高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (7): 1291.doi: 10.7503/cjcu20150100
陈伟, 魏巍, 刘明, 华学文, 李玉新, 李永红, 张晓, 李正名()
收稿日期:
2015-01-29
出版日期:
2015-07-10
发布日期:
2015-05-22
作者简介:
联系人简介: 李正名, 男, 教授, 博士生导师, 中国工程院院士, 从事有机化学和农药化学研究. E-mail:基金资助:
CHEN Wei, WEI Wei, LIU Ming, HUA Xuewen, LI Yuxin, LI Yonghong, ZHANG Xiao, LI Zhengming*()
Received:
2015-01-29
Online:
2015-07-10
Published:
2015-05-22
Contact:
LI Zhengming
E-mail:nkzml@vip.163.com
Supported by:
摘要:
将二甲氧基甲基引入到嘧啶环的4位, 设计并合成了15个结构新颖的磺酰脲类衍生物. 初步生物活性测试结果表明, 目标化合物具有较好的除草活性. 在75 g/ha的剂量下, 化合物6a和6g对油菜的芽前除草活性为100%, 与对照药单嘧磺隆和氯磺隆相当; 在50 mg/L的浓度下, 化合物6i和6o对3种病菌的离体抑制率都超过80%, 与对照药百菌清和多菌灵接近.
中图分类号:
TrendMD:
陈伟, 魏巍, 刘明, 华学文, 李玉新, 李永红, 张晓, 李正名. 新型含二甲氧基甲基嘧啶基磺酰脲衍生物的合成及生物活性. 高等学校化学学报, 2015, 36(7): 1291.
CHEN Wei, WEI Wei, LIU Ming, HUA Xuewen, LI Yuxin, LI Yonghong, ZHANG Xiao, LI Zhengming. Design, Synthesis and Biological Activity of Novel Sulfonylurea Derivatives Containing Dimethoxymethyl-substituted Pyrimidine Moiety†. Chem. J. Chinese Universities, 2015, 36(7): 1291.
Compd. | m. p./℃ | Compd. | m. p./℃ | Compd. | m. p./℃ |
---|---|---|---|---|---|
5a | 146—147(151—153[ | 5e | 129—130(132—134[ | 5l | 140—141(140—141[ |
5b | 114—115(115—117[ | 5f | 128—129(128—129[ | 5m | 137—139(143—144[ |
5c | 175—177(175—177[ | 5g | 73—74(70—72.5[ | 5n | 129—130(130[ |
5d | 151—152(153—155[ | 5i | 132—133(131—133[ | 5o | 103—104(102—104[ |
Table 1 Melting points of intermediates 5a—5g, 5i, 5l—5o
Compd. | m. p./℃ | Compd. | m. p./℃ | Compd. | m. p./℃ |
---|---|---|---|---|---|
5a | 146—147(151—153[ | 5e | 129—130(132—134[ | 5l | 140—141(140—141[ |
5b | 114—115(115—117[ | 5f | 128—129(128—129[ | 5m | 137—139(143—144[ |
5c | 175—177(175—177[ | 5g | 73—74(70—72.5[ | 5n | 129—130(130[ |
5d | 151—152(153—155[ | 5i | 132—133(131—133[ | 5o | 103—104(102—104[ |
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ | Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ |
---|---|---|---|---|---|---|---|---|---|
6a | White soild | 76.3 | 165—167 | 387.0532(387.0530) | 6i | White soild | 84.1 | 124—125 | 421.0789(421.0793) |
6b | White soild | 73.3 | 171—173 | 387.0526(387.0530) | 6j | White soild | 74.7 | 167—169 | 437.0739(437.0743) |
6c | White soild | 65.3 | 186—188 | 432.0380(432.0381) | 6k | White soild | 59.4 | 170—171 | 431.0790(431.0792) |
6d | White soild | 75.3 | 169—171 | 398.0770(3980770) | 6l | White soild | 76.8 | 167—168 | 452.0849(452.0852) |
6e | White soild | 65.7 | 193—195 | 398.0767(398.0770) | 6m | White soild | 69.1 | 167—168 | 485.0910(485.0913) |
6f | White soild | 74.7 | 207—209 | 403.0632(403.0633) | 6n | White soild | 50.0 | 161—162 | 449.0643(449.0646) |
6g | White soild | 70.3 | 169—171 | 412.0927(412.0927) | 6o | White soild | 65.7 | 150—151 | 429.1196(429.1192) |
6h | White soild | 65.4 | 191—193 | 536.9930(536.9941) |
Table 2 Appearance, yields, melting points and HRMS data of compounds 6a—6o
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ | Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ |
---|---|---|---|---|---|---|---|---|---|
6a | White soild | 76.3 | 165—167 | 387.0532(387.0530) | 6i | White soild | 84.1 | 124—125 | 421.0789(421.0793) |
6b | White soild | 73.3 | 171—173 | 387.0526(387.0530) | 6j | White soild | 74.7 | 167—169 | 437.0739(437.0743) |
6c | White soild | 65.3 | 186—188 | 432.0380(432.0381) | 6k | White soild | 59.4 | 170—171 | 431.0790(431.0792) |
6d | White soild | 75.3 | 169—171 | 398.0770(3980770) | 6l | White soild | 76.8 | 167—168 | 452.0849(452.0852) |
6e | White soild | 65.7 | 193—195 | 398.0767(398.0770) | 6m | White soild | 69.1 | 167—168 | 485.0910(485.0913) |
6f | White soild | 74.7 | 207—209 | 403.0632(403.0633) | 6n | White soild | 50.0 | 161—162 | 449.0643(449.0646) |
6g | White soild | 70.3 | 169—171 | 412.0927(412.0927) | 6o | White soild | 65.7 | 150—151 | 429.1196(429.1192) |
6h | White soild | 65.4 | 191—193 | 536.9930(536.9941) |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(101 MHz), δ |
---|---|---|
6aa | 13.11(br, 1H, SO2NH), 9.70(s, 1H, CONH—Pyrim), 8.82(d, J=4.9 Hz, 1H, Pyrim—H), 8.29(d, J=7.2 Hz, 1H, Ph—H), 7.80—7.62(m, 3H, Ph—H), 7.38(d, J=4.9 Hz, 1H, Pyrim—H), 5.38(s, 1H, CH), 3.49(s, 6H, 2×OCH3) | 166.58, 159.61, 157.09, 148.53, 136.91, 134.94, 132.72, 131.66, 131.46, 127.33, 113.08, 101.98, 53.42 |
6ba | 12.84(br, 1H, SO2NH), 9.68(s, 1H, CONH—Pyrim), 8.79(d, J=4.6 Hz, 1H, Pyrim—H), 8.14(d, J=8.0 Hz, 2H, Ph—H), 7.71(d, J=7.9 Hz, 2H, Ph—H), 7.35(d, J=4.6 Hz, 1H, Pyrim—H), 5.36(s, 1H, CH), 3.48(s, 6H, 2×OCH3) | 166.64, 159.39, 157.08, 148.88, 139.36, 138.60, 130.12, 129.08, 113.00, 101.92, 53.38 |
6cb | 13.47(br, 1H, SO2NH), 11.09(s, 1H, CONH—Pyrim), 8.52(d, J=6.6 Hz, 1H, Pyrim—H), 8.09—7.94(m, 3H, Ph—H), 7.17(d, J=6.6 Hz, 1H, Pyrim—H), 5.35(s, 1H, CH), 3.36(s, 6H, 2×OCH3) | 163.76, 159.11, 156.88, 146.38, 137.82, 134.07, 129.36, 128.66, 127.23, 124.13, 107.02, 101.61, 54.07 |
6da | 13.16(br, 1H, SO2NH), 9.76(br, 1H, CONH—Pyrim), 8.79(d, J=5.1 Hz, 1H, Pyrim—H), 8.40(d, J=7.4 Hz, 1H, Ph—H), 8.03—7.93(m, 3H, Ph—H), 7.35(d, J=5.1 Hz, 1H, Pyrim—H), 5.33(s, 1H, CH), 3.45(s, 6H, 2×OCH3) | 166.91, 159.34, 156.95, 148.73, 148.40, 135.32, 133.26, 132.26, 131.44, 124.76, 113.06, 102.24, 53.56 |
6eb | 12.95(br, 1H, SO2NH), 10.89(s, 1H, CONH—Pyrim), 8.74(d, J=4.9 Hz, 1H, Pyrim—H), 8.44(d, J=8.4 Hz, 2H, Ph—H), 8.26(d, J=8.4 Hz, 2H, Ph—H),7.25(d, J=4.9 Hz, 1H, Pyrim—H), 5.32(s, 1H, CH), 3.36(s, 6H, 2×OCH3) | 165.92, 158.71, 156.75, 150.14, 129.35, 127.22, 124.39, 112.91, 106.54, 101.37, 53.61 |
6fa | 13.18(br, 1H, SO2NH), 9.80(s, 1H, CONH—Pyrim), 8.79(d, J=4.9 Hz, 1H, Pyrim—H), 7.80(t, J=7.8 Hz, 1H, Ph—H), 7.71—7.61(m, 2H, Ph—H), 7.35(d, J=5.1 Hz, 1H, Pyrim—H), 5.35(s, 1H, CH), 3.45(s, 6H, 2×OCH3), 2.91(s, 3H, CH3) | 167.59, 160.47, 157.84, 152.35, 150.00, 143.27, 136.70, 135.17, 130.18, 123.39, 114.07, 102.83, 54.34, 21.98 |
6ga | 12.73(br, 1H, SO2NH), 9.83(br, 1H, CONH—Pyrim), 8.81(d, J=4.2 Hz, 1H, Pyrim—H), 8.30(d, J=5.7 Hz, 1H, Ph—H), 7.86—7.70(m, 3H, Ph—H), 7.34(d, J=4.3 Hz, 1H, Pyrim—H), 5.37(s, 1H, CH), 3.94(s, 3H, COOCH3), 3.45(s, 6H, 2×OCH3) | 167.16, 166.94, 159.21, 157.04, 148.94, 136.99, 133.71, 132.59, 131.94, 130.64, 129.40, 112.96, 102.25, 53.54, 52.60 |
6ha | 12.84(br, 1H, SO2NH), 9.72(br, 1H, CONH—Pyrim), 8.83(d, J=4.4 Hz, 1H, Pyrim—H), 8.66(s, 1H, Ph—H), 8.25(d, J=7.4 Hz, 1H, Ph—H), 7.59(d, J=7.7 Hz, 1H, Ph—H), 7.37(d, J=4.4 Hz, 1H, Pyrim—H), 5.39(s, 1H, CH), 3.96(s, 3H, COOCH3), 3.49(s, 6H, 2×OCH3) | 167.00, 166.55, 159.14, 156.99, 148.78, 142.65, 140.27, 138.28, 131.88, 131.07, 113.00, 102.32, 95.58, 53.55, 52.71 |
6ia | 13.08(s, 1H, SO2NH), 9.78(s, 1H, CONH—Pyrim), 8.79(d, J=4.9 Hz, 1H, Pyrim—H), 8.53(d, J=4.9 Hz, 1H, Ph—H), 8.03—7.98(m, 3H, Ph—H), 7.35(d, J=4.8 Hz, 1H, Pyrim—H), 5.32(s, 1H, CH), 3.45(s, 6H, 2×OCH3) | 167.33, 159.94, 157.63, 149.20, 138.24, 134.73, 134.65, 133.24, 128.85(q, 3JFC=6.3 Hz), 127.79(q, 2JFC=33.2 Hz), 123.74(q, 1JFC=273.5 Hz), 113.63, 102.58, 53.97 |
6ja | 13.04(br, 1H, SO2NH), 9.75(s, 1H, CONH—Pyrim), 8.78(d, J=4.0 Hz, 1H, Pyrim—H), 8.14(d, J=7.4 Hz, 1H, Ph—H), 7.88(t, J=7.6 Hz, 1H, Ph—H), 7.67—7.62(m, 2H, Ph—H), 7.27(d, J=4.0 Hz, 1H, Pyrim—H), 5.29(s, 1H, CH), 3.44(s, 6H, 2×OCH3) | 167.83, 160.11, 157.98, 149.56, 146.72, 136.83, 133.60, 132.46, 127.99, 121.47, 121.27(d,J=259.3 Hz), 113.96, 102.96, 54.29 |
6kb | 12.54(br, 1H, SO2NH), 10.76(s, 1H, CONH—Pyrim), 8.76(d, J=6.6 Hz, 1H, Pyrim—H), 8.27—7.68(m, 4H, Ph—H), 7.27(d, J=6.6 Hz, 1H, Pyrim—H), 5.29(s, 1H, CH), 4.39(t, J=7.1 Hz, 2H, OCH2CH2Cl), 3.80(t, J=7.1 Hz, 2H, OCH2CH2Cl), 3.38(s, 6H, 2×OCH3) | 159.12, 158.65, 157.02, 148.74, 135.74, 131.16, 120.64, 113.95, 112.70, 106.56, 102.76, 101.66, 69.13, 53.76, 53.32 |
6la | 12.76(s, 1H, SO2NH), 9.64(s, 1H, CONH—Pyrim), 8.78(d, J=5.1 Hz, 1H, Pyrim—H), 8.31(d, J=4.2 Hz, 1H, Py—H), 7.92(d, J=8.5 Hz, 1H, Py—H), 7.73(dd, J=8.4, 4.4 Hz, 1H, Py—H), 7.34(d, J=5.1 Hz, 1H, Pyrim—H), 5.30(s, 1H, CH), 4.93(q, 3JFH=8.4 Hz, 2H, OCH2CF3), 3.43(s, 6H, 2×OCH3) | 167.62, 159.96, 158.00, 152.37, 150.04, 145.93, 142.72, 129.84, 124.73, 124.24(q, 1JFC=277.5 Hz), 113.62, 102.88, 66.83(q, 2JFC=36.0 Hz), 54.16 |
6mb | 13.60(br, 1H, SO2NH), 11.02(s, 1H, CONH—Pyrim), 9.18(d, J=6.7 Hz, 1H, Py—H), 8.76(d, J=4.9 Hz, 1H, Pyrim—H), 8.00(d, J=8.7 Hz, 1H, Py—H), 7.79(t, J=7.7 Hz, 1H, Py—H), 7.48(t, J=6.7 Hz, 1H, Py—H), 7.27(d, J=4.9 Hz, 1H, Pyrim—H), 5.29(s, 1H, CH), 3.61(d, J=7.3 Hz, 2H, SO2CH2CH3), 3.36(s, 6H, 2×OCH3), 1.16(t, J=7.1 Hz, 3H, SO2CH2CH3) | 167.50, 159.49, 156.79, 145.92, 144.79, 130.98, 128.75, 126.25, 118.96, 117.25, 113.40, 108.20, 102.09, 54.33, 49.06, 7.15 |
6na | 13.24(s, 1H, SO2NH), 10.01(s, 1H, CONH—Pyrim), 8.86(d, J=5.1 Hz, 1H, Pyrim—H), 7.39(d, J=5.1 Hz, 1H, Pyrim—H), 5.39(s, 1H, CH), 4.31(s, 3H, Pyrazole—CH3), 3.86(s, 3H, COOCH3), 3.47(s, 6H, 2×OCH3) | 167.03, 160.16, 159.23, 156.75, 149.80, 139.69, 138.28, 113.37, 113.19, 102.10, 53.52, 51.94, 41.11 |
6oa | 13.11(s, 1H, SO2NH), 9.92(s, 1H, CONH—Pyrim), 8.81(d, J=4.8 Hz, 1H, Pyrim—H), 7.93(s, 1H, Pyrazole—H), 7.37(d, J=4.8 Hz, 1H, Pyrim—H), 5.38(s, 1H, CH), 4.32(s, 3H, Pyrazole—CH3), 4.25(q, J=7.0 Hz, 2H, CO2CH2CH3), 3.47(s, 6H, 2×OCH3), 1.26(t, J=7.0 Hz, 3H, CO2CH2CH3) | 167.83, 161.27, 159.99, 157.55, 150.52, 140.71, 139.45, 116.73, 113.89, 103.15, 61.44, 54.43, 41.58, 29.84 |
Table 3 1H NMR and 13C NMR data of compounds 6a—6o
Compd. | 1H NMR(400 MHz), δ | 13C NMR(101 MHz), δ |
---|---|---|
6aa | 13.11(br, 1H, SO2NH), 9.70(s, 1H, CONH—Pyrim), 8.82(d, J=4.9 Hz, 1H, Pyrim—H), 8.29(d, J=7.2 Hz, 1H, Ph—H), 7.80—7.62(m, 3H, Ph—H), 7.38(d, J=4.9 Hz, 1H, Pyrim—H), 5.38(s, 1H, CH), 3.49(s, 6H, 2×OCH3) | 166.58, 159.61, 157.09, 148.53, 136.91, 134.94, 132.72, 131.66, 131.46, 127.33, 113.08, 101.98, 53.42 |
6ba | 12.84(br, 1H, SO2NH), 9.68(s, 1H, CONH—Pyrim), 8.79(d, J=4.6 Hz, 1H, Pyrim—H), 8.14(d, J=8.0 Hz, 2H, Ph—H), 7.71(d, J=7.9 Hz, 2H, Ph—H), 7.35(d, J=4.6 Hz, 1H, Pyrim—H), 5.36(s, 1H, CH), 3.48(s, 6H, 2×OCH3) | 166.64, 159.39, 157.08, 148.88, 139.36, 138.60, 130.12, 129.08, 113.00, 101.92, 53.38 |
6cb | 13.47(br, 1H, SO2NH), 11.09(s, 1H, CONH—Pyrim), 8.52(d, J=6.6 Hz, 1H, Pyrim—H), 8.09—7.94(m, 3H, Ph—H), 7.17(d, J=6.6 Hz, 1H, Pyrim—H), 5.35(s, 1H, CH), 3.36(s, 6H, 2×OCH3) | 163.76, 159.11, 156.88, 146.38, 137.82, 134.07, 129.36, 128.66, 127.23, 124.13, 107.02, 101.61, 54.07 |
6da | 13.16(br, 1H, SO2NH), 9.76(br, 1H, CONH—Pyrim), 8.79(d, J=5.1 Hz, 1H, Pyrim—H), 8.40(d, J=7.4 Hz, 1H, Ph—H), 8.03—7.93(m, 3H, Ph—H), 7.35(d, J=5.1 Hz, 1H, Pyrim—H), 5.33(s, 1H, CH), 3.45(s, 6H, 2×OCH3) | 166.91, 159.34, 156.95, 148.73, 148.40, 135.32, 133.26, 132.26, 131.44, 124.76, 113.06, 102.24, 53.56 |
6eb | 12.95(br, 1H, SO2NH), 10.89(s, 1H, CONH—Pyrim), 8.74(d, J=4.9 Hz, 1H, Pyrim—H), 8.44(d, J=8.4 Hz, 2H, Ph—H), 8.26(d, J=8.4 Hz, 2H, Ph—H),7.25(d, J=4.9 Hz, 1H, Pyrim—H), 5.32(s, 1H, CH), 3.36(s, 6H, 2×OCH3) | 165.92, 158.71, 156.75, 150.14, 129.35, 127.22, 124.39, 112.91, 106.54, 101.37, 53.61 |
6fa | 13.18(br, 1H, SO2NH), 9.80(s, 1H, CONH—Pyrim), 8.79(d, J=4.9 Hz, 1H, Pyrim—H), 7.80(t, J=7.8 Hz, 1H, Ph—H), 7.71—7.61(m, 2H, Ph—H), 7.35(d, J=5.1 Hz, 1H, Pyrim—H), 5.35(s, 1H, CH), 3.45(s, 6H, 2×OCH3), 2.91(s, 3H, CH3) | 167.59, 160.47, 157.84, 152.35, 150.00, 143.27, 136.70, 135.17, 130.18, 123.39, 114.07, 102.83, 54.34, 21.98 |
6ga | 12.73(br, 1H, SO2NH), 9.83(br, 1H, CONH—Pyrim), 8.81(d, J=4.2 Hz, 1H, Pyrim—H), 8.30(d, J=5.7 Hz, 1H, Ph—H), 7.86—7.70(m, 3H, Ph—H), 7.34(d, J=4.3 Hz, 1H, Pyrim—H), 5.37(s, 1H, CH), 3.94(s, 3H, COOCH3), 3.45(s, 6H, 2×OCH3) | 167.16, 166.94, 159.21, 157.04, 148.94, 136.99, 133.71, 132.59, 131.94, 130.64, 129.40, 112.96, 102.25, 53.54, 52.60 |
6ha | 12.84(br, 1H, SO2NH), 9.72(br, 1H, CONH—Pyrim), 8.83(d, J=4.4 Hz, 1H, Pyrim—H), 8.66(s, 1H, Ph—H), 8.25(d, J=7.4 Hz, 1H, Ph—H), 7.59(d, J=7.7 Hz, 1H, Ph—H), 7.37(d, J=4.4 Hz, 1H, Pyrim—H), 5.39(s, 1H, CH), 3.96(s, 3H, COOCH3), 3.49(s, 6H, 2×OCH3) | 167.00, 166.55, 159.14, 156.99, 148.78, 142.65, 140.27, 138.28, 131.88, 131.07, 113.00, 102.32, 95.58, 53.55, 52.71 |
6ia | 13.08(s, 1H, SO2NH), 9.78(s, 1H, CONH—Pyrim), 8.79(d, J=4.9 Hz, 1H, Pyrim—H), 8.53(d, J=4.9 Hz, 1H, Ph—H), 8.03—7.98(m, 3H, Ph—H), 7.35(d, J=4.8 Hz, 1H, Pyrim—H), 5.32(s, 1H, CH), 3.45(s, 6H, 2×OCH3) | 167.33, 159.94, 157.63, 149.20, 138.24, 134.73, 134.65, 133.24, 128.85(q, 3JFC=6.3 Hz), 127.79(q, 2JFC=33.2 Hz), 123.74(q, 1JFC=273.5 Hz), 113.63, 102.58, 53.97 |
6ja | 13.04(br, 1H, SO2NH), 9.75(s, 1H, CONH—Pyrim), 8.78(d, J=4.0 Hz, 1H, Pyrim—H), 8.14(d, J=7.4 Hz, 1H, Ph—H), 7.88(t, J=7.6 Hz, 1H, Ph—H), 7.67—7.62(m, 2H, Ph—H), 7.27(d, J=4.0 Hz, 1H, Pyrim—H), 5.29(s, 1H, CH), 3.44(s, 6H, 2×OCH3) | 167.83, 160.11, 157.98, 149.56, 146.72, 136.83, 133.60, 132.46, 127.99, 121.47, 121.27(d,J=259.3 Hz), 113.96, 102.96, 54.29 |
6kb | 12.54(br, 1H, SO2NH), 10.76(s, 1H, CONH—Pyrim), 8.76(d, J=6.6 Hz, 1H, Pyrim—H), 8.27—7.68(m, 4H, Ph—H), 7.27(d, J=6.6 Hz, 1H, Pyrim—H), 5.29(s, 1H, CH), 4.39(t, J=7.1 Hz, 2H, OCH2CH2Cl), 3.80(t, J=7.1 Hz, 2H, OCH2CH2Cl), 3.38(s, 6H, 2×OCH3) | 159.12, 158.65, 157.02, 148.74, 135.74, 131.16, 120.64, 113.95, 112.70, 106.56, 102.76, 101.66, 69.13, 53.76, 53.32 |
6la | 12.76(s, 1H, SO2NH), 9.64(s, 1H, CONH—Pyrim), 8.78(d, J=5.1 Hz, 1H, Pyrim—H), 8.31(d, J=4.2 Hz, 1H, Py—H), 7.92(d, J=8.5 Hz, 1H, Py—H), 7.73(dd, J=8.4, 4.4 Hz, 1H, Py—H), 7.34(d, J=5.1 Hz, 1H, Pyrim—H), 5.30(s, 1H, CH), 4.93(q, 3JFH=8.4 Hz, 2H, OCH2CF3), 3.43(s, 6H, 2×OCH3) | 167.62, 159.96, 158.00, 152.37, 150.04, 145.93, 142.72, 129.84, 124.73, 124.24(q, 1JFC=277.5 Hz), 113.62, 102.88, 66.83(q, 2JFC=36.0 Hz), 54.16 |
6mb | 13.60(br, 1H, SO2NH), 11.02(s, 1H, CONH—Pyrim), 9.18(d, J=6.7 Hz, 1H, Py—H), 8.76(d, J=4.9 Hz, 1H, Pyrim—H), 8.00(d, J=8.7 Hz, 1H, Py—H), 7.79(t, J=7.7 Hz, 1H, Py—H), 7.48(t, J=6.7 Hz, 1H, Py—H), 7.27(d, J=4.9 Hz, 1H, Pyrim—H), 5.29(s, 1H, CH), 3.61(d, J=7.3 Hz, 2H, SO2CH2CH3), 3.36(s, 6H, 2×OCH3), 1.16(t, J=7.1 Hz, 3H, SO2CH2CH3) | 167.50, 159.49, 156.79, 145.92, 144.79, 130.98, 128.75, 126.25, 118.96, 117.25, 113.40, 108.20, 102.09, 54.33, 49.06, 7.15 |
6na | 13.24(s, 1H, SO2NH), 10.01(s, 1H, CONH—Pyrim), 8.86(d, J=5.1 Hz, 1H, Pyrim—H), 7.39(d, J=5.1 Hz, 1H, Pyrim—H), 5.39(s, 1H, CH), 4.31(s, 3H, Pyrazole—CH3), 3.86(s, 3H, COOCH3), 3.47(s, 6H, 2×OCH3) | 167.03, 160.16, 159.23, 156.75, 149.80, 139.69, 138.28, 113.37, 113.19, 102.10, 53.52, 51.94, 41.11 |
6oa | 13.11(s, 1H, SO2NH), 9.92(s, 1H, CONH—Pyrim), 8.81(d, J=4.8 Hz, 1H, Pyrim—H), 7.93(s, 1H, Pyrazole—H), 7.37(d, J=4.8 Hz, 1H, Pyrim—H), 5.38(s, 1H, CH), 4.32(s, 3H, Pyrazole—CH3), 4.25(q, J=7.0 Hz, 2H, CO2CH2CH3), 3.47(s, 6H, 2×OCH3), 1.26(t, J=7.0 Hz, 3H, CO2CH2CH3) | 167.83, 161.27, 159.99, 157.55, 150.52, 140.71, 139.45, 116.73, 113.89, 103.15, 61.44, 54.43, 41.58, 29.84 |
Compd. | Herbicidal activity(%) | |||||||
---|---|---|---|---|---|---|---|---|
Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitaria sanguinalis | |||||
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
6a | 97.0 | 100 | 91.5 | 50.2 | 62.0 | 36.1 | 10.0 | 33.5 |
6b | 86.6 | 90.5 | 37.4 | 27.7 | 41.6 | 19.3 | 32.5 | 52.7 |
6c | 80.8 | 100 | 86.6 | 52.9 | 61.3 | 41.5 | 25.0 | 48.2 |
6d | 82.4 | 100 | 90.6 | 89.4 | 83.6 | 56.1 | 87.4 | 55.4 |
6e | 83.6 | 98 | 48.9 | 26.2 | 58.7 | 26.1 | 45.1 | 49.1 |
6f | 100 | 100 | 95.7 | 43.7 | 82.3 | 70.7 | 35.8 | 31.3 |
6g | 94.5 | 100 | 91.5 | 79.1 | 88.2 | 62.2 | 67.9 | 67.9 |
6h | 83.4 | 45.4 | 92.6 | 22.9 | 42.9 | 30.0 | 20.2 | 25.9 |
6i | 94.8 | 100 | 100 | 86.1 | 60.6 | 39.3 | 58.9 | 74.2 |
6j | 87.2 | 100 | 91.5 | 33.8 | 39.7 | 25.6 | 25.0 | 32.1 |
6k | 99.0 | 96.5 | 100 | 47.2 | 49.5 | 6.1 | 37.0 | 16.1 |
6l | 89.9 | 33.9 | 98.2 | 36.8 | 42.3 | 34.1 | 36.8 | 31.3 |
6m | 83.6 | 95.2 | 78.7 | 32.6 | 46.2 | 41.5 | 35.0 | 32.1 |
6n | 83.1 | 82.1 | 85.7 | 43.2 | 58.7 | 50.4 | 49.7 | 58.4 |
6o | 80.2 | 79.4 | 84.1 | 60.4 | 63.2 | 64.0 | 45.1 | 50.1 |
Monosulfuron | 87 | 85 | 100 | 100 | 100 | 100 | 81 | 100 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 99 | 100 | 100 | 100 |
Table 4 Herbicidal activity of compounds 6a—6o by pot-culture method at dosage of 1500 g/ha
Compd. | Herbicidal activity(%) | |||||||
---|---|---|---|---|---|---|---|---|
Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitaria sanguinalis | |||||
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
6a | 97.0 | 100 | 91.5 | 50.2 | 62.0 | 36.1 | 10.0 | 33.5 |
6b | 86.6 | 90.5 | 37.4 | 27.7 | 41.6 | 19.3 | 32.5 | 52.7 |
6c | 80.8 | 100 | 86.6 | 52.9 | 61.3 | 41.5 | 25.0 | 48.2 |
6d | 82.4 | 100 | 90.6 | 89.4 | 83.6 | 56.1 | 87.4 | 55.4 |
6e | 83.6 | 98 | 48.9 | 26.2 | 58.7 | 26.1 | 45.1 | 49.1 |
6f | 100 | 100 | 95.7 | 43.7 | 82.3 | 70.7 | 35.8 | 31.3 |
6g | 94.5 | 100 | 91.5 | 79.1 | 88.2 | 62.2 | 67.9 | 67.9 |
6h | 83.4 | 45.4 | 92.6 | 22.9 | 42.9 | 30.0 | 20.2 | 25.9 |
6i | 94.8 | 100 | 100 | 86.1 | 60.6 | 39.3 | 58.9 | 74.2 |
6j | 87.2 | 100 | 91.5 | 33.8 | 39.7 | 25.6 | 25.0 | 32.1 |
6k | 99.0 | 96.5 | 100 | 47.2 | 49.5 | 6.1 | 37.0 | 16.1 |
6l | 89.9 | 33.9 | 98.2 | 36.8 | 42.3 | 34.1 | 36.8 | 31.3 |
6m | 83.6 | 95.2 | 78.7 | 32.6 | 46.2 | 41.5 | 35.0 | 32.1 |
6n | 83.1 | 82.1 | 85.7 | 43.2 | 58.7 | 50.4 | 49.7 | 58.4 |
6o | 80.2 | 79.4 | 84.1 | 60.4 | 63.2 | 64.0 | 45.1 | 50.1 |
Monosulfuron | 87 | 85 | 100 | 100 | 100 | 100 | 81 | 100 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 99 | 100 | 100 | 100 |
Compd. | Dosage/ (g·ha-1) | Herbicidal activity(%) | Compd. | Dosage/ (g·ha-1) | Herbicidal activity(%) | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Brassica napus | Amaranthus retroflexus | Brassica napus | Amaranthus retroflexus | ||||||||
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | ||||
6a | 300 | 100 | 100.0 | 85.0 | 6i | 300 | 100 | 75.9 | 100 | 85.5 | |
75 | 100 | 78.1 | 60.0 | 75 | 54.8 | 43.3 | 56.9 | 32.5 | |||
6b | 300 | 45.3 | 34.6 | 6j | 300 | 88.0 | 75.6 | 85.0 | |||
75 | 12.4 | 15 | 75 | 55.1 | 35.4 | 45.1 | |||||
6c | 300 | 45.3 | 100 | 42.7 | 6k | 300 | 100 | 97.5 | 86.6 | ||
75 | 12.1 | 10 | 12.1 | 75 | 64.5 | 51.0 | 50.0 | ||||
6d | 300 | 100 | 100 | 94.6 | 90.6 | 6l | 300 | 74.9 | 82.1 | ||
75 | 87.3 | 73 | 74.2 | 60.6 | 75 | 17.4 | 23.3 | ||||
6e | 300 | 51.7 | 45.7 | 6m | 300 | 75.6 | 71.2 | 62.3 | |||
75 | 20.4 | 10 | 75 | 45.9 | 33.3 | 10.0 | |||||
6f | 300 | 100 | 90.9 | 93.8 | 6n | 300 | 67.3 | 66.3 | 77.1 | ||
75 | 81.2 | 30.2 | 85.7 | 75 | 31 | 10 | 32.7 | ||||
6g | 300 | 100 | 100 | 81.2 | 71.1 | 6o | 300 | 64.8 | 58.8 | 72.2 | |
75 | 100 | 97.1 | 63.1 | 29.1 | 75 | 40.2 | 10 | 30.1 | |||
6h | 300 | 76.2 | 82.1 | MSa | 75 | 100 | 100 | 100 | 100 | ||
75 | 44.8 | 50.6 | CSb | 75 | 100 | 100 | 100 | 100 |
Table 5 Herbicidal activity of compounds 6a—6o at lower dosage
Compd. | Dosage/ (g·ha-1) | Herbicidal activity(%) | Compd. | Dosage/ (g·ha-1) | Herbicidal activity(%) | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Brassica napus | Amaranthus retroflexus | Brassica napus | Amaranthus retroflexus | ||||||||
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | ||||
6a | 300 | 100 | 100.0 | 85.0 | 6i | 300 | 100 | 75.9 | 100 | 85.5 | |
75 | 100 | 78.1 | 60.0 | 75 | 54.8 | 43.3 | 56.9 | 32.5 | |||
6b | 300 | 45.3 | 34.6 | 6j | 300 | 88.0 | 75.6 | 85.0 | |||
75 | 12.4 | 15 | 75 | 55.1 | 35.4 | 45.1 | |||||
6c | 300 | 45.3 | 100 | 42.7 | 6k | 300 | 100 | 97.5 | 86.6 | ||
75 | 12.1 | 10 | 12.1 | 75 | 64.5 | 51.0 | 50.0 | ||||
6d | 300 | 100 | 100 | 94.6 | 90.6 | 6l | 300 | 74.9 | 82.1 | ||
75 | 87.3 | 73 | 74.2 | 60.6 | 75 | 17.4 | 23.3 | ||||
6e | 300 | 51.7 | 45.7 | 6m | 300 | 75.6 | 71.2 | 62.3 | |||
75 | 20.4 | 10 | 75 | 45.9 | 33.3 | 10.0 | |||||
6f | 300 | 100 | 90.9 | 93.8 | 6n | 300 | 67.3 | 66.3 | 77.1 | ||
75 | 81.2 | 30.2 | 85.7 | 75 | 31 | 10 | 32.7 | ||||
6g | 300 | 100 | 100 | 81.2 | 71.1 | 6o | 300 | 64.8 | 58.8 | 72.2 | |
75 | 100 | 97.1 | 63.1 | 29.1 | 75 | 40.2 | 10 | 30.1 | |||
6h | 300 | 76.2 | 82.1 | MSa | 75 | 100 | 100 | 100 | 100 | ||
75 | 44.8 | 50.6 | CSb | 75 | 100 | 100 | 100 | 100 |
Compd. | Antifungal activity(%, inhibition) | ||||||
---|---|---|---|---|---|---|---|
C. arachidicola | P. piricola | F. moniliforme | S. sclerotiorum | R. cerealis | C. lagenarium | R. solani | |
6a | 25.0 | 27.3 | 8.3 | 51.6 | 59.5 | 30.0 | 29.4 |
6b | 12.5 | 72.7 | 25.0 | 21.9 | 61.9 | 50.0 | 21.6 |
6c | 25.0 | 18.2 | 25.0 | 18.8 | 61.9 | 40.0 | 9.8 |
6d | 75.0 | 27.3 | 25.0 | 31.3 | 57.1 | 30.0 | 21.6 |
6e | 12.5 | 45.5 | 25.0 | 32.8 | 59.5 | 40.0 | 15.7 |
6f | 25.0 | 27.3 | 16.7 | 40.6 | 61.9 | 50.0 | 21.6 |
6g | 12.3 | 9.1 | 16.7 | 28.1 | 54.8 | 40.0 | 13.7 |
6h | 26.9 | 10.5 | 33.3 | 17.4 | 57.4 | 38.2 | 19.4 |
6i | 45.0 | 87.5 | 40.0 | 89.3 | 88.0 | 32.3 | 65.9 |
6j | 12.5 | 50.0 | 25.0 | 21.9 | 59.5 | 40.0 | 16.7 |
6k | 12.5 | 45.5 | 25.0 | 12.5 | 64.3 | 55.0 | 13.7 |
6l | 23.1 | 15.8 | 18.5 | 13.0 | 36.1 | 20.6 | 16.7 |
6m | 50.0 | 50.0 | 11.1 | 17.4 | 41.0 | 20.6 | 22.2 |
6n | 42.1 | 45.1 | 33.3 | 10.6 | 58.5 | 45.2 | 11.2 |
6o | 70.0 | 87.5 | 64.0 | 67.9 | 89.3 | 32.3 | 82.9 |
Bensulfuron-methyl | 3.8 | 15.8 | 25.0 | 45.5 | 46.9 | 29.4 | 35.0 |
Chlorothalonil | 75 | <50.0 | <50.0 | 100 | 100 | 95 | 100 |
Carbendazim | <50.0 | 100 | 99.2 | <50.0 | 100 | 100 | <50.0 |
Table 6 Antifungal activity of compounds 6a—6o at the dosage of 50 mg/L(in vitro)
Compd. | Antifungal activity(%, inhibition) | ||||||
---|---|---|---|---|---|---|---|
C. arachidicola | P. piricola | F. moniliforme | S. sclerotiorum | R. cerealis | C. lagenarium | R. solani | |
6a | 25.0 | 27.3 | 8.3 | 51.6 | 59.5 | 30.0 | 29.4 |
6b | 12.5 | 72.7 | 25.0 | 21.9 | 61.9 | 50.0 | 21.6 |
6c | 25.0 | 18.2 | 25.0 | 18.8 | 61.9 | 40.0 | 9.8 |
6d | 75.0 | 27.3 | 25.0 | 31.3 | 57.1 | 30.0 | 21.6 |
6e | 12.5 | 45.5 | 25.0 | 32.8 | 59.5 | 40.0 | 15.7 |
6f | 25.0 | 27.3 | 16.7 | 40.6 | 61.9 | 50.0 | 21.6 |
6g | 12.3 | 9.1 | 16.7 | 28.1 | 54.8 | 40.0 | 13.7 |
6h | 26.9 | 10.5 | 33.3 | 17.4 | 57.4 | 38.2 | 19.4 |
6i | 45.0 | 87.5 | 40.0 | 89.3 | 88.0 | 32.3 | 65.9 |
6j | 12.5 | 50.0 | 25.0 | 21.9 | 59.5 | 40.0 | 16.7 |
6k | 12.5 | 45.5 | 25.0 | 12.5 | 64.3 | 55.0 | 13.7 |
6l | 23.1 | 15.8 | 18.5 | 13.0 | 36.1 | 20.6 | 16.7 |
6m | 50.0 | 50.0 | 11.1 | 17.4 | 41.0 | 20.6 | 22.2 |
6n | 42.1 | 45.1 | 33.3 | 10.6 | 58.5 | 45.2 | 11.2 |
6o | 70.0 | 87.5 | 64.0 | 67.9 | 89.3 | 32.3 | 82.9 |
Bensulfuron-methyl | 3.8 | 15.8 | 25.0 | 45.5 | 46.9 | 29.4 | 35.0 |
Chlorothalonil | 75 | <50.0 | <50.0 | 100 | 100 | 95 | 100 |
Carbendazim | <50.0 | 100 | 99.2 | <50.0 | 100 | 100 | <50.0 |
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