Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals
2.2. General Procedure for the Synthesis of Compound (3)
2.3. General Procedure for the Synthesis of Intermediates Compounds (4)
2.4. General Procedure for the Synthesis of Title Compounds (5)
2.5. X-ray Diffraction
2.6. Biological Assay
2.7. Computational Methods
3. Results and Discussion
3.1. Synthesis
3.2. The Structure–Activity Relationships
3.3. Molecular Docking Studies
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Compound | R1 | R2 | R3 | R4 | Melting Point (°C) | Yield (%) |
---|---|---|---|---|---|---|
5a | H | H | CH3 | - | 204–205 | 66 |
5b | 4-Cl | H | CH3 | - | 205–207 | 55 |
5c | 4-CH3 | H | CH3 | - | 194–196 | 75 |
5d | 2,4-Cl | H | CH3 | - | 195–196 | 50 |
5e | 4-Br | H | CH3 | - | 214–215 | 51 |
5f | 3-CH3 | H | CH3 | - | 203–205 | 77 |
5g | 4-OCH3 | H | CH3 | - | 210–212 | 70 |
5h | 4-C(CH3)3 | H | CH3 | - | 212–214 | 80 |
5i | 4-CH2CH3 | H | CH3 | - | 199–201 | 82 |
5j | H | CH3 | CH3 | - | 199–200 | 79 |
5k | 4-CH3 | CH3 | CH3 | - | 198–200 | 77 |
5l | 2,4-Cl | CH3 | CH3 | - | 194–196 | 55 |
5m | 4-CH2CH3 | CH3 | CH3 | - | 213–215 | 81 |
5n | 4-H | H | H | - | 189–191 | 55 |
5o | 4-CH3 | H | H | - | 196–198 | 78 |
5p | H | - | - | - | 249–250 | 51 |
5q | 4-CH3 | - | - | - | 202–204 | 59 |
5r | - | - | - | H | 185–187 | 70 |
5s | - | - | - | CH3 | 196–198 | 76 |
5t | - | - | - | H | 175–177 | 54 |
5u | - | - | - | CH3 | 182–183 | 67 |
Compound | Recovery of Root Length (%) | Recovery of Plant Weight (%) | Recovery of Chlorophyll (%) |
---|---|---|---|
Fenchlorazole | 37.16 ± 0.63 | 130.05 ± 0.44 | 97.52 ± 0.13 |
5a | 20.50 ± 0.59 | 68.61 ± 0.95 | 44.90 ± 0.29 |
5b | 20.55 ± 0.71 | 57.84 ± 0.94 | 20.12 ± 0.25 |
5c | 71.72 ± 1.16 | 109.87 ± 1.57 | 55.37 ± 0.17 |
5d | 1.22 ± 0.84 | 51.56 ± 0.34 | 14.32 ± 0.30 |
5e | 13.78 ± 0.91 | 65.46 ± 0.70 | 21.23 ± 0.66 |
5f | 31.72 ± 0.86 | 90.59 ± 1.27 | 44.92 ± 0.61 |
5g | 25.59 ± 1.37 | 78.49 ± 0.63 | 35.80 ± 0.75 |
5h | 35.19 ± 0.42 | 65.91 ± 0.55 | 43.83 ± 0.84 |
5i | 47.41 ± 0.42 | 100.90 ± 1.56 | 48.75 ± 0.48 |
5j | 39.64 ± 1.16 | 107.63 ± 0.80 | 39.12 ± 0.80 |
5k | 44.48 ± 0.78 | 129.62 ± 1.00 | 46.29 ± 0.23 |
5l | 54.79 ± 1.02 | 70.38 ± 1.00 | 48.21 ± 0.22 |
5m | 48.90 ± 0.52 | 129.13 ± 1.17 | 65.84 ± 0.04 |
5n | 30.27 ± 1.06 | 159.18 ± 0.75 | 28.93 ± 0.35 |
5o | 70.76 ± 0.43 | 143.51 ± 0.82 | 99.77 ± 0.93 |
5p | 18.23 ± 0.59 | 78.48 ± 1.09 | 26.98 ± 0.74 |
5q | 34.34 ± 0.81 | 113.46 ± 0.45 | 30.31 ± 0.34 |
5r | 2.39 ± 0.31 | 79.84 ± 0.68 | 23.43 ± 0.36 |
5s | 41.22 ± 0.88 | 105.84 ± 0.82 | 55.63 ± 0.62 |
5t | 27.66 ± 0.54 | 71.31 ± 0.98 | 26.98 ± 0.74 |
5u | 24.89 ± 0.15 | 78.03 ± 0.31 | 32.51 ± 0.04 |
Name | Log p a | ARs b | SA b | RBs b | HBAs b | Electronegativity c |
---|---|---|---|---|---|---|
Fenoxaprop-P-ethyl | 4.64 | 3 | 335 | 7 | 5 | |
Fenchlorazole | 6.07 | 2 | 344 | 5 | 4 | |
5o | 6.02 | 3 | 431 | 3 | 4 |
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Guo, K.-L.; Zhao, L.-X.; Wang, Z.-W.; Rong, S.-Z.; Zhou, X.-L.; Gao, S.; Fu, Y.; Ye, F. Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener. Biomolecules 2019, 9, 438. https://doi.org/10.3390/biom9090438
Guo K-L, Zhao L-X, Wang Z-W, Rong S-Z, Zhou X-L, Gao S, Fu Y, Ye F. Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener. Biomolecules. 2019; 9(9):438. https://doi.org/10.3390/biom9090438
Chicago/Turabian StyleGuo, Ke-Liang, Li-Xia Zhao, Zi-Wei Wang, Shu-Zhe Rong, Xiao-Lin Zhou, Shuang Gao, Ying Fu, and Fei Ye. 2019. "Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener" Biomolecules 9, no. 9: 438. https://doi.org/10.3390/biom9090438