CN102503851A - 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 ferulic acid 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 FLA Phenethanolamine derivative and application.
[background technology]
Plant virus have the title of " plant cancer ", and present known plant virus has 716 kinds (Zhang Chengliang etc., plant virus taxonomy, Chinese agriculture press, 1996,283), and the document that also has is thought more than 1000 kinds.
Plant virus harm unifacial leaf, various plants and mikrobe 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 all has, and harm is only second to fungal disease.Virus is not only fought for the necessary for plant growth nutritive ingredient 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 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; Like yellow stunt of wheat, nineteen fifty-one is found in the U.S. first, has become worldwide disease at present; Begin the beginning of the sixties to endanger in Shaanxi; 1960, the average year underproduction 30% reached 60% individually 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 leat 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 have instant effect, easy to use, farming this low, easy to use and suppress the virus spectrum wide etc. many a bit.A large amount of facts shows that plant virus chemical prevention agent is the same with sterilant and in the control of Plant diseases, occupies critical role.
The control of plant virus chemical prevention agent spectrum is quite extensive, yet from actual production, sees, usually between 30～70%, and great majority are biological and complex agent type chemical classes to the control effect of plant virus in the chemical prevention agent.Its staple is that, deactivation matter, defense response exciton and physiologically active of plant are regulated one type of mixed thing such as material.Mainly uses moroxydine hydrochloride, virazole, Ningnanmycin and amino-oligosaccharide etc.
It is the cell walls that material constitutes that yet the vegetable cell outermost layer has with the Mierocrystalline cellulose, is enough to resist the intrusion of virus, thereby one of characteristics of plant virus are can invade through host's wound.At occurring in nature, the most important communication media of plant virus is insect and the mite class 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, reach the effect of integrated control with insecticidal activity.
[summary of the invention]
The objective of the invention is to provides a kind of FLA Phenethanolamine derivative with insecticidal activity and anti-phytoviral activity to above-mentioned technical Analysis, is used to prepare sterilant and anti-plant virus agent.
Technical scheme of the present invention:
A kind of FLA Phenethanolamine 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
1Be 1-12 carbon alkyl, 1-12 carbene base, 1-12 carbyne base or substituted benzyl; R
2Be 1-6 carbon alkyl, 1-6 carbon alkoxyl group, 1-6 carbon alkylamino radical, 1-6 carbon alkylthio, substituted benzyloxy, halogen, hydroxyl, cyanic acid, nitro or carboxyl; Substituting group quantity is 1～5.
Said 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 said FLA Phenethanolamine derivative is used to prevent and treat Homoptera and cicada Acarina as sterilant.
A kind of application of said FLA Phenethanolamine derivative, as anti-plant virus agent be used 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 preparation route of The compounds of this invention (I) was:
, concrete preparation process is following:
1) NaOH is soluble in water, add FLA, be stirred to dissolving fully, ice-water bath is reduced 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, and suction filtration, recrystallization get the acetyl FLA;
2) add the acetyl FLA in the thionyl chloride, reflux 4h sloughs thionyl chloride, obtains yellow solid acetyl FLA acyl chlorides 3;
3) the substituted acetophenone hydrochloride joins in the anhydrous tetrahydro furan, and cryosel is bathed and is cooled to below-10 ℃, adds triethylamine; After stirring 10min, the tetrahydrofuran solution of acetyl FLA 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, adds Peng Qinghuana, and reaction 4h adds entry; Be heated to 60 ℃ and stir 1h, remove methyl alcohol, 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)-acrylic amide 5;
5) compound 5 is dissolved in the aqueous ethanolic solution, adds 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) acrylic amide 6;
6) compound 6 is dissolved in the anhydrous tetrahydro furan, adds sodium hydride, adds alkylating reagent; TLC monitoring reaction terminal point adds the shrend reaction of going out, and removes THF; Add the dissolving of NaOH solution, extraction, drying; Precipitation can make (E)-N-[2-(4-substituted-phenyl)-2-replaces ethyl]-3-(3-methoxyl group-4-substituted-phenyl) acrylamides 7.
When X-X was carbon-carbon single bond, the preparation route of The compounds of this invention (I) was:
, concrete preparation process is following:
1) FLA is dissolved in the mixing solutions of absolute ethyl alcohol and THF, adds 10mL concentrated hydrochloric acid and 10% palladium carbon, 40 ℃ continue to feed hydrogen down 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 the 4-Dimethylamino pyridine, 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, adds 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, adds sodium hydride, backflow 10min; Add alkylating reagent, the TLC monitoring is during reaction end; Add the shrend reaction of going out, reducing pressure removes THF, ethyl acetate extraction; Drying, precipitation can make the synthetic of product N-[2-substituted-phenyl-2-replaces ethyl]-3-(3-methoxyl group-4-alkoxyl phenyl) Propionamides compound 11.
Advantage of the present invention is: compound of the present invention has good inhibitory effect to the insect of plant virus and transmitted virus; As sterilant, can prevent and treat 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 various crop such as tobacco, grain, vegetables, beans.
[embodiment]
Embodiment 1: the preparation of FLA Phenethanolamine derivative
1) preparation of acetyl FLA 2
0.52mol (20.8g) sodium hydroxide is dissolved in the 200mL water, adds 0.20mol (38.8g) FLA, be stirred to dissolving fully, ice-water bath is reduced 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 room temperature subsequently 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.The acetyl FLA is a 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)-preparation of 4-[3-(2-(4-chloro-phenyl-)-2-carbonyl ethylamino-)-3-carbonyl-1-propylene]-2-p-methoxy-phenyl Acetyl Chloride 98Min. 3
Put into 50mmol (11.8g) acetyl FLA in the 250mL there-necked flask, add 200mmol (23.8g) thionyl chloride and stirring again, be heated to 78 ℃ and begin to reflux.Holding temperature stirs 4h, reacts complete basically, heated, and take thionyl chloride out of with stream of nitrogen gas, obtain yellow solid acetyl FLA acyl chlorides 3.It is subsequent use under the room temperature this solid to be dissolved in the 100mL anhydrous tetrahydro furan.
3) (E)-preparation of 4-[3-(2-(4-chloro-phenyl-)-2-carbonyl ethylamino-)-3-carbonyl-1-propylene]-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 THF suspension liquid is reduced 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 a 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 a 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) preparation of N-[2-(4-chloro-phenyl-)-2-hydroxyethyl]-3-(3-methoxyl group-4-hydroxy phenyl)-acrylic amide 5-1
2.5mmol (1.0g) 4-1 is dissolved in the 40mL anhydrous methanol, slowly adds 10mmol (0.4g) Peng Qinghuana 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.Decompression removes methyl alcohol, transfers pH=6～7 with concentrated hydrochloric acid, separates out white solid, suction filtration, and drying obtains product 5-1.Product is a 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)-acrylic amide 5-2.Product is a 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) acrylic amide 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, other compounds 6 of the present invention be can synthesize, table 1 and table 2 seen.
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 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, other compounds 7 of the present invention be can synthesize, table 3 and table 4 seen.
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 absolute ethyl alcohol and 60mL THF, adds the 10mL concentrated hydrochloric acid under the room temperature, stir.Standard atmosphere is depressed feeding nitrogen and is removed the air in the reaction system, adds 1g 10% palladium carbon subsequently.40 ℃ of temperature of reaction are kept in hot water bath, and hydrogen replacement nitrogen continues to feed, with bubbler keep watch on gas feed 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 ETHYLE ACETATE merge organic phase, drying, and precipitation obtains light brown oily matter, productive rate: 98%.
2) preparation of N-[2-substituted-phenyl-2-hydroxyethyl]-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 (4-Dimethylamino pyridine).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 ETHYLE 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, adds N-methylmorpholine 7.18mmol (0.696g) successively, isobutyl chlorocarbonate 6.84mmol (0.892g); A large amount of white suspension things occur, raw material point disappeared after cryosel was bathed and stirred 30min down.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.Reaction finishes back decompression precipitation and removes THF, 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 quick preparative hplc to obtain product in crossing.
Under the similarity condition, use compound 2-amino-1-substituted-phenyl ethylate hydrochlorate to be raw material,, can synthesize other compounds 10-2～10-8 of the present invention with the reaction of 3-(3, the 4-Dimethoxyphenyl) propionic acid.See table 5 and table 6.
3) preparation of N-[2-substituted-phenyl-2-hydroxyethyl]-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 is 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 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, other compounds 11 of the present invention be can synthesize, table 7 and table 8 seen.
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
To have grow about 60 to adult a few days ago the confession examination broad bean plant (the bean seedlings mounted blade is about plant height 12cm) of the bean aphid nymph of individual neat and consistent from potted plant, cut, cultivating in the good finite concentration soup 3 seconds of dipping in advance; Surplus liquid is got rid of in taking-up; Be inserted on the 12 hole plastic foamboards preserve moisture (porous plastics thickness of slab 3.5cm is placed in the porcelain dish of 35 * 45cm, uses water-soaked); Treat that the dried back of soup is with on lens (gauze of using suitable for reading, the bungee is sealed) cover.Dispose, in constant temperature, the constant humidity condition held of standard.96h " Invest, Then Investigate " examination worm death condition is touched polypide to dial pin, 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, generally is controlled at about the 60-100 head.Connect worm and carry out chemicals treatment after 24 hours, supply the examination plant to cut, connect worm band seedling and together blade is immersed in the soup of being tested, soak the medicine time to be controlled at for 5 seconds from basal part of stem.After plant was taken out from soup, unnecessary soup was removed in shake gently, moves into then in the water planting cylinder.Plant after the processing is placed in 25 ℃ of thermostatic chambers.Movable mite is handled back 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 in writing brush and to get viral liquid, dabs 2 times along the offshoot direction on full blade face, and the blade below is supported with palm, virus concentration 10 μ g/mL, and the inoculation back is washed with flowing water.Record scab number calculates preventive effect behind the 3d.
Live body provide protection activity >=30% that invent compound 7-16 in this experiment, when the 7-17 active material concentration is 500ppm tobacco mosaic virus(TMV) is infected.
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, and the inoculation back is washed with flowing water.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.
Live body therapeutic action activity >=30% 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.
Claims (4)
1. FLA Phenethanolamine 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 or substituted benzyl; R
1Be 1-12 carbon alkyl, 1-12 carbene base, 1-12 carbyne base or substituted benzyl; R
2Be 1-6 carbon alkyl, 1-6 carbon alkoxyl group, 1-6 carbon alkylamino radical, 1-6 carbon alkylthio, substituted benzyloxy, halogen, hydroxyl, cyanic acid, nitro or carboxyl; Substituting group quantity is 1 ~ 5.
2. according to the said FLA Phenethanolamine derivative of claim 1, it is characterized in that: said 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.
3. the application of FLA Phenethanolamine derivative according to claim 1 is used to prevent and treat Homoptera and cicada Acarina as sterilant.
4. application of FLA Phenethanolamine derivative according to claim 1, as anti-plant virus agent be used 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.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102796023A (en) * | 2012-07-27 | 2012-11-28 | 浙江工业大学 | Hydrogenated amide ferulate compounds, and synthesis method and application thereof |
| US9988352B2 (en) | 2014-06-06 | 2018-06-05 | Board Of Trustees Of Michigan State University | Compounds for inhibition of fungal toxin production |
| CN108191629A (en) * | 2018-01-18 | 2018-06-22 | 刘策 | A kind of ferulic acid derivative and its application |
| 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 |
| CN113233993A (en) * | 2021-05-18 | 2021-08-10 | 贵州大学 | Ferulic acid amide derivative and synthetic method thereof |
| CN113461639A (en) * | 2021-07-08 | 2021-10-01 | 贵州大学 | Piperazine-containing ferulic acid derivative, and preparation method and application thereof |
| CN113801022A (en) * | 2021-07-23 | 2021-12-17 | 贵州大学 | Ferulic acid eugenol and isoeugenol heterozygote 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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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102796023A (en) * | 2012-07-27 | 2012-11-28 | 浙江工业大学 | Hydrogenated amide ferulate compounds, and synthesis method and application thereof |
| US9988352B2 (en) | 2014-06-06 | 2018-06-05 | Board Of Trustees Of Michigan State University | Compounds for inhibition of fungal toxin production |
| US10450271B2 (en) | 2014-06-06 | 2019-10-22 | Board Of Trustees Of Michigan State University | Compounds for inhibition of fungal toxin production |
| CN108191629A (en) * | 2018-01-18 | 2018-06-22 | 刘策 | A kind of ferulic acid derivative and its application |
| 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 |
| CN113233993A (en) * | 2021-05-18 | 2021-08-10 | 贵州大学 | Ferulic acid amide derivative and synthetic method thereof |
| CN113233993B (en) * | 2021-05-18 | 2022-07-01 | 贵州大学 | Ferulic acid amide derivative and synthetic method thereof |
| CN113461639A (en) * | 2021-07-08 | 2021-10-01 | 贵州大学 | Piperazine-containing ferulic acid derivative, and preparation method and application thereof |
| CN113461639B (en) * | 2021-07-08 | 2022-11-01 | 贵州大学 | Piperazine-containing ferulic acid derivative, and preparation method and application thereof |
| CN113801022A (en) * | 2021-07-23 | 2021-12-17 | 贵州大学 | Ferulic acid eugenol and isoeugenol heterozygote 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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|---|---|
| CN102503851B (en) | 2013-10-16 |
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