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Preparation and application of 4-chlorine-3-ethyl-1-methyl-N'-(2-substituted phenoxy acetyl)-1H-pyrazol-5-carbohydrazide compounds

A technology of phenoxyacetylhydrazine and phenoxyacetyl, applied in 4-chloro-3-ethyl-1-methyl-N'-(2-substituted phenoxyacetyl)-1H-pyrazole- The preparation and application fields of 5-carbohydrazide compounds achieve the effects of convenient operation, improved purity and yield, and improved reaction efficiency

Active Publication Date: 2014-12-10
YIFAN AGRI CHEM PLANT ZHEJIANG PROV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, no information on 4-chloro-3-ethyl-1-methyl- N' -(2-substituted phenoxyacetyl)-1 H -Reports on the Synthesis of Pyrazole-5-carbohydrazides and Their Biological Activities

Method used

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  • Preparation and application of 4-chlorine-3-ethyl-1-methyl-N'-(2-substituted phenoxy acetyl)-1H-pyrazol-5-carbohydrazide compounds
  • Preparation and application of 4-chlorine-3-ethyl-1-methyl-N'-(2-substituted phenoxy acetyl)-1H-pyrazol-5-carbohydrazide compounds
  • Preparation and application of 4-chlorine-3-ethyl-1-methyl-N'-(2-substituted phenoxy acetyl)-1H-pyrazol-5-carbohydrazide compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0036] 4-chloro-3-ethyl-1-methyl- N' -(2,4-Dichlorophenoxyacetyl)-1 H -Pyrazole-5-carbohydrazide (1): beige, yield: 81%, melting point: 161-163°C; 1 H NMR (CDCl 3 , 400MHz), : 1.27(t, J =4.0Hz,3H,CH 3 ), 2.59-2.70(m,2H,CH 2 ),4.09(s,3H,NCH 3 ),4.71(s,2H,COCH 2 O), 6.87-6.90 (m, 1H, Ar-H), 7.43-7.82 (m, 1H, Ar-H), 7.24 (m, 1H, Ar-H), 9.13 (s, 2H, CONH).

Embodiment 2

[0038] 4-chloro-3-ethyl-1-methyl- N' -(2,3-Dichlorophenoxyacetyl)-1 H -Pyrazole-5-carbohydrazide (2): white, yield: 88%, melting point: 238-240°C; 1 H NMR(CDCl 3 ,400MHz), :1.26(t,J=4.0Hz, 3H,CH 3 ),2.56-2.69(m,2H,CH 2 ), 4.10(s, 3H, NCH 3 ),4.73(s, 2H, COCH 2 O), 6.87-6.90(m, 1H, Ar-H), 7.40-7.81(m, 1H, Ar-H), 7.20(m, 1H, Ar-H), 9.13(s, 2H, CONH).

Embodiment 3

[0040] 4-chloro-3-ethyl-1-methyl- N' -(2-Chlorophenoxyacetyl)-1 H -Pyrazole-5-carbohydrazide (3): off-white, yield: 86%, melting point: 149-151 ? C; 1 H NMR (CDCl 3 , 400MHz), : 1.26(t, J =7.60Hz,3H,CH 3 ),2.64-2.69(m,2H,CH 2 ),4.16(s, 3H,NCH 3 ),4.74(s,2H,COCH 2 O), 6.95-7.00 (m, 1H, Ar-H), 7.01-7.05 (m, 1H, Ar-H), 7.27-7.31 (m, 1H, Ar-H), 7.43-7.45 (m, 1H, Ar-H), 9.12 (s, 1H, CONH), 9.23 (s, 1H, CONH).

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Abstract

The invention discloses preparation and application of 4-chlorine-3-ethyl-1-methyl-N'-(2-substituted phenoxy acetyl)-1H-pyrazol-5-carbohydrazide compounds. The preparation comprises the following steps: carrying out backflow reaction on thionyl chloride and N-methyl-3-ethyl-4-chloride pyrazole carboxylic acid for 1h to obtain a compound (II), putting the mixed liquor of a compound (III), an organic solvent and an acid-binding agent in a round-bottom flask, dropwise adding the compound (II) at 20-30 DEG C while stirring, then heating up to backflow reaction, carrying out TLC tracing until the raw materials are completely reacted, stopping the reaction, respectively extracting by using 50ml of water twice, drying the organic layer by anhydrous NaSO4, evaporating out the solvent under reduced pressure, and carrying out recrystallization to obtain the target compound shown in the formula (I). According to the preparation and the application, the reaction conditions are mild, the postprocessing is convenient and the total yield of the reaction is as high as 81%; and the compound has a herbicidal activity, thus laying a foundation for the research and development of new pesticides.

Description

technical field [0001] The present invention relates to a kind of 4-chloro-3-ethyl-1-methyl- N' -(2-substituted phenoxyacetyl)-1 H - Preparation and application of pyrazole-5-carbohydrazide compounds. Background technique [0002] Dihydrazide compounds are attractive due to their rapid development and wide range of applications. Among them, the biological activity of dihydrazide structural units as insect growth regulators has been widely recognized. They are widely used in pesticides, biomedical materials, electroluminescence, Liquid crystal materials and other fields also have important application value. For example, in the field of pesticides, commercialized N-tert-butyl-N'-4-ethylbenzoyl-N-3,5-dimethylbenzoylhydrazide (compound 1 , also known as tebufenozide) is safe for mammals and non-target organisms, and has high insecticidal activity against resistant pests, and has a better stomach poisoning effect on oriental armyworm and Spodoptera litura; [0003] [000...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/16A01N43/56A01P13/00
CPCA01N43/56C07D231/16
Inventor 吴克崇吴贯中谭成侠王学胜
Owner YIFAN AGRI CHEM PLANT ZHEJIANG PROV
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