101200-48-0

Usage

Uses

Used in Agricultural Industry:
Tribenuron methyl is used as a herbicide for the protection of crops such as corn, citrus, potatoes, tomatoes, rice, and vines. It is employed to control annual grasses and broadleaf weeds on barley, blueberries, oats, wheat, flax, and rape seed (canola). It is applied as a foliar spray and directly to the soil, as it is rapidly absorbed by the foliage and the roots, and is translocated throughout the plant to the growing points. The herbicide acts by inhibiting the synthesis of amino acids, specifically valine and isoleucine, which prevents cell division and cell growth. Selectivity occurs due to the differences in the metabolism of sulfonylureas between crops and weeds.
Registered for use in EU countries and the U.S., with maximum allowable residue levels set for various raw agricultural commodities, including barley, canola, cotton, flax, oat, and wheat. Tolerances with regional registration are established as per the regulations.

Air & Water Reactions

Hydrolysis occurs rapidly at pH <7 or >12.

Reactivity Profile

A sulfonylurea derivative.

Trade name

ALLY?; CANVAS?; DPX-L-5300?; EXPRESS?; EXPRESS?-75 DF; HARMONY EXTRA?; INL-5300?; L 5300?; MATRIX?

Metabolic pathway

The chemical structure of tribenuron methyl possesses a mono-N-methyl group in the sulfonylurea linkage which is a unique sulfonylurea herbicide and undergoes complex degradation reactions in the environment. Tribenuron methyl degrades into many degradation products, as indicated in the pathways by photolytic and hydrolytic chemical reactions and by biological degradations by mammal, plant, and soil. It is interesting to note that photolysis in different solvents yields diverse products depending on the individual solvents.

Degradation

Methomyl (1) was hydrolysed under alkaline conditions at 25 °C (DT50 ca. 14 days) and was stable under neutral to acidic conditions [DT50 > 30 days at pH 5 and 7 (Friedman, 1983)l. Cleavage of the carbamate ester bond is the primary degradation pathway, yielding S-methyl N-hydroxy-thioacetimidate (2). Irradiation of methomyl in dilute aqueous solution at 254 nrn yielded acetonitrile (3), dimethyl disulfide, acetone, N-ethylidenethylamine and carbon dioxide (Freeman and Ndip, 1984). Methomyl does not absorb sunlight but underwent degradation to acetonitrile by indirect photolytic reactions in/on soil surfaces (Swanson, 1986).

InChI:InChI=1/C15H17N5O6S/c1-9-16-13(18-14(17-9)26-4)20(2)15(22)19-27(23,24)11-8-6-5-7-10(11)12(21)25-3/h5-8H,1-4H3,(H,19,22)

Synthetic route

tribenuron methyl (101200-48-0) → 2-[4-methoxy-6-methyl-1,3,5-triazin-2-yl(methyl)carbamoylsulfamoyl]benzoic acid (101200-48-0)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 1h; Hydrolysis;

Upstream product

• 74222-95-0 2-(methoxycarbonyl)benzenesulfonyl isocyanate 
• 5248-39-5 2-methoxy-4-methyl-6-methylamino-1,3,5-triazine 

Downstream Products

• 5248-39-5 2-methoxy-4-methyl-6-methylamino-1,3,5-triazine 

Relevant academic research and scientific papers

Light-induced transformations of tribenuron-methyl in aqueous solution

Tribenuron-methyl a sulfonylurea herbicide, readily photodegraded in aqueous solution under sunlight and UV light. The photoproducts identified were N-methyl-4-methoxy-6-methyl-1,3,5-triazine-2-amine, methyl 2- (aminosulfonyl) benzoate, o-benzoic sulfimide, N-(4-methoxy-6-methyl-1,3,5- triazin-2-yl)-N-methyl urea and N-(2-carbomethoxyphenyl)-N-(4-methoxy-6- methyl-1,3,5-triazin-2-yl)-N'-methyl urea. The rate of photodegradation of tribenuron-methyl in different types of water followed first-order kinetics with significant correlation coefficient, increased with increase in pH and was also dependent upon the dissolved impurities.

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.

Form of tribenuron-methyl, a process for its preparation and use of the same

A crystalline form of tribenuron-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.

Synergistic herbicidal composition and use thereof

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 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]sulfonyl]benzoate (tribenuron-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 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]sulfonyl]benzoate (tribenuron-methyl).

Halopyridyl triazolinone herbicides and herbicidal use thereof

Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.

Herbicidal heterocyclic sulfonylurea compositions safened by herbicidal acids such as 2,4-D below a pH of 5

Disclosed are herbicidal concentrate formulation compositions having reduced grass crop plant phytotoxicity comprising certain sulfonamide or sulfonylurea herbicides in admixture with a herbicidal organic acid from the group consisting of clopyralid, 2,4-D, 2,4-DP, dicamba, dichlorprop-P, fluroxypyr MCPA, MCPP, mecoprop-P, picloram, triclopyr or mixtures of said acids; also disclosed is the preparation of said compositions and the pre- and post-emergent agricultural uses thereof in water diluted form.

Soybean plants with dominant selectable trait for herbicide resistance

The utilization of a positive selection seed screening process to isolate rate variants with resistance to a herbicide is described. The ability to screen large numbers of mutagenized seed has made it feasible to pursue and isolate plants with low frequency dominant herbicide-resistance mutations. The dominant herbicide resistance mutations are useful for many applications including expanding the utility of sulfonylurea herbicides for soybean weed control, production of F1 and F2 seeds, and as selectable markers for efficient seed purification.

N-phenylpyrrolidines

The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives of the formula I below are suitable for protecting crop plants against the phytotoxic action of herbicides and for regulating the plant growth. The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives are those of the formula I STR1 wherein A is --COOR1, --COSR1, --COO? M≈, --CONR2 R3 or --COCl; R1 is hydrogen, C1 -C4 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl; R2 and R3 independently of one another are hydrogen, C1 -C4 alkyl or C3 -C7 cycloalkyl; or R2 and R3 together with the nitrogen atom to which they are bonded are a saturated 3- to 7-membered heterocycle which can contain an additional hetero atom selected from the group comprising O, N and S and which is unsubstituted or up to trisubstituted by C1 14 C4 alkyl; and M≈ is the equivalent of an alkali metal cation or an alkaline earth metal cation or HN≈ (R2)3, and their isomers in optically pure or enriched form.

Herbicidal compound concentrate

There is provided a novel herbicidal compound concentrate in the form of compressed solid formulations that disintegrate in water to form a sprayable dispersion.

Process for preparing sulfonylurea salts

A process for preparing salts of herbicidal sulfonylureas comprises contacting a solution of the corresponding sulfonylurea in a water-immiscible halogenated hydrocarbon solvent under reaction conditions with the corresponding alkali metal or alkaline earth metal hydroxide and separating the sulfonylurea salt.