141573-95-7Relevant articles and documents
Crystal structure and molecular docking studies of new pyrazole-4-carboxamides
Qiao, Li,Cai, Peng-Peng,Shen, Zhong-Hua,Wu, Hong-Ke,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai
, p. 66 - 72 (2019)
Two pyrazol-4-carboxamides, 3-(difluoromethyl)-N-(mesitylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxa-mide (7a) and 3-(difluoromethyl)-N-((3,5-dimethylphenyl) carbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7b) were synthesized and their structures were confirmed by the aid of 1H NMR and HRMS analyses. The structure of the pyrazole-4-carboxamide, 7a was also determined by X-ray diffraction. The preliminary activity results demonstrate that these two compounds exhibit good inhibitory activity against Botrytis cinerea. Further docking results indicated that the key active group is difluoromethyl pyrazole moiety.
An atom-efficient route to ethyl 3-(difluoromethyl)-1-methyl-1 H-pyrazole-4-carboxylate (DFMMP)-A key building block for a novel fungicide family
Jaunzems, Janis,Braun, Max
, p. 1055 - 1059 (2014)
A growing number of fluorine-containing active ingredients in the pharmaceutical and agrochemical industries inevitably raises the demand for new fluorinated building blocks. Their availability is mainly constricted by suitable chemistry and available bulk fluorine containing starting materials. Because of the high cost impact especially in the agrochemical industry, the choice of a synthetic route is heavily driven by economic aspects; thus, the environmental profile often is handled as a "secondary factor" or finally falls aside. DFMMP is a key building block for a fast growing new fungicide family, like Syngenta's Sedaxane, and BASF's Fluxapyroxad and Bayer's Bixafen currently made by environmetally less friendly routes. Herein we present a cost-competitive and green route, developed at Solvay laboratories, displaying significantly lower environmental impact.
Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties
Liu, Xing-Hai,Zhao, Wen,Shen, Zhong-Hua,Xing, Jia-Hua,Xu, Tian-Ming,Peng, Wei-Li
, p. 881 - 889 (2017)
A series of novel difluoromethylpyrazole carboxamides derivatives were synthesized by introduction of flexible alkyl chain. Nematicidal bioassay results showed that some of them exhibited good control efficacy against M. incognita, which indicated that these difluoromethylpyrazole carboxamides derivatives might be potential novel lead compounds for discovery new nematicides. The nematicidal activity was affected by the substituted position in the molecule, especially the substitution group on the alkyl chain. It was found that the compound 6-9 and 6-23 possess about 50% inhibition effect against M. incognita even at 5.0 and 1.0 mg L?1. Meanwhile, greenhouse field trial showed the nematicidal activity of compound 6-9 is a litter weaker than that of Abamectin. The mammalian toxicology results indicated that compound 6-9 was a low-toxicity and low-sensitive compound. In conclusion compound 6-9 is a potential candidate for further development. In addition, the molecular docking simulations revealed that compounds 6 with a flexible NHCOO show its binding affinities for the acetylcholine receptor (AChR), which may provide useful information for further design novel nematicides.
Synthesis and biological activity of acyl thiourea containing difluoromethyl pyrazole motif
Min, Li-Jing,Zhai, Zhi-Wen,Shi, Yan-Xia,Han, Liang,Tan, Cheng-Xia,Weng, Jian-Quan,Li, Bao-Ju,Zhang, Yong-Gang,Liu, Xing-Hai
, p. 22 - 28 (2020)
A series of new acyl thiourea derivatives containing difluoromethyl pyrazole moiety were designed and synthesized. Their structures were confirmed by 1H NMR, 31C NMR, MS and HRMS. The bioassay results showed that some of title compounds exhibited good in vivo fungicidal activity against Botrytis cinerea and Fusarium oxysporum and good antibacterial activity against Pseudomonas syringae pv. Lachrymans at 50 mg/L respectively.
Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives
Qiao, Li,Zhai, Zhi-Wen,Cai, Peng-Peng,Tan, Cheng-Xia,Weng, Jian-Quan,Han, Liang,Liu, Xing-Hai,Zhang, Yong-Gang
, p. 2536 - 2541 (2019)
Nine novel difluoromethylpyrazole acyl urea derivatives were synthesized via seven steps conveniently. All the structures were determined by 1H-NMR, 13C-NMR, HRMS, and X-ray diffraction. The in vivo fungicidal activities were determined against Corynespora mazei, Botrytis cinerea, Fusarium oxysporum, and Pseudomonas syringae, respectively. The bioassay results indicated that some of them displayed good control effective (around 50 and 80%) against P. syringae and B. cinerea at 50 mg/L, respectively, which is better than control. It is possible that difluoromethylpyrazole acyl urea derivatives can be a leading compound for the development of new fungicides against the two fungi with further structure optimization. Furthermore, docking model was studied to establish structure–activity relationship of difluoromethylpyrazole acyl urea derivatives.
PRODUCING METHOD FOR 3-DIFLUOROMETHYLPYRAZOLE COMPOUND, PRODUCING METHOD FOR 3-DIFLUOROMETHYLPYRAZOLE-4-CARBOXYLIC ACID COMPOUND, AND PYRAZOLIDINE COMPOUND
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Paragraph 0147-0184; 0190-0191, (2021/03/05)
Provided are producing methods for a 3-difluoromethylpyrazole compound and a 3-difluoromethylpyrazole-4-carboxylic acid compound, which include, in a reaction solvent containing a specific solvent, subjecting a difluoroacetyl group-containing compound, a hydrazine compound, and formaldehyde to a cyclocondensation reaction, and subsequently oxidizing the obtained pyrazole compound precursor, and a pyrazolidine compound represented by a specific formula in these producing methods.
Synthesis and preparation method of 4-pyrazole ethyl formate
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, (2021/03/13)
The invention discloses a synthesis and preparation method of 4-pyrazole ethyl formate. The method comprises the following steps: dissolving ethyl 2-dichloroacetyl-3-(dimethylamino) acrylate in an organic solvent, and reacting with methylhydrazine to obtain ethyl 1-methyl-3-dichloromethyl-4-pyrazole formate; reacting the obtained ethyl 1-methyl-3-dichloromethyl-4-pyrazole formate with a fluorination reagent to obtain 1-methyl- 3-difluoromethyl-4-pyrazole ethyl formate; mixing 1-methyl- 3-difluoromethyl-4-pyrazole ethyl formate with glacial acetic acid, dropwise adding a strong acidic solutionat the temperature of 0 DEG C, and then adding dichloromethane and water for stirring and layering to obtain an organic layer; and recrystallizing the organic layer by using a mixed solvent of petroleum ether and ethyl acetate to obtain the 4-pyrazole ethyl formate. The method has the advantages of wide raw material source, low raw material price and simple preparation process, and the obtained product is easy to purify, low in production cost and suitable for large-scale industrial production.
Expanding the Chemical Space of Succinate Dehydrogenase Inhibitors via the Carbon-Silicon Switch Strategy
Wei, Ge,Huang, Ming-Wei,Wang, Wen-Jie,Wu, Yuan,Mei, Shu-Fen,Zhou, Li-Ming,Mei, Long-Can,Zhu, Xiao-Lei,Yang, Guang-Fu
, p. 3965 - 3971 (2021/05/04)
The carbon-silicon switch strategy has become a key technique for structural optimization of drugs to widen the chemical space, increase drug activity against targeted proteins, and generate novel and patentable lead compounds. Flubeneteram, targeting succinate dehydrogenase (SDH), is a promising fungicide candidate recently developed in China. We describe the synthesis of novel SDH inhibitors with enhanced fungicidal activity to enlarge the chemical space of flubeneteram by employing the C-Si switch strategy. Several of the thus formed flubeneteram-silyl derivatives exhibited improved fungicidal activity against porcine SDH compared with the lead compound flubeneteram and the positive controls. Disease control experiments conducted in a greenhouse showed that trimethyl-silyl-substituted compound W2 showed comparable and even higher fungicidal activities compared to benzovindiflupyr and flubeneteram, respectively, even with a low concentration of 0.19 mg/L for soybean rust control. Furthermore, compound W2 encouragingly performed slightly better control than azoxystrobin and was less active than benzovindiflupyr at the concentration of 100 mg/L against soybean rust in field trials. The computational results showed that the silyl-substituted phenyl moiety in W2 could form strong van der Waals (VDW) interactions with SDH. Our results indicate that the C-Si switch strategy is an effective method for the development of novel SDH inhibitors.
3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds, and preparation method and application thereof
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Paragraph 0028-0030, (2020/01/25)
The invention discloses 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds, and a preparation method and an application thereof. The 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylatecompounds are 2-(benzoyloxy)ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds, and have a structural formula represented by formula (I) shown in the description; and in the formula(I), a substituent group R is a phenyl group or a substituted phenyl group, and a substituent group on the benzene ring of the substituted phenyl group is halogen or a C1-C3 alkyl group. The 2-(benzoyloxy)ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds are new compounds with bactericidal activity, have a good inhibition rate on Fusarium graminerum at the concentration of 50ppm, and provide a basis for research and development of new pesticides.
Preparation method and application of -4- (S)-2-(1H- pyrazolecarboxamide)-P-methylbenzoate compound as well as preparation method and application thereof (by machine translation)
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Paragraph 0030-0032, (2020/02/14)
The invention discloses (S)- 2 - (1 a system. H-pyrazol-4 (propyl-formamide)-based) propyl benzoate compound as well as preparation method, (S)- 2 - (1 and application thereofHThe structural formula of the-pyrazol-4-formamide)-based ethyl (I) benzoate compound is shown in a formula shown: in the specification. Substituent groups R in the (I) formula (No.No. STR3No.No., No.No. STR7No.No.No.). 1 The number of substituents on the, phenyl ring, which is a phenyl group or a substituted phenyl group, is, each independently selected from the group consisting of one, C1 - C4 or, more, C1 - C4 substituents, C1 - C3 each; of which R is independently selected from the group consisting of a halogen atom, an alkyl group, an alkyl group, an alkyl group, and a substituted phenyl group. 2 The preparation method of the novel compound with the. bactericidal activity is simple, and the compound obtained by the method, disclosed by the invention, is simple, in preparation method, 50mg/mL and the compound obtained by, the method disclosed by the invention has a good inhibition activity on. cucumber Botrytis cinerea and pathogenic bacteria such as cucumbers. (by machine translation)
