- Synthesis, characterization and antimicrobial evaluation of new 3-(Alkyl/Arylamino)benzo[d]isothiazole 1,1-derivatives
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The saccharine nucleus has long been recognized as a significant component in medicine. A series of pseudo-saccharine amines derivatives (7a-j) were synthesized and examined for their antibacterial activity. After testing all compounds, 7b, 7f, 7g, 7i and 7j were found most effective against Escherichia coli, Streptococcus aureus and Bacillus subtilis strains. The MIC of the compound was found from 4.6 to 16.1 μM. Further, compound 7f and 7i exhibited excellent activity against E.coli and Bacillus subtilis with MIC value 4.6 and 4.7 μM respectively. The compound 7b and 7i was found active against all the three bacteria. The zone inhibition was observed at 10 μM against Escherichia coli, Staphylococcus aureus and Bacillus subtilis at 0.9, 1.8, 3.9 respectively for 7b and 1.0, 1.8 and 2.0 cm respectively for 7i.
- Kamble, Dhanraj P.,Shankarwar, Anil G.,Mane, Yogesh D.,Tigote, Radhakrishna M.,Sarnikar, Yuvaraj P.,Madje, Balaji R.
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p. 797 - 804
(2021/09/08)
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- Preparation method of foramsulfuron or foramsulfuron derivative intermediate
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The invention provides a preparation method of a foramsulfuron or foramsulfuron derivative intermediate. The preparation method is characterized in that saccharin used as a raw material undergoes ammonification and nitration reactions to obtain 2-dimethylaminocarbonyl-5-nitrobenzenesulfonamide that is the foramsulfuron intermediate. The foramsulfuron intermediate compound is prepared from the saccharin, so the method has the advantages of less pollution, low cost, few preparation reaction steps, mild reaction conditions, safety, easiness in operation, environmentally friendly production, and suitableness for large-scale industrial production. .
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Paragraph 0085-0090; 0105-0108
(2019/11/20)
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- Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties
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A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.
- Wang, Bao-Lei,Shi, Yan-Xia,Zhang, Shu-Jun,Ma, Yi,Wang, Hong-Xue,Zhang, Li-Yuan,Wei, Wei,Liu, Xing-Hai,Li, Yong-Hong,Li, Zheng-Ming,Li, Bao-Ju
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p. 167 - 178
(2016/04/26)
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- Application of liquid chromatography/electrospray ionization tandem mass spectrometry for the elucidation of hydroxyl radical oxidation of metsulfuron methyl and related sulfonylurea pesticide products: evidence for the triazine skeleton scission
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Rationale Sulfonylureas are among the most important class of antidiabetic and herbicides. Solar light excitation and Advanced Oxidation Processes may result in the formation of a wide array of products owing to the relative complex structure. These products, that should be identified, may present a more toxic effect than the parent compound. Methods Liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry (LC/ESI-QTOFMS) with accurate mass determination emerges as a valuable technique for the precise elucidation of all possible byproducts. The hydroxyl radical was generated by excitation of the iron(III) aquacomplex [Fe(H2O)OH]2+ and hydrogen peroxide at pH3.5. Three different sulfonylureas were studied: metsulfuron methyl, cinosulfuron and thifensulfuron methyl. Results Several products owing to the reactivity of hydroxyl radicals with sulfonylurea were obtained. They arise from scission of the sulfonylurea bridge, hydroxylation of the aromatic ring, demethylation of the methoxy group and more importantly and unequivocally from the rupture of the triazine skeleton. To reach such scission, a primary demethylation of the methoxy group on the triazine moiety seems to act as a precursor process. Such a process was observed with the three studied sulfonylurea compounds. Conclusions The reported results demonstrated the usefulness of accurate mass measurements undertaken by LC/ESI-QTOFMS for structural elucidation of the unknown byproducts that were generated during hydroxyl radical reactions with some sulfonylureas. It has been possible herein to identify the structures of products arising from the opening of the recalcitrant triazine structure via hydrolysis processes in acidic solutions.
- Chahboune, Rajae,Mountacer, Hafida,Sarakha, Mohamed
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p. 1370 - 1380
(2015/07/15)
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- Design and synthesis of triazolopyrimidine acylsulfonamides as novel anti-mycobacterial leads acting through inhibition of acetohydroxyacid synthase
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Novel triazolopyrimidine acylsulfonamides class of antimycobacterial agents, which are mycobacterial acetohydroxyacid synthase (AHAS) inhibitors were designed by hybridization of known AHAS inhibitors such as sulfonyl urea and triazolopyrimidine sulfonamides. This Letter describes the synthesis and SAR studies of this class of molecules by variation of two parts of the molecule, the phenyl and triazolopyrimidine rings. SAR study describes optimisation of enzyme potency, whole cell potency and evidence of mechanism of action.
- Patil, Vikas,Kale, Manoj,Raichurkar, Anandkumar,Bhaskar, Brahatheeswaran,Prahlad, Dwarakanath,Balganesh, Meenakshi,Nandan, Santosh,Shahul Hameed
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supporting information
p. 2222 - 2225
(2014/05/06)
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- Sulfonylureas have antifungal activity and are potent inhibitors of Candida albicans acetohydroxyacid synthase
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The sulfonylurea herbicides exert their activity by inhibiting plant acetohydroxyacid synthase (AHAS), the first enzyme in the branched-chain amino acid biosynthesis pathway. It has previously been shown that if the gene for AHAS is deleted in Candida albicans, attenuation of virulence is achieved, suggesting AHAS as an antifungal drug target. Herein, we have cloned, expressed, and purified C. albicans AHAS and shown that several sulfonylureas are inhibitors of this enzyme and possess antifungal activity. The most potent of these compounds is ethyl 2-(N-((4-iodo-6-methoxypyrimidin-2-yl)carbamoyl) sulfamoyl)benzoate (10c), which has a Ki value of 3.8 nM for C. albicans AHAS and an MIC90 of 0.7 μg/mL for this fungus in cell-based assays. For the sulfonylureas tested there was a strong correlation between inhibitory activity toward C. albicans AHAS and fungicidal activity, supporting the hypothesis that AHAS is the target for their inhibitory activity within the cell.
- Lee, Yu-Ting,Cui, Chang-Jun,Chow, Eve W. L.,Pue, Nason,Lonhienne, Thierry,Wang, Jian-Guo,Fraser, James A.,Guddat, Luke W.
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supporting information
p. 210 - 219
(2013/02/23)
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- Study of the hydrolysis of a sulfonylurea herbicide using liquid chromatography with diode array detection and mass spectrometry by three-way multivariate curve resolution - Alternating least squares
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This research is focused on the development of a novel, automated chemometric method for obtaining relevant chemical information from time-course measurements of an evolving chemical system. This paper describes an investigation of the hydrolysis of Ally, which is a sulfonylurea herbicide. The hydrolysis of this compound is observed at different pHs and temperatures by reversed-phase liquid chromatography using a diode array detector. The data are analyzed using a three-way, multivariate curve resolution technique. Of special interest was the application of a closure constraint in the kinetic dimension followed by the determination of the rate constants for each step of the pathway by using a differential equation solver and nonlinear fitting of the data.
- Bezemer,Rutan
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p. 4403 - 4409
(2007/10/03)
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- Light induced transformation of tribenuron-methyl
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To study the photostability of sulfonylurea herbicide tribenuron-methyl (methyl 2-[[[[ N-(4- methoxy-6-methyl-1,3,5-triazin-2-yl) methylamino] carbonyl]amino]sulfonyl] benzoate), in the field, model experiments with organic solvents were performed. Irradiation of tribenuron-methyl in methanol, isopropanol and cyclohexane yielded 4-methoxy-6-methyl-2-aminomethyl-1,3,5-triazine; methyl-2-(aminosulfonyl) benzoate; N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N-methyl urea; N-(2-carbomethoxy phenyl)-N-(4- methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-methyl urea; 2-(aminosulfonyl) benzoic acid, N-methyl saccharin and saccharin in considerable amounts. The rate of degradation in different solvents followed first-order kinetics with a statistically significant correlation coefficient.
- Bhattacharjee,Dureja
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p. 741 - 749
(2007/10/03)
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- Light-induced transformations of tribenuron-methyl in aqueous solution
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Tribenuron-methyl a sulfonylurea herbicide, readily photodegraded in aqueous solution under sunlight and UV light. The photoproducts identified were N-methyl-4-methoxy-6-methyl-1,3,5-triazine-2-amine, methyl 2- (aminosulfonyl) benzoate, o-benzoic sulfimide, N-(4-methoxy-6-methyl-1,3,5- triazin-2-yl)-N-methyl urea and N-(2-carbomethoxyphenyl)-N-(4-methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-methyl urea. The rate of photodegradation of tribenuron-methyl in different types of water followed first-order kinetics with significant correlation coefficient, increased with increase in pH and was also dependent upon the dissolved impurities.
- Bhattacherjee,Dureja
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p. 183 - 188
(2007/10/03)
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- Application of the sulfonamide functional groups as an anchor for solid phase organic synthesis (SPOS)
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Sulfonyl chlorides have been found to readily couple to an amino functionalized resin. The resulting sulfonamide anchoring group is stable to a variety of reactions commonly used in SPOS. Acid induced cleavage is facile, affording functionalized sulfonamides in high yields.
- Beaver,Siegmund,Spear
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p. 1145 - 1148
(2007/10/03)
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- Collection of ion-trap mass spectre of sulfonylurea pyrolysis products
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The pyrograms of 14 sulfonylureas, i.e. herbicides characterized by high biological activity and low application dose are discussed and the mass spectra of over 30 relevant pyrolysis products as obtained with a heated filament pyrolyzer interfaced to a capillary gas chromatograph/ion-trap detector mass spectrometer are presented. Such a data compilation is useful for diagnostic purposes for both intact sulfonylureas and their metabolites after degradation in soil, because metabolites and pyrolysis products are often identical and most of their mass spectra are lacking in commercially available mass spectral libraries. The performance of the ion-trap detector based on the quality of the mass spectra is briefly discussed.
- Galletti,Dinelli,Chiavari
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p. 333 - 338
(2007/10/02)
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- Kinetics and Hydrolysis Mechanism of Chlorsulfuron and Metsulfuron-Methyl
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In acidic media, hydrolysis of chlorsulfuron and metsulfuron-methyl occurs via two consecutive reactions which were followed by ultraviolet spectrophotometry. For these two reactions, the pseudo-first-order rate constants increase proportionally to the concentration of hydronium ion in the more acidic media and to the square of this concentration at higher pH values. A kinetic study by HPLC shows that the first reaction leads to the formation of 4-methoxy-6-methyl-1,3,5-triazin-2-amine and (o-chlorophenylsulfonyl) carbamic acid for chlorsulfuron or (o-methoxycarbonylphenylsulfonyl) carbamic acid for metsulfuron-methyl. The second reaction is the conversion of these sulfonylcarbamic acids to sulfonamides and carbon dioxide. The complete lack of saccharin and of o-sulfamoyl benzoic acid proves that the ester function of the methoxycarbonyl group is stable. The lack of general acid-base catalysis and a solvent deuterium isotope effect less than unity are consistent with a rate-determining cleavage of the protonated substrate. In the basic pH range (10-14) a single reaction occurs, the nucleophilic substitution of the methoxy group on the triazine by a hydroxide group.
- Hemmamda, Saadi,Calmon, Michelle,Calmon, Jean P.
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