高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (3): 486.doi: 10.7503/cjcu20150729
收稿日期:
2015-09-17
出版日期:
2016-03-10
发布日期:
2016-01-24
基金资助:
XU Gaofei, LIU Yanhong, YANG Xinling, WANG Daoquan, YUAN Dekai*()
Received:
2015-09-17
Online:
2016-03-10
Published:
2016-01-24
Contact:
YUAN Dekai
E-mail:yuandekai@aliyun.com
Supported by:
摘要:
以含氰基及环丙烷的酰胺类杀菌剂为先导, 设计合成了结构全新的双氰基环丙烷甲酰胺类化合物. 通过Strecker反应获得中间体2-氨基-2-(取代)苯基乙(丙)腈(1a~1n), 以氰乙酸乙酯和1,2-二溴乙烷环经环化、 水解得到1-氰基环丙烷-1-甲酸(3), 由化合物3和1经缩合反应得到目标化合物4a~4n, 其结构均经NMR和HRMS表征. 生物活性测试结果表明, 在离体条件下, 50 μg/mL的化合物4f对瓜果腐霉和稻瘟菌的抑制活性分别为55.3%和67.1%; 盆栽实验中, 400 μg/mL的化合物4f对黄瓜霜霉病和小麦白粉病的抑制活性分别为50%和85%, 化合物4m对玉米锈病的抑制活性达100%; 5 μg/mL的化合物4c, 4d, 4g, 4j和4m对蚊幼虫的致死率均>60%, 600 μg/mL的化合物 4h和4j对粘虫的致死率分别为66.7%和50%.
中图分类号:
TrendMD:
徐高飞, 刘艳红, 杨新玲, 王道全, 袁德凯. 含有双氰基环丙烷甲酰胺类化合物的合成及生物活性. 高等学校化学学报, 2016, 37(3): 486.
XU Gaofei, LIU Yanhong, YANG Xinling, WANG Daoquan, YUAN Dekai. Synthesis and Biological Activity of Novel Dicyano-containning Cyclopropane-1-carboxamides†. Chem. J. Chinese Universities, 2016, 37(3): 486.
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(Calcd.), m/z |
---|---|---|---|---|
4a | White solid | 50.0 | 99—101 | 248.0791(248.0800)[M+Na]+ |
4b | White solid | 47.9 | 138—140 | 266.0706(266.0706)[M+Na]+ |
4c | Yellow solid | 43.6 | 91—93 | 258.0434(258.0436)[M-H]- |
4d | Yellow solid | 29.3 | 124—126 | 301.9929(301.9931)[M-H]- |
4e | White solid | 69.8 | 135—137 | 238.0980(238.0983)[M-H]- |
4f | White solid | 67.5 | 100—102 | 304.1426(304.1416)[M+Na]+ |
4g | White solid | 60.9 | 84—86 | 254.0930(254.0936)[M-H]- |
4h | White solid | 23.8 | 148—150 | 268.0722(268.0728)[M-H]- |
4i | White solid | 58.9 | 112—114 | 238.0980(238.0989)[M-H]- |
4j | Yellow solid | 54.5 | 136—138 | 296.0567(296.0560)[M+Na]+ |
4k | White solid | 45.3 | 116—118 | 316.0086(316.0092)[M-H]- |
4l | White solid | 46.5 | 150—152 | 316.0086(316.0090)[M-H]- |
4m | White solid | 33.1 | 184—186 | 276.1113(276.1112)[M+Na]+ |
4n | Yellow solid | 43.0 | 122—124 | 292.1062(292.1058)[M+Na]+ |
Table 1 Appearance, yield, melting points and HRMS data of compounds 4a—4h
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(Calcd.), m/z |
---|---|---|---|---|
4a | White solid | 50.0 | 99—101 | 248.0791(248.0800)[M+Na]+ |
4b | White solid | 47.9 | 138—140 | 266.0706(266.0706)[M+Na]+ |
4c | Yellow solid | 43.6 | 91—93 | 258.0434(258.0436)[M-H]- |
4d | Yellow solid | 29.3 | 124—126 | 301.9929(301.9931)[M-H]- |
4e | White solid | 69.8 | 135—137 | 238.0980(238.0983)[M-H]- |
4f | White solid | 67.5 | 100—102 | 304.1426(304.1416)[M+Na]+ |
4g | White solid | 60.9 | 84—86 | 254.0930(254.0936)[M-H]- |
4h | White solid | 23.8 | 148—150 | 268.0722(268.0728)[M-H]- |
4i | White solid | 58.9 | 112—114 | 238.0980(238.0989)[M-H]- |
4j | Yellow solid | 54.5 | 136—138 | 296.0567(296.0560)[M+Na]+ |
4k | White solid | 45.3 | 116—118 | 316.0086(316.0092)[M-H]- |
4l | White solid | 46.5 | 150—152 | 316.0086(316.0090)[M-H]- |
4m | White solid | 33.1 | 184—186 | 276.1113(276.1112)[M+Na]+ |
4n | Yellow solid | 43.0 | 122—124 | 292.1062(292.1058)[M+Na]+ |
Compd. | 1H NMR(300 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ | |
---|---|---|---|
4a | 1.57—1.64, 1.76—1.85(dm, 4H, CH2CH2), 6.03, 6.06[d, 1H, (CN)CH], 6.88, 6.91(d, 1H, CONH), 7.46—7.52(m, 5H, Ar—H) | 13.62, 18.72, 18.97, 45.02, 116.73, 119.20, 127.22, 129.50, 129.88, 132.33, 165.25 | |
4b | 1.58—1.65, 1.75—1.83(dm, 4H, CH2CH2), 6.02, 6.05[d, 1H, (CN)CH], 6.98—7.01(m, 1H, CONH), 7.13—7.52(m, 4H, Ar—H) | 13.59, 18.79, 19.02, 44.32, 116.41, 116.63, 119.17, 128.40, 128.43, 129.28, 129.37, 162.11, 164.60, 165.27 | |
4c | 1.62—1.66, 1.78—1.83(dm, 4H, CH2CH2), 6.04, 6.07[d, 1H, (CN)CH], 7.12, 7.15(d, 1H, CONH), 7.40—7.50(m, 4H, Ar—H) | 13.61, 18.94, 19.15, 44.36, 116.25, 119.14, 125.45, 127.51, 130.05, 130.72, 134.35, 135.33, 165.36 | |
4d | 1.57—1.67, 1.75—1.84(dm, 4H, CH2CH2), 6.01, 6.04[d, 1H, (CN)CH], 7.06, 7.08(d, 1H, NH), 7.35—7.63(m, 4H, Ar—H ) | 13.60, 18.86, 19.09, 44.43, 116.32, 119.12, 124.17, 128.91, 131.50, 132.64, 165.31 | |
4e | 1.55—1.64, 1.75—1.84(dm, 4H, CH2CH2), 2.40(s, 3H, CH3), 5.96, 5.99[d, 1H, (CN)CH], 6.82, 6.85(d, 1H, CONH), 7.26—7.39(m, 4 H, Ar—H) | 13.62, 18.65, 18.92, 21.22, 44.85, 116.86, 119.23, 127.14, 129.33,130.15, 140.06, 165.16 | |
4f | 1.34[s, 9 H, C(CH3)3], 1.56—1.66, 1.70—1.85(dm, 4H, CH2CH2), 5.97, 5.99[d, 1H, (CN)CH], 6.88,6.90(d, 1H, CONH), 7.40—7.50(m, 4H, Ar—H) | 13.62, 18.64, 18.92, 26.18, 30.96, 31.20, 34.80, 44.85, 116.83, 119.25, 126.54, 127.01, 129.17, 153.30, 165.13 | |
Compd. | 1H NMR(300 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ | |
4g | 1.58—1.63, 1.77—1.83(dm, 4H, CH2CH2), 3.85(s, 3H, OCH3), 5.94, 5.96[d, 1H, (CN)CH], 6.78, 6.80(d, 1H, CONH), 6.95—7.44(m, 4 H, Ar—H) | 13.61, 18.64, 18.90, 44.59, 55.47, 114.79, 116.98, 119.24, 124.29, 128.73, 160.66, 165.14 | |
4h | 1.56—1.64, 1.75—1.82(dm, 4H, CH2CH2), 5.90, 5.93[d, 1H, (CN)CH], 6.04(s, 2H, OCH2O), 6.85—7.02(m, 4 H, Ar—H) | 13.63, 18.66, 18.96, 44.80, 101.93, 107.58, 108.88, 116.60, 119.17, 121.24, 125.63, 148.73, 149.11, 164.98 | |
4i | 1.55—1.68, 1.70—1.80(dm, 4H, CH2CH2), 2.03[s, 3H, (CN)C(CH3)], 6.82(s, 1H, CONH), 7.25—7.58(m, 5H, Ar—H) | 13.58, 18.48, 18.56, 29.33, 54.76, 118.86, 119.61, 124.50, 129.14, 129.33, 138.45, 164.55 | |
4j | 1.55—1.78(dm, 4H, CH2CH2), 1.99[s, 3H, (CN)C(CH3)], 6.91(s, 1H, CONH), 7.26—7.50(m, 4H, Ar—H) | 13.53, 18.59, 18.74, 29.51, 54.30, 118.53, 119.52, 125.98, 129.46, 135.03, 137.15, 164.64 | |
4k | 1.57—1.80(dm, 4H, CH2CH2), 1.99[s, 3H, (CN)C(CH3)], 6.91(s, 1H, CONH), 7.26—7.66(m, 4H, Ar—H) | 13.54, 18.70, 18.82, 29.61, 54.26, 118.39, 119.51, 123.29, 127.57, 130.80, 132.21, 140.84, 164.68 | |
4l | 1.54—1.79(dm, 4H, CH2CH2), 1.99[s, 3H, (CN)C(CH3)], 6.85(s, 1H, CONH), 7.40—7.58(m, 4H, Ar—H) | 13.52, 18.60, 18.75, 29.49, 54.36, 118.47, 119.51, 123.15, 126.24, 132.41, 137.71, 164.63 | |
4m | 1.54—1.58, 1.67—1.75(dm, 4H, CH2CH2), 2.01[s, 3H, (CN)C(CH3)], 2.37(s, 3H, Ar—CH3), 5.79(s, 1H, CONH), 7.23—7.45(m, 4H, Ar—H) | 19.26, 22.04, 22.09, 25.74, 34.78, 59.01, 124.90, 125.14, 129.23, 134.49, 142.50, 142.64, 170.29 | |
4n | 1.54—1.57, 1.71—1.76(dm, 4H, CH2CH2), 2.05[s, 3H, (CN)C(CH3)], 3.83(s, 3H, OCH3), 6.74(s, 1H, CONH), 6.94—7.50(m, 4H, Ar—H) | 13.62, 18.41, 18.48, 28.84, 54.23, 55.43, 114.63, 118.98, 119.63, 126.08, 130.20, 160.09, 164.47 |
Table 2 1H NMR data of compounds 4a—4h
Compd. | 1H NMR(300 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ | |
---|---|---|---|
4a | 1.57—1.64, 1.76—1.85(dm, 4H, CH2CH2), 6.03, 6.06[d, 1H, (CN)CH], 6.88, 6.91(d, 1H, CONH), 7.46—7.52(m, 5H, Ar—H) | 13.62, 18.72, 18.97, 45.02, 116.73, 119.20, 127.22, 129.50, 129.88, 132.33, 165.25 | |
4b | 1.58—1.65, 1.75—1.83(dm, 4H, CH2CH2), 6.02, 6.05[d, 1H, (CN)CH], 6.98—7.01(m, 1H, CONH), 7.13—7.52(m, 4H, Ar—H) | 13.59, 18.79, 19.02, 44.32, 116.41, 116.63, 119.17, 128.40, 128.43, 129.28, 129.37, 162.11, 164.60, 165.27 | |
4c | 1.62—1.66, 1.78—1.83(dm, 4H, CH2CH2), 6.04, 6.07[d, 1H, (CN)CH], 7.12, 7.15(d, 1H, CONH), 7.40—7.50(m, 4H, Ar—H) | 13.61, 18.94, 19.15, 44.36, 116.25, 119.14, 125.45, 127.51, 130.05, 130.72, 134.35, 135.33, 165.36 | |
4d | 1.57—1.67, 1.75—1.84(dm, 4H, CH2CH2), 6.01, 6.04[d, 1H, (CN)CH], 7.06, 7.08(d, 1H, NH), 7.35—7.63(m, 4H, Ar—H ) | 13.60, 18.86, 19.09, 44.43, 116.32, 119.12, 124.17, 128.91, 131.50, 132.64, 165.31 | |
4e | 1.55—1.64, 1.75—1.84(dm, 4H, CH2CH2), 2.40(s, 3H, CH3), 5.96, 5.99[d, 1H, (CN)CH], 6.82, 6.85(d, 1H, CONH), 7.26—7.39(m, 4 H, Ar—H) | 13.62, 18.65, 18.92, 21.22, 44.85, 116.86, 119.23, 127.14, 129.33,130.15, 140.06, 165.16 | |
4f | 1.34[s, 9 H, C(CH3)3], 1.56—1.66, 1.70—1.85(dm, 4H, CH2CH2), 5.97, 5.99[d, 1H, (CN)CH], 6.88,6.90(d, 1H, CONH), 7.40—7.50(m, 4H, Ar—H) | 13.62, 18.64, 18.92, 26.18, 30.96, 31.20, 34.80, 44.85, 116.83, 119.25, 126.54, 127.01, 129.17, 153.30, 165.13 | |
Compd. | 1H NMR(300 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ | |
4g | 1.58—1.63, 1.77—1.83(dm, 4H, CH2CH2), 3.85(s, 3H, OCH3), 5.94, 5.96[d, 1H, (CN)CH], 6.78, 6.80(d, 1H, CONH), 6.95—7.44(m, 4 H, Ar—H) | 13.61, 18.64, 18.90, 44.59, 55.47, 114.79, 116.98, 119.24, 124.29, 128.73, 160.66, 165.14 | |
4h | 1.56—1.64, 1.75—1.82(dm, 4H, CH2CH2), 5.90, 5.93[d, 1H, (CN)CH], 6.04(s, 2H, OCH2O), 6.85—7.02(m, 4 H, Ar—H) | 13.63, 18.66, 18.96, 44.80, 101.93, 107.58, 108.88, 116.60, 119.17, 121.24, 125.63, 148.73, 149.11, 164.98 | |
4i | 1.55—1.68, 1.70—1.80(dm, 4H, CH2CH2), 2.03[s, 3H, (CN)C(CH3)], 6.82(s, 1H, CONH), 7.25—7.58(m, 5H, Ar—H) | 13.58, 18.48, 18.56, 29.33, 54.76, 118.86, 119.61, 124.50, 129.14, 129.33, 138.45, 164.55 | |
4j | 1.55—1.78(dm, 4H, CH2CH2), 1.99[s, 3H, (CN)C(CH3)], 6.91(s, 1H, CONH), 7.26—7.50(m, 4H, Ar—H) | 13.53, 18.59, 18.74, 29.51, 54.30, 118.53, 119.52, 125.98, 129.46, 135.03, 137.15, 164.64 | |
4k | 1.57—1.80(dm, 4H, CH2CH2), 1.99[s, 3H, (CN)C(CH3)], 6.91(s, 1H, CONH), 7.26—7.66(m, 4H, Ar—H) | 13.54, 18.70, 18.82, 29.61, 54.26, 118.39, 119.51, 123.29, 127.57, 130.80, 132.21, 140.84, 164.68 | |
4l | 1.54—1.79(dm, 4H, CH2CH2), 1.99[s, 3H, (CN)C(CH3)], 6.85(s, 1H, CONH), 7.40—7.58(m, 4H, Ar—H) | 13.52, 18.60, 18.75, 29.49, 54.36, 118.47, 119.51, 123.15, 126.24, 132.41, 137.71, 164.63 | |
4m | 1.54—1.58, 1.67—1.75(dm, 4H, CH2CH2), 2.01[s, 3H, (CN)C(CH3)], 2.37(s, 3H, Ar—CH3), 5.79(s, 1H, CONH), 7.23—7.45(m, 4H, Ar—H) | 19.26, 22.04, 22.09, 25.74, 34.78, 59.01, 124.90, 125.14, 129.23, 134.49, 142.50, 142.64, 170.29 | |
4n | 1.54—1.57, 1.71—1.76(dm, 4H, CH2CH2), 2.05[s, 3H, (CN)C(CH3)], 3.83(s, 3H, OCH3), 6.74(s, 1H, CONH), 6.94—7.50(m, 4H, Ar—H) | 13.62, 18.41, 18.48, 28.84, 54.23, 55.43, 114.63, 118.98, 119.63, 126.08, 130.20, 160.09, 164.47 |
Compd.a | SSb | BCb | PAb | POb | PASb | RSb |
---|---|---|---|---|---|---|
4a | 22.4 | 13.7 | 13.4 | 30.2 | 18.3 | 8.4 |
4b | 16.1 | 4.3 | 30.8 | 44.3 | 33.3 | 6.3 |
4c | 11.5 | 14.3 | 16.5 | 20.1 | 41.7 | 10.2 |
4d | 17.3 | 22.6 | 33.5 | 32.9 | 28.2 | 10.0 |
4e | 8.5 | 21.0 | 26.7 | 26.9 | 15.6 | 17.0 |
4f | 19.4 | 36.8 | 55.3 | 67.1 | 40.9 | 29.6 |
4g | 9.9 | 15.1 | 23.5 | 25.5 | 20.2 | 11.2 |
4h | 6.8 | 19.4 | 28.4 | 19.5 | 22.0 | 6.3 |
4i | 32.8 | 55.7 | 10.29 | 0.05 | 0.05 | 7.51 |
4j | 47.5 | 47.5 | 7.84 | 0.83 | 0.83 | 3.62 |
4k | 37.7 | 45.9 | 5.64 | 17.36 | 17.36 | 5.45 |
4l | 49.2 | 65.6 | 4.66 | 0.31 | 0.31 | 12.32 |
4m | 41.0 | 49.2 | 0.49 | 2.89 | 2.89 | 7.28 |
4n | 44.3 | 39.3 | 32.35 | 1.86 | 1.86 | 8.42 |
Carbendazim | 94.1 | 83.1 | 41.0 | 40.9 | 91.9 | 93.0 |
Chlorothalonil | 71.6 | 78.0 | 55.8 | 70.5 | 91.9 | 77.0 |
Tricyclazole | 15.7 | 28.8 | 26.7 | 25.5 | 64.5 | 41.9 |
Table 3 In vitro fungicidal activity of title compounds
Compd.a | SSb | BCb | PAb | POb | PASb | RSb |
---|---|---|---|---|---|---|
4a | 22.4 | 13.7 | 13.4 | 30.2 | 18.3 | 8.4 |
4b | 16.1 | 4.3 | 30.8 | 44.3 | 33.3 | 6.3 |
4c | 11.5 | 14.3 | 16.5 | 20.1 | 41.7 | 10.2 |
4d | 17.3 | 22.6 | 33.5 | 32.9 | 28.2 | 10.0 |
4e | 8.5 | 21.0 | 26.7 | 26.9 | 15.6 | 17.0 |
4f | 19.4 | 36.8 | 55.3 | 67.1 | 40.9 | 29.6 |
4g | 9.9 | 15.1 | 23.5 | 25.5 | 20.2 | 11.2 |
4h | 6.8 | 19.4 | 28.4 | 19.5 | 22.0 | 6.3 |
4i | 32.8 | 55.7 | 10.29 | 0.05 | 0.05 | 7.51 |
4j | 47.5 | 47.5 | 7.84 | 0.83 | 0.83 | 3.62 |
4k | 37.7 | 45.9 | 5.64 | 17.36 | 17.36 | 5.45 |
4l | 49.2 | 65.6 | 4.66 | 0.31 | 0.31 | 12.32 |
4m | 41.0 | 49.2 | 0.49 | 2.89 | 2.89 | 7.28 |
4n | 44.3 | 39.3 | 32.35 | 1.86 | 1.86 | 8.42 |
Carbendazim | 94.1 | 83.1 | 41.0 | 40.9 | 91.9 | 93.0 |
Chlorothalonil | 71.6 | 78.0 | 55.8 | 70.5 | 91.9 | 77.0 |
Tricyclazole | 15.7 | 28.8 | 26.7 | 25.5 | 64.5 | 41.9 |
Compd.a | PCb | EGb | PSb |
---|---|---|---|
4f | 50 | 85 | 0 |
4j | 40 | 0 | 0 |
4m | 0 | 0 | 100 |
SYP-1620c | 100 | 100 | 90 |
Table 4 In vivo fungicidal activity of some title compounds
Compd.a | PCb | EGb | PSb |
---|---|---|---|
4f | 50 | 85 | 0 |
4j | 40 | 0 | 0 |
4m | 0 | 0 | 100 |
SYP-1620c | 100 | 100 | 90 |
Compd. | Lethal rate(%) | Compd. | Lethal rate(%) | ||
---|---|---|---|---|---|
Army wormsa | Larvae of Mosquitob | Army wormsa | Larvae of Mosquitob | ||
4a | 33.3 | 36.7 | 4g | 10 | 66.7 |
4b | 10 | 36.7 | 4h | 66.7 | 46.7 |
4c | 40 | 63.3 | 4i | 10 | 46.7 |
4d | 26.7 | 60 | 4j | 16.7 | 56.7 |
4e | 16.7 | 43.3 | 4l | 20 | 40 |
4f | 16.7 | 26.7 | 4m | 50 | 50 |
Table 5 Larvicidal activity of title compounds
Compd. | Lethal rate(%) | Compd. | Lethal rate(%) | ||
---|---|---|---|---|---|
Army wormsa | Larvae of Mosquitob | Army wormsa | Larvae of Mosquitob | ||
4a | 33.3 | 36.7 | 4g | 10 | 66.7 |
4b | 10 | 36.7 | 4h | 66.7 | 46.7 |
4c | 40 | 63.3 | 4i | 10 | 46.7 |
4d | 26.7 | 60 | 4j | 16.7 | 56.7 |
4e | 16.7 | 43.3 | 4l | 20 | 40 |
4f | 16.7 | 26.7 | 4m | 50 | 50 |
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