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Styryl-containing 1,3,4-oxadiazole thioether compound, as well as preparation method and application thereof

A technology based on oxadiazole sulfide and styrene, which is applied in the chemical industry to achieve the effect of great development and application value and simple method

Inactive Publication Date: 2017-05-17
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The nematicide activity of styrene 1,3,4-oxadiazole sulfide compounds has not been reported yet

Method used

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  • Styryl-containing 1,3,4-oxadiazole thioether compound, as well as preparation method and application thereof
  • Styryl-containing 1,3,4-oxadiazole thioether compound, as well as preparation method and application thereof
  • Styryl-containing 1,3,4-oxadiazole thioether compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1, the synthesis of (E)-2-methylthio-5-styryl-1,3,4-oxadiazole (the compound number is a):

[0049] (1) Synthesis of (E)-cinnamic acid hydrazide:

[0050]Add (6.00g, 40.50mmol) cinnamic acid to a 100mL three-necked flask, add 80mL acetonitrile as a solvent, stir until uniform at room temperature, then take (6.57g, 48.60mmol) HOBt and add it to a three-necked flask, and weigh (9.23g , 48.60mmol) EDCI was added to the reaction system portion by portion, and the reaction system changed from white turbidity to clear transparent liquid, followed by a large amount of white solid, which was an active intermediate salt. The reaction progress was tracked by TLC. The developer was ethyl acetate (v):petroleum ether (v)=10:1, and the cinnamic acid was completely consumed after 2 hours of reaction. Keeping the reaction temperature at 5° C., 80% hydrazine hydrate (5.07 g, 80.99 mmol) solution was slowly added dropwise to the system, and the dropwise addition was completed wi...

Embodiment 2

[0055] Example 2, the synthesis of (E)-2-ethylthio-5-styryl-1,3,4-oxadiazole (the compound number is b):

[0056] (1) with embodiment 1 (1) step;

[0057] (2) with embodiment 1 (2) step;

[0058] (3) Add (0.30g, 1.47mmol) 5-styryl-1,3,4-oxadiazole-2-thiol and (0.10g, 2.45mmol) KOH in sequence to a 50mL three-necked flask, and then add 20mL of water As a solvent, stir at room temperature until all mercaptans are dissolved. Then weigh (0.23g, 2.45mmol) diethyl sulfate and dissolve it in 2mL of absolute ethanol, and slowly drop it into the above reaction system in a constant pressure funnel. After the completion of the reaction, suction filtration was performed directly, and the filter cake was recrystallized with absolute ethanol to obtain a white solid with a yield of 80.6%.

Embodiment 3

[0059] Embodiment 3, the synthesis of (E)-2-styryl-5-((3,4,4-trifluoro-3-en-1-yl)sulfur)-1,3,4-oxadiazole ( Compound number is c):

[0060] (1) with embodiment 1 (1) step;

[0061] (2) with embodiment 1 (2) step;

[0062] (3) Add (0.3g, 1.47mmol) (E)-5-styryl-1,3,4-oxadiazole-2-thiol and (0.27g, 2.00mmol) potassium carbonate successively to the reactor, Use 20mL of acetonitrile as solvent, then take 0.02g of 1,1,2-trifluoro-4-bromo-1-butene, and heat to reflux for 4h to complete the reaction. After the reaction was completed, 5 mL of distilled water was added to the system, the mixed solution was extracted with 3×20 mL of dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and recrystallized from absolute ethanol to obtain a light yellow solid, which was collected The rate is 81.5%.

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Abstract

The invention discloses a styryl-containing 1,3,4-oxadiazole thioether compound. The structural general formula (I) is as follows: R1 is hydrogen, 4-methoxyl, 4-chlorine, 4-fluorine or 4-bromine; R is methyl, ethyl, benzyl, 2,5-dichlorobenzyl, 4-fluorobenzyl, 4-hlorobenzyl, 2-methylbenzyl, 4-nitrobenzyl, 1,1,2-trifluoro-butenyl or the like. The styryl-containing 1,3,4-oxadiazole thioether compound has activities of killing citrus nematode and meloidogyne incognita chitwood. (The formula (I) is as shown in the description.).

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a preparation method of 1,3,4-oxadiazole sulfide compounds containing styryl, and also to the 1,3,4-oxadiazole containing styryl Use of oxadiazole sulfide compounds in preventing and controlling citrus nematode (Tylenchulus semipenetrans Cobb.) and southern root-knot nematode (Meloidogyne spp.). Background technique [0002] Plant parasitic nematodes are one of the infectious pathogens of plants. It has the characteristics of wide spread, wide host range, serious damage and long survival time, which brings huge losses to agricultural and forestry production. A loss of about $100 billion. Among all the plant-parasitic nematodes, citrus nematode and root-knot nematode incognita are the two most important nematodes for economic crops in my country. Citrus nematode is a plant parasitic nematode that mainly harms citrus. It mainly infects the roots of citrus and forms a la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/113A01N43/824A01P5/00
CPCC07D271/113A01N43/82
Inventor 宋宝安陈永中陈吉祥王艳娇王珍珍周大贵甘秀海
Owner GUIZHOU UNIV
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