Substituted (hetero) arylmethylene pyrimidine ether compound and preparation method and application thereof

A technology of methyl pyrimidine ether and heteroaryl, which is applied in the field of substituted aryl methylene pyrimidine ether compounds and their preparation, and can solve problems such as unsatisfactory effects

Active Publication Date: 2019-09-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] However, in many cases, the compounds described in these documents have unsatisfactory effects on animal pests.

Method used

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  • Substituted (hetero) arylmethylene pyrimidine ether compound and preparation method and application thereof
  • Substituted (hetero) arylmethylene pyrimidine ether compound and preparation method and application thereof
  • Substituted (hetero) arylmethylene pyrimidine ether compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0164] Embodiment 1: the synthesis of compound 39

[0165] Dissolve 1.3g (0.005mol) of 1a in 10ml of N,N-dimethylformamide, add 0.83g of potassium carbonate, stir for 0.5h, add 1.26g of 2a in batches, heat up to 80°C after addition, and stir for 8h . After the reaction was detected by TLC, the reaction solution was poured into 50 ml of saturated saline, extracted three times with 100 ml of ethyl acetate, and dried. After precipitation, it was purified by column chromatography to obtain 2.1 g of an oily product.

[0166]

Embodiment 2

[0167] Embodiment 2: the synthesis of compound 15

[0168] Dissolve 1.15g (0.005mol) of 1b in 10ml of N,N-dimethylformamide, add 0.83g of potassium carbonate, stir for 0.5h, add dropwise the DMF solution of 2b (1.4g), and heat up to 80°C after adding , Stir the reaction for 8h. After the reaction was detected by TLC, the reaction solution was poured into 50 ml of saturated saline, extracted three times with 100 ml of ethyl acetate, and dried. After precipitation, it was purified by column chromatography with petroleum ether: ethyl acetate 1000:1-300 eluent to obtain 1.75 g of an oily product.

[0169]

Embodiment 3

[0170] Embodiment 3: the synthesis of compound 207

[0171] Dissolve 2.0g (0.005mol) of 1c in 10ml of N,N-dimethylformamide, add 0.83g of potassium carbonate, stir for 0.5h, add 1.45g of 2c in batches, heat up to 80°C after addition, and stir for 8h . After the reaction was detected by TLC, the reaction solution was poured into 50 ml of saturated saline, extracted three times with 100 ml of ethyl acetate, and dried. After precipitation, it was purified by column chromatography with petroleum ether: ethyl acetate 1000:1-200 eluent to obtain 2.6 g of an oily product.

[0172]

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PUM

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Abstract

The invention discloses a substituted (hetero) arylmethylene pyrimidine ether compound, the structure is shown in a formula (I), and the definitions of various substituents in the formula are shown inthe specification. The formula (I) compound shows high insecticidal activity to adults, larvae and eggs of harmful mites and insects in the fields of agriculture, civil use and animal technology. Atthe same time, the compound shows good bactericidal activity. Therefore, the formula (I) compound can be widely used in agriculture and other fields as pesticides and/or fungicides.

Description

technical field [0001] The invention belongs to the field of agricultural insecticide, acaricide and bactericide. It specifically relates to substituted (hetero)aryl methylene pyrimidine ether compounds and their preparation methods and applications. Background technique [0002] Researchers have long discovered that methoxyacrylates are biologically active. The following documents have reported that this type of compound has insecticidal and acaricidal activity: EP242081 / EP299694 / EP335519 / US2006235075 / CN101311170 and so on. [0003] In addition, pyrimidine methoxyacrylate compounds have also been reported as crop insecticides, acaricides or fungicides: [0004] Patent US005106852 relates to compounds of the following general formula as insecticides: [0005] [0006] In the patent US005378711, the following general formula compounds are involved as fungicides: [0007] [0008] Patent US005935965 relates to the compound of the following general formula as an acari...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34C07D239/56C07D401/06A01N43/54A01P3/00A01P7/02A01P7/04
CPCA01N43/54C07D239/34C07D239/56C07D401/06
Inventor 杜晓华郝树林
Owner ZHEJIANG UNIV OF TECH
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