Chem. J. Chinese Universities ›› 2016, Vol. 37 ›› Issue (9): 1649.doi: 10.7503/cjcu20160145
• Organic Chemistry • Previous Articles Next Articles
LI Lin1,2, LI Miao3, CHAI Baoshan4, YANG Jichun3, SONG Yuquan3, LIU Changling3,*()
Received:
2016-03-11
Online:
2016-09-10
Published:
2016-08-17
Contact:
LIU Changling
E-mail:liuchangling@vip.163.com
CLC Number:
TrendMD:
LI Lin, LI Miao, CHAI Baoshan, YANG Jichun, SONG Yuquan, LIU Changling. Design, Synthesis and Biological Activity of Novel Substituted Diamides Derivatives Containing Thiophene Ring[J]. Chem. J. Chinese Universities, 2016, 37(9): 1649.
Scheme 1 Synthetic routes of compounds 1—3 Reagents and conditions: a. S, NHEt2, CH3CN, 50 ℃, 1—5 h; b. NaOH, CH3CH2OH/H2O, reflux, 2 h; c. CH3SO2Cl, pyridine, CH3CN, 2 h; d. R1R2NH, CH3CN, 1—6 h.
Compd. | Yield (%) | m.p./℃ | Elemental analysis(%, calcd.) | IR, | ||
---|---|---|---|---|---|---|
C | H | N | ||||
1a | 23 | 221—222 | 42.38 (43.56) | 3.44 (3.23) | 15.03 (14.94) | 3460(m, N—H), 2980, 2960(m, C—H), 1620(s, C=O), 1565, 1455(m, aromatic rings), 1450, 1360(m, C—H), 1320(s, C—O), 830, 750, 720(m, Ph-H) |
1b | 29 | 238—239 | 45.65 (44.78) | 3.50 (3.55) | 14.34 (14.51) | 3440(m, N—H), 2970, 2940(m, C—H), 1610(s, C=O), 1555, 1440(m, aromatic rings), 1440, 1370(m, C—H), 1310(s, C—O), 810, 770, 730(m, Ph-H) |
1c | 21 | 224—225 | 46.524 (45.9) | 3.73 (3.86) | 14.02 (14.10) | 3450(m, N—H), 2980(m, C—H), 1620(s, C=O), 1560, 1440(m, aromatic rings), 1450, 1370(m, C—H), 1330(s, C—O), 820, 760, 700(m, Ph-H) |
1d | 25 | 238—239 | 45.43 (46.12) | 3.58 (3.46) | 14.27 (14.15) | 3440(m, N—H), 2950(m, C—H), 1600(s, C=O), 1555, 1435(m, aromatic rings), 1450, 1360(m, C—H), 1320(s, C—O), 800, 770, 720(m, Ph-H) |
1e | 32 | 217—218 | 47.36 (48.12) | 3.55 (3.56) | 16.63 (16.51) | 3460(m, N—H), 2975, 2960(m, C—H), 1620(s, C=O), 1560, 1450(m, aromatic rings), 1470, 1370(m, C—H), 1330(s, C—O), 830, 760, 690(m, Ph-H) |
1f | 58 | 235—236 | 49.28 (49.32) | 3.89 (3.91) | 15.99 (15.98) | 3440(m, N—H), 2970(m, C—H), 1610(s, C=O), 1565, 1455(m, aromatic rings), 1460, 1350(m, C—H), 1310(s, C—O), 820, 750, 710(m, Ph-H) |
1g | 41 | 217—218 | 51.78 (50.45) | 4.16 (4.23) | 15.38 (15.48) | 3430(m, N—H), 2980, 2960(m, C—H), 1630(s, C=O), 1570, 1460(m, aromatic rings), 1470, 1365(m, C—H), 1320(s, C—O), 820, 770, 730(m, Ph-H) |
1h | 50 | 257—258 | 51.11 (50.01) | 3.82 (3.99) | 14.50 (14.58) | 3420(m, N—H), 2980, 2960(m, C—H), 1600(s, C=O), 1550, 1440(m, aromatic rings), 1440, 1370(m, C—H), 1300(s, C—O), 800, 760, 740(m, Ph-H) |
2a | 25 | 170—171 | 57.84 (56.64) | 4.67 (4.75) | 13.86 (13.91) | 3420(m, N—H), 2980, 2960(m, C—H), 1600(s, C=O), 1550, 1440(m, aromatic rings), 1440, 1370(m, C—H), 1300(s, C—O), 800, 760, 740(m, Ph-H) |
2b | 38 | 175—176 | 56.90 (57.62) | 5.21 (5.08) | 13.52 (13.44) | 3440(m, N—H), 2980, 2950(m, C—H), 1620(s, C=O), 1530(m, aromatic rings), 1420, 1350(m, C—H), 1330(s, C—O), 820, 780, 720(m, Ph-H) |
2c | 30 | 234—235 | 57.46 (58.53) | 5.44 (5.38) | 13.15 (13.00) | 3430(m, N—H), 2960(m, C—H), 1610(s, C=O), 1540(m, aromatic rings), 1440, 1370(m, C—H), 1300(s, C—O), 800, 760, 740(m, Ph-H) |
2d | 40 | 245—246 | 57.69 (58.80) | 5.02 (4.94) | 13.13 (13.06) | 3450(m, N—H), 2980(s, C—H), 1620(s, C=O), 1520(s, aromatic rings), 1450, 1390(m, C—H), 1220, 1200(s, C—O), 840, 760(s, Ph-H) |
3a | 52 | 127—128 | 54.63 (53.93) | 4.18 (4.24) | 7.78 (7.86) | 3440(m, N—H), 2970(m, C—H), 1670(s, C=O), 1620, 1560, 1510(s, aromatic rings), 1400, 1310(m, C—H), 1130(s, C—F), 780, 710(m, Ph-H) |
3b | 50 | 185—186 | 56.87 (55.13) | 4.57 (4.63) | 7.42 (7.56) | 3430(m, N—H), 2950(m, C—H), 1660(s, C=O), 1610, 1550, 1500(s, aromatic rings), 1410, 1320(m, C—H), 1120(s, C—F), 820, 790, 700(m, Ph-H) |
3c | 52 | 147—148 | 55.30 (56.24) | 5.07 (4.98) | 7.35 (7.29) | 3440(m, N—H), 2960(m, C—H), 1670(s, C=O), 1600, 1550(s, aromatic rings), 1420, 1320(m, C—H), 1110(s, C—F), 760, 700(m, Ph-H) |
3d | 58 | 151—152 | 56.58 (56.54) | 4.49 (4.48) | 7.34 (7.33) | 3420(m, N—H), 2970(m, C—H), 1650(s, C=O), 1620, 1540(s, aromatic rings), 1430, 1320(m, C—H), 1130(s, C—F), 830, 780, 720(m, Ph-H) |
3e | 33 | 187—188 | 55.90 (55.33) | 4.71 (4.64) | 6.68 (6.79) | 3430(m, N—H), 2950(m, C—H), 1660(s, C=O), 1630, 1580, 1520(s, aromatic rings), 1410, 1300(m, C—H), 1120(s, C—F), 800, 770, 710(m, Ph-H) |
Table 1 Yields, melting points, elemental analysis and IR data of compounds 1—3
Compd. | Yield (%) | m.p./℃ | Elemental analysis(%, calcd.) | IR, | ||
---|---|---|---|---|---|---|
C | H | N | ||||
1a | 23 | 221—222 | 42.38 (43.56) | 3.44 (3.23) | 15.03 (14.94) | 3460(m, N—H), 2980, 2960(m, C—H), 1620(s, C=O), 1565, 1455(m, aromatic rings), 1450, 1360(m, C—H), 1320(s, C—O), 830, 750, 720(m, Ph-H) |
1b | 29 | 238—239 | 45.65 (44.78) | 3.50 (3.55) | 14.34 (14.51) | 3440(m, N—H), 2970, 2940(m, C—H), 1610(s, C=O), 1555, 1440(m, aromatic rings), 1440, 1370(m, C—H), 1310(s, C—O), 810, 770, 730(m, Ph-H) |
1c | 21 | 224—225 | 46.524 (45.9) | 3.73 (3.86) | 14.02 (14.10) | 3450(m, N—H), 2980(m, C—H), 1620(s, C=O), 1560, 1440(m, aromatic rings), 1450, 1370(m, C—H), 1330(s, C—O), 820, 760, 700(m, Ph-H) |
1d | 25 | 238—239 | 45.43 (46.12) | 3.58 (3.46) | 14.27 (14.15) | 3440(m, N—H), 2950(m, C—H), 1600(s, C=O), 1555, 1435(m, aromatic rings), 1450, 1360(m, C—H), 1320(s, C—O), 800, 770, 720(m, Ph-H) |
1e | 32 | 217—218 | 47.36 (48.12) | 3.55 (3.56) | 16.63 (16.51) | 3460(m, N—H), 2975, 2960(m, C—H), 1620(s, C=O), 1560, 1450(m, aromatic rings), 1470, 1370(m, C—H), 1330(s, C—O), 830, 760, 690(m, Ph-H) |
1f | 58 | 235—236 | 49.28 (49.32) | 3.89 (3.91) | 15.99 (15.98) | 3440(m, N—H), 2970(m, C—H), 1610(s, C=O), 1565, 1455(m, aromatic rings), 1460, 1350(m, C—H), 1310(s, C—O), 820, 750, 710(m, Ph-H) |
1g | 41 | 217—218 | 51.78 (50.45) | 4.16 (4.23) | 15.38 (15.48) | 3430(m, N—H), 2980, 2960(m, C—H), 1630(s, C=O), 1570, 1460(m, aromatic rings), 1470, 1365(m, C—H), 1320(s, C—O), 820, 770, 730(m, Ph-H) |
1h | 50 | 257—258 | 51.11 (50.01) | 3.82 (3.99) | 14.50 (14.58) | 3420(m, N—H), 2980, 2960(m, C—H), 1600(s, C=O), 1550, 1440(m, aromatic rings), 1440, 1370(m, C—H), 1300(s, C—O), 800, 760, 740(m, Ph-H) |
2a | 25 | 170—171 | 57.84 (56.64) | 4.67 (4.75) | 13.86 (13.91) | 3420(m, N—H), 2980, 2960(m, C—H), 1600(s, C=O), 1550, 1440(m, aromatic rings), 1440, 1370(m, C—H), 1300(s, C—O), 800, 760, 740(m, Ph-H) |
2b | 38 | 175—176 | 56.90 (57.62) | 5.21 (5.08) | 13.52 (13.44) | 3440(m, N—H), 2980, 2950(m, C—H), 1620(s, C=O), 1530(m, aromatic rings), 1420, 1350(m, C—H), 1330(s, C—O), 820, 780, 720(m, Ph-H) |
2c | 30 | 234—235 | 57.46 (58.53) | 5.44 (5.38) | 13.15 (13.00) | 3430(m, N—H), 2960(m, C—H), 1610(s, C=O), 1540(m, aromatic rings), 1440, 1370(m, C—H), 1300(s, C—O), 800, 760, 740(m, Ph-H) |
2d | 40 | 245—246 | 57.69 (58.80) | 5.02 (4.94) | 13.13 (13.06) | 3450(m, N—H), 2980(s, C—H), 1620(s, C=O), 1520(s, aromatic rings), 1450, 1390(m, C—H), 1220, 1200(s, C—O), 840, 760(s, Ph-H) |
3a | 52 | 127—128 | 54.63 (53.93) | 4.18 (4.24) | 7.78 (7.86) | 3440(m, N—H), 2970(m, C—H), 1670(s, C=O), 1620, 1560, 1510(s, aromatic rings), 1400, 1310(m, C—H), 1130(s, C—F), 780, 710(m, Ph-H) |
3b | 50 | 185—186 | 56.87 (55.13) | 4.57 (4.63) | 7.42 (7.56) | 3430(m, N—H), 2950(m, C—H), 1660(s, C=O), 1610, 1550, 1500(s, aromatic rings), 1410, 1320(m, C—H), 1120(s, C—F), 820, 790, 700(m, Ph-H) |
3c | 52 | 147—148 | 55.30 (56.24) | 5.07 (4.98) | 7.35 (7.29) | 3440(m, N—H), 2960(m, C—H), 1670(s, C=O), 1600, 1550(s, aromatic rings), 1420, 1320(m, C—H), 1110(s, C—F), 760, 700(m, Ph-H) |
3d | 58 | 151—152 | 56.58 (56.54) | 4.49 (4.48) | 7.34 (7.33) | 3420(m, N—H), 2970(m, C—H), 1650(s, C=O), 1620, 1540(s, aromatic rings), 1430, 1320(m, C—H), 1130(s, C—F), 830, 780, 720(m, Ph-H) |
3e | 33 | 187—188 | 55.90 (55.33) | 4.71 (4.64) | 6.68 (6.79) | 3430(m, N—H), 2950(m, C—H), 1660(s, C=O), 1630, 1580, 1520(s, aromatic rings), 1410, 1300(m, C—H), 1120(s, C—F), 800, 770, 710(m, Ph-H) |
Compd. | 1H NMR(300 MHz), δ |
---|---|
1a | 13.14(s, 1H, NH), 8.49(dd, J=1.5, 4.5 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.5, 1.8 Hz, 1H, pyridin-4-H), 7.42(dd, J=4.5, 8.4 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 6.11(s, 1H, NH), 3.03(d, J=3.0 Hz, 3H, CH3), 2.30(s, 3H, thiophene-5-CH3), 2.25(s, 3H, thiophene-4-CH3) |
1b | 11.97(s, 1H, NH), 8.52(dd, J=1.5, 4.8 Hz, 1H, pyridin-6-H), 8.23(dd, J=1.5, 4.8 Hz, 1H, pyridin-4-H), 7.66(dd, J=4.8, 8.4 Hz, 1H, pyridin-5-H), 7.34(s, 1H, pyrazole), 2.87(s, 3H, CH3), 2.79(s, 3H, CH3), 2.21(s, 3H, thiophene-5-CH3), 1.91(s, 3H, thiophene-4-CH3) |
1c | 13.11(s, 1H, NH), 8.49(dd, J=1.8, 5.1 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.8, 5.1 Hz, 1H, pyridin-4-H), 7.42(dd, J=5.1, 8.1 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 5.89(br, 1H, NH), 4.28(m, 1H, CH), 2.27(s, 3H, thiophene-5-CH3), 2.23(s, 3H, thiophene-4-CH3), 1.28(d, J=5.1 Hz, 6H, 2CH3) |
1d | 11.91(s, 1H, NH), 8.54(dd, J=1.2, 4.8 Hz, 1H, pyridin-6-H), 8.25(dd, J=1.5, 4.5 Hz, 1H, pyridin-4-H), 7.68(dd, J=4.8, 8.1 Hz, 1H, pyridin-5-H), 7.29(s, 1H, pyrazole), 6.98(s, 1H, NH), 2.81(m, 1H, CH), 2.10(s, 3H, thiophene-5-CH3), 2.06(s, 3H, thiophene-4-CH3), 0.70(m, 2H, CH2), 0.55(m, 2H, CH2) |
1e | 13.14(s, 1H, NH), 8.49(dd, J=1.5, 5.1 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.2, 5.1 Hz, 1H, pyridin-4-H), 7.42(dd, J=4.8, 8.7 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 6.11(s, 1H, NH), 3.03(d, J=3.3 Hz, 3H, CH3), 2.30(s, 3H, thiophene-5-CH3), 2.25(s, 3H, thiophene-4-CH3) |
1f | 10.45(s, 1H, NH), 8.50(dd, J=1.8, 4.5 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.8, 4.8 Hz,1H, pyridin-4-H), 7.42(dd, J=4.5, 8.4 Hz, 1H, pyridin-5-H), 6.99(s, 1H, pyrazole-H), 3.03(s, 6H, 2CH3), 2.23(s, 3H, thiophene-5-CH3), 2.03(s, 3H, thiophene-4-CH3) |
1g | 13.11(s, 1H, NH), 8.49(dd, J=1.2, 5.1 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.5, 5.1 Hz, 1H, pyridin-4-H), 7.42(dd, J=5.1, 8.7 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 5.89(br, 1H, NH), 4.28(m, 1H, CH), 2.27(s, 3H, thiophene-5-CH3), 2.23(s, 3H, thiophene-4-CH3), 1.28(d, J=6.9 Hz, 6H, 2CH3) |
1h | 10.43(s, 1H, NH), 8.49(dd, J=1.5, 4.8 Hz, 1H, pyridin-6-H), 7.91(dd, J=1.2, 4.8 Hz, 1H, pyridin-4-H), 7.43(dd, J=4.8, 8.4 Hz, 1H, pyridin-5-H), 6.96(s, 1H, pyrazole-H), 3.71(m, 4H, morpholine-2,6-2CH2), 3.54(m, 4H, morpholine-3,5-2CH2), 2.22(s, 3H, thiophene-5-CH3), 2.04(s, 3H, thiophene-4-CH3) |
2a | 8.33(s, 1H, pyrazole-H), 7.70(s, 1H, NH), 7.65(d, J=6.6 Hz, 2H, Ph-2,6-2H), 7.47(d, J=6.6 Hz, 2H, Ph-3,5-2H), 3.93(s, 3H, pyrazole-CH3), 2.93(s, 3H, CH3), 2.23(s, 3H, thiophene-5-CH3), 1.92(s, 3H, thiophene-4-CH3) |
2b | 8.23(s, 1H, pyrazole-H), 7.71(s, 1H, NH), 7.68(d, J=6.9 Hz, 2H, Ph-2,6-2H), 7.47(d, J=6.9 Hz, 2H, Ph-3,5-2H), 3.93(s, 3H, pyrazole-CH3), 2.83(s, 6H, 2CH3), 2.23(s, 3H, thiophene-5-CH3), 1.92(s, 3H, thiophene-4-CH3) |
2c | 12.01(s, 1H, NH), 8.31(s, 1H, pyrazole-H), 7.68(d, J=6.3 Hz, 2H, Ph-2,6-2H), 7.47(d, J=6.3 Hz, 2H, Ph-3,5-2H), 3.96(m, 1H, CH), 3.95(s, 3H, pyrazole-CH3), 2.23(s, 3H, thiophene-5-CH3), 2.15(s, 3H, thiophene-4-CH3), 1.13(s, 3H, CH3), 1.11(s, 3H, CH3) |
2d | 8.29(s, 1H, pyrazole-H), 7.71(s, 1H, NH), 7.66(d, J=6.6 Hz, 2H, Ph-2,6-2H), 7.43(d, J=6.6 Hz, 2H, Ph-3,5-2H), 3.93(s, 3H, pyrazole-CH3), 2.32(m, 1H, CH), 2.23(s, 3H, thiophene-5-CH3), 1.92(s, 3H, thiophene-4-CH3), 0.83(m, 4H, 2CH2) |
3a | 12.40(s, 1H, NH), 7.77—7.58(m, 4H, Ph), 6.05(s, 1H, NH), 2.95(d, J=3.0 Hz, 3H, CH3), 2.32(s, 6H, thiophene-2CH3) |
3b | 9.19(s, 1H, NH), 7.75—7.59(m, 4H, Ph), 3.02(s, 6H, 2CH3), 2.32(s, 3H, thiophene-5-CH3), 2.06(s, 3H, thiophene-4-CH3) |
3c | 12.31(s, 1H, NH), 7.76—7.58(m, 4H, Ph), 5.85(br, 1H, NH), 4.19(m, 1H, CH), 2.31(s, 6H, thiophene-2CH3), 1.24(d, J=5.1 Hz, 6H, 2CH3) |
3d | 12.39(s, 1H, NH), 7.77—7.58(m, 4H, Ph), 6.19(s, 1H, NH), 2.80(m, 1H, CH), 2.31(s, 3H, thiophene-5-CH3), 2.26(s, 3H, thiophene-4-CH3), 0.85(m, 4H, 2CH2) |
3e | 9.26(s, 1H, NH), 7.76—7.64(m, 4H, Ph), 3.78—3.46(m, 8H, morpholine), 2.31(s, 3H, thiophene-5-CH3), 2.07(s, 3H, thiophene-4-CH3) |
Table 2 1H NMR data of compounds 1—3*
Compd. | 1H NMR(300 MHz), δ |
---|---|
1a | 13.14(s, 1H, NH), 8.49(dd, J=1.5, 4.5 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.5, 1.8 Hz, 1H, pyridin-4-H), 7.42(dd, J=4.5, 8.4 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 6.11(s, 1H, NH), 3.03(d, J=3.0 Hz, 3H, CH3), 2.30(s, 3H, thiophene-5-CH3), 2.25(s, 3H, thiophene-4-CH3) |
1b | 11.97(s, 1H, NH), 8.52(dd, J=1.5, 4.8 Hz, 1H, pyridin-6-H), 8.23(dd, J=1.5, 4.8 Hz, 1H, pyridin-4-H), 7.66(dd, J=4.8, 8.4 Hz, 1H, pyridin-5-H), 7.34(s, 1H, pyrazole), 2.87(s, 3H, CH3), 2.79(s, 3H, CH3), 2.21(s, 3H, thiophene-5-CH3), 1.91(s, 3H, thiophene-4-CH3) |
1c | 13.11(s, 1H, NH), 8.49(dd, J=1.8, 5.1 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.8, 5.1 Hz, 1H, pyridin-4-H), 7.42(dd, J=5.1, 8.1 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 5.89(br, 1H, NH), 4.28(m, 1H, CH), 2.27(s, 3H, thiophene-5-CH3), 2.23(s, 3H, thiophene-4-CH3), 1.28(d, J=5.1 Hz, 6H, 2CH3) |
1d | 11.91(s, 1H, NH), 8.54(dd, J=1.2, 4.8 Hz, 1H, pyridin-6-H), 8.25(dd, J=1.5, 4.5 Hz, 1H, pyridin-4-H), 7.68(dd, J=4.8, 8.1 Hz, 1H, pyridin-5-H), 7.29(s, 1H, pyrazole), 6.98(s, 1H, NH), 2.81(m, 1H, CH), 2.10(s, 3H, thiophene-5-CH3), 2.06(s, 3H, thiophene-4-CH3), 0.70(m, 2H, CH2), 0.55(m, 2H, CH2) |
1e | 13.14(s, 1H, NH), 8.49(dd, J=1.5, 5.1 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.2, 5.1 Hz, 1H, pyridin-4-H), 7.42(dd, J=4.8, 8.7 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 6.11(s, 1H, NH), 3.03(d, J=3.3 Hz, 3H, CH3), 2.30(s, 3H, thiophene-5-CH3), 2.25(s, 3H, thiophene-4-CH3) |
1f | 10.45(s, 1H, NH), 8.50(dd, J=1.8, 4.5 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.8, 4.8 Hz,1H, pyridin-4-H), 7.42(dd, J=4.5, 8.4 Hz, 1H, pyridin-5-H), 6.99(s, 1H, pyrazole-H), 3.03(s, 6H, 2CH3), 2.23(s, 3H, thiophene-5-CH3), 2.03(s, 3H, thiophene-4-CH3) |
1g | 13.11(s, 1H, NH), 8.49(dd, J=1.2, 5.1 Hz, 1H, pyridin-6-H), 7.89(dd, J=1.5, 5.1 Hz, 1H, pyridin-4-H), 7.42(dd, J=5.1, 8.7 Hz, 1H, pyridin-5-H), 6.98(s, 1H, pyrazole-H), 5.89(br, 1H, NH), 4.28(m, 1H, CH), 2.27(s, 3H, thiophene-5-CH3), 2.23(s, 3H, thiophene-4-CH3), 1.28(d, J=6.9 Hz, 6H, 2CH3) |
1h | 10.43(s, 1H, NH), 8.49(dd, J=1.5, 4.8 Hz, 1H, pyridin-6-H), 7.91(dd, J=1.2, 4.8 Hz, 1H, pyridin-4-H), 7.43(dd, J=4.8, 8.4 Hz, 1H, pyridin-5-H), 6.96(s, 1H, pyrazole-H), 3.71(m, 4H, morpholine-2,6-2CH2), 3.54(m, 4H, morpholine-3,5-2CH2), 2.22(s, 3H, thiophene-5-CH3), 2.04(s, 3H, thiophene-4-CH3) |
2a | 8.33(s, 1H, pyrazole-H), 7.70(s, 1H, NH), 7.65(d, J=6.6 Hz, 2H, Ph-2,6-2H), 7.47(d, J=6.6 Hz, 2H, Ph-3,5-2H), 3.93(s, 3H, pyrazole-CH3), 2.93(s, 3H, CH3), 2.23(s, 3H, thiophene-5-CH3), 1.92(s, 3H, thiophene-4-CH3) |
2b | 8.23(s, 1H, pyrazole-H), 7.71(s, 1H, NH), 7.68(d, J=6.9 Hz, 2H, Ph-2,6-2H), 7.47(d, J=6.9 Hz, 2H, Ph-3,5-2H), 3.93(s, 3H, pyrazole-CH3), 2.83(s, 6H, 2CH3), 2.23(s, 3H, thiophene-5-CH3), 1.92(s, 3H, thiophene-4-CH3) |
2c | 12.01(s, 1H, NH), 8.31(s, 1H, pyrazole-H), 7.68(d, J=6.3 Hz, 2H, Ph-2,6-2H), 7.47(d, J=6.3 Hz, 2H, Ph-3,5-2H), 3.96(m, 1H, CH), 3.95(s, 3H, pyrazole-CH3), 2.23(s, 3H, thiophene-5-CH3), 2.15(s, 3H, thiophene-4-CH3), 1.13(s, 3H, CH3), 1.11(s, 3H, CH3) |
2d | 8.29(s, 1H, pyrazole-H), 7.71(s, 1H, NH), 7.66(d, J=6.6 Hz, 2H, Ph-2,6-2H), 7.43(d, J=6.6 Hz, 2H, Ph-3,5-2H), 3.93(s, 3H, pyrazole-CH3), 2.32(m, 1H, CH), 2.23(s, 3H, thiophene-5-CH3), 1.92(s, 3H, thiophene-4-CH3), 0.83(m, 4H, 2CH2) |
3a | 12.40(s, 1H, NH), 7.77—7.58(m, 4H, Ph), 6.05(s, 1H, NH), 2.95(d, J=3.0 Hz, 3H, CH3), 2.32(s, 6H, thiophene-2CH3) |
3b | 9.19(s, 1H, NH), 7.75—7.59(m, 4H, Ph), 3.02(s, 6H, 2CH3), 2.32(s, 3H, thiophene-5-CH3), 2.06(s, 3H, thiophene-4-CH3) |
3c | 12.31(s, 1H, NH), 7.76—7.58(m, 4H, Ph), 5.85(br, 1H, NH), 4.19(m, 1H, CH), 2.31(s, 6H, thiophene-2CH3), 1.24(d, J=5.1 Hz, 6H, 2CH3) |
3d | 12.39(s, 1H, NH), 7.77—7.58(m, 4H, Ph), 6.19(s, 1H, NH), 2.80(m, 1H, CH), 2.31(s, 3H, thiophene-5-CH3), 2.26(s, 3H, thiophene-4-CH3), 0.85(m, 4H, 2CH2) |
3e | 9.26(s, 1H, NH), 7.76—7.64(m, 4H, Ph), 3.78—3.46(m, 8H, morpholine), 2.31(s, 3H, thiophene-5-CH3), 2.07(s, 3H, thiophene-4-CH3) |
Compd. | Mortality(%) | |
---|---|---|
600 mg/L | 20 mg/L | |
1a | 100 | 70 |
1b | 100 | 40 |
1c | 100 | 50 |
1d | 100 | 30 |
1e | 100 | 60 |
1f | 100 | 50 |
1g | 100 | 50 |
1h | 100 | 20 |
Chlomtraniliprole | 100 | 100 |
Table 3 Insecticidal activity against Plutella xylostella of the target compounds 1
Compd. | Mortality(%) | |
---|---|---|
600 mg/L | 20 mg/L | |
1a | 100 | 70 |
1b | 100 | 40 |
1c | 100 | 50 |
1d | 100 | 30 |
1e | 100 | 60 |
1f | 100 | 50 |
1g | 100 | 50 |
1h | 100 | 20 |
Chlomtraniliprole | 100 | 100 |
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