120923-37-7

Basic information

• Product Name: Amidosulfuron
• Synonyms: AMIDOSULFURON;GRATIL;n-(((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-n-methylmethanesulfonamide;Amidosulfuron PESTANAL;METHYLMETHANESULFONAMIDE;1-(4,6-Dimethoxypyrimidin-2-yl)-3-(N-mesyl-N-methylsulfamoyl)urea;Amidosulfuron [iso];3,5-Dithia-2,4-diazahexanaMide,N-(4,6-diMethoxy-2-pyriMidinyl)-4-Methyl-, 3,3,5,5-tetraoxide
• CAS NO: 120923-37-7
• Molecular Formula: C₉H₁₅N₅O₇S₂
• Molecular Weight: 369.37
• EINECS: 407-380-0
• Product Categories: NULL
• Mol File: 120923-37-7.mol

Chemical Properties

• Melting Point: 160-163°C
• Appearance: /
• Density: 1.594 g/cm³
• Refractive Index: 1.587
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 0.12±0.40(Predicted)
• Stability: Hygroscopic, Unstable in Solution
• CAS DataBase Reference: Amidosulfuron(CAS DataBase Reference)
• NIST Chemistry Reference: Amidosulfuron(120923-37-7)
• EPA Substance Registry System: Amidosulfuron(120923-37-7)

Safety Data

• Statements: 52/53
• Safety Statements: 61
• WGK Germany: 1
• Hazardous Substances Data: 120923-37-7(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Amidosulfuron is used as a herbicide for controlling broad-leaved weeds in various agricultural settings. Its effectiveness in managing these weeds contributes to improved crop yield and reduced competition for resources such as nutrients, water, and sunlight.
Used in Pesticide Formulations:
Amidosulfuron is also utilized as a component in pesticide formulations, where it serves to enhance the overall effectiveness of the product. By targeting broad-leaved weeds specifically, it helps to minimize the growth of unwanted plants, thereby supporting a healthier and more productive agricultural ecosystem.

Toxicity

Amidosulfuron has a low mammalian toxicity and would not be expected to bioaccumulate. Amidosulfuron is moderately toxic to most terrestrial and aquatic species.

Metabolic pathway

The hydrolysis of 14C-amidosulfuron in buffer aqueous solutions under various conditions results in 2-amino- 4,6-dimethoxypyrimidine as the major hydrolyzed product. In soils, O-demethylated amidosulfuron is the major degradation product. In mammals and plants, primary hydroxylation at the pyrimidine ring is a characteristic degradation reaction yielding 5-hydroxyamidosulfuron.

InChI:InChI=1/C9H15N5O7S2/c1-14(22(4,16)17)23(18,19)13-9(15)12-8-10-6(20-2)5-7(11-8)21-3/h5H,1-4H3,(H2,10,11,12,13,15)

Upstream product

• 36315-01-2 4,6-dimethoxy-2-aminopyrimidine 
• 144851-58-1 N-[(N'-methyl-N'-methylsulfonyl-aminosulfonyl)-aminocarbonyl]-morpholine 
• 53203-08-0 (N-methylsulfonyl-N-methylamino)sulfonamide 
• 89392-03-0 O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate 

Downstream Products

• 36315-01-2 4,6-dimethoxy-2-aminopyrimidine 

Relevant articles and documents

HERBICIDAL COMPOSITIONS

The present invention provides compositions comprising herbicidally active compounds (A) and (B), where (A) represents one or more compounds of the general formula (I) or agrochemically compatible salts thereof [component (A)], and (B) represents one or more herbicides [component (B)]. The application further relates to a method and to the use of the herbicidal composition according to the invention for controlling harmful plants or for regulating growth.

Method for producing a solid herbicide formulation

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.

Herbicidal mixtures having a synergistic effect

PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.

Process for the preparation of sulfonylureas

Herbicidal sulfonylureas of the formula I, STR1 in which X is --O--, --O--NR2 -- or --SO2 --NR2 --, Y is --N-- or CH, R1 is (substituted) alkyl, (substituted) alkenyl or (substituted) alkynyl, or else, where X=O, (substituted) phenyl, R2 is H, alkyl, alkenyl, alkynyl or cycloalkyl, R3, R4 are H, (substituted) alkyl or (substituted) alkoxy, halogen, alkylthio, alkylamino or dialkylamino and R5, R6 are H or alkyl, and their salts with acids or bases, are prepared by reacting compounds of the formula II STR2 with compounds of the formula III STR3

Process for the preparation of sulfonylureas

A compound of formula I or salt thereof can be prepared in a process which comprises reacting a compound of formula II with a compound of formula III: STR1 wherein the formulae I-III the radical X is O, ONR2 or SO2 NR2 ; Y is N or CH; R1 is (subst.) alkyl, (subst.) alkenyl, (subst.) alkynyl, or in case X=O, also (subst.) phenyl; R2 is H, alkyl, alkenyl, alkynyl or cycloalkyl, R3 -R6 are defined in claim 1; Z is S or NR8 ; R7, R8 are H, alkyl, (subst.) phenyl or (subst.) benzyl, or, in case Z=NR8, R7 and NR8 are also a 5- to 7-membered heterocycle.

Processes for preparing sulfonylureas

Compounds of the formula I or salts thereof, STR1 in which X is oxygen, --O--NR2 -- or --SO2 --NR2 --, and Y is N or CH, R1 is (C1 -C6)alkyl, (C2 -C6)alkenyl or (C2 -C6)alkynyl, which are in each case optionally substituted, or, in the case where X=oxygen, also (subst.) phenyl, R2 is H, (C1 -C6)alkyl, (C2 -C6)alkenyl or -alkynyl or (C3 -C6) cycloalkyl, R3 and R4 are H, (subst.) (C1 -C4)alkyl or (subst.) (C1 -C4)alkoxy or halogen, (C1 -C4)alkylthio, (C1 -C4)alkylamino or di[(C1 -C4)alkyl]-amino, R5 is H or (C1 -C4)alkyl and R6 is hydrogen, may be prepared by reacting compounds of the formula II, with compounds of the formulae III, IV and V

Process for the preparation of N-alkylsulfonylaminosulfonylureas

Known herbicides of the formula (I) STR1 in which R1 is alkyl, alkenyl or alkynyl, which are optionally substituted by halogen, alkoxy or alkoxycarbonyl, R2 is H, alkyl, alkenyl, alkynyl or cycloalkyl, R3 and R4 are H or alkyl, R5 and R6 are H, alkyl or alkoxy, each of which can be substituted by halogen, alkoxy or alkylthio, or are halogen, alkylthio, alkylamino or dialkylamino, or, if R2 or R3 is H, their salts with bases, can be obtained when compounds of the formula II in which R1, R2 and R3 are as defined above, are reacted with compounds of the formula III STR2 in which R4, R5 and R6 are as defined above and R7 is alkyl, haloalkyl or optionally substituted phenyl, in an inert organic solvent, to give the compounds of the formula I.

Process for the preparation of N-alkylsulfonylaminosulfonylureas

Known herbicides of the formula (I) STR1 in which R1 is alkyl, alkenyl or alkynyl, which are optionally substituted by halogen, alkoxy or alkoxycarbonyl, R2 is H, alkyl, alkenyl, alkynyl or cycloalkyl, R3 and R4 are H or alkyl, R5 and R6 are H, alkyl or alkoxy, each of which can be substituted by halogen, alkoxy or alkylthio, or are halogen, alkylthio, alkylamino or dialkylamino, or, if R2 or R3 is H, their salts with bases, can be obtained when compounds of the formula II in which R1, R2 and R3 are as defined above, are reacted with compounds of the formula III STR2 in which R4, R5 and R6 are as defined above and R7 is alkyl, haloalkyl or optionally substituted phenyl, in an inert organic solvent, to give the compounds of the formula I.