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Aryloxy anilino propionic ester compound and application thereof as herbicide

A technology of aryloxyanilinyl propionate and compound, which is applied in the field of preparation of pesticide compounds, can solve the problems of limited application range and unsatisfactory effect on broad-leaved weeds, and achieve the effect that resistance is not easily produced

Inactive Publication Date: 2016-03-30
YANGTZE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although the above-mentioned herbicides have the characteristics of high efficiency, quick-acting, and not easy to produce resistance, the herbicide spectrum of this type of herbicide is mainly gramineous weeds, and the effect on broad-leaved weeds is not ideal, and the scope of application is limited.

Method used

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  • Aryloxy anilino propionic ester compound and application thereof as herbicide
  • Aryloxy anilino propionic ester compound and application thereof as herbicide
  • Aryloxy anilino propionic ester compound and application thereof as herbicide

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1,2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy) anilino] synthesis of ethyl propionate

[0027] 1. In a 100mL three-necked flask with a nitrogen device, add 40mL of DMF, then add 2.76g (0.02mol) of p-nitrophenol and 1.92g (0.02mol) of sodium tert-butoxide (STB), and stir at room temperature About 2h, then add 4.32g (0.02mol) 2,3-dichloro-5-trifluoromethylpyridine and 2.76g (0.02mol) K 2 CO 3 , continue to stir the reaction at room temperature, use TLC to detect the reaction, after the reaction is over, distill off the DMF solvent under reduced pressure, dissolve it with 50ml chloroform, extract with distilled water, take the chloroform layer, add anhydrous sodium sulfate to dry, stand overnight, filter and concentrate Obtain a dark brown powder; add 120 mL of absolute ethanol, 24 mL of distilled water, 9.6 g of ammonium chloride, and 6.5 g of reduced iron powder to the above dark brown powder, heat to reflux, and detect the reaction by TLC. Wash with disti...

Embodiment 2

[0033] Embodiment 2,2-[4-(5-trifluoromethyl-2-pyridyloxy) anilino] synthetic of ethyl propionate

[0034] 1. In a 100mL three-necked flask with a nitrogen device, add 40mL of DMF, and then add 2.18g (0.02mol) of p-nitrophenol and 1.92g (0.02mol) of sodium tert-butoxide (STB), and stir at room temperature React for about 1h, then add 3.63g (0.02mol) 2-chloro-5-trifluoromethylpyridine and 2.76g (0.02mol) K 2 CO 3 , continue to stir the reaction at room temperature (about 20 ° C); use TLC to detect the reaction, after the reaction is over, distill off the DMF solvent under reduced pressure, dissolve it with 50ml chloroform, extract with distilled water, take the chloroform layer, add anhydrous sodium sulfate to dry, static Leave overnight, filter and concentrate to obtain a dark brown powder; add 120 mL of absolute ethanol, 24 mL of distilled water, 9.6 g of ammonium chloride, and 6.5 g of reduced iron powder to the above dark brown powder, heat to reflux, and detect the reactio...

Embodiment 3

[0040] Embodiment 3,2-[4-(3-trifluoromethyl-2-pyridyloxy) anilino base] the synthesis of ethyl propionate

[0041] 1. In a 100mL three-necked flask with a nitrogen device, add 40mL of DMF, then add 2.18g (0.02mol) of p-aminophenol and 1.92g (0.02mol) of sodium tert-butoxide (STB), and stir the reaction at room temperature About 1h, then add 3.63g (0.02mol) 2-chloro-3-trifluoromethylpyridine and 2.76g (0.02mol) K 2 CO 3 , continue to stir the reaction at room temperature; use TLC to detect the reaction, after the reaction is over, distill off the DMF solvent under reduced pressure, dissolve it with 50ml chloroform, extract with distilled water, take the chloroform layer, add anhydrous sodium sulfate to dry, let stand overnight, filter and concentrate To obtain a dark brown powder, add 120 mL of absolute ethanol, 24 mL of distilled water, 9.6 g of ammonium chloride, and 6.5 g of reduced iron powder to the above dark brown powder, heat to reflux, and detect the reaction by TLC. ...

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Abstract

An aryloxy anilino propionic ester compound comprises the structure shown in the general formula (I), wherein Ar is aromatic heterocycle or fused heterocycle. Please see the specification for the chemical formula of the aromatic heterocycle and the chemical formula of the fused heterocycle, wherein R1, R2, R3 and R4 are one or more of H, halogen, nitro, methoxy group, methyl, methyl formate group, cyanogroup and trihalomethyl, R5 is the alkyl group on the linear chain or branched chain of H and C1-C4, hydrogen on the alkyl group is substituted by hydroxyl, carboxyl, mercapto group, amino, guanidyl and phenyl, and R6 is one of methyl, ethyl, butyl and the substance specified in the specification. The compound has the advantages that the characteristics of being efficient, capable of acting quickly and not prone to resistance generation of (aryloxy) phenoxypropionate herbicides can be maintained, amino acid functional groups in molecules can be designed to serve as adulterate amino acid so as to restrain the biosynthesis of protein of plants, and all weeds can be controlled.

Description

technical field [0001] The invention relates to the technical field of preparing pesticide compounds, in particular to an aryloxyanilino propionate compound and its application as a herbicide. Background technique [0002] Aryloxyphenoxypropionate compounds are an important class of herbicides, the main control objects are grass weeds, and the target is the acetyl-CoA carboxylase (ACCase) of plants, by inhibiting the lipids in grass plants Synthesis of grass weeds control; [0003] Although the above-mentioned herbicides are highly effective, quick-acting, and not easy to produce resistance, the herbicide spectrum of this type of herbicide is mainly gramineous weeds, and the effect on broad-leaved weeds is not ideal, and the scope of application is limited. Contents of the invention [0004] In order to overcome the deficiencies in the prior art, the object of the present invention is to provide a kind of aryloxyanilinopropionate compound and its application as a herbicid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/643C07D213/73C07D239/34C07D333/32C07D263/58C07D241/44C07D277/68A01N43/76A01N43/40A01N43/54A01N43/10A01N43/60A01N43/78A01P13/00
CPCC07D213/643A01N43/10A01N43/40A01N43/54A01N43/60A01N43/76A01N43/78C07D213/73C07D239/34C07D241/44C07D263/58C07D277/68C07D333/32
Inventor 李俊凯徐志红陈然李黎张涛王少康牛俊凡
Owner YANGTZE UNIVERSITY
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