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

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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Activity of Alkanediol Alkanoates against Pathogenic Plant Fungi Rhizoctonia solani and Sclerotium rolfsii

Natural Product Communications ◽

10.1177/1934578x1200700930 ◽

2012 ◽

Vol 7 (9) ◽

pp. 1934578X1200700 ◽

Cited By ~ 2

Author(s):

Paraj Shukla ◽

Suresh Walia ◽

Vivek Ahluwalia ◽

Balraj S. Parmar ◽

Muraleedharan G. Nair

Keyword(s):

Antifungal Activity ◽

Ethylene Glycol ◽

Rhizoctonia Solani ◽

Diethylene Glycol ◽

Sclerotium Rolfsii ◽

Phytopathogenic Fungi ◽

Dependent Manner ◽

Acyl Chlorides ◽

Mass Spectral ◽

Dose Dependent

Thirty known dialkanoates of ethylene, propylene and diethylene glycols were synthesized by reacting the glycols with acyl chlorides and their structures confirmed by IR, NMR and mass spectral analyses. They exhibited significant antifungal activity against two phytopathogenic fungi Rhizoctonia solani Kuehn and Sclerotium rolfsii Sacc in a dose dependent manner. Propylene glycol dipentanoate was the most active against R. solani. followed by diethylene glycol dibutanoate and ethylene glycol dibutanoate. Against S. rolfsii ethylene glycol diheptanoate was found to be most active followed by diethylene glycol diisobutanoate As compared to the standard reference benomyl (EC50 5.16 μg/mL), the potential alkanediol dialkanoates showed EC50 in the range of 33 – 60 μg/mL.

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In vitro Antifungal Activity of Plant Extracts, Hydrolates and Essential Oils of Some Medicinal Plants and Control of Cucumber Anthracnose

European Journal of Medicinal Plants ◽

10.9734/ejmp/2019/v28i430139 ◽

2019 ◽

pp. 1-9

Author(s):

Amanda P. Mattos ◽

Fabricio P. Povh ◽

Bruna B. Rissato ◽

Vítor V. Schwan ◽

Kátia R. F. Schwan-Estrada

Keyword(s):

Antifungal Activity ◽

Medicinal Plants ◽

Curcuma Longa ◽

Sclerotium Rolfsii ◽

Phytopathogenic Fungi ◽

In Vivo Test ◽

Activity Effect ◽

In Vitro Antifungal Activity

Aims: This study is aimed to evaluate the in vitro antifungal activity effect of the crude aqueous extract (CAE), hydrolate (HY) and essential oil (EO) of Corymbia citriodora, Cymbopogon citratus, Cymbopogon flexuosus and Curcuma longa against the phytopathogenic fungi Alternaria steviae, Botryosphaeria dothidea, Colletotrichum gloeosporioides and Sclerotium rolfsii, and assess, in situ, the effectiveness of CAE of medicinal plants in reducing the severity of the cucumber anthracnose. Methodology: The EOs and HYs were obtained by hydrodistillation. The CAEs were prepared by the turbolysis method. Mycelial growth of the fungi was measured daily, by the diametrically opposite method. In the in vivo test, the CAEs were sprayed on the cotyledon leaves of healthy cucumber plants with three days after were inoculated with C. lagenarium. The severity of assessment of the disease was based on a scale of notes. Results: The medicinal plants studied showed antifungal activity against all or almost all pathogens. In general, treatment with CAE and HY of C. longa revealed the highest inhibition against the fungi tested. With the exception of the EO of C. longa, the other EOs showed total inhibition against all the fungi and in all the concentrations tested. Compared to control, in in vivo assays CAE of C. citratus presents a potential for control of cucumber anthracnose reducing the severity of the disease. Conclusion: The medicinal plants studied produce compounds associated with antimicrobial activity.

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In Vitro Antifungal Activity of Citrus aurantifolia Linn Plant Extracts against Phytopathogenic Fungi Macrophomina phaseolina

International Letters of Natural Sciences ◽

10.18052/www.scipress.com/ilns.13.70 ◽

2014 ◽

Vol 13 ◽

pp. 70-74 ◽

Cited By ~ 1

Author(s):

S. Balamurugan

Keyword(s):

Antifungal Activity ◽

Root Rot ◽

Field Experiments ◽

Macrophomina Phaseolina ◽

Phytopathogenic Fungi ◽

Citrus Aurantifolia ◽

Dependent Inhibition ◽

Dose Dependent Inhibition ◽

Dose Dependent

The aqueous extracts of leaf of Citrus aurantifolia L were assessed in vitro for inhibitory activity against Macrophominaphaseolina isolated from dry root rot specimens of Gingelly. The antifungal activity was determined by poison food technique. The extracts have shown dose dependent inhibition of mycelial growth of test fungi. The extracts were more effective in inhibiting Macrophominaphaseolina. The extracts of Citrus aurantifolia were found effective against Gingelly dry root rot pathogens. Further field experiments are to be carried out to recommend the extracts against the disease.

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In vitro antifungal activity of three Saudi plant extracts against some Phytopathogenic fungi

Journal of Plant Protection Research ◽

10.2478/v10045-012-0073-9 ◽

2012 ◽

Vol 52 (4) ◽

pp. 458-462 ◽

Cited By ~ 12

Author(s):

Abdul Aziz A. Al-Askar

Keyword(s):

Antifungal Activity ◽

Plant Extracts ◽

Sclerotium Rolfsii ◽

Ethanolic Extract ◽

Punica Granatum ◽

Phytopathogenic Fungi ◽

Plant Diseases ◽

High Concentration ◽

In Vitro Antifungal Activity

Abstract The antifungal activities of ethanolic extracts of three Saudi plants; camel thorn (Alhagi maurorum Medic.), caper (Capparisspinosa L.), and pomegranate (Punica granatum L.) were investigated in vitro against Alternaria alternata, Fusarium oxysporum, Phomadestructiva, Rhizoctonia solani, and Sclerotium rolfsii at concentrations of 0, 3, 6, and 9% (v/v). All tested plant extracts; seeds, roots, and rinds had different degrees of antifungal activity against the tested fungi. When compared with the control, the highest antifungal activity was recorded for camel thorn seeds extract at a concentration of 9%, while, pomegranate rinds extract at 9% came in second. Camel thorn rinds extract came in last even when used at a high concentration. The ethanolic extract of camel thorn seeds may be recommended as a potent bio-fungicide. Extensive studies should be undertaken for the ethanolic extract of camel thorn seeds as a strong antifungal agent against fungal plant diseases.

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