010402 general chemistry ,01 natural sciences ,Laurel wilt ,Article ,Analytical Chemistry ,insecticidal activity ,Trees ,Xyleborus ,Neonicotinoids ,QD241-441 ,Drug Discovery ,Animals ,Physical and Theoretical Chemistry ,Plant Diseases ,biology ,Host (biology) ,Chemistry ,Organic Chemistry ,Fungi ,Hydrogen Bonding ,biology.organism_classification ,0104 chemical sciences ,chiral ,Coleoptera ,010602 entomology ,nitroguanidines ,Chemistry (miscellaneous) ,Docking (molecular) ,Molecular Medicine ,Weevils ,Ericaceae ,Ambrosia ,Tree species - Abstract
Xyleborus sp beetles are types of ambrosia beetles invasive to the United States and recently also to Mexico. The beetle can carry a fungus responsible for the Laurel Wilt, a vascular lethal disease that can host over 300 tree species, including redbay and avocado. This problem has a great economic and environmental impact. Indeed, synthetic chemists have recently attempted to develop new neonicotinoids. This is also due to severe drug resistance to “classic” insecticides. In this research, a series of neonicotinoids analogs were synthesized, characterized, and evaluated against Xyleborus sp. Most of the target compounds showed good to excellent insecticidal activity. Generally, the cyclic compounds also showed better activity in comparison with open-chain compounds. Compounds R-13, 23, S-29, and 43 showed a mortality percent of up to 73% after 12 h of exposure. These results highlight the enantioenriched compounds with absolute R configuration. The docking results correlated with experimental data which showed both cation-π interactions in relation to the aromatic ring and hydrogen bonds between the search cavity 3C79 and the novel molecules. The results suggest that these sorts of interactions are responsible for high insecticidal activity. more...
- Published
- 2021
7. Hafnium(IV) Chloride Catalyzes Highly Efficient Acetalization of Carbonyl Compounds
- Author
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José Luis Olivares-Romero, Emizael López-Hernández, Israel Bonilla-Landa, Felipe Barrera-Méndez, and Nadia C. Salas
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chemistry.chemical_classification ,Aldehydes ,Ketone ,Trimethyl orthoformate ,Organic Chemistry ,Acetal ,Cyclohexanone ,Ketones ,Biochemistry ,Aldehyde ,Catalysis ,Heating ,chemistry.chemical_compound ,Acetals ,chemistry ,Benzophenone ,Organic chemistry ,Microwaves ,Hafnium ,Acetophenone - Abstract
Background: Hafnium(IV) tetrachloride efficiently catalyzes the protection of a variety of aldehydes and ketones, including benzophenone, acetophenone, and cyclohexanone, to the corresponding dimethyl acetals and 1,3-dioxolanes, under microwave heating. Substrates possessing acid-labile protecting groups (TBDPS and Boc) chemoselectively generated the corresponding acetal/ketal in excellent yields. Aim and Objective: In this study. the selective protection of aldehydes and ketones using a Hafnium(IV) chloride, which is a novel catalyst, under microwave heating was observed. Hence, it is imperative to find suitable conditions to promote the protection reaction in high yields and short reaction times. This study was undertaken not only to find a novel catalyst but also to perform the reaction with substrates bearing acid-labile protecting groups, and study the more challenging ketones as benzophenone. Materials and Methods: Using a microwave synthesis reactor Monowave 400 of Anton Paar, the protection reaction was performed on a raging temperature of 100°C ±1, a pressure of 2.9 bar, and an electric power of 50 W. More than 40 substrates have been screened and protected, not only the aldehydes were protected in high yields but also the more challenging ketones such as benzophenone were protected. All the products were purified by simple flash column chromatography, using silica gel and hexanes/ethyl acetate (90:10) as eluents. Finally, the protected substrates were characterized by NMR 1H, 13C and APCI-HRMS-QTOF. Results: Preliminary screening allowed us to find that 5 mol % of the catalyst is enough to furnish the protected aldehyde or ketone in up to 99% yield. Also it was found that substrates with a variety of substitutions on the aromatic ring (aldehyde or ketone), that include electron-withdrawing and electrondonating group, can be protected using this methodology in high yields. The more challenging cyclic ketones were also protected in up to 86% yield. It was found that trimethyl orthoformate is a very good additive to obtain the protected acetophenone. Finally, the protection of aldehydes with sensitive functional groups was performed. Indeed, it was found that substrates bearing acid labile groups such as Boc and TBDPS, chemoselectively generated the corresponding acetal/ketal compound while keeping the protective groups intact in up to 73% yield. Conclusion: Hafnium(IV) chloride as a catalyst provides a simple, highly efficient, and general chemoselective methodology for the protection of a variety of structurally diverse aldehydes and ketones. The major advantages offered by this method are: high yields, low catalyst loading, air-stability, and non-toxicity. more...
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- 2019
- Full Text
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8. l-Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs
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Alfonso Reyes-Luna, Ulises Cuapio-Muñoz, José Luis Olivares-Romero, Axel Luna-Hernández, Ramón E. Díaz de León, Israel Bonilla-Landa, Gabriel Suarez-Mendez, J. Francisco Enríquez-Medrano, Felipe Barrera-Méndez, Alfredo Rodríguez-Hernández, Arturo Ibarra-Juarez, and Nadia L. Caram-Salas more...
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0106 biological sciences ,Scaffold ,Insecticides ,Molecular Structure ,Proline ,Stereochemistry ,Xyleborus affinis ,Chemistry ,010401 analytical chemistry ,Neonicotinoid ,General Chemistry ,01 natural sciences ,0104 chemical sciences ,Coleoptera ,Molecular Docking Simulation ,Neonicotinoids ,Docking (dog) ,Enantiopure drug ,Animals ,General Agricultural and Biological Sciences ,010606 plant biology & botany - Abstract
In this research, six neonicotinoid analogs derived from l-proline were synthesized, characterized, and evaluated as insecticides against Xyleborus affinis. Most of the target compounds showed good... more...
- Published
- 2021
9. Increased insecticidal activity by photoprotection of microencapsulated spinosad in a dry phagostimulant formulation against Drosophila suzukii
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Irving D. Pérez-Landa, Rodrigo Lasa, P.I. Gonzalez-Chi, Israel Bonilla-Landa, José L. Olivares-Romero, and Felipe Barrera-Méndez
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Agronomy and Crop Science - Published
- 2022
- Full Text
- View/download PDF
10. Propiconazole nanoencapsulation in biodegradable polymers to obtain pesticide controlled delivery systems
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Juan Luis Monribot Villanueva, José Benjamín Rodríguez Haas, José Luis Olivares Romero, Felipe Barrera Méndez, Israel Bonilla Landa, Diana Sánchez Rangel, and Diter Augusto Miranda Sánchez
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Active ingredient ,0303 health sciences ,Chemistry ,Environmental pollution ,04 agricultural and veterinary sciences ,General Chemistry ,Pesticide ,Pulp and paper industry ,Biodegradable polymer ,Lactic acid ,Fungicide ,Propiconazole ,03 medical and health sciences ,chemistry.chemical_compound ,Controlled delivery ,040102 fisheries ,0401 agriculture, forestry, and fisheries ,030304 developmental biology - Abstract
The nanoencapsulation of pesticides in biodegradable polymers confers several advantages to conventional agrochemicals, such as protection against losses due volatilization and degradation of the active ingredient, as well as the augment of water dispersion, allowing for their application on crops without requiring the use of organic solvents that could harm the user and the environment. This characteristics could enhance the productivity, reducing both costs and environmental pollution. In this work the propiconazole fungicide, forming part of a commercial formulation as well as in its pure state, was encapsulated using as carriers the biodegradable polymer poly lactic acid (PLA) and the biodegradable co-polymer poly (lactic-co-glicolic) acid, all with the aim of generate controlled fungicide release systems to augment the efficiency of the treatments of the Fusarium dieback disease. The most efficient system obtained presented nanospheres of 146.28 nm and an encapsulation efficiency over 42%. The antifungal activity tests showed that the use of this nanoencapsulated fungicide system enhances the growth inhibition percentage in 5%, obtaining a formulation that presents good dispersion in water without the need of organic emulsifier agents. more...
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- 2019
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11. Design, synthesis and biological evaluation of novel fungicides for the management of Fusarium DieBack disease
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Ramon Enrique Diaz De Leon Gomez, Felipe Barrera Méndez, Randy Ortiz Castro, Israel Bonilla Landa, Osvaldo León de la Cruz, José Luis Olivares Romero, Francisco Javier Enriquez Medrano, Benjamin Rodriguez Haas, and Diana Sánchez Rangel more...
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Antifungal ,Fusarium ,biology ,Traditional medicine ,medicine.drug_class ,General Chemistry ,biology.organism_classification ,Fungicide ,Fusarium euwallaceae ,Design synthesis ,medicine ,Fusarium solani ,Tree species ,Biological evaluation - Abstract
Fusarium Dieback, a new and lethal insect-vectored disease can host over 300 tree species including the avocado trees. This problem has recently attracted the attention of synthetic chemist not only to develop new triazol antifungal agents but also due to severe drug resistance to “classic” triazol antifungal agents. Here, a series of novel antifungal triazoles with a p-trifluoromethylphenyl moiety were synthesized and characterized by spectroscopic and spectrometric methods. Most of the target compounds synthesized showed from modest to good inhibitory activity and less phytotoxicity in comparison with the commercially available propiconazol; in particular, compounds 7 and 13 were active against both Fusarium solani and Fusarium euwallaceae. The results showed that compounds 7, 13, and 4 have great potential to be developed as new antifungal agents because of both good antifungal activity and low phytotoxicity. SAR showed that free alcohols and not O-protected compounds significantly influence the activity. Hence, a-methyl-a-1,2,4-triazole emerged as novel compound to develop new ketone-triazole-type antifungal agents for the management of Fusarium Dieback disease Resumen. Fusarium Dieback es una nueva enfermedad letal transmitida por insectos que actúan como vectores y puede atacar a más de 300 especies de árboles, incluidos los árboles de aguacate. Recientemente, este problema ha atraído la atención de los químicos sintéticos para desarrollar nuevos agentes antifúngicos triazólicos debido a la resistencia severa que desarrollan los insectos a los agentes antifúngicos triazólicos "clásicos". Durante este trabajo, se sintetizaron nuevos triazoles antifúngicos que contienen un grupo p-trifluorometilfenilo y se caracterizaron por métodos espectroscópicos y espectrométricos. La mayoría de los compuestos diana sintetizados mostraron una actividad inhibidora de modesta a buena y menos fitotoxicidad en comparación con el propiconazol que es comercialmente disponible; en particular, los compuestos 7 y 13 mostraron ser activos contra Fusarium solani y Fusarium euwallaceae. Los resultados mostraron que los compuestos 7, 13 y 4 tienen un gran potencial para desarrollarse como nuevos agentes antifúngicos debido a la buena actividad antifúngica y su baja fitotoxicidad. SAR mostró que los alcoholes libres y no los compuestos O-protegidos influyen significativamente en la actividad. Por lo tanto, el α-metil-α-1,2,4-triazol surgió como un nuevo compuesto líder para desarrollar nuevos agentes antifúngicos tipo cetona-triazol para el tratamiento de la enfermedad Fusarium Dieback. more...
- Published
- 2019
- Full Text
- View/download PDF
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