CN112341506A - Acetyl glucose thiadiazole benzamide compound and synthesis method and application thereof - Google Patents
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Abstract
The invention discloses an acetyl glucose thiadiazole 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 thiadiazole benzamide compound is as follows:
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to an acetyl glucose thiadiazole 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 embodiment of the invention aims to provide an acetyl glucose thiadiazole benzamide compound so as to solve the problems in the background technology.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
an acetyl glucose thiadiazole 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 aforementioned acetylglucose thiadiazole benzamide compound, which comprises the following steps:
reacting the raw material A with the raw material B to obtain an intermediate C;
reacting the intermediate C with a raw material D to obtain the acetylglucose thiadiazole benzamide compound;
the structural formulas of the raw material A, the raw material B, the intermediate C and the raw material D are respectively shown as a formula A, a formula B, a formula C and a formula D:
preferably, the step of reacting the raw material a with the raw material B to obtain the intermediate C specifically includes:
mixing B, NaOH raw materials, distilled water and acetone to obtain a first mixed solution;
and preparing the raw material A into a solution, dropwise adding the solution into the first mixed solution for reaction, and then purifying and separating to obtain an intermediate C.
Preferably, in the step, the raw material A is prepared into an acetone solution of the raw material A.
Preferably, the step of reacting the intermediate C with the raw material D to obtain the acetylglucose thiadiazole benzamide compound specifically includes:
mixing the intermediate C, dichloromethane and triethylamine to obtain a second mixed solution;
and (3) mixing the raw material D with thionyl chloride, reacting completely, removing the thionyl chloride, preparing the residue into triethylamine solution, dropwise adding the triethylamine solution into the second mixed solution, reacting, and purifying and separating to obtain the acetylglucose thiadiazole 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 acetylglucose thiadiazole benzamide compound in inhibiting potato late blight pathogenic bacteria.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
the acetyl glucose thiadiazole 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 thiadiazole benzamide compound, and the reaction route is as follows, wherein R is a substituent on a ring where R is located, and is specifically 4-CH3：
Specifically, the synthesis method comprises the following steps:
s1, synthesis of intermediate (2-amino-5- (thio-1, 3, 4-thiadiazolyl) -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 1.33g (0.01mol) of 2-amino-5-mercapto-1, 3, 4-thiadiazole 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).
S2, dissolving 2.54mmol (0.345g) of raw material D with the structural formula of the following formula D 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-thiadiazolyl) -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 acetylglucose thiadiazole benzamide compound. Wherein the structural formula of the raw material D is as follows:
example 2
The material embodiment provides a synthesis method of an acetyl glucose thiadiazole benzamide compound, which has the following reaction route, wherein R is a substituent on a ring where the R is located, and specifically is 4-F:
specifically, the synthesis method comprises the following steps:
s1, synthesis of intermediate (2-amino-5- (thio-1, 3, 4-thiadiazolyl) -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 1.33g (0.01mol) of 2-amino-5-mercapto-1, 3, 4-thiadiazole 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).
S2, dissolving 2.54mmol (0.355g) of raw material D with the structural formula shown as the following formula D 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-thiadiazolyl) -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 acetylglucose thiadiazole benzamide compound. Wherein the structural formula of the raw material D is as follows:
example 3
The material embodiment provides a synthesis method of an acetyl glucose thiadiazole benzamide compound, which has the following reaction route, wherein R is a substituent on a ring where the R is located, and is specifically 4-Br:
specifically, the synthesis method comprises the following steps:
s1, synthesis of intermediate (2-amino-5- (thio-1, 3, 4-thiadiazolyl) -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 1.33g (0.01mol) of 2-amino-5-mercapto-1, 3, 4-thiadiazole 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).
S2, dissolving 2.54mmol (0.508g) of raw material D with the structural formula shown as the following formula D 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-thiadiazolyl) -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 acetylglucose thiadiazole benzamide compound. Wherein the structural formula of the raw material D is as follows:
the synthesis of the acetyl bromo-glucose thiadiazole 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 acetyl glucose thiadiazole 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 acetylglucose thiadiazole benzamide compound. Specifically, a potato dextrose agar medium (PDA medium: 200g of potato, 20g of agar, 20g of glucose and 1000mL of distilled water) is heated to a molten state (50 ℃), 10mL of a liquid medicine (a liquid medicine containing 10 times of the final concentration of the acetylglucose thiadiazole benzamide compound) is poured into 90mL of the PDA medium, the mixture is fully shaken, and the mixture is uniformly poured into a culture dish with the diameter of 9cm, horizontally placed and cooled and solidified. 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 calculation, the EC of the acetylglucose thiadiazole benzamide compound synthesized in the example 1 on potato late blight pathogenic bacteria506.02. 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 (8)
1. The acetyl glucose thiadiazole benzamide compound is characterized by having a structural general formula as shown in formula I:
wherein R is a substituent at any position on the ring.
2. The acetylglucose thiadiazole benzamide compound according to claim 1, wherein 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).
3. A method for synthesizing the acetylglucosamine thiadiazole benzamide compound according to any one of claims 1-2, which comprises the following steps:
reacting the raw material A with the raw material B to obtain an intermediate C;
reacting the intermediate C with a raw material D to obtain the acetylglucose thiadiazole benzamide compound;
the structural formulas of the raw material A, the raw material B, the intermediate C and the raw material D are respectively shown as a formula A, a formula B, a formula C and a formula D:
4. the method for synthesizing the acetylglucose thiadiazole benzamide compound according to claim 3, wherein the step of reacting the raw material A with the raw material B to obtain the intermediate C specifically comprises:
mixing B, NaOH raw materials, distilled water and acetone to obtain a first mixed solution;
and preparing the raw material A into a solution, dropwise adding the solution into the first mixed solution for reaction, and then purifying and separating to obtain an intermediate C.
5. The method for synthesizing acetylglucose thiadiazole benzamide compound according to claim 4, wherein in the step (A), raw material A is prepared into an acetone solution of raw material A.
6. The method for synthesizing the acetylglucose thiadiazole benzamide compound according to claim 3, wherein the step of reacting the intermediate C with the raw material D to obtain the acetylglucose thiadiazole benzamide compound specifically comprises:
mixing the intermediate C, dichloromethane and triethylamine to obtain a second mixed solution;
and (3) mixing the raw material D with thionyl chloride, reacting completely, removing the thionyl chloride, preparing the residue into a solution, dropwise adding the solution into the second mixed solution, reacting, and purifying and separating to obtain the acetyl bromo glucose thiadiazole benzamide compound.
7. The method for synthesizing acetylglucose thiadiazole benzamide compound according to claim 6, wherein in the step (A), the residue is prepared as a dichloromethane solution of acid chloride.
8. Use of the acetylglucosamine thiadiazole benzamide compound as defined in any one of claims 1-2 for inhibiting potato late blight pathogenic bacteria.
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| CN113896722A (en) * | 2021-09-28 | 2022-01-07 | 内蒙古民族大学 | Benzamide compound containing thiadiazole group and preparation method and application thereof |
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| WO2009037485A1 (en) * | 2007-09-20 | 2009-03-26 | Prolysis Ltd | Antibacterial agents |
| CN105828610A (en) * | 2013-10-22 | 2016-08-03 | 美国陶氏益农公司 | Pesticidal compositions and related methods |
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| CN113896722A (en) * | 2021-09-28 | 2022-01-07 | 内蒙古民族大学 | Benzamide compound containing thiadiazole group and preparation method and application thereof |
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