- Discovery of ortho-Alkoxy Substituted Novel Sulfonylurea Compounds That Display Strong Herbicidal Activity against Monocotyledon Grasses
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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.
- 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
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p. 8415 - 8427
(2021/08/03)
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- Synthesis method of rimsulfuron
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The invention relates to the technical field of herbicide synthesis, and discloses a rimsulfuron synthesis method, which comprises the following steps of: S1, preparation of raw materials; S2, condensation; and S3, purification: A, adding a rimsulfuron crude product obtained in S2 into a first solvent, heating to 40-100 DEG C, and keeping the temperature for 2-5 hours, wherein the mass ratio of the rimsulfuron crude product to the first solvent is 1: 2; B, adding a second solvent into the liquid treated in the step A, then cooling a liquid system to -10 to 20 DEG C, then filtering precipitates, and taking a filter cake for later use, wherein the mass ratio of the second solvent to the first solvent in the step A is 1: 2; C, adding the filter cake obtained in the step B into a third solvent, stirring and pulping, and keeping the pulping temperature at 0-50 DEG C for 2-6 hours, wherein the mass ratio of the third solvent to the first solvent in the step A is 1: 2.5; and D, filtering anddrying the substance treated in the step C to obtain the rimsulfuron active compound. The purity of the finally prepared rimsulfuron can be improved.
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Paragraph 0030; 0032; 0036; 0037; 0072-0079
(2020/09/20)
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- Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics
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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.
- Gilbile, Rohidas,Bhavani, Ram,Vyas, Ritu
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p. 1477 - 1481
(2017/05/29)
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- METHOD FOR PRODUCING PYRIMIDINE COMPOUND
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To provide a method for producing pyrimidine compound useful as an intermediate for agricultural chemicals or pharmaceuticals, which is simple in operation, presents high yield and produces only a small amount of by-products. The method comprises reacting a compound represented by the formula (I) with a compound represented by the formula (II) in the presence of a pyridine compound to produce a compound represented by the formula (III), a compound represented by the formula (IV) or their mixture.
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Page/Page column 16
(2011/01/11)
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- Process for the preparation of 4,6-disubstituted 2-isocyanatopyrimidines and their use as intermediates for active compound syntheses
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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.
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