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A dichloroacetic acid-containing dihydroxy quaternary ammonium salt herbicide, its preparation method and application

A technology of dihydroxy, dihydroxy quaternary ammonium salt of dichloroacetic acid, applied in the field of pesticides, can solve the problems of loss of herbicidal activity, no herbicidal activity of dihydroxy quaternary ammonium salt compounds of dichloroacetic acid, limited application, etc. Tension, the protection of agricultural ecological security, the effect of good herbicidal activity

Active Publication Date: 2021-06-22
INST OF COTTON RES CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, under ultraviolet UV radiation, dichloroacetic acid is easy to dechlorinate and lose its herbicidal activity, which limits its application in agricultural production.
[0003] At present, there are no bibliographical reports on dihydroxy quaternary ammonium salts of dichloroacetic acid and their herbicidal activity

Method used

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  • A dichloroacetic acid-containing dihydroxy quaternary ammonium salt herbicide, its preparation method and application
  • A dichloroacetic acid-containing dihydroxy quaternary ammonium salt herbicide, its preparation method and application
  • A dichloroacetic acid-containing dihydroxy quaternary ammonium salt herbicide, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Containing the preparation (numbering is A) of dichloroacetic acid dodecylmethyl dihydroxyethyl ammonium salt herbicide, comprises the following steps:

[0027] (1) Mix 1-bromododecane and N-methyldiethanolamine (MEDA) evenly at a molar ratio of 1.1:1.0, add them into a three-necked round-bottomed flask, and control the temperature at 110°C for 2 hours to obtain the crude product Recrystallize and purify with a mixture of ethyl acetate and ethanol, and dry in vacuo to obtain white N-methyl-N-dodecyl-N,N-dihydroxyethylammonium bromide;

[0028] (2) Weigh 3.68g (10mmol) of N-methyl-N-dodecyl-N,N-dihydroxyethylammonium bromide and add it to a round-necked flask equipped with a magnetic stirrer. Dissolve in water and methanol, slowly dropwise add methanol solution containing equimolar potassium hydroxide under stirring for anion replacement, and react at room temperature.

[0029] (3) After 2 hours, the reaction solution was checked with silver nitrate solution to determin...

Embodiment 2

[0031] The preparation (numbering is B) that contains dichloroacetic acid tetradecylmethyl dihydroxyethyl ammonium salt herbicide comprises the following steps:

[0032] (1) Mix 1-bromotetradecane and N-methyldiethanolamine (MEDA) at a molar ratio of 1.15: 1.0, add it into a three-necked round-bottomed flask, and control the temperature at 114°C for 2 hours to obtain the crude product Recrystallize and purify with a mixture of ethyl acetate and ethanol, and dry in vacuo to obtain white N-methyl-N-tetradecyl-N,N-dihydroxyethylammonium bromide;

[0033] (2) Weigh 3.96g (10mmol) of N-methyl-N-tetradecyl-N,N-dihydroxyethylammonium bromide into a round-necked flask equipped with a magnetic stirrer, and use 20mL without Dissolve in water and methanol, slowly add methanol solution containing equimolar potassium hydroxide dropwise under stirring for anion replacement, and react at room temperature:

[0034] (3) After 2 hours, the reaction solution is tested with silver nitrate soluti...

Embodiment 3

[0036] Contain the preparation (numbering is C) of dichloroacetic acid cetylmethyl dihydroxyethyl ammonium salt herbicide, comprises the following steps:

[0037] (1) Mix 1-bromohexadecane and N-methyldiethanolamine (MEDA) at a molar ratio of 1.2: 1.0, add it into a three-necked round-bottomed flask, control the temperature at 120°C for 2 hours, and obtain the crude product Recrystallize and purify with a mixture of ethyl acetate and ethanol, and dry in vacuo to obtain white N-methyl-N-hexadecyl-N,N-dihydroxyethylammonium bromide;

[0038] (2) Weigh 4.24g (10mmol) of N-methyl-N-hexadecyl-N,N-dihydroxyethylammonium bromide and add it to a round-necked flask equipped with a magnetic stirrer. Dissolve in water and methanol, slowly add methanol solution containing equimolar potassium hydroxide dropwise under stirring for anion replacement, and react at room temperature

[0039] (3) After 2 hours, the reaction solution is tested with silver nitrate solution to determine whether th...

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Abstract

The invention discloses a dichloroacetic acid dihydroxy quaternary ammonium salt herbicide, its preparation method and application. The general structural formula of the dichloroacetic acid dihydroxy quaternary ammonium salt herbicide is represented by: wherein R is selected from C6-C18 saturated straight-chain alkyl groups, and this type of compound is prepared by ion exchange, acid-base neutralization, and the preparation method Simple, high yield, high purity, easy scale production. The compound has excellent post-emergence stem and leaf treatment activity, can selectively control broad-leaved weeds, and is suitable as a herbicide for controlling broad-leaved weeds in plant crops.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a dichloroacetic acid dihydroxy quaternary ammonium salt herbicide, and also relates to a preparation method of the dichloroacetic acid dihydroxy quaternary ammonium salt herbicide, and the dichloroacetic acid dihydroxy quaternary ammonium salt herbicide. Application of quaternary ammonium herbicides in controlling broad-leaved weeds. Background technique [0002] Dichloroacetic acid belongs to α-chlorinated fatty acid and is a photosynthetic photosystem II (Photosystem II, PSII) inhibitor, which inhibits or hinders the electron transfer between plastoquinone QA and QB. Its main target is the 32kDaD1 polypeptide protein in PS II. After dichloroacetic acid enters the soil, it is easily degraded and disappeared by dechlorination bacteria, non-accumulative, low-toxic and safe. It can be seen that dichloroacetic acid can be used as a lead compound or an active interm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C215/12C07C51/41C07C53/16A01N33/12A01N37/02A01P13/00
CPCA01N33/12A01N37/02C07C53/16C07C215/12
Inventor 李欢欢马艳姜伟丽宋贤鹏马小艳胡红岩任相亮王丹马亚杰
Owner INST OF COTTON RES CHINESE ACAD OF AGRI SCI
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