高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (5): 892.doi: 10.7503/cjcu20160065
贾长青1, 杨冬燕1, 车传亮1, 马永强1, 芮昌辉2, 闫晓静2, 覃兆海1()
收稿日期:
2016-01-26
出版日期:
2016-05-10
发布日期:
2016-04-18
作者简介:
联系人简介: 覃兆海, 男, 博士, 教授, 博士生导师, 主要从事新农药创制研究. E-mail:基金资助:
JIA Changqing1, YANG Dongyan1, CHE Chuanliang1, MA Yongqiang1, RUI Changhui2, YAN Xiaojing2, QIN Zhaohai1,*()
Received:
2016-01-26
Online:
2016-05-10
Published:
2016-04-18
Contact:
QIN Zhaohai
E-mail:qinzhaohai@263.net
Supported by:
摘要:
通过活性基团拼接的方法, 将氨基甲酸酯结构和1H-1,2,4-三唑-5-胺有机结合, 设计合成了一系列结构新颖的多取代1H-1,2,4-三唑-5-氨基甲酸酯类化合物(5和6), 所有化合物的结构经核磁共振(NMR), 红外光谱(IR), 高分辨质谱(HRMS)及元素分析等方法确证.初步杀虫活性测定结果表明, 大部分化合物对桃蚜[Myzus persicae(Sulzer)]具有良好的杀虫活性, 致死率大于90%. 精密毒力测试结果表明, 化合物5b的半致死浓度(LC50)为9.49 μg/mL, 具有进一步研究开发的价值.抑菌活性初步测试结果表明该类化合物的抑菌活性一般, 在50 μg/mL浓度下少数化合物也表现出一定的离体抑菌活性. 对此类化合物的构效关系进行了讨论.
中图分类号:
TrendMD:
贾长青, 杨冬燕, 车传亮, 马永强, 芮昌辉, 闫晓静, 覃兆海. 1H-1,2,4-三唑-5-氨基甲酸酯类化合物的合成、 结构表征及杀虫、 抑菌活性. 高等学校化学学报, 2016, 37(5): 892.
JIA Changqing, YANG Dongyan, CHE Chuanliang, MA Yongqiang, RUI Changhui, YAN Xiaojing, QIN Zhaohai. Synthesis, Structural Characterization, Insecticidal and Fungicidal Activity of (1H-1,2,4-Triazol-5-yl)carbamates†. Chem. J. Chinese Universities, 2016, 37(5): 892.
Compd. | m.p./℃ | Compd. | m.p./℃ | Compd. | m.p./℃ |
---|---|---|---|---|---|
4a | 125—127 | 4k | 149—151(149—150[ | 4u | 157—159 |
4b | 121—123 | 4l | 130—132(130—131[ | 4v | 107—109 |
4c | 99—101(99—100[ | 4m | 118—120(118—119[ | 4w | 110—112 |
4d | 101—103(101—102[ | 4n | 162—164(162—163[ | 4x | 213—215 |
4e | 148—150(149—150[ | 4o | 151—153(151—152[ | 4y | 144—146(144—145[ |
4f | 149—151(148—149[ | 4p | 128—130(128—129[ | 4z | 190—192(190—191[ |
4g | 136—138(136—137[ | 4q | 254—256 | 4aa | 141—143(141—142[ |
4h | 154—156(154—155[ | 4r | 227—229 | 4ab | 115—117(115—116[ |
4i | 161—163(161—162[ | 4s | 236—238 | 4ac | 108—110(108—109[ |
4j | 137—139(137—138[ | 4t | 156—158 | 4ad | 148—150(142—144[ |
Table 1 Melting point data of intermediate compounds 4
Compd. | m.p./℃ | Compd. | m.p./℃ | Compd. | m.p./℃ |
---|---|---|---|---|---|
4a | 125—127 | 4k | 149—151(149—150[ | 4u | 157—159 |
4b | 121—123 | 4l | 130—132(130—131[ | 4v | 107—109 |
4c | 99—101(99—100[ | 4m | 118—120(118—119[ | 4w | 110—112 |
4d | 101—103(101—102[ | 4n | 162—164(162—163[ | 4x | 213—215 |
4e | 148—150(149—150[ | 4o | 151—153(151—152[ | 4y | 144—146(144—145[ |
4f | 149—151(148—149[ | 4p | 128—130(128—129[ | 4z | 190—192(190—191[ |
4g | 136—138(136—137[ | 4q | 254—256 | 4aa | 141—143(141—142[ |
4h | 154—156(154—155[ | 4r | 227—229 | 4ab | 115—117(115—116[ |
4i | 161—163(161—162[ | 4s | 236—238 | 4ac | 108—110(108—109[ |
4j | 137—139(137—138[ | 4t | 156—158 | 4ad | 148—150(142—144[ |
Compd. | 1H NMR(DMSO-d6, 300 MHz), δ |
---|---|
4a | 8.29(d, J=2.46 Hz, 1H), 7.52—7.39(m, 1H), 7.33(d, J=8.25 Hz, 1H), 5.05(s, 2H), 4.99(brs, 2H), 2.52(t, |
J=7.05 Hz, 3H), 1.76—1.64(m, 2H), 0.96(t, J=8.05 Hz, 3H) | |
4b | 8.26(d, J=2.46 Hz, 1H), 7.51—7.37(m, 1H), 7.32(d, J=8.24 Hz, 1H), 5.05(s, 2H), 5.00(brs, 2H), 2.54(t, |
J=7.84 Hz, 2H), 1.69—1.59(m, 2H), 1.42—1.29(m, 2H), 0.91(t, J=7.67 Hz, 3H) | |
4q | 8.29—8.07(m, 4H), 6.49(brs, 2H), 3.99(q, J=7.17 Hz, 2H), 1.30(t, J=7.14 Hz, 3H) |
4r | 8.29—8.06(m, 4H), 6.48(brs, 2H), 3.91(t, J=6.90 Hz, 2H), 1.74—1.56(m, 2H), 0.88(t, J=7.35 Hz, 3H) |
4s | 8.29—8.06(m, 4H), 6.47(brs, 2H), 3.95(t, J=7.04 Hz, 2H), 1.70—1.54(m, 2H), 1.33—1.21(m, 2H), 0.91(t, |
J=7.31 Hz, 3H) | |
4t | 7.90—7.18(m, 4H), 6.30(brs, 2H), 3.93(q, J=7.17 Hz, 2H), 1.27(t, J=7.14 Hz, 3H) |
4u | 7.91—7.18(m, 4H), 6.30(brs, 2H), 3.85(t, J=6.97 Hz, 2H), 1.71(m, 2H), 0.87(t, J=7.35 Hz, 3H) |
4v | 7.90—7.18(m, 4H), 6.35(brs, 2H), 5.97—5.86(m, 1H), 5.20—5.06(m, 2H), 4.57—4.56(m, 2H) |
4w | 7.91—7.17(m, 4H), 6.30(brs, 2H), 3.89(t, J=7.03 Hz, 2H), 1.70—1.63(m, 2H), 1.33—1.25(m, 2H), 0.90(t, |
J=7.30 Hz, 3H) | |
4x | 8.28—8.07(m, 4H), 6.51(brs, 2H), 5.95—5.90(m, 1H), 5.22—5.08(m, 2H), 4.63—4.61(m, 2H) |
Table 2 1H NMR data of intermediate compounds 4a, 4b and 4q—4x
Compd. | 1H NMR(DMSO-d6, 300 MHz), δ |
---|---|
4a | 8.29(d, J=2.46 Hz, 1H), 7.52—7.39(m, 1H), 7.33(d, J=8.25 Hz, 1H), 5.05(s, 2H), 4.99(brs, 2H), 2.52(t, |
J=7.05 Hz, 3H), 1.76—1.64(m, 2H), 0.96(t, J=8.05 Hz, 3H) | |
4b | 8.26(d, J=2.46 Hz, 1H), 7.51—7.37(m, 1H), 7.32(d, J=8.24 Hz, 1H), 5.05(s, 2H), 5.00(brs, 2H), 2.54(t, |
J=7.84 Hz, 2H), 1.69—1.59(m, 2H), 1.42—1.29(m, 2H), 0.91(t, J=7.67 Hz, 3H) | |
4q | 8.29—8.07(m, 4H), 6.49(brs, 2H), 3.99(q, J=7.17 Hz, 2H), 1.30(t, J=7.14 Hz, 3H) |
4r | 8.29—8.06(m, 4H), 6.48(brs, 2H), 3.91(t, J=6.90 Hz, 2H), 1.74—1.56(m, 2H), 0.88(t, J=7.35 Hz, 3H) |
4s | 8.29—8.06(m, 4H), 6.47(brs, 2H), 3.95(t, J=7.04 Hz, 2H), 1.70—1.54(m, 2H), 1.33—1.21(m, 2H), 0.91(t, |
J=7.31 Hz, 3H) | |
4t | 7.90—7.18(m, 4H), 6.30(brs, 2H), 3.93(q, J=7.17 Hz, 2H), 1.27(t, J=7.14 Hz, 3H) |
4u | 7.91—7.18(m, 4H), 6.30(brs, 2H), 3.85(t, J=6.97 Hz, 2H), 1.71(m, 2H), 0.87(t, J=7.35 Hz, 3H) |
4v | 7.90—7.18(m, 4H), 6.35(brs, 2H), 5.97—5.86(m, 1H), 5.20—5.06(m, 2H), 4.57—4.56(m, 2H) |
4w | 7.91—7.17(m, 4H), 6.30(brs, 2H), 3.89(t, J=7.03 Hz, 2H), 1.70—1.63(m, 2H), 1.33—1.25(m, 2H), 0.90(t, |
J=7.30 Hz, 3H) | |
4x | 8.28—8.07(m, 4H), 6.51(brs, 2H), 5.95—5.90(m, 1H), 5.22—5.08(m, 2H), 4.63—4.61(m, 2H) |
Compd. | Appearance | m. p./℃ | Yield(%) | Elemental analysis(%, calcd.) | IR(KBr), | |||||
---|---|---|---|---|---|---|---|---|---|---|
C | H | N | ||||||||
5a | Light yellow solid | 88—89 | 45 | 51.68 (51.93) | 5.42 (5.59) | 21.60 (21.63) | 3439, 3160, 2959, 1727, 1580, 1503, 1462, 1445, 1358, 1271, 1244, 1108, 1066, 818, 744 | |||
5b | Light yellow solid | 90—91 | 55 | 53.21 (53.33) | 5.97 (5.97) | 21.49 (21.73) | 3438, 3169, 2956, 2872, 1727, 1579, 1505, 1463, 1445, 1359, 1273, 1245, 1108, 818, 749 | |||
5c | White solid | 102—103 | 42 | 59.77 (59.97) | 6.30 (6.20) | 21.19 (21.52) | 3183, 3068, 2974, 1742, 1562, 1472, 1443, 1424, 1264, 1232, 1059, 771, 726, 693 | |||
5d | White Powder | 93—94 | 50 | 61.53 (61.75) | 6.02 (5.92) | 20.29 (20.58) | 3182, 3065, 2978, 1743, 1585, 1559, 1470, 1443, 1418, 1357, 1230, 1063, 774, 726, 694 | |||
5e | Yellow solid | 188—189 | 41 | 51.22 (51.14) | 5.09 (4.95) | 22.85 (22.94) | 3451, 3127, 2988, 1728, 1594, 1534, 1476, 1438, 1369, 1243, 1059, 791, 964 | |||
5f | Yellow solid | 128—129 | 45 | 52.31 (52.66) | 5.35 (5.37) | 21.83 (21.93) | 3450, 3213, 2989, 1731, 1534, 1473, 1363, 1241, 1063, 789, 741 | |||
5g | Yellow solid | 93—94 | 49 | 54.20 (54.05) | 5.75 (5.75) | 20.98 (21.01) | 3447, 3175, 2964, 1732, 1583, 1566, 1535, 1470, 1424, 1362, 1259, 1229, 1057, 784, 740 | |||
5h | Yellow solid | 127—128 | 44 | 52.73 (52.91) | 4.77 (4.76) | 21.92 (22.07) | 3460, 3171, 2940, 1740, 1582, 1563, 1530, 1421, 1360, 1265, 1232, 1059, 787, 744 | |||
5i | White powder | 117—118 | 50 | 52.78 (52.98) | 5.30 (5.13) | 18.75 (19.01) | 3463, 3207, 2987, 2900, 1736, 1596, 1518, 1474, 1234, 1232, 1094, 1063, 781, 752 | |||
5j | White powder | 98—99 | 46 | 55.82 (55.81) | 5.87 (5.93) | 17.31 (17.36) | 3442, 3174, 3059, 2962, 1729, 1576, 1460, 1420, 1264, 1244, 1218, 1064, 1052, 779, 755 | |||
5k | White powder | 83—84 | 51 | 55.04 (54.82) | 4.90 (4.93) | 18.23 (18.26) | 3453, 3188, 3064, 2975, 1736, 1575, 1562, 1471, 1411, 1351, 1265, 1244, 1064, 748 | |||
5l | White solid | 110—111 | 53 | 58.16 (57.92) | 6.26 (6.25) | 19.34 (19.30) | 3460, 3183, 3062, 2977, 1742, 1614, 1553, 1467, 1434, 1304, 1253, 1234, 1173, 1032, 940, 757 | |||
5m | White solid | 106—107 | 55 | 60.51 (60.36) | 7.02 (6.97) | 17.77 (17.60) | 3467, 3184, 3065, 2962, 1742, 1614, 1559, 1466, 1432, 1249, 1226, 1173, 1028, 848, 757 | |||
5n | White powder | 114—115 | 44 | 52.79 (52.98) | 5.11 (5.13) | 18.88 (19.01) | 3166, 2977, 1741, 1580, 1462, 1430, 1260, 1233, 1132, 1089, 837, 750 | |||
5o | White powder | 115—116 | 48 | 54.50 (54.46) | 5.50 (5.55) | 17.90 (18.15) | 3448, 3191, 2970, 2937, 1777, 1744, 1464, 1586, 1426, 1374, 1324, 1259, 1288, 1092, 857, 751 | |||
5p | White powder | 80—81 | 53 | 54.71 (54.82) | 5.11 (4.93) | 18.20 (18.26) | 3468, 3184, 3079, 2982, 1743, 1579, 1557, 1457, 1428, 1256, 1230, 1064, 838, 751 | |||
5q | Yellow solid | 197—198 | 56 | 51.17 (51.14) | 4.98 (4.95) | 22.90 (22.94) | 3463, 3209, 2986, 1699, 1605, 1568, 1521, 1341, 1274, 1237, 1068, 854, 727 | |||
5r | Yellow solid | 169—170 | 54 | 52.61 (52.66) | 5.46 (5.37) | 21.77 (21.93) | 3216, 3083, 2978, 2944, 1699, 1604, 1561, 1523, 1342, 1265, 1227, 1065, 854, 727 | |||
5s | Yellow solid | 150—151 | 46 | 54.33 (54.05) | 5.92 (5.75) | 20.76 (21.01) | 3237, 3090, 2960, 2874, 1704, 1604, 1561, 1524, 1468, 1341, 1263, 1070, 866, 727 | |||
5t | White powder | 114—115 | 53 | 56.26 (56.11) | 5.59 (5.43) | 20.08 (20.13) | 3183, 3069, 2976, 2941, 1745, 1601, 1561, 1466, 1431, 1262, 1233, 1058, 845, 755 | |||
5u | White powder | 115—116 | 47 | 57.44 (57.52) | 5.99 (5.86) | 19.08 (19.17) | 3473, 3186, 3066, 2976, 2941, 1745, 1601, 1563, 1467, 1428, 1255, 1229, 1150, 1061, 848, 757 | |||
5v | White powder | 89—90 | 49 | 58.11 (57.92) | 5.43 (5.21) | 19.29 (19.30) | 3186, 3066, 2980, 2938, 1744, 1601, 1562, 1467, 1431, 1256, 1228, 1188, 1062, 848, 756 | |||
5wa | White powder | 54—55 | 48 | 3194, 3067, 2962, 2932, 2876, 1742, 1609, 1567, 1469, 1431, 1249, 1226, 1060, 850, 755 | ||||||
5xb | Yellow solid | 175—176 | 46 | 3434, 3210, 2984, 1701, 1604, 1653, 1524, 1464, 1324, 1206, 1066, 855, 727 | ||||||
6a | White powder | 83—84 | 44 | 59.71 (59.99) | 6.73 (6.71) | 15.54 (15.55) | 3453, 2981, 2960, 2874, 1778, 1645, 1589, 1580, 1447, 1370, 1323, 1264, 1208, 1099, 855, 775, 702 | |||
6b | White powder | 96—97 | 45 | 52.24 (52.39) | 5.28 (5.22) | 15.33 (15.27) | 3445, 3050, 2988, 1781, 1657, 1613, 1582, 1562, 1471, 1367, 1324, 1252, 1201, 1150, 1073, 857, 773 | |||
6c | White powder | 93—94 | 40 | 56.40 (56.34) | 6.20 (6.12) | 15.54 (15.46) | 3438, 2973, 2939, 2841, 1774, 1658, 1601, 1445, 1372, 1305, 1264, 1202, 1075, 850, 775 | |||
6d | White powder | 104—105 | 41 | 57.73 (57.75) | 6.01 (5.92) | 15.00 (14.96) | 3440, 2904, 1775, 1658, 1603, 1469, 1437, 1327, 1215, 1140, 1045, 927, 773 | |||
6e | White solid | 107—108 | 42 | 57.46 (57.74) | 6.54 (6.43) | 14.93 (14.88) | 3443, 2971, 2935, 2842, 1776, 1645, 1615, 1587, 1562, 1508, 1372, 1325, 1259, 1210, 1180, 1068, 857, 736 | |||
6f | White powder | 98—99 | 42 | 57.77 (57.75) | 5.81 (5.92) | 15.03 (14.96) | 3442, 2978, 2840, 1778, 1646, 1589, 1563, 1507, 1372, 1327, 1264, 1212, 1179, 1067, 858, 764 | |||
6gc | White powder | 89—90 | 49 | 3439, 3091, 2983, 2937, 2899, 2875, 1778, 1647, 1587, 1442, 1370, 1321, 1265, 1204, 1100, 857, 730 |
Table 3 Appearance, melting point, yield, elemental analysis and IR data of target compounds
Compd. | Appearance | m. p./℃ | Yield(%) | Elemental analysis(%, calcd.) | IR(KBr), | |||||
---|---|---|---|---|---|---|---|---|---|---|
C | H | N | ||||||||
5a | Light yellow solid | 88—89 | 45 | 51.68 (51.93) | 5.42 (5.59) | 21.60 (21.63) | 3439, 3160, 2959, 1727, 1580, 1503, 1462, 1445, 1358, 1271, 1244, 1108, 1066, 818, 744 | |||
5b | Light yellow solid | 90—91 | 55 | 53.21 (53.33) | 5.97 (5.97) | 21.49 (21.73) | 3438, 3169, 2956, 2872, 1727, 1579, 1505, 1463, 1445, 1359, 1273, 1245, 1108, 818, 749 | |||
5c | White solid | 102—103 | 42 | 59.77 (59.97) | 6.30 (6.20) | 21.19 (21.52) | 3183, 3068, 2974, 1742, 1562, 1472, 1443, 1424, 1264, 1232, 1059, 771, 726, 693 | |||
5d | White Powder | 93—94 | 50 | 61.53 (61.75) | 6.02 (5.92) | 20.29 (20.58) | 3182, 3065, 2978, 1743, 1585, 1559, 1470, 1443, 1418, 1357, 1230, 1063, 774, 726, 694 | |||
5e | Yellow solid | 188—189 | 41 | 51.22 (51.14) | 5.09 (4.95) | 22.85 (22.94) | 3451, 3127, 2988, 1728, 1594, 1534, 1476, 1438, 1369, 1243, 1059, 791, 964 | |||
5f | Yellow solid | 128—129 | 45 | 52.31 (52.66) | 5.35 (5.37) | 21.83 (21.93) | 3450, 3213, 2989, 1731, 1534, 1473, 1363, 1241, 1063, 789, 741 | |||
5g | Yellow solid | 93—94 | 49 | 54.20 (54.05) | 5.75 (5.75) | 20.98 (21.01) | 3447, 3175, 2964, 1732, 1583, 1566, 1535, 1470, 1424, 1362, 1259, 1229, 1057, 784, 740 | |||
5h | Yellow solid | 127—128 | 44 | 52.73 (52.91) | 4.77 (4.76) | 21.92 (22.07) | 3460, 3171, 2940, 1740, 1582, 1563, 1530, 1421, 1360, 1265, 1232, 1059, 787, 744 | |||
5i | White powder | 117—118 | 50 | 52.78 (52.98) | 5.30 (5.13) | 18.75 (19.01) | 3463, 3207, 2987, 2900, 1736, 1596, 1518, 1474, 1234, 1232, 1094, 1063, 781, 752 | |||
5j | White powder | 98—99 | 46 | 55.82 (55.81) | 5.87 (5.93) | 17.31 (17.36) | 3442, 3174, 3059, 2962, 1729, 1576, 1460, 1420, 1264, 1244, 1218, 1064, 1052, 779, 755 | |||
5k | White powder | 83—84 | 51 | 55.04 (54.82) | 4.90 (4.93) | 18.23 (18.26) | 3453, 3188, 3064, 2975, 1736, 1575, 1562, 1471, 1411, 1351, 1265, 1244, 1064, 748 | |||
5l | White solid | 110—111 | 53 | 58.16 (57.92) | 6.26 (6.25) | 19.34 (19.30) | 3460, 3183, 3062, 2977, 1742, 1614, 1553, 1467, 1434, 1304, 1253, 1234, 1173, 1032, 940, 757 | |||
5m | White solid | 106—107 | 55 | 60.51 (60.36) | 7.02 (6.97) | 17.77 (17.60) | 3467, 3184, 3065, 2962, 1742, 1614, 1559, 1466, 1432, 1249, 1226, 1173, 1028, 848, 757 | |||
5n | White powder | 114—115 | 44 | 52.79 (52.98) | 5.11 (5.13) | 18.88 (19.01) | 3166, 2977, 1741, 1580, 1462, 1430, 1260, 1233, 1132, 1089, 837, 750 | |||
5o | White powder | 115—116 | 48 | 54.50 (54.46) | 5.50 (5.55) | 17.90 (18.15) | 3448, 3191, 2970, 2937, 1777, 1744, 1464, 1586, 1426, 1374, 1324, 1259, 1288, 1092, 857, 751 | |||
5p | White powder | 80—81 | 53 | 54.71 (54.82) | 5.11 (4.93) | 18.20 (18.26) | 3468, 3184, 3079, 2982, 1743, 1579, 1557, 1457, 1428, 1256, 1230, 1064, 838, 751 | |||
5q | Yellow solid | 197—198 | 56 | 51.17 (51.14) | 4.98 (4.95) | 22.90 (22.94) | 3463, 3209, 2986, 1699, 1605, 1568, 1521, 1341, 1274, 1237, 1068, 854, 727 | |||
5r | Yellow solid | 169—170 | 54 | 52.61 (52.66) | 5.46 (5.37) | 21.77 (21.93) | 3216, 3083, 2978, 2944, 1699, 1604, 1561, 1523, 1342, 1265, 1227, 1065, 854, 727 | |||
5s | Yellow solid | 150—151 | 46 | 54.33 (54.05) | 5.92 (5.75) | 20.76 (21.01) | 3237, 3090, 2960, 2874, 1704, 1604, 1561, 1524, 1468, 1341, 1263, 1070, 866, 727 | |||
5t | White powder | 114—115 | 53 | 56.26 (56.11) | 5.59 (5.43) | 20.08 (20.13) | 3183, 3069, 2976, 2941, 1745, 1601, 1561, 1466, 1431, 1262, 1233, 1058, 845, 755 | |||
5u | White powder | 115—116 | 47 | 57.44 (57.52) | 5.99 (5.86) | 19.08 (19.17) | 3473, 3186, 3066, 2976, 2941, 1745, 1601, 1563, 1467, 1428, 1255, 1229, 1150, 1061, 848, 757 | |||
5v | White powder | 89—90 | 49 | 58.11 (57.92) | 5.43 (5.21) | 19.29 (19.30) | 3186, 3066, 2980, 2938, 1744, 1601, 1562, 1467, 1431, 1256, 1228, 1188, 1062, 848, 756 | |||
5wa | White powder | 54—55 | 48 | 3194, 3067, 2962, 2932, 2876, 1742, 1609, 1567, 1469, 1431, 1249, 1226, 1060, 850, 755 | ||||||
5xb | Yellow solid | 175—176 | 46 | 3434, 3210, 2984, 1701, 1604, 1653, 1524, 1464, 1324, 1206, 1066, 855, 727 | ||||||
6a | White powder | 83—84 | 44 | 59.71 (59.99) | 6.73 (6.71) | 15.54 (15.55) | 3453, 2981, 2960, 2874, 1778, 1645, 1589, 1580, 1447, 1370, 1323, 1264, 1208, 1099, 855, 775, 702 | |||
6b | White powder | 96—97 | 45 | 52.24 (52.39) | 5.28 (5.22) | 15.33 (15.27) | 3445, 3050, 2988, 1781, 1657, 1613, 1582, 1562, 1471, 1367, 1324, 1252, 1201, 1150, 1073, 857, 773 | |||
6c | White powder | 93—94 | 40 | 56.40 (56.34) | 6.20 (6.12) | 15.54 (15.46) | 3438, 2973, 2939, 2841, 1774, 1658, 1601, 1445, 1372, 1305, 1264, 1202, 1075, 850, 775 | |||
6d | White powder | 104—105 | 41 | 57.73 (57.75) | 6.01 (5.92) | 15.00 (14.96) | 3440, 2904, 1775, 1658, 1603, 1469, 1437, 1327, 1215, 1140, 1045, 927, 773 | |||
6e | White solid | 107—108 | 42 | 57.46 (57.74) | 6.54 (6.43) | 14.93 (14.88) | 3443, 2971, 2935, 2842, 1776, 1645, 1615, 1587, 1562, 1508, 1372, 1325, 1259, 1210, 1180, 1068, 857, 736 | |||
6f | White powder | 98—99 | 42 | 57.77 (57.75) | 5.81 (5.92) | 15.03 (14.96) | 3442, 2978, 2840, 1778, 1646, 1589, 1563, 1507, 1372, 1327, 1264, 1212, 1179, 1067, 858, 764 | |||
6gc | White powder | 89—90 | 49 | 3439, 3091, 2983, 2937, 2899, 2875, 1778, 1647, 1587, 1442, 1370, 1321, 1265, 1204, 1100, 857, 730 |
Compd. | 1H NMR(DMSO-d6, 300 MHz), δ | 13C NMR(DMSO-d6, 75 MHz), δ |
---|---|---|
5a | 9.43(brs, 1H, NH), 8.34—7.26(m, 3H, pyridine), 5.26(s, 2H, CH2N), 4.21(q, J=7.14 Hz, 2H, OCH2), 2.58(t, J=7.31 Hz, 2H, CH2), 1.72—1.67(m, 2H, CH2), 1.30(t, J=7.14 Hz, 3H, OCH2CH3), 0.94(t, J=7.35 Hz, 3H, CH3) | 162.11, 153.91, 149.75, 149.41, 147.10, 139.46, 131.51, 124.29, 61.55, 47.58, 30.02, 20.96, 14.42, 13.70 |
5b | 9.44(brs, 1H, NH), 8.34—7.26(m, 3H, pyridine), 5.25(s, 2H, CH2N), 4.21(q, J=7.12 Hz, 2H, OCH2), 2.61(t, J=7.31 Hz, 2H, CH2), 1.67—1.63(m, 2H, CH2), 1.37—1.33(m, 2H, CH2), 1.30(t, J=7.11 Hz, 3H, OCH2CH3), 0.94(t, J=7.28Hz, 3H, CH3) | 161.42, 154.71, 151.02, 149.15, 148.21, 138.56, 130.00, 124.49, 62.31, 49.16, 29.86, 27.60, 22.19, 14.30, 13.64 |
5c | 10.08(brs, 1H, NH), 7.96—7.92(m, 5H, Ph), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.05(q, J=7.20 Hz, 2H, CH2N), 1.38(t, J=7.20 Hz, 3H, OCH2CH3), 1.24(t, J=7.11 Hz, 3H, CH3) | 158.76, 153.96, 147.11, 131.14, 129.18, 128.82, 125.53, 61.57, 42.89, 14.48, 14.45 |
5d | 10.15(brs, 1H, NH), 7.95—7.40(m, 5H, Ph), 6.02—5.91(m, 1H, | 158.85, 153.75, 147.66, 132.42, 130.98, 129.27, 128.84, 125.56, 118.34, 61.57, 50.40, 14.48 |
5e | 10.18(brs, 1H, NH), 7.96—7.63(m, 4H, NO2Ph), 4.17(q, J=7.11 Hz, 2H, OCH2), 4.04(q, J=7.23 Hz, 2H, CH2N), 1.35(t, J=7.17 Hz, 3H, OCH2CH3), 1.24(t, J=7.08 Hz, 3H, CH3) | 155.15, 153.81, 148.88, 147.28, 132.27, 130.49, 129.86, 123.73, 123.63, 61.67, 43.15, 14.45, 14.36 |
5f | 10.17(brs, 1H, NH), 7.95—7.63(m, 4H, NO2Ph), 4.15(q, J=7.08 Hz, 2H, OCH2), 3.98(t, J=7.08 Hz, 2H, CH2N), 1.79—1.75(m, 2H, CH2), 1.24(t, J=7.08 Hz, 3H, OCH2CH3), 0.84(t, J=7.35 Hz, 3H, CH3) | 155.14, 153.74, 148.92, 147.72, 132.27, 130.47, 129.90, 123.73, 123.71, 61.44, 49.42, 22.16, 14.44, 10.84 |
5g | 10.19(brs, 1H, NH), 7.95—7.63(m, 4H, NO2Ph), 4.15(q, J=7.11 Hz, 2H, OCH2), 4.01(t, J=7.05 Hz, 2H, CH2N), 1.75—1.71(m, 2H, CH2), 1.29—1.25(m, 2H, CH2), 1.23(t, J=7.29 Hz, 3H, OCH2CH3), 0.88(t, J=7.26 Hz, 3H, CH3) | 155.11, 153.74, 148.91, 147.63, 132.25, 130.45, 129.88, 123.71, 123.69, 61.64, 47.56, 30.70, 19.13, 14.44, 13.46 |
5h | 10.08(brs, 1H, NH), 7.77—7.47(m, 4H, NO2Ph), 5.84—5.72(m, 1H, =CH), 5.08—4.93(m, 2H, CH2 =), 4.56—4.54(m, 2H, CH2N), 3.98(q, J=7.11 Hz, 2H, OCH2), 1.06(t, J=7.11 Hz, 3H, CH3) | 157.62, 155.49, 150.65, 149.14, 133.24, 132.67, 131.81, 131.44, 125.88, 124.96, 118.91, 63.38, 51.94, 14.70 |
5i | 10.13(brs, 1H, NH), 7.82—7.42(m, 4H, ClPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.07(q, J=7.20 Hz, 2H, CH2N), 1.38(t, J=7.20 Hz, 3H, OCH2CH3), 1.25(t, J=7.08 Hz, 3H, CH3) | 157.37, 153.92, 146.61, 131.50, 131.14, 130.69, 130.51, 130.03, 127.27, 61.57, 42.96, 14.48, 14.42 |
5j | 8.57(brs, 1H, NH), 7.84—7.26(m, 4H, ClPh), 4.19(q, J=7.12 Hz, 2H, OCH2), 4.11(t, J=7.37 Hz, 2H, CH2N), 1.93—1.89(m, 2H, CH2), 1.39—1.35(m, 2H, CH2), 1.24(t, J=7.06 Hz, 3H, OCH2CH3), 0.94(t, J=7.30 Hz, 3H, CH3) | 157.36, 153.92, 147.00, 131.56, 131.21, 130.75, 130.60, 130.06, 127.36, 61.62, 47.45, 30.86, 19.27, 14.55, 13.57 |
5k | 10.21(brs, 1H, NH), 7.82—7.40(m, 4H, ClPh), 6.05—5.91(m, 1H, =CH), 5.26—5.14(m, 2H, CH2 =), 4.76—4.73(m, 2H, CH2N), 4.16(q, J=7.08 Hz, 2H, OCH2), 1.24(t, J=7.08 Hz, 3H, CH3) | 159.56, 155.61, 148.60, 134.04, 132.76, 132.48, 131.69, 131.47, 131.24, 127.92, 119.05 , 63.37, 51.89, 14.73 |
5l | 10.03(brs, 1H, NH), 7.88—6.99(m, 4H, OCH3Ph), 4.15(q, J=7.11 Hz, 2H, OCH2), 4.01(q, J=7.20 Hz, 2H, CH2N), 3.97(s, 3H, OCH3), 1.36(t, J=7.20 Hz, 3H, OCH2CH3), 1.24(t, J=7.08 Hz, 3H, CH3) | 160.10, 158.69, 153.96, 146.85, 126.99, 123.78, 114.21, 61.51, 55.31, 42.73, 14.93, 14.85 |
5m | 10.01(brs, 1H, NH), 7.88—6.98(m, 4H, OCH3Ph), 4.15(q, J=7.08 Hz, 2H, OCH2), 3.99(t, J=7.11 Hz, 2H, CH2N), 3.79(s, 3H, OCH3), 1.78—1.74(m, 2H, CH2), 1.28—1.24(m, 2H, CH2), 1.24(t, J=7.08 Hz, 3H, OCH2CH3), 0.80(t, J=7.29 Hz, 3H, CH3) | 162.00, 160.56, 159.19, 154.17, 146.81, 126.84, 122.82 , 113.30, 61.60, 54.07, 30.53, 18.97, 13.04, 12.14 |
5n | 10.13(brs, 1H, NH), 7.96—7.50(m, 4H, ClPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.05(q, J=7.20 Hz, 2H, CH2N), 1.37(t, J=7.20 Hz, 3H, OCH2CH3), 1.24(t, J=7.08 Hz, 3H, CH3) | 157.84, 153.90, 147.32, 133.85, 129.98, 128.97, 127.27, 61.61, 42.98, 14.48, 14.42 |
5o | 10.11(brs, 1H, NH), 7.96—7.50(m, 4H, ClPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 3.99(t, J=7.02 Hz, 2H, CH2N), 1.83—1.78(m, 2H, CH2), 1.24(t, J=7.05 Hz, 3H, OCH2CH3), 0.86(t, J=7.35 Hz, 3H, CH3) | 157.78, 153.80, 147.73, 133.83, 129.96, 128.95, 127.27, 61.56, 49.28, 22.20, 14.46, 10.95 |
5p | 8.27(brs, 1H, NH), 7.99—7.35(m, 4H, ClPh), 6.06—5.96(m, 1H, =CH), 5.32—5.25(m, 2H, CH2 =), 4.80—4.77(m, 2H, CH2N), 4.26(q, J=7.14 Hz, 2H, OCH2), 1.31(t, J=7.11 Hz, 3H, CH3) | 158.51, 153.73, 147.44, 135.22, 131.33, 129.05, 128.68, 127.52, 119.08, 62.60, 51.94, 14.36 |
5q | 10.26(brs, 1H, NH), 8.35—8.31(m, 4H, NO2Ph), 4.18(q, J=7.08 Hz, 2H, OCH2), 4.10(q, J=7.20 Hz, 2H, CH2N), 1.40(t, J=7.20 Hz, 3H, OCH2CH3), 1.25(t, J=7.08 Hz, 3H, CH3) | 157.03, 153.78, 147.86, 147.76, 136.99, 126.53, 124.33, 61.69, 43.23, 14.49, 14.38 |
5r | 10.23(brs, 1H, NH), 8.34—8.16(m, 4H, NO2Ph), 4.17(q, J=7.08 Hz, 2H, OCH2), 4.03(t, J=7.02 Hz, 2H, CH2N), 1.84—1.80(m, 2H, CH2), 1.25(t, J=7.08 Hz, 3H, OCH2CH3), 0.87(t, J=7.35 Hz, 3H, CH3) | 156.99, 153.70, 148.28, 147.78, 136.98, 126.55, 124.35, 61.66, 49.50, 22.19, 14.47, 10.95 |
5s | 10.24(brs, 1H, NH), 8.35—8.17(m, 4H, NO2Ph), 4.18(q, J=7.05 Hz, 2H, OCH2), 4.08(t, J=7.11 Hz, 2H, CH2N), 1.82—1.78(m, 2H, CH2), 1.32—1.28(m, 2H, CH2), 1.26(t, J=7.11 Hz, 3H, OCH2CH3), 0.90(t, J=7.29 Hz, 3H, CH3) | 157.03, 153.76, 148.23, 147.79, 137.00, 126.58, 124.39, 61.72, 47.71, 30.83, 19.30, 14.52, 13.56 |
5t | 10.10(brs, 1H, NH), 7.99—7.25(m, 4H, FPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.04(q, J=7.20 Hz, 2H, CH2N), 1.37(t, J=7.20 Hz, 3H, OCH2CH3), 1.25(t, J=7.08 Hz, 3H, CH3) | 164.43, 161.17, 157.99, 153.93, 147.20, 127.77, 127.66, 115.99, 115.70, 61.60, 42.90, 14.51, 14.47 |
5u | 10.09(brs, 1H, NH), 7.99—7.25(m, 4H, FPh), 4.16(q, J=7.02 Hz, 2H, OCH2), 3.98(t, J=7.08 Hz, 2H, CH2N), 1.83—1.79(m, 2H, CH2), 1.24(t, J=7.05 Hz, 3H, OCH2CH3), 0.86(t, J=7.32 Hz, 3H, CH3) | 164.45, 161.19, 157.97, 153.88, 147.65, 127.80, 127.69, 116.01, 115.72, 61.60, 49.24, 22.27, 14.52, 11.01 |
5v | 10.17(brs, 1H, NH), 7.99—7.26(m, 4H, FPh), 6.01—5.93(m, 1H, =CH), 5.25—5.15(m, 2H, CH2 =), 4.72—4.70(m, 2H, CH2N), 4.16(q, J=7.11 Hz, 2H, OCH2), 1.24(t, J=7.11 Hz, 3H, CH3) | 164.46, 161.20, 158.10, 153.72, 147.75, 132.39, 127.81, 127.53, 118.38, 115.97, 115.69, 61.59, 50.41, 14.47 |
5w | 10.09(brs, 1H, NH), 7.99—7.25(m, 4H, FPh), 4.16(q, J=7.11 Hz, 2H, OCH2), 4.01(t, J=7.11 Hz, 2H, CH2N), 1.80—1.75(m, 2H, CH2), 1.34—1.26(m, 2H, CH2), 1.24(t, J=7.08 Hz, 3H, OCH2CH3), 0.88(t, J=7.29 Hz, 3H, CH3) | 164.40, 161.15, 157.93, 153.85, 147.53, 127.76, 127.65, 115.95, 115.66, 61.54, 47.36, 30.80, 19.25, 14.48, 13.50 |
5x | 10.31(brs, 1H, NH), 8.34—8.16(m, 4H, NO2Ph), 6.03—5.94(m, 1H, =CH), 5.28—5.17(m, 2H, CH2 =), 4.77(d, J=5.73 Hz, 2H, CH2N), 4.17(q, J=7.11 Hz, 2H, OCH2), 1.25(t, J=7.08 Hz, 3H, CH3) | 157.13, 153.57, 148.37, 147.82, 136.82, 132.15, 126.59, 124.35, 118.69, 61.69, 50.67, 14.46 |
6a | 7.62—7.50(m, 5H, Ph), 4.21(q, J=7.21 Hz, 2H, OCH2), 3.98(q, J=7.08 Hz, 2H, OCH2), 3.95(t, J=7.07 Hz, 2H, CH2N), 1.75—1.71(m, 2H, CH2), 1.35—1.31(m, 2H, CH2), 1.18(t, J=7.09 Hz, 3H, OCH2CH3), 1.12(t, J=7.12 Hz, 3H, OCH2CH3), 0.91(t, J=7.30 Hz, 3H, CH3) | 160.00, 149.77, 147.33, 145.50, 131.14, 129.10, 128.68, 125.27, 65.45, 60.51, 46.32, 29.61, 19.24, 14.65, 13.54, 13.34 |
6b | 7.69—7.49(m, 5H, ClPh), 4.13(q, J=7.11 Hz, 2H, OCH2), 3.98(q, J=7.24 Hz, 2H, OCH2), 3.97(t, J=7.10 Hz, 2H, CH2N), 1.31(t, J=7.20 Hz, 3H, OCH2CH3), 1.17(t, J=7.09 Hz, 3H, OCH2CH3), 1.02(t, J=7.13 Hz, 3H, CH3) | 159.78, 148.90, 146.95, 143.01, 133.47, 133.07, 132.58, 129.51, 127.74, 125.68, 65.31, 60.57, 42.02, 14.66, 13.27, 13.16 |
6c | 7.51—6.96(m, 4H, OCH3Ph), 4.26(q, J=7.20 Hz, 2H, OCH2), 4.14(q, J=7.13 Hz, 2H, OCH2), 4.08(t, J=7.23 Hz, 2H, CH2N), 3.78(s, 3H, OCH3), 1.42(t, J=7.22 Hz, 3H, OCH2CH3), 1.32(t, J=7.17 Hz, 3H, OCH2CH3), 1.20(t, J=7.16 Hz, 3H, CH3) | 159.90, 157.04, 149.13, 147.45, 143.77, 133.11, 130.83, 121.07, 114.74, 111.35, 65.03, 60.47, 55.66, 41.87, 14.71, 13.48, 13.24 |
6d | 7.51—6.90(m, 4H, OCH3Ph), 6.03—5.93(m, 1H, =CH), 5.38—5.27(m, 2H, CH2 =), 4.65—4.62(m, 2H, CH2N), 4.26(q, J=7.20 Hz, 2H, OCH2), 4.14(t, J=7.12 Hz, 2H, OCH2), 3.77(s, 3H, OCH3), 1.31(t, J=7.11 Hz, 3H, OCH2CH3), 1.20(t, J=7.17 Hz, 3H, CH3) | 160.62, 157.20, 149.98, 147.57, 144.52, 132.54, 131.02, 130.61, 121.00, 119.48, 115.37, 110.34, 64.77, 61.23, 55.18, 49.32, 14.59, 13.45 |
6e | 7.54—7.05(m, 4H, OCH3Ph), 4.22(q, J=7.14 Hz, 2H, OCH2), 3.97(q, J=7.07 Hz, 2H, OCH2), 3.89(t, J=6.96 Hz, 2H, CH2N), 3.82(s, 3H, OCH3), 1.77—1.73(m, 2H, CH2), 1.82(t, J=7.08 Hz, 3H, OCH2CH3), 1.52(t, J=7.15 Hz, 3H, OCH2CH3), 0.90(t, J=7.36 Hz, 3H, CH3) | 161.40, 160.08, 149.89, 147.48, 145.48, 130.78, 117.18, 114.12, 65.40, 60.45, 55.53, 48.14, 21.05, 14.63, 13.40, 10.96 |
6f | 7.55—7.04(m, 4H, OCH3Ph), 5.99—5.88(m, 1H, =CH), 5.28—5.21(m, 2H, CH2 =), 4.57(d, J=5.55 Hz, 2H, CH2N), 4.22(q, J=7.14 Hz, 2H, OCH2), 3.98(t, J=7.08 Hz, 2H, OCH2), 3.82(s, 3H, OCH3), 1.20(t, J=7.08 Hz, 3H, OCH2CH3), 1.15(t, J=7.11 Hz, 3H, CH3) | 161.42, 159.99, 149.70, 147.43, 145.72, 131.52, 130.83, 118.69, 117.12, 114.13, 65.45, 60.52, 55.56, 48.81, 14.63, 13.42 |
6g | 7.61—7.26(m, 4H, ClPh), 4.32(q, J=7.17 Hz, 2H, OCH2), 4.16(q, J=7.14 Hz, 2H, OCH2), 4.02(t, J=7.41 Hz, 2H, CH2N), 1.85—1.80(m, 2H, CH2), 1.39—1.33(m, 2H, CH2), 1.32(t, J=7.11 Hz, 3H, OCH2CH3), 1.26(t, J=7.14 Hz, 3H, OCH2CH3), 0.95(t, J=7.29 Hz, 3H, CH3) | 161.01, 150.53, 147.53, 145.13, 137.39, 130.67, 128.68, 123.69, 65.55, 61.35, 47.02, 30.01, 19.70, 14.56, 13.54, 13.48 |
Table 4 1H NMR and 13C NMR data of target compounds
Compd. | 1H NMR(DMSO-d6, 300 MHz), δ | 13C NMR(DMSO-d6, 75 MHz), δ |
---|---|---|
5a | 9.43(brs, 1H, NH), 8.34—7.26(m, 3H, pyridine), 5.26(s, 2H, CH2N), 4.21(q, J=7.14 Hz, 2H, OCH2), 2.58(t, J=7.31 Hz, 2H, CH2), 1.72—1.67(m, 2H, CH2), 1.30(t, J=7.14 Hz, 3H, OCH2CH3), 0.94(t, J=7.35 Hz, 3H, CH3) | 162.11, 153.91, 149.75, 149.41, 147.10, 139.46, 131.51, 124.29, 61.55, 47.58, 30.02, 20.96, 14.42, 13.70 |
5b | 9.44(brs, 1H, NH), 8.34—7.26(m, 3H, pyridine), 5.25(s, 2H, CH2N), 4.21(q, J=7.12 Hz, 2H, OCH2), 2.61(t, J=7.31 Hz, 2H, CH2), 1.67—1.63(m, 2H, CH2), 1.37—1.33(m, 2H, CH2), 1.30(t, J=7.11 Hz, 3H, OCH2CH3), 0.94(t, J=7.28Hz, 3H, CH3) | 161.42, 154.71, 151.02, 149.15, 148.21, 138.56, 130.00, 124.49, 62.31, 49.16, 29.86, 27.60, 22.19, 14.30, 13.64 |
5c | 10.08(brs, 1H, NH), 7.96—7.92(m, 5H, Ph), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.05(q, J=7.20 Hz, 2H, CH2N), 1.38(t, J=7.20 Hz, 3H, OCH2CH3), 1.24(t, J=7.11 Hz, 3H, CH3) | 158.76, 153.96, 147.11, 131.14, 129.18, 128.82, 125.53, 61.57, 42.89, 14.48, 14.45 |
5d | 10.15(brs, 1H, NH), 7.95—7.40(m, 5H, Ph), 6.02—5.91(m, 1H, | 158.85, 153.75, 147.66, 132.42, 130.98, 129.27, 128.84, 125.56, 118.34, 61.57, 50.40, 14.48 |
5e | 10.18(brs, 1H, NH), 7.96—7.63(m, 4H, NO2Ph), 4.17(q, J=7.11 Hz, 2H, OCH2), 4.04(q, J=7.23 Hz, 2H, CH2N), 1.35(t, J=7.17 Hz, 3H, OCH2CH3), 1.24(t, J=7.08 Hz, 3H, CH3) | 155.15, 153.81, 148.88, 147.28, 132.27, 130.49, 129.86, 123.73, 123.63, 61.67, 43.15, 14.45, 14.36 |
5f | 10.17(brs, 1H, NH), 7.95—7.63(m, 4H, NO2Ph), 4.15(q, J=7.08 Hz, 2H, OCH2), 3.98(t, J=7.08 Hz, 2H, CH2N), 1.79—1.75(m, 2H, CH2), 1.24(t, J=7.08 Hz, 3H, OCH2CH3), 0.84(t, J=7.35 Hz, 3H, CH3) | 155.14, 153.74, 148.92, 147.72, 132.27, 130.47, 129.90, 123.73, 123.71, 61.44, 49.42, 22.16, 14.44, 10.84 |
5g | 10.19(brs, 1H, NH), 7.95—7.63(m, 4H, NO2Ph), 4.15(q, J=7.11 Hz, 2H, OCH2), 4.01(t, J=7.05 Hz, 2H, CH2N), 1.75—1.71(m, 2H, CH2), 1.29—1.25(m, 2H, CH2), 1.23(t, J=7.29 Hz, 3H, OCH2CH3), 0.88(t, J=7.26 Hz, 3H, CH3) | 155.11, 153.74, 148.91, 147.63, 132.25, 130.45, 129.88, 123.71, 123.69, 61.64, 47.56, 30.70, 19.13, 14.44, 13.46 |
5h | 10.08(brs, 1H, NH), 7.77—7.47(m, 4H, NO2Ph), 5.84—5.72(m, 1H, =CH), 5.08—4.93(m, 2H, CH2 =), 4.56—4.54(m, 2H, CH2N), 3.98(q, J=7.11 Hz, 2H, OCH2), 1.06(t, J=7.11 Hz, 3H, CH3) | 157.62, 155.49, 150.65, 149.14, 133.24, 132.67, 131.81, 131.44, 125.88, 124.96, 118.91, 63.38, 51.94, 14.70 |
5i | 10.13(brs, 1H, NH), 7.82—7.42(m, 4H, ClPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.07(q, J=7.20 Hz, 2H, CH2N), 1.38(t, J=7.20 Hz, 3H, OCH2CH3), 1.25(t, J=7.08 Hz, 3H, CH3) | 157.37, 153.92, 146.61, 131.50, 131.14, 130.69, 130.51, 130.03, 127.27, 61.57, 42.96, 14.48, 14.42 |
5j | 8.57(brs, 1H, NH), 7.84—7.26(m, 4H, ClPh), 4.19(q, J=7.12 Hz, 2H, OCH2), 4.11(t, J=7.37 Hz, 2H, CH2N), 1.93—1.89(m, 2H, CH2), 1.39—1.35(m, 2H, CH2), 1.24(t, J=7.06 Hz, 3H, OCH2CH3), 0.94(t, J=7.30 Hz, 3H, CH3) | 157.36, 153.92, 147.00, 131.56, 131.21, 130.75, 130.60, 130.06, 127.36, 61.62, 47.45, 30.86, 19.27, 14.55, 13.57 |
5k | 10.21(brs, 1H, NH), 7.82—7.40(m, 4H, ClPh), 6.05—5.91(m, 1H, =CH), 5.26—5.14(m, 2H, CH2 =), 4.76—4.73(m, 2H, CH2N), 4.16(q, J=7.08 Hz, 2H, OCH2), 1.24(t, J=7.08 Hz, 3H, CH3) | 159.56, 155.61, 148.60, 134.04, 132.76, 132.48, 131.69, 131.47, 131.24, 127.92, 119.05 , 63.37, 51.89, 14.73 |
5l | 10.03(brs, 1H, NH), 7.88—6.99(m, 4H, OCH3Ph), 4.15(q, J=7.11 Hz, 2H, OCH2), 4.01(q, J=7.20 Hz, 2H, CH2N), 3.97(s, 3H, OCH3), 1.36(t, J=7.20 Hz, 3H, OCH2CH3), 1.24(t, J=7.08 Hz, 3H, CH3) | 160.10, 158.69, 153.96, 146.85, 126.99, 123.78, 114.21, 61.51, 55.31, 42.73, 14.93, 14.85 |
5m | 10.01(brs, 1H, NH), 7.88—6.98(m, 4H, OCH3Ph), 4.15(q, J=7.08 Hz, 2H, OCH2), 3.99(t, J=7.11 Hz, 2H, CH2N), 3.79(s, 3H, OCH3), 1.78—1.74(m, 2H, CH2), 1.28—1.24(m, 2H, CH2), 1.24(t, J=7.08 Hz, 3H, OCH2CH3), 0.80(t, J=7.29 Hz, 3H, CH3) | 162.00, 160.56, 159.19, 154.17, 146.81, 126.84, 122.82 , 113.30, 61.60, 54.07, 30.53, 18.97, 13.04, 12.14 |
5n | 10.13(brs, 1H, NH), 7.96—7.50(m, 4H, ClPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.05(q, J=7.20 Hz, 2H, CH2N), 1.37(t, J=7.20 Hz, 3H, OCH2CH3), 1.24(t, J=7.08 Hz, 3H, CH3) | 157.84, 153.90, 147.32, 133.85, 129.98, 128.97, 127.27, 61.61, 42.98, 14.48, 14.42 |
5o | 10.11(brs, 1H, NH), 7.96—7.50(m, 4H, ClPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 3.99(t, J=7.02 Hz, 2H, CH2N), 1.83—1.78(m, 2H, CH2), 1.24(t, J=7.05 Hz, 3H, OCH2CH3), 0.86(t, J=7.35 Hz, 3H, CH3) | 157.78, 153.80, 147.73, 133.83, 129.96, 128.95, 127.27, 61.56, 49.28, 22.20, 14.46, 10.95 |
5p | 8.27(brs, 1H, NH), 7.99—7.35(m, 4H, ClPh), 6.06—5.96(m, 1H, =CH), 5.32—5.25(m, 2H, CH2 =), 4.80—4.77(m, 2H, CH2N), 4.26(q, J=7.14 Hz, 2H, OCH2), 1.31(t, J=7.11 Hz, 3H, CH3) | 158.51, 153.73, 147.44, 135.22, 131.33, 129.05, 128.68, 127.52, 119.08, 62.60, 51.94, 14.36 |
5q | 10.26(brs, 1H, NH), 8.35—8.31(m, 4H, NO2Ph), 4.18(q, J=7.08 Hz, 2H, OCH2), 4.10(q, J=7.20 Hz, 2H, CH2N), 1.40(t, J=7.20 Hz, 3H, OCH2CH3), 1.25(t, J=7.08 Hz, 3H, CH3) | 157.03, 153.78, 147.86, 147.76, 136.99, 126.53, 124.33, 61.69, 43.23, 14.49, 14.38 |
5r | 10.23(brs, 1H, NH), 8.34—8.16(m, 4H, NO2Ph), 4.17(q, J=7.08 Hz, 2H, OCH2), 4.03(t, J=7.02 Hz, 2H, CH2N), 1.84—1.80(m, 2H, CH2), 1.25(t, J=7.08 Hz, 3H, OCH2CH3), 0.87(t, J=7.35 Hz, 3H, CH3) | 156.99, 153.70, 148.28, 147.78, 136.98, 126.55, 124.35, 61.66, 49.50, 22.19, 14.47, 10.95 |
5s | 10.24(brs, 1H, NH), 8.35—8.17(m, 4H, NO2Ph), 4.18(q, J=7.05 Hz, 2H, OCH2), 4.08(t, J=7.11 Hz, 2H, CH2N), 1.82—1.78(m, 2H, CH2), 1.32—1.28(m, 2H, CH2), 1.26(t, J=7.11 Hz, 3H, OCH2CH3), 0.90(t, J=7.29 Hz, 3H, CH3) | 157.03, 153.76, 148.23, 147.79, 137.00, 126.58, 124.39, 61.72, 47.71, 30.83, 19.30, 14.52, 13.56 |
5t | 10.10(brs, 1H, NH), 7.99—7.25(m, 4H, FPh), 4.16(q, J=7.08 Hz, 2H, OCH2), 4.04(q, J=7.20 Hz, 2H, CH2N), 1.37(t, J=7.20 Hz, 3H, OCH2CH3), 1.25(t, J=7.08 Hz, 3H, CH3) | 164.43, 161.17, 157.99, 153.93, 147.20, 127.77, 127.66, 115.99, 115.70, 61.60, 42.90, 14.51, 14.47 |
5u | 10.09(brs, 1H, NH), 7.99—7.25(m, 4H, FPh), 4.16(q, J=7.02 Hz, 2H, OCH2), 3.98(t, J=7.08 Hz, 2H, CH2N), 1.83—1.79(m, 2H, CH2), 1.24(t, J=7.05 Hz, 3H, OCH2CH3), 0.86(t, J=7.32 Hz, 3H, CH3) | 164.45, 161.19, 157.97, 153.88, 147.65, 127.80, 127.69, 116.01, 115.72, 61.60, 49.24, 22.27, 14.52, 11.01 |
5v | 10.17(brs, 1H, NH), 7.99—7.26(m, 4H, FPh), 6.01—5.93(m, 1H, =CH), 5.25—5.15(m, 2H, CH2 =), 4.72—4.70(m, 2H, CH2N), 4.16(q, J=7.11 Hz, 2H, OCH2), 1.24(t, J=7.11 Hz, 3H, CH3) | 164.46, 161.20, 158.10, 153.72, 147.75, 132.39, 127.81, 127.53, 118.38, 115.97, 115.69, 61.59, 50.41, 14.47 |
5w | 10.09(brs, 1H, NH), 7.99—7.25(m, 4H, FPh), 4.16(q, J=7.11 Hz, 2H, OCH2), 4.01(t, J=7.11 Hz, 2H, CH2N), 1.80—1.75(m, 2H, CH2), 1.34—1.26(m, 2H, CH2), 1.24(t, J=7.08 Hz, 3H, OCH2CH3), 0.88(t, J=7.29 Hz, 3H, CH3) | 164.40, 161.15, 157.93, 153.85, 147.53, 127.76, 127.65, 115.95, 115.66, 61.54, 47.36, 30.80, 19.25, 14.48, 13.50 |
5x | 10.31(brs, 1H, NH), 8.34—8.16(m, 4H, NO2Ph), 6.03—5.94(m, 1H, =CH), 5.28—5.17(m, 2H, CH2 =), 4.77(d, J=5.73 Hz, 2H, CH2N), 4.17(q, J=7.11 Hz, 2H, OCH2), 1.25(t, J=7.08 Hz, 3H, CH3) | 157.13, 153.57, 148.37, 147.82, 136.82, 132.15, 126.59, 124.35, 118.69, 61.69, 50.67, 14.46 |
6a | 7.62—7.50(m, 5H, Ph), 4.21(q, J=7.21 Hz, 2H, OCH2), 3.98(q, J=7.08 Hz, 2H, OCH2), 3.95(t, J=7.07 Hz, 2H, CH2N), 1.75—1.71(m, 2H, CH2), 1.35—1.31(m, 2H, CH2), 1.18(t, J=7.09 Hz, 3H, OCH2CH3), 1.12(t, J=7.12 Hz, 3H, OCH2CH3), 0.91(t, J=7.30 Hz, 3H, CH3) | 160.00, 149.77, 147.33, 145.50, 131.14, 129.10, 128.68, 125.27, 65.45, 60.51, 46.32, 29.61, 19.24, 14.65, 13.54, 13.34 |
6b | 7.69—7.49(m, 5H, ClPh), 4.13(q, J=7.11 Hz, 2H, OCH2), 3.98(q, J=7.24 Hz, 2H, OCH2), 3.97(t, J=7.10 Hz, 2H, CH2N), 1.31(t, J=7.20 Hz, 3H, OCH2CH3), 1.17(t, J=7.09 Hz, 3H, OCH2CH3), 1.02(t, J=7.13 Hz, 3H, CH3) | 159.78, 148.90, 146.95, 143.01, 133.47, 133.07, 132.58, 129.51, 127.74, 125.68, 65.31, 60.57, 42.02, 14.66, 13.27, 13.16 |
6c | 7.51—6.96(m, 4H, OCH3Ph), 4.26(q, J=7.20 Hz, 2H, OCH2), 4.14(q, J=7.13 Hz, 2H, OCH2), 4.08(t, J=7.23 Hz, 2H, CH2N), 3.78(s, 3H, OCH3), 1.42(t, J=7.22 Hz, 3H, OCH2CH3), 1.32(t, J=7.17 Hz, 3H, OCH2CH3), 1.20(t, J=7.16 Hz, 3H, CH3) | 159.90, 157.04, 149.13, 147.45, 143.77, 133.11, 130.83, 121.07, 114.74, 111.35, 65.03, 60.47, 55.66, 41.87, 14.71, 13.48, 13.24 |
6d | 7.51—6.90(m, 4H, OCH3Ph), 6.03—5.93(m, 1H, =CH), 5.38—5.27(m, 2H, CH2 =), 4.65—4.62(m, 2H, CH2N), 4.26(q, J=7.20 Hz, 2H, OCH2), 4.14(t, J=7.12 Hz, 2H, OCH2), 3.77(s, 3H, OCH3), 1.31(t, J=7.11 Hz, 3H, OCH2CH3), 1.20(t, J=7.17 Hz, 3H, CH3) | 160.62, 157.20, 149.98, 147.57, 144.52, 132.54, 131.02, 130.61, 121.00, 119.48, 115.37, 110.34, 64.77, 61.23, 55.18, 49.32, 14.59, 13.45 |
6e | 7.54—7.05(m, 4H, OCH3Ph), 4.22(q, J=7.14 Hz, 2H, OCH2), 3.97(q, J=7.07 Hz, 2H, OCH2), 3.89(t, J=6.96 Hz, 2H, CH2N), 3.82(s, 3H, OCH3), 1.77—1.73(m, 2H, CH2), 1.82(t, J=7.08 Hz, 3H, OCH2CH3), 1.52(t, J=7.15 Hz, 3H, OCH2CH3), 0.90(t, J=7.36 Hz, 3H, CH3) | 161.40, 160.08, 149.89, 147.48, 145.48, 130.78, 117.18, 114.12, 65.40, 60.45, 55.53, 48.14, 21.05, 14.63, 13.40, 10.96 |
6f | 7.55—7.04(m, 4H, OCH3Ph), 5.99—5.88(m, 1H, =CH), 5.28—5.21(m, 2H, CH2 =), 4.57(d, J=5.55 Hz, 2H, CH2N), 4.22(q, J=7.14 Hz, 2H, OCH2), 3.98(t, J=7.08 Hz, 2H, OCH2), 3.82(s, 3H, OCH3), 1.20(t, J=7.08 Hz, 3H, OCH2CH3), 1.15(t, J=7.11 Hz, 3H, CH3) | 161.42, 159.99, 149.70, 147.43, 145.72, 131.52, 130.83, 118.69, 117.12, 114.13, 65.45, 60.52, 55.56, 48.81, 14.63, 13.42 |
6g | 7.61—7.26(m, 4H, ClPh), 4.32(q, J=7.17 Hz, 2H, OCH2), 4.16(q, J=7.14 Hz, 2H, OCH2), 4.02(t, J=7.41 Hz, 2H, CH2N), 1.85—1.80(m, 2H, CH2), 1.39—1.33(m, 2H, CH2), 1.32(t, J=7.11 Hz, 3H, OCH2CH3), 1.26(t, J=7.14 Hz, 3H, OCH2CH3), 0.95(t, J=7.29 Hz, 3H, CH3) | 161.01, 150.53, 147.53, 145.13, 137.39, 130.67, 128.68, 123.69, 65.55, 61.35, 47.02, 30.01, 19.70, 14.56, 13.54, 13.48 |
Compd. | Mortality(%) | Compd. | Mortality(%) | Compd. | Mortality(%) |
---|---|---|---|---|---|
5a | 94.6 | 5l | 36.0 | 5w | 94.2 |
5b | 90.2 | 5m | 44.2 | 5x | 95.7 |
5c | 48.7 | 5n | 52.3 | 6a | 93.2 |
5d | 57.1 | 5o | 69.4 | 6b | 83.2 |
5e | 50.5 | 5p | 76.3 | 6c | 91.0 |
5f | 91.0 | 5q | 93.9 | 6d | 81.6 |
5g | 57.1 | 5r | 89.1 | 6e | 94.9 |
5h | 63.8 | 5s | 92.7 | 6f | 83.2 |
5i | 67.9 | 5t | 90.2 | 6g | 79.5 |
5j | 93.1 | 5u | 93.1 | Imidachloprid | 100 |
5k | 71.4 | 5v | 91.3 |
Table 5 Corrected mortality of synthesized compounds to Myzus perscicae Sulzer at 500 μg/mL
Compd. | Mortality(%) | Compd. | Mortality(%) | Compd. | Mortality(%) |
---|---|---|---|---|---|
5a | 94.6 | 5l | 36.0 | 5w | 94.2 |
5b | 90.2 | 5m | 44.2 | 5x | 95.7 |
5c | 48.7 | 5n | 52.3 | 6a | 93.2 |
5d | 57.1 | 5o | 69.4 | 6b | 83.2 |
5e | 50.5 | 5p | 76.3 | 6c | 91.0 |
5f | 91.0 | 5q | 93.9 | 6d | 81.6 |
5g | 57.1 | 5r | 89.1 | 6e | 94.9 |
5h | 63.8 | 5s | 92.7 | 6f | 83.2 |
5i | 67.9 | 5t | 90.2 | 6g | 79.5 |
5j | 93.1 | 5u | 93.1 | Imidachloprid | 100 |
5k | 71.4 | 5v | 91.3 |
Compd. | LC50/(μg·mL-1) | Compd. | LC50/(μg·mL-1) |
---|---|---|---|
5a | 22.72 | 5u | 57.26 |
5b | 9.49 | 5v | 53.08 |
5f | 72.29 | 5w | 129.31 |
5j | 60.98 | 5x | 31.93 |
5q | 56.64 | 6a | 34.86 |
5r | 112.68 | 6c | 49.17 |
5s | 53.59 | 6e | 37.39 |
5t | 56.95 | Imidachloprid | 0.55 |
Table 6 Precision insecticidal activity of selected compounds against Myzus perscicae Sulzer(48 h, LC50)
Compd. | LC50/(μg·mL-1) | Compd. | LC50/(μg·mL-1) |
---|---|---|---|
5a | 22.72 | 5u | 57.26 |
5b | 9.49 | 5v | 53.08 |
5f | 72.29 | 5w | 129.31 |
5j | 60.98 | 5x | 31.93 |
5q | 56.64 | 6a | 34.86 |
5r | 112.68 | 6c | 49.17 |
5s | 53.59 | 6e | 37.39 |
5t | 56.95 | Imidachloprid | 0.55 |
Compd. | P.infestans | S.scleotiorum | A.mali | P.capsici | C.orbiculare | B.cinerea | ClgPa |
---|---|---|---|---|---|---|---|
5a | NA | NA | 3.6 | 0.8 | NA | NA | 3.93 |
5b | NA | NA | 3.9 | 1.1 | NA | NA | 4.35 |
5c | NA | 5.8 | 16.3 | 0.3 | NA | 4.2 | 3.64 |
5d | 0.3 | NA | 22.8 | 1.1 | 0.3 | 2.5 | 3.99 |
5e | NA | NA | 31.8 | NA | 8.4 | 5.8 | / |
5f | NA | NA | 7.7 | NA | NA | NA | / |
5g | NA | NA | 4.7 | NA | NA | NA | / |
5h | 0.3 | 4.0 | 22.6 | NA | 32.9 | 10.2 | / |
5i | 8.9 | 22.1 | 33.8 | 30.2 | 46.7 | NA | 4.20 |
5j | 13.5 | 11.1 | 41.2 | NA | 40.1 | 0.0 | 5.10 |
5k | 2.9 | 8.6 | 35.0 | 5.8 | 41.6 | 2.5 | 4.55 |
5l | NA | NA | 3.9 | NA | 2.1 | NA | 3.51 |
5m | 20.9 | 0.4 | 21.7 | NA | 13.5 | NA | 4.42 |
5n | 28.1 | 30.3 | 25.5 | 9.8 | 14.1 | 0.3 | 4.20 |
5o | 36.4 | 38.5 | 31.5 | NA | 16.2 | 26.6 | 4.68 |
5p | 33.0 | 23.2 | 33.5 | NA | 16.2 | 18.8 | 4.55 |
5q | 19.7 | 11.1 | 23.8 | 7.2 | 12.5 | 9.7 | / |
5r | 20.2 | 27.6 | 74.7 | 2.1 | 11.2 | 14.3 | / |
5s | 22.4 | 21.3 | 22.3 | 5.3 | 7.2 | 13.4 | / |
5t | 8.2 | 12.0 | 20.2 | 4.9 | 12.1 | 13.0 | 3.80 |
5u | 6.7 | 20.4 | 24.7 | NA | 5.8 | 9.2 | 4.28 |
5v | 9.4 | 15.9 | 20.5 | 5.9 | 7.5 | 10.8 | 4.15 |
5w | 24.0 | 24.0 | 29.5 | 2.5 | NA | 7.9 | 4.70 |
5x | 23.1 | 19.5 | 22.9 | 1.7 | NA | 1.2 | / |
6a | 19.2 | 24.1 | 29.4 | NA | 9.9 | NA | 4.65 |
6b | 14.3 | 9.1 | 6.5 | 4.8 | 2.1 | NA | 4.30 |
6c | 8.6 | 5.5 | 13.1 | 1.9 | NA | NA | 3.62 |
6d | 6.6 | 3.1 | 11.9 | NA | NA | NA | 3.97 |
6e | 7.4 | 13.3 | 11.0 | NA | 4.8 | NA | 4.10 |
6f | 7.7 | 6.6 | 2.7 | NA | 1.8 | NA | 3.97 |
6g | 46.4 | 52.0 | 46.0 | 18.8 | 24.9 | 36.6 | 5.20 |
Carbendazol | 100 | 100 | 49.5 | 33.8 | 74.1 | 76.1 | 1.29 |
Benomyl | 2.38 |
Table 7 Fungicidal activity of target compounds at 50 μg/mL in vitro inhibitory rate(%)
Compd. | P.infestans | S.scleotiorum | A.mali | P.capsici | C.orbiculare | B.cinerea | ClgPa |
---|---|---|---|---|---|---|---|
5a | NA | NA | 3.6 | 0.8 | NA | NA | 3.93 |
5b | NA | NA | 3.9 | 1.1 | NA | NA | 4.35 |
5c | NA | 5.8 | 16.3 | 0.3 | NA | 4.2 | 3.64 |
5d | 0.3 | NA | 22.8 | 1.1 | 0.3 | 2.5 | 3.99 |
5e | NA | NA | 31.8 | NA | 8.4 | 5.8 | / |
5f | NA | NA | 7.7 | NA | NA | NA | / |
5g | NA | NA | 4.7 | NA | NA | NA | / |
5h | 0.3 | 4.0 | 22.6 | NA | 32.9 | 10.2 | / |
5i | 8.9 | 22.1 | 33.8 | 30.2 | 46.7 | NA | 4.20 |
5j | 13.5 | 11.1 | 41.2 | NA | 40.1 | 0.0 | 5.10 |
5k | 2.9 | 8.6 | 35.0 | 5.8 | 41.6 | 2.5 | 4.55 |
5l | NA | NA | 3.9 | NA | 2.1 | NA | 3.51 |
5m | 20.9 | 0.4 | 21.7 | NA | 13.5 | NA | 4.42 |
5n | 28.1 | 30.3 | 25.5 | 9.8 | 14.1 | 0.3 | 4.20 |
5o | 36.4 | 38.5 | 31.5 | NA | 16.2 | 26.6 | 4.68 |
5p | 33.0 | 23.2 | 33.5 | NA | 16.2 | 18.8 | 4.55 |
5q | 19.7 | 11.1 | 23.8 | 7.2 | 12.5 | 9.7 | / |
5r | 20.2 | 27.6 | 74.7 | 2.1 | 11.2 | 14.3 | / |
5s | 22.4 | 21.3 | 22.3 | 5.3 | 7.2 | 13.4 | / |
5t | 8.2 | 12.0 | 20.2 | 4.9 | 12.1 | 13.0 | 3.80 |
5u | 6.7 | 20.4 | 24.7 | NA | 5.8 | 9.2 | 4.28 |
5v | 9.4 | 15.9 | 20.5 | 5.9 | 7.5 | 10.8 | 4.15 |
5w | 24.0 | 24.0 | 29.5 | 2.5 | NA | 7.9 | 4.70 |
5x | 23.1 | 19.5 | 22.9 | 1.7 | NA | 1.2 | / |
6a | 19.2 | 24.1 | 29.4 | NA | 9.9 | NA | 4.65 |
6b | 14.3 | 9.1 | 6.5 | 4.8 | 2.1 | NA | 4.30 |
6c | 8.6 | 5.5 | 13.1 | 1.9 | NA | NA | 3.62 |
6d | 6.6 | 3.1 | 11.9 | NA | NA | NA | 3.97 |
6e | 7.4 | 13.3 | 11.0 | NA | 4.8 | NA | 4.10 |
6f | 7.7 | 6.6 | 2.7 | NA | 1.8 | NA | 3.97 |
6g | 46.4 | 52.0 | 46.0 | 18.8 | 24.9 | 36.6 | 5.20 |
Carbendazol | 100 | 100 | 49.5 | 33.8 | 74.1 | 76.1 | 1.29 |
Benomyl | 2.38 |
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