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Preparation method and use of pentadiene ketone compound containing 1,3,4-oxadiazole sulfo-ethyoxyl

A technology of oxadiazole thioethoxy and pentadienone, which is applied in the field of chemistry and can solve problems such as no anti-plant virus activity and the like

Active Publication Date: 2015-06-03
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there is no relevant report on 1,3,4-oxadiazole-containing pentadienone compounds with anti-plant virus activity

Method used

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  • Preparation method and use of pentadiene ketone compound containing 1,3,4-oxadiazole sulfo-ethyoxyl
  • Preparation method and use of pentadiene ketone compound containing 1,3,4-oxadiazole sulfo-ethyoxyl
  • Preparation method and use of pentadiene ketone compound containing 1,3,4-oxadiazole sulfo-ethyoxyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Example 1: (1 E ,4 E )-1-(4-fluoro-phenyl)-5-(4-((5-(4-fluorophenyl)-1,3,4-oxadiazole)-2-thio)ethoxyphenyl )-1,4-Pentadien-3-one synthesis:

[0109] (1) Preparation of methyl p-fluorobenzoate

[0110] Put 0.1 mol of p-fluorobenzoic acid and 50 mL of anhydrous methanol into a 100 mL three-neck flask, slowly add 0.1 mol of concentrated sulfuric acid dropwise at room temperature, and then raise the temperature to reflux, and the reaction was completed for 8 hours. Recover methanol under reduced pressure, add 50 mL of water, wash the solution with saturated sodium bicarbonate solution until neutral, and recrystallize with methanol after extraction.

[0111] (2) Preparation of p-fluorobenzoic hydrazide

[0112] Put 0.05 mol of methyl p-fluorobenzoate and 50 mL of methanol into a 100 mL three-necked round-bottomed flask, slowly add 80% hydrazine hydrate (0.06 mol) at room temperature, and heat up to reflux for 7 hours to complete the reaction. Methanol was recovered un...

Embodiment 2

[0123] Example 2 :(1 E ,4 E )-1-(4-chloro-phenyl)-5-(4-((5-(4-fluorophenyl)-1,3,4-oxadiazole)-2-thio)ethoxyphenyl )-1,4-Pentadien-3-one synthesis:

[0124] Steps (1)-(4) are the same as in Example 1;

[0125] The difference between step (5) and embodiment 1 step (5) is: adding 4-chlorobenzaldehyde instead of 4-fluorobenzaldehyde;

[0126] The difference between step (6) and embodiment 1 step (6) is: add (1 E ,4 E )-1-(4-chlorophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one instead of (1 E ,4 E )-1-(4-fluorophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one;

[0127] The difference between step (7) and embodiment 1 step (7) is: add (1 E ,4 E )-1-(4-(2-bromoethoxy)-phenyl)-5-(4-chlorophenyl)-1,4-pentadien-3-one instead of (1 E ,4 E )-1-(4-(2-bromoethoxy)-phenyl)-5-(4-fluorophenyl)-1,4-pentadien-3-one.

Embodiment 3

[0128] Example 3 :(1 E ,4 E )-1-(4-bromo-phenyl)-5-(4-((5-(4-fluorophenyl)-1,3,4-oxadiazole)-2-thio)ethoxyphenyl Synthesis of )-1,4-pentadien-3-one

[0129] Steps (1)-(4) are the same as in Example 1;

[0130] The difference between step (5) and embodiment 1 step (5) is: adding 4-bromobenzaldehyde instead of 4-fluorobenzaldehyde;

[0131] The difference between step (6) and embodiment 1 step (6) is: add (1 E ,4 E )-1-(4-bromophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one instead of (1 E ,4 E )-1-(4-fluorophenyl)-5-(4-hydroxyphenyl)-1,4-pentadien-3-one;

[0132] The difference between step (7) and embodiment 1 step (7) is: add (1 E ,4 E )-1-(4-(2-bromoethoxy)-phenyl)-5-(4-bromophenyl)-1,4-pentadien-3-one instead of (1 E ,4 E )-1-(4-(2-bromoethoxy)-phenyl)-5-(4-fluorophenyl)-1,4-pentadien-3-one.

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Abstract

The invention discloses a preparation method and biological activity of a pentadiene ketone compound, containing 1,3,4-oxadiazole sulfo-ethyoxyl, with a function of preventing and treating a plant virus disease, namely a compound expressed in a general formula (I) and a preparation method of the compound. According to the method, by using substituted carboxylic acid, hydrazine hydrate, carbon disulfide, acetone, 4-substituted hydroxy benzaldehyde, substituted aromatic aldehyde, 1,2-dibromoethane and the like as raw materials, methanol, ethanol and N,N-dimethylformamide as solvents and potassium carbonate, sodium hydroxide and potassium hydroxide as catalysts, pentadiene ketone compound containing 1,3,4-oxadiazole sulfo-ethyoxyl is prepared through seven-step synthesis. The compounds I3, I4, I6, I11, I13, I14, I16 and I17 have good functions in cucumber mosaic virus, tobacco mosaic virus, southern rice black-streaked dwarf virus and the like. The formula is shown in the specification.

Description

technical field [0001] The invention relates to the field of chemical technology, in particular to a pentadienone compound containing 1,3,4-oxadiazolethioethoxy, a preparation method of the compound and a method for treating cucumber mosaic virus disease, tobacco Mosaic virus disease, southern rice black-streaked dwarf virus disease and rice stripe leaf blight virus have inhibitory uses. Background technique [0002] Plant virus disease is the second largest disease after fungus. Because of its serious harm and difficult control, it is often called "plant cancer". At present, inhibitors such as Ningnanmycin, morpholinidine hydrochloride, ribavirin and amino oligosaccharides are widely used to prevent and control plant virus diseases, but these agents have problems such as poor control effect and high use cost. For this reason, there is an urgent need to create new high-efficiency, low-toxic anti-plant virus agents to meet the needs of agricultural production. [0003] Nat...

Claims

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Application Information

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IPC IPC(8): C07D271/113A01P1/00
CPCA01N43/82C07D271/113
Inventor 宋宝安甘秀海胡德禹金林红薛伟李向阳吴剑陈学文
Owner GUIZHOU UNIV
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