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Trifluorobutenyl-containing 1,3,4-oxadiazole (thiadiazole) thioether (sulfide sulfone) derivatives and preparation method and application thereof

A technology of oxadiazole sulfide and trifluorobutene, applied in the field of chemistry, can solve the problems of crop yield reduction, commodity value reduction, loss of farmers' income and the like

Inactive Publication Date: 2016-06-08
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Plant nematodes have always been difficult to control due to their wide distribution, small size, hidden underground, and severe damage to the root system, resulting in a 10-20% reduction in crop yields and a reduction in commodity value, resulting in loss of farmers' income

Method used

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  • Trifluorobutenyl-containing 1,3,4-oxadiazole (thiadiazole) thioether (sulfide sulfone) derivatives and preparation method and application thereof
  • Trifluorobutenyl-containing 1,3,4-oxadiazole (thiadiazole) thioether (sulfide sulfone) derivatives and preparation method and application thereof
  • Trifluorobutenyl-containing 1,3,4-oxadiazole (thiadiazole) thioether (sulfide sulfone) derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Synthesis of 2-phenyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfur]-13,4-oxadiazole (compound number is A1):

[0081]Add 2-mercapto-5-phenyl-1,3,4-oxadiazole (0.40g, 1.53mmol) and potassium carbonate (0.25g, 1.83mmol) into a 50mL three-necked flask and add 15mL of acetonitrile, start stirring, The reaction system was a white turbid liquid, and a mixed solution of 4-bromo1,1,2-trifluoro-1-butene (0.32 g, 1.68 mmol) and 5 mL of acetonitrile was added thereto. Heated to reflux, TLC tracked the reaction process, after the raw material point disappeared, stopped the reaction, filtered out the insoluble salt, and the crude product of vacuum distillation, the crude product was recrystallized with dichloromethane to obtain the target compound, which was a white solid with a quality of 0.20g (theoretical mass of 0.23 g), the yield is 86.6%, and the melting point is 34-35°C.

Embodiment 2

[0083] Synthesis of 2-(4-fluorophenyl)-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfur]-13,4-oxadiazole (Compound No. A2) :

[0084] Synthesized as in Example 1, with the difference that 2-mercapto-5-(4-fluorophenyl)-1,3,4-oxadiazole (0.60g, 3.06mmol) and 4-bromo-1, 1,2-Trifluoro-1-butene as (0.63g, 3.36mmol) to give 2-(4-fluorophenyl)-5-[(3,4,4-trifluoro-3-butene-1 -yl)sulfur]-13,4-oxadiazole, yield 77.9%, melting point 42-43°C.

Embodiment 3

[0086] Synthesis of 2-(4-nitrophenyl)-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfur]-13,4-oxadiazole (compound number is A3 ):

[0087] Synthesized as in Example 1, except that 2-mercapto-5-(4-nitrophenyl)-1,3,4-oxadiazole (0.31g, 1.39mmol) and 4-bromo-1 , 1,2-Trifluoro-1-butene (0.28g, 1.53mmol) to give 2-(4-nitrophenyl)-5-[(3,4,4-trifluoro-3-butene- 1-yl)thio]-13,4-oxadiazole, yield 78.9%, melting point 84-86°C.

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Abstract

The invention discloses trifluorobutenyl-containing 1,3,4-oxadiazole (thiadiazole) thioether (sulfide sulfone) derivatives and a preparation method and application thereof. The trifluorobutenyl-containing 1,3,4-oxadiazole (thiadiazole) thioether (sulfide sulfone) derivatives are shown as the general structural formula (I) below, wherein R refers to one or more of methoxyl, nitryl, methyl, hydroxyl, trifluoromethyl and halogen atom, the halogen atom can be fluorine and chlorine, X refers to O and S, and Y refers to S and O=S=O. The trifluorobutenyl-containing 1,3,4-oxadiazole (thiadiazole) thioether (sulfide sulfone) derivatives have the advantages of high activity and low toxicity.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a trifluorobutene-containing 1,3,4-oxa(thia)diazole sulfide (sulfone) derivative, and also to a trifluorobutene-containing 1 , The preparation method of 3,4-oxa(thia)adiazole sulfide (sulfone) derivatives, and the application in killing nematodes. Background technique [0002] Plant nematodes have always been difficult to control because of their wide distribution, small size, hidden underground, and severe damage to the root system, resulting in a 10-20% reduction in crop yields and a reduction in commodity value, causing farmers to lose income. Worldwide, plant nematodes are estimated to cause agricultural losses in excess of $50 billion per year. In order to minimize economic losses, farmers have to use a large number of nematocide products with high toxicity of the original drug many times, which not only damages the environment, threatens food safety, but also r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/113C07D285/125A01N43/824A01P5/00
CPCC07D271/113A01N43/82C07D285/125
Inventor 宋宝安陈学文陈永中胡德禹薛伟陈吉祥王艳娇王珍珍
Owner GUIZHOU UNIV
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