1-substituted pyridyl-pyrazol acid amide compounds and use thereof

A technology for pyrazole amides and compounds, which is applied in the field of 1-substituted pyridyl-pyrazole amides, and can solve the problems that 1-substituted pyridyl-pyrazole amides have no insecticidal and bactericidal activities.

Active Publication Date: 2008-12-31
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, the preparation of 1-substituted pyridyl-pyrazole amide compounds as show

Method used

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  • 1-substituted pyridyl-pyrazol acid amide compounds and use thereof
  • 1-substituted pyridyl-pyrazol acid amide compounds and use thereof
  • 1-substituted pyridyl-pyrazol acid amide compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0131] Example 1, the preparation of compound 1.2

[0132] (1) Preparation of 2,4-dicarbonyl pentanoic acid methyl ester

[0133]

[0134] Add 25% methanol solution of sodium methylate (43.2 grams, 0.200 moles), 200 milliliters of methanol in the reaction flask, add dimethyl oxalate (23.6 grams, 0.200 moles) and acetone (11.6 grams, 0.200 moles) dropwise under ice-salt bath moles), the reaction system was maintained at 0-5°C and stirred for 8 hours. The reaction solution was poured into 200 ml of water, extracted with 150 ml of ethyl acetate to remove organic impurities, kept the inorganic phase, adjusted to pH 2-3 with concentrated hydrochloric acid, extracted with 3×200 ml of ethyl acetate, and the organic phase was washed with water, After washing with saturated brine, drying with anhydrous magnesium sulfate, and concentrating to obtain 25.9 g of yellow oil, the yield is 90%.

[0135] 1 H NMR (300MHz, CDCl 3 ): 6.396 (s, 1H, enol form), 3.906 (s, 3H), 2.279 (s, 3H). ...

example 2

[0153] Example 2, the preparation of compound 1.11

[0154] (1), 3,5, the synthesis of 6-trichloro-2-hydrazinopyridine

[0155]

[0156] Add 2,3,4,5-tetrachloropyridine (10 g, 46 mmol), 80% hydrazine hydrate (14 g, 230 mmol) and 100 milliliters of dioxane successively in the reaction flask, and stir at reflux temperature 20 hours. The reaction solution was cooled overnight, white crystals were precipitated, filtered and dried to obtain 6.1 g of solid, yield: 63%, melting point: 187-189°C.

[0157] 1 H NMR (300MHz, CDCl 3 ): 7.553 (s, 1H), 6.347 (br s, 1H), 3.927 (br s, 2H).

[0158] (2), the synthesis of 1-(3,5,6-trichloropyridin-2-yl)-5-(2-furyl)-3-trifluoromethyl-1H-pyrazole

[0159]

[0160] Add 4,4,4-trifluoro-1-(2-furyl)butane-1,3-dione (10 g, 48 mmol), 3,5,6-trichloro-2 -Hydrazinopyridine (10 g, 48 mmol), add glacial acetic acid (100 ml), heat to reflux, the reaction is complete, evaporate the solvent under reduced pressure, add ethyl acetate (300 ml), and se...

example 3

[0172] Example 3, the preparation of compound 1.17

[0173](1), 3, the synthesis of 5-dichloro-2-hydrazinopyridine

[0174]

[0175] 2,3,5-Trichloropyridine (20 g, 0.11 mol), 80% hydrazine hydrate (34 g, 0.55 mol) and 200 ml of dioxane were successively added to the reaction flask, and stirred at reflux temperature for 20 hours. The reaction solution was cooled overnight, white crystals were precipitated, filtered, and dried to obtain 14 g of solid, yield: 72%, melting point: 187-189°C.

[0176] 1 H NMR (300MHz, DMSO-d 6 ): 8.123(d, 1H), 7.849(d, 1H).

[0177] (2), the synthesis of 1-(3,5-dichloropyridin-2-yl)-3-pyrazolidinone-5-carboxylic acid ethyl ester

[0178]

[0179] Add 300 milliliters of absolute ethanol and sodium ethylate (4.1 grams, 61 mmoles), 3,5-dichloro-2-hydrazinopyridine (10 grams, 56 mmoles) in the reaction bottle, the mixture is heated to reflux for 5 minutes, drop Add diethyl maleate (10 g, 61 mmol). Heating to reflux was continued for 10 minut...

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Abstract

The invention discloses a novel-structured 1-substituent pyridyl-lactam pyrazole compound, with the structure shown in the general formula I; the definitions of each substituent group are stated in the instruction book. The compound in the general formula I is provided with excellent insecticidal and sterilizing activity and can be used to control pests and diseases. The technical proposal of the invention also comprises an intermediate for preparing the compound in the general formula I; the structure of the intermediate is shown in the general formula IV, and the definitions of each substituent group in the formula IV are stated in the instruction book.

Description

technical field [0001] The invention belongs to the field of insecticides and fungicides. It relates to a 1-substituted pyridyl-pyrazole amide compound and application thereof. Background technique [0002] Since insecticides and fungicides are used for a period of time, pests and germs will develop resistance to them, so it is necessary to continuously invent new and improved compounds and compositions with insecticidal and fungicidal activities. Simultaneously, along with people's increasing demand for agricultural and livestock products and the increasing emphasis on environmental protection, new insecticides and fungicides with lower cost and environmental friendliness have always been required. [0003] US2005 / 0075372A1 and WO2006102025A1 reported the preparation and insecticidal activity of the following compound (KC), which has a high control effect on armyworm and other pests at a concentration of 50 ppm: [0004] [0005] In the prior art, the preparation of th...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/56A01P7/00
CPCA01N43/56A61P3/00A61P7/00C07D401/04
Inventor 李斌杨辉斌王军锋于海波张弘李志念
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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