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Acyl thiourea compound containing 1-methyl-3-trifluoromethyl-1H-parazole structure, as well as preparation method and application thereof

A technology of trifluoromethyl and acylthiourea, which is applied in the field of preparation of acylthiourea compounds, can solve problems such as molecular structure changes, and achieve the effects of convenient post-processing, high product yield, and simple raw materials

Inactive Publication Date: 2017-07-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The molecular structure of this type of fungicides has relatively large changes, and most of the fungicides discovered in recent years contain pyrazole rings.

Method used

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  • Acyl thiourea compound containing 1-methyl-3-trifluoromethyl-1H-parazole structure, as well as preparation method and application thereof
  • Acyl thiourea compound containing 1-methyl-3-trifluoromethyl-1H-parazole structure, as well as preparation method and application thereof
  • Acyl thiourea compound containing 1-methyl-3-trifluoromethyl-1H-parazole structure, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] N-((2-fluorophenyl)aminothiocarbonyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-ylthiourea, white solid, yield 51.9%, m.p.181 ~182℃; FTIR(ν,cm -1 ): 3246(N-H),3144(N-H),3025(Ar,C-H),1684(C=O),1618(Ar),1599(Ph,C=C),1546(C-N),1504(C=S ), 1485(Ph,C=C), 1321(C-N), 1291(C-N), 1000-1200(C-F), 772(Ar-H), 759(Ph,C-H). 1 H NMR (CDCl 3 ,400MHz),δ:3.99(s,3H,CH 3 ),7.23-7.27(m,1H,Ph),7.31-7.36(m,2H,Ph),7.91(t, J=7.5Hz,1H,Ph),8.83(s,1H,CH),11.76(s ,1H,NH),12.24(s,1H,NH).HRMS(ESI)for C 13 h 10 f 4 N 4 OS m / z: Calculated, 347.0584, Found, 347.0581 [M+H] + .

Embodiment 2

[0033] N-((3,4-difluorophenyl)aminothiocarbonyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-ylthiourea, white solid, yield 53.4% , m.p.114~115℃; FTIR(ν,cm -1 ): 3293(N-H),3135(N-H),3038(Ar,C-H),1694(C=O),1616(Ar),1530(C-N), 1524(Ph,C=C),1498(C=S ), 1435(Ph,C=C), 1304(C-N), 1292(C-N), 1000-1200(C-F), 774(Ar-H), 735(Ph,C-H). 1 H NMR (CDCl 3 ,400MHz),δ: 4.07(s,3H,CH 3),7.21(m,1H,Ph),7.30-7.33(m,1H,Ph),7.80-7.81(m,1H,Ph),8.10(s,1H,CH),8.96(s,1H,NH) ,12.36(s,1H,NH).HRMS(ESI)for C 13 h 9 f 5 N 4 OS m / z: Calculated, 365.0490, Found, [M+H] + .

Embodiment 3

[0035] N-((2,6-difluorophenyl)aminothiocarbonyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-ylthiourea, white solid, yield 28.6% , m.p.186~187℃; FTIR(ν,cm -1 ): 3245(N-H),3104(N-H),1692(C=O),1599(Ar),1530(C-N)(Ph,C=C), 1497(C=S),1295(C-N),1000- 1200(C-F),774(Ar-H),785,735(Ph,C-H). 1 H NMR (CDCl 3 ,400MHz), δ:4.07(s,3H,CH 3 ),7.03-7.13(m,2H,Ph),7.33-7.41(m,1H,Ph),8.10(s,1H,CH),9.14(s,1H,NH),11.58(s,1H,NH) .HRMS(ESI)forC 13 h 9 f 5 N 4 OS m / z: Calculated, 365.0490, Found, 365.0487 [M+H] + .

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Abstract

The invention discloses an acyl thiourea compound containing 1-methyl-3-trifluoromethyl-1H-parazole structure, as well as a preparation method and application thereof. The preparation method comprises the following steps: firstly, synthesizing 1-methyl-(trifluoromethyl)-1H-parazole-4-formic acid from ethyl 4,4,4-trifluoroacetoacetate, triethyl orthoformate and methylhydrazine serving as raw materials; secondly, performing acylating chlorination to obtain 1-methyl-(trifluoromethyl)-1H-parazole-4-formyl chloride; and finally, reacting with potassium thiocyanate and substituted aniline to obtain a final product (I). The compound is simple and easily available in raw materials, simple in preparation method, convenient in post treatment and high in product yield, has an antifungal activity, especially has an excellent sterilizing effect for fusarium wilt, bacterial angular leaf spot, grey mold and brown spots of cucumber, and lays foundation for novel pesticide research and development.

Description

technical field [0001] The invention belongs to the technical field of preparation of acylthiourea compounds, and in particular relates to an acylthiourea compound containing a 1-methyl-3-trifluoromethyl-1H-pyrazole structure, a preparation method and application thereof. Background technique [0002] The heterocyclic structure is an important key factor in the synthesis of drugs, pesticides and other substances, which is determined by the characteristics of high efficiency, low toxicity and diverse substitutions of heterocyclic rings. It has become a research hotspot in the field of medicine and pesticide. Succinate dehydrogenase inhibitors act on protein complex II in the mitochondrial respiratory electron transport chain of pathogenic bacteria, namely succinate dehydrogenase or succinate-ubiquinone reductase, which is newly classified by the Fungicide Resistance Action Committee (FRAC) A class of compounds with similar mechanism of action and resistance mechanism emerged...

Claims

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Application Information

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IPC IPC(8): C07D231/14A01N47/34A01P3/00A01P1/00
CPCA01N47/34C07D231/14
Inventor 刘幸海金涛翟志文沈钟华谭成侠翁建全武宏科
Owner ZHEJIANG UNIV OF TECH
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