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2,4-dimethyl oxazole acrylonitrile compound and application thereof

A compound and alkyl technology, applied in the field of insecticides and acaricides, can solve the problems that the insecticidal and acaricidal activities have not been disclosed, etc.

Active Publication Date: 2015-05-27
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, the preparation of 2,4-dimethyloxazolylacrylonitrile compounds and their insecticidal and acaricidal activities as shown in the present invention have not been disclosed

Method used

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  • 2,4-dimethyl oxazole acrylonitrile compound and application thereof
  • 2,4-dimethyl oxazole acrylonitrile compound and application thereof
  • 2,4-dimethyl oxazole acrylonitrile compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Embodiment 1, the preparation of compound 137

[0102] (1) Preparation of 2-bromothiobenzamide

[0103]

[0104] Add 2-bromobenzamide (50.00 g, 0.25 mol), Lawesson's reagent (109.10 g, 0.27 mol), and 200 ml of toluene into the three-necked flask, heat up to reflux, and react at reflux for 8 hours. After the reaction was completed, it was lowered to room temperature and filtered. The filtrate was washed with 2×200 ml of water, concentrated, and directly used in the next reaction without further purification.

[0105] (2) Preparation of 4-chloromethyl-2-(2-bromophenyl)thiazole

[0106]

[0107] Add the 2-bromothiobenzamide prepared in the previous step, 200 ml of methanol, and 1,3-dichloroacetone (34.30 g, 0.27 mol) into the three-necked flask, raise the temperature to reflux, and react under reflux for 16 hours. After the reaction was completed, it was lowered to room temperature and filtered. The filtrate was concentrated, and the residue was separated by colu...

Embodiment 2

[0117] Embodiment 2, the preparation of compound 375

[0118] (1) Preparation of 4-chloromethyl-2-(2-chlorophenyl)oxazole

[0119]

[0120] Add 2-chlorobenzamide (2.80 g, 0.018 mol) and 1,3-dichloroacetone (4.60 g, 0.036 mol) into a 100 ml round bottom flask, heat to melt, then continue to heat up to reflux and keep the reaction at 4 hours at reflux. After stopping the reaction, cool to room temperature naturally, pour into 50 ml of water, extract with 3 × 10 ml of ethyl acetate, wash the organic phase with 3 × 20 ml of saturated aqueous sodium chloride solution, dry with anhydrous magnesium sulfate, concentrate and column Chromatographic separation (eluent: ethyl acetate:petroleum ether=1:3) gave 3.10 g of 4-chloromethyl-2-(2-chlorophenyl)oxazole as a yellow solid with a yield of 77%.

[0121] (2) Preparation of 2-(2-chlorophenyl)-4-cyanomethyl oxazole

[0122]

[0123] Add 4-chloromethyl-2-(2-chlorophenyl) oxazole (45.50 g, 0.20 mol), 200 ml of dimethyl sulfoxide, s...

Embodiment 3

[0130] Embodiment 3, the preparation of compound 471

[0131] (1) 3-(2,4-dimethyloxazol-5-yl)-3-hydroxy-2-(2-(2,6-difluorophenyl)oxazol-4-yl)acrylonitrile preparation

[0132]

[0133] Under an ice-water bath, 2-(2-(2,6-difluorophenyl)oxazol-4-yl)acetonitrile (1.32 g, 0.006 mol), (2,4-dimethyloxa Azol-5-yl)(1H-pyrazol-1-yl)methanone (1.15 g, 0.006 mol), 20 ml of tetrahydrofuran, after stirring for about 30 minutes, potassium tert-butoxide (1.35 g, 0.012 mol) was added in batches After the addition, the reaction solution was warmed up to room temperature and reacted at room temperature for 2 hours. After stopping the reaction, the solvent in the system was distilled off under reduced pressure. After the residue was fully dissolved with 200 milliliters of water, the acid was adjusted to pH 2 to 3 with concentrated hydrochloric acid. Solids were precipitated in the system, filtered and dried to obtain 2.00 grams of 3-( 2,4-Dimethyloxazol-5-yl)-3-hydroxy-2-(2-(2,6-difluoroph...

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PUM

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Abstract

The invention discloses a 2,4-dimethylthiazole acrylonitrile compound or a stereoisomer thereof with a novel structure. The structure of the compound is shown in the general formal (I) in the specification, wherein R is selected from alkyl of C1-C6, halogenated alkyl of C1-C6, naphthene of C3-C8 or alkoxy of C1-C6; Q is selected from the group as shown in the specification; R1 is selected from H, halogen, methyl or trifluoromethyl; R2 is selected from H, halogen, methyl or trifluoromethyl; or the stereoisomer of the compound is selected. The compound in the general formula I has excellent insect and mite killing activity, and can be used for preventing and controlling insects and mites.

Description

technical field [0001] The invention belongs to the field of insecticides and acaricides. It specifically relates to a 2,4-dimethyloxazolyl acrylonitrile compound and an application thereof. Background technique [0002] Since insecticides and acaricides are used for a period of time, pests and harmful mites will develop resistance to them. Therefore, it is necessary to continuously invent new and improved compounds and compositions with insecticidal and acaricidal activities. Simultaneously, along with people's increasing demand for agricultural and livestock products and the increasing emphasis on environmental protection, new insecticides and acaricides with lower cost and environmental friendliness have always been required. [0003] In WO9740009, Nissan Chemical Industry Co., Ltd. disclosed ethylene derivatives having insecticidal, acaricidal or fungicidal activities. In the JP2003201280 application, the insecticidal activity of compound KC (No. 91 in the patent) is f...

Claims

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Application Information

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IPC IPC(8): C07D417/06C07D263/32C07D413/06A01N43/78A01N43/76A01N47/04A01N53/04A01P7/04A01P7/02
CPCA01N43/76A01N43/78A01N47/06A01N53/00C07D263/32C07D413/06C07D417/06
Inventor 李斌陈霖范晓溪英君伍班兰凤杨辉斌
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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