高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (7): 1315.doi: 10.7503/cjcu20150036
王子剑1, 孙晓红1,2(), 刘源发3, 陈邦3, 沈生强1, 靳如意2, 马海霞2
收稿日期:
2015-01-12
出版日期:
2015-07-10
发布日期:
2015-06-11
作者简介:
联系人简介: 孙晓红, 女, 博士, 研究员, 博士生导师, 主要从事有机合成研究. E-mail:基金资助:
WANG Zijian1, SUN Xiaohong1,2,*(), LIU Yuanfa3, CHEN Bang3, SHEN Shengqiang1, JIN Ruyi2, MA Haixia2
Received:
2015-01-12
Online:
2015-07-10
Published:
2015-06-11
Contact:
SUN Xiaohong
E-mail:xhsun888@sohu.com
Supported by:
摘要:
以自制的4-氨基-4,5-二氢-3-[(3,5-二甲基吡唑-1-基)甲基]-1,2,4-三唑-5-硫酮衍生物为中间体, 与取代苯甲醛反应合成了一系列新型含吡唑环的1,2,4-三唑希夫碱衍生物. 通过红外光谱、 核磁共振波谱、 高分辨质谱、 元素分析及X射线单晶衍射对目标化合物进行了结构表征, 并初步测试了其生物活性. 结果表明, 大部分化合物表现出较好的抑菌活性, 其中化合物G9, G10和G15的抑菌效果优于对照药三唑酮.
中图分类号:
TrendMD:
王子剑, 孙晓红, 刘源发, 陈邦, 沈生强, 靳如意, 马海霞. 含吡唑环的1,2,4-三唑希夫碱类衍生物的合成及生物活性. 高等学校化学学报, 2015, 36(7): 1315.
WANG Zijian, SUN Xiaohong, LIU Yuanfa, CHEN Bang, SHEN Shengqiang, JIN Ruyi, MA Haixia. Synthesis and Biological Activities of 1,2,4-Triazole Schiff Bases Containing Pyrazole Rings†. Chem. J. Chinese Universities, 2015, 36(7): 1315.
Compd. | Appearance | m.p./℃ | Yield(%) | HRMS(ESI) [M+Na]+ (calcd.), m/z | IR(KBr), | Elemental analysis (%, calcd.) | ||
---|---|---|---|---|---|---|---|---|
C | H | N | ||||||
G1 | White solid | 242.2—242.7 | 65.3 | 365.1246 (365.1283) | 3423(N—H), 3041(=C—H), 1583(C=N), 1352(C=S), 1415, 1495, 1583(C=C) | 56.67 (56.14) | 5.13 (5.26) | 24.87 (24.56) |
G2 | Light yellow solid | 243.5—244.2 | 72.1 | 364.1438 (364.1413) | 3434(N—H), 3021(=C—H), 1585(C=N), 1369(C=S), 1430, 1482, 1529(C=C) | 56.83 (56.30) | 5.21 (5.57) | 29.01 (28.74) |
G3 | Light yellow solid | 254.6—255.8 | 66.4 | 369.0792 (369.0757) | 3415(N—H), 3039(=C—H), 1594(C=N), 1341(C=S), 1428, 1486, 1556(C=C) | 51.88 (52.02) | 4.65 (4.34) | 24.72 (24.28) |
G4 | White solid | 249.7—250.4 | 58.7 | 349.1322 (349.1314) | 3435(N—H), 3024(=C—H), 1598(C=N), 1344(C=S), 1419, 1486, 1554(C=C) | 58.54 (58.90) | 5.31 (5.52) | 25.26 (25.77) |
G5 | White solid | 273.2—274.1 | 70.6 | 351.1093 (351.1106) | 3431(N—H), 3035(=C—H), 1588(C=N), 1346(C=S), 1422, 1485, 1552(C=C) | 54.54 (54.88) | 5.01 (4.88) | 25.34 (25.61) |
G6 | White solid | 244.3—245.5 | 66.5 | 381.1236 (381.1212) | 3429(N—H), 3028(=C—H), 1592(C=N), 1348(C=S), 1422, 1483, 1541(C=C) | 53.72 (53.63) | 5.28 (5.03) | 23.74 (23.46) |
G7 | Light yellow solid | 246.1—247.3 | 68.1 | 425.1458 (425.1474) | 3418(N—H), 3031(=C—H), 1594(C=N), 1346(C=S), 1420, 1471, 1562(C=C) | 53.42 (53.73) | 5.85 (5.47) | 21.13 (20.90) |
G8 | White solid | 238.5—239.3 | 55.2 | 381.1230 (381.1212) | 3424(N—H), 3033(=C—H), 1588(C=N), 1452(C=S), 1418, 1477, 1548(C=C) | 53.72 (53.63) | 5.12 (5.03) | 23.71 (23.46) |
G9 | Light yellow solid | 99.6—100.5 | 74.4 | 425.0872 (425.0859) | 3430(N—H), 3029(=C—H), 1594(C=N), 1356(C=S), 1426, 1471, 1566(C=C) | 44.42 (44.78) | 3.65 (3.48) | 27.62 (27.86) |
G10 | Yellow solid | 248.3—249.4 | 57.3 | 380.1032 (380.1008) | 3432(N—H), 3033(=C—H), 1594(C=N), 1347(C=S), 1424, 1464, 1553(C=C) | 50.71 (50.42) | 4.42 (4.20) | 27.86 (27.45) |
G11 | Yellow solid | 199.5—200.8 | 64.7 | 353.1042 (353.1063) | 3433(N—H), 3029(=C—H), 1596(C=N), 1350(C=S), 1423, 1471, 1563(C=C) | 54.77 (54.55) | 4.32 (4.55) | 25.23 (25.45) |
G12 | White solid | 230.2—231.5 | 59.2 | 349.1323 (349.1314) | 3419(N—H), 3032(=C—H), 1588(C=N), 1348(C=S), 1426, 1478, 1544(C=C) | 59.16 (58.90) | 5.62 (5.52) | 25.83 (25.77) |
G13 | Yellow solid | 203.4—204.7 | 78.5 | 369.0795 (369.0757) | 3438(N—H), 3027(=C—H), 1591(C=N), 1366(C=S), 1419, 1444, 1558(C=C) | 52.32 (52.02) | 4.32 (4.34) | 24.56 (24.28) |
G14 | White solid | 208.7—210.2 | 77.4 | 335.1088 (335.1157) | 3423(N—H), 3035(=C—H), 1595(C=N), 1344(C=S), 1422, 1453, 1565(C=C) | 57.88 (57.69) | 5.31 (5.13) | 27.11 (26.92) |
G15 | Yellow solid | 240.5—242.3 | 67.9 | 387.0642 (387.0673) | 3432(N—H), 3027(=C—H), 1589(C=N), 1355(C=S), 1422, 1471, 1561(C=C) | 49.32 (49.45) | 3.69 (3.85) | 23.12 (23.08) |
Table 1 Appearance, melting points, yields, HRMS, IR and elemental analysis data of compounds G1—G15
Compd. | Appearance | m.p./℃ | Yield(%) | HRMS(ESI) [M+Na]+ (calcd.), m/z | IR(KBr), | Elemental analysis (%, calcd.) | ||
---|---|---|---|---|---|---|---|---|
C | H | N | ||||||
G1 | White solid | 242.2—242.7 | 65.3 | 365.1246 (365.1283) | 3423(N—H), 3041(=C—H), 1583(C=N), 1352(C=S), 1415, 1495, 1583(C=C) | 56.67 (56.14) | 5.13 (5.26) | 24.87 (24.56) |
G2 | Light yellow solid | 243.5—244.2 | 72.1 | 364.1438 (364.1413) | 3434(N—H), 3021(=C—H), 1585(C=N), 1369(C=S), 1430, 1482, 1529(C=C) | 56.83 (56.30) | 5.21 (5.57) | 29.01 (28.74) |
G3 | Light yellow solid | 254.6—255.8 | 66.4 | 369.0792 (369.0757) | 3415(N—H), 3039(=C—H), 1594(C=N), 1341(C=S), 1428, 1486, 1556(C=C) | 51.88 (52.02) | 4.65 (4.34) | 24.72 (24.28) |
G4 | White solid | 249.7—250.4 | 58.7 | 349.1322 (349.1314) | 3435(N—H), 3024(=C—H), 1598(C=N), 1344(C=S), 1419, 1486, 1554(C=C) | 58.54 (58.90) | 5.31 (5.52) | 25.26 (25.77) |
G5 | White solid | 273.2—274.1 | 70.6 | 351.1093 (351.1106) | 3431(N—H), 3035(=C—H), 1588(C=N), 1346(C=S), 1422, 1485, 1552(C=C) | 54.54 (54.88) | 5.01 (4.88) | 25.34 (25.61) |
G6 | White solid | 244.3—245.5 | 66.5 | 381.1236 (381.1212) | 3429(N—H), 3028(=C—H), 1592(C=N), 1348(C=S), 1422, 1483, 1541(C=C) | 53.72 (53.63) | 5.28 (5.03) | 23.74 (23.46) |
G7 | Light yellow solid | 246.1—247.3 | 68.1 | 425.1458 (425.1474) | 3418(N—H), 3031(=C—H), 1594(C=N), 1346(C=S), 1420, 1471, 1562(C=C) | 53.42 (53.73) | 5.85 (5.47) | 21.13 (20.90) |
G8 | White solid | 238.5—239.3 | 55.2 | 381.1230 (381.1212) | 3424(N—H), 3033(=C—H), 1588(C=N), 1452(C=S), 1418, 1477, 1548(C=C) | 53.72 (53.63) | 5.12 (5.03) | 23.71 (23.46) |
G9 | Light yellow solid | 99.6—100.5 | 74.4 | 425.0872 (425.0859) | 3430(N—H), 3029(=C—H), 1594(C=N), 1356(C=S), 1426, 1471, 1566(C=C) | 44.42 (44.78) | 3.65 (3.48) | 27.62 (27.86) |
G10 | Yellow solid | 248.3—249.4 | 57.3 | 380.1032 (380.1008) | 3432(N—H), 3033(=C—H), 1594(C=N), 1347(C=S), 1424, 1464, 1553(C=C) | 50.71 (50.42) | 4.42 (4.20) | 27.86 (27.45) |
G11 | Yellow solid | 199.5—200.8 | 64.7 | 353.1042 (353.1063) | 3433(N—H), 3029(=C—H), 1596(C=N), 1350(C=S), 1423, 1471, 1563(C=C) | 54.77 (54.55) | 4.32 (4.55) | 25.23 (25.45) |
G12 | White solid | 230.2—231.5 | 59.2 | 349.1323 (349.1314) | 3419(N—H), 3032(=C—H), 1588(C=N), 1348(C=S), 1426, 1478, 1544(C=C) | 59.16 (58.90) | 5.62 (5.52) | 25.83 (25.77) |
G13 | Yellow solid | 203.4—204.7 | 78.5 | 369.0795 (369.0757) | 3438(N—H), 3027(=C—H), 1591(C=N), 1366(C=S), 1419, 1444, 1558(C=C) | 52.32 (52.02) | 4.32 (4.34) | 24.56 (24.28) |
G14 | White solid | 208.7—210.2 | 77.4 | 335.1088 (335.1157) | 3423(N—H), 3035(=C—H), 1595(C=N), 1344(C=S), 1422, 1453, 1565(C=C) | 57.88 (57.69) | 5.31 (5.13) | 27.11 (26.92) |
G15 | Yellow solid | 240.5—242.3 | 67.9 | 387.0642 (387.0673) | 3432(N—H), 3027(=C—H), 1589(C=N), 1355(C=S), 1422, 1471, 1561(C=C) | 49.32 (49.45) | 3.69 (3.85) | 23.12 (23.08) |
Compd. | 1H NMR(DMSO, 400 MHz), δ | 13C NMR(DMSO, 100 MHz), δ |
---|---|---|
G1 | 2.01(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 3.72(s, 3H, OCH3), 5.77(s, 1H, pyrazole), 5.31(s, 2H, CH2), 7.12—7.82(m, 4H, phenyl), 9.52(s, 1H, CH =N) | 164.65, 163.26, 162.21, 147.64, 147.19, 140.55, 130.32, 126.89, 115.17, 105.42, 52.35, 42.98, 13.64, 11.13 |
G2 | 2.32(s, 3H, Py—CH3), 2.52(s, 3H, Py—CH3), 6.06(s, 1H, pyrazole), 5.57(s, 2H, CH2), 14.20(s, 1H, SH), 7.11—7.93(m, 4H, phenyl), 9.48(s, 1H, CH=N) | 164.71, 162.52, 148.24, 147.80, 147.31, 140.39, 130.74, 123.32, 113.25, 105.36, 43.61, 26.88, 13.57, 11.23 |
G3 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.72(s, 1H, pyrazole), 5.33(s, 2H, CH2), 14.13(s, 1H, SH), 7.46—7.76(m, 4H, phenyl), 9.72(s, 1H, CH=N) | 163.96, 162.13, 147.73, 147.29, 140.38, 136.58, 131.26, 130.19, 129.43, 105.52, 43.33, 13.68, 11.15 |
G4 | 2.02(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 3.67(s, 3H, Ph—CH3), 5.76(s, 1H, pyrazole), 5.38(s, 2H, CH2), 14.11(s, 1H, SH), 7.23—7.61(m, 4H, phenyl), 9.87(s, 1H, CH=N) | 164.82, 162.32, 147.56, 147.30, 143.63, 140.37, 130.17, 129.71, 129.18, 105.46, 43.08, 21.74, 13.74, 11.08 |
G5 | 2.01(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 10.15(s, 1H, OH), 5.71(s, 1H, pyrazole), 5.34(s, 2H, CH2), 14.12(s, 1H, SH), 7.14—7.45(m, 4H, phenyl), 9.97(s, 1H, CH=N) | 164.21, 162.37, 160.17, 147.82, 147.21, 140.58, 129.89, 126.11, 116.25, 105.61, 42.89, 13.35, 11.09 |
G6 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 3.83(s, 1H, Ph—CH3), 5.76(s, 1H, pyrazole), 5.32(s, 2H, CH2), 13.97(s, 1H, SH), 7.19—7.51(m, 3H, phenyl), 9.86(s, 1H, CH=N), 10.07(s, 1H, OH) | 164.35, 162.41, 151.71, 148.08, 147.92, 147.34, 140.27, 126.94, 123.11, 117.25, 114.68, 105.56, 53.67, 43.12, 13.60, 11.14 |
G7 | 2.02(s, 3H, Py—CH3), 2.25(s, 3H, Py—CH3), 3.37, 3.76, 3.85(s, 3H, OCH3), 5.79(s, 1H, pyrazole), 5.34(s, 2H, CH2), 7.16—7.18(m, 2H, phenyl), 9.67(s, 1H, CH=N) | 163.85, 161.91, 151.12, 147.92, 147.22, 141.63, 140.81, 128.34, 106.71, 105.46, 55.62, 55.49, 43.27, 13.39, 11.08 |
G8 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 3.85(s, 1H, Ph—CH3), 5.78(s, 1H, pyrazole), 5.32(s, 2H, CH2), 13.99(s, 1H, SH), 7.15—7.40(m, 3H, phenyl), 9.80(s, 1H, CH=N), 10.04(s, 1H, OH) | 164.18, 161.97, 152.09, 150.13, 147.81, 147.23, 140.66, 123.32, 121.87, 120.45, 118.79, 105.38, 54.26, 43.09, 13.29, 11.26 |
G9 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.75(s, 1H, pyrazole), 5.33(s, 2H, CH2), 7.23—7.61(m, 3H, Phenyl), 9.97(s, 1H, CH=N) | 164.16, 162.42, 151.68, 149.57, 147.87, 147.23, 140.62, 133.19, 131.41, 127.48, 118.36, 105.72, 43.37, 13.32, 10.95 |
G10 | 2.02(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 5.77(s, 1H, pyrazole), 5.35(s, 2H, CH2), 14.10(s, 1H, SH), 7.44—7.68(m, 4H, phenyl), 9.94(s, 1H, CH=N) | 163.98, 162.12, 148.76, 147.73, 147.27, 140.61, 135.34, 134.62, 130.73, 124.34, 123.27, 105.47, 43.58, 13.69, 11.11 |
G11 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.79(s, 1H, pyrazole), 5.37(s, 2H, CH2), 14.08(s, 1H, SH), 7.50—7.74(m, 4H, phenyl), 9.95(s, 1H, CH=N) | 164.35, 163.31, 162.67, 147.69, 147.13, 140.78, 135.28, 130.83, 125.17, 118.01, 114.24, 105.27, 42.98, 13.81, 11.06 |
G12 | 2.02(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 3.64(s, 3H, Ph—CH3), 5.76(s, 1H, pyrazole), 5.36(s, 2H, CH2), 14.13(s, 1H, SH), 7.21—7.63(m, 4H, phenyl), 9.85(s, 1H, CH=N) | 164.11, 161.87, 147.18, 146.84, 139.93, 138.51, 133.46, 131.95129.02, 128.98, 126.06, 105.05, 42.67, 20.82, 13.29, 10.63 |
G13 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.73(s, 1H, pyrazole), 5.34(s, 2H, CH2), 7.44—7.72(m, 4H, phenyl), 9.74(s, 1H, CH=N) | 162.34, 161.89, 147.74, 147.27, 140.32, 135.36, 134.38, 131.48, 130.62, 128.18, 127.98, 105.54, 43.21, 13.72, 11.07 |
G14 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.77(s, 1H, pyrazole), 5.36(s, 2H, CH2), 14.09(s, 1H, SH), 7.21—7.73(m, 5H, phenyl), 9.66(s, 1H, CH=N) | 164.56, 161.95, 147.98, 147.23, 140.15, 134.05, 131.23, 129.42, 128.37, 105.71, 43.42, 13.69, 11.10 |
G15 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.79(s, 1H, pyrazole), 5.32(s, 2H, CH2), 14.11(s, 1H, SH), 7.46—7.68(m, 3H, phenyl), 10.58(s, 1H, CH=N) | 164.18, 162.41, 161.07, 147.88, 147.12, 140.28, 135.41, 134.71, 125.25, 118.13, 113.47, 105.63, 43.47, 13.52, 10.89 |
Table 2 1H NMR and 13C NMR data of compounds G1—G15
Compd. | 1H NMR(DMSO, 400 MHz), δ | 13C NMR(DMSO, 100 MHz), δ |
---|---|---|
G1 | 2.01(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 3.72(s, 3H, OCH3), 5.77(s, 1H, pyrazole), 5.31(s, 2H, CH2), 7.12—7.82(m, 4H, phenyl), 9.52(s, 1H, CH =N) | 164.65, 163.26, 162.21, 147.64, 147.19, 140.55, 130.32, 126.89, 115.17, 105.42, 52.35, 42.98, 13.64, 11.13 |
G2 | 2.32(s, 3H, Py—CH3), 2.52(s, 3H, Py—CH3), 6.06(s, 1H, pyrazole), 5.57(s, 2H, CH2), 14.20(s, 1H, SH), 7.11—7.93(m, 4H, phenyl), 9.48(s, 1H, CH=N) | 164.71, 162.52, 148.24, 147.80, 147.31, 140.39, 130.74, 123.32, 113.25, 105.36, 43.61, 26.88, 13.57, 11.23 |
G3 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.72(s, 1H, pyrazole), 5.33(s, 2H, CH2), 14.13(s, 1H, SH), 7.46—7.76(m, 4H, phenyl), 9.72(s, 1H, CH=N) | 163.96, 162.13, 147.73, 147.29, 140.38, 136.58, 131.26, 130.19, 129.43, 105.52, 43.33, 13.68, 11.15 |
G4 | 2.02(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 3.67(s, 3H, Ph—CH3), 5.76(s, 1H, pyrazole), 5.38(s, 2H, CH2), 14.11(s, 1H, SH), 7.23—7.61(m, 4H, phenyl), 9.87(s, 1H, CH=N) | 164.82, 162.32, 147.56, 147.30, 143.63, 140.37, 130.17, 129.71, 129.18, 105.46, 43.08, 21.74, 13.74, 11.08 |
G5 | 2.01(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 10.15(s, 1H, OH), 5.71(s, 1H, pyrazole), 5.34(s, 2H, CH2), 14.12(s, 1H, SH), 7.14—7.45(m, 4H, phenyl), 9.97(s, 1H, CH=N) | 164.21, 162.37, 160.17, 147.82, 147.21, 140.58, 129.89, 126.11, 116.25, 105.61, 42.89, 13.35, 11.09 |
G6 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 3.83(s, 1H, Ph—CH3), 5.76(s, 1H, pyrazole), 5.32(s, 2H, CH2), 13.97(s, 1H, SH), 7.19—7.51(m, 3H, phenyl), 9.86(s, 1H, CH=N), 10.07(s, 1H, OH) | 164.35, 162.41, 151.71, 148.08, 147.92, 147.34, 140.27, 126.94, 123.11, 117.25, 114.68, 105.56, 53.67, 43.12, 13.60, 11.14 |
G7 | 2.02(s, 3H, Py—CH3), 2.25(s, 3H, Py—CH3), 3.37, 3.76, 3.85(s, 3H, OCH3), 5.79(s, 1H, pyrazole), 5.34(s, 2H, CH2), 7.16—7.18(m, 2H, phenyl), 9.67(s, 1H, CH=N) | 163.85, 161.91, 151.12, 147.92, 147.22, 141.63, 140.81, 128.34, 106.71, 105.46, 55.62, 55.49, 43.27, 13.39, 11.08 |
G8 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 3.85(s, 1H, Ph—CH3), 5.78(s, 1H, pyrazole), 5.32(s, 2H, CH2), 13.99(s, 1H, SH), 7.15—7.40(m, 3H, phenyl), 9.80(s, 1H, CH=N), 10.04(s, 1H, OH) | 164.18, 161.97, 152.09, 150.13, 147.81, 147.23, 140.66, 123.32, 121.87, 120.45, 118.79, 105.38, 54.26, 43.09, 13.29, 11.26 |
G9 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.75(s, 1H, pyrazole), 5.33(s, 2H, CH2), 7.23—7.61(m, 3H, Phenyl), 9.97(s, 1H, CH=N) | 164.16, 162.42, 151.68, 149.57, 147.87, 147.23, 140.62, 133.19, 131.41, 127.48, 118.36, 105.72, 43.37, 13.32, 10.95 |
G10 | 2.02(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 5.77(s, 1H, pyrazole), 5.35(s, 2H, CH2), 14.10(s, 1H, SH), 7.44—7.68(m, 4H, phenyl), 9.94(s, 1H, CH=N) | 163.98, 162.12, 148.76, 147.73, 147.27, 140.61, 135.34, 134.62, 130.73, 124.34, 123.27, 105.47, 43.58, 13.69, 11.11 |
G11 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.79(s, 1H, pyrazole), 5.37(s, 2H, CH2), 14.08(s, 1H, SH), 7.50—7.74(m, 4H, phenyl), 9.95(s, 1H, CH=N) | 164.35, 163.31, 162.67, 147.69, 147.13, 140.78, 135.28, 130.83, 125.17, 118.01, 114.24, 105.27, 42.98, 13.81, 11.06 |
G12 | 2.02(s, 3H, Py—CH3), 2.21(s, 3H, Py—CH3), 3.64(s, 3H, Ph—CH3), 5.76(s, 1H, pyrazole), 5.36(s, 2H, CH2), 14.13(s, 1H, SH), 7.21—7.63(m, 4H, phenyl), 9.85(s, 1H, CH=N) | 164.11, 161.87, 147.18, 146.84, 139.93, 138.51, 133.46, 131.95129.02, 128.98, 126.06, 105.05, 42.67, 20.82, 13.29, 10.63 |
G13 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.73(s, 1H, pyrazole), 5.34(s, 2H, CH2), 7.44—7.72(m, 4H, phenyl), 9.74(s, 1H, CH=N) | 162.34, 161.89, 147.74, 147.27, 140.32, 135.36, 134.38, 131.48, 130.62, 128.18, 127.98, 105.54, 43.21, 13.72, 11.07 |
G14 | 2.02(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.77(s, 1H, pyrazole), 5.36(s, 2H, CH2), 14.09(s, 1H, SH), 7.21—7.73(m, 5H, phenyl), 9.66(s, 1H, CH=N) | 164.56, 161.95, 147.98, 147.23, 140.15, 134.05, 131.23, 129.42, 128.37, 105.71, 43.42, 13.69, 11.10 |
G15 | 2.03(s, 3H, Py—CH3), 2.22(s, 3H, Py—CH3), 5.79(s, 1H, pyrazole), 5.32(s, 2H, CH2), 14.11(s, 1H, SH), 7.46—7.68(m, 3H, phenyl), 10.58(s, 1H, CH=N) | 164.18, 162.41, 161.07, 147.88, 147.12, 140.28, 135.41, 134.71, 125.25, 118.13, 113.47, 105.63, 43.47, 13.52, 10.89 |
Compd. | EC50 value/(g·L-1 ) | EC95 value/(g·L-1 ) | ||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Gibberlla nicotiancola | Gibberlla saubinetii | F.o.f.sp. niveum* | Pythium solani | Gibberlla nicotiancola | Gibberlla saubinetii | F.o.f.sp. niveum* | Pythium solani | |||||||||
G1 | 0.92 | 2.67 | 1.13 | 0.12 | 7.28 | 12.60 | 21.80 | 11.83 | ||||||||
G2 | 0.14 | 0.10 | 1.40 | 0.23 | 5.54 | 2.90 | 23.34 | 10.42 | ||||||||
G3 | 0.40 | 0.06 | 6.54 | 0.83 | 3.31 | 2.03 | 24.32 | 7.54 | ||||||||
G4 | 0.65 | 2.43 | 1.86 | 0.87 | 7.22 | 14.23 | 25.33 | 10.28 | ||||||||
G5 | 0.73 | 2.33 | 1.71 | 0.27 | 12.05 | 18.23 | 26.70 | 11.63 | ||||||||
G6 | 2.06 | 2.02 | 0.63 | 1.03 | 6.66 | 14.81 | 27.22 | 9.57 | ||||||||
G7 | 3.48 | 45.78 | ||||||||||||||
G8 | 1.05 | 2.12 | 3.09 | 0.21 | 6.41 | 12.70 | 26.19 | 8.40 | ||||||||
G9 | 0.10 | 0.04 | 0.01 | 0.07 | 1.12 | 0.31 | 7.18 | 1.06 | ||||||||
G10 | 0.13 | 0.12 | 0.02 | 0.09 | 1.82 | 0.35 | 16.47 | 2.36 | ||||||||
G11 | 0.02 | 0.02 | 0.03 | 0.08 | 1.43 | 0.38 | 18.09 | 4.21 | ||||||||
G12 | ||||||||||||||||
G13 | 0.97 | 0.42 | 2.57 | 0.12 | 2.11 | 0.59 | 20.11 | 4.75 | ||||||||
G14 | 212.60 | |||||||||||||||
G15 | 0.05 | 0.05 | 0.04 | 0.67 | 1.35 | 0.26 | 9.38 | 1.44 | ||||||||
Triazolone | 0.13 | 0.02 | 0.03 | 0.01 | 1.89 | 0.39 | 20.01 | 2.35 |
Table 3 Biological test results of compounds G1—G15 against four vegetable pathogens
Compd. | EC50 value/(g·L-1 ) | EC95 value/(g·L-1 ) | ||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Gibberlla nicotiancola | Gibberlla saubinetii | F.o.f.sp. niveum* | Pythium solani | Gibberlla nicotiancola | Gibberlla saubinetii | F.o.f.sp. niveum* | Pythium solani | |||||||||
G1 | 0.92 | 2.67 | 1.13 | 0.12 | 7.28 | 12.60 | 21.80 | 11.83 | ||||||||
G2 | 0.14 | 0.10 | 1.40 | 0.23 | 5.54 | 2.90 | 23.34 | 10.42 | ||||||||
G3 | 0.40 | 0.06 | 6.54 | 0.83 | 3.31 | 2.03 | 24.32 | 7.54 | ||||||||
G4 | 0.65 | 2.43 | 1.86 | 0.87 | 7.22 | 14.23 | 25.33 | 10.28 | ||||||||
G5 | 0.73 | 2.33 | 1.71 | 0.27 | 12.05 | 18.23 | 26.70 | 11.63 | ||||||||
G6 | 2.06 | 2.02 | 0.63 | 1.03 | 6.66 | 14.81 | 27.22 | 9.57 | ||||||||
G7 | 3.48 | 45.78 | ||||||||||||||
G8 | 1.05 | 2.12 | 3.09 | 0.21 | 6.41 | 12.70 | 26.19 | 8.40 | ||||||||
G9 | 0.10 | 0.04 | 0.01 | 0.07 | 1.12 | 0.31 | 7.18 | 1.06 | ||||||||
G10 | 0.13 | 0.12 | 0.02 | 0.09 | 1.82 | 0.35 | 16.47 | 2.36 | ||||||||
G11 | 0.02 | 0.02 | 0.03 | 0.08 | 1.43 | 0.38 | 18.09 | 4.21 | ||||||||
G12 | ||||||||||||||||
G13 | 0.97 | 0.42 | 2.57 | 0.12 | 2.11 | 0.59 | 20.11 | 4.75 | ||||||||
G14 | 212.60 | |||||||||||||||
G15 | 0.05 | 0.05 | 0.04 | 0.67 | 1.35 | 0.26 | 9.38 | 1.44 | ||||||||
Triazolone | 0.13 | 0.02 | 0.03 | 0.01 | 1.89 | 0.39 | 20.01 | 2.35 |
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