CN1102146C - 含取代呋喃环的酰胺基硫脲的合成 - Google Patents
含取代呋喃环的酰胺基硫脲的合成 Download PDFInfo
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Abstract
本发明是含取代呋喃环的酰胺基硫脲的合成,其通式为式中L2,L3,L4,R2,R3,R4选自硝基,卤素,烷基,烷氧基,羟基,氢。该化合物可促进植物根的生长。
Description
本发明是一含呋喃环的化合物,可异构化形成一大共轭体系,具有促进植物生长作用。
已知酰胺基硫脲类化合物具有杀虫,植物生长调节等生物活性(PottaK.T.,Chem.Rev.,1961,61(2):87),而5-芳基-2-呋喃甲酸及其衍生物亦具有多种生物活性,如,U.S.Pat.3 856 825报道的化合物具有镇痉作用。故创制了含呋喃环的酰胺基硫脲类化合物。
本发明的目的是合成一种既能促进植物生长,又不会对环境造成危害的植物生长调节剂。
含取代呋喃环的酰胺基硫脲在有机化合物中是一类较为简单的化合物.本发明中,它的通式为式中L2,L3,L4,R2,R3,R4选自硝基,卤素,烷基,烷氧基,羟基,氢。
本发明中化合物可进行优选.其通式中L2的电荷要小,R2的电荷,体积要大,例如,L2可为氯,R2可为硝基。
本发明的化合物为固体,可通过5-芳基-2-呋喃甲酰基异硫氰酸酯同芳酰基肼加成得到。
本发明创制了一类结构简单,在合成上易于操作的化合物,适于在农业上作为一种新的植物生长调节剂使用。
以下为本发明的合成实例:
实施例一
将20ml 0.005mol的5-(2-氯苯基)-2-呋喃甲酰基异硫氰酸酯的乙腈溶液滴入20ml 0.0045mol2-羟基苯甲酰肼的乙腈溶液中,搅拌,室温反应2小时。过滤,得白色固体,即为产物3。
实施例二
将20ml 0.005mol的5-(2-硝基苯基)-2-呋喃甲酰基异硫氰酸酯的乙腈溶液滴入20ml 0.0045mol2-氯苯甲酰肼的乙腈溶液中,搅拌,室温反应2小时。过滤,得白色固体,即为产物10。
实施例三
将20ml 0.005mol的5-(3-硝基苯基)-2-呋喃甲酰基异硫氰酸酯的乙腈溶液滴入20ml 0.0045mol苯甲酰肼的乙腈溶液中,搅拌,室温反应2小时。过滤,得黄色固体,即为产物24。
实施例四
将20ml 0.005mol的5-(4-硝基苯基)-2-呋喃甲酰基异硫氰酸酯的乙腈溶液滴入20ml 0.0045mol3-氯苯甲酰肼的乙腈溶液中,搅拌,室温反应2小时。过滤,得黄色固体,即为产物2。
产物 | L2 | L3 | L4 | R2 | R3 | R |
1 | NO2 | H | H | H | CH3 | H |
2 | H | H | NO2 | H | Cl | H |
3 | Cl | H | H | OH | H | H |
4 | NO2 | H | H | H | Br | H |
5 | NO2 | H | H | H | H | CH3 |
6 | Cl | H | H | Cl | H | Cl |
7 | NO2 | H | H | H | H | Br |
8 | NO2 | H | H | H | H | H |
9 | H | NO2 | H | H | H | Cl |
10 | NO2 | H | H | Cl | H | H |
11 | Cl | H | H | H | H | Cl |
12 | Cl | H | H | H | CH3 | H |
13 | NO2 | H | H | H | Cl | H |
14 | H | NO2 | H | H | H | CH3O |
15 | H | H | NO2 | H | H | CH3 |
16 | H | NO2 | H | H | H | CH3 |
17 | H | NO2 | H | H | H | Br |
18 | Cl | H | H | H | H | CH3O |
19 | Cl | H | H | H | H | CH3 |
20 | Cl | H | H | H | Cl | H |
21 | Cl | H | H | H | H | Br |
22 | Cl | H | H | H | H | CH3CH2O |
23 | NO2 | H | H | H | H | CH3O |
24 | H | NO2 | H | H | H | H |
25 | NO2 | H | H | I | H | H |
26 | Cl | H | H | I | H | H |
27 | NO2 | H | H | H | H | Cl |
28 | NO2 | H | H | Cl | H | Cl |
29 | Cl | H | H | H | Br | H |
30 | Cl | H | H | Cl | H | H |
化合物的物理常数见表-1,表-2。表-1 化合物物理性质与1HNMR数据
**:4.11(2H,q,OEt).1.36(3H,t,OEt)
产物 | m.p.(℃) | 1HNMR(δppm)[Ha,Hb,Hc,H苯及呋喃环] |
1 | 192~194 | 12.13(s),11.75(s),11.07(s),7.81~8.04(m,10H),2.39(3H,s,CH3) |
2 | 233~235 | 12.19(s),12.00(s),11.30(s),7.56~8.39(m,10H) |
3 | 231~233 | 13.54(s),12.04(s),11.97(s),7.02~8.19(m,10H),11.85(1H,s,OH) |
4 | 204~206 | 12.09(s),11.79(s),11.28(s),7.12~8.09(m,10H) |
5 | 203~205 | 12.15(s),11.75(s),11.06(s),7.11~8.05(m,10H),2.38(3H,s,CH3) |
6 | 206~208 | 12.26(s),11.86(s),11.30(s),7.36~8.21(m,9H) |
7 | 208~210 | 12.11(s),11.78(s),11.25(s),7.11~8.05(m,10H) |
8 | 197~200 | 12.13(s),11.74(s),11.12(s),7.12~8.05(m,10H) |
9 | 238~240 | 12.12(s),11.98(s),11.25(s),7.56~8.39(m,10H) |
10 | 180~182 | 12.18(s),11.76(s),11.21(s),7.10~8.04(m,10H) |
11 | 196~198 | 12.20(s),11.83(s),11.23(s),7.36~8.21(m,10H) |
12 | 203~205 | 12.21(s),11.84(s),11.07(s),7.36~8.22(m,10H),2.39(3H,s,CH3) |
13 | 202~204 | 12.10(s),11.74(s),11.26(s),7.10~8.05(m,10H) |
14 | 222~224 | 12.25(s),11.92(s),11.00(s),7.05~8.82(m,10H),3.86(3H,s,CH3O) |
15 | 234~236 | 12.24(s),11.95(s),11.06(s),7.33~8.39(m,10H),2.39(3H,s,CH3) |
16 | 217~219 | 12.24(s),11.93(s),11.05(s),7.33~8.81(m 10H),2.39(3H,s,CH3) |
17 | 221~223 | 12.21(s),11.95(s),11.25(s),7.54~8.82(m,10H) |
18 | 186~188 | 12.22(s),11.80(s),10.97(s),7.05~8.22(m,10H),3.84(3H,s,CH3O) |
19 | 182~184 | 12.22(s),11.84(s),11.06(s),7.33~8.22(m,10H),2.39(3H,s,CH3) |
20 | 213~215 | 12.17(s),11.87(s),11.29(s),7.37~8.22(m,10H) |
21 | 205~207 | 12.19(s),11.96(s),11.25(s),7.37~8.23(m,10H) |
22 | 189~191 | 12.23(s),11.83(s),10.98(s),7.03~8.23(m,10H),** |
23 | 194~196 | 12.15(s),11.70(s),10.96(s),7.05~8.05(m,10H),3.84(3H,s,CH3O) |
24 | 217~219 | 12.24(s),11.93(s),11.14(s),7.53~8.82(m,10H) |
25 | 202~204 | 11.86(s),11.79(s),11.20(s),7.12~8.05(m,10H) |
26 | 203~205 | 12.26(s),11.89(s),11.20(s),7.33~7.96(m,10H) |
27 | 208~210 | 12.19(s),11.86(s),11.24(s),7.10~8.02(m,10H) |
28 | 188~190 | 12.20(s),11.77(s).11.20(s),7.10~8.19(m,9H) |
29 | 215~217 | 12.16(s),11.86(s),11.28(s),7.37~8.21(m,10H) |
30 | 193~195 | 12.27(s),11.88(s),11.24(s),7.37~8.20(m,10H) |
表-2 化合物IR与元素分析数据
生物活性测定
产物 | IR(C=S) | N%(计算) | C%(计算) | H%(计算) |
1 | 1215 | 13.20(13.21) | 56.47(56.60) | 3.77(3.77) |
2 | 1220 | 12.45(12.60) | 51.35(51.29) | 3.09(2.92) |
3 | 1210 | 10.42(10.10) | 54.84(54.87) | 3.47(3.37) |
4 | 1220 | 11.14(11.45) | 46.63(46.62) | 2.63(2.66) |
5 | 1220 | 12.83(13.21) | 56.56(56.60) | 3.79(3.77) |
6 | 1220 | 8.93(8.96) | 48.73(48.67) | 2.51(2.56) |
7 | 1510 | 11.22(11.45) | 46.5 7(46.62) | 2.63(2.66) |
8 | 1220 | 13.21(13.65) | 55.63(55.61) | 3.49(3.41) |
9 | 1220 | 12.27(12.60) | 50.97(5 1.29) | 3.16(2.92) |
10 | 1220 | 12.37(12.60) | 51.38(51.29) | 2.97(2.92) |
11 | 1230 | 9.51(9.68) | 52.48(52.53) | 3.37(3.00) |
12 | 1230 | 10.17(10.16) | 58.25(58.04) | 4.12(3.87) |
13 | 1220 | 12.22(12.60) | 51.08(51.29) | 3.14(2.92) |
14 | 1215 | 12.41(12.73) | 54.42(54.55) | 3.71(3.64) |
15 | 1220 | 13.03(13.21) | 56.61(56.60) | 3.83(3.77) |
16 | 1220 | 12.86(13.21) | 56.22(56.60) | 4.00(3.77) |
17 | 1215 | 11.16(11.45) | 46.66(46.63) | 3.00(2.66) |
18 | 1230 | 9.49(9.78) | 55.70(55.88) | 3.73(3.73) |
19 | 1220 | 10.34(10.15) | 58.13(58.04) | 3.87(3.87) |
20 | 1230 | 9.77(9.68) | 52.76(52.53) | 3.11(3.00) |
21 | 1220 | 8.56(8.78) | 47.27(47.64) | 2.92(2.72) |
22 | 1220 | 9.74(9.74) | 56.89(56.82) | 4.13(4.06) |
23 | 1220 | 12.42(12.72) | 54.48(54.54) | 3.95(3.66) |
24 | 1220 | 13.27(13.66) | 55.52(55.61) | 3.49(3.41) |
25 | 1220 | 10.32(10.45) | 42.41(42.54) | 2.43(2.43) |
26 | 1230 | 8.36(7.99) | 43.71(43.39) | 2.57(247) |
27 | 1220 | 12.25(12.60) | 51.42(51.29) | 2.66(2.92) |
28 | 1220 | 11.93(11.69) | 47.85(47.65) | 2.45(2.72) |
29 | 1220 | 8.74(8.77) | 47.63(47.65) | 2.75(2.72) |
30 | 1230 | 9.54(9.68) | 52.66(52.53) | 3.10(3.00) |
在直径15厘米的培养皿中放入滤纸,加入配好的药液9毫升,放入15粒刚出芽的水稻种子(或15粒黄瓜种子),用水作为对照。将其放入光照恒温培养箱里,温度为282。72小时后测其根长,芽长。
10ppm时的促进率
产物 | 水稻(根)% | 水稻(芽)% | 黄瓜(根)% |
1 | 58.29 | -1.06 | 16.98 |
2 | 90.88 | -4.96 | 51.60 |
3 | 95.53 | 0.00 | 75.34 |
4 | 80.94 | 0.00 | 0.00 |
5 | 55.59 | -1.66 | 95.77 |
6 | 36.22 | 0.00 | 36.96 |
7 | 92.83 | 0.00 | 58.26 |
8 | 17.97 | -4.88 | 25.01 |
9 | 30.35 | 1.46 | 59.44 |
10 | 18.34 | 4.47 | 50.04 |
11 | 50.28 | -3.33 | 44.22 |
12 | 62.29 | -1.26 | 35.51 |
13 | 71.14 | 2.52 | 93.07 |
14 | 25.70 | 0.00 | 56.28 |
15 | 26.35 | -4.13 | 69.48 |
16 | 62.94 | -4.13 | 56.74 |
17 | 56.98 | 4.67 | 52.17 |
18 | 46.28 | -4.13 | 67.39 |
19 | 62.94 | -3.21 | 14.13 |
20 | 29.50 | -4.13 | 47.41 |
21 | 61.08 | -10.70 | 84.36 |
22 | 47.67 | 0.00 | 47.11 |
23 | 22.25 | -7.14 | 56.28 |
24 | 21.04 | 14.37 | 55.98 |
25 | 56.98 | -6.60 | 57.42 |
26 | 68.81 | -4.65 | 73.59 |
27 | 50.28 | 2.07 | 39.73 |
28 | 64.28 | 2.41 | 50.99 |
29 | 35.01 | 2.90 | 60.16 |
30 | 33.15 | -6.60 | 39.50 |
1ppm时的促进率
产物 | 水稻(根)% | 水稻(芽)% | 黄瓜(根)% |
1 | 89.08 | 5.99 | 45.74 |
2 | 100.0 | 0.00 | 53.76 |
3 | 79.00 | 2.20 | 43.90 |
4 | 53.50 | 2.05 | 33.18 |
5 | 46.41 | 16.86 | 42.19 |
6 | 88.21 | 2.52 | 40.81 |
7 | 74.95 | 4.86 | 57.43 |
8 | 35.08 | 3.18 | 37.23 |
9 | 75.97 | 0.00 | 27.94 |
10 | 67.03 | 7.32 | 63.19 |
11 | 63.72 | 0.00 | 31.94 |
12 | 89.03 | 5.29 | 43.98 |
13 | 19.71 | 0.00 | 63.19 |
14 | 92.36 | 0.00 | 38.14 |
15 | 85.45 | 0.00 | 21.25 |
16 | 77.99 | 6.39 | 32.96 |
17 | 63.75 | 1.24 | 54.62 |
18 | 61.14 | 0.00 | 43.29 |
19 | 81.12 | 0.00 | 44.48 |
20 | 37.11 | 3.82 | 22.82 |
21 | 63.44 | 0.00 | 23.53 |
22 | 70.35 | 0.00 | 33.45 |
23 | 43.37 | 0.00 | 76.71 |
24 | 46.32 | 2.86 | 57.37 |
25 | 74.95 | 6.07 | 41 22 |
26 | 35.82 | 0.00 | 55.22 |
27 | 25.87 | 2.52 | 36.23 |
28 | 43.92 | 0.00 | 35.02 |
29 | 82.14 | 0.00 | 39.35 |
30 | 28.91 | 0.00 | 35.38 |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US3856825A (en) * | 1973-11-02 | 1974-12-24 | Morton Norwich Products Inc | 3-diethylamino-2,2-dimethylpropyl 5-(substituted phenyl)-2-furoates |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3856825A (en) * | 1973-11-02 | 1974-12-24 | Morton Norwich Products Inc | 3-diethylamino-2,2-dimethylpropyl 5-(substituted phenyl)-2-furoates |
Non-Patent Citations (3)
Title |
---|
化学通报 1994年第1期 1994-01-01 贾学顺等人,1-苯氧乙酰基-4-芳酰基氨基硫脲的合成 * |
高等学校化学学报.1997年VOL18N 1997-03-01 金桂玉等人,1-芳酰基-4-取代吡唑甲酰基氨基硫脲和环环产物的合成及生物活性 * |
高等学校化学学报.1997年VOL18N 1997-03-01 金桂玉等人,1-芳酰基-4-取代吡唑甲酰基氨基硫脲和环环产物的合成及生物活性;化学通报 1994年第1期 1994-01-01 贾学顺等人,1-苯氧乙酰基-4-芳酰基氨基硫脲的合成 * |
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