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Application of halogenated indole-3-acetic acid as herbicide

A halogenated indole, herbicide technology, applied in the field of pesticide chemistry, can solve the problem of unmentioned herbicides, etc., and achieve the effects of low toxicity, good environmental compatibility, and high-efficiency herbicidal activity

Inactive Publication Date: 2014-03-12
SOUTHEAST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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But overall, use as a herbicide is never mentioned

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  • Application of halogenated indole-3-acetic acid as herbicide
  • Application of halogenated indole-3-acetic acid as herbicide
  • Application of halogenated indole-3-acetic acid as herbicide

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Embodiment 1

[0026] The preparation of embodiment 1 halogenated indole-3-acetic acid

[0027] The present invention utilizes the involved compound halogenated indole-3-acetic acid, which can be realized by the following methods.

[0028] Option One:

[0029]Halogenated indole-3-acetic acids can be prepared by Fischer indole ring method, specifically:

[0030] (1) React glutamic acid with NaClO under acidic conditions to obtain 3-formyl propionic acid;

[0031] (2) Diazotize the corresponding substituted aniline compound with sodium nitrite under acidic conditions, and then reduce the product to obtain the corresponding halophenylhydrazine;

[0032] (3) Reaction of the corresponding halophenylhydrazine with 3-formylpropionic acid to generate the corresponding halophenylhydrazone, and the corresponding halophenylhydrazone is rearranged to generate the corresponding haloindole-3-acetic acid.

[0033] This process is described in: Fox SW and Bullock MW, Journal of the American Chemical Soci...

preparation example 14

[0046] Preparation 14-fluoroindole-3-acetic acid

[0047] Slowly add 8.8g of 37% formaldehyde solution (0.11mol) dropwise to a solution of 16.5g of 33% dimethylamine solution (0.12mol) and 25mL of glacial acetic acid, and keep it at 0-5°C for 1 hour. At 0-5°C, 10 g of 4-fluoroindole (0.074 mol) was added dropwise and reacted for 1 hour. Rise to room temperature, keep stirring for 24 hours, take samples and control until the reaction is completed, the reaction mixture is acidified with 4N hydrochloric acid solution, and extracted three times with ethyl acetate. The aqueous layer was washed with 4N sodium hydroxide solution and extracted three times with ethyl acetate, and the ethyl acetate layers were combined. The ethyl acetate layer was washed successively with water, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated ethyl acetate in vacuo, and finally recrystallized from ethyl acetate and n-hexane to obtain 4-fluoro-3-N,N-dimethylaminomethyl ba...

preparation example 25

[0050] Preparation 25,7-Difluoroindoleacetic acid

[0051] At 0°C, add 100.0g of 2,4-difluoroaniline (0.78mol) to 400mL of concentrated hydrochloric acid, and after stirring for 30 minutes, slowly drop a solution consisting of 84.0g of sodium nitrite (1.21mol) and 120mL of water into the above In the reactants, the reaction system was stirred for 1 hour. A solution consisting of 360 g of stannous chloride (1.90 mol) dissolved in 400 mL of concentrated hydrochloric acid was added to the above system, the entire reaction system was stirred for 1.5 hours, and the pH was adjusted to 10 with 4N sodium hydroxide solution. Extracted three times with ethyl acetate, combined the ethyl acetate layers, washed the organic layer with water and saturated brine successively, dried over anhydrous sodium sulfate, concentrated ethyl acetate in vacuo, and finally recrystallized with ethyl acetate and n-hexane to obtain 2,4- Difluorophenylhydrazine.

[0052] With 800mL of benzene and 200mL of w...

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Abstract

The invention provides an application of halogenated indole-3-acetic acid as herbicide and further provides novel herbicide. According to the invention, halogenated indole-3-acetic acid has efficient herbicidal activity and wide herbicide controlling spectrum. Meanwhile, halogenated indole-3-acetic acid is free of harmful effect to afterreap crops. In addition, halogenated indole-3-acetic acid stays in soil for a short period of time and is low in toxicity, good in environmental compatibility and high in safety.

Description

technical field [0001] The invention belongs to the field of pesticide chemistry, and particularly relates to the application of a halogenated indole-3-acetic acid as an agricultural chemical herbicide, and also relates to a novel herbicide. Background technique [0002] Indole acetic acid derivatives, which are an important class of auxins, have always been the focus of attention. In order to seek more efficient auxins, monohalogenated and polyhalogenated indole acetic acids have been developed successively. They have the potential to be developed into excellent plant auxins, and some monohalogenated and polyhalogenated indole acetic acid compounds have been directly applied to promote plant growth, such as 4-chloroindole-3-acetic acid. [0003] Ernst ED and Zvi P, Journal of the Chemical Society (1959), May: 1913-1914 reported the synthesis of 5-fluoroindole-3-acetic acid and 6-fluoro-indole-3-acetic acid, the corresponding fluorinated Indole first undergoes a Mannich re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/38A01P13/00
Inventor 葛裕华陈玲芳潘东辉
Owner SOUTHEAST UNIV
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