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6-aryloxy acetoxy aurone compound and application thereof on pesticide

A kind of technology of aryloxyacetoxy aurone and compound, which is applied in the field of herbicides, can solve the problems that 6-aryloxy acetoxy arurone compounds have not been disclosed, and achieve high herbicidal activity, high control effect and herbicidal activity Improved effect

Inactive Publication Date: 2014-10-01
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 CN 101402622B and CN 101914081A, but the 6-aryloxyacetoxy aurones shown in the present invention have not been disclosed

Method used

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  • 6-aryloxy acetoxy aurone compound and application thereof on pesticide
  • 6-aryloxy acetoxy aurone compound and application thereof on pesticide
  • 6-aryloxy acetoxy aurone compound and application thereof on pesticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: 2,4-dihydroxy- a - Chloroacetophenone ( A ) preparation:

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

Embodiment 2

[0038] Embodiment 2: 6-hydroxyl-4 '-dimethylamino aurone ( B1 ) preparation:

[0039] 2.0 g (10.7 mmol) A Add to a round-bottomed flask filled with ethanol (5 mL) and newly prepared 10% KOH solution (15 mL), then add 2.24 g (15.0 mmol) 4-dimethylaminobenzaldehyde, stir at room temperature, and after the reaction is complete , acidified with 1.0 mol / L dilute hydrochloric acid, allowed to stand for 1-3 h, filtered with suction, dried, and recrystallized with dichloromethane and ethanol to obtain 6-hydroxy-4′-dimethylaminoaurone ( B1 ) 1.86 g, yield 61.8%, m.p. 178~180 °C.

Embodiment 3

[0040] Embodiment 3: 6-hydroxyl-3 '-fluoro orange ketone ( B2 ) preparation:

[0041] 2.0 g (10.7 mmol) A Add it to a round-bottomed flask filled with ethanol (5 mL) and newly prepared 10% KOH solution (15 mL), then add 1.86 g (15.0 mmol) m-fluorobenzaldehyde, stir at room temperature, and after the reaction is complete, use 1.0 mol / L dilute hydrochloric acid for acidification, standing for 1-3 h, suction filtration, drying, and recrystallization with dichloromethane and ethanol to obtain 6-hydroxy-3'-fluoroorangeone ( B2 ) 2.04 g, 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 CN 101402622B and CN 101914081A, but the 6-aryloxyacetoxy aurones shown in the present in...

Claims

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Application Information

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Patent Type & Authority Applications(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
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