Research Article
Synthesis, Structure, and Antifungal Activities of 3-(Difluoromethyl)-Pyrazole-4-Carboxylic Oxime Ester Derivatives
Table 2
The fungicidal activity of compounds 5a∼5o at 50 ppm.
| | No. | R | AS | GZ | PO | PC | SS | BC | RS | FO | CA | PP |
| | 5a | H | 27.8 ± 0.1 | 12.2 ± 0.1 | 28.6 ± 0.4 | 5.3 ± 0.1 | 17.9 ± 0.3 | 9.4 ± 0.3 | 32.8 ± 0.2 | 7.7 ± 0.1 | 17.6 ± 0.1 | 15.6 ± 0.2 | | 5b | 2-CH3 | 11.1 ± 0.2 | 12.2 ± 0.1 | 17.1 ± 0.4 | 10.5 ± 0.1 | 44.6 ± 0.3 | 12.5 ± 0.4 | 20.7 ± 0.1 | 19.2 ± 0.3 | 17.6 ± 0.1 | 25.0 ± 0.2 | | 5c | 3-CH3 | 16.7 ± 0.2 | 12.2 ± 0.1 | 14.3 ± 0.5 | 10.5 ± 0.2 | 17.9 ± 0.1 | 3.1 ± 0.3 | 43.1 ± 0.3 | 15.4 ± 0.1 | 23.5 ± 0.1 | 31.3 ± 0.2 | | 5d | 4-CH3 | 33.3 ± 0.3 | 12.2 ± 0.3 | 17.1 ± 0.2 | 5.3 ± 0.1 | 25.0 ± 0.4 | 9.4 ± 0.3 | 37.9 ± 0.1 | 7.7 ± 0.1 | 17.6 ± 0.1 | 31.3 ± 0.1 | | 5e | 2- OCH3 | 27.8 ± 0.3 | 29.3 ± 0.1 | 14.3 ± 0.1 | 13.2 ± 0.1 | 17.9 ± 0.3 | 12.5 ± 0.1 | 62.1 ± 0.3 | 19.2 ± 0.4 | 29.4 ± 0.1 | 53.1 ± 0.1 | | 5f | 4- OCH3 | 16.7 ± 0.1 | 22.0 ± 0.1 | 28.6 ± 0.1 | 5.3 ± 0.2 | 60.7 ± 0.1 | 18.8 ± 0.1 | 44.8 ± 0.1 | 19.2 ± 0.4 | 17.6 ± 0.1 | 9.4 ± 0.2 | | 5g | 3,4,5-tri-OCH3 | 33.3 ± 0.1 | 12.2 ± 0.1 | 85.7 ± 0.1 | 7.9 ± 0.2 | 44.6 ± 0.4 | 18.8 ± 0.1 | 29.3 ± 0.1 | 15.4 ± 0.1 | 17.6 ± 0.1 | 3.1 ± 0.1 | | 5h | 2-Br | 16.7 ± 0.2 | 17.1 ± 0.3 | 14.3 ± 0.1 | 5.3 ± 0.1 | 53.6 ± 0.1 | 75.0 ± 0.3 | 50.0 ± 0.3 | 23.1 ± 0.3 | 29.4 ± 0.3 | 46.9 ± 0.3 | | 5i | 4-Br | 11.1 ± 0.4 | 12.2 ± 0.1 | 28.6 ± 0.4 | 5.3 ± 0.1 | 71.4 ± 0.1 | 18.8 ± 0.1 | 37.9 ± 0.1 | 15.4 ± 0.1 | 11.8 ± 0.1 | 31.3 ± 0.1 | | 5j | 2-NO2 | 5.6 ± 0.2 | 12.2 ± 0.1 | 71.4 ± 0.1 | 18.4 ± 0.2 | 7.1 ± 0.3 | 25.0 ± 0.4 | 55.2 ± 0.1 | 23.1 ± 0.1 | 47.1 ± 0.1 | 62.5 ± 0.1 | | 5k | 4-NO2 | 5.6 ± 0.1 | 12.2 ± 0.2 | 42.9 ± 0.1 | 5.3 ± 0.1 | 50.0 ± 0.1 | 12.5 ± 0.1 | 27.6 ± 0.5 | 19.2 ± 0.1 | 17.6 ± 0.4 | 3.1 ± 0.3 | | 5l | 4-F | 11.1 ± 0.1 | 12.2 ± 0.1 | 28.6 ± 0.2 | 10.5 ± 0.3 | 21.4 ± 0.3 | 34.4 ± 0.1 | 34.5 ± 0.1 | 7.7 ± 0.3 | 17.6 ± 0.1 | 12.5 ± 0.1 | | 5m | 4-CF3 | 5.6 ± 0.3 | 12.2 ± 0.1 | 14.3 ± 0.1 | 5.3 ± 0.1 | 32.1 ± 0.1 | 9.4 ± 0.5 | 17.2 ± 0.3 | 7.7 ± 0.3 | 5.9 ± 0.3 | 28.1 ± 0.3 | | 5n | 4-Cl | 16.7 ± 0.3 | 17.1 ± 0.1 | 17.1 ± 0.3 | 5.3 ± 0.1 | 44.6 ± 0.1 | 25.0 ± 0.1 | 37.9 ± 0.1 | 19.2 ± 0.1 | 17.6 ± 0.1 | 28.1 ± 0.3 | | 5o | 2,4-di-Cl | 11.1 ± 0.2 | 12.2 ± 0.1 | 14.3 ± 0.1 | 5.3 ± 0.1 | 7.1 ± 0.3 | 12.5 ± 0.2 | 20.7 ± 0.5 | 15.4 ± 0.4 | 17.6 ± 0.2 | 56.3 ± 0.4 | | CK | | 88.9 ± 0.2 | 28.6 ± 0.2 | 27.3 ± 0.2 | 16.7 ± 0.2 | 96.4 ± 0.2 | 63.6 ± 0.2 | 88.4 ± 0.2 | 29.4 ± 0.2 | 100 ± 0.2 | 63.6 ± 0.2 |
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