CN110622973B

CN110622973B - Application of 1-aryl-4-pyridone compounds

Info

Publication number: CN110622973B
Application number: CN201911075725.6A
Authority: CN
Inventors: 孙然锋; 俞秀强; 朱新月; 周杨; 李庆林
Original assignee: Hainan University
Current assignee: Hainan University
Priority date: 2019-11-06
Filing date: 2019-11-06
Publication date: 2020-11-10
Anticipated expiration: 2039-11-06
Also published as: CN110622973A

Abstract

The invention provides application of a 1-aryl-4-pyridone compound and provides application of a compound with a structure shown in a formula (I) in inhibiting activity of phytopathogen. The compound with the structure shown in the formula (I) has excellent broad-spectrum antifungal activity on plant pathogenic fungi in agricultural production, and simultaneously has control effect on bacterial diseases of crops. In vivo bioassay proves that the structural compound shown in the formula (I) realizes the prevention and treatment effects of more than 95 percent on cucumber downy mildew, cucumber target spot, wheat scab and tomato gray mold. Meanwhile, the mango postharvest preservation experiment result shows that the compound can effectively control mango postharvest diseases and prolong the mango preservation time. In addition, the compound can be found to be effective in controlling bacterial leaf blight of rice in a pot experiment, which is more effective than zhongshengmycin serving as a commercial bactericide. In conclusion, the 1-aryl-4-pyridone derivative shown in the formula (I) has broad-spectrum activity against plant pathogenic fungi and bacteria, and is a lead compound with wide biological activity.

Description

Application of 1-aryl-4-pyridone compounds

Technical Field

The invention relates to the technical field of biology, in particular to application of a 1-aryl-4-pyridone compound.

Background

For decades, phytopathogenic fungi have caused serious damage to crop production. Over 8000 known fungal species can cause plant disease. Diseases caused by plant pathogenic fungi are important factors for restricting agricultural production in China, and the diseases are often generated in a large scale and cause huge loss on agricultural production in China. The existing agricultural pesticide mainly comprises chemical synthetic pesticides, chemical bactericide pesticides are required to be produced and used by China for more than 80 ten thousand tons every year, the loss caused by diseases is reduced to a great extent by using the pesticides, but a series of problems and hidden dangers are caused by the large-scale use of the chemical pesticides, such as: pesticide residue, environmental pollution, ecological balance damage, drug resistance generation and the like. In the control of agricultural diseases, many strains of phytopathogenic fungi that are resistant or cross-resistant to some commonly used pesticides (e.g., carbendazim, thiophanate-methyl, thiabendazole, benomyl, metalaxyl, oxadixyl, azoxystrobin, kresoxim-methyl, pyraclostrobin, trifloxystrobin, famoxadone, etc.) have been found to be up to several hundred times more resistant. The development of these resistances has caused a great hindrance to the production of agricultural chemicals and the control of agricultural diseases, and therefore, the development of novel fungicides is urgently required to solve these problems.

Disclosure of Invention

In view of the above, the technical problem to be solved by the present invention is to provide a compound having excellent broad-spectrum antifungal activity against plant pathogenic fungi in agricultural production and simultaneously having control effect against bacterial diseases of crops.

The invention provides application of a structural compound shown in a formula (I) in inhibiting the activity of phytopathogen;

in the formula, R¹Selected from H, hydroxyl or alkoxy of C1-C10; r²Is C1-C10 alkyl; r³An alkyl group selected from H, C1 to C10; x is selected from alkyl of H, C1-C10, C6-An aryl group having C30, a heterocyclic group having C6-C30.

Preferably, said R is¹Selected from H, hydroxyl or alkoxy of C1-C6; r²Is C1-C6 alkyl; r³Selected from H, C1-C6 alkyl; x is selected from H, C1-C6 alkyl, C6-C20 aryl and C6-C30 aryl heterocyclic group.

Preferably, said R is¹Selected from H, hydroxy or methoxy; r²Is methyl or ethyl; r³Selected from H or methyl; x is selected from H, methyl or one of the following a-1-a-29 structures:

preferably, the phytopathogen is a phytopathogenic fungus or a phytopathogenic bacterium.

Preferably, the phytopathogenic fungus is selected from the group consisting of mango stem rot (Botryodiplodia theobromae), Fusarium graminearum (Fusarium graminearum), dragon fruit canker (neospora dimyrium), rice blast (Pyricularia oryzae), banana wilt (Fusarium oxysporum), banana anthracnose (colletotrichum musae), Phytophthora capsici (Phytophthora capsici), Botrytis cinerea (Botrytis cinerea), Sclerotinia sclerotiorum (sclerotiorum), cucumber downy mildew (Pseudoperonospora cubensis), cucumber target spot (Corynespora cassiacola) and rice sheath blight (Rhizoctonia solani) and the plant pathogen is Xanthomonas flava xanthosa pvaeae.

The invention provides application of a compound with a structure shown in a formula (I) in preventing and treating plant diseases caused by phytopathogens;

in the formula (I), the compound is shown in the specification,R¹selected from H, hydroxyl or alkoxy of C1-C10; r²Is C1-C10 alkyl; r³An alkyl group selected from H, C1 to C10; x is selected from H, C1-C10 alkyl, C6-C30 aryl and C6-C30 heterocyclic radical.

Preferably, the plant disease is selected from the group consisting of mango base rot, wheat scab, dragon fruit canker, rice blast, banana wilt, banana anthracnose, phytophthora capsici leonian, tomato gray mold, sclerotinia rot of colza, cucumber downy mildew, cucumber target spot, rice sheath blight, and rice bacterial leaf blight.

The invention provides application of a compound with a structure shown in a formula (I) in preparation of an inhibitor for inhibiting activity of phytopathogen;

in the formula, R¹Selected from H, hydroxyl or alkoxy of C1-C10; r²Is C1-C10 alkyl; r³An alkyl group selected from H, C1 to C10; x is selected from H, C1-C10 alkyl, C6-C30 aryl and C6-C30 heterocyclic radical.

The invention provides a plant pathogenic bacteria activity inhibitor, which comprises a structural compound shown in a formula (I);

The invention provides a method for preventing and treating plant diseases, which applies the inhibitor in the technical scheme.

Compared with the prior art, the invention provides the application of the structural compound shown in the formula (I) in inhibiting the activity of phytopathogen. The compound with the structure shown in the formula (I) has excellent broad-spectrum antifungal activity on plant pathogenic fungi in agricultural production, and simultaneously has control effect on bacterial diseases of crops.

In vivo bioassay proves that the structural compound shown in the formula (I) realizes the prevention and treatment effects of more than 95 percent on cucumber downy mildew, cucumber target spot, wheat scab and tomato gray mold. Meanwhile, the mango postharvest preservation experiment result shows that the structural compound shown in the formula (I) can effectively control mango postharvest diseases and prolong the mango preservation time. In addition, the compound can be found to be effective in controlling bacterial leaf blight of rice in a pot experiment, which is more effective than zhongshengmycin serving as a commercial bactericide. In conclusion, the 1-aryl-4-pyridone derivative shown in the formula (I) has broad-spectrum activity against plant pathogenic fungi and bacteria, and is a lead compound with wide biological activity.

Detailed Description

The invention provides an application of 1-aryl-4-pyridone compounds, and persons skilled in the art can use the contents to appropriately modify other related applications to realize the application. It is expressly intended that all such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the scope of the invention. While the methods and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications in the methods and applications described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of this invention without departing from the spirit and scope of the invention.

in the formula, R¹Selected from H, hydroxyl or alkoxy of C1-C10; h, hydroxyl or alkoxy of C1-C6 is preferred; more preferably H, hydroxy or alkoxy of C1-C3; most preferably H, hydroxy, methoxy or ethoxy; h, hydroxyl and methoxy are particularly preferred.

R²Is C1-C10 alkyl;preferably C1-C6 alkyl; more preferably a C1-C3 alkyl group; most preferably methyl or ethyl.

R³An alkyl group selected from H, C1 to C10; preferably H, C1 to C6 alkyl; more preferably H, C1 to C3 alkyl; most preferably H, methyl or ethyl; h or methyl is particularly preferred.

X is selected from H, C1-C10 alkyl, C6-C30 aryl and C6-C30 heterocyclic radical. Preferably, X is selected from H, C1-C6 alkyl, C6-C20 aryl, and C6-C30 aryl heterocyclic group, more preferably, X is selected from H, methyl or one of the following a-1-a-29 structures:

in a part of preferable embodiments of the invention, the structural compound shown in the formula (I) is specifically a structure shown in the following I-1 to I-37 (the following examples are abbreviated as 1 to 37):

the invention also provides a preparation method of the compound with the structure shown in the formula (I), which comprises the following steps:

heating pyrone with a structure shown in a formula (II) and amine compound with a structure shown in a formula (III) in water for reflux reaction to obtain a compound with a structure shown in a formula (I); or

Reacting pyrone with a structure shown in a formula (II) and amine compound with a structure shown in a formula (III) in a mixed solution of water, ethanol and hydrochloric acid under high pressure and heating to obtain a compound with a structure shown in a formula (I);

formula (II); X-NH₂Formula (III);

One preparation method of the compound with the structure shown in the formula (I) provided by the invention preferably comprises the following steps: heating pyrone with a structure shown in a formula (II) and amine compound with a structure shown in a formula (III) in water for reflux reaction to obtain a compound with a structure shown in a formula (I).

The method specifically comprises the following steps: dissolving pyrone with the structure of formula (II) in water, adding excessive amine with the structure of formula (III), and refluxing the reaction mixture to obtain the 1-aryl-4-pyridone derivative

Wherein the heating reflux reaction is carried out for overnight; preferably 10-15 h;

after the reflux reaction, ammonia and solvent were also removed under reduced pressure and the mixture was cooled to room temperature overnight. The solid product obtained was recrystallized from a 50% water/methanol mixture in the presence of activated carbon. The activated carbon was filtered off and the product was concentrated under reduced pressure. The final product was dried in a desiccator with phosphorous pentoxide.

The invention provides a compound with a structure shown in formula (I), wherein another preparation method preferably comprises the following steps:

and (2) reacting pyrone with a structure shown in a formula (II) and amine compound with a structure shown in a formula (III) in a mixed solution of water, ethanol and hydrochloric acid under high pressure and heating to obtain the compound with the structure shown in the formula (I).

Dissolving pyrone with a structure shown in formula (II) and amine with a structure shown in formula (III) in an acidic mixed solution of water, ethanol and hydrochloric acid, and heating the reaction mixture in a high-pressure reaction kettle for reaction.

According to the invention, the pressure of the high-pressure heating reaction is 0.15MPa, and the heating temperature is 160-170 ℃; the reaction time is 10-12 h.

The pyrone of formula (II) is not limited in the source, and may be commercially available or prepared by methods known to those skilled in the art.

According to the invention, the phytopathogen is a phytopathogenic fungus or a phytopathogenic bacterium.

Specifically, the phytopathogenic fungi include, but are not limited to, mango stem rot (Botryodiplodia theobroma), gibberella zeae (Fusarium graminearum), dragon fruit canker (neospora dimyrium), Pyricularia oryzae (Pyricularia oryzae), banana Fusarium oxysporum (Fusarium oxysporum), banana anthracnose (Colletotrichum muscae), Phytophthora capsici (Phytophthora capsici), Botrytis cinerea (Botrytis cinerea), Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), cucumber downy mildew (Pseudoperonospora cubensis), cucumber target spot (Corynespora cassiaca), and rice sheath blight (Rhizoctonia solani) including, but not limited to, Xanthomonas oryzae.

According to the present invention, the plant diseases include, but are not limited to, mango base rot, wheat scab, dragon fruit canker, rice blast, banana wilt, banana anthracnose, phytophthora capsici, tomato gray mold, sclerotinia rot of colza, cucumber downy mildew, cucumber target spot, rice sheath blight and rice bacterial leaf blight.

The compound with the structure can be used as an inhibitor for inhibiting the activity of phytopathogen, an antibacterial agent and the like.

The structural compound shown in the formula (I) is clearly described in the invention, and the description is omitted. The inhibitor may comprise the above compound and conventional adjuvants and ingredients.

The method for preventing and treating the plant diseases comprises the steps of applying the inhibitor in the technical scheme; the above application method is preferably embodied as follows:

spray treatment: the sprayer is a crop sprayer with a spray pressure of 1.5kg/cm²The amount of the sprayed liquid is about 675L/hm². After the test material is treated, the test material is naturally dried and inoculated with pathogenic bacteria after 20-24 hours.

The invention provides application of a structural compound shown in a formula (I) in inhibiting activity of phytopathogen. The compound with the structure shown in the formula (I) has excellent broad-spectrum antifungal activity on plant pathogenic fungi in agricultural production, and simultaneously has control effect on bacterial diseases of crops. In vivo bioassay proves that the structural compound shown in the formula (I) realizes the prevention and treatment effects of more than 95 percent on cucumber downy mildew, cucumber target spot, wheat scab and tomato gray mold. Meanwhile, the mango postharvest preservation experiment result shows that the structural compound shown in the formula (I) can effectively control mango postharvest diseases and prolong the mango preservation time. In addition, the compound can be found to be effective in controlling bacterial leaf blight of rice in a pot experiment, which is more effective than zhongshengmycin serving as a commercial bactericide. In conclusion, the 1-aryl-4-pyridone derivative shown in the formula (I) has broad-spectrum activity against plant pathogenic fungi and bacteria, and is a lead compound with wide biological activity.

In order to further illustrate the present invention, the following examples are provided to describe the application of the 1-aryl-4-pyridone compounds provided by the present invention in detail.

Example 1 preparation of target compounds 5, 6.

Maltol (10mmol) was dissolved in 15mL of water and excess aqueous ammonia (6mL) was added. The reaction mixture was refluxed for 10 hours, the ammonia and solvent were removed under reduced pressure, and the mixture was cooled to room temperature overnight. The solid product obtained was recrystallized from a 50% water/methanol mixture in the presence of activated carbon. Filtering to obtain active carbon, and concentrating under reduced pressureAnd (3) obtaining the product. The final product was dried in a desiccator with phosphorous pentoxide. The aimed compound 5(1.01g, 7.93mmol) was obtained. Grey solid, mp 285-287 ℃ yield 79%.¹H NMR(600MHz,DMSO-d₆)8.01(d,J＝5.5Hz,1H,pyridinone),6.33(d,J＝5.5Hz,1H,pyridinone),2.23(s,3H,CH₃).¹³C NMR(150MHz,DMSO-d₆)172.6,154.6,149.2,143.0,113.6,14.0.ESI-HRMS:m/z[M+H]⁺calcd.for[C₆H₈NO₂]:126.1243；found:126.1238.

Synthesis of target compound 6 reference was made to the synthesis of target compound 5.

Target compound 6: white solid, mp 259-.¹H NMR(600MHz,DMSO-d₆)7.55(d,J＝7.2Hz,1H,pyridinone),6.08(d,J＝7.2Hz,1H,pyridinone),3.62(s,3H,N-CH₃),2.26(s,3H,pyridinone-CH₃).¹³C NMR(150MHz,DMSO-d₆)168.7,145.3,138.0,129.4,110.2,40.9,11.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₇H₁₀NO₂]:139.1509；found:139.1491.

Example 2: preparation of target compounds 7-37.

Maltol (10mmol) and excess aniline (15mmol) were added to an acidic solution of 18.0mL water, 0.4mL HCl and 2.0mL ethanol (pH 5). And the resulting mixture was heated at 160 ℃ for 12 hours in an autoclave. After completion of the reaction, the reaction mixture was adjusted to pH 7 using sodium hydroxide solution (2N), and the product was collected by filtration. Finally, by silica gel column Chromatography (CH)₂Cl₂：CH₃OH ═ 50:1) to give the title compound 7(1.67g, 8.3 mmol). White solid, mp 206-.¹H NMR(500MHz,Chloroform-d)7.53(m,J＝4.8,1.8Hz,3H,Ph),7.30(d,J＝7.3Hz,1H,pyridinone),7.29–7.26(m,2H,Ph),6.46(d,J＝7.3Hz,1H,pyridinone),2.10(s,3H,CH₃).¹³C NMR(125MHz,Chloroform-d)170.3,145.8,141.9,137.6,130.0,129.7,128.5,126.9,111.0,13.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₂NO₂]:202.0863；found:202.0858.

Synthesis of target Compounds 8-37 reference was made to the synthesis of target Compound 7.

Target compound 8: grey solid, mp 311-.¹H NMR(600MHz,DMSO-d₆)7.48(d,J＝7.3Hz,1H,pyridinone),7.23–7.20(m,2H,Ph),6.89–6.86(m,2H,Ph),6.18(d,J＝7.3Hz,1H,pyridinone),1.95(s,3H,CH₃).¹³C NMR(150MHz,DMSO-d₆)169.4,157.8,145.0,138.2,133.1,129.3,128.0,115.8,110.6,13.3.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₂NO₃]:218.0812；found:218.0807.

Target compound 9: brown solid, mp 185-.¹H NMR(500MHz,Chloroform-d)7.60–7.45(m,1H,pyridinone),7.22–7.09(m,3H,Ph),6.50(d,J＝6.3Hz,1H,pyridinone),2.10(s,3H,CH₃).¹³C NMR(125MHz,Chloroform-d)171.0,158.2(d,J＝254.7Hz),145.7,138.0,131.7,128.8,118.7,112.7(d,J＝19.8Hz),111.9,12.4.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₀F₂NO₂]:238.0674；found:238.0679.

Target compound 10: light yellow solid, mp 256-.¹H NMR(500MHz,Chloroform-d)7.28(d,J＝8.0Hz,2H,Ph),7.24(d,J＝2.5Hz,1H,pyridinone),7.11(d,J＝8.2Hz,2H,Ph),6.42(d,J＝7.3Hz,1H,pyridinone),2.42(s,3H,Ph-CH₃),2.07(s,3H,pyridinone-CH₃).¹³C NMR(125MHz,Chloroform-d)170.2,145.8,139.8,139.4,137.6,130.5,128.8,126.6,110.9,21.3,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₃H₁₄NO₂]:216.1019；found:216.1023.

Target compound 11: off-white solid, mp 264-.¹H NMR(600MHz,DMSO-d₆)7.85(d,J＝8.3Hz,2H,Ph),7.75(d,J＝7.5Hz,2H,Ph),7.60(d,J＝7.3Hz,1H,pyridinone),7.55(d,J＝8.3Hz,2H,Ph),7.51(t,J＝7.6Hz,2H,Ph),7.42(t,J＝7.3Hz,1H,Ph),6.23(d,J＝7.3Hz,1H,pyridinone),2.02(s,3H,CH₃).¹³C NMR(150MHz,DMSO-d₆)169.7,145.1,140.9,137.9,129.1,128.6,128.0,127.8,127.5,126.9,110.9,13.4.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₈H₁₆NO₂]:278.1176；found:278.1182.

Target compound 12: off-white solid, mp 191-.¹H NMR(500MHz,Chloroform-d)7.31–7.28(m,2H,Ph),7.27(s,1H,pyridinone),7.25–7.20(m,2H,Ph),6.46(d,J＝7.3Hz,1H,pyridinone),2.10(s,3H,CH₃).¹³C NMR(125MHz,Chloroform-d)170.4,163.7,162.7(d,J＝251.0Hz),145.8,137.6(d,J＝3.4Hz),128.8(d,J＝8.9Hz),117.2,117.0(d,J＝23.1Hz),111.2,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₁FNO₂]:220.0768；found:220.0765.

Target compound 13: white solid, mp 210-.¹H NMR(600MHz,DMSO-d₆)7.63(d,J＝8.6Hz,2H,Ph),7.55(d,J＝7.3Hz,1H,pyridinone),7.51(d,J＝8.6Hz,2H,Ph),6.21(d,J＝7.3Hz,1H,pyridinone),1.96(s,3H,CH₃).¹³C NMR(150MHz,DMSO-d₆)169.7,145.0,140.4,137.9,133.7,129.6,129.0,128.5,111.0,13.3.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₁ClNO₂]:236.0473；found:236.0479.

Target compound 14: white solid, mp 216-.¹H NMR(600MHz,DMSO-d₆)7.76(d,J＝8.6Hz,2H,Ph),7.54(d,J＝7.3Hz,1H,pyridinone),7.44(d,J＝8.6Hz,2H,Ph),6.21(d,J＝7.3Hz,1H,pyridinone),1.96(s,3H,CH₃).¹³C NMR(150MHz,DMSO-d₆)169.7,140.8,137.8,132.5,129.3,128.4,122.2,118.5,111.0,13.3.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₁BrNO₂]:279.9968；found:279.9971.

Target compound 15: brown solid, mp 121-.¹H NMR(500MHz,Chloroform-d)7.33(d,J＝7.5Hz,2H,Ph),7.28(d,J＝6.8Hz,1H,pyridinone),7.16(d,J＝7.6Hz,2H,Ph),6.44(d,J＝6.6Hz,1H,pyridinone),2.73(q,J＝7.6Hz,2H,CH₂),2.09(s,3H,pyridinone-CH₃),1.29(t,J＝7.6Hz,3H,CH₃).¹³C NMR(125MHz,Chloroform-d)170.2,145.7,139.5,137.6,129.3,128.8,126.7,110.9,28.6,15.5,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₄H₁₆NO₂]:230.1176；found:230.1184.

Target compound 16: a red-brown solid, mp 146-.¹H NMR(500MHz,Chloroform-d)7.30(s,3H,Ph and pyridinone),7.15(s,2H,Ph),6.44(s,1H,pyridinone),2.66(t,J＝6.9Hz,2H,CH₂),2.09(s,3H,pyridinone-CH₃),1.72–1.64(m,2H,CH₂),0.97(t,J＝6.9Hz,3H,CH₃).¹³C NMR(125MHz,Chloroform-d)170.1,145.6,144.5,139.4,137.6,129.8,128.7,126.5,110.8,37.6,24.4,13.8,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₅H₁₈NO₂]:244.1332；found:244.1335.

Target compound 17: light brown solid, mp 193-.¹H NMR(500MHz,Chloroform-d)7.35(d,J＝7.9Hz,2H,Ph),7.28(d,J＝7.1Hz,1H,pyridinone),7.16(d,J＝8.0Hz,2H,Ph),6.44(d,J＝7.0Hz,1H,pyridinone),2.99(hept,J＝6.9Hz,1H,CH),2.10(s,3H,pyridinone-CH₃),1.29(d,J＝6.9Hz,6H,Ph-CH(CH ₃)₂).¹³C NMR(125MHz,Chloroform-d)170.2,150.6,145.7,139.5,137.6,128.9,127.9,126.7,110.9,34.0,24.0,13.8.ESI-HRMS:m/z[M+Na]⁺calcd.for[C₁₅H₁₇NO₂Na]:266.1151；found:266.1155.

Target compound 18: a red-brown solid, mp 167-.¹H NMR(600MHz,Chloroform-d)7.32(s,3H,Ph and pyridinone),7.16(s,2H,Ph),6.45(s,1H,pyridinone),2.70(t,J＝6.9Hz,2H,CH₂),2.10(s,3H,pyridinone-CH₃),1.65(s,2H,CH₂),1.43–1.36(m,2H,CH₂),0.96(t,J＝6.9Hz,3H,CH₃).¹³C NMR(150MHz,Chloroform-d)170.1,145.6,144.7,139.4,137.6,129.7,128.8,126.5,110.8,35.2,33.4,22.3,13.9,13.6.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₆H₂₀NO₂]:258.1489；found:258.1485.

Target compound 19: white solid, mp 197 ℃ and 198 ℃ in 74% yield.¹H NMR(500MHz,Chloroform-d)7.51(d,J＝8.4Hz,2H,Ph),7.29(d,J＝7.2Hz,1H,pyridinone),7.17(d,J＝8.4Hz,2H,Ph),6.44(d,J＝7.2Hz,1H,pyridinone),2.10(s,3H,pyridinone-CH₃),1.37(s,9H,Ph-C(CH ₃)₃).¹³C NMR(125MHz,Chloroform-d)170.2,153.0,145.7,139.3,137.7,128.8,126.9,126.4,110.9,35.0,31.4,13.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₆H₂₀NO₂]:258.1489；found:258.1491.

Target compound 20: the brown solid was mp 214-.¹H NMR(500MHz,Chloroform-d)7.28(d,J＝7.0Hz,1H,pyridinone),7.06(d,J＝8.1Hz,2H,Ph),6.72(d,J＝8.1Hz,2H,Ph),6.42(d,J＝6.8Hz,1H,pyridinone),3.02(s,6H,N-(CH ₃)₂),2.09(s,3H,pyridinone-CH₃).¹³C NMR(125MHz,Chloroform-d)170.0,150.7,145.6,138.2,130.6,129.5,127.3,112.2,110.7,40.5,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₄H₁₇N₂O₂]:245.1285；found:245.1282.

Target compound 21: brown solid, mp 188-.¹H NMR(500MHz,Chloroform-d)7.81(s,1H,Ph),7.78–7.68(m,1H,Ph),7.59(s,1H,pyridinone),7.57–7.49(m,1H,Ph),7.29(d,J＝10.9Hz,1H,Ph),6.49(s,1H,pyridinone),2.12(s,3H,CH₃).¹³C NMR(125MHz,Chloroform-d)170.5,146.0,142.2,137.3,132.6(q,J＝33.2Hz),130.8,130.4,128.2,126.5(d,J＝3.6Hz),124.1,124.0(d,J＝3.6Hz),111.6,13.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₃H₁₁F₃NO₂]:270.0736；found:270.0737.

Target compound 22: off-white solid, mp 185-.¹H NMR(500MHz,Chloroform-d)7.52(d,J＝8.7Hz,1H,Ph),7.44(t,J＝7.8Hz,1H,Ph),7.31(d,J＝7.3Hz,1H,pyridinone),7.23(t,J＝1.9Hz,1H,Ph),7.06(d,J＝8.8Hz,1H,Ph),6.46(d,J＝7.3Hz,1H,pyridinone),2.09(s,3H,CH₃),1.34(s,9H,Ph-C(CH ₃)₃).¹³C NMR(125MHz,Chloroform-d)170.2,153.8,145.8,141.7,137.6,129.6,128.6,126.6,123.9,123.8,110.9,35.1,31.3,13.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₆H₂₀NO₂]:258.1489；found:258.1482.

Target compound 23: off-white solid, mp 229-.¹H NMR(500MHz,Chloroform-d)7.63(d,J＝8.2Hz,2H,Ph),7.30(d,J＝8.3Hz,2H,Ph),7.24(s,1H,pyridinone),6.44(d,J＝7.2Hz,1H,pyridinone),2.09(s,3H,pyridinone-CH₃),1.77(s,6H,Ph-C(CH ₃)₂CN).¹³C NMR(125MHz,Chloroform-d)170.4,145.9,143.2,141.4,137.4,128.3,127.5,126.9,123.9,111.2,37.2,29.2,13.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₆H₁₇N₂O₂]:269.1285；found:269.1284.

Target compound 24: off-white solid, mp 220-.¹H NMR(600MHz,Chloroform-d)7.27(d,J＝2.0Hz,1H,pyridinone),7.02–6.98(m,3H,Ph),6.44(d,J＝7.3Hz,1H,pyridinone),3.92–3.87(m,4H,morpholine),3.19–3.14(m,4H,morpholine),2.12(s,3H,CH₃).¹³C NMR(150MHz,Chloroform-d)170.2,154.81(d,J＝251.1Hz),145.7,141.2(d,J＝8.0Hz),137.6,135.26(d,J＝9.4Hz),128.8,123.2(d,J＝3.4Hz),119.0(d,J＝4.1Hz),115.5(d,J＝23.1Hz),111.1,66.9,50.6(d,J＝3.7Hz),13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₆H₁₈FN₂O₃]:305.1296；found:305.1299.

Target compound 25: brown solid, mp 158-.¹H NMR(500MHz,Chloroform-d)7.52(s,1H,Ph),7.32(d,J＝5.5Hz,2H,Ph),7.29(d,J＝9.0Hz,1H,Ph),7.24(d,J＝7.2Hz,1H,pyridinone),6.48(d,J＝7.1Hz,1H,pyridinone),2.09(s,3H,CH₃).¹³C NMR(125MHz,Chloroform-d)170.7,156.4(d,J＝252.9Hz),145.7,137.7,131.9(d,J＝7.5Hz),129.0(d,J＝12.9Hz),128.9,128.8(d,J＝4.3Hz),125.5(d,J＝4.0Hz),117.4(d,J＝19.4Hz),111.5,12.9.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₁FNO₂]:220.0768；found:220.0773.

Target compound 26: a reddish brown solid, mp 180-.¹H NMR(600MHz,Chloroform-d)7.66–7.40(m,4H,Ph),7.17(s,1H,pyridinone),6.48(s,1H,pyridinone),2.03(s,3H,CH₃).¹³C NMR(150MHz,Chloroform-d)170.5,145.6,139.0,137.1,132.5,131.3,130.9,129.1,128.7,111.3,29.7,12.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₁ClNO₂]:236.0473；found:236.0475.

Target compound 27: light brown solid, mp 173-.¹H NMR(600MHz,Chloroform-d)7.50(dt,J＝15.4,7.8Hz,2H,Ph),7.33(s,1H,Ph),7.28(d,J＝5.0Hz,1H,Ph),7.21(d,J＝6.9Hz,1H,pyridinone),6.47(d,J＝7.0Hz,1H,pyridinone),2.13(s,3H,CH₃).¹³C NMR(150MHz,Chloroform-d)170.4,145.9,142.7,137.2,135.7,131.0,130.0,128.4,127.4,125.3,111.4,13.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₁ClNO₂]:236.0473；found:236.0471.

Target compound 28: brick red solid, mp 142-.¹H NMR(500MHz,Chloroform-d)7.40(s,1H,pyridinone),7.34–7.26(m,2H,Ph),7.08(s,2H,Ph),6.46(s,1H,pyridinone),2.44(s,3H,Ph-CH₃),2.11(s,3H,pyridinone-CH₃).¹³C NMR(125MHz,Chloroform-d)170.2,145.7,141.8,140.3,137.4,130.3,129.7,128.7,127.4,123.8,110.9,21.4,13.7.ESI-HRMS:m/z[M+Na]⁺calcd.for[C₁₃H₁₃NO₂Na]:238.0838；found:238.0831.

Target compound 29: brown solid, mp 195-196 ℃ in 60% yield.¹H NMR(600MHz,Chloroform-d)7.53(s,1H,pyridinone),7.23(s,3H,Ph),6.45(d,J＝5.9Hz,1H,pyridinone),2.14(s,3H,CH₃).¹³C NMR(150MHz,Chloroform-d)170.6,145.9,143.2,137.1,136.4,130.2,127.9,125.9,111.6,13.8.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₂H₁₀Cl₂NO₂]:270.0083；found:270.0086.

Target compound 30: light brown solid, mp 193-.¹H NMR(600MHz,Chloroform-d)7.28(d,J＝7.6Hz,1H,pyridinone),7.13(s,1H,Ph),6.87(s,2H,Ph),6.44(d,J＝7.2Hz,1H,pyridinone),2.39(s,6H,Ph-CH₃),2.11(s,3H,pyridinone-CH₃).¹³C NMR(150MHz,Chloroform-d)170.2,145.7,141.7,139.9,137.4,131.1,128.8,124.4,110.9,21.3,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₄H₁₆NO₂]:230.1176；found:230.1172.

Target compound 31: brown solid, mp 205-.¹H NMR(600MHz,Chloroform-d)7.27(s,2H,Ph),7.25(s,1H,pyridinone),6.46(s,1H,pyridinone),2.55(s,3H,Ph-CH₃),2.14(s,3H,pyridinone-CH₃).¹³C NMR(150MHz,Chloroform-d)170.5,145.9,140.0,137.2,136.7,136.5,128.1,126.3,111.5,17.5,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₃H₁₂Cl₂NO₂]:284.0240；found:284.0237.

Target compound 32: brown solid, mp 182-.¹H NMR(600MHz,Chloroform-d)7.31(d,J＝7.5Hz,1H,pyridinone),7.27(d,J＝6.9Hz,1H,Ph),7.08(s,1H,Ph),6.98(d,J＝7.4Hz,1H,Ph),6.43(d,J＝6.7Hz,1H,pyridinone),2.97(t,J＝7.1Hz,4H,Ar-CH₂),2.16(p,J＝6.8Hz,2H,Ar-CH₂),2.10(s,3H,CH₃).¹³C NMR(150MHz,Chloroform-d)170.1,146.4,145.9,145.6,134.0,137.6,128.8,125.3,124.5,122.7,110.7,32.9,32.6,25.6,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₅H₁₆NO₂]:242.1176；found:242.1180.

Target compound 33: brown solid, mp 243-.¹H NMR(600MHz,Chloroform-d)7.82(d,J＝7.6Hz,1H,Ph),7.78–7.76(m,1H,Ph),7.49–7.47(m,1H,Ph),7.41–7.37(m,3H,Ph),7.30(s,1H,Ph),7.22(d,J＝7.3Hz,1H,pyridinone),6.49(d,J＝7.1Hz,1H,pyridinone),2.14(s,3H,pyridinone-CH₃),1.52(s,6H,Ar-(CH ₃)₂).¹³C NMR(150MHz,Chloroform-d)170.1,155.5,153.8,145.7,140.6,140.5,137.7,137.4,128.6,128.4,127.4,125.6,122.8,121.2,120.9,120.6,110.8,47.3,27.0,13.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₂₁H₂₀NO₂]:318.1489；found:318.1481.

Target compound 34: off-white solid, mp 190-.¹H NMR(600MHz,Chloroform-d)7.38(d,J＝8.1Hz,2H,Ph),7.31(d,J＝6.4Hz,1H,pyridinone),6.95(d,J＝8.2Hz,2H,Ph),6.43(d,J＝6.5Hz,1H,pyridinone),5.05(s,2H,CH₂),2.29(s,3H,pyridinone-CH₃),1.30(s,9H,Ph-C(CH₃)₃).¹³C NMR(150MHz,Chloroform-d)170.0,151.8,146.5,137.8,132.3,128.6,126.3,125.9,111.3,57.1,34.7,31.4,12.3.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₇H₂₂NO₂]:272.1645；found:272.1639.

Target compound 35: light yellow solid, mp 172-.¹H NMR(600MHz,Chloroform-d)7.48(d,J＝8.4Hz,2H,Ph),7.23(d,J＝7.5Hz,1H,pyridinone),7.15(d,J＝8.4Hz,2H,Ph),6.41(d,J＝7.5Hz,1H,pyridinone),3.89(s,3H,pyridinone-OCH₃),2.05(s,3H,pyridinone-CH₃),1.34(s,9H,Ph-C(CH₃)₃).¹³C NMR(150MHz,Chloroform-d)173.8,152.9,147.5,140.8,139.3,138.8,126.9,126.4,117.0,59.5,35.0,31.3,14.2.ESI-HRMS:m/z[M+Na]⁺calcd.for[C₁₇H₂₁NO₂Na]:294.1465；found:294.1461.

Target compound 36: white solid, mp 198-.¹H NMR(600MHz,Chloroform-d)7.50(d,J＝8.4Hz,2H,Ph),7.23(d,J＝7.3Hz,1H,pyridinone),7.20(d,J＝8.4Hz,2H,Ph),6.42(d,J＝7.3Hz,1H,pyridinone),2.53(q,J＝7.5Hz,2H,CH₂),1.37(s,9H,Ph-C(CH₃)₃),1.01(t,J＝7.5Hz,3H,CH₃).¹³C NMR(150MHz,Chloroform-d)170.4,153.1,145.4,139.1,137.8,134.5,126.7,126.6,110.9,35.0,31.4,20.5,12.6.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₇H₂₂NO₂]:272.1645；found:272.1649.

Target compound 37: light yellow solid, mp 209-210 ℃, yield 86%.¹H NMR(600MHz,Chloroform-d)7.52(d,J＝8.3Hz,2H,Ph),7.10(d,J＝8.3Hz,2H,Ph),6.34(s,2H,pyridinone),1.91(s,6H,pyridinone-CH₃),1.36(s,9H,Ph-C(CH₃)₃).¹³C NMR(150MHz,Chloroform-d)179.2,153.2,149.6,136.8,127.3,127.2,117.2,35.0,31.4,21.7.ESI-HRMS:m/z[M+H]⁺calcd.for[C₁₇H₂₂NO]:256.1696；found:256.1698.

Example 3: the activity against plant pathogenic fungi is determined by the following procedure:

test strains: mango stem rot (Botryodiplodia theobroma), wheat scab (Fusarium graminearum), dragon fruit canker (neospora dimyrium), rice blast (Pyricularia oryzae), banana wilt (Fusarium oxysporum), banana anthracnose (Colletotrichum musae), Phytophthora capsici (Phytophthora capsici), Botrytis cinerea (Botrytis cinerea) and Sclerotinia sclerotiorum (sclerotiorum).

A hypha growth rate method is adopted. Dissolving a sample to be tested by using a proper amount of acetone, diluting the sample to be tested to a required concentration by using an aqueous solution containing 200 mug/mL of emulsifier, adding 9mL of culture medium and 1mL of diluted sample to be tested into a culture dish, shaking the culture dish uniformly to prepare a drug-containing flat plate with the concentration of 50 mug/mL, adding 1mL of sterilized water into a blank control to prepare a flat plate, cutting a bacteria disc along the periphery of hypha by using a puncher with the diameter of 4mm, and transferring the bacteria disc onto the drug-containing flat plate. Each treatment was repeated three times. The culture dish is placed in a constant temperature incubator at 24 +/-1 ℃ for culture. And 3d, measuring the expanded diameter of the bacterial disc by a cross method, calculating an average value, and comparing the average value with a blank control to calculate the relative bacteriostasis rate. The calculation formula is as follows:

table 1 shows the test results of the compounds.

TABLE 1

^aB.T, Rhizopus Mangifera; F.G Fusarium graminearum; N.D. Pitaya canker; P.O Magnaporthe grisea; F.O banana fusarium wilt; C.M BananaAnthrax bacteria; P.C Phytophthora capsici; B.C, Botrytis cinerea; S.S. Sclerotinia sclerotiorum.

Example 4: the test program of the compound for the prevention and treatment effect of the plant pathogenic fungi living body is as follows:

test strains: cucumber downy mildew (Pseudoperonospora cubensis), cucumber target spot (Corynespora cassiicola), wheat scab (Fusarium graminearum), rice sheath blight (Rhizoctonia solani), tomato gray mold (Botrytis cinerea).

The test method comprises the following steps:

1) host plant culture

Cucumber, wheat, rice and tomato seedlings are cultivated in a greenhouse (18-28 ℃ and RH 50-75%) and grow to the 2-leaf stage for later use.

2) Preparation of medicinal liquid

Accurately weighing a sample to be tested and a control medicament, adding acetone (solvent: liquid medicine ═ 1: 20) and 0.5% tween-80 tap water, preparing 20ml of each test liquid medicine for researching the bactericidal activity of the live vaccine, and taking tween water containing the same amount of solvent as a blank control. The natural product uses a mixture of acetone and methanol as solvent (ratio 1: 1).

3) Spray treatment

The sprayer is a crop sprayer with a spray pressure of 1.5kg/cm²The amount of the sprayed liquid is about 675L/hm². After the test material is treated, the test material is naturally air-dried and inoculated with pathogenic bacteria after 24 hours.

4) Inoculation of pathogenic bacteria

Respectively inoculating 5-8 × 10 sporangium suspension of cucumber downy mildew fungus by using inoculator⁴One/ml), cucumber leaf spot germ spore suspension (5-8X 10)⁶Per ml), wheat scab germ spore suspension (3-5X 10)⁵Perilla frutescens spore suspension (5-8X 10)⁶One/ml) and a suspension of Botrytis cinerea spores (5-8X 10)⁶One/ml) is sprayed onto the host crop and then transferred into a climatic chamber for cultivation (24 + -1 deg.C, RH)>90, no light). After 24h, the test material was moved to a greenhouse for normal management, and the bactericidal activity of the test samples was investigated after 5-7 d.

5) Results survey

The bactericidal activity of the test samples was investigated by visual inspection based on the extent of control development. The results are expressed as 100-0, with "100" representing no disease and "0" representing the most severe degree of disease or similar to the blank control.

Table 2 shows the test results of the compounds.

TABLE 2

^a"//" indicates that biological activity was not tested.

Example 5: the compound is used for measuring the disease control effect of mango after picking, and the measuring program is as follows:

the mango variety to be tested is the royal mango which is purchased in the Haikou north-south fruit market, the fruit has no mechanical damage and no plant diseases and insect pests, the physiological maturity is reached, and the mango is returned to a laboratory for treatment on the same day.

The compound is prepared into a solution of 200 mu g/mL, mango is put into the solution to be soaked for 5-8 minutes and naturally dried, and 15 fruits are treated for 3 times. Clear water is used as a control, and a 200 mu g/mL azoxystrobin solution is used as a medicament control. The samples were stored at 20 ℃ and RH > 90%, and observed 1 time every 3d to record maturity and disease onset.

And (3) grading the maturity:

level 1: the surface of the fruit is dark green, and the pulp is hard;

and 2, stage: the surface of the fruit is slightly discolored, and the pulp is hard;

and 3, level: the fruit shoulders of the fruits are light yellow (or light red), and the fruits begin to become soft;

4, level: the fruit is yellow (or red), the pulp is soft and edible.

Grading standard of mango post-harvest disease conditions:

level 0: no disease;

level 1: the area of the disease spots accounts for less than 5% of the area of the fruits;

and 3, level: the area of the disease spot accounts for 6 to 15 percent of the area of the fruit;

and 5, stage: the area of the disease spots accounts for 16 to 25 percent of the area of the fruits;

and 7, stage: the area of the disease spots accounts for 26-50% of the area of the fruits;

and 9, stage: the area of the disease spot accounts for more than 50% of the area of the fruit.

Disease index [ sigma (number of diseased fruits at each level × corresponding number of levels) ]/(number of total fruits × highest level value) × 100

Control effect (control disease index-treatment disease index)/control disease index x 100%

Table 3 shows the test results of the compounds.

TABLE 3

^aValues are the average of 3 replicates.^b'a' indicates that the difference is significant at the 0.01 level; 'a' indicates that the difference is significant at the 0.05 level

Example 6: the bacteriostatic activity of the compound on Xanthomonas oryzae pv. oryzae (Xoo) is determined by the following procedure:

to a 15mL tube was added 4mL of Nutrient Broth (NB) medium, 1mL of test compound (final concentration 100 and 50. mu.g mL)^-1) And 40. mu.L of Xoo bacterial solution, zhongshengmycin, a commercial fungicide, as a positive control. The tubes were then incubated in a constant temperature shaker at 180rpm and 28. + -. 1 ℃ for 24-48 hours. The Optical Density (OD) of NB medium in each tube was measured on a microplate reader (model 680, BIO-RAD, Hercules, Calif.)₆₀₀) Until the bacteria in untreated NB medium were in logarithmic growth. The in vitro inhibition I (%) was calculated by the following formula, wherein C represents the corrected absorbance value (OD) of untreated NB medium₆₀₀) And T represents the corrected absorbance value (OD) of the treated NB medium₆₀₀)。

Inhibition ratio I (%) - (C-T)/Cx 100

Table 4 shows the measurement results of the compounds.

TABLE 4

Example 7: the activity of the compound on a rice bacterial leaf blight living body is determined by the following procedure:

the pathogenicity of the Xoo strain was studied by the leaf cutting method. Rice line IR24 (susceptible) was used as the host for virulence tests. By immersing in freshly diluted bacterial suspension (OD) with sterile scissors₆₀₀0.8, about 4 × 109 CFU mL-1) leaf tips were cut to seed fully expanded leaves. Control inoculation was performed simultaneously by dipping the leaves into sterilized M210 liquid medium. At least 25 leaves were inoculated per test Xoo strain and scored. Symptoms were scored by measuring lesion length 14 days after inoculation and values were expressed as mean lesion length ± SD. The whole experiment was repeated three times independently. The control efficiency I (%) of the treatment and protection activities is calculated by the following equation. In this equation, C is the disease index of the negative control and T is the disease index of the treated group.

Inhibition ratio I (%) - (C-T)/Cx 100

Table 5 shows the measurement results of the compounds.

TABLE 5

^aValues are the average of 5 replicates.^b'a' indicates that the difference is significant at the 0.01 level; 'a' indicates that the difference is significant at the 0.05 level

Evaluation of results

The 1-aryl-4-pyridone derivatives have novel structures, and most of the derivatives show remarkable in-vitro fungicidal activity. In particular, compound 19 was present at 50. mu.g mL^-1The inhibitor has over 90 percent of inhibitory activity on 9 plant pathogenic fungi at concentration, and is superior to azoxystrobin. In addition, in vivo bioassay also demonstrated that Compound 19 was present at 400. mu.g mL^-1The control effect of more than 95 percent on cucumber downy mildew, cucumber target spot, wheat scab and tomato gray mold is realized. Meanwhile, the experiment result of the preservation after mango picking shows that the compound 19 is 200 mug mL^-1The mango postharvest disease can be effectively controlled under the concentration (the control effect is 87.91 percent, day 14) and the preservation time of the mango is prolonged. In addition, compounds 18 and 19 were found to be effective in controlling bacterial leaf blight of rice in potting experiments, which is more effective than zhongshengmycin, a commercial fungicide. In summary, the 1-aryl-4-pyridone derivatives have broad-spectrum activity against plant pathogenic fungi and bacteria, and are lead compounds with wide biological activity. In particular, the target compound 19 has great potential for developing pesticides against phytopathogenic fungi and bacteria.

The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.

Claims

1. The application of the compound with the structure shown in the formula (I) in inhibiting the activity of phytopathogen; the plant pathogenic bacteria are plant pathogenic fungi or plant pathogenic bacteria; the phytopathogenic fungi are selected from the group consisting of mango stem rot (Botryodiplodia theobroma), gibberella graminis (Fusarium graminearum), dragon fruit canker (neospora dimyrium), Pyricularia oryzae (Pyricularia oryzae), banana Fusarium oxysporum (Fusarium oxysporum), banana anthracnose (Colletotrichum musae), Phytophthora capsici (Phytophthora capsici), Botrytis cinerea (Botrytis cinerea), Sclerotinia sclerotiorum (sclerotiorum), cucumber downy mildew (Pseudoperonospora cubensis), cucumber target spot (Corynespora cassiacola), and rice sheath blight (Rhizoctonia solani);

the plant pathogenic bacteria are Xanthomonas oryzae pv. Oryzae;

in the formula (I), the compound is shown in the specification,

the structural compound shown in the formula (I) is specifically a structure shown in the following I-15-I-37:

2. the application of the compound with the structure shown in the formula (I) in preventing and treating plant diseases caused by phytopathogens; the plant diseases are selected from mango stem rot, wheat scab, dragon fruit canker, rice blast, banana wilt, banana anthracnose, phytophthora capsici leonian, tomato gray mold, sclerotinia rot of colza, cucumber downy mildew, cucumber target spot, rice sheath blight and rice bacterial leaf blight;

in the formula (I), the compound is shown in the specification,

3. the application of the compound with the structure shown in the formula (I) in preparing an inhibitor for inhibiting the activity of phytopathogen;

in the formula