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Malononitrile oxime ether compound and use thereof

A technology of ether compounds and malononitrile oxime, which is applied in the fields of application, organic chemistry, and biocides, and can solve the problems that the bactericidal activity of malononitrile oxime ether compounds has not been reported.

Active Publication Date: 2017-07-04
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, malononitrile oxime ether compounds and their bactericidal activity as shown in the present invention have not been reported

Method used

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  • Malononitrile oxime ether compound and use thereof
  • Malononitrile oxime ether compound and use thereof
  • Malononitrile oxime ether compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0200] Embodiment 1: the preparation of compound 4

[0201]

[0202] Add p-chlorobenzyl chloride (0.3 g, 1.86 mmol), malononitrile oxime ether sodium salt (0.22 g, 1.86 mmol) and 15 ml of acetonitrile in a 50 ml reaction flask, stir the reaction at room temperature, TLC (ethyl acetate: Petroleum ether=1:8) monitoring, after the completion of the reaction, acetonitrile was evaporated under reduced pressure, and the residue column chromatography (ethyl acetate:petroleum ether=1:10 was used as eluent, 100 -140 mesh silica gel) to obtain 0.21 g of yellow oil, with a yield of 51%.

Embodiment 2

[0203] Embodiment 2: the preparation of compound 25

[0204]

[0205] Add p-trifluoromethoxybenzyl bromide (0.25 gram, 0.98 mmol), malononitrile oxime ether sodium salt (0.12 gram, 0.98 mmol) and 15 milliliters of acetonitrile in 50 milliliters of reaction flasks, stir reaction at room temperature, TLC ( Ethyl acetate:petroleum ether=1:8) monitoring, after the completion of the reaction, acetonitrile was evaporated under reduced pressure, and the residue column chromatography (ethyl acetate:petroleum ether=1:10 was used as eluent, Qingdao Marine Biochemical Factory 100-140 mesh silica gel produced in the factory) was purified to obtain 0.16 g of white solid, with a yield of 61%.

Embodiment 3

[0206] Embodiment 3: the preparation of compound 37

[0207]

[0208] Add p-cyanobenzyl bromide (0.3 g, 1.53 mmol), malononitrile oxime ether sodium salt (0.18 g, 1.53 mmol) and 15 ml of acetonitrile in a 50 ml reaction flask, stir the reaction at room temperature, TLC (ethyl acetate : Petroleum ether=1:8) monitoring, after the completion of the reaction, acetonitrile was evaporated under reduced pressure, and the residue column chromatography (ethyl acetate: petroleum ether=1:10 was used as eluent, produced by Qingdao Marine Biochemical Factory Branch Factory 100-140 mesh silica gel) was purified to obtain 0.18 g of white solid with a yield of 56%.

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PUM

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Abstract

The invention discloses a malononitrile oxime ether compound with a novel structure. The structure of the compound is represented by general formula I, and all substituent groups in the formula are defined as in the description. The compound of general formula I has excellent sterilization activity, and has very good prevention and control effects on bacterium diseases and fungus diseases of plants. The invention also discloses a use of the compound of the general formula I in the agriculture and other fields as a bactericide.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a malononitrile oxime ether compound and its application. Background technique [0002] Oxime ether derivatives are a class of compounds with broad-spectrum biological activity, and are widely used in pesticides, herbicides and fungicides. Since Cymoxan, the first commercialized oxime ether fungicide developed by Federal Corporation of the United States, came out in 1974, new commercialized varieties have appeared continuously, such as acetoxime, kysstrobin, and orysastrobin. Oxime ether compounds have always been the research focus of major companies because of their high efficiency, low toxicity, and low residue. [0003] In the prior art, there is no report on malononitrile oxime ether compounds and their fungicidal activity as shown in the present invention. Contents of the invention [0004] The object of the present invention is to provide a malononitr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/62C07D277/24C07D277/64C07D231/14C07D277/82C07D215/14C07D231/12C07D213/61A01N43/40A01N43/56A01N37/50A01N43/42A01N43/78A01P3/00
CPCA01N37/50A01N43/40A01N43/42A01N43/56A01N43/78C07C255/62C07D213/61C07D215/14C07D231/12C07D231/14C07D277/24C07D277/64C07D277/82C07C255/64C07D277/28A01N33/24
Inventor 程学明张立新陈亮孙芹刘君丽李志念赵杰徐靖博吴鸿飞
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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