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A class of benzothiadiazines methoxyacrylate derivatives and their preparation methods and uses

A technology of benzothiadiazines methoxyacrylic acid and its derivatives, applied in botany equipment and methods, chemicals for biological control, biocides, etc., can solve unreasonable use, single action site, etc. problem, to achieve the effect of delaying the generation of resistance and novel structure

Active Publication Date: 2022-03-29
TIANJIN AGRICULTURE COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the single site of action of methoxyacrylate fungicides and the wide and unreasonable use of them, the problem of resistance has emerged

Method used

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  • A class of benzothiadiazines methoxyacrylate derivatives and their preparation methods and uses
  • A class of benzothiadiazines methoxyacrylate derivatives and their preparation methods and uses
  • A class of benzothiadiazines methoxyacrylate derivatives and their preparation methods and uses

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Step 1, prepare 2-aminobenzenesulfonamide

[0025] Add 4.04g (20.00mmol) of 2-nitrobenzenesulfonamide into a 150mL double-necked round-bottomed flask at room temperature, add 70mL of absolute ethanol and 6.78g (30mmol) of stannous chloride dihydrate in sequence, heat to reflux for 1h, and decompress In addition to absolute ethanol, 30 mL of ethyl acetate was added to the flask, and after stirring for 5 minutes, the mixture was poured into ice water, and solid sodium bicarbonate was added to adjust the pH to 8, filtered under reduced pressure, washed with ethyl acetate, and the filtrate was collected. Precipitation under reduced pressure gave 3.26 g of white solid 2-aminobenzenesulfonamide, with a yield of 95%.

[0026] Step 2. Preparation of 4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide

[0027] Add 1.72g (10.00mmol) of 2-aminobenzenesulfonamide into a 50mL double-necked round-bottomed flask at room temperature, add 25mL of triethyl orthoformate, heat to reflux for 3h, low...

Embodiment 2

[0033] Step 1, preparation of 2-amino-5-fluorobenzenesulfonamide

[0034] Add 4.40g (20mmol) of 5-fluoro-2-nitrobenzenesulfonamide into a 150mL double-necked round bottom flask at room temperature, add 70mL of absolute ethanol and 6.78g (30mmol) of stannous chloride dihydrate in sequence, and heat to reflux for 1.2h , remove absolute ethanol under reduced pressure, add 30 mL of ethyl acetate to the flask, stir for 10 min, pour the mixture into ice water, add solid sodium bicarbonate, adjust the pH to 8, filter under reduced pressure, wash with ethyl acetate, The filtrate was collected and precipitated under reduced pressure to obtain 3.65 g of white solid 2-amino-5-fluorobenzenesulfonamide with a yield of 96%.

[0035] Step 2. Preparation of 7-fluoro-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide

[0036]Add 1.9g (10mmol) 2-amino-5-fluorobenzenesulfonamide to a 50mL double-necked round bottom flask at room temperature, add 25mL triethyl orthoformate, heat to reflux for 2.5h, TLC m...

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Abstract

The present invention proposes a class of benzothiadiazine methoxy acrylate derivatives and its preparation method and application. The substance has the following chemical structure formula VII: wherein, R 1 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy or nitro; R 2 is hydrogen, methyl or benzyl. In the present invention, the active group 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxy is replaced by the side chain part of the methoxyacrylate fungicide and its medicinal effect A class of novel structure, broad-spectrum, high-efficiency, and low-toxicity fungicides have been synthesized through reasonable splicing of groups, which can be used alternately with existing fungicides to avoid or delay the development of resistance. The preparation conditions are conventional, and the follow-up treatment is simple and easy to implement. industrialization.

Description

technical field [0001] The invention belongs to the technical field of agricultural fungicides, and relates to N- and S-containing benzothiadiazine methoxyacrylate derivatives, especially 3,4-dihydro-2H-1,2,4-benzothiazine Diazine-1,1-dioxymethoxy acrylate derivatives and their preparation method and application. Background technique [0002] Methoxyacrylate fungicides not only have high efficiency, low toxicity, and broad-spectrum fungicide activity, but also have strong systemic properties, and have become one of the most important agricultural fungicides in the world. In 2016, methoxyacrylate fungicides accounted for 22.2% of the global fungicide market with a total sales of 3.396 billion US dollars. They are new agricultural fungicides with great development potential and market vitality. This type of fungicide is a type of mitochondrial respiratory chain inhibitor, which mainly inhibits the growth of fungi by inhibiting the cytochrome bel complex in the mitochondrial r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/24A01N43/88A01P3/00
CPCC07D285/24A01N43/88
Inventor 刘敬波王远宏张立田小卫
Owner TIANJIN AGRICULTURE COLLEGE
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