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Pyrazolopyridine ureide compound and application thereof

A technique for pyridylpyrazole urea and compounds, which is applied in the field of agricultural pesticides and can solve the problems that pyridylpyrazole urea compounds have not been disclosed.

Inactive Publication Date: 2015-12-16
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the compounds disclosed in the above-mentioned patents have similarities with the compounds of the present invention, in the prior art, the pyridine pyrazole urea compounds (formula I) described in the present invention have not been disclosed

Method used

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  • Pyrazolopyridine ureide compound and application thereof
  • Pyrazolopyridine ureide compound and application thereof
  • Pyrazolopyridine ureide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0023] The preparation of example 1, compound 1

[0024] (1) Synthesis of 2-amino-N-furanmethylbenzamide

[0025]

[0026] Add 16.3g (0.1mol) isatoic anhydride and 180mL water to a 250mL reaction flask, drop in 14.55g (0.15mol) furfurylamine (2-furylmethylamine), react at room temperature for 12h, filter with suction, filter cake in 10mL×2 Washed with tap water and dried to obtain 18.4 g of white solid with a yield of 85%.

[0027] (2) Synthesis of 2-amino-3,5-dichloro-N-furanmethylbenzamide

[0028]

[0029] Add 21.6g (0.1mol) of 2-amino-N-furylmethylbenzamide and 150g of ethyl acetate to a 250mL reaction flask, add 33.75g (0.25mol) of sulfuryl chloride dropwise at a temperature below 15°C, and control the temperature after dropping After reacting at 15°C for 4-5 hours, TLC detected that the raw materials disappeared, filtered with suction, washed the filter cake with 20 mL×2 ethyl acetate, and dried to obtain 22.37 g of white solid, with a yield of 78.5%.

[0030] (...

example 2

[0039] The preparation of example 2, compound 2

[0040] (1) Preparation of 2-amino-N-isopropylbenzamide

[0041]

[0042] Add 16.3g (0.1mol) isatoic anhydride, 100ml ethyl acetate, 1.5g glacial acetic acid to a 250mL reaction flask, add 0.15mol isopropylamine dropwise at 40-50°C, continue to react at room temperature for 2 hours, and evaporate the solvent , to obtain a white powdery solid, washed with water to remove isopropylamine hydrochloride, and dried to obtain 15.1 g of a white solid, with a yield of 85.8%.

[0043] (2) Synthesis of 2-amino-3,5-dichloro-N-isopropylbenzamide

[0044]

[0045] Add 17.8 g (0.1 mol) of 2-amino-N-isopropylbenzamide and 100 mL of ethyl acetate to a 250 mL reaction flask, and add SO 2 Cl 2 33.75g (0.25mol), after dropping, stirred for 4h, suction filtered and washed with water to obtain 20.7g of off-white solid with a yield of 83.8%.

[0046] (3) Synthesis of Compound 2

[0047]

[0048] Add 2.47g (0.01mol) 2-amino-3,5-dichloro-N...

example 3

[0049] The preparation of example 3, compound 3

[0050] (1) Synthesis of 2-amino-3,5-dichloro-N-isopropylthiobenzamide

[0051]

[0052] Add P to the 500mL reaction bottle 2 S 5 11.1g (0.05mol), 150mL of dichloromethane, stirred at room temperature, added 24.7g (0.1mol) of 2-amino-3,5-dichloro-N-isopropylbenzamide, heated to reflux for 1h until the reaction of raw materials was completed , add 150mL of water, neutralize pH 6-7 with 20% NaOH aqueous solution, evaporate dichloromethane to obtain 24.2g of yellow solid, yield 92%.

[0053] (2) Synthesis of compound 3

[0054]

[0055] Add 2.63g (0.01mol) 2-amino-3,5-dichloro-N-isopropylthiobenzamide and 10mL dichloroethane to a 100mL reaction flask, add 3.61g (0.011mol) 1-( 3-Chloropyridin-2-yl)-3-difluoroethoxy-1-H-pyrazole-5-formyl isocyanate diluted in 6mL dichloroethane, reacted at room temperature for 4h to 2-amino-3,5 Dichloro-N-furanmethylbenzamide disappeared, added 20g of water, distilled out dichloromethane, ...

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PUM

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Abstract

The invention discloses a pyrazolopyridine ureide compound. In a structural general formula I, R1 is selected from CH(CH3)2 or furfuryl, and Y is selected from O or S. The compound shown in the general formula I has an excellent insecticidal activity, has an unexpected ultrahigh activity on the lepidoptera pests such as diamond back moths, beet armyworms and rice stem borers, also has a good killing effect on the piercing-sucking type pests such as trialeurodes vaporariorum and pest mites, and can be used for preventing and controlling agricultural or forest pests.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides, and relates to a pyridine pyrazole urea compound and an application thereof. Background technique [0002] The resistance of pests is the main source of their difficulty in control, and the development of new control agents is an important way to control resistance. Anthranilamide compounds (ryanodine receptor inhibitors) are effective insecticides developed in recent years to control Lepidoptera pests. [0003] Patent application CN2013 / 10043844 discloses the following difluoroethoxy-containing compounds with insecticidal activity: [0004] [0005] Although the compounds disclosed in the above patents have similarities with the compounds of the present invention, in the prior art, the pyridine pyrazole urea compounds (formula I) described in the present invention have not been disclosed. Contents of the invention [0006] The object of the present invention is to provide a pyridi...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D405/14A01N47/34A01P7/04A01P7/02
CPCA01N47/34C07D401/04C07D405/14
Inventor 许良忠王明慧张画轻杨曦黄雪松
Owner QINGDAO UNIV OF SCI & TECH
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