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2-(2-benzyl hydrazono)-4-(benzofuran-5-yl) thiazole and preparation method and application thereof

A technology of dichlorobenzylhydrazine and nitrobenzylhydrazine, which is applied in the field of new compounds and their preparation, and can solve problems such as high toxicity

Inactive Publication Date: 2013-06-12
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Carbamate pesticides have high activity and are widely used, but they are highly toxic. Therefore, it is necessary to develop alternative products with lower toxicity and better activity to meet market demand

Method used

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  • 2-(2-benzyl hydrazono)-4-(benzofuran-5-yl) thiazole and preparation method and application thereof
  • 2-(2-benzyl hydrazono)-4-(benzofuran-5-yl) thiazole and preparation method and application thereof
  • 2-(2-benzyl hydrazono)-4-(benzofuran-5-yl) thiazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of 2-bromo-1-(7-ethoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone (C1)

[0038]

[0039] C1

[0040] 4.66 g of 1-(7-ethoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, 80 mL of ethanol, stirred and refluxed, added 8.96 g of copper bromide, After reacting for 2 h, the reaction solution was filtered while it was hot, and the solvent was recovered by rotary evaporation, dissolved in ethyl acetate, washed with dilute acid, filtered, washed with water, separated, dried, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain a white solid C1; yield 72.0 %, m.p. 98~100 ℃.

Embodiment 2

[0042] Preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone (C2)

[0043]

[0044] C2

[0045] 4.38 g of 1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, 80 mL of ethanol, stirred and refluxed, added 8.96 g of copper bromide, After reacting for 2 h, the reaction solution was filtered while it was hot, and the solvent was recovered by rotary evaporation, dissolved in ethyl acetate, washed with dilute acid, filtered, washed with water, separated, dried, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain a white solid C2; yield 50.0 %, m.p. 90~91 ℃.

Embodiment 3

[0047] Preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)acetone (C3)

[0048]

[0049] C3

[0050] 9.37 g of 1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)acetone, 120 mL of ethanol were stirred and refluxed, and 18.02 g (0.08 mol) of bromine were added in batches Copper chloride, reacted for 2 h, filtered the reaction solution while it was hot, evaporated the solvent, dissolved in ethyl acetate, washed with dilute acid, filtered, washed the filtrate with water, separated, and distilled under reduced pressure to obtain a crude product, which was recrystallized from ethanol to obtain a white solid C3; Rate 97.8%, m.p. 85~87 ℃.

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Abstract

The invention relates to 2-(2-benzyl hydrazono)-4-(benzofuran-5-yl) thiazole as shown in the chemical structural formula I and salt thereof, wherein R and R1 are selected from H, C1-C2 alkyl, C3-C4 straight chain alkyl or branch chain alkyl; X1-X5 are selected from hydrogen, C1-C2 alkyl, hydroxyl, methoxyl, ethoxyl, trifluoromethyl, fluorine, chlorine, bromine and nitryl; thiosemicarbazone is reacted with 2-holo-1-(7-methoxyl-2, 2-dimethyl-2, 3-dihydrobenzofuran-5-yl) alkyl ketone, and is neutralized to prepare 2-(2-benzyl hydrazono)-4-(2,2-dimethly-2, 3-dihydrobenzofuran-5-yl) thiazole. The compound is applied to preparing bactericide.

Description

technical field [0001] The present invention relates to a class of new compounds and their preparation methods and applications, specifically 2-(2-benzylhydrazono)-4-(2,2-dimethyl-2,3-dihydrobenzofuran-5- Base) thiazoles and their preparation methods and applications as fungicides. Background technique [0002] Furanol (chemical name 2,2-dimethyl-2,3-dihydrobenzofuranphenol) is an important intermediate in the production of large-tonnage carbamate pesticides such as carbofuran, haoanwei and carbofuran. Carbamate pesticides have high activity and are widely used, but they are more toxic. Therefore, it is necessary to develop alternative products with lower toxicity and better activity to meet the market demand. As we all know, it takes 8-10 years to develop a new pesticide variety. In addition, there are many data and projects required for the registration of new pesticide varieties, and the cost is hundreds of millions of dollars. Therefore, the world's new pesticide creati...

Claims

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Application Information

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IPC IPC(8): C07D417/04A01N43/78A01P3/00
Inventor 胡艾希魏莉叶姣沈芳李婉欧晓明
Owner HUNAN UNIV
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