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Application of 1-aryl-4-pyridone compound

A compound and aryl technology, applied in the application field of 1-aryl-4-pyridone compounds, can solve problems such as agricultural disease prevention and control obstacles, and achieve the effect of prolonging the preservation time

Active Publication Date: 2019-12-31
HAINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The emergence of these resistances has created a huge obstacle to the production of pesticides and the control of agricultural diseases. Therefore, it is urgent to develop new fungicides to solve these problems.

Method used

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  • Application of 1-aryl-4-pyridone compound
  • Application of 1-aryl-4-pyridone compound
  • Application of 1-aryl-4-pyridone compound

Examples

Experimental program
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preparation example Construction

[0038] The present invention also provides a preparation method of the structural compound shown in formula (I), comprising:

[0039] The pyrone of the structure of formula (II) and the amine compound of the structure of formula (III) are heated and refluxed in water to obtain the compound of structure shown in formula (I); or

[0040] The pyrone with the structure of formula (II) and the amine compound with the structure of formula (III) are reacted under high pressure and heated in a mixed solution of water, ethanol and hydrochloric acid to obtain the compound with the structure shown in formula (I);

[0041]

[0042] In the formula, R 1 Alkoxy selected from H, hydroxyl or C1~C10; R 2 is C1~C10 alkyl; R 3 Selected from H, C1-C10 alkyl; X is selected from H, C1-C10 alkyl, C6-C30 aryl, C6-C30 heterocyclic group.

[0043]One of the preparation methods of the compound with the structure shown in formula (I) provided by the present invention preferably can be: heating and r...

Embodiment 1

[0071] Example 1 Preparation of Target Compounds 5 and 6.

[0072] Maltol (10 mmol) was dissolved in 15 mL of water, and excess ammonia (6 mL) was added. The reaction mixture was refluxed for 10 hours, ammonia and solvent were removed under reduced pressure, and the mixture was cooled to room temperature overnight. The solid product obtained is recrystallized from a 50% water / methanol mixture in the presence of activated carbon. Activated carbon was filtered off, and the product was concentrated under reduced pressure. The final product is dried over phosphorus pentoxide in a desiccator. The target compound 5 (1.01 g, 7.93 mmol) was obtained. Gray solid, mp 285-287°C, yield 79%. 1 H NMR (600MHz, DMSO-d 6 )δ8.01(d, J=5.5Hz, 1H, pyridinone), 6.33(d, J=5.5Hz, 1H, pyridinone), 2.23(s, 3H, CH 3 ). 13 C NMR (150MHz, DMSO-d 6 )δ172.6, 154.6, 149.2, 143.0, 113.6, 14.0.ESI-HRMS: m / z[M+H] + calcd.for[C 6 h 8 NO 2 ]: 126.1243; found: 126.1238.

[0073] The synthesis of targe...

Embodiment 2

[0075] Example 2: Preparation of target compound 7-37.

[0076] Maltol (10 mmol) and excess aniline (15 mmol) were added to an acidic solution of 18.0 mL of water, 0.4 mL of HCl and 2.0 mL of ethanol (pH=5). The resulting mixture was heated in an autoclave at 160° C. for 12 hours. 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 2 Cl 2 :CH 3 OH=50:1) to purify the residue to obtain the target compound 7 (1.67g, 8.3mmol). White solid, mp 206-207°C, yield 83%. 1 HNMR (500MHz, Chloroform-d) δ7.53 (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,CH 3 ). 13C NMR (125MHz, Chloroform-d) δ170.3, 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[C 12 h 12 NO 2 ]: 202.0863; found: 202.0858.

[0...

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Abstract

The invention discloses application of a 1-aryl-4-pyridone compound, and provides application of a compound of a structure of a formula (I) shown in the description in inhibiting activity of plant pathogenic bacteria. The compound of the structure of the formula (I) shown in the description has outstanding broad-spectrum antifungal activity upon plant pathogenic bacteria in agricultural production, and meanwhile, has a prevention and treatment effect on bacterial disease of crops. In-vivo biological assay shows that the compound of the structure of the formula (I) shown in the description hasa prevention and control effect greater than 95% on cucumber downy mildew, cucumber target leaf spot, wheat scab and tomato gray mold. Meanwhile, results of postharvest fresh-keeping tests of mangos show that the compound is capable of effectively controlling postharvest diseases of mangos and in addition, prolonging the fresh-keeping time of the mangos. In addition, results show that the compoundis also capable of effectively controlling bacterial leaf blight of rice in pot experiments, and is more effective than a commercial fungicide zhongshengmycin. In conclusion, the 1-aryl-4-pyridone derivative of the formula (I) shown in the description has broad-spectrum plant pathogenic fungus resistance and bacterial activity, and is a type of lead compounds with wide bioactivity.

Description

technical field [0001] The invention relates to the field of biotechnology, in particular to the application of a 1-aryl-4-pyridone compound. Background technique [0002] For decades, phytopathogenic fungi have caused serious damage to crop production. There are more than 8,000 known species of fungi that can cause plant diseases. my country is a large agricultural country. Diseases caused by plant pathogenic fungi are an important factor restricting my country's agricultural production. These diseases often occur on a large scale and cause huge losses to my country's agricultural production. Currently, chemically synthesized pesticides are mainly used in agriculture. Our country needs to produce and use more than 800,000 tons of chemical fungicides and pesticides every year. The use of these pesticides has greatly reduced the losses caused by diseases, but the large-scale use of chemical pesticides has also caused A series of problems and hidden dangers have been identif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/16A01N43/40A01N43/84A01P3/00A01P1/00
CPCA01N43/16A01N43/40A01N43/84
Inventor 孙然锋俞秀强朱新月周杨李庆林
Owner HAINAN UNIVERSITY
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