高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (8): 1442.doi: 10.7503/cjcu20160335
收稿日期:
2016-05-12
出版日期:
2016-07-19
发布日期:
2016-07-19
作者简介:
联系人简介: 胡艾希, 男, 博士, 教授, 博士生导师, 主要从事药物化学研究. E-mail:
基金资助:
YANG Zihui, LI Beibei, YE Jiao, HU Aixi*()
Received:
2016-05-12
Online:
2016-07-19
Published:
2016-07-19
Contact:
HU Aixi
E-mail:axhu@hnu.edu.cn
摘要:
以呋喃酚为原料, 采用2条合成路线制备2种关键中间体2-氨基-1-(2,2-二甲基-7-烷氧基-2,3-二氢苯并呋喃-5-基)乙酮盐酸盐(2)和n-(2,2-二甲基-2,3-苯并呋喃-7-氧基)烷胺(9), 再经2-(4-芳氧苯氧基)丙酰化合成了17种基于呋喃酚的2-(4-芳氧苯氧基)丙酰胺, 其化学结构经核磁共振谱、 高分辨率质谱和旋光度确证. 除草活性测试结果表明, 在1500 g/hm2剂量下, 大部分化合物对单子叶杂草马唐(Crabgrass)和稗草(Barnyard grass)均具有较高的抑制活性. 在化合物4和5中, 有7个化合物对单子叶杂草表现为A级除草活性, 如化合物4a, 4b, 4i, 5a, 5c, 5e和5h对马唐和稗草的抑制率为100%. 初筛结果显示, 在375 g/hm2剂量下, 化合物4a, 4b, 4i, 5e和5h对稗草的茎叶处理抑制率达96%以上.
TrendMD:
杨子辉, 李贝贝, 叶姣, 胡艾希. 基于呋喃酚构建2-(4-芳氧苯氧基)丙酰胺及除草活性. 高等学校化学学报, 2016, 37(8): 1442.
YANG Zihui,LI Beibei,YE Jiao,HU Aixi. Synthesis and Herbicidal Activity of 2-(4-Arylxoyphenoxy)propionamide Derivatived from Benzofuranol†. Chem. J. Chinese Universities, 2016, 37(8): 1442.
Compd. | t/h | Appearance | m. p./℃ | Yield(%) | [α | HRMS(EI)(calcd.), m/z |
---|---|---|---|---|---|---|
4a | 1.5 | Yellow solid | 146—148 | 71.1 | +27.80 | 578.1424(578.1431) |
4b | 1.5 | White solid | 123—125 | 61.1 | +39.10 | 592.1578(592.1588) |
4c | 1.5 | Yellow solid | 113—115 | 62.8 | +15.00 | 518.1850(518.1853) |
4d | 1.0 | White solid | 125—126 | 78.6 | +36.20 | 532.2005(532.2010) |
4e | 1.0 | Yellow solid | 68—70 | 67.9 | +37.50 | 544.1811(544.1821) |
4f | 1.5 | Yellow solid | 130—132 | 73.2 | +43.30 | 558.1965(558.1978) |
4g | 1.0 | Yellow solid | 129—131 | 62.8 | +57.50 | 528.1452(528.1463) |
4h | 1.0 | Yellow solid | 66—68 | 70.2 | +28.50 | 542.1600(542.1620) |
4i | 1.5 | Yellow solid | 58—60 | 64.7 | +27.40 | 572.2134(572.2134) |
5a | 2.0 | Yellow solid | 49—51 | 59.1 | +15.50 | 500.1502(500.1514) |
5b | 3.0 | White solid | 53—55 | 64.1 | +27.80 | 516.1870(516.1872) |
5c | 3.0 | Yellow solid | 68—70 | 58.0 | +15.05 | 550.1478(550.1482) |
5d | 2.0 | Yellow solid | 84—86 | 62.8 | +20.00 | 533.1715(533.1717) |
5e | 3.0 | Yellow solid | 80—82 | 63.7 | +20.30 | 514.1649(514.1671) |
5f | 3.0 | Yellow solid | 63—65 | 50.8 | +20.25 | 530.2020(530.2029) |
5g | 2.0 | White solid | 93—95 | 52.4 | +24.90 | 564.1619(564.1639) |
5h | 2.0 | Brown solid | 74—76 | 65.4 | +15.00 | 547.1852(547.1874) |
Table 1 Reaction time, appearance, yields, melting points, optical rotations and HRMS data for compounds 4 and
Compd. | t/h | Appearance | m. p./℃ | Yield(%) | [α | HRMS(EI)(calcd.), m/z |
---|---|---|---|---|---|---|
4a | 1.5 | Yellow solid | 146—148 | 71.1 | +27.80 | 578.1424(578.1431) |
4b | 1.5 | White solid | 123—125 | 61.1 | +39.10 | 592.1578(592.1588) |
4c | 1.5 | Yellow solid | 113—115 | 62.8 | +15.00 | 518.1850(518.1853) |
4d | 1.0 | White solid | 125—126 | 78.6 | +36.20 | 532.2005(532.2010) |
4e | 1.0 | Yellow solid | 68—70 | 67.9 | +37.50 | 544.1811(544.1821) |
4f | 1.5 | Yellow solid | 130—132 | 73.2 | +43.30 | 558.1965(558.1978) |
4g | 1.0 | Yellow solid | 129—131 | 62.8 | +57.50 | 528.1452(528.1463) |
4h | 1.0 | Yellow solid | 66—68 | 70.2 | +28.50 | 542.1600(542.1620) |
4i | 1.5 | Yellow solid | 58—60 | 64.7 | +27.40 | 572.2134(572.2134) |
5a | 2.0 | Yellow solid | 49—51 | 59.1 | +15.50 | 500.1502(500.1514) |
5b | 3.0 | White solid | 53—55 | 64.1 | +27.80 | 516.1870(516.1872) |
5c | 3.0 | Yellow solid | 68—70 | 58.0 | +15.05 | 550.1478(550.1482) |
5d | 2.0 | Yellow solid | 84—86 | 62.8 | +20.00 | 533.1715(533.1717) |
5e | 3.0 | Yellow solid | 80—82 | 63.7 | +20.30 | 514.1649(514.1671) |
5f | 3.0 | Yellow solid | 63—65 | 50.8 | +20.25 | 530.2020(530.2029) |
5g | 2.0 | White solid | 93—95 | 52.4 | +24.90 | 564.1619(564.1639) |
5h | 2.0 | Brown solid | 74—76 | 65.4 | +15.00 | 547.1852(547.1874) |
Compd. | 1H NMR( CDCl3), δ* | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
4a | 1.56(s, 6H, 2×CH3), 1.62(d, J=6.8 Hz, 3H, CH3), 3.09(s, 2H, CH2), 3.92(s, 3H, OCH3), 4.63—4.69(m, 1H, CH), 4.74—4.80(m, 2H, COCH2), 7.05(d, J=8.8 Hz, 2H, C6H4), 7.12(d, J=8.8 Hz, 2H, C6H4), 7.42(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.62(t, J=4.0 Hz, 1H, NH), 7.97(s, 1H, C5H2N), 8.26(s, 1H, C5H2N) | 19.0, 28.4, 42.4, 45.9, 56.1, 75.8, 89.8, 110.9, 116.7, 118.8, 119.2, 122.8, 124.2, 127.8, 128.3, 132.9, 136.5, 142.7, 144.8, 147. 1, 153.0, 154.9, 161.4, 172.3, 191.7 |
4b | 1.46(t,J=7.0 Hz, 3H, CH2CH3), 1.55(s, 6H, 2×CH3), 1.65(d, J=6.5 Hz, 3H, CH3), 3.07(s, 2H, CH2), 4.13(q, J=7.0 Hz, 2H, OCH2), 4.62—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH2), 7.04(d, J=9.0 Hz, 2H, C6H4), 7.12(d, J=9.0 Hz, 2H, C6H4), 7.42(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.62(t, J=4.0 Hz, 1H, NH), 7.96(d, J=1.5 Hz, 1H, C5H3N), 8.25(d, J=1.5 Hz, 1H, C5H3N) | 14.7, 19.0, 28.4, 43.0, 45.6, 64.9, 75.5, 89.8, 112.5, 114.8, 116.8, 118.7, 119.2, 122.9, 127.3, 127.7, 128.8, 134.0, 136.2, 142.4, 143.6, 147.2, 155.0, 172.3, 164.2, 191.8 |
4c | 1.53(s, 6H, 2×CH3), 1.63(d, J=6.5 Hz, 3H, CH3), 3.07(s, 2H, CH2), 3.90(s, 3H, OCH3), 4.68—4.69(m, 1H, CH), 4.69—4.74(m, 2H, COCH2), 7.00(d, J=9.5 Hz, 2H, C6H4), 7.09(d, J=9.5 Hz, 2H, C6H4), 7.40(s, 1H, C6H2), 7.44(s, 1H. C6H2), 7.47(dd, J1=2.5 Hz, J2=9.0 Hz, 1H, C6H3), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C6H3) | 19.0, 28.1, 42.7, 45.5, 56.1, 76.2, 90.1, 106.0, 110.8, 117.3, 117.6, 118.7, 118.9, 120.6, 120.7, 121.2, 127.7, 128.3, 129.4, 144.8, 149.0, 151.2, 153.0, 153.6, 154.6, 172.2, 191.9 |
4d | 1.41(t, J=7.0 Hz, 3H, CH2CH3), 1.51(s, 6H, 2×CH3), 1.61(d, J=6.5 Hz, 3H, CH3), 3.04(s, 2H , CH2), 4.72(q, J=7.0 Hz, 1H, CH2), 4.66—4.67(m, 1H, CH), 4.68—4.73(m, 2H, COCH2), 6.86(t, J=8.5 Hz, 1H, C6H3), 6.98—7.01(m, 4H, C6H4), 7.30(d, J=8.5 Hz, 1H, C6H3), 7.37(s, 1H, C6H2), 7.41(s, 1H, C6H2), 7.41—7.43(m, 1H, C6H3), 7.59(t, J=4.5 Hz, 1H, NH) | 15.0, 18.8, 28.1, 42.4, 45.5, 64.6, 75.8, 90.5, 106.1, 112.3 117.2, 118.7 120.5, 120.7, 121.3, 127.6, 128.5, 129.4, 143.9, 149.0, 150.3, 150.4, 151.1, 153.3, 154.5, 171.9, 191.9 |
Compd. | 1H NMR( CDCl3), δ* | 13C NMR(100 MHz, CDCl3), δ |
4e | 1.55(s, 6H, 2×CH3), 1.64(d, J=6.5 Hz, 3H, CH3), 3.08(s, 2H, CH2), 3.91(s, 3H, OCH3), 4.63—4.68(m, 1H, CH), 4.73—4.78(m, 2H , COCH2), 6.98(d, J=8.5 Hz, 1H, C5H3N), 7.03(d, J=9.0 Hz, 2H, C6H4), 7.09(d, J=9.0 Hz, 2H, C6H4), 7.41(s, 1H, C6H2), 7.45(s 1H, C6H2), 7.60(t, J=4.0 Hz, 1H, NH), 7.87(dd, J1=8.5 Hz, J2=2.5 Hz, 1H, C5H3N), 8.42(d, J=2.5 Hz, 1H, C5H3N) | 18.7, 28.4, 42.7, 45.5, 56.1, 75.8, 90.1, 110.9, 111.5, 116.7, 118.9, 122.7, 123.1, 127.8, 128.2, 136.7, 144.9, 145.3, 147.6, 150.8, 152.9, 154.7, 166.5, 172.4, 191.8 |
4f | 1.46(t, J=7.0 Hz, 3H, CH2CH3), 1.55(s, 6H, 2×CH3), 1.65(d, J=6.5 Hz, 3H, CH3), 3.07(s, 2H, CH2), 4.13(q, J=7.0 Hz, 2H, OCH2), 4.63—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH2), 6.98—7.00(m, 1H, C5H3N), 6.98(d, J =8.5 Hz, 1H, C5H3N), 7.03(d, J=9.0 Hz, 2H, C6H4), 7.09(d, J=9.0 Hz, 2H, C6H4), 7.41(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.60(t, J=4.0 Hz, 1H, NH), 7.87—7.90(m, 1H, C5H3N), 8.42(d, J=3.5 Hz, 1H, C5H3N) | 14.7, 18.8, 28.1, 42.7, 45.5, 64.6 75.8, 90.1, 111.3, 112.5, 116.9, 118.9, 121.4, 122.4, 122.6, 127.7, 128.7, 136.7, 144.0, 145.4, 147.7, 153.1, 154.7, 165.9, 172.4, 191.7 |
4g | 1.53(s, 6H, 2×CH3), 1.62(d, J=6.5 Hz, 3H, CHCH3), 3.07(s, 2H, CH2), 3.90(s, 3H, OCH3), 4.60—4.65(m, 1H, CH), 4.71—4.77(m, 2H, COCH2), 7.00(d, J=9.5 Hz, 2H, C6H4), 7.09(d, J=9.5 Hz, 2H, C6H4), 7.40(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.47(dd, J1=9.0 Hz, J2=2.5 Hz, 1H, C5H2N), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C5H2N) | 18.8, 28.1, 42.4, 45.5, 56.1, 75.8, 89.8, 110.8, 116.7, 118.9, 122.5, 124.9, 125.1, 127.8, 128.2, 140.2, 144.7, 145.7, 147.4, 148.3, 152.9, 154.5, 172.3, 191.8 |
4h | 1.44(t, J=6.8 Hz, 3H, CH2CH3), 1.53(s, 6H, 2×CH3), 1.62(d, J=6.4 Hz, 3H, CH3), 3.05(s, 2H, CH2), 4.13(q, J=6.8 Hz, 2H, OCH2), 4.59—4.67(m, 1H, CH), 4.71—4.77(m, 2H, COCH2), 7.00(d, J=9.2 Hz, 2H, C6H4), 7.09(d, J=9.2 Hz, 2H, C6H4), 7.40(s, 1H, C6H2), 7.42(s, 1H, C6H2 6-H), 7.47(dd, J1=9.2 Hz, J2=2.0 Hz, 1H, C5H3N), 7.61(t, J=4.0 Hz, 1H, NH), 8.42(d, J=2.0 Hz, 1H, C5H3N) | 14.7, 19.1, 28.1, 42.7, 45.5, 64.6, 75.8, 89.9, 112.3, 116.7, 118.7, 122.4, 124.9, 125.2, 127.7, 128.5, 140.3, 144.0, 147.4, 148.4, 151.4, 153.2, 154.5, 172.3, 191.7 |
4i | 1.41(t, J=7.5 Hz, 3H, CH2CH3), 1.55(s, 6H, 2×CH3), 1.65(d, J=6.5 Hz, 3H, CH3), 1.82—1.89(m, 2H, CH2), 3.07(s, 2H, ArCH2), 4.04(t, J=7.0 Hz, 2H, OCH2), 4.65—4.69(m, 1H, CH), 4.74—4.79(m, 2H, COCH2), 6.98(d, J=6.0 Hz, 1H, C5H3N, 6-H), 7.04(d, J=8.5 Hz, 2H, C6H4), 7.10(d, J=8.5 Hz, 2H, C6H4), 7.42(s, 1H, C6H2), 7.45(s, 1H, C6H2), 7.69(s, 1H, NH), 7.89(d, J=8.5 Hz, 1H, C5H3N), 8.43(d, J=8.5 Hz, 1H, C5H3N) | 10.5, 18.5, 22.2, 28.4, 42.4, 45.2, 70.8, 75.6, 89.9, 105.8, 112.6, 117.0 117.5, 118.7, 120.1, 120.6, 121.2, 127.5 128.2, 129.2, 143.7, 148.7, 150.4, 151.1, 153.3, 154.2, 171.9, 191.7 |
5a | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.58(d, J=6.8 Hz, 3H, CH3), 3.02(s, 2H, CH2), 3.66—3.72(m, 2H, NHCH2), 4.08—4.15(m, 2H, OCH2), 4.66(q, J=6.8 Hz, 1H, CH), 6.69—6.81(m, 3H, C6H3), 6.94(d, J=8.8 Hz, 2H, C6H4), 7.05(d, J=8.8 Hz, 2H, C6H4), 7.50(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, C5H2N), 7.86(d, J=2.0 Hz, 1H, C5H2N) | 18.6, 28.3, 38.9, 43.2, 68.4, 75.8, 87.6,114.4, 116.6, 118.4, 120.6, 122.2, 124.7, 125.0, 128.7, 140.1, 143.0, 145.6, 147.3, 148.1, 151.1, 151.3, 172.2 |
5b | 1.48(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(d, J=6.8 Hz, 3H, CH3), 3.02(s, 2H, CH2), 3.68—3.72(m, 2H, NHCH2), 4.09—4.15(m, 2H, OCH2), 4.65—4.70(m, 1H, CH), 6.71—6.81(m, 3H, C6H3), 6.89—6.98(m, 3H, C6H4, C5H3N), 7.04(d, J=8.8 Hz, 2H, C6H4), 7.87(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, C5H2N), 8.42(s, 1H, C5H2N) | 18.3, 27.7, 38.0, 42.6, 67.9 ,75.2 87.0, 113.8, 116.1, 118.0, 120.0, 121.9, 124.4, 124.6, 128.2, 139.5, 142.4, 145.1, 146.7, 147.5, 147.8, 150.6, 153.8, 171.7 |
5c | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(d, J=6.8 Hz, 3H), 3.03(s, 2H, CH2), 3.65—3.72(m, 2H, NHCH2), 4.07—4.14(m, 2H, OCH2), 4.68(q, J=6.8 Hz, 1H, CH), 6.68—6.81(m, 3H, C6H3), 6.96(d, J=8.8 Hz, 2H, C6H4), 7.05(d, J=8.8 Hz, 2H, C6H4), 7.97(s, 1H, C5H2N), 8.24(s, 1H, C5H2N) | 18,8, 28.1, 36.2, 43.0, 55.7, 74.7, 88.3, 110.1, 116.3, 116.6, 122.5, 123.1, 124.9, 125.3, 127.2, 128.0, 139.8, 144.4, 146.6, 148.2, 148.7, 154.5, 156.0, 171.8 |
Compd. | 1H NMR( CDCl3), δ* | 13C NMR(100 MHz, CDCl3), δ |
5d | 1.48(s, 3H, CH3), 1.50(s, 3H, CH3), 1.61(d, J=6.4 Hz, 3H, CH3), 3.01(s, 2H, CH2), 3.68—3.72(m, 2H, NHCH2), 4.10—4.15(m, 2H, OCH2), 4.67—4.73(m, 1H, CH), 6.71—6.80(m, 3H, C6H3), 6.98(d, J=9.2 Hz, 2H, C6H4), 7.15(d, J=9.2 Hz, 3H, C6H4), 7.59(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.04(d, J=2.0 Hz, 1H, quinoxalin-H), 8.67(s, 1H, quinoxalin-H) | 19.0. 28.0, 34.2, 43.2, 61.2, 75.6, 87.7, 112.7, 114.6, 116.9, 118.7, 119.5, 120.9, 121.0, 122.0, 122.6, 127.9, 128.8, 130.2, 131.1, 140.1, 144.7, 145.7, 151.9, 157.1, 170.0 |
5e | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.58(d, J=6.8 Hz, 3H, CH3), 1.93—2.02(m, 2H, CCH2C), 3.02(s, 2H, CH2), 3.48—3.53(m, 2H, NHCH2), 3.99—4.09(m, 2H, OCH2), 4.65(q, J=6.8 Hz, 1H, CH), 6.67—6.79(m, 3H, C6H3), 6.90(d, J=8.8 Hz, 2H, C6H4), 7.06(d, J=8.8 Hz, 2H, C6H4), 7.50(dd, J1=9.2 Hz, J2=2.4 Hz, 1H, C5H2N), 7.85(d, J=2.4 Hz, 1H, C5H2N) | 13.7, 23.0, 23.7, 31.5, 38.0, 62.0, 70.4, 82.1, 108.2, 111.0, 111.8, 112.8, 115.0, 117.2, 119.6, 119.8, 123.3, 134.9, 138.1, 141.8, 142.6, 143.0, 149.1, 160.3 |
5f | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(d, J=6.8 Hz, 3H, CH3), 1.95—2.04(m, 2H, CCH2C), 3.02(s, 2H, CH2, CH2), 3.48—3.53(m, 2H, NHCH2), 4.00—4.10(m, 2H, OCH2), 4.63—4.68(m, 1H, CH), 6.68—6.79(m, 3H, C6H3), 6.92(d, J=8.4 Hz, 2H, C6H4), 6.99(d, J=8.8 Hz, 1H, C5H3N), 7.05(d, J=8.4 Hz, 2H, C6H4), 7.88(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, C5H3N), 8.42(s, 1H, C5H3N) | 18.8, 28.2, 28.8, 35.0,43.4, 65.4, 73.1, 87.3, 113.2, 115.9, 117.8, 119.1, 120.3, 122.7, 128.5, 133.0, 136.3, 142.6, 143.5, 146.8, 147.8, 149.2, 155.3, 161.4, 172.1 |
5g | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(s, J=6.8 Hz, 3H, CH3), 1.94—2.04(m, 2H, CCH2C), 3.02(s, 2H, CH2), 3.48—3.53(m, 2H, NHCH2), 4.00—4.09(m, 2H, OCH2), 4.65—4.69(m, 1H, CH), 6.67—6.79(m, 3H, C6H3), 6.93(d, J=8.8 Hz, 2H, C6H4), 7.06(d, J=8.8 Hz, 2H, C6H4), 7.97(d, J=2.0 Hz, 1H, C5H2N), 8.24(s, 1H, C5H2N) | 19.0, 28.3, 29.8, 36.8, 43.4, 67.4, 75.7, 87.5, 113.6, 116.4, 118.1, 119.2, 120.4, 122.8, 128.7, 136.2, 136.3, 142.6, 142.7, 143.4, 147.0, 147.9, 154.8, 161.3, 172.2 |
5h | 1.49(s, 3H, CH3), 1.51(s, 3H, CH3), 1.61(d, J=6.8 Hz, 3H, CH3), 1.97—2.04(m, 2H, CCH2C), 3.02(s, 2H, CH2), 3.50—3.55(m, 2H, NHCH2), 4.03—4.10(m, 2H, OCH2), 4.66—4.71(m, 1H, CH), 6.68—6.78(m, 3H, C6H3), 6.95(d, J=8.8 Hz, 2H, C6H4), 7.17(d, J=8.8 Hz, 2H, C6H4), 7.59(d, J1=8.8 Hz, J2=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.06(s, 1H, quinoxalin-H), 8.68(s, 1H, quinoxalin-H) | 19.1, 28.5, 29.2, 39.0, 43.4, 66.5, 75.9, 87.4, 113.8, 114.5, 116.5, 116.6 118.1, 120.4, 121.2, 122.6, 127.9, 128.8, 129.4, 131.2, 140.2, 143.4, 146.9, 151.0, 154.5, 158.3, 172.2 |
Table 2 1H NMR and 13C NMR data for compounds 4 and 5
Compd. | 1H NMR( CDCl3), δ* | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
4a | 1.56(s, 6H, 2×CH3), 1.62(d, J=6.8 Hz, 3H, CH3), 3.09(s, 2H, CH2), 3.92(s, 3H, OCH3), 4.63—4.69(m, 1H, CH), 4.74—4.80(m, 2H, COCH2), 7.05(d, J=8.8 Hz, 2H, C6H4), 7.12(d, J=8.8 Hz, 2H, C6H4), 7.42(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.62(t, J=4.0 Hz, 1H, NH), 7.97(s, 1H, C5H2N), 8.26(s, 1H, C5H2N) | 19.0, 28.4, 42.4, 45.9, 56.1, 75.8, 89.8, 110.9, 116.7, 118.8, 119.2, 122.8, 124.2, 127.8, 128.3, 132.9, 136.5, 142.7, 144.8, 147. 1, 153.0, 154.9, 161.4, 172.3, 191.7 |
4b | 1.46(t,J=7.0 Hz, 3H, CH2CH3), 1.55(s, 6H, 2×CH3), 1.65(d, J=6.5 Hz, 3H, CH3), 3.07(s, 2H, CH2), 4.13(q, J=7.0 Hz, 2H, OCH2), 4.62—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH2), 7.04(d, J=9.0 Hz, 2H, C6H4), 7.12(d, J=9.0 Hz, 2H, C6H4), 7.42(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.62(t, J=4.0 Hz, 1H, NH), 7.96(d, J=1.5 Hz, 1H, C5H3N), 8.25(d, J=1.5 Hz, 1H, C5H3N) | 14.7, 19.0, 28.4, 43.0, 45.6, 64.9, 75.5, 89.8, 112.5, 114.8, 116.8, 118.7, 119.2, 122.9, 127.3, 127.7, 128.8, 134.0, 136.2, 142.4, 143.6, 147.2, 155.0, 172.3, 164.2, 191.8 |
4c | 1.53(s, 6H, 2×CH3), 1.63(d, J=6.5 Hz, 3H, CH3), 3.07(s, 2H, CH2), 3.90(s, 3H, OCH3), 4.68—4.69(m, 1H, CH), 4.69—4.74(m, 2H, COCH2), 7.00(d, J=9.5 Hz, 2H, C6H4), 7.09(d, J=9.5 Hz, 2H, C6H4), 7.40(s, 1H, C6H2), 7.44(s, 1H. C6H2), 7.47(dd, J1=2.5 Hz, J2=9.0 Hz, 1H, C6H3), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C6H3) | 19.0, 28.1, 42.7, 45.5, 56.1, 76.2, 90.1, 106.0, 110.8, 117.3, 117.6, 118.7, 118.9, 120.6, 120.7, 121.2, 127.7, 128.3, 129.4, 144.8, 149.0, 151.2, 153.0, 153.6, 154.6, 172.2, 191.9 |
4d | 1.41(t, J=7.0 Hz, 3H, CH2CH3), 1.51(s, 6H, 2×CH3), 1.61(d, J=6.5 Hz, 3H, CH3), 3.04(s, 2H , CH2), 4.72(q, J=7.0 Hz, 1H, CH2), 4.66—4.67(m, 1H, CH), 4.68—4.73(m, 2H, COCH2), 6.86(t, J=8.5 Hz, 1H, C6H3), 6.98—7.01(m, 4H, C6H4), 7.30(d, J=8.5 Hz, 1H, C6H3), 7.37(s, 1H, C6H2), 7.41(s, 1H, C6H2), 7.41—7.43(m, 1H, C6H3), 7.59(t, J=4.5 Hz, 1H, NH) | 15.0, 18.8, 28.1, 42.4, 45.5, 64.6, 75.8, 90.5, 106.1, 112.3 117.2, 118.7 120.5, 120.7, 121.3, 127.6, 128.5, 129.4, 143.9, 149.0, 150.3, 150.4, 151.1, 153.3, 154.5, 171.9, 191.9 |
Compd. | 1H NMR( CDCl3), δ* | 13C NMR(100 MHz, CDCl3), δ |
4e | 1.55(s, 6H, 2×CH3), 1.64(d, J=6.5 Hz, 3H, CH3), 3.08(s, 2H, CH2), 3.91(s, 3H, OCH3), 4.63—4.68(m, 1H, CH), 4.73—4.78(m, 2H , COCH2), 6.98(d, J=8.5 Hz, 1H, C5H3N), 7.03(d, J=9.0 Hz, 2H, C6H4), 7.09(d, J=9.0 Hz, 2H, C6H4), 7.41(s, 1H, C6H2), 7.45(s 1H, C6H2), 7.60(t, J=4.0 Hz, 1H, NH), 7.87(dd, J1=8.5 Hz, J2=2.5 Hz, 1H, C5H3N), 8.42(d, J=2.5 Hz, 1H, C5H3N) | 18.7, 28.4, 42.7, 45.5, 56.1, 75.8, 90.1, 110.9, 111.5, 116.7, 118.9, 122.7, 123.1, 127.8, 128.2, 136.7, 144.9, 145.3, 147.6, 150.8, 152.9, 154.7, 166.5, 172.4, 191.8 |
4f | 1.46(t, J=7.0 Hz, 3H, CH2CH3), 1.55(s, 6H, 2×CH3), 1.65(d, J=6.5 Hz, 3H, CH3), 3.07(s, 2H, CH2), 4.13(q, J=7.0 Hz, 2H, OCH2), 4.63—4.67(m, 1H, CH), 4.73—4.77(m, 2H, COCH2), 6.98—7.00(m, 1H, C5H3N), 6.98(d, J =8.5 Hz, 1H, C5H3N), 7.03(d, J=9.0 Hz, 2H, C6H4), 7.09(d, J=9.0 Hz, 2H, C6H4), 7.41(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.60(t, J=4.0 Hz, 1H, NH), 7.87—7.90(m, 1H, C5H3N), 8.42(d, J=3.5 Hz, 1H, C5H3N) | 14.7, 18.8, 28.1, 42.7, 45.5, 64.6 75.8, 90.1, 111.3, 112.5, 116.9, 118.9, 121.4, 122.4, 122.6, 127.7, 128.7, 136.7, 144.0, 145.4, 147.7, 153.1, 154.7, 165.9, 172.4, 191.7 |
4g | 1.53(s, 6H, 2×CH3), 1.62(d, J=6.5 Hz, 3H, CHCH3), 3.07(s, 2H, CH2), 3.90(s, 3H, OCH3), 4.60—4.65(m, 1H, CH), 4.71—4.77(m, 2H, COCH2), 7.00(d, J=9.5 Hz, 2H, C6H4), 7.09(d, J=9.5 Hz, 2H, C6H4), 7.40(s, 1H, C6H2), 7.44(s, 1H, C6H2), 7.47(dd, J1=9.0 Hz, J2=2.5 Hz, 1H, C5H2N), 7.59(t, J=4.0 Hz, 1H, NH), 7.84(d, J=2.5 Hz, 1H, C5H2N) | 18.8, 28.1, 42.4, 45.5, 56.1, 75.8, 89.8, 110.8, 116.7, 118.9, 122.5, 124.9, 125.1, 127.8, 128.2, 140.2, 144.7, 145.7, 147.4, 148.3, 152.9, 154.5, 172.3, 191.8 |
4h | 1.44(t, J=6.8 Hz, 3H, CH2CH3), 1.53(s, 6H, 2×CH3), 1.62(d, J=6.4 Hz, 3H, CH3), 3.05(s, 2H, CH2), 4.13(q, J=6.8 Hz, 2H, OCH2), 4.59—4.67(m, 1H, CH), 4.71—4.77(m, 2H, COCH2), 7.00(d, J=9.2 Hz, 2H, C6H4), 7.09(d, J=9.2 Hz, 2H, C6H4), 7.40(s, 1H, C6H2), 7.42(s, 1H, C6H2 6-H), 7.47(dd, J1=9.2 Hz, J2=2.0 Hz, 1H, C5H3N), 7.61(t, J=4.0 Hz, 1H, NH), 8.42(d, J=2.0 Hz, 1H, C5H3N) | 14.7, 19.1, 28.1, 42.7, 45.5, 64.6, 75.8, 89.9, 112.3, 116.7, 118.7, 122.4, 124.9, 125.2, 127.7, 128.5, 140.3, 144.0, 147.4, 148.4, 151.4, 153.2, 154.5, 172.3, 191.7 |
4i | 1.41(t, J=7.5 Hz, 3H, CH2CH3), 1.55(s, 6H, 2×CH3), 1.65(d, J=6.5 Hz, 3H, CH3), 1.82—1.89(m, 2H, CH2), 3.07(s, 2H, ArCH2), 4.04(t, J=7.0 Hz, 2H, OCH2), 4.65—4.69(m, 1H, CH), 4.74—4.79(m, 2H, COCH2), 6.98(d, J=6.0 Hz, 1H, C5H3N, 6-H), 7.04(d, J=8.5 Hz, 2H, C6H4), 7.10(d, J=8.5 Hz, 2H, C6H4), 7.42(s, 1H, C6H2), 7.45(s, 1H, C6H2), 7.69(s, 1H, NH), 7.89(d, J=8.5 Hz, 1H, C5H3N), 8.43(d, J=8.5 Hz, 1H, C5H3N) | 10.5, 18.5, 22.2, 28.4, 42.4, 45.2, 70.8, 75.6, 89.9, 105.8, 112.6, 117.0 117.5, 118.7, 120.1, 120.6, 121.2, 127.5 128.2, 129.2, 143.7, 148.7, 150.4, 151.1, 153.3, 154.2, 171.9, 191.7 |
5a | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.58(d, J=6.8 Hz, 3H, CH3), 3.02(s, 2H, CH2), 3.66—3.72(m, 2H, NHCH2), 4.08—4.15(m, 2H, OCH2), 4.66(q, J=6.8 Hz, 1H, CH), 6.69—6.81(m, 3H, C6H3), 6.94(d, J=8.8 Hz, 2H, C6H4), 7.05(d, J=8.8 Hz, 2H, C6H4), 7.50(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, C5H2N), 7.86(d, J=2.0 Hz, 1H, C5H2N) | 18.6, 28.3, 38.9, 43.2, 68.4, 75.8, 87.6,114.4, 116.6, 118.4, 120.6, 122.2, 124.7, 125.0, 128.7, 140.1, 143.0, 145.6, 147.3, 148.1, 151.1, 151.3, 172.2 |
5b | 1.48(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(d, J=6.8 Hz, 3H, CH3), 3.02(s, 2H, CH2), 3.68—3.72(m, 2H, NHCH2), 4.09—4.15(m, 2H, OCH2), 4.65—4.70(m, 1H, CH), 6.71—6.81(m, 3H, C6H3), 6.89—6.98(m, 3H, C6H4, C5H3N), 7.04(d, J=8.8 Hz, 2H, C6H4), 7.87(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, C5H2N), 8.42(s, 1H, C5H2N) | 18.3, 27.7, 38.0, 42.6, 67.9 ,75.2 87.0, 113.8, 116.1, 118.0, 120.0, 121.9, 124.4, 124.6, 128.2, 139.5, 142.4, 145.1, 146.7, 147.5, 147.8, 150.6, 153.8, 171.7 |
5c | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(d, J=6.8 Hz, 3H), 3.03(s, 2H, CH2), 3.65—3.72(m, 2H, NHCH2), 4.07—4.14(m, 2H, OCH2), 4.68(q, J=6.8 Hz, 1H, CH), 6.68—6.81(m, 3H, C6H3), 6.96(d, J=8.8 Hz, 2H, C6H4), 7.05(d, J=8.8 Hz, 2H, C6H4), 7.97(s, 1H, C5H2N), 8.24(s, 1H, C5H2N) | 18,8, 28.1, 36.2, 43.0, 55.7, 74.7, 88.3, 110.1, 116.3, 116.6, 122.5, 123.1, 124.9, 125.3, 127.2, 128.0, 139.8, 144.4, 146.6, 148.2, 148.7, 154.5, 156.0, 171.8 |
Compd. | 1H NMR( CDCl3), δ* | 13C NMR(100 MHz, CDCl3), δ |
5d | 1.48(s, 3H, CH3), 1.50(s, 3H, CH3), 1.61(d, J=6.4 Hz, 3H, CH3), 3.01(s, 2H, CH2), 3.68—3.72(m, 2H, NHCH2), 4.10—4.15(m, 2H, OCH2), 4.67—4.73(m, 1H, CH), 6.71—6.80(m, 3H, C6H3), 6.98(d, J=9.2 Hz, 2H, C6H4), 7.15(d, J=9.2 Hz, 3H, C6H4), 7.59(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.04(d, J=2.0 Hz, 1H, quinoxalin-H), 8.67(s, 1H, quinoxalin-H) | 19.0. 28.0, 34.2, 43.2, 61.2, 75.6, 87.7, 112.7, 114.6, 116.9, 118.7, 119.5, 120.9, 121.0, 122.0, 122.6, 127.9, 128.8, 130.2, 131.1, 140.1, 144.7, 145.7, 151.9, 157.1, 170.0 |
5e | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.58(d, J=6.8 Hz, 3H, CH3), 1.93—2.02(m, 2H, CCH2C), 3.02(s, 2H, CH2), 3.48—3.53(m, 2H, NHCH2), 3.99—4.09(m, 2H, OCH2), 4.65(q, J=6.8 Hz, 1H, CH), 6.67—6.79(m, 3H, C6H3), 6.90(d, J=8.8 Hz, 2H, C6H4), 7.06(d, J=8.8 Hz, 2H, C6H4), 7.50(dd, J1=9.2 Hz, J2=2.4 Hz, 1H, C5H2N), 7.85(d, J=2.4 Hz, 1H, C5H2N) | 13.7, 23.0, 23.7, 31.5, 38.0, 62.0, 70.4, 82.1, 108.2, 111.0, 111.8, 112.8, 115.0, 117.2, 119.6, 119.8, 123.3, 134.9, 138.1, 141.8, 142.6, 143.0, 149.1, 160.3 |
5f | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(d, J=6.8 Hz, 3H, CH3), 1.95—2.04(m, 2H, CCH2C), 3.02(s, 2H, CH2, CH2), 3.48—3.53(m, 2H, NHCH2), 4.00—4.10(m, 2H, OCH2), 4.63—4.68(m, 1H, CH), 6.68—6.79(m, 3H, C6H3), 6.92(d, J=8.4 Hz, 2H, C6H4), 6.99(d, J=8.8 Hz, 1H, C5H3N), 7.05(d, J=8.4 Hz, 2H, C6H4), 7.88(dd, J1=8.8 Hz, J2=2.0 Hz, 1H, C5H3N), 8.42(s, 1H, C5H3N) | 18.8, 28.2, 28.8, 35.0,43.4, 65.4, 73.1, 87.3, 113.2, 115.9, 117.8, 119.1, 120.3, 122.7, 128.5, 133.0, 136.3, 142.6, 143.5, 146.8, 147.8, 149.2, 155.3, 161.4, 172.1 |
5g | 1.49(s, 3H, CH3), 1.50(s, 3H, CH3), 1.59(s, J=6.8 Hz, 3H, CH3), 1.94—2.04(m, 2H, CCH2C), 3.02(s, 2H, CH2), 3.48—3.53(m, 2H, NHCH2), 4.00—4.09(m, 2H, OCH2), 4.65—4.69(m, 1H, CH), 6.67—6.79(m, 3H, C6H3), 6.93(d, J=8.8 Hz, 2H, C6H4), 7.06(d, J=8.8 Hz, 2H, C6H4), 7.97(d, J=2.0 Hz, 1H, C5H2N), 8.24(s, 1H, C5H2N) | 19.0, 28.3, 29.8, 36.8, 43.4, 67.4, 75.7, 87.5, 113.6, 116.4, 118.1, 119.2, 120.4, 122.8, 128.7, 136.2, 136.3, 142.6, 142.7, 143.4, 147.0, 147.9, 154.8, 161.3, 172.2 |
5h | 1.49(s, 3H, CH3), 1.51(s, 3H, CH3), 1.61(d, J=6.8 Hz, 3H, CH3), 1.97—2.04(m, 2H, CCH2C), 3.02(s, 2H, CH2), 3.50—3.55(m, 2H, NHCH2), 4.03—4.10(m, 2H, OCH2), 4.66—4.71(m, 1H, CH), 6.68—6.78(m, 3H, C6H3), 6.95(d, J=8.8 Hz, 2H, C6H4), 7.17(d, J=8.8 Hz, 2H, C6H4), 7.59(d, J1=8.8 Hz, J2=2.0 Hz, 1H, quinoxalin-H), 7.67(d, J=8.8 Hz, 1H, quinoxalin-H), 8.06(s, 1H, quinoxalin-H), 8.68(s, 1H, quinoxalin-H) | 19.1, 28.5, 29.2, 39.0, 43.4, 66.5, 75.9, 87.4, 113.8, 114.5, 116.5, 116.6 118.1, 120.4, 121.2, 122.6, 127.9, 128.8, 129.4, 131.2, 140.2, 143.4, 146.9, 151.0, 154.5, 158.3, 172.2 |
Compd. | Pre-emergence treatment | Postemergence treatment | ||||||
---|---|---|---|---|---|---|---|---|
Rape | Amaranth | Barnyard grass | Crabgrass | Rape | Amaranth | Barnyard grass | Crabgrass | |
4a | 0 | 10.0 | 100 | 100 | 20.0 | 64.2 | 100 | 100 |
4b | 0 | 30.0 | 100 | 100 | 15.0 | 0 | 100 | 100 |
4c | 0 | 30.0 | 0 | 5.0 | 10.0 | 10.0 | 6.9 | 42.1 |
4d | 15.0 | 62.8 | 16.0 | 15.0 | 10.0 | 0 | 0 | 42.8 |
4e | 15.0 | 0 | 100 | 100 | 10.0 | 0 | 100 | 42.1 |
4f | 20.0 | 0 | 100 | 100 | 31.1 | 0 | 85.1 | 74.3 |
4g | 15.0 | 0 | 100 | 100 | 32.2 | 0 | 100 | 99.3 |
4h | 10.0 | 15.0 | 100 | 100 | 31.8 | 0 | 100 | 95.4 |
4i | 10.0 | 5.0 | 100 | 100 | 5.0 | 20.0 | 100 | 100 |
5a | 0 | 0 | 100 | 100 | 15.0 | 10.0 | 100 | 87.2 |
5b | 10.0 | 0 | 100 | 99.6 | 5.0 | 10.0 | 100 | 99.4 |
5c | 0 | 0 | 99.7 | 100 | 0 | 15.0 | 100 | 100 |
5d | 5.0 | 0 | 97.9 | 100 | 0 | 0 | 100 | 80.8 |
5e | 0 | 0 | 100 | 100 | 0 | 0 | 100 | 100 |
5f | 15.0 | 0 | 99.3 | 77.0 | 0 | 10.0 | 92.0 | 65.4 |
5g | 0 | 5.0 | 78.5 | 100 | 0 | 15.0 | 100 | 100 |
5h | 0 | 0 | 100 | 100 | 0 | 20.0 | 100 | 100 |
Metamifop | 0 | 0 | 100 | 100 | 0 | 0 | 100 | 100 |
Table 3 Herbicidal activities(%) of compounds 4 and 5(1500 g/hm2)
Compd. | Pre-emergence treatment | Postemergence treatment | ||||||
---|---|---|---|---|---|---|---|---|
Rape | Amaranth | Barnyard grass | Crabgrass | Rape | Amaranth | Barnyard grass | Crabgrass | |
4a | 0 | 10.0 | 100 | 100 | 20.0 | 64.2 | 100 | 100 |
4b | 0 | 30.0 | 100 | 100 | 15.0 | 0 | 100 | 100 |
4c | 0 | 30.0 | 0 | 5.0 | 10.0 | 10.0 | 6.9 | 42.1 |
4d | 15.0 | 62.8 | 16.0 | 15.0 | 10.0 | 0 | 0 | 42.8 |
4e | 15.0 | 0 | 100 | 100 | 10.0 | 0 | 100 | 42.1 |
4f | 20.0 | 0 | 100 | 100 | 31.1 | 0 | 85.1 | 74.3 |
4g | 15.0 | 0 | 100 | 100 | 32.2 | 0 | 100 | 99.3 |
4h | 10.0 | 15.0 | 100 | 100 | 31.8 | 0 | 100 | 95.4 |
4i | 10.0 | 5.0 | 100 | 100 | 5.0 | 20.0 | 100 | 100 |
5a | 0 | 0 | 100 | 100 | 15.0 | 10.0 | 100 | 87.2 |
5b | 10.0 | 0 | 100 | 99.6 | 5.0 | 10.0 | 100 | 99.4 |
5c | 0 | 0 | 99.7 | 100 | 0 | 15.0 | 100 | 100 |
5d | 5.0 | 0 | 97.9 | 100 | 0 | 0 | 100 | 80.8 |
5e | 0 | 0 | 100 | 100 | 0 | 0 | 100 | 100 |
5f | 15.0 | 0 | 99.3 | 77.0 | 0 | 10.0 | 92.0 | 65.4 |
5g | 0 | 5.0 | 78.5 | 100 | 0 | 15.0 | 100 | 100 |
5h | 0 | 0 | 100 | 100 | 0 | 20.0 | 100 | 100 |
Metamifop | 0 | 0 | 100 | 100 | 0 | 0 | 100 | 100 |
Compd. | Dosage/(g·hm-2) | Pre-emergence treatment | Postemergence treatment | ||
---|---|---|---|---|---|
Barnyard grass | Crabgrass | Barnyard grass | Crabgrass | ||
4a | 750 | 96.1 | 74.5 | 99.5 | 6.3 |
375 | 17.1 | 66.4 | 99.0 | 0 | |
4b | 750 | 74.5 | 100 | 100 | 59.0 |
375 | 72.8 | 38.6 | 99.6 | 36.0 | |
4i | 750 | 100 | 100 | 100 | 74.3 |
375 | 85.6 | 85.1 | 98.0 | 24.3 | |
5e | 750 | 83.0 | 99.8 | 100 | 0 |
375 | 82.3 | 29.0 | 96.0 | 0 | |
5h | 750 | 29.6 | 52.4 | 100 | 34.8 |
375 | 23.7 | 36.4 | 98.7 | 12.4 |
Table 4 Herbicidal activities(%) of compounds 4a, 4b, 4i, 5e and 5h
Compd. | Dosage/(g·hm-2) | Pre-emergence treatment | Postemergence treatment | ||
---|---|---|---|---|---|
Barnyard grass | Crabgrass | Barnyard grass | Crabgrass | ||
4a | 750 | 96.1 | 74.5 | 99.5 | 6.3 |
375 | 17.1 | 66.4 | 99.0 | 0 | |
4b | 750 | 74.5 | 100 | 100 | 59.0 |
375 | 72.8 | 38.6 | 99.6 | 36.0 | |
4i | 750 | 100 | 100 | 100 | 74.3 |
375 | 85.6 | 85.1 | 98.0 | 24.3 | |
5e | 750 | 83.0 | 99.8 | 100 | 0 |
375 | 82.3 | 29.0 | 96.0 | 0 | |
5h | 750 | 29.6 | 52.4 | 100 | 34.8 |
375 | 23.7 | 36.4 | 98.7 | 12.4 |
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