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Acyl thiourea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof
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A technology for acylthiourea compounds, 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, simple preparation methods, and high product yields
Inactive Publication Date: 2017-08-11
ZHEJIANG UNIV OF TECH
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The molecular structure of this type of fungicides has relatively large changes, and most of the fungicides discovered in recent years contain pyrazole rings.
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Embodiment 1
[0031] N-((2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-ylthiourea, white crystal, yield 54.4%, m.p.222-224℃; 1 H NMR (CDCl 3 ,500MHz),: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-CH 3 ),2.57(s,3H,pyrazole CH 3 ); HRMS calcd for C 13 h 13 FN 4 OS 293.0867, found 293.0860 [M+1] + .
Embodiment 2
[0033] N-((3-fluorophenyl)-1,3-dimethyl-1H-pyrazole-4-ylthiourea, white crystal, yield 30.7%, m.p.186-188℃; 1 H NMR (CDCl 3 ,500MHz),δ:11.34(s,1H,-NH-), 10.02(s,1H,Ar-NH-),8.27(s,1H,pyrazole H),7.90(s,1H,Ar-H), 7.74 (d, J = 8.29Hz, 1H, Ar-H), 7.49 (t, J = 7.87, 7.87Hz, 1H, Ar-H), 7.42 (d, J = 7.76 Hz, 1H, Ar-H), 3.73(s,3H,N-CH 3 ),2.53(s,3H,pyrazole CH 3 ); HRMS calcd for C 13 h 13 FN 4 OS 293.0867, found 293.0891[M+1] + .
Embodiment 3
[0035]N-((3,4-difluorophenyl)-1,3-dimethyl-1H-pyrazole-4-ylthiourea, light yellow solid, yield 40.9%, m.p.201-203℃; 1 H NMR (CDCl 3 ,500MHz),δ:11.26(s, 1H,-NH-),10.18(s,1H,Ar-NH-),8.38(s,1H,pyrazole H),7.76(s,1H,Ar-H), 7.32-7.27(m, 2H, Ar-H), 7.14(d, J=7.43Hz, 1H, Ar-H), 3.81(s, 3H, N-CH 3 ), 2.52(s,3H,pyrazole CH 3 ); HRMS calcd for C 13 h 12 f 2 N 4 OS 311.0773, found 311.0768[M+1] + .
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Abstract
The invention discloses an acyl thiourea 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 acylating chlorination to obtain 1,3-dimethyl-1H-pyrazole-4-formyl chloride, and reacting with ammoniumthiocyanate 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 preparation of acylthiourea compounds, and in particular relates to an acylthiourea 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 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. Since th...
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