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Acyl urea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof

A compound, dimethyl technology

Inactive Publication Date: 2017-08-11
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 urea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof
  • Acyl urea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof
  • Acyl urea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0032] N-((4-ethylphenyl)-1,3-dimethyl-1H-pyrazole-4-acylurea, white crystals, yield 40.2%, m.p.235-236℃; 1 H NMR(CDCl 3 ,400MHz),δ:10.98(s,1H,-NH-),10.14(s,1H,Ar-NH-),8.41(s,1H,pyrazole H),7.49(d,J=8.1Hz,2H, Ar-H), 7.21 (d, J = 8.1 Hz, 2H, Ar-H), 3.77 (s, 3H, N-CH 3 ), 2.67(q,J=7.6Hz,2H,-CH 2 -),2.54(s,3H,pyrazole-CH 3 ),1.25(t,J=7.6Hz,3H,CH 3 ); ESI-HRMS calcd for C 15 H 18 N 4 O 2 287.1503,found 287.1499[M+1] + .

Embodiment 2

[0034] N-((2-nitro-4-chlorophenyl)-1,3-dimethyl-1H-pyrazole-4-acylurea, yellow solid, yield 47.5%, m.p.197-199°C; 1 H NMR(CDCl 3 ,400MHz),:12.53(s,1H,-NH-),8.52(d,J=9.1Hz,1H,Ar-NH-)8.31(s,1H,pyrazole H),8.18(s,1H,Ar- H),,7.93(s,1H,Ar-H),7.57(d,J=9.1Hz,1H,Ar-H),3.86(s,3H,N-CH 3 ),2.54(s,3H,pyrazole-CH 3 ); ESI-HRMS calcd forC 13 H 12 ClN 5 O 4 338.0651,found 338.0648[M+1] + .

Embodiment 3

[0036] N-((2,5-Difluorophenyl)-1,3-dimethyl-1H-pyrazole-4-acylurea, white crystals, yield 54.4%, m.p.222-224℃; 1 H NMR(CDCl 3 ,400MHz),:11.46(s,1H,-NH-), 9.52(s,1H,Ar-NH-), 8.28(s,1H,pyrazole H), 8.09-8.00(m,1H,Ar-H) ,7.17-7.11(m,1H,Ar-H), 6.81(s,1H,Ar-H), 3.92(s,3H,N-CH3), 2.57(s,3H,pyrazole-CH 3 ); ESI-HRMS calcd for C 13 H 12 F 2 N 4 O 2 295.1001,found 295.1004[M+1] + .

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Abstract

The invention discloses an acyl urea compound containing a 1,3-dimethyl-1H-pyrazole structure and a preparation method and application thereof. The preparation method comprises the following steps: firstly using ethyl acetoacetate, triethyl orthoformate and methylhydrazine as raw materials to synthesize 1,3-dimethyl-1H-pyrazole-4-formic acid, performing the amidation to obtain 1,3-dimethyl-1H-pyrazole-4-formamide, and reacting with oxalyl chloride and substituted anilines to obtain a final product (I). The raw materials are simple and are easily obtained, the preparation method is simple, the aftertreatment is convenient, and the product yield is high. The compound has the antifungal activity, and has the good sterilizing effect in allusion to sclerotinia sclerotiorum, rhizoctonia solani, Cercospora arachidicola Hori, Macrophoma kawatsukai, and alternaria solani especially. The foundation is provided for new pesticide research and development.

Description

Technical field [0001] The invention belongs to the technical field of acylurea compound preparation, and specifically relates to an acylurea compound containing a 1,3-dimethyl-1H-pyrazole structure, and a preparation method and application thereof. Background technique [0002] The heterocyclic structure is an important key factor for the synthesis of drugs, pesticides and other substances, which is determined by the high efficiency, low toxicity and diversified substitution characteristics of the heterocyclic ring. It has become a research hotspot in the fields of medicine and pesticides. Succinate dehydrogenase inhibitors act on the protein complex II in the 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 action mechanism and resistance mechanism. Since the advent of carboxin and oxycarb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/14A01N47/34A01P3/00A01P1/00
CPCC07D231/14A01N47/34
Inventor 刘幸海王翰翟志文沈钟华谭成侠翁建全武宏科孙娜波
Owner ZHEJIANG UNIV OF TECH
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