89392-03-0Relevant articles and documents
Discovery of ortho-Alkoxy Substituted Novel Sulfonylurea Compounds That Display Strong Herbicidal Activity against Monocotyledon Grasses
Wang, Hai-Lian,Li, Hao-Ran,Zhang, Yi-Chi,Yang, Wen-Tao,Yao, Zheng,Wu, Ren-Jun,Niu, Cong-Wei,Li, Yong-Hong,Wang, Jian-Guo
, p. 8415 - 8427 (2021/08/03)
In the present study, we have designed and synthesized a series of 42 novel sulfonylurea compounds with ortho-alkoxy substitutions at the phenyl ring and evaluated their herbicidal activities. Some target compounds showed excellent herbicidal activity against monocotyledon weed species. When applied at 7.5 g ha-1, 6-11 exhibited more potent herbicidal activity against barnyard grass (Echinochloa crus-galli) and crab grass (Digitaria sanguinalis) than commercial acetohydroxyacid synthase (AHAS; EC 2.2.1.6) inhibitors triasulfuron, penoxsulam, and nicosulfuron at both pre-emergence and postemergence conditions. 6-11 was safe for peanut for postemergence application at this ultralow dosage, suggesting that it could be considered a potential herbicide candidate for peanut fields. Although 6-11 and triasulfuron share similar chemical structures and have close Ki values for plant AHAS, a significant difference has been observed between their LUMO maps from DFT calculations, which might be a possible factor that leads to their different behaviors toward monocotyledon weed species.
Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics
Gilbile, Rohidas,Bhavani, Ram,Vyas, Ritu
, p. 1477 - 1481 (2017/05/29)
A modified synthesis of methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulphuron) is described. The merits of the synthesis are (i) one pot chlorination of methyl 1-methyl-1 H-pyrazole-4-carboxylate (1) in presence of sulphuryl chloride resulting in methyl 3,5-dichloro-1-methyl-1 H-pyrazole-4-carboxylate (2) (ii) conversion of 3-chloro-5-mercapto-1-methyl-1 H-pyrazole-4-carboxylate (3) to 3-chloro-1-methyl-5-sulfamoyl pyrazole-4-carboxylate (4) under mild reaction conditions utilizing tetrabutyl ammonium chloride, N-chlorosuccinimide and ammonium carbonate (iii) condensation of sulphonamide (4) with carbamate (6) by microwave irradiation. Efforts were made to calculate, atom economy, reaction mass efficiency and E-factor for all the reaction steps involved in the synthesis of halosulfuron. The E-factor values in step 2 and step 4 reaction is lower, indicating that these reactions are greener (generation of less waste) when compared to the remaining steps in the synthesis.
Process for the preparation of 4,6-disubstituted 2-isocyanatopyrimidines and their use as intermediates for active compound syntheses
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Example 2, (2008/06/13)
Isocyanates of the formula (I) in which X and Y are defined as in formula (I) of claim 1 can be prepared by reacting a compound of the formula (II) or its salts in which X and Y are defined as in formula (I), with 1 to 6 mol of phosgene per mole of compound of the formula (II), in the presence of 2 to 3.5 molar equivalents of a base per mole of compound of the formula (II) and in the presence of an aprotic organic solvent at a reaction temperature in the range from ?30 to +60° C. to give the compound of the formula (I). The compounds (I) can be converted by reaction with nucleophiles to give addition products, such as carbamates, ureas and sulfonylureas and corresponding products, e.g. herbicidal sulfonylureas.
