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Crystal of phenyl ketoenol derivative, method for producing the same, and pesticide composition containing the crystal

A kind of pesticide composition, the technology of phenyl ketone enol, which is applied to the crystal of phenyl ketone enol derivative and its preparation, and the field of pesticide composition containing the crystal, can solve the problem that it is difficult to prepare a high-content emulsifiable concentrate preparation, solubility Problems such as low stability of phenyl ketone enol derivatives need to be improved

Active Publication Date: 2022-02-11
HEBEI LANSHENG BIOTECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The phenyl ketone enol derivative shown in formula (1) is a kind of insecticide disclosed in the patent document CN103102346A, but the phenyl keto enol derivative shown in the formula (1) disclosed and prepared in this document is An oil, which is used in the form of an emulsifiable concentrate with an organic solvent in practical applications, and has low solubility in solvents such as solvent naphtha, cyclohexanone, xylene, vegetable oil, etc. commonly used to prepare emulsifiable concentrates, so The content of this compound in the emulsifiable concentrate can only reach 6%, and it is difficult to make a high-content emulsifiable concentrate. The low content leads to the need to increase the dosage to obtain a good effect when applying it. Correspondingly, it will lead to a large amount of organic The adverse effects of solvents on the environment also cause difficulties in production, transportation and storage
Due to the increasingly stringent environmental protection restrictions in recent years, the use of this type of emulsifiable pesticide has been greatly restricted
In addition, there is also the problem that the stability of the phenyl ketone enol derivatives represented by the formula (1) in the form of oil in the emulsifiable concentrate preparation needs to be improved

Method used

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  • Crystal of phenyl ketoenol derivative, method for producing the same, and pesticide composition containing the crystal
  • Crystal of phenyl ketoenol derivative, method for producing the same, and pesticide composition containing the crystal
  • Crystal of phenyl ketoenol derivative, method for producing the same, and pesticide composition containing the crystal

Examples

Experimental program
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Effect test

Embodiment 1

[0066]

[0067] 30g of the compound of formula (2) (can be synthesized with reference to the method described in CN1692099A, for example), 16g of the compound of formula (3) and 15g of potassium carbonate in 300ml of acetonitrile, reacted at 55-60°C for 2 hours, and the liquid phase monitored the completion of the reaction , filtered, and the filtrate was concentrated to dryness to obtain an oil, which was separated by silica gel column chromatography and eluted with ethyl acetate, and the solvent was distilled off under reduced pressure to obtain 29 g of an oil of compound (1). Yield: 70%.

Embodiment 2

[0069] Dissolve 5 g of the oily substance obtained in Example 1 in 10 ml of methanol, add dropwise 5 ml of water, stir for one day, crystallization occurs, then cool to 5° C. in an ice-water bath, filter with suction, and dry at 60° C. to obtain 4.05 g of the formula ( 1) The compound is a white crystalline solid, melting point: 148.5°C to 150°C. Yield: 81%.

Embodiment 3

[0071] Dissolve 5g of the oil obtained in Example 1 in 10ml of methanol, slowly add 5ml of water dropwise, add 0.1g of the crystal obtained in Example 2 as a seed crystal, stir and crystallize for 3 hours, cool to 5°C in an ice-water bath, and filter with suction , and dried at 60°C to obtain 4.15g of the compound of formula (1) as a white crystalline solid with a melting point of 148°C to 150°C. Yield: 83%.

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Abstract

The present invention provides crystals of phenyl ketoenol derivatives represented by formula (1), methods for preparing the crystals, pesticide compositions containing the crystals, and uses of the crystals as insecticides. In the X-ray powder diffraction pattern of the crystal, the 2θ angles are 10.2±0.2°, 14.2±0.2°, 15.1±0.2°, 17.5±0.2°, 18.1±0.2°, 19.0±0.2°, 21.1±0.2° have characteristic peaks.

Description

technical field [0001] The present invention relates to a crystal of a phenyl ketoenol derivative represented by formula (1), a preparation method thereof, and an agricultural chemical composition containing the crystal. Background technique [0002] The phenyl ketone enol derivative shown in formula (1) is a kind of insecticide disclosed in the patent document CN103102346A, but the phenyl keto enol derivative shown in the formula (1) disclosed and prepared in this document is An oil, which is used in the form of an emulsifiable concentrate with an organic solvent in practical applications, and has low solubility in solvents such as solvent naphtha, cyclohexanone, xylene, vegetable oil, etc. commonly used to prepare emulsifiable concentrates, so The content of this compound in the emulsifiable concentrate can only reach 6%, and it is difficult to make a high-content emulsifiable concentrate. The low content leads to the need to increase the dosage to obtain a good effect whe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A01N43/38A01P7/04
CPCA01N43/38C07D405/12C07B2200/13
Inventor 郭庆春董志鹏张志虎许峰刘海龙
Owner HEBEI LANSHENG BIOTECH CO LTD
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