- Synthesis and structure of 2-ethoxy- and 2-aminomethylidene-3-fluoroalkyl- 3-oxopropionates
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Condensation of ethyl 3-polyfluoroalkyl-3-oxopropionates with excess triethyl orthoformate gave ethyl 3-polyfluoroalkyl-2-ethoxymethylidene-3- oxopropionates which reacted with primary aliphatic, aromatic, and heterocyclic amines to form ethyl 2-alkyl(ary
- Pryadeina,Burgart,Saloutin,Slepukhin,Kazheva,Shilov,D'yachenko,Chupakhin
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Read Online
- Synthesis and Bioactivities of Novel 1-(3-Chloropyridin-2-yl)-N-Substituted-5-(Trifluoromethyl)-Pyrazole Carboxamide Derivatives
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A series of novel 1-(3-chloropyridin-2-yl)-N-substituted-5-(trifluoromethyl)-pyrazole carboxamide derivatives TC1, TC2, TC3, TC4, TC5, TC6, TC7, TC8, TC9, T
- Wu, Zhibing,Wu, Shixi,Ye, Yiqiang,Zhou, Xiang,Wang, Peiyi,Xue, Wei,Hu, Deyu
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Read Online
- Unexpected formation of diethyl 2-ethoxy-6-CF3-2H-pyran-3,5-dicarboxylate from the condensation of ethyl 4,4,4-trifluoroacetoacetate with CH(OEt)3
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The one-step preparation of diethyl 2-ethoxy-6-CF3-2H-pyran-3,5-dicarboxylate via the condensation of ethyl 4,4,4-trifluoroacetoacetate with CH(OEt)3 has been reported and a plausible mechanism for this transformation is discussed. T
- Kudyakova, Yulia S.,Bazhin, Denis N.,Slepukhin, Pavel A.,Burgart, Yanina V.,Saloutin, Victor I.,Charushin, Valery N.
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Read Online
- DNDI-6148: A Novel Benzoxaborole Preclinical Candidate for the Treatment of Visceral Leishmaniasis
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Visceral leishmaniasis (VL) is a parasitic disease endemic across multiple regions of the world and is fatal if untreated. Current therapies are unsuitable, and there is an urgent need for safe, short-course, and low-cost oral treatments to combat this ne
- Bello, Davide,Braillard, Stéphanie,Caljon, Guy,Carvalho, Sandra,Corpas-Lopez, Victoriano,Freund, Yvonne,Gilbert, Ian H.,Glossop, Paul A.,Jacobs, Robert T.,Lukac, Iva,Maes, Louis,Mowbray, Charles E.,Nare, Bakela,Pandi, Bharathi,Patterson, Stephen,Speake, Jason,Van Den Kerkhof, Magali,Wall, Richard J.,Whitlock, Gavin A.,Wyllie, Susan,Yardley, Vanessa,Zuccotto, Fabio
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p. 16159 - 16176
(2021/11/16)
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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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- Process for preparing 2- polyhaloacetyl -3- alkoxyacrylates (by machine translation)
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The invention discloses a preparation method 2 - of, polyhalogenated acetyl - 3 3-alkoxy acrylate, wherein the compound II with the chemical structural formula, is dissolved in an organic solvent, for, times and then is heated to I for a certain time . to generate first polyhaloacetyl - 3 3-alkoxyacrylic acid ester, with the chemical structural formula 0.5 - 4h, after reaction for a certain period of time. 0 - 50 °C, The preparation method of the, invention is reasonable second operation and . atomic economical efficiency III, in an 2 -phase reaction, reaction with an acid-binding agent to react for a certain time. (by machine translation)
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Paragraph 0055-0056
(2020/05/30)
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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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Paragraph 0087-0089
(2020/01/08)
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- Novel trifluoromethylpyrazole acyl thiourea derivatives: Synthesis, antifungal activity and docking study
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Background: In recent years, pyrazole carboxamide derivatives possessed excellent fungicidal activity. In the process of designing new fungicides, the carboxamide group was modified in order to find novel structure pyrazole carboxamide derivatives. Methods: Ten novel trifluoromethyl pyrazole acyl thiourea derivatives were designed and synthesized. In vivo fungicidal activities of these compounds were tested against Fusarium oxysporum, Corynespora mazei and Botrytis cinerea, respectively Results: Particularly compounds exhibited significant control effective at 100 mg/L. More importantly, some compounds showed the good control effective at 10 mg/L. Furthermore, docking was established to study the structure-activity relationship of the title compounds. Conclusion: It is possible that trifluoromethylpyrazole acyl thiurea derivatives, which possess good control effective against Botrytis cinerea, may become novel lead compounds for the development of fungicides with further structure modification.
- Wang, Han,Zhai, Zhi-Wen,Shi, Yan-Xia,Tan, Cheng-Xia,Weng, Jian-Quan,Han, Liang,Li, Bao-Ju,Liu, Xing-Hai
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p. 785 - 791
(2019/08/26)
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- HERBICIDALLY ACTIVE PYRIDYL-/PYRIMIDYL-PYRIMIDINE DERIVATIVES
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The present invention relates to herbicidally active pyridyl-/pyrimidyl-pyrimidine derivatives. The invention further provides processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.
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Page/Page column 32
(2019/04/16)
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- HERBICIDALLY ACTIVE PYRIDYL-/PYRIMIDYL-PYRIMIDINE DERIVATIVES
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The present invention relates to herbicidally active pyridyl-/pyrimidyl-pyridine derivatives, as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.
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Page/Page column 32; 33
(2019/04/16)
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- A 1, 3, 4 - oxa (thia) oxadiazolyl imidazole compound and its preparation and use
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The invention relates to a 1, 3, 4 - oxa (thia) oxadiazolyl imidazole compound and its preparation and use. The compounds have the general formula (I) indicated by the structure: This compound to the plant pathogenic pathogenic bacteria, such as [...] Pha
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Paragraph 0065; 0067; 0068
(2019/07/10)
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- PYRIMIDIN-4-CARBAMATE OR UREA DERIVATIVES AS HERBICIDES
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The present invention relates to herbicidally active pyridyl-/pyrimidyl-pyrimidine derivatives, as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.
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Page/Page column 35
(2019/04/16)
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- PYRAZOLE DERIVATIVES AS MALT1 INHIBITORS
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Disclosed are compounds, compositions and methods for treating of diseases, syndromes, conditions, and disorders that are affected by the modulation of MALT1. Such compounds are represented by Formula (I) as follows: wherein R1, R2, R3, R4, R5, R6, R5, G1, and G2 are defined herein.
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Paragraph 0824; 0825
(2018/07/05)
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- Novel trifluoromethylpyrazole acyl urea derivatives: Synthesis, crystal structure, fungicidal activity and docking study
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Thirteen novel trifluoromethylpyrazole acyl urea derivatives were designed and synthesized. In vivo fungicidal activities of these compounds were tested against Fusarium oxysporum, Corynespora mazei, Botrytis cinerea and Pseudomonas syringae respectively, particularly compounds exhibited significant control effective at 100 mg/L. More importantly, some compounds showed the good control effective at 10 mg/L. Furthermore, docking was established to study the structure-activity relationship of the title compounds. It is possible that trifluoromethylpyrazole acyl urea derivatives, which possess good control effective against Fusarium oxysporum, Corynespora mazei and Botrytis cinerea, may become novel lead compounds for the development of fungicides with further structure modification.
- Wang, Han,Zhai, Zhi-Wen,Shi, Yan-Xia,Tan, Cheng-Xia,Weng, Jian-Quan,Han, Liang,Li, Bao-Ju,Liu, Xing-Hai
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p. 631 - 638
(2018/07/06)
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- Trifluoromethyl group-containing pyridylpyrazole carboxamide derivative, and preparation method and application thereof
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The invention discloses a trifluoromethyl group-containing pyridylpyrazole carboxamide derivative, and a preparation method and an application thereof. The trifluoromethyl group-containing pyridylpyrazole methanamide derivative is 1-(3-chloro-2-pyridyl)-N
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Paragraph 0031; 0032
(2017/06/30)
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- Method for synthesizing 1-substituted phenyl-5-trifluoromethyl (difluoromethyl)-4-pyrazole carboxylic acid
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The invention relates to a method for synthesizing 1-substituted phenyl-5-trifluoromethyl (difluoromethyl)-4-pyrazole carboxylic acid. The method is as follows: performing a ring-forming reaction of phenylhydrazine or substituted phenylhydrazine with inte
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Paragraph 0032; 0033; 0040; 0047; 0054; 0061; 0068
(2018/01/11)
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- Design, synthesis and insecticidal activities of novel 1-substituted-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives
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A series of novel 5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives (6a–6n, 7a, 7b, and 8a-8f) were synthesised by placing the amide bond at the 4-position of the pyrazole ring. These derivatives differed from the structure of chlorantraniliprole analogues with the amide bond at the 5-position of the pyrazole ring. Preliminary bioassay results revealed that a few title compounds exhibited good insecticidal activities against lepidopteran pests, such as Plutella xylostella, Mythimna separate, Heliothis armigera, and Ostrinia nubilalis. Some title compounds also elicited broad-spectrum insecticidal activities against dipterous insects including Culex pipiens pallens after altering the amide position. Similar to pyrazole-5-carboxamide analogues, compounds 6b and 6e showed 100% insecticidal activity against P. xylostella, C. pipiens pallens, and M. separate at concentrations of 200, 2, and 200?μg/mL, respectively. This finding suggested that 5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives are potential alternative insecticides for management of agriculture pests.
- Wu, Zhi-Bing,Zhou, Xiang,Ye, Yi-Qiang,Wang, Pei-Yi,Yang, Song
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p. 121 - 125
(2017/01/13)
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- Synthesis and bioactivities of novel 2-(thioether/sulfone)-5-pyrazolyl-1,3,4-oxadiazole derivatives
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By introducing the pyrazole moiety into the 5-position of 1,3,4-oxadiazole, a series of novel 2-(thioether/sulfone)-5-pyrazolyl-1,3,4-oxadiazole derivatives were synthesized. Preliminary bioassays suggested that target compounds exhibited appreciable activity against pathogenic bacteria Xanthomonas oryzae pv. oryzae (Xoo) and five phytopathogenic fungi in vitro. Among them, the half-maximal effective concentration (EC50) values of 6c, 7a, 7b and 7c against Xoo were within 16.6 μg/mL and 65.7 μg/mL, which were better than those of commercial agricultural antibacterial bismerthiazol (92.6 μg/mL) and thiodiazole copper (121.8 μg/mL). While compounds 7a, 7b, and 7c exerted comprehensive antifungal activity toward five plant fungi, which were comparable with that of hymexazol. The results demonstrated that this kind of compounds can be further studied and developed as promising antifungal and antibacterial agents.
- Zheng, Yu-Tao,Zhang, Teng-Teng,Wang, Pei-Yi,Wu, Zhi-Bing,Zhou, Lei,Ye, Yi-Qiang,Zhou, Xiang,He, Ming,Yang, Song
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p. 253 - 256
(2017/01/28)
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- Antibacterial and Antifungal Activities of 2-(substituted ether)-5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,4-oxadiazole Derivatives
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By replacing the amide bond into 1,3,4-oxadiazole moiety, a series of 1-phenyl-5-(trifluoromethyl)-1H-pyrazole derivatives bearing 1,3,4-oxadiazole were synthesized and evaluated their antibacterial and antifungal activity. The bioassay results revealed that compounds 7a and 7b showed the strongest antibacterial activity toward pathogen Xanthomonas oryzae pv. oryzae with the EC50 values of 15.0 and 6.4 μg/mL, respectively; compound 6a exhibited comprehensive antifungal activity toward six kinds of fungi; compound 6f could selectively inhibit the growth of Sclertinia sclerotiorum and Rhizoctonia solani with the inhibition rates of 82.5 and 80.3% at the concentrate of 100 μg/mL, respectively; compound 7b exerted good antifungal activity toward Fusarium oxysporum, Cytospora mandshurica, and Rhizoctonia solani with the inhibition rates of 70.8, 69.5, and 71.5%, respectively. The results suggested that this kind of compounds could be further studied as promising antimicrobial agents.
- Zhang, Teng-Teng,Wang, Pei-Yi,Zhou, Jian,Shao, Wu-Bin,Fang, He-Shu,Zhou, Xiang,Wu, Zhi-Bing
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p. 2319 - 2325
(2017/07/25)
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- Triazole compound containing trifluoromethyl pyrazol and preparation method and application thereof
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The invention relates to a triazole compound containing trifluoromethyl pyrazol and a preparation method and application thereof. The triazole compound containing the trifluoromethyl pyrazol, namely 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl)-4-phenyl-4H-1,2,4-triazole-3-thioether compound, is applied to herbicides for preventing and controlling radishes, cucumbers, rape, wheat, sorghum, barnyard grass and the like, the compound is a novel compound having herbicidal activity, and a basis is provided for research and development of novel pesticides.
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Paragraph 0023; 0028; 0029
(2017/08/28)
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- Phenyl bispyrazole carboxamide derivatives and preparation method and application thereof
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The invention provides phenyl bispyrazole carboxamide derivatives and a preparation method and an application thereof; the compounds show relatively good inhibition performance on armyworm under the concentration of 500-100 ppm, a target compound I-6, a c
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Paragraph 0035; 0036
(2017/06/02)
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- FUSED BICYCLIC COMPOUNDS FOR THE TREATMENT OF DISEASE
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Described herein are fused bicyclic compounds, compositions, and methods for their use for the treatment of disease.
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Paragraph 00520
(2016/10/11)
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- Aromatic imide compounds and preparation method and application thereof
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The invention discloses aromatic imide derivatives with the chemical structure shown as the general formula (I) and a preparation method and anticancer activity thereof. R1 and R2 are defined in the specification. Part of the compounds have good anticance
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Paragraph 0029
(2016/10/09)
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- Synthesis of novel ethyl 2,4-disubstituted 8-(trifluoromethyl)pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidine-9-carboxylate derivatives as promising anticancer agents
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A series of novel pyrido[2',3':3,4] pyrazolo[1,5-a]pyrimidine derivatives 6–9 were prepared in single step starting from 3-amino-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 5 on reaction with symmetrical and unsymmetrical aliphatic and ar
- Ravi Kumar,Poornachandra,Krishna Swaroop,Jitender Dev,Ganesh Kumar,Narsaiah
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p. 5203 - 5206
(2016/11/09)
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- Application of triazole compound containing trifluoromethylpyrazole in preparation of bactericides
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The invention relates to application of a triazole compound containing trifluoromethylpyrazole in preparation of bactericides. The triazole compound containing trifluoromethylpyrazole obtained by the invention, i.e. 5-(1-methyl-3-trifluoromethyl-1H-parazole-4-yl)-4-phenyl-4H-1, 2, 4-triazole-3-thioether compound has significant efficacy in control of rice sheath blight fungi, tomato early blight, cucurbits anthracnose, and Borrytis cinerea. The compound is a new compound with fungicidal activity, and provides the basis for research and development of new pesticides.
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Paragraph 0029
(2017/02/09)
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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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- A PROCESS FOR THE PREPARATION OF ALKYL 3-DIFLUOROMETHYL-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE AND ITS ANALOGS
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The disclosure provides a process for the preparation of alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylate and its analogs. The process includes a reaction workup method for Claisen condensation, wherein the enolate salt is acidified after removing remaining starting material and byproducts such as, ethanol and excessive ethyl acetate. The process also includes a method for completely drying alkyl difluoroacetoacetate and its analogs before use in the next step by reacting trialkyl orthoformate with the residual water. The process includes using Na2CO3 and/or K2CO3 to promote the ring-closure reaction to produce the alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylate. The process also includes effectively removing the regioisomer, alkyl 3-difluoromethyl-2-methyl-1H-pyrazole-4-carboxylate formed as a byproduct of the ring closure by a precipitation in a mixed solvent system and thereby eliminating the need for recrystallization of the final product.
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Paragraph 0073-0074
(2015/06/17)
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- PROCESS FOR PREPARING ALKYL 3-DIFLUOROMETHYL-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE AND ITS ANALOGS
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The disclosure provides a process for the preparation of alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylate and its analogs. The process includes a reaction workup method for Claisen condensation, wherein the enolate salt is acidified after removing remaining starting material and byproducts such as, ethanol and excessive ethyl acetate. The process also includes a method for completely drying alkyl difluoroacetoacetate and its analogs before use in the next step by reacting trialkyl orthoformate with the residual water. The process includes using Na2CO3 and /or K2CO3 to promote the ring-closure reaction to produce the alkyl 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylate. The process also includes effectively removing the regioisomer, alkyl 3-difluoromethyl-2-methyl-1H-pyrazole-4-caboxylate formed as a byproduct of the ring closure by a precipitation in a mixed solvent system and thereby eliminating the need for recrystallization of the final product.
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Paragraph 70
(2015/06/25)
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- "Reported, but still unknown." A closer look into 3,4-bis- and 3,4,5-tris(trifluoromethyl)pyrazoles
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Straightforward practical synthetic approaches to 3,4-bis- and 3,4,5-tris(trifluoromethyl)pyrazoles have been developed. The key step of the both syntheses is a transformation of the carboxylic group in a pyrazole core into the trifluoromethyl group by sulfur tetrafluoride. The elaborated synthetic protocols allow gram-scale preparation of the target products. The obtained compounds are comprehensively characterized by means of crystallographic analysis, determination of pKa values and fluorescence measurements.
- Gerus, Igor I.,Mironets, Roman V.,Kondratov, Ivan S.,Bezdudny, Andrei V.,Dmytriv, Yurii V.,Shishkin, Oleg V.,Starova, Viktoriia S.,Zaporozhets, Olga A.,Tolmachev, Andrey A.,Mykhailiuk, Pavel K.
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experimental part
p. 47 - 56
(2012/03/10)
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- Regioselective synthesis of 5-ethoxycarbonyl-, 5-acetyl- and 5-trifluoroacetyl-6-trifluoromethylsalicylates by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-alkoxy-2-alken-1-ones
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5-Ethoxycarbonyl-, 5-trifluoroacetyl-, and 5-acetyl-6- trifluoromethylsalicylates were prepared by one-pot cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-alkoxy-2-alken-1-ones. The reactions proceeded with very good regioselectivity by c
- Ladzik, Simone,Lubbe, Mathias,Kelzhanova, Nazken K.,Abilov, Zharylkasyn A.,Feist, Holger,Langer, Peter
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scheme or table
p. 38 - 42
(2012/06/01)
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- Synthesis and antifungal activity of n-(substituted pyridinyl)- 1-methyl(phenyl)-3-(trifluoromethyl)-1h-pyrazole-4- carboxamide derivatives
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A series of N-(substituted pyridinyl)-1-methyl(phenyl)-3-trifluoromethyl- 1Hpyrazole- 4-carboxamide derivatives were synthesized. All target compounds were characterized by spectral data (1H-NMR, 13C-NMR, IR, MS) and elemental analysis and were bioassayed in vitro against three kinds of phytopathogenic fungi (Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica). The results showed that some of the synthesized N-(substituted pyridinyl)-1-methyl-3- trifluoromethyl-1H-pyrazole-4-carboxamides exhibited moderate antifungal activities, among which compounds 6a, 6b and 6c displayed more than 50% inhibition activities against G. zeae at 100 μg/mL, which was better than that of the commercial fungicides carboxin and boscalid.
- Wu, Zhibing,Hu, Deyu,Kuang, Jiqing,Cai, Hua,Wu, Shixi,Xue, Wei
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p. 14205 - 14218
(2013/02/26)
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- A novel series of piperazinyl-pyridine ureas as antagonists of the purinergic P2Y12 receptor
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A novel series of P2Y12 antagonists for development of drugs within the antiplatelet area is presented. The synthesis of the piperazinyl-pyridine urea derivatives and their structure-activity relationships (SAR) are described. Several compounds
- Bach, Peter,Bostr?m, Jonas,Brickmann, Kay,Van Giezen,Hovland, Ragnar,Petersson, Annika U.,Ray, Asim,Zetterberg, Fredrik
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supporting information; experimental part
p. 2877 - 2881
(2011/06/24)
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- Acylated Aminopyridine and Aminopyridazine Insecticides
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The present invention relates to aminopyridine and aminopyridazine derivatives of the general formula (I) in which R1, X, W and Q have the definitions given in the description, to a number of processes for preparing them, and to their use as in
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Page/Page column 16
(2010/12/29)
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- Process for preparing difluoromethylpyrazolyl carboxylates
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The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; andR2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than ?0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.325 kPa); and b) the reaction mixture from step a) is reacted with a compound of the general formula III [in-line-formulae]R2HN—NH2 ??(III)[/in-line-formulae] in which R2 has one of the meanings given above.
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Page/Page column 8
(2010/04/23)
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- New carboxylic acid amides of the pyrrole series: Synthetic routes and biological aspects
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Complex II inhibitors play an important role in agrochemical fungicide research and have been known for more than 40 years. With the introduction of ortho-substituted heterocyclic amides, a breakthrough in activity level and spectrum within this class was achieved. In the meantime all major agrochemical companies have entered this field. In this paper, a special complex II subclass, the pyrrole carboxamides, will be introduced in more detail and the synthesis of selected compounds as well as a short biological SAR analysis of the pyrrole subclass will be discussed.
- Walter, Harald
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scheme or table
p. 351 - 362
(2009/01/31)
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- Amide bridged piphenyl or biazaphenyl derivatives
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This invention is concerned with compounds of the formula wherein one of R5, R6 and R7 is and R1 to R13, X1, X2, m and n are defined in the description, and all pharmaceutically
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Page/Page column 29
(2008/06/13)
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- Inhibitors of NF-kappaB and AP-1 gene expression: SAR studies on the pyrimidine portion of 2-chloro-4-trifluoromethylpyrimidine-5-[N-(3', 5'-bis(trifluoromethyl)phenyl)carboxamide].
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We investigated the structure-activity relationship studies of N-[3, 5-bis(trifluoromethyl)phenyl][2-chloro-4-(trifluoromethyl)pyrimidin-5 -yl]carboxamide (1), an inhibitor of transcription mediated by both NF-kappaB and AP-1 transcription factors, with the goal of improving its potential oral bioavailability. Compounds were examined for cell-based activity, were fit to Lipinski's rule of 5, and were examined for potential gastrointestinal permeability using the intestinal epithelial cell line, Caco-2. Selected groups were substituted at the 2-, 4-, and 5-positions of the pyrimidine ring using solution-phase combinatorial methodology. The introduction of a fluorine in the place of 2-chlorine of 1 resulted in a compound with comparable activity. However, other substitutions at the 2-position resulted in a loss of activity. The trifluoromethyl group at the 4-position could be replaced with a methyl, ethyl, chlorine, or phenyl without a substantial loss of activity. The carboxamide group at the 5-position is critical for activity. If it was moved to the 6-position, the activity was lost. The 2-methyl analogue of 1 (81) showed comparable in vitro activity and improved Caco-2 permeability compared to 1.
- Palanki,Erdman,Gayo-Fung,Shevlin,Sullivan,Goldman,Ransone,Bennett,Manning,Suto
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p. 3995 - 4004
(2007/10/03)
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