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Home > Encyclopedia > Linuron

Linuron

Linuron structure

Linuron 

structure
  • CAS No:

    330-55-2

  • Formula:

    C9H10Cl2N2O2

  • Chemical Name:

    Linuron

  • Synonyms:

    Urea,N′-(3,4-dichlorophenyl)-N-methoxy-N-methyl-;Urea,3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-;N′-(3,4-Dichlorophenyl)-N-methoxy-N-methylurea;Afalon;Afalon inuron;3-(3,4-Dichlorophenyl)-1-methoxy-1-methylurea;N-(3,4-Dichlorophenyl)-N′-methyl-N′-methoxyurea;Du Pont 326;Herbicide 326;Lorox;1-Methoxy-1-methyl-3-(3,4-dichlorophenyl)urea;Sinuron;Aphalon;Linuron;Cephalon;N-(3,4-Dichlorophenyl)-N′-methoxy-N′-methylurea;1-(3,4-Dichlorophenyl)-3-methoxy-3-methylurea;3-(3,4-Dichlorophenyl)-1-methyl-1-methoxyurea;Lorex;Du Pont Herbicide 326;Methoxydiuron;3-(3′,4′-Dichlorophenyl)-1-methoxy-1-methylurea;Sarclex;Alfalone;Alfalon;Linurex;Linex;Liron;Afalon Dys. 450SC;Galolin Mono;Linex (herbicide);Afalon 450 SC;56645-87-5

  • Categories:

    Agrochemicals  >  Herbicides

Description

White crystalline solid or powder. Odorless. Commercial product may be available a water soluble or emulsifiable concentrate.


Linuron appears as colorless crystals. Non corrosive. Used as an herbicide.|COLOURLESS CRYSTALS.


Linuron appears as colorless crystals. Non corrosive. Used as an herbicide.|Linuron is a member of the class of phenylureas that is N-methyl urea substituted by a methoxy group at position 1 and a 3,4-dichlorophenyl group at position 3. It has a role as a xenobiotic, an environmental contaminant, a herbicide and an agrochemical. It is a dichlorobenzene and a member of phenylureas. It derives from a N-methyl urea.|A selective pre- and post-emergence herbicide. (From Merck Index, 11th ed)

Linuron Basic Attributes

249.09

249.09

206-356-5

01XP1SU59O

1300

3077|2588

DTXSID2024163

White crystalline solid|Colorless crystals|Fine flakes or coarse powder

2928000032

Characteristics

41.6

3.2

White Crystalline Solid

1.49 g/cm3 @ Temp: 20 °C

93-94 °C

180-190°C

11 °C

1.556

H2O: 0.0075 g/100 mL

APPROX 4°C

Vapour pressure, Pa at 24°C: 0.002

Oral-Rat LD50: 1146 mg/kg; Oral-Mouse LD50: 2400 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

ODORLESS

Henry's Law constant= 1.97X10-9 atm-cu m/mol @ 25 °C

149.63 Ų [M+H]+ [CCS Type: TW]|152.6 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated]|151.01 Ų [M+H]+

Hydrolyzed slowly by acids and bases.

Amides and Imides

A urea derivative.

Non-corrosive

Safety Information

UN 3077

3

61-22-40-48/22-50/53-62-39/23/24/25-23/24/25-11

53-45-60-61-36/37-16-7

YS9100000

T;N,N,T,F

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

Hydrolyzed slowly by acids and alkalis at normal temperatures, and more rapidly at higher temperatures.

P201-P273-P281-P308 + P313-P501

H302-H351-H360Df-H373-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.|Linuron should be incinerated in a unit operating at 850 °C equipped with offgas scrubbing equipment. ... Recommendable methods: Incineration.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)|Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P273, P281, P301+P312, P308+P313, P314, P330, P391, P405, and P501|Warning|P260, P264, P270, P301+P312, P314, P330, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)|Use water spray, powder, foam, carbon dioxide.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

AVOID BREATHING DUST OR SPRAY MIST. AVOID CONTACT WITH SKIN, EYES, & CLOTHING.|Wash contaminated clothing with soap & hot water before re-use.|Avoid contact with skin, eyes, and clothing. ... Keep out of lakes, streams, or ponds.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

MAY IRRITATE EYES, NOSE, THROAT, & SKIN.

Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: self-contained breathing apparatus.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

The substance may have effects on the blood. This may result in anaemia.

NO open flames.

PREVENT DISPERSION OF DUST! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN!

Use local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

Runoff was collected after each rainfall or series of rainfalls from test plots (silty clay loam graded to a slope of 0.2%) planted with soybeans in the 2 to 4 month period following treatment with linuron as a preemergence herbicide. Concns of linuron in runoff in three years were: trace - 28 ppb, trace - 14 ppb, and trace - 124 ppb (trace = <10 ppb), respectively(1).

In a 1989 survey of 12 vegetable farms, four with each of 3 soil types in British Columbia, Canada, linuron was detected in 3 of 4 muck farms at levels ranging from 331-1260 ppb (dry wt), but it was not detected in farms with loamy sand or silt loam soil (DL 10 ppb)(1). While linuron is used on corn and soybean fields bordering the Chesapeake Bay and its tributaries, including one drainage basin in which an estimated 45,000 kg of linuron was applied, <10 ppb of linuron was found in 79 mud samples in tributaries of Chesapeake Bay during two successive summers(2). The concns of linuron taken from two soybean fields bordering one tributary, on which 0.55 kg/ha of linuron was applied between mid-May and mid-June, were 41 pb in July and <10 and 14 ppb in September(2).

Toxicity

moderately toxic

LD50 Rabbit percutaneous greater than 5000 mg ai (as 50% wettable powder)/kg|LD50 Rat female oral 4000 mg/kg in starch mucilage /Technical linuron/|LC50 Rat inhalation >4.06 mg/l air/4 hr|LD50 Rabbit oral 2250 mg/kg|For more Non-Human Toxicity Values (Complete) data for LINURON (11 total), please visit the HSDB record page.

Linuron's use as an herbicide(1) is expected to result in its direct release to the environment(SRC). In 1992, 1,974,832 pounds of linuron were applied to soybeans, cotton, potatoes, carrots, asparagus, and celery(3).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value ranging from 555 to 987(2), indicates that linuron is expected to have low mobility in soil(SRC). Volatilization of linuron from moist soil surfaces is not expected to be an important fate process(SRC) given an experimental Henry's Law constant of 1.97X10-9 atm-cu m/mol(3). Linuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1.43X10-6 mmHg(4). The dissipation of linuron was followed in field plots planted with potatoes and treated at 1 and 2 kg/ha(5). The disappearance of linuron was very fast and followed first-order kinetics with a half-life of 25 and 22 days, respectively, at the two application rates. After about 75 days, the residual concentration of linuron in the soil was constant, suggesting that a small amount of linuron is strongly absorbed to soil colloids and not available to microbial attack(5). Most evidence indicates that linuron's loss in soil is due to biodegradation(6). For example linuron, at 4 ppm, degraded with half-lives of 22-86 days when incubated at 25 °C in 18 mineral soils(7). Photolysis of linuron on surface soils may also be an important degradation pathway. Phenyl-labeled C-14 linuron degraded with a half-life >15 days on silt loam soil irradiated continuously with a Pyrex glass filtered xenon arc light at 25 deg(8). After 15 days of irradiation, the soil contained 78.8% of the recovered radioactivity as parent linuron.|TERRESTRIAL FATE: The half-life of linuron in cropped fields was 8-25 weeks; residues were undetectable after 6 mo(1-2). No progressive buildup was observed after repeated treatment(1-2). Four weeks after a half normal, normal, and double normal spray of linuron in May on corn, carrots, bean and potato crops planted in loamy soil, an average of 40% of the applied dose was recovered(3). After 3 months, only 25% of the linuron was recovered(3). At the end of the winter months, <0.4% of the linuron was recovered(3). In Greenhouse experiments linuron's persistence was 25-60 weeks(3). In test field plots in a vegetable growing area of Ontario, 64% of linuron had dissipated in 5 months from the organic soil (92% organic matter)(4). It was concluded that linuron residues did not accumulate in soil in vegetable farms of area growers(4).|AQUATIC FATE: Based on a classification scheme(1), an experimental Koc value ranging from 555 to 987(2), indicates that linuron is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.97X10-9 atm-cu m/mole(4). According to a classification scheme(5), a BCF ranging from 13 to 49(6,7), suggests the potential for bioconcentration in aquatic organisms is low to moderate. Hydrolysis of linuron is not expected to occur in water except at high alkaline conditions (pH> 9)(8). There was no evidence of hydrolysis products after 4 months in buffered solutions at pH 5, 7, and 9(8). Biodegradation of linuron in surface waters appears to be site specific. Although linuron did not biodegrade when incubated with river water and sewage for 4 months(8), when it was applied as an emulsifiable formulation to ditch water, it degraded with half-lives ranging from 7.2 to 11.8 days during the stagnant period (1 week), and an average half-life of 3.8 days during the flow period (3 weeks)(9). Disappearance of linuron was slower in the higher treatment rate ditches, and in those studied during lower temperature periods(9). Photolysis of linuron is expected to occur in surface waters. In one experiment, 43% of linuron exposed to sunlight outdoors was photolyzed in 24 days(8). After 1 ppm of linuron was added to each of three 1 cu m outdoor ecosystems, linuron concns in the water columns declined exponentially over the 42-day experiment; the calculated half-lives ranged from 16 to 42 days(10). The half-life of linuron in Lake Balatan (Hungary) water was 10 weeks(11).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semi-volatile organic compounds in the atmosphere(1), linuron, which has a vapor pressure of 1.43X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phase in the ambient atmosphere. Vapor-phase linuron is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 12 hours(SRC), calculated from its rate constant of 1.0X10-11 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3). Particulate-phase linuron may be removed from the air by wet and dry deposition(SRC). Linuron may undergo photolysis in air based upon its absorption maximas at 210, 245, and 280 nm with some overlap at > 290 nm(4). The rate of photolysis in the environment appears to be slow. Phenyl-labeled C-14 linuron degraded with a half-life > 30 days in sterile aqueous pH 5 buffer solution irradiated with natural sunlight at 25 °C(4).

AFTER EXPOSURE TO SUNLIGHT FOR SEVERAL MO, LINURON YIELDED 3,4-DICHLOROPHENYLUREA, DE-METHOXY LINURON & 3-(3-CHLORO-4-HYDROXYPHENYL)-1-METHOXY-1-METHYLUREA ... .|... LINURON /WAS SUBMITTED/ ... TO HIGH TEMP TREATMENTS IN ... AQ SLURRIES OF SOILS & CLAY COLLOIDS. VELOCITY CONSTANTS OF DECOMP REACTIONS ... AT 85, 95, & 107 °F WERE EXTRAPOLATED TO 20 °C. HALF-LIVES EST FOR ... LINURON AT THIS TEMP WERE OF ORDER OF 10-70 YR.|... LOSSES BY PHOTODECOMPOSITION ... PROBABLY ARE INSIGNIFICANT EXCEPT WHEN LINURON IS EXPOSED ON THE SOIL SURFACE FOR SEVERAL DAYS OR WK UNDER HOT, DRY CONDITIONS.|The 4-halogen substituent was replaced by hydroxyl when linuron and monuron were exposed to sunlight in aqueous solutions; demethylation also occured.|For more Environmental Abiotic Degradation (Complete) data for LINURON (7 total), please visit the HSDB record page.

17.78|Linuron residues accumulated in bluegill fish during 28 days of exposure to water treated at 0.1 and 1.0 ppm [C14] linuron(1). Maximum bioconcentration factors were 49 for whole fish, 34 for a muscle and 39 for carcass tissues. After 28 days of exposure, linuron residues in the viscera were identified as desmethyl linuron, norlinuron, and glucuronide conjugates. The edible tissues were not analyzed for linuron residues. Residues rapidly declined to approximately 10% of maximum levels after the 14-day depuration period(1). In one bioaccumulation study, orange-red killifish were exposed to 0.02 to 0.2 mg/l of linuron for 28 days(2). At the end of the experiment, the BCF of linuron in the fish ranged from 13 to 23. According to a classification scheme(3), BCF values ranging from 13 to 49 suggest the potential for bioconcentration in aquatic organisms ranges from low to moderate.

501.19 L/kg|ADSORPTION INCR AS CLAY CONTENT &/OR ORG MATTER CONTENT OF SOIL INCR; CLAYS OF HIGH /CATION/ EXCHANGE CAPACITY ABSORB MORE LINURON THAN THOSE OF LOW EXCHANGE CAPACITY. ... LEACHING IS NOT BELIEVED TO BE AN IMPORTANT FACTOR IN DISAPPEARANCE FROM MOST SOILS.|Linuron adsorbs strongly to soil; adsorption increases with the organic carbon content of the soil(6-7). The Freundlich K for a sandy loam soil (1.45% OC, pH 7.3) was 30.0(1). The Koc at 1 ug/ml is 2,070 (1). In six soils the Freundlich K varied from 35.0 in a sandy clay loam soil to 315 in a light peat soil(2). The individual Freundlich 1/n values were not reported; however, the average 1/n was 0.75(2). For a concn of 1 ug/ml, the Koc's ranged from 538 to 2440. There was no correlation between adsorption and clay content of the soil or cation exchange capacity. The distribution coefficients of linuron in 18 mineral soils ranged from 4.20 to 21.70; the corresponding Koc's were 555-987(5). The mean Koc for 17 Australian soils was 319, with a range of 114 to 519(4). The Koc values for 12 sediments ranged from 362 to 877(3). Adsorption and desorption of linuron to sediment is rapid(3).|In a sandy soil with a Koc of 519 after 10 cm of rain had fallen, all linuron remained in the upper 2.5 cm(1). Leaching of linuron into deeper soil levels has been found to be relatively insignificant(2). In a soil column experiment designed to simulate field conditions and a seasonal rainfall of 600 mm, 98% of linuron remained in the upper 1 cm(3). The upper section of the soil contained 500 mg/kg(3). In a field study, some linuron did leach into the 2-4 cm soil layer of soil; results were not conclusive due to variability of residues in core samples(4). Many studies have shown that after spraying linuron, residues are most commonly found in the top 5 cm, and generally not deeper than 10 cm(5). The mean adsorption of linuron to 10 New Jersey soils taken from the A horizon was 1,498 and 2,964 ug/100 g of soil loadings of 500 ug/100 ml and 1,000 ug/100 ml, respectively(6). Adsorption to B horizon soils were lower, underscoring the importance of organic matter for adsorption.

The Henry's Law constant for linuron is 1.97X10-9 atm-cu m/mole(1). This Henry's Law constant indicates that linuron is expected to be essentially nonvolatile from water surfaces and moist soils(2). Linuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1.43X10-6(3).

GROUNDWATER: In a British study in which 700 samples of rivers, reservoirs and groundwaters were analyzed, linuron was not detected in any groundwater (detection limit of 0.2 ug/l)(1). In a survey of 201 rural wells in 8 agricultural areas of Missouri, linuron was found in 2 wells at 1.8 and 1.9 ppb(2). These wells were located in areas planted with soybeans. Sampling was performed in December. In a 1986-1987 study of 179 farm wells in Ontario with suspected contamination, 28 wells contained linuron above the 0.1 ppb detection limit(3). According to EPA's Pesticides in Groundwater database, linuron has been found only in Wisconsin groundwater; the contamination was judged to result from normal agricultural use(4). The concn median and maximum were 1.9 and 2.7 ppb, respectively(4).|SURFACE WATER: The concn of linuron was monitored at 7 stations on Lake Erie tributaries draining agricultural watersheds from 1983 to 1991, during which time over 4000 samples were analyzed(1). The maximum and 95th percentile linuron concns at these stations ranged from 1.36-24.77 ppb and 0.27-2.07 ppb, respectively(1). The time-weighted average and flow-weighted average concns ranged from 0.04-0.17 ppb and 0.00-0.20 ppb(1). Twenty five water samples taken from 4 Michigan rivers during runoff season, from April to September 1985, and analyzed for linuron were above the detection limit and linuron levels ranged from 0.146-2.813 ppb(2). While linuron is used on corn and soybean fields bordering Chesapeake Bay and its tributaries, including one in which an estimated 45,000 kg of linuron drains into the discharge basin, <0.2 ppb of linuron was found in 79 water samples from tributaries of Chesapeake Bay during two successive summers(3). A farm pond in Ontario contained 12 ppb of linuron that was attributed to runoff(4).|GROUNDWATER: In a study conducted in Missouri, linuron was detected in groundwater in rural agricultural wells at levels ranging from 0.48 to 0.9 ug/l(1). Monitoring wells in Wisconsin located in areas that were highly vulnerable to groundwater contamination, were also analyzed for linuron(1). At one site, concentrations ranged from 1.3 to 2.7 ug/l. In a 1986-1987 study, linuron was detected in 28 of 179 farm wells with suspected contamination in Ontario, at concentrations above the 0.1 ppb detection limit(2). Eight monitoring wells and 4 household wells were sampled for a suite of pesticides including linuron(1). There were no indications of point source contamination or problems with the wells during the study. Linuron was detected in 50% of the monitoring wells (4 of 8 wells) with levels ranging from 0.35 to 1.31 ug/l(1).|SURFACE WATER: Linuron was monitored in 4000 samples collected at 7 stations on Lake Erie tributaries draining agricultural watersheds from 1983 to 1991(1). The maximum and 95th percentile linuron concns at these stations were respective ranges of 1.36-24.77 ppb and 0.27-2.07 ppb(1). The time-weighted average and flow-weighted average concns were respective ranges of 0.04-0.17 ppb and not detected-0.20 ppb(1). Linuron was detected in 25 water samples taken from 4 Michigan rivers during runoff season (from April to September 1985) at concns of 0.146-2.813 ppb(2). Linuron was detected in a farm pond in Ontario at a concn of 12 ppb; the presence of linuron in the pond was attributed to runoff(3). The USGS sampled 8 widely spread locations within the Mississippi Basin at frequent intervals from April 1991 to April 1992(4). Linuron was detected at a concentration of approximately 0.1 ug/l in one of the 46 samples collected from the White River. Linuron was not detected above the detection limit of 0.01 ug/l in any of the samples collected from the other 7 locations(4).

Of the 1044 composites analyzed in the FDA Adult Total Diet Study in FY1978-82, 19 contained linuron(1). In the FY1978-82 FDA'S Adult Total Diet Study Survey, the mean concn of linuron in root vegetable composites was 0.0089 ppm(2). Linuron dietary intakes estimated from the July 1986-April 1991 FDA Total Diet Study were 0.0018 ug/kg body wgt/day for a 6-11 month old; 0.0024 ug/kg body wgt/day for 2 yr old; and ranged from 0.0005 to 0.0008 ug/kg body wgt/day for respective groups of 14-16 yr, 25-30 yr, and 60-65 yr males and females (3). In a pesticide screening survey of 6970 produce samples, linuron was detected in 226 carrot samples (detection limit = 0.2 ppm); all of the samples containing linuron were carrots(4). Of the 6,568 samples of domestic food and feed the FDA analyzed between 1982 and 1986, 30 (29 of them carrots) contained linuron with levels up to 0.5 ppm(5). None of the 13,283 imported agricultural commodities tested contained linuron(5). No linuron residues (detection limit = 0.1 ppm) were found in 13 potatoes from farms in NJ, 9 from FL, and 3 from CA(6). In a 1994 surveillance study of domestic food samples collected from the U.S. and Puerto Rico, and import food samples from 101 countries, in which 329 pesticides were monitored and only 94 were found, linuron was detected in an unspecified number of samples(7).

Occupational exposure to linuron may occur through inhalation and dermal contact with this compound at workplaces where linuron is produced or used, or by dermal contact with soil and vegetation that were sprayed with linuron(1). Monitoring data indicate that the general population may be exposed to linuron via ingestion of vegetables, primarily carrots (2,SRC).

Drug Information

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.)

IN CHRONIC TOXICITY STUDIES ... LINURON ... CONTINUOUSLY FED TO RATS & DOGS FOR ... TWO YR AT DIETARY LEVELS ... FROM 25 TO 2500 PPM ... TOTAL ANILINE-CONTAINING RESIDUES IN BLOOD & ... (MUSCLE, FAT, LIVER, KIDNEY, SPLEEN) WERE A FEW TO 100 PPM. ... RESIDUES REPRESENTED ONLY MINUTE FRACTION OF ... HERBICIDE INGESTED BY ANIMALS.|LINURON IS MOST READILY ABSORBED THROUGH THE ROOT SYSTEM; LESS SO THROUGH FOLIAGE & STEMS. HOWEVER, FOLIAR ABSORPTION ... IS SIGNIFICANTLY GREATER THAN THAT OF DIURON, MONURON, OR FENURON. ... TRANSLOCATION IS PRIMARILY UPWARD IN THE XYLEM.|... RESIDUE DATA ... OBTAINED IN SHORT TERM ELIMINATION EXPERIMENTS ... . AMT OFRADIOACTIVITY WHICH PERSISTED IN BLOOD & DIFFERENT TISSUES AT END OF 72 HR ... PERIODS WERE NO MORE & USUALLY MUCH LESS THAN 1% OF DOSE APPLIED.

... LINURON-INDUCIBLE ENZYME WAS OBTAINED FROM BACILLUS SPHAERICUS. THIS ACYLAMIDASE DEGRADED LINURON BY HYDROLYSIS OF AMIDE BOND WITH ... RELEASE OF CARBON DIOXIDE & N,O-DIMETHYL HYDROXYLAMINE. ... ENZYME WAS SPECIFIC FOR METHOXY-SUBSTITUTED PHENYLUREAS & DID NOT HYDROLYZE 1,1-DIMETHYL PHENYLUREAS ... .|IN GREENHOUSE STUDIES, LINURON ENTERED CORN (ZEA MAYS L), SOYBEAN (GLYCINE MAX L) & CRABGRASS (DIGITARIA SANGUINALIS L) WITH ABSORBED WATER. DEMETHYL LINURON & 3,4-DICHLORO-ANILINE WERE FOUND IN TISSUES. ... SOME LINURON BOUND WITHIN PLANT ... .|LINURON ... FED TO ALBINO RATS. URINE ... ANALYZED FOR METABOLITES /&/ N-(3,4-DICHLOROPHENYL)UREA, N-(3,4-DICHLOROPHENYL)-N'-METHYLUREA & 3,4-DICHLOROANILINE WERE FOUND FREE. N-(2-HYDROXY-4,5-DICHLOROPHENYL)-N'-METHYLUREA, N-(5-HYDROXY-3,4-DICHLOROPHENYL)UREA & 6-ACETAMIDO-2,3-DICHLOROPHENOL ... /WERE IDENTIFIED/ AS GLUCURONIDES OR SULFATES.|In rats linuron is metabolized by demethoxylation followed by hydroxylation of the benzene ring. Major urinary metabolites are urea derivatives; no unchanged linuron could be demonstrated. Only trace amounts of 3,4-dichloroaniline were found. If metabolism to dichloroaniline is major pathway in humans, ... methemoglobinemia should be anticipated after toxic doses.|For more Metabolism/Metabolites (Complete) data for LINURON (9 total), please visit the HSDB record page.

0.11 Days

Inhibits photosynthesis.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)|Carcinogens, Teratogens

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)


Fresh air, rest.


Rinse skin with plenty of water or shower.


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

1. SKIN CONTAMINATION SHOULD BE REMOVED PROMPTLY BY WASHING WITH SOAP AND WATER. CONTAMINATION OF THE EYES SHOULD BE TREATED IMMEDIATELY BY PROLONGED FLUSHING OF THE EYES WITH COPIOUS AMOUNTS OF CLEAN WATER. IF DERMAL OR OCULAR IRRITATION PERSISTS, MEDICAL ATTENTION SHOULD BE OBTAINED WITHOUT DELAY. /OTHER HERBICIDES/|2. INGESTIONS OF THESE HERBICIDES ARE LIKELY TO BE FOLLOWED BY VOMITING AND DIARRHEA DUE TO THE IRRITANT PROPERTIES OF MOST OF THE TOXICANTS. ... A. IF LARGE AMOUNTS OF HERBICIDE HAVE BEEN INGESTED, AND IF THE PATIENT IS FULLY ALERT, INDUCE EMESIS WITH SYRUP OF IPECAC, FOLLOWED BY SEVERAL GLASSES OF WATER. DOSAGE FOR ADULTS AND CHILDREN OVER 12 YEARS: 30 ML; DOSAGE FOR CHILDREN UNDER 12 YEARS 15 ML. WHEN VOMITING HAS STOPPED, GIVE ACTIVATED CHARCOAL. ADD SORBITOL TO THE CHARCOAL SLURRY UNLESS DIARRHEA HAS ALREADY COMMENCED. IF, FOR SOME REASON, THE PATIENT IS NOT FULLY ALERT, PUT IN PLACE A CUFFED ENDOTRACHEAL TUBE TO PROTECT THE AIRWAY, THEN ASPIRATE AND LAVAGE THE STOMACH WITH A SLURRY OF ACTIVATED CHARCOAL. LEAVE A QUANTITY OF CHARCOAL, WITH SORBITOL, IN THE STOMACH BEFORE WITHDRAWING THE STOMACH TUBE. REPEATED ADMINISTRATION OF CHARCOAL AT HALF OR MORE THE INITIAL DOSAGE EVERY 2-4 HOURS MAY BE BENEFICIAL. /OTHER HERBICIDES/|2. B. IF THE AMOUNT OF INGESTED HERBICIDES WAS SMALL, IF EFFECTIVE EMESIS HAS ALREADY OCCURRED, OR IF TREATMENT IS DELAYED, ADMINISTER THE ACTIVATED CHARCOAL AND SORBITOL BY MOUTH. C. IF SERIOUS DEHYDRATION AND ELECTROLYTE DEPLETION HAVE OCCURRED AS A RESULT OF VOMITING AND DIARRHEA, MONITOR BLOOD ELECTROLYTES AND AND FLUID BALANCE AND ADMINISTER INTRAVENOUS INFUSIONS OF GLUCOSE, NORMAL SALINE RINGER'S SOLUTION, OR RINGER'S LACTATE TO RESTORE EXTRACELLULAR FLUID VOLUME AND ELECTROLYTES. FOLLOW THIS WITH ORAL NUTRIENTS AS SOON AS FLUIDS CAN BE RETAINED. FLUIDS SERVE TO SUPPORT EXCRETION OF THE TOXICANTS. D. SUPPORTIVE MEASURES ARE ORDINARILY SUFFICIENT FOR SUCCESSFUL MANAGEMENT OF EXCESSIVE EXPOSURES TO THESE HERBICIDES. /OTHER HERBICIDES/

SUBSTITUTED UREAS ARE CHARACTERISTICALLY HIGHLY STABLE, NONVOLATILE, NONCORROSIVE, OF LOW MAMMALIAN TOXICITY, PRESENT NO DRIFT HAZARD ... /&/ CAN BE CONSIDERED AS NONHAZARDOUS TO HUMANS, ... . /SUBSTITUTED UREA HERBICIDES/|The herbicides atrazine and linuron, ... were tested alone and in combination, both in vivo and in vitro, to determine their individual and combined genotoxic effects. Human lymphocytes exposed in vitro to either 1 ug/ml linuron or 0.001 ug/ml atrazine showed little chromosome damage, whereas significant chromosome damage was observed in lymphocytes simultaneously exposed to 0.5 ug/ml linuron and 0.0005 ug/ml atrazine, suggesting at least an additive model. ...|MAY IRRITATE EYES, NOSE, THROAT, & SKIN.

Afalon

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

Linuron Use and Manufacturing

Methods of Manufacturing

The reaction of 3, 4-dichlorobenzene isocyanate with hydroxylamine sulfate produces 3, 4-dichlorobenzene hydroxyurea, which is then reacted with dimethyl sulfate to produce Rigulone. 1.3 Preparation of 4, 4-dichlorobenzene hydroxyurea 3, 4-dichlorobenzene isocyanate-toluene solution, hydroxylamine sulfate aqueous solution and sodium hydroxide solution were pumped into each metering tank according to the calculated amount. Add water and hydroxylamine sulfate to the glass-lined reaction pot at the same time, stir and cool, and start to add sodium hydroxide solution dropwise at about 20℃. After about 1 hour, the temperature is controlled at about 20℃, and the pH is between 7.5-7.9 ( Otherwise, add sodium hydroxide or hydroxylamine sulfate). Then, the dropwise addition of 3, 4-dichlorobenzene isocyanate-toluene solution was performed. At this time, the temperature was controlled at 30±2°C, and the dropping was completed within about 1.5 hours, and the reaction was continued at this temperature for 2 hours. After standing for 2h, the upper layer of toluene clear solution was withdrawn. The lower layer material is stirred with water and then centrifuged to obtain a solid wet product 3, 4-dichlorophenylhydroxyurea. The yield is 87%. 2. Preparation of Ligurone Add the above wet hydroxyurea to the sloped glass reactor, then add the calculated amount of dimethyl sulfate and stir for 20min. 20% sodium hydroxide solution was added dropwise, the temperature was controlled at 20-30°C, and the addition was completed within about 1.5 hours. The reaction is carried out at about 30°C for 2h until pH 7 is the end point of the reaction. If it is acidic, sodium hydroxide can be added appropriately. After the reaction is completed, water is added, stirred, filtered and dried to obtain Ligulong original powder. The yield is 90%.

Uses

Herbicide.

In 1992, 1,974,832 pounds of linuron were applied to soybeans, cotton, potatoes, carrots, asparagus, and celery. Approximately 80% of linuron was used on soybeans, 11% on cotton, 4% on potatoes, 4% on carrots, < 1% on asparagus, and < 1% on celery.

USEPA/OPP Pesticide Code 035506; Trade Names: Lorox; Afalon; Linorox; h 326; Linex 4L; Linex 50% DF; Cephalon; Dupont 326; lorox L; Garnitan; Hoe 2810; Linurex; lorox DF; Premalin; Sarclex.|Dry flowable, flowable, water dispersible granule, wettable powder. Trifluron* Twin Pack: emulsifiable concentrate and suspension concentrate|LIQ FORMULATIONS & MIXTURES WITH OTHER HERBICIDES, EG LENACIL, MONOLINURON ... METOXURON, /CHLORPROPHAM, CYANAZINE, POTABLAN S (200 G MONALIDE + 50 G LINURON/L), TRIETAZINE (A WETTABLE POWDER), & TRINULAN OR CHANDOR (240 G TRIFLURALIN + 120 G LINURON/L)/ ARE ALSO AVAIL.|Mixtures include: (linuron +) alachlor; atrazine; chlorpropham; cyanazine; ioxynil; lenacil; metribuzin; monolinuron; propachlor; trietazine; trifluralin; terbutryn; terbacil; amitrole; nitralin; metoxuron; monalide; bromoxynil + ioxynil + mecoprop; bromoxynil + ioxynil + dichlorprop; trietazine + trifluralin; butralin; pendimethalin; simazine.|For more Formulations/Preparations (Complete) data for LINURON (8 total), please visit the HSDB record page.

Urea, N'-(3,4-dichlorophenyl)-N-methoxy-N-methyl-: ACTIVE|... Compatible with most other herbicides with which they might be mixed. Certain ester formulations of hormone weed killers may create a physical problem in the spray tank.|... RECOMMENDED FOR PRE-EMERGENCE USE ON SOYBEANS AT 0.5 TO 2.5 KG AI/HA, COTTON(LAY-BY) AT 0.5 TO 1.5 KG AI/HA, ON POTATOES AT 0.5 TO 2.0 KG AI/HA, ON MAIZE, BEANS & PEAS AT 0.75 TO 1.0 KG AI/HA, ON ASPARAGUS AT 1.0 TO 1.5 KG AI/HA; FOR PRE- & POST-EMERGENCE USE ON CARROTS & WINTER WHEAT AT 0.5 TO 1.0 KG AI/HA.|... USED FOR SHORT TERM CONTROL OF ANNUAL WEEDS IN NONCROP AREAS SUCH AS ROADSIDES & FENCE ROWS.

ELECTRON AFFINITY RESIDUE DETERMINATION BY DIRECT HYDROLYSIS & BROMINATION; COLORIMETRIC DETERMINATION IN PRODUCE.|TLC SEPARATION OF LINURON & SOME OF ITS KNOWN OR SUSPECTED SOIL METABOLITES.|Product analysis is by hydrolysis to 2,4-dichloroaniline ... which is measured colorimetrically, or by non-aqueous titration with perchloric acid. Residues may be detemined by HPLC or GLC.|Product analysis is hydrolysis, followed by titration with perchloric acid in glacial acetic acid; by HPLC; by IR spectroscopy; or by UV spectroscopy. Residueanalysis is by alkaline hydrolysis to 3,4-dichloroaniline, and colorimetric determination of a derivative, or by GLC with ECD.|For more Analytic Laboratory Methods (Complete) data for LINURON (7 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|Health Hazards -> Carcinogens, Teratogens|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)|HERBICIDES

Linuron has known environmental transformation products that include 3,4-dichloroaniline, Desmethoxy-linuron , Desmethyl-linuron , Maleic acid, Maleic hydrazide, Maleimide, Norlinuron , and Succinic acid.

Computed Properties

Molecular Weight:249.09
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:248.0119330
Monoisotopic Mass:248.0119330
Topological Polar Surface Area:41.6
Heavy Atom Count:15
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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