CN102090412A - 阿魏酸及其衍生物抗植物病毒剂 - Google Patents

阿魏酸及其衍生物抗植物病毒剂 Download PDF

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CN102090412A
CN102090412A CN2009102291123A CN200910229112A CN102090412A CN 102090412 A CN102090412 A CN 102090412A CN 2009102291123 A CN2009102291123 A CN 2009102291123A CN 200910229112 A CN200910229112 A CN 200910229112A CN 102090412 A CN102090412 A CN 102090412A
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CN102090412B (zh
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汪清民
王开亮
王兹稳
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Nankai University
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Abstract

本发明涉及通式如(I)所示的阿魏酸及其衍生物在农药上的应用，用作新型抗植物病毒剂，能很好地抑制烟草花叶病毒、辣椒病毒、番茄病毒、甘薯病毒、马铃薯病毒和瓜类病毒及玉米矮花叶病毒等，可有效防治烟草、辣椒、番茄、瓜菜、粮食、蔬菜、豆类等多种作物的病毒病，尤其适合于防治烟草花叶病。(其中各基团的意义见说明书)

Description

阿魏酸及其衍生物抗植物病毒剂
技术领域
本发明涉及一类新型抗植物病毒剂及其应用，具体涉及阿魏酸及其衍生物作为抗植物病毒剂，阿魏酸及其衍生物与具有抗植物病毒活性成分的互作组合物作为抗植物病毒剂，以及它们在防治植物病毒病上的应用，属农药技术领域。
背景技术
阿魏酸(ferulic acid(FA)，化学名称为4-羟基-3-甲氧基苯丙烯酸)是普遍存在的一种酚酸，在植物细胞壁中与多糖和木质素交联构成细胞壁的的一部分，是阿魏、当归、川芎、升麻等中药的有效成分之一，因其具有较强的抗氧化活性和防腐作用而已经被广泛应用于医药、保健品、化妆品原料和食品添加剂方面。近年来对其药理药效方面的广泛深入研究发现阿魏酸及其衍生物还具有很好的解热镇痛、抗血栓、降血脂、抗菌消炎、防癌、抗突变、增强免疫功能以及增强人体***活力和运动性等生物活性，其毒性极低，几乎无副作用。
目前，除了阿魏酸可作为食品、粮食防腐剂在农业上的相关应用以外，有关阿魏酸及其衍生物在农业上用于抗植物病毒病活性的研究实属空白。迄今尚未见以阿魏酸及其衍生物作为植物病毒抑制剂的相关报道，也未见阿魏酸及其衍生物抗植物病毒活性的相关研究报道。
由于植物病毒病种类繁多(常见种类2000余种)，防治极为困难，素有“植物癌症”之称，其危害仅次于真菌病害，给农业生产已造成极大损失。据统计，全世界每年农作物因此造成的经济损失达200亿美元，其中仅烟草花叶病毒(Tobacco mosaic virus，TMV)每年造成的经济损失超过1亿美元(Bos L.100 years of virology：from vitalism via molecular biology to geneticengineering.Trends in microbiology，2000，8(2)：82-87)。抗植物病毒药剂的需求和开发一直受到很大关注，已发现的抗植物病毒药剂主要有(表1)：苯并噻二唑(BTH)、噻酰菌胺(TDL)、4-甲基-1，2，3-噻二唑-5-甲酸(TDLA)、DL-β-氨基丁酸(BABA)、病毒唑、宁南霉素、菲并吲哚里西啶生物碱安托芬、联***类化合物XY-13和XY-30、病毒A(有效成分为盐酸吗啉双胍和醋酸铜)、水杨酸、多羟基双萘醛、氨基寡糖素(几丁寡糖，学名为β-1，4-寡聚葡萄糖胺)。而现有的这些抗植物病毒剂中实用化品种并不多，而且防治效果差，一般低于60％，质量控制较为困难，长期使用都存在一定的环境风险。因此，开发以天然植物活性物质为有效成分的高效、低毒的绿色抗植物病毒农药新品种意义非常重大。
表1.部分具有抗病毒活性化合物的化学结构
Figure G2009102291123D00021
发明内容
本发明目的在于提供一类新型、高效、低毒的抗植物病毒剂及其抗植物病毒应用。本发明首次发现天然阿魏酸及其衍生物具有高效抗植物病毒活性。
本发明抗植物病毒剂有效成分为阿魏酸及其衍生物，其结构通式为(I)所示结构的化合物：
式中，R1，R2，R3分别代表氢、羟基、1-6碳烷氧基、卤素原子、甲酰基、羧基、1-4碳烷基羰基、1-4碳烷基羰氧基、1-4碳烷氧基羰氧基、硝基；或者R1和R2，R2和R3分别代表OCH2O，OCH2CH2O；R4代表氢、羟基、ONa、OK、ONH4、葡萄糖基、烃氧基、烃胺基、二烃胺基、1-6碳烃基、(3-6)碳烯基、(3-6)卤代碳烯基、(3-6)碳炔基、1-4碳卤代烷基、1-4碳烷氧烷基、1-4碳烷硫烷基、苯基、萘基、色满、2，3-二氢-1，4-苯并二噁嗪、4H-1，3-苯并二噁嗪、2，3-二氢-苯并呋喃、苯并呋喃、苯并噻唑、1，3-苯并噁唑、1，2-苯并异噁唑或苯并咪唑，各基团是未取代的，或是被一个或一个以上下述基团取代：卤素、1-4碳烷基、1-4碳烷氧基、1-4碳卤代烷基、1-4碳卤代烷氧基、1-4碳烷氧烷基、1-4碳烷硫基、1-4碳烷基亚磺酰基、1-4碳烷基磺酰基、硝基、氰基、羟基、羧基、1-4碳烷基羰基、1-4碳烷氧基羰基或亚胺基。双键的构型为反式、或顺式、或顺反混合。
本发明所述的阿魏酸及其衍生物中R1，R2，R3分别代表H，OH，OCH3，OCH2CH3，OCOCH3，F，Cl，Br，CHO，CO2H，NO2或者R1和R2，R2和R3分别代表OCH2O，OCH2CH2O；R4代表OH，OCH3，OCH2CH3，CH2CH＝CH2，NEt2，p-Cl-C6H4NH，ONa，OK，ONH4，葡萄糖基。
本发明通式(I)的化合物具有优异的抗植物病毒活性，能很好地抑制烟草花叶病毒、辣椒病毒、番茄病毒、甘薯病毒、马铃薯病毒和瓜类病毒及玉米矮花叶病毒等，可有效防治烟草、辣椒、番茄、瓜菜、粮食、蔬菜、豆类等多种作物的病毒病，尤其适合于防治烟草花叶病。
本发明通式(I)的部分化合物在500ug/mL的浓度对烟草花叶病毒的抑制率高达80％以上，超过商品化品种病毒A、病毒唑、DADHT和DHT抑制烟草花叶病毒的活性(在500ug/mL抑制率都只有50％)。
本发明通式(I)的化合物作为植物病毒抑制剂可以直接使用，也可以加上农业上接受的载体使用，也可以和其他抗植物病毒剂如苯并噻二唑(BTH)、噻酰菌胺(TDL)、4-甲基-1，2，3-噻二唑-5-甲酸(TDLA)、DL-β-氨基丁酸(BABA)、病毒唑、宁南霉素、菲并吲哚里西啶生物碱安托芬、联***类化合物XY-13和XY-30、病毒A、水杨酸、多羟基双萘醛、氨基寡糖素形成互作组合物使用，这些组合物有的表现增效作用，有的表现相加作用。
本发明的阿魏酸及其衍生物抗植物病毒剂较现有使用的病毒抑制剂，具有很大的优势：化学结构简单，抗植物病毒活性显著，且对多种植物病毒具有抑制作用；毒性极低，环境兼容性好，对非靶标生物安全。
具体实施方式
以下通过实施例对本发明作进一步的详细说明，但本发明不限于这些实施例。
实施例1：阿魏酸及其衍生物的化学结构式和物理常数，见表1：
表1.部分阿魏酸及其衍生物的化学结构式和物理常数
Figure G2009102291123D00041
Figure G2009102291123D00051
Figure G2009102291123D00061
Figure G2009102291123D00071
实施例2：反式阿魏酸(1)的合成
在50mL圆底烧瓶中，依次加入香兰醛(10g，0.065mol)、丙二酸(7.5g，0.07mol)、甲苯(15mL)、吡啶和苯胺，于85-95℃反应2小时。加入25％碳酸钾水溶液(35mL)，搅拌。分出水层，用浓盐酸调pH，析出大量固体，过滤，用水洗涤，干燥得淡黄色针状结晶反式阿魏酸(11.6g，92％)，mp 172-173℃。
实施例3：目标化合物20的合成
在100mL圆底烧瓶中加入反式阿魏酸0.5g，无水乙醇30mL，10％Pd-C催化剂0.1g，室温下由氢气球鼓入氢气6小时，过滤除去Pd-C催化剂，脱溶得白色固体0.48g，收率96％，mp 91-92℃。
实施例4：目标化合物25的合成
在50mL圆底烧瓶中加入8.8g(E)-3-[(4-羟基-3-甲氧基-5-溴)苯基]丙烯酸，10mL乙酸酐，10滴无水吡啶，搅拌加热回流3小时，冷至室温，析出沉淀，抽滤，滤饼用蒸馏水洗涤，得白色粉末，干燥，用冰醋酸重结晶得(E)-3-[(4-乙酰氧基-3-甲氧基-5-溴)苯基]丙烯酸白色晶体7.6g，收率75.0％，熔点208-212℃。
在装有尾气吸收装置的50mL圆底烧瓶中加入3.14g(0.01mol)(E)-3-[(4-乙酰氧基-3-甲氧基-5-溴)苯基]丙烯酸，10mL无水苯，3mL二氯亚砜，搅拌下加热回流至无气体放出为止，反应完毕，减压除去过量二氯亚砜和溶剂，再将所得酰氯溶于10mL苯用于下一步反应。
在装有滴液漏斗和尾气吸收装置的150mL反应瓶中加入0.02mol对氯苯胺，15mL无水苯，室温搅拌下缓慢滴加上述酰氯溶液，滴毕，反应物继续搅拌8小时，有沉淀析出，抽滤得粉末状固体，干燥，经乙醇重结晶得25白色针状晶体3.7g，收率87.1％，熔点223-226℃。
实施例5：以抗烟草花叶病毒(Tobacco mosaic virus，TMV)活性为例，阿魏酸及其衍生物抗烟草花叶病毒活性的测定程序如下：
离体半叶枯斑法(Half-leaf necrosis)筛选方法：取新鲜具有典型TMV病毒症状的三生烟叶，加入磷酸缓冲溶液(0.01M，pH 7.2)，在研钵中研碎，在撒有金刚砂的珊西烟叶上接种，并用清水快速冲洗。接种1.5-2小时后，将接种叶片沿主脉剪成两个相等半叶，一半叶片用待测样品的DMF溶液浸叶处理，另一半浸于清水中作对照，72小时后，统计半叶枯斑数，计算病斑抑制率。
活体保护作用筛选方法：选长势一致的5-6叶期心叶烟，用毛笔轻轻在左半叶分别涂施一定浓度的试样和对照样，右半叶片涂施溶媒作对照，24小时后，汁液摩擦接种病毒于处理叶片，每处理3株(共计9片叶片)，重复3次，72h后调查心叶烟枯斑数，计算病斑抑制率。
活体钝化作用筛选方法：选长势一致的5-6叶期心叶烟，将一定浓度的试样和对照样分别与病毒汁液1∶1(V/V)混合钝化0.5h，摩擦接种于处理左半叶片，病毒液汁与溶媒1∶1(V/V)混合摩擦接种于右半叶，每处理3株(共计9片叶片)，重复3次，72h后调查心叶烟枯斑数，计算病斑抑制率。
活体治疗作用筛选方法：选长势一致的5-6叶期心叶烟，先用病毒汁液摩擦接种于处理叶片，一定时间后分别涂施一定浓度的试样和对照样在左半叶，右半叶以溶媒为对照，每处理3株(共计9片叶片)，重复3次，72h后调查心叶烟枯斑数，计算病斑抑制率。
抑制率(％)＝[(对照枯斑数-处理枯斑数)/对照枯斑数]×100％
表2，表3为部分化合物的抗烟草花叶病毒(Tobacco mosaic virus，TMV)活性测试结果：
表2.离体半叶枯斑法测定各试样抗TMV活性
化合物   浓度(μg/mL)   抑制率(％) 化合物   浓度(μg/mL)   抑制率(％)
  1   500   90.2   11   500   ＞50
  2   500   ＞50   12   500   ＞50
  3   500   93.6   17   500   ＞50
  5   500   ＞50   18   500   ＞50
  6   500   ＞50   26   500   ＞50
  7   500   ＞50   28   500   ＞50
  9   500   ＞50   30   500   ＞50
表3.活体测试各试样抗TMV活性
化合物   浓度(μg/mL)   保护效果(％)   治疗效果(％)   钝化效果(％)
  1   100   70.5   44.8   53.3

Claims (6)

1.阿魏酸及其衍生物抗植物病毒剂，其特征在于它具有如下通式(I)所示结构：
Figure F2009102291123C00011
式中，R1，R2，R3分别代表氢、羟基、1-6碳烷氧基、卤素原子、甲酰基、羧基、1-4碳烷基羰基、1-4碳烷基羰氧基、1-4碳烷氧基羰氧基、硝基；或者R1和R2，R2和R3分别代表OCH2O，OCH2CH2O；R4代表氢、羟基、ONa、OK、ONH4、葡萄糖、烃氧基、烃胺基、二烃胺基、1-6碳烃基、(3-6)碳烯基、(3-6)卤代碳烯基、(3-6)碳炔基、1-4碳卤代烷基、1-4碳烷氧烷基、1-4碳烷硫烷基、苯基、萘基、色满、2，3-二氢-1，4-苯并二噁嗪、4H-1，3-苯并二噁嗪、2，3-二氢-苯并呋喃、苯并呋喃、苯并噻唑、1，3-苯并噁唑、1，2-苯并异噁唑或苯并咪唑，各基团是未取代的，或是被一个或一个以上下述基团取代：卤素、1-4碳烷基、1-4碳烷氧基、1-4碳卤代烷基、1-4碳卤代烷氧基、1-4碳烷氧烷基、1-4碳烷硫基、1-4碳烷基亚磺酰基、1-4碳烷基磺酰基、硝基、氰基、羟基、羧基、1-4碳烷基羰基、1-4碳烷氧基羰基或亚胺基。双键的构型为反式、或顺式、或顺反混合。
2.根据权利要求1所述的阿魏酸及其衍生物抗植物病毒剂，其特征在于R1，R2，R3分别代表H，OH，OCH3，OCH2CH3，OCOCH3，F，Cl，Br，CHO，CO2H，NO2；或者R1和R2，R2和R3分别代表OCH2O、OCH2CH2O；R4代表OH，OCH3，OCH2CH3，CH2CH＝CH2，NEt2，p-Cl-C6H4NH，ONa，OK，ONH4，葡萄糖；双键的构型为反式、或顺式、或顺反混合。
3.根据权利要求1和2所述的阿魏酸及其衍生物抗植物病毒剂，其特征在于优选的通式I所示的化合物是反式阿魏酸。
4.权利要求1所述的阿魏酸及其衍生物抗植物病毒剂，其特征在于它作为抗植物病毒剂，能很好地抑制烟草花叶病毒、辣椒病毒、番茄病毒、甘薯病毒、马铃薯病毒和瓜类病毒及玉米矮花叶病毒等，可有效防治烟草、辣椒、番茄、瓜菜、粮食、蔬菜、豆类等多种作物的病毒病，尤其适合于防治烟草花叶病。
5.权利要求1所述的阿魏酸及其衍生物抗植物病毒剂，其特征在于它作为抗植物病毒剂直接使用。
6.权利要求1所述的阿魏酸及其衍生物抗植物病毒剂，其特征在于它作为抗植物病毒剂和其他抗植物病毒剂如苯并噻二唑(BTH)、噻酰菌胺(TDL)、4-甲基-1，2，3-噻二唑-5-甲酸(TDLA)、DL-β-氨基丁酸(BABA)、病毒唑、宁南霉素、菲并吲哚里西啶生物碱安托芬、联***类化合物XY-13和XY-30、病毒A、水杨酸、多羟基双萘醛、氨基寡糖素形成互作组合物使用。
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CN106977464B (zh) * 2016-01-15 2019-12-10 雷海民 具有神经保护活性的川芎嗪取代肉桂酸类衍生物(lqc-w)及其应用
CN106977464A (zh) * 2016-01-15 2017-07-25 雷海民 具有神经保护活性的川芎嗪取代肉桂酸类衍生物(lqc-w)及其应用
CN105777654B (zh) * 2016-03-28 2018-03-27 贵州大学 一种含喹唑啉的阿魏酸酯类衍生物、其制备方法和用途
CN105777654A (zh) * 2016-03-28 2016-07-20 贵州大学 一种含喹唑啉的阿魏酸酯类衍生物、其制备方法和用途
CN106718887A (zh) * 2016-11-30 2017-05-31 云南省农业科学院生物技术与种质资源研究所 一种快速脱除马铃薯病毒的方法
CN108684669A (zh) * 2018-06-21 2018-10-23 北京清源保生物科技有限公司 一种含有反式阿魏酸与大黄素甲醚的农药组合物及其应用
CN109041658A (zh) * 2018-08-30 2018-12-21 北京清源保生物科技有限公司 一种抗植物病毒种衣剂及其应用
CN109984133A (zh) * 2019-04-03 2019-07-09 江西鑫邦科技有限责任公司 一种含有芸苔素内酯类化合物的防治病毒病的农药组合物
CN111035632A (zh) * 2019-12-27 2020-04-21 天津市肿瘤医院 一种Nrf2的激活剂及制备防治环境有毒物质的药物用途
CN113801022A (zh) * 2021-07-23 2021-12-17 贵州大学 阿魏酸丁香酚及异丁香酚杂合体及应用
CN113801022B (zh) * 2021-07-23 2023-07-28 贵州大学 阿魏酸丁香酚及异丁香酚杂合体及应用
CN114195691A (zh) * 2021-12-16 2022-03-18 贵州大学 一种含酰胺的阿魏酸衍生物及其制备方法和应用
CN114195691B (zh) * 2021-12-16 2023-10-20 贵州大学 一种含酰胺的阿魏酸衍生物及其制备方法和应用

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