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Method for improving stability of clethodim

A technology for clethodim and stability, applied in the field of improving the stability of clethodim, can solve problems such as reducing the reaction yield and increasing the preparation cost, and achieves the effects of high reaction yield, suitability for industrial production, and mild reaction conditions

Active Publication Date: 2012-03-21
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the chemical properties of the finally obtained clethodim sodium salt are stable, in the preparation process of clethodim sodium salt, clethodim is easily decomposed by water produced as a by-product (Chinese invention patent publication CN1846493 There are exact data descriptions for this in ), therefore, only the water generated by the reaction can be removed to obtain stable clethodim sodium salt (III), however, the dehydration operation not only increases the preparation cost, but also significantly reduces the reaction yield

Method used

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  • Method for improving stability of clethodim
  • Method for improving stability of clethodim
  • Method for improving stability of clethodim

Examples

Experimental program
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Effect test

Embodiment 1

[0020] The preparation of embodiment 1 clethodim methylamine salt

[0021] Add 36g of clethodim technical substance (86%, 0.086mol) and 90g of n-hexane into the reaction flask, and stir evenly at room temperature. Under cooling conditions, slowly introduce methylamine gas. Control the temperature at 0-5°C, and stir at 20°C for 1.5 hours after the addition. The reaction was filtered to give an off-white solid. After drying under reduced pressure, 34 g of the product was obtained with a melting point of 131°C. After detection and analysis by high-pressure liquid chromatography (HPLC), the converted clethodim content is 95.1%, and the reaction yield is 96.2%.

Embodiment 2

[0022] The preparation of embodiment 2 clethodim ethylamine salt

[0023] Add 36g of clethodim technical substance (86%, 0.086mol) and 80g of petroleum ether into the reaction flask, and stir evenly at room temperature. Under cooling conditions, slowly introduce ethylamine gas. Control the temperature at 5-10°C, and stir at 20°C for 1.5 hours after the addition. The reaction was filtered to give an off-white solid. After drying under reduced pressure, 35 g of the product was obtained, with a melting point of 137° C., detected and analyzed by high-pressure liquid chromatography (HPLC), and the converted clethodim content was 95.1%, and the reaction yield was 95.9%.

Embodiment 3

[0024] The preparation of embodiment 3 clethodim propylamine salt

[0025] Add 36g of clethodim technical substance (86%, 0.086mol) and 70g of cyclohexane into the reaction flask, and stir evenly at room temperature. Under cooling conditions, slowly add propylamine liquid dropwise. Control the temperature at 10-20°C, and stir at 20°C for 1.5 hours after the addition. The reaction was filtered to give an off-white solid. After drying under reduced pressure, 36 g of the product was obtained, with a melting point of 142°C. After detection and analysis by high-pressure liquid chromatography (HPLC), the converted clethodim content is 95.1%, and the reaction yield is 95.1%.

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Abstract

The invention relates to a method for improving stability of clethodim, which includes steps of enabling clethodim and amine compounds to react to generate clethodim amine salt in organic solvent at the temperature ranging from 10 DEG C to 80 DEG C and then to be kept in the form of clethodim amine salt. The amine compounds include amine, primary amine, secondary amine or tertiary amine. During conversion of clethodim into clethodim amine salt, the method is high in reaction yield without generating water, mild in reaction condition, simple and convenient in operation, and lower in cost and more suitable for industrialized production as compared with the form in the prior art of converting clethodim into clethodim amine salt. Besides, the clethodim amine salt generated by the method is high in high-temperature stability and capable of effectively solving the problem of pyrolysis of clethodim technical during long-time transportation.

Description

technical field [0001] The invention relates to a method for improving the stability of clethodim. Background technique [0002] Clethodim, the chemical name is 2-{1-[(3-chloro-2-allyl)oxy]iminopropyl}-5-[2-(ethylthio)propyl]-3-hydroxy -2-cyclohexen-1-one is a broad-spectrum post-emergent herbicide for controlling gramineous weeds in broad-leaf crops released by Chevron Chemical Company of the United States, which has a strong effect on various annual and perennial weeds Killing effect, mainly suitable for weeding of more than 40 kinds of crops such as soybean, flax, tobacco, watermelon, etc., and can control more than 30 kinds of gramineous weeds such as barnyard grass. The molecular structure of clethodim contains functional groups such as hydroxyl, double bond, and oxime. According to literature reports, factors such as moisture, oxygen, ultraviolet rays, and temperature in the daily environment can easily cause the decomposition of clethodim. To avoid moisture, oxygen ...

Claims

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Application Information

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IPC IPC(8): C07C323/47C07C319/20
Inventor 陶伟周炜崔华
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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