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Isophthalamide compound and application thereof

A technology of isophthalamide and compound, which is applied in the field of isophthalamide compounds, and can solve problems such as unreported insecticidal activity.

Active Publication Date: 2021-03-02
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, there is no report on the compounds shown in the general formula I of the present invention and their insecticidal activity

Method used

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  • Isophthalamide compound and application thereof
  • Isophthalamide compound and application thereof
  • Isophthalamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0164]Example 1: Preparation of intermediate compound II.1

[0165]

[0166]To 30 ml of DMF was added 1.00 g (1.80 mmol) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (Intermediate IV-1 , Prepared by referring to the method reported in WO2011093415 or WO2010018714), 0.37 g (2.68 mmol) of potassium carbonate, 0.27 g (1.80 mmol) of sodium iodide and 0.26 g (2.19 mmol) of bromoacetonitrile, heated to 100 degrees for reaction. After the reaction was monitored by TLC, water and ethyl acetate were added for extraction, the organic phase was desolvated under reduced pressure, and the residue was purified by column chromatography to obtain 0.50 g of a white solid, that is, intermediate II.1. The NMR and MS data of Intermediate II.1 are as follows:

[0167]1H NMR (600 MHz, Chloroform-d) δ 8.11 (d, 1H), 7.88 (s, 2H), 7.64-7.58(m, 1H), 7.29 (t, 1H), 7.05 (td, 1H), 4.52 -4.44(br, 1H), 4.24 ( d, 2H). LC-MS(m / z, ESI): 594.01(M+H)+.

Embodiment 2

[0168]Example 2: Preparation of intermediate compound II.2.

[0169]

[0170]To 50 ml of DMF was added 1.50 g (2.70 mmol) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (Intermediate IV-1 ), 0.56 g (4.05 mmol) of potassium carbonate, 0.41 g (2.74 mmol) of sodium iodide and 0.43 g (3.21 mmol) of bromopropionitrile, the temperature is raised to 100 degrees for reaction. After the reaction was monitored by TLC, water and ethyl acetate were added for extraction, the organic phase was desolvated under reduced pressure, and the residue was purified by column chromatography to obtain 0.25 g of a white solid, namely Intermediate II.2. The NMR and MS data of Intermediate II.2 are as follows:

[0171]1H NMR (600 MHz, Chloroform-d) δ 8.16 (d, 1H), 7.87 (s, 2H), 7.52 – 7.46(m, 1H), 7.20 (t, 1H), 6.90 (td, 1H), 4.46-4.40 (m, 1H), 3.66 – 3.60 (m,2H), 2.72 (t, 2H). LC-MS(m / z, ESI): 608.01(M+H)+.

Embodiment 3

[0172]Example 3: Preparation of Intermediate Compound II.3

[0173]

[0174]To 30 ml of DMF was added 1.00 g (1.80 mmol) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (Intermediate IV-1 ), 0.37 g (2.68 mmol) of potassium carbonate, 0.27 g (1.80 mmol) of sodium iodide and 0.32 g (2.16 mmol) of bromobutyronitrile, heated to 100 degrees for reaction. After the reaction was monitored by TLC, water and ethyl acetate were added for extraction, the organic phase was desolventized under reduced pressure, and the residue was purified by column chromatography to obtain 0.12 g of white solid, which is intermediate II.3. The NMR and MS data of Intermediate II.3 are as follows:

[0175]1H NMR (600 MHz, Chloroform-d) δ 8.16 (d, 1H), 7.87 (s, 2H), 7.46-7.42 (m, 1H), 7.18 (t, 1H), 6.94 (td, 1H), 4.17-4.10 (m, 1H), 3.43 ( q, 2H), 2.54(t, 2H), 2.08-2.02 (m, 2H). LC-MS(m / z, ESI): 622.03(M+H)+.

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Abstract

The invention discloses an isophthalamide compound and application thereof. The structure of the compound is shown as a general formula I, wherein the definition of each substituent group in the formula is shown in the specification; the specification also discloses the uses of the compound as insecticides and animal parasite control agents.

Description

Technical field[0001]The invention relates to a compound, in particular to a novel isophthalamide compound and its application.Background technique[0002]Patent CN102112437A discloses compound CK1 (Compound No. 5-108), which has insecticidal activity.[0003][0004]In the prior art, the compound represented by the general formula I of the present invention and its insecticidal activity have not been reported.Summary of the invention[0005]The object of the present invention is to provide an isophthalamide compound with excellent insecticidal activity. It can be used to prepare drugs for controlling pests in agriculture and other fields, and for preparing drugs for controlling animal parasites in the field of veterinary medicine.[0006]In order to achieve the purpose of the present invention, the present invention provides the following technical solutions:[0007]An isophthalamide compound, as shown in general formula I:[0008][0009]In the general formula I:[0010]R1Selected from halogen;[001...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82C07D213/84C07C237/40C07C255/42A01N43/40A01P7/00A61K31/44A61P33/00
CPCC07D213/82C07D213/84C07C237/40C07C255/42A01N43/40A61K31/44A61P33/00C07C2601/02C07D213/26A01P7/04A01N37/44C07C255/57Y02A50/30A01N37/22C07D213/16
Inventor 张立新张静裴鸿艳汪杰盛祝波康卓
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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