CN115108974A - 一种类2，6-二氟苯甲酰脲类衍生物及其制备方法和应用 - Google Patents

一种类2，6-二氟苯甲酰脲类衍生物及其制备方法和应用 Download PDF

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CN115108974A
CN115108974A CN202210835472.3A CN202210835472A CN115108974A CN 115108974 A CN115108974 A CN 115108974A CN 202210835472 A CN202210835472 A CN 202210835472A CN 115108974 A CN115108974 A CN 115108974A
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difluorobenzoylurea
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邵倩
刘殿卿
何东贤
侯媛芳
王光明
余佳
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Chongqing Medical and Pharmaceutical College
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Abstract

本发明提供了一种类2,6‑二氟苯甲酰脲类衍生物及其制备方法和应用，取2，6二氟苯甲酰胺投入甲苯中搅拌，在10℃以下滴加草酰氯。在90℃以上回流保温反应，回流至后期，温度保持100‑107℃之间，回流保温结束，减压脱除甲苯，得异氰酸酯甲苯溶液，降温至50‑60℃待用；称取等摩尔量的芳香氨基化合物配成甲苯溶液，控制温度不高于30℃下，滴加制备好的异氰酸酯甲苯溶液，滴加毕，升温到80℃保温反应4‑6小时，冷却到室温，过滤，滤饼烘干得到目标产物。本发明以2，6‑二氟苯甲酰胺为原料，首先合成2，6‑二氟苯甲酰异氰酸酯，再与对应的芳香胺衍生物缩合得到以下全新的一类2，6‑二氟苯甲酰脲类衍生物。具有较强的杀虫效果，为农药行业提供新的杀虫药物。

Description

一种类2，6-二氟苯甲酰脲类衍生物及其制备方法和应用
技术领域
本发明属于化合物领域，具体涉及一种2，6-二氟苯甲酰脲类衍生物及其制备方法和应用。
背景技术
现代农药的发展是以高效低毒、低残留、环境友好为导向，苯甲酰脲类生物农药以其独特的作用机制、较高的环境安全性、广谱高效的杀虫活性等特性，符合现代绿色农药的发展方向，已经逐渐成为治理抗性害虫的主流杀虫剂。
目前已经上市生产的2,6-二氟苯甲酰脲类有虱螨脲、氟啶脲、氟苯脲、氟铃脲等品种，且都表现出较好的杀虫活性。然而由于长期使用单一农药带来的抗药性以及农药施药成本控制的影响，使得新型品种的不断开发创新具有重要意义。
发明内容
针对现有技术问题，本发明的第一目的在于提供了一种类2，6-二氟苯甲酰脲类衍生物，第二目的在于提供该2，6-二氟苯甲酰脲类衍生物的制备方法，第三目的在于提供2，6-二氟苯甲酰脲类衍生物的应用。
为实现以上第一目的，本发明通过以下技术方案予以实现：一种类2,6-二氟苯甲酰脲类衍生物，其特征在于，结构式分别为：
BJXN-1
Figure BDA0003747809310000011
BJXN-2
Figure BDA0003747809310000012
BJXN-3
Figure BDA0003747809310000021
BJXN-4
Figure BDA0003747809310000022
BJXN-5
Figure BDA0003747809310000023
BJXN-6
Figure BDA0003747809310000024
BJXN-7
Figure BDA0003747809310000025
BJXN-8
Figure BDA0003747809310000026
BJXN-9
Figure BDA0003747809310000027
BJXN-10
Figure BDA0003747809310000028
本发明的第二目的是这样实现的：一种类2，6-二氟苯甲酰脲类衍生物的制备方法，其特征在于，按照如下方法制备：取2，6二氟苯甲酰胺投入100mL甲苯中搅拌，在10℃以下滴加草酰氯。在90℃以上回流保温4小时，回流至后期，温度保持100-107℃之间，回流保温结束，减压脱除甲苯，控制真空度在-0.085Mpa以下，得异氰酸酯甲苯溶液，降温至50-60℃待用；
称取等摩尔量的芳香氨基化合物配成甲苯溶液，控制温度不高于30℃下，滴加制备好的异氰酸酯甲苯溶液，滴加毕，升温到80℃保温反应4-6小时，冷却到室温，过滤，滤饼烘干得到目标产物。
一种类2，6-二氟苯甲酰脲类衍生物在制作杀虫剂中的应用。
有益效果：本发明以2，6-二氟苯甲酰胺为原料，首先合成2，6-二氟苯甲酰异氰酸酯，再与对应的芳香胺衍生物缩合得到以下全新的一类2，6-二氟苯甲酰脲类衍生物。具有较强的杀虫效果，为农药行业提供新的杀虫药物。
附图说明
图1为BJXN-1的氢谱。
图2为BJXN-1的质谱。
图3为BJXN-2的氢谱。
图4为BJXN-2的质谱。
图5为BJXN-3的氢谱。
图6为BJXN-3的质谱。
图7为BJXN-4的氢谱。
图8为BJXN-4的质谱；
图9为BJXN-5的氢谱。
图10为BJXN-5的质谱。
图11为BJXN-6的氢谱。
图12为BJXN-6的质谱。
图13为BJXN-7的氢谱。
图14为BJXN-7的质谱。
图15为BJXN-8的氢谱。
图16为BJXN-8的质谱。
图17为BJXN-9的氢谱；
图18为BJXN-9的质谱。
图19为BJXN-10的氢谱。
图20为BJXN-10的质谱。
具体实施方式
下面将结合实施例，对本发明做进一步的描述。
本发明的化合物为：
Figure BDA0003747809310000041
Figure BDA0003747809310000051
实施例1
Figure BDA0003747809310000052
反应通式如下：
Figure BDA0003747809310000053
1、2,6-二氟苯甲酰异氰酸酯的制备
32.2g(0.205mmol)2,6二氟苯甲酰胺投入100mL甲苯中搅拌，在10℃以下滴加1.6mL(0.0197mmol)草酰氯。在90℃以上回流保温4小时，回流至后期，温度保持100-107℃之间。回流保温结束，减压脱除甲苯，控制真空度在-0.085Mpa以下，蒸出约80mL甲苯，得异氰酸酯甲苯溶液，降温至50-60℃待用。
2、称取等摩尔量的BJXN-1到BJXN-10对应的芳香氨基化合物配成甲苯溶液，控制温度不高于30℃，滴加制备好的异氰酸酯甲苯溶液，滴加毕，升温到80℃保温反应4-6小时，冷却到室温，过滤，滤饼烘干得到目标产物。
Figure BDA0003747809310000061
BJXN-1白色粉末，收率86％。1H NMR(400MHz,DMSO-d6)δ11.68(s,1H),10.25(s,1H),8.28(dt,J＝4.8,1.3Hz,1H),7.83(ddd,J＝10.0,8.2,1.5Hz,1H),7.71–7.57(m,1H),7.39(ddd,J＝8.3,4.7,3.7Hz,1H),7.26(t,J＝8.3Hz,2H).13C NMR(101MHz,DMSO-d6)δ162.72,160.34,157.85,153.17,150.61,149.93,144.31,139.35,133.75,125.33,123.55,113.87,112.52.LCMS,m/z＝296.1[M+H]+.
Figure BDA0003747809310000062
BJXN-2白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.64(s,1H),10.66(s,1H),8.37(d,J＝3.0Hz,1H),8.02(dd,J＝9.2,4.1Hz,1H),7.81(ddd,J＝9.1,8.2,3.0Hz,1H),7.65(ddd,J＝8.6,6.6,1.9Hz,1H),7.27(t,J＝8.3Hz,2H).13C NMR(101MHz,DMSO-d6)δ162.98,160.35,157.71,155.24,150.15,147.51,136.34,136.08,133.89,126.15,114.89,113.70,112.74.LCMS,m/z＝296.1[M+H]+.
Figure BDA0003747809310000063
BJXN-3白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.72(d,J＝102.4Hz,2H),8.27(s,1H),7.81–7.50(m,3H),7.28(t,J＝8.3Hz,2H).13C NMR(101MHz,DMSO-d6)δ162.64,160.43,157.94,155.24,150.15,147.51,136.34,136.08,133.89,126.15,118.85,117.66,114.89,113.70,112.74.LCMS,m/z＝411.9,413.2[M+H]+.
Figure BDA0003747809310000071
BJXN-4白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.66(s,1H),10.62(s,1H),7.95(d,J＝8.8Hz,1H),7.73(d,J＝8.7Hz,1H),7.63(tt,J＝8.5,6.5Hz,1H),7.24(t,J＝8.3Hz,2H),2.49(s,3H).13C NMR(101MHz,DMSO-d6)δ162.87,160.41,157.92,155.64,150.10,149.50,142.42,133.79,114.86,113.71,112.81,112.67,112.5,24.50.LCMS,m/z＝369.9[M+H]+.
Figure BDA0003747809310000072
BJXN-5白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.69(s,1H),10.56(s,1H),7.98–7.54(m,3H),7.25(t,J＝8.3Hz,2H),7.00(d,J＝7.4Hz,1H),2.41(s,3H).13CNMR(101MHz,DMSO-d6)δ162.80,160.39,157.90,157.32,150.44,150.13,139.30,133.71,119.54,113.87,112.66,112.53,110.57,23.99.LCMS,m/z＝292.1[M+H]+.
Figure BDA0003747809310000073
BJXN-6白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.60–11.19(m,1H),9.62(s,1H),7.76–7.50(m,1H),7.25(t,J＝8.3Hz,2H),7.13(s,3H),2.24(s,6H).13C NMR(101MHz,DMSO-d6)δ162.68,160.42(d,J＝7.2Hz),157.94(d,J＝7.2Hz),150.98,135.65,134.36,133.49,128.30,127.33,114.15,112.65,112.43,18.50.LCMS,m/z＝305.1[M+H]+.
Figure BDA0003747809310000074
BJXN-7白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.55(s,1H),10.42(d,J＝3.7Hz,1H),8.74(d,J＝2.7Hz,1H),8.31(d,J＝4.7Hz,1H),8.11–7.94(m,1H),7.67–7.56(m,1H),7.37(dd,J＝8.4,4.7Hz,1H),7.23(t,J＝8.3Hz,2H).13C NMR(101MHz,DMSO-d6)未162.32,160.35(d,J＝7.0Hz),157.86(d,J＝7.1Hz),150.70,149.08(d,J＝18.4Hz),145.18,142.04,134.82,133.52,127.82,124.17,112.64,112.41.LCMS,m/z＝278.1[M+H]+.
Figure BDA0003747809310000081
BJXN-8白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.42(s,1H),10.12(s,1H),7.62(tt,J＝8.4,6.6Hz,1H),7.43–7.04(m,4H),6.93(d,J＝8.7Hz,1H),3.76(d,J＝10.0Hz,6H).13C NMR(101MHz,DMSO-d6)未162.63,160.45,160.38,157.96,157.89,150.47,149.26,146.02,133.56,131.05,113.99,112.74,112.67,112.48,56.12,55.94.LCMS,m/z＝337.1[M+H]+.
Figure BDA0003747809310000082
BJXN-9白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.52(s,1H),10.29(s,1H),7.94(d,J＝2.4Hz,1H),7.61(tt,J＝8.5,6.5Hz,1H),7.55–7.46(m,1H),7.35–7.27(m,2H),7.23(t,J＝8.2Hz,2H).13C NMR(101MHz,DMSO-d6)δ162.61,160.43,157.95,150.50,139.45,133.64,131.19,127.08,122.93,122.14,119.47,113.87,112.67,112.43.LCMS,m/z＝376.9[M+Na]+.
Figure BDA0003747809310000083
BJXN-10白色粉末，收率90％。1H NMR(400MHz,DMSO-d6)δ11.89(s,1H),9.34(s,1H),7.65(tt,J＝8.5,6.6Hz,1H),7.52(d,J＝8.0Hz,1H),7.26(td,J＝8.2,2.1Hz,3H),7.00(d,J＝8.0Hz,1H),3.91(s,3H).13C NMR(101MHz,DMSO-d6)δ162.49,160.37,157.88,156.55,152.02,150.61,138.16,134.02,133.39,125.34,114.04,113.59,112.77,112.57,108.35,56.19.LCMS,m/z＝364.1[M+H]+。通过图1-20的氢谱和质谱可以判定，合成的化合物为BJXN-1到BJXN-10。
实施例2
将化合物BJXN-1到BJXN-10配制成5g/100公斤水中，分别对30只家蝇和秋粘虫进行喷雾，12h后观察死亡情况，BJXN-1和BJXN-2对家蝇和秋粘虫的死亡率均在90％以上，BJXN-4和BJXN-7对家蝇的死亡率为85％以上，对秋粘虫的死亡率大于90％，BJXN-3、BJXN-5、BJXN-6、BJXN-8到BJXN-10也都表现出杀虫活性。
尽管已经示出和描述了本发明的实施例，对于本领域的普通技术人员而言，可以理解在不脱离本发明的原理和精神的情况下可以对这些实施例进行多种变化、修改、替换和变型，本发明的范围由所附权利要求及其等同物限定。

Claims (4)

1.一种类2,6-二氟苯甲酰脲类衍生物，其特征在于，结构式分别为：
BJXN-1
Figure FDA0003747809300000011
BJXN-2
Figure FDA0003747809300000012
BJXN-3
Figure FDA0003747809300000013
BJXN-4
Figure FDA0003747809300000014
BJXN-5
Figure FDA0003747809300000015
BJXN-6
Figure FDA0003747809300000016
BJXN-7
Figure FDA0003747809300000017
BJXN-8
Figure FDA0003747809300000018
BJXN-9
Figure FDA0003747809300000019
BJXN-10
Figure FDA0003747809300000021
2.一种类2，6-二氟苯甲酰脲类衍生物的制备方法，其特征在于，按照如下方法制备：取2，6二氟苯甲酰胺投入100mL甲苯中搅拌，在10℃以下滴加草酰氯，在90℃以上回流保温4小时，回流至后期，温度保持100-107℃之间，回流保温结束，减压脱除甲苯，控制真空度在-0.085Mpa以下，得异氰酸酯甲苯溶液，降温至50-60℃待用；
称取等摩尔量的芳香氨基化合物配成甲苯溶液，控制温度不高于30℃下，滴加制备好的异氰酸酯甲苯溶液，滴加毕，升温到80℃保温反应4-6小时，冷却到室温，过滤，滤饼烘干得到目标产物。
3.一种类2，6-二氟苯甲酰脲类衍生物在制作杀虫剂中的应用。
4.一种类2，6-二氟苯甲酰脲类衍生物在制作抗杀秋粘虫和家蝇活性的药物中的应用。
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