高等学校化学学报 ›› 2023, Vol. 44 ›› Issue (10): 20230179.doi: 10.7503/cjcu20230179
陈伟(), 兰雨欣, 金彦西, 陈阳, 吴润, 储承文, 高焉凤
收稿日期:
2023-04-06
出版日期:
2023-10-10
发布日期:
2023-04-30
通讯作者:
陈伟
E-mail:chenweicstq@163.com
基金资助:
CHEN Wei(), LAN Yuxin, JIN Yanxi, CHEN Yang, WU Run, CHU Chengwen, GAO Yanfeng
Received:
2023-04-06
Online:
2023-10-10
Published:
2023-04-30
Contact:
CHEN Wei
E-mail:chenweicstq@163.com
Supported by:
摘要:
以天然的四氢喹啉生物碱和氢化中氮茚类化合物为先导, 结合螺环类化合物显著的生物活性, 通过合理的药效团拼接, 将巴比妥酸引入四氢喹啉母核, 设计并合成了12个结构新颖的螺环四氢喹啉衍生物(Ia~Il). 离体抑菌活性测试结果显示, 在50 mg/L的浓度下, 目标化合物Ia~Il对6种植物病原真菌具有中等的抑制活性, 其中化合物Ik对所有受试菌种的抑制率都大于51.0%, 化合物Il对玉米小斑病菌和西瓜炭疽病菌的抑制率分别为78.1%和77.8%, 与对照药百菌清相当. 初步构效关系研究表明, 螺环四氢喹啉衍生物具有抑菌潜力, 引入吡唑药效团可以增强抑菌活性和扩大抑菌谱.
中图分类号:
TrendMD:
陈伟, 兰雨欣, 金彦西, 陈阳, 吴润, 储承文, 高焉凤. 新型螺环四氢喹啉衍生物的设计、合成及抑菌活性. 高等学校化学学报, 2023, 44(10): 20230179.
CHEN Wei, LAN Yuxin, JIN Yanxi, CHEN Yang, WU Run, CHU Chengwen, GAO Yanfeng. Design, Synthesis and Antifungal Activity of Novel Spiro-tetrahydroquinoline Derivatives. Chem. J. Chinese Universities, 2023, 44(10): 20230179.
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS (cacld.), m/z [M-Br-]+ | Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(cacld.), m/z [M-Br-]+ |
---|---|---|---|---|---|---|---|---|---|
Ia | White solid | 61.2 | 166—168 | 314.1505(314.1523) | Ig | Orange solid | 54.2 | 140—142 | 404.1013(404.1019) |
Ib | White solid | 52.1 | 205—206 | 348.1115(348.1126) | Ih | Orange solid | 49.8 | 179—180 | 404.1013(404.1021) |
Ic | White solid | 58.9 | 189—190 | 348.1115(348.1126) | Ii | White solid | 35.8 | 176—178 | 438.1277(438.1286) |
Id | White solid | 41.3 | 186—187 | 382.1379(382.1384) | Ij | Yellow solid | 23.0 | 168—170 | 415.1254(415.1263) |
Ie | White solid | 46.0 | 181—182 | 392.0610(392.0615) | Ik | White solid | 41.0 | 124—126 | 706.1460(706.1475) |
If | White solid | 41.8 | 102—104 | 370.1403(370.1408) | Il | White solid | 56.2 | 118—120 | 636.1385(636.1397) |
Table 1 Appearance, yields, melting points and HRMS data of target compounds Ia—Il
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS (cacld.), m/z [M-Br-]+ | Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(cacld.), m/z [M-Br-]+ |
---|---|---|---|---|---|---|---|---|---|
Ia | White solid | 61.2 | 166—168 | 314.1505(314.1523) | Ig | Orange solid | 54.2 | 140—142 | 404.1013(404.1019) |
Ib | White solid | 52.1 | 205—206 | 348.1115(348.1126) | Ih | Orange solid | 49.8 | 179—180 | 404.1013(404.1021) |
Ic | White solid | 58.9 | 189—190 | 348.1115(348.1126) | Ii | White solid | 35.8 | 176—178 | 438.1277(438.1286) |
Id | White solid | 41.3 | 186—187 | 382.1379(382.1384) | Ij | Yellow solid | 23.0 | 168—170 | 415.1254(415.1263) |
Ie | White solid | 46.0 | 181—182 | 392.0610(392.0615) | Ik | White solid | 41.0 | 124—126 | 706.1460(706.1475) |
If | White solid | 41.8 | 102—104 | 370.1403(370.1408) | Il | White solid | 56.2 | 118—120 | 636.1385(636.1397) |
Compd. | 1H NMR (CDCl3, 400 MHz, TMS), δ | 13C NMR (CDCl3, 100 MHz, TMS), δ |
---|---|---|
Ia a | 7.37—7.26(m, 1H), 7.23(d, J=8.1 Hz, 1H), 7.16—7.07(m, 1H), 6.75(dd, J=8.1, 3.5 Hz, 1H), 4.14—4.06(m, 1H), 3.80—3.75(m, 1H), 3.62—3.53(m, 1H), 3.60(s, 3H), 3.46(s, 3H), 3.39—3.33(m, 1H), 3.20—3.10(m, 1H), 2.33—2.26(m, 1H), 2.25—2.13(m, 2H), 1.76—1.64(m, 1H) | Ref. [ |
Ib b | 6.96(d, J=8.0 Hz, 1H), 6.54(dd, J=7.9, 1.7 Hz, 1H), 6.49(d, J=1.5 Hz, 1H), 3.66(dd, J=9.4, 6.0 Hz, 1H), 3.52—3.44(m, 1H), 3.28—3.15(m, 2H), 3.21(s, 3H), 3.12—3.07(m, 1H), 3.05(s, 3H), 2.04—1.96(m, 1H), 1.93—1.84(m, 2H), 1.48—1.38(m, 1H) | 170.82, 167.41, 151.51, 144.87, 131.55, 129.50, 118.99, 115.04, 110.39, 63.83, 48.67, 47.84, 35.47, 29.18, 28.36, 27.76, 23.11 |
Ic | 7.34(d, J=8.7 Hz, 1H), 7.24(s, 1H), 6.75(d, J=8.6 Hz, 1H), 4.11(dd, J=9.2, 5.9 Hz, 1H), 3.84—3.74(m, 2H), 3.63(s, 3H), 3.57—3.52(m, 1H), 3.48(s, 3H), 3.20(d, J=16.5 Hz, 1H), 2.36—2.29(m, 1H), 2.27—2.19(m, 2H), 1.77—1.66(m, 1H) | 170.46, 166.81, 151.04, 141.89, 127.74, 127.26, 120.72, 119.94, 112.16, 64.08, 48.70, 47.89, 36.59, 29.12, 28.37, 27.97, 23.19 |
Id | 7.40(q, J=8.9 Hz, 1H), 7.23(s, 1H), 6.59(dt, J=17.2, 7.9 Hz, 1H), 4.00—3.86(m, 1H), 3.69—3.59(m, 1H), 3.52(d, J=16.5 Hz, 1H), 3.41(s, 3H), 3.32(d, J=21.4 Hz, 1H), 3.23(s, 3H), 3.05(t, J=16.6 Hz, 1H), 2.14—1.96(m, 3H), 1.58—1.42(m, 1H) | 170.38, 166.69, 150.94, 145.60, 129.20, 126.51, 125.17(q, 1JFC=270.3 Hz), 124.97, 123.83, 121.14, 118.05, 117.69, 117.37, 117.21(q, 2JFC=32.4 Hz), 117.05, 116.73, 110.30, 63.65, 48.24, 47.68, 36.98, 29.14, 28.34, 27.90, 23.21 |
Ie | 6.86(d, J=7.9 Hz, 1H), 6.75(d, J=7.9 Hz, 1H), 6.69(s, 1H), 3.88(dd, J=9.4, 5.8 Hz, 1H), 3.58—3.51(m, 1H), 3.49—3.35(m, 1H), 3.38(s, 3H), 3.27(q, J=8.2 Hz, 1H), 3.22(s, 3H), 2.96(d, J=16.3 Hz, 1H), 2.10—2.03(m, 1H), 2.02—1.93(m, 2H), 1.51—1.39(m, 1H) | 170.53, 166.73, 151.04, 144.35, 129.23, 121.22, 118.80, 117.15, 113.76, 63.64, 48.60, 47.74, 36.85, 29.13, 28.37, 27.94, 23.24 |
If | 7.05(t, J=7.7 Hz, 2H), 6.61(t, J=7.3 Hz, 1H), 6.54(d, J=8.0 Hz, 1H), 3.68—3.62(m, 1H), 3.46—3.42(m, 1H), 3.39(s, 1H), 3.29(d, J=16.8 Hz, 1H), 3.23—3.15(m, 1H), 2.60(s, 3H), 2.45(s, 3H), 2.25—2.18(m, 1H), 2.02—1.93(m, 2H), 1.84—1.76(m, 1H) | 170.65, 170.48, 168.88, 166.74, 165.44, 129.23, 128.21, 118.82, 117.56, 116.76, 111.57, 64.57, 50.11, 48.61, 47.70, 36.86, 35.88, 27.85, 23.23 |
Ig b | 7.05(d, J=8.0 Hz, 1H), 6.59(d, J=7.9 Hz, 1H), 6.51(s, 1H), 3.67(dd, J=9.0, 6.1 Hz, 1H), 3.45(dt, J=8.9, 4.3 Hz, 1H), 3.33(s, 1H), 3.13(q, J=8.2 Hz, 1H), 2.59(s, 3H), 2.55—2.46(m, 1H), 2.44(s, 3H), 2.22—2.16(m, 1H), 2.01—1.91(m, 2H), 1.81—1.69(m, 1H) | 173.57, 171.89, 169.94, 168.60, 166.95, 144.26, 131.07, 129.04, 118.46, 114.58, 109.95, 62.81, 48.55, 47.27, 33.84, 27.28, 22.65, 21.93, 20.70 |
Compd. | 1H NMR (CDCl3, 400 MHz, TMS), δ | 13C NMR (CDCl3, 100 MHz, TMS), δ |
Ih | 7.08(t, J=8.1 Hz, 1H), 6.77(d, J=7.9 Hz, 1H), 6.51(d, J=8.2 Hz, 1H), 3.78(dd, J=8.5, 6.3 Hz, 1H), 3.57(td, J=8.7, 3.7 Hz, 1H), 3.39(d, J=3.2 Hz, 2H), 3.35(t, J=8.1 Hz, 1H), 2.62(s, 3H), 2.47(s, 3H), 2.33—2.26(m, 1H), 2.12—2.06(m, 1H), 2.04—1.95(m, 1H), 1.86—1.76(m, 1H) | 170.66, 170.45, 168.52, 165.52, 146.34, 144.11, 133.74, 127.94, 117.46, 116.19, 110.05, 64.31, 60.56, 53.48, 50.41, 47.90, 32.97, 27.84, 23.21 |
Ii | 7.40(s, 1H), 7.35(d, J=9.2 Hz, 1H), 6.62(d, J=8.6 Hz, 1H), 3.74(dd, J=9.2, 6.1 Hz, 1H), 3.54(dt, J=9.0, 4.3 Hz, 1H), 3.33(d, J=9.9 Hz, 1H), 3.22—3.14(m, 1H), 2.63—2.48(m, 1H), 2.60(s, 3H), 2.44(s, 3H), 2.23—2.20(m, 1H), 2.03—1.94(m, 2H), 1.82—1.73(m, 1H) | 172.24, 170.72, 169.00, 167.43, 150.49, 146.46, 127.25, 125.91(d, 1JFC=269.8 Hz), 124.97, 124.30, 120.13, 115.44, 115.75, 115.28(q, 2JFC=32.1 Hz), 115.12, 114.80, 110.51, 63.00, 57.82, 47.50, 35.00, 27.80, 23.18, 22.40, 21.46, 21.17 |
Ij b | 8.01(t, J=3.7 Hz, 1H), 7.96(dt, J=7.8, 2.7 Hz, 1H), 6.62(d, J=9.1 Hz, 1H), 3.88(dd, J=10.1, 6.0 Hz, 1H), 3.65(t, J=9.4 Hz, 1H), 3.55—3.45(m, 1H), 3.45—3.38(m, 1H), 3.27—3.20(m, 1H), 2.61(s, 3H), 2.44(s, 3H), 2.28—2.17(m, 1H), 2.08—1.96(m, 2H), 1.79—1.64(m, 1H) | 174.13, 172.47, 171.94, 170.80, 169.98, 167.40, 148.99, 135.90, 124.40, 120.09, 110.12, 63.32, 48.01, 34.73, 27.74, 23.02, 22.46, 21.49, 21.22 |
Ik b | 9.04(s, 1H), 8.98(s, 1H), 7.46(s, 1H), 7.37(d, J=8.6 Hz, 1H), 6.65(d, J=8.5 Hz, 1H), 4.07(s, 3H), 4.00(s, 3H), 3.93—3.88(m, 1H), 3.68(d, J=16.9 Hz, 1H), 3.60—3.50(m, 2H), 3.24—3.15(m, 1H), 2.38—2.30(m, 1H), 2.13—2.07(m, 1H), 2.04—1.95(m, 2H) | 169.38, 166.40, 161.28, 158.96, 152.75, 147.63, 146.03, 141.77, 141.39, 141.23(q, 2JFC =31.3 Hz), 141.08, 140.76, 125.18, 124.74, 123.29(d, 1JFC=291.7 Hz), 121.84, 119.21, 114.98, 110.99, 105.90, 103.65, 63.84, 59.25, 56.84, 49.99, 48.92, 47.75, 46.38, 35.29, 32.59, 27.84, 23.22, 18.99, 14.53 |
Il | 8.10(s, 1H), 7.83(s, 1H), 7.06(t, J=8.1 Hz, 2H), 6.91(d, J=12.8 Hz, 1H), 6.72(d, J=7.8 Hz, 1H), 6.49(d, J=8.2 Hz, 1H), 3.97(s, 3H), 3.89(s, 3H), 3.60(d, J=6.0 Hz, 1H), 3.58—3.56(m, 1H), 3.39(d, J=17.2 Hz, 1H), 3.34—3.27(m, 1H), 2.95(s, 1H), 2.88(s, 1H), 2.40—2.32(m, 1H), 2.18—2.10(m, 1H), 2.03—1.97(m, 1H) | 163.40, 156.70, 146.91, 146.65(t, 2JFC=51.2 Hz), 146.40, 145.76, 145.52(t, 2JFC=23.8 Hz), 145.28, 138.82, 136.57, 113.49, 113.46(t, 3JFC=3.5 Hz), 113.43, 112.42, 112.37, 110.53, 110.08, 110.04, 107.74, 107.70, 98.78, 78.86, 67.42, 34.63, 31.40, 26.78, 25.21, 22.87, 22.50, 19.03 |
Table 2 1H NMR and 13C NMR data of target compounds Ia—Il
Compd. | 1H NMR (CDCl3, 400 MHz, TMS), δ | 13C NMR (CDCl3, 100 MHz, TMS), δ |
---|---|---|
Ia a | 7.37—7.26(m, 1H), 7.23(d, J=8.1 Hz, 1H), 7.16—7.07(m, 1H), 6.75(dd, J=8.1, 3.5 Hz, 1H), 4.14—4.06(m, 1H), 3.80—3.75(m, 1H), 3.62—3.53(m, 1H), 3.60(s, 3H), 3.46(s, 3H), 3.39—3.33(m, 1H), 3.20—3.10(m, 1H), 2.33—2.26(m, 1H), 2.25—2.13(m, 2H), 1.76—1.64(m, 1H) | Ref. [ |
Ib b | 6.96(d, J=8.0 Hz, 1H), 6.54(dd, J=7.9, 1.7 Hz, 1H), 6.49(d, J=1.5 Hz, 1H), 3.66(dd, J=9.4, 6.0 Hz, 1H), 3.52—3.44(m, 1H), 3.28—3.15(m, 2H), 3.21(s, 3H), 3.12—3.07(m, 1H), 3.05(s, 3H), 2.04—1.96(m, 1H), 1.93—1.84(m, 2H), 1.48—1.38(m, 1H) | 170.82, 167.41, 151.51, 144.87, 131.55, 129.50, 118.99, 115.04, 110.39, 63.83, 48.67, 47.84, 35.47, 29.18, 28.36, 27.76, 23.11 |
Ic | 7.34(d, J=8.7 Hz, 1H), 7.24(s, 1H), 6.75(d, J=8.6 Hz, 1H), 4.11(dd, J=9.2, 5.9 Hz, 1H), 3.84—3.74(m, 2H), 3.63(s, 3H), 3.57—3.52(m, 1H), 3.48(s, 3H), 3.20(d, J=16.5 Hz, 1H), 2.36—2.29(m, 1H), 2.27—2.19(m, 2H), 1.77—1.66(m, 1H) | 170.46, 166.81, 151.04, 141.89, 127.74, 127.26, 120.72, 119.94, 112.16, 64.08, 48.70, 47.89, 36.59, 29.12, 28.37, 27.97, 23.19 |
Id | 7.40(q, J=8.9 Hz, 1H), 7.23(s, 1H), 6.59(dt, J=17.2, 7.9 Hz, 1H), 4.00—3.86(m, 1H), 3.69—3.59(m, 1H), 3.52(d, J=16.5 Hz, 1H), 3.41(s, 3H), 3.32(d, J=21.4 Hz, 1H), 3.23(s, 3H), 3.05(t, J=16.6 Hz, 1H), 2.14—1.96(m, 3H), 1.58—1.42(m, 1H) | 170.38, 166.69, 150.94, 145.60, 129.20, 126.51, 125.17(q, 1JFC=270.3 Hz), 124.97, 123.83, 121.14, 118.05, 117.69, 117.37, 117.21(q, 2JFC=32.4 Hz), 117.05, 116.73, 110.30, 63.65, 48.24, 47.68, 36.98, 29.14, 28.34, 27.90, 23.21 |
Ie | 6.86(d, J=7.9 Hz, 1H), 6.75(d, J=7.9 Hz, 1H), 6.69(s, 1H), 3.88(dd, J=9.4, 5.8 Hz, 1H), 3.58—3.51(m, 1H), 3.49—3.35(m, 1H), 3.38(s, 3H), 3.27(q, J=8.2 Hz, 1H), 3.22(s, 3H), 2.96(d, J=16.3 Hz, 1H), 2.10—2.03(m, 1H), 2.02—1.93(m, 2H), 1.51—1.39(m, 1H) | 170.53, 166.73, 151.04, 144.35, 129.23, 121.22, 118.80, 117.15, 113.76, 63.64, 48.60, 47.74, 36.85, 29.13, 28.37, 27.94, 23.24 |
If | 7.05(t, J=7.7 Hz, 2H), 6.61(t, J=7.3 Hz, 1H), 6.54(d, J=8.0 Hz, 1H), 3.68—3.62(m, 1H), 3.46—3.42(m, 1H), 3.39(s, 1H), 3.29(d, J=16.8 Hz, 1H), 3.23—3.15(m, 1H), 2.60(s, 3H), 2.45(s, 3H), 2.25—2.18(m, 1H), 2.02—1.93(m, 2H), 1.84—1.76(m, 1H) | 170.65, 170.48, 168.88, 166.74, 165.44, 129.23, 128.21, 118.82, 117.56, 116.76, 111.57, 64.57, 50.11, 48.61, 47.70, 36.86, 35.88, 27.85, 23.23 |
Ig b | 7.05(d, J=8.0 Hz, 1H), 6.59(d, J=7.9 Hz, 1H), 6.51(s, 1H), 3.67(dd, J=9.0, 6.1 Hz, 1H), 3.45(dt, J=8.9, 4.3 Hz, 1H), 3.33(s, 1H), 3.13(q, J=8.2 Hz, 1H), 2.59(s, 3H), 2.55—2.46(m, 1H), 2.44(s, 3H), 2.22—2.16(m, 1H), 2.01—1.91(m, 2H), 1.81—1.69(m, 1H) | 173.57, 171.89, 169.94, 168.60, 166.95, 144.26, 131.07, 129.04, 118.46, 114.58, 109.95, 62.81, 48.55, 47.27, 33.84, 27.28, 22.65, 21.93, 20.70 |
Compd. | 1H NMR (CDCl3, 400 MHz, TMS), δ | 13C NMR (CDCl3, 100 MHz, TMS), δ |
Ih | 7.08(t, J=8.1 Hz, 1H), 6.77(d, J=7.9 Hz, 1H), 6.51(d, J=8.2 Hz, 1H), 3.78(dd, J=8.5, 6.3 Hz, 1H), 3.57(td, J=8.7, 3.7 Hz, 1H), 3.39(d, J=3.2 Hz, 2H), 3.35(t, J=8.1 Hz, 1H), 2.62(s, 3H), 2.47(s, 3H), 2.33—2.26(m, 1H), 2.12—2.06(m, 1H), 2.04—1.95(m, 1H), 1.86—1.76(m, 1H) | 170.66, 170.45, 168.52, 165.52, 146.34, 144.11, 133.74, 127.94, 117.46, 116.19, 110.05, 64.31, 60.56, 53.48, 50.41, 47.90, 32.97, 27.84, 23.21 |
Ii | 7.40(s, 1H), 7.35(d, J=9.2 Hz, 1H), 6.62(d, J=8.6 Hz, 1H), 3.74(dd, J=9.2, 6.1 Hz, 1H), 3.54(dt, J=9.0, 4.3 Hz, 1H), 3.33(d, J=9.9 Hz, 1H), 3.22—3.14(m, 1H), 2.63—2.48(m, 1H), 2.60(s, 3H), 2.44(s, 3H), 2.23—2.20(m, 1H), 2.03—1.94(m, 2H), 1.82—1.73(m, 1H) | 172.24, 170.72, 169.00, 167.43, 150.49, 146.46, 127.25, 125.91(d, 1JFC=269.8 Hz), 124.97, 124.30, 120.13, 115.44, 115.75, 115.28(q, 2JFC=32.1 Hz), 115.12, 114.80, 110.51, 63.00, 57.82, 47.50, 35.00, 27.80, 23.18, 22.40, 21.46, 21.17 |
Ij b | 8.01(t, J=3.7 Hz, 1H), 7.96(dt, J=7.8, 2.7 Hz, 1H), 6.62(d, J=9.1 Hz, 1H), 3.88(dd, J=10.1, 6.0 Hz, 1H), 3.65(t, J=9.4 Hz, 1H), 3.55—3.45(m, 1H), 3.45—3.38(m, 1H), 3.27—3.20(m, 1H), 2.61(s, 3H), 2.44(s, 3H), 2.28—2.17(m, 1H), 2.08—1.96(m, 2H), 1.79—1.64(m, 1H) | 174.13, 172.47, 171.94, 170.80, 169.98, 167.40, 148.99, 135.90, 124.40, 120.09, 110.12, 63.32, 48.01, 34.73, 27.74, 23.02, 22.46, 21.49, 21.22 |
Ik b | 9.04(s, 1H), 8.98(s, 1H), 7.46(s, 1H), 7.37(d, J=8.6 Hz, 1H), 6.65(d, J=8.5 Hz, 1H), 4.07(s, 3H), 4.00(s, 3H), 3.93—3.88(m, 1H), 3.68(d, J=16.9 Hz, 1H), 3.60—3.50(m, 2H), 3.24—3.15(m, 1H), 2.38—2.30(m, 1H), 2.13—2.07(m, 1H), 2.04—1.95(m, 2H) | 169.38, 166.40, 161.28, 158.96, 152.75, 147.63, 146.03, 141.77, 141.39, 141.23(q, 2JFC =31.3 Hz), 141.08, 140.76, 125.18, 124.74, 123.29(d, 1JFC=291.7 Hz), 121.84, 119.21, 114.98, 110.99, 105.90, 103.65, 63.84, 59.25, 56.84, 49.99, 48.92, 47.75, 46.38, 35.29, 32.59, 27.84, 23.22, 18.99, 14.53 |
Il | 8.10(s, 1H), 7.83(s, 1H), 7.06(t, J=8.1 Hz, 2H), 6.91(d, J=12.8 Hz, 1H), 6.72(d, J=7.8 Hz, 1H), 6.49(d, J=8.2 Hz, 1H), 3.97(s, 3H), 3.89(s, 3H), 3.60(d, J=6.0 Hz, 1H), 3.58—3.56(m, 1H), 3.39(d, J=17.2 Hz, 1H), 3.34—3.27(m, 1H), 2.95(s, 1H), 2.88(s, 1H), 2.40—2.32(m, 1H), 2.18—2.10(m, 1H), 2.03—1.97(m, 1H) | 163.40, 156.70, 146.91, 146.65(t, 2JFC=51.2 Hz), 146.40, 145.76, 145.52(t, 2JFC=23.8 Hz), 145.28, 138.82, 136.57, 113.49, 113.46(t, 3JFC=3.5 Hz), 113.43, 112.42, 112.37, 110.53, 110.08, 110.04, 107.74, 107.70, 98.78, 78.86, 67.42, 34.63, 31.40, 26.78, 25.21, 22.87, 22.50, 19.03 |
Compd. | Antifungal activity(%) | |||||
---|---|---|---|---|---|---|
F. oxysporum | R. cerealis | H. maydis | P. piricola | F. graminearum | C. lagenarium | |
Ia | 0 | 0 | 26.3±1.0 | 6.1±0.0 | 4.2±0.2 | 15.1±0.5 |
Ib | 0 | 0 | 16.2±0.4 | 5.1±0.2 | 8.4±0.3 | 15.1±0.0 |
Ic | 0 | 0 | 23.8±0.5 | 0 | 3.6±1.0 | 13.2±0.5 |
Id | 0 | 39.7±1.5 | 25.7±0.6 | 0 | 32.7±0.2 | 14.0±0.2 |
Ie | 7.1±0.2 | 9.2±0.4 | 23.0±0.6 | 10.1±0.2 | 14.8±0.5 | 35.8±0.5 |
If | 5.8±0.4 | 0 | 57.7±0.4 | 2.1±0.2 | 9.1±0.9 | 62.6±0.0 |
Ig | 41.7±1.4 | 42.7±0.9 | 79.4±0.2 | 34.7±0.6 | 34.2±0.6 | 27.4±0.4 |
Ih | 28.0±0.2 | 21.7±0.2 | 64.3±1.9 | 40.8±0.5 | 45.4±1.0 | 54.6±0.2 |
Ii | 22.1±0.2 | 33.3±0.4 | 55.6±0.4 | 47.8±0.5 | 39.1±0.8 | 60.9±0.7 |
Ij | 3.2±0.5 | 0 | 39.0±0.2 | 0 | 32.4±0.7 | 33.5±0.9 |
Ik | 59.7±0.7 | 54.9±0.6 | 70.0±0.4 | 51.7±0.2 | 53.0±0.0 | 72.7±0.4 |
Il | 42.6±1.2 | 31.1±0.3 | 78.1±0.5 | 42.6±1.0 | 36.9±0.3 | 77.8±0.3 |
Chlorothalonil | 74.5±0.0 | 80.3±0.5 | 81.1±0.2 | 78.0±1.3 | 84.0±0.5 | 76.6±0.2 |
Carbendazim | 100.0 | 35.4±0.0 | 84.1±1.9 | 100.0 | 100.0 | 100.0 |
Table 3 Antifungal activity of compounds Ia—Il*
Compd. | Antifungal activity(%) | |||||
---|---|---|---|---|---|---|
F. oxysporum | R. cerealis | H. maydis | P. piricola | F. graminearum | C. lagenarium | |
Ia | 0 | 0 | 26.3±1.0 | 6.1±0.0 | 4.2±0.2 | 15.1±0.5 |
Ib | 0 | 0 | 16.2±0.4 | 5.1±0.2 | 8.4±0.3 | 15.1±0.0 |
Ic | 0 | 0 | 23.8±0.5 | 0 | 3.6±1.0 | 13.2±0.5 |
Id | 0 | 39.7±1.5 | 25.7±0.6 | 0 | 32.7±0.2 | 14.0±0.2 |
Ie | 7.1±0.2 | 9.2±0.4 | 23.0±0.6 | 10.1±0.2 | 14.8±0.5 | 35.8±0.5 |
If | 5.8±0.4 | 0 | 57.7±0.4 | 2.1±0.2 | 9.1±0.9 | 62.6±0.0 |
Ig | 41.7±1.4 | 42.7±0.9 | 79.4±0.2 | 34.7±0.6 | 34.2±0.6 | 27.4±0.4 |
Ih | 28.0±0.2 | 21.7±0.2 | 64.3±1.9 | 40.8±0.5 | 45.4±1.0 | 54.6±0.2 |
Ii | 22.1±0.2 | 33.3±0.4 | 55.6±0.4 | 47.8±0.5 | 39.1±0.8 | 60.9±0.7 |
Ij | 3.2±0.5 | 0 | 39.0±0.2 | 0 | 32.4±0.7 | 33.5±0.9 |
Ik | 59.7±0.7 | 54.9±0.6 | 70.0±0.4 | 51.7±0.2 | 53.0±0.0 | 72.7±0.4 |
Il | 42.6±1.2 | 31.1±0.3 | 78.1±0.5 | 42.6±1.0 | 36.9±0.3 | 77.8±0.3 |
Chlorothalonil | 74.5±0.0 | 80.3±0.5 | 81.1±0.2 | 78.0±1.3 | 84.0±0.5 | 76.6±0.2 |
Carbendazim | 100.0 | 35.4±0.0 | 84.1±1.9 | 100.0 | 100.0 | 100.0 |
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