Chlortoluron

212.68

212.68

239-592-2

SUW8L8G38A

1327

DTXSID8052853

COLORLESS CRYSTALS|white powder

2924299035

32.3

2.5

1.4 g/cm³

147-148 °C

367.8±42.0 °C(Predicted)

2 °C

1.6000 (estimate)

Solubility in water, g/100ml at 25°C: 0.0074 (very poor)

APPROX 4°C

Vapour pressure at 20°C: negligible

Oral-Rat LD50: 5800 mg/kg; inhalation-rat LC50: 1300 mg/m3

Combustion produces toxic nitrogen oxides and chloride gases

ODORLESS

145.96 Ų [M+H]+ [CCS Type: TW]|147.5 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated]

Stable to heat and UV light. Slowly hydrolyzed by strong acids and alkalis. DT50 (calculated) > 200 days (pH 5,7,9 and at 30 °C)

Noncorrosive

UN 3077

3

40-50/53-63-36-20/21/22-11

26-36/37-46-60-61-16

YS7230000

Xn;N,N,Xn,F

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable under normal conditions in neutral media. Hydrolyzed by strong acids and alkalis.

P273-P281-P501

H351-H361d-H410

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Collected Data on Herbicide Toxicology; Verlag Chemie GmBH, Postfach 1260/1280, 6940 Weinheim, Fed Rep of Germany, 4th instalment 2: 272 pages (1983). A loose-leaf collection published by the pesticides Committee of the German Research Association. A statement of the criteria involved in toxicological assessment of pesticides is followed by monographs on several herbicides, their applications, their toxicity to animals and man, and their metabolism or transformation in plants, soil and water. Each monograph is completed by a toxicological evaluation and a bibliography. The 4th supplement offers new or updated information on chlortoluron.|Geissbuhler H; How Safe are Pesticides; Experientia 38 (8): 890-5 (1982). The safety of the pesticides, chlortoluron and atrazine, is discussed in relation to use, exposure, pollution, etc.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H351: Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|Aggregated GHS information provided by 470 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Use water spray, foam, dry powder, carbon dioxide.

Avoid contact with skin, clothing and eyes.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder.

Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Separated from strong bases, strong acids and food and feedstuffs.

A harmful concentration of airborne particles can be reached quickly when dispersed.

Tumours have been detected in experimental animals but may not be relevant to humans.

Use local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

IN TEMPERATE CLIMATES, AN INITIAL SOIL APPLICATION OF 6 KG AI/HA HAD T/2 OF 30 TO 40 DAYS.

practically nontoxic

Levels of cytochrome p450s and rates of monooxygenase activities were studied in microsomes prepared from wheat cell suspension cultures. Cytochrome contents and enzymatic activities, namely, the enzymatic systems responsible for chlorotoluron ring-methy1 hydroxy1ation and N-demethylation, were enhanced after pretreatment of cells with 2,4-D, procloraz, mecoprop, chlorotoluron, and oxime ether safeners. Effects of various agrochemicals were also determined on chlorotoluron ring-methyl hydroxylase and N-demethylase, following their direct addition to microsomal preparations. Plant growth regulators and fungicide, as well as piperonyl butoxide decreased both activities, tetcyclacis, and procloraz being marked1y inhibitory. Naphthalic anhydride, oxime ether safeners, dich1ormid, and tridiphane had only weak effects. The substrate specificities of chlorotoluron ring-methyl hydroxylase and N-demethylase were also investigated using structural analogues of the herbicide. Diuron was the strongest inhibitor among the tested phenylureas. Other herbicides that can be metabolized by wheat affected both activities to different extents. However, diclofop enhanced only chlorotoluron N-demethylase.

LD50 Rat oral greater than 10000 mg/kg|LD50 Rat subcutaneous greater than 2000 mg/kg

Chlortoluron's production and use (not marketed in U.S.)(1) as a herbicide(2) would result in its release directly to the environment(SRC).

TERRESTRIAL FATE: Measured Koc values ranging from 1 to 3467(1) were obtained in a study of seventeen soils from Australia; generally, measured Koc values averaged from 150-420(2-4) with adsorption dependent on the percentage of organic matter present in the soil(1). Based on a recommended classification scheme(5), these values indicate that chlortoluron will generally have moderate mobility in soil(SRC). Absorption follows an L-isotherm indicating a decrease in site availability as the solution concentration of this compound increases(6). Biodegradation is expected to be the major fate process for chlortoluron in soil(7-9). In an outdoor lysimeter experiment, half-lives of 49 days and 52 days were reported for a silty loam and silty sand soil, respectively(7). Major metabolites of monomethyl chlortoluron(8) and N-demethylated chlortoluron(7) indicate that degradation of chlortoluron proceeds via cleavage of the C-N bond(10). Biodegradation may be slightly attenuated in soils containing higher concentrations of organic matter as sorption may have a protective effect(11). Volatilization of chlortoluron will not be important from moist or dry soil surfaces(SRC) based on an estimated value for its Henry's Law constant(12,13,SRC), and its measured vapor pressure, 3.6X10-8 mm Hg(12), respectively. Half-lives from 4-16 weeks have been determined for chlortoluron in soil(14).|AQUATIC FATE: Based on a recommended classification scheme(1), measured Koc values averaging 150-420(2-4) indicate that chlortoluron may adsorb to suspended solids and sediment(SRC) in the water column. Based on results from soil studies(5-7), biodegradation may be an important fate process for this compound in water(SRC). Half-lives from 4-16 weeks have been determined for chlortoluron in soil(5); monomethyl chlortoluron(6) and N-demethylated chlortoluron(5) were the major metabolites of this process. Chlortoluron should not volatilize from water surfaces(8,SRC) based on an estimated Henry's Law constant of 1.4X10-10 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(9) and water solubility(10). An estimated BCF value of 40(11,SRC), from an experimental log Kow(11), suggests that chlortoluron will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(12).|ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 3.6X10-8 mm Hg at 25 °C(2,SRC) indicates that chlortoluron will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase chlortoluron may be physically removed from the air by wet and dry deposition(SRC).

Water, spiked with chlortoluron at 1 ug/L, was used to measure transport of this compound in groundwater from a sand-gravel aquifer(2). Chlortoluron was not detected at a flow distance of 10 m and a depth of 6 m; at 14 m and 18 m depths chlortoluron had a relative residence time 7 times (retention capacity of 400 ng/kg) and 1.75 times (retention capacity of 50 ng/kg) that of the mean residence time for a conservative tracer(2). A semi-quantitative mass-balance over a 175 day period shows that 70% to 90% of this compound was transported either convectively or dispersively. From 7-10% was adsorbed by sediment and from 2-20%, depending on the depth from the surface, was degraded biologically or abiotically(2).

An estimated BCF value of 40 was calculated for chlortoluron(SRC), using an experimental log Kow of 2.41(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme, this BCF value suggests that bioconcentration in aquatic organisms is moderate, not high(3). Winter wheat grown in soil containing 4.7 mg chlortoluron/kg dry soil had bioconcentration factors of 21 and 22 for root material and for shoots, respectively (bioconcentration factor is the concentration of 14C from the chlortoluron in the plant versus the soil)(4).

104.71 L/kg|An average organic matter-water distribution of 60 was measured for seven soils (organic matter range 1.09-5.92%; pH range 5.9-7.5)(1). Seventeen soils from Australia had a range of organic matter-water distribution values for this compound from 25-85, giving Koc values ranging from 1-3467 (organic matter range 0.19-6.62; pH range 4.8-8.4)(2). Leaching was studied following field application of chlortoluron to a sandy soil; after 10 cm of rain had fallen, >2 mg/kg, 1 mg/kg, 0.5 mg/kg, and a trace remained in the 0-2.5, 2.5-5, 5-7.5, and 7.5-10 cm depth, respectively(2). Chlortoluron has measured Koc values ranging from 146-346 for eight Czechoslovakian soils (mean=228), with higher values corresponding to soils with a greater content of organic matter(3). Koc values of 271 and 419 were measured for a loamy sand and a mucky peat soil, respectively, at 25 °C(4). According to a recommended classification scheme(5), these estimated Koc values suggest that chlortoluron has moderate mobility in soil(SRC). Adsorption of chlortoluron corresponds to an L-isotherm indicating that as the solution concentration increases, there is a decrease in site availability(6). Chlortoluron, applied at a rate of 2.0 kg/ha to sandy soil monoliths containers, had a measured Koc of 160 and 113 in the A and B horizons, respectively(7). The addition of liquid manure, increasing the organic carbon content, resulted in reduced mobility(7).

The Henry's Law constant for chlortoluron is estimated as 1.4X10-10 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 3.6X10-8 mm Hg(1), and water solubility, 70 mg/L(2). This value indicates that chlortoluron will be essentially nonvolatile from water surfaces(3,SRC). Chlortoluron's vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that this compound should not volatilize from either dry or moist soil surfaces, respectively(SRC).

SURFACE WATER: Chlortoluron was detected in the Rhine River, Germany, in water samples obtained during 1990 and 1991 (Range = <0.03-0.21 mg/L, 10 monitoring sites; detection limit = 0.03 mg/L)(1). Chlortoluron was detected in Main River, Germany, water at unreported concentrations(2). Lippe River, Germany, water samples contained chlortoluron with maximum concentrations found in December, 1988(3). Chlortoluron was detected in surface water from The Netherlands at an unreported location and concentration(4). The Rhine River at Cologne, Germany, had a concentration of 0.62 ug/L(4) at an unspecified location. The concentration of chlortoluron was below the detection limit of 0.01 ug/L for all samples in a survey of estuarine water from the Mediterranean(5). An analysis of 677 surface water samples in Germany resulted in 84 samples positive for chlortoluron(6). Chlortoluron was occasionally detected in surface water during a study of 10 clay-based catchments in the UK; the highest concentration recorded was 1.5 ug/L in winter(7).|GROUNDWATER: Chlortoluron was detected in 7% of the groundwater samples in Northrhine-Westphalia in Germany at concentrations equal to or greater than 0.1 ug/L(1). An analysis of 1325 groundwater samples in Germany resulted in 6 samples positive for chlortoluron(2). Chlortoluron was detected in groundwater which feeds the Granta River, UK, at concentrations from <0.13 to 0.35 ug/cu dm (detection limit = 0.13 ug/cu dm)(3).|DRINKING WATER: Chlortoluron was detected in British drinking water at an unreported location and concentration(1).

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

...(TOLYL-(14)C)CHLORTOLURON WAS ADMIN DAILY TO RATS FOR...2 WK...CONCN OF RADIOACTIVITY IN BLOOD & VARIOUS ORGANS REACHED THEIR HIGHEST LEVEL ON 1ST OR 2ND DAY...& DID NOT INCR FOR REMAINDER OF EXPT. ...WHEN FEEDING OF LABEL WAS ABANDONED, RADIOACTIVITY IN ALL TISSUES DECR BELOW DETECTABLE LEVELS WITHIN...9 DAYS.|...PHENYLUREAS LABELED WITH (14)C IN DIFFERENT POSITIONS WERE ADMIN ORALLY TO RATS, IT WAS OBSERVED THAT TOTAL RADIOACTIVITY WAS RAPIDLY & EFFICIENTLY ELIMINATED IN URINE & FECES. ...90% OR MORE OF RADIOACTIVITY APPLIED WAS ACCOUNTED FOR IN EXCRETA WITHIN 72 HR AFTER ADMIN...(TOLYL-(14)C)CHLORTOLURON. WITH MOST MENTIONED CMPD /(TOLYL-(14)C)CHLORTOLURON/ MAJOR PORTION OF LABEL WAS ELIMINATED IN URINE, WHEREAS AMT OF FECAL RADIOACTIVITY WAS USUALLY NO MORE THAN 20% IN TERMS OF DOSE APPLIED.

RECOGNIZED N-DEMETHYLATION &/OR N-DEMETHOXYLATION REACTIONS OF PHENYLUREA HERBICIDES IN BIOLOGICAL ENVIRONMENTS--CHLORTOLURON-- SOIL/MICROBIAL MEDIA: IN SILTY CLAY SOIL; PLANTS: IN WHEAT; MAMMALS: IN RAT /FROM TABLE/|...FATE OF (14)C-TOLYL-LABELED HERBICIDE /CHLORTOLURON/ IN RAT. ...METHYL RING SUBSTITUENT WAS SUBJECTED TO STEPWISE OXIDATION, YIELDING FIRST CORRESPONDING HYDROXYMETHYL AND THEN CARBOXY DERIVATIVE. ... COMBINED N-DEMETHYLATION/SIDE-CHAIN OXIDATION PATHWAY IN RATS IS /SRP: 3-(3-CHLORO-4-HYDROXYMETHYLPHENYL)-1,1-DIMETHYLUREA; 3-(3-CHLORO-4-CARBOXYPHENYL)-1,1-DIMETHYLUREA; 3-(3-CHLORO-4-HYDROXYMETHYLPHENYL)-1-METHYLUREA; 3-(3-CHLORO-4-CARBOXYPHENYL)-1-METHYLUREA; 3-(3-CHLORO-4-HYDROXYMETHYLPHENYL)UREA AND 3-(3-CHLORO-4-CARBOXYPHENYL)UREA/.|THE METABOLISM OF CHLORTOLURON IN WHEAT EXHIBITED ESSENTIALLY THE SAME QUALITATIVE PATTERN OF DEGRADATION. HOWEVER, THE MAJOR PORTION OF THE HYDROXYMETHYL METABOLITE (3-(3-CHLORO-4-HYDROXYMETHYLPHENYL)-1,1-DIMETHYLUREA) WAS FIRST TRAPPED AS WATER-SOL CONJUGATE(S). FURTHER OXIDATION TO CORRESPONDING CARBOXY DERIVATIVE OCCURRED ONLY IN LATER STAGES OF PLANT GROWTH. IN ADDN, N-DEMETHYLATION DID NOT PROCEED BEYOND N-MONOMETHYL STAGE.|The metabolism of chlortoluron was investigated in several plant species. Chlortoluron was degraded via both N-demethylation and ring-methyl oxidation reactions. The latter pathway was the major degradative route in wheat and barley. Since the products of ring-methyl oxidation are nonphytotoxic, the existence of such a detoxification mechanism in these cereals may account for their enhanced resistance to chlortoluron. The major metabolites in the susceptible cereal weeds, Avena fatua, Alopecurus myosuroides and Lolium perenne, and in resistant cotton were products of N-demethylation. This reaction in the cereal weeds proceeded only very slightly beyond the state the mono-N-demethylated metabolites some of which retain considerable phytotoxicity. In cotton, however, N-demethylation was more efficient, giving rise to substantial amounts of N-didemethylated metabolites which are non-phytotoxic.|For more Metabolism/Metabolites (Complete) data for CHLORTOLURON (7 total), please visit the HSDB record page.

Inhibits photosynthesis.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

1. WASH CONTAMINATED SKIN WITH SOAP & WATER. 2. FLUSH CONTAMINATED EYES WITH COPIOUS AMOUNTS OF FRESH WATER FOR 15 MINUTES. 3. INGESTIONS OF SMALL AMOUNTS (LESS THAN 10 MG/KG BODY WEIGHT) OCCURRING LESS THAN AN HOUR BEFORE TREATMENT, ARE PROBABLY BEST TREATED BY: A. SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER. DOSE FOR ADULTS & CHILDREN OVER 12 YEARS: 30 ML. DOSE FOR CHILDREN UNDER 12 YEARS: 15 ML. B. ACTIVATED CHARCOAL: /PRC: 30 G ACTIVATED CHARCOAL IN 3-4 OZ WATER (CHILDREN), 100 G IN 8-10 OZ WATER (ADULT)/...AFTER VOMITING STOPS. C. SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG IN TAP WATER, AS A CATHARTIC. /PESTICIDES OF LOW OR MODERATE TOXICITY/|4. INGESTIONS OF LARGE AMOUNTS (MORE THAN 10 MG/KG) OCCURRING LESS THAN AN HR BEFORE TREATMENT, SHOULD PROBABLY BE TREATED BY GASTRIC LAVAGE: A. INTUBATE STOMACH & ASPIRATE CONTENTS. B. LAVAGE STOMACH WITH SLURRY OF ACTIVATED CHARCOAL.../&/ LEAVE 30-50 G ACTIVATED CHARCOAL IN THE STOMACH BEFORE WITHDRAWING TUBE. C. SODIUM SULFATE, 0.25 G/KG IN TAP WATER, AS A CATHARTIC. CAUTION: HYDROCARBONS (KEROSENE, PETROLEUM DISTILLATES) ARE INCLUDED IN SOME FORMULATIONS OF THESE CHEMICALS. INGESTION OF VERY LARGE AMOUNTS MAY CAUSE CNS DEPRESSION. IN THIS CASE, IPECAC IS CONTRAINDICATED. ALSO, GASTRIC INTUBATION INCURS A RISK OF HYDROCARBON PNEUMONITIS. FOR THIS REASON OBSERVE THE FOLLOWING PRECAUTIONS: (1) IF THE VICTIM IF UNCONSCIOUS OR OBTUNDED & FACILITIES ARE AT HAND, INSERT AN ENDOTRACHEAL TUBE (CUFFED, IF AVAILABLE) PRIOR TO GASTRIC INTUBATION. (2) KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING INTUBATION & LAVAGE /PRC: TAP WATER IN CHILDREN, ISOTONIC SALINE IN ADULTS/ (TRENDELENBURG, OR LEFT LATERAL DECUBITUS, WITH HEAD OF TABLE TIPPED DOWNWARD). KEEP VICTIM'S HEAD TURNED TO THE LEFT. (3) ASPIRATE PHARYNX AS REGULARLY AS POSSIBLE TO REMOVE GAGGED OR VOMITED STOMACH CONTENTS. /PESTICIDES OF LOW OR MODERATE TOXICITY/|5. INGESTIONS OCCURRING MORE THAN AN HR BEFORE TREATMENT ARE PROBABLY BEST TREATED ONLY BY ACTIVATED CHARCOAL /PRC: 30 G ACTIVATED CHARCOAL IN 3-4 OZ WATER (CHILDREN), 100 G IN 8-10 OZ WATER (ADULT)/...& SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG... 6. THERE ARE NO SPECIFIC ANTIDOTES FOR THESE CHEMICALS. BECAUSE MANIFESTATIONS OF TOXICITY DO OCCASIONALLY OCCUR IN PECULIARLY PREDISPOSED INDIVIDUALS, MAINTAIN CONTACT WITH VICTIM FOR AT LEAST 72 HR SO THAT UNEXPECTED ADVERSE EFFECTS CAN BE TREATED PROMPTLY. /PESTICIDES OF LOW OR MODERATE TOXICITY/

chlorotoluron

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Redness.

Dicuran 80 wettable powder (800 g ai/kg) and 500 flowable (500 g/l)|...in combination with mecoprop (Lumeton forte 60 wettable powder)|Chlortoluron is combined with mecoprop to improve the control of Galium, Papaver and Veronica spp.|(Chlortoluron +) bifenox; mecoprop; pendimethalin; terbutryn; trifluralin; terbuthylazine + terbutryn|Suspension concentrate; Wettable powder; Granule

Urea, N'-(3-chloro-4-methylphenyl)-N,N-dimethyl-: ACTIVE|IT WAS INTRODUCED, IN 1969, BY CIBA AG...UNDER CODE NUMBER C2242, TRADE MARK DICURAN & PROTECTED BY BELGIAN PATENT 728267. ITS HERBICIDAL PROPERTIES WERE FIRST DESCRIBED BY L'HERMITE Y ET AL; CR JOURN ETUD HERBIC CONF, COLUMA, 5TH, 1969, II, 349.|IT IS EFFECTIVE BOTH AS RESIDUAL SOIL-ACTING HERBICIDE & AS CONTACT FOLIAR-ACTING SPRAY AGAINST GRASS WEEDS & MANY BROAD-LEAVED WEEDS OF CEREAL CROPS, PARTICULARLY AGAINST BLACK GRASS (ALOPECURUS MYOSUROIDES). IT IS USED ON WINTER CEREALS IMMEDIATELY AFTER SOWING AT 1.5 TO 3 KG AI/HA; FOR POST-EMERGENCE, AT SAME RATES WHEN CEREAL IS AT THE 3-LEAF STAGE TO END OF TILLERING. IT IS COMBINED WITH MECOPROP (LUMETON FORTE) TO IMPROVE THE CONTROL OF GALLIUM, VERONICA & PAPAVER SPP.|Not marketed in the United States.

PRODUCT ANALYSIS /IS BY/ SOLVENT EXTRACTION FOLLOWED BY HYDROLYSIS & TITRATION OF DIMETHYLAMINE.|RESIDUES MAY BE DETERMINED BY HPLC OR BY ALKALINE HYDROLYSIS, DIAZOTIZATION OF THE 3-CHLORO-P-TOLUIDINE WHICH IS EITHER COUPLED WITH N-(1-NAPHTHYL)ETHYLENEDIAMINE & MEASURED COLORIMETRICALLY OR DETERMINED BY GLC AFTER CONVERSION TO A VOLATILE DERIVATIVE.|THIN LAYER CHROMATOGRAPHY /FOR DETERMINATION OF CHLOROTOLURON IN PESTICIDE FORMULATIONS/.|Urea and carbamate herbicides were determined by high-pressure liquid chromatography with a wall jet electrode for electrochemical detection.|For more Analytic Laboratory Methods (Complete) data for CHLORTOLURON (12 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|Pharmaceuticals|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Chlorotoluron has known environmental transformation products that include Chlorotoluron benzoic acid (CGA 15140).