Antifungal Activities of Fluorinated Pyrazole Aldehydes on Phytopathogenic Fungi, and Their Effect on Entomopathogenic Nematodes, and Soil-Beneficial Bacteria
Abstract
:1. Introduction
2. Results
2.1. Biological Activity Evaluation
2.1.1. Antifungal Activity
2.1.2. Antibacterial Activity
2.1.3. Nematicidal Activity
Code of Molecule 1 | Antifungal Activity a,2 | Antibacterial Activity b | Nematicidal Activity c | Inhibition of AChE/% d,3 | |||||
---|---|---|---|---|---|---|---|---|---|
Macrophomina phaseolina | Sclerotinia sclerotiorum | Fusarium oxysporum f. sp. lycopersici | Fusarium culmorum | Bacillus mycoides | Bradyrhizobium japonicum | Heterorhabditis bacteriophora | Steinernema feltiae | ||
H1 | 23.81 ± 14.78 * | 17.74 ± 10.46 * | 9.42 ± 1.57 * | 23.37 ± 3.89 * | >512 | >512 | 0.00 ± 0.00 | 1.25 ± 0.00 | 44.20 ± 0.00 * |
H2 | 10.42 ± 1.72 * | 14.36 ± 10.46 * | 18.05 ± 4.05 * | 38.62 ± 5.25 * | >512 | >512 | 0.00 ± 0.00 | 0.00 ± 0.00 | 50.00 ± 5.18 * |
H3 | 7.44 ± 2.98 | 5.91 ± 1.69 | 3.92 ± 4.44 | 28.46 ± 6.64 * | >512 | >512 | 0.00 ± 0.00 | 1.25 ± 0.00 | 37.00 ± 4.94 * |
H4 | 8.18 ± 2.85 | 36.32 ± 4.25 * | 17.27 ± 6.47 * | 26.42 ± 5.25 * | >512 | >512 | 0.00 ± 0.00 | 0.00 ± 0.00 | 60.00 ± 0.00 * |
H5 | 16.37 ± 5.70 * | 39.70 ± 12.75 * | 1.57 ± 6.69 | 31.50 ± 6.94 * | >512 | >512 | 0.00 ± 0.00 | 0.00 ± 0.00 | 74.40 ± 0.00 * |
H6 | 11.16 ± 4.46 * | 28.72 ± 6.47 * | 22.76 ± 4.44 * | 28.46 ± 3.32 * | >512 | >512 | 0.00 ± 0.00 | 0.00 ± 0.00 | 55.70 ± 0.02 * |
H7 | 13.39 ± 7.87 * | 42.23 ± 1.95 * | 26.39 ± 1.57 * | 29.47 ± 3.89 * | >512 | >512 | 0.00 ± 0.00 | 0.00 ± 0.00 | 63.30 ± 6.00 * |
H8 | 20.83 ± 5.43 * | 10.98 ± 7.49 | 25.90 ± 9.24 * | 33.54 ± 3.89 * | >512 | >512 | 0.00 ± 0.00 | 2.50 ± 0.00 | 59.60 ± 0.00 * |
H9 | 29.76 ± 9.41 * | 43.07 ± 10.46 * | 34.54 ± 10.37 * | 46.75 ± 4.07 * | >512 | >512 | 18.75 ± 0.00 | 0.25 ± 0.00 | 79.50 ± 0.00 * |
H10 | 15.63 ± 7.83 * | 13.51 ± 18.09 | 20.67 ± 3.95 * | 25.41 ± 2.03 * | >512 | >512 | 0.00 ± 0.00 | 0.00 ± 0.00 | 72.60 ± 5.88 * |
Control 4 | 0 ± 0.00 | 0 ± 0.00 | 0 ± 0.00 | 0 ± 0.00 | / | / | / | / | / |
Donepezil 5 | / | / | / | / | / | / | / | / | 99.89 ± 0.01 |
LSD | 10.54 | 14.01 | 8.66 | 6.84 | / | / | / | / | 4.51 |
2.1.4. AChE Inhibition
2.2. In-Silico Analyses
2.2.1. “Pesticide-Likeness” and Toxicity Parameters
Code of Molecule | Oral Rat LD50 (mg/kg bw) a | Tetrahymena pyriformis pIGC50 48-h (mol/L) b | Fathead Minnow pLC50 96-h (mol/L) c | Mutagenicity Value (Result) d | Bioaccumulation Factor (logBAF/L kg−1) e |
---|---|---|---|---|---|
H1 | 977.34 (NN) | 4.69 (NN) | 5.78 | 0.70 (pos) | 1.37 |
H2 | 977.34 (NN) | 4.69 (NN) | 5.82 | 0.67 (pos) | 1.39 |
H3 | 937.90 (NN) | 4.58 (NN) | 5.37 | 0.57 (pos) | 1.51 |
H4 | 464.23 (NN) | 5.10 (NN) | 8.24 | 0.37 (neg) | 1.30 |
H5 | 977.34 (NN) | 4.69 (NN) | 5.80 | 0.69 (pos) | 1.40 |
H6 | 931.38 (NN) | 4.58 (NN) | 5.26 | 0.64 (pos) | 1.27 |
H7 | 1075.71 (NN) | 4.69 (NN) | 6.13 | 0.45 (neg) | 1.42 |
H8 | 1137.40 (NN) | 4.58 (NN) | 5.89 | 0.63 (pos) | 1.55 |
H9 | 991.78 (NN) | 4.58 (NN) | 5.90 | 0.63 (pos) | 1.63 |
H10 | 1020.09 (NN) | 4.58 (NN) | 5.33 | 0.31 (neg) | 1.34 |
2.2.2. Molecular Docking
3. Discussion
4. Materials and Methods
4.1. Biological Assays
4.1.1. Antifungal Assays
4.1.2. Antibacterial Assays
4.1.3. Nematicidal Assays
4.1.4. Acetylcholinesterase Inhibition Assays
4.2. Computational Methods
4.2.1. Calculation of Pesticide-Likeness Molecular Descriptors
4.2.2. Calculation of Toxicity
4.2.3. Molecular Docking
4.2.4. Statistical Analysis
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Code of Molecule | MW | MLOGP | HBA | HBD | RB | AB |
---|---|---|---|---|---|---|
H1 | 298.34 | 3.211 | 5 | 0 | 3 | 12 |
H2 | 298.34 | 3.211 | 5 | 0 | 3 | 12 |
H3 | 286.3 | 3.899 | 5 | 0 | 2 | 12 |
H4 | 370.45 | 5.007 | 4 | 0 | 4 | 18 |
H5 | 298.34 | 3.211 | 5 | 0 | 3 | 12 |
H6 | 284.31 | 2.971 | 5 | 1 | 2 | 12 |
H7 | 328.37 | 2.926 | 6 | 0 | 4 | 12 |
H8 | 347.2 | 4.137 | 4 | 0 | 2 | 12 |
H9 | 302.75 | 4.019 | 4 | 0 | 2 | 12 |
H10 | 311.39 | 3.446 | 5 | 0 | 3 | 12 |
Demethylase | Chitinase | Transferase | Endoglucanase I | Proteinase K | Pectinase | AChE | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Code of Mol. | Total E | Code of Mol. | Total E | Code of Mol. | Total E | Code of Mol. | Total E | Code of Mol. | Total E | Code of Mol. | Total E | Code of Mol. | Total E |
H4 | −85.20 | 38f * | −120.51 | 3lp * | −87.65 | H4 | −106.52 | H2 | −97.70 | H10 | −76.66 | e20 * | −117.34 |
H1 | −81.74 | H4 | −104.99 | H4 | −82.74 | H5 | −103.78 | H10 | −94.29 | H1 | −75.23 | H4 | −108.34 |
5lw * | −80.98 | H6 | −98.86 | H6 | −81.44 | in1 * | −101.69 | H9 | −92.93 | H4 | −74.98 | H1 | −100.08 |
H7 | −79.88 | H5 | −97.41 | H5 | −77.38 | H6 | −101.60 | H5 | −87.31 | H6 | −73.74 | H10 | −99.86 |
H2 | −78.71 | H1 | −96.77 | H1 | −76.96 | H2 | −101.03 | H8 | −86.93 | Nag * | −73.49 | H5 | −95.48 |
H5 | −78.21 | H3 | −96.74 | H7 | −76.42 | H1 | −99.22 | H6 | −86.36 | H3 | −73.31 | H9 | −95.08 |
H8 | −77.94 | H7 | −96.31 | H3 | −75.19 | H9 | −96.67 | H3 | −86.33 | H8 | −73.26 | H7 | −94.89 |
H6 | −77.39 | H10 | −95.94 | H10 | −73.74 | H8 | −92.21 | H4 | −81.16 | H5 | −72.97 | H6 | −93.44 |
H10 | −76.52 | H8 | −94.86 | H8 | −73.14 | H7 | −91.48 | H1 | −81.08 | H7 | −71.24 | H2 | −93.09 |
H9 | −76.42 | H2 | −89.52 | H2 | −72.15 | H10 | −90.50 | H7 | −76.08 | H9 | −70.82 | H3 | −92.24 |
H3 | −75.40 | H9 | −88.97 | H9 | −68.58 | H3 | −83.88 | Cou * | −72.31 | H2 | −70.26 | H8 | −90.52 |
Residue | Energy (kcal mol−1) | Residue | Energy (kcal mol−1) |
---|---|---|---|
Hydrogen bond | Van der Waals interactions | ||
S-Asn161 | −6.68 | M-Ala159 | −2.35 |
M-Thr223 | −2.76 | M-Gly160 | −7.12 |
S-Thr223 | −1.10 | M-Asn161 | −4.47 |
M-Ser224 | −3.50 | S-Asn161 | −3.05 |
S-Ser224 | −9.50 | S-Asn162 | −3.02 |
Van der Waals interactions | S-Tyr169 | -3.46 | |
S-Asn67 | −0.85 | M-Thr223 | −1.60 |
S-Leu96 | −0.69 | M-Ser224 | −1.93 |
M-Asn99 | −1.14 | S-Ser224 | −3.55 |
M-Ser132 | −5.26 | Fluorine interactions | |
M-Leu133 | −8.13 | M-Gly100 | −1.32 |
M-Gly134 | −6.89 | ||
M-Gly135 | −3.01 | π–π T−shaped interactions | |
M-Ala158 | −2.11 | S-His69 | −8.06 |
Residue | Energy (kcal mol−1) |
---|---|
hydrogen bond | |
S-Tyr121 | −7.07 |
S-Tyr121 | −6.07 |
Van der Waals interactions | |
S-Tyr70 | −1.31 |
M-Trp84 | −0.02 |
M-Gly117 | −0.45 |
S-His440 | −3.87 |
S-Trp279 | −1.09 |
π–π stacked interactions | |
S-Phe290 | −1.09 |
π–π T-shaped interactions | |
M-Phe331 | −5.43 |
π-alkyl interactions | |
S-Phe330 | −13.08 |
M-Phe331 | −15.11 |
S-Tyr334 | −10.83 |
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Rastija, V.; Vrandečić, K.; Ćosić, J.; Kanižai Šarić, G.; Majić, I.; Agić, D.; Šubarić, D.; Karnaš, M.; Bešlo, D.; Brahmbhatt, H.; et al. Antifungal Activities of Fluorinated Pyrazole Aldehydes on Phytopathogenic Fungi, and Their Effect on Entomopathogenic Nematodes, and Soil-Beneficial Bacteria. Int. J. Mol. Sci. 2023, 24, 9335. https://doi.org/10.3390/ijms24119335
Rastija V, Vrandečić K, Ćosić J, Kanižai Šarić G, Majić I, Agić D, Šubarić D, Karnaš M, Bešlo D, Brahmbhatt H, et al. Antifungal Activities of Fluorinated Pyrazole Aldehydes on Phytopathogenic Fungi, and Their Effect on Entomopathogenic Nematodes, and Soil-Beneficial Bacteria. International Journal of Molecular Sciences. 2023; 24(11):9335. https://doi.org/10.3390/ijms24119335
Chicago/Turabian StyleRastija, Vesna, Karolina Vrandečić, Jasenka Ćosić, Gabriella Kanižai Šarić, Ivana Majić, Dejan Agić, Domagoj Šubarić, Maja Karnaš, Drago Bešlo, Harshad Brahmbhatt, and et al. 2023. "Antifungal Activities of Fluorinated Pyrazole Aldehydes on Phytopathogenic Fungi, and Their Effect on Entomopathogenic Nematodes, and Soil-Beneficial Bacteria" International Journal of Molecular Sciences 24, no. 11: 9335. https://doi.org/10.3390/ijms24119335