Chem. J. Chinese Universities ›› 2020, Vol. 41 ›› Issue (4): 716.doi: 10.7503/cjcu20190504
• Organic Chemistry • Previous Articles Next Articles
LI Kangming1,LI Yansai1,YI Yangjie1,XU Leitao1,YE Jiao1,OU Xiaoming2,LI Jianming2,HU Aixi1,*()
Received:
2019-09-27
Online:
2020-04-10
Published:
2020-02-07
Contact:
Aixi HU
E-mail:axhu@hnu.edu.cn
Supported by:
CLC Number:
TrendMD:
LI Kangming, LI Yansai, YI Yangjie, XU Leitao, YE Jiao, OU Xiaoming, LI Jianming, HU Aixi. Design, Synthesis and Biological Activity of 5-Pyrazole Carboxamides †[J]. Chem. J. Chinese Universities, 2020, 41(4): 716.
Compd. | Reaction time/h | Feature | m. p./℃ | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
A1 | 4.0 | Grey solid | 148—149 | 68.8 | 364.1012(364.1310) |
A2 | 1.0 | White solid | 149—150 | 66.0 | 378.1209(378.1507) |
A3 | 1.0 | White solid | 157—158 | 59.5 | 392.1405(392.1707) |
A4 | 0.5 | Yellow solid | 138—139 | 61.4 | 440.0810(440.1714) |
A5 | 0.5 | White solid | 173—174 | 32.7 | 522.1002(522.0701) |
A6 | 8.0 | Yellow solid | 250—252 | 48.2 | 491.0907(491.0421) |
Compd. | Reaction time/h | Feature | m. p./℃ | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
A1 | 4.0 | Grey solid | 148—149 | 68.8 | 364.1012(364.1310) |
A2 | 1.0 | White solid | 149—150 | 66.0 | 378.1209(378.1507) |
A3 | 1.0 | White solid | 157—158 | 59.5 | 392.1405(392.1707) |
A4 | 0.5 | Yellow solid | 138—139 | 61.4 | 440.0810(440.1714) |
A5 | 0.5 | White solid | 173—174 | 32.7 | 522.1002(522.0701) |
A6 | 8.0 | Yellow solid | 250—252 | 48.2 | 491.0907(491.0421) |
Compd. | Reaction time/h | Feature | m. p./℃ | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
B1 | 4 | White solid | 177—179 | 28.1 | 447.0534(447.1229) |
B2 | 10 | White solid | 185—187 | 30.9 | 461.0247(461.1349) |
B3 | 10 | White solid | 135—138 | 31.6 | 560.0925(560.0139) |
B4 | 10 | White solid | 218—220 | 52.4 | 574.0826(574.0229) |
Compd. | Reaction time/h | Feature | m. p./℃ | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
B1 | 4 | White solid | 177—179 | 28.1 | 447.0534(447.1229) |
B2 | 10 | White solid | 185—187 | 30.9 | 461.0247(461.1349) |
B3 | 10 | White solid | 135—138 | 31.6 | 560.0925(560.0139) |
B4 | 10 | White solid | 218—220 | 52.4 | 574.0826(574.0229) |
Compd. | Reaction time/h | Feature | m. p./℃ | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
C1 | 8 | White solid | 126—128 | 43.6 | 327.1037(327.0640) |
C2 | 16 | White solid | 151—152 | 69.4 | 356.0103(356.0902) |
C3 | 4 | White solid | 126—128 | 62.0 | 357.0416(357.0717) |
C4 | 4 | Grey solid | 164—166 | 44.2 | 394.0312(394.1113) |
C5 | 4 | Grey solid | 177—179 | 33.5 | 432.0509(432.9812) |
C6 | 5 | White solid | 92—94 | 58.6 | 357.0615(357.0718) |
C7 | 4 | Yellow solid | 166—168 | 35.6 | 447.0609(447.1213) |
C8 | 10 | White solid | 174—176 | 42.6 | 461.0913(461.1319) |
C9 | 4 | White solid | 220—222 | 57.3 | 470.0309(469.9612) |
C10 | 6 | White solid | 222—224 | 52.1 | 507.0629(507.0031) |
C11 | 4 | White solid | 147—150 | 40.7 | 470.0425(469.9617) |
C12 | 10 | White solid | 158—160 | 50.2 | 560.0523(560.0121) |
C13 | 10 | White solid | 131—133 | 63.4 | 574.0009(574.0213) |
Compd. | Reaction time/h | Feature | m. p./℃ | Yield(%) | HRMS(calcd.), m/z* |
---|---|---|---|---|---|
C1 | 8 | White solid | 126—128 | 43.6 | 327.1037(327.0640) |
C2 | 16 | White solid | 151—152 | 69.4 | 356.0103(356.0902) |
C3 | 4 | White solid | 126—128 | 62.0 | 357.0416(357.0717) |
C4 | 4 | Grey solid | 164—166 | 44.2 | 394.0312(394.1113) |
C5 | 4 | Grey solid | 177—179 | 33.5 | 432.0509(432.9812) |
C6 | 5 | White solid | 92—94 | 58.6 | 357.0615(357.0718) |
C7 | 4 | Yellow solid | 166—168 | 35.6 | 447.0609(447.1213) |
C8 | 10 | White solid | 174—176 | 42.6 | 461.0913(461.1319) |
C9 | 4 | White solid | 220—222 | 57.3 | 470.0309(469.9612) |
C10 | 6 | White solid | 222—224 | 52.1 | 507.0629(507.0031) |
C11 | 4 | White solid | 147—150 | 40.7 | 470.0425(469.9617) |
C12 | 10 | White solid | 158—160 | 50.2 | 560.0523(560.0121) |
C13 | 10 | White solid | 131—133 | 63.4 | 574.0009(574.0213) |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
A1 | 8.28(s, 1H, NH), 7.05(s, 1H, benzofuran-H), 7.00(s, 1H, benzofuran-H), 4.16(s, 3H, NCH3), 3.89(s, 3H, OCH3), 3.04(s, 2H, CH2), 2.67(q, J=7.6 Hz, 2H, CH2), 1.51(s, 6H, 2CH3), 1.26(t, J=7.6 Hz, 3H, CH3) | 156.42, 149.64, 144.90, 144.30, 131.29, 129.89, 128.13, 110.45, 107.36, 104.92, 87.94, 56.02, 43.41, 40.78, 28.19, 19.29, 12.82 |
A2 | 8.25(s, 1H, NH), 7.02(s, 2H, benzofuran-H), 4.14(d, J=6.8 Hz, 2H, CH2), 4.16(s, 3H, CH3), 3.03(s, 2H, CH2), 2.67(q, J=7.5 Hz, 2H, CH2), 1.51(s, 6H, 2CH3), 1.44(t, J=7.0 Hz, 3H, CH3), 1.27(t, J=7.5 Hz, 3H, CH3) | 156.38, 149.62, 145.28, 143.50, 131.33, 129.78, 128.42, 110.45, 107.33, 106.51, 87.74, 64.66, 43.47, 40.77, 28.18, 19.30, 14.85, 12.83 |
A3 | 8.25(s, 1H, NH), 7.01(s, 2H, benzofuran-H), 4.17(s, 3H, NCH3), 4.03(t, J=6.9 Hz, 2H, OCH2), 3.02(s, 2H, CH2), 2.67(q, J=7.6 Hz, 2H, CH2), 1.90—1.80(m, 2H, CH2), 1.51(s, 6H, 2 CH3), 1.27(t, J=7.6 Hz, 3H, CH3), 1.02(t, J=7.4 Hz, 3H, CH3) | |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
A4 | 8.19(s, 1H, NH), 7.45(d, J=7.5 Hz, 2H, Ph-H), 7.38—7.27(m, 3H, Ph-H), 7.08(s, 1H, benzofuran-H), 6.99(s, 1H, benzofuran-H), 5.19(s, 2H, OCH2), 4.15(s, 3H, NCH3), 3.03(s, 2H, CH2), 2.66(q, J=7.6 Hz, 2H, CH2), 1.52(s, 6H, 2CH3), 1.26(t, J=7.6 Hz, 3H, CH3) | 156.45, 149.72, 145.69, 143.24, 137.13, 131.42, 129.88, 128.92, 128.59, 128.01, 127.73, 111.25, 107.99, 107.45, 87.99, 71.43, 43.49, 40.84, 28.29, 19.40, 12.95 |
A5 | 8.32(s, 1H, NH), 8.07(d, J=8.4 Hz, 1H, C6H3), 7.54(s, 1H, benzofuran-H), 7.37(d, J=8.4 Hz, 2H, C6H3), 7.26(s, 1H, benzofuran-H), 4.16(s, 3H, NCH3), 3.09(s, 2H, CH2), 2.67(q, J=7.5 Hz, 2H, CH2), 1.49(s, 6H, 2CH3), 1.26(t, J=7.5 Hz, 3H, CH3) | 162.03, 156.55, 149.80, 147.93, 136.04, 133.67, 133.47, 131.39, 130.52, 129.67, 127.24, 116.42, 114.81, 107.62, 89.30, 43.36, 40.97, 28.18, 19.42, 12.96 |
A6 | 8.47—7.39(m, 3H, pyridine-H), 6.91(s, 1H, benzofuran-H), 6.83(s, 1H, pyrazole-H), 6.78(s, 1H, benzofuran-H), 4.01(q, J=7.0 Hz, 2H, CH2), 2.94(s, 2H, CH2), 1.47(s, 6H, 2CH3), 1.37(t, J=7.0 Hz, 3H, CH3) | 155.50, 148.85, 146.66, 145.22, 143.34, 139.99, 139.52, 129.40, 129.20, 128.27, 127.98, 125.80, 110.66, 110.14, 106.42, 87.80, 64.49, 43.38, 28.15, 14.79 |
B1 | 10.11(s, 1H, NH), 7.27—7.03(m, 3H, benzofuran-H+thiazole-H), 4.21(s, 3H, NCH3), 3.95(s, 3H, OCH3), 3.07(s, 2H, CH2), 2.68(q, J=7.6 Hz, 2H, CH2), 1.54(s, 6H, 2CH3), 1.27(t, J=7.5 Hz, 3H, CH3) | 156.08, 155.58, 150.89, 150.07, 147.58, 144.54, 129.15, 128.41, 127.39, 115.47, 109.30, 108.94, 106.20, 88.18, 55.95, 43.26, 41.14, 28.25, 19.22, 12.71 |
B2 | 10.38(s, 1H, NH), 7.30(s, 1H, benzofuran-H), 7.28(s, 1H, benzofuran-H), 7.02(s, 1H, thiazole-H), 4.22(t, 2H, J=7.2 Hz, CH2), 4.21(s, 3H, CH3), 3.06(s, 2H, CH2), 2.69(q, J=7.6 Hz, 2H, CH2), 1.54(s, 6H, 2CH3), 1.47(t, J=7.0 Hz, 3H, CH3), 1.28(t, J=7.6 Hz, 3H, CH3) | 156.10, 155.62, 154.05, 150.97, 150.12, 148.07, 143.79, 129.23, 128.74, 127.29, 115.55, 111.16, 106.14, 88.02, 64.59, 43.36, 41.17, 28.28, 19.21, 14.95, 12.69 |
B3 | 8.54—7.44(m, 3H, pyridine-H), 6.98(s, 1H, pyrazole-H), 7.19—6.86(m, 3H, benzofuran-H+thiazole-H), 3.90(s, 3H, CH3), 3.06(s, 2H, CH2), 1.52(s, 6H, 2CH3) | 157.53, 154.97, 150.65, 148.37, 147.80, 146.87, 144.58, 139.56, 137.26, 128.86, 128.51, 128.05, 126.92, 125.89, 115.56, 111.40, 109.32, 106.60, 88.27, 55.83, 43.17, 28.23 |
B4 | 10.83(s, 1H, NH), 8.55—7.43(m, 3H, pyridine-H), 6.97(s, 1H, pyrazole-H), 7.18—6.76(m, 3H, benzofuran-H+ thiazole-H), 4.14(q, J=7.0 Hz, 2H, CH2), 3.04(s, 2H, CH2), 1.50(s, 6H, 2CH3), 1.43(t, J=7.0 Hz, 3H, CH3) | 157.61, 155.02, 150.71, 148.41, 148.16, 146.90, 143.80, 139.54, 137.24, 128.87, 128.77, 128.02, 126.87, 125.88, 115.55, 111.38, 111.06, 106.54, 88.08, 64.45, 43.22, 28.22, 14.92 |
C1 | 10.00(s, 1H, NH), 4.22(s, 3H, NCH3), 2.69(t, 2H, J=7.6 Hz, CH2), 2.67(s, 3H, CH3), 2.54(s, 3H, COCH3), 1.27(t, J=7.6 Hz, 3H, CH3) | 190.46, 157.35, 155.72, 155.51, 150.25, 128.64, 126.17, 109.39, 41.26, 30.43, 19.17, 18.09, 12.65 |
C2 | 4.21(s, 3H, NCH3), 3.96—3.97[2s, (2.25+0.75)H, OCH3], 2.69(t, 2H, J=7.6 Hz, CH2), 2.46—2.51[2s, (0.75+2.25)H, CH3], 2.25, 2.31[2s, (2.25+0.75) H, CH3], 1.27(t, J=7.6 Hz, 3H, CH3) | |
C3 | 10.06(s, 1H, NH), 4.32(q, J=6.9 Hz, 2H, OCH2), 4.20(s, 3H, NCH3), 2.69—2.65(m, 5H, CH3+CH2), 1.36(t, J=7.0 Hz, 3H, CH3), 1.26(t, J=7.4 Hz, 3H, CH3) | 162.52, 157.92, 156.72, 155.70, 150.22, 128.72, 116.74, 109.31, 60.96, 41.25, 19.18, 17.10, 14.34, 12.67 |
C4 | 9.88(s, 1H, NH), 8.27(s, 1H, 1,2,4-triazole-H), 8.11(s, 1H, 1,2,4-triazole-H), 4.18(s, 3H, NCH3), 2.69(q, J=7.5 Hz, 2H, CH2), 1.27(t, J=7.6 Hz, 3H, CH3), 1.16(s, 9H, 3CH3) | 156.73, 155.70, 152.53, 152.48, 150.22, 147.36, 128.68, 119.78, 109.18, 41.19, 35.95, 29.58, 19.20, 12.70 |
C5 | 10.16(s, 1H, NH), 7.82(d, 1H, C6H2), 7.50(d, 1H, C6H2), 7.26(s, 1H, thiazole-H), 4.20(s, 3H, NCH3), 2.68(q, J=7.6 Hz, 2H, CH2), 1.27(t, J=7.6 Hz, 3H, CH3) | 158.02, 155.64(d), 155.55, 150.17, 144.75, 132.77(d), 131.91, 128.90, 126.87(d), 120.87(d), 12.67, 19.21, 41.15, 109.14, 114.53, 118.55(d) |
C6 | 9.98(s, 1H, NH), 6.89(s, 1H, thiazole-H), 4.20(s, 5H, COCH2+NCH3), 3.73—3.70(m, 2H, CH2), 2.71—2.61(m, 2H, CH2), 1.32—1.22(m, 6H, CH3+CH3) | 170.17, 156.39, 155.51, 150.10, 144.01, 129.08, 111.54, 109.03, 61.13, 41.12, 37.01, 19.1, 14.18, 12.68 |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
C7 | 10.06(s, 1H, NH), 7.89(d, J=8.5 Hz, 1H, benzofuran-H), 7.57(s, 1H, thiazole-H), 6.48(d, J=8.5 Hz, 1H, benzofuran-H), 4.22(s, 3H, NCH3), 3.86(s, 3H, OCH3), 3.00(s, 2H, CH2), 2.68(q, J=7.3 Hz, 2H, CH2), 1.55(s, 6H, 2CH3), 1.27(t, J=7.4 Hz, 3H, CH3) | 157.30, 156.15, 155.52, 155.15, 150.04, 146.24, 129.31, 127.67, 114.18, 111.09, 109.72, 108.87, 102.80, 88.27, 55.41, 41.14, 40.08, 28.67, 19.23, 12.73 |
C8 | 10.02(s, 1H, NH), 7.88(d, J=8.6 Hz, 1H, benzofuran-H), 7.57(s, 1H, thiazole-H), 6.47(d, J=8.7 Hz, 1H, benzofuran-H), 4.22(s, 3H, CH3), 4.09(q, J=7.0 Hz, 2H, CH2), 3.01(s, 2H, CH3), 2.69(q, J=7.6 Hz, 2H, CH2), 1.55(s, 6H, 2CH3), 1.41(t, J=7.0 Hz, 3H, CH3), 1.28(t, J=7.6 Hz, 3H, CH3) | 157.33, 155.59, 155.56, 155.20, 150.04, 146.31, 129.38, 127.57, 114.4, 110.86, 109.61, 108.88, 103.77, 88.19, 63.59, 41.10, 40.19, 28.69, 19.23, 14.96, 12.72 |
C9 | 8.58—7.48(m, 3H, pyridine-H), 6.95(s, 1H, pyrazole-H), 4.27(q, J=7.0 Hz, 2H, CH2), 2.61(s, 3H, CH3), 1.31(t, J=7.1 Hz, 3H, CH3) | 162.25, 158.79, 155.90, 155.24, 148.22, 147.00, 140.00, 137.25, 128.98, 128.35, 126.08, 116.73, 111.84, 61.02, 16.92, 14.27 |
C10 | 8.47(s, 1H, 1,2,4-triazole-H), 8.09(s, 1H, 1,2,4-triazole-H), 8.77—7.52(m, 3H, pyridine-H), 6.86(s, 1H, pyrazole-H), 1.10(s, 9H, 3CH3) | |
C11 | 8.54—7.45(m, 3H, pyridine-H), 6.91(s, 1H, pyrazole-H), 6.82(s, 1H, thiazole-H), 4.18(q, J=7.1 Hz, 2H, CH2), 3.67(s, 2H, CH2), 1.26(t, J=7.0 Hz, 3H, CH3) | 170.21, 157.07, 154.83, 148.35, 146.99, 143.50, 139.67, 137.67, 128.91, 128.23, 126.02, 111.72, 111.44, 61.25, 36.90, 14.15 |
C12 | 7.69(d, J=8.6 Hz, 1H, benzofuran), 8.55—7.43(m, 3H, pyridine-H), 7.40(s, 1H, thiazole-H), 6.92(s, 1H, pyrazole-H), 6.47(d, J=8.7 Hz, 1H, benzofuran-H), 3.84(s, 3H, OCH3), 2.98(s, 2H, CH2), 1.54(s, 6H, 2CH3) | 157.71, 157.13, 156.37, 155.90, 148.62, 146.87, 144.74, 139.49, 138.17, 129.00, 128.08, 127.23, 125.84, 114.38, 111.49, 110.02, 109.05, 103.08, 88.55, 55.42, 40.02, 28.64 |
C13 | 10.74(s, 1H, NH), 7.65(d, J=8.6 Hz, 1H, benzofuran-H), 8.55—7.43(m, 3H, pyridine-H), 7.39(s, 1H, thiazole-H), 6.85(s, 1H, pyrazole-H), 6.43(d, J=8.7 Hz, 1H, benzofuran-H), 4.07(q, J=7.0 Hz, 2H, CH2), 2.99(s, 2H, CH2), 1.54(s, 6H, 2CH3), 1.40(t, J=7.0 Hz, 3H, CH3) | 157.85, 157.10, 156.09, 155.85, 148.65, 146.85, 146.48, 139.49, 138.45, 129.03, 128.12, 127.10, 125.83, 114.62, 111.51, 109.66, 108.69, 104.05, 88.54, 63.63, 40.12, 28.66, 14.93 |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
A1 | 8.28(s, 1H, NH), 7.05(s, 1H, benzofuran-H), 7.00(s, 1H, benzofuran-H), 4.16(s, 3H, NCH3), 3.89(s, 3H, OCH3), 3.04(s, 2H, CH2), 2.67(q, J=7.6 Hz, 2H, CH2), 1.51(s, 6H, 2CH3), 1.26(t, J=7.6 Hz, 3H, CH3) | 156.42, 149.64, 144.90, 144.30, 131.29, 129.89, 128.13, 110.45, 107.36, 104.92, 87.94, 56.02, 43.41, 40.78, 28.19, 19.29, 12.82 |
A2 | 8.25(s, 1H, NH), 7.02(s, 2H, benzofuran-H), 4.14(d, J=6.8 Hz, 2H, CH2), 4.16(s, 3H, CH3), 3.03(s, 2H, CH2), 2.67(q, J=7.5 Hz, 2H, CH2), 1.51(s, 6H, 2CH3), 1.44(t, J=7.0 Hz, 3H, CH3), 1.27(t, J=7.5 Hz, 3H, CH3) | 156.38, 149.62, 145.28, 143.50, 131.33, 129.78, 128.42, 110.45, 107.33, 106.51, 87.74, 64.66, 43.47, 40.77, 28.18, 19.30, 14.85, 12.83 |
A3 | 8.25(s, 1H, NH), 7.01(s, 2H, benzofuran-H), 4.17(s, 3H, NCH3), 4.03(t, J=6.9 Hz, 2H, OCH2), 3.02(s, 2H, CH2), 2.67(q, J=7.6 Hz, 2H, CH2), 1.90—1.80(m, 2H, CH2), 1.51(s, 6H, 2 CH3), 1.27(t, J=7.6 Hz, 3H, CH3), 1.02(t, J=7.4 Hz, 3H, CH3) | |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
A4 | 8.19(s, 1H, NH), 7.45(d, J=7.5 Hz, 2H, Ph-H), 7.38—7.27(m, 3H, Ph-H), 7.08(s, 1H, benzofuran-H), 6.99(s, 1H, benzofuran-H), 5.19(s, 2H, OCH2), 4.15(s, 3H, NCH3), 3.03(s, 2H, CH2), 2.66(q, J=7.6 Hz, 2H, CH2), 1.52(s, 6H, 2CH3), 1.26(t, J=7.6 Hz, 3H, CH3) | 156.45, 149.72, 145.69, 143.24, 137.13, 131.42, 129.88, 128.92, 128.59, 128.01, 127.73, 111.25, 107.99, 107.45, 87.99, 71.43, 43.49, 40.84, 28.29, 19.40, 12.95 |
A5 | 8.32(s, 1H, NH), 8.07(d, J=8.4 Hz, 1H, C6H3), 7.54(s, 1H, benzofuran-H), 7.37(d, J=8.4 Hz, 2H, C6H3), 7.26(s, 1H, benzofuran-H), 4.16(s, 3H, NCH3), 3.09(s, 2H, CH2), 2.67(q, J=7.5 Hz, 2H, CH2), 1.49(s, 6H, 2CH3), 1.26(t, J=7.5 Hz, 3H, CH3) | 162.03, 156.55, 149.80, 147.93, 136.04, 133.67, 133.47, 131.39, 130.52, 129.67, 127.24, 116.42, 114.81, 107.62, 89.30, 43.36, 40.97, 28.18, 19.42, 12.96 |
A6 | 8.47—7.39(m, 3H, pyridine-H), 6.91(s, 1H, benzofuran-H), 6.83(s, 1H, pyrazole-H), 6.78(s, 1H, benzofuran-H), 4.01(q, J=7.0 Hz, 2H, CH2), 2.94(s, 2H, CH2), 1.47(s, 6H, 2CH3), 1.37(t, J=7.0 Hz, 3H, CH3) | 155.50, 148.85, 146.66, 145.22, 143.34, 139.99, 139.52, 129.40, 129.20, 128.27, 127.98, 125.80, 110.66, 110.14, 106.42, 87.80, 64.49, 43.38, 28.15, 14.79 |
B1 | 10.11(s, 1H, NH), 7.27—7.03(m, 3H, benzofuran-H+thiazole-H), 4.21(s, 3H, NCH3), 3.95(s, 3H, OCH3), 3.07(s, 2H, CH2), 2.68(q, J=7.6 Hz, 2H, CH2), 1.54(s, 6H, 2CH3), 1.27(t, J=7.5 Hz, 3H, CH3) | 156.08, 155.58, 150.89, 150.07, 147.58, 144.54, 129.15, 128.41, 127.39, 115.47, 109.30, 108.94, 106.20, 88.18, 55.95, 43.26, 41.14, 28.25, 19.22, 12.71 |
B2 | 10.38(s, 1H, NH), 7.30(s, 1H, benzofuran-H), 7.28(s, 1H, benzofuran-H), 7.02(s, 1H, thiazole-H), 4.22(t, 2H, J=7.2 Hz, CH2), 4.21(s, 3H, CH3), 3.06(s, 2H, CH2), 2.69(q, J=7.6 Hz, 2H, CH2), 1.54(s, 6H, 2CH3), 1.47(t, J=7.0 Hz, 3H, CH3), 1.28(t, J=7.6 Hz, 3H, CH3) | 156.10, 155.62, 154.05, 150.97, 150.12, 148.07, 143.79, 129.23, 128.74, 127.29, 115.55, 111.16, 106.14, 88.02, 64.59, 43.36, 41.17, 28.28, 19.21, 14.95, 12.69 |
B3 | 8.54—7.44(m, 3H, pyridine-H), 6.98(s, 1H, pyrazole-H), 7.19—6.86(m, 3H, benzofuran-H+thiazole-H), 3.90(s, 3H, CH3), 3.06(s, 2H, CH2), 1.52(s, 6H, 2CH3) | 157.53, 154.97, 150.65, 148.37, 147.80, 146.87, 144.58, 139.56, 137.26, 128.86, 128.51, 128.05, 126.92, 125.89, 115.56, 111.40, 109.32, 106.60, 88.27, 55.83, 43.17, 28.23 |
B4 | 10.83(s, 1H, NH), 8.55—7.43(m, 3H, pyridine-H), 6.97(s, 1H, pyrazole-H), 7.18—6.76(m, 3H, benzofuran-H+ thiazole-H), 4.14(q, J=7.0 Hz, 2H, CH2), 3.04(s, 2H, CH2), 1.50(s, 6H, 2CH3), 1.43(t, J=7.0 Hz, 3H, CH3) | 157.61, 155.02, 150.71, 148.41, 148.16, 146.90, 143.80, 139.54, 137.24, 128.87, 128.77, 128.02, 126.87, 125.88, 115.55, 111.38, 111.06, 106.54, 88.08, 64.45, 43.22, 28.22, 14.92 |
C1 | 10.00(s, 1H, NH), 4.22(s, 3H, NCH3), 2.69(t, 2H, J=7.6 Hz, CH2), 2.67(s, 3H, CH3), 2.54(s, 3H, COCH3), 1.27(t, J=7.6 Hz, 3H, CH3) | 190.46, 157.35, 155.72, 155.51, 150.25, 128.64, 126.17, 109.39, 41.26, 30.43, 19.17, 18.09, 12.65 |
C2 | 4.21(s, 3H, NCH3), 3.96—3.97[2s, (2.25+0.75)H, OCH3], 2.69(t, 2H, J=7.6 Hz, CH2), 2.46—2.51[2s, (0.75+2.25)H, CH3], 2.25, 2.31[2s, (2.25+0.75) H, CH3], 1.27(t, J=7.6 Hz, 3H, CH3) | |
C3 | 10.06(s, 1H, NH), 4.32(q, J=6.9 Hz, 2H, OCH2), 4.20(s, 3H, NCH3), 2.69—2.65(m, 5H, CH3+CH2), 1.36(t, J=7.0 Hz, 3H, CH3), 1.26(t, J=7.4 Hz, 3H, CH3) | 162.52, 157.92, 156.72, 155.70, 150.22, 128.72, 116.74, 109.31, 60.96, 41.25, 19.18, 17.10, 14.34, 12.67 |
C4 | 9.88(s, 1H, NH), 8.27(s, 1H, 1,2,4-triazole-H), 8.11(s, 1H, 1,2,4-triazole-H), 4.18(s, 3H, NCH3), 2.69(q, J=7.5 Hz, 2H, CH2), 1.27(t, J=7.6 Hz, 3H, CH3), 1.16(s, 9H, 3CH3) | 156.73, 155.70, 152.53, 152.48, 150.22, 147.36, 128.68, 119.78, 109.18, 41.19, 35.95, 29.58, 19.20, 12.70 |
C5 | 10.16(s, 1H, NH), 7.82(d, 1H, C6H2), 7.50(d, 1H, C6H2), 7.26(s, 1H, thiazole-H), 4.20(s, 3H, NCH3), 2.68(q, J=7.6 Hz, 2H, CH2), 1.27(t, J=7.6 Hz, 3H, CH3) | 158.02, 155.64(d), 155.55, 150.17, 144.75, 132.77(d), 131.91, 128.90, 126.87(d), 120.87(d), 12.67, 19.21, 41.15, 109.14, 114.53, 118.55(d) |
C6 | 9.98(s, 1H, NH), 6.89(s, 1H, thiazole-H), 4.20(s, 5H, COCH2+NCH3), 3.73—3.70(m, 2H, CH2), 2.71—2.61(m, 2H, CH2), 1.32—1.22(m, 6H, CH3+CH3) | 170.17, 156.39, 155.51, 150.10, 144.01, 129.08, 111.54, 109.03, 61.13, 41.12, 37.01, 19.1, 14.18, 12.68 |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
C7 | 10.06(s, 1H, NH), 7.89(d, J=8.5 Hz, 1H, benzofuran-H), 7.57(s, 1H, thiazole-H), 6.48(d, J=8.5 Hz, 1H, benzofuran-H), 4.22(s, 3H, NCH3), 3.86(s, 3H, OCH3), 3.00(s, 2H, CH2), 2.68(q, J=7.3 Hz, 2H, CH2), 1.55(s, 6H, 2CH3), 1.27(t, J=7.4 Hz, 3H, CH3) | 157.30, 156.15, 155.52, 155.15, 150.04, 146.24, 129.31, 127.67, 114.18, 111.09, 109.72, 108.87, 102.80, 88.27, 55.41, 41.14, 40.08, 28.67, 19.23, 12.73 |
C8 | 10.02(s, 1H, NH), 7.88(d, J=8.6 Hz, 1H, benzofuran-H), 7.57(s, 1H, thiazole-H), 6.47(d, J=8.7 Hz, 1H, benzofuran-H), 4.22(s, 3H, CH3), 4.09(q, J=7.0 Hz, 2H, CH2), 3.01(s, 2H, CH3), 2.69(q, J=7.6 Hz, 2H, CH2), 1.55(s, 6H, 2CH3), 1.41(t, J=7.0 Hz, 3H, CH3), 1.28(t, J=7.6 Hz, 3H, CH3) | 157.33, 155.59, 155.56, 155.20, 150.04, 146.31, 129.38, 127.57, 114.4, 110.86, 109.61, 108.88, 103.77, 88.19, 63.59, 41.10, 40.19, 28.69, 19.23, 14.96, 12.72 |
C9 | 8.58—7.48(m, 3H, pyridine-H), 6.95(s, 1H, pyrazole-H), 4.27(q, J=7.0 Hz, 2H, CH2), 2.61(s, 3H, CH3), 1.31(t, J=7.1 Hz, 3H, CH3) | 162.25, 158.79, 155.90, 155.24, 148.22, 147.00, 140.00, 137.25, 128.98, 128.35, 126.08, 116.73, 111.84, 61.02, 16.92, 14.27 |
C10 | 8.47(s, 1H, 1,2,4-triazole-H), 8.09(s, 1H, 1,2,4-triazole-H), 8.77—7.52(m, 3H, pyridine-H), 6.86(s, 1H, pyrazole-H), 1.10(s, 9H, 3CH3) | |
C11 | 8.54—7.45(m, 3H, pyridine-H), 6.91(s, 1H, pyrazole-H), 6.82(s, 1H, thiazole-H), 4.18(q, J=7.1 Hz, 2H, CH2), 3.67(s, 2H, CH2), 1.26(t, J=7.0 Hz, 3H, CH3) | 170.21, 157.07, 154.83, 148.35, 146.99, 143.50, 139.67, 137.67, 128.91, 128.23, 126.02, 111.72, 111.44, 61.25, 36.90, 14.15 |
C12 | 7.69(d, J=8.6 Hz, 1H, benzofuran), 8.55—7.43(m, 3H, pyridine-H), 7.40(s, 1H, thiazole-H), 6.92(s, 1H, pyrazole-H), 6.47(d, J=8.7 Hz, 1H, benzofuran-H), 3.84(s, 3H, OCH3), 2.98(s, 2H, CH2), 1.54(s, 6H, 2CH3) | 157.71, 157.13, 156.37, 155.90, 148.62, 146.87, 144.74, 139.49, 138.17, 129.00, 128.08, 127.23, 125.84, 114.38, 111.49, 110.02, 109.05, 103.08, 88.55, 55.42, 40.02, 28.64 |
C13 | 10.74(s, 1H, NH), 7.65(d, J=8.6 Hz, 1H, benzofuran-H), 8.55—7.43(m, 3H, pyridine-H), 7.39(s, 1H, thiazole-H), 6.85(s, 1H, pyrazole-H), 6.43(d, J=8.7 Hz, 1H, benzofuran-H), 4.07(q, J=7.0 Hz, 2H, CH2), 2.99(s, 2H, CH2), 1.54(s, 6H, 2CH3), 1.40(t, J=7.0 Hz, 3H, CH3) | 157.85, 157.10, 156.09, 155.85, 148.65, 146.85, 146.48, 139.49, 138.45, 129.03, 128.12, 127.10, 125.83, 114.62, 111.51, 109.66, 108.69, 104.05, 88.54, 63.63, 40.12, 28.66, 14.93 |
Compd. | Inhibition rate(%) | Mortality rate(%) | |||
---|---|---|---|---|---|
Aa | Gz | Ss | Ms | Af | |
A1 | 45.00 | 40.00 | 56.30 | 100 | 50.68 |
A2 | 30.00 | 14.30 | 45.80 | 0 | 22.93 |
A3 | 50.00 | 17.10 | 33.30 | 0 | 49.69 |
A4 | 30.00 | 11.40 | 54.20 | 0 | 19.64 |
A5 | 45.00 | 22.90 | 31.30 | 0 | 58.91 |
A6 | 0 | 0 | | 0 | 54.16 |
B1 | 6.82 | 40.58 | 12.98 | 100 | 18.21 |
B2 | 0.00 | 5.80 | | 0 | 62.32 |
B3 | 7.50 | 23.19 | | 0 | 100 |
B4 | 0.00 | 0 | | 0 | 100 |
C1 | 6.82 | 14.49 | 9.87 | 0 | 41.85 |
C2 | | | | | |
C3 | 22.50 | 28.99 | | 0 | 18.27 |
C4 | 13.64 | 40.58 | 42.36 | 4.55 | 12.66 |
C5 | 0.00 | 47.83 | 25.41 | 5.56 | 19.93 |
C6 | 15.91 | 33.33 | 42.81 | 0 | 36.09 |
C7 | 0.00 | 53.62 | 37.68 | 3.85 | 16.90 |
C8 | 0.00 | 8.70 | | 0 | 47.00 |
C9 | 0.00 | 11.59 | | 0 | 95.54 |
C10 | 5.00 | 10.14 | | 0 | 67.21 |
C11 | 7.50 | 0 | | 0 | 56.04 |
C12 | | | | | |
C13 | | | | | |
Boscalid | | 37.00 | 100 | | |
Azoxystrobin | | | 93.50 | | |
Dimethachlon | 100 | | | | |
Chlorantraniliprole | | | | 100 | |
Imidacloprid | | | | | 100 |
Compd. | Inhibition rate(%) | Mortality rate(%) | |||
---|---|---|---|---|---|
Aa | Gz | Ss | Ms | Af | |
A1 | 45.00 | 40.00 | 56.30 | 100 | 50.68 |
A2 | 30.00 | 14.30 | 45.80 | 0 | 22.93 |
A3 | 50.00 | 17.10 | 33.30 | 0 | 49.69 |
A4 | 30.00 | 11.40 | 54.20 | 0 | 19.64 |
A5 | 45.00 | 22.90 | 31.30 | 0 | 58.91 |
A6 | 0 | 0 | | 0 | 54.16 |
B1 | 6.82 | 40.58 | 12.98 | 100 | 18.21 |
B2 | 0.00 | 5.80 | | 0 | 62.32 |
B3 | 7.50 | 23.19 | | 0 | 100 |
B4 | 0.00 | 0 | | 0 | 100 |
C1 | 6.82 | 14.49 | 9.87 | 0 | 41.85 |
C2 | | | | | |
C3 | 22.50 | 28.99 | | 0 | 18.27 |
C4 | 13.64 | 40.58 | 42.36 | 4.55 | 12.66 |
C5 | 0.00 | 47.83 | 25.41 | 5.56 | 19.93 |
C6 | 15.91 | 33.33 | 42.81 | 0 | 36.09 |
C7 | 0.00 | 53.62 | 37.68 | 3.85 | 16.90 |
C8 | 0.00 | 8.70 | | 0 | 47.00 |
C9 | 0.00 | 11.59 | | 0 | 95.54 |
C10 | 5.00 | 10.14 | | 0 | 67.21 |
C11 | 7.50 | 0 | | 0 | 56.04 |
C12 | | | | | |
C13 | | | | | |
Boscalid | | 37.00 | 100 | | |
Azoxystrobin | | | 93.50 | | |
Dimethachlon | 100 | | | | |
Chlorantraniliprole | | | | 100 | |
Imidacloprid | | | | | 100 |
Fig.1 LUMO(A, C, E) and LUMO(B, D, F) maps for imidacloprid(A, B), B3(C, D) and B1(E, F) The green parts represent positive molecular orbital, and the red parts represent negative molecular orbital.
DFT | Δ | ΔELUMO/Hartree | ΔEHOMO/Hartree | ΔEb/Hartree | Mortality rate(%) |
---|---|---|---|---|---|
Imidacloprid | -4613.41817 | -0.06741 | -0.23952 | 0.17211 | 100 |
B1 | -2117.50553782 | -0.06094 | -0.19678 | 0.13584 | 18.21 |
B4 | -4859.53075761 | -0.06146 | -0.20170 | 0.14024 | 100 |
B3 | -4820.20321025 | -0.06211 | -0.20260 | 0.14049 | 100 |
DFT | Δ | ΔELUMO/Hartree | ΔEHOMO/Hartree | ΔEb/Hartree | Mortality rate(%) |
---|---|---|---|---|---|
Imidacloprid | -4613.41817 | -0.06741 | -0.23952 | 0.17211 | 100 |
B1 | -2117.50553782 | -0.06094 | -0.19678 | 0.13584 | 18.21 |
B4 | -4859.53075761 | -0.06146 | -0.20170 | 0.14024 | 100 |
B3 | -4820.20321025 | -0.06211 | -0.20260 | 0.14049 | 100 |
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