Isoxazoline compound and application thereof

A technology of isoxazolines and compounds, which is applied in the field of isoxazoline compounds, can solve the problems that insecticidal and acaricidal activities have not been reported.

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

[0007] In the prior art, there is no report on the compounds shown in the general formula I of the present invention and their insecticidal and acaricidal activities

Method used

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  • Isoxazoline compound and application thereof
  • Isoxazoline compound and application thereof
  • Isoxazoline compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Embodiment 1: the preparation of compound 1

[0114]

[0115] Add 0.50 g (0.90 mmol) 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) to the one-necked bottle -2-methyl-N-(2-oxo-2-(2,2,2-trifluoroethyl)amino)ethylbenzamide, 25 ml toluene and 0.18 g (1.80 mmol) triethylamine, Then add 0.14 g (1.35 mmol) cyclopropylformyl chloride, and heat up to reflux for 3 hours. 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 0.30 g of a white solid.

[0116] The NMR and mass spectrometry data of compound 1 are as follows:

[0117] 1 H NMR (600 MHz, DMSO- d 6 ) δ 8.82 (t, 1H), 7.81 (t, 1H), 7.69 – 7.60 (m,4H), 7.54 (d, 1H), 4.47 (s, 2H), 4.39 (d, 1H), 4.30 (d, 1H), 3.99 – 3.88 (m,2H), 2.38 (s, 3H), 1.77 – 1.68 (m, 1H), 0.84 –0.64 (m, 4H). ESI-MS, m / Z :646.24 [M+H+Na] + .

Embodiment 2

[0118] Embodiment 2: the preparation of compound 2

[0119]

[0120] Compound 2 (yellow solid) was prepared according to the synthesis method of Example 1. The NMR and mass spectrometry data of compound 2 are as follows:

[0121] 1 H NMR (600 MHz, DMSO- d 6 ) δ 8.86 (t, 1H), 7.85 (d, 2H), 7.71 – 7.63 (m,2H), 7.58 (d, 1H), 4.51 (s, 2H), 4.42 (d, 1H), 4.35 (d, 1H), 4.04 – 3.93 (m,2H), 2.42 (s, 3H), 1.83 – 1.74 (m, 1H), 0.88 –0.70 (m, 4H). ESI-MS, m / Z :664.15 [M+H+Na] + .

Embodiment 3

[0122] Embodiment 3: the preparation of compound 19

[0123]

[0124] Add 0.50 g (0.90 mmol) 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl) to the one-necked bottle -2-methyl-N-(2-oxo-2-(2,2,2-trifluoroethyl)amino)ethylbenzamide, 20 ml toluene and 0.18 g (1.80 mmol) triethylamine, Then add 0.15 g (1.35 mmol) of methoxyacetyl chloride, and heat up to reflux for 3 hours. 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 0.27 g of a brown oil.

[0125] The NMR and mass spectrometry data of compound 19 are as follows:

[0126] 1 H NMR (600 MHz, DMSO- d 6 ) δ 8.75 (t, 1H), 7.82 (t, 1H), 7.68 (s, 1H),7.66 – 7.60 (m, 3H), 7.50 (d, 1H), 4.38 (d, 1H), 4.32 (s, 2H), 4.31 (d, 1H), 4.25 (s, 2H), 3.96 – 3.84 (m, 2H), 3.26 (s, 3H), 2.34 (s, 3H). ESI-MS, m / Z :626.22 [M-H] - .

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Abstract

The invention discloses an isoxazoline compound and application thereof. The structure of the isoxazoline compound is shown as a general formula I, wherein the definitions of the substituent groups inthe 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 a compound, in particular to a novel isoxazoline compound and its application. Background technique [0002] Patent CN1930136A discloses the following specific compound KC1 (CAS: 930108-84-2; substituent (X) of general formula [I]-11 in Table 2 m 3, 5-Cl 2 , R 3 for CF 3 , R 2 for C(O)OCH 3 , R 1 for CH 2 C(O)NHCH 2 CF 3 (line 1 on page 146 of the description)), KC2 (the substituent (X) of the general formula [I]-11 in Table 2 m 3, 5-Cl 2 , R 3 for CF 3 , R 2 for C(O)CH 3 , R 1 for CH 2 C(O)NHCH 2 CF 3 (the penultimate line on page 145 of the instruction manual)), KC3 (the substituent (X) of the general formula [I]-11 in Table 2 m 3,5-Cl 2 , R 3 for CF 3 , R 2 for C(O)Et, R 1 for CH 2 C(O)NHCH 2 CF 3 (the penultimate line on page 145 of the instructions)), it has certain insecticidal activity. [0003] [0004] [0005] [0006] However, the insecticidal and acaricidal effects of these discl...

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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