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Substituted aryloxy pyridine compound and use thereof

A technology for aryloxypyridines and compounds, applied in applications, organic chemistry, biocides, etc., can solve problems such as structural compounds that have not been reported

Active Publication Date: 2014-05-07
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0028] In the prior art, the structure of the compound shown in the general formula I of the present invention has not been reported

Method used

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  • Substituted aryloxy pyridine compound and use thereof
  • Substituted aryloxy pyridine compound and use thereof
  • Substituted aryloxy pyridine compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0341] Embodiment 1: the preparation of intermediate 4,5-dichloro-6-methylpyrimidine

[0342] 1) Preparation of 4-hydroxy-5-chloro-6-methylpyrimidine

[0343]

[0344] Slowly add 8.80 g (0.16 mol) of sodium methoxide in methanol solution dropwise to 11.30 g (0.11 mol) of formamidine acetate in 50 ml of methanol solution under stirring at room temperature, and continue stirring at room temperature for 2 h after dropping. Then add 11.17g (0.068mol) intermediate ethyl 2-chloroacetoacetate dropwise to the above solution, and continue to stir the reaction at room temperature for 5-7 hours. After the reaction is monitored by TLC, the solvent is evaporated under reduced pressure, and the pH is adjusted to 5 with hydrochloric acid. ~6, suction filtered to get an orange solid, the aqueous phase was extracted with (3×50ml) ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and precipitated. The residue was dissolved in 50ml of ethyl acetate, left overnight, and filtere...

Embodiment 2

[0348] Embodiment 2: Preparation of intermediate 4,5-dichloro-6-difluoromethylpyrimidine

[0349] 1) Preparation of 4-hydroxy-5-chloro-6-difluoromethylpyrimidine

[0350]

[0351] Take 71.9g (0.70mol) of formamidine acetate in a 1000ml three-neck flask, add 150ml of methanol, stir at 5-10°C, and then put the pre-configured and cooled to room temperature 30 % methanol solution of sodium methoxide, pour it into the reaction flask, and then add 100g (0.50mol) of 2-chloro-4,4-difluoroacetoacetate in 100ml of methanol solution to the reaction mixture. The reaction mixture was stirred and reacted for 3-4 hours. After the completion of the reaction as monitored by TLC, the solvent was evaporated under reduced pressure, the pH was adjusted to 5-6 with hydrochloric acid, and 65 g of white solid was obtained by suction filtration. The yield is 73%, and the melting point is 204~206°C.

[0352] 2) Preparation of 4,5-dichloro-6-difluoromethylpyrimidine

[0353]

[0354] Dissolve ...

Embodiment 3

[0355] Embodiment 3: the preparation of intermediate 2-(6-(4-chlorophenoxy)pyridin-3-yl)ethylamine

[0356] 1) Preparation of methyl 6-(4-chlorophenoxy)nicotinate

[0357]

[0358] To 25.6g (0.2mol) of p-chlorophenol in 350mlN, N-dimethylformamide solution, add 103g (3.0mol) of 70% sodium hydride in batches, stir the reaction at room temperature for 4h, then add 34.2 g (0.2mol) methyl 6-chloronicotinate, after the addition is complete, the reaction mixture is heated to 100°C for 10 hours. After the reaction is monitored by TLC, the reaction solution is poured into water, extracted with ethyl acetate, and the organic phase is successively washed with water to saturate Wash with brine, dry, filter, and remove the solvent. After the residue is cooled and solidified, filter, wash with petroleum ether, and dry to obtain 42.0 g of light brown solid, namely methyl 6-(4-chlorophenoxy)nicotinate. Melting point: 64-66°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(pp...

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Abstract

The invention discloses a substituted aryloxy pyridine compound. The structure of the compound is shown in a general formula I, wherein each substituent is described in the specification. The compound with the general formula I has broad-spectrum sterilization and insecticidal activity in the agricultural field, has good prevention effects on a plurality of germs such as cucumber downy mildew, wheat powdery mildew, puccinia sorghi, rice blast and cucumber gray mold, and particularly has good prevention and control effects on the cucumber downy mildew and the puccinia sorghi under the condition of small dosage. In addition, a part of the compound has high insecticidal activity, and can be used for preventing and controlling armyworms, diamondback moths, myzus persicae, tetranychus cinnabarinus and the like.

Description

technical field [0001] The invention belongs to the field of agricultural sterilization and insecticide. Specifically, it relates to a substituted aryloxypyridine compound and its use. Background technique [0002] Patents EP0370704 and JP2009161472 disclose the following general formula and specific compounds (numbers in the two patents are respectively compound 47 and compound A), which have bactericidal and insecticidal activities. Now it has been developed into a commercial fungicide, the common name in English is diflumetorim, and the common name in Chinese is fluoxamethanil. Pesticide Science.1999,55:896-902 also discloses the following specific compound (numbered as compound 5 in the literature), and the bioassay results show that it has certain activity against wheat rust and barley powdery mildew. [0003] [0004] Fluoxin [0005] Patents JP11012253, JP11049759, and EP0665225 disclose the preparation method of the following compound (numbered as compound 7 in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A01N43/54A01P3/00A01P7/04A01P7/02
CPCA01N43/54C07D401/12
Inventor 刘长令关爱莹周继中孙旭峰王斌陈伟兰杰张金波宋玉泉
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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