cas 176969-34-9, 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

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PRODUCING METHOD FOR 3-DIFLUOROMETHYLPYRAZOLE COMPOUND, PRODUCING METHOD FOR 3-DIFLUOROMETHYLPYRAZOLE-4-CARBOXYLIC ACID COMPOUND, AND PYRAZOLIDINE COMPOUND
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.
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Paragraph 0185-0189

(2021/03/05)

Expanding the Chemical Space of Succinate Dehydrogenase Inhibitors via the Carbon-Silicon Switch Strategy
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.
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)

Synthesis and biological activity of acyl thiourea containing difluoromethyl pyrazole motif
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.
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
(2019/07/12)

3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate compounds, and preparation method and application thereof
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.
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Paragraph 0028; 0031-0032

(2020/01/25)

Preparation method and application of -4- (S)-2-(1H- pyrazolecarboxamide)-P-methylbenzoate compound as well as preparation method and application thereof (by machine translation)
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)
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Paragraph 0030; 0033; 0034

(2020/02/14)

Expedient discovery for novel antifungal leads targeting succinate dehydrogenase: Pyrazole-4-formylhydrazide derivatives bearing a diphenyl ether fragment
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
p. 14426 - 14437
(2020/12/22)

Preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid
The invention discloses a preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, and belongs to the technical field of organic synthesis. The preparation method comprises thefollowing steps: by taking 2, 2-difluoroacetyl halide as a raw material, performing addition with alpha, beta-unsaturated ester, performing alkaline hydrolysis to obtain alpha-difluoroacetyl intermediate carboxylic acid, condensing and cyclizing the 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid with a methylhydrazine aqueous solution in the presence of a catalyst to obtain a 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid crude product, and recrystallizing to obtain a pure product of the 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid. The method has the advantages of simple operation, easily available raw materials, high reaction yield, reduction of isomers through a plurality of ways in the reaction process, and convenience in product purification.
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Paragraph 0036; 0039-0040

(2020/07/15)

Preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid
The invention discloses a preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, and belongs to the technical field of organic synthesis. The preparation method comprises thefollowing steps: reacting N-methyl-3-aminopyrazole as a raw material with bromine/iodine to replace pyrazole at site 4, then carrying out diazotizing and coupling with potassium difluoromethyl trifluoroborate to obtain 4-bromo-3-(difluoromethyl)-1-methyl-1H-pyrazole, then performing Grignard exchange by adopting isopropyl magnesium chloride and the like, and performing reaction with carbon dioxide to obtain 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid. The method is simple and convenient to operate, the total yield of the three steps is as high as 64%, the product purity can reach 99.5% or above, the situation in which isomers exist in a traditional process is avoided, and the method has potential process amplification prospects.
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Paragraph 0022; 0028-0029

(2020/07/15)

Preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid
The invention discloses a preparation method of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, and belongs to the field of pesticide organic synthesis. The preparation method comprises thefollowing steps: step 1, enabling 1-methyl-3-(trimethylsilyl) pyrazole to react with halogen to obtain 4-halogen-1-methyl-3-(trimethylsilyl) pyrazole; step 2, after exchange is conducted through a Grignard reagent, enabling the 4-halogen-1-methyl-3-(trimethylsilyl) pyrazole to react with chloroformate to obtain 1-methyl-3-trimethylsilyl-1H-pyrazole-4-carboxylic acid; step 3, then carrying out a heating reaction with bromine, so as to obtain 3-bromo-1-methyl-1H-pyrazole-4-carboxylic acid; and step 4, finally, carrying out heating coupling on the 3-bromo-1-methyl-1H-pyrazole-4-carboxylic acid and difluoromethylboronic acid by adopting a palladium catalyst, and performing recrystallization to obtain the 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid. The invention provides a new synthesis path for the synthesis of the compound, and has a potential industrial method prospect.
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Paragraph 0045-0053

(2020/07/13)

Preparation method and application of pyrazole derivative
The invention relates to a preparation method of a pyrazole derivative. The compound shown in the formula I reacts with a silanization reagent shown in a formula II to generate an intermediate productshown in a formula III, the intermediate product shown in the formula III reacts with a halogenated acid derivative shown in a formula IV to generate a halogenated compound shown in a formula V, andthe halogenated compound shown in the formula V reacts under acidic conditions to generate a pyrazole derivative shown in a formula VI. The preparation method of the pyrazole derivative is suitable for industrial production.
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(2020/05/08)

Method for synthesizing 3- difluoro methyl -1- methyl -1H- pyrazole -4- carboxylic acid by one-pot method
The invention discloses a method for synthesizing 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid by a one-pot method, wherein the method includes the following steps: in xylene, carrying outa condensation reaction of 4,4-difluoroethylacetoacetate and triethyl orthoformate under heating and catalysis of metal carboxylate, cooling, then dropwise adding a methylhydrazine aqueous solution, then heating up, carrying out a ring closing reaction, carrying out saponification and acidification of the obtained ring-closed reaction liquid, and thus obtaining the 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid. The method is reasonable in design, high in yield, simple in process operation, low in cost, and suitable for industrialized production.
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Paragraph 0027-0060

(2020/04/09)

METHOD FOR PRODUCING HALOGEN-CONTAINING PYRAZOLE CARBOXYLIC ACID AND INTERMEDIATE THEREOF
The invention provides a method capable of more simply and efficiently producing halogen-containing pyrazolecarboxylic acids and intermediates thereof, which are useful as pharmaceutical or agrochemical intermediates, in a manner suitable for industrial production. In particular, the invention provides a method of producing a compound represented by the formula (b), which comprises reacting a compound represented by the formula (a) with a halogenating agent selected from the group consisting of a compound represented by X2 (formula (1)), a compound represented by SOX2 (formula (2)), and a compound represented by SO2X2 (formula (3)) to obtain the compound represented by the formula (b): formula (1) X2 formula (2) SOX2 formula (3) SO2X2 wherein each symbol is as described in the description.
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Paragraph 0080-0081

(2020/01/24)

PRODUCTION METHOD FOR HALOGENATED PYRAZOLECARBOXYLIC ACID
The invention provides a method capable of more simply and efficiently producing halogen-containing pyrazolecarboxylic acids useful as pharmaceutical or agrochemical intermediates, in a manner suitable for industrial production. In particular, the invention provides a method of producing a compound represented by the formula (b), which comprises reacting a compound represented by the formula (a) with oxygen in the presence of a compound containing a transition metal atom to obtain the compound represented by the formula (b): wherein each symbol is as described in the description.
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Page/Page column 0081-0095

(2020/01/24)

Halogen substituted compound and preparation method and application thereof
The invention relates to a preparation method of a halogen substituted compound. A piperazine derivative shown as a formula I reacts with a halogenated acetyl halide derivative shown as a formula VI to generate the halogen substituted compound shown as a formula II. The invention further relates to a preparation method of a pyrazole derivative from the halogen substituted compound, the halogen substituted compound shown in the formula II reacts with methylhydrazine, a pyrazole ring is closed, and a halogen substituted alkyl-1-methylpyrazole derivative shown in a formula IV is generated; or thehalogen substituted compound shown in the formula II reacts with methylhydrazine benzaldehyde hydrazone to generate a hydrazone compound as shown in a formula III, the pyrazole ring is closed, and the halogen substituted alkyl-1-methylpyrazole derivative shown in the formula IV is generated. The invention also relates to the structure of an intermediate compound. The preparation methods of the halogen substituted compound and the pyrazole derivative are suitable for industrial production.
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Paragraph 0023; 0025

(2019/12/29)

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives
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.
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
(2019/08/16)

Crystal structure and molecular docking studies of new pyrazole-4-carboxamides
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.
Qiao, Li,Cai, Peng-Peng,Shen, Zhong-Hua,Wu, Hong-Ke,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai
p. 66 - 72
(2019/05/29)

Halogen substituted intermediate compound and preparation method and application thereof
The invention relates to a preparation method of a halogen-substituted intermediate compound. The halogen-substituted intermediate compound shown as a formula VIII is generated by reacting a compoundshown as a formula VII with a halogenated acetyl halide derivative shown as a formula VI. The invention relates to a preparation method for preparing a pyrazole derivative from the halogen substitutedintermediate compound, and the preparation method comprises the following steps: reacting the halogen substituted intermediate compound as shown in the formula VIII with methylhydrazine, and closinga pyrazole ring to generate a halogen substituted alkyl-1-methylpyrazole derivative as shown in a formula IV; or reacting the halogen substituted intermediate compound as shown in the formula VIII with methylhydrazine benzaldehyde hydrazone to generate a hydrazone compound as shown in a formula III, and closing the pyrazole ring under the action of an acid to generate the halogen substituted alkyl-1-methylpyrazole derivative as shown in the formula IV. The invention also relates to the structure of the intermediate compound. The preparation methods of the halogen-substituted intermediate compound and the pyrazole derivative are suitable for industrial production.
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Paragraph 0023; 0024; 0025

(2019/12/29)

(1H-pyrazole-4-carboxamido) ethyl benzoate compound as well as preparation method and application thereof
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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Paragraph 0031; 0036; 0037

(2020/01/08)

N-(2-benzamide)-1H-pyrazole-4-formamide compound as well as preparation method and application thereof
The invention discloses an N-(2-benzamide)-1H-pyrazole-4-formamide compound as well as a preparation method and application thereof. The N-(2-benzamide)-1H-pyrazole-4-formamide compound, namely a N-(2-benzamide)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-formamide compound, has a structural formula which is shown as a formula (I); wherein R is phenyl or substituted phenyl, the number of substituents on a benzene ring of the substituted phenyl is one or more, and each substituent is independently selected from halogen, C1-C3 alkyl or C1-C3 alkoxy group. The N-(2-benzamide)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-formamide compound disclosed by the invention is a new compound with bactericidal activity, has a relatively good inhibition rate on rhizoctonia solani at the concentration of 50 ppm, and provides a basis for research and development of new pesticides.
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Paragraph 0031; 0034-0035

(2020/01/08)

PROCESS FOR THE MANUFACTURE OF IMINIUM COMPOUNDS AND THEIR APPLICATION IN THE MANUFACTURE OF PYRAZOLE DERIVATIVES
Process for the manufacture of iminium compounds and their application in the manufacture of pyrazole derivatives The present invention concerns processes for the manufacture of iminium compounds and their application in the manufacture of pyrazole derivatives, in particular in processes for the manufacture of pharmaceutically or agrochemically active compounds.
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(2019/07/13)

Development of Cyanopyrazoles as Building Blocks to Fungicide Fluxapyroxad and Analogues
Herein, we present a facile approach to a diverse collection of 1,4-disubstituted 3-di- or mono-fluoromethylpyrazoles utilizing our previously developed cyanopyrazoles as key building blocks. This method features several merits, such as easily accessible starting materials, broad substrate scope, mild reaction conditions, and simple operation. This protocol further deserves to be highlighted by the successful translation into the synthesis of commercialized fungicide fluxapyroxad and its analogues.
Zhang, Yue,Chen, Zhen,Nie, Jing,Zhang, Fa-Guang,Ma, Jun-An
p. 7148 - 7158
(2019/06/14)

Heterocycle-containing two fragrant amines pyrazoles carboxamides and preparation method and application thereof (by machine translation)
The present invention provides a kind of formula (I) indicated by the heterocycle-containing two fragrant amines pyrazoles carboxamides and its preparation method and application, this compound to the agricultural, civil and animal in the technical field of the imago harmful mite and insects, nit and egg demonstrate high insecticidal activity, while at the same time the compound exhibits a good bactericidal activity; (by machine translation)
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Paragraph 0082; 0083; 0084

(2019/02/04)

Synthesis method for allylbenzene triflumizole intermediate 3-(difluoromethyl)-1-metyl-1H-pyrazol-4-carboxylic acid
The invention discloses a synthesis method for allylbenzene triflumizole intermediate 3-(difluoromethyl)-1-metyl-1H-pyrazol-4-carboxylic acid, and belongs to the field of pesticide pharmacy. The synthesis method is characterized in that 3-(difluoromethyl)-1-metyl-1H-pyrazol-4-carboxylic acid is obtained by reacting 3-difluoromethyl-1-methyl-1H-pyrazol and chloro-formate under the action of a catalyst, and a reaction process comprises the following steps: 1) uniformly mixing 3-difluoromethyl-1-methyl-1H-pyrazol, the catalyst and a solvent A, introducing protective gas, controlling pressure to 10-15 barometric pressures, controlling the temperature to 80-110 DEG C, adding chloro-formate, and controlling adding time of chloro-formate to be 40-60 minutes; increasing the reaction temperature to130-150 DEG C after adding is completed, slowly controlling to reduce pressure to 7-9 barometric pressures within 60-90 minutes, and continuously reacting for 40-62 hours; 2) cooling a system, filtering to remove solid, adding filtrate into water with the volume being 6-10 times of that of the filtrate, regulating pH to 2-3 with acid, extracting with a solvent B, washing extracting liquor with water, drying with a drying agent, and concentrating to obtain a product. The synthesis method has the advantages of relatively short steps and relatively low process cost.
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Paragraph 0039; 0040; 0041; 0042

(2019/02/04)

PROCESS FOR THE MANUFACTURE OF PYRAZOLE CARBOXYLIC DERIVATIVES AND PRECURSORS THEREOF
The present invention concerns processes for the manufacture of pyrazole carboxylic derivatives and precursors thereof.
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(2019/07/13)

PROCESS FOR THE MANUFACTURE OF PYRAZOLE COMPOUNDS
Disclosed are processes for the manufacture of pyrazole compounds of formula (I) and their application in the manufacture of pyrazole derivatives, in particular in processes for the manufacture of pharmaceutically or agrochemically active compounds, wherein in the processes, at least two steps are conducted in the presence of at least one solvent which is the same in the at least two steps, wherein the at least one same solvent is selected from the group consisting of aromatic hydrocarbons, alkanes, carboxylic acid esters, ethers, nitriles and dimethylformamide.
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(2019/07/13)

OXIDATION OF A PYRAZOLYL KETONE COMPOUND TO THE CORRESPONDING CARBOXYLIC ACID
This invention concerns a process for the manufacture of carboxylic acids or carboxylic acid derivatives and a process for the manufacture of agrochemically and pharmaceutically active compounds comprising the process for the manufacture of carboxylic acids or their derivatives. The process for the manufacture of carboxylic acids or carboxylic acid derivatives of formula (II) comprises a step of oxidizing a compound of formula (I) in the presence of at least one compound of formula (III) R6-C(O)O-OH. (I) (II)
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Page/Page column 12; 13

(2019/06/23)

A process for preparing pyrazole derivatives (by machine translation)
The invention relates to a process for preparing pyrazole derivatives, type IV the intermediate compounds shown in formula V shown in fluoro acetyl halogen derivatives of formula VI of the fluorine-containing intermediate compounds shown, type VI of the fluorine-containing intermediate compounds shown in under the action of acid, after hydrolysis generates closes the pyrazole tipm shown in VII 3 - solvates - 1 - methyl pyrazole derivatives, as shown in formula VII 3 - solvates - 1 - methyl pyrazole derivatives in the reaction under alkaline conditions, then acidifying, of formula VIII shown 3 - solvates - 1 - methyl - 1 H - pyrazole - 4 - carboxylic acid, the invention also relates to a process for preparing pyrazole derivatives of the intermediate structure of the compound. Pyrazole derivatives of the present invention method is suitable for the preparation of industrial production. (by machine translation)
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Paragraph 0042; 0043; 0044

(2018/03/01)

A 1 - methyl - 3 - difluoromethyl - 1 H - pyrazole - 4 - carboxamide derivatives and preparation method and application thereof (by machine translation)
The invention discloses a 1 - methyl - 3 - difluoromethyl - 1H- Pyrazole - 4 - carboxamide derivatives and preparation method and application thereof. The difluoro-acetyl-acetic acid ethyl ester with the original carboxylic acid triethyl after refluxing in acetic anhydride is added to the prepared methyl hydrazine in 1 - methyl - 3 - difluoromethyl - 1 H - pyrazole - 4 - carboxylic acid ethyl ester, 1 - methyl - 3 - difluoromethyl - 1 H - pyrazole - 4 - carboxylic acid ethyl ester hydrolysis after adding hydrochloric acid to obtain 1 - methyl - 3 - difluoromethyl - 1H- Pyrazole - 4 - carboxylic acid, 1 - methyl - 3 - difluoromethyl - 1H- Pyrazole - 4 - carboxylic acid with thionyl chloride is added after the reaction of methylene chloride dilution, then adding aryl amine and triethylamine to obtain 1 - methyl - 3 - difluoromethyl - 1H- Pyrazole - 4 - amide derivatives. Its preparation method is simple, easy to operate, the obtained compound in 50 ppm under such as rice sheath blight fungus has good inhibitory activity; new pesticide research provides the basis. (by machine translation)
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Paragraph 0031; 0034-0035

(2018/06/15)

Application of 1-methyl-3-difluoromethyl-1H-pyrazol-4-amide derivative in preparing herbicide
The invention discloses application of a 1-methyl-3-difluoromethyl-1H-pyrazol-4-amide derivative in preparing herbicide. Lettuce and agrostis are taken as seed test objects; before biological assay, seeds are subjected with surface sterilization for 10 minutes with a 5-10% Chlorox solution, are completely flushed with deionized water of a Millipore system, and are air-dried in a sterile environment. Samples are treated as follows: all samples use acetone as a solvent to prepare a solution with concentration being 1 mM; and the tested compound has relatively good inhibition on lettuce and agrostis according to the biological assay. The compound is a novel compound with herbicidal activity, and provides foundation for developing novel pesticides.
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Paragraph 0013; 0016; 0017

(2018/12/13)

METHOD FOR PREPARING PYRAZOLECARBOXYLIC ACID DERIVATIVE, AND INTERMEDIATE THEREOF
Provided are a preparation method for synthesizing a pyrazolecarboxylic acid derivative of the following formula (I), which is suitable for industrial production, and an intermediate as shown by the following formula (II). The method is high in reaction yield in each step, low in waste gas and waste water and low in cost, and requires no special reaction equipment.
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Paragraph 0126

(2018/07/31)

METHOD FOR PRODUCING 3-HALOALKYL PYRAZOLE DERIVATIVE
PROBLEM TO BE SOLVED: To provide a method for producing a 3-haloalkyl pyrazole derivative from an inexpensive raw material compound in a high yield without requiring inefficient separation operation by suppressing the production of isomers. SOLUTION: The method for producing a 3-haloalkyl pyrazole derivative of the following formula (3) comprises reacting a compound of the following formula (1) with a compound of the following formula (2) and then reacting it with a base or an acid. [R1 is a 1-6C haloalkyl group; R2 and R3 are each independently H, a 1-6C alkyl group, a 6-18C aryl group, a 6-26C aryl group having a substituent, a 4-12C heteroaryl group or a 4-30C heteroaryl group having a substituent; X is -CN, -CONR4R5 or COOR6; and R4, R5 and R6 are each independently a 1-6C alkyl group.] SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0077-0078

(2018/06/26)

Method for preparing 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid
The invention provides a method for preparing 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid. The method comprises the following steps: under the action of an alkali, enabling 1,1,1-trichlorine-3-(substituted amino methylene)-5,5-difluoro-2,4-pentanedione to react with n-alcohol to generate 2-(substituted amino methylene)-4,4-difluoro-3-oxo-butyrate, further reacting with a methylhydrazinesolution to generate 3-difluoromethyl-1-methyl-1H-pyrazolyl-4-formate, and finally performing hydrolysis under an alkali condition, thereby obtaining the 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid. The invention provides a novel economic method, and 2-(substituted amino methylene)-4,4-difluoro-3-oxo-butyrate which is high in yield and high in purity is firstly prepared, and is furtherhighly selectively converted into a target product, namely 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid.
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Paragraph 0046; 0047; 0048; 0049

(2018/05/16)

PROCESS FOR THE MANUFACTURE OF CARBOXYLIC ACIDS OR CARBOXYLIC ACID DERIVATIVES
This invention concerns a process for the manufacture of carboxylic acids or carboxylic acid derivatives and a process for the manufacture of agrochemically and pharmaceutically active compounds comprising the process for the manufacture of carboxylic acids or their derivatives. The process for the manufacture of carboxylic acids or carboxylic acid derivatives comprises the steps of: a) halogenating a compound of formula (I): R1-C(O)-CHX2, to obtain a compound of formula (II): R1-C(O)-CX2X', b) transforming the compound of formula (II) in the presence of a compound A into a compound of formula (III): R1C(O)Z, wherein Z is a residue selected from the group consisting of -OH, -O-, -NR'R'. The process can optionally comprise additional steps.
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Page/Page column 14

(2018/05/24)

MANUFACTURE OF HYDRAZINYL COMPOUNDS USEFUL IN THE MANUFACTURE OF PYRAZOLE CARBOXYLIC ACID AND DERIVATIVES, HYDRAZINYL COMPOUNDS AND THEIR USE
The present invention concerns the manufacture of hydrazinyl compounds useful in the manufacture of pyrazole carboxylic acid and derivatives thereof and processes for the manufacture of agrochemical or pharmaceutical compounds. The invention also concerns hydrazinyl compounds and their use.
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(2018/03/28)

PROCESS FOR THE MANUFACTURE OF CARBOXYLIC ACIDS OR CARBOXYLIC ACID DERIVATIVES
This invention concerns a process for the manufacture of carboxylic acids or carboxylic acid derivatives and a process for the manufacture of agrochemically and pharmaceutically active compounds comprising the process for the manufacture of carboxylic acids or their derivatives. The process for the manufacture of carboxylic acids or carboxylic acid derivatives comprises a step of catalytic oxidation in the presence of at least one catalyst and at least one oxidant, of compound number (I) to obtain a compound of formula (II).
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Page/Page column 11; 12; 13; 14

(2018/12/03)

METHOD FOR THE PREPARATION OF 3-FLUOROALKYL-1-METHYLPYRAZOL-4-CARBOXYLIC ACID
The present invention relates to method for the preparation of 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid, wherein it comprises the following steps: step 1, fluoroacetyl fluoride derivative shown in Formula I undergoes condensation with dimethylamino vinyl methyl ketone, as a result, 3-dimethylamino methylene-fluoro-2,4-pentanedione derivative shown in Formula II is formed; step 2, ring closing reaction takes place between said 3-dimethylamino methylene-fluoro-2,4-pentanedione shown in Formula II and methylhydrazine, in this way, 3-fluoroalkyl-1-methyl-4-acetyl pyrazol derivative shown in Formula III is obtained; step 3, the said 3-fluoroalkyl-1-methyl-4-acetyl pyrazol derivative shown in Formula III is oxidized in the presence of alkali, and then acidified, in this way, 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid shown in Formula IV is formed. Preparing method of present invention, wherein the required preparing route is simple, the raw material cost is low, the resulting yield of each step is high, and it is suitable for industrialization.
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Paragraph 0041-0044; 0053

(2018/10/19)

METHOD FOR PRODUCING FLUORINE-CONTAINING PYRAZOLE CARBOXYLIC ACID
PROBLEM TO BE SOLVED: To provide a production method that makes it possible to easily produce a fluorine-containing pyrazole carboxylic acid useful as a medical and agrochemical intermediate. SOLUTION: A method for producing a fluorine-containing pyrazole carboxylic acid represented by formula (a) includes oxidizing a compound represented by formula (b), using at least one inorganic oxo acid selected from the group consisting of an oxo acid of boron, an oxo acid of phosphorus, an oxo acid of sulfur, and an oxo acid of nitrogen. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0030-0033

(2018/05/29)

Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties
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.
Liu, Xing-Hai,Zhao, Wen,Shen, Zhong-Hua,Xing, Jia-Hua,Xu, Tian-Ming,Peng, Wei-Li
p. 881 - 889
(2016/10/25)

Synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modi?ed scaffold as potent antifungal agents
Twenty-seven novel pyrazole carboxamides with diarylamine-modi?ed scaffold were designed, synthesized and characterized in detail via 1H NMR, 13C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani, Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC50 values of 0.013, 1.608 and 1.874?μg/mL, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC50 value of 22.21?μg/mL. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.
Zhang, Xiao-Xiao,Jin, Hong,Deng, Yuan-Jie,Gao, Xu-Heng,Li, Yong,Zhao, Yong-Tian,Tao, Ke,Hou, Tai-Ping
p. 1731 - 1736
(2017/07/27)

1-methyl-3-difluromethylation-1H-pyrazole-4-methanamide thiourea compound and preparation method and application thereof
The invention discloses a 1-methyl-3-difluromethylation-1H-pyrazole-4-methanamide thiourea compound and a preparation method and application thereof. The preparation method includes: difluoro ethyl acetoacetate has reaction with triethyl orthoformate to obtain intermediate (E)-2-ethoxy methylene-4, 4-difluoro-3-methyl acetoacetate; the intermediate has reaction with methylhydrazine to obtain methylhydrazine intermediate (III), and the methylhydrazine intermediate (III) is hydrolyzed to obtain 1-methyl-3-difluromethyl-1H-pyrazole-4-carboxylic acid; the 1-methyl-3-difluromethyl-1H-pyrazole-4-carboxylic acid sequentially has reaction with thionyl chloride, ammonium thiocyanate and aniline derivatives with different substituents to obtain the 1-methyl-3-difluromethylation-1H-pyrazole-4-methanamide thiourea compound. The 1-methyl-3-difluromethylation-1H-pyrazole-4-methanamide thiourea compound is used for preparing bactericides for preventing and treating mycosphaerella arachidicola, bacterial xanthomonas malvacearum, botrytis cinerea and oxysporum, is a novel compound with bactericidal activity and provides a foundation for the research and development of novel pesticides.
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Paragraph 0023; 0031; 0032

(2017/09/05)

1-methyl-3-difluromethylation-1H-pyrazole-4-methanamide urea compound, preparation method thereof and application
The invention discloses a 1-methyl-3-difluromethylation-1H-pyrazole-4-methanamide urea compound, a preparation method thereof and an application of the compound to prevention and treatment of cucumber spot diseases, cucumber bacterial angular leaf spots, cucumber fusarium wilt and botrytis cinerea pers. Difluoro ethyl acetoacetate and triethyl orthoformate react to obtain intermediate (E)-2-ethoxy methylene-4,4-difluoro-3-methyl acetoacetate. The intermediate sequentially reacts with methyl hydrazine, is hydrolyzed and then reacts with ammonia water to obtain 1-methyl-3-difluromethylation-1H-pyrazole-4-amide, finally, the 1-methyl-3-difluromethylation-1H-pyrazole-4-amide sequentially reacts with oxalyl chloride and aniline derivatives with different substituents in an overnight manner, and reduced pressure distillation and recrystallization are performed after reaction to obtain the target compound. The compound is a novel compound with bactericidal activity and provides the foundation for research and development of novel pesticides.
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Paragraph 0030; 0031

(2017/09/05)

3-difluromethyl-1-methyl-pyrazole-4-formic acid and synthetic method thereof
The present invention relates to the field of chemical industry, and more specifically, relates to 3-difluromethyl-1-methyl-pyrazole-4-formic acid and a synthetic method thereof, the synthetic method comprises the steps: DFKE synthesis; DFVKE synthesis; DFPE synthesis; and DFPA synthesis. The synthesis method has the advantages of cheap and easily-obtained materials, greenness, environmental-friendliness, simple reaction conditions, less impurities and high yield, the prepared 3-difluromethyl-1-methyl-pyrazole-4-formic acid has high quality and high purity, and the yield is 90% or more.
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Paragraph 0026; 0031; 0036; 0041

(2017/08/29)

COMPOSITION COMPRISING 3-(HALOALKYL OR FORMYL)-1H-PYRAZOLE-4-CARBOXYLIC ACIDS OR ESTERS, ITS MANUFACTURE AND ITS USE FOR THE PREPARATION OF CARBOXAMIDES
The present invention concerns compositions comprising (i) a 3-(haloalkyl or formyl)-1H-pyrazole wherein R1 is a halogenated C1-4alkyl group, or the group -C(O)H, R2 is selected from the group consisting of H, C1-C12 alkyl, C2-C6 alkenyl, cycloalkyl, aryl, heteroaryl, aralkyl, each of which is optionally substituted, R3 is selected from the group consisting of H, C1-C12 alkyl, C2- C6 alkenyl, aryl or C3-C8 cycloalkyl, each of which is optionally substituted, and R4 is selected from the group consisting of H, X', COOR', OR', SR', C(O)NR'2, and (ii) at least one of the pyrazole derivatives of the formulae (II) - (X), (XVIIIa), (XVIIIb), (XIX) and (XX), wherein the chemical composition comprises equal to or more than 95 w% of compound of formula (I), its manufacture and use in processes for the manufacture of agrochemical or pharmaceutical pyrazole-4-carboxamide compounds.
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Page/Page column 21; 22

(2017/12/01)

HALOGEN SUBSTITUTED DIKETONES, PYRAZOLE COMPOUNDS AND PROCESSES FOR THE MANUFACTURE OF PYRAZOLE COMPOUNDS
The present invention concerns new halogen substituted diketone compounds, new pyrazole compounds, processes for the manufacture of pyrazole compounds and processes for the manufacture of agrochemical or pharmaceutical compounds.
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Page/Page column 46

(2017/08/21)

Preparation method for polyfluoromethylpyrazole compound, and intermediate of compound and preparation method thereof
The invention discloses a preparation method for a polyfluoromethylpyrazole compound, and an intermediate of the compound and a preparation method thereof. The invention provides a preparation method for a compound 1 as defined in the specification. The preparation method comprises a step of subjecting a compound 2 as defined in the specification and methylhydrazine to a ring-closure reaction in an organic solvent so as to obtain the compound 1, wherein R is a C1-4 alkyl group, R is a methyl or ethyl group and x is 2 or 3. The preparation method provided by the invention uses cheap and easily available raw materials and is mild in reaction conditions, safe to operate, environment friendly, low in production cost, high in reaction conversion rate, low in the content of isomer in by-products, high in reaction yield and product purity and suitable for industrial production.
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(2017/06/30)

3-difluoromethyl-1-methyl-1H-pyrazol-4-formic acid and preparation method of intermediate and intermediate
The invention discloses 3-difluoromethyl-1-methyl-1H-pyrazol-4-formic acid and a preparation method of an intermediate thereof and the intermediate. The preparation method of the intermediate comprises the following step: in the absence of a solvent or in the presence of a solvent, a compound 1 and KF undergo a fluoridation reaction under the action of a catalyst so as to obtain a compound 2. The preparation method also comprises the following step: the compound 2 is subjected to a hydrolysis reaction under the action of alkali so as to obtain a compound 3. The preparation method has the following advantages: raw materials are cheap and easily available; operation is simple; and security risk is low. The preparation method is suitable for industrial production.
-
(2017/05/02)

Synthesis method of 3-difluoromethyl-1-methylpyrazole-4-formic acid
The invention discloses a synthesis method of 3-difluoromethyl-1-methylpyrazole-4-formic acid, and belongs to the technical field of difluoromethyl pyrazole synthesis. According to the synthesis method, 3-difluoromethyl-1-methylpyrazole-4-formic acid is prepared from 1-dimethylamino-1-butylene-3-one, difluoroacetyl fluoride, and methyl hydrazine through a series of reactions. The provided synthesis method has the advantages of easily available raw materials and high yield, can be applied to industry, and has a comprehensive yield more than 65%.
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Paragraph 0015; 0017; 0018; 0020; 0021; 0023

(2017/08/28)

Preparation method of 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid
The invention relates to a preparation method of 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid. The method comprises the following steps: step 1, making a fluoroacetyl halide derivative shown in the formula I and dimethylamino vinyl methyl ketone to undergo a condensation reaction to generate a 3-dimethylamino methylene-1,1-difluoro-2,4-pentanedione derivative shown in the formula II; step 2, reacting the 3-dimethylamino methylene-1,1-difluoro-2,4-pentanedione derivative shown in the formula II with methylhydrazine for a ring-closing reaction to generate a 3-fluoroalkyl-1-methyl-4-acetyl pyrazole derivative shown in the formula III; and step 3, oxidizing the 3-fluoroalkyl-1-methyl-4-acetyl pyrazole derivative shown in the formula III in an alkaline condition, and performing acidification to generate 3-fluoroalkyl-1-methylpyrazol-4-carboxylic acid. The preparation method is short in reaction route, low in raw material cost, high in reaction yield of each step, and suitable for industrial production.
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Paragraph 0054; 0055; 0068; 0069; 0070; 0076; 0077

(2017/08/28)

New process for preparing pyrazole carboxylic acid derivatives
The present invention relates to a method for preparing a pyrazole carboxylic acid derivative. More particularly, the present invention relates to a novel method for preparing 1-alkyl-3-haloalkyl pyrazole-4-carboxylic acid represented by chemical formula (I) and useful for an intermediate for the preparation of a pyrazole carboxanilide-based sterilizing agent. In chemical formula (I), R_1 represents a C1-C3 lower alkyl group, R_2 represents any one of CHF_2, CF_3, CHCl_2 and CCl_2.COPYRIGHT KIPO 2017
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Paragraph 0060; 0086-0088

(2017/04/03)

Novel process for preparing 4,4-difluoro-((2-dialkylamino) methylene)-3-oxobutanic acid alkyl ester
The present invention relates to a novel method for preparing 4,4-difluoro-((2-dialkylamino) methylene)-3-oxobutanic acid alkyl ester which is represented by the following chemical formula ( I ) and useful as a manufacturing intermediate for fungicides such as isopyrazam, sedaxane, bixafen and the like. In the formula ( I ), R 1 and R 2 are each a C 1 to C 4 alkyl group, and R is a methyl group or an ethyl group. The compound of the formula ( I ) is produced by reacting dialkylformamide dialkyl acetal with a difluoro ketoester.
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Paragraph 0061

(2017/01/31)

Chemical Properties

Boiling Point: 315.9 °C at 760 mmHg
Flash Point:144.851 °C
Density: 1.524 g/cm³
Solubility:DMSO (Slightly), Methanol (Sparingly)
Storage Temp.:Sealed in dry,Room Temperature
Vapor Pressure: 0.000179mmHg at 25°C
Refractive Index: 1.533
PKA: 3.12±0.36(Predicted)
PSA: 55.12000
LogP: 1.05590

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176969-34-9

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Chemical Properties

Boiling Point: 315.9 °C at 760 mmHg

Flash Point:144.851 °C

Density: 1.524 g/cm³

Solubility:DMSO (Slightly), Methanol (Sparingly)

Storage Temp.:Sealed in dry,Room Temperature

Vapor Pressure: 0.000179mmHg at 25°C

Refractive Index: 1.533

PKA: 3.12±0.36(Predicted)

PSA: 55.12000

LogP: 1.05590

Global suppliers and manufacturers of 176969-34-9total 121 suppliers on LookChem

Article Database

176969-34-9

Articles about 176969-34-9Total 75 be found

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Chemical Properties

Boiling Point: 315.9 °C at 760 mmHg

Flash Point:144.851 °C

Density: 1.524 g/cm3

Solubility:DMSO (Slightly), Methanol (Sparingly)

Storage Temp.:Sealed in dry,Room Temperature

Vapor Pressure: 0.000179mmHg at 25°C

Refractive Index: 1.533

PKA: 3.12±0.36(Predicted)

PSA: 55.12000

LogP: 1.05590

Global suppliers and manufacturers of 176969-34-9total 121 suppliers on LookChem

Density: 1.524 g/cm³