P.Z. Zhang et al. / Chinese Chemical Letters 23 (2012) 1381–1384
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Table 1
The in vitro antifungal activity of the target compounds 3 and 4.
Entry
R
Botrytis cinerea
Sclerotinia sclerotiorum
Regression equations
r
EC50 (mg/mL)
Regression equations
r
EC50 (mg/mL)
4a
4b
4c
CH3
y = 4.0885x + 0.7168
y = 3.8902x + 0.8483
y = 4.0806x + 0.7926
y = 4.0421x + 0.7163
y = 4.2795x + 0.6036
y = 4.2795x + 0.6036
y = 3.6630x + 1.0806
y = 3.7482x + 1.0928
y = 3.8794x + 1.9462
0.9689
0.9823
0.9611
0.9709
0.9943
0.9669
0.9809
0.9738
0.9746
18.69 Æ 1.27
20.33 Æ 1.31
14.45 Æ 1.16
21.74 Æ 1.34
15.62 Æ 1.19
7.96 Æ 0.90
17.27 Æ 1.24
13.98 Æ 1.14
30.15 Æ 1.60
y = 4.4775x + 0.3502
y = 4.6581x + 0.2264
y = 4.1568x + 0.5610
y = 4.1257x + 0.6825
y = 3.8573x + 0.6522
y = 4.0346x + 0.7849
y = 4.1708x + 0.5371
y = 4.5170x + 0.4133
y = 4.3606x + 0.9256
0.9890
0.9807
0.9916
0.9833
0.9935
0.9919
0.9907
0.9749
0.9875
31.04 Æ 1.49
32.37 Æ 1.51
31.84 Æ 1.50
19.10 Æ 1.28
46.51 Æ 1.75
16.98 Æ 1.23
34.99 Æ 1.54
14.74 Æ 1.67
4.91 Æ 0.69
C2H5
n-C4H9
CH2C6H5
CH3
4d
5a
5b
5c
C2H5
n-C4H9
CH2C6H5
5d
CK
0.9611–0.9943. On the other hand, the EC50 values of the target compounds against B. cinerea were ranged from 7.96
to 21.74 mg/mL, less than that of carbendazim, which means compounds 4 and 5 possess high antifungal activities to
this kind of pathogen; among them, 5b exhibits the highest activity. Compared with carbendazim, however, the target
compounds showed larger EC50 values (14.74–46.51 mg/mL) against S. sclerotiorum, suggesting that their activities
are lower than that of carbendazim. In addition, it was also found from Table 1, to the same pathogen, there was no
significant difference in EC50 values between compounds 4 and 5, indicating that 1H-benzimidazol-1-yl acetate and
propionate analogue display the similar antifungal activity.
Acknowledgment
This project was supported by Shandong Province Natural Science Foundation (No. ZR2009BM044).
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[17] Analytic data for target compounds. 4a: white solid, yield: 91%; mp: 173.4–175.2 8C; 1H NMR (400 Hz, CDCl3): d 3.74 (s, 3H), 5.18 (s, 2H),
5.68 (s, 2H), 7.27–7.78 (m, 4H), 7.93 (s, 1H), 8.28 (s, 1H); IR (KBr): y 1736, 1229 cmÀ1; ESI-MS m/z: 272.5 (M+H)+. Anal. Calcd. for
C13H13N5O2: C 57.56, H 4.83, N 25.82; found: C 57.84, H 5.07, N25.49. 4b: white solid, yield: 94%; mp: 177.8–179.1 8C; 1H NMR (400 Hz,
CDCl3): d 1.26 (t, 3H, J = 7.2 Hz), 4.20 (q, 2H, J = 7.2 Hz), 5.15 (s, 2H), 5.68 (s, 2H), 7.27–7.34 (m, 4H), 7.93 (s, 1H), 8.28 (s, 1H); IR (KBr): y
1735, 1220 cmÀ1; ESI-MS m/z: 286.4 (M+H)+. Anal. Calcd. for C14H15N5O2: C 58.94, H 5.30, N 24.55; found: C 59.22, H 5.08, N 24.35. 4c:
white solid, yield: 93%; mp: 125.4.4–126.1 8C; 1H NMR (400 Hz, CDCl3): d 0.88 (t, 3H, J = 7.2 Hz), 1.24–1.33 (m, 2H), 1.54–1.69 (m, 2H),
4.13 (t, 2H, J = 7.2 Hz), 5.15 (s, 2H), 5.68 (s, 2H), 7.26–7.79 (m, 4H), 7.93 (s, 1H), 8.27 (s, 1H); IR (KBr): y 1731, 1217 cmÀ1; ESI-MS m/z:
314.6 (M+H)+. Anal. Calcd. for C16H19N5O2: C 61.33, H 6.11, N 22.35; found: C 61.65, H 6.04, N 22.63. 4d: white solid, yield: 94%; mp:
152.4–153.6 8C; 1H NMR (400 Hz, CDCl3): d 5.17 (s, 2H), 5.20 (s, 2H), 5.64 (s, 2H), 7.26–7.79 (m, 9H), 7.83 (s, 1H), 8.23 (s, 1H); IR (KBr): y
1725, 1203 cmÀ1; ESI-MS m/z: 348.4 (M+H)+. Anal. Calcd. for C19H17N5O2: C 65.69, H 4.93, N 20.16; found: C 65.41, H 4.75, N 20.48. 5a:
pale yellow oil, yield: 89%; 1H NMR (400 Hz, CDCl3): d 2.84 (t, 2H, J = 7.2 Hz), 3.60 (s, 3H), 4.63 (t, 2H, J = 7.2 Hz), 5.88 (s, 2H), 7.18–7.61