Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Activities
2.2.1. Acaricidal Activity
2.2.2. Insecticidal Activities
3. Experimental Section
3.1. Chemistry
3.1.1. General Procedures
3.1.2. Synthesis of 4-(5-Trifluoromethylpyridin-2-yloxy)benzaldehyde (2)
3.1.3. Synthesis of 4-(5-Trifluoromethylpyridin-2-yloxy)phenylmethanol (3)
3.1.4. Synthesis of 2-(4-Chloromethylphenoxy)-5-(trifluoromethyl)pyridine (4)
3.1.5. General Procedure for the Preparation of 6d–6w
3.1.6. General Procedure for the Preparation of 8a–8w
3.2. Biological Tests
3.2.1. Bioassay Methods
3.2.2. Acaricidal Activity against Tetranychus cinnabarinus
3.2.3. Insecticidal Activity against Plutella xylostella
3.2.4. Insecticidal Activity against Aphis craccivora
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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- Sample Availability: Samples of the compounds 8a–8w are available from the authors.
Compd. | R | Tetranychus cinnabarinus | |||
---|---|---|---|---|---|
200 μg/mL | 100 μg/mL | 50 μg/mL | 10 μg/mL | ||
8a | Me | 0 | — b | — | — |
8b | Et | 0 | — | — | — |
8c | t-Bu | 0 | — | — | — |
8d | 2-FC6H4 | 100.00 ± 0.00 | 90.32 ± 1.38 | 70.43 ± 0.82 | 0 |
8e | 3-FC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
8f | 4-FC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
8g | 2-ClC6H4 | 70.28 ± 1.33 a | 0 | — | — |
8h | 3-ClC6H4 | 100.00 ± 0.00 | 30.39 ± 0.67 | — | — |
8i | 4-ClC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 50.49 ± 1.78 |
8j | 2-BrC6H4 | 80.16 ± 0.38 | 30.46 ± 1.52 | 0 | — |
8k | 3-BrC6H4 | 70.33 ± 1.22 | 0 | — | — |
8l | 4-BrC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
8m | 4-IC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
8n | C6H5 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
8o | 2-OMeC6H4 | 0 | — | — | — |
8p | 4-OMeC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
8q | 4-MeC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
8r | 4-t-BuC6H4 | 0 | — | — | — |
8s | 4-OCF3C6H4 | 100.00± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 95.29 ± 1.45 |
8t | 2,3-F2C6H3 | 100.00 ± 0.00 | 100.00 ± 0.00 | 80.42 ± 1.56 | — |
8u | 2,4-Cl2C6H3 | 80.17 ± 0.82 | 50.23 ± 1.43 | 0 | — |
8v | 2,3-Me2C6H3 | 0 | — | — | — |
8w | 2,4-Me2C6H3 | 100.00 ± 0.00 | 100.00 ± 0.00 | 60.35 ± 1.45 | — |
Fenpyroximate | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 | 100.00 ± 0.00 |
Compd. | R | Plutella xylostella | Aphis craccivora | ||
---|---|---|---|---|---|
200 μg/mL | 50 μg/mL | 200 μg/mL | 100 μg/mL | ||
8a | Me | 100.00 ± 0.00 | 0 | 30.26 ± 1.56 | — |
8b | Et | 0 | — b | 0 | — |
8c | t-Bu | 0 | — | 0 | — |
8d | 2-FC6H4 | 0 | — | 0 | — |
8e | 3-FC6H4 | 100.00 ± 0.00 | 86.42 ± 0.88 | 100.00 ± 0.00 | 60.18 ± 1.33 |
8f | 4-FC6H4 | 100.00 ± 0.00 | 43.36 ± 1.07 | 60.29 ± 1.52 | 30.41 ± 0.71 |
8g | 2-ClC6H4 | 0 | — | 0 | — |
8h | 3-ClC6H4 | 30.29 ± 1.55 a | 0 | 85.33 ± 1.25 | 50.27 ± 1.06 |
8i | 4-ClC6H4 | 100.00 ± 0.00 | 71.23 ± 0.95 | 95.28 ± 1.32 | 60.26 ± 1.69 |
8j | 2-BrC6H4 | 0 | — | 20.41 | — |
8k | 3-BrC6H4 | 57.35 ± 0.54 | 29.16 ± 1.86 | 0 | — |
8l | 4-BrC6H4 | 100.00 ± 0.00 | 100.00 ± 0.00 | 50.37 ± 1.32 | 0 |
8m | 4-IC6H4 | 100.00 ± 0.00 | 71.39 ± 1.53 | 0 | — |
8n | C6H5 | 100.00 ± 0.00 | 71.18 ± 0.65 | 70.25 ± 1.63 | 50.43 ± 1.38 |
8o | 2-OMeC6H4 | 0 | — | 0 | — |
8p | 4-OMeC6H4 | 100.00 ± 0.00 | 43.41 ± 1.71 | 70.32 ± 1.95 | 20.17 ± 0.71 |
8q | 4-MeC6H4 | 100.00 ± 0.00 | 71.22 ± 1.24 | 0 | — |
8r | 4-t-BuC6H4 | 0 | — | 100.00 ± 0.00 | 40.09 ± 0.36 |
8s | 4-OCF3C6H4 | 57.27 ± 0.83 | 43.35 ± 1.65 | — | — |
8t | 2,3-F2C6H3 | 43.09 ± 1.26 | 0 | — | — |
8u | 2,4-Cl2C6H3 | 43.25 ± 1.07 | 0 | — | — |
8v | 2,3-Me2C6H3 | 0 | — | — | — |
8w | 2,4-Me2C6H3 | 43.18 ± 0.92 | 0 | — | — |
Pyridalyl | 100.00 ± 0.00 | 100.00 ± 0.00 | — | — | |
Imidacloprid | — | — | 100.00 ± 0.00 | 100.00 ± 0.00 |
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Dai, H.; Chen, J.; Li, H.; Dai, B.; He, H.; Fang, Y.; Shi, Y. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety. Molecules 2016, 21, 276. https://doi.org/10.3390/molecules21030276
Dai H, Chen J, Li H, Dai B, He H, Fang Y, Shi Y. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety. Molecules. 2016; 21(3):276. https://doi.org/10.3390/molecules21030276
Chicago/Turabian StyleDai, Hong, Jia Chen, Hong Li, Baojiang Dai, Haibing He, Yuan Fang, and Yujun Shi. 2016. "Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety" Molecules 21, no. 3: 276. https://doi.org/10.3390/molecules21030276