Substituted benzisothiazole compound and preparation method and application thereof

A technology for benzisothiazoles and compounds, which is applied in the field of substituted benzisothiazoles and their preparations, and can solve the problems that structural benzisothiazoles have not been reported.

Active Publication Date: 2019-03-19
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the structure of the benzisothiazole compound as shown i

Method used

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  • Substituted benzisothiazole compound and preparation method and application thereof
  • Substituted benzisothiazole compound and preparation method and application thereof
  • Substituted benzisothiazole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0193] Example 1: 3-(((2-chlorothiazol-5-yl)methyl)(methyl)amino)benzisothiazole 1,1-dioxide (Compound 1)

[0194]

[0195] The first step reaction: 3-chlorobenzisothiazole 1,1-dioxide

[0196] At room temperature, 36.6g (0.20mol) of benzisothiazol-3(2H)-one 1,1 dioxide and 71.4g (0.6mol) of thionyl chloride were successively dissolved in 100ml of dioxane and refluxed for 12 Hours, TLC plate monitoring, a small amount of raw material remained. The solvent was removed under reduced pressure, and the residue was recrystallized with 60ml of toluene, filtered, and dried to obtain 30g of white solid, yield: 75%, melting point 148-149°C.

[0197] The second step reaction: 1-(2-chlorothiazol-5-yl)-nitrogen-methylmethanamine

[0198] At room temperature, add 82g (0.8mol) of 30% methylamine aqueous solution into 120ml of 95% ethanol, and cool to 0°C. 34g (0.2mol) 2-chloro-5-chloromethylthiazole was added dropwise to the above solution, the temperature was controlled below 5°C, th...

Embodiment 2

[0202] Example 2: 3-(((2-chlorothiazol-5-yl)methyl)(methyl)amino)benzisothiazole 1,1-dioxide (Compound 16)

[0203]

[0204] The first step reaction: N-((2-chlorothiazol-5-yl)-methyl)ethylamine

[0205] At room temperature, add 13.8g (0.2mol) of 65% ethylamine aqueous solution into 50ml of 95% ethanol, and cool to 0°C. Add 8.5g (0.05mol) of 2-chloro-5-chloromethylthiazole dropwise to the above solution, the temperature is controlled below 5°C, the dropwise addition takes 1h, and after the drop is complete, continue to stir at 0°C for 1h. Gradually rose to room temperature and continued to stir for 5h. TLC detects that a small amount of raw material remains. The reaction solution was concentrated under reduced pressure, 50ml of water was added to the residue, extracted with ethyl acetate (3x30ml), the combined extracts were washed with 30ml of saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain 7.5g of the pr...

Embodiment 3

[0209] Example 3: 3-(((2-chlorothiazol-5-yl)methyl)(methoxy)amino)benzisothiazole 1,1-dioxide (Compound 106)

[0210]

[0211] The first step reaction: N-((2-chlorothiazol-5-yl)-methyl)-oxygen-methylhydroxylamine

[0212] At room temperature, add 8.5g (0.1mol) of methoxyamine hydrochloride and 22g (0.21mol) of triethylamine into 80ml of acetonitrile, and cool to 0°C. 16.8g (0.1mol) 2-chloro-5-chloromethylthiazole was added dropwise to the above solution, the temperature was controlled below 5°C, and the dropwise addition took 1.5h. After the dropping was completed, it was gradually raised to room temperature and continued to stir for 2h. The temperature was raised to 50°C and stirring was continued for 4h. A small amount of raw material was detected by TLC. The reaction solution was lowered to room temperature, concentrated under reduced pressure, 50ml of water was added to the residue, extracted with ethyl acetate (3x50ml), the combined extracts were washed with 50ml of ...

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Abstract

The invention discloses a substituted benzisothiazole compound or salt thereof, having the structural formula as shown in the description, wherein substituent groups thereof are as shown in specifications. The compound has good activity to various germs, insect pests and pest mites in the field of agriculture. As the compound has high biological activity, even a small dose of compound has good effect, and can be used for preparing bactericide and insecticidal acaricide in the fields such as agriculture.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, insecticides and acaricides, and specifically relates to a novel substituted benzisothiazole compound and its preparation method and application. Background technique [0002] In agricultural production, with the promotion of straw returning to the field and no-tillage technology, the treatment of plant residues in production is insufficient, and many pathogens survive winter and summer through plants, resulting in a large number of plant pathogenic bacteria remaining in the soil. Under suitable growth conditions, pathogenic bacteria will grow rapidly in the soil and infect plants, seriously affecting the growth and development of plants. [0003] In addition, the most likely problem in the control of pests and diseases is resistance. In order to prevent the occurrence of resistance, new pesticides can be developed or existing pesticides can be used for compounding, but the effect of using ...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D275/06A01N43/80A01P3/00A01P7/02A01P7/04A01P5/00
CPCA01N43/80C07D275/06C07D417/12
Inventor 许辉唐剑峰迟会伟刘莹乔思佳吴建挺韩君
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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