CN103265527A - 邻氨基苯甲酰胺化合物及其制备方法和应用 - Google Patents
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Abstract
本发明公开了一种邻氨基苯甲酰胺化合物及其制备方法和应用，该化合物的化学名称为3-溴-1-（3-氯-2-吡啶基）-N-[4-硫代甲酰胺基-2-甲基-6-（甲胺基甲酰基）-苯基]-1H-吡唑-5-甲酰胺，它是由溴氰虫酰胺与硫化剂在极性有机溶剂以及催化剂的存在下，在0～100℃的温度下反应得到。本发明的化合物可以单独制备杀虫剂，也可以与阿维菌素类杀虫剂、新烟碱类杀虫剂或者菊酯类杀虫剂制备混合杀虫剂，单独制备的杀虫剂用于防治鳞翅目害虫、双翅目害虫或者半翅目害虫。
Description
技术领域
本发明属于农药杀虫剂领域，具体涉及一种可以制备杀虫剂的邻氨基苯甲酰胺化合物及其制备方法和应用。
背景技术
害虫的防治是农药科学研究的核心领域之一，这个领域涉及到人类赖以生存的粮食增产和丰收。
随着科学的进步，农药领域不断开发新的高效、低毒杀虫剂替代高毒性杀虫剂，如有机磷类杀虫剂、氨基甲酸酯类杀虫剂等等。
作为高效、低毒杀虫剂的代表，新烟碱类杀虫剂也已经有了二十多年的历史，目前很多都已产生了抗性。
而邻氨基苯甲酰胺类杀虫剂则是目前比较新的一类高效、低毒杀虫剂。
溴氰虫酰胺（又名氰虫酰胺，CAS登录号为736994-63-1）就是邻氨基苯甲酰胺类杀虫剂中最具代表性的一种杀虫剂，其化学名称为：3-溴-1-（3-氯-2-吡啶基）-N-[4-氰基-2-甲基-6-（甲胺基甲酰基）-苯基]-1H-吡唑-5-甲酰胺。
结构式如下：
溴氰虫酰胺主要通过诱导昆虫鱼尼丁受体，调控胞内钙离子释放而表现出触杀和胃毒作用。主要用于水稻、蔬菜、果树、棉花等作物防治鳞翅目害虫、双翅目害虫或者半翅目害虫。不过其单剂在防治鳞翅目害虫如螟虫、粘虫等效果并不好。
发明内容
本发明的第一目的在于解决上述问题，提供一种对多种害虫均具有防治效果，尤其是对鳞翅目害虫具有显著防治效果的邻氨基苯甲酰胺化合物。
本发明的第二目的在于提供上述邻氨基苯甲酰胺化合物的制备方法。
本发明的第三目的在于提供上述邻氨基苯甲酰胺化合物的应用。
实现本发明第一目的的技术方案是：一种邻氨基苯甲酰胺化合物，其化学名称为：3-溴-1-（3-氯-2-吡啶基）-N-[4-硫代甲酰胺基-2-甲基-6-（甲胺基甲酰基）-苯基]-1H-吡唑-5-甲酰胺，其结构式如下：
实现本发明第二目的的技术方案是：一种邻氨基苯甲酰胺化合物的制备方法：它是由溴氰虫酰胺与硫化剂在极性有机溶剂以及催化剂的存在下，在0～100℃的温度下反应得到。
上述反应温度优选25～60℃。
所述的催化剂为氯化镁、氯化锌或者氯化锡，优选氯化镁；溴氰虫酰胺与催化剂的摩尔比为1∶1～1∶2，优选1∶1。
所述的硫化剂为NaSH、Na2S203或者H2S，优选NaSH；溴氰虫酰胺与硫化剂的摩尔比为1∶1～1∶3，优选1∶1.5～1∶2。
所述的极性有机溶剂为N,N-二甲基甲酰胺（DMF）、四氢呋喃、乙二醇二甲醚、二氧六环、丙酮、丁酮中的一种或者两种。
实现本发明第三目的的技术方案是：上述邻氨基苯甲酰胺化合物在制备杀虫剂上的应用。
上述邻氨基苯甲酰胺化合物可以单独制备杀虫剂，也可以与阿维菌素类杀虫剂、新烟碱类杀虫剂或者菊酯类杀虫剂制备混合杀虫剂。
上述邻氨基苯甲酰胺化合物与其它杀虫剂制备混合杀虫剂时，其重量百分比为0.1%～99.9%。新烟碱类杀虫剂为吡虫啉、噻虫啉、噻虫嗪或者噻虫胺；菊酯类杀虫剂为高效氯氰菊酯或者功夫菊酯。
上述邻氨基苯甲酰胺化合物单独制备杀虫剂时，其作为活性成份，通过加入助剂和载体制成农药上的常规剂型，如水乳剂、水分散粒剂、悬浮剂、可湿性粉剂等等，其有效含量为0.1～99.9wt%，优选30～99wt%，更优选70～99wt%。所制备的杀虫剂用于防治作物中的鳞翅目害虫、双翅目害虫或者半翅目害虫，优选用于防治鳞翅目害虫，如粘虫、螟虫、叶蝉、飞虱等。所述作物包括玉米、棉花、小麦、水稻、果树、蔬菜、花卉等。
对于所制备的杀虫剂的使用，可选择常用施药方法，如叶面喷洒、水面施用、土壤处理及种子处理等。
本发明具有的积极效果：本发明的化合物作为邻氨基苯甲酰胺类杀虫剂中的一个新品种，其相对于现有的溴氰虫酰胺在防治鳞翅目害虫上具有显著效果，而且该化合物制备方法简单，成本较低。
附图说明
图1为本发明的化合物的液谱图。
图2为本发明的化合物的质谱图。
图3为本发明的化合物的核磁共振图谱。
具体实施方式
（实施例1）
本实施例的邻氨基苯甲酰胺化合物的化学名称为：3-溴-1-（3-氯-2-吡啶基）-N-[4-硫代甲酰胺-2-甲基-6-（甲氨基甲酰基）-苯基]-1H-吡唑-5-甲酰胺，其结构式如下：
该邻氨基苯甲酰胺化合物的制备方法如下：
在250mL的四口瓶内加入3.0g浓度为70wt%的NaSH（0.0375mol）、1.9g的氯化镁（0.02mol）以及50mL的乙二醇二甲醚，搅拌溶解完全，然后将9.5g的溴氰虫酰胺（0.02mol）加入到反应体系中，搅拌下升温至25℃，保温反应10～11h。
反应结束后，先真空下蒸出乙二醇二甲醚，然后加入100mL水，并用盐酸调节pH为6～7，接着在10℃以下搅拌1h，过滤，得到9.8g的土黄色的粗品，收率为86.7%，纯度为90%（HPLC）。粗品经重结晶后得到纯度为98%以上的精品，其熔点为225.6～226.5℃。
该化合物的液谱图见图1，质谱图见图2，核磁共振图谱见图3。
通过液质联用测得其分子量为506，结合核磁共振确定上述结构式。
（实施例2～实施例4）
各实施例的化合物与实施例1相同。
各实施例的制备方法与实施例1基本相同，不同之处见表1。
表1
（应用例）
本应用例为本发明的化合物（以下简称新化合物）的杀虫活性试验。
1、试验条件。
1.1、供试靶标。
粘虫、二化螟。
1.2、培养条件。
试验温度为25～28℃。
1.3、仪器设备。
电子天平、玻璃试管、烧杯、移液器、恒温培养箱、喷雾器、WM-4无油空气压缩机、直尺、平皿等。
2、试验设计。
2.1、试验药剂。
测试药剂：96%的新化合物。
对照药剂：95%的溴氰虫酰胺。
以上样品均由江苏省农用激素工程技术研究中心有限公司提供。
2.2、试验处理。
2.2.1、粘虫。
新化合物：0.390625mg/L、0.78125mg/L、1.5625mg/L、3.125mg/L、6.25mg/L、12.5mg/L、25mg/L、50mg/L、100mg/L。
溴氰虫酰胺：0.390625mg/L、0.78125mg/L、1.5625mg/L、3.125mg/L、6.25mg/L、12.5mg/L、25mg/L、50mg/L、100mg/L。
2.2.2、二化螟。
新化合物：6.25mg/L、12.5mg/L、25mg/L、50mg/L、100mg/L；
溴氰虫酰胺：12.5mg/L、25mg/L、50mg/L、100mg/L、200mg/L。
2.3、试验方法。
粘虫采用玉米叶浸渍法，在预先配制的药液处理浓度中浸渍5秒，然后将玉米叶上药液晾干后，剪取玉米叶，喂饲三龄幼虫，48小时后，检查死虫数，计算死虫率。
二化螟采用综合独立测试法，将水稻浸种催芽后置于搪瓷盘中避光无土培养，待芽长至1～2cm时，在各处理药液中浸渍5秒后晾干，然后放入50mL磨口瓶中喂饲三龄幼虫，同时放入润湿棉球保湿，药后2天、4天和7天检查死虫数，计算死虫率，共调查3次。每处理均设3次重复。
3、数据调查与统计分析。
3.1、统计分析方法。
调查并计算各测试靶标的死亡率并用数据处理系统（DPS）软件进行统计分析，计算各药剂的LC50，r值等及其95%置信限。
3.2、试验结果。
3.2.1、粘虫的试验结果。
药后2天调查粘虫的死亡情况，计算出死亡率并进行统计分析，具体情况见表2和表3。
表2
表3
| 回归方程 | r值 | LC50 | 95%置信限 | |
| 新化合物 | y=4.2989+1.3438 | 0.9934 | 3.2483 | 2.8955～3.8611 |
| 溴氰虫酰胺 | y=4.1466+0.6505 | 0.9850 | 20.5140 | 16.3610～25.7212 |
由表2和表3可以看出，新化合物的LC50大大低于对照药剂溴氰虫酰胺的LC50，说明新化合物对粘虫的药效明显优于溴氰虫酰胺。
3.2.2、二化螟的试验结果。
药后2天、4天和7天调查二化螟的死亡情况，计算出死亡率并进行统计分析，具体情况分别见表4（药后2天）、表5（药后4天）、表6（药后7天）以及表7。
表4
表5
表6
表7
| 回归方程 | r值 | LC50 | 95%置信限 | |
| 新化合物 | y=2.0421+2.0722 | 0.9853 | 26.7545 | 21.8037～32.8240 |
| 溴氰虫酰胺 | y=2.1473+1.3713 | 0.9949 | 120.3107 | 103.4107～139.9726 |
由表4～表7可知，药后2天新化合物和溴氰虫酰胺对水稻二化螟基本无防效，药后4天防效也均较低，药后7天药效有较大改善，其中新化合物的LC50大大低于对照药剂溴氰虫酰胺的LC50，说明新化合物对二化螟的药效明显优于溴氰虫酰胺。
Claims (10)
1.一种邻氨基苯甲酰胺化合物，其特征在于结构式如下：
2.权利要求1所述的邻氨基苯甲酰胺化合物的制备方法，其特征在于：它是由溴氰虫酰胺与硫化剂在极性有机溶剂以及催化剂的存在下，在0～100℃的温度下反应得到。
3.根据权利要求2所述的邻氨基苯甲酰胺化合物的制备方法，其特征在于：所述的催化剂为氯化镁、氯化锌或者氯化锡；所述的溴氰虫酰胺与所述的催化剂的摩尔比为1∶1～1∶2。
4.根据权利要求2或3所述的邻氨基苯甲酰胺化合物的制备方法，其特征在于：所述的硫化剂为NaSH、Na2S203或者H2S；所述的溴氰虫酰胺与所述的硫化剂的摩尔比为1∶1～1∶3。
5.根据权利要求4所述的邻氨基苯甲酰胺化合物的制备方法，其特征在于：所述的极性有机溶剂为N,N-二甲基甲酰胺、四氢呋喃、乙二醇二甲醚、二氧六环、丙酮、丁酮中的一种或者两种。
6.权利要求1所述的邻氨基苯甲酰胺化合物在制备杀虫剂上的应用。
7.根据权利要求6所述的邻氨基苯甲酰胺化合物在制备杀虫剂上的应用，其特征在于：所述的邻氨基苯甲酰胺化合物为单独制备杀虫剂，其有效含量为0.1～99.9wt%。
8.根据权利要求7所述的邻氨基苯甲酰胺化合物在制备杀虫剂上的应用，其特征在于：所制备的杀虫剂用于防治鳞翅目害虫、双翅目害虫或者半翅目害虫。
9.根据权利要求8所述的邻氨基苯甲酰胺化合物在制备杀虫剂上的应用，其特征在于：所制备的杀虫剂用于防治鳞翅目害虫。
10.根据权利要求6所述的邻氨基苯甲酰胺化合物在制备杀虫剂上的应用，其特征在于：所述邻氨基苯甲酰胺化合物与阿维菌素类杀虫剂、新烟碱类杀虫剂或者菊酯类杀虫剂制备混合杀虫剂；所述新烟碱类杀虫剂为吡虫啉、噻虫啉、噻虫嗪或者噻虫胺；所述菊酯类杀虫剂为高效氯氰菊酯或者功夫菊酯；制备混合杀虫剂时，所述邻氨基苯甲酰胺化合物的重量百分比为0.1%～99.9%。
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