CN1803780A - Triazole compounds and preparing process and use thereof - Google Patents
Triazole compounds and preparing process and use thereof Download PDFInfo
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- CN1803780A CN1803780A CN 200610018175 CN200610018175A CN1803780A CN 1803780 A CN1803780 A CN 1803780A CN 200610018175 CN200610018175 CN 200610018175 CN 200610018175 A CN200610018175 A CN 200610018175A CN 1803780 A CN1803780 A CN 1803780A
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Abstract
The disclosed preparation method for a ditriazole compound with general formula as the right comprises: dissolving the 5-azido-1, 2, 4-triazole-3-amidomethyl ester and different hydrocarbon compound into THF or mixed with water; obtaining ditriazole compound with R' as methoxy by Huisgen reaction with Cu(I) as catalyst; dissolving the former product into methanol solution contained ammonia to convert R' into amido. This product can be used to treat the plant attacked by tobacco mosaic virus and provide precursor drug for high efficient pesticide.
Description
Technical field
The invention belongs to organic chemistry and biochemical field, specifically belong to a kind of bi-triazole compound, also belong to the preparation method of this compound simultaneously, also relate to the purposes of this compound in the Antiphytoviral medicine simultaneously.
Background technology
The viroses of plant have the title of " plant cancer ", and ratio shared in Plant diseases is only second to fungal disease, causes serious threat to agriculture production.Only (Tobacco mosaic virus, the loss that TMV) causes just reaches more than 100,000,000 dollars by tobacco mosaic virus (TMV) every year in the whole world according to estimates.Because virus obligatory parasitism in vegetable cell, it duplicates required material, energy and place and relies on the host fully, and plant do not have complete immune metabolic system, makes the control difficulty particularly of the viroses of plant.In order to prevent and treat the viroses of plant effectively; people attempted many useful schemes; as utilize the generation of agricultural measures (crop rotation, rotate crops, select for use resistant variety and seed detoxification treatment etc.) prevention virus disease, or utilize cross protection between virus to select for use biotechnological formulations such as low virulent strain system and satellite RNA to come the dip-dye of viral interference and propagation etc.Yet these measures are to use separately or integrated application all can not overcome the harm that virus disease causes effectively.
Utilizing antiviral agent is the another kind of mode that people prevent and treat the viroses of plant, in order to develop ideal Antiphytoviral medicament, the chemical science worker has also carried out the synthetic and screening trial of many orientations, and developed two big class Anti-virus agents: the one, crude substance such as microorganism, mushroom and plant milk extract are (to Gu Xi etc., a kind of new agricultural antibiotic----Ningnanmycin, microorganism journal, 1995,35,368-374; Hu Houzhi etc., Ningnanmycin prevent and treat the research of tobacco mosaic disease, use and the environmental organism journal, and 1998,4,390-395; An etc., Alkaloids from Cynanchum komarovii with inhibitoryactivity against the tobacco mosaic virus.Phytochemistry, 2001,58,1267-1269; Yao Yucheng etc., the chemical ingredients of Niuxin Pozicao plant pesticide and bioactivity research, organic chemistry, 2001,21,1024-1028.), and the 2nd, the synthetic chemical substance.The former mainly is that protective plant is not subjected to virus infection, and some also can passivation virus, and their antiviral spectrum are narrower.And synthetic medicament has preventive and therapeutic effect concurrently to virus disease, can passivation virus, also can suppress the propagation with viral interference, though their antiviral spectrum broad is also limited after all.Up to now, we also do not develop the similarly efficient or ultra-high efficiency of picture sterilant and weedicide and sterilant etc. and eco-friendly medicament.
In the process of the discovery of agricultural chemicals guide thing and optimization, people are also many as the research of Anti-virus agent to triazole derivative in recent years.Most typical representative is exactly virazole (Ribavirin) to triazole compounds as antiviral agent.Virazole is that first is found the triazole compounds (Sidwell etc. that numerous DNA and RNA viruses had the broad-spectrum antiviral effect, Broad-Spectrum Antiviral Activity of Virazole:1-β-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide.Science, 1972,177,705.).Since before its more than 30 years, being found, virazole has become one of potent agent of the multiple virus infection of treatment, it also is one of medicament of the Antiphytoviral preferably (comprising animal) of generally acknowledging at present, so it is believed that and can go develop how safe and efficient as an effective structural models virazole and the medicine guide of broad-spectrum antiviral effect is arranged.People have obtained a series of derivative by virazole is modified.CN 1420723 the triazole derivative of CN 85108679 and CN1063183 report be exactly the analogue of virazole, this compounds has antiviral preferably and antitumous effect usually.In some external nearest patents relevant report is arranged also, just reported the triazole compounds that some are used for the treatment of cell disease and have anticancer effect as WO 2004037809, WO 02088108, AU 2003256003.
More than Bao Dao compound only contains a triazole unit usually.It is then less relatively to introduce two unitary reports of triazole in compound.CN 1195288 has reported a kind of pharmaceutical composition for the treatment of mammalian cancer or tumour, wherein comprises 2-(2,4 difluorobenzene base)-1, two (1H-1,2,4-triazol-1-yl) propan-2-ol and the derivatives thereof of 3-.Can with certain chemotherapeutics the same with synergistic agent with 2-(2,4 difluorobenzene base)-1, two (1H-1,2,4-triazol-1-yl) propan-2-ols of 3-and derivative thereof share.2-(2,4 difluorobenzene base)-1, two (1H-1,2,4-triazol-1-yl) propan-2-ols of 3-and derivative thereof can also be used for the treatment of animal virus to be infected, and perhaps uses separately, perhaps share with other antiviral and synergistic agent.Its concrete structure is as follows:
EP 113509-A and US 4466974 have also reported two triazole compounds that similar structures is arranged in addition, and these compounds can be used for treatment to be infected by fungus-caused part or system, is the effective antifungal compound of a class.
But the triazole compounds of above patent report does not all relate to the structural unit that is directly linked to each other by two triazole ring, is not applied to the research of Antiphytoviral yet.Recently, this laboratory utilizes click chemistry (Click Chemistry) (H.C.Kolb etc., Click Chemistry:Diverse Chemical Function from a Few Good Reactions.Angew.Chem.Int.Ed., 2001,40,2004-2021.) in most widely used Huisgen cycloaddition reaction synthesized a series of novel bi-triazole compound, the primary structure unit of this compounds is directly linked to each other by two triazole ring and constitutes.Because tobacco mosaic virus (TMV) is a kind of important model of agricultural plants virus research, so we utilize tobacco mosaic virus (TMV) that the synthetic compound has been carried out preliminary screening, test-results shows that this compounds of part has the better prevention effect to tobacco mosaic virus (TMV).This part is worked, and we apply for a patent (number of patent application: 200510018608.8).Recently, on the basis of this work, we have carried out existing compound again, and structure is expanded and optimization, thereby has obtained a series of new bi-triazole compounds.These compounds also have the better prevention effect to tobacco mosaic virus (TMV).Especially compound 1c, the effect that suppresses tobacco mosaic virus (TMV) under similarity condition will be much better than commercial Antiphytoviral reagent-virazole, the outstanding preventive and therapeutic effect to tobacco mosaic virus (TMV) that it shows in preliminary screening, the Antiphytoviral medicament of developing new class for us provides the guide.Compound provided by the invention, synthetic method is simple, inexpensive, environmental friendliness, has broad application prospects.
Summary of the invention
The object of the present invention is to provide a kind of bi-triazole compound, this compound is guide's thing of antiviral, and is with low cost, can suppress the activity of tobacco mosaic virus (TMV) effectively.
Another object of the present invention has been to provide a kind of method for preparing bi-triazole compound.This synthetic method is simple, environmentally safe.
The invention still further relates to bi-triazole compound as the application in the tobacco mosaic virus (TMV) inhibitor.
In order to realize above-mentioned task, problem to be solved by this invention provides class bi-triazole compound and its production and use, the gained bi-triazole compound not only prepares simpler, inexpensive, and can suppress the activity of plant mosaic virus, can be used for being subjected to the therapeutical agent of mosaic virus invasion and attack plant.
Technical scheme provided by the invention is: bi-triazole compound, and its general formula is:
Wherein R is an ethoxycarbonyl, the cyclopentanol base, and phenyl, p-methylphenyl, to fluorophenyl, second hydroxyl, cyclohexenyl or to the amyl group phenyl; R ' is amino or methoxyl group.
R can be divided into R in the general formula of compound
1, R
2, R ' or be OCH
3, NH
2
The general formula of this bi-triazole compound can be following two kinds of modes:
Wherein in the compound of 1 series, R
1For ethoxycarbonyl (1a), cyclopentanol base (1b), phenyl (1c), p-methylphenyl (1d) with to fluorophenyl (1e).In the compound of 2 series, R
2For second hydroxyl (2a), cyclopentanol base (2b), cyclohexenyl (2c), p-methylphenyl (2d) with to amyl group phenyl (2e).
The preparation method of above-claimed cpd is: with 5-azido--1,2,4 triazoles-3-acyl methyl esters and ethyl propiolate, cyclopentanol alkynes, phenylacetylene, to methylbenzene acetylene or the mixture of fluorobenzene acetylene is dissolved in the mixed solvent of tetrahydrofuran (THF) that tetrahydrofuran (THF) or volume ratio are 1/2-1/4 and water, 5-azido--1 wherein, the mol ratio of the consumption of 2,4 triazoles-3-acyl methyl esters and alkynes is 1: 1.2,5-azido--1,2, the 4 triazoles-concentration of 3-acyl methyl esters in reaction solution is 0.03mo1/L.Be reflected at 40-100 ℃ by the catalytic Huisgen of Cu (I) again and react the first kind bi-triazole compound that obtains 1 required series down; Next be with resulting R ' for the compound dissolution of methoxyl group in the methanol solution of ammonia, the compound dissolution of just resulting 1 series is in the methanol solution of ammonia then, reaction can obtain R ' for amino or be the compound of oxygen base under 35-50 ℃ of condition, can also obtain the compound of 2 series.
The bi-triazole compound that the present invention makes not only prepares simple, inexpensive, and can directly suppress the activity of tobacco mosaic virus (TMV), thereby can be used as the inhibitor of tobacco mosaic virus (TMV), and as guide's thing of antiviral.
Description of drawings
Fig. 1 is a kind of design sketch of bi-triazole compound resisting tobacco mosaic virus.
Embodiment
After 5-azido--1,2,4-triazoles-3-acyl methyl esters and all kinds of alkynes being dissolved in the mixed solvent of tetrahydrofuran (THF) and water, under Cu (I) catalysis, reacting and obtain 1 required serial bi-triazole compound.The bi-triazole compound of 1 series is dissolved in the compound that carries out to obtain after ammonia is separated 2 series in the methyl alcohol of ammonia.
Embodiment 1:
(50mg 0.297mmol) places two-mouth bottle, adds 10mL mixed solvent (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/4), obtain water white solution.Under the Ar gas shiled, add again ethyl propiolate (29.2mg, 0.36mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 80 ℃ the reaction 1 hour after, stopped reaction, this moment reaction system be yellow turbid solution, remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1a) is white solid 67.5mg, productive rate 85.3% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ9.30(s，1H)，4.34(q，2H，J＝7.0Hz)，3.95(s，3H)，1.32(t，3H，J＝7.0Hz).
13C NMR(150MHz，DMSO-d
6)：δ160.1 157.1，154.5，147.8，140.5，126.7，61.9，53.8，14.2；MS(ESI)：m/z 265.0(M-H).
Embodiment 2:
(50mg 0.297mmol) places two-mouth bottle, adds mixed solvent 10mL (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/2), material dissolution obtains water white solution.Under the Ar gas shiled, add again cyclopentanol alkynes (39.6mg, 0.36mmoi).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 80 ℃ the reaction 2 hours after, stopped reaction, this moment reaction system be pale brown look turbid solution, directly remove solvent under reduced pressure after, obtain pale brown look solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1b) is white solid 64.1mg, productive rate 77.5% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ8.41(s，1H)，5.07(br s，1H)，3.93(s，3H)，1.89-1.96(m，2H)，1.66-1.77(m，3H)，1.42-1.50(m，3H)，1.21-1.30(m，2H)；
13C NMR(150MHz，DMSO-d
6)：δ157.9，157.2，121.0，68.6，53.7，38.2，25.8，22.3；MS(ESI)：m/z 291.1(M-H).
Embodiment 3:
(50mg 0.297mmol) places two-mouth bottle, adds tetrahydrofuran (THF) 10mL after handling 20 minutes vacuumizing on the oil pump, and material dissolution obtains water white solution with 5-azido--1,2,4-triazoles-3-acyl methyl esters.Under the Ar gas shiled, add again phenylacetylene (36.7mg, 0.36mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 90 ℃ the reaction 3 hours after, stopped reaction, this moment reaction system be faint yellow turbid solution, directly remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1c) is white solid 68.3mg, productive rate 85% after vacuum-drying.
1HNMR(300MHz，DMSO-d
6)：δ9.33(s，1H)，8.00(d，2H，J＝7.8Hz)，7.47(t，2H，J1＝7.2Hz，J2＝7.8Hz)，7.37(t，1H，J1＝J2＝7.5Hz)，3.95(s，3H)；
13C NMR(150MHz，DMSO-d
6)：δ157.7，148.2，147.7，130.3，129.7，129.2，126.3，121.2，53.7；MS(FAB)：m/z 270(M).
Embodiment 4:
(50mg 0.297mmol) places two-mouth bottle, adds mixed solvent 10mL (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/4), material dissolution obtains water white solution.Under the Ar gas shiled, add again to methylbenzene acetylene (41.8mg, 0.36mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 80 ℃ the reaction 5 hours after, stopped reaction, this moment reaction system be yellow turbid solution, directly remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2C1
2/ MeOH=30/1), the product that obtains (1d) is white solid 71.6mg, productive rate 84.5% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ9.26(s，1H)，7.89(d，2H，J＝8.1Hz)，7.28(d，2H，J＝8.1Hz)，3.95(s，3H)，2.33(s，3H)；
13C NMR(150MHz，DMSO-d
6)：δ156.8，146.5，137.5，129.0，126.3，125.1，119.5，52.6，20.4；MS(FAB)：m/z 285.0(M+H).
Embodiment 5:
(50mg 0.297mmol) places two-mouth bottle, adds mixed solvent 10mL (THF/H after handling 20 minutes vacuumizing on the oil pump with 5-azido--1,2,4-triazoles-3-acyl methyl esters
2O=1/2), material dissolution obtains water white solution.Under the Ar gas shiled, add again to fluorobenzene acetylene (43.2mg, 0.36mmol).In addition with cupric sulfate pentahydrate (11.8mg, 0.047mmol) and SODIUM ASCORBATE (29.5mg, 0.148mmol) be dissolved in the 200 μ L water respectively after, the above-mentioned reaction system of reinjecting.Be reflected at 80 ℃ the reaction 4 hours after, stopped reaction, this moment reaction system be faint yellow turbid solution, directly remove solvent under reduced pressure after, obtain yellow solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=30/1), the product that obtains (1e) is white solid 73.6mg, productive rate 70% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ9.33(s，1H)，8.04(dd，2H，
4J
HF＝5.4Hz，
3J
HH＝8.7Hz)，7.31(dd，2H，
3J
HF＝8.7Hz，
3J
HH＝8.7Hz)，3.94(s，3H)；
13C NMR(150MHz，DMSO-d
6)：δ162.8(
1J
CF＝245.2Hz)，157.7，146.8，128.3(
3J
CF＝8.3Hz)，126.8，121.1，116.6(
2J
CF＝20.4Hz)，53.7；MS(FAB)：m/z 289.0(M+H).
Embodiment 6:
Will (80mg 0.30mmol) be dissolved in the methanol solution of 15mL saturated ammonia stirring reaction under the Ar gas shiled by 5-azido--1,2,4-triazoles-3-acyl methyl esters and acetate propine alcohol ester synthetic bi-triazole compound.Be reflected at carry out 48 hours under 40 ℃ after, stopped reaction, this moment reaction system be colourless transparent liquid, directly remove solvent under reduced pressure after, obtain white solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=5/1), the product that obtains (2a) is white solid 44.9mg, productive rate 71.5% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ8.38(s，1H)，8.11(s，br，1H)，7.80(s，br，1H)，5.28(s，br.1H)，4.59(s，2H)；
13C NMR(150MHz，DMSO-d
6)：δ159.6，155.3，152.6，149.1，122.6，55.4；MS(ESI)：m/z 208.0(M-H)
Embodiment 7:
(80mg 0.28mmol) is dissolved in the methanol solution of 15mL saturated ammonia stirring reaction under the Ar gas shiled with 1b.Be reflected at carry out 48 hours under 35 ℃ after, stopped reaction, this moment reaction system be colourless transparent liquid, directly remove solvent under reduced pressure after, obtain white solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=5/1), the product that obtains (2b) is white solid 61.3mg, productive rate 81% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ8.34(s，br，1H)，8.33(s，1H)，8.06(s，br，1H)，5.21(s，br，1H)，1.98-2.03(m，3H)，1.82-1.91(m，3H)，1.72-1.73(m，2H)；MS(ESI)：m/z 262.0(M-H).
Embodiment 8:
Will (80mg 0.29mmol) be dissolved in the methanol solution of 15mL saturated ammonia stirring reaction under the Ar gas shiled by 5-azido--1,2,4-triazoles-3-acyl methyl esters and hexamethylene eneyne synthetic bi-triazole compound.Be reflected at carry out 36 hours under 35 ℃ after, stopped reaction, this moment reaction system be colourless transparent liquid, directly remove solvent under reduced pressure after, obtain white solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=6/1), the product that obtains (2c) is white solid 67.9mg, productive rate 89.8% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ8.58(s，1H)，8.35(s，br，1H)，8.04(s，br，1H)，6.58(s，br，1H)，2.36-2.37(m，2H)，2.16-2.17(m，2H)，1.69-1.72(m，2H)，1.59-1.63(m，2H)；
13C NMR(150MHz，DMSO-d
6)：δ157.8，154.3，150.8，148.3，126.5，125.1，118.7，25.6，24.6，21.9，21.7；MS(ESI)：m/z 258.2(M-H).
Embodiment 9:
(80mg 0.28mmol) is dissolved in the methanol solution of 15mL saturated ammonia stirring reaction under the Ar gas shiled with 1d.Be reflected at carry out 48 hours under 35 ℃ after, stopped reaction, this moment reaction system be colourless transparent liquid, directly remove solvent under reduced pressure after, obtain white solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=6/1), the product that obtains (2d) is white solid 58.3mg, productive rate 77% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ9.07(s，1H)，8.21(s，br，1H)，7.85(d，3H，J＝8.1Hz)，7.27(d，2H，J＝8.1Hz)，2.32(s，3H)；
13C NMR(150MHz，DMSO-d
6)：δ160.6，155.5，153.7，147.2，138.4，130.2，127.9，126.1，120.7，21.6；MS(ESI)：m/z 268.1(M-H).
Embodiment 10:
Will be by 5-azido--1,2,4-triazoles-3-acyl methyl esters with (80mg 0.23mmol) be dissolved in the methanol solution of 15mL saturated ammonia stirring reaction under the Ar gas shiled to amylbenzene acetylene synthetic bi-triazole compound.Be reflected at carry out 40 hours under 35 ℃ after, stopped reaction, this moment reaction system be colourless transparent liquid, directly remove solvent under reduced pressure after, obtain white solid.By column chromatogram chromatography product separation (CH
2Cl
2/ MeOH=6/1), the product that obtains (2e) is white solid 68.8mg, productive rate 90% after vacuum-drying.
1H NMR(300MHz，DMSO-d
6)：δ9.09(s，1H)，8.26(s，br，1H)，7.97(s，br，1H)，7.88(d，2H，J＝8.1Hz)，7.29(d，2H，J＝7.8Hz)，2.60(t，2H，J＝7.5Hz)，1.57-1.62(m，2H)，1.27-1.30(m，4H)，0.86(t，3H，J1＝6.6Hz，J2＝6.3Hz).
13C NMR(150MHz，DMSO-d
6)：158.9，155.1，147.5，143.4，129.6，127.9，126.2，120.8，35.5，31.5，31.2，29.4，22.6，14.6；MS(ESI)：m/z 324.1(MH).
Embodiment 11:
The active mensuration of the anti-TMV of compound (the withered spot method of half leaf)
On the tobacco plant of the coral of 5～6 leaf ages west, choose the blade (leaf normal, anosis no worm) that is applicable to test, first blade is evenly sprinkled fine emery powder, with writing brush with standby malicious source (3.0 * 10
-3) evenly be put on the blade that spreads powder emery, after treating that the blade that selects in all connects the poison end, immediately with handling 20 minutes in the culture dish that fills the soup that has The compounds of this invention, take out, the globule and soup on the drop defoliation sheet restore two and half leaves to be emitted in the enamel tray that is covered with the toilet paper insulation and add cover glass, 23 ± 2 ℃ of controlled temperature, be placed on the greenhouse natural lighting and get final product, can manifest withered spot in 2～3 days.Each processing all has its corresponding half leaf in contrast, and the processing that one group of commodity virus of A also is set in addition as a comparison.
X: relative effect (%); CK: be soaked in the withered spot number (individual) that half sheet in the clear water connects malicious leaf;
T: the withered spot number (individual) that is dipped in half sheet leaf in the soup
Embodiment 12:
The active mensuration of the anti-TMV of compound (live body revulsion)
The screening method of new compound evoking tobacco live body activity of resisting tobacco mosaic virus: the method with reference to (2005) such as model will gold is carried out, common cigarette seedling with the seedling age unanimity, 3 basins are one group, the chemicals treatment mode comprises: the solution 2 to 3 times that sprays The compounds of this invention, each 10mL, or root irrigation cigarette seedling 2 to 3 times, each 20mL, behind the certain hour on tobacco leaf frictional inoculation TMV, after cultivating 3d, check incidence, comprehensive scab number is calculated as follows out the inducing anti-disease toxic effect fruit of The compounds of this invention to TMV, 3 repetitions are established in each processing, and contrast divides blank and standard chemicals treatment to contrast 2 kinds; The effect of inducing of test compounds is divided into 5 grades: A, B, C, D and E, and concrete data are the A level: induce effect＞90%, for excellent; B level: induce effect 90～70%, for very; C level: induce effect 70～50%, for better; The D level: induce effect 50～3 (0%, for poor; E level: induce effect＜30% to be considered as not having and induce effect.
What wherein, R was medicament or The compounds of this invention to the anti-TMV of tobacco induces (or live body) effect, unit: %
CK is the average withered spot number of clear water contrast blade, unit: individual
I is the average withered spot number through medicament or The compounds of this invention processing (or inducing processing) rear blade, unit: individual
The bi-triazole compound of the invention described above gained has been carried out the screening of 500 μ g/mL according to the normal experiment that screens, experimental result (seeing the following form) shows, the bi-triazole compound of gained of the present invention has certain inhibition effect to tobacco mosaic virus (TMV), compound 1c particularly, its inhibiting rate (is seen accompanying drawing) about 60%, be a very potential tobacco mosaic virus (TMV) inhibitor.The plant inducing anti-disease activator diazosulfide of standard itself does not have the activity of anti-TMV, but it can produce lasting to TMV and resistance that lag behind by evoking tobacco, and by comparison, compound 1c does not but have tangible induced activity.
| Compound | Concentration Mg/mL | The effect % of direct anti-TMV virus | The active % of the anti-TMV of evoking tobacco | |
| Foliar spray | Soil treatment | |||
| 1a 1b 1c 1d 1e 2a 2b 2c 2d 2e virazole diazosulfide | 500 500 500 500 500 500 500 500 500 500 500 100 | 15 7 60 10 11 8 12 7 6 21 30 0 | - - 10 - - - - - - - - 85 | - - 10 - - - - - - - - 96 |
Claims (6)
1, bi-triazole compound, its general formula is:
Wherein R is ethoxycarbonyl, cyclopentanol base, phenyl, p-methylphenyl, and to fluorophenyl, second hydroxyl, cyclohexenyl or to the amyl group phenyl; R ' is amino or methoxyl group.
2, the preparation method of the described a kind of bi-triazole compound of claim 1, it comprises the following steps: at first with 5-azido-1,2,4 triazoles-3-acyl methyl esters and ethyl propiolate, cyclopentanol piece, phenylacetylene, be dissolved in the mixed solvent of tetrahydrofuran (THF) or tetrahydrofuran (THF) and water to methylbenzene acetylene or to the mixture of fluorobenzene acetylene, by the catalytic Huisgen reaction of Cu (I), reaction obtains required bi-triazole compound under 40-100 ℃; Next be with resultant R ' for the compound dissolution of methoxyl group in the methanol solution of ammonia, reaction obtains R ' and is amino compound under 35-50 ℃ condition again.
3, the preparation method of a kind of bi-triazole compound according to claim 2 is characterized in that the consumption mol ratio of 5-azido--1,2,4-triazoles 3 acyl methyl esters and alkynes is 1: 1.2.
4, the preparation method of a kind of bi-triazole compound according to claim 2 is characterized in that the concentration of 5-azido--1,2,4-triazoles 3 acyl methyl esters in reaction solution is 0.03mol/L.
5, the preparation method of a kind of bi-triazole compound according to claim 1, the consumption volume ratio that it is characterized in that the mixed solvent of tetrahydrofuran (THF) and water is 1/2-1/4.
6, the application of the described bi-triazole compound of claim 1 in the tobacco mosaic virus (TMV) inhibitor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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