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Aryl-oxazole-oxazoline compound as well as preparation method and application thereof

An oxazoline and compound technology, applied in the field of aryl-oxazole-oxazoline compounds and their preparation, can solve problems such as endangering human health and food safety, and achieve excellent inhibitory activity, novel structure and antibacterial activity improved effect

Active Publication Date: 2022-03-22
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, chemical pesticides are still the most effective way to control crop diseases, but due to the long-term repeated use of chemical pesticides, various plant pathogens have developed varying degrees of resistance to fungicides on the market (Microorganisms, 2021, 9, 119; phytopathology, 2021,111,819-830), and pesticide residues will also endanger human health and food safety

Method used

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  • Aryl-oxazole-oxazoline compound as well as preparation method and application thereof
  • Aryl-oxazole-oxazoline compound as well as preparation method and application thereof
  • Aryl-oxazole-oxazoline compound as well as preparation method and application thereof

Examples

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preparation example Construction

[0046] The present invention also provides the preparation method of aryl-oxazole-oxazoline compound described in above-mentioned technical scheme, comprises the following steps:

[0047] (1) mixing the compound having the structure shown in formula II, triethylamine, L-serine methyl ester hydrochloride, tetrahydrofuran and molecular sieves for condensation reaction to obtain the first reaction precursor;

[0048] (2) The first reaction precursor obtained in the step (1), trichlorobromomethane, 1,8-diazabicycloundec-7-ene and dichloromethane are mixed for condensation reaction to obtain an intermediate A;

[0049]

[0050] (3) The intermediate A obtained in the step (2), sodium hydroxide, methanol and water are mixed for a hydrolysis reaction to obtain a second reaction precursor;

[0051] (4) The second reaction precursor obtained in the step (3), 4-dimethylaminopyridine, aminoalcohol, methylene chloride and 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride ...

Embodiment 1

[0097]

[0098] Aryl-oxazole-oxazoline compound (compound C1, has in the chemical structure shown in formula I is phenyl, R 1 is S-phenyl, R 2 is a hydrogen atom) preparation method

[0099] (1) first L-serine methyl ester hydrochloride (5.9g, 37.7mmol) and tetrahydrofuran (60mL) are mixed to obtain the tetrahydrofuran (60mL) solution of L-serine methyl ester hydrochloride (5.9g, 37.7mmol), then Triethylamine (10.5mL, 75.4mmol) and benzaldehyde (4.0g, 37.7mmol) were successively added to a solution of L-serine methyl ester hydrochloride (5.9g, 37.7mmol) in tetrahydrofuran (60mL) at room temperature, And add 3A molecular sieves (0.5g) and stir at room temperature to carry out condensation reaction, TLC tracking monitoring, after 12h, the reaction is complete, the product of the condensation reaction is successively filtered and concentrated to obtain 7.0g light yellow first reaction precursor;

[0100] (2) Mix the first reaction precursor (7.0g, 33.8mmol) obtained in the...

Embodiment 2～24

[0105] Compounds C2-C24 were prepared according to the method of Example 1;

[0106] The difference from Example 1 is that the raw materials benzaldehyde and L-serine methyl ester hydrochloride were replaced with raw materials corresponding to compounds C2-C24.

[0107] Table 1 The structures of the compounds prepared in Examples 1 to 24 and the statistics of the H NMR and C NMR spectra detected

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

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Abstract

The aryl-oxazole-oxazoline compound provided by the invention has a chemical structure as shown in a formula I, has a specific aryl-oxazole-oxazoline skeleton, and is novel in structure; the compound shows excellent inhibitory activity on various agricultural harmful pathogenic bacteria including rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, phytophthora capsici, pyricularia grisea and colletotrichum capsici. Results of the embodiment show that according to the aryl-oxazole-oxazoline compounds provided by the invention, the bacteriostatic activity of part of the compounds on fusarium graminearum can reach 95.9%, the median inhibitory concentration of most of the compounds is smaller than that of positive control carbendazim, the median inhibitory concentration of part of the compounds on fusarium graminearum is 14.8 mu M, and the median inhibitory concentration of part of the compounds on fusarium graminearum can reach 95.9%. And compared with the positive control carbendazim, the antibacterial activity on fusarium graminearum is improved by 2.2 times.

Description

technical field [0001] The invention relates to the field of chemical pesticides, in particular to an aryl-oxazole-oxazoline compound and a preparation method and application thereof. Background technique [0002] Plant diseases seriously threaten global food security and ecosystems. At present, chemical pesticides are still the most effective way to control crop diseases, but due to the long-term repeated use of chemical pesticides, various plant pathogens have developed varying degrees of resistance to fungicides on the market (Microorganisms, 2021, 9, 119; phytopathology, 2021,111,819-830), and pesticide residues will also endanger human health and food safety. Therefore, how to design and synthesize fungicide molecules with novel structures and excellent inhibitory activity against various harmful agricultural pathogens is particularly important. Contents of the invention [0003] The object of the present invention is to provide a kind of aryl-oxazole-oxazoline comp...

Claims

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Application Information

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IPC IPC(8): C07D263/32C07D413/14A01N43/76A01P3/00A01P1/00
CPCC07D263/32C07D413/14A01N43/76Y02A50/30
Inventor 李圣坤孔文龙
Owner GUIZHOU UNIV
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