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CN103524418B - 一组3-甲基吡唑化合物 - Google Patents

一组3-甲基吡唑化合物 Download PDF

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CN103524418B
CN103524418B CN201310527240.2A CN201310527240A CN103524418B CN 103524418 B CN103524418 B CN 103524418B CN 201310527240 A CN201310527240 A CN 201310527240A CN 103524418 B CN103524418 B CN 103524418B
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CN103524418A (zh
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孙家隆
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Qingdao Agricultural University
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Abstract

本发明提供了一组3-甲基吡唑化合物，该化合物通式为

Description

一组3-甲基吡唑化合物
技术领域
本发明属于农药领域，技术方案涉及一组3-甲基吡唑化合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
吡唑类化合物具有高的生物活性，作为农药方面的应用越来越引人注目。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，以1，3-二甲基-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-甲基吡唑化合物，生物活性试验结果表明，所制备的化合物具有很好的杀菌、抑菌作用。
发明内容
本发明的目的是提供一组3-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-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1，3-二甲基-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20～50℃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中与化合物编号相对应的任意一种。
表2制备本发明3-甲基吡唑化合物所需RXH
具体的，制备化合物T111021、T111022、T120604和T120605时，RXH分别为2-亚硫基咪唑烷、N-硝基亚氨基咪唑烷、2-巯基-5-氨基3，4-噻二唑和2,5-二氨基3，4-噻二唑，而且1，3-二甲基-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1，3-二甲基-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。
本发明的另一个目的是提供所述3-甲基吡唑化合物为农用杀菌剂应用。
本发明的有益效果是：本发明的3-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-甲基吡唑化合物用于防治农业病害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提供3-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T110906的制备
在装配有温度计、搅拌器和冷凝器的100毫升的三口瓶中加入5毫摩尔无水K2CO3粉末、5毫摩尔2,6-二甲基苯胺、35毫升氯仿，低温(0±5℃)下缓慢滴加5毫摩尔1-甲基-3-三氟甲基-5-氯-4-吡唑甲酰氯溶于25毫升氯仿所配成的溶液，滴加完毕，缓慢升温至室温(20±5℃)，并于室温搅拌反应6小时。减压过滤反应混合物，将所得滤液减压脱溶，制得化合物T110906粗品，用乙醇-石油醚(体积比3：1)对化合物T110906粗品重结晶，制得针状白色晶体化合物T110906纯品，收率94％。
实施例2～30表1中其他29种化合物的制备
具体操作如表3。
表3实施例2～24具体操作
实施例31实施例1-30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1-30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1-30所制备的3-甲基吡唑化合物物理化学性质及收率
表5实施例1-30所制备的3-甲基吡唑化合物核磁共振氢谱数据
表6实施例1-30所制备的3-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
T110906 3224，3033，2921，1635，1540，1515，1457，1373，1304
T110907 3253，2037，2934，1635，1532，1399，1376，1270
T110908 3406，3257，3095，2929，1673，1652，1586，1544，1441，1377，1308
T110911 3274，3170，3100，2925，1947，1648，1582，1572，1474，1403，1373
T110913 3440，3178，2983，1677，1573，1532，1432，1374
T110915 3390，3282，2988，2925，2855，1764，1652，1586，1499，1436，1378
T110916 3361，3095，2988，2934，1685，1602，1544，1494，1378，1374
T110917 3378，3012，2922，1926，1768，1661，1542，1408，1369
T110918 3153，3050，2929，1677，1598，1548，1528，1445，1370，1378
T110919 3120，3046，2983，2925，1660，1519，1416，1362，1370
T110920 3323，3098，2987，1668，1518，1416，1376
T110921 3502，3211，3021，2704，1627，1515，1378
T110922 3344，3017，2942,2884,2187，1681，1573，1465，1370
T110923 3382，2975，2921，1698，1673，1602，1544，1515，1490，1436，1370
T111013 3236，3166,3062,2909，1685，1598，1553，1519，1482，1432，1376
T111014 3153，2979,2943，2908,2839，1673，1530，1441，1373
T111015 3315，3129,2992，1664，1503，1403，1374
T111016 3382，2958,2921，1673，1577，1511，1378，1374
T111019 3070，2963，2871，2842，1652，1598，1507，1461，1366
T111020 2992，2929，1685，1664，1519，1474，1378，1366
T111021 3432，2942，1706，1664，1582，1515，1461，1395
T111022 3423，2938，1685，1664，1582，1515，1461，1395
T111023 3427，3270,3054,2954，1727，1615，1569，1478，1387
T111024 3427，3270,3054,2954，1727，1615，1596，1478，1387
T120601 3448，3236,3141，2934,2793，1677，1573，1523，1436，1366
T120602 3402，2975，2929,2788，1660，1569，1424,1371
T120603 3423，3108,2988,2954，1652，1573，1436，1333
T120604 3377，3116，2954，1644，1511，1441，1304
T120605 3440，2996,2954，1648，1573，1519，1445
T130422 3440，2067，1640，1573，1523，1432，1304，1266
由表5和表6可见，实施例1-30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32实施例1-30所制备的3-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1-30所制备的3-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1-30所制备的3-甲基吡唑化合物杀菌活性
从表7中数据看出，实施例1-30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T110915对番茄早疫病菌的抑菌率分别达到93.95％、T111015对梨黑斑病菌的抑菌率达到100.00％、T111020对西瓜枯萎病菌的抑菌率达到100.00％、T120603和T120604对苹果腐烂病菌抑菌率分别达到89.66％和100.00％，抑菌率高于对照农药嘧菌酯。

Claims (6)

1.一组3-甲基吡唑化合物，所述化合物及其结构式选自下表中的任意一种：
2.权利要求1所述化合物的制备方法：在室温将1，3-二甲基-5-氯-4-吡唑甲酰氯的乙腈或氯仿或甲苯溶液中滴加入RXH和K2CO3的乙腈或氯仿或甲苯溶液中，滴加完毕后，升至20～50℃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，所述RXH选自下表中的任意一种：
3.根据权利要求2所述的制备方法，其特征在于：制备权利要求1中化合物T111021、T111022、T120604和T120605时，RXH分别为2-亚硫基咪唑烷、N-硝基亚氨基咪唑烷、2-巯基-5-氨基3，4-噻二唑和2，5-二氨基3，4-噻二唑，而且1，3-二甲基-5-氯-4-吡唑甲酰氯、RXH和K2CO3的摩尔数比为2∶1∶2，制备权利要求1中其它化合物时，1，3-二甲基-5-氯-4-吡唑甲酰氯、RXH和K2CO3的摩尔数比为1∶1∶1。
4.权利要求1所述的3-甲基吡唑化合物在防治农作物农业病害中的应用。
5.权利要求1所述的3-甲基吡唑化合物在抑制病原菌生长或杀灭病原菌中的应用，其中所述病原菌引起的疾病不包括人体或动物体的疾病。
6.权利要求1所述的3-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应用，其中所述病原菌引起的疾病不包括人体或动物体的疾病。
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