The Effect of Terbinafine and Its Ionic Salts on Certain Fungal Plant Pathogens
Abstract
:1. Introduction
2. Results and Discussion
2.1. Salt Preparation
2.2. Solubilities
2.3. Surface Activity
2.4. In Vitro Assays of Fungicidal Activities
2.5. In Vivo Activity
3. Materials and Methods
3.1. Chemicals and Instrumentation
3.2. Preparation of Terbinafine Salts
3.3. Solubility
3.4. Surface Tension
3.5. In Vitro Assays of Fungicidal Activities
3.6. In Vivo Experiment
3.7. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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API Combination | N-CH3 (ppm) | N-CH2-Ar (ppm) | N-CH2-CH (ppm) |
---|---|---|---|
TIS 1 (CDCl3) | 2.51 | 4.51 | 3.66 |
TIS 2 (DMSO) | 2.19 | 3.98 | 3.24 |
TIS 3 (CDCl3) | 2.66 | 4.66 | 3.82 |
TIS 4 (DMSO) | 2.16 | 3.94 | 3.18 |
TIS 5 (CDCl3) | 2.5 | 4.49 | 3.59 |
Terbinafine (CDCl3) | 2.21 | 3.88 | 3.12 |
Terbinafine (DMSO) | 2.11 | 3.86 | 3.1 |
Salt | Water | Methanol | DMSO | Acetonitrile | Acetone | Isopropanol | Ethyl acetate | Chloroform | Toluene | n-Hexane |
---|---|---|---|---|---|---|---|---|---|---|
9.0 a | 6.6 | 6.5 | 6.2 | 5.1 | 4.3 | 4.3 | 4.1 | 2.3 | 0.0 | |
T | − b | + c | + | + | + | + | + | + | + | + |
TIS 1 | − | + | + | + | + | − | + | + | + | − |
TIS 2 | − | − | + | − | − | − | − | − | − | − |
TIS 3 | − | + | + | − | − | − | − | + | − | − |
TIS 4 | − | − | + | − | − | − | − | − | − | − |
TIS 5 | − | + | + | + | + | + | + | + | + | − |
Drug | Inhibition Rate at 50 mg/L (%) | |||||||
---|---|---|---|---|---|---|---|---|
V. m | B. c | P. o | P. c | A. s | R. s | F. g | P. a | |
T | 100 ± 0 | 100 ± 0 | 99.64 ± 0.36 | 48.75 ± 0.45 | 100 ± 0 | 84.21 ± 0.53 | 100 ± 0 | 68.21 ± 1.87 |
TIS 1 | 100 ± 0 | 100 ± 0 | 99.05 ± 0.21 | 46.97 ± 1.18 | 100 ± 0 | 84.79 ± 1.25 | 100 ± 0 | 74.61 ± 0.38 |
TIS 2 | 100 ± 0 | 100 ± 0 | 96.09 ± 0.36 | 43.85 ± 1.61 | 98.8 ± 0 | 80.75 ± 0.72 | 100 ± 0 | 69.65 ± 1.7 |
TIS 3 | 100 ± 0 | 100 ± 0 | 99.29 ± 0 | 33.16 ± 2.52 | 100 ± 0 | 83.4 ± 0.35 | 100 ± 0 | 69.54 ± 0 |
TIS 4 | 100 ± 0 | 100 ± 0 | 98.7 ± 0.54 | 47.64 ± 1.58 | 100 ± 0 | 85.82 ± 1.51 | 100 ± 0 | 65.23 ± 0.47 |
TIS 5 | 100 ± 0 | 100 ± 0 | 96.68 ± 0.42 | 55.88 ± 1.89 | 98.67 ± 0.61 | 82.02 ± 0.91 | 100 ± 0 | 71.96 ± 2.68 |
Fungi | Drugs | Regression Equation | r2 | EC50 | 95% Confidence Intervals (mg/L) | |
---|---|---|---|---|---|---|
(mg/L) | (μmol/L) | |||||
V. m | Terbinafine | y = 2.62x − 0.22 | 0.969 | 1.25 | 4.28 | 0.98–1.57 |
TIS 1 | y = 2.12x − 0.77 | 0.985 | 2.24 | 5.21 | 1.93–2.57 | |
TIS 2 | y = 2.87x − 1.87 | 0.955 | 4.28 | 6.29 | 3.16–6.00 | |
TIS 3 | y = 2.15x − 0.66 | 0.986 | 2.03 | 4.98 | 1.77–2.34 | |
TIS 4 | y = 2.17x − 0.59 | 0.997 | 1.88 | 4.60 | 1.64–2.14 | |
TIS 5 | y = 2.28x − 0.39 | 0.986 | 1.49 | 3.69 | 1.30–1.73 | |
Pyraclostrobin | y = 0.59x + 0.06 | 0.995 | 0.79 | 2.02 | 0.03–1.71 | |
B. c | Terbinafine | y = 3.18x + 3.16 | 0.976 | 0.10 | 0.34 | 0.09–0.11 |
TIS 1 | y = 3.03x + 2.6 | 0.959 | 0.14 | 0.32 | 0.11–0.17 | |
TIS 2 | y = 3.53x + 2.12 | 0.990 | 0.25 | 0.37 | 0.23–0.28 | |
TIS 3 | y = 3.53x + 3.09 | 0.942 | 0.13 | 0.33 | 0.10–0.18 | |
TIS 4 | y = 3.7x + 3.07 | 0.974 | 0.15 | 0.36 | 0.12–0.18 | |
TIS 5 | y = 4.27x + 3.77 | 0.966 | 0.13 | 0.33 | 0.11–0.15 | |
Pyraclostrobin | y = 1.88x + 1.74 | 0.993 | 0.12 | 0.31 | 0.01–0.15 | |
P. o | Terbinafine | y = 0.98x + 0.55 | 0.998 | 0.28 | 0.95 | 0.13–0.43 |
TIS 1 | y = 1.02x + 0.33 | 0.991 | 0.47 | 1.10 | 0.28–0.66 | |
TIS 2 | y = 1.15x + 0.07 | 0.991 | 0.88 | 1.29 | 0.65–1.11 | |
TIS 3 | y = 1.17x + 0.28 | 0.969 | 0.58 | 1.41 | 0.39–0.76 | |
TIS 4 | y = 1.32x + 0.17 | 0.993 | 0.75 | 1.84 | 0.57–0.94 | |
TIS 5 | y = 1.1x + 0.34 | 0.997 | 0.49 | 1.22 | 0.31–0.68 | |
Pyraclostrobin | y = 0.56x + 0.13 | 0.991 | 0.60 | 1.54 | 0.25–0.99 | |
A. s | Terbinafine | y = 1.25x + 1.43 | 0.998 | 0.07 | 0.25 | 0.05–0.09 |
TIS 1 | y = 1.42x + 1.25 | 0.936 | 0.13 | 0.30 | 0.07–0.19 | |
TIS 2 | y = 0.92x + 0.68 | 0.987 | 0.18 | 0.27 | 0.13–0.24 | |
TIS 3 | y = 0.99x + 0.83 | 0.965 | 0.15 | 0.36 | 0.11–0.19 | |
TIS 4 | y = 1.23x + 1.16 | 0.986 | 0.11 | 0.28 | 0.09–0.14 | |
TIS 5 | y = 1.1x + 1.19 | 0.996 | 0.08 | 0.20 | 0.06–0.11 | |
Pyraclostrobin | y = 0.3x + 0.2 | 0.981 | 0.23 | 0.59 | 0.07–0.56 | |
R. s | Terbinafine | y = 1.29x − 0.33 | 0.961 | 1.73 | 5.94 | 1.41–2.10 |
TIS 1 | y = 1.8x − 0.78 | 0.931 | 2.49 | 5.81 | 1.69–3.72 | |
TIS 2 | y = 1.48x − 0.78 | 0.975 | 3.32 | 4.88 | 2.78–4.03 | |
TIS 3 | y = 1.44x − 0.39 | 0.984 | 1.84 | 4.51 | 1.53–2.19 | |
TIS 4 | y = 1.49x − 0.56 | 0.972 | 2.30 | 5.65 | 1.93–2.75 | |
TIS 5 | y = 1.49x − 0.59 | 0.980 | 2.43 | 6.02 | 2.04–2.90 | |
Pyraclostrobin | y = 0.55x + 0.62 | 0.999 | 0.07 | 0.19 | 0.01–0.21 | |
F. g | Terbinafine | y = 1.4x + 1.66 | 0.943 | 0.07 | 0.25 | 0.06–0.09 |
TIS 1 | y = 1.25x + 1.27 | 0.988 | 0.10 | 0.23 | 0.07–0.12 | |
TIS 2 | y = 1.37x + 1.08 | 0.995 | 0.16 | 0.24 | 0.12–0.21 | |
TIS 3 | y = 1.32x + 1.35 | 0.984 | 0.10 | 0.24 | 0.08–0.12 | |
TIS 4 | y = 1.3x + 1.38 | 0.995 | 0.09 | 0.21 | 0.06–0.11 | |
TIS 5 | y = 1.33x + 1.29 | 0.983 | 0.11 | 0.27 | 0.08–0.13 | |
Pyraclostrobin | y = 0.74x − 0.12 | 0.993 | 1.43 | 3.68 | 0.91–3.27 |
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Wang, T.; Wang, Q.; Zhou, Y.; Shi, Y.; Gao, H. The Effect of Terbinafine and Its Ionic Salts on Certain Fungal Plant Pathogens. Molecules 2023, 28, 4722. https://doi.org/10.3390/molecules28124722
Wang T, Wang Q, Zhou Y, Shi Y, Gao H. The Effect of Terbinafine and Its Ionic Salts on Certain Fungal Plant Pathogens. Molecules. 2023; 28(12):4722. https://doi.org/10.3390/molecules28124722
Chicago/Turabian StyleWang, Tao, Qiuxiao Wang, Yifei Zhou, Yaolin Shi, and Haixiang Gao. 2023. "The Effect of Terbinafine and Its Ionic Salts on Certain Fungal Plant Pathogens" Molecules 28, no. 12: 4722. https://doi.org/10.3390/molecules28124722