Novel Pyridyl–Oxazole Carboxamides: Toxicity Assay Determination in Fungi and Zebrafish Embryos
Abstract
:1. Introduction
2. Results and Discussion
2.1. Biological Activities of Target Compounds
2.2. Toxicity to Zebrafish Embryos
3. Materials and Methods
3.1. Materials
3.2. Fish Husbandry and Embryo Collection
3.3. Ethics Statement
3.4. Fungicidal Activity and Toxicity Determination
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compd. | R | Botrytis cinereal | |||
---|---|---|---|---|---|
100 mg/L | 50 mg/L | 25 mg/L | 12.5 mg/L | ||
6a | 2-F | 100 | 45.88 | 12.36 | nt |
6b | 4-F | 100 | 52.06 | 41.18 | 30.08 |
6c | 2,4-di-F | 100 | 63.83 | 40.30 | 29.71 |
6d | 2,6-di-F | 100 | 62.06 | 49.41 | 32.94 |
6e | 3-Cl | 100 | 66.47 | 14.71 | nt |
6f | 3-Cl-2-CH3 | 90 | 65.00 | 44.71 | 17.36 |
6g | 4-CH3 | 100 | 41.76 | 7.65 | 3.83 |
6h | 2,4-di-CH3 | 100 | 64.41 | 28.83 | 7.06 |
Azoxystrobin | 100 | 40 | 20 | 0 |
Compd. | R | Rhizoctonia solani | |||
---|---|---|---|---|---|
100 mg/L | 50 mg/L | 25 mg/L | 12.5 mg/L | ||
6a | 2-F | 90 | 47.06 | 29.31 | 17.69 |
6b | 4-F | 100 | 51.77 | 41.71 | 31.77 |
6c | 2,4-di-F | 80 | 79.12 | 18.24 | 16.77 |
6d | 2,6-di-F | 80 | 50.00 | 42.06 | 20.06 |
6e | 3-Cl | 90 | 57.90 | 18.83 | 11.77 |
6f | 3-Cl-2-CH3 | 80 | 66.77 | 36.77 | 6.18 |
6g | 4-CH3 | 70 | nt | nt | nt |
6h | 2,4-di-CH3 | 90 | 55.30 | 34.41 | 4.41 |
Azoxystrobin | 100 | 60 | 20 | 0 |
Compd. | R | 1H-NMR | 13C-NMR | HRMS |
---|---|---|---|---|
6a | 2-F | 1H-NMR (600 MHz, DMSO-d6) δ:9.92 (s, 1H, NH), 8.98 (s, 1H, oxazole-H), 8.77 (d, J = 4.8 Hz, 1H, Py-H), 8.22 (d, J = 7.8 Hz, 1H, Py-H), 8.07 (m, 1H, Py-H), 7.81–7.82 (m, 1H, Ph-H), 7.62–7.63 (m, 1H, Py-H), 7.34–7.35 (m, 1H, Ph-H), 7.27–7.28 (m, 2H, Ph-H) | 13C-NMR (151 MHz, DMSO-d6) δ: 160.4, 158.9, 156.3, 154.6, 150.6, 145.1, 144.5, 138.2, 137.3, 127.2 (d, J = 7.6 Hz), 126.3 (d, J = 26.0 Hz), 125.5 (d, J = 11.9 Hz), 125.0 (d, J = 3.3 Hz), 123.1, 116.2 (d, J = 19.6 Hz) | calcd for C15H11FN3O2 ([M + H]+) 284.0830, found 284.0822 |
6b | 4-F | 1H-NMR (600 MHz, DMSO-d6) δ: 10.32 (s, 1H, NH), 8.95 (s, 1H, oxazole-H), 8.77 (d, J = 4.8 Hz, 1H, Py-H), 8.23 (d, J = 8.0 Hz, 1H, Py-H), 8.07 (td, J = 8.0, 1.5 Hz, 1H, Py-H), 7.84–7.87 (m, 2H, Ph-H), 7.61–7.62 (m, 1H, Py-H), 7.21 (t, J = 9.0 Hz, 2H, Ph-H) | 13C-NMR (151 MHz, DMSO-d6) δ: 160.28, 159.79, 158.97, 158.19, 150.58, 145.25, 144.44, 138.18, 137.87, 135.10, 126.28, 123.01, 123.0, 122.9, 115.70 (d, J = 22.1 Hz) | calcd for C15H11FN3O2 ([M + H]+) 284.0830 found 284.0820 |
6c | 2,4-di-F | 1H-NMR (500 MHz, DMSO-d6) δ: 10.06 (s, 1H, NH), 8.97 (s, 1H, oxazole-H), 8.77 (d, J = 5.0, 1H, Py-H), 8.21 (d, J = 8.0 Hz, 1H, Py-H), 8.06–8.07 (m, 1H, Py-H), 7.71–7.72 (m, 1H, Ph-H), 7.61 (q, J = 3.0 Hz, 1H, Py-H), 7.39–7.40 (m, 1H, Ph-H), 7.14 (t, J = 4.5 Hz, 1H, Ph-H) | 13C-NMR (126 MHz, DMSO-d6) δ: 159.87, 158.57, 150.09, 144.68, 144.02, 137.70, 136.73, 127.60 (d, J = 11.0 Hz), 125.81, 122.55, 111.33 (d, J = 3.4 Hz), 111.15 (d, J = 3.4 Hz), 104.54, 104.33 (d, J = 2.8 Hz), 104.13 | calcd for C15H10F2N3O2 ([M + H]+) 302.0736 found 302.0731 |
6d | 2,6-di-F | 1H-NMR (600 MHz, DMSO-d6) δ: 10.03 (s, 1H, NH), 8.97 (s, 1H, oxazole-H), 8.77–8.79 (m, 1H, Py-H), 8.21 (d, J = 7.8 Hz, 1H, Py-H), 8.06–8.07 (m, 1H, Py-H), 7.72–7.73 (m, 1H, Ph-H), 7.61–7.63 (m, 1H, Py-H), 7.39–7.41 (m, 1H, Ph-H), 7.15–7.16 (m, 1H, Ph-H) | 13C-NMR (151 MHz, DMSO-d6) δ: 160.4, 159.1, 150.6, 145.2, 144.5, 138.2, 137.2, 128.2 (d, J = 9.5 Hz), 126.3, 123.1, 111.7 (dd, J = 22.1, 3.5 Hz), 104.8 (dd, J = 26.6, 24.2 Hz) | calcd for C15H10F2N3O2 ([M + H]+) 302.0736, found 302.0726 |
6e | 3-Cl | 1H-NMR (600 MHz, DMSO-d6) δ: 10.44 (s, 1H, NH), 8.98 (s, 1H, oxazole-H), 8.77 (d, J = 4.8 Hz, 1H, Py-H), 8.24 (d, J = 7.8 Hz, 1H, Py-H), 8.07–8.08 (m, 1H, Py-H), 8.03–8.04 (m, 1H, Ph-H), 7.80 (d, J = 8.2, 2.4 Hz, 1H, Ph-H), 7.62–7.63 (m, 1H, Py-H), 7.40 (t, J = 8.2 Hz, 1H, Ph-H), 7.19–7.20 (m, 1H, Ph-H) | 13C-NMR (126 MHz, DMSO) δ: 159.8, 158.8, 150.1, 144.7, 144.2, 139.8, 137.7, 137.2, 132.9, 130.3, 125.8, 123.0, 122.6, 120.0, 118.9 | calcd for C15H11ClN3O2 ([M + H]+) 300.0534, found 300.0522 |
6f | 3-Cl-2-CH3 | 1H-NMR (500 MHz, DMSO-d6) δ: 10.15 (s, 1H, NH), 8.95 (s, 1H, oxazole-H), 8.77 (d, J = 5.0 Hz, 1H, Py-H), 8.22 (d, J = 7.8 Hz, 1H, Py-H), 8.07–8.08 (m, 1H, Py-H), 7.62–7.63 (m, 1H, Py-H), 7.43 (dd, J = 7.8, 1.2 Hz, 1H, Ph-H), 7.38–7.39 (m, 1H, Ph-H), 7.26 (t, J = 7.8 Hz, 1H, Ph-H), 2.28 (s, 3H, CH3) | 13C-NMR (126 MHz, DMSO) δ: 160.3, 159.1, 150.6, 145.2, 144.4, 138.2, 137.6, 137.6, 134.2, 132.0, 127.4, 127.2, 126.3, 125.7, 123.0, 15.7 | calcd for C16H13ClN3O2 ([M + H]+) 314.0691, found 314.0690 |
6g | 4-CH3 | 1H-NMR (600 MHz, DMSO-d6) δ: 10.12 (s, 1H, NH), 8.92 (s, 1H, oxazole-H), 8.76 (d, J = 4.2 Hz, 1H, Py-H), 8.24 (d, J = 7.8 Hz, 1H, Py-H), 8.06–8.07 (m, 1H, Py-H), 7.70 (d, J = 8.4 Hz, 2H, Ph-H), 7.60–7.61 (m, 1H, Py-H), 7.17 (d, J = 17.2 Hz, 2H, Ph-H), 2.29 (s, 3H, CH3) | 13C-NMR (151 MHz, DMSO-d6) δ: 160.2, 158.8, 150.6, 145.3, 144.2, 138.2, 138.0, 136.2, 133.5, 129.5, 126.3, 123.1, 121.0, 21.0 | calcd for C16H14N3O2 ([M + H]+) 280.1081, found 280.1065 |
6h | 2. 4-di-CH3 | 1H-NMR (500 MHz, DMSO-d6) δ: 9.73 (s, 1H, NH), 8.91 (s, 1H, oxazole-H), 8.76–8.78 (m, 1H, Py-H), 8.22 (d, J = 8.0 Hz, 1H, Py-H), 8.06–8.08 (m, 1H, Py-H), 7.61–7.63 (m, 1H, Py-H), 7.36–7.37 (m, 1H, Ph-H), 7.10 (d, J = 2.0 Hz, 1H, Ph-H), 7.03 (d, J = 8.0 Hz, 1H, Ph-H), 2.29 (s, 3H, CH3), 2.23 (s, 3H, CH3) | 13C-NMR (126 MHz, CDCl3) δ: 159.8, 158.3, 150.1, 144.8, 143.4, 137.6, 137.4, 134.9, 132.9, 132.2, 130.9, 126.6, 125.7, 125.3, 20.5, 17.6 | calcd for C17H16N3O2 ([M + H]+) 294.1237, found 294.1226 |
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Chen, S.; Zhang, D.-L.; Ren, C.-L.; Zou, W.-Q.; Tian, X.-Y.; Du, X.-H.; Tan, C.-X. Novel Pyridyl–Oxazole Carboxamides: Toxicity Assay Determination in Fungi and Zebrafish Embryos. Molecules 2021, 26, 3883. https://doi.org/10.3390/molecules26133883
Chen S, Zhang D-L, Ren C-L, Zou W-Q, Tian X-Y, Du X-H, Tan C-X. Novel Pyridyl–Oxazole Carboxamides: Toxicity Assay Determination in Fungi and Zebrafish Embryos. Molecules. 2021; 26(13):3883. https://doi.org/10.3390/molecules26133883
Chicago/Turabian StyleChen, Shu, Dong-Lin Zhang, Chao-Li Ren, Wen-Qian Zou, Xiao-Yu Tian, Xiao-Hua Du, and Cheng-Xia Tan. 2021. "Novel Pyridyl–Oxazole Carboxamides: Toxicity Assay Determination in Fungi and Zebrafish Embryos" Molecules 26, no. 13: 3883. https://doi.org/10.3390/molecules26133883