CN1098719A - 六氢三嗪化合物的制备方法 - Google Patents

六氢三嗪化合物的制备方法 Download PDF

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CN1098719A
CN1098719A CN94103331A CN94103331A CN1098719A CN 1098719 A CN1098719 A CN 1098719A CN 94103331 A CN94103331 A CN 94103331A CN 94103331 A CN94103331 A CN 94103331A CN 1098719 A CN1098719 A CN 1098719A
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福兰克·吴
苅谷昭范
葛山登义
辻敦
高须贺清司
濑上繁则
南倏腾美
佐藤润子
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Abstract

公开了六氢三嗪化合物及其制备方法以及含有 这种物质的杀虫剂。本发明的化合物对害虫具有极 高的抑制活性，对温血动物、鱼类和甲壳纲毒性很低， 而且在不同的植物中不产生植物毒性。本发明的化 合物的结构及各基团的定义参见说明书。

Description

说明书
本发明涉及六氢三嗪化合物的制备方法本发明提供的六氢三嗪化合物由以下通式（Ⅰ）表示：
Figure 941033317_IMG16
其中R代表低级烷基或低级链烯基;R1代表氢、低级烷基、低级链烯基、低级炔基或由
Figure 941033317_IMG17
表示的基团;R2代表由
Figure 941033317_IMG18
或
Figure 941033317_IMG19
表示的基团。
已研制出各种化学药品作为控制害虫的杀虫剂。这种化学药品的代表性实例有有机磷化合物、氨基甲酸盐化合物和合成拟除虫菊酯。但是，由于重复使用这些杀虫剂，许多害虫已获得耐药性，从而使其难以控制这些昆虫。另一方面，虽然某些常用的农药具有很高的杀虫活性，但因其对温血动物或鱼类和甲壳纲具有很高的毒性、或者以大剂量施用很长时间之后存留在环境中，可能会造成环境污染，从而使生态系统混乱。所以，需要开发出新的杀虫剂，这些杀虫剂能有效地控制对常用化学药品已获耐药性的害虫，而且不仅对温血动物毒性很低，对鱼类及甲壳纲亦如此。还需要用后能以低剂量存留在植物和土壤中且对各种植物不产生毒性的新型的杀虫剂。
本发明的一个目的是提供新的化合物，其特点是：①能更有效地控制已对常用化学药品有耐药性的害虫，②对温血动物、鱼类及甲壳纲毒性很低，③施用该药物后以低剂量留在植物和土壤中。此外，这类新的化合物在各种植物中不产生植物毒性。
本发明的另一目的是提供一种制备这类化合物的方法。
本发明的又一目的是提供改进的杀虫剂，它能有效地控制对常用杀虫剂已获耐药性的害虫，对温血动物、鱼类及甲壳纲的毒性很低，以及在其施用后以低剂量留在植物和土壤中。此外，这种改进的杀虫剂对各种植物不产生植物毒性。
通过对各种新型的六氢三嗪化合物的开发进行调研后，本发明人发现由以下通式（Ⅰ）表示的六氢三嗪化合物可用作极有力的杀虫剂且见效快：
其中R代表低级烷基或低级链烯基;R1代表氢、低级烷基、低级链烯基、低级炔基或由
Figure 941033317_IMG21
表示的基团;R2代表 或
Figure 941033317_IMG23
基。
正是这种发现才开发出了本发明。
结合代表性实例，从以下优选方案详细说明中将容易地理解本发明的特点和优点。
由通式（Ⅰ）表示的本发明的化合物是在任何现有技术文献中从未介绍过的新型化合物，且是由本发明人首次合成出的。
制备法（a）
Figure 941033317_IMG24
其中R代表低级烷基或低级链烯基;R1代表氢、低级烷基、低级链烯基、低级炔基或由 表示的基团;R2代表由
Figure 941033317_IMG26
表示的基团，且X代表卤素。
从上述反应式可以看出，在制备法（a）中，本发明的化合物可通过在一种碱性存在下使通式（Ⅱ）表示的化合物在一溶剂中与通式（Ⅲ）表示的化合物如双（氯甲基）甲胺，双（氯甲基）乙胺和双（氯甲基）丙胺反应容易地制备。
可用于该反应的合适的溶剂的例子是醚类，如乙醚和四氢呋喃;乙腈;芳烃;氯代烃;DMF;和DMSO。这些溶剂可单独使用，也可混合使用。可用作碱性物的化合物是例如无机碱，如氢氧化钠和碳酸钾和有机碱，如吡啶和三乙胺。这些碱可以过量使用，特别优选的是每摩尔化合物（Ⅱ）2.1-4摩尔。
反应温度可在-20℃-100℃内自由调节，最好是-5℃-10℃。
制备法（b）
Figure 941033317_IMG27
其中R，R1和R2定义如上。
从上述反应式可以看出，在制备法（b）中，本发明的化合物可通过在一溶剂中使通式（Ⅱ）表示的化合物与通式R-NH（Ⅳ）表示的伯胺反应容易地制备，式（Ⅳ）中R定义如上，且伯胺的例子有甲胺、乙胺和烯丙胺和37%甲醛水溶剂或仲甲醛。
可用于该反应的合适的溶剂的例子是醇类，如甲醇和乙醇;醚类，如二恶烷和四氢呋喃;和水。这些溶剂可单独或混合使用。反应温度可在室温至所用溶剂的沸点内自由调节，但最好是50℃-100℃。
制备法（c）
Figure 941033317_IMG28
其中R，R1和R2的定义如上，Y代表卤素和由-OS2CH3或
Figure 941033317_IMG29
表示的基团。
从上述反应式可以看出，在制备法（c）中，本发明的化合物可通过在一溶剂中、在一种碱性物存在下使通式（Ⅴ）表示的化合物与通式（Ⅵ）表示的化合物反应容易地制备。
可用于该反应的合适的溶剂的例子是DMF;DMSO;乙腈;和醚类，如四氢呋喃和二噁烷。这些溶剂可单独使用或混合使用。举例来说，可用作碱性物的化合物是氢化钠、碳酸钾、氢氧化钠等等。每摩尔化合物（Ⅴ）最好用1.1-2.5摩尔的这类碱。反应温度可在室温-150℃自由调节，最好是40℃-100℃。
本发明的六氢三嗪化合物是新型的化合物。本发明的典型的化合物列于表1。
本发明的任何化合物均可以有效量直接作为杀虫剂施用，也可按传统技术配制成乳液、可湿粉末、粉末、颗粒或可流动形式，然后以配制成的产物施用。液体或固体载体可用于制备含一种或多种本发明化合物的配制的产物。举例来说，可用于此目的液体载体有机溶剂，方便使用的载体是二甲苯、氯苯、甲基萘、环己酮、异佛尔酮、醇类、二甲基甲酰胺和N-甲基吡咯烷酮。固体载体的例子有高岭土、滑石、膨润土、硅藻土和粘土，也可使用合成化合物类，如氧化铝、沸石和硅酸盐类。在制备配的产品中，可以使用各种助剂如乳化性、分散性、铺展剂、湿润剂和渗透剂，以提供具有所需乳化剂、分散剂、悬浮性和渗透性的产品。
以上面通式（Ⅰ）表示的本发明的化合物对各种害虫（包括半翅目，鳞翅目，鞘翅目，双翅目，直翅目和等翅目在内）具有很强的杀虫活性，对人类和动物的毒性很低，且在不同植物中不产生植物毒性，从而可实用作优异的杀虫剂。
可用本发明的化合物有效控制的害虫的例子如下：
半翅目，如褐飞虱、灰飞虱、黑尾叶蝉、康氏粉蚧、矢尖盾蚧、桃蚜、棉蚜、萝卜蚜、梨冠网蝽、稻墨蝽和温室粉虱;鳞翅目，如小菜粉蝶、海灰翅夜蛾、甘蓝夜蛾、二化螟、棉褐带卷蛾、黄地老虎、稻纵卷叶野螟和秆野螟;鞘翅目，如马铃薯瓢虫、黄守瓜、黄曲条跳甲、稻根象、玉米象和红铜丽金龟;双翅目，如家蝇和尖音库蚊;直翅目，如非洲蝼蛄、德国蠊和飞蝗;和等翅目，如家白蚁和黄胸散白蚁。
以下用非限制性实施例进一步说明本发明。
实施例
以下用合成例详细介绍制备本发明化合物的方法。
合成例1
合成1-（2-氯-5-吡啶基甲基）-5-甲基-2-硝基亚氨基六氢-1，3，5-三嗪
将0.6克1-（2-氯-5-吡啶基甲基）-3-硝基胍和0.4克双（氯甲基）甲胺悬浮在无水THF中。冷却下，往悬浮液中滴加入0.52克三乙胺和THF的溶液。反应混合物搅拌1小时，然后倒入冰水中。用二氯甲烷萃取混合物。萃取物用无水硫酸镁干燥之后，蒸掉二氯甲烷。残余物用甲醇重结晶，得到0.78克标题化合物。在表1中，该化合物是1号，m.p.：150-154℃。
合成例2
合成1-（2-氯-5-吡啶基甲基）-5-乙基-2-硝基亚氨基六氢-1，3，5-三嗪
往搅拌着的1克1-（2-氯-5-吡啶基甲基）-3-硝基胍、0.28克70%乙胺于水和20ml乙醇的混合物中，边加热边滴加0.71克37%甲醛水溶液。反应混合物加热回流2小时。冷却到室温后，形成晶体，将其过滤出并用甲醇重结晶，得到1.15克标题化合物。在表1中，该化合物是2号，m.p.：124-125℃。
合成例3
合成1-（2-氯-5-吡啶基甲基）-3，5-二甲基-2-硝基亚氨基六氢-1，3，5-三嗪
将1克1，5-二甲基-2-硝基亚氨基六氢-1，3，5-三嗪溶于20ml无水THF。冷却下，往溶液中加入0.27克60%氢化钠。室温下，搅拌混合物1小时，直至氢气挥发中止，然后在搅拌下将混合物再于50℃搅拌1小时。于40-50℃，往混合物中滴加0.9克2-氯-5-吡啶基甲基氯于8ml无水DMF的溶液。加入完毕后，于70-80℃搅拌下加热反应混合物2小时。反应混合物倒入冰水中并用二氯甲烷萃取。萃取物用无水硫酸镁干燥，并蒸掉二氯甲烷。残余物用色谱柱纯化，得到1.3克标题化合物。在表1中，该化合物是5号，m.p.：116-117℃。
合成例4
合成1-（2-氯-5-噻唑基甲基）-3，5-二甲基-2-硝基亚氨基六氢-1，3，5-三嗪。
将1.7克1，5-二甲基-2-硝基亚氨基六氢-1，3，5-三嗪溶于20ml无水DMF。冷却下，分批加入0.28克60%氢化钠。混合物于室温搅拌1小时，直至氢气挥发中止，然后在搅拌下于50℃将混合物再加热1小时。在40-50℃，往混合物中滴加1.7克2-氯-5-噻唑基甲基氯于8ml无水DMF的溶液。加入完毕后，反应混合物再于70-80℃搅拌加热2小时。将混合物倒入冰水中并用二氯甲烷萃取。萃取物用无水硫酸镁干燥，并蒸掉二氯甲烷。残余物用色谱柱纯化，得到0.82克标题化合物。在表1中，该化合物是6号，m.p.：125-126℃。
以下示出某些具体配制例。但是，应指出，可用于配制本发明的杀虫剂的载体、表面活性剂和其它添加剂并不限于以下配制例。在以下配制例中，“份数”代表“重量份”。
配制例1
在制粉过程中，将32.5份表1中1号化合物、3份木质素磺酸、4份聚氧乙烯烷基苯酚醚、2份二氧化硅水合物和58.5份粘土均匀混合，得到可湿粉末。
配制例2
在制粉过程中，将5.4份表1中2号化合物、2份二氧化硅水合物和92.6份滑石均匀混合，得到粉剂。
配制例3
在制粉过程中，将5.4份表1中3号化合物、3份木质素磺酸盐、1份十二烷基苯磺酸钠、30份膨胀土和60.6份粘土均匀混合。然后，将混合物与水一起捏合、造粒并干燥，得到颗粒。
参考以下试验例说明本发明化合物的杀虫效果
试验例1
将5株高度约为7cm的稻苗浸入可湿粉末的稀释水溶液中10秒，所述可湿粉末各含预定浓度的各样品化合物（按配制例1介绍的工序制得的）。风干之后，将这5株稻苗的根部用含水卫生棉包住，放在直径3cm、高20cm的玻璃容器中。将10个已获耐化学药品性的绿稻叶蝉的二龄幼虫放入各玻璃容器中。该容器放置在保持在26℃的室内。处置48小时后，测定幼虫死亡率。结果示于表2。
Figure 941033317_IMG30
Figure 941033317_IMG31
表 2
化合物号 死亡率（％），500  ppm
123456789101112对照化合物 10010010010010010010010010010010010070
注：表2中的对照化合物是Sumithion（商标），其分子式如下：
Figure 941033317_IMG32
试验例2
将5株高度约为7cm的稻苗浸入可湿粉末的稀释水溶液中，该可湿粉末分别含有预定浓度的各样品化合物（按配制例1介绍的工序制得的）。风干后，将这5株稻苗的根部用含水卫生棉包住，放置在直径3cm、高度20cm的玻璃容器中。将10个已获耐化学药品性的棕稻飞虱的二龄幼虫放入各玻璃容器中。将容器置于保持在26℃的室温内。处置48小时后，测定幼虫死亡率。结果示于表3。
表 3
化合物号 死亡率（％），500  ppm
123456789101112对照化合物 10010010010010010010010010010010010065
注：表3中的对照化合物与表2中的相同。
从以上说明可以看出，本发明的化合物对控制各种害虫具有极高的活性，对温血动物、鱼类和甲壳纲毒性很低，而且在不同的植物中不产生植物毒性。

Claims (3)

1、一种制备由以下通式(Ⅰ)表示的六氢三嗪化合物的方法：
其中R代表低级烷基或低级链烯基；R1代表氢、低级烷基、低级链烯基、低级炔基或由
Figure 941033317_IMG2
表示的基团；R2代表由
Figure 941033317_IMG3
或
Figure 941033317_IMG4
表示的基团，
该方法包括以下步骤：使通式(Ⅱ)表示的化合物
Figure 941033317_IMG5
(其中R1和R2定义如上)与通式(Ⅲ)表示的化合物反应
(其中R的定义如上且X代表卤素)。
2、一种制备由以下通式（Ⅰ）表示的六氢三嗪化合物的方法：
Figure 941033317_IMG6
其中R代表低级烷基或低级链烯基;R1代表氢、低级烷基、低级链烯基、低级炔基或
Figure 941033317_IMG7
表示的基团;R2代表 或
Figure 941033317_IMG9
表示的基团
该方法包括以下步骤：使通式（Ⅱ）表示的化合物
Figure 941033317_IMG10
（其中R1和R2定义如下）与通式（Ⅳ）的伯胺
（其中R的定义如上）和甲醛溶液或仲甲醛进行反应。
3、一种制备由以下通式（Ⅰ）表示的六氢三嗪化合物的方法：
Figure 941033317_IMG11
（Ⅰ）其中R代表低级烷基或低级链烯基;R1代表氢、低级烷基、低级链烯基、低级炔基或
Figure 941033317_IMG12
表示的基团;R2代表
Figure 941033317_IMG13
表示的基团，
该方法包括以下步骤：使通式（Ⅴ）表示的化合物
Figure 941033317_IMG14
（Ⅴ）（其中R和R1定义如上）与通式（Ⅵ）表示的化合物反应
（其中R2的定义如上且Y代表卤素或由-SO2CH3或 表示的基团）。
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