147150-35-4CCOc1nc(F)cc2nc(S(=O)(=O)Nc3c(Cl)cccc3C(=O)OC)nn12BIKACRYIQSLICJ-UHFFFAOYSA-NCloransulam-methyl is the methyl ester of cloransulam. An inhibitor of acetohydroxyacid synthase (AHAS), it prevents the synthesis of amino acids in plants and is used as a herbicide for the control of post-emergence control of broad-leaved weeds in soybeans. It is not approved for use within the European Area. It has a role as an EC 2.2.1.6 (acetolactate synthase) inhibitor, a herbicide and an agrochemical. It is a methyl ester, a sulfonamide, an organofluorine compound, a member of triazolopyrimidines and a member of monochlorobenzenes. It is functionally related to a cloransulam.
In water, 3 ppm (pH 5),184 ppm (pH 7) at 25 °C
In water (25 °C) = 3430 mg/L (pH 9)
Solubility (all in mg/L): acetone 4360; acetonitrile 550; dichloromethane 3980; ethyl acetate 980; methanol 470; hexane <10; octanol <10; toluene 14
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
This chemical does not meet GHS hazard criteria for 4.3% (3 of 69) of reports.
Warning
H332 (55.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P261, P271, P273, P304+P340, P317, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
USEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Cloransulam-methyl, Reason for Issuance: Conditional Registration (October 29, 1997).[Available from, as of October 11, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]
Tolerances are established for residues of the herbicide, cloransulam-methyl, N-(2-carboxymethyl-6-chlorophenyl)-5-ethoxy-7-fluoro-(1,2,4)-triazolo[1,5c]-pyrimidine-2-sulfonamide, plus its acid, cloransulam, calculated as parent ester in or on the following raw agricultural commodities:[Table#6603]
... Studies were conducted with (14)C-radiolabeled cloransulam-methyl in the F344 rat using dose levels of 5 or 1000 mg/kg. At 5 mg/kg, over 90% of either a single dose or repeated (15 days doses was absorbed. At 1000 mg/kg, only 28-30% of a single dose was absorbed. Urinary elimination was rapid in both cases with half-lives of approximately 6-9 hr.
Metabolism studies were conducted with (14)C-radiolabeled cloransulam-methyl in the F344 rat using dose levels of 5 or 1000 mg/kg. At 5 mg/kg, over 90% of either a single dose or repeated (15 days) doses was absorbed... Analyses of urine and fecal extracts indicated that parent cloransulam-methyl accounted for the majority of the excreted radiolabeled material. The only metabolite present at amounts greater than 5% was identified as the 4-OH phenyl derivative of cloransulam-methyl. Other minor metabolites included a hydroxylation of the pyrimidine ring, though the position of hydroxylation was not identified, and an N-acetyl cysteine conjugate of the parent material. Due to rapid elimination , cloransulam-methyl has little potential to accumulate upon repeated administration.
A rat metabolism study showed that radio labeled cloransulam-methyl was excreted mainly via urine in females & urine & feces in males. Less than 0.1% of admin dose was found in any tissue at 72 hr post-dose.
Two lactating goats were given a daily oral dose of either (UL-aniline-(14)C; AN) or (triazolopyrimidine-7,9-(14)C; TP)-cloransulam-methyl for 5 consecutive days. Each animal received a dietary equivalent of approx 10 mg/kg of test material, approx 2225 times the realistic max dietary exposure for a dairy animal. Milk, urine, & feces samples were collected in the morning & afternoon for each animal. Each goat was sacrificed within 23 hr of receiving the last dose, & the liver, kidneys, samples of blood, fat, muscle, & GI tract contents, & urine from the bladder were collected. All of these samples were analyzed for (14)C content. Cloransulam-methyl (CM) was rapidly excreted by the animals, with 99.9% of the recovered radioactivity appearing in the urine & feces. Radiochemical analysis showed very low residues, with the highest being in the kidneys at 0.122 and 0.128 mg equiv of CM/kg (AN & TP labeled compounds, respectively). Radioactive residues were extracted & fractionated from kidney, liver, and milk. Analysis showed approx 0.066 mg/kg CM in the kidney but <0.003 mg/kg in the liver. Only one metabolite, cloransulam, was identified (in liver, 9.5% of total radioactive residue; 0.005 mg/kg). All other metabolites were present at lower levels. Sulfonanilide bridge cleavage was not a significant degradation route for cloransulam-methyl in ruminants. These data indicated a very low bioaccumulation potential for cloransulam-methyl & its metabolites in ruminants. For a ruminant exposed to anticipated levels of cloransulam-methyl in its diet, parent & metabolites, in total, would not be expected to exceed 50 ng/kg in the kidney & liver.
Wird geladen…
147150-35-4DTXSID8034372CHEBI:3760Extinguishing Media: Use water fog, foam, CO2, or dry chemical. /FirstRate Herbicide/
Fire-fighting Equipment: Wear positive-pressure, self-contained breathing apparatus and full protective clothing. /FirstRate Herbicide/
Do not contaminate water when disposing of equipment washwaters or rinsate. /FirstRate Herbicide/
In case of leak or spill, contain material with absorbent materials and dispose as waste. /FirstRate Herbicide/
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Wastes resulting from the use of this product may be disposed of on site according to label use directions or at an approved waste disposal facility. /FirstRate Herbicide/
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /FirstRate Herbicide/
Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application. /FirstRate Herbicide/
Do not apply directly to water, to areas where surface water is present or to intertidal areas below the mean high water mark. /FirstRate Herbicide/
Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of twelve (12) hours. /FirstRate Herbicide/
For more Preventive Measures (Complete) data for CLORANSULAM-METHYL (8 total), please visit the HSDB record page.
Tolerances are established for residues of the herbicide, cloransulam-methyl, N-(2-carboxymethyl-6-chlorophenyl)-5-ethoxy-7-fluoro-(1,2,4)-triazolo[1,5c]-pyrimidine-2-sulfonamide, plus its acid, cloransulam, calculated as parent ester in or on the following raw agricultural commodities:[Table#6602]
Applicators and other handlers must wear: long-sleeved shirt and long pants; chemical-resistant gloves such as butyl rubber greater than or equal to 14 mils, or natural rubber greater than or equal to 14 mils, or neoprene rubber greater than or equal to 14 mils or nitrile rubber greater than or equal to 14 mils; shoes plus socks. /FirstRate Herbicide/
/Restricted entry interval (REI) of twelve (12) hours/ PPE required for early entry to the treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, is: coveralls, chemical-resistant gloves, shoes plus socks. /FirstRate Herbicide/
Safety glasses should be sufficient for most operations; however, for dusty operations wear chemical goggles. /FirstRate Herbicide/
In dusty atmospheres, use a NIOSH approved particulate respirator. /FirstRate Herbicide/
LD50; Species: /Colinus virginianus/ (Bobwhite quail) >2250 mg/kg bw
LC50; Species: /Colinus virginianus/ (Bobwhite quail) diet >5620 ppm for 5 days /Conditions of bioassay not specified/
LC50; Species: /Anas platyrhynchos/ (Mallard duck) diet >5620 ppm for 5 days /Conditions of bioassay not specified./
LD50; Species: /Apis mellifera/ (Honey bee) contact >25 ug ai/bee
For more Ecotoxicity Values (Complete) data for CLORANSULAM-METHYL (24 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 12 to 915(2-3) indicate that cloransulam-methyl is expected to have very high to low mobility in soil(SRC). The pKa of cloransulam-methyl is 4.81(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Cloransulam-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 3.0X10-16 mm Hg(4). A photodegradation half-life of 13 days was reported for cloransulam-methyl in moist soil(6). Biodegradation of cloransulam-methyl in soil may be important based upon reported half-lives of 9 to 21 days(7). In field dissipation studies, cloransulam-methyl had reported half-lives ranging from 4.2 to 24.1 days(6).
AQUATIC FATE: Based on a classification scheme(1), Koc values of 12 to 915(2-3), indicate that cloransulam-methyl is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.81(4) indicates cloransulam-methyl will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -0.365(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). An anaerobic aquatic biodegradation rate of 0.043/day with a half-life of 16 days was reported for cloransulam-methyl(8). Based upon an aqueous photodegradation half-life of 54 minutes, cloransulam-methyl may photodegrade rapidly in shallow sunlit water(8). Hydrolysis of cloransulam-methyl may be expected based upon a reported half-life of 10 days in natural water(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cloransulam-methyl, which has a vapor pressure of 3.0X10-16 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase cloransulam-methyl may be removed from the air by wet or dry deposition(SRC).
/AQUATIC SPECIES/ No mortality or sublethal effects from cloransulam-methyl exposure were reported for the grass shrimp; the 96-hr LC50 was >121 mg a.i./L. In contrast, effects on mean shell deposition to the Eastern oyster were reported at the limit concentration (111 mg a.i./L) tested. Mean shell deposition was decreased 18% compared to the negative control, and no additional adverse effects were noted. The 96-hr EC50 for Eastern oyster was >111 mg a.i./L (most sensitive estuarine/marine invertebrate acute toxicity endpoint) and the 96-hr NOAEC was < 111 mg a.i./L based on mean shell deposition.
Assessment in the field indicates little movement of cloransulam-methyl into the soil profile; residues are contained in the upper 12 to 18 inches of soil(1). Observed cloransulam-methyl Koc values ranged from 54.4 to 915 after three months incubation on six different soil types(1); greater adsorption at low versus high soil pH(1); sorption tends to increase with time associated with the soil(1). In a 55-day incubation study using 16 different soil types(2), time-averaged Koc values ranged from 12 to 262; apparent sorption (as measured by Kd) was observed to generally increase by as much as 10-fold over time(2). According to a classification scheme(3), these Koc values suggest that cloransulam-methyl is expected to have very high to low mobility in soil. Field studies conducted in Wisconsin, Mississippi, Indiana and North Carolina between 1993 and 1995 found that cloransulam-methyl exhibited low mobility in soil(4); cloransulam-methyl was rarely detected below 30 cm depth and was generally confined in the upper 5 cm(4); even with extreme leaching conditions at the WI and NC sites, cloransulam-methyl did not leach below 30 cm(4).
AEROBIC: Aerobic studies using Cecil loamy sand and Hanford loam soils incubated at 25 °C in the dark observed 14C labeled cloransulam-methyl half-lives of 9 and 13 days, respectively, using a biphasic pattern model(1). Using a first-order model, respective half-lives were 16 and 21 days(1). Degradation rates decreased about 10-fold when the soils were incubated at 5 °C or when sterilized by gamma-irradiation(1). Evolved 14CO2 accounted for up to 10% of applied 14C; other metabolites included cloransulam, 5-hydroxycloransulam-methyl and 5-hydroxycloransulam(1). Influence of temperature on the mineralization rate was dependent upon the location of the radio-label within the cloransulam-methyl molecule, suggesting that distinct groups of microorganisms degrade different parts of the molecule at different temperatures(2). Mineralization of radio-labeled cloransulam-methyl measured by 14CO2 was less in sterilized soil as compared to non-sterile soil(2).
ANAEROBIC: An anaerobic aquatic biodegradation rate of 0.043/day with a half-life of 16 days was reported for cloransulam-methyl(1).
An estimated BCF of 3 was calculated in fish for cloransulam-methyl(SRC), using a log Kow of -0.365(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
A pKa of 4.81(1) indicates cloransulam-methyl will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water and moist soil surfaces is not expected to be an important fate process. Cloransulam-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor of 3.0X10-16 mm Hg(1).
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 90-day dietary (mice): NOEL= 50 mg/kg/day (males). LOEL= 100 mg/kg/day for males based on increased levels of alkaline phosphatase and increased liver weights and an increase in the size of hepatocytes.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 21-day dermal (Rabbit): Dermal Irritation NOEL >or= 1000 mg/kg/day. Systemic NOEL = 500 mg/kg/day. Systemic LOEL = 1000 mg/kg/day based on decreased red cell count, hemoglobin and hematocrit, anisocytosis and macrocytosis of red cells for females.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In the Fischer 344 (F344) rat, dosages of 100-1000 mg/kg/day for 2 weeks produced slight decreases in red blood cell parameters and urine specific gravity in males, and slightly increased cecal and liver weights in females at 1000 mg/kg/day. The no-observed-effect level (NOEL) was 500 mg/kg/day. Dosages of 100-1000 mg/kg/dy for 13 weeks produced treatment-related kidney changes consisting of very slight to moderate hypertrophy of collecting tubule epithelial cells and/or slight vacuolation of the renal proximal tubular epithelium consistent with fatty changes in all dosage groups. Decreased body weight gain and feed consumption, very slight hepatocellular vacuolation, and slight thyroid follicular hypertrophy were also seen at 500 and 1000 mg/kd/day.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Dosages of 100, 500, or 1000 mg/kg/day fed to B6C3F1 mice for 2 weeks produced slight hepatocellular hypertrophy at 500 mg/kg/day and above in males, and at 1000 mg/kg/day in females. The NOEL was 100 mg/kg/day. Dosages ranging from 50 to 1000 mg/kg/day given for 13 weeks produced slight centrilobular and midzonal hepatocellular hypertrophy at 100 mg/kg/day and above in males, and at 500 mg/kg/day and above in females. Electron microscopy characterized the hypertrophy as an increase in rough endoplasmic reticulum (RER) with a decrease in cytoplasmic glycogen content. Kidney effects in mice consisted of decreased vacuolation of the renal tubules, consistent with decreased cytoplasmic lipid, accompanied by lower kidney weights at 500 mg/kg/day and higher. The subchronic lowest observed effect level (LOEL) and NOEL values in mice were 100 and 50 mg/kg/day, respectively.
For more Non-Human Toxicity Excerpts (Complete) data for CLORANSULAM-METHYL (14 total), please visit the HSDB record page.
The aqueous hydrolysis half-life of cloransulam-methyl is reported as >365, 118 to 231 and 3 days at pH 5, 7 and 9, respectively(1). A hydrolysis half-life of 10 days in natural water at an approximate pH of 8 and 67 days in a soil slurry at an approximate pH 6.5 were also reported(1). Photolysis half-lives of cloransulam-methyl were reported as 54 minutes and 13 days for aqueous and moist soil, respectively(1).
Tolerances are established for residues of the herbicide, cloransulam-methyl, N-(2-carboxymethyl-6-chlorophenyl)-5-ethoxy-7-fluoro-(1,2,4)-triazolo[1,5c]-pyrimidine-2-sulfonamide, plus its acid, cloransulam, calculated as parent ester in or on the following raw agricultural commodities:[Table#6603]
Metabolism studies were conducted with (14)C-radiolabeled cloransulam-methyl in the F344 rat using dose levels of 5 or 1000 mg/kg. At 5 mg/kg, over 90% of either a single dose or repeated (15 days doses was absorbed. At 1000 mg/kg, only 28-30% of a single dose was absorbed. Urinary elimination was rapid in both cases with half-lives of approximately 6-9 hr. A higher percentage of the 5 mg/kg dose was excreted in the urine by females (68-80%) than by males (40-50%) and these sex-dependent differences in disposition of the 5 mg/kg dose were attributed to more efficient elimination of unchanged cloarnsulam-methyl in the female versus male kidney.
Used as herbicide to control broadleaf weeds in soy beans; [HSDB]
Farming (Pesticides) [Category: Industry]
For cloransulam-methyl (USEPA/OPP Pesticide Code: 129116) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Herbicide
... Used pre- and post-emergence for the control of broad-leaved weeds in soya beans and other crops. It is applied only on the ground.
USEPA/OPP Pesticide Code 129116; Trade Names: XDE-565.
... Formulated as a 84% water dispersable granular in water soluble packaging. ... Cloransulam-methyl Technical is a 97.5% manufacturing use product.
Premix Partners: Sulfentrazone
XR-565, PACTO (South America), SUPRA (South America)
For more Formulations/Preparations (Complete) data for CLORANSULAM-METHYL (11 total), please visit the HSDB record page.
DefinitionChEBI: The methyl ester of cloransulam. An inhibitor of acetohydroxyacid synthase (AHAS), it prevents the synthesis of amino acids in plants and is used as a herbicide for the control of post-emergence control of broad-leaved weeds in soybeans. It is not approved for use within the European Area.