- 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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- Synergistic herbicidal composition and use thereof
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A herbicidal composition is provided, the composition comprising: (A) the crystalline modification I of 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione); and (B) the crystalline modification I of methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulfuron-methyl). A method of controlling plant growth at a locus comprises applying to the locus herbicidally effective amounts of both (A) the crystalline modification I of 2-(4-mesyl-2-nitrobenzoyl)cyclohexane-1,3-dione (mesotrione); and (B) the crystalline modification I of methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulfuron-methyl).
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Page/Page column 13
(2017/05/14)
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- Form of halosulfuron-methyl, a process for its preparation and use of the same
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The present invention describes the crystalline form of halosulfuron-methyl of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods and using the crystal to prepare stable agrochemical formulation. The invention also describes the use of various solvents towards the crystalline form preparation conditions.
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- Method for producing a solid herbicide formulation
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The invention relates to a method for producing a solid herbicide formulation containing a) a herbicide from the group of sulfonylurea, or the salts thereof which are useful in the agricultural domain, b) optionally at least one other herbicide, c) optionally a safener, and d) at least one formulation adjuvant. A suspension is formed in water, consisting of the sulfonylurea a), optionally at least one other herbicide b), optionally a safener c) and at least one formulation adjuvant d). The suspension is adjusted to a pH value between 6.5 and 8 by adding an acid or a base, and is then dried to obtain the solid formulation.
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- Synthesis of Halosulfuron-methyl via Selective Chlorination at 3- and/or 5-Position of Pyrazole-4-carboxylates
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Reactions of methyl pyrazole-4-carboxylates 4b-d with N-chlorosuccinimide under heating conditions without a solvent gave methyl 3,5-dichloro-1-methylpyrazole-4-carboxylate 4a in good yields. The reaction of 4a with sodium hydrosulfide led to a nucleophilic substitution on the 5-position regioselectively to afford methyl 3-chloro-1-methyl-5-mercaptopyrazole-4-carboxylate 6a, which was followed by oxidative chlorination and amination to obtain 3-chloro-1-methyl-5-sulfamoylpyrazole-4-carboxylate 2a. Finally, the reaction of 2a with phenyl 4,6-dimethoxypyrimidin-2-yl carbamate 7 provided methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4- carboxylate (halosulfuron-methyl) 1a promising herbicide in corn.
- Morimoto, Katsushi,Sato, Toshiaki,Yamamoto, Susumu,Takeuchi, Hiroshi
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p. 537 - 540
(2007/10/03)
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- Herbicide antidotes as safeners for reducing phytotoxicity resulting from synergistic interaction between herbicides and other pesticides
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The disclosure herein relates to means for combatting the adverse phytotoxic action to crops arising from the interaction of various herbicidal compounds and biocidal compounds, e.g., insecticidal and/or fungicidal compounds. The means employed to reduce said interaction involves the safening action of various antidotal compounds.
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