- Synthesis method of 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid
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The invention relates to a synthesis method of 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid, and the method comprises the following steps: 1, carrying out condensation reaction on N, N-dimethylamino ethyl acrylate, triethylamine and acetyl chloride to generate ethyl 2-dimethylamino-3-oxobutyrate and triethylamine hydrochloride; 2, carrying out a cyclization reaction on 2-dimethylamino ethyl-3-oxobutyrate and methylhydrazine to generate 1, 3-dimethyl-1H-pyrazole ethyl-4-formate and a dimethylamine aqueous solution; 3, carrying out a reaction on formic acid, ethyl acetoacetate and dimethylamine generated in the step 2 cyclization reaction to generate 2-dimethylamino ethyl-3-oxobutyrate and water, wherein the ethyl 2-dimethylamino-3-oxobutyrate generated in the step 3 is recycled as a reactantin the step 2; 4, hydrolyzing the ethyl 1, 3-dimethyl-1H-pyrazole-4-formate to obtain the 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid. The 1, 3-dimethyl-1H-pyrazole-4-carboxylic acid has the advantages of few synthesis steps, safe reaction process and no three-waste pollution, and is suitable for industrial batch large-scale preparation.
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- Expedient discovery for novel antifungal leads targeting succinate dehydrogenase: Pyrazole-4-formylhydrazide derivatives bearing a diphenyl ether fragment
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The pyrazole-4-carboxamide scaffold containing a flexible amide chain has emerged as the molecular skeleton of highly efficient agricultural fungicides targeting succinate dehydrogenase (SDH). Based on the above vital structural features of succinate dehydrogenase inhibitors (SDHI), three types of novel pyrazole-4-formylhydrazine derivatives bearing a diphenyl ether moiety were rationally conceived under the guidance of a virtual docking comparison between bioactive molecules and SDH. Consistent with the virtual verification results of a molecular docking comparison, the in vitro antifungal bioassays indicated that the skeleton structure of title compounds should be optimized as an N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide scaffold. Strikingly, N′-(4-phenoxyphenyl)-1H-pyrazole-4-carbohydrazide derivatives 11o against Rhizoctonia solani, 11m against Fusarium graminearum, and 11g against Botrytis cinerea exhibited excellent antifungal effects, with corresponding EC50 values of 0.14, 0.27, and 0.52 μg/mL, which were obviously better than carbendazim against R. solani (0.34 μg/mL) and F. graminearum (0.57 μg/mL) as well as penthiopyrad against B. cinerea (0.83 μg/mL). The relative studies on an in vivo bioassay against R. solani, bioactive evaluation against SDH, and molecular docking were further explored to ascertain the practical value of compound 11o as a potential fungicide targeting SDH. The present work provided a non-negligible complement for the structural optimization of antifungal leads targeting SDH.
- Chen, Min,Li, Guohua,Lu, Aimin,Qiu, Lingling,Wang, An,Wang, Xiaobin,Xue, Wei,Yang, Chunlong
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p. 14426 - 14437
(2020/12/22)
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- Method for synthesizing 1,3-dimethyl-1H-pyrazole-4-carboxylic acid
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The invention relates to a method for synthesizing 1,3-dimethyl-1H-pyrazole-4-carboxylic acid. The method comprises the step that 1,3-dimethyl-1H-pyrazole-4-carboxylic acid is prepared from the raw material: ethyl acetoacetate through condensation and ring closure, formylation, reductive dechlorination and oxidation. Compared with an existing method, the method has lower reaction cost, a higher yield and better economic performance; and the problems such as cost and environmental pollution caused by heavy metal oxidation are solved, and conditions are created for industrialization.
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Paragraph 0022; 0035; 0039-0041; 0058-0063
(2019/11/12)
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- (1H-pyrazole-4-carboxamido) ethyl benzoate compound as well as preparation method and application thereof
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The invention discloses an ethyl (1H-pyrazole-4-carboxamido) benzoate compound as well as a preparation method and application thereof. The structural formula of the (1H-pyrazole-4-carboxamido) ethylbenzoate compound is as shown in the formula (I), wherein the substituent groups R1 are phenyl or substituted phenyl, the number of substituent groups on a benzene ring of the substituted phenyl is one or more, and each substituent group is independently selected from H, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 halogenated alkyl or nitro; and the substituent R2 is methyl, monofluoromethyl, difluoromethyl or trifluoromethyl. The invention discloses a novel compound with bactericidal activity, which is simple in preparation method and convenient to operate, and the obtained compound has betterinhibitory activity on pathogenic bacteria such as cucumber botrytis cinerea, fusarium oxysporum, cucumber corynespora leaf spot and the like under the concentration of 50 mg/mL.
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- Application of 1,3-dimethyl-1H-pyrazole-4-amide derivatives to herbicide preparation
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The invention relates to an application of 1,3-dimethyl-1H-pyrazole-4-amide derivatives to herbicide preparation. Lettuce and Agrostis seeds are taken as test objects, and the following steps are carried out: sample treatment: the seeds are subjected to surface sterilization with 5%-10% Chlorox solution for 10 min before bioassay, and then the seeds are washed thoroughly by deionized water in a Millipore system and aired in an aseptic environment; sample treatment: 1 mM solutions are prepared from all samples by adopting acetone as a solvent; bioassay: bioassay is performed finally, and obtained compounds show better inhibition for lettuce and Agrostis. The compounds are new compounds with herbicidal activity, and the basis is provided for research and development of new pesticides.
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Paragraph 0013; 0016; 0017
(2019/01/16)
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- Synthesis and Nematocidal Activity of N-Substituted 3-Methyl-1H-pyrazole-4-carboxamide Derivatives Against Meloidogyne incognita
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A series of novel pyrazole carboxamides were designed and synthesized through multi-step reactions from ethyl acetoacetate and triethyl orthoformate, and their structures were characterized by Fourier transform infrared, 1H-NMR, 13C-NMR, mass spectrometry, and elemental analysis. The preliminary insecticidal activity showed that some of them possessed good insecticidal activities against Meloidogyne incognita.
- Cheng, Long,Shen, Zhong-Hua,Xu, Tian-Ming,Tan, Cheng-Xia,Weng, Jian-Quan,Han, Liang,Peng, Wei-Li,Liu, Xing-Hai
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p. 946 - 950
(2018/02/12)
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- 1,3-dimethyl-1H-pyrazole-4-amide derivative as well as preparation method and application thereof
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The invention relates to a 1,3-dimethyl-1H-pyrazole-4-amide derivative as well as a preparation method and application thereof. The derivative is prepared by the steps of carrying out reflux on ethylacetoacetate and triethyl orthoformate in acetic anhydride, adding into methylhydrazine so as to prepare 1,3-dimethyl-1H-pyrazole-4-ethyl formate, carrying out hydrolysis, adding hydrochloric acid soas to prepare 1,3-dimethyl-1H-pyrazole-4-carboxylic acid, reacting by virtue of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid and sulfoxide chloride, adding dichloromethane for dilution, and adding arylalkylamine and triethylamine, so as to prepare the 1,3-dimethyl-1H-pyrazole-4-amide derivative. The preparation method is simple and convenient in operation; the obtained compound has optimal inhibitory activity to sclerotinia sclerotiorum at 50ppm, and the inhibition ratio reaches 87.5%; the obtained compound has relatively good inhibitory activity to macrophoma kawatsukai, and the inhibition ratio is equal to that of a contrast medicament; and the compound is a novel compound with bactericidal activity, and the foundation is provided for the research and development of novel pesticides.
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Paragraph 0030; 0033; 0034
(2018/06/16)
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- Acyl thiourea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof
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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 orthoforma
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- Acyl urea compound containing 1,3-dimethyl-1H-pyrazole structure and preparation method and application thereof
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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.
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- Amide compound containing methylpyrazole and preparation method the application thereof
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The invention discloses an amide compound containing methylpyrazole and a preparation method the application thereof. The compound, namely the N-substituted-(1,3-dimethyl-1H-pyrazol-4-yl) is a new compound having nematocidal activity and is especially used for preventing and controlling meloidogyn incognita and the like, and a foundation is provided for research and development of new pesticides.
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- Synthesis and antifungal activity of the derivatives of novel pyrazole carboxamide and isoxazolol pyrazole carboxylate
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A series of pyrazole carboxamide and isoxazolol pyrazole carboxylate derivatives were designed and synthesized in this study. The structures of the compounds were elucidated based on spectral data (infrared, proton nuclear magnetic resonance and mass spectroscopy). Then, all of the compounds were bioassayed in vitro against four types of phytopathogenic fungi (Alternaria porri, Marssonina coronaria, Cercospora petroselini and Rhizoctonia solani ) using the mycelium growth inhibition method. The results showed that some of the synthesized pyrazole carboxamides displayed notable antifungal activity. The isoxazole pyrazole carboxylate 7ai exhibited significant antifungal activity against R. solani, with an EC50 value of 0.37 μg/mL. Nonetheless, this value was lower than that of the commercial fungicide, carbendazol.
- Sun, Jialong,Zhou, Yuanming
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p. 4383 - 4394
(2015/05/06)
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- Electrosynthesis of pyrazole-4-carboxylic acids by oxidation of 4-formylpyrazoles on NiO(OH)-electrode in aqueous alkaline solution
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Electrochemical oxidation of di- and trisubstituted 4-formylpyrazoles on a Ni-anode in aqueous alkali led to the formation of the corresponding pyrazole-4-carboxylic acid in 60-90% yields. The yields of the target products depend on position of substituent in the pyrazole ring and are decreased in the following sequence of substituent at position 1 Me > Et > Ph, as well as when the aqueous medium was replaced with aqueous alcohol (50% Bu tOH). Oxidation of 4-formylpyrazoles containing Me groups at the carbon atoms of the pyrazole ring led, to monoacids and also pyrazoledicarboxylic acids in small (1.5-14%) amounts; the latter were the oxidation products of the aldehyde and the Me groups.
- Lyalin,Petrosyan
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p. 1148 - 1153
(2013/07/26)
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- A one-pot process for the regioselective synthesis of 1,3,4-trisubstituted-1H-pyrazoles
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This Letter reports a facile and regioselective one-pot synthesis of 1,3,4-trisubstituted-1H-pyrazoles. It comprises a three-step telescoped sequence, which has been utilised in the production of a variety of differentially substituted pyrazoles.
- Raw, Steven A.,Turner, Andrew T.
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experimental part
p. 696 - 699
(2011/02/27)
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- AMIDE COMPOUNDS AND MEDICINAL USE THEREOF
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The present invention relates to a compound of the formula wherein R1 is substituted aryl, heteroaryl and the like, R2 and R3 are hydrogen, alkyl, halogen, hydroxyl group and the like, Q is N, CH and the like, W is hydrogen, alkyl, hydroxycarbonylalkyl and the like, X is halogen, cyano, nitro, amino and the like, X' is hydrogen, halogen, cyano, nitro, and Y is alkyl, hydroxyl group, alkoxy, mercapto and the like and a salt thereof, and a medicine containing the said compound. The compound of the present invention shows a superior inhibitory effect on activated lymphocytes proliferation and is useful as an agent for the prophylaxis or treatment of various autoimmune diseases.
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- Pyrazole carboxanilide fungicides and use
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Novel N-[2-(cyclic alkyl)phenyl]pyrazole-4-carboxamides useful as fungicides, methods of using said compounds, and fungicidal compositions containing them.
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- CONVERSION DE L'ACETYL-5 URACILE EN DERIVES PYRAZOLIQUES PAR L'HYDRAZINE ET LES HYDRAZINES MONOSUBSTITUEES
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5-Acetyl uracile 1 is easily transformed by hydrazine and methylhydrazine into 4-allophanoyl-3-methyl pyrazole 2 (R=H) and 4-allophanoyl-1,3-dimethyl pyrazole 2 (R=CH3).The pyrazoles 2, in boiling butanol and in the presence of hydrochloric acid lead resp
- Bajnati, Abdelilah,Hubert-Habart, Michel
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p. 540 - 547
(2007/10/02)
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- Pyrazolecarbonylamine derivatives and agricultural and horticultural fungicides containing said compounds
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Novel pyrazole derivatives of the general formula (I) STR1 wherein R1 represents an alkyl, haloalkyl, alkenyl, haloalkenyl or phenyl group, R2 and R3 each represent a hydrogen or halogen atom, or an alkyl, haloalkyl, alkoxy, alkoxyalkyl or phenyl group, and R4 represents an alkyl, alkenyl, haloalkenyl or phenyl group, or a heterocyclic aromatic group which contains at least one of oxygen, nitrogen and sulfur atoms and may be unsubstituted or substituted, which are useful as agricultural and horticultural fungicides. The pyrazole derivatives can be produced by reacting compounds of the general formula (III) STR2 wherein R1, R2 and R3 are as defined above, and X represents a halogen atom, with aminoacetonitriles of the general formula (IV) STR3 wherein R4 is as defined above, or salts thereof.
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