METHOD OF PRODUCING SULPHONYLUREA HERBICIDES CONTAINING A 4-METHOXY-6-METHYL-1,3,5-TRIAZINE FRAGMENT Russian patent published in 2024 - IPC A01N41/06 A01N43/66 A01N47/36 C07D251/12 C07D251/42 C07D333/18 

FIELD: chemistry.

SUBSTANCE: invention relates to production of pesticides, more specifically to a method of producing herbicides from the class of sulphonylureas. Method of producing herbicides from the class of sulphonylureas containing 4-methoxy-6-methyl-1,3,5-triazine fragment, such as chlorsulfuron, triasulfuron, prosulfuron, iofensulfuron, metsulfuron-methyl, iodosulfuron-methyl, tribenuron-methyl or thifensulfuron-methyl, involves initial reaction of 2-amino- or 2-methylamino-4-methoxy-6-methyl-1,3,5-triazine with N,N'-disuccinimidyl carbonate in a medium of an anhydrous organic solvent while heating in a nitrogen or argon atmosphere, leading to formation of corresponding N'-succinimidylcarbamates, of general formula V

where R = H or Me, each of which is isolated individually. Further, the obtained N'-succinimidyl carbamates are used in reaction with sulphonamide or its sodium or potassium salt of general formula II or II-Na/K

where R' = Cl, OCH₂CH₂Cl, CH₂CH₂CF₃, I or CO₂Me; R" = H or I; or sulphonamide of formula in a polar organic solvent in the presence or absence of a base at temperature of 20–25 °C for 1–3 hours with subsequent treatment of the obtained reaction mass with water and acid to obtain the corresponding herbicides. Anhydrous organic solvent used is acetonitrile or tetrahydrofuran. Polar organic solvent used is acetone, acetonitrile, 1,4-dioxane, tetrahydrofuran, dimethyl sulphoxide, N,N-dimethylformamide or N,N-dimethylacetamide. Base used is 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, triethylamine, tributylamine, N,N-diisopropylethylamine, sodium or potassium hydroxide or sodium or potassium carbonate at the step of reacting N'-succinimidyl carbamates of general formula V with sulphonamides of general formula II. Acid used is hydrochloric, sulfuric, formic or acetic acid.

EFFECT: disclosed method of producing herbicides from the class of sulphonylureas containing 4-methoxy-6-methyl-1,3,5-triazine fragment, provides for reduction of number of technological operations, elimination of use of high temperatures, hazardous and toxic starting compounds and intermediate products, reduced duration of the process and higher safety, simplified design of the process.

5 cl, 3 tbl, 22 ex