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WO2011069444A1 - 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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WO2011069444A1
WO2011069444A1 PCT/CN2010/079539 CN2010079539W WO2011069444A1 WO 2011069444 A1 WO2011069444 A1 WO 2011069444A1 CN 2010079539 W CN2010079539 W CN 2010079539W WO 2011069444 A1 WO2011069444 A1 WO 2011069444A1
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carbon
virus
ferulic acid
och
plant virus
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French (fr)
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汪清民
王开亮
王兹稳
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Nankai University
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Nankai University
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C59/40—Unsaturated compounds
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    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings

Definitions

  • the invention relates to a novel anti-plant virus agent and application thereof, in particular to ferulic acid and its derivative as anti-plant virus agent, ferulic acid and its derivative and anti-plant virus active ingredient interaction composition as anti-vegetation Plant viral agents, and their use in the control of plant viral diseases, are in the field of pesticide technology.
  • Ferulic acid chemical name 4-hydroxy-3- Methoxybenzoic acid
  • F is a ubiquitous phenolic acid that crosslinks with polysaccharides and lignin in plant cell walls to form part of the cell wall. It is Awei, Angelica, and Chuan.
  • One of the active ingredients of traditional Chinese medicines such as medlar and cohosh has been widely used in medicine, health care products, cosmetic raw materials and food additives because of its strong antioxidant activity and antiseptic effect.
  • ferulic acid and its derivatives also have excellent antipyretic and analgesic, antithrombotic, hypolipidemic, antibacterial, anti-inflammatory, anti-cancer, anti-mutation, immune function enhancement and enhancement.
  • Biological activity such as human sperm motility and motility has extremely low toxicity and almost no side effects.
  • the anti-plant virus agents that have been found are mainly (Table 1): benzothiadiazole (BTH), thiazolamide (TDL), 4-methyl- 1, 2, 3-thiadiazole-5-carboxylic acid (TDLA), DL- ⁇ -aminobutyric acid (BABA), ribavirin, nymidine, phenanthroline alkaloids antoine, lian Triazole compounds XY-13 and XY-30, virus A (active components are morpholinium dihydrochloride and copper acetate), salicylic acid, polyhydroxy bis naphthaldehyde, amino oligosaccharide (chitin oligosaccharide, scientific name -1-1, 4-oligoglucosamine).
  • the present invention aims to provide a new class of high-efficiency, low-toxic anti-plant virus agents and their anti-plant virus applications.
  • the present invention finds for the first time that natural ferulic acid and its derivatives have high activity against plant viruses.
  • the active ingredient of the anti-plant virus agent of the present invention is ferulic acid and a derivative thereof, and the compound having the structure of the formula ( I ):
  • R 1 , R 2 and R 3 each represent hydrogen, hydroxy, 1 - 6 carkolkoxy, halogen atom, formyl group, carboxyl group, 1 - 4 carbon alkylcarbonyl group, 1 - 4 carbon alkylcarbonyloxy group , 1 - 4 carboalkoxycarbonyloxy or nitro; or R 1 and R 2 , R 2 and R 3 represent OCH 2 O , OCH 2 CH 2 O, respectively; R 4 represents hydrogen, hydroxy, ONa, OK, ONH 4 , glucosyl, alkoxy, hydrocarbon amine, dihydrocarbylamino, 1 - 6 carbon hydrocarbyl, ( 3 - 6 ) hexenyl, ( 3 - 6 ) haloalkenyl, ( 3 - 6 ) Carboalkynyl, 1 - 4 carbohaloalkyl, 1 - 4 carbon alkoxyalkyl, 1 - 4 carbon alkylthioalkyl, phenyl
  • R 1 , R 2 and R 3 represent H, OH and OCH 3 , respectively.
  • R 2 and R 3 represent OCH 2 O , OCH 2 CH 2 O , respectively;
  • R 4 represents OH , OCH 3 , OCH 2 CH 3 ,
  • CH 2 CH CH 2 , NEt 2 , p-Cl-C 6 H 4 NH , ONa, OK, ONH 4 , or glucosyl.
  • the compound of the formula ( I ) of the invention has excellent anti-plant virus activity, and can well inhibit tobacco mosaic virus, capsivirus, tomato virus, sweet potato virus, potato virus and melon virus, and corn dwarf mosaic virus, etc. It can effectively control viral diseases of tobacco, pepper, tomato, melon, food, vegetables, beans and other crops, especially suitable for controlling tobacco mosaic disease.
  • the partial compound of the formula ( I ) of the present invention inhibits tobacco mosaic virus at a concentration of 500 ug/mL as high as 80% or more, and inhibits the activity of tobacco mosaic virus over the commercial varieties of virus A, ribavirin, DADHT and DHT. (The inhibition rate is only 50% at 500 ug/mL).
  • the compound of the formula ( I ) of the present invention can be used as a plant virus inhibitor as it is, or it can be used together with an agriculturally acceptable carrier, and can also be combined with other anti-plant virus agents such as benzothiadiazole (BTH) and thiaform bacteria.
  • BTH benzothiadiazole
  • TDL 4-methyl-1 , 2 , 3-thiadiazole-5-carboxylic acid
  • BABA DL- ⁇ -aminobutyric acid
  • ribavirin nymidine, phenanthrene
  • the ferulic acid and its derivative anti-plant virus agent of the invention have great advantages over the existing virus inhibitors: simple chemical structure, significant anti-plant virus activity, and inhibition to various plant viruses; toxicity Very low, environmentally compatible, safe for non-target organisms.
  • Example 1 Chemical structural formula and physical constant of ferulic acid and its derivatives, see Table 2:
  • vanillin (10 g, 0.065 mol) and malonic acid (7.5 g) were added in sequence. , 0.07 mol ), toluene (15 mL), pyridine and aniline were reacted at 85-95 ° C for 2 hours.
  • the aqueous layer was separated, the pH was adjusted with concentrated hydrochloric acid, and a large amount of solid was precipitated, filtered, washed with water, and dried to give pale yellow needle crystals of trans ferulic acid ( 11.6 g, 92% ), mp 172-173 °C.
  • Example 5 Taking Tobacco mosaic virus (TMV) activity as an example, the procedure for measuring the activity of ferulic acid and its derivatives against tobacco mosaic virus is as follows:
  • Half-leaf necrosis screening method take fresh with typical TMV The three-year-old tobacco leaves with virus symptoms were added with phosphate buffer solution (0.01M, pH 7.2), ground in a mortar, inoculated on the emery leaves of the emery, and quickly rinsed with water. Vaccination 1.5-2 After the hour, the inoculated leaves were cut into two equal half leaves along the main vein, half of the leaves were treated with the DMF solution of the sample to be tested, and the other half was immersed in clear water for comparison. After the hour, the number of dead leaves was counted and the lesion inhibition rate was calculated.
  • phosphate buffer solution (0.01M, pH 7.2
  • Screening method for in vivo protection select the same 5-6 Leaf leaf heart leaf tobacco, gently apply a certain concentration of the sample and the control sample in the left half of the leaf with a brush, and apply the solvent to the right half of the leaf as a control. After 24 hours, the juice is rubbed and inoculated with the virus to treat the leaves, and each treatment 3 Strain ( Total 9 The leaf blade was repeated 3 times. After 72 hours, the number of leaves and leaves of the heart leaf was investigated, and the inhibition rate of the lesion was calculated.
  • Screening method for in vivo passivation select 5-6 leaf stage heart leaf smoke with consistent growth, and separate certain concentrations of samples and control samples with virus juice 1:1 (V/V) mixed passivation for 0.5 h, rubbed inoculated in the left half of the leaves, and virus juice and solvent 1:1 (V/V) mixed friction inoculated in the right half of the leaves, 3 plants per treatment (9 pieces in total) blade ), repeated 3 times, 72 hours later, the number of heart leaf smoke spots was investigated, and the lesion inhibition rate was calculated.
  • V/V virus juice 1:1
  • V/V virus juice and solvent 1:1
  • Screening method for in vivo treatment selection of the same 5-6 Leaf leaf heart leaf tobacco was first inoculated with the virus juice in the treated leaves. After a certain period of time, a certain concentration of the sample and the control sample were applied to the left half of the leaf, and the right half of the leaf was used as the control. Each treatment was 3 (9 in total) Blade Repeated 3 times. After 72 hours, the number of dead leaves of heart leaf was investigated, and the inhibition rate of lesions was calculated.
  • Inhibition rate (%) [(control plaque number - number of treated plaques) / number of control plaques] ⁇ 100%
  • Table 3 and Table 4 are some of the compounds against Tobacco mosaic virus (TMV). ) Activity test results:
  • Compound Concentration ( ⁇ g/mL) Inhibition rate (%) Compound Concentration ( ⁇ g/mL) Inhibition rate (%) 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

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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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精子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 genetic engineering. 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、联三唑类化合物 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
名称（代号） 苯并噻二唑（ BTH ） 噻酰菌胺（ TDL ） 4- 甲基 -1 ， 2 ， 3- 噻二唑 -5- 甲酸（ TDLA ） β- 氨基丁酸（ BABA ）
化学结构
Figure PCTCN2010079539-appb-C000001
Figure PCTCN2010079539-appb-C000002
Figure PCTCN2010079539-appb-C000003
Figure PCTCN2010079539-appb-C000004
名称（代号） 宁南霉素 安托芬 XY-13
化学结构
Figure PCTCN2010079539-appb-C000005
Figure PCTCN2010079539-appb-C000006
Figure PCTCN2010079539-appb-C000007
名称（代号） 病毒唑 XY-30 水杨酸
化学结构
Figure PCTCN2010079539-appb-C000008
Figure PCTCN2010079539-appb-C000009
Figure PCTCN2010079539-appb-C000010
名称（代号） 多羟基双萘醛
化学结构
Figure PCTCN2010079539-appb-C000011
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：
Figure PCTCN2010079539-appb-C000012
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 碳烷氧基羰氧基或硝基；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 或 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 ，或葡萄糖基。
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 500 ug/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 500 ug/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、联三唑类化合物 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 2 ：
表 2. 部分阿魏酸及其衍生物的化学结构式和物理常数
化合物编号 化学结构式 熔点 (°C)
1
Figure PCTCN2010079539-appb-C000013
 		172-173
2
Figure PCTCN2010079539-appb-C000014
 		黄色油状物
3
Figure PCTCN2010079539-appb-C000015
 		194-198
4
Figure PCTCN2010079539-appb-C000016
 		132-133
5
Figure PCTCN2010079539-appb-C000017
 		184-185
6
Figure PCTCN2010079539-appb-C000018
 		240-242
7
Figure PCTCN2010079539-appb-C000019
 		191-193
8
Figure PCTCN2010079539-appb-C000020
 		126-128
9
Figure PCTCN2010079539-appb-C000021
 		186-189
10
Figure PCTCN2010079539-appb-C000022
 		230-232
11
Figure PCTCN2010079539-appb-C000023
 		230-232
12
Figure PCTCN2010079539-appb-C000024
 		154-157
13
Figure PCTCN2010079539-appb-C000025
 		200-202
14
Figure PCTCN2010079539-appb-C000026
 		198-200
15
Figure PCTCN2010079539-appb-C000027
 		211-214
16
Figure PCTCN2010079539-appb-C000028
 		184-187
17
Figure PCTCN2010079539-appb-C000029
 		62-63
18
Figure PCTCN2010079539-appb-C000030
 		75-76
19
Figure PCTCN2010079539-appb-C000031
 		216-218
20
Figure PCTCN2010079539-appb-C000032
 		91-92
21
Figure PCTCN2010079539-appb-C000033
 		192-194
22
Figure PCTCN2010079539-appb-C000034
 		172-174
23
Figure PCTCN2010079539-appb-C000035
 		118-119
24
Figure PCTCN2010079539-appb-C000036
 		133-134
25
Figure PCTCN2010079539-appb-C000037
 		223-226
26
Figure PCTCN2010079539-appb-C000038
 		＞ 300
27
Figure PCTCN2010079539-appb-C000039
 		＞ 300
28
Figure PCTCN2010079539-appb-C000040
 		＞ 300
29
Figure PCTCN2010079539-appb-C000041
 		白色固体
30
Figure PCTCN2010079539-appb-C000042
 		白色固体
31
Figure PCTCN2010079539-appb-C000043
 		182-184
32
Figure PCTCN2010079539-appb-C000044
 		白色固体
33
Figure PCTCN2010079539-appb-C000045
 		199-202
34
Figure PCTCN2010079539-appb-C000046
 		白色固体
35
Figure PCTCN2010079539-appb-C000047
 		白色固体
36
Figure PCTCN2010079539-appb-C000048
 		白色固体
37
Figure PCTCN2010079539-appb-C000049
 		白色固体
38
Figure PCTCN2010079539-appb-C000050
 		白色固体
39
Figure PCTCN2010079539-appb-C000051
 		白色固体
40
Figure PCTCN2010079539-appb-C000052
 		149-151
41
Figure PCTCN2010079539-appb-C000053
 		白色固体
42
Figure PCTCN2010079539-appb-C000054
 		白色固体
43
Figure PCTCN2010079539-appb-C000055
 		170-172
44
Figure PCTCN2010079539-appb-C000056
 		135-136
45
Figure PCTCN2010079539-appb-C000057
 		白色固体
46
Figure PCTCN2010079539-appb-C000058
 		160-165
47
Figure PCTCN2010079539-appb-C000059
 		208-210
实施例 2 ： 反式阿魏酸（ 1 ）的合成
在 50 mL 圆底烧瓶中，依次加入香兰醛（ 10 g ， 0.065 mol ）、丙二酸（ 7.5 g ， 0.07 mol ）、甲苯（ 15 mL ）、吡啶和苯胺，于 85-95 °C 反应 2 小时。加入 25% 碳酸钾水溶液（ 35 mL ），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（ 11.6 g ， 92% ）， mp 172-173 °C 。
实施例 3 ： 目标化合物 20 的合成
在 100 mL 圆底烧瓶中加入反式阿魏酸 0.5 g ，无水乙醇 30 mL ， 10% Pd-C 催化剂 0.1 g ，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 0.48 g ，收率 96% ， mp 91-92 °C 。
实施例 4 ： 目标化合物 25 的合成
在 50 mL 圆底烧瓶中加入 8.8 g (E)-3-[(4- 羟基 -3- 甲氧基 -5- 溴 ) 苯基 ] 丙烯酸， 10 mL 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 °C 。
在装有尾气吸收装置的 50 mL 圆底烧瓶中加入 3.14 g （ 0.01 mol ） (E)-3-[(4- 乙酰氧基 -3- 甲氧基 -5- 溴 ) 苯基 ] 丙烯酸， 10 mL 无水苯， 3 mL 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 10 mL 苯用于下一步反应。
在装有滴液漏斗和尾气吸收装置的 150 mL 反应瓶中加入 0.02 mol 对氯苯胺， 15 mL 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 3.7 g ，收率 87.1% ，熔点 223-226°C 。
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 3 ，表 4 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 3. 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 4. 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 PCTCN2010079539-appb-I000001
    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 碳烷氧基羰氧基或硝基；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。
  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 或 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 或葡萄糖基；双键的构型为反式、或顺式、或顺反混合。
  3. 根据权利要求 1 或 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. 一种权利要求 1 所述的阿魏酸及其衍生物抗植物病毒剂的应用，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，可有效防治烟草、辣椒、番茄、瓜菜、粮食、蔬菜、豆类作物的病毒病。
  5. 根据权利要求 4 所述的阿魏酸及其衍生物抗植物病毒剂的应用，其特征在于，它作为抗植物病毒剂直接使用。
  6. 根据权利要求 4 所述的阿魏酸及其衍生物抗植物病毒剂的应用，其特征在于，它作为抗植物病毒剂和下述抗植物病毒剂苯并噻二唑 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、联三唑类化合物 XY-13 和 XY-30 、病毒 A 、水杨酸、多羟基双萘醛或氨基寡糖素形成互作组合物使用。
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