scholarly journals Facile synthesis and antifungal activity of dithiocarbamate derivatives bearing an amide moiety

2015 ◽  
Vol 80 (11) ◽  
pp. 1367-1374 ◽  
Author(s):  
Yu-Wen Li ◽  
Shu-Tao Li
Keyword(s):  
Antifungal Activity ◽  
Fusarium Solani ◽  
High Resolution Mass Spectrometry ◽  
Alternaria Solani ◽  
Phytopathogenic Fungi ◽  
Gibberella Zeae ◽  
Significant Activity ◽  
Facile Synthesis ◽  
Dithiocarbamate Derivatives

A series of novel dithiocarbamate derivatives bearing amide moiety 3a-3i and 4a-4i were synthesized by a facile method, and the structures of these derivatives were confirmed by 1H NMR, 13C NMR, elemental analysis and high-resolution mass spectrometry (HRMS). Their antifungal activity against five phytopathogenic fungi were evaluated, and the results showed that most of the target compounds displayed low antifungal activity in vitro against Gibberella zeae, Cytospora sp., Collectotrichum gloeosporioides, Alternaria solani, and Fusarium solani at concentration of 100 mg/L. Compound 4f and 4g exhibited significant activity against Alternaria solani and Collectotrichum gloeosporioides, respectively.

scholarly journals Synthesis and Bio-Evaluation of Natural Butenolides-Acrylate Conjugates

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1304 ◽  
Author(s):  
Longzhu Bao ◽  
Shuangshuang Wang ◽  
Di Song ◽  
Jingjing Wang ◽  
Xiufang Cao ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antifungal Activity ◽  
13C Nmr ◽  
Pathogenic Fungi ◽  
Phytopathogenic Fungi ◽  
Gibberella Zeae ◽  
Ionization Mass ◽  
Activity Screening ◽  
In Vitro Antifungal Activity

A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L−1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

Synthesis and Antifungal Activities of 2-(N-Arylsulfonylindol-3-yl)-3-aryl-1,3-thiazinan-4-ones

2013 ◽  
Vol 68 (3-4) ◽  
pp. 77-81 ◽  
Author(s):  
Huan Qu ◽  
Rui Zhang ◽  
Ying Hu ◽  
Yazhen Ke ◽  
Zhinan Gao ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Fusarium Graminearum ◽  
Alternaria Alternata ◽  
Alternaria Solani ◽  
Phytopathogenic Fungi ◽  
Pyricularia Oryzae ◽  
Alternaria Brassicae ◽  
Antifungal Activities ◽  
Valsa Mali

4j A series of 2-(N-arylsulfonylindol-3-yl)-3-aryl-1,3-thiazinan-4-one derivatives were synthesized and evaluated in vitro against seven phytopathogenic fungi, namely Fusarium graminearum, Alternaria solani, Fusarium oxysporium f. sp. vasinfectum, Alternaria brassicae, Valsa mali, Alternaria alternata, and Pyricularia oryzae. Among all derivatives, especially compound exhibited a potential antifungal activity against four phytopathogenic fungi.

scholarly journals Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1708
Author(s):  
Ming Chen ◽  
Wen-Gui Duan ◽  
Gui-Shan Lin ◽  
Zhong-Tian Fan ◽  
Xiu Wang
Keyword(s):  
Antifungal Activity ◽  
Alternaria Solani ◽  
3D Qsar ◽  
Qsar Model ◽  
Gibberella Zeae ◽  
Cercospora Arachidicola ◽  
Qsar Study ◽  
Structure Activity ◽  
Better Than

A series of novel nopol derivatives bearing the 1,3,4-thiadiazole-thiourea moiety were designed and synthesized by multi-step reactions in search of potent natural product-based antifungal agents. Their structures were confirmed by FT-IR, NMR, ESI-MS, and elemental analysis. Antifungal activity of the target compounds was preliminarily evaluated by in vitro methods against Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis, and Colleterichum orbicalare at 50 µg/mL. All the target compounds exhibited better antifungal activity against P. piricola, C. arachidicola, and A. solani. Compound 6j (R = m, p-Cl Ph) showed the best broad-spectrum antifungal activity against all the tested fungi. Compounds 6c (R = m-Me Ph), 6q (R = i-Pr), and 6i (R = p-Cl Ph) had inhibition rates of 86.1%, 86.1%, and 80.2%, respectively, against P. piricola, much better than that of the positive control chlorothalonil. Moreover, compounds 6h (R = m-Cl Ph) and 6n (R = o-CF3 Ph) held inhibition rates of 80.6% and 79.0% against C. arachidicola and G. zeae, respectively, much better than that of the commercial fungicide chlorothalonil. In order to design more effective antifungal compounds against A. solani, analysis of the three-dimensional quantitative structure–activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r2 = 0.992, q2 = 0.753) has been established. Furthermore, some intriguing structure–activity relationships were found and are discussed by theoretical calculation.

scholarly journals Molecular Design, Synthesis, and Biological Evaluation of 2-Hydroxy-3-Chrysino Dithiocarbamate Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3038
Author(s):  
Ramesh ◽  
Rao ◽  
Hong ◽  
Reddy
Keyword(s):  
Antibacterial Activity ◽  
Molecular Docking ◽  
Antifungal Activity ◽  
Molecular Design ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Significant Activity ◽  
Lipinski’S Rule ◽  
Dithiocarbamate Derivatives

A series of 2-hydroxy-3-chrysino dithiocarbamate derivatives (3a–k) were designed, synthesized, and characterized for their structure determination by 1H NMR, 13C NMR, and HRMS (ESI) spectral data. They were screened for their in vitro biological activities against a panel of selected bacterial and fungal strains. These antimicrobial studies indicate that some of the analogues manifested significant activity compared to standard drugs. Among the synthetic analogues (3a–k), compounds 3d, 3f, and 3j exhibited very good antibacterial activity and compounds 3d, 3f, and 3h showed very good antifungal activity compared to the standard drugs penicillin and itrazole, respectively. The compounds 3e, 3g, and 3h showed moderate antibacterial activity and the compounds 3j and 3k showed moderate antifungal activity. Molecular docking studies were performed and the experimental antimicrobial screening results were also correlated with the binding energy values obtained by molecular docking. The synthesized chrysin analogues (3a–k) have obeyed Lipinski’s “rule of five” and have drug-likeness.

scholarly journals In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi

Molecules ◽  
2012 ◽  
Vol 17 (11) ◽  
pp. 13026-13035 ◽  
Author(s):  
Xin-Juan Yang ◽  
Fang Miao ◽  
Yao Yao ◽  
Fang-Jun Cao ◽  
Rui Yang ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Phytopathogenic Fungi ◽  
Sanguinarine And Chelerythrine ◽  
In Vitro Antifungal Activity

Bactericidal and Fungicidal Activities of Calia secundiflora (Ort.) Yakovlev

2008 ◽  
Vol 63 (9-10) ◽  
pp. 653-657 ◽  
Author(s):  
Dolores Pérez-Laínez ◽  
Rosario García-Mateos ◽  
Ruben San Miguel-Chávez ◽  
Marcos Soto-Hernández ◽  
Enrique Rodríguez-Pérez ◽  
...  
Keyword(s):  
Xanthomonas Campestris ◽  
Alternaria Solani ◽  
Erwinia Carotovora ◽  
Phytopathogenic Fungi ◽  
Quinolizidine Alkaloids ◽  
Liquid Chromatography Mass Spectrometry ◽  
In Vitro Bioassay ◽  
Organic Extract ◽  
Phytopathogenic Fungi And Bacteria

Calia secundiflora (Ortega) Yakovlev (Fabaceae) is considered a medicinal plant in Mexico but has scarcely been used because of the toxicity of its quinolizidine alkaloids. Several quinolizidine alkaloids have shown bactericidal, nematicidal, and fungicidal activities. The purpose of this study was to identify the alkaloids in the seeds and evaluate the activity of the organic extract on several phytopathogenic fungi and bacteria. An in vitro bioassay was conducted with species of the following phytopathogenic fungi: Alternaria solani, Fusarium oxysporum and Monilia fructicola; and of the following bacteria Pseudomonas sp., Xanthomonas campestris and Erwinia carotovora. Cytisine, lupinine, anagyrine, sparteine, N-methylcytisine, 5,6-dehydrolupanine, and lupanine were identified by liquid chromatography-mass spectrometry in the extract of seeds; the most abundant compound of the extract was cytisine. It was observed that the crude extract of Calia secundiflora was moderately active on bacteria and more potent on phytopathogenic fungi. In contrast cytisine showed the opposite effects.

Design, Synthesis and Evaluate In Vitro Antifungal Activity of Novel Benzamide Derivatives

2019 ◽  
Vol 41 (3) ◽  
pp. 549-549
Author(s):  
Xuesong Wang and Xiaorong Tang Xuesong Wang and Xiaorong Tang
Keyword(s):  
Antifungal Activity ◽  
Pathogenic Fungi ◽  
Gibberella Zeae ◽  
Design Synthesis ◽  
Carboxylic Acid Amides ◽  
Almost All ◽  
Negative Controls ◽  
New Compounds ◽  
Benzamide Derivatives

A series of novel benzamide derivatives according to fluopicolide were designed and synthesized following the rule of combination carboxylic acid amides and amines derivatives together. The antifungal activity of the 15 new compounds were evaluated in vitro against five pathogenic fungi, including Sclerotinia sclerotiorum, Gibberella zeae, Rhizoctonia solani, Helminthosporium maydis and Botrytis cinerea. Almost all the structure have not been reported, except compounds 3, 5 and 6. A surprising finding is that all the five tested fungi breed faster than negative controls when supplementary with compound 715 , respectively.

Antifungal activity of Trichoderma harzianum and T. koningiopsis against Fusarium solani in seed germination and vigor of Miahuateco chili seedlings

2021 ◽  
Vol 39 (2) ◽  
Author(s):  
Leydi Miguel-Ferrer ◽  
Omar Romero-Arenas ◽  
Petra Andrade-Hoyos ◽  
Primo Sánchez-Morales ◽  
José Antonio Rivera-Tapia ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Seed Germination ◽  
Trichoderma Harzianum ◽  
Fusarium Solani ◽  
Para Determinar ◽  
Santa Maria

El chile es la segunda hortaliza de mayor producción en México. El objetivo de la investigación fue evaluar la actividad antagónica <em>in vitro</em> e <em>in vivo</em> de <em>Trichoderma harzianum</em> (T-H4) y <em>T. koningiopsis</em> (T-K11) <em>versus Fusarium solani</em> (MX-MIC 798) en la germinación y establecimiento de plántula de chile Miahuateco. Se utilizó la técnica de cultivo dual para determinar el porcentaje de inhibición de crecimiento radial (PICR) de la cepa MX-MIC 798. Además, se analizó el porcentaje de germinación en semillas de chile Miahuateco en vivero, así como la mortalidad de plántulas y grado de severidad a los 40 días después del trasplante (ddt) en Santa María Tecomavaca, Oaxaca, a través de biocontrol y control químico (Mancozeb 80®). La cepa T-H4 presentó el nivel antagónico PICR más alto (53.3%) <em>in vitro</em> y clase II en la escala de Bell, asimismo obtuvo 82% de germinación en semillas de chile Miahuateco en vivero y 48% de mortalidad en campo; de manera que igualó al control químico y superó a <em>T. koningiopsis</em> T-K11. La actividad antifúngica de <em>Trichoderma</em> spp., ofrecen una alternativa para el biocontrol de la marchitez y necrosis en raíz del cultivo de chile Miahuateco causada por <em>F. solani</em> MX-MIC 798.

scholarly journals Synthesis, Antifungal Activity and Structure-Activity Relationships of Vanillin Oxime-N-O-Alkanoates

2012 ◽  
Vol 7 (12) ◽  
pp. 1934578X1200701 ◽  
Author(s):  
Vivek Ahluwalia ◽  
Nandini Garg ◽  
Birendra Kumar ◽  
Suresh Walia ◽  
Om P. Sati
Keyword(s):  
Antifungal Activity ◽  
Chain Length ◽  
Acyl Chain ◽  
Sclerotium Rolfsii ◽  
Hydroxylamine Hydrochloride ◽  
Macrophomina Phaseolina ◽  
Phytopathogenic Fungi ◽  
Acyl Chlorides ◽  
Acyl Chain Length

Vanillin oxime- N-O-alkanoates were synthesized following reaction of vanillin with hydroxylamine hydrochloride, followed by reaction of the resultant oxime with acyl chlorides. The structures of the compounds were confirmed by IR, 1H, 13C NMR and mass spectral data. The test compounds were evaluated for their in vitro antifungal activity against three phytopathogenic fungi Macrophomina phaseolina, Rhizoctonia solani and Sclerotium rolfsii by the poisoned food technique. The moderate antifungal activity of vanillin was slightly increased following its conversion to vanillin oxime, but significantly increased after conversion of the oxime to oxime- N-O-alkanoates. While vanillin oxime- N-O-dodecanoate with an EC50 value 73.1 μg/mL was most active against M. phaseolina, vanillin oxime- N-O-nonanoate with EC50 of value 66.7 μg/mL was most active against R. solani. The activity increased with increases in the acyl chain length and was maximal with an acyl chain length of nine carbons.

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