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2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as preparation method and application thereof

A technology of oxadiazole sulfones and oxadiazoles, which is applied to 2,5-substituent-1,3,4-oxadiazole sulfone derivatives, their preparation and application fields, and can solve the problems of microorganisms, insects and pests Natural enemies poisoning, endangering a variety of biological resources, insufficient control effect, etc., to achieve the effects of excellent activity, simple structure and low production cost

Active Publication Date: 2018-06-05
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the use of chemical agents is a commonly used and effective method for preventing plant bacterial diseases such as rice bacterial blight and citrus canker, but the control effect of traditional chemical agents is not high enough, the cost is high, and it has brought problems Many problems: (1) The mode of action of most traditional chemical fungicides is non-specific. While killing pathogenic bacteria, it also poisons beneficial microorganisms and natural enemies of insects and pests, thereby endangering various biological resources and destroying ecological balance.
(2) The long-term use of traditional chemical pesticides makes pathogens gradually develop resistance, and resistance can easily spread among different pathogen groups

Method used

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  • 2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as preparation method and application thereof
  • 2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as preparation method and application thereof
  • 2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A preparation method of 2-methylthio-5-(((4-fluorophenyl)sulfone)methyl)-1,3,4-oxadiazole (compound 5a), comprising the following steps:

[0033] (1) Synthesis of ((4-fluorophenyl) thio) ethyl acetate

[0034] Add 4-fluorothiophenol (0.21mol) and potassium carbonate (0.23mol) into a 250mL three-neck flask, add 100mL of acetonitrile, then add ethyl chloroacetate (0.22mol) dropwise into the three-necked flask, and turn on the heating , TLC tracking reaction (developing agent: sherwood oil: ethyl acetate=10:1), after the reaction finishes, suction filtration, the acetonitrile in the filtrate is removed under reduced pressure to obtain intermediate ((4-fluorophenyl) thio) acetic acid ethyl ester.

[0035] (2) Synthesis of ((4-fluorophenyl) sulfone group) ethyl acetate

[0036]The synthetic intermediate ((4-fluorophenyl)thio)ethyl acetate (43mmol) was added to a 100mL three-necked flask, 20mL of absolute ethanol was added, and ammonium molybdate (2.2mmol) was dissolved in ...

Embodiment 2

[0044] A preparation method of 2-ethylthio-5-(((4-fluorophenyl)sulfone)methyl)-1,3,4-oxadiazole (compound 5b), comprising the following steps:

[0045] (1) Synthesis of ((4-fluorophenyl) thio) ethyl acetate

[0046] Add 4-fluorothiophenol (0.21mol) and potassium carbonate (0.23mol) into a 250mL three-neck flask, add 100mL of acetonitrile, then add ethyl chloroacetate (0.22mol) dropwise into the three-necked flask, and turn on the heating , TLC tracking reaction (developing agent: sherwood oil: ethyl acetate=10:1), after the reaction finishes, suction filtration, the acetonitrile in the filtrate is removed under reduced pressure to obtain intermediate ((4-fluorophenyl) thio) acetic acid ethyl ester.

[0047] (2) Synthesis of ((4-fluorophenyl) sulfone group) ethyl acetate

[0048] The synthetic intermediate ((4-fluorophenyl)thio)ethyl acetate (43mmol) was added to a 100mL three-necked flask, 20mL of absolute ethanol was added, and ammonium molybdate (2.2mmol) was dissolved in ...

Embodiment 3

[0056] A preparation method of 2-benzylthio-5-(((4-fluorophenyl)sulfone)methyl)-1,3,4-oxadiazole (compound 5c), comprising the following steps:

[0057] (1) Synthesis of ((4-fluorophenyl) thio) ethyl acetate

[0058] Add 4-fluorothiophenol (0.21mol) and potassium carbonate (0.23mol) into a 250mL three-neck flask, add 100mL of acetonitrile, then add ethyl chloroacetate (0.22mol) dropwise into the three-necked flask, and turn on the heating , TLC tracking reaction (developing agent: sherwood oil: ethyl acetate=10:1), after the reaction finishes, suction filtration, the acetonitrile in the filtrate is removed under reduced pressure to obtain intermediate ((4-fluorophenyl) thio) acetic acid ethyl ester.

[0059] (2) Synthesis of ((4-fluorophenyl) sulfone group) ethyl acetate

[0060] The synthetic intermediate ((4-fluorophenyl)thio)ethyl acetate (43mmol) was added to a 100mL three-necked flask, 20mL of absolute ethanol was added, and ammonium molybdate (2.2mmol) was dissolved in...

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Abstract

The invention discloses a 2,5-substituent-1,3,4-oxadiazole sulfone derivative as well as a preparation method and application thereof. The 2,5-substituent-1,3,4-oxadiazole sulfone derivative has a general formula shown in a formula (I), wherein R1 is 4-chlorine or 4-fluorine; and R2 is methyl, ethyl, propyl, n-butyl, n-pentyl, benzyl, 4-chlorobenzyl or 4-fluorobenzyl. The 2,5-substituent-1,3,4-oxadiazole sulfone derivative disclosed by the invention has good activity on rice bacterial leaf blight and xanthomonas citri and is simple in structure, simple in preparation technology and low in production cost. (The formula (I) is described in the specification).

Description

technical field [0001] The present invention relates to the field of chemical technology, specifically to 2,5-substituent-1,3,4-oxadiazole sulfone derivatives, and also to the 2,5-substituent-1,3,4-oxadiazole Preparation method of oxadiazole sulfone derivatives, and use of the 2,5-substituent-1,3,4-oxadiazole sulfone derivatives in preparing and preventing bacterial diseases such as rice bacterial blight and citrus canker drug application. Background technique [0002] Plant bacterial disease is a kind of third largest plant disease caused by bacteria infecting plants after fungal diseases and virus diseases, such as rice bacterial blight, rice bacterial streak, citrus canker, Bacterial diseases such as tobacco bacterial wilt and tomato bacterial wilt are important diseases worldwide. Bacteria that infringe plants can invade through natural orifices (stomata, lenticels, water holes, etc.) and wounds, spread by running water, rain, and insects, and spend the winter in disea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/113A01N43/824A01P1/00
CPCA01N43/82C07D271/113
Inventor 宋宝安李培胡德禹金林红张阿伟谢丹丹殷利民昝宁宁
Owner GUIZHOU UNIV
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