Pyrazole cyclohexanediol ether compounds and applications thereof

A technology of pyrazole cyclohexanediol ether and compound, applied in application, organic chemistry, biocide, etc.

Active Publication Date: 2016-07-20
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compound of general formula I in the present invention has a novel structure, and there is no related literature report

Method used

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  • Pyrazole cyclohexanediol ether compounds and applications thereof
  • Pyrazole cyclohexanediol ether compounds and applications thereof
  • Pyrazole cyclohexanediol ether compounds and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Embodiment 1: the preparation of compound 5-1

[0130]

[0131] (1) Preparation of intermediate 3-(4-chlorophenyl)-1-methyl-5-pyrazolol

[0132] A solution of 10.60 g of methyl p-chlorobenzoylacetate in 50 ml of methanol was heated to reflux. A slight excess of methylhydrazine was added dropwise and refluxed for 3 hours. After the reaction was monitored by TLC, it was concentrated, cooled, and crystals were precipitated. Filter and rinse the crystals with a small amount of methanol. After drying, 7.5 g of crystalline 3-(4-chlorophenyl)-1-methyl-5-pyrazolol was obtained.

[0133] (2) Preparation of Compound 5-1

[0134] In a 500mL three-necked flask, add 23.05g (0.10mol) intermediate 3-(4-chlorophenyl)-1-methyl-5-pyrazolol and 10.78g (0.11mol) epoxycyclohexane, and then add 0.4 g (0.01mol) NaOH is used as a catalyst, and toluene is used as a solvent, and the reaction is carried out at 105-108° C. for 8 hours by heating. Cool to room temperature, add water, separ...

Embodiment 2

[0135] Embodiment 2: the preparation of compound 5-99

[0136]

[0137] In the 100mL flask, add 0.66g (2mmol) intermediate 2-(3-(4-chlorophenyl)-1-methyl-1H-pyrazol-5-yloxy)cyclohexanol (5-1) and 0.10g (60%, 2.4mmol) NaH, then add 20mL DMF as a solvent, react at room temperature for 30min, then add dropwise 0.29g (2.4mmol) allyl bromide solution in DMF to the bottle, then heat up to 80°C React left and right. After the reaction was monitored by TLC, after cooling to room temperature, the reaction mixture was poured into 20 mL of water, extracted with 200 mL of ethyl acetate, and the residue was separated by column chromatography to obtain 0.37 g of a colorless oil with a yield of 53.6%.

Embodiment 3

[0138] Embodiment 3: the preparation of compound 5-206

[0139]

[0140] In a 250mL flask, add 6.57g (20.0mmol) intermediate 2-(3-(4-chlorophenyl)-1-methyl-1H-pyrazol-5-yloxy)cyclohexanol and 3.03g (30.0mmol ) triethylamine, then add 100mL of dichloromethane as a solvent, add dropwise a solution of 2.71g (24mmol) of chloroacetyl chloride in dichloromethane to the bottle under stirring at room temperature, and then continue to stir the reaction at room temperature. After the reaction was monitored by TLC, the solvent was spin-dried, the mixture was poured into 50 mL of water, 200 mL of ethyl acetate was added for extraction, the organic layer was separated, washed with 10 mL of saturated brine, dried over anhydrous magnesium sulfate, and precipitated under reduced pressure. Column chromatography separated 6.89 g of brown oil, yield 85.1%.

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Abstract

The invention discloses pyrazole cyclohexanediol ether compounds; the structure of the compounds is represented by the formula (I), and the definitions of each substituent are listed in the description. The compounds (I) can be used to control plant diseases caused by pathogenic bacteria such as oomycota, basidiomycetes, ascomycetes, fungi imperfecti, and the like, and especially has a good activity on controlling diseases such as cucumber downy mildew, corn rust, rice blast, and the like.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a pyrazole cyclohexanediol ether compound and its application and its use as a fungicide. Background technique [0002] The U.S. Uniroyal Company disclosed in the patent US3179682 an organosulfur acaricide Propargite with high efficiency, low toxicity, low residue, and dual effects of contact killing and stomach toxicity. [0003] [0004] Patent EP2149556 discloses compounds of the following general formula, which have herbicidal activity. [0005] [0006] In order to find and discover new types of pesticides that are more efficient, broad-spectrum, low-toxic, and low-ecological risk, we combined pyrazole rings with cyclohexanediol to design and synthesize a series of pyrazole cyclohexanediols with novel structures Ether compounds. The compound of general formula I in the present invention has a novel structure, and there is no relevant literature repo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/20C07D401/12A01N43/56A01P3/00A01P13/00
Inventor 关爱莹黄志王军锋王秀丽孙芹陈伟杨帆刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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