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Isoxazoline compound as well as preparation method and application thereof

A technology of isoxazolines and compounds, applied in the field of isoxazoline compounds and their preparation

Active Publication Date: 2021-01-05
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since insecticides and acaricides are used for a period of time, pests and mites will develop resistance to them, so new and improved new compounds with insecticide and acaricide activities need to be continuously developed; The growing demand for products and the increasing emphasis on environmental protection have also required the use of new insecticides and acaricides that are highly efficient, broad-spectrum and environmentally friendly

Method used

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  • Isoxazoline compound as well as preparation method and application thereof
  • Isoxazoline compound as well as preparation method and application thereof
  • Isoxazoline compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0143] Embodiment 1: the preparation of compound 109

[0144]

[0145] Add 0.30 g (0.57 mmol) of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) to the reaction flask -N-((R)-2-ethyl-3-oxooxazolidin-4-yl)-2-methylbenzamide, 20 ml toluene and 0.11 g (1.09 mmol) triethylamine, then add 66.35 mg (0.85 mmol) of acetyl chloride was heated to reflux for reaction. After the reaction was monitored by TLC, water was added to the reaction solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography to obtain 0.13 g of an oily substance.

[0146] The NMR and mass spectrometry data of compound 109 are as follows:

[0147] 1 H NMR (600 MHz, DMSO- d 6 ) δ 7.83 (t, 1H), 7.71 (s, 1H), 7.67 (dt, 1H),7.64 (d, 2H), 7.55 (d, 1H), 5.21 (t, 1H), 4.52 – 4.29 (m, 4H), 3.56 – 3.40(m, 2H), 2.40 (s, 3H), 2.15 (s, 3H), 1.13 (t, 3H). ESI-MS, m / Z: 594.23 [M+H+Na] + . ...

Embodiment 2

[0148] Embodiment 2: the preparation of compound 112

[0149]

[0150] Add 0.50 g (0.95 mmol) of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) to the reaction flask -N-((R)-2-ethyl-3-oxooxazolidin-4-yl)-2-methylbenzamide, 25 ml toluene and 0.19 g (1.88 mmol) triethylamine, then add 0.15 g (1.44 mmol) of cyclopropylformyl chloride was heated to reflux for reaction. After the reaction was monitored by TLC, water was added to the reaction solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography to obtain 0.29 g of a yellow solid.

[0151] The NMR and mass spectrometry data of compound 112 are as follows:

[0152] 1 H NMR (600 MHz, Chloroform- d ) δ 7.63 (d, 1H), 7.60 (s, 1H), 7.56 – 7.49(m, 3H), 7.44 (t, 1H), 5.56 (t, 1H), 4.56 – 4.42 (m, 2H), 4.08 ( d, 1H), 3.75– 3.56 (m, 3H), 2.52 (s, 3H), 1.40 – 1.15 (m, 4H), 1.11 – 0.94 (m, 2H), 0.60(...

Embodiment 3

[0153] Embodiment 3: the preparation of compound 113

[0154]

[0155] Add 1.00 g (1.89 mmol) of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) to the reaction flask -N-((R)-2-ethyl-3-oxooxazolidin-4-yl)-2-methylbenzamide, 30 ml toluene and 0.38 g (3.76 mmol) triethylamine, then add 0.31 g (2.87 mmol) of methoxyacetyl chloride was heated to reflux for reaction. After the reaction was monitored by TLC, water was added to the reaction solution and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography to obtain 0.53 g of an oily substance.

[0156] The NMR and mass spectrometry data of compound 113 are as follows:

[0157] 1 H NMR (600 MHz, DMSO- d 6) δ 7.82 (t, 1H), 7.72 (t, 1H), 7.68 – 7.65 (m,1H), 7.63 (d, 2H), 7.57 (dd, 1H), 5.08 (t, 1H), 4.49 – 4.28 ( m, 4H), 4.15 (s,2H), 3.57 – 3.36 (m, 2H), 3.22 (s, 3H), 2.39 (s, 3H), 1.12 (t, 3H). ESI-MS,m / ...

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Abstract

The invention discloses an isoxazoline compound as well as a preparation method and application thereof. The structure of the compound is shown as a general formula I, wherein the definitions of the substituent groups in the formula are shown in the specification. Also disclosed in the specification is the use of the compound shown as the general formula I as an insecticide, an acaricide and an animal parasite control agent.

Description

technical field [0001] The invention relates to an isoxazoline compound, in particular to a novel isoxazoline compound and a preparation method and application thereof. Background technique [0002] Patent CN102639529A relates to certain isoxazoline derivatives with insecticidal activity. However, since insecticides and acaricides are used for a period of time, pests and mites will develop resistance to them, so new and improved new compounds with insecticide and acaricide activities need to be continuously developed; The increasing demand for products and the increasing emphasis on environmental protection have also required the use of new insecticides and acaricides with high efficiency, broad spectrum and environmental friendliness. Contents of the invention [0003] The object of the present invention is to provide an isoxazoline compound with good insecticidal and acaricidal activity and its preparation method and application. The isoxazoline compound can be used fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/04C07D275/02C07D261/12C07D417/12C07D413/12A01N43/80A01P7/04A01P7/02
CPCC07D261/04C07D275/02C07D261/12C07D417/12C07D413/12A01N43/80A01N53/00A01N47/12A01P7/04Y02A50/30A61P33/14A61K31/42
Inventor 张立新张静高一星康卓
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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