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A kind of ether compound containing cinnoline ring and its application

A technology of ether compound and cinnoline ring, applied in the field of ether compound containing cinnoline ring, can solve the problem that the insecticidal activity of ether compound is not disclosed and the like

Active Publication Date: 2014-10-22
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, the ether compounds containing cinnoline ring and their insecticidal activity involved in the present invention have not been disclosed

Method used

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  • A kind of ether compound containing cinnoline ring and its application
  • A kind of ether compound containing cinnoline ring and its application
  • A kind of ether compound containing cinnoline ring and its application

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0059] The preparation of example 1 compound 2:

[0060]

[0061] Add 3-(2,6-dichloro-4-(3,3-dichloro-allyloxy)phenoxy)propan-1-ol (0.69 g, 2.00 mmol, synthetic method refer to Example 1, 2, 3) in the patent CN1860874A), tetrahydrofuran (15mL), sodium hydride (0.10 g, 4.00 mmol), stirred until no bubbles were released, added 3,7-dichlorocinnoline (0.40 g, 2.00 mmol , the synthesis method refers to Journal of Medicinal Chemistry, 2010, 53(8): 3330-3348), and reacted overnight at room temperature. After the reaction was complete, the reaction solution was put into water (50mL), extracted with ethyl acetate (3×100mL), the organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. got leftovers. The residue was purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:1.5) to obtain 0.28 g of compound 2, a yellow solid, yield 26%,...

example 2

[0062] The preparation of example 2 compound 4:

[0063]

[0064] Add 3-(2,6-dichloro-4-(3,3-dichloro-allyloxy)phenoxy)propan-1-ol (0.35 g, 1.00 mmol), tetrahydrofuran (10 mL ), sodium hydride (0.14 g, 2.00 mmol), stirred until no bubbles are released, added 4-chlorocinnoline (0.16 g, 2.00 mmol, synthetic method with reference to Journal of Organic Chemistry, 1946, 11:419-428), React overnight at room temperature. After the reaction was complete, the reaction solution was put into water (50mL), extracted with ethyl acetate (3×100mL), the organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. got leftovers. The residue was purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:2) to obtain 0.08 g of compound 4, a yellow solid, yield 6%, melting point: 96-98°C

example 3

[0065] The preparation of example 3 compound 7:

[0066]

[0067] Add 3-(2,6-dichloro-4-(3,3-dichloro-allyloxy)phenoxy)propan-1-ol (0.50 g, 1.44 mmol), tetrahydrofuran ( 15mL), sodium hydride (0.05 g, 1.44 mmol), stirred until no bubbles were emitted, added 4-chloro-7-trifluoromethylcinnoline (0.33 g, 1.44 mmol, the synthetic method refers to Journal of Organic Chemistry, 1946 , 11:419-428), react overnight at room temperature. After the reaction was complete, the reaction solution was put into water (50mL), extracted with ethyl acetate (3×100mL), and the organic layer was washed with saturated sodium bicarbonate (50mL) and saturated sodium chloride solution (50mL), and dried over anhydrous magnesium sulfate. , filtered, and concentrated under reduced pressure to obtain a residue. The residue was purified by column chromatography (eluent: ethyl acetate:petroleum ether=1:3) to obtain 0.18 g of compound 7, a yellow solid, yield 23%, melting point: 85-87°C

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Abstract

The invention discloses a cinnoline ring contained ether compound. The structure of the ether compound is represented by general formula I shown in the specification, wherein R1 and R2 in the general formula I are respectively selected from hydrogen, halogens or Q, at least one of the R1 and the R2 is Q, and Q is defined in the specification; and R3, R4, R5 and R6 can be same or different, and are respectively selected from hydrogen, the halogens, a cyan group, a nitro group, C1-C3 alkyl groups, C1-C3 halogenated alkyl groups, C1-C3 alkoxy groups or C1-C3 halogenated alkoxy groups. The compound of the general formula I has an excellent insecticidal activity and can be used for controlling agricultural or forestall insect attack.

Description

technical field [0001] The invention belongs to the field of pesticides, and relates to an ether compound containing a cinnoline ring and its application. Background technique [0002] Since insecticides are used for a period of time, pests will develop resistance to them, so there is a constant need to invent new or improved compounds and compositions with insecticidal activity. [0003] Patent US4125613 reports that the cinnoline ring compound shown in the following general formula has certain insecticidal activity against aphids and Tetranychus urticae, and the No. 3 compound (code name KC) has a lethality rate of 50% against aphids at 600 ppm. [0004] [0005] In the prior art, the ether compounds containing cinnoline ring and their insecticidal activity involved in the present invention have not been disclosed. Contents of the invention [0006] The object of the present invention is to provide a novel ether compound containing a cinnoline ring, which can be appl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D237/28A01N43/58A01P7/04
Inventor 李斌吕亮梁博梁松军宋玉泉谷旭林关爱莹朱党强
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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