Pyrimidine piperazinone compound containing amide as well as preparation method and application of pyrimidine piperazinone compound

Abstract

The invention discloses an amide-containing pyrimidine piperazinone bactericidal compound, a preparation method thereof and an application of the amide-containing pyrimidine piperazinone bactericidal compound in an agricultural bactericide. The structural general formula of the compound is as shown in a formula I in the specification. The compound is applied to prevention and treatment of diseases caused by fungi and oomycetes in agricultural production. The compound disclosed by the invention is novel in structure, simple in preparation method and broad in antibacterial spectrum, and has obvious antibacterial activity on various fungi and oomycetes; as a potential bactericide, the compound is used for preventing and treating diseases caused by plant pathogenic fungi and oomycetes. Formula I

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to fungicidal compounds of the amide-containing pyrimidine piperazine ketone class, their preparation methods, and their application in agricultural fungicides. Background Technology

[0002] With the continuous expansion of agricultural production, plant diseases pose a serious threat to food security and the stable production of cash crops. Diseases caused by plant pathogenic microorganisms, in particular, are characterized by rapid spread and difficulty in control, and have long relied on chemical pesticides for prevention and control. However, the long-term and large-scale use of existing pesticides has gradually revealed problems such as increased resistance, decreased efficacy, and ecological safety risks, urgently requiring the development of highly efficient and low-toxicity compounds with new structural types and potential new mechanisms of action.

[0003] Among numerous nitrogen-containing heterocyclic compounds, pyrimidine compounds exhibit broad bioactivity in both pesticides and pharmaceuticals due to their excellent biocompatibility and diverse substitution mechanisms. Meanwhile, piperazine structures, as important pharmacophores, can improve the physicochemical properties and bioavailability of molecules and are widely used in various bioactive molecules. Furthermore, structural units such as pyrazole rings, aryl groups, and small cyclic alkyl groups play a positive role in regulating molecular conformation and enhancing interactions with biological targets.

[0004] While some compounds containing pyrimidine or piperazine structures have been reported to possess certain biological activities in the prior art, research on the systematic combination and optimization of substituted pyrimidine or piperazine skeletons with different acyl or ketone structural units remains relatively limited. In particular, there is still room for further improvement in terms of structural diversity, activity stability, and applicability. Therefore, designing and synthesizing a novel class of substituted pyrimidine piperazine ketones, and systematically studying their preparation methods and potential applications, has significant theoretical and practical value. A search revealed no prior art reports of substituted pyrimidine piperazine ketones with structures resembling the general formula I of this invention. Summary of the Invention

[0005] This invention provides a class of pyrimidine piperazine ketone compounds, which, while maintaining the pyrimidine-piperazine core skeleton, achieve structural diversity by structurally controlling the substituents on the other side of the amide or ketone group and the pyrimidine cyclic aryl substituents.

[0006] In one aspect, this invention provides a substituted pyrimidine piperazine ketone compound, the general structural formula of which is shown in Formula I:

[0007] In Formula I:

[0008] R1 is a substituted organic group selected from one or a combination of the following groups: heterocyclic group, substituted aryl or heteroaryl-substituted alkyl acyl group, alicyclic-substituted acyl group. The heterocycle is selected from one or more of the following heterocycles: furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole, pyridine, pyrimidine, pyrazine, quinoline. Preferably, the heterocyclic group is a nitrogen-containing or sulfur-containing five- or six-membered heterocycle, wherein the five-membered nitrogen-containing heterocycle is preferably furan, thiophene, thiazole, imidazole, pyrazole, pyridine, pyrimidine, pyrazine, etc., and the heterocycle may be substituted by one or more substituents selected from fluorine and methyl; the substituted aryl or heteroaryl-substituted alkyl acyl group is substituted benzyl, phenethyl, phenylpropyl, substituted phenyl ether, etc., and the substituted group is selected from hydrogen, halogen (F, Cl, Br), hydroxyl, amino, cyano, nitro, C1-C 12 Alkyl, halogenated C1-C 12 One or more alkyl groups, etc.; the alicyclic group is substituted with cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0009] R2 is a substituted organic group selected from one or a combination of the following groups: heterocyclic group, substituted aryl group. The heterocycle is selected from one or more of the following heterocycles: furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole, pyridine, pyrimidine, pyrazine, quinoline. Preferably, the heterocyclic group is a nitrogen-containing or sulfur-containing five- or six-membered heterocycle, the five-membered nitrogen-containing heterocycle being preferably thiophene, pyridine, pyrimidine, etc., and the heterocycle may be substituted by one or more substituents selected from hydrogen and methyl; the substitution of the substituted aryl group is selected from hydrogen, halogen (F, Cl, Br), hydroxyl, amino, cyano, nitro, C1-C... 12 Alkyl, halogenated C1-C 12 One or more alkyl groups, etc.

[0010]

[0011] The substituent R2 in Formula I can be selected from: (H, 2-F, 3-F, 4-F, 3-Cl, 4-Cl, 2-CH3, 3-CH3, 4-CH3, 2-CF3, 3-CF3, 4-CF3, 2-OCH3, 3-OCH3, 4-OCH3, 2-OCF3, 3-OCF3, 4-OCF3, 2-CN, 3-CN, 4-CN, 2-NO2, 3-NO2, 4-NO2, 4-CH2CH3, 4-C(CH3)3, 2,3-2F, 2,4-2F, 2,5-2F)phenyl, 2-thiophene, 3-thiophene, 3-pyridine, 4-pyridine, 5-pyrimidine, piperonyl, etc.

[0012] The method for preparing the compound of formula I provided by the present invention includes the following steps:

[0013]

[0014] The compound shown in Formula II and the compound shown in Formula III are mixed in a solvent and subjected to a Suzuki coupling reaction to obtain the compound shown in Formula I; in Formulas II and III, the definitions of R1 and R2 are the same as in Formula I.

[0015] The above reaction needs to be carried out under catalytic conditions. The catalyst is preferably a 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex, tetra(triphenylphosphine)palladium, bis(triphenylphosphine)palladium chloride, etc. The above reaction is carried out in a mixed system of organic solvent / ethanol / water. The organic solvent includes 1,4-dioxane, tetrahydrofuran, acetonitrile, or toluene, etc. The above reaction needs to be carried out under alkaline conditions. The base is preferably K2CO3, Cs2CO3, Na2CO3, K3PO4, etc. The coupling reaction temperature is 80-120℃, preferably 100℃, and the reaction time is 12-24 hours, preferably 16-18 hours. In the above reaction, the molar ratio of the compound shown in Formula II to the compound shown in Formula III is 1:(1-2).

[0016] The present invention also provides applications of the compounds shown in Formula I above. In particular, the applications of the compounds shown in Formula I provided by the present invention are their use in controlling plant pathogenic fungi and oomycetes that harm agricultural production, and their use in the preparation of fungicides.

[0017] Preferably, the plant pathogens are *Fusarium wilt*, *Fusarium graminearum*, *Sclerotinia sclerotiorum*, *Gyromitra esculenta*, *Pseudomonas aeruginosa*, *Alternaria alternata*, *Colletotrichum gloeosporioides*, *Bakanae bakanae*, *Early blight*, *Pythium spp.*, *Phytophthora indicum ...

[0018] The compound shown in Formula I exhibits excellent antifungal (oomycete) activity against plant pathogens that cause serious harm in agricultural production. Preferably, the concentration of the active ingredient in the fungicide is 0.1 μg / mL to 500 μg / mL.

[0019] This invention discloses a novel, easily prepared substituted pyrimidine piperazine one compound. This class of compounds exhibits broad-spectrum inhibitory activity against fungi and oomycetes, particularly against pathogenic fungi such as wheat sheath blight, wheat scab, tomato gray mold, pepper anthracnose, and rice blast, as well as pathogenic oomycetes such as pepper phytophthora and fruit pyrethrum. Furthermore, it can serve as a potential fungicide for the control of these plant pathogenic fungi and oomycete diseases. Detailed Implementation

[0020] The present invention will be further described below with reference to specific embodiments, but the present invention is not limited to the following embodiments. Unless otherwise specified, the methods described are conventional methods. Unless otherwise specified, the raw materials are all available from publicly available commercial sources.

[0021] Example 1: Preparation of Compound I (IA-01)

[0022]

[0023] 1-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)-2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethyl-1-one (388.78 mg, 1.00 mmol) and phenylboronic acid (145.36 mg, 1.20 mmol) were added sequentially to a sealed 10 mL Shrek tube, followed by the addition of 10 mL of 1,4-dioxane to dissolve it. Then, an aqueous solution of sodium carbonate (105.99 mg, 1.00 mmol, dissolved in 1 mL of water) was added. Finally, 1,1′-bis(diphenylphosphine)ferrocene palladium dichloromethane dichloride complex [PdCl2(dppf)·CH2Cl2, 81.6 mg, 0.1 mmol] was added to the reaction system. After purging with nitrogen, the reaction mixture was heated under reflux for 16 hours. After the reaction was completed and cooled to room temperature, the mixture was extracted with ethyl acetate (3 × 20 mL), and the organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound IA-01 of formula I, with a yield of 58.41%.

[0024] By replacing phenylboronic acid with the corresponding substituted phenylboronic acid according to the above method, products IA-01 to IA-26 can be obtained.

[0025] Example 2: Preparation of Compound I (IB-01)

[0026]

[0027] To a sealed 10 mL Shrek tube, (4-(6-chloropyrimidin-4-yl)piperazin-1-yl)(4-(difluoromethyl)-1-methyl-1H-pyrrolo-3-yl) methyl ketone (355.78 mg, 1.00 mmol) and phenylboronic acid (145.36 mg, 1.20 mmol) were added sequentially, followed by 10 mL of 1,4-dioxane to dissolve it. Then, an aqueous solution of sodium carbonate (105.99 mg, 1.00 mmol, dissolved in 1 mL of water) was added. Finally, 1,1′-bis(diphenylphosphine)ferrocene palladium dichloromethane complex [PdCl2(dppf)·CH2Cl2, 81.6 mg, 0.1 mmol] was added to the reaction system. After purging with nitrogen, the reaction mixture was heated under reflux for 16 hours. After the reaction was completed and cooled to room temperature, the mixture was extracted with ethyl acetate (3 × 20 mL), and the organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound IA-01 of formula I, with a yield of 58.41%.

[0028] By replacing phenylboronic acid with the corresponding substituted phenylboronic acid according to the above method, products IB-01 to IB-20 can be obtained.

[0029] Example 3: Preparation of Compound I (IIA-09)

[0030]

[0031] In a 50 mL single-necked flask, phenylpropionic acid (150.18 mg, 1.00 mmol) was dissolved in 30 mL of anhydrous CH2Cl2. 1-hydroxybenzotriazole (HOBT, 162.14 mg, 1.20 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 230.04 mg, 1.20 mmol) were added sequentially at room temperature. The mixture was stirred for 1 hour to form an activated ester. 4-(piperazin-1-yl)-6-(m-tolyl)pyrimidine (305.21 mg, 1.20 mmol) was added to the reaction solution. The reaction system was continued to react at room temperature for 8 hours until the reaction was complete. Approximately 30 mL of water was added to the reaction solution to dissolve all the residue. The aqueous phase was extracted with CH2Cl2 (30 mL × 3). The organic phases were combined, dried over anhydrous magnesium sulfate, and some ethyl acetate was removed under reduced pressure. The resulting residue was purified by column chromatography to obtain compound II-09 of formula I, with a yield of 46.13%.

[0032] By replacing phenylpropionic acid with a substituted acid according to the above method, products IIA-01~IIA-31 and IIB-01~IIB-24 can be obtained.

[0033] Example 4: Preparation of Compound I (IIC-01)

[0034]

[0035] 1-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)-3-(2-fluorophenyl)prop-1-one (348.81 mg, 1.00 mmol) and phenylboronic acid (145.36 mg, 1.20 mmol) were added sequentially to a sealed 10 mL Shrek tube, followed by the addition of 10 mL of 1,4-dioxane to dissolve it. Then, an aqueous solution of sodium carbonate (105.99 mg, 1.00 mmol, dissolved in 1 mL of water) was added. Finally, 1,1′-bis(diphenylphosphine)ferrocene palladium dichloromethane dichloride complex (PdCl2(dppf)·CH2Cl2, 81.6 mg, 0.1 mmol) was added to the reaction system. After purging with nitrogen, the reaction mixture was heated under reflux for 16 h. After the reaction was completed and cooled to room temperature, the mixture was extracted with ethyl acetate (3 × 20 mL), and the organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound IIC-01 of formula I, with a yield of 83.54%.

[0036] By replacing phenylboronic acid with the corresponding substituted phenylboronic acid as described above, products IIC-01 to IIC-24 can be obtained.

[0037] Example 5: Preparation of Compound I (IVA-01)

[0038]

[0039] In a 50 mL single-necked flask, pyrazole (81.70 mg, 1.20 mmol) was dissolved in 20 mL of anhydrous DMF. Potassium carbonate (165.60 mg, 1.20 mmol) was added at room temperature and stirred for 10 minutes. 2-chloro-1-(4-(6-(m-tolyl)pyrimidin-4-yl)piperazin-1-yl)ethyl-1-one (330.82 mg, 1.00 mmol) was added to the reaction solution, and the mixture was reacted at room temperature for 12 h until complete. Approximately 30 mL of water was added to the reaction solution to dissolve all residues. The aqueous phase was extracted with ethyl acetate (30 mL × 3). The organic phases were combined, dried over anhydrous magnesium sulfate, and partially ethyl acetate was removed under reduced pressure. The resulting residue was purified by column chromatography to give compound IVA-01 of formula I, in 76.99% yield.

[0040] By replacing the pyrazole with the corresponding substituted aromatic ring according to the above method, products IVA-01 to IVA-30 can be obtained.

[0041] Example 6: Preparation of Compound I (IVB-01)

[0042]

[0043] 2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)-1-(4-(6-chloropyrimidin-4-yl)piperazin-1-yl)ethyl-1-one (406.79 mg, 1.00 mmol) and phenylboronic acid (145.36 mg, 1.20 mmol) were added sequentially to a sealed 10 mL Shrek tube, followed by the addition of 10 mL of 1,4-dioxane to dissolve it. Then, an aqueous solution of sodium carbonate (105.99 mg, 1.00 mmol, dissolved in 1 mL of water) was added. Finally, 1,1′-bis(diphenylphosphine)ferrocene palladium dichloromethane complex [PdCl2(dppf)·CH2Cl2, 81.6 mg, 0.1 mmol] was added to the reaction system. After purging with nitrogen, the reaction mixture was heated under reflux for 16 h. After the reaction was completed and cooled to room temperature, the mixture was extracted with ethyl acetate (3 × 20 mL), and the organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound IIC-01 of formula I, with a yield of 83.54%.

[0044] By replacing the pyrazole with the corresponding substituted aromatic ring according to the above method, products IVB-01 to IVB-24 can be obtained.

[0045] The appearance, melting point and yield of some of the compounds of general formula I of this invention are listed in Table 1, and the NMR data are listed in Table 2.

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] Example 7: Inhibitory activity of some compounds of Formula I against plant pathogenic fungi and oomycetes

[0066] The compounds of this invention were used to test the in vitro antibacterial activity against various plant pathogenic fungi and oomycetes. The tested fungal species included *Gyromyces lutea* (tomato gray mold), *Fusarium graminearum* (wheat scab), *Pseudomonas ulcerans* (apple rot), *Sclerotinia sclerotiorum* (rapeseed sclerotium), *Phytophthora capsici* (pepper phytophthora), *Phytophthora spp.* (soybean phytophthora), and *Pythium spp.* (melon fruit rot).

[0067] 10 mg of a portion of the compound of this invention was dissolved in 1 mL of dimethyl sulfoxide (DMSO) to prepare a stock solution of 10000 μg / mL. This stock solution was then further prepared into a drug-containing PDA medium with a concentration of 50 μg / mL using an equivalent amount of potato dextrose agar (PDA). The solution was poured into 9 cm diameter petri dishes, with three replicates for each agent and each pathogen. After the agar solidified, pre-activated mycelial pellets of the tested pathogen were inoculated and incubated in the dark at (25±2)℃. DMSO was used as a negative control, and sterile water as a blank control. All operations were performed under strict aseptic conditions in a laminar flow hood. After the blank control colonies had grown sufficiently, the diameter of each colony was measured using the cross-sectional method, and the average value was taken. The mycelial growth inhibition rate was calculated using the following formula:

[0068] Inhibition rate (%) = (Diameter of DMSO control colonies - Diameter of treated colonies) / (Diameter of DMSO control colonies - Diameter of mycelial cake (5 mm)) × 100%

[0069] Table 3 shows the in vitro antibacterial activity data of some compounds of this invention against pathogens at 50 μg / mL. The median inhibitory concentration (EC50) against pathogens is also included. 50The test results are shown in Table 4. This invention exhibits excellent inhibitory activity against a variety of plant pathogenic fungi and oomycetes, and can be used as a potential fungicide for the control of these plant pathogenic fungi and oomycetes.

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] As shown in Table 4, compounds IIC-01, IIC-03, IID-01, IID-02, IID-03, IID-04, and IVB-15 exhibited significant in vitro inhibitory activity against *Phytophthora capsici*, with the median inhibitory concentration (EC50) reaching [a certain value]. 50 The values ​​were all below 5 μg / mL, with compound IID-02 showing the best activity and EC50. 50 The concentration was below 3 μg / mL; compounds IVB-12 and IVB15 exhibited excellent in vitro antibacterial activity against various Pythium species (Pythium citrinum, Pythium terrestris, and Pythium kunmingense), with EC5 values ​​below 3 μg / mL. 50 The values ​​were all below 1 μg / mL; compounds V-09, IIB-01, IIB-21, IIB-23, IIC-03, and IIC-15 exhibited excellent in vitro antibacterial activity against *Botrytis cinerea*, the causal agent of tomato gray mold, with EC50 values ​​below 1 μg / mL. 50 Compounds IA-26, IIB-01, IIB-14, IIB-21, IIC-03, IIC-06, and IIC-15 exhibited excellent in vitro antibacterial activity against *Colletotrichum gloeosporioides* when their concentrations were below 1 μg / mL. 50 Compounds IA-26, IIB-01, and IIB-04 exhibited excellent in vitro antibacterial activity against rice blast fungus when their concentrations were below 5 μg / mL. 50 The values ​​were below 5 μg / mL, and IIB-01 showed good activity against all three.

[0077]

[0078]

[0079]

[0080]

[0081] Although the present invention has been described in detail above with general descriptions and specific embodiments, modifications or improvements can be made to it, which will be obvious to those skilled in the art. Therefore, all such modifications or improvements made without departing from the spirit of the present invention fall within the scope of protection claimed by the present invention.

Claims

1. An amide-containing pyrimidine piperazine one compound, characterized in that, The general structural formula of the compound is shown in Formula I: In Formula I: R ¹ The substituted organic group is selected from one or a combination of the following groups: heterocyclic group, substituted aryl or heteroaryl substituted alkyl acyl group, alicyclic substituted acyl group; The heterocycle is selected from one or more of the following heterocycles: furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole, pyridine, pyrimidine, pyrazine, quinoline; preferably, the heterocyclic group is a nitrogen-containing or sulfur-containing five-membered or six-membered heterocycle, the five-membered nitrogen-containing heterocycle is preferably furan, thiophene, thiazole, imidazole, pyrazole, pyridine, pyrimidine, pyrazine, etc., and the heterocycle may be substituted by one or more substituents, the substituents being selected from fluorine and methyl; The substituted aryl or heteroaryl substituted alkyl acyl group is substituted benzyl, phenethyl, phenylpropyl, or substituted phenyl ether, and the substitution is selected from hydrogen, halogen (F, Cl, Br), hydroxyl, amino, cyano, nitro, C1-C. 12 Alkyl, halogenated C1-C 12 One or more alkyl groups, etc.; the alicyclic group is substituted with cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; R2 is a substituted organic group selected from one or a combination of the following groups: heterocyclic group, substituted aryl group; The heterocycle is selected from one or more of the following heterocycles: furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole, pyridine, pyrimidine, pyrazine, quinoline; preferably, the heterocyclic group is a nitrogen-containing or sulfur-containing five-membered or six-membered heterocycle, the five-membered nitrogen-containing heterocycle is preferably thiophene, pyridine, or pyrimidine, and the heterocycle may be substituted by one or more substituents selected from hydrogen and methyl; The substitution of the substituted aryl group is selected from hydrogen, halogen (F, Cl, Br), hydroxyl, amino, cyano, nitro, C1-C. 12 Alkyl, halogenated C1-C 12 One or more alkyl groups.

2. The compound according to claim 1, wherein formula R1 is specifically selected from: , , , , , , , , , , , , , , , , , , , , ,, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , (H, 4-Cl)phenethyl, (H, 2-F, 3-F, 4-F, 2-Cl, 3-Cl, 4-Cl, 2-CH3, 3-CH3, 4-CH3, 2-CF3, 3-CF3, 4-CF3, 2-Br, 3-Br, 2-OCH3, 3-OCH3, 4-OCH3, 2-CN, 3-CN, 2-NO2, 3-NO2, 2, 3-2F)phenylpropyl; 2-pyridinylpropyl, 3-pyridinylpropyl, (H, 4-Cl)phenylbutyl; R2 is specifically selected from: (H, 2-F, 3-F, 4-F, 3-Cl, 4-Cl, 2-CH3, 3-CH3, 4-CH3, 2-CF3, 3-CF3, 4-CF3, 2-OCH3, 3-OCH3, 4-OCH3, 2-OCF3, 3-OCF3, 4-OCF3, 2-CN, 3-CN, 4-CN, 2-NO2, 3-NO2, 4-NO2, 4-CH2CH3, 4-C(CH3)3, 2,3-2F, 2,4-2F, 2,5-2F)phenyl, 2-thiophene, 3-thiophene, 3-pyridine, 4-pyridine, 5-pyrimidine, piperine.

3. In the compound according to claim 1, the R1 substituent is preferably selected from: , , Phenylacetyl; R2 substituent is selected from: H, 3-F, 4-CF3, 4-OCF3 phenyl.

4. A method for preparing the compound according to any one of claims 1-3, comprising the following steps: mixing the compound shown in formula II with the compound shown in formula III, and performing a condensation reaction to obtain the compound shown in formula I; In Equations II and III, R1 and R2 are the same as in Equation I.

5. The preparation method according to claim 4, characterized in that: The reaction is carried out under catalyst-free or alkaline catalytic conditions; the reaction is carried out in an alcohol solvent at a temperature of 18-50°C for a time of 0.5-24 hours.

6. The preparation method according to claim 5, characterized in that: The reaction is carried out under the conditions of a catalyst, an alkaline environment, and a solvent. The catalyst is a 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex, tetra(triphenylphosphine)palladium, and / or bis(triphenylphosphine)palladium chloride. The alkaline environment is K2CO3, Cs2CO3, Na2CO3, or K3PO4. The solvent is a mixture of organic solvent / ethanol / water, and the organic solvent is 1,4-dioxane, tetrahydrofuran, acetonitrile, or toluene. The reaction temperature is 80-120℃, the reaction time is 12-24 hours, and the molar ratio of the compound shown in Formula II to the compound shown in Formula III is 1:(1-2).

7. The use of the compound according to any one of claims 1-3 in the prevention and control of plant pathogenic fungi and oomycetes that harm agricultural production.

8. The application according to claim 7, characterized in that: The plant pathogens mentioned are one or more of the following: wheat sheath blight fungus, wheat scab fungus, tomato gray mold fungus, tomato early blight fungus, collodion anthracnose fungus, rice blast fungus, pepper blight fungus, soybean blight fungus, fruit blight fungus, ultimate blight fungus, Kunming blight fungus, and gorgeous blight fungus.

9. A bactericide, characterized in that: The active ingredient of the bactericide is one or more of the compounds described in any one of claims 1-3.

10. The bactericide according to claim 9, wherein the concentration of the active ingredient in the bactericide is 0.1 μg / mL to 500 μg / mL.

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