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

A kind of methyl pyrazole ether and heteroaryl technology, applied in the field of substituted aryl methylene pyrazole ether compounds and their preparation, can solve the problems such as unsatisfactory effect

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0163] Example 1: Synthesis of compound 111

[0164] Dissolve 1.3g (0.005mol) of 1a in 10ml of N,N-dimethylformamide, add 0.83g of potassium carbonate, stir for 0.5h, add 2a (1.26g) in batches, increase the temperature to 80℃, stir Reaction for 8h. After the reaction was detected by TLC, the reaction solution was poured into 50 ml of saturated brine, extracted three times with 100 ml of ethyl acetate, and dried. After desolvation, use petroleum ether: ethyl acetate 1000:1-500 as the eluent to obtain 1.86 g oily product by column chromatography.

[0165]

Embodiment 2

[0166] Example 2: Synthesis of compound 87

[0167] Dissolve 1.1g (0.005mol) 1b in 10ml of N,N-dimethylformamide, add 0.83g potassium carbonate, stir for 0.5h, add dropwise 2b (1.4g) DMF solution, and increase the temperature to 80℃ , Stir the reaction for 8h. After the reaction was detected by TLC, the reaction solution was poured into 50 ml of saturated brine, extracted three times with 100 ml of ethyl acetate, and dried. After desolvation, use petroleum ether: ethyl acetate 1000:1-200 as the eluent to obtain 1.68 g oily product by column chromatography.

[0168]

[0169] Other compounds of the present invention can be prepared with reference to the above examples.

[0170] NMR data of some compounds:

[0171] Compound 37: 1 HNMR (400MHz, DMSO) δ (ppm): 3.51 (s, 3H, CH 3 ), 3.60(s, 3H, CH 3 ),3.80(s,3H,CH 3 ),5.01(s,2H,CH 2 ), 5.94(s,1H,pyrazolyl1-H),7.13-7.53(m,9H,Ar-H), 7.67(s,1H,CH)

[0172] Compound 39: 1 HNMR (400MHz, DMSO) δ (ppm): 3.58 (s, 3H, CH 3 ),3.59(s,3H,CH 3 ),3.79(s,...

Embodiment 3

[0178] Example 3: 30% wettable powder

[0179]

[0180] The compound and other components are fully mixed and pulverized by an ultrafine pulverizer to obtain a 30% wettable powder product.

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PUM

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Abstract

The invention discloses a substituted (hetero) arylmethylene pyrazole ether compound and a preparation method and application thereof. The structure is shown in a formula (I), and definitions of various substituents in the formula are shown in the 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. At the 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 insecticides, acaricides and fungicides. Specifically, it relates to a substituted (hetero)aryl methylene pyrazole ether compound, and a preparation method and application thereof. Background technique [0002] Researchers have long ago discovered that methoxy acrylate compounds have biological activity. The following documents have reported that these compounds have insecticidal activity: EP242081 / EP299694 / EP335519 / US2006235075 / CN101311170 and so on. [0003] In addition, pyrimidine methoxy acrylate compounds have also reported crop insecticides, mites or fungicides: [0004] Patent US005106852 involves the following general formula compounds as pesticides: [0005] [0006] Patent US005378711 involves the following general formula compounds as fungicides: [0007] [0008] Patent US005935965 relates to compounds of the following general formula as acaricides and fungicides: [0009] [0010] Patent US006114342...

Claims

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Application Information

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IPC IPC(8): C07D231/20C07D261/12A01N43/56A01N47/24A01N43/80A01P7/04A01P7/02A01P3/00
CPCA01N43/56A01N43/80A01N47/24C07D231/20C07D261/12
Inventor 杜晓华郝树林
Owner ZHEJIANG UNIV OF TECH
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