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Pyrazole spiro derivatives as well as preparation method and bactericide application thereof

A technology of pyrazole spiro and derivatives, applied in the field of pyrazole compounds

Active Publication Date: 2014-06-18
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the reported synthetic methods and biological activity studies focus on monocyclic and cyclic pyrazole derivatives, and there are few reports on the synthesis and biological activity of pyrazole spiro compounds.

Method used

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  • Pyrazole spiro derivatives as well as preparation method and bactericide application thereof
  • Pyrazole spiro derivatives as well as preparation method and bactericide application thereof
  • Pyrazole spiro derivatives as well as preparation method and bactericide application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis and structural identification of pyrazole spiro derivatives, in the general structural formula R 1 = H, R 2 =CO 2 Et, R 3 =Et, X=NBn.

[0030] In a 25mL schlenk bottle equipped with a magnetic stir bar, add 1.0mL tetrahydrofuran, electron-deficient olefin II (R 1 = H, R 2 =CO 2 Et, X=NBn) 61mg (0.2mmol), ethyl azodicarboxylate 52mg (0.3mmol) and triphenylphosphine 79mg (0.3mmol), the resulting reaction mixture was stirred at room temperature under nitrogen protection for 24 hours, after the completion of the reaction The solvent was removed by rotary evaporation, and the crude product was purified by 200-300 mesh silica gel column chromatography. The eluent was petroleum ether (boiling range 60-90 degrees Celsius): ethyl acetate, and the volume ratio was 10:1-5:1. 92 mg of the pure product was obtained as light yellow solid, and the yield was 99%. The amount of target compound I prepared and the volume of the reaction vessel can be expanded or reduced i...

Embodiment 2

[0032] Synthesis and structural identification of pyrazole spiro derivatives, in the general structural formula R 1 =5-Cl, R 2 =CO 2 Et, R 3 =Et, X=NBn.

[0033] Synthetic steps and process parameter are basically the same as embodiment 1, and difference is listed as follows:

[0034] The electron-deficient olefin II used as raw material is R 1 =5-Cl, R 2 =CO 2 Et, X=NBn, the dosage is 68mg (0.2mmol); 97mg of the pure white solid product is obtained, and the yield is 97%.

Embodiment 3

[0036] Synthesis and structural identification of pyrazole spiro derivatives, in the general structural formula R 1 =5-Br, R 2 =CO 2 Et, R 3 =Et, X=NBn.

[0037] Synthetic steps and process parameter are basically the same as embodiment 1, and difference is listed as follows:

[0038] The electron-deficient olefin II used as raw material is R 1 =5-Br, R 2 =CO 2 Et, X=NBn, the dosage is 77mg (0.2mmol); 108mg of pure white solid is obtained, and the yield is 99%.

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Abstract

The invention provides pyrazole spiro derivatives as well as a preparation method and bactericide application thereof. The pyrazole spiro compounds have chemical structural formula as shown in formula I which is as shown in the specification. The invention discloses a structural formula, a synthesis method and bactericide application of the compounds, and discloses biological activity of the compounds used as agricultural fungicides and a measuring method thereof. The synthesis method is as follows: dissolving azo diformate, electron-deficient olefin derived from isatin or benzofuran diketone as well as triphenylphosphine in an organic solvent, stirring the obtained reaction mixture in the presence of a nitrogen gas at a room temperature, and carrying out column chromatography isolation after the reaction is completed, thereby obtaining the pyrazole spiro compounds. The 15 pyrazole spiro derivatives disclosed by the invention are excellent in bactericidal activity and can be mainly applied as active ingredients for being applied to the agricultural fungicides.

Description

technical field [0001] The technical scheme of the present invention relates to pyrazole compounds, in particular to a class of novel pyrazole spirocyclic compounds with fungicidal activity. Background technique [0002] Pyrazole derivatives are an important class of five-membered nitrogen heterocyclic compounds with rich medicinal and pesticide activities. For example, it has good monoamine oxidase inhibitory function, high antidepressant and anticonvulsant activity (Secci D., et al. Curr. Med. Chem. 2011, 18, 5114-5144; Schmidt A., Curr. Org. Chem.2011, 15, 1423-1463.), and this type of compound also has higher insecticidal, bactericidal and herbicidal activities (Lamberth C., Heterocycles 2007, 71, 1467-1502.). The development of efficient methods for preparing such compounds has received long-term attention from chemists, and a series of effective synthetic methods have also been established. Existing method comprises at present: by the mode of condensation, through mu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/10C07D491/107A01P3/00
CPCA01N47/16C07D487/10C07D491/107
Inventor 贺峥杰周荣杨昌江
Owner NANKAI UNIV