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Benzothiadiazine methoxy acrylate derivatives and preparation method and application thereof

A technology of benzothiadiazine methoxy acrylic acid and derivatives, which is applied in the fields of botanical equipment and methods, chemicals for biological control, biocides, etc., can solve the problem of single action site, unreasonable use, etc problem, to achieve the effect of delaying the generation of resistance and novel structure

Active Publication Date: 2020-07-14
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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  • Benzothiadiazine methoxy acrylate derivatives and preparation method and application thereof
  • Benzothiadiazine methoxy acrylate derivatives and preparation method and application thereof
  • Benzothiadiazine methoxy acrylate derivatives and preparation method and application thereof

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 30mL ethyl acetate to the flask, stir for 10min, 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 monito...

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Abstract

The invention provides benzothiadiazine methoxy acrylate derivatives and a preparation method and application thereof, and the benzothiadiazine methoxy acrylate derivatives have the following chemicalstructural general formula VII as shown in the description, wherein R1 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy or nitro; and R2 is hydrogen, methyl or benzyl. According to the invention, an active group 3, 4-dihydro-2H-1, 2, 4-benzothiadiazine-1, 1-dioxo substitutes the side chain part of the methoxy acrylate bactericide and then is reasonably spliced with the pharmacophore of the methoxy acrylate bactericide, so that the bactericide with novel structure, broad spectrum, high efficiency and low toxicity is synthesized, the bactericide can be alternately used with the existing bactericide, the generation of resistance is avoided or delayed, the preparation conditions are conventional, the subsequent treatment is simple and convenient, and the industrialization is easy to realize.

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 use. 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 respirato...

Claims

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Application Information

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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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