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1.
Chembiochem ; 25(7): e202300742, 2024 Apr 02.
Artículo en Inglés | MEDLINE | ID: mdl-38426686

RESUMEN

Pesticides are essential in agricultural development. Controlled-release pesticides have attracted great attentions. Base on a principle of spatiotemporal selectivity, we extended the photoremovable protective group (PRPG) into agrochemical agents to achieve controllable release of active ingredients. Herein, we obtained NP-TBZ by covalently linking o-nitrobenzyl (NP) with thiabendazole (TBZ). Compound NP-TBZ can be controlled to release TBZ in dependent to light. The irradiated and unirradiated NP-TBZ showed significant differences on fungicidal activities both in vitro and in vivo. In addition, the irradiated NP-TBZ displayed similar antifungal activities to the directly-used TBZ, indicating a factual applicability in controllable release of TBZ. Furthermore, we explored the action mode and microcosmic variations by SEM analysis, and demonstrated that the irradiated NP-TBZ retained a same action mode with TBZ against mycelia growth.


Asunto(s)
Plaguicidas , Tiabendazol , Tiabendazol/farmacología , Tiabendazol/análisis , Preparaciones de Acción Retardada , Antifúngicos/farmacología
2.
Int Microbiol ; 2024 Aug 26.
Artículo en Inglés | MEDLINE | ID: mdl-39186133

RESUMEN

Dermatophyte infections globally account for 20 to 25% of fungal infections. Dermatophytes have begun exhibiting antifungal drug resistance, making it challenging to treat this particular infection. Essential oils could be used as alternative solutions as they have been used for a long period to treat different infections. The research has demonstrated the antifungal efficacy of cinnamon, clove, lemongrass, tea tree, thyme, and garlic essential oils, and the impact of their combinations was assayed against Microsporum canis, Trichophyton tonsurans, T. violaceum, T. verrucosum, and Epidermophyton floccosum. Polymerase chain reaction (PCR)-restriction fragment length polymorphism (RFLP) was used to identify the most prevalent M. canis. The accession number of M. canis was obtained as ON007275. All tested essential oils exhibited antidermatophytic action except garlic. A synergistic effect was attained by cinnamon + clove, cinnamon + lemongrass, clove + lemongrass, clove + tea tree, and thyme + tea tree combinations. Concerning antifungal activity, M. canis was the most susceptible dermatophytic species, except in the case of thyme T. violaceum, which was the most susceptible dermatophytic species. The maximum inhibition was recorded in the cases of cinnamon and cinnamon + lemongrass combination against M. canis. The least minimum inhibitory concentrations were attained by cinnamon and clove against M. canis, cinnamon + clove against M. canis and T. violaceum, and cinnamon + lemongrass against M. canis, T. violaceum, T. verrucosum, and E. floccosum. The least minimum fungicidal concentration showed by cinnamon against M. canis, cinnamon + clove against M. canis and T. violaceum, cinnamon + lemongrass against M. canis, T. violaceum, T. verrucosum, and E. floccosum, and clove + lemongrass against M. canis.

3.
Bioorg Med Chem Lett ; 108: 129813, 2024 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-38788964

RESUMEN

Succinate dehydrogenase inhibitors are essential fungicides used in agriculture. To explore new pyrazole-carboxamides with high fungicidal activity, a series of N-substitutedphenyl-3-di/trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamides bearing a branched alkyl ether moiety were designed and synthesized. The in vitro bioassay indicated that some target compounds displayed appreciable fungicidal activity. For example, compounds 5d and 5e showed high efficacy against S. sclerotiorum with EC50 values of 3.26 and 1.52 µg/mL respectively, and also exhibited excellent efficacy against R. solani with EC50 values of 0.27 and 0.06 µg/mL respectively, which were comparable or superior to penflufen. The further in vivo bioassay on cucumber leaves demonstrated that 5e provided strong protective activity of 94.3 % against S. sclerotiorum at 100 µg/mL, comparable to penflufen (99.1 %). Cytotoxicity assessment against human renal cell lines (239A cell) revealed that 5e had low cytotoxicity within the median effective concentrations. Docking study of 5e with succinate dehydrogenase illustrated that R-5e formed one hydrogen bond and two π-π stacking interactions with amino acid residues of target enzyme, while S-5e formed only one π-π stacking interaction with amino acid residue. This study provides a valuable reference for the design of new succinate dehydrogenase inhibitor.


Asunto(s)
Fungicidas Industriales , Simulación del Acoplamiento Molecular , Pirazoles , Succinato Deshidrogenasa , Pirazoles/química , Pirazoles/farmacología , Pirazoles/síntesis química , Humanos , Relación Estructura-Actividad , Fungicidas Industriales/farmacología , Fungicidas Industriales/síntesis química , Fungicidas Industriales/química , Succinato Deshidrogenasa/antagonistas & inhibidores , Succinato Deshidrogenasa/metabolismo , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Ascomicetos/efectos de los fármacos , Amidas/química , Amidas/farmacología , Amidas/síntesis química , Relación Dosis-Respuesta a Droga , Éteres/química , Éteres/farmacología , Éteres/síntesis química , Rhizoctonia
4.
Bioorg Chem ; 153: 107757, 2024 Aug 29.
Artículo en Inglés | MEDLINE | ID: mdl-39226649

RESUMEN

Diseases caused by plant viruses and pathogens pose a serious threat to crop yield and quality. Traditional pesticides have gradually developed drug resistance and brought certain environmental safety issues during long-term overuse. There is an urgent need to discover new candidate compounds to address these issues. In this study, we achieved the efficient synthesis of iheyamine A and its derivatives, and discovered their excellent antiviral activities against tobacco mosaic virus (TMV). Most compounds displayed higher antiviral activities against TMV than commercial ribavirin at 500 µg/mL, with compounds 3a (Inactive effect IC50: 162 µg/mL), 3d (Inactive effect IC50: 249 µg/mL), 6p (Inactive effect IC50: 254 µg/mL), and 7a (Inactive effect IC50: 234 µg/mL) exhibiting better antiviral activities than ningnanmycin at 500 µg/mL (Inactive effect IC50: 269 µg/mL). Meanwhile, the structure-activity relationships of this type of compounds were systematically studied. We chose 3a for further antiviral mechanism research and found that it can directly act on viral coat protein (CP). The interaction of 3a and CP was further verified via molecular docking. These compounds also showed broad-spectrum fungicidal activities against 8 plant pathogenic fungi, especially for P. piricola. This study provides a reference for the role of iheyamine alkaloids in combating plant pathogenic diseases.

5.
Environ Res ; 246: 118061, 2024 Apr 01.
Artículo en Inglés | MEDLINE | ID: mdl-38157967

RESUMEN

This research was performed to investigate the bactericidal and fungicidal competence of extracts (methanol and petroleum ether extract) of Polyalthia longifolia leaf. Moreover, the major active compounds present in the effective crude extract (either methanol or petroleum ether extract) was determined through initially with UV-Vis spectra, FTIR, and GC-MS analyses. The methanol extract alone showed remarkable bactericidal and fungicidal activity against the bacterial (S. pyogenes > E. coli > S. aureus > S. pneumoniae > C. difficile > P. aeruginosa) and fungal (A. clavatus > C. albicans > A. niger > A. fumigatus > C. tropicalis > C. auris) pathogens at increased concentration (12.5 mg mL-1) than petroleum ether extract. The MIC and MBC values of methanol extract were found as 10-20 mg mL-1 and 30-40 mg mL-1 respectively. The MFC value of methanol extract was found as 10-20 mg mL-1. These MIC, MBC, and MFC values of methanol extract were considerably greater than petroleum ether extract. The FTIR and GC-MS characterization studies revealed that the presence of more acre functional groups belonging to bioactive compounds such as Z)-7-Hexadecenal, Aromandendrene, α-Curcumene, Caryophyllene, Methyl 14-methyl Pentadecanoat, Methyl trans-13-Octadecenoate, 9-Octadecenoic acid (Z)-, and 2-hydroxy-1- (hydroxymethyl)ethyl. As a result of these findings, it is possible that P. longifolia leaf methanol extract contains medicinally important bioactive substances with bactericidal and fungicidal properties.


Asunto(s)
Alcanos , Antiinfecciosos , Clostridioides difficile , Fungicidas Industriales , Polyalthia , Extractos Vegetales/farmacología , Metanol , Escherichia coli , Staphylococcus aureus , Antiinfecciosos/farmacología , Antibacterianos/farmacología , Solventes , Candida albicans
6.
Food Microbiol ; 121: 104523, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38637085

RESUMEN

This study investigated the fungicidal efficiency and mechanism of action of dielectric barrier discharge cold atmosphere plasma (DBD-CAP) in inactivating Aspergillus niger (A. niger) spores. The disinfection efficacy and quality of dried jujube used as the processing application object were also studied. The results indicated that the Weibull + Tail model performed better for spore inactivation curves at different voltages among various treatment times, and the spore cells were reduced by 4.05 log (cfu/mL) in spores suspension at 70 kV after 15 min of treatment. This disinfection impact was further supported by scanning electron microscope (SEM) and transmission electron microscopy (TEM) images, which showed that the integrity of the cell membrane was damaged, and the intracellular content leaked out after DBD-CAP treatment. Elevated levels of reactive oxygen species (ROS) during the treatment increased the relative conductivity of cells, and leakage of nucleic acids and proteins further supported the disinfection impact. Additionally, the growth and toxicity of surviving A. niger spores after treatment were also greatly reduced. When DBD-CAP was applied to disinfecting dried jujube, the spore number exhibited a 2.67 log cfu/g reduction after treatment without significant damage observed onto the quality (P > 0.05).


Asunto(s)
Aspergillus , Gases em Plasma , Ziziphus , Aspergillus niger , Gases em Plasma/farmacología , Desinfección/métodos
7.
Pestic Biochem Physiol ; 203: 106025, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-39084764

RESUMEN

Peanut web blotch (PWB) caused by Phoma arachidicola, is one of the most serious foliar diseases of peanut. Although prochloraz is an active fungicide with broad anti-fungal spectrum, it has not been registered for the control of PWB in China. The activity of prochloraz against P. arachidicola and the risk of resistance to prochloraz in P. arachidicola are still unclear. In current study, the inhibitory activity of prochloraz against 96 P. arachidicola strains was determined with the average EC50 value of 1.2700 ± 0.7786 µg/mL. Prochloraz exhibited excellent protective and curative effect on detached peanut leaves, and the effect was obviously better than that of carbendazim and difenoconazole at the same concentration. After prochloraz treatment, the mycelium of P. arachidicola contorted, shrunk and ruptured, with shrinking of cell wall and membrane, enhanced cell membrane permeability, and reduced ergosterol content. Totally 80 prochloraz-resistant mutants were obtained by fungicide adaptation with the frequency of 6.7 × 10-3. All the selected 12 prochloraz-resistant mutants lost their resistance to prochloraz after 10 transfers on PDA plates. And these mutants exhibited decreased biological fitness in mycelial growth and pathogenicity. Moreover, there was positive cross-resistance between prochloraz and other demethylation inhibitor (DMI) fungicides, such as tebuconazole, triflumizole and difenoconazole, but no cross-resistance was found between prochloraz and other classes of fungicides, such as carbendazim, pydiflumetofen or fludioxonil. Overexpression of PaCYP51 and PaAtrB genes were detected in the resistant mutants. All the above results demonstrated that prochloraz has a great potential in management of PWB. The risk of P. arachidicola developing resistance to prochloraz is relatively low-to-medium. Overexpressing of PaCYP51 and PaAtrB might be linked to prochloraz resistance in P. arachidicola.


Asunto(s)
Arachis , Ascomicetos , Farmacorresistencia Fúngica , Fungicidas Industriales , Imidazoles , Enfermedades de las Plantas , Ascomicetos/efectos de los fármacos , Ascomicetos/genética , Fungicidas Industriales/farmacología , Imidazoles/farmacología , Farmacorresistencia Fúngica/genética , Enfermedades de las Plantas/microbiología , Arachis/microbiología , Medición de Riesgo , Carbamatos/farmacología , Mutación , Bencimidazoles
8.
Chem Biodivers ; 21(5): e202400311, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38494946

RESUMEN

Phytopathogenic fungi is the most devastating reason for the decrease of the agricultural production and food safety. To develop new fungicidal agents for resistance concerning, a novel series of aminocoumarin derivatives were synthesized and their fungicidal activity were investigated both in vitro and in vivo. Transmission electron microscope (TEM), scanning electron microscope (SEM), RNA-Seq, 3D-QSAR and molecular docking were applied to reveal the underlying anti-fungal mechanisms. Most of the compounds exhibited significant fungicidal activity. Notably, compound 10c had a more extensive fungicidal effect than positive control. TEM indicated that compound 10c could cause abnormal morphology of cell walls, vacuoles and release of cellular contents. Transcriptional analysis data indicated that 895 and 653 out of 1548 differential expressed genes (DEGs) were up-regulated and down-regulated respectively. The Go and KEGG enrichment indicated that the coumarin derivatives could induce significant changes of succinate dehydrogenase (SDH), Acetyl-coenzyme A synthetase (ACCA) and pyruvate dehydrogenase (PDH) genes, which contributed to the disorders of glucolipid metabolism and the dysfunction of mitochondrial. The results demonstrated that aminocoumarins with schiff-base as core moieties could be the promising lead compounds for the discovery of novel fungicides.


Asunto(s)
Cumarinas , Diseño de Fármacos , Cumarinas/farmacología , Cumarinas/química , Cumarinas/síntesis química , Relación Estructura-Actividad , Simulación del Acoplamiento Molecular , Pruebas de Sensibilidad Microbiana , Antifúngicos/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Estructura Molecular , Fungicidas Industriales/farmacología , Fungicidas Industriales/síntesis química , Fungicidas Industriales/química , Relación Estructura-Actividad Cuantitativa , Botrytis/efectos de los fármacos
9.
Int J Mol Sci ; 25(18)2024 Sep 19.
Artículo en Inglés | MEDLINE | ID: mdl-39337565

RESUMEN

A preliminary in silico screening of 94 compounds, including colchicine, caffeine, gramine, and their derivatives, was conducted to identify potential herbicides, insecticides, and fungicides. Among the compounds tested, only gramine and its 13 derivatives exhibited potential activity. These compounds were further tested against eight species of insects, three species of weeds, and four species of fungi. All of the tested alkaloids were found to be ineffective as herbicides and insecticides, but they did exhibit some fungicidal activity. Four gramine derivatives showed some activity against Phytophthora infestans, Botrytis cinerea, Zymoseptoria tritici, and Fusarium culmorum.


Asunto(s)
Cafeína , Colchicina , Fungicidas Industriales , Herbicidas , Insecticidas , Herbicidas/farmacología , Herbicidas/química , Cafeína/farmacología , Cafeína/química , Fungicidas Industriales/farmacología , Fungicidas Industriales/química , Insecticidas/farmacología , Insecticidas/química , Colchicina/farmacología , Colchicina/química , Animales
10.
Molecules ; 29(13)2024 Jul 02.
Artículo en Inglés | MEDLINE | ID: mdl-38999100

RESUMEN

Plant diseases caused by pathogenic fungi seriously affect the yield and quality of crops, cause huge economic losses, and pose a considerable threat to global food security. Phenylpyrrole analogues were designed and synthesized based on alkaloid lycogalic acid. All target compounds were characterized by 1H NMR, 13C NMR, and HRMS. Their antifungal activities against seven kinds of phytopathogenic fungi were evaluated. The results revealed that most compounds had broad-spectrum fungicidal activities at 50 µg/mL; 14 compounds displayed more than 60% fungicidal activities against Rhizoctonia cerealis and Sclerotinia sclerotiorum, and in particular, the fungicidal activities of compounds 8g and 8h against Rhizoctonia cerealis were more than 90%, which could be further developed as lead agents for water-soluble fungicides. The molecular docking results indicate that compounds 8g and 8h can interact with 14α-demethylase (RcCYP51) through hydrogen bonding with strong affinity.


Asunto(s)
Alcaloides , Antifúngicos , Diseño de Fármacos , Simulación del Acoplamiento Molecular , Pirroles , Rhizoctonia , Antifúngicos/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Pirroles/química , Pirroles/farmacología , Pirroles/síntesis química , Alcaloides/química , Alcaloides/farmacología , Alcaloides/síntesis química , Rhizoctonia/efectos de los fármacos , Relación Estructura-Actividad , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Ascomicetos/efectos de los fármacos
11.
Bioorg Chem ; 136: 106538, 2023 07.
Artículo en Inglés | MEDLINE | ID: mdl-37079988

RESUMEN

In spite of several attempts to develop newer pharmacophores as potential antimicrobial agents, the benzimidazole scaffold is still considered as one of the most sought after structural component towards the design of compounds that act against a wide spectrum of microbes. Herein, we report the design and synthesis of a new structural class of 4-(1,3-thiazol-2-yl)morpholine-benzimidazole hybrids as antimicrobial agents. The most potent analog, 6g shows IC50 of 1.3 µM, 2.7 µM, 10.8 µM, 5.4 µM and 10.8 µM against Cryptococcus neoformans, Candida albicans, Candida parapsilosis, Escherichia coli and Staphylococcus aureus, respectively. Interestingly 6g exhibits selectivity towards the cryptococcal cells with fungicidal behavior. Propidium iodide uptake study shows permeabilization of pathogenic cells in the presence of 6g. Flow cytometric analysis confirms that cell death is predominantly due to apoptosis. Moreover, electron microscopic analysis specifies that it shrinks, disrupts and initiate pore(s) formation in the cell membrane leading to cell lysis.


Asunto(s)
Antiinfecciosos , Criptococosis , Cryptococcus neoformans , Humanos , Bencimidazoles/farmacología , Candida albicans , Morfolinas , Pruebas de Sensibilidad Microbiana , Antifúngicos/farmacología
12.
Bioorg Chem ; 135: 106508, 2023 06.
Artículo en Inglés | MEDLINE | ID: mdl-37023583

RESUMEN

Fungal and viral diseases account for 70-80% of agricultural production losses caused by microbial diseases. Synthetic fungicides and antiviral agents have been used to treat plant diseases caused by plant pathogenic fungi and viruses, but their use has been criticized due to their adverse side effects. As alternative strategies, natural fungicides and antiviral agents have attracted many researchers' interest in recent years. Herein, we designed and synthesized a series of novel polycarpine simplified analogues. Antiviral activity research against tobacco mosaic virus (TMV) revealed that most of the designed compounds have good antiviral activities. The virucidal activities of 4, 6d, 6f, 6h, and 8c are higher than that of polycarpine and similar to that of ningnanmycin. The structure simplified compound 8c was selected for further antiviral mechanism research which showed that compound 8c could inhibit the formation of 20S protein discs by acting on TMV coat protein. These compounds also displayed broad-spectrum fungicidal activities against 7 kinds of plant fungi. This work lays the foundation for the application of polycarpine simplified analogues in crop protection.


Asunto(s)
Fungicidas Industriales , Virus del Mosaico del Tabaco , Antivirales/química , Fungicidas Industriales/química , Relación Estructura-Actividad , Hongos , Diseño de Fármacos
13.
Bioorg Chem ; 141: 106896, 2023 12.
Artículo en Inglés | MEDLINE | ID: mdl-37806050

RESUMEN

The reaction of aromatic ring-substituted isoselenocyanates with 2-thiopheacetic and 4-pyridinecarboxylic acid hydrazides yielded selenosemicarbazides which were further converted into previously unknown 1,2,4-triazole-3-selones and 3,3'-di(4H-1, 2,4-triazolyl)diselenides. The structures of the obtained compounds were studied by NMR spectroscopy, IR spectroscopy, and high-resolution mass spectroscopy (HR-MS). The bactericidal and fungicidal activity of some obtained compounds was evaluated in molecular modeling studies such as docking and simulation studies. The compound 3ba was reported as the most promising compound to show robust binding energy with different antibacterial and antifungal compounds. The compounds were observed in strong hydrophilic and hydrophobic interactions and remained in stable binding conformation with the receptor enzymes. Furthermore, the interatomic interaction energies were dominated by Van der Waals and electrostatic energies indicating the formation of stable complexes.


Asunto(s)
Antibacterianos , Fungicidas Industriales , Antibacterianos/química , Antifúngicos/química , Espectrometría de Masas , Simulación del Acoplamiento Molecular , Estructura Molecular , Relación Estructura-Actividad , Triazoles/química , Compuestos de Organoselenio/farmacología
14.
Pestic Biochem Physiol ; 194: 105502, 2023 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-37532322

RESUMEN

Rice sheath blight caused by Rhizoctonia solani Kühn is a major fungal disease that plagues commercially grown rice. Occurring mainly in leaf sheaths and leaves, the disease leads to great losses in food production. ß-amino-butyric acid (BABA) has been demonstrated to activate an induced resistance response and is a potent inducer of broad-spectrum disease resistance in different plant species. In this study, ß-amino-butyric acid conjugate of phenazine-1-carboxylic acid (PCA) with prominent induced resistance to rice sheath blight was tested. The in vitro fungicidal activity, as well as in vivo efficacy, systemicity, induced resistance and defense enzyme activity of BABA conjugate of PCA against R. solani in rice seedlings was systematically evaluated. The results indicated that in vitro fungicidal activity of PCA-ß-aminobutyric acid (4e) against R. solani was lower than that of PCA, but in vivo curative ability of 4e was the highest among all tested compounds. The systemicity tests in rice seedlings revealed that PCA did not possess phloem mobility, while 4e exhibited moderate phloem mobility but much lower thanα-amino-butyric acid conjugate of PCA (4d). In addition, Compound 4e showed the highest induced activity against rice sheath blight. The observed effects of defense enzymes help to explain this high level of induced activity. The current research results indicate that in rice seedlings, BABA conjugate of PCA induce observable resistance to rice sheath blight and exhibit moderate phloem mobility, which could be used as an induced resistance fungicide against rice sheath blight in commercial rice production. The BABA conjugate of PCA might provide a useful example of induced resistance to R. solani.


Asunto(s)
Oryza , Oryza/microbiología , Enfermedades de las Plantas/prevención & control , Enfermedades de las Plantas/microbiología , Rhizoctonia , Plantones
15.
Chem Biodivers ; 20(1): e202200971, 2023 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-36418220

RESUMEN

Dimethomorph is a kind of cinnamamide fungicide with high fungicidal activities for oomycete diseases. The commercially available dimethomorph is a mixture of two isomers, in which (Z)-dimethomorph possessing higher activity and (E)-dimethomorph possessing lower activity. Herein, we reported the design, synthesis and fungicidal activities of a series of novel indole-modified cinnamamide derivatives, which used the indole group to 'fix' the cis-styrene group in (Z)-dimethomorph. The modification of the molecular structure of cinnamamide compounds could be beneficial to improve its practical application performance. Tested the fungicidal activities, it was found that compounds 8j, 9a, 9e, 9i and 9j showed excellent in vivo fungicidal activities (80-100 %) against Pseudoperonospora cubensis at a concentration of 100 mg L-1 , while dimethomorph and flumorph were noneffective. Moreover, parts of synthesized indole-modified cinnamamide derivatives 8 (8a, 8c, 8d and 8j) and 9 (9c and 9j) exhibited the same in vivo fungicidal activities against Phytophthora infestans with dimethomorph or flumorph at a concentration of 50 mg L-1 with 100 % inhibition. The biological assay results indicated that indole-modified cinnamamide derivatives have promising applications in the prevention and treatment of Phytophthora infestans.


Asunto(s)
Fungicidas Industriales , Phytophthora infestans , Bioensayo , Cinamatos/farmacología , Fungicidas Industriales/farmacología , Indoles/farmacología , Relación Estructura-Actividad
16.
Chem Biodivers ; 20(7): e202300533, 2023 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-37272455

RESUMEN

In our previous work, two dopamine derivatives with benzothiazole fragment were isolated and identified from Polyrhachis dives (P. dives). Based on their characteristic structure, we used them as lead compound to carry out structural optimization and subsequent fungicidal evaluation. Here 20 dopamine derivatives with benzothiazole fragment were designed and synthesized by a facile method, and their structures were characterized by 1 H-NMR, 13 CNMR and HMRS. In bioassays, most of the title compounds possess potential fungicidal activities against Altenaia alternala (A. alternala) and Botrytis cinerea (B. cinerea). Especially, (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(p-tolyl)acrylamide and (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(4-(trifluoromethyl)phenyl)acrylamide displayed 29.3 mg/L and 10.7 mg/L EC50 value against A. alternala, respectively, which possessed equivalent fungicidal activities level to hymexazol.


Asunto(s)
Hormigas , Fungicidas Industriales , Animales , Dopamina , Relación Estructura-Actividad , Fungicidas Industriales/química , Benzotiazoles/farmacología , Botrytis , Acrilamidas , Antifúngicos/farmacología , Antifúngicos/química
17.
Int J Mol Sci ; 24(3)2023 Jan 25.
Artículo en Inglés | MEDLINE | ID: mdl-36768684

RESUMEN

Frequently touched surfaces (FTS) that are contaminated with pathogens are one of the main sources of nosocomial infections, which commonly include hospital-acquired and healthcare-associated infections (HAIs). HAIs are considered the most common adverse event that has a significant burden on the public's health worldwide currently. The persistence of pathogens on contaminated surfaces and the transmission of multi-drug resistant (MDR) pathogens by way of healthcare surfaces, which are frequently touched by healthcare workers, visitors, and patients increase the risk of acquiring infectious agents in hospital environments. Moreover, not only in hospitals but also in high-traffic public places, FTS play a major role in the spreading of pathogens. Consequently, attention has been devoted to developing novel and alternative methods to tackle this problem. This study planned to produce and characterize innovative functionalized enameled coated surfaces supplemented with 1% AgNO3 and 2% AgNO3. Thus, the antimicrobial properties of the enamels against relevant nosocomial pathogens including the Gram-positive Staphylococcus aureus and the Gram-negative Escherichia coli and the yeast Candida albicans were assessed using the ISO:22196:2011 norm.


Asunto(s)
Antiinfecciosos , Infección Hospitalaria , Humanos , Antifúngicos/farmacología , Plata/farmacología , Antiinfecciosos/farmacología , Antibacterianos/farmacología , Infección Hospitalaria/prevención & control , Infección Hospitalaria/microbiología , Pruebas de Sensibilidad Microbiana
18.
Int J Mol Sci ; 24(6)2023 Mar 17.
Artículo en Inglés | MEDLINE | ID: mdl-36982829

RESUMEN

A series of S-alkyl substituted thioglycolurils was prepared through the alkylation of corresponding thioglycolurils with halogenoalkanes and tested for their fungicidal activity against six phytopathogenic fungi from different taxonomic classes: Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum, and two pathogenic yeasts: Candida albicans and Cryptococcus neoformans var. grubii. A number of S-alkyl substituted thioglycolurils exhibited high activity against Venturia inaequalis and Rhizoctonia solani (85-100% mycelium growth inhibition), and moderate activity against other phytopathogens. S-Ethyl substituted thioglycolurils possessed a high activity against Candida albicans. Additionally, the hemolytic and cytotoxic properties of promising derivatives were determined using human red blood cells and human embryonic kidney cells, respectively. Two S-ethyl derivatives possessed both low cytotoxicity against normal human cells and high fungicidal activity against Candida albicans.


Asunto(s)
Antineoplásicos , Rhizoctonia , Humanos , Hongos del Género Venturia , Antineoplásicos/farmacología , Candida albicans , Antifúngicos/farmacología , Relación Estructura-Actividad
19.
Molecules ; 28(23)2023 Dec 04.
Artículo en Inglés | MEDLINE | ID: mdl-38067660

RESUMEN

The identification of natural and environmentally friendly pesticides is a key area of interest for the agrochemical industry, with many potentially active compounds being sourced from numerous plant species. In this study, we report the bioassay-guided isolation and identification of phytotoxic and antifungal compounds from the ethyl acetate extract of Helietta parvifolia stems. We identified eight compounds, consisting of two coumarins and six alkaloids. Among these, a new alkaloid, 2-hydroxy-3,6,7-trimethoxyquinoline-4-carbaldehyde (6), was elucidated, along with seven known compounds. The phytotoxicity of purified compounds was evaluated, and chalepin (4) was active against Agrostis stolonifera at 1 mM with 50% inhibition of seed germination and it reduced Lemna pausicotata (duckweed) growth by 50% (IC50) at 168 µM. Additionally, we evaluated the antifungal activity against the fungal plant pathogen Colletotrichum fragariae using a thin-layer chromatography bioautography assay, which revealed that three isolated furoquinoline alkaloids (flindersiamine (3), kokusagenine (7), and maculine (8)) among the isolated compounds had the strongest inhibitory effects on the growth of C. fragariae at all tested concentrations. Our results indicate that these active natural compounds, i.e., (3), (4), (7), and (8), could be scaffolds for the production of more active pesticides with better physicochemical properties.


Asunto(s)
Alcaloides , Plaguicidas , Antifúngicos/farmacología , Extractos Vegetales/química , Alcaloides/farmacología , Plantas
20.
Molecules ; 28(17)2023 Aug 31.
Artículo en Inglés | MEDLINE | ID: mdl-37687210

RESUMEN

Bleached and cationized cotton fabrics were chemically modified with reactive organoselenium compounds through the nucleophilic aromatic substitution (SNAr) reaction, which allowed for organo-selenium attachment onto the surface of cotton fabrics via covalent bonds and, in the case of the cationized cotton fabric, additional ionic interactions. The resulting textiles exhibited potent bactericidal activity against S. aureus (99.99% reduction), although only moderate activity was observed against E. coli. Fabrics treated with reactive organo-selenium compounds also exhibited fungicidal activities against C. albicans, and much higher antifungal activity was observed when organo-selenium compounds were applied to the cationized cotton in comparison to the bleached cotton. The treatment was found to be durable against rigorous washing conditions (non-ionic detergent/100 °C). This paper is the first report on a novel approach integrating the reaction of cotton fabrics with an organo-selenium antimicrobial agent. This approach is attractive because it provides a method for imparting antimicrobial properties to cotton fabrics which does not disrupt the traditional production processes of a textile mill.


Asunto(s)
Antiinfecciosos , Compuestos de Selenio , Selenio , Antiinfecciosos/farmacología , Candida albicans , Escherichia coli , Ácido Hipocloroso , Selenio/farmacología , Staphylococcus aureus , Textiles
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