19937-59-8

Basic information

• Product Name: METOXURON
• Synonyms: 3-(3-Chlor-4-methoxyphenyl)-1,1-dimethylharnstoff;3-(3-chloro-4-methoxyphenyl)-1,1-dimethyl-ure;Dosagran;Dosanex fl;Dosanex mg;dosanexfl;dosanexmg;Herbicide 6602
• CAS NO: 19937-59-8
• Molecular Formula: C₁₀H₁₃ClN₂O₂
• Molecular Weight: 228.68
• EINECS: 243-433-2
• Product Categories: ACTIVE AGROCHEMICAL INGREDIENTS;Plant growth regulatorsPesticides&Metabolites;Alpha sort;Herbicides;H-MAlphabetic;M;METI - MZPesticides&Metabolites;Pesticides;Pesticides&Metabolites;Urea structure
• Mol File: 19937-59-8.mol

Chemical Properties

• Melting Point: 124-127 °C
• Boiling Point: 391.6 °C at 760 mmHg
• Flash Point: 2 °C
• Appearance: /
• Density: 1.3100 (rough estimate)
• Vapor Pressure: 2.43E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: 13.83±0.70(Predicted)
• Water Solubility: 678mg/L(23 oC)
• CAS DataBase Reference: METOXURON(CAS DataBase Reference)
• NIST Chemistry Reference: METOXURON(19937-59-8)
• EPA Substance Registry System: METOXURON(19937-59-8)

Safety Data

• Hazard Codes: N,Xn,F
• Statements: 50/53-36-20/21/22-11
• Safety Statements: 60-61-36-26-16-36/37
• RIDADR: UN3077 9/PG 3
• RTECS: YS5775000
• Hazardous Substances Data: 19937-59-8(Hazardous Substances Data)

Usage

Metabolic pathway

Photodegradation of metoxuron with UV irradiation in the presence of UV-H2O2 and -TiO2 primarily proceeds with the replacement of the chlorine atom with the hydroxy group and the attack of OH radicals at the 6-position on the phenyl ring. The principal photoproducts identified are 3-(4-methoxy-2,5- paraquinone)-1,1-dimethylurea, hydroxymetoxuron, 3-(3-hydroxy-4-methoxyphenyl)-1,1-dimethylurea, 3-(3-chloro-4-hydroxyphenyl)-1,1-dimethylurea, and 3-(3-chloro-4-methoxyphenyl)-1,1dimethylurea.

InChI:InChI=1/C10H13ClN2O2/c1-13(2)10(14)12-7-4-5-9(15-3)8(11)6-7/h4-6H,1-3H3,(H,12,14)

Upstream product

• 75-44-5 phosgene 
• 5345-54-0 3-chloro-4-methoxyaniline 
• 124-40-3 dimethyl amine 
• 28395-76-8 3-chloro-4-methoxyphenylisocyanate 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 74-89-5 methylamine 
• 124-40-3 dimethyl amine 
• 5345-54-0 3-chloro-4-methoxyaniline 
• 2908-80-7 3-(4-hydroxyphenyl)-1,1-dimethylurea 
• 7260-94-8 N,N-dimethylcarbamic acid 

Relevant articles and documents

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.

Improved method for the preparation of 1,1-dimethyl-3-arylureas using chlorocarbonylsulfenyl chloride

A convenient procedure for preparing some arylureas having herbicidal properties is reported. The method has two steps: (1) reaction of arylamine with chlorocarbonylsulfenyl chloride in the presence of nonpolar solvent to produce aryl carbonylsulfenyl chloride and (2) reaction with dimethylamine in a two-phase reaction catalysed by phase-transfer catalyst to produce the corresponding aryl ureas. Taylor & Francis Group, LLC.

Phenylureas. Part 1. Mechanism of the basic hydrolysis of phenylureas

The mechanism of the hydrolytic decomposition of phenylureas in basic media in the pH range 12 to 14 is investigated. In this pH range a levelling of the rate-pH curve is observed as well as a change of the substituent influence on the hydrolysis rate. These experimental findings suggest the formation of an unreactive side product of the phenylurea in a parasitic side equilibrium at sufficiently high pH. The urea dissociates at the aryl-NH group to give its conjugate base. For the hydrolytic decomposition of phenylureas an addition-elimination mechanism is proposed as has been established for the alkaline hydrolysis of carboxylic acid esters and amides.

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.

Biocide composition and use

A stable liquid dispersion in an non-polar organic solvent containing an alkylsulphonylhalopyridine and a dispersing agent which is the reaction product of a hydroxyalkylcarboxylic acid and an amine or salt thereof. The alkylsulphonylhalopyridine may be 2,3,5,6-tetrachloro-4-(methylsulphenyl)pyridine and the hydroxycarboxylic acid may be poly(12-hydroxystearic acid) and the amine may be either dimethylamino propylamine or polyethyleneimine. The solvent may be white spirit or an ester or vegetable oil which is a plasticiser for PVC.

Process of improving activity of herbicides and fertilizers using N-(2-hydroxyethyl)-acetamide or -propanamide

The invention is related to the use of certain water-soluble compounds known as such and having the Formula for the modulation of membrane dependent metabolism processes within living cells, in particular with relation to transport phenomena and cell procedures which are induced or influenced by active agents supplied from outside the cell, products containing these substances for the above described uses and processes using these products.

Process for preparation of substituted phenylureas

Process for preparing a substituted phenylurea. A suitably substituted aniline, excess urea in a mole ratio of at least 1.1 with respect to the aniline, and a secondary amine are reacted simultaneously in a non-hydroxyl-containing organic solvent at a temperature of 130° to 250° C., with removal of ammonia as it forms. The phenylureas obtained are used as herbicides.

Composition for defoliating plants

New compositions for defoliating plants possessed of synergistic activity comprising (A) a compound of formula I STR1 in which R1 is hydrogen or C1 -C4 -alkyl, R2 is hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or C1 -C4 -alkylthio, R3 is hydrogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkylthio or C3 -C8 -cycloalkyl, wherein R2 and R3 taken together with the nitrogen atom to which they are attached is a morpholino- piperidino- or pyrrolidino-group, X is oxygen or sulfur, Y can be the same or different and is hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C2 -alkyl, C1 -C4 -alkylthio, trifluoromethyl or nitro, and n is the number 1, 2, 3, 4 or 5, in combination with (B) a defoliant for plants in a proportion of 1 to 99 parts by weight of component (A) to 99 to 1 parts by weight of component (B). As the defoliant there can be employed 1,2,3-thiadiazole-5-yl-urea derivatives, 1,2,3-thiadiazole-5-carboxylic acid derivatives, benzylaminopurine derivatives, 2,3-dihydro-5,6-dimethyl-1,4-dithiine-1,1,4,4-tetroxide, 1,1'-dimethyl-4,4'-bipyridilium-dichloride, sodium chlorate and S,S,S-tributylphosphortrithioate. The compositions of the invention are especially suitable for use in the defoliation of cotton plants.

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.