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Pyrazole amide derivative and application thereof

A technology of pyrazole amides and derivatives is applied in the field of agrochemical pesticide synthesis, which can solve the problems of increased consumer spending and reduced productivity, and achieve the effects of improving fat solubility and increasing insecticidal activity.

Inactive Publication Date: 2010-03-03
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Invertebrate pest damage to growing and stored crops can cause significant reductions in productivity and consequently increased costs to consumers

Method used

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  • Pyrazole amide derivative and application thereof
  • Pyrazole amide derivative and application thereof
  • Pyrazole amide derivative and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] 3-Acetoxy-1-(3-chloro-2-pyridyl)-N-[4-chloro-2-methyl-6-[((methyl)amino)-carbonyl]phenyl]-1H- Synthesis of pyrazole-5-carboxamide (derivative 01):

[0030] Step A: Preparation of 3-chloro-2-hydrazinopyridine

[0031] 200 mL of 50% hydrazine hydrate was slowly added to a solution of 2,3-dichloropyridine (73.5 g, 0.5 mol) in ethanol (300 mL) at room temperature, the reaction mixture was refluxed for 36 h, and cooled to room temperature; the white needle-like solid was collected by filtration, The solid was washed with cold ethanol (3×50 mL) to obtain 67.5 g of 3-chloro-2-hydrazinopyridine.

[0032] Step B: Preparation of ethyl 1-(3-chloro-2-pyridyl)-3-pyrazolidinone-5-carboxylate

[0033] Add 200mL of ethanol to a 500mL three-neck round bottom flask, slowly add sodium metal (6.9g, 0.3mol), when all the sodium metal has reacted completely, the reaction solution is heated to reflux, and 3-chloro- 2-Hydrazinopyridine (39.82 g, 0.277 mol). After the reaction mixture was r...

Embodiment 2

[0043] 3-Acetoxy-1-(3-chloro-2-pyridyl)-N-[4-bromo-2-methyl-6-[((isopropyl)amino)-carbonyl]phenyl]-1H - Synthesis of pyrazole-5-carboxamide (derivative 15):

[0044] Step A: Preparation of 2-amino-3-methyl-5-bromobenzoic acid

[0045] Dissolve 2-amino-3-methylbenzoic acid (10g, 66mmol) in 50mL DMF, slowly add NBS (11.7g, 66mmol) to it in portions, then heat to 100°C, react for 2h, pour into 200mL ice In the water, a white solid appeared, filtered, dissolved the solid with ethyl acetate, dried, and precipitated to obtain an off-white solid, which was washed with ether to obtain 12.9 g of 2-amino-3-methyl-5-bromobenzoic acid as a white solid.

[0046] Step B: Preparation of N-isopropyl-2-amino-3-methyl-5-bromobenzamide

[0047] Dissolve 2-amino-3-methyl-5-bromobenzoic acid (3.7g, 20mmol) in 40 mL of thionyl chloride, reflux for 4 hours, remove thionyl chloride under reduced pressure, and dissolve the residue in 20 mL of tetrahydrofuran, Slowly drop into the tetrahydrofuran so...

Embodiment 3

[0051] 3-Trifluoroethoxy-1-(3-chloro-2-pyridyl)-N-[4-chloro-2-methyl-6-[((cyclopropyl)amino)-carbonyl]phenyl] - Synthesis of 1H-pyrazole-5-carboxamide (derivative 18):

[0052] Step A: Preparation of ethyl 3-trifluoroethoxy-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylate

[0053] 3-Hydroxy-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid ethyl ester (1.0 g, 3.7 mmol) was dissolved in 20 mL DMF and potassium carbonate (0.76 g, 5.5 mmol) was added , heated to 100°C and added trifluoroiodoethane (0.94g, 4.4mmol) dropwise, continued reaction for 3h after dropping, diluted with water, extracted with ethyl acetate, dried, and precipitated to obtain 3-trifluoroethoxy-1- (3-Chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid ethyl ester 1.30 g.

[0054] Step B: Preparation of 3-trifluoroethoxy-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid

[0055] Dissolve ethyl 3-trifluoroethoxy-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylate (1.3g, 3.7mmol) in 20mL of methanol, add hydro...

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Abstract

The invention provides a pyrazole amide derivative. Based on the existing pyrazole amide compound, ether bonds or ester bonds are introduced; furthermore, nitryl or heptafluoro-iso-propyl is introduced into the pyrazole amide compound; and the pyrazole amide compound has a general formula shown at the right-lower part. The pyrazole amide compound has the technical effects that the fat-solubility of the existing compound is improved, simultaneously the insecticidal activity is also improved, the pyrazole amide compound is particularly effective to the lepidopterous pests such as oriental armyworm, diamondback moth, beet armyworm and the like, and is a pesticide with wide application prospects.

Description

technical field [0001] The invention relates to the synthesis technology of agricultural chemical insecticides, in particular to a class of pyrazole amide derivatives and applications thereof. Background technique [0002] Control of invertebrate pests is extremely important in achieving high planting efficiency. Damage to growing and stored crops by invertebrate pests can cause significant reductions in productivity and, consequently, increased costs to consumers. At the same time, the control of pests is also very important in forestry, animal husbandry, sideline, fishery and public health. Although there are many pest control agents on the market, due to the continuous expansion of the market, the resistance of pests, the service life of drugs and other issues and people's increasing attention to the environment, scientists need to continue to study, and then develop more effective and low-cost pesticides. , low toxicity, environmental safety and insecticide varieties w...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/56A01P7/04
Inventor 李正名赵毓冯启王宝雷李玉新李永强熊丽霞王素华
Owner NANKAI UNIV
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