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Cloransulam-methyl

Cloransulam-methyl structure

Cloransulam-methyl 

structure
  • CAS No:

    147150-35-4

  • Formula:

    C15H13ClFN5O5S

  • Chemical Name:

    Cloransulam-methyl

  • Synonyms:

    Benzoic acid,3-chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfonyl]amino]-,methyl ester;[1,2,4]Triazolo[1,5-c]pyrimidine,benzoic acid deriv.;Cloransulam-methyl;DE 565;Cloransulam methyl ester;FirstRate;Chloransulam-methyl

  • Categories:

    Agrochemicals  >  Herbicides

Description

ChEBI: 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.


Cloransulam-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 a herbicide, an EC 2.2.1.6 (acetolactate synthase) inhibitor and an agrochemical. It is a methyl ester, a sulfonamide, a member of monochlorobenzenes, an organofluorine compound and a member of triazolopyrimidines. It derives from a cloransulam.

Cloransulam-methyl Basic Attributes

429.81

429.81

604-573-3

N9P737Z6HO

DTXSID8034372

Off-white powder

2935009011

Characteristics

133

3.05670

1.538 g/cm3 @ Temp: 20 °C

216-218 °C

1.677

Solubility (all in mg/L): acetone 4360; acetonitrile 550; dichloromethane 3980; ethyl acetate 980; methanol 470; hexane <10; octanol <10; toluene 14

0-6°C

3.0X10-16 mm Hg (4.0X10-11 mPa) at 25 deg C

Slight mint

Henry's Law constant = 9.2X10-19 atm-cu m/mol at 25 °C (est)

pKa = 4.81 at 20 °C

Does not react with mild steel or stainless steel at 50 °C

Safety Information

UN 3077 9 / PGIII

3

20-50

61

Xn,N

Stable after 28 days at room temp alone and 122 deg F alone and with 304 and 306 stainless steel, mild steel, brass, ferric chloride & magnesium chloride.

P273-P501

H332-H410

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.

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]

|Warning|H332 (29.92%): Harmful if inhaled [Warning Acute toxicity, inhalation]|P261, P271, P273, P304+P312, P304+P340, P312, P391, and P501|Aggregated GHS information provided by 130 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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/

Extinguishing 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/

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.

Toxicity

LD50 Rat oral >5000 mg/kg|LD50 Rabbit dermal >2000 mg/kg

/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.

Cloransulam-methyl's production may result in its release to the environment through various waste streams; its use as a herbicide(1) will result in its direct release to the environment(SRC).

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).

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).

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).

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).

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).

Occupational exposure to cloransulam-methyl may occur through inhalation and dermal contact with this compound at workplaces where cloransulam-methyl is produced or used. (SRC)

Drug Information

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.|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.

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.

... 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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

cloransulam-methyl

Cloransulam-methyl Use and Manufacturing

Methods of Manufacturing

Cloransulam-methyl is produced by condensation of 5-oxyethyl-7-fluoro-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonyl chloride with 2-carboxymethyl-6-chloroaniline.

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.

Applied by ground only at 0.6 to 0.75 ounces per acre ... Maximum use rate of 0.40 lb per acre.

In soil by gas chromatography/MSD. In water by gas chromatography/mass spectrometry.

Computed Properties

Molecular Weight:429.8
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:7
Exact Mass:429.0309956
Monoisotopic Mass:429.0309956
Topological Polar Surface Area:133
Heavy Atom Count:28
Complexity:668
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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