CN112175030B - Acetyl glucose triazole benzamide compound and synthesis method and application thereof - Google Patents
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Abstract
The invention discloses an acetyl glucose triazole benzamide compound and a synthesis method and application thereof, belonging to the technical field of chemical synthesis, wherein the structural general formula of the acetyl glucose triazole benzamide compound is as follows:
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to an acetyl glucose triazole benzamide compound and a synthesis method and application thereof.
Background
The potato late blight is a destructive disease caused by phytophthora infestans, has the characteristics of wide occurrence range, high epidemic speed and serious harm, can reduce the yield by 10-20% in general years, can reach 50-70% in serious harm years, and even cannot be harvested. At present, due to the degeneration of disease resistance of varieties and imperfect agricultural management, the prevention and treatment of the potato late blight mainly depends on chemical prevention and treatment. The medicaments for preventing and treating potato late blight mainly comprise protective medicaments such as copper hydroxide, mancozeb, fentin, iprodione, chlorothalonil, fluopicolide, cyazofamid and the like; propamocarb, metalaxyl, cymoxanil, dimethomorph and other therapeutic agents, and matrine, eugenol and other biological source bactericides. However, the use of these chemicals for controlling potato late blight brings about problems such as: the long-term use of the traditional chemical pesticide can lead pathogens to gradually generate resistance, and the use amount of the pesticide is continuously increased, thus leading the problem of more serious ecological environment; and most of the traditional chemical bactericides kill pathogenic bacteria and poison beneficial microorganisms and natural enemies of insects and pests.
Therefore, creating a novel, efficient and environmentally friendly bactericide is a real problem that needs to be solved urgently in the current agricultural production.
Disclosure of Invention
The purpose of the embodiments of the present invention is to provide an acetyl glucose triazole benzamide compound, so as to solve the problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
an acetyl glucose triazole benzamide compound has a structural general formula as shown in formula I:
wherein R is a substituent at any position on the ring.
Preferably, in the formula, R is H or 2-CH3、3-CH3、4-CH3、2-OCH3、3-OCH3、4-OCH3、2,3-(CH3)2、2,4-(CH3)2、2,5-(CH3)2、2,6-(CH3)2、2,3-(OCH3)2、2,4-(OCH3)2、2,5-(OCH3)2、2,6-(OCH3)2、2-F、3-F、4-F、2-Cl、3-Cl、4-Cl、2-Br、3-Br、4-BrPh、2-NO2、3-NO2、4-NO2、2-CF3、3-CF3、4-CF3At least one of (1).
Another objective of the embodiments of the present invention is to provide a method for synthesizing the above acetylglucosamine triazole benzamide compound, which comprises the following steps:
reacting 2 ', 3', 4 ', 6' -tetra-O-acetyl-alpha-D-bromoglucose with the raw material A to obtain an intermediate (2-amino-5- (sulfo-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose);
reacting the intermediate (2-amino-5- (sulfo-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose) with a raw material B to obtain the acetyl glucose triazole benzamide compound;
wherein, the structural formula of the raw material A is respectively shown as a formula A, and the structural formula of the raw material B is respectively shown as a formula B:
preferably, the step of reacting 2 ', 3', 4 ', 6' -tetra-O-acetyl- α -D-bromoglucose with the raw material a to obtain the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl- β -D-glucose) specifically comprises:
mixing A, NaOH raw materials, distilled water and acetone to obtain a first mixed solution;
preparing 2 ', 3', 4 ', 6' -tetra-O-acetyl-alpha-D-bromoglucose into a solution, dropwise adding the solution into the first mixed solution for reaction, and then purifying and separating to obtain an intermediate (2-amino-5- (sulfo-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose).
Preferably, in said step, 2 ', 3', 4 ', 6' -tetra-O-acetyl- α -D-bromoglucose is prepared as an acetone solution of 2 ', 3', 4 ', 6' -tetra-O-acetyl- α -D-bromoglucose.
Preferably, the step of reacting the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl- β -D-glucose) with the raw material B to obtain the acetylglucose triazole benzamide compound specifically comprises:
mixing the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose), dichloromethane and triethylamine to obtain a second mixed solution;
and (3) after the raw material B and thionyl chloride are mixed and react completely, removing the thionyl chloride, preparing the residue into a solution, dropwise adding the solution into the second mixed solution for reaction, and then carrying out purification and separation to obtain the acetyl glucose triazole benzamide compound.
Preferably, in this step, the residue is formulated as a solution of the acid chloride in methylene chloride.
Specifically, the reaction route of the synthesis method is as follows:
the embodiment of the invention also aims to provide application of the acetyl glucose triazole benzamide compound in inhibition of potato late blight pathogenic bacteria.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
the acetyl glucose triazole benzamide compound provided by the embodiment of the invention is simple in synthesis method, is an efficient and environment-friendly bactericide, can be applied to agricultural sterilization, particularly has a good inhibition effect on the activity of potato late blight pathogenic bacteria, and can be used for preventing and reducing the occurrence of potato late blight.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1
The material embodiment provides a synthesis method of an acetyl glucose triazole benzamide compound, and the reaction route is as follows, wherein R is a substituent on a ring where the R is located, and is specifically 2-CH3：
Specifically, the synthesis method comprises the following steps:
s1, synthesis of intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl- β -D-glucose): adding 400mg (0.01mol) of NaOH, 10mL of distilled water, 50mL of acetone solution and 0.01mol of raw material A into a 50mL three-necked bottle, and stirring for 30min to obtain a first mixed solution; 0.98g (2.4mmo1) of 2 ', 3', 4 ', 6' -tetra-O-acetyl-. alpha. -D-bromoglucose was dissolved in 5mL of acetone solution and added dropwise to the first mixed solution to conduct a reaction, stirred at room temperature, checked by TLC, developing solvent: v (ethyl acetate): v (petroleum ether) ═ 1: 2. When the reaction was complete, the solvent was removed by rotary evaporation under reduced pressure, 200mL of dichloromethane were added to the bottle containing the residue, washed 2 times with water (2X 20mL), the aqueous phase was extracted 2 times with dichloromethane (2X 20mL), and the organic phases were combined. Drying the organic phase by anhydrous magnesium sulfate, filtering, decompressing, spin-drying and removing the solvent to obtain a crude product, and separating by silica gel column chromatography to obtain an intermediate (2-amino-5- (sulfo-1, 3, 4-thiadiazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose). Wherein the structural formula of the raw material A is as follows:
s2, dissolving 2.54mmol (0.345g) of raw material B with a structural formula shown as the following formula B in 4 mL of thionyl chloride in a 50mL three-neck flask, carrying out reflux reaction at 60 ℃ for 2 hours, fully spin-drying a reaction system, adding 1.0mmol of the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose), 10mL of dichloromethane and triethylamine (TEA, 1.0mmol), stirring at room temperature, slowly dropwise adding a dichloromethane solution of 1.2mmol of acyl chloride, stirring for three hours, carrying out TLC tracking reaction, after the reaction is completed, quenching with water, separating out an organic phase, spin-drying, and recrystallizing a crude product with isopropanol to obtain the acetyl glucose triazole benzamide compound. Wherein the structural formula of the raw material B is as follows:
example 2
The material embodiment provides a synthesis method of an acetyl glucose triazole benzamide compound, and the reaction route is as follows, wherein R is a substituent on a ring where the R is located, and is specifically 2-Cl:
specifically, the synthesis method comprises the following steps:
s1, synthesis of intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl- β -D-glucose): adding 400mg (0.01mol) of NaOH, 10mL of distilled water, 50mL of acetone solution and 0.01mol of raw material A into a 50mL three-necked bottle, and stirring for 30min to obtain a first mixed solution; 0.98g (2.4mmo1) of 2 ', 3', 4 ', 6' -tetra-O-acetyl-. alpha. -D-bromoglucose was dissolved in 5mL of acetone solution and added dropwise to the first mixed solution to conduct a reaction, stirred at room temperature, checked by TLC, developing solvent: v (ethyl acetate): v (petroleum ether) ═ 1: 2. When the reaction was complete, the solvent was removed by rotary evaporation under reduced pressure, 200mL of dichloromethane were added to the bottle containing the residue, washed 2 times with water (2X 20mL), the aqueous phase was extracted 2 times with dichloromethane (2X 20mL), and the organic phases were combined. Drying the organic phase by anhydrous magnesium sulfate, filtering, decompressing, spin-drying and removing the solvent to obtain a crude product, and separating by silica gel column chromatography to obtain an intermediate (2-amino-5- (sulfo-1, 3, 4-thiadiazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose). Wherein the structural formula of the raw material A is as follows:
s2, dissolving 2.54mmol (0.396g) of raw material B with a structural formula shown as the following formula B in 4 mL of thionyl chloride in a 50mL three-neck flask, carrying out reflux reaction at 60 ℃ for 2 hours, fully spinning the reaction system, adding 1.0mmol of the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose), 10mL of dichloromethane and triethylamine (TEA, 1.0mmol), stirring at room temperature, slowly dropwise adding a dichloromethane solution of 1.2mmol of acyl chloride, stirring for three hours, carrying out TLC tracking reaction, after the reaction is completed, quenching with water, separating out an organic phase, spinning, and recrystallizing a crude product with isopropanol to obtain the acetyl glucose triazole benzamide compound. Wherein the structural formula of the raw material B is as follows:
example 3
The material embodiment provides a synthesis method of an acetyl glucose triazole benzamide compound, and the reaction route is as follows, wherein R is a substituent on a ring where the R is located, and is specifically 2-NO2：
Specifically, the synthesis method comprises the following steps:
s1, synthesis of intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl- β -D-glucose): adding 400mg (0.01mol) of NaOH, 10mL of distilled water, 50mL of acetone solution and 0.01mol of raw material A into a 50mL three-necked bottle, and stirring for 30min to obtain a first mixed solution; 0.98g (2.4mmo1) of 2 ', 3', 4 ', 6' -tetra-O-acetyl-. alpha. -D-bromoglucose was dissolved in 5mL of acetone solution and added dropwise to the first mixed solution to conduct a reaction, stirred at room temperature, checked by TLC, developing solvent: v (ethyl acetate): v (petroleum ether) ═ 1: 2. When the reaction was complete, the solvent was removed by rotary evaporation under reduced pressure, 200mL of dichloromethane were added to the bottle containing the residue, washed 2 times with water (2X 20mL), the aqueous phase was extracted 2 times with dichloromethane (2X 20mL), and the organic phases were combined. Drying the organic phase by anhydrous magnesium sulfate, filtering, decompressing, spin-drying and removing the solvent to obtain a crude product, and separating by silica gel column chromatography to obtain an intermediate (2-amino-5- (sulfo-1, 3, 4-thiadiazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose). Wherein the structural formula of the raw material A is as follows:
s2, dissolving 2.54mmol (0.355g) of raw material B with the structural formula of the following formula B in 4 mL of thionyl chloride in a 50mL three-neck flask, carrying out reflux reaction at 60 ℃ for 2 hours, then fully spinning the reaction system, adding 1.0mmol of the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose), 10mL of dichloromethane and triethylamine (TEA, 1.0mmol), stirring at room temperature, slowly dropwise adding a dichloromethane solution of 1.2mmol of acyl chloride, stirring for three hours, carrying out TLC tracking reaction, after the reaction is completed, quenching with water, separating out an organic phase, spinning, and recrystallizing a crude product with isopropanol to obtain the acetyl glucose triazole benzamide compound. Wherein the structural formula of the raw material B is as follows:
the synthesis of the acetylglucosamine triazole benzamide compounds containing different R substituents can be performed according to the synthesis methods provided in the above embodiments 1 to 3, wherein the spectral data of part of the acetylglucosamine triazole benzamide compounds are shown in table 1.
TABLE 1
In addition, the in vitro growth rate method in the prior art is adopted to determine the bacteriostatic activity of the acetyl glucose triazole benzamide compound. Specifically, a potato dextrose agar medium (PDA medium: 200g of potato, 20g of agar, 20g of glucose and 1000mL of distilled water) was heated to a molten state (50 ℃ C.), 10mL of a liquid medicine (a liquid medicine containing 10-fold final concentration of acetylglucosamine triazole benzamide compounds) was poured into 90mL of the PDA medium, sufficiently shaken, uniformly poured into a petri dish with a diameter of 9cm, horizontally placed, and allowed to cool and solidify. And (3) punching a bacterium dish with the diameter of 4mm on the edge of the colony of the fresh pathogenic bacterium cultured for 4d by using a puncher, inversely placing the bacterium dish in the center of a PDA (personal digital assistant) plate containing a medicament, then placing the bacterium dish in a constant-temperature constant-humidity incubator at 27 ℃ for inverted culture, observing when a blank control colony grows to a position close to two thirds of the plate, measuring the diameter of the colony by using a cross method, and taking an average value. The blank was dosed with no agent, but contained the same concentration of solvent and 0.5% Tween 20, in triplicate for each treatment. The inhibition rate of the agent on the growth of hyphae is calculated by the following formula:
I(％)＝(C-T)/(C-0.4)×100％；
wherein I is the inhibition, C is the blank control diameter (cm), and T is the treatment diameter (cm). 5 samples were assayed, dose-inhibition curves were plotted, and the EC was calculated50The value is obtained. Each sample was assayed in triplicate and the results expressed as mean ± standard deviation.
Through the calculation, the method has the advantages that,EC of the acetyl-glucosotriazole benzamide compound synthesized in the above example 1 against pathogenic bacteria of potato late blight50It was 5.60. mu.g/mL.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (7)
1. The acetyl glucose triazole benzamide compound is characterized in that the structural general formula of the acetyl glucose triazole benzamide compound is shown as a formula I:
wherein R is a substituent at any position on the ring, specifically, R is H, 2-CH3、3-CH3、4-CH3、2-OCH3、3-OCH3、4-OCH3、2,3-(CH3)2、2,4-(CH3)2、2,5-(CH3)2、2,6-(CH3)2、2,3-(OCH3)2、2,4-(OCH3)2、2,5-(OCH3)2、2,6-(OCH3)2、2-F、3-F、4-F、2-Cl、3-Cl、4-Cl、2-Br、3-Br、2-NO2、3-NO2、4-NO2、2-CF3、3-CF3、4-CF3At least one of (1).
2. A method of synthesizing the acetylglucosamine triazole benzamide compound according to claim 1, comprising the steps of:
reacting 2 ', 3', 4 ', 6' -tetra-O-acetyl-alpha-D-bromoglucose with the raw material A to obtain an intermediate (2-amino-5- (sulfo-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose);
reacting the intermediate (2-amino-5- (sulfo-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose) with a raw material B to obtain the acetyl glucose triazole benzamide compound;
wherein, the structural formula of the raw material A is respectively shown as a formula A, and the structural formula of the raw material B is respectively shown as a formula B:
3. the method for synthesizing an acetylglucosamine triazole benzamide compound according to claim 2, wherein the step of reacting 2 ', 3', 4 ', 6' -tetra-O-acetyl- α -D-bromoglucose with the raw material a to obtain an intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl- β -D-glucose) specifically comprises:
mixing A, NaOH raw materials, distilled water and acetone to obtain a first mixed solution;
preparing 2 ', 3', 4 ', 6' -tetra-O-acetyl-alpha-D-bromoglucose into a solution, dropwise adding the solution into the first mixed solution for reaction, and then purifying and separating to obtain an intermediate (2-amino-5- (sulfo-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose).
4. The method for synthesizing an acetylglucosamine triazole benzamide compound according to claim 3, wherein in the step, 2 ', 3', 4 ', 6' -tetra-O-acetyl- α -D-bromoglucose is prepared as an acetone solution of 2 ', 3', 4 ', 6' -tetra-O-acetyl- α -D-bromoglucose.
5. The method for synthesizing the acetyl glucose triazole benzamide compound according to claim 2, wherein the step of reacting the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl- β -D-glucose) with the raw material B to obtain the acetyl glucose triazole benzamide compound specifically comprises:
mixing the intermediate (2-amino-5- (thio-1, 3, 4-triazolyl) -2 ', 3', 4 ', 6' -tetra-O-acetyl-beta-D-glucose), dichloromethane and triethylamine to obtain a second mixed solution;
and (3) after the raw material B and thionyl chloride are mixed and react completely, removing the thionyl chloride, preparing the residue into a solution, dropwise adding the solution into the second mixed solution for reaction, and then carrying out purification and separation to obtain the acetyl glucose triazole benzamide compound.
6. The method for synthesizing acetyl glucose triazole benzamide compound according to claim 5, wherein in the step, the residue is prepared as a dichloromethane solution of acyl chloride.
7. Use of the acetylglucosamine triazole benzamide compound as claimed in claim 1 for inhibiting potato late blight pathogenic bacteria.
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