Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea
Abstract
:1. Introduction
2. Result and Discussion
2.1. Chemistry
2.2. Biological Activity and Structure–Activity Relationship Study
3. Materials and Method
3.1. Materials and Instrumentation
3.2. Synthesis
3.2.1. Synthesis of N-(2-Trifluoromethyl-4-chlorophenyl)-2-aminocyclohexyl Sulfonamide L-2
3.2.2. Synthesis of Substituted Chloroacetamide I
3.2.3. Synthesis of 2-Glycinamide Cyclohexyl Sulfonamide Derivatives II-1 to II-28
3.2.4. Synthesis of N-(2-Trifluoromethyl-4-chlorophenyl)-2-ethoxyacylmethyl Amino Cyclohexyl Sulfonamide L-4 and N-(2-Trifluoromethyl-4-chlorophenyl)-2-carboxymethyl Amino Cyclohexyl Sulfonamide L-5
3.2.5. Synthesis of 2-Glycinamide Cyclohexyl Sulfonamide Derivatives II-29 to II-33
3.3. Fungal Bioassay
3.3.1. Evaluation of Target Compounds II on the Inhibition of B. cinerea
3.3.2. Evaluation of the Fungicidal Activity on B. cinerea by Concentration Gradient Test
3.3.3. In Vivo Fungicidal Activity against B. cinerea (CY-09) by Greenhouse Pot Experiments
(1). Evaluation of Fungicidal Activity on Cucumber Leaves
(2). Evaluation of Fungicidal Activity on Tomato Leaves
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Compd. | R | Inhibition Rate (%) | EC50 Values |
---|---|---|---|
II-1 | C6H5– | 12.49 | >100 |
II-2 | 3-F–C6H4– | 51.08 | >100 |
II-3 | 4-F–C6H4– | 76.89 | 16.23 |
II-4 | 2,4-2F–C6H3– | 90.66 | 4.01 |
II-5 | 2,5-2F–C6H3– | 85.74 | 3.38 |
II-6 | 2-F–4-Cl–C6H3– | 89.18 | 3.38 |
II-7 | 2-F–4-Br–C6H3– | 81.32 | 9.44 |
II-8 | 3-F–4-Br–C6H3– | 84.76 | 7.23 |
II-9 | 2-CF3–4-F–C6H3– | 84.51 | 23.57 |
II-10 | 2-F–5-CF3–C6H3– | 69.27 | 13.66 |
II-11 | 3-Br–4F–C6H3– | 72.71 | 12.68 |
II-12 | 3-CN–4-F–C6H3– | 90.41 | 16.27 |
II-13 | 2,3,4-3F–C6H2– | 90.90 | 14.67 |
II-14 | 2,4,5-3F–C6H2– | 88.94 | 8.9 |
II-15 | 2-Br–C6H4– | 85.25 | 4.99 |
II-16 | 3-Br–C6H4– | 53.05 | >100 |
II-17 | 2,4-2Br–C6H3– | 73.45 | 16.48 |
II-18 | 2-CH3–C6H4– | 33.87 | >100 |
II-19 | 2-CF3–C6H4– | 82.79 | 3.26 |
II-20 | 3-CF3–C6H4– | 6.59 | >100 |
II-21 | 3,5-2CF3–C6H3– | 31.91 | >100 |
II-22 | 3-CH3O–C6H4– | 14.70 | >100 |
II-23 | 4-CH3O–C6H4– | 33.38 | >100 |
II-24 | 2-CF3O–C6H4– | 51.57 | >100 |
II-25 | 2-Cl-C6H4-CH2– | 56.00 | 8.02 |
II-26 | 2-Br–C6H4–CH2– | 88.20 | 3.4 |
II-27 | 2-CH3–C6H4–CH2– | 66.81 | 15.13 |
II-28 | 2-Br–C6H4–CH2CH2– | 75.42 | 3.57 |
II-29 | CH3CH2– | 55.75 | 34.18 |
II-30 | CH3(CH2)2– | 75.42 | 5.9 |
II-31 | 69.52 | 3.77 | |
II-32 | 81.32 | 14.07 | |
II-33 | CH3(CH2)3– | 83.78 | 6.5 |
Carbendazim | / | 33.87 | 867.82 |
Procymidone | / | 69.27 | 10.31 |
Boscalid | / | 89.18 | 4.46 |
Compd. | R | HLD-15 | DL-11 | ||
---|---|---|---|---|---|
Inhibition Rate (%) | EC50 Values | Inhibition Rate (%) | EC50 Values | ||
II-4 | 2,4-2F–C6H3– | 83.41 | 1.88 | 89.47 | 2.07 |
II-5 | 2,5-2F–C6H3– | 83.93 | 2.3 | 87.63 | 2.55 |
II-6 | 2-F–4-Cl–C6H3– | 71.75 | 2.13 | 91.57 | 3.94 |
II-26 | 2-Br–C6H4–CH2– | 70.19 | 2.96 | 94.47 | 2.92 |
II-27 | 2-CH3–C6H4–CH2– | 79.52 | 7.25 | 78.94 | 5.55 |
II-28 | 2-Br–C6H4–CH2CH2– | 96.89 | 2.26 | 95.00 | 2.47 |
II-30 | CH3(CH2)2– | 84.19 | 7.12 | 86.05 | 5.79 |
II-31 | 75.12 | 5.31 | 65.24 | 4.36 | |
II-33 | CH3(CH2)3– | 76.67 | 6.34 | 95.26 | 2.97 |
Carbendazim | / | 10.32 | 427.78 | 10.48 | 673.38 |
Procymidone | / | 79.00 | 10.13 | 75.25 | 8.61 |
Boscalid | / | 87.82 | 2.44 | 86.57 | 2.27 |
Compd. | Inhibition Rate (%) | Compd. | Inhibition Rate (%) |
---|---|---|---|
II-2 | 33.33 | II-17 | 59.52 |
II-3 | 79.76 | II-18 | 20.83 |
II-4 | 90.48 | II-20 | 64.88 |
II-5 | 93.45 | II-23 | 27.38 |
II-6 | 86.31 | II-24 | 71.43 |
II-7 | 80.36 | II-25 | 35.71 |
II-8 | 79.17 | II-26 | 53.57 |
II-9 | 73.81 | II-27 | 37.50 |
II-10 | 72.62 | II-28 | 51.19 |
II-11 | 62.50 | II-29 | 66.07 |
II-12 | 92.86 | II-30 | 42.86 |
II-13 | 91.07 | II-31 | 63.09 |
II-14 | 75.60 | II-32 | 71.43 |
II-15 | 88.69 | II-33 | 75.00 |
II-16 | 30.95 | Pyrimethanil | 82.14 |
Carbendazim | 59.52 | Boscalid | 88.10 |
Procymidone | 83.33 | Cyprodinil | 88.69 |
Compd. | 500 μg mL−1 | 200 μg mL−1 | ||
---|---|---|---|---|
Disease Index | Control Efficacy (%) | Disease Index | Control Efficacy (%) | |
II-2 | 5.82 | 74.43 | 11.37 | 70.98 |
II-4 | 7.47 | 67.19 | 8.42 | 78.51 |
II-5 | 7.19 | 68.43 | 8.26 | 78.91 |
II-6 | 18.66 | 18.04 | / | / |
II-7 | 5.96 | 73.83 | 12.10 | 69.11 |
II-8 | 4.52 | 80.14 | 4.71 | 87.98 |
II-10 | 12.69 | 44.27 | / | / |
II-11 | 11.28 | 50.46 | / | / |
II-13 | 21.39 | 6.04 | / | / |
II-14 | 9.73 | 57.27 | / | / |
II-15 | 5.25 | 76.96 | 4.71 | 87.97 |
II-16 | 19.71 | 13.43 | / | / |
II-17 | 14.52 | 36.25 | / | / |
II-18 | 14.72 | 35.33 | / | / |
II-19 | 17.21 | 24.40 | / | / |
II-20 | 21.71 | 4.66 | / | / |
II-24 | 20.99 | 7.81 | / | / |
II-26 | 13.30 | 41.57 | / | / |
II-28 | 8.21 | 63.93 | 12.61 | 67.83 |
II-29 | 9.17 | 59.74 | / | / |
II-30 | 11.56 | 49.21 | / | / |
II-31 | 8.58 | 62.33 | 15.08 | 61.51 |
II-32 | 16.02 | 29.63 | / | / |
II-33 | 6.37 | 72.02 | 9.74 | 75.15 |
Pyrimethanil | 15.25 | 33.00 | 19.62 | 49.93 |
Procymidone | 5.91 | 74.05 | 13.45 | 65.67 |
Boscalid | 5.23 | 77.05 | 8.58 | 78.10 |
CK | 22.77 | / | 39.18 | / |
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Cai, N.; Liu, C.; Feng, Z.; Li, X.; Qi, Z.; Ji, M.; Qin, P.; Ahmed, W.; Cui, Z. Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea. Molecules 2018, 23, 740. https://doi.org/10.3390/molecules23040740
Cai N, Liu C, Feng Z, Li X, Qi Z, Ji M, Qin P, Ahmed W, Cui Z. Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea. Molecules. 2018; 23(4):740. https://doi.org/10.3390/molecules23040740
Chicago/Turabian StyleCai, Nan, Caixiu Liu, Zhihui Feng, Xinghai Li, Zhiqiu Qi, Mingshan Ji, Peiwen Qin, Wasim Ahmed, and Zining Cui. 2018. "Design, Synthesis, and SAR of Novel 2-Glycinamide Cyclohexyl Sulfonamide Derivatives against Botrytis cinerea" Molecules 23, no. 4: 740. https://doi.org/10.3390/molecules23040740