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Table 1 Antifungal effects of title compounds 5a–5w at 10 μg/mL

From: Design and synthesis of novel 3-(thiophen-2-yl)-1,5-dihydro-2H-pyrrol-2-one derivatives bearing a hydrazone moiety as potential fungicides

Compd. R1 R2 R3 Rs Bc Cc Fg
5a H 4-CH3 H 10.5 ± 0.5 0.0 ± 8.2 16.4 ± 2.6 7.5 ± 0.5
5b H 4-CH3 2-F 67.7 ± 0.5 32.3 ± 0.9 57.3 ± 2.7 28.4 ± 1.1
5c H 4-CH3 2-Cl 12.6 ± 1.7 25.3 ± 1.8 21.1 ± 1.3 12.2 ± 1.7
5d H 4-CH3 3-Cl 70.6 ± 2.1 49.0 ± 1.6 61.3 ± 1.8 40.6 ± 2.3
5e H 4-CH3 4-F 83.9 ± 1.2 49.5 ± 2.2 90.7 ± 1.7 98.6 ± 0.5
5f H 4-CH3 4-Cl 76.7 ± 1.5 34.4 ± 0.5 74.7 ± 1.2 69.0 ± 0.6
5g H 4-CH3 4-Br 66.7 ± 0.6 66.4 ± 2.1 74.7 ± 1.9 67.4 ± 1.7
5h H 4-CH3 4-CF3 44.1 ± 3.0 38.4 ± 2.4 43.2 ± 2.1 42.3 ± 1.2
5i H 4-CH3 2,4-di-Cl 47.5 ± 2.4 40.2 ± 3.1 18.9 ± 2.7 10.8 ± 3.5
5j H 4-CH3 4-CH3 40.7 ± 1.8 27.8 ± 0.7 38.9 ± 1.8 40.5 ± 1.9
5k H 4-CH3 4-OCH3 20.0 ± 3.5 7.3 ± 1.4 25.1 ± 1.0 9.4 ± 2.8
5l H H 4-F 52.8 ± 1.1 30.5 ± 3.2 40.7 ± 2.1 38.1 ± 2.1
5m H 2-Cl 4-F 66.3 ± 1.4 37.5 ± 2.2 50.2 ± 2.8 47.3 ± 1.3
5n H 2-Br 4-F 91.5 ± 2.0 47.2 ± 1.0 93.0 ± 1.3 53.1 ± 1.1
5o H 3-Cl 4-F 70.2 ± 1.8 36.1 ± 0.9 73.8 ± 1.2 74.6 ± 3.2
5p H 4-F 4-F 100.0 ± 0.3 61.1 ± 3.5 100.0 ± 0.2 100.0 ± 0.3
5q H 4-Cl 4-F 76.4 ± 0.5 37.5 ± 1.4 83.8 ± 1.6 68.6 ± 2.3
5r H 4-Br 4-F 55.0 ± 1.8 34.7 ± 2.2 48.5 ± 1.6 67.6 ± 3.0
5s H 2,4-di-Cl 4-F 70.6 ± 3.3 45.8 ± 1.6 43.8 ± 3.0 47.8 ± 1.6
5t H 4-OCH3 4-F 67.5 ± 1.2 51.3 ± 2.9 86.0 ± 3.6 92.7 ± 2.5
5u 4-CH3 4-F 4-F 84.7 ± 1.1 48.5 ± 2.1 53.8 ± 3.3 47.9 ± 1.4
5v 4-CH3 4-CH3 4-F 64.7 ± 2.1 36.3 ± 1.8 36.1 ± 1.1 39.6 ± 3.1
5w 4-CH3 4-CH3 4-CH3 37.1 ± 0.1 25.8 ± 0.4 31.2 ± 1.1 35.2 ± 2.1
Drazoxolon a / / / 84.5 ± 1.8 91.2 ± 2.2 46.8 ± 1.9 67.2 ± 0.9
  1. Average of three replicates
  2. a A commercial agricultural fungicide drazoxolon was used for comparison of antifungal activity