Synthesis, Structural Characterization, Insecticidal and Fungicidal Activity of (1H-1,2,4-Triazol-5-yl)carbamates†

doi:10.7503/cjcu20160065

Abstract

Abstract:

A series of novel (1H-1,2,4-triazol-5-yl)carbamates(5 and 6) was synthesized via the method of combining the crucial sub-structures of carbamates and 1H-1,2,4-triazole-5-amines in one molecules. Their structures were characterized by nuclear magnetic resonance(NMR), infrared(IR) spectrometry, high resolution mass spectrometry(HRMS) and elemental analysis. The preliminary insecticidal activity assays indicated that the lethal rates of target compounds to Myzus persicae were good at the concentration of 500 μg/mL. And the lethal rate of several compounds was more than 90%. Further research of these compounds against Myzus persicae indicated that compound 5b showed considerably high activity with a LC₅₀ of 9.49 μg/mL, which confirmed that these compounds are valuable for further study. The preliminary fungicidal activity assays indicated that these compounds exhibited low fungicidal activity against tested fugi in vitro. At a dose of 50 μg/mL, only a few of compounds gave limited inhibition on mycelium growth. In addition, the structure-activity relationship was also discussed.

Key words: 1H-1,2,4-triazole-5-amine, Carbamate, Insecticidal activity, Fungicidal activity

CLC Number:

O626

TrendMD:

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^†[J]. Chem. J. Chinese Universities, 2016, 37(5): 892.

Figures/Tables 9

Fig.1 Structrue of compounds 1—3

Scheme 1 Design and synthesis of target compounds 5 and 6

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^[19])	4u	157—159
4b	121—123	4l	130—132(130—131^[19])	4v	107—109
4c	99—101(99—100^[19])	4m	118—120(118—119^[19])	4w	110—112
4d	101—103(101—102^[19])	4n	162—164(162—163^[19])	4x	213—215
4e	148—150(149—150^[19])	4o	151—153(151—152^[19])	4y	144—146(144—145^[19])
4f	149—151(148—149^[19])	4p	128—130(128—129^[19])	4z	190—192(190—191^[19])
4g	136—138(136—137^[19])	4q	254—256	4aa	141—143(141—142^[19])
4h	154—156(154—155^[19])	4r	227—229	4ab	115—117(115—116^[19])
4i	161—163(161—162^[19])	4s	236—238	4ac	108—110(108—109^[19])
4j	137—139(137—138^[19])	4t	156—158	4ad	148—150(142—144^[19])

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)

Table 3 Appearance, melting point, yield, elemental analysis and IR data of target compounds

Compd.	Appearance	m. p./℃	Yield(%)	Elemental analysis(%, calcd.)					IR(KBr), $ν ˙$ /cm^-1
Compd.	Appearance	m. p./℃	Yield(%)	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
5w^a	White powder	54—55	48				3194, 3067, 2962, 2932, 2876, 1742, 1609, 1567, 1469, 1431, 1249, 1226, 1060, 850, 755
5x^b	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
6g^c	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), $ν ˙$ /cm^-1
Compd.	Appearance	m. p./℃	Yield(%)	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
5w^a	White powder	54—55	48				3194, 3067, 2962, 2932, 2876, 1742, 1609, 1567, 1469, 1431, 1249, 1226, 1060, 850, 755
5x^b	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
6g^c	White powder	89—90	49				3439, 3091, 2983, 2937, 2899, 2875, 1778, 1647, 1587, 1442, 1370, 1321, 1265, 1204, 1100, 857, 730

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, CH), 5.25—5.14(m, 2H, CH₂ ), 4.73—4.70(m, 2H, CH₂N), 4.16(q, J=7.08 Hz, 2H, OCH₂), 1.24(t, J=7.05 Hz, 3H, CH₃)	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, CH), 5.25—5.14(m, 2H, CH₂ ), 4.73—4.70(m, 2H, CH₂N), 4.16(q, J=7.08 Hz, 2H, OCH₂), 1.24(t, J=7.05 Hz, 3H, CH₃)	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 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

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

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	ClgP^a
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

References 20

[1]	Velikordov A. V., Ionova V. A., Degtyarev O. V., Sukhenko L.T., Pharm. Chem.J., 2013, 46(12), 715—719
[2]	Ma H. J., Xie R. L., Zhao Q. F., Mei X. D., Ning J., J. Agric. FoodChem., 2010, 58(24), 12817—12821
[3]	Yang J. C., Ma S. C., Jiang M. F., Zhang X., Liu C. L., Agrochemicals Research and Application, 2009, 13(6), 1—5
	(杨吉春, 马士存, 姜美峰, 张茜, 刘长令. 农药研究与应用, 2009, 13(6), 1—5)
[4]	Hou C. Q., Li Z. L., Liu C. L., Pesticides, 2002, 41(6), 41—44
	(候春青, 李志念, 刘长令.农药, 2002, 41(6), 41—44)
[5]	Fan Z. J., Yang Z. K., Zhang H. K., Mi N., Wang H., Cai F., Zuo X., Zheng Q. X., Song H. B., J. Agric. FoodChem., 2010, 58(5), 2630—2636
[6]	Wang Z. J., Sun X. H., Liu Y. F., Chen B., Shen S. Q., Jin R. Y., Ma H. X., Chem. J. Chinese Universities,2015, 36(7), 1315—1320
	(王子剑, 孙晓红, 刘源发, 陈邦, 沈生强, 靳如意, 马海霞. 高等学校化学学报, 2015, 36(7), 1315—1320)
[7]	Cao X. F., Hu M., Zhang J., Li F., Yang Y. H., Liu D. L., Liu S. H., J. Agric. FoodChem., 2009, 57(15), 6914—6919
[8]	Wang B. L., Shi Y. X., Ma Y., Liu X. H., Li Y. H., Song H. B., Li B. J., Li Z. M., J. Agric. FoodChem., 2010, 58(9), 5515—5522
[9]	Cao X. F., Li F., Hu M., Lu W. C., Yu G., Liu S.H., J. Agric. FoodChem., 2008, 56(23), 11367—11375
[10]	Duan Z. F., Fu L., Li C. B., Chem. J. Chinese Universities,2015, 36(1), 102—109
	(段志芳, 付莉, 李充璧. 高等学校化学学报, 2015, 36(1), 102—109)
[11]	Li Y. D., Mao W. T., Fan Z. J., Li J. J., Fang Z., Ji X.T., Zong G. G., Li F. Y., Chem. Res. ChineseUniversities, 2014, 30(3), 390—395
[12]	XuL. Z., Bi W. Z., Shang Y. Q., Zhai Z. W., Yi X., Chem. Res. ChineseUniversities, 2008, 24(3), 299—302
[13]	Bayrak H., Demirbas A., Bektas H., Turk. J.Chem., 2010, 34, 835—846
[14]	Qian Y. M., Hamilton M., Sidduri. A., Gabriel S., Ren Y. L., Peng R. Q., Rama K., Narayannan A., Truitt T., Hamid R., Chen Y., J. Med.Chem., 2012, 55, 7920—7939
[15]	Colombano G., Albani C., Ottonello G., Ottonello G., Riberio A., ChemMedChem, 2015, 10, 380—395
[16]	Radwan A. M., El-Zemity S. R., Pest. Manag.Sci., 2001, 57, 707—712
[17]	Liu W.D., Deng Y., Lan Z. L., Wang X. G., Gao B. D., Chin. J. Pestic.Sci., 2004, 6(4), 13—17
	(刘卫东, 邓义, 兰支利, 王晓光. 高必达. 农药学学报, 2004, 6(4), 13—17)
[18]	Jian F. F., Xiao H. L., Zhu C. Y., Xu L. Z., J. Heterocyclic.Chem., 2006, 43, 925—929
[19]	Jia C.Q., Su W. C., Xu Y. J., Liu J. P., Qin Z. H.,Chin. J. Org. Chem., doi: 10.6023/cioc2015/0021
	(贾长青, 苏旺苍, 徐彦军, 刘吉平, 覃兆海. 有机化学, doi10.6023/cioc2015/0021)
[20]	Raymond M., Cah. Orstom Ser. Ent. Med. Parasitol., 1985, 23, 117—121