Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Materials and Measurements
3.2. General Synthetic Method for Compounds 3
3.3. Insecticidal Activity
3.4. Enzyme Activity
3.5. Antifungal Activity
3.6. Quantitative Structure–Activity Relationship (QSAR) Analyses
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 8a–8t are available from the authors. |
Compound | H. armigera (Hübner) | T. truncatus | T. turkestani | |||
---|---|---|---|---|---|---|
Mortality Rate % (48 h) | Growth and Development | Mortality Rate % (24 h) | Mortality Rate % (48 h) | Mortality Rate % (24 h) | Mortality Rate % (48 h) | |
3a | 0 | ND | 15.56 | 63.33 | 10.41 | 40.62 |
3b | 3 | dysplasia | 13.33 | 48.89 | 8.93 | 50.00 |
3c | 10 | dysplasia | 27.78 | 45.56 | 22.29 | 46.87 |
3d | 37 | dysplasia | 55.56 | 83.33 | 26.75 | 35.94 |
3e | 30 | dysplasia | 30.00 | 40.00 | 25.27 | 71.87 |
3f | 23 | dysplasia | 38.89 | 52.22 | 47.57 | 70.31 |
3g | 60 | dysplasia | 64.44 | 93.33 | 28.24 | 48.44 |
3h | 13 | dysplasia | 17.89 | 35.67 | 60.95 | 79.69 |
3i | 17 | dysplasia | 84.44 | 93.33 | 53.51 | 64.06 |
3j | 7 | dysplasia | 33.33 | 37.78 | 74.33 | 82.81 |
3k | 0 | ND | 18.89 | 33.33 | 11.89 | 37.50 |
3l | 0 | ND | 15.56 | 32.22 | 16.36 | 62.50 |
3m | 0 | ND | 65.56 | 82.22 | 13.37 | 31.25 |
3n | 10 | dysplasia | 15.56 | 30.00 | 13.37 | 62.50 |
3o | 10 | dysplasia | 12.22 | 16.67 | 5.94 | 18.75 |
3p | 7 | dysplasia | 11.11 | 17.78 | 25.27 | 21.87 |
3q | 10 | dysplasia | 13.23 | 15.36 | 41.62 | 59.37 |
3r | 0 | ND | 15.56 | 51.11 | - | - |
3s | 7 | dysplasia | 12.22 | 22.22 | 35.67 | 50.00 |
3t | 0 | ND | 17.78 | 41.11 | 5.95 | 0.00 |
chlorantraniliprole | 100 | ND | - | - | - | - |
biflenazate | - | - | 85.56 | 95.56 | 61.11 | 65.62 |
pyridaben | - | - | 61.11 | 71.21 | 97.78 | 98.44 |
hexythiazox | - | - | 83.33 | 83.33 | 67.19 | 71.11 |
Compound | Inhibition Ratio (%) | ||||||
---|---|---|---|---|---|---|---|
CL | RS | FF | PG | AK | SSR | RSR | |
3a | 17.89 | 20.87 | 31.74 | 21.09 | 37.32 | 32.32 | 56.75 |
3b | 0.00 | −4.81 | 4.63 | 32.43 | 11.97 | 55.49 | 67.86 |
3c | 0.00 | −9.40 | 8.37 | 23.36 | 37.32 | 39.23 | 36.31 |
3d | 0.00 | 40.04 | 29.64 | 37.19 | 40.85 | 49.39 | 22.62 |
3e | 0.00 | 10.02 | 50.44 | 60.09 | 57.04 | 49.59 | 29.56 |
3f | 1.42 | −3.76 | 15.38 | 19.73 | 25.35 | 1.22 | 11.71 |
3g | 0.00 | −2.72 | 3.46 | 31.97 | 22.54 | 42.89 | 4.96 |
3h | 0.00 | 6.89 | 14.91 | 24.49 | 37.32 | 36.18 | 41.87 |
3i | 0.00 | −8.98 | 17.02 | 27.44 | 41.55 | 26.63 | 73.81 |
3j | 0.00 | −8.98 | 8.60 | 29.71 | 31.69 | 7.72 | 80.95 |
3k | 19.51 | 4.17 | 22.86 | 24.94 | 40.85 | 13.21 | 18.85 |
3l | 15.04 | −5.22 | 31.98 | 32.43 | 33.10 | 46.34 | 16.27 |
3m | 28.46 | −6.06 | 26.60 | 35.83 | 41.55 | 57.93 | 50.60 |
3n | 0.00 | 17.32 | 32.21 | 36.51 | 11.97 | 22.97 | 16.27 |
3o | 0.00 | −10.03 | 15.61 | 24.94 | 26.76 | 17.80 | 8.13 |
3p | 0.00 | −5.43 | 13.51 | 30.61 | 38.03 | 2.85 | 14.29 |
3q | 0.00 | 7.30 | 4.63 | 31.29 | 63.38 | 55.49 | 78.57 |
3r | 73.17 | 57.41 | 50.44 | 56.43 | 60.14 | 65.04 | 84.33 |
3s | 7.11 | 5.22 | 22.86 | 34.92 | 42.25 | 31.10 | 84.13 |
3t | 6.30 | −2.72 | 17.02 | 33.33 | 7.04 | 3.46 | 4.96 |
azoxystrobin | 66.54 | 18.37 | 55.61 | 73.92 | 61.97 | 89.63 | 90.48 |
kresoxim-methyl | 0.00 | 1.25 | 25.20 | 21.54 | 19.25 | 2.24 | 75.00 |
trifloxystrobin | 46.54 | 28.60 | 52.55 | 71.28 | 65.39 | 86.79 | 17.26 |
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Zhou, Y.; Wang, C.; Xin, F.; Han, X.; Zhang, J.; Sun, K. Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs. Molecules 2018, 23, 1473. https://doi.org/10.3390/molecules23061473
Zhou Y, Wang C, Xin F, Han X, Zhang J, Sun K. Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs. Molecules. 2018; 23(6):1473. https://doi.org/10.3390/molecules23061473
Chicago/Turabian StyleZhou, Yueting, Chunjuan Wang, Fang Xin, Xiaoqiang Han, Jie Zhang, and Ke Sun. 2018. "Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs" Molecules 23, no. 6: 1473. https://doi.org/10.3390/molecules23061473
APA StyleZhou, Y., Wang, C., Xin, F., Han, X., Zhang, J., & Sun, K. (2018). Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs. Molecules, 23(6), 1473. https://doi.org/10.3390/molecules23061473