2164-17-2

Usage

Uses

Used in Agriculture:
Fluometuron is used as a herbicide for controlling many annual broad-leaved weeds in sugarcane and cotton crops. It is a selective herbicide that acts on susceptible plants by inhibiting photosynthesis. The EPA has registered Fluometuron exclusively for use on cotton and sugarcane. It can be applied pre-emergence, for weed control before planting, or post-emergence, after target crops and weeds come up, and may have residual activity for several months. Fluometuron is available in liquid, dry flowable, and wettable powder formulations.

Reactivity Profile

Fluometuron is a trifluoromethyl urea derivative. May react with hypochlorites to form nitrogen trichloride which explodes spontaneously in air [J. Am. Chem. Soc. 63:3530-32]. May reacts with azo and diazo compounds to generate toxic gases. Reacts with strong reducing agents to form flammable gases.

Hazard

Toxic by ingestion. Questionable carcinogen.

Health Hazard

SYMPTOMS: Symptoms of exposure to Fluometuron may include possible convulsions or coma; irritation to the skin, gastrointestinal tract, respiratory tract; and lowered blood pressure.

Fire Hazard

Flash point data are not available for Fluometuron, but Fluometuron is probably combustible.

Flammability and Explosibility

Nonflammable

Trade name

C 2059?; CIBA 2059?; COTORAN?; COTORAN? 50SC; COTORAN MULTI 50WP?; COTOREX?; COTTONEX?; COTTONEX? 50SC; DREXEL CROAK?; FLO-MET?; FLUOMETURON? 50SC; HERBICIDE C-2059?; HIGALCOTON?; LANEX?[C]; METURON 80 DF?; PAKHTARAN?; SETRE FLUOMETURON 80 WP?

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of Fand NOx

Potential Exposure

This material is used as a herbicide.

Environmental Fate

Soil. In soils, ?uometuron rapidly degrades (half-life approximately 30 days) to carbon dioxide, polar and nonextractable compounds (Hartley and Kidd, 1987; Humburg et al., 1989).Groundwater. According to the U.S. EPA (1986) ?uometuron has a high potential to leach to groundwaterPlant. In plants, ?uometuron degrades to a demethylated intermediate which subsequently is degraded to the aniline moiety (possibly m-tri?uoromethylaniline) (Hartley and Kidd, 1987; Humburg et al., 1989). Duke et al. (1991) reported that ?uometurChemical/Physical. Emits toxic fumes of nitrogen oxides and ?uorine when heated to decomposition (Sax and Lewis, 1987).

Shipping

UN2767 Phenyl urea pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

Liquid solutions are incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materi als, strong bases, strong acids, oxoacids, epoxides.

InChI:InChI=1/C10H11F3N2O/c1-15(2)9(16)14-8-5-3-4-7(6-8)10(11,12)13/h3-6H,1-2H3,(H,14,16)

Upstream product

• 370-56-9 m-Trifluoromethyl-carbanilic acid isopropyl ester 
• 124-40-3 dimethyl amine 
• 13114-87-9 N-(3-trifluoromethylphenyl)urea 
• 329-01-1 1-isocyanato-3-trifluoromethyl-benzene 
• 201230-82-2 carbon monoxide 
• 722-07-6 N-(3-trichloromethylphenyl)-N',N'-dimethylurea 
• 657-78-3 N-(3-(trifluoromethyl)phenyl)formamide 
• 506-59-2 N,N-dimethylammonium chloride 
• 15249-51-1 N,N-dimethylcarbamoyl bromide 
• 98-16-8 3-trifluoromethylaniline 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Downstream Products

• 85413-32-7 C₁₀H₁₀ClF₃N₂O 
• 124-40-3 dimethyl amine 
• 329-01-1 1-isocyanato-3-trifluoromethyl-benzene 
• 74-89-5 methylamine 
• 61208-74-0 N-(dimethylcarbamoyl) ethyl-3'-trifluromethyl oxanilate 
• 61208-49-9 N-(3-trifluoromethyl phenyl)-N-isopropylthio-N',N'-dimethyl-urea 

Relevant academic research and scientific papers

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

Synthesis method of phenylurea herbicide or deuteration-labeled phenylurea herbicide

The invention relates to a synthesis method of a phenylurea herbicide or a deuteration-labeled phenylurea herbicide (a compound of a formula (I)). The compound of the formula (I) is obtained by reacting a compound of a formula (II) with a dimethylamine salt or D6-dimethylamine salt in the presence of an organic base. According to the synthesis method, the side reaction of substituted phenyl isocyanate and water or alcohol is avoided, the leakage of dimethylamine or dimethylamine-D6 is reduced, and the synthesis method has the advantages of simple operation, low requirements for equipment, low cost, high yield, and fewer by-products. The formula I is shown in the description.

Preparation of N,N-Dimethyl-N′-arylureas using S,S-dimethyl dithio-carbonate as a carbonylating reagent

A new, general method for the preparation of N,N-di-methyl-N′- arylureas using S,S-dimethyl dithiocarbonate as a phosgene substitute is reported. The method has been set up according to four procedures, all including three steps: (1) reaction of S,S-di- methyl dithiocarbonate with dimethylamine to give S-methyl N,N-dimethylthiocarbamate; (2) halogenation with various halogenating reagents (chlorine, methanesulfenyl chloride, bromine, and meth-anesulfenyl bromide) to give N,N-dimethylcarbamoyl chloride or bromide; (3) in situ reaction with primary arylamines. All the target products were obtained in high yields (85-98%; 16 reactions, average yield 93%) and with high purity. Also noteworthy is the recovery of byproducts of industrial interest, namely methanethiol and dimethyl disulfide, with complete exploitation of the reagent S,S- dimethyl dithiocarbonate. Georg Thieme Verlag Stuttgart.

Distinct reactivity of Pd(OTs)2: The intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes

A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl ureas and 1,3-dienes that proceeds under mild conditions in relatively nonacidic media, is presented. The in situ generation, or preformation, of a palladium tosylate emerges as a key parameter in gaining the requisite reactivity for the C-H insertion/carbopalladation/nucleophilic displacement process. Copyright

Synthesis of aromatic urea herbicides by the selenium-assisted carbonylation using carbon monoxide with sulfur

Commercially useful aromatic urea herbicides were synthesized in good yields from lithium amides of aromatic amines with thiocarbamates, which were prepared by the selenium-assisted carbonylation of secondary amines with carbon monoxide and sulfur under mild conditions.

Herbicidal composition for upland farming and weeding method

A herbicidal composition for upland farming which can control weeds that have been difficult to control, for example, cleavers, chickweed, birdseye speedwell and violet, said composition containing as active ingredients a 3-substituted phenylpyrazole derivative represented by the general formula (I): STR1 (wherein R is a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a C1-6 haloalkyl group, a C2-6 alkenyl group or a C2-6 alkynyl group, R1 is a C1-6 alkyl group, X1 and X2, which may be the same or different, are halogen atoms, and Y is an oxygen atom or a sulfur atom) and at least one compound selected from the group consisting of sulfonylurea derivatives, phenylurea derivatives and phenoxy fatty acid derivatives; and a weeding method using said composition.

Substituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same

A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): STR1 wherein A is CH or N; when A is CH, R1 and R2 may be either each independently a member selected from the group consisting of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkenyl groups, unsubstituted or substituted cycloalkyl groups, and unsubstituted or substituted phenyl groups; when A is N, R1 is an unsubstituted or substituted alkyl group, R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.

Substituted pyridinesulfonamide compounds or their salts, process for preparing the same, and herbicides containing the same

A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): wherein R1 is an unsubstituted or substituted alkyl group; R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.

REACTION OF AMINES WITH N-ARYLUREAS, ALKYL N-ARYLCARBAMATES, AND SALTS OF THIOCARBAMIC ACIDS

The reaction of amines with N-arylureas, alkyl N-arylcarbamates, and salts of thiocarbamic acids is studied. The regularities found are explained by the characteristic features of hydrogen bond formation.

Process for the preparation of pure, unsymmetrically disubstituted ureas

Process for the preparation of pure, unsymmetrically disubstituted ureas of the general formula STR1 in which R denotes a phenyl radical which is unsubstituted, or monosubstituted or polysubstituted by halogen atoms or alkyl, alkoxy, aryloxy or trifluoromethyl groups, an oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, benzoxazolyl or benzothiazolyl radical which is unsubstituted, or monosubstituted or polysubstituted by halogen atoms or alkyl, alkoxy or trifluoromethyl groups and R1 and R2 independently of one another denote a hydrogen atom or an alkyl group, where R1 and R2 are not simultaneously hydrogen or R1 and R2 together denote a butylene or pentylene group, by reaction of an N-alkyl- or N,N-dialkylurea with an unsubstituted or substituted arylamine or a heterocyclic amine in the presence of that amine which is already present in the starting material, the respective N-alkyl- or N,N-dialkylurea.