CN102060818A - 一种新型螺螨酯类化合物及其制法与用途 - Google Patents
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Abstract
本发明涉及一种新型螺螨酯类化合物及其合成方法与应用，该螺螨酯类化合物的结构如通式Ⅰ所示。其合成方法为在缚酸剂存在下，于非质子性溶剂中，室温条件下使结构式为Ⅱ的化合物与结构式为
的氯甲酸酯反应，产物经分离提纯制得。本发明的螺螨酯类化合物可用于杀虫或杀螨
Description
技术领域
本发明属于农药领域，涉及一种新型螺螨酯类化合物及其合成方法，适用作杀虫、杀螨剂。
背景技术
螺螨酯(结构式为III)是拜耳公司开发的季酮酸类高效杀螨剂，与现有的杀虫杀螨剂具有不同的作用机制，通过抑制害螨体内脂质的合成，对若螨尤其对螨卵具有优异的抑杀作用。
CN101255147A报道了用结构式
的化合物与菊酰氯反应合成了系列螺螨酯类衍生物，并对螨和蚕豆蚜做了生物活性测试。
由于大量、频繁地用药，有害虫、螨对众多杀虫、杀螨剂产生了严重抗药性。开发新型结构及其作用机制的杀虫、杀螨剂，是克服或延缓抗药性有效手段。现有技术中，如本发明的新型螺螨酯类化合物的结构、制备方法及杀螨(螨卵)活性未见报道。
发明内容
本发明的目的在于提供一种结构新颖的螺螨酯类杀虫、杀螨剂及其制备方法。
技术方案：
本发明提供一种新型螺螨酯类化合物，如通式I所示。
其中R为
本发明还提供了上述螺螨酯类化合物的制备方法：在敷酸剂存在下，于非质子性溶剂中，使结构式为
的化合物与结构式为
的氯甲酸酯在室温下反应1～2h制得，其中R为：
作为本发明新型螺螨酯类化合物制备方法的改进：所述的非质子性溶剂为烷烃类、醚类、芳香烃类。所述的缚酸剂为三级胺类化合物。烷烃类为石油醚或环己烷；醚类为甲基叔丁基醚；芳香烃类为甲苯或苯；取代烷烃类为二氯甲烷，1，2-二氯乙烷；三级胺类化合物为三乙胺、吡啶或甲基吡啶等。
作为本发明新型螺螨酯类化合物的制备方法的进一步改进：氯甲酸酯以滴加方式加入，滴加温度为0～5℃；提纯方法为重结晶，重结晶溶剂选用C1～C3中任意一级醇，优选甲醇或乙醇。
本发明所述的新型螺螨酯类化合物的用途：用于杀虫或杀螨。
本发明的目的是从结构式II的化合物出发与不同的氯甲酸酯反应，制备系列螺螨酯类化合物，并通过生物活性测试，期望从中筛选出高活性的化合物。结构式为II的化合物在US6436988B1中已经报道并合成。
本发明的新型螺螨酯类化合物的制备方法可以用下列方程式加以说明：
为方便表述，将
中的R做如下标注：
将上述所得的新型螺螨酯类化合物进行室内杀螨卵生测试验，在5ppm下，所有新化合物与对照药剂(螺螨酯)均有100％的杀灭率；在1ppm浓度下，新化合物均同于或优于螺螨酯的杀螨效果。
本发明的优点在于：制备了未见报道的新型螺螨酯类化合物，在相同的药剂浓度下，制备的新化合物对螨卵的抑杀效果优于或同于螺螨酯。
具体实施例
实施例1、一种新型螺螨酯类化合物的合成方法，其反应为：
在装有电磁搅拌、冷凝管、恒压滴液漏斗和温度计的100ml反应瓶中依次加入60ml二氯甲烷，6.3g(0.02mol)3-(2，4-二氯苯基)-2-氧代-1-氧杂螺[4，5]-癸-3-烯-4-醇和7.5g(0.075mol)三乙胺，搅拌溶解后，冰水浴下滴加氯甲酸仲丁酯3.3g(0.024mol)，然后在室温条件下继续搅拌，薄层板控制反应时间。反应结束后将反应液倒入饱和NaHCO3溶液(PH 8左右)，搅拌十分钟，分液，用40～60ml水洗有机层，有机相用无水Na2SO4干燥，减压除去溶剂二氯甲烷得到淡黄色粘稠状液体，用50ml甲醇重结晶，得到无色晶体7.08g(即为表1中的I a)，收率：86％。熔点：100～102℃.
1H NMR(500Hz，CDCl3，δppm)：7.41～7.21(3H，Ar-H)，4.13(m，1H，CH)，1.8～1.39(10H，Cyclohexyl-H)1.57(m，2H，CH2)，1.1(d，3H，CH3)，0.87(t，3H，CH3).
实施例2、一种新型螺螨酯类化合物的合成方法，其反应为：
在装有电磁搅拌、冷凝管、恒压滴液漏斗和温度计的100ml反应瓶中依次加入60ml 1，2-二氯乙烷，6.3g(0.02mol)3-(2，4-二氯苯基)-2-氧代-1-氧杂螺[4，5]-癸-3-烯-4-醇和7.5g(0.075mol)三乙胺，搅拌溶解后，冰水浴下滴加氯甲酸正丁酯3.3g(0.024mol)，然后在室温条件下继续搅拌，薄层板控制反应时间。反应结束后将反应液倒入饱和NaHCO3溶液(PH 8左右)，搅拌十分钟，分液，用40～60ml水洗有机层，有机相用无水Na2SO4干燥，减压除去溶剂1，2-二氯甲烷得到淡黄色油状液体，用50ml甲醇重结晶，得到无色晶体6.59g(即为表1中的I b)，收率：80％。熔点：92～93℃。
1H NMR(500Hz，CDCl3，δppm)：7.41～7.21(3H，Ar-H)，4.16(t，2H，CH2)，1.8～1.39(m，10H，Cyclohexyl-H)，1.55(m.2H，CH2)，1.35(m，2H，CH2)，0.92(t，3H，CH3).
实施例3、一种新型螺螨酯类化合物的合成方法，其反应为：
在装有电磁搅拌、冷凝管、恒压滴液漏斗和温度计的100ml反应瓶中依次加入60ml苯，6.3g(0.02mol)3-(2，4-二氯苯基)-2-氧代-1-氧杂螺[4，5]-癸-3-烯-4-醇和5.9g(0.075mol)吡啶，搅拌溶解后，冰水浴下滴加氯甲酸异戊酯3.6g(0.024mol)，然后在室温条件下继续搅拌，薄层板控制反应时间。反应结束后将反应液倒入饱和NaHCO3溶液(PH 8左右)，搅拌十分钟，分液，用40～60ml水洗有机层，有机相用无水Na2SO4干燥，减压除去溶剂苯得到淡黄色油状液体，用50ml甲醇重结晶，得到无色晶体6.9g(即为表1中的I c)，收率：82％。熔点：95～96℃.
1H NMR(500Hz，CDCl3，δppm)：7.41～7.21(3H，Ar-H)，4.16(t，2H，CH2)，1.8(m，1H，CH)，1.8～1.39(m，10H，C-yclohexyl-H)，1.54(m，2H，CH2)，0.99(d，6H，2CH3)
实施例4、一种新型螺螨酯类化合物的合成方法，其反应为：
在装有电磁搅拌、冷凝管、恒压滴液漏斗和温度计的100ml反应瓶中依次加入60ml甲苯，6.3g(0.02mol)3-(2，4-二氯苯基)-2-氧代-1-氧杂螺[4，5]-癸-3-烯-4-醇和7.5g(0.075mol)三乙胺，搅拌溶解后，冰水浴下滴加氯甲酸异丙酯2.9g(0.024mol)，然后在室温条件下继续搅拌，薄层板控制反应时间。反应结束后将反应液倒入饱和NaHCO3溶液(PH 8左右)，搅拌十分钟，分液，用40～60ml水洗有机层，有机相用无水Na2SO4干燥，减压除去溶剂甲苯得到淡黄色油状液体，用50ml甲醇重结晶，得到无色晶体5.7g(即为表1中的I d)，收率：71％。熔点：93～95℃.
1H NMR(500Hz，CDCl3，δppm)：7.41～7.21(3H，Ar-H)，4.31(m，1H，CH)，1.8～1.39(10H，Cyclohexyl-H)，1.35(d，6H，2CH3)
实施例5、一种新型螺螨酯类化合物的合成方法，其反应为：
在装有电磁搅拌、冷凝管、恒压滴液漏斗和温度计的100ml反应瓶中依次加入60ml石油醚，6.3g，(0.02mol)3-(2，4-二氯苯基)-2-氧代-1-氧杂螺[4，5]-癸-3-烯-4-醇和5.9g(0.075mol)吡啶，搅拌溶解后，冰水浴下滴加氯甲酸甲酯2.2g(0.024mol)，然后在室温条件下继续搅拌，薄层板控制反应时间。反应结束后将反应液倒入饱和NaHCO3溶液(PH 8左右)，搅拌十分钟，分液，用40～60ml水洗有机层，有机相用无水Na2SO4干燥，减压除去溶剂石油醚得到淡黄色油状液体，用50ml甲醇重结晶，得到无色晶体5.0g(即为表1中的I e)，收率：68％。熔点：91～93℃.
1H NMR(500Hz，CDCl3，δppm)：7.41～7.21(3H，Ar-H)，3.76(s，3H，CH3)，1.8～1.39(10H，Cyclohexyl-H)
实施例6、
采用浸渍法和统计校正害虫死亡率的方法测定杀螨卵活性。具体过程是：将供试药剂按有效成分分别稀释至所需浓度，在无菌条件下各吸取50ml药液注入培养皿内，再分别浸入有朱砂螨卵(螨卵按室内标准化方法正常饲养的群体)的叶片，以添加50ml灭菌水的平板做空白对照。将培养皿放在24±1℃恒温培养箱内。48h后调查统计死亡率。
表1系列化合物的杀虫杀螨活性测试结果
根据表中所列的测试结果，我们可以得知，在相同剂量下，本发明所得的化合物I a～I e的活性均高于或同于螺螨酯。
当然，需要注意的是，本发明中所提到的只是若干实施实例，本发明不限于以上实施实例，其他与之类似的发明均属于该专利的保护范围。
Claims (6)
1.一种新型螺螨酯类化合物，其特征在于结构式（Ⅰ）为：
其中R为：
2.权利要求1所述的螺螨酯类化合物的合成方法，其特征在于：在敷酸剂存在下，于非质子性溶剂中，使结构式为的化合物与结构式为
的氯甲酸酯在室温下反应1～2h，经过分离提纯即得，
其中R为：
、
、
、
或
。
3.根据权利2所述的螺螨酯类化合物的合成方法，其特征在于：非质子性溶剂为烷烃类、醚类、取代烷烃类或芳烃类；所述缚酸剂为三乙胺或者吡啶。
4.根据权利要求2或3所述的螺螨酯类化合物的合成方法，其特征在于：所述烷烃类为石油醚或环己烷，取代烷烃类为二氯甲烷或1,2-二氯乙烷，芳烃类为苯或甲苯，醚类为甲基叔丁基醚。
5.根据权利要求2或3所述的螺螨酯类化合物的合成方法，其特征在于：所述的氯甲酸酯以滴加方式加入，滴加温度为0～5℃；所述分离方法为重结晶，重结晶溶剂选用C1～C3中任意一级醇。
6.权利要求1所述螺螨酯类化合物的用途，其特征在于：用于杀虫或杀螨。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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