高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (12): 2759.doi: 10.7503/cjcu20200462
收稿日期:
2020-07-16
出版日期:
2020-12-10
发布日期:
2020-12-09
通讯作者:
李华斌
E-mail:lihuabinnk@163.com
基金资助:
DONG Xinrui, XIA Zhe, WANG Zhenxue, BIAN Qiang, LI Huabin()
Received:
2020-07-16
Online:
2020-12-10
Published:
2020-12-09
Contact:
LI Huabin
E-mail:lihuabinnk@163.com
Supported by:
摘要:
通过活性亚结构拼接的方法, 设计合成了一系列含四取代苯基的吡唑-4-甲酰胺类化合物, 所有化合物的结构均通过高分辨质谱(HRMS)和核磁共振氢谱(1H NMR)确证. 生物活性测试结果表明, 部分化合物对苹果纹轮病菌、 水稻纹枯病菌、 油菜菌核病菌和黄瓜灰霉病菌表现出较好的杀菌活性. 化合物5c表现出较广的杀菌谱, 在浓度为50 μg/mL时对苹果纹轮病菌的抑制活性高达95.5%. 初步构效关系分析发现, 吡唑环N取代基为甲基或叔丁基时, 化合物表现出较好的活性; 含并环结构的化合物5′杀菌活性低于含单个苯环的化合 物5; 苯环取代基R2为低于4个碳的脂肪链时, 化合物杀菌活性更高.
中图分类号:
TrendMD:
董心睿, 夏喆, 王桢学, 边强, 李华斌. 含1,2,4,5-四取代苯基的吡唑-4-甲酰胺类化合物的设计、 合成及生物活性. 高等学校化学学报, 2020, 41(12): 2759.
DONG Xinrui, XIA Zhe, WANG Zhenxue, BIAN Qiang, LI Huabin. Design, Synthesis and Biological Activity of Pyrazole-4-carboxamides Compounds Containing 1,2,4,5-Tetrasubstituted Phenyl. Chem. J. Chinese Universities, 2020, 41(12): 2759.
Compd. | Appearance | m. p. /℃ | Yield(%) | HRMS(calcd.), m/z |
---|---|---|---|---|
5a | White solid | 217—219 | 57.9 | 327.0655 (327.0654) |
5b | White solid | 199—201 | 73.0 | 379.0582 (379.0580) |
5c | White solid | 204—206 | 75.0 | 327.1015 (327.1019) |
5d | White solid | 184—186 | 61.9 | 325.0863 (325.0862) |
5e | White solid | 167—168 | 87.8 | 337.0868 (337.0874) |
5f | Yellow solid | 189—191 | 70.4 | 355.1335 (355.1332) |
5g | White solid | 177—179 | 70.9 | 353.1176 (353.1175) |
5h | White solid | 147—148 | 55.6 | 381.1489 (381.1488) |
5i | White solid | 169—171 | 57.5 | 407.0685 (407.0682) |
5j | White solid | 175—177 | 69.8 | 453.0735 (453.0736) |
5′a | White solid | 175—177 | 56.4 | 414.1190 (414.1184) |
5′b | White solid | 179—182 | 74.9 | 348.1465 (348.1466) |
5′c | White solid | 153—155 | 95.7 | 346.1315 (346.1310) |
5′d | White solid | 186—187 | 75.7 | 358.1321 (358.1322) |
5′e | White solid | 232—234 | 67.1 | 344.1157 (344.1153) |
5′f | White solid | 186—188 | 83.9 | 374.1623 (374.1623) |
5′g | White solid | 190—192 | 80.8 | 394.1289 (394.1286) |
5′h | White solid | 206—208 | 59.8 | 400.1788 (400.1791) |
5′i | White solid | 188—189 | 57.9 | 384.1485 (384.1478) |
5′j | White solid | 180—182 | 87.8 | 410.1625 (410.1623) |
5′k | White solid | 207—209 | 83.1 | 408.1465 (408.1466) |
5′l | Yellow solid | 156—158 | 75.3 | 476.1343 (476.1340) |
5′m | White solid | 174—176 | 71.5 | 474.1185 (474.1184) |
Table 1 Appearance, melting points, yields and HRMS data of compounds 5a—5j and 5′a—5′m*
Compd. | Appearance | m. p. /℃ | Yield(%) | HRMS(calcd.), m/z |
---|---|---|---|---|
5a | White solid | 217—219 | 57.9 | 327.0655 (327.0654) |
5b | White solid | 199—201 | 73.0 | 379.0582 (379.0580) |
5c | White solid | 204—206 | 75.0 | 327.1015 (327.1019) |
5d | White solid | 184—186 | 61.9 | 325.0863 (325.0862) |
5e | White solid | 167—168 | 87.8 | 337.0868 (337.0874) |
5f | Yellow solid | 189—191 | 70.4 | 355.1335 (355.1332) |
5g | White solid | 177—179 | 70.9 | 353.1176 (353.1175) |
5h | White solid | 147—148 | 55.6 | 381.1489 (381.1488) |
5i | White solid | 169—171 | 57.5 | 407.0685 (407.0682) |
5j | White solid | 175—177 | 69.8 | 453.0735 (453.0736) |
5′a | White solid | 175—177 | 56.4 | 414.1190 (414.1184) |
5′b | White solid | 179—182 | 74.9 | 348.1465 (348.1466) |
5′c | White solid | 153—155 | 95.7 | 346.1315 (346.1310) |
5′d | White solid | 186—187 | 75.7 | 358.1321 (358.1322) |
5′e | White solid | 232—234 | 67.1 | 344.1157 (344.1153) |
5′f | White solid | 186—188 | 83.9 | 374.1623 (374.1623) |
5′g | White solid | 190—192 | 80.8 | 394.1289 (394.1286) |
5′h | White solid | 206—208 | 59.8 | 400.1788 (400.1791) |
5′i | White solid | 188—189 | 57.9 | 384.1485 (384.1478) |
5′j | White solid | 180—182 | 87.8 | 410.1625 (410.1623) |
5′k | White solid | 207—209 | 83.1 | 408.1465 (408.1466) |
5′l | Yellow solid | 156—158 | 75.3 | 476.1343 (476.1340) |
5′m | White solid | 174—176 | 71.5 | 474.1185 (474.1184) |
Compd. | 1H NMR(CDCl3), δ |
---|---|
5a | 8.92(d, J=8.5 Hz, 1H), 7.55(s, 1H), 7.37(brs, 1H), 7.25(d, J=9.0 Hz, 1H), 5.28(brs, 2H), 3.92(s, 3H), 3.66(s, 3H) |
5b | 8.44 (d, J=7.4 Hz, 1H), 7.52(s, 1H), 7.39(brs, 1H), 7.22(d, J=10.4 Hz, 1H), 5.24(brs, 2H), 4.33(q, J=7.1Hz, 2H), 3.63(s, 3H), 1.39(t, J=7.1 Hz, 3H) |
5c | 8.15(d, J=7.4 Hz, 1H), 7.54(s, 1H), 7.36(brs, 1H), 7.15(d, J=10.5 Hz, 1H), 5.23(brs, 2H), 4.60—4.52(m, 1H), 3.66(s, 3H), 1.41(s, 3H), 1.37(s, 3H) |
5d | 8.16(d, J=7.3 Hz, 1H), 7.53(s, 1H), 7.38(brs, 1H), 7.15(d, J=10.3 Hz, 1H), 6.06(ddt, J=17.1, 10.3, 5.1 Hz, 1H), 5.49(d, J=17.2 Hz, 1H), 5.32(d, J=10.5 Hz, 1H), 5.23(brs, 2H), 4.62(d, J=4.3 Hz, 2H), 3.65(s, 3H) |
5e | 8.17(d, J=7.3 Hz, 1H), 7.58(s, 1H), 7.42(brs, 1H), 7.19(d, J=10.4 Hz, 1H), 5.26(brs, 2H), 5.21(s, 1H), 5.05(s, 1H), 4.54(s, 2H), 3.69(s, 3H), 1.89(s, 3H) |
5f | 8.13(d, J=7.3 Hz, 1H), 7.54(s, 1H), 7.37(brs, 1H), 7.15(d, J=10.4 Hz, 1H), 5.23(brs, 2H), 4.07(t, J=6.5 Hz, 2H), 3.66(s, 3H), 1.94—1.85(m, 1H), 1.76—1.70(m, 2H), 0.99(s, 3H), 0.97(s, 3H) |
Compd. | 1H NMR(CDCl3), δ |
5g | 8.14(d, J=7.4 Hz, 1H), 7.53(s, 1H), 7.36(brs, 1H), 7.13(d, J=10.5 Hz, 1H), 5.23(brs, 2H), 4.84—4.82(m, 1H), 3.66(s, 3H), 1.91—1.61(m, 8H) |
5h | 8.13(d, J=7.2 Hz, 1H), 7.53(s, 1H), 7.40(brs, 1H), 7.18(d, J=10.4 Hz, 1H), 5.56(brs, 2H), 5.21(s, 1H), 5.04(s, 1H), 4.54(s, 2H), 1.89(s, 3H), 1.68(s, 9H) |
5i | 8.30(d, J=7.3 Hz, 1H), 7.73(s, 1H), 7.55—7.51(m, 4H), 7.45—7.42(m, 1H), 7.40(brs, 1H), 7.19(d, J=10.3 Hz, 1H), 5.60(brs, 2H), 4.80(s, 2H), 2.57(s, 1H) |
5j | 8.29(d, J=7.2 Hz, 1H), 7.89(s, 1H), 7.81—7.80(m, 1H), 7.79(s, 1H), 7.69—7.68(m, 2H), 7.49(brs, 1H), 7.20(d, J=10.3 Hz, 1H), 5.66(brs, 2H), 4.80(d, J=2.4 Hz, 2H), 2.57(d, J=2.4 Hz, 1H) |
5′a | 7.93(d, J=7.4 Hz, 1H), 7.53(s, 1H), 7.27(brs, 1H), 6.83(d, J=10.8 Hz, 1H), 5.21(brs, 2H), 4.67(s, 2H), 4.66(s, 2H), 4.26(q, J=7.1Hz, 2H), 3.65(s, 3H, CH3), 1.30(t, J=7.1 Hz, 3H) |
5′b | 8.10(d, J=7.6 Hz, 1H), 7.54(s, 1H), 7.28(brs, 1H), 6.80(d, J=10.8 Hz, 1H), 5.23(brs, 2H), 4.58(s, 2H), 3.92(t, J=7.4 Hz, 2H), 3.66(s, 3H), 1.78—1.71(m, 2H), 0.98(t, J=7.4 Hz, 3H) |
5′c | 8.11(d, J=7.6 Hz, 1H), 7.52(s, 1H), 7.26(brs, 1H), 6.80(d, J=10.5 Hz, 1H), 5.89(ddt, J=17.2, 10.4, 5.2 Hz, 1H), 5.31(d, J=15.7 Hz, 1H), 5.28(d, J=9.6 Hz, 1H), 5.22(brs, 2H), 4.62(s, 2H), 4.57(d, J=5.0 Hz, 2H), 3.65(s, 3H) |
5′d | 8.04(d, J=7.6 Hz, 1H), 7.53(s, 1H), 7.28(brs, 1H), 6.81(d, J=10.9 Hz, 1H), 5.23(brs, 2H), 4.97(s, 1H), 4.87(s, 1H), 4.64(s, 2H), 4.50(s, 2H), 3.66(s, 3H), 1.80(s, 3H) |
5′e | 8.24(d, J=7.4 Hz, 1H), 7.54(s, 1H), 7.29(brs, 1H), 6.83(d, J=10.8 Hz, 1H), 5.24(brs, 2H), 4.72(d, J=1.6 Hz, 2H), 4.62(s, 2H), 3.65(s, 3H), 2.29(t, J=1.6 Hz, 1H) |
5′f | 8.10(d, J=7.7 Hz, 1H), 7.54(s, 1H), 7.26(brs, 1H), 6.80(d, J=10.9 Hz, 1H), 5.89(ddt, J=16.4, 10.9, 5.1 Hz, 1H), 5.31(d, J=16.0 Hz, 1H), 5.28(d, J=10.1 Hz, 1H), 5.22(brs, 2H), 4.62(s, 2H), 4.57(d, J=4.3 Hz, 2H), 3.86(t, J=7.3 Hz, 2H), 1.89—1.80(m 2H), 0.96(t, J=7.4 Hz, 3H) |
5′g | 8.23(d, J=7.5 Hz, 1H), 7.56(s, 1H), 7.30(brs, 1H), 6.82(d, J=10.8 Hz, 1H), 5.24(brs, 2H), 4.71(d, J=2.1 Hz, 2H), 4.62(s, 2H), 3.86(t, J=7.3 Hz, 2H), 2.28(t, J=1.6 Hz, 1H), 1.89—1.81(m 2H), 0.96(t, J=7.4 Hz, 3H) |
5′h | 8.02(d, J=7.6 Hz, 1H), 7.51(s, 1H), 7.28(brs, 1H), 6.82(d, J=10.8 Hz, 1H), 5.55(brs, 2H), 4.98(s, 1H), 4.88(s, 1H), 4.66(s, 2H), 4.52(s, 2H), 1.81(s, 3H), 1.67(s, 9H) |
5′i | 8.22(d, J=7.4 Hz, 1H), 7.55(s, 1H), 7.33(brs, 1H), 6.85(d, J=10.6 Hz, 1H), 5.57(brs, 2H), 4.75(d, J=2.1 Hz, 2H), 4.64(s, 2H), 3.65(s, 3H), 2.31(t, J=2.1 Hz, 1H), 1.67(s, 9H) |
5′j | 7.98(d, J=7.5 Hz, 1H), 7.77(s, 1H), 7.58—7.55(m, 4H), 7.48—7.45(m, 1H), 7.43(brs, 1H), 6.81(d, J=10.1 Hz, 1H), 5.70(brs, 2H), 4.58(s, 2H), 3.90(t, J=5.6 Hz, 2H), 1.78—1.71(m, 2H), 0.98(t, J=5.7 Hz, 3H) |
5′k | 8.13(d, J=7.5 Hz, 1H), 7.60(s, 1H), 7.55—7.58(m, 4H), 7.45—7.48(m, 1H), 7.41(brs, 1H), 6.85(d, J=10.8 Hz, 1H), 5.93(ddt, J=17.0, 10.7, 4.8 Hz, 1H), 5.62(brs, 2H), 5.35(d, J=16.0 Hz, 1H), 5.32(d, J=9.3 Hz, 1H), 4.66(s, 2H), 4.61(d, J=4.5 Hz, 2H) |
5′l | 8.07(d, J=7.6 Hz, 1H), 7.89(s, 1H), 7.83(s, 1H), 7.80—7.79(m, 1H), 7.70—7.68(m, 2H), 7.45(brs, 1H), 6.83(d, J=10.8 Hz, 1H), 5.90(ddt, J=17.2, 10.3, 5.2 Hz, 1H), 5.66(brs, 2H), 5.32(d, J=16.0 Hz, 1H), 5.29(d, J=9.4 Hz, 1H), 4.58(d, J=5.2 Hz, 2H) |
5′m | 8.24(d, J=7.5 Hz, 1H), 7.89(s, 1H), 7.78—7.81(m, 1H), 7.76(s, 1H), 7.69—7.67(m, 2H), 7.37(brs, 1H), 6.85(d, J=10.8 Hz, 1H), 5.65(brs, 2H), 4.74(d, J=1.7 Hz, 2H), 4.63(s, 2H), 2.29(t, J=1.6 Hz, 1H) |
Table 2 1H NMR data of compounds 5a—5j and 5′a—5′m*
Compd. | 1H NMR(CDCl3), δ |
---|---|
5a | 8.92(d, J=8.5 Hz, 1H), 7.55(s, 1H), 7.37(brs, 1H), 7.25(d, J=9.0 Hz, 1H), 5.28(brs, 2H), 3.92(s, 3H), 3.66(s, 3H) |
5b | 8.44 (d, J=7.4 Hz, 1H), 7.52(s, 1H), 7.39(brs, 1H), 7.22(d, J=10.4 Hz, 1H), 5.24(brs, 2H), 4.33(q, J=7.1Hz, 2H), 3.63(s, 3H), 1.39(t, J=7.1 Hz, 3H) |
5c | 8.15(d, J=7.4 Hz, 1H), 7.54(s, 1H), 7.36(brs, 1H), 7.15(d, J=10.5 Hz, 1H), 5.23(brs, 2H), 4.60—4.52(m, 1H), 3.66(s, 3H), 1.41(s, 3H), 1.37(s, 3H) |
5d | 8.16(d, J=7.3 Hz, 1H), 7.53(s, 1H), 7.38(brs, 1H), 7.15(d, J=10.3 Hz, 1H), 6.06(ddt, J=17.1, 10.3, 5.1 Hz, 1H), 5.49(d, J=17.2 Hz, 1H), 5.32(d, J=10.5 Hz, 1H), 5.23(brs, 2H), 4.62(d, J=4.3 Hz, 2H), 3.65(s, 3H) |
5e | 8.17(d, J=7.3 Hz, 1H), 7.58(s, 1H), 7.42(brs, 1H), 7.19(d, J=10.4 Hz, 1H), 5.26(brs, 2H), 5.21(s, 1H), 5.05(s, 1H), 4.54(s, 2H), 3.69(s, 3H), 1.89(s, 3H) |
5f | 8.13(d, J=7.3 Hz, 1H), 7.54(s, 1H), 7.37(brs, 1H), 7.15(d, J=10.4 Hz, 1H), 5.23(brs, 2H), 4.07(t, J=6.5 Hz, 2H), 3.66(s, 3H), 1.94—1.85(m, 1H), 1.76—1.70(m, 2H), 0.99(s, 3H), 0.97(s, 3H) |
Compd. | 1H NMR(CDCl3), δ |
5g | 8.14(d, J=7.4 Hz, 1H), 7.53(s, 1H), 7.36(brs, 1H), 7.13(d, J=10.5 Hz, 1H), 5.23(brs, 2H), 4.84—4.82(m, 1H), 3.66(s, 3H), 1.91—1.61(m, 8H) |
5h | 8.13(d, J=7.2 Hz, 1H), 7.53(s, 1H), 7.40(brs, 1H), 7.18(d, J=10.4 Hz, 1H), 5.56(brs, 2H), 5.21(s, 1H), 5.04(s, 1H), 4.54(s, 2H), 1.89(s, 3H), 1.68(s, 9H) |
5i | 8.30(d, J=7.3 Hz, 1H), 7.73(s, 1H), 7.55—7.51(m, 4H), 7.45—7.42(m, 1H), 7.40(brs, 1H), 7.19(d, J=10.3 Hz, 1H), 5.60(brs, 2H), 4.80(s, 2H), 2.57(s, 1H) |
5j | 8.29(d, J=7.2 Hz, 1H), 7.89(s, 1H), 7.81—7.80(m, 1H), 7.79(s, 1H), 7.69—7.68(m, 2H), 7.49(brs, 1H), 7.20(d, J=10.3 Hz, 1H), 5.66(brs, 2H), 4.80(d, J=2.4 Hz, 2H), 2.57(d, J=2.4 Hz, 1H) |
5′a | 7.93(d, J=7.4 Hz, 1H), 7.53(s, 1H), 7.27(brs, 1H), 6.83(d, J=10.8 Hz, 1H), 5.21(brs, 2H), 4.67(s, 2H), 4.66(s, 2H), 4.26(q, J=7.1Hz, 2H), 3.65(s, 3H, CH3), 1.30(t, J=7.1 Hz, 3H) |
5′b | 8.10(d, J=7.6 Hz, 1H), 7.54(s, 1H), 7.28(brs, 1H), 6.80(d, J=10.8 Hz, 1H), 5.23(brs, 2H), 4.58(s, 2H), 3.92(t, J=7.4 Hz, 2H), 3.66(s, 3H), 1.78—1.71(m, 2H), 0.98(t, J=7.4 Hz, 3H) |
5′c | 8.11(d, J=7.6 Hz, 1H), 7.52(s, 1H), 7.26(brs, 1H), 6.80(d, J=10.5 Hz, 1H), 5.89(ddt, J=17.2, 10.4, 5.2 Hz, 1H), 5.31(d, J=15.7 Hz, 1H), 5.28(d, J=9.6 Hz, 1H), 5.22(brs, 2H), 4.62(s, 2H), 4.57(d, J=5.0 Hz, 2H), 3.65(s, 3H) |
5′d | 8.04(d, J=7.6 Hz, 1H), 7.53(s, 1H), 7.28(brs, 1H), 6.81(d, J=10.9 Hz, 1H), 5.23(brs, 2H), 4.97(s, 1H), 4.87(s, 1H), 4.64(s, 2H), 4.50(s, 2H), 3.66(s, 3H), 1.80(s, 3H) |
5′e | 8.24(d, J=7.4 Hz, 1H), 7.54(s, 1H), 7.29(brs, 1H), 6.83(d, J=10.8 Hz, 1H), 5.24(brs, 2H), 4.72(d, J=1.6 Hz, 2H), 4.62(s, 2H), 3.65(s, 3H), 2.29(t, J=1.6 Hz, 1H) |
5′f | 8.10(d, J=7.7 Hz, 1H), 7.54(s, 1H), 7.26(brs, 1H), 6.80(d, J=10.9 Hz, 1H), 5.89(ddt, J=16.4, 10.9, 5.1 Hz, 1H), 5.31(d, J=16.0 Hz, 1H), 5.28(d, J=10.1 Hz, 1H), 5.22(brs, 2H), 4.62(s, 2H), 4.57(d, J=4.3 Hz, 2H), 3.86(t, J=7.3 Hz, 2H), 1.89—1.80(m 2H), 0.96(t, J=7.4 Hz, 3H) |
5′g | 8.23(d, J=7.5 Hz, 1H), 7.56(s, 1H), 7.30(brs, 1H), 6.82(d, J=10.8 Hz, 1H), 5.24(brs, 2H), 4.71(d, J=2.1 Hz, 2H), 4.62(s, 2H), 3.86(t, J=7.3 Hz, 2H), 2.28(t, J=1.6 Hz, 1H), 1.89—1.81(m 2H), 0.96(t, J=7.4 Hz, 3H) |
5′h | 8.02(d, J=7.6 Hz, 1H), 7.51(s, 1H), 7.28(brs, 1H), 6.82(d, J=10.8 Hz, 1H), 5.55(brs, 2H), 4.98(s, 1H), 4.88(s, 1H), 4.66(s, 2H), 4.52(s, 2H), 1.81(s, 3H), 1.67(s, 9H) |
5′i | 8.22(d, J=7.4 Hz, 1H), 7.55(s, 1H), 7.33(brs, 1H), 6.85(d, J=10.6 Hz, 1H), 5.57(brs, 2H), 4.75(d, J=2.1 Hz, 2H), 4.64(s, 2H), 3.65(s, 3H), 2.31(t, J=2.1 Hz, 1H), 1.67(s, 9H) |
5′j | 7.98(d, J=7.5 Hz, 1H), 7.77(s, 1H), 7.58—7.55(m, 4H), 7.48—7.45(m, 1H), 7.43(brs, 1H), 6.81(d, J=10.1 Hz, 1H), 5.70(brs, 2H), 4.58(s, 2H), 3.90(t, J=5.6 Hz, 2H), 1.78—1.71(m, 2H), 0.98(t, J=5.7 Hz, 3H) |
5′k | 8.13(d, J=7.5 Hz, 1H), 7.60(s, 1H), 7.55—7.58(m, 4H), 7.45—7.48(m, 1H), 7.41(brs, 1H), 6.85(d, J=10.8 Hz, 1H), 5.93(ddt, J=17.0, 10.7, 4.8 Hz, 1H), 5.62(brs, 2H), 5.35(d, J=16.0 Hz, 1H), 5.32(d, J=9.3 Hz, 1H), 4.66(s, 2H), 4.61(d, J=4.5 Hz, 2H) |
5′l | 8.07(d, J=7.6 Hz, 1H), 7.89(s, 1H), 7.83(s, 1H), 7.80—7.79(m, 1H), 7.70—7.68(m, 2H), 7.45(brs, 1H), 6.83(d, J=10.8 Hz, 1H), 5.90(ddt, J=17.2, 10.3, 5.2 Hz, 1H), 5.66(brs, 2H), 5.32(d, J=16.0 Hz, 1H), 5.29(d, J=9.4 Hz, 1H), 4.58(d, J=5.2 Hz, 2H) |
5′m | 8.24(d, J=7.5 Hz, 1H), 7.89(s, 1H), 7.78—7.81(m, 1H), 7.76(s, 1H), 7.69—7.67(m, 2H), 7.37(brs, 1H), 6.85(d, J=10.8 Hz, 1H), 5.65(brs, 2H), 4.74(d, J=1.7 Hz, 2H), 4.63(s, 2H), 2.29(t, J=1.6 Hz, 1H) |
Compd | Inhibition rate(%) | |||||||||
---|---|---|---|---|---|---|---|---|---|---|
C. cucumerinum | C. rachidicola | P. piricola | A. solani | G. zeae | P. infestans | S. sclerotiorum | B. cinerea | R. solani | P. capsici | |
5a | 6.3 | 7.7 | 27.3 | 14.3 | 31.6 | 7.7 | 21.7 | 0 | 4.5 | 38.1 |
5b | 12.5 | 23.1 | 0 | 21.4 | 15.8 | 7.7 | 21.7 | 3.8 | 27.3 | 23.8 |
5c | 18.8 | 69.2 | 95.5 | 64.3 | 15.8 | 53.8 | 47.8 | 38.5 | 65.9 | 47.6 |
5d | 18.8 | 30.8 | 59.1 | 35.7 | 31.6 | 30.8 | 10.9 | 30.8 | 40.9 | 28.6 |
5e | 30.8 | 45.5 | 21.4 | 25.0 | 23.8 | 22.2 | 23.8 | 7.1 | 30.3 | 40.6 |
5f | 37.5 | 30.8 | 31.8 | 28.6 | 31.6 | 23.1 | 13.0 | 15.4 | 18.2 | 19.0 |
5g | 18.8 | 15.4 | 31.8 | 35.7 | 31.6 | 30.8 | 17.4 | 15.4 | 29.5 | 14.3 |
5h | 30.8 | 36.4 | 64.3 | 25.0 | 23.8 | 16.7 | 33.3 | 53.6 | 36.4 | 59.4 |
5i | 31.3 | 30.8 | 0 | 21.4 | 31.6 | 15.4 | 0 | 19.2 | 70.5 | 33.3 |
5j | 18.8 | 15.4 | 22.7 | 7.1 | 5.3 | 15.4 | 82.6 | 0 | 4.5 | 42.9 |
5′a | 6.3 | 15.4 | 36.4 | 21.4 | 10.5 | 0 | 8.7 | 50.0 | 63.6 | 19.0 |
5′b | 12.5 | 15.4 | 40.9 | 14.3 | 10.5 | 0 | 17.4 | 3.8 | 6.8 | 19.0 |
5′c | 18.8 | 30.8 | 27.3 | 21.4 | 26.3 | 7.7 | 52.2 | 19.2 | 4.5 | 19.0 |
5′d | 7.7 | 27.3 | 21.4 | 8.3 | 9.5 | 11.1 | 23.8 | 10.7 | 6.1 | 4.3 |
5′e | 18.8 | 0 | 18.2 | 14.3 | 15.8 | 30.8 | 26.1 | 7.7 | 0 | 14.3 |
5′f | 25.0 | 15.4 | 40.9 | 14.3 | 15.8 | 15.4 | 39.1 | 11.5 | 4.5 | 23.8 |
5′g | 31.3 | 30.8 | 22.7 | 14.3 | 21.1 | 23.1 | 8.7 | 19.2 | 0 | 23.8 |
5′h | 23.1 | 36.4 | 42.9 | 16.7 | 9.5 | 11.1 | 23.8 | 7.1 | 3.0 | 10.1 |
5′i | 7.7 | 45.5 | 14.3 | 8.3 | 14.3 | 11.1 | 14.3 | 23.2 | 15.2 | 11.6 |
5′j | 18.8 | 15.4 | 18.2 | 28.6 | 15.8 | 7.7 | 21.7 | 11.5 | 61.4 | 19.0 |
5′k | 0 | 15.4 | 63.6 | 35.7 | 15.8 | 30.8 | 17.4 | 19.2 | 36.4 | 23.8 |
5′l | 18.8 | 7.7 | 27.3 | 21.4 | 5.3 | 15.4 | 17.4 | 11.5 | 13.6 | 23.8 |
5′m | 31.3 | 15.4 | 0 | 14.3 | 26.3 | 15.4 | 17.4 | 50.0 | 0 | 23.8 |
Table 3 Fungicidal activities of target compounds at 50 μg/mL
Compd | Inhibition rate(%) | |||||||||
---|---|---|---|---|---|---|---|---|---|---|
C. cucumerinum | C. rachidicola | P. piricola | A. solani | G. zeae | P. infestans | S. sclerotiorum | B. cinerea | R. solani | P. capsici | |
5a | 6.3 | 7.7 | 27.3 | 14.3 | 31.6 | 7.7 | 21.7 | 0 | 4.5 | 38.1 |
5b | 12.5 | 23.1 | 0 | 21.4 | 15.8 | 7.7 | 21.7 | 3.8 | 27.3 | 23.8 |
5c | 18.8 | 69.2 | 95.5 | 64.3 | 15.8 | 53.8 | 47.8 | 38.5 | 65.9 | 47.6 |
5d | 18.8 | 30.8 | 59.1 | 35.7 | 31.6 | 30.8 | 10.9 | 30.8 | 40.9 | 28.6 |
5e | 30.8 | 45.5 | 21.4 | 25.0 | 23.8 | 22.2 | 23.8 | 7.1 | 30.3 | 40.6 |
5f | 37.5 | 30.8 | 31.8 | 28.6 | 31.6 | 23.1 | 13.0 | 15.4 | 18.2 | 19.0 |
5g | 18.8 | 15.4 | 31.8 | 35.7 | 31.6 | 30.8 | 17.4 | 15.4 | 29.5 | 14.3 |
5h | 30.8 | 36.4 | 64.3 | 25.0 | 23.8 | 16.7 | 33.3 | 53.6 | 36.4 | 59.4 |
5i | 31.3 | 30.8 | 0 | 21.4 | 31.6 | 15.4 | 0 | 19.2 | 70.5 | 33.3 |
5j | 18.8 | 15.4 | 22.7 | 7.1 | 5.3 | 15.4 | 82.6 | 0 | 4.5 | 42.9 |
5′a | 6.3 | 15.4 | 36.4 | 21.4 | 10.5 | 0 | 8.7 | 50.0 | 63.6 | 19.0 |
5′b | 12.5 | 15.4 | 40.9 | 14.3 | 10.5 | 0 | 17.4 | 3.8 | 6.8 | 19.0 |
5′c | 18.8 | 30.8 | 27.3 | 21.4 | 26.3 | 7.7 | 52.2 | 19.2 | 4.5 | 19.0 |
5′d | 7.7 | 27.3 | 21.4 | 8.3 | 9.5 | 11.1 | 23.8 | 10.7 | 6.1 | 4.3 |
5′e | 18.8 | 0 | 18.2 | 14.3 | 15.8 | 30.8 | 26.1 | 7.7 | 0 | 14.3 |
5′f | 25.0 | 15.4 | 40.9 | 14.3 | 15.8 | 15.4 | 39.1 | 11.5 | 4.5 | 23.8 |
5′g | 31.3 | 30.8 | 22.7 | 14.3 | 21.1 | 23.1 | 8.7 | 19.2 | 0 | 23.8 |
5′h | 23.1 | 36.4 | 42.9 | 16.7 | 9.5 | 11.1 | 23.8 | 7.1 | 3.0 | 10.1 |
5′i | 7.7 | 45.5 | 14.3 | 8.3 | 14.3 | 11.1 | 14.3 | 23.2 | 15.2 | 11.6 |
5′j | 18.8 | 15.4 | 18.2 | 28.6 | 15.8 | 7.7 | 21.7 | 11.5 | 61.4 | 19.0 |
5′k | 0 | 15.4 | 63.6 | 35.7 | 15.8 | 30.8 | 17.4 | 19.2 | 36.4 | 23.8 |
5′l | 18.8 | 7.7 | 27.3 | 21.4 | 5.3 | 15.4 | 17.4 | 11.5 | 13.6 | 23.8 |
5′m | 31.3 | 15.4 | 0 | 14.3 | 26.3 | 15.4 | 17.4 | 50.0 | 0 | 23.8 |
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