Bisamide compound and application thereof

A compound and bisamide technology, applied in the field of compounds, 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

[0003] 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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  • Bisamide compound and application thereof
  • Bisamide compound and application thereof
  • Bisamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Embodiment 1: the preparation of intermediate compound II.1

[0139]

[0140] Add 2.00 g (3.60 mmol) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (Intermediate IV-1 , prepared according to the method reported in WO2011093415 or WO2010018714), 0.74 g (5.35 mmol) of potassium carbonate and 0.58 g (4.30 mmol) of bromomethylcyclopropane, heated to 100°C for reaction. After the reaction was monitored by TLC, water and ethyl acetate were added for extraction, the organic phase was precipitated under reduced pressure, and the residue was purified by column chromatography to obtain 0.90 g of a white solid, namely intermediate II.1.

[0141] The NMR and mass spectrometry data of Intermediate II.1 are as follows:

[0142] 1 H NMR (600 MHz, Chloroform- d ) δ 8.21 (d, 1H), 7.87 (s, 2H), 7.42 – 7.36(m, 1H), 7.14 (t, 1H), 6.89 (td, 1H), 4.24 - 4.17 (br, 1H),3.07 - 3.02 (m,2H), 1.19 – 1.11 (m, 1H), 0.65 – 0.59 (m, 2H), 0.33 - 0.27 (m, 2H). LC-MS(m / z, E...

Embodiment 2

[0143] Embodiment 2: the preparation of intermediate compound II.2

[0144]

[0145]

[0146] Add 10 grams of N-(2-bromo-6-iodo-4-heptafluoroisopropylphenyl)-2-fluoro-3-nitrobenzamide (obtained with reference to the method reported in CN109206335A), 15 grams of anhydrous Stannous chloride, 200 ml of 1,4-dioxane and 8 ml of concentrated hydrochloric acid were heated to 60°C and stirred for reaction. After the reaction was monitored by TLC, the organic solvent was distilled off under reduced pressure. Add 500 ml of ethyl acetate, and add an appropriate amount of saturated aqueous sodium hydroxide solution to adjust the pH to 10. After stirring thoroughly, use diatomaceous earth to filter out the precipitated insoluble matter. After the filtrate is extracted with ethyl acetate and water, the organic layer is washed with anhydrous sulfuric acid. Dried over magnesium, filtered and concentrated under reduced pressure gave a beige solid, the crude product was purified by colum...

Embodiment 3

[0150] Embodiment 3: the preparation of intermediate compound II.3

[0151]

[0152] To 60 mL of DMF was added 2.00 g (3.67 mmol) of N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide (middle Body IV-3, prepared with reference to methods reported in WO2011093415, WO20110201687, WO2010013567 or WO2010018714), 0.76 g (5.50 mmol) of potassium carbonate and 0.60 g (4.44 mmol) of bromomethylcyclopropane, 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 precipitated under reduced pressure, and the residue was purified by column chromatography to obtain 0.73 g of a white solid, namely intermediate II.3.

[0153] The NMR and mass spectrometry data of intermediate II.3 are as follows:

[0154] 1 H NMR (600 MHz, Chloroform- d ) δ 8.27 (d, 1H), 8.14 (d, 1H), 7.91 (d,1H), 7.41 – 7.35 (m, 1H), 7.14 (t, 1H), 6.89 (td, 1H), 4.25 – 4.17 ( br, 1H),3.07 -...

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Abstract

The invention discloses a bisamide compound and application thereof. The structure of the compound is shown as a general formula I, wherein definitions of substituent groups in the formula are 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 bisamide compound and its application. Background technique [0002] Bisamide insecticides have been popular products in the market since their inception, and their representative varieties are flubendiamide and chlorantraniliprole, etc.; however, due to the long-term and irrational use of existing pesticides, the problem of resistance has intensified . On the other hand, the insecticidal effect of existing insecticides, especially the activity against rice stem borer, is still unsatisfactory, and it is difficult to meet the ever-increasing use requirements of insecticides in reality. In this field, it is still necessary to actively develop new insecticides with higher activity to meet the needs of agriculture and other fields. [0003] In the prior art, there is no report on the compound represented by the general formula I of the present invention and its insecticidal activity. Content...

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 张立新张静汪杰裴鸿艳盛祝波康卓
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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