26308-42-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Ethyl-1-methyl-1H-pyrazole-5-carboxylic acid is utilized as a key intermediate in the preparation of various bioactive compounds, including potential drugs. Its structural properties make it instrumental in the development of new pharmaceutical agents, contributing to the advancement of treatments for a range of medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Ethyl-1-methyl-1H-pyrazole-5-carboxylic acid serves as a crucial intermediate for the synthesis of agricultural products. Its application is vital for the creation of substances that can enhance crop protection and contribute to more efficient and sustainable agricultural practices.
Used in Organic Chemistry:
3-Ethyl-1-methyl-1H-pyrazole-5-carboxylic acid is employed as a versatile starting material in organic chemistry. Its functional groups and structural attributes facilitate the synthesis of diverse chemical substances, broadening the scope of chemical research and development.

InChI:InChI=1/C7H10N2O2/c1-3-9-4-6(7(10)11)5(2)8-9/h4H,3H2,1-2H3,(H,10,11)

Upstream product

• 26308-40-7 ethyl 3-ethyl-1H-pyrazole-5-carboxylate 
• 13246-52-1 ethyl-2,4-dioxohexanoate 
• 128537-26-8 3-ethyl-1-methylpyrazole-5-carboxylic acid ethyl ester 

Downstream Products

• 1005784-40-6 3-ethyl-N-{2-fluoro-5-[(2-{[(2-methylcyclopropyl)carbonyl]amino}imidazo[1,2-b]pyridazin-6-yl)oxy]phenyl}-1-methyl-1H-pyrazole-5-carboxamide 
• 1005783-44-7 N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide 
• 1186415-59-7 C₁₇H₂₀ClN₃O₃ 
• 1359764-25-2 C₁₉H₂₇N₃O₂ 
• 1359764-26-3 C₂₁H₂₃N₃O₃ 
• 1359764-27-4 C₂₀H₂₉N₃O₃ 
• 1359764-29-6 C₁₅H₁₈ClN₃O₂ 
• 1359764-40-1 C₁₉H₂₆ClN₃O 
• 1359764-42-3 C₂₁H₂₂ClN₃O₂ 
• 1359764-44-5 C₂₀H₂₈ClN₃O₂ 
• 1359764-46-7 C₁₅H₁₇Cl₂N₃O 
• 1359764-53-6 C₁₉H₂₅N₃O 
• 1359764-54-7 C₂₁H₂₁N₃O₂ 
• 1359764-55-8 C₂₀H₂₇N₃O₂ 

Relevant academic research and scientific papers

Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring

Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.

Pyrazole amide compound, and preparation method and application thereof

The invention discloses a pyrazole amide compound represented by the formula (I), and a preparation method and an application thereof, wherein R, R1, R2 and W have the definitions indicated in the specification. The compound represented by the formula (I) has bactericidal, insecticidal or acaricidal biological activities, and specially has quite high activity on pathogenic bacteria such as sphaerotheca fuliginea, botrytis cinerea, melampsora lini and the like.

5-pyrazole amide compound, and preparation method and application thereof

The invention discloses a 5-pyrazole amide compound as shown in a formula (I) which is described in the specification, and a preparation method and application thereof. In the formula (I), R, R1, R2, R3 and n are as defined in the specification. The 5-pyrazole amide compound as shown in the formula (I) has bactericidal, insecticidal or acaricidal bioactivity and especially has good activity to insects like aphids belonging to Homoptera and pathogens like Sphaerotheca fuliginea, Botrytis cinerea and rust pathogens.

Design, synthesis and biological evaluation of 1H-pyrazole-5-carboxamide derivatives as potential fungicidal and insecticidal agents

A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides. Graphical Abstract: A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides.[Figure not available: see fulltext.]

Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl-N-benzyl carboxamide, α-chloromethyl-N- benzyl carboxamide, and 4,5-dihydrooxazole moieties

On the basis of commercial insecticides tebufenpyrad and tolfenpyrad, two series of novel pyrazole-5-carboxamides containing α-hydroxymethyl-N- benzyl or α-chloromethyl-N-benzyl and pyrazoles containing 4,5-dihydrooxazole moieties were designed and synthesized via the key intermediate 2-amino-1-(4-substituted) phenyl ethanol. The structures of target compounds were confirmed by 1H NMR and elemental analysis or high-resolution mass spectrum (HRMS), and their activities against cotton bollworm (Helicoverpa armigera), diamondback moth (Plutella xylostella), bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), and spider mite (Tetranychus cinnabarinus) were tested. The results of bioassays indicated that compounds containing α-chloromethyl-N-benzyl and compounds containing 4,5-dihydrooxazole showed high insecticidal activity against cotton bollworm. Especially, stomach activities of compounds Ij, Il, and IIe were 60% at 5 mg kg-1. Moreover, the target compounds exhibited high selectivity between cotton bollworm and diamondback moth, although both of them belong to the order Lepidoptera. Although the activities against diamondback moth were at a low level, some of the target compounds exhibited antifeedant activity. The compounds also had good activities against bean aphid, mosquito, and spider mite. The foliar contact activity of compounds Ic, Id, Ie, and IIf against bean aphid were 95, 95, 100, and 95%, respectively, at 200 mg kg-1. The miticidal and ovicidal activities of compound IIi against spider mite were both 95% at 200 mg kg-1. Furthermore, a trivial change at 4-position of pyrazole ring would lead to great changes in properties and activities, which can easily be deduced by comparing the activities of compounds in series I (4-chloro-pyrazole compounds) with corresponding compounds in series II (4-hydro-pyrazole compounds), especially from the miticidal and ovicidal activities of Ii and IIi against spider mite.

Pyrazolodiazepines. 1,3 (and 2,3) dialkyl 4,6 dihydro 8 arylpyrazolo[4,3 e][1,4] diazepin 5 ones as antianxiety agents

A series of 1, 3 (and 2, 3) dialkyl 4, 6 dihydro 8 arylpyrazolo [4, 3 e][1, 4] diazepin 5 ones was synthesized and evaluated for psychotropic activity. Intermediates are new dialkylnitropyrazolyl aryl ketones prepared from dialkylnitropyrazolecarboxylic acids. Many of these pyrazolodiazepines exhibit high CNS activity in animals. One compound, 1 ethyl 4, 6 dihydro 3 methyl 8 phenylpyrazolo [4, 3 e] [1, 4] diazepin 5 (1H) one is about as potent as diazepam as an antianxiety agent with less sedative properties and is being studied in the clinic.