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6-Aryloxyacetoxy orange ketones and their application in pesticides

A technology of aryloxyacetoxy orange ketone and compound, applied in the field of herbicides, can solve the problem that 6-aryloxyacetoxy orange ketone compounds have not been disclosed, and achieve high herbicidal activity, high control effect and herbicidal activity improved effect

Inactive Publication Date: 2016-06-15
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some aurones and their herbicidal activity have been reported, see CN101402622B and CN101914081A, but the 6-aryloxyacetoxy aurones shown in the present invention have not been disclosed

Method used

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  • 6-Aryloxyacetoxy orange ketones and their application in pesticides
  • 6-Aryloxyacetoxy orange ketones and their application in pesticides
  • 6-Aryloxyacetoxy orange ketones and their application in pesticides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Preparation of 2,4-dihydroxy-a-chloroacetophenone (A):

[0036] Dissolve 20.0g (181.6mmol) of anhydrous resorcinol and 13.0mL (205.0mmol) of chloroacetonitrile in 300mL of dry diethyl ether, cool the reaction flask below 0°C with an ice-salt bath, stir, and add 12.0g (88.0 mmol) dry molten zinc chloride, continue to pass into dry hydrogen chloride gas for 3h, then seal the reaction bottle, place it in the refrigerator for 1d, and the bottom layer is a red oily substance; continue to pass into dry hydrogen chloride gas for 4h, and then place it in the refrigerator 1d, the bottom layer precipitated out as a pale yellow solid. Filter, wash the filter cake twice with anhydrous ether, then transfer it to a round bottom flask, hydrolyze it with 250mL water at a temperature lower than 100°C until it becomes transparent yellow-brown, put it in the refrigerator for 3h, and precipitate a yellow-brown solid. Filter, dry, and recrystallize from ethanol to obtain 17.2 g ...

Embodiment 2

[0037] Example 2: Preparation of 6-Hydroxy-4'-dimethylaminoaurone (B1):

[0038] Add 2.0g (10.7mmol) A into a round bottom flask filled with ethanol (5mL) and fresh 10% KOH solution (15mL), then add 2.24g (15.0mmol) 4-dimethylaminobenzaldehyde, Stir at room temperature, after the reaction is complete, acidify with 1.0mol / L dilute hydrochloric acid, let stand for 1-3 hours, filter with suction, dry, and recrystallize with dichloromethane and ethanol to obtain 6-hydroxy-4'-dimethylaminoaurone ( B1) 1.86g, yield 61.8%, m.p.178~180°C.

Embodiment 3

[0039] Example 3: Preparation of 6-Hydroxy-3'-Fluorinone (B2):

[0040] Add 2.0g (10.7mmol) A into a round bottom flask filled with ethanol (5mL) and fresh 10% KOH solution (15mL), then add 1.86g (15.0mmol) m-fluorobenzaldehyde, stir at room temperature, After the reaction is complete, acidify with 1.0mol / L dilute hydrochloric acid, let stand for 1-3h, filter with suction, dry, and recrystallize with dichloromethane and ethanol to obtain 2.04g of 6-hydroxy-3'-fluoroorange (B2). Yield 74.4%, m.p.272~274°C.

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PUM

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Abstract

The invention relates to a 6-aryloxy acetoxy aurone compound and an application thereof on a pesticide, and belongs to the technical field of herbicides. The general formula of the 6-aryloxy acetoxy aurone compound is as shown in the specification, wherein R1 is hydrogen, halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 alkylamino, and R2 is the hydrogen and the C1-C4 alkyl. The invention provides a lot of novel chemical structures and novel compounds. A biological activity measurement result indicates that the compound I has very high weeding activity.

Description

technical field [0001] The invention relates to 6-aryloxyacetoxy orange ketone compounds and their application in pesticides, belonging to the technical field of herbicides. Background technique [0002] If a herbicide or its composition is used in large quantities for a long time, weeds will develop resistance to it. Therefore, it is necessary to continuously invent new herbicide compounds. Herbicides developed based on natural products often have the characteristics of high efficiency, low toxicity and slow resistance development. Orange ketone is a secondary metabolite of plants, which not only participates in the process of plant growth and reproduction, but also gives plants a yellow or orange color; it also helps plants inhibit the growth of competitive weeds and defend against the invasion of pathogens and pests. Some aurones and their herbicidal activity have been reported, see CN101402622B and CN101914081A, but the 6-aryloxyacetoxy aurones shown in the present inve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/83A01N43/12A01P13/00
CPCA01N43/12C07D307/83
Inventor 张敏李婷王福赵婷鲍永团陈国燕仰榴青徐效华
Owner JIANGSU UNIV