CN111349038A - 一类吲哚酰腙化合物及其制备方法和在防治植物病害中的应用 - Google Patents

一类吲哚酰腙化合物及其制备方法和在防治植物病害中的应用 Download PDF

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CN111349038A
CN111349038A CN201811584242.4A CN201811584242A CN111349038A CN 111349038 A CN111349038 A CN 111349038A CN 201811584242 A CN201811584242 A CN 201811584242A CN 111349038 A CN111349038 A CN 111349038A
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indole
acylhydrazone
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CN111349038B (zh
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王兹稳
廖安财
张铭君
康锦
汪清民
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Tianjin Normal University
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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Abstract

本发明公开一类吲哚酰腙化合物及其制备方法和在防治植物病害中的应用，吲哚酰肼与相应的醛的乙醇溶液进行反应，缩合得本发明的化合物。本发明的吲哚酰腙类化合物显示出特别优异的抗植物病毒活性，能很好地抑制烟草花叶病毒，同时表现出广谱的抗植物病菌活性。

Description

一类吲哚酰腙化合物及其制备方法和在防治植物病害中的 应用
技术领域
本发明属于农业防护技术领域，更加具体地说，涉及一类吲哚酰腙化合物的制备及其在防治植物病害中的应用。
背景技术
酰腙类化合物是由酰肼与醛或酮缩合而成的一类Schiff碱类化合物，表现出良好的生物活性、较强的配位能力和多样的配位方式，因此在医药、农药、材料和分析试剂等方面受到了广泛的关注。近年来,研究人员发现，酰腙类化合物具有抗菌、消炎和除草等多种生物活性,某些酰腙还具有抗癌作用。目前已商品化的品种有杀菌剂嘧菌腙和玉米田苗后除草剂氟吡草腙。
发明内容
本发明目的在于克服现有技术的不足，提供一类吲哚酰腙类化合物I、制备方法及其在防治植物病害中的应用。本发明的吲哚酰腙类化合物I具有较很好的抗植物病毒和病菌活性。
本发明的一类吲哚酰腙化合物为通式I所示结构的化合物：
Figure BDA0001918696110000011
取代基R如下结构式所示。
R
Figure BDA0001918696110000021
其中Me为甲基。
针对不同取代基R，化合物标记为a—t，取代基中带有曲线标记的分子键为与通式I键接的位置。
本发明的化合物I按照如下步骤进行制备：
Figure BDA0001918696110000022
将吲哚酰肼与醛进行反应，以得到化合物I，其中吲哚酰肼与醛为等摩尔比，选择无水乙醇作为反应溶剂，先在室温20—25摄氏度下搅拌以混合均匀，如100—200转/min的搅拌速度下搅拌10—30min，然后保持搅拌速度不变在80—90摄氏度下进行反应，如3—8小时，优选4—6小时；自然冷至室温，旋蒸除去无水乙醇，抽滤得化合物I。
参与反应的醛，具有醛基，即RCHO，在取代基R中带有曲线标记的分子键为与醛基CHO键接的位置，这样以来，为得到相应的取代基，选择相应醛进行反应即可。
本发明的吲哚酰腙类化合物I表现出很好的抗植物病毒和病菌活性，能很好地抑制烟草花叶病毒(TMV)和黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，马铃薯晚疫，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯14种植物病菌，即在制备治疗或者抑制各个相应植物病毒和病菌药物中的应用。
具体实施方式
下述的实施例和生测试验结果可用来进一步说明本发明，但不意味着限制本发明。
实施例1：吲哚酰腙类化合物I的合成
Figure BDA0001918696110000031
在250mL圆底烧瓶中，将吲哚酰肼(6mmol)、醛(6mmol)溶于80mL无水乙醇中。室温搅拌30min，搅拌速度保持为每分钟120转，在90℃搅拌反应4h。冷至室温，旋蒸除去40mL乙醇，抽滤得化合物I。
取代基R采用如发明内容所示的取代基，与取代基R相应的醛作为反应物质和吲哚酰肼等摩尔比进行反应，以得到化合物I，化合物标记为a—t(即Ia—It)。对化合物a—t进行熔点和核磁共振表征，数据如下：
Ia.白色固体，熔点233-234℃，收率79％，1H NMR(400MHz,DMSO-d6)δ11.74(s,1H,NH),11.38(s,1H,NH),8.20–8.33(m,3H,Ar-H),7.72(d,J＝7.3Hz,2H,Ar-H),7.47(s,1H,Ar-CH),7.38–7.49(m,3H,Ar-H),7.14–7.22(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ134.7,129.5,128.8,126.7,122.2,120.8,111.9.
Ib.白色固体，熔点242-243℃，收率90％，1H NMR(400MHz,DMSO-d6)δ11.72(s,1H,NH),11.27(s,1H,NH),8.20–8.29(m,3H,Ar-H,Ar-CH),7.66(d,J＝8.6Hz,2H,Ar-H),7.45(d,J＝7.8Hz,1H,Ar-H),7.15–7.20(m,2H,Ar-H),7.03(d,J＝8.7Hz,2H,Ar-H),3.82(s,3H,OCH3)；13C NMR(100MHz,DMSO-d6)δ160.4,128.3,127.3,122.2,120.7,114.3,111.9,55.2.
Ic.白色固体，熔点294-296℃，收率92％，1H NMR(400MHz,DMSO-d6)δ11.81(s,1H,NH),11.71(s,1H,NH),8.68(s,1H,Ar-H),8.30(s,1H,Ar-CH),8.23(d,J＝7.3Hz,1H,Ar-H),8.02(dd,J＝6.6,1.2Hz,1H,Ar-H),7.70(d,J＝8.0Hz,1H,Ar-H),7.46–7.51(m,2H,Ar-H),7.33–7.37(m,1H,Ar-H),7.16–7.24(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ136.0,133.5,130.1,131.2,128.0,127.0,123.1,122.3,120.9,112.0；HRMS(ESI)calcd for C16H13BrN3O(M+H)+342.0237,found 342.0239.
Id.黄色固体，熔点287-288℃，收率92％，1H NMR(400MHz,DMSO-d6)δ11.83(d,J＝1.4Hz,1H,NH),11.73(s,1H,NH),8.38–8.43(m,1H,Ar-H),8.31(d,J＝8.8Hz,2H,Ar-H),8.29(s,1H,Ar-CH),8.21(d,J＝7.5Hz,1H,Ar-H),7.98(d,J＝8.8Hz,2H,Ar-H),7.51(d,J＝7.5Hz,1H,Ar-H),7.16–7.24(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ147.4,141.2,136.0,127.6,124.1,122.4,121.1,120.9,112.0.
Ie.白色固体，熔点298-300℃，收率53％，1H NMR(400MHz,DMSO-d6)δ11.80(s,1H,NH),11.61(s,1H,NH),8.20–8.39(m,3H,Ar-H,Ar-CH),7.94(d,J＝8.1Hz,2H,Ar-H),7.82(d,J＝8.2Hz,2H,Ar-H),7.49(d,J＝8.1Hz,1H,Ar-H),7.15–7.23(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ139.2,129.9,129.5,127.8,126.3,126.19,126.15,126.0,122.9,121.4,112.5；HRMS(ESI)calcd for C17H13F3N3O(M+H)+332.1005,found 332.1001.
If.白色固体，熔点284-286℃，收率89％，1H NMR(400MHz,DMSO-d6)δ11.77(s,1H,NH),11.35(s,1H,NH),8.10–8.30(m,3H,Ar-H,NHN-CH),7.84(s,1H,Ar-H),7.48(d,J＝7.8Hz,1H,Ar-H),7.13–7.21(m,2H,Ar-H),6.88(d,J＝3.3Hz,1H,Ar-H),6.64(dd,J＝3.0,1.6Hz,1H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ149.8,144.6,122.2,120.8,112.3,112.1,111.9；HRMS(ESI)calcd for C14H12N3O2(M+H)+254.0924,found 254.0925.
Ig.白色固体，熔点279-281℃，收率86％，1H NMR(400MHz,DMSO-d6)δ11.80(s,1H,NH),11.52(s,1H,NH),8.90–9.10(m,2H,Ar-H,NCH),8.20–8.30(m,2H,Ar-H),8.00–8.04(m,2H,Ar-H),7.94(d,J＝7.0Hz,1H,Ar-H),7.68(d,J＝7.1Hz,1H,Ar-H),7.60–7.63(m,2H,Ar-H),7.50(d,J＝7.5Hz,1H,Ar-H),7.16–7.24(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ133.5,130.1,130.0,128.8,127.1,126.2,125.6,122.3,120.8,112.0；HRMS(ESI)calcdfor C20H16N3O(M+H)+314.1288,found 314.1284.
Ih.棕色固体230-231℃，收率78％，1H NMR(400MHz,DMSO-d6)δ11.74(s,2H,NH),11.19(s,1H,NH),8.53(d,J＝4.8Hz,2H,Ar-H),8.24(d,J＝7.4Hz,1H,Ar-H),8.20(s,1H,Ar-CH),7.87(s,1H,Ar-H),7.15–7.51(m,5H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ136.2,131.3,126.4,125.5,122.6,121.1.114.3,113.4,112.4.
Ii.白色固体，熔点284-286℃，收率67％，1H NMR(400MHz,DMSO-d6)δ11.66(s,1H,NH),10.90(s,1H,NH),8.02–8.14(m,2H,Ar-H),7.53(s,1H,NHN-CH),7.45(d,J＝7.8Hz,1H,Ar-H),7.11–7.19(m,2H,Ar-H),2.22–2.32(m,1H,NCH-CH),1.63–1.82(m,5H,CH2),1.19–1.36(m,5H,CH2)；13C NMR(100MHz,DMSO-d6)δ122.1,120.6,111.8,29.8,25.5,25.0；HRMS(ESI)calcd for C16H20N3O(M+H)+270.1601,found 270.1607.
Ij.白色固体，熔点260-266℃，收率56％，1H NMR(400MHz,DMSO-d6)δ11.66(s,1H,NH),10.93(s,1H,NH),8.12–8.16(m,2H,Ar-H,NCH),7.55–7.64(m,1H,Ar-H),7.45(d,J＝7.9Hz,1H,Ar-H),7.10–7.19(m,2H,Ar-H),2.24–2.28(m,2H,CH2),1.49–1.52(m,2H,CH2),1.20–1.35(m,8H,CH2),0.87(t,J＝5.5Hz,3H,CH3)；13C NMR(100MHz,DMSO-d6)δ122.1,120.5,111.8,31.9,31.2,28.6,28.5,26.2,22.0,13.9；HRMS(ESI)calcd for C17H24N3O(M+H)+286.1914,found 286.1910.
Ik.白色固体，熔点243-245℃，收率77％，1H NMR(400MHz,DMSO-d6)δ11.79(s,1H,NH),11.43(s,1H,NH),8.21–8.28(m,3H,Ar-H,Ar-CH),7.49(d,J＝7.9Hz,1H,Ar-H),7.14–7.22(m,2H,Ar-H),7.02(s,2H,Ar-H),3.85(s,6H,CH3),3.71(s,3H,CH3)；13C NMR(100MHz,DMSO-d6)δ153.2,138.7,130.3,122.3,120.8,112.0,103.9,60.1,55.9.
Il.白色固体，熔点248-250℃，收率88％，1H NMR(400MHz,DMSO-d6)δ11.74(s,1H,NH),11.25(s,1H,NH),9.49(s,1H,OH),8.15–8.30(m,3H,Ar-H,NHNC-H),7.48(d,J＝8.0Hz,1H,Ar-H),7.31(s,1H,Ar-H),7.13–7.21(m,2H,Ar-H),7.07(dd,J＝8.1,1.4Hz,1H,Ar-H),6.85(d,J＝8.1Hz,1H,Ar-H),3.84(s,3H,OCH3)；13C NMR(100MHz,DMSO-d6)δ148.4,148.0,126.2,122.2,120.7,115.4,111.9,108.8,55.5；HRMS(ESI)calcd for C17H16N3O3(M+H)+310.1186,found 310.1191.
Im.白色固体，熔点296-298℃，收率88％，1H NMR(400MHz,DMSO-d6)δ11.71(s,1H,NH),11.22(s,1H,NH),9.88(s,1H,OH),8.12–8.30(m,3H,Ar-H,NHNC-H),7.55(d,J＝8.5Hz,2H,Ar-H),7.48(d,J＝7.8Hz,1H,Ar-H),7.13–7.21(m,2H,Ar-H),6.85(d,J＝8.5Hz,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ158.9,128.5,125.7,122.2,120.7,115.7,111.9；HRMS(ESI)calcd for C16H14N3O2(M+H)+280.1081,found 280.1086.
In.白色固体，熔点248-252℃，收率91％，1H NMR(400MHz,DMSO-d6)δ11.75(s,1H,NH),11.42(s,1H,NH),8.19–8.40(m,3H,Ar-H,NHNC-H),7.78(dd,J＝8.6,5.7Hz,2H,Ar-H),7.48(d,J＝7.6Hz,1H,Ar-H),7.27–7.32(m,2H,Ar-H),7.13–7.22(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ164.0,161.5,131.3,128.9,128.8,122.2,121.1,120.8,115.9,115.7,111.9；HRMS(ESI)calcd for C16H13FN3O(M+H)+282.1037,found 282.1042.
Io.黄色固体，熔点275-277℃，收率86％，1H NMR(400MHz,DMSO-d6)δ11.83(s,1H,NH),11.79(s,1H,NH),8.73(s,1H,Ar-H),8.30(s,1H,Ar-CH),8.23(d,J＝7.5Hz,1H,Ar-H),8.16(d,J＝7.7Hz,1H,Ar-H),8.08(dd,J＝8.2,1.0Hz,1H,Ar-H),7.82(t,J＝7.7Hz,1H,Ar-H),7.64–7.68(m,1H,Ar-H),7.50(d,J＝7.9Hz,1H,Ar-H),7.16–7.24(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ148.0,136.0,133.6,130.1,129.1,127.7.124.6,122.3,121.1,120.9,112.0；HRMS(ESI)calcd for C16H13N4O3(M+H)+309.0982,found 309.0985.
Ip.灰色固体，熔点253-255℃，收率52％；1H NMR(400MHz,DMSO-d6)δ11.68(s,1H,NH),11.45(s,1H,NH),11.09(s,1H,NH),8.13–8.20(m,3H,Ar-H,NHNC-H),7.47(d,J＝7.8Hz,1H,Ar-H),7.12–7.20(m,2H,Ar-H),6.92(s,1H,Ar-H),6.45(s,1H,Ar-H),6.15(s,1H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ128.0,122.6,122.3,121.1,112.9,112.4,109.6；HRMS(ESI)calcd for C14H13N4O(M+H)+253.1084,found 253.1080.
Iq.黄色固体，熔点265-267℃，收率93％，1H NMR(400MHz,DMSO-d6)δ11.78(s,1H,NH),11.36(s,1H,NH),8.58(s,1H,Ar-H),8.21(s,2H,Ar-H,NHNC-H),7.63(s,1H,Ar-H),7.48(d,J＝7.1Hz,1H,Ar-H),7.43(s,1H,Ar-H),7.14–7.20(m,3H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ128.0,122.6,122.3,121.1,112.9,112.4,109.6.
Ir.灰色固体，熔点>300℃，收率54％，1H NMR(400MHz,DMSO-d6)δ11.83(s,1H,NH),11.70(s,1H,NH),8.65(d,J＝5.6Hz,2H,Ar-H),8.28–8.39(m,2H,Ar-H,NHNC-H),8.23(d,J＝7.4Hz,1H,Ar-H),7.67(d,J＝5.7Hz,2H,Ar-H),7.51(d,J＝7.8Hz,1H,Ar-H),7.16–7.24(m,2H,Ar-H)；13C NMR(100MHz,DMSO-d6)δ150.6,142.4,122.9,121.5,121.3,112.5；HRMS(ESI)calcd for C15H13N4O(M+H)+265.1084,found 265.1086.
Is.白色固体，熔点238-240℃，收率77％，1H NMR(400MHz,DMSO-d6)δ11.67(s,1H,NH),10.95(s,1H,NH),8.02–8.34(m,2H,Ar-H),7.60(s,1H,NHN-CH),7.45(d,J＝7.8Hz,1H,Ar-H),7.11–7.19(m,2H,Ar-H),2.25(dd,J＝6.9,13.1Hz,2H,NCH-CH2),1.49–1.58(m,2H,CH3-CH2),0.95(t,J＝7.3Hz,3H,CH3)；13C NMR(100MHz,DMSO-d6)δ122.1,120.6,111.8,33.9,19.5,13.6；HRMS(ESI)calcd for C13H16N3O(M+H)+230.1288,found 230.1283.
It.白色固体，熔点197-199℃，收率81％，1H NMR(400MHz,DMSO-d6)δ11.68(s,1H,NH),10.93(s,1H,NH),8.10–8.30(m,2H,Ar-H),7.16(s,1H,NHNC-H),7.44–7.47(m,1H,Ar-H),7.12–7.19(m,2H,Ar-H),2.50–2.55(m,1H,(CH3)2C-H),1.10(s,3H,CH3),1.08(s,3H,CH3)；13C NMR(100MHz,DMSO-d6)δ122.6,121.1,112.3,31.4,20.2；HRMS(ESI)calcd forC13H16N3O(M+H)+230.1288,found 230.1283.
实施例2：抗烟草花叶病毒活性的测定
1、病毒提纯及浓度测定：病毒提纯及浓度测定参照南开大学元素所生测室编制烟草花叶病毒SOP规范执行。病毒粗提液经2次聚乙二醇离心处理后，测定浓度，4℃冷藏备用。
2、化合物溶液配制：称量后，原药加入DMF溶解，制得1×105μg/mL母液，后用含1‰吐温80水溶液稀释至所需浓度；宁南霉素制剂直接兑水稀释。
3、活体保护作用：选长势均匀一致的3–5叶期珊西烟，全株喷雾施药，每处理3次重复，并设1‰吐温80水溶液对照。24h后，叶面撒布金刚砂(500目)，用毛笔蘸取病毒液，在全叶面沿支脉方向轻擦2次，叶片下方用手掌支撑，病毒浓度10μg/mL，接种后用流水冲洗。3d后记录病斑数，计算防效。
4、活体治疗作用：选长势均匀一致的3–5叶期珊西烟，用毛笔全叶接种病毒，病毒浓度为10μg/mL，接种后用流水冲洗。叶面收干后，全株喷雾施药，每处理3次重复，并设1‰吐温80水溶液对照。3d后记录病斑数，计算防效。
5、活体钝化作用：选长势均匀一致的3–5叶期珊西烟，将药剂与等体积的病毒汁液混合钝化30min后，摩擦接种，病毒浓度20μg/mL，接种后即用流水冲洗，重复3次，设1‰吐温80水溶液对照。3d后数病斑数，计算结果。
抑制率(％)＝[(对照枯斑数-处理枯斑数)/对照枯斑数]×100％
表1吲哚酰腙类化合物I的抗烟草花叶病毒(TMV)活性测试结果：
Figure BDA0001918696110000071
Figure BDA0001918696110000081
Figure BDA0001918696110000091
从表1中可见吲哚酰腙类化合物I表现出很好的抗烟草花叶病毒活性，大部分化合物抑制活性超过病毒唑，化合物Ih抑制活性和宁南霉素相当。该类化合物合成简单，原料易得，具备极大的开发价值。
实施例3：抗菌活性测试离体杀菌测试，菌体生长速率测定法(平皿法)：将一定量药剂溶解在适量丙酮内，然后用含有200ug/mL乳化剂水溶液稀释至所需浓度，然后各吸取1mL药液注入培养皿内，再分别加入9mL培养基，摇匀后制成50ug/mL的含药平板，以添加1mL灭菌水的平板做空白对照。用直径4mm的打孔器沿菌丝外缘切取菌盘，移至含药平板上。每处理重复三次。将培养皿放在24±1℃恒温培养箱内培养。48小时后调查各处理菌盘扩展直径，求平均值，与空白对照比较计算相对抑菌率。
表2吲哚酰腙化合物I的抗植物病菌活性测试结果：
Figure BDA0001918696110000092
Figure BDA0001918696110000101
从表2中可以看出，吲哚酰腙类化合物I表现出广谱的抗植物病菌活性，部分化合物表现出优于商品化品种的水平，具备进一步开发的价值。
根据本发明工艺参数进行调整，均可实现本发明化合物的制备，且表现出与本发明基本一致的性能，即在制备治疗或者抑制烟草花叶病毒，黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，马铃薯晚疫，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯的药物中的应用。以上对本发明做了示例性的描述，应该说明的是，在不脱离本发明的核心的情况下，任何简单的变形、修改或者其他本领域技术人员能够不花费创造性劳动的等同替换均落入本发明的保护范围。

Claims (7)

1.一类吲哚酰腙化合物，其特征在于，通式I所示结构的化合物：
Figure FDA0001918696100000011
取代基R如下结构式所示，为其中一种R
Figure FDA0001918696100000012
Figure FDA0001918696100000013
其中Me为甲基。
2.一类吲哚酰腙化合物的制备方法，其特征在于，按照如下步骤进行制备：将吲哚酰肼与醛进行反应，以得到化合物I，其中吲哚酰肼与醛为等摩尔比；参与反应的醛，具有醛基，即RCHO，取代基R如下结构式所示，为其中一种R
Figure FDA0001918696100000021
Figure FDA0001918696100000022
其中Me为甲基。
3.根据权利要求2所述一类吲哚酰腙化合物的制备方法，其特征在于，选择无水乙醇作为反应溶剂。
4.根据权利要求2所述一类吲哚酰腙化合物的制备方法，其特征在于，在室温20—25摄氏度下搅拌以混合均匀，保持搅拌速度不变在80—90摄氏度下进行反应。
5.根据权利要求2所述一类吲哚酰腙化合物的制备方法，其特征在于，搅拌速度为100200转/min，搅拌时间为1030min，以实现搅拌均匀。
6.根据权利要求2所述一类吲哚酰腙化合物的制备方法，其特征在于，在8090摄氏度下进行反应38小时，优选46小时。
7.如权利要求1所述的一类吲哚酰腙化合物在防治植物病害中的应用，其特征在于，植物病害为烟草花叶病毒，黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，马铃薯晚疫，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯。
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