CN102090412B - Ferulic acid and ferulic acid derivative anti-phytoviral agents - Google Patents
Ferulic acid and ferulic acid derivative anti-phytoviral agents Download PDFInfo
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- CN102090412B CN102090412B CN200910229112.3A CN200910229112A CN102090412B CN 102090412 B CN102090412 B CN 102090412B CN 200910229112 A CN200910229112 A CN 200910229112A CN 102090412 B CN102090412 B CN 102090412B
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Abstract
The invention relates to a ferulic acid shown in a general formula (I) and the application of derivatives thereof to pesticides. When used as novel anti-phytoviral agents, the derivatives can well inhibit tobacco mosaic viruses, pepper viruses, tomato viruses, sweet potato viruses, potato viruses, melon viruses, maize dwarf mosaic viruses and the like, and effectively prevent and control the virus diseases of various crops such as tobacco, peppers, tomatoes, melons, grains, vegetables, beans and the like, and are particularly suitable for preventing and controlling tobacco mosaic. Meanings of each group are shown in specifications.
Description
Technical field
The present invention relates to the novel anti-plant virus agent of a class and application thereof, be specifically related to ferulic acid and its derivatives as anti-plant virus agent, ferulic acid and its derivatives with the interacting composition with anti-phytoviral activity composition as anti-plant virus agent, and they are in the application preventing and treating in the viroses of plant, belong to technical field of pesticide.
Background technology
Forulic acid (ferulic acid (FA), chemical name is FA) be ubiquitous a kind of phenolic acid, in plant cell wall with polysaccharide and lignin crosslinked form cell wall a part, be one of the effective elements of the medicine in asafoetide, Radix Angelicae Sinensis, Ligusticum wallichii, rattletop etc., because it has compared with strong antioxidation activity and antisepsis, be widely used in medicine, health products, cosmetic material and food additives aspect.In recent years the research extensively and profoundly of its pharmacological effect aspect is found to ferulic acid and its derivatives also has good antipyretic-antalgic, antithrombotic, reducing blood lipid, anti-inflammation, anti-cancer, anti-sudden change, strengthens immunologic function and strengthen the biologically actives such as human sperm vigor and motility, its toxicity is extremely low, almost has no side effect.
At present, except forulic acid can be used as food, the related application of grain preservative in agricultural, relevant ferulic acid and its derivatives real genus of research for anti-plant viral disease activity in agricultural is blank.There is not yet so far and using ferulic acid and its derivatives as the relevant report of plant virus inhibitor, also have no the correlative study report of ferulic acid and its derivatives anti-phytoviral activity.
Due to the viroses of plant (frequent species more than 2000 is planted) of a great variety, control is difficulty very, have the title of " plant cancer ", and its harm is only second to fungal disease, has caused very big loss to agricultural production.According to statistics, the economic loss that therefore the annual crops in the whole world cause reaches 20,000,000,000 dollars, tobacco mosaic virus (Tobacco mosaic virus only wherein, TMV) economic loss causing every year surpasses 100,000,000 dollars, and (Bos is years of virology:from vitalism via molecular biology to geneticengineering.Trends in microbiology L.100,2000,8 (2): 82-87).The demand of Antiphytoviral medicament and exploitation receive very large concern always, the Antiphytoviral medicament of having found mainly contains (table 1): diazosulfide (BTH), tiadinil (TDL), 4-methyl isophthalic acid, 2, 3-thiadiazoles-5-formic acid (TDLA), DL-beta-aminobutyric acid (BABA), virazole, Ningnanmycin, phenanthroindolizididerivative pyridine alkaloid antofine, connection triazole class compounds XY-13 and XY-30, virus A (active ingredient is moroxydine hydrochloride and Schweinfurt green), salicylic acid, the two naphthaldehydes of polyhydroxy, amino-oligosaccharide (chitin oligo saccharide, formal name used at school is β-1, 4-oligomerization gucosamine).And practical kind few in existing these anti-plant virus agents, and control efficiency is poor, and generally lower than 60%, quality control is difficulty comparatively, and all there is certain environmental risk in long-term use.Therefore, to take the green Antiphytoviral pesticide new variety meaning efficient, low toxicity that natural plants active substance is active ingredient very great in exploitation.
Table 1. part has the chemical constitution of antiviral activity compound
Summary of the invention
The object of the invention is to provide that a class is novel, efficient, the anti-plant virus agent of low toxicity and Antiphytoviral application thereof.The present invention finds that natural ferulaic acid and derivative thereof have high efficiency anti plant virus activity first.
Anti-plant virus agent active ingredient of the present invention is ferulic acid and its derivatives, and its general structure is the compound of structure shown in (I):
In formula, R
1, R
2, R
3represent respectively hydrogen, hydroxyl, 1-6 carbon alkoxyl, halogen atom, formoxyl, carboxyl, 1-4 carbon alkyl-carbonyl, 1-4 carbon alkyl carbonyl oxy, 1-4 carbon alkoxyl carbonyl oxygen base, nitro, or R
1and R
2, R
2and R
3represent respectively OCH
2o, OCH
2cH
2o, R
4represent hydrogen, hydroxyl, ONa, OK, ONH
4, glucosyl group, oxyl, hydroxylamine base, two hydroxylamine bases, 1-6 carbon alkyl, (3-6) carbene base, (3-6) halo carbene base, (3-6) carbyne base, 1-4 halocarbon substituted alkyl, 1-4 carbon alkoxyalkyl, 1-4 carbon alkane sulfanyl, phenyl, naphthyl, chroman, 2, 3-dihydro-1, 4-Ben Bing dioxazine, 4H-1, 3-Ben Bing dioxazine, 2, 3-dihydro-benzofuran, benzofuran, benzothiazole, 1, 3-benzoxazole, 1, 2-benzoisoxazole or benzimidazole, each group is unsubstituted, or replaced by one or more following radicals: halogen, 1-4 carbon alkyl, 1-4 carbon alkoxyl, 1-4 halocarbon substituted alkyl, 1-4 carbon halogenated alkoxy, 1-4 carbon alkoxyalkyl, 1-4 carbon alkylthio group, 1-4 carbon alkyl sulphinyl, 1-4 carbon alkyl sulphonyl, nitro, cyano group, hydroxyl, carboxyl, 1-4 carbon alkyl-carbonyl, 1-4 carbon alkoxy carbonyl or imido grpup.Being configured as trans or cis or closing along back mixing of two keys.
R in ferulic acid and its derivatives of the present invention
1, R
2, R
3represent respectively H, OH, OCH
3, OCH
2cH
3, OCOCH
3, F, Cl, Br, CHO, CO
2h, NO
2or R
1and R
2, R
2and R
3represent respectively OCH
2o, OCH
2cH
2o; R
4represent OH, OCH
3, OCH
2cH
3, CH
2cH=CH
2, NEt
2, p-Cl-C
6h
4nH, ONa, OK, ONH
4, glucosyl group.
The compound of general formula of the present invention (I) has excellent anti-phytoviral activity, can suppress well that tobacco mosaic virus, capsicum virus, tomato are viral, sweet potato viruses, Potyvirus and melon virus and maize dwarf mosaic virus etc., the virus disease that can effectively prevent and treat the various crop such as tobacco, capsicum, tomato, melon dish, grain, vegetables, beans, is particularly suitable for preventing and treating tobacco mosaic.
The part of compounds of general formula of the present invention (I) in the concentration of 500ug/mL to the inhibiting rate of tobacco mosaic virus up to more than 80%, surpass the activity (all only having 50% at 500ug/mL inhibiting rate) that commercialization kind virus A, virazole, DADHT and DHT suppress tobacco mosaic virus.
The compound of general formula of the present invention (I) can directly be used as plant virus inhibitor, also can add that the upper carrier of accepting of agricultural is used, also can be with other anti-plant virus agents as diazosulfide (BTH), tiadinil (TDL), 4-methyl isophthalic acid, 2, 3-thiadiazoles-5-formic acid (TDLA), DL-beta-aminobutyric acid (BABA), virazole, Ningnanmycin, phenanthroindolizididerivative pyridine alkaloid antofine, connection triazole class compounds XY-13 and XY-30, virus A, salicylic acid, the two naphthaldehydes of polyhydroxy, amino-oligosaccharide forms interacting composition and uses, the performance synergistic effect that these compositions have, some performance summation actions.
The viral inhibitors of the more existing use of ferulic acid and its derivatives anti-plant virus agent of the present invention, has very large advantage: chemical constitution is simple, and anti-phytoviral activity is remarkable, and inhibited to various plants virus; Toxicity is extremely low, and environment compatibility is good, to non-target organism safety.
Embodiment
The present invention is described in further detail by the following examples, but the invention is not restricted to these embodiment.
Embodiment 1: the chemical structural formula of ferulic acid and its derivatives and physical constant, in Table 1:
Chemical structural formula and the physical constant of table 1. part ferulic acid and its derivatives
Embodiment 2: trans-ferulaic acid (1) synthetic
In 50mL round-bottomed flask, add successively 4-hydroxyl-3-methoxylbenxaldehyde (10g, 0.065mol), malonic acid (7.5g, 0.07mol), toluene (15mL), pyridine and aniline, in 85-95 ℃ of reaction 2 hours.Add 25% wet chemical (35mL), stir.Divide water-yielding stratum, with concentrated hydrochloric acid, adjust pH, separate out a large amount of solids, filter, wash with water, dry faint yellow acicular crystal trans-ferulaic acid (11.6g, 92%), the mp 172-173 ℃ of obtaining.
Embodiment 3: target compound 20 synthetic
In 100mL round-bottomed flask, add trans-ferulaic acid 0.5g, absolute ethyl alcohol 30mL, 10%Pd-C catalyzer 0.1g, blasts hydrogen 6 hours by hydrogen balloon under room temperature, removes by filter Pd-C catalyzer, and precipitation obtains white solid 0.48g, yield 96%, mp 91-92 ℃.
Embodiment 4: target compound 25 synthetic
In 50mL round-bottomed flask, add 8.8g (E)-3-[(4-hydroxy-3-methoxy-5-bromine) phenyl] acrylic acid, 10mL acetic anhydride, 10 anhydrous pyridines, agitating heating refluxes 3 hours, be chilled to room temperature, separate out precipitation, suction filtration, filter cake washs with distilled water, white powder, dry, with glacial acetic acid (E)-3-[(4-acetoxy-3-methoxyl group-5-bromine that is recrystallized to obtain) phenyl] acrylic acid white crystal 7.6g, yield 75.0%, fusing point 208-212 ℃.
In the 50mL round-bottomed flask of device for absorbing tail gas is housed, add 3.14g (0.01mol) (E)-3-[(4-acetoxy-3-methoxyl group-5-bromine) phenyl] acrylic acid, 10mL anhydrous benzene, 3mL thionyl chloride, till under stirring, heating is back to and emits without gas, react complete, excessive thionyl chloride and solvent are removed in decompression, then gained acyl chlorides is dissolved in to 10mL benzene for next step, reacts.
In being housed, the 150mL reaction bulb of dropping funel and device for absorbing tail gas adds 0.02mol parachloroanilinum, 15mL anhydrous benzene, under stirring at room, slowly drip above-mentioned solution of acid chloride, drip and finish, reactant continues to stir 8 hours, there is Precipitation, suction filtration obtains pulverulent solids, dry, through ethyl alcohol recrystallization, obtains 25 white needle-like crystals 3.7g, yield 87.1%, fusing point 223-226 ℃.
Embodiment 5: resisting tobacco mosaic virus (Tobacco mosaic virus, the TMV) activity of take is example, and the mensuration program of ferulic acid and its derivatives activity of resisting tobacco mosaic virus is as follows:
The withered spot method of in vitro half leaf (Half-leaf necrosis) screening technique: get the fresh three lives tobacco leaf with typical TMV virus symptom, add phosphate buffer solution (0.01M, pH 7.2), in mortar, grind, on the western tobacco leaf of the coral sprinkled with diamond dust, inoculate, and get express developed with clear water.Inoculate after 1.5-2 hour, inoculation blade is cut into two along master pulse and equates half leaf, a half vane soaks leaf processing with the DMF solution of testing sample, and second half is dipped in clear water and compares, and after 72 hours, statistics half leaf withered spot number, calculates scab inhibiting rate.
Live body protective effect screening technique: select the 5-6 leaf phase Nicotiana glutinosa that growing way is consistent; with writing brush, at Zuo Banye, spread respectively certain density sample and control sample gently; right half vane spreads solvent and compares; after 24 hours; juice frictional inoculation virus is in processing blade, and every processing 3 strains (amounting to 9 blades), repeat 3 times; 72h " Invest, Then Investigate " Nicotiana glutinosa withered spot number, calculates scab inhibiting rate.
Live body passivation screening technique: select the 5-6 leaf phase Nicotiana glutinosa that growing way is consistent, certain density sample and control sample are mixed to passivation 0.5h with viral juice 1: 1 (V/V) respectively, frictional inoculation is in processing left half vane, virus juice and 1: 1 (V/V) mixed film friction of solvent are inoculated in right half leaf, every processing 3 strains (amounting to 9 blades), repeat 3 times, 72h " Invest, Then Investigate " Nicotiana glutinosa withered spot number, calculates scab inhibiting rate.
Live body therapeutic action screening technique: select the 5-6 leaf phase Nicotiana glutinosa that growing way is consistent, first with viral juice frictional inoculation in processing blade, after certain hour, spread respectively certain density sample and control sample at Zuo Banye, right half leaf be take solvent as contrast, every processing 3 strains (amounting to 9 blades), repeat 3 times, 72h " Invest, Then Investigate " Nicotiana glutinosa withered spot number, calculates scab inhibiting rate.
Inhibiting rate (%)=[(contrast withered spot number-processing withered spot number)/contrast withered spot number] * 100%
Table 2, the resisting tobacco mosaic virus that table 3 is part of compounds (Tobacco mosaic virus, TMV) active testing result:
It is active that the withered spot method of in vitro half leaf of table 2. is measured the anti-TMV of each sample
| Compound | Concentration (μ g/mL) | Inhibiting rate (%) | Compound | Concentration (μ g/mL) | Inhibiting 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 |
It is active that table 3. live body is tested the anti-TMV of each sample
| Compound | Concentration (μ g/mL) | Protection effect (%) | Result for the treatment of (%) | Passivation effect (%) |
| 1 | 100 | 70.5 | 44.8 | 53.3 |
Claims (3)
1. the ferulic acid and its derivatives with structure shown in following general formula (I) is the purposes aspect sick at resisting tobacco mosaic virus,
In formula, R
1, R
2, R
3represent respectively H, OH, OCH
3, OCH
2cH
3, OCOCH
3, F, Cl, Br, CHO, CO
2h, NO
2; Or R
1and R
2, R
2and R
3represent respectively OCH
2o, OCH
2cH
2o; R
4represent OH, OCH
3, OCH
2cH
3, NEt
2, p-Cl-C
6h
4nH, ONa, OK, ONH
4, glucose; Being configured as trans or cis or closing along back mixing of two keys, is characterized in that it can suppress tobacco mosaic virus well, can effectively prevent and treat the tobacco mosaic virus disease of tobacco, capsicum, tomato, melon dish, beans various crop.
2. purposes according to claim 1, is characterized in that trans-ferulaic acid can suppress tobacco mosaic virus well, can effectively prevent and treat the tobacco mosaic virus disease of tobacco, capsicum, tomato, melon dish, beans various crop.
3. purposes claimed in claim 1, it is characterized in that it as resisting tobacco mosaic virus agent directly use.
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| CN200910229112.3A CN102090412B (en) | 2009-12-11 | 2009-12-11 | Ferulic acid and ferulic acid derivative anti-phytoviral agents |
| PCT/CN2010/079539 WO2011069444A1 (en) | 2009-12-11 | 2010-12-07 | Anti-plant virus agent of ferulic acid and derivatives thereof |
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| CN102503851B (en) * | 2011-09-28 | 2013-10-16 | 南开大学 | Ferulic acid phenethyl alcohol amine derivative and application thereof |
| CN103626652B (en) * | 2012-08-29 | 2016-05-18 | 南开大学 | 3-aromatic substituted acrylic acid and derivative anti-plant virus agent thereof |
| CN104412972B (en) * | 2013-08-26 | 2016-06-29 | 南开大学 | Trans-ferulaic acid microemulsion and preparation method thereof and the application preventing and treating Nicotiana tabacum L., Oryza sativa L., tomato virus disease |
| CA2951435A1 (en) | 2014-06-06 | 2015-12-10 | Board Of Trustees Of Michigan State University | Compounds for inhibition of fungal toxin production |
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| CN106977464B (en) * | 2016-01-15 | 2019-12-10 | 雷海民 | Ligustrazine substituted cinnamic acid derivative (LQC-W) with neuroprotective activity and application thereof |
| CN105777654B (en) * | 2016-03-28 | 2018-03-27 | 贵州大学 | A kind of ferulic acid ester analog derivative, preparation method and use containing quinazoline |
| CN106718887B (en) * | 2016-11-30 | 2018-12-14 | 云南省农业科学院生物技术与种质资源研究所 | A kind of method of fast eliminating Potyvirus |
| CN108684669A (en) * | 2018-06-21 | 2018-10-23 | 北京清源保生物科技有限公司 | A kind of composition pesticide containing trans-ferulaic acid and Physcion and its application |
| CN109041658A (en) * | 2018-08-30 | 2018-12-21 | 北京清源保生物科技有限公司 | A kind of Antiphytoviral seed coat agent and its application |
| CN109984133A (en) * | 2019-04-03 | 2019-07-09 | 江西鑫邦科技有限责任公司 | A kind of composition pesticide of the prevention and treatment virosis containing brassin lactones class compound |
| CN111035632A (en) * | 2019-12-27 | 2020-04-21 | 天津市肿瘤医院 | Activator of Nrf2 and application of activator in preparation of drugs for preventing and treating environmental toxic substances |
| CN113801022B (en) * | 2021-07-23 | 2023-07-28 | 贵州大学 | Eugenol ferulate and isoeugenol hybrid and application thereof |
| CN117645560A (en) * | 2021-12-16 | 2024-03-05 | 贵州大学 | Ferulic acid derivative containing amide and preparation method and application thereof |
| CN115581233A (en) * | 2022-11-11 | 2023-01-10 | 中国农业科学院烟草研究所(中国烟草总公司青州烟草研究所) | Combined use method of tobacco root secretion methyl ferulate and chitosan oligosaccharide and application thereof |
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Non-Patent Citations (8)
| Title |
|---|
| In vivo inactivatioin of rice tungro virus by ferulic acid;Sridhar, R. et al.;《Phytopathologische Zeitschrift》;19791231;第94卷(第3期);279-281 * |
| Sridhar, R. et al..In vivo inactivatioin of rice tungro virus by ferulic acid.《Phytopathologische Zeitschrift》.1979,第94卷(第3期),279-281. |
| 胡志中等.阿魏酸酰胺类化合物的合成.《内蒙古医学院学报》.2007,第29卷(第6期),407-410. |
| 阿魏酸及其类似物的合成及其清除自由基活性研究;黄华永;《中国新药杂志》;20061231;第15卷(第6期);454-458 * |
| 阿魏酸衍生物及其生物活性;马逢时等;《药学进展》;20081231;第32卷(第8期);345-349 * |
| 阿魏酸酰胺类化合物的合成;胡志中等;《内蒙古医学院学报》;20071231;第29卷(第6期);407-410 * |
| 马逢时等.阿魏酸衍生物及其生物活性.《药学进展》.2008,第32卷(第8期),345-349. |
| 黄华永.阿魏酸及其类似物的合成及其清除自由基活性研究.《中国新药杂志》.2006,第15卷(第6期),454-458. |
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