Quinoline 4-hydroxypicolinate compound and application thereof in prevention and treatment of magnaporthe oryzae

A technology of hydroxypicolinic acid and rice blast fungus, applied in application, fungicide, organic chemistry and other directions, can solve the problem of no research and development report on the activity of rice blast fungus, and achieve the effect of improving comprehensive performance and good environmental compatibility

Inactive Publication Date: 2020-09-11
杨子辉
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In this subject, the author uses the commercialized variety tebufloquin as the lead compound, and introduces the picolinate group into the 4-quinoline phenol core. The synthesis of the compounds of formula I and formula II of the present invention and the activity of controlling rice blast fungus No R&D reports

Method used

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  • Quinoline 4-hydroxypicolinate compound and application thereof in prevention and treatment of magnaporthe oryzae
  • Quinoline 4-hydroxypicolinate compound and application thereof in prevention and treatment of magnaporthe oryzae
  • Quinoline 4-hydroxypicolinate compound and application thereof in prevention and treatment of magnaporthe oryzae

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Preparation of 6-(trifluoromethyl)-quinolin-4-yl(2-fluoropyridine)carboxylate (I-a)

[0031] 2-Fluoropyridine-3-carboxylic acid (1.1 mol) and intermediate 6-trifluoromethyl-4-quinolinol (1.0 mmol) were dissolved in 3 mLofCH 2 Cl 2 The solvent was stirred and cooled down to 0°C, and EDCI (1.2 mmol) and DMAP (1.2 mmol) were added to the above system. The reaction was carried out at 40°C under nitrogen protection for 15h-20h. After the reaction was completed, the reaction solution was washed with saturated brine (2×2mL), and washed with water (2×2mL), dried over sodium sulfate, filtered with suction, and the crude product was obtained by flash column chromatography (petroleum ether / ethyl acetate, v / v=10 :1–1:1) to obtain compound 6-(trifluoromethyl)-quinolin-4-yl(2-fluoropyridine)carboxylate, white powder, yield 51%, 1 H NMR (400MHz, CDCl 3 )δ: 9.08 (d, J = 4.8Hz, 1H), 8.62–8.67 (m, 1H), 8.58 (d, J = 4.4Hz, 1H), 8.45 (s, 1H), 8.29 (d, J 1 =8.8Hz,1H),7.95(dd,J 1 =8.8Hz...

Embodiment 2

[0033] Preparation of 6-(trifluoromethyl)-quinolin-4-yl(2-chloropyridine)carboxylate (I-b)

[0034] White powder, yield 37%, 1 H NMR (400MHz, CDCl 3 )δ: 9.11(d,J=4.8Hz,1H), 8.70(dd,J 1 =4.8Hz,J 2 =2.0Hz,1H),8.51(dd,J 1 =8.0Hz,J 2 =2.0Hz,1H),8.41(s,1H),8.31(d,J 1 =8.8Hz,1H),7.96(dd,J 1 =8.8Hz,J 1 =1.5Hz,1H),7.64(d,J=4.8Hz,1H),7.53(dd,J 1 =8.0Hz,J 2 = 4.8Hz, 1H).

Embodiment 3

[0036] Preparation of 6-(trifluoromethyl)-quinolin-4-yl(2-methoxypyridine)carboxylate (I-c)

[0037] White powder, yield 26%, 1 H NMR (400MHz, CDCl 3 )δ:9.07(d,J=4.6Hz,1H), 8.63(s,1H),8.48(dd,J 1 =4.8Hz,J 2 =1.7Hz,1H),8.44(dd,J 1 =7.5Hz,J 2 1.7 Hz, 1H), 8.28(d, J=8.8Hz, 1H), 7.95(d, J=8.8Hz, 1H), 7.72(d, J=4.9Hz, 1H), 7.11 (dd, J 1 =7.5Hz,J 2 =4.9Hz, 1H), 4.19(s, 3H).

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Abstract

The invention discloses a quinoline 4-hydroxypicolinate compound. The compound has the following structure shown in the specification, wherein R is F, Cl or OCH3. The preparation method comprises thefollowing specific preparation steps: enabling 6-trifluoromethyl-4-quinolinol and 7, 8-dimethoxy-4-quinolinol to respectively react with 2-substituted pyridine-3-formic acid under the conditions of acatalyst, a condensing agent and an organic solvent so as to prepare quinoline 4-hydroxypicolinate compounds (I) and (II). The compounds (I) and (II) have a good prevention effect on magnaporthe oryzae. The preparation methods of the compounds (I) and (II) are simple to operate, high in yield and stable in product property.

Description

technical field [0001] The invention relates to a class of novel compounds and applications thereof, in particular to a quinoline 4-hydroxypicolinate compound and its application in preventing and treating rice blast fungus. Background technique [0002] Quinolines have a wide range of biological activities, such as insecticide, fungicide and herbicide. In the field of fungicides, two varieties of phenoxyquin and tebufloquin have been listed. It has gradually become a research hotspot for major pesticide companies at home and abroad. [0003] The first variety of quinoline fungicides is phenoxyquinoline, English name quioxyfen, developed by Dow AgroSciences, which exerts its medicinal effect by disturbing the germination of spores. It is mainly used for strawberry powdery mildew and wheat powdery mildew. Since the 1970s Since it was launched in the 1990s, it has been widely used in crops such as vegetables and wheat, and it has systemic and protective characteristics. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/42A01P3/00C07D401/12
CPCA01N43/42C07D401/12
Inventor 杨子辉杨树林刘畅白玉凤
Owner 杨子辉
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