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Title: SYNTHESIS OF 4-HYDROXYAZOBENZENE, A PROMISING AZO DYE FOR ANTIFUNGAL ACTIVITY AGAINST MACROPHOMINA PHASEOLINA
Authors: Aqsa Zafar, Arshad Javaid, Ejaz Ahmed, Iqra Haider Khan, Hamza Shehzad, Aneela Anwar
Journal: Plant Protection
Publisher: Center for Community Learning
Country: Pakistan
Year: 2022
Volume: 6
Issue: 2
Language: English
Keywords: AntifungalMacrophomina phaseolinaAzo dye4-Hydroxyazobenzene
In the present study, an azo dye 4-hydroxyazobenzene was synthesized and its antifungal activity against a notorious soil-borne plant pathogen Macrophomina phaseolina was evaluated. The 4-hydroxyazobenzene was synthesized by azo coupling reaction between aniline diazonium salt and activated phenol. The azo coupling preferably occurred at para position of the phenol ring since the charge density get reinforced at this position and to minimize the steric hindrance between ortho positioned hydroxyl group. Azo coupling involved an electrophilic substitution reaction of phenyl diazonium cation with phenolate ion, the coupling partner. In vitro antifungal activity of the compound was assessed by dissolving the compound in dimethyl sulfoxide (DMSO) and preparing its different concentrations (ranging from 0.78 to 100 mg mL -1 ) in malt extract broth. All the concentrations of synthesized compound significantly (P≤0.05) reduced biomass of M. phaseolina by 31–49%. This study concludes that 4-hydroxyazobenzene can be used for control of M. phaseolina.
To synthesize 4-hydroxyazobenzene and evaluate its in vitro antifungal activity against the plant pathogen Macrophomina phaseolina.
The study involved the synthesis of 4-hydroxyazobenzene through an azo coupling reaction between aniline diazonium salt and activated phenol. The antifungal activity was assessed in vitro by dissolving the synthesized compound in dimethyl sulfoxide (DMSO) and preparing serial dilutions in malt extract broth. Macrophomina phaseolina was cultured and inoculated into the prepared media. Fungal biomass was measured after incubation. Statistical analysis was performed using ANOVA and the LSD test.
graph TD
A[Synthesis of 4-Hydroxyazobenzene] --> B[Preparation of Compound Solutions];
B --> C[Preparation of Fungal Inoculum];
C --> D[Inoculation of Media with Compound and Fungus];
D --> E[Incubation];
E --> F[Harvesting and Drying of Fungal Biomass];
F --> G[Weighing of Fungal Biomass];
G --> H[Statistical Analysis];
H --> I[Conclusion on Antifungal Activity];
The study suggests that 4-hydroxyazobenzene can be used for the control of Macrophomina phaseolina. The antifungal activity is attributed to the conjugated double bonds in azo dyes, which can interact with fungal cell membranes, leading to ion leakage and cell death. The results align with previous research on the antifungal properties of various azo dyes.
The synthesized 4-hydroxyazobenzene appeared as orange-yellow crystalline solid with a melting point of around 155°C. All tested concentrations (0.78 to 100 mg mL-1) of the compound significantly reduced the biomass of Macrophomina phaseolina by 31-49%.
4-Hydroxyazobenzene exhibits pronounced antifungal activity against Macrophomina phaseolina, with significant growth reduction observed across a range of concentrations. Further research is recommended to prepare derivatives of this compound to enhance its antifungal efficacy.
1. Concentration Range: The study evaluated concentrations of the synthesized compound ranging from 0.78 to 100 mg mL-1.
2. Biomass Reduction: All tested concentrations significantly reduced the biomass of M. phaseolina by 31-49%.
3. Melting Point: The synthesized 4-hydroxyazobenzene had a sharp melting point at around 155°C.
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