CN102503851B - Ferulic acid phenethyl alcohol amine derivative and application thereof - Google Patents
Ferulic acid phenethyl alcohol amine derivative and application thereof Download PDFInfo
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Abstract
A ferulic acid phenethyl alcohol amine derivative is a compound having the general formula (I) in the original text, wherein R and R1 refer to 1-12 carbon alkyl, carbon alkenyl, carbon alkynyl or substituted benzyl; and R2 refers to 1-6 carbon alkyl, carbon alkoxy, carbon alkane amide, carbon alkyl sulphanyl, substituted benzyloxy group, halogen, hydroxyl, cyan, nitryl or carboxyl. When X-X is a carbon-to-carbon double bond, the configuration of the double bond is of a trans-form, a cis-form or a cis-trans mixed form; and when X-X is a carbon-to-carbon single bond, the compound is the ferulicacid phenethyl alcohol amine derivative. The ferulic acid phenethyl alcohol amine derivative has the advantages that the compound plays a fine inhibitory role in plant viruses and insects for transmitting the viruses, serves as insecticide to be capable of preventing and treating injurious insects such as homoptera, acarina and the like, serves as anti-plant viral agent to be capable of effectively inhibiting tobacco mosaic viruses, pepper viruses, tomato viruses, sweet potato viruses and the like, and is capable of effectively preventing and treating viral diseases of various crops such as tobacco, grains, vegetables, beans and the like.
Description
[technical field]
The invention belongs to technical field of pesticide, particularly a kind of ferulic acid phenethyl alcohol amine derivative and application.
[background technology]
Plant virus have the title of " plant cancer ", and known plant virus has 716 kinds (Zhang Chengliang etc., plant virus taxonomy, Chinese agriculture press, 1996,283) at present, and the document that also has is thought more than 1000 kinds.
Plant virus harm unifacial leaf, various plants and the microorganism such as dicotyledonous, it is very general to distribute, and it is a kind of to multiple virus harm that every kind of crop of common cultivated plant has, and endangers to be only second to fungal disease.Virus is not only fought for the necessary nutritive ingredient of plant-growth with the host after infecting the host, and the nutrient that destroys plant conducts, change some metabolic balance of host plant and the activity of some enzymes, cause the plant-growth difficulty, produce the symptoms such as deformity, yellow, the serious death that also causes host plant causes crop failure and quality to descend.Its harm is very serious, such as yellow stunt of wheat, nineteen fifty-one is found in the U.S. first, now become worldwide disease, begin the beginning of the sixties to endanger in Shaanxi, 1960, the average year underproduction 30% reached individually 60% in the popular harm in northern China wheat district in 1964,1966,1970,1973,1978,1980,1999.
The outstanding disease of harm mainly contains in China: yellow stunt of wheat, yellow stunt of rice, Wheat Yellow leaf disease, potato degeneration disease, tomato, rape and Chinese cabbage mosaic disease, wheat rosette stunt, corn striped mosaic disease, millet red-leaf disease, black streaked dwarf virus of rice, tobacco mosaic disease, yellow virosis of beets disease, soybean mosaic, apple rough skin disease, apple mosaic, citrus yellow shoot disease, melon mosaic disease and peanut withes broom etc.Plant diseases has seriously hindered the further raising of level of agricultural production, how to control, alleviates or the harm of killing off plant virus has become the problem that the universe pays close attention to.The chemical prevention plant virus has instant effect, originally low, easy to use and inhibition virus easy to use, agricultural is composed many having a few such as wide.A large amount of facts shows that plant virus chemical prevention agent is the same with sterilant and occupy critical role in the control of Plant diseases.
The control of plant virus chemical prevention agent spectrum is quite extensive, yet from actual production, usually between 30～70%, and great majority are biological and complex agent type chemical classes to the prevention effect of plant virus in the chemical prevention agent.Its main component is class mixed things such as, deactivation matter, defense response exciton and physiologically active of plant Auto-regulator.mainly uses moroxydine hydrochloride, virazole, Ningnanmycin and amino-oligosaccharide etc.
Yet the vegetable cell outermost layer has take Mierocrystalline cellulose as material the cell walls that consists of, and is enough to antiviral intrusion, thereby one of characteristics of plant virus are can invade by host's wound.At occurring in nature, the most important communication media of plant virus is the insects and mites in the Arthropoda.Known nearly 400 kinds of insects can be propagated the virus more than 200 kinds, and are wherein main with leafhopper and aphid, and only black peach aphid just can be propagated about 70 kinds of viruses.
Therefore, be necessary to provide a kind of plant virus controlling medicament with insecticidal activity, reach the effect of integrated control.
[summary of the invention]
The object of the invention is to for above-mentioned technical Analysis, provide a kind of ferulic acid phenethyl alcohol amine derivative with insecticidal activity and anti-phytoviral activity, for the preparation of sterilant and anti-plant virus agent.
Technical scheme of the present invention:
A kind of ferulic acid phenethyl alcohol amine derivative has the compound of following general formula (I):
In the formula: R is 1-12 carbon alkyl, 1-12 carbene base, 1-12 carbyne base or substituted benzyl; R
11-12 carbon alkyl, 1-12 carbene base, 1-12 carbyne base or substituted benzyl; R
21-6 carbon alkyl, 1-6 carbon alkoxyl group, 1-6 carbon alkylamino radical, 1-6 carbon alkylthio, substituted benzyloxy, halogen, hydroxyl, cyano group, nitro or carboxyl; Substituting group quantity is 1～5.
Described X-X is carbon-carbon single bond or carbon-carbon double bond, and when X-X was carbon-carbon double bond, being configured as of two keys was trans, cis or close along back mixing; When X-X was carbon-carbon single bond, this compound was the Hydroferulic acid Phenethanolamine derivative.
A kind of application of described ferulic acid phenethyl alcohol amine derivative is used for control Homoptera and cicada Acarina as sterilant.
A kind of application of described ferulic acid phenethyl alcohol amine derivative, as anti-plant virus agent be used for to suppress that tobacco mosaic virus (TMV), capsicum virus, tomato are viral, the virus disease of sweet potato viruses, potato virus and control tobacco, grain, vegetables, legume crop.
When X-X was carbon-carbon double bond, the syntheti c route of the compounds of this invention (I) was:
, concrete preparation process is as follows:
1) NaOH is soluble in water, add forulic acid, be stirred to fully dissolving, ice-water bath is down to temperature of reaction system below 10 ℃, slowly drips diacetyl oxide, rises to room temperature and continues to stir 2h, transfers reaction solution pH=4～5 with acid, suction filtration, recrystallization gets Acetyl-ferulic acid;
2) add Acetyl-ferulic acid in the thionyl chloride, reflux 4h sloughs thionyl chloride, obtains yellow solid Acetyl-ferulic acid acyl chlorides 3;
3) the substituted acetophenone hydrochloride joins in the anhydrous tetrahydro furan, cryosel is bathed and is cooled to below-10 ℃, add triethylamine, after stirring 10min, the tetrahydrofuran solution of Acetyl-ferulic acid acyl chlorides 3 slowly is added dropwise in the above-mentioned suspension liquid stirred overnight at room temperature, suction filtration, washing, drying gets compound (E)-4-[3-(2-(4-substituted-phenyl)-2-carbonyl ethylamino-)-3-carbonyl-1-propylene]-2-anisole yl acetate 4;
4) compound 4 is dissolved in the anhydrous methanol, add sodium borohydride, reaction 4h adds entry, is heated to 60 ℃ and stirs 1h, methanol removal, transfer pH=6～7, separate out white solid, suction filtration, drying gets N-[2-(4-substituted-phenyl)-2-hydroxyethyl]-3-(3-methoxyl group-4-hydroxy phenyl)-acrylamide 5;
5) compound 5 is dissolved in the aqueous ethanolic solution, add NaOH, add haloalkane, be warming up to 65～70 ℃ of reactions to fully, transfer pH=6-7, remove ethanol, the adularescent solid is separated out, suction filtration, drying obtains white solid product (E)-N-[2-(4-substituted-phenyl)-2-hydroxyethyl]-3-(3-methoxyl group-4-alkoxyl phenyl) acrylamide 6;
6) compound 6 is dissolved in the anhydrous tetrahydro furan, add sodium hydride, add alkylating reagent, TLC monitoring reaction terminal point adds the shrend reaction of going out, remove tetrahydrofuran (THF), add the dissolving of NaOH solution, extraction, drying, precipitation can make (E)-N-[2-(4-substituted-phenyl)-2-and replace ethyl]-3-(3-methoxyl group-4-substituted-phenyl) acrylamides 7.
When X-X was carbon-carbon single bond, the syntheti c route of the compounds of this invention (I) was:
, concrete preparation process is as follows:
1) forulic acid is dissolved in the mixing solutions of dehydrated alcohol and tetrahydrofuran (THF), add 10mL concentrated hydrochloric acid and 10% palladium carbon, continue to pass into hydrogen under 40 ℃ to reacting completely, suction filtration, organic solvent is sloughed in decompression, adds the saturated common salt water washing, ethyl acetate extraction, drying, precipitation obtains 3-methoxyl group-4-hydroxy-benzenepropanoic acid ethylester 8;
2) compound 8 and the amino substituted benzene ethylate of 2-hydrochlorate are put into the microwave reaction pipe, add DMAP, microwave heating reaction 30min, ethyl acetate extraction, drying, precipitation gets N-[2-substituted-phenyl-2-hydroxyethyl]-3-(3-methoxyl group-4-hydroxy phenyl) propionic acid amide 9;
3) compound 9 is dissolved in the aqueous ethanolic solution, add NaOH, stir, add haloalkane, 65～70 ℃ were reacted 6 hours, transferred pH=6～7, decompression removes ethanol, suction filtration, drying obtains white solid product N-[2-substituted-phenyl-2-hydroxyethyl]-3-(3-methoxyl group-4-alkoxyl phenyl) propionic acid amide 10;
4) compound 10 is dissolved in the anhydrous tetrahydro furan, add sodium hydride, backflow 10min adds alkylating reagent, the TLC monitoring, during reaction end, add the shrend reaction of going out, reducing pressure removes tetrahydrofuran (THF), ethyl acetate extraction, drying, precipitation can make product N-[2-substituted-phenyl-2-and replace ethyl]-3-(3-methoxyl group-4-alkoxyl phenyl) Propionamides compound 11 synthetic.
Advantage of the present invention is: compound of the present invention has preferably restraining effect to the insect of plant virus and transmitted virus; As sterilant, can prevent and treat the insects such as Homoptera and cicada Acarina; As anti-plant virus agent, can suppress well that tobacco mosaic virus (TMV), capsicum virus, tomato are viral, sweet potato viruses, potato virus etc., can effectively prevent and treat the virus disease of the various crop such as tobacco, grain, vegetables, beans.
[embodiment]
Embodiment 1: the preparation of ferulic acid phenethyl alcohol amine derivative
1) preparation of Acetyl-ferulic acid 2
0.52mol (20.8g) sodium hydroxide is dissolved in the 200mL water, adds 0.20mol (38.8g) forulic acid, be stirred to fully dissolving, ice-water bath is down to temperature of reaction system below 10 ℃.Other gets 0.25mol (25.4g) diacetyl oxide and slowly is added dropwise in the cold reaction solution, dropwises to stir 1h, rises to subsequently room temperature and continues to stir 2h.Transfer reaction solution pH=4～5 with concentrated hydrochloric acid, have a large amount of white solids to separate out, suction filtration, the solid that obtains with ethyl alcohol recrystallization is product.Acetyl-ferulic acid is white solid, 200～202 ℃ of fusing points.
1HNMR(DMSO)δ(ppm)400MHz：2.24(s，3H，COCH
3)，3.80(s，3H，OCH
3)，6.57(d，1H，J＝16.0Hz，COCH)，7.08-7.53(m，3H，Ar-H)，7.55(d，1H，J＝16.0Hz，Ar-CH)，12.39(br，1H，COOH)。
2) (E)-4-[3-(2-(4-chloro-phenyl-)-2-carbonyl ethylamino-)-3-carbonyl-1-propylene]-preparation of 2-p-methoxy-phenyl Acetyl Chloride 98Min. 3
Put into 50mmol (11.8g) Acetyl-ferulic acid in the 250mL there-necked flask, add again 200mmol (23.8g) thionyl chloride and stirring, be heated to 78 ℃ and begin to reflux.Holding temperature stirs 4h, reacts substantially complete, slightly heats, and takes thionyl chloride out of with stream of nitrogen gas, obtains yellow solid Acetyl-ferulic acid acyl chlorides 3.It is for subsequent use under the room temperature this solid to be dissolved in the 100mL anhydrous tetrahydro furan.
3) (E)-4-[3-(2-(4-chloro-phenyl-)-2-carbonyl ethylamino-)-3-carbonyl-1-propylene]-preparation of 2-anisole yl acetate 4-1
Other gets the 1000mL round-bottomed flask, adds 60mmol (12.4g) alpha-amino group parachloroacetophenone hydrochloride and 400mL anhydrous tetrahydro furan, and vigorous stirring forms suspension liquid, and cryosel is bathed the tetrahydrofuran (THF) suspension liquid is down to low temperature below-10 ℃.Add 120mmol (12.1g) triethylamine, stir 10min.
Tetrahydrofuran solution with 3 slowly is added dropwise in the above-mentioned suspension liquid, and stirred overnight at room temperature obtains yellow suspension liquid.Suction filtration, the washing solid, drying obtains product 4-1.Product is white solid, 183～185 ℃ of fusing points.
1H?NMR(DMSO)δ(ppm)400MHz：2.24(s，3H，COCH
3)，3.80(s，3H，OCH
3)，4.72-4.73(m，2H，NHCH
2)，6.83(d，1H，J＝16.0Hz，COCH)，7.10-7.34(m，3H，Ar-H)，7.42(d，1H，J＝16.0Hz，Ar-CH)，7.52-7.76(m，4H，Ar-H)，8.48(br，1H，NH)。
Under the similarity condition, use alpha-amino group that methyl phenyl ketone is raw material, can prepare (E)-4-[3-(2-phenyl-2-carbonyl ethylamino-)-3-carbonyl-1-propylene]-2 anisole yl acetate 4-2, product is white solid, productive rate 58%, 149～151 ℃ of fusing points.
1HNMR(DMSO)δ(ppm)400MHz：2.31(s，3H，COCH
3)，3.94(s，3H，OCH
3)，4.91-4.92(m，2H，NHCH
2)，5.89(br，1H，NH)，6.43(d，1H，J＝16.0Hz，COCH)，6.75(br，1H，OH)，6.91-7.10(m，3H，Ar-H)，7.50-7.66(m，4H，Ar-CH+Ar-H)，8.01-8.03(m，2H，Ar-H)。
4) N-[2-(4-chloro-phenyl-)-2-hydroxyethyl]-preparation of 3-(3-methoxyl group-4-hydroxy phenyl)-acrylamide 5-1
2.5mmol (1.0g) 4-1 is dissolved in the 40mL anhydrous methanol, slowly adds 10mmol (0.4g) sodium borohydride under the room temperature in batches, reaction 4h, raw material completely dissolve.Add 10mL water, be heated to 60 ℃ and stir 1h, pH value of solution=9.The decompression methanol removal is transferred pH=6～7 with concentrated hydrochloric acid, separates out white solid, suction filtration, and drying obtains product 5-1.Product is white solid, productive rate: 77%, and 186～189 ℃ of fusing points.
1H?NMR(DMSO)δ(ppm)400MHz：3.14-3.44(m，3H，NHCH
2+CHOH)，3.77(s，3H，OCH
3)，4.63(dd，1H，J＝4.8Hz，J＝7.6Hz，OCH)，6.02(br，1H，NH)，6.26(d，1H，J＝16.0Hz，COCH)，6.84-7.09(m，3H，Ar-H)，7.26-7.33(m，4H，Ar-H)，7.60(d，1H，J＝16.0Hz，Ar-CH)，9.42(br，1H，ArOH)。
Under the similarity condition, use compound 4-2 to be raw material, can prepare N-[2-phenyl-2-hydroxyethyl]-3-(3-methoxyl group-4-hydroxy phenyl)-acrylamide 5-2.Product is white solid, productive rate: 75%, and 150～153 ℃ of fusing points.
1H?NMR(DMSO)δ(ppm)400MHz：3.94(s，3H，OCH
3)，4.91-4.92(m，3H，NHCH
2+CHOH)，5.89(br，1H，NH)，6.43(d，1H，J＝16.0Hz，COCH)，6.75(br，1H，OH)，6.91-7.10(m，3H，Ar-H)，7.50-7.66(m，4H，Ar-CH+Ar-H)，8.01-8.03(m，2H，Ar-H)。
5) (E)-N-[2-substituted-phenyl-2-hydroxyethyl]-3-(3-methoxyl group-4-alkoxyl phenyl) acrylamide 6 synthetic
20mmol compound 5 is dissolved in 160mL aqueous ethanolic solution (EtOH/H
2O 3/1v/v) in, adds 22mmol sodium hydroxide, be stirred to solid and dissolve fully.Add the 30mmol alkylating reagent, stir and be warming up to 65～70 ℃.About 10h reacts completely.Concentrated hydrochloric acid is transferred pH=6～7, and decompression removes most of ethanol under the room temperature, and the adularescent solid is separated out.Suction filtration, with the NaOH solution washing solid of pH=10, with the clear water washing, drying obtains compound 6 subsequently.
Under the similarity condition, can synthesize other compounds 6 of the present invention, see Table 1 and table 2.
Table 1: the physical and chemical parameter of compound 6
Table 2: the nuclear magnetic data of compound 6
6) (E)-N-[2-substituted-phenyl-2-replaces ethyl]-3-(3-methoxyl group-4-substituted-phenyl) acrylamides 7 is synthetic
2.5mmol (0.97g) compound 6 is dissolved in the 70mL anhydrous tetrahydro furan, is heated to backflow, solid dissolves gradually.Add 3.0mmol (0.07g) sodium hydride, solution is acutely boiling immediately, backflow 10min, and solution colour is deepened gradually, adds the alkylating reagent of 3.7mmol (1.5eq), TLC monitoring reaction terminal point; Reaction is during near terminal point, adds the shrend reaction of going out, and decompression removes tetrahydrofuran (THF) and obtains the thickness soup compound under the room temperature, with the NaOH solution dissolving of pH=10,30mL ethyl acetate extraction 3 times, merging organic phase, drying, precipitation.The decompression column chromatography is separated, and obtains target compound 7.
Under the similarity condition, can synthesize other compounds 7 of the present invention, see Table 3 and table 4.
Table 3: the physical and chemical parameter of compound 7
Table 4: the nuclear magnetic data of compound 7
Embodiment 2: the preparation of Hydroferulic acid Phenethanolamine derivative
1) preparation of 3-methoxyl group-4-hydroxy-benzenepropanoic acid ethylester 8
0.1mol (20g) 1 is dissolved in the mixing solutions of 170mL dehydrated alcohol and 60mL tetrahydrofuran (THF), adds the 10mL concentrated hydrochloric acid under the room temperature, stir.Standard atmosphere is depressed and is passed into nitrogen and remove air in the reaction system, adds subsequently 1g 10% palladium carbon.40 ℃ of temperature of reaction are kept in hot water bath, and hydrogen is replaced nitrogen and continued to pass into, with bubbler monitor gas pass into situation and once with isolate from outer air; About 20h reacts completely, and suction filtration separates wherein palladium carbon, and organic solvent is sloughed in decompression, and with saturated common salt water washing residual mixed liquor, three extractions of 100mL ethyl acetate merge organic phase, drying, and precipitation obtains light brown oily matter, productive rate: 98%.
2) N-[2-substituted-phenyl-2-hydroxyethyl]-preparation of 3-(3-methoxyl group-4-hydroxy phenyl) propionic acid amide 9-1
Method A: 20mmol (4.5g) 8 is put into the microwave reaction pipe with 21mmol (3.6g) 2-amino to the chlorophenethylol hydrochloride, add catalytic amount DMAP (DMAP).The microwave reaction parameter setting is: power 30W, and 130 ℃ of temperature, the reaction times, 30min was advisable.With acidic aqueous solution washing reaction liquid, three extractions of 100mL ethyl acetate merge organic phase, drying, precipitation.The decompression column chromatography is separated, and obtains lilac solid product 9-1.Productive rate: 60%, 108～110 ℃ of fusing points.
1HNMR(CDCl
3)δ(ppm)400MH：2.40(t，2H，J＝7.2Hz，COCH
2)，2.83(t，2H，J＝6.8Hz，Ar-CH
2)，3.15-3.21(m，2H，NHCH
2)，3.54-3.58(m，2H，NHCH
2)，3.80(s，3H，OCH
3)，4.68-4.69(m，1H，OCH)，5.65(br，1H，NH)，6.60-6.79(m，3H，Ar-H)，7.13-7.24(m，4H，Ar-H)。
Method B: with 6.84mmol (1.44g) 3-(3, the 4-Dimethoxyphenyl) propionic acid dissolves with 15mL THF, cryosel is bathed and it is cooled to-20 ℃, under this temperature, add successively N-methylmorpholine 7.18mmol (0.696g), isobutyl chlorocarbonate 6.84mmol (0.892g), a large amount of white suspension things occur, raw material point disappeared after cryosel was bathed the lower 30min of stirring.The amino substituted benzene ethanol of compound 7.18mmol 2-is dissolved in the anhydrous THF of 25mL, slowly is added drop-wise in the above-mentioned reaction solution, dropwise, about-10 ℃, stir 1h, rise to room temperature, continue to stir 12h.The decompression precipitation was removed THF after reaction finished, and the solid with 40mL methylene dichloride dissolving precipitation obtains adds the 35mL saturated nacl aqueous solution, and extraction merges organic layer, and anhydrous magnesium sulfate drying filters precipitation.Press combiflash companion to obtain product in crossing.
Under the similarity condition, use compound 2-amino-1-substituted-phenyl ethylate hydrochlorate to be raw material, with the reaction of 3-(3,4-Dimethoxyphenyl) propionic acid, can synthesize other compounds 10-2～10-8 of the present invention.See Table 5 and table 6.
3) N-[2-substituted-phenyl-2-hydroxyethyl]-preparation of 3-(3-methoxyl group-4-alkoxyl phenyl) propionic acid amide 10
15mmol 9 is dissolved in 160mL aqueous ethanolic solution (EtOH/H
2O 3/1v/v) in, add 18mmol (0.7g) NaOH, stir, solid dissolves fully; Add the 23mmol bromoalkane, stir and be warming up to 65～70 ℃.About 6h reacts completely; Concentrated hydrochloric acid is transferred pH=6～7, and decompression removes most of ethanol under the room temperature, and the adularescent solid is separated out.Suction filtration, drying obtains target compound 10.
Equally, can synthesize other compounds 10 of the present invention.See Table 5 and table 6.
Table 5: the physical and chemical parameter of compound 10
Table 6: the nuclear magnetic data of compound 10
4) N-[2-substituted-phenyl-2-replaces ethyl]-3-(3-methoxyl group-4-alkoxyl phenyl) Propionamides compound 11 synthetic
2.0mmol compound 10 is dissolved in the 50mL anhydrous tetrahydro furan, is heated to backflow, solid dissolves gradually.Add 2.4mmol (0.06g) sodium hydride, solution is acutely boiling immediately, backflow 10min, and solution colour is deepened gradually; The alkylating reagent that adds 3.0mmol (1.5eq), the TLC monitoring reaction; Reaction is during near terminal point, adds the shrend reaction of going out; Decompression removes tetrahydrofuran (THF) and obtains the thickness soup compound under the room temperature, and with the sodium hydroxide solution dissolving of pH=10,30mL ethyl acetate extraction 3 times merges organic phase, drying, precipitation.The decompression column chromatography is separated, and obtains target product.
Under the similarity condition, can synthesize other compounds 11 of the present invention, see Table 7 and table 8.
Table 7: the physical and chemical parameter of compound 11
Table 8: the nuclear magnetic data of compound 11
Embodiment 3: the aphid biological activity determination
Will with about 60 grow to adult a few days ago individual neat and consistent the bean aphid nymph for examination bean plant (bean seedlings mounted blade, about plant height 12cm) from potted plant, cut, 3 seconds of dipping in cultivating in advance good finite concentration liquid, remaining liquid is got rid of in taking-up, be inserted in moisturizing on the 12 hole plastic foamboards (porous plastics thickness of slab 3.5cm is placed in the porcelain dish of 35 * 45cm, uses water-soaked), after doing, liquid uses on lens (gauze of using suitable for reading, the bungee is sealed) cover.Be disposed, under the constant temperature of standard, constant humidity condition, place.96h " Invest, Then Investigate " examination worm death condition is touched polypide with pulling needle, and motionless person is dead.Calculate mortality ratio.
Invention compound 7-2,7-3,7-4,7-7,7-8,7-9,7-10,10-1,11-2,11-3, insecticidal activity 〉=60% when the 11-6 active material concentration is 200ppm in this experiment.
Embodiment 4: red spider (carmine spider mite) biological activity determination
When the bean seedlings that are for experiment grow to two true leaves, select that growing way is relatively more neat, the plant of about 10 centimetres of the about 4-5 square centimeters of leaf area, plant height connects worm, every strain worm amount is no less than 60, general control is about the 60-100 head.Connect worm and carry out chemicals treatment after 24 hours, cut from basal part of stem for the examination plant, connect worm and together blade is immersed in the tested liquid with seedling, soak the medicine time to be controlled at for 5 seconds.After plant was taken out from liquid, unnecessary liquid was removed in shake gently, then moves in the water planting cylinder.Plant after the processing is placed in 25 ℃ of thermostatic chambers.Movable mite is processed rear 96 hours inspection life or death borer populations under paired eyepiece, calculate mortality ratio.
Invention compound 7-2,7-3,7-4, insecticidal activity 〉=60% when the 7-9 active material concentration is 200ppm in this experiment.
Embodiment 5: the live body provide protection that tobacco mosaic virus (TMV) is infected
Select the 3-5 leaf phase coral west cigarette of growing way uniformity, the complete stool spray pesticide, every processing repeats for 3 times, and establishes the contrast of the 1 ‰ tween 80 aqueous solution.Behind the 24h, blade face spreading silicon carbide (500 order) dips virus liquid with writing brush, dabs 2 times along the offshoot direction on full blade face, and the blade below is supported with palm, and virus concentration 10 μ g/mL wash with flowing water after the inoculation.Record scab number calculates preventive effect behind the 3d.
Invention compound 7-16 in this experiment, the live body provide protection of when the 7-17 active material concentration is 500ppm tobacco mosaic virus (TMV) being infected be active 〉=and 30%.
Embodiment 6: the live body therapeutic action that tobacco mosaic virus (TMV) is infected
Select the 3-5 leaf phase coral west cigarette of growing way uniformity, with the full leaf virus inoculation of writing brush, virus concentration is 10 μ g/mL, washes with flowing water after the inoculation.After the blade face is received and is done, the complete stool spray pesticide, every processing repeats for 3 times, and establishes the contrast of the 1 ‰ tween 80 aqueous solution.Record scab number calculates preventive effect behind the 3d.
The live body therapeutic action activity that when invention compound 7-4,7-6,7-7,7-17,7-18 and 11-18 active material concentration are 500ppm in this experiment tobacco mosaic virus (TMV) is infected 〉=30%.
Claims (3)
1. ferulic acid phenethyl alcohol amine derivative is characterized in that having the compound of following general formula (I):
In the formula: R is 1-12 carbon alkyl, 1-12 carbene base, 1-12 carbyne base; R
11-12 carbon alkyl, 1-12 carbene base, 1-12 carbyne base; R
2Be halogen, X-X is carbon-carbon single bond or two key.
2. as claimed in claim 1 application of ferulic acid phenethyl alcohol amine derivative is characterized in that: be used for control Homoptera and cicada Acarina as sterilant.
3. as claimed in claim 1 application of ferulic acid phenethyl alcohol amine derivative is characterized in that: be used for suppressing tobacco mosaic virus disease as anti-plant virus agent.
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| CN102796023A (en) * | 2012-07-27 | 2012-11-28 | 浙江工业大学 | Hydrogenated amide ferulate compounds, and synthesis method and application thereof |
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| CN108191629B (en) * | 2018-01-18 | 2020-12-29 | 刘策 | Ferulic acid derivative and application thereof |
| CN108191691A (en) * | 2018-01-19 | 2018-06-22 | 常州大学 | The preparation of ferulic acid dimers derivative and its application in senile dementia is treated |
| CN113233993B (en) * | 2021-05-18 | 2022-07-01 | 贵州大学 | Ferulic acid amide derivative and synthetic method thereof |
| CN113461639B (en) * | 2021-07-08 | 2022-11-01 | 贵州大学 | Piperazine-containing ferulic acid derivative, and preparation method and application thereof |
| CN113801022B (en) * | 2021-07-23 | 2023-07-28 | 贵州大学 | Eugenol ferulate and isoeugenol hybrid and application thereof |
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| CN102090412A (en) * | 2009-12-11 | 2011-06-15 | 南开大学 | Ferulic acid and ferulic acid derivative anti-phytoviral agents |
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| CN102090412A (en) * | 2009-12-11 | 2011-06-15 | 南开大学 | Ferulic acid and ferulic acid derivative anti-phytoviral agents |
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