CN103524419A - 一组3-三氟甲基吡唑化合物 - Google Patents
一组3-三氟甲基吡唑化合物 Download PDFInfo
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Abstract
本发明提供了一组3-三氟甲基吡唑化合物,该化合物通式为
Description
技术领域
本发明属于农药领域,技术方案涉及一组3-三氟甲基吡唑化合物,具体涉及一组3-三氟甲基吡唑衍生物及其制备方法和以其为活性成分的杀菌剂应用。
背景技术
由于具有高的生物活性,吡唑类化合物用作农药,越来越引人注目。例如,日本住友公司开发的内吸性杀菌剂呋吡菌胺、日本三井化学公司开发的吡噻菌胺都是优良的农用杀菌剂。我们对吡唑类化合物结构进行了深入的研究分析,根据生物电等排原理,将三氟甲基、氯原子同时引入吡唑环,以1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯为母体,分别与不同的亲核试剂反应,合成了系列3-三氟甲基吡唑化合物。
发明内容
本发明的目的是提供一组3-三氟甲基吡唑化合物,结构式如式I所示:
其中,X为NH、O或S,R基团选自苯基衍生物、萘基衍生物或杂环基衍生物。
具体的,式I所示化合物为表1中的任意一种。
表1本发明提供的3-三氟甲基吡唑化合物
本发明的再一个目的是提供所述化合物的制备方法如下:
反应方程式:
包括以下步骤:在室温将1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯的惰性溶剂溶液滴加入RXH和K2CO3的惰性溶剂溶液中,滴加完毕后,升至40~60℃温度下反应,反应完毕后抽滤、去除反应溶剂,经重结晶纯化后即得所述化合物。
具体的,所述RXH选自表2中与化合物编号对应的任意一种。
表2制备本发明所述3-三氟甲基吡唑化合物所需RXH
具体的,制备化合物T120301和T120528时,所述RXH分别为2,5-二巯基-3,4-噻二唑和2-氨基-5-巯基-3,4-噻二唑,而且1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯、RXH和K2CO3的摩尔质量比为2:1:2;制备表1中其他化合物时,所述1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯、RXH和K2CO3的摩尔质量比为1:1:1。
具体的,所述惰性溶剂为乙腈、氯仿或甲苯。
本发明的第三个目的是提供所述3-三氟甲基吡唑化合物为农用杀菌剂应用。
本发明的第四个目的是提供一种农用组合物作为农用杀菌剂中的应用,该农用组合物包含0.1~99.9重量%本发明所述3-三氟甲基吡唑化合物以及农药学上可接受的载体和/或赋形剂。
本发明的有益效果是:本发明所述的3-三氟甲基吡唑化合物可用于防治农业病害,部分化合物具有抑制病原菌生长的活性,并可取得很好的效果。
本发明提供的3-三氟甲基吡唑化合物用于防治农业病害的应用是本发明的重要特征之一。
本发明所述新化合物制备过程中产生的“三废”较少,易于处理,作为杀菌剂农药生产时比较环保。
具体实施方式
本发明通过特定制备和生物活性测定实施例具体的说明本发明所述3-三氟甲基吡唑化合物的制备和生物活性,所述实施例仅用于具体的说明本发明而非限制本发明。
下述实施例中所使用的实验方法如无特殊说明,均为常规方法。
下述实施例中所用的材料、试剂等,如无特殊说明,均可从商业途径得到。
实施例1化合物T111025的制备
在装配有磁力搅拌器、温度计和冷凝器的100毫升的三口瓶中加入4毫摩尔无水K2CO3粉末、4毫摩尔苯胺、30毫升氯仿,室温(20~30℃)下缓慢滴加4毫摩尔1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯溶于20毫升氯仿所配成的溶液,滴加完毕,缓慢升温至50±5℃,保温搅拌反应3小时,冷却至室温。减压过滤反应混合物,将所得滤液减压脱溶,制得化合物T111025粗品,用乙醇对化合物T111025粗品重结晶,制得白色片状晶体化合物T111025,收率89%。
实施例2~39表1中其他38种化合物的制备
具体操作如表3。
表3实施例2~39具体操作
实施例40实施例1-39所制备化合物的理化参数测定和化学结构鉴定
测定实施例1-39所制备化合物的熔点、1H-NMR和IR,其化学结构式和理化参数见表4、表5和表6。
表4实施例1-39所制备的3-三氟甲基吡唑化合物物理化学性质及收率
表5实施例1-39所制备的3-三氟甲基吡唑化合物核磁共振氢谱数据
表6实施例1-39所制备的3-三氟甲基吡唑化合物红外光谱数据
编号 | 红外光谱(特征吸收峰)数据(IR)/cm-1 |
T111025 | 3290,3037,2958,2772,1963,1665,1656,1594,1548,1499,1441 |
T111026 | 3406,3025,2958,1669,1586,1523,1453,1321 |
T111027 | 3406,3025,2982,2934,1951,1880,1677,1553,1494,1372 |
T111028 | 3319,3191,3120,3041,2550,1897,1652,1598,1544,1445,1374 |
T111029 | 3220,3037,2979,2913,1855,1332,1938,1868,1656,1548,1461,1370 |
T111030 | 3398,3377,3124,1888,1685,1582,1519,1486,1453,1372 |
T111031 | 3332,3178,3124,3079,2963,1685,1594,1528,1490,1445,1379 |
T111103 | 3448,3286,3087,3050,2950,1640,1573,1499,1445,1373 |
T111104 | 3299,3153,3079,3037,2950,1660,1548,1499,1465,1373 |
T111105 | 3411,3282,2958,2934,1681,1652,1602,1569,1432,1379 |
T111112 | 3290,3174,3066,2938,1915,1864,1797,1652,1586,1478,1382 |
T111113 | 3415,3070,2954,2788,1926,1797,1689,1619,1532,1478,1461,1378 |
T111114 | 3294,2954,2788,1660,1602,1548,1523,1486,1441,1374 |
TX111121 | 3415,3290,3058,1872,1656,1569,1548,1486,1432,1333 |
T111122 | 3299,3083,3088,2963,1893,1664,1557,1528,1428,1376 |
T111125 | 3440,3278,2958,1652,1569,1441,1370 |
TX111127 | 3348,3124,3091,2958,2788,1967,1669,1561,1494,1424,1373 |
T111129 | 3448,3270,2983,2929,2855,1955,1644,1569,1499,1432,1371 |
T111202 | 3431,3187,3116,2992,1986,1669,1586,1432,1372 |
T111208 | 3377,3079,3050,3000,1959,1681,1573,1548,1449,1371,1295 |
T111209 | 3452,3162,3062,2963,2929,1685,1573,1449,1374 |
T111210 | 3452,3386,2996,2954,1689,1577,1449,1375 |
T111211 | 3456,3126,3070,2958,2867,1685,1573,1441,1370 |
T111213 | 3447,3165,3111,3049,2863,1772,1606,1568,1510,1436,1377 |
T111215 | 3294,3058,2954,1971,1921,1651,1527,1490,1436,1379 |
T111216 | 3443,3178,3107,3041,2929,2821,2365,1697,1573,1440,1374 |
T120201 | 3447,3170,3103,3037,2929,2746,1693,1568,1436,1370 |
T120203 | 3452,2995,2946,2361,1676,1577,1498,1432,1375 |
T120210 | 3447,3178,3041,2958,2357,1763,1618,1577,1523,1427,1373 |
T120211 | 3452,3079,3041,2958,1731,1611,1569,1416,1374 |
T120212 | 3444,2996,2954,2884,1785,1694,1569,1536,1436,1376 |
T120228 | 3427,3046,2954,2614,2258,2187,1698,1565,1432,1378 |
T120229 | 3046,2954,2876,2838,2751,1660,1494,1428,1371 |
T120301 | 3420,3000,2958,2934,1573,1428 |
T120303 | 3456,3004,2958,1781,1727,1685,1577,1507,1420 |
T120525 | 3435,3166,3041,2954,2938,2847,1689,1569,1432,1320 |
T120526 | 3440,3166,2975,2938,2842,2747,1685,1573,1436,1320 |
T120528 | 3473,3091,2954,2896,1681,1577,1486,1382 |
T130423 | 3456,2067,1656,1573,1532,1461,1432,1300,1266 |
由表5和表6可见,实施例1-39所制备的3-三氟甲基吡唑化合物的1H-NMR显示与其结构相应的化学位移、H的数目与其结构吻合,IR出现相应的骨架吸收峰。
实施例41实施例1-39所制备的3-三氟甲基吡唑化合物对7种常见代表性病害病原的抑菌活性测定
(1)PDA培养基制备:将200g马铃薯去皮切块,加1000mL蒸馏水,煮沸10-20min。用纱布过滤,补加蒸馏水至1000mL。加入20g葡萄糖和17g琼脂,加热融化,分装,高压蒸汽灭菌2h,备用。
(2)病原真菌的培养:用接种针挑取少量病原菌菌丝于PDA培养基上,置于25℃恒温培养箱中培养2-4天,菌丝长好后待用。
(3)测定方法:采用菌丝生长速率法(一定时间内菌落直径的大小)测定化合物的抑菌活性。在离心管中准确称取5mg供试目标化合物,先用适量丙酮溶解,再加入计算量的含有1%吐温20乳化剂的水溶液,稀释成1000mg/L的药液。取1mL药液加入9mL培养基中摇匀,配制成100mg/L的含药培养基,均匀倒入培养皿。同时添加不含共试目标化合物、含有相同量的丙酮及吐温20乳化剂培养基的培养皿做空白对照。用灭菌的打孔器(直径4mm)在生长良好,无污染,长势均匀菌落边缘打取菌饼,在无菌条件下接入含药培养基中心(每个培养皿接种一个菌饼),盖上皿盖,皿盖朝下,每处理重复3次。将培养基置于25℃恒温培养箱中培养,待对照培养皿中菌落直径扩展到4-5cm后用十字交叉法测量各处理菌饼扩展直径,求平均值,与空白对照比较计算相对抑菌率。
(4)抑菌率的计算:
菌落增长直径(mm)=菌落测量直径(mm)-菌饼直径(mm)
相对抑制率(%)=[对照菌落增长直径(mm)-含药培养基上菌落增长直径(mm)]/对照菌落增长直径(mm)×100
按照上述方法,测定实施例1-39所制备的3-三氟甲基吡唑化合物对七种常见代表性病害病原的抑菌效果,测定结果见表7(表中数据为各化合物在100mg/L时对病原菌生长的抑制百分率)。
其中,设嘧菌酯为对照农药。
表7实施例1-39所制备的3-三氟甲基吡唑化合物抑菌活性
从表7中数据看出,实施例1-39所制备化合物在100mg/L浓度下,对所选七种病原菌大多数具有不同程度的抑菌活性,其中T111027和T120210对苹果炭疽病菌的抑菌率分别达到89.99%和90.17%,T111031和T111215对苹果腐烂病菌的抑菌率达到100.00%和97.80%,T120201和T120210对黄瓜灰霉病菌的抑菌率达到83.33%和86.67%,T120201对梨黑斑病菌抑菌率达到87.84%,抑菌率高于对照农药嘧菌酯。
Claims (11)
3.权利要求1或2所述化合物的制备方法,包括以下步骤:在室温将1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯的惰性溶剂溶液滴加入RXH和K2CO3的惰性溶剂溶液中,滴加完毕后,升至40~60℃温度下反应,反应完毕后抽滤、去除反应溶剂,经重结晶纯化后即得所述化合物。
5.根据权利要求3或4所述的制备方法,其特征在于:制备权利要求2中化合物T120301和T120528时,RXH分别为2,5-二巯基-3,4-噻二唑和2-氨基-5-巯基-3,4-噻二唑,而且1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯、RXH和K2CO3的摩尔质量比为2:1:2;制备权利要求2中其他化合物时,所述1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯、RXH和K2CO3的摩尔质量比为1:1:1。
6.根据权利要求3或4所述的制备方法,其特征在于:所述惰性溶剂为乙腈、氯仿或甲苯。
7.权利要求1或2所述的3-三氟甲基吡唑化合物在防治农作物农业病害中的用途。
8.权利要求1或2所述的3-三氟甲基吡唑化合物在抑制病原菌生长或杀灭病原菌中的用途。
9.权利要求1或2所述的3-三氟甲基吡唑化合物在制备抑制病原菌生长或杀灭病原菌药物中的用途。
10.一种农用组合物,其包含0.1~99.9重量%的权利要求1或权利要求2中任一项所述的化合物以及农药学上可接受的载体和/或赋形剂。
11.根据权利要求10所述的农用组合物的用途,其特征在于:作为农用杀菌剂中的用途。
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