O-formylamino benzamide derivative containing N-cyano sulfone(sulfur) imine and preparation method and use thereof

A technology of o-formamidobenzamide and cyanosulfone, applied in the field of o-formamidobenzamide derivatives, can solve the problem of no activity exceeding the activity of the target molecule parent

Active Publication Date: 2013-06-26
NANKAI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many domestic research institutes are carrying out related creative research work, and there is no report that the activity exceeds the activity of the target molecule parent

Method used

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  • O-formylamino benzamide derivative containing N-cyano sulfone(sulfur) imine and preparation method and use thereof
  • O-formylamino benzamide derivative containing N-cyano sulfone(sulfur) imine and preparation method and use thereof
  • O-formylamino benzamide derivative containing N-cyano sulfone(sulfur) imine and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of 3-methyl-5-halo-2-aminobenzoic acid III:

[0055]

[0056] In a 100 ml round bottom flask, add 3.0 g, 20 mmol 3-methyl-2-aminobenzoic acid X, 30 ml DMF, 6.7 g, 30 mmol NCS (or 30 mmol NBS), and stir at reflux for 3 hours , pour the reaction solution into ice water, acidify with dilute hydrochloric acid to pH=6, filter, and wash the obtained solid with a small amount of ethanol to obtain 2-amino-3-methyl-5-halo-benzoic acid III, gray solid, more than 4.6 g , the yield is greater than 83%. Y is selected from: chlorine, bromine, and the 2-amino-3-methyl-5-halo-benzoic acid III is selected from the group consisting of -2-amino-3-methyl-5-chlorobenzoic acid, 2-amino-3 -Methyl-5-bromo-benzoic acid; where, 2-amino-3-methyl-5-chlorobenzoic acid 1 H NMR (400MHz, DMSO-d 6 ): δ: 7.96(s, 1H), 7.56(d, 1H), 7.23(d, 1H), 2.11(s, 3H); 2-amino-3-methyl-5-bromobenzoic acid 1 H NMR (300MHz, DMSO-d 6 ): δ: 7.70 (s, 1H), 7.31 (s, 1H), 2.10 (s, 3H).

Embodiment 2

[0058] 3-Halo-1-(3-chloropyridin-2-yl)-N-(4-halo-2-methyl-6-((2-(methylthio)alkyl)carbamoyl)benzene base)-1H-pyrazole-5-carboxamide preparation

[0059] (1) Synthesis of 3-chloro-2-hydrazinopyridine VI:

[0060]

[0061] Add 50 mmoles of 2,3-pyridine V, 100 mmoles of hydrazine hydrate, and 50 ml of ethanol into a 100 ml three-necked round-bottomed flask, heat and reflux at 80 degrees Celsius for 20 hours, evaporate the solvent under reduced pressure, and weigh the obtained solid with ethanol Crystallization gave 6.5 g of needle-like crystals of 3-chloro-2-hydrazinopyridine VI, with a yield of 90%.

[0062] (2) Synthesis of ethyl 5-oxo-2-(3-chloropyridin-2-yl)pyrazoline-3-carboxylate VII:

[0063]

[0064] Add 100 ml of absolute ethanol to a 250 ml single-necked round-bottom flask, add 1.77 g or 55 mmol of sodium metal in batches, the temperature rises slightly, and form a homogeneous transparent solution after stirring for 10 minutes; add 7.1 g or 50 mmol of 3-chloro ...

Embodiment 3

[0081] 1-(3-Chloropyridin-2-yl)-3-halo-1H-pyrazole-5-formyl-2-methyl-4-halo-6-(2-((N-cyanomethyl Synthesis of (sulfimino)alkyl)carbamoyl)aniline IB

[0082]

[0083]In a 50 ml three-neck round bottom flask, add 0.53 g, namely 1.0 mmol 3-halo-1-(3-chloropyridin-2-yl)-N-(4-halo-2-methyl-6-(2 -(methylthioalkyl)carbamoyl)phenyl)-1H-pyrazole-5-carboxamide IA was added to 30 ml of dry tetrahydrofuran, stirred, and cooled to 0°C in an ice-water bath. Then add 0.16 g, 4 mmol cyanamide and 0.33 g, 1.0 mmol iodobenzene acetate respectively, stir at this temperature for 3 hours, then stir overnight at room temperature, the next day, the reaction solution is directly decompressed to remove the solvent, and the residue is subjected to 200~ Purified by 300-mesh silica gel column chromatography to obtain white solid IB, the eluent was ethyl acetate, and the physical and chemical parameters of IB are shown in Table 1. The 1-(3-chloropyridin-2-yl)-3-halo-1H-pyrazole-5-formyl-2-methyl-4-ha...

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Abstract

The invention provides an o-formylamino benzamide derivative containing N-cyano sulfone(sulfur) imine and a preparation method and use thereof. The invention relates to a bisamide derivative containing pyrazole formamide, wherein the bisamide derivative containing pyrazole formamide has a chemical structural general formula shown in I. The invention discloses structural general formulae and synthesis methods of the compounds, use of the compounds serving as insecticide, bactericide, plant virus resisting agents and plant activators and processing processes for the compounds in the preparation of insecticide, bactericide, plant virus resisting agents and plant activators in a manner of being mixed with agriculturally-acceptable assistants or synergists. The invention further discloses use of the compounds in the prevention and treatment of the diseases, insect pests and viral diseases of agriculture, forestry and horticulture in a manner of being combined with the commercial insecticide, bactericide, plant virus resisting agents and plant activators and preparation methods thereof.

Description

technical field [0001] The technical scheme of the present invention relates to pyrazole compounds, specifically o-formamidobenzamide derivatives containing N-cyanosulfone (sulfur) imine. Background technique [0002] Since Dr. Tsuda reported that a series of pyrazine diamides have certain insecticidal activity at Osaka Prefecture University in Japan in 1989, diamides have become the research hotspots of major pesticide companies and research institutes in the world. It was not until 1998 that the Japanese pesticide company discovered the first bisamide insecticide --- flubendiamide (EP1006107). In addition to the advantages of excellent activity, no cross-resistance with existing insecticides, and safety to mammals, this type of insecticide also has a unique mechanism of action. The unique action mechanism of the bisamide insecticide may be to inhibit the release of calcium ions and become a ryanodine receptor activator. This unique mechanism of action quickly attracted t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A01N47/40A01N43/56A01P3/00A01P7/04A01P7/02A01P1/00
Inventor 范志金华学文陈旭艳毛武涛陈晓燕梁小文刘细平姬晓恬李娟娟宗广宁李凤云李岳东房震王曙华周立峰黄亮文
Owner NANKAI UNIV
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