Unlock instant, AI-driven research and patent intelligence for your innovation.
A class of pyrazole spiro derivatives and its preparation method and fungicide use
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A technology of pyrazole spiro and derivatives, applied in the field of pyrazole compounds
Active Publication Date: 2019-04-09
NANKAI UNIV
View PDF1 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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%.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
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 better monoamine oxidase inhibitory function, higher 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 multi...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More