15545-48-9

Basic information

• Product Name: Chlorotoluron
• Synonyms: 3-(3-chlor-4-methylphenyl)-1,1-dimethylharnstoff;3-(3-chloro-4-methylphenyl)-1,1-dimethyl-urea;3-(3-Chloro-4-methylphenyl)-N,N-dimethylurea;3-(3-chloro-p-tolyl)-1,1-dimethyl-ure;c2242;cga15646;clortokem;dicuran
• CAS NO: 15545-48-9
• Molecular Formula: C₁₀H₁₃ClN₂O
• Molecular Weight: 212.68
• EINECS: 239-592-2
• Product Categories: ACTIVE AGROCHEMICAL INGREDIENTS;HERBICIDE;CHPesticides&Metabolites;Alphabetic;C;Herbicides;Urea structure;Agro-Products;Amines;Aromatics
• Mol File: 15545-48-9.mol

Chemical Properties

• Melting Point: 148.3°
• Boiling Point: 367.8 °C at 760 mmHg
• Flash Point: 2 °C
• Appearance: /
• Density: 1.2426 (rough estimate)
• Vapor Pressure: 1.33E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: 14.43±0.70(Predicted)
• Water Solubility: 70.43mg/L(20 oC)
• Merck: 13,2191
• BRN: 2647688
• CAS DataBase Reference: Chlorotoluron(CAS DataBase Reference)
• NIST Chemistry Reference: Chlorotoluron(15545-48-9)
• EPA Substance Registry System: Chlorotoluron(15545-48-9)

Safety Data

• Hazard Codes: Xn;N,N,Xn,F
• Statements: 40-50/53-63-36-20/21/22-11
• Safety Statements: 26-36/37-46-60-61-16
• RIDADR: UN 3077
• WGK Germany: 3
• RTECS: YS7230000
• Hazardous Substances Data: 15545-48-9(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Chlorotoluron is used as a herbicide for controlling various types of weeds in agricultural settings. Its selective action allows it to be effective against specific weed species without causing harm to the desired crop or beneficial insects like honeybees. This selective herbicidal property makes it a valuable tool in modern agriculture for maintaining crop health and yield.
Used in Environmental Management:
Due to its moderate toxicity to certain non-target organisms, Chlorotoluron can be used in environmental management practices to control invasive plant species or manage vegetation in ecologically sensitive areas. Its application in these contexts helps maintain ecological balance and protect native flora and fauna from the negative impacts of invasive species.

Metabolism

Chlortoluron is rapidly metabolized in winter wheat. Hydroxylation of the methyl group on the phenyl ring has been demonstrated as a detoxification mechanism for chlortoluron resistance in winter wheat, whereas in the susceptible weed blackgrass (Alopecurus myosuroides Huds.), the main metabolite is the mono N-demethylated metabolite (107). In a tolerant weed, Persian speedwell (Veronica persica Poir.), chlortoluron is rapidly transformed to the nonphytotoxic di-N-demethylated metabolite (107).

InChI:InChI=1/C10H13ClN2O/c1-7-4-5-8(6-9(7)11)12-10(14)13(2)3/h4-6H,1-3H3,(H,12,14)

Upstream product

• 201230-82-2 carbon monoxide 
• 124-40-3 dimethyl amine 
• 28479-22-3 2-chloro-4-isocyanato-1-methylbenzene 
• 506-59-2 N,N-dimethylammonium chloride 
• 53170-19-7 d6-dimethylamine hydrochloride 

Downstream Products

• 13142-64-8 3-(3-chloro-4-methyl)phenylurea 
• 22175-22-0 N'-(3-chloro-4-methylphenyl)-N-methylurea 
• 59587-00-7 N'-(3-chloro-4-hydroxymethylphenyl)-N-methylurea 
• 59587-03-0 N'-(3-chloro-4-hydroxymethylphenyl)-N,N-dimethylurea 
• 59587-01-8 2-Chloro-4-(3,3-dimethyl-ureido)-benzoic acid 
• 74-89-5 methylamine 
• 124-40-3 dimethyl amine 
• 95-74-9 3-chloro-p-toluidine 
• 7160-01-2 N,N-dimethyl-N'-(4-tolyl)urea 
• 1182602-42-1 butyl (E)-3-(4-chloro-2-(3,3-dimethylureido)-5-methylphenyl)acrylate 
• 28479-22-3 2-chloro-4-isocyanato-1-methylbenzene 
• 7260-94-8 N,N-dimethylcarbamic acid 

Related news

The influence of diphenylcarbazide and hydrazobenzene on the binding of the herbicide Chlorotoluron (cas 15545-48-9) to isolated thylakoids09/04/2019

To investigate the overlap of the effects of QB site inhibitors and donors of Photosystem II we analyzed the binding of [14C]chlorotoluron, a representative of QB site inhibitors, to isolated thylakoids in the presence of two electron donors, sym-diphenylcarbazide or hydrazobenzene. Chlorotoluro...detailed

THz spectroscopic investigation of Chlorotoluron (cas 15545-48-9) by solid-state density functional theory09/01/2019

The terahertz time–domain spectrum (THz–TDS) of chlorotoluron has been simulated and assigned with solid-state density functional theory (DFT) in the range of 0.5–2.2 THz. The calculations based on the hybrid density functionals B3LYP and PW91 are performed to analyze the origins of observed ...detailed

Impact of atrazine and nitrogen fertilizers on the sorption of Chlorotoluron (cas 15545-48-9) in soil and model sorbents08/31/2019

Sorption of chlorotoluron in ammonium sulfate, urea and atrazine multi-solutes system was investigated by batch experiments. The results showed application of nitrogen fertilizers to the soil could affect the behavior of chlorotoluron. At the same concentration of N, sorption of chlorotoluron de...detailed

Biological responses of wheat (Triticum aestivum) plants to the herbicide Chlorotoluron (cas 15545-48-9) in soils08/30/2019

Chlorotoluron is a phenylurea herbicide that is widely used for controlling grass weeds in the land of cereal, cotton and fruit production. However, extensive use of this herbicide may lead to its accumulation in ecosystems, thus inducing the toxicity to crops and vegetables. To assess chlorotol...detailed

Effect of dissolved organic matter on mobility and activation of Chlorotoluron (cas 15545-48-9) in soil and wheat08/29/2019

Chlorotoluron is a pesticide that is moderately absorbed and fairly mobile and leaching in soils. Dissolved organic matter (DOM) plays a critical role in affecting the environmental behavior of pesticides. In this study, we report the effect of DOM extracted from sludge (SL) and straw (ST) on ch...detailed

Impact of dissolved organic matter on bioavailability of Chlorotoluron (cas 15545-48-9) to wheat08/28/2019

Chlorotoluron (Chl) is a phenylurea herbicide and is widely used for controlling weeds. While it has brought great benefits to crop production, it has also resulted in contamination to ecosystem. In this study, we investigated accumulation of chlorotoluron (Chl) and biological responses of wheat...detailed

Chlorotoluron (cas 15545-48-9) mobility in compost amended soil08/27/2019

Knowledge about the impact that various organic amendments have on the behavior of pesticides in soils is essential when assessing groundwater contamination risk. The aim of this study was to evaluate the impact of a compost amendment on chlorotoluron mobility in the A horizon of the Luvic Chern...detailed

Relevant articles and documents

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.

Comparative catalytic C-H vs. C-Si activation of arenes with Pd complexes directed by urea or amide groups

Analysis of regiocontrol in Pd-catalysed C-H activation leads to observations of aryltrimethylsilyl activation and to superior results with urea-based substrates.

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.

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 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.

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 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.

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.