n1-(3-substituted pyrazole-5-formyl)-substituted phenoxyalkylhydrazide derivatives and their application

A technology of phenoxyalkyl hydrazide and formyl, which can be applied in application, biocide, animal repellent, etc., can solve the problem of reducing the sensitivity of pest populations, and achieve the effect of enriching species and alleviating the problem of drug resistance.

Inactive Publication Date: 2018-10-12
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, due to the long-term and large-scale use of existing insecticides, the sensitivity of pest populations to pesticides has decreased, making the resistance problems faced by many current insecticide varieties increasingly prominent, and more insecticide varieties with novel structures have been developed. , becomes an important way to solve the problem of resistance

Method used

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  • n1-(3-substituted pyrazole-5-formyl)-substituted phenoxyalkylhydrazide derivatives and their application
  • n1-(3-substituted pyrazole-5-formyl)-substituted phenoxyalkylhydrazide derivatives and their application
  • n1-(3-substituted pyrazole-5-formyl)-substituted phenoxyalkylhydrazide derivatives and their application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Compound I-1: 1 N-[5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole)-formyl]-4-chlorophenoxyacetylhydrazide

[0021]

[0022] (1) Take 0.0055mol 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid III, 3mL of thionyl chloride and 7mL of toluene and add it into a container equipped with a reflux condenser and a thermometer In a 25mL three-necked flask, heat up to 50-80°C for 4-5 hours, then distill off the remaining thionyl chloride and toluene to obtain 3-bromo-1-(3-chloropyridin-2-yl)- 1H-pyrazole-5-formyl chloride IV, directly used in the next step reaction;

[0023] (2) In a 50mL round bottom flask, add (0.005mol) intermediate 4-chlorophenoxyalkylhydrazide II, (0.003mol) K 2 CO 3 , 10 mL THF and 10 mL water. Add the intermediate 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride IV dropwise under stirring at room temperature, after the addition is complete, follow the reaction by TLC, stir at room temperature for 0.5~3h, and filter with...

Embodiment 2

[0097] Compound I-11: 1 N-[5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole)-formyl]-4-fluorophenoxyisopropionylhydrazide

[0098]

[0099] (1) Take 0.0055mol 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid III and 5mL of thionyl chloride and add it into a 25mL three- In the flask, the temperature was raised to 50-80°C for 4-5 hours, and then excess thionyl chloride was evaporated to obtain 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole- 5-Formyl chloride IV is directly used in the next step reaction;

[0100] (2) Add (0.005 mol) intermediate 4-fluorophenoxyisopropionohydrazide II, (0.006 mol) triethylamine, 10 mL THF and 10 mL water into a 50 mL round bottom flask. Add the intermediate 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride IV dropwise under stirring at room temperature, after the addition is complete, follow the reaction by TLC, stir at room temperature for 0.5~3h, and filter with suction , washed with water, recrystallized from et...

Embodiment 3

[0158] Compound I-19: 1 N-[5-(3-Trifluoromethyl-1-(pyridin-2-yl)-1H-pyrazole)-formyl]-4-chlorophenoxyacetylhydrazide

[0159]

[0160] (1) Take 0.0055mol 3-trifluoromethyl-1-(pyridin-2-yl)-1H-pyrazole-5-carboxylic acid III, 5mL of thionyl chloride, and 6mL of toluene and add them into a container equipped with a reflux condenser and a thermometer. In a 25mL three-necked flask, heat up to 50-80°C and react for 4-5 hours, then evaporate excess thionyl chloride to obtain 3-trifluoromethyl-1-(pyridin-2-yl)-1H- Pyrazole-5-carbonyl chloride IV was directly used in the next reaction.

[0161] (2) Add (0.005mol) intermediate 4-chlorophenoxyacetylhydrazide II in a 50mL round bottom flask, (0.006mol) K 2 CO 3 , 15 mL of water. Add the intermediate 3-trifluoromethyl-1-(pyridin-2-yl)-1H-pyrazole-5-carbonyl chloride IV dropwise under stirring at room temperature, after the addition is complete, follow the reaction by TLC, stir at room temperature for 0.5~3h, and filter with suction ...

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Abstract

The invention discloses a N1-(3-substituted pyrazol-5-formyl)-substituted oxygen alkyl benzene N-hydrazide derivative. The general formula of the derivative is I, (Please see the description for formula I.) wherein R represents halogen, hydrogen, nitryl, methyl, methoxyl and trifluoromethyl; R1 represents methyl, ethyl and hydrogen; R2 represents trifluoromethyl, chlorine, bromine and the like; R3 represents halogen and hydrogen. The type of compound has an obvious inhibition function on two insecticide targets including armyworms and plutella xylostella and can be used as an effective ingredient of insecticide.

Description

technical field [0001] The present invention relates to a kind of N 1 -(3-substituted pyrazole-5-formyl)-substituted phenoxyalkyl hydrazide derivatives and active components with insecticidal effect are used in the field of insecticides. Background technique [0002] In recent decades, heterocyclic compounds have attracted widespread attention from pesticide workers due to their high biological activity, and many commercial pesticides containing pyrazole and pyridine heterocycles have been continuously reported. Such as the herbicides Azimsulfuron, Pyrazolate, and Nipyraclofen; the insecticides Fenpyroximate, Chlorantraniliprole, and Nipyramide (Cyantraniliprole) etc. and fungicide pyraclostrobin (Pyraclostrobin) etc. In addition, compounds with active substructure bishydrazides often have good insecticidal activity, and have extensive research and important applications in the creation of new pesticides. Such as the insecticides Tebufenozide, Halofenozide and Methoxyfeno...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A01N43/56A01P7/04
CPCA01N43/56C07D401/04
Inventor 王威宁斌科王列平李秉擘毛明珍薛超
Owner XIAN MODERN CHEM RES INST
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