高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (5): 907.doi: 10.7503/cjcu20141121
陈伟, 魏巍, 李玉新, 万莹莹, 刘巧霞, 李永红, 于淑晶, 李正名()
收稿日期:
2014-12-22
出版日期:
2015-05-10
发布日期:
2015-04-08
作者简介:
联系人简介: 李正名, 男, 博士, 教授, 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, LI Yuxin, WAN Yingying, LIU Qiaoxia, LI Yonghong, YU Shujing, LI Zhengming*()
Received:
2014-12-22
Online:
2015-05-10
Published:
2015-04-08
Contact:
LI Zhengming
E-mail:nkzml@vip.163.com
Supported by:
摘要:
设计合成了一系列2-甲基-6-硝基苯磺酰脲衍生物(4a~4p), 通过核磁共振氢谱(1H NMR)和高分辨质谱(HRMS)对其结构进行了确认. 盆栽法除草测试结果表明, 在300 g/ha剂量下, 目标化合物具有优异的芽前或芽后除草活性. 进一步筛选发现, 在75 g/ha剂量下, 化合物4b, 4g, 4h, 4l和4p对油菜、 反枝苋和稗草具有98%以上的除草活性, 与对照药单嘧磺隆(100%)和氯磺隆(≥96.3%)相当. 另外, 部分化合物对真菌也表现出一定的抑制效果, 其中化合物4l对油菜菌核病菌的半最大效应浓度EC50=9.20 mg/L(对照药多菌灵的EC50=5.79 mg/L).
中图分类号:
TrendMD:
陈伟, 魏巍, 李玉新, 万莹莹, 刘巧霞, 李永红, 于淑晶, 李正名. 2-甲基-6-硝基苯磺酰脲衍生物的合成及生物活性. 高等学校化学学报, 2015, 36(5): 907.
CHEN Wei, WEI Wei, LI Yuxin, WAN Yingying, LIU Qiaoxia, LI Yonghong, YU Shujing, LI Zhengming. Synthesis and Biological Activity of 2-Methyl-6-nitrobenzenesulfonylurea Derivatives†. Chem. J. Chinese Universities, 2015, 36(5): 907.
Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ | Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ |
---|---|---|---|---|---|---|---|
4a | 64.0 | 228—230 | 372.0166(372.0169) | 4i | 84.7 | 191—193 | 398.0589(398.0593) |
4b | 76.2 | 212—214 | 352.0712(352.0716) | 4j | 63.4 | 211—212 | 386.0326(386.0326) |
4c | 73.2 | 198—199 | 368.0663(368.0665) | 4k | 49.6 | 209—210 | 402.0275(402.0275) |
4d | 80.1 | 203—205 | 382.0817(382.0821) | 4l | 68.4 | 221—223 | 398.0768(398.0770) |
4e | 58.4 | 220—221 | 384.0433(384.0436) | 4m | 74.4 | 179—180 | 414.0538(414.0542) |
4f | 63.2 | 226—227 | 406.0432(406.0433) | 4n | 63.2 | 208—209 | 368.0656(368.0665) |
4g | 73.0 | 216—218 | 366.0870(366.0872) | 4o | 71.3 | 191—193 | 383.0763(383.0774) |
4h | 74.3 | 183—184 | 380.0820(380.0821) | 4p | 67.5 | 195—197 | 412.1031(412.1039) |
Table 1 Yields, melting points and HRMS data of compounds 4a—4p*
Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ | Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ |
---|---|---|---|---|---|---|---|
4a | 64.0 | 228—230 | 372.0166(372.0169) | 4i | 84.7 | 191—193 | 398.0589(398.0593) |
4b | 76.2 | 212—214 | 352.0712(352.0716) | 4j | 63.4 | 211—212 | 386.0326(386.0326) |
4c | 73.2 | 198—199 | 368.0663(368.0665) | 4k | 49.6 | 209—210 | 402.0275(402.0275) |
4d | 80.1 | 203—205 | 382.0817(382.0821) | 4l | 68.4 | 221—223 | 398.0768(398.0770) |
4e | 58.4 | 220—221 | 384.0433(384.0436) | 4m | 74.4 | 179—180 | 414.0538(414.0542) |
4f | 63.2 | 226—227 | 406.0432(406.0433) | 4n | 63.2 | 208—209 | 368.0656(368.0665) |
4g | 73.0 | 216—218 | 366.0870(366.0872) | 4o | 71.3 | 191—193 | 383.0763(383.0774) |
4h | 74.3 | 183—184 | 380.0820(380.0821) | 4p | 67.5 | 195—197 | 412.1031(412.1039) |
Compd. | 1H NMR(400 MHz), δ |
---|---|
4aa | 12.42(br, 1H, SO2NH),10.97(s, 1H, CONH-Pyrim), 8.69(d, J=5.4 Hz, 1H, Pyrim-H), 7.82—7.75(m, 2H, Ph-H), 7.71(dd, J=6.6, 2.1 Hz, 1H, Ph-H), 7.41(d, J=5.4 Hz, 1H, Pyrim-H), 2.76(s, 3H, Ph-CH3) |
4bb | 13.40(s, 1H, SO2NH), 9.58(s, 1H, CONH-Pyrim), 8.57(d, J=5.1 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.73—7.62(m, 2H, Ph-H), 7.15(d, J=5.1 Hz, 1H, Pyrim-H), 2.91(s, 3H, Ph-CH3), 2.54(s, 3H, Pyrim-CH3) |
4cb | 13.40(br, 1H, SO2NH), 9.60(br, 1H, CONH-Pyrim), 8.43(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(d, J=7.9 Hz, 1H, Ph-H), 7.70—7.64(m, 2H, Ph-H), 6.64(d, J=6.0 Hz, 1H, Pyrim-H), 3.99(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4db | 13.44(br, 1H, SO2NH), 9.57(br, 1H, CONH-Pyrim), 8.42(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(t, J=7.8 Hz, 1H, Ph-H), 7.63—7.69(m, 2H, Ph-H), 6.61(d, J=6.0 Hz, 1H, Pyrim-H), 4.43(q, J=7.0 Hz, 2H, OCH2CH3), 2.89(s, 3H, Ph-CH3), 1.38(t, J=7.0 Hz, 3H, OCH2CH3) |
4eb | 13.15(br, 1H, SO2NH), 9.67(br, 1H, CONH-Pyrim), 8.35(d, J=5.6 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 7.15(d, J=5.6 Hz, 1H, Pyrim-H), 2.90(s, 3H, Ph-CH3), 2.60(s, 3H, SCH3) |
4fa | 12.31(br, 1H, SO2NH), 10.91(s, 1H, CONH-Pyrim), 9.04(d, J=4.5 Hz, 1H, Pyrim-H), 7.81—7.62(m, 4H, Ph-H), 2.75(s, 3H, Ph-CH3) |
4gb | 13.72(br, 1H, SO2NH), 9.40(s, 1H, CONH-Pyrim), 7.77(d, J=7.7 Hz, 1H, Ph-H), 7.71—7.65(m, 2H, Ph-H), 7.01(s, 1H, Pyrim-H), 2.92(s, 3H, Ph-CH3), 2.47(s, 6H, 2Pyrim-CH3) |
4hb | 13.75(br, 1H, SO2NH), 9.50(br, 1H, CONH-Pyrim), 7.79(t, J=7.8 Hz, 1H, Ph-H), 7.71—7.66(m, 2H, Ph-H), 6.51(s, 1H, Pyrim-H), 3.95(s, 3H, Pyrim-OCH3), 2.92(s, 3H, Ph-CH3), 2.47(s, 3H, Pyrim-CH3) |
4ia | 13.62(s, 1H, SO2NH), 10.87(s, 1H, CONH-Pyrim), 7.74—7.68(m, 3H, Ph-H), 7.11(s, 1H, Pyrim-H), 2.76(s, 3H, SCH3), 2.55(s, 3H, Ph-CH3), 2.38(s, 3H, Pyrim-CH3) |
4jb | 13.02(br, 1H, SO2NH), 9.77(br, 1H, CONH-Pyrim), 7.81(t, J=7.8 Hz, 1H, Ph-H), 7.73—7.68(m, 2H, Ph-H), 7.26(s, 1H, Pyrim-H), 2.93(s, 3H, Ph-CH3), 2.59(s, 3H, Pyrim-CH3) |
4kb | 12.48(br, 1H, SO2NH), 9.81(br, 1H, CONH-Pyrim), 7.83(t, J=7.8 Hz, 1H, Ph-H), 7.75—7.70(m, 2H, Ph-H), 6.74(s, 1H, Pyrim-H), 4.08(s, 3H, Pyrim-OCH3), 2.94(s, 3H, Ph-CH3) |
4lc | 12.88(s, 1H, CONH-Pyrim), 7.59—7.52(m, 2H, Ph-H), 7.44(d, J=7.5 Hz, 1H, Ph-H), 7.30(br, 1H, SO2NH), 5.81(s, 1H, Pyrim-H), 3.97(s, 6H, 2Pyrim-OCH3), 2.98(s, 3H, Ph-CH3) |
4mc | 12.91(s, 1H, SO2NH), 7.58(t, J=7.7 Hz, 1H, Ph-H), 7.52(d, J=7.4 Hz, 1H, Ph-H), 7.43(d, J=7.5 Hz, 1H, Ph-H), 7.37(s, 1H, CONH-Pyrim), 6.32(s, 1H, Pyrim-H), 3.96(s, 3H, Pyrim-OCH3), 2.96(s, 3H, Pyrim-SCH3), 2.55(s, 3H, Ph-CH3) |
4nb | 12.40(br, 1H, SO2NH), 9.44(s, 1H, CONH-Pyrim), 8.61(s, 1H, Pyrim-H), 7.80(t, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 6.68(s, 1H, Pyrim-H), 3.97(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4ob | 13.07(br, 1H, SO2NH), 9.92(s, 1H, CONH-Pyrim), 7.82—7.72(m, 3H, Ph-H), 4.03(s, 3H, Triazine-OCH3), 2.92(s, 3H, Ph-CH3), 2.55(s, 3H, Triazine-CH3) |
4pa | 13.63(br, 1H, SO2NH), 10.81(s, 1H, CONH-Pyrim), 8.36(br, 1H, NHCH3), 7.71—7.63(m, 3H, Ph-H), 4.30(q, J=7.1 Hz, 2H, OCH2CH3), 2.83(s, 3H, NHCH3), 2.75(s, 3H, Ph-CH3), 1.30(t, J=7.1 Hz, 3H, OCH2CH3) |
Table 2 1H NMR data of compounds 4a—4p
Compd. | 1H NMR(400 MHz), δ |
---|---|
4aa | 12.42(br, 1H, SO2NH),10.97(s, 1H, CONH-Pyrim), 8.69(d, J=5.4 Hz, 1H, Pyrim-H), 7.82—7.75(m, 2H, Ph-H), 7.71(dd, J=6.6, 2.1 Hz, 1H, Ph-H), 7.41(d, J=5.4 Hz, 1H, Pyrim-H), 2.76(s, 3H, Ph-CH3) |
4bb | 13.40(s, 1H, SO2NH), 9.58(s, 1H, CONH-Pyrim), 8.57(d, J=5.1 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.73—7.62(m, 2H, Ph-H), 7.15(d, J=5.1 Hz, 1H, Pyrim-H), 2.91(s, 3H, Ph-CH3), 2.54(s, 3H, Pyrim-CH3) |
4cb | 13.40(br, 1H, SO2NH), 9.60(br, 1H, CONH-Pyrim), 8.43(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(d, J=7.9 Hz, 1H, Ph-H), 7.70—7.64(m, 2H, Ph-H), 6.64(d, J=6.0 Hz, 1H, Pyrim-H), 3.99(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4db | 13.44(br, 1H, SO2NH), 9.57(br, 1H, CONH-Pyrim), 8.42(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(t, J=7.8 Hz, 1H, Ph-H), 7.63—7.69(m, 2H, Ph-H), 6.61(d, J=6.0 Hz, 1H, Pyrim-H), 4.43(q, J=7.0 Hz, 2H, OCH2CH3), 2.89(s, 3H, Ph-CH3), 1.38(t, J=7.0 Hz, 3H, OCH2CH3) |
4eb | 13.15(br, 1H, SO2NH), 9.67(br, 1H, CONH-Pyrim), 8.35(d, J=5.6 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 7.15(d, J=5.6 Hz, 1H, Pyrim-H), 2.90(s, 3H, Ph-CH3), 2.60(s, 3H, SCH3) |
4fa | 12.31(br, 1H, SO2NH), 10.91(s, 1H, CONH-Pyrim), 9.04(d, J=4.5 Hz, 1H, Pyrim-H), 7.81—7.62(m, 4H, Ph-H), 2.75(s, 3H, Ph-CH3) |
4gb | 13.72(br, 1H, SO2NH), 9.40(s, 1H, CONH-Pyrim), 7.77(d, J=7.7 Hz, 1H, Ph-H), 7.71—7.65(m, 2H, Ph-H), 7.01(s, 1H, Pyrim-H), 2.92(s, 3H, Ph-CH3), 2.47(s, 6H, 2Pyrim-CH3) |
4hb | 13.75(br, 1H, SO2NH), 9.50(br, 1H, CONH-Pyrim), 7.79(t, J=7.8 Hz, 1H, Ph-H), 7.71—7.66(m, 2H, Ph-H), 6.51(s, 1H, Pyrim-H), 3.95(s, 3H, Pyrim-OCH3), 2.92(s, 3H, Ph-CH3), 2.47(s, 3H, Pyrim-CH3) |
4ia | 13.62(s, 1H, SO2NH), 10.87(s, 1H, CONH-Pyrim), 7.74—7.68(m, 3H, Ph-H), 7.11(s, 1H, Pyrim-H), 2.76(s, 3H, SCH3), 2.55(s, 3H, Ph-CH3), 2.38(s, 3H, Pyrim-CH3) |
4jb | 13.02(br, 1H, SO2NH), 9.77(br, 1H, CONH-Pyrim), 7.81(t, J=7.8 Hz, 1H, Ph-H), 7.73—7.68(m, 2H, Ph-H), 7.26(s, 1H, Pyrim-H), 2.93(s, 3H, Ph-CH3), 2.59(s, 3H, Pyrim-CH3) |
4kb | 12.48(br, 1H, SO2NH), 9.81(br, 1H, CONH-Pyrim), 7.83(t, J=7.8 Hz, 1H, Ph-H), 7.75—7.70(m, 2H, Ph-H), 6.74(s, 1H, Pyrim-H), 4.08(s, 3H, Pyrim-OCH3), 2.94(s, 3H, Ph-CH3) |
4lc | 12.88(s, 1H, CONH-Pyrim), 7.59—7.52(m, 2H, Ph-H), 7.44(d, J=7.5 Hz, 1H, Ph-H), 7.30(br, 1H, SO2NH), 5.81(s, 1H, Pyrim-H), 3.97(s, 6H, 2Pyrim-OCH3), 2.98(s, 3H, Ph-CH3) |
4mc | 12.91(s, 1H, SO2NH), 7.58(t, J=7.7 Hz, 1H, Ph-H), 7.52(d, J=7.4 Hz, 1H, Ph-H), 7.43(d, J=7.5 Hz, 1H, Ph-H), 7.37(s, 1H, CONH-Pyrim), 6.32(s, 1H, Pyrim-H), 3.96(s, 3H, Pyrim-OCH3), 2.96(s, 3H, Pyrim-SCH3), 2.55(s, 3H, Ph-CH3) |
4nb | 12.40(br, 1H, SO2NH), 9.44(s, 1H, CONH-Pyrim), 8.61(s, 1H, Pyrim-H), 7.80(t, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 6.68(s, 1H, Pyrim-H), 3.97(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4ob | 13.07(br, 1H, SO2NH), 9.92(s, 1H, CONH-Pyrim), 7.82—7.72(m, 3H, Ph-H), 4.03(s, 3H, Triazine-OCH3), 2.92(s, 3H, Ph-CH3), 2.55(s, 3H, Triazine-CH3) |
4pa | 13.63(br, 1H, SO2NH), 10.81(s, 1H, CONH-Pyrim), 8.36(br, 1H, NHCH3), 7.71—7.63(m, 3H, Ph-H), 4.30(q, J=7.1 Hz, 2H, OCH2CH3), 2.83(s, 3H, NHCH3), 2.75(s, 3H, Ph-CH3), 1.30(t, J=7.1 Hz, 3H, OCH2CH3) |
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 98.0 | 100 | 100 | 100 | 39.1 | 29.8 | 26.5 | 43.0 |
4b | 100 | 100 | 100 | 100 | 100 | 85.7 | 100 | 100 |
4c | 100 | 100 | 100 | 100 | 94.1 | 32.2 | 40.7 | 10.4 |
4d | 100 | 100 | 81.0 | 77.4 | 50.8 | 30.7 | 15.8 | 11.3 |
4e | 100 | 100 | 100 | 73.2 | 30.0 | 0 | 9.1 | 0 |
4f | 100 | 100 | 100 | 100 | 40.9 | 29.8 | 17.0 | 21.8 |
4g | 100 | 100 | 100 | 100 | 100 | 80.7 | 49.1 | 90.4 |
4h | 100 | 100 | 100 | 100 | 100 | 48.0 | 100 | 88.4 |
4i | 100 | 100 | 93.8 | 100 | 80.8 | 32.2 | 47.9 | 37.9 |
4j | 100 | 96.1 | 100 | 100 | 47.0 | 45.6 | 15.3 | 46.3 |
4k | 100 | 100 | 100 | 92.6 | 99.5 | 82.1 | 12.3 | 17.5 |
4l | 100 | 100 | 100 | 100 | 99.1 | 42.0 | 29.8 | 35.8 |
4m | 100 | 100 | 85.0 | 80.1 | 82.7 | 46.1 | 24.5 | 23.5 |
4n | 100 | 100 | 28.6 | 89.6 | 45.7 | 21.2 | 14.2 | 18.2 |
4o | 100 | 100 | 94.6 | 100 | 38.7 | 26.1 | 71.2 | 25.4 |
4p | 100 | 100 | 100 | 100 | 100 | 42.0 | 37.2 | 80.9 |
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Table 3 Herbicidal activities(%) of compounds 4a—4p by pot-culture method(300 g/ha)
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 98.0 | 100 | 100 | 100 | 39.1 | 29.8 | 26.5 | 43.0 |
4b | 100 | 100 | 100 | 100 | 100 | 85.7 | 100 | 100 |
4c | 100 | 100 | 100 | 100 | 94.1 | 32.2 | 40.7 | 10.4 |
4d | 100 | 100 | 81.0 | 77.4 | 50.8 | 30.7 | 15.8 | 11.3 |
4e | 100 | 100 | 100 | 73.2 | 30.0 | 0 | 9.1 | 0 |
4f | 100 | 100 | 100 | 100 | 40.9 | 29.8 | 17.0 | 21.8 |
4g | 100 | 100 | 100 | 100 | 100 | 80.7 | 49.1 | 90.4 |
4h | 100 | 100 | 100 | 100 | 100 | 48.0 | 100 | 88.4 |
4i | 100 | 100 | 93.8 | 100 | 80.8 | 32.2 | 47.9 | 37.9 |
4j | 100 | 96.1 | 100 | 100 | 47.0 | 45.6 | 15.3 | 46.3 |
4k | 100 | 100 | 100 | 92.6 | 99.5 | 82.1 | 12.3 | 17.5 |
4l | 100 | 100 | 100 | 100 | 99.1 | 42.0 | 29.8 | 35.8 |
4m | 100 | 100 | 85.0 | 80.1 | 82.7 | 46.1 | 24.5 | 23.5 |
4n | 100 | 100 | 28.6 | 89.6 | 45.7 | 21.2 | 14.2 | 18.2 |
4o | 100 | 100 | 94.6 | 100 | 38.7 | 26.1 | 71.2 | 25.4 |
4p | 100 | 100 | 100 | 100 | 100 | 42.0 | 37.2 | 80.9 |
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 95.0 | 100 | 100 | 100 | 5.0 | |||
4b | 100 | 100 | 100 | 100 | 100 | 55.4 | 65.4 | 99 |
4c | 100 | 100 | 35.0 | 79.2 | 15.0 | |||
4d | 100 | 97.1 | 63.1 | 23.7 | ||||
4e | 100 | 93.7 | 20.0 | 31.8 | ||||
4f | 100 | 100 | 100 | 77.5 | ||||
4g | 100 | 100 | 100 | 100 | 100 | 55.4 | 48.3 | |
4h | 100 | 100 | 100 | 100 | 100 | 78.7 | 58.4 | |
4i | 100 | 60.5 | 85.7 | 63.4 | 20.8 | |||
4j | 95.1 | 80.1 | 70.0 | 77.9 | ||||
4k | 100 | 100 | 100 | 53.4 | 69.7 | 23.5 | ||
4l | 100 | 100 | 100 | 100 | 98.2 | |||
4m | 100 | 78.0 | 10.0 | 14.7 | 10.0 | |||
4n | 100 | 93.1 | 5.0 | 35.8 | ||||
4o | 100 | 85.4 | 65.7 | 81.0 | 30.2 | |||
4p | 100 | 100 | 100 | 99.0 | 98.6 | 56.6 | ||
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Table 4 Herbicidal activities(%) of compounds 4a—4p by pot-culture method(75 g/ha)*
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 95.0 | 100 | 100 | 100 | 5.0 | |||
4b | 100 | 100 | 100 | 100 | 100 | 55.4 | 65.4 | 99 |
4c | 100 | 100 | 35.0 | 79.2 | 15.0 | |||
4d | 100 | 97.1 | 63.1 | 23.7 | ||||
4e | 100 | 93.7 | 20.0 | 31.8 | ||||
4f | 100 | 100 | 100 | 77.5 | ||||
4g | 100 | 100 | 100 | 100 | 100 | 55.4 | 48.3 | |
4h | 100 | 100 | 100 | 100 | 100 | 78.7 | 58.4 | |
4i | 100 | 60.5 | 85.7 | 63.4 | 20.8 | |||
4j | 95.1 | 80.1 | 70.0 | 77.9 | ||||
4k | 100 | 100 | 100 | 53.4 | 69.7 | 23.5 | ||
4l | 100 | 100 | 100 | 100 | 98.2 | |||
4m | 100 | 78.0 | 10.0 | 14.7 | 10.0 | |||
4n | 100 | 93.1 | 5.0 | 35.8 | ||||
4o | 100 | 85.4 | 65.7 | 81.0 | 30.2 | |||
4p | 100 | 100 | 100 | 99.0 | 98.6 | 56.6 | ||
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Compd. | Inhibition(%) | ||||||
---|---|---|---|---|---|---|---|
C. arachidicola | P. piricola | S. sclerotiorum | P. capsici | R. cerealis | C. lagenarium | B. cinerea | |
4a | 0.0 | 31.8 | 31.3 | 40.6 | 66.7 | 45.0 | 50.0 |
4b | 0.0 | 13.6 | 35.9 | 46.9 | 71.4 | 35.0 | 26.5 |
4c | 0.0 | 22.7 | 28.1 | 46.9 | 71.4 | 40.0 | 50.0 |
4d | 60.0 | 50.8 | 47.8 | 18.8 | 67.5 | 40.0 | 50.0 |
4e | 0 | 0 | 7.8 | 37.5 | 66.7 | 40.0 | 29.4 |
4f | 12.5 | 4.5 | 0 | 40.6 | 59.5 | 30.0 | 26.5 |
4g | 0.0 | 18.2 | 43.8 | 50.0 | 71.4 | 35.0 | 50.0 |
4h | 25.0 | 45.5 | 75.0 | 43.8 | 71.4 | 35.0 | 52.9 |
4i | 36.7 | 32.8 | 10.9 | 21.9 | 71.3 | 32.5 | 11.4 |
4j | 12.5 | 0.0 | 18.8 | 46.9 | 66.7 | 30.0 | 52.9 |
4k | 25.0 | 27.3 | 34.4 | 40.6 | 61.9 | 55.0 | 58.8 |
4l | 0 | 31.8 | 81.3 | 46.9 | 71.4 | 50.0 | 61.8 |
4m | 0.0 | 8.2 | 21.7 | 15.6 | 8.8 | 15.0 | 18.2 |
4n | 25.0 | 9.1 | 42.2 | 43.8 | 66.7 | 45.0 | 29.4 |
4o | 0.0 | 22.7 | 28.1 | 46.9 | 61.9 | 35.0 | 35.3 |
4p | 36.7 | 23.0 | 19.6 | 15.6 | 36.3 | 22.5 | 11.4 |
Chlorothalonil | 75.0 | <50.0 | <50.0 | 100 | 100 | 95.0 | 100 |
Carbendazim | <50.0 | 100 | 99.2 | <50.0 | 100 | 100 | <50.0 |
Table 5 Fungicidal activities of compounds 4a—4p at the dosage of 50 mg/L in vitro
Compd. | Inhibition(%) | ||||||
---|---|---|---|---|---|---|---|
C. arachidicola | P. piricola | S. sclerotiorum | P. capsici | R. cerealis | C. lagenarium | B. cinerea | |
4a | 0.0 | 31.8 | 31.3 | 40.6 | 66.7 | 45.0 | 50.0 |
4b | 0.0 | 13.6 | 35.9 | 46.9 | 71.4 | 35.0 | 26.5 |
4c | 0.0 | 22.7 | 28.1 | 46.9 | 71.4 | 40.0 | 50.0 |
4d | 60.0 | 50.8 | 47.8 | 18.8 | 67.5 | 40.0 | 50.0 |
4e | 0 | 0 | 7.8 | 37.5 | 66.7 | 40.0 | 29.4 |
4f | 12.5 | 4.5 | 0 | 40.6 | 59.5 | 30.0 | 26.5 |
4g | 0.0 | 18.2 | 43.8 | 50.0 | 71.4 | 35.0 | 50.0 |
4h | 25.0 | 45.5 | 75.0 | 43.8 | 71.4 | 35.0 | 52.9 |
4i | 36.7 | 32.8 | 10.9 | 21.9 | 71.3 | 32.5 | 11.4 |
4j | 12.5 | 0.0 | 18.8 | 46.9 | 66.7 | 30.0 | 52.9 |
4k | 25.0 | 27.3 | 34.4 | 40.6 | 61.9 | 55.0 | 58.8 |
4l | 0 | 31.8 | 81.3 | 46.9 | 71.4 | 50.0 | 61.8 |
4m | 0.0 | 8.2 | 21.7 | 15.6 | 8.8 | 15.0 | 18.2 |
4n | 25.0 | 9.1 | 42.2 | 43.8 | 66.7 | 45.0 | 29.4 |
4o | 0.0 | 22.7 | 28.1 | 46.9 | 61.9 | 35.0 | 35.3 |
4p | 36.7 | 23.0 | 19.6 | 15.6 | 36.3 | 22.5 | 11.4 |
Chlorothalonil | 75.0 | <50.0 | <50.0 | 100 | 100 | 95.0 | 100 |
Carbendazim | <50.0 | 100 | 99.2 | <50.0 | 100 | 100 | <50.0 |
[1] | Levitt, G. , Synthesis and Chemistry of Agrochemicals Ⅱ, , American Chemistry, Society , Washington DC, 1991, 16-31 |
[2] | Hay J., V. , Pesti. Sci., 1990, 29( 3), 247- 261 |
[3] | 潘里, 刘卓, 陈有为, 李永红, 李正名. 高等学校化学学报, 2013, 34( 6), 1416- 1422 |
Pan, L. , Liu, Z. , Chen Y., W. , Li Y., H. , Li Z., M. , Chem. J. Chinese Universities, 2013, 34( 6), 1416- 1422 | |
[4] | Langenfeld H. J., W. , Odenthal K. K., Process for Preparation of Alkoxytriazolinoes, US 5599945, 1997- 03-14 |
[5] | 李正名, 贾国锋, 王玲秀, 杨志强, 赖城明. 防治玉米田杂草组合物, CN 1080116A, 1994- 1-5) |
Li Z., M. , Jia G. F., Wang L. X., Yang Z. Q., Lai C. M., Composite for Preventing and Killing Weeds in the Corn Field, CN 1080116A, 1994- 1-5( | |
[6] | 李正名, 贾国锋, 王玲秀, 范传文, 杨炤. 新型磺酰脲类化合物除草剂, CN 1106393A, 1995- 08-09) |
Li Z., M. , Jia G. F., Wang L. X., Fan C. W., Yang Z., New Sulfonylureas Herbicide, CN 1106393A, 1995- 08-09( | |
[7] | Li, Z.M. , Ma, Y. , Guddat, L. , Cheng P., Q. , Wang J., G. , Pang S., S. , Dong Y., H. , Lai C., M. , Wang L., X. , Jia G., F. , Li Y., H. , Wang S., H. , Liu, J. , Zhao W., G. , Wang B., L. , Pest Manag. Sci., 2014, 68( 4), 618- 628 |
[8] | |
[9] | 李秉华, 王贵启, 李香菊. 云南农业大学学报, 2005, 20( 6), 835- 839 |
Li B., H. , Wang G., Q. , Li X., J. , J. Yunnan Agri. Univ., 2005, 20( 6), 835- 839 | |
[10] | 祝春强, 陈会柱, 刘明熙, 万贤宗. 钱国华. 农药科学与管理, 2005, 26( 5), 25- 27 |
Zhu C., Q. , Chen H., Z. , Liu M., X. , Wan X., Z. , Qian G., H. , Pesti. Sci. Admin., 2005, 26( 5), 25- 27 | |
[11] | 刘金胜, 寇俊杰, 刘桂龙. 农药, 2007, 46( 3), 145- 147 |
Liu J., S. , Kou J., J. , Liu G., L. , Agrochemicals, 2007, 46( 3), 145- 147 | |
[12] | 朱荷锄. 中国植保导刊, 2012, 32( 8), 49- 50 |
Zhu H., C. , China Plant Protection, 2012, 32( 8), 49- 50 | |
[13] | 苏少泉. 农药, 1998, 37( 12), 4- 7 |
Su S., Q. , Pesticides, 1998, 37( 12), 4- 7 | |
[14] | 刘刚, 阳光. 农药市场信息, 2014, 1, 13) |
Liu, G. , Yang, G. , Pesticides Market News, 2014, 1, 13( | |
[15] | Chaleff R., S. , Mauvais C., J. , Science, 1984, 224( 4656), 1443- 1445 |
[16] | Liu, Z. , Pan, L. , Li Y., H. , Wang S., H. , Li Z., M. , Chem. Res. Chinese Universities, 2013, 29( 3), 466- 472 |
[17] | Hoffman R., V. , Org. Synth., 1981, 60, 121- 126 |
[18] | 刘卓, 潘里, 于淑晶, 李正名. 高等学校化学学报, 2013, 34( 8), 1868- 1872 |
Liu, Z. , Pan, L. , Yu S., J. , Li Z., M. , Chem. J. Chinese Universities, 2013, 34( 8), 1868- 1872 | |
[19] | 王红学, 李芳, 许丽萍, 李永红, 王素华, 李正名. 高等学校化学学报, 2010, 31( 1), 64- 67 |
Wang H., X. , Li, F. , Xu L., P. , Li Y., H. , Wang S., H. , Li Z., M. , Chem. J. Chinese Universities, 2010, 31( 1), 64- 67 | |
[20] | Peng, H. , Deng X., Y. , Gao, L. , Tan X., S. , He H., W. , Chem. Res. Chinese Universities, 2014, 30( 1), 82- 86 |
[21] | 范世丽, 张博, 高丽叶, 王兰芝, 边艳青, 李媛. 高等学校化学学报, 2014, 35( 12), 2574- 2583 |
Fan S., L. , Zhang, B. , Gao L., Y. , Wang L., Z. , Bian Y., Q. , Li, Y. , Chem. J. Chinese Universities, 2014, 35( 12), 2574- 2583 |
[1] | 左怀龙, 雷思敏, 张锐, 李玉新, 陈伟. 新型异喹啉衍生物的设计合成及抑菌活性[J]. 高等学校化学学报, 2021, 42(9): 2766. |
[2] | 胡皓程, 李文利, 张嘉宁, 刘宇博. 黑木耳寡糖的提取、 结构表征及生物活性[J]. 高等学校化学学报, 2021, 42(8): 2465. |
[3] | 李普, 陈英, 夏榕娇, 郭涛, 张敏, 仕春, 汤旭, 贺鸣, 薛伟. 含喹喔啉杨梅素衍生物的合成及生物活性[J]. 高等学校化学学报, 2019, 40(5): 909. |
[4] | 李冰, 王学敏, 白凤英, 刘淑清. 稀土氮杂环配合物的合成、 结构及抑菌活性[J]. 高等学校化学学报, 2019, 40(4): 632. |
[5] | 常俊朋, 赵佳瑞, 陈思佳, 孟凯, 石微妮, 李瑞芳. 抗菌肽SAMP1及其类似肽的构效关系[J]. 高等学校化学学报, 2019, 40(4): 705. |
[6] | 万金林, 巫受群, 甘宜远, 孟娇, 王贞超, 欧阳贵平. 含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物的合成及抗细菌活性[J]. 高等学校化学学报, 2018, 39(8): 1683. |
[7] | 谭英, 肖梦武, 叶姣, 胡艾希, 曾子清, 欧晓明. (Z)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮肟(5-芳基-1,3,4-噁二唑-2-基)甲基醚的合成和抑菌活性[J]. 高等学校化学学报, 2017, 38(8): 1375. |
[8] | 肖维, 阮祥辉, 李琴, 张菊平, 钟新敏, 谢艳, 王晓斌, 黄民国, 薛伟. 酰胺类杨梅素衍生物的合成及抑菌活性[J]. 高等学校化学学报, 2017, 38(1): 35. |
[9] | 王美怡, 马翼, 王海英, 曹刚, 李正名. 苯环5位取代磺酰脲类化合物的水解动力学及三维定量构效关系初步研究[J]. 高等学校化学学报, 2016, 37(9): 1636. |
[10] | 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[J]. 高等学校化学学报, 2016, 37(8): 1442. |
[11] | 贾长青, 杨冬燕, 车传亮, 马永强, 芮昌辉, 闫晓静, 覃兆海. 1H-1,2,4-三唑-5-氨基甲酸酯类化合物的合成、 结构表征及杀虫、 抑菌活性[J]. 高等学校化学学报, 2016, 37(5): 892. |
[12] | 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[J]. 高等学校化学学报, 2015, 36(7): 1291. |
[13] | 陈伟, 魏巍, 周莎, 李永红, 张晓, 童军, 李玉新, 李正名. 新型含苯基取代嘧啶基磺酰脲衍生物的设计、 合成及生物活性[J]. 高等学校化学学报, 2015, 36(4): 672. |
[14] | 王娇, 田克情, 薛子桥, 武云云, 杨田, 赵惠敏, 张萍. 4-取代苯基-1,5-苯并硫氮杂䓬-2-甲酸的合成及抑菌活性[J]. 高等学校化学学报, 2015, 36(3): 505. |
[15] | 武瑶, 梁雯婧, 李成, 商旭, 丛丽娜. 热处理对海参溶菌酶C端多肽的抑菌活性和结构的影响[J]. 高等学校化学学报, 2014, 35(5): 1044. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||