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Salicylaldoxime ester compounds as well as preparation method and application thereof

A technology of ester compound and salicylaldoxime, which is applied in the field of drug synthesis, can solve the problems of lack of industrial development, insecticidal or bactericidal activity is not ideal, and achieves good market development prospects, outstanding bacteriostatic effect, and mild reaction conditions. Effect

Inactive Publication Date: 2018-04-24
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the research, 4-methoxy salicylaldehyde exhibits certain antibacterial activity against various plant pathogens such as Fusarium oxysporum and Alternaria spp. Is it that its insecticidal or bactericidal activity is not ideal enough, and it does not yet have the value of industrial development

Method used

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  • Salicylaldoxime ester compounds as well as preparation method and application thereof
  • Salicylaldoxime ester compounds as well as preparation method and application thereof
  • Salicylaldoxime ester compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of (E)-2(((2-chloroacetoxy)imino)methyl)-5-methoxyphenyl-2-chloroacetate

[0038]

[0039] Weigh respectively 997.12mg of 4-methoxy salicylaldehyde (6.56mmol) and 548mg of hydroxylamine hydrochloride (7.89mmol) into an eggplant-shaped reaction flask, add a mixed solution of ethanol and water (22mL of ethanol, 44mL of water), Add 1.3mL of 50% NaOH at 0°C, react at room temperature for one hour after the dropwise addition, and use CH2 Cl 2 After extraction, the organic phase was washed with brine and dried over anhydrous sodium sulfate. After rotary evaporation under reduced pressure, silica gel column chromatography separated to obtain 4-methoxy salicylaldehyde hydroxylamine. White crystals, yield 71%, m.p.138.4-139.6°C. 1H NMR (DMSO-D6, 500MHz), δ: 3.73(s, 3H), 6.44~6.48(m, 2H), 7.36(d, J=8.0Hz, 1H), 8.25(s, 1H), 10.24(s , 1H), 11.07 (s, 1H); 13C NMR (DMSO-D6, 125MHz), δ: 55.65, 101.55, 106.59, 111.68, 129.92, 148.59, 158.14, 161.73. MS (ESI), m / z: 167 ...

Embodiment 2

[0042] Synthesis of (E)-2-(((butyryloxy)imino)methyl)-5-methoxyphenyl-butyrate

[0043]

[0044] Weigh 167mg of 4-methoxysalicylaldehyde hydroxylamine (1mmol) into a dry 50mL eggplant-shaped reaction bottle, add 15mL of dichloromethane, stir until the substrate is completely dissolved, add 200μL of triethylamine, and heat at 0~5℃ A solution of 127 mg of butyryl chloride (1.2 mmol dissolved in an appropriate amount of dry dichloromethane) was slowly added dropwise under ice-cooling. After the dropwise addition was completed, the mixture was followed and monitored by TLC at room temperature. When the raw material point disappeared, it was washed three times with 20 mL of saturated sodium bicarbonate, water and saturated NaCl aqueous solution, and dried over anhydrous sodium sulfate. After rotary evaporation under reduced pressure, it was separated by silica gel column chromatography to obtain (E)-2(((2-butyryloxy)imine)methyl)-5-methoxyphenyl-2-butyrate. Pale yellow oily liq...

Embodiment 3

[0046] Synthesis of (E)-2-(((benzoyloxy)imino)methyl)-5-methoxyphenyl-benzoate

[0047]

[0048] Referring to the synthetic method described in Example 1, using 4-methoxy salicylaldehyde hydroxylamine and benzoyl chloride as raw materials, prepare (E)-2(((benzoyloxy)imine)methyl)- 5-Methoxyphenyl-2-benzoate. White solid, yield 71%, m.p.136.5-137.0°C. 1 H NMR (CDCl 3 , 500MHz), δ: 8.60(s, 1H), 8.27~8.25(m, 2H), 8.14~8.11(m, 2H), 8.08~8.06(m, 2H), 7.71~7.67(m, 1H), 7.63 ~7.52(m, 2H), 7.50~7.43(m, 3H), 6.93(dd, J=9.0, 2.5Hz, 1H), 6.82(s, 1H), 3.88(s, 3H); 13 C NMR (CDCl 3 ,125MHz),δ:164.69,164.01,163.31,151.60,151.47,134.16,133.74,133.34,132.30,130.48,130.22,129.75,129.34,128.86,128.77,128.70,128.51,115.4,113.18,108.37,55.77。 ESI-MS m / z:376([M+H] + ).

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Abstract

The invention discloses salicylaldoxime ester compounds with a structure shown in formula I. A substituent group R of the salicylaldoxime ester compounds is selected from C1-C8 alkyl, or selected fromcyanogroup, halogen, phenyl, C1-C4 alkoxy, C1-C4 alkyl sulphanyl substituted C1-C8 alkyl, or selected from phenyl, or selected from phenyl with 1-3 substituent groups, wherein the 1-3 substituent groups on phenyl are selected from halogen, hydroxyl, carboxyl, nitryl, cyano group, phenyl, phenoxyl, benzoyl, C1-C8 alkyl, C3-C8 naphthenic base, C1-C4 alkoxy, C1-C4 halogenated alkyl, C1-C4 halogenated alkoxy, C1-C4 halogenated alkyl sulphanyl and C1-C4 halogenated alkyl sulfonyl. According to a synthesis route of the salicylaldoxime ester compounds, 4-methoxyl salicylaldehyde and hydroxylamine hydrochloride are taken as raw materials. The method is used for the first time for synthesis of the compounds and has the advantages that the yield is high, separation is easy and the like. The compounds have better bacteriostatic activity for multiple agricultural pathogenic fungi.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and specifically relates to various salicylaldoxime ester compounds, their preferred preparation methods and their application in plant disease control. Background technique [0002] With the enhancement of people's awareness of environmental protection and social sustainable development, it has become a worldwide consensus to minimize the side effects of pesticides and to develop biologically rational pesticides. Botanical pesticides have the advantages of low toxicity, low residue, basically harmless to non-target organisms, and no pollution to the environment. The development and application of botanical pesticides has gradually become a trend. And as the public's demand for green food and pollution-free food is increasing, the market's demand for botanical pesticides is also increasing day by day. The development of botanical pesticides has become an inevitable trend of social and...

Claims

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Application Information

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IPC IPC(8): C07C251/66C07C251/64C07C251/68C07C249/12A01N47/02A01N37/16A01P3/00
CPCA01N37/16A01N47/02C07C251/64C07C251/66C07C251/68
Inventor 姬志勤魏少鹏
Owner NORTHWEST A & F UNIV
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