Clethodim

359.91

359.91

619-396-7

DTXSID3034458

Clear amber liquid

2914700090

80.7

4.21 (est)

Light Yellow Liquid

1.2±0.1 g/cm3

<25 °C

Decomposes below boiling point

162 deg F (72 deg C) (Closed cup) /Select Max Herbicide/

1.531

In water, 11.9 mg/L at 25 deg C (est)

0-6°C

2.66X10-9 mm Hg at 25 deg C (est)

LD50 in male, female rats (mg/kg): 1630, 1360 orally; LC50 in trout: 56 mg/l; 8 day feeding in quail: > 6000 ppm (Kincade)

Henry's Law constant = 1.16X10-11 atm-cu m/mol at 25 °C (est)

NONH for all modes of transport

3

22-24/25

Unstable at extreme pH's, temperature and upon exposure to UV light. /Select Max Herbicide/

P273

H412

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.|Nonrefillable container. Do not reuse or refill the container. Clean container promptly after emptying. Triple rinse as follows: Empty the remaining contents into application equipment or a mix tank and drain for 10 seconds after the flow begins to drip. Fill the container 1/4 full with water and recap. Shake for 10 seconds. Pour rinsate into application equipment or a mix tank or store rinsate for later use or disposal. Drain for 10 seconds after the flow begins to drip. Repeat this procedure two more times. Then offer for recycling, if available or puncture and dispose of in a sanitary landfill, or by incineration, or if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Select Max Herbicide/|Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. /Select Max 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.

May react with strong oxidizing agents, such as chlorates, nitrates, peroxides, etc. /Select Max Herbicide/

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501|H302 (88.07%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 327 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Applicators and other handlers must wear: longsleeved shirt and long pants, chemical-resistant gloves such as barrier laminate or viton > or = 14 mils, shoes plus socks and protective eyewear. /Select Max Herbicide/|Chemical-resistant gloves ...protective eyewear.|... Restricted-entry interval (REI) of 24 hours. Personal protective equipment (PPE) required for early entry to 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 over short-sleeved shirt and short pants, chemical-resistant gloves such as barrier laminate or viton > or = 14 mils and shoes plus socks. /Select Max Herbicide/|Use this material only in well ventilated areas. Unless ventilation is adequate to keep airborne concentrations below recommended exposure standards, approved respiratory protection should be worn. /Select Max Herbicide/

Products of combustion from fires involving this material may be toxic. Avoid breathing smoke and mists. Avoid personnel and equipment contact with fallout and runoff. Minimize the amount of water used for fire fighting. Do not enter any enclosed area without full protective equipment, including self-contained breathing equipment. Contain and isolate runoff and debris for proper disposal. Decontaminate personal protective equipment and fire fighting equipment before reuse. /Select Max Herbicide/|Liquid evaporates and forms vapor (fumes) which can catch fire and burn with explosive violence. Invisible vapor spreads easily and can be set on fire by many sources such as pilot lights, welding equipment, and electrical motors and switches. Fire hazard is greater as liquid temperature rises above 85 degrees F. /Select Max Herbicide/

Stop the source of the spill if safe to do so. Contain the spill to prevent further contamination of the soil, surface water, or ground water. /Select Max Herbicide/|Do not contaminate water when disposing of equipment washwater or rinsate. /Select Max Herbicide/|Avoid runoff into storm sewers and ditches which lead to waterways. Contain spilled liquids with dry sorbents. Clean up spill immediately. Absorb spill with inert material (such as dry sand or earth), then place in a chemical waste container. Wash area with soap and water. Pick up wash liquid with additional absorbent and place in a chemical waste container. This material forms an emulsion in water. Stop or reduce contamination of any water. Isolate contaminated water. Remove contaminated water for treatment or disposal. /Select Max Herbicide/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Select Max Herbicide/|Do not apply directly to water, or to areas where surface water is present or to intertidal areas below the mean high water mark. Do not apply where runoff is likely to occur. Do not apply where weather conditions favor drift from areas treated. /Select Max Herbicide/|Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Remove personal protective equipment (PPE) immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Select Max Herbicide/|Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them. Follow manufacturer's instructions for cleaning/maintaining personal protective equipment (PPE). If there are no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Select Max Herbicide/|For more Preventive Measures (Complete) data for Clethodim (10 total), please visit the HSDB record page.

LC50 Rat inhalation 3.9 mg/L/4 hr|LD50 Rabbit dermal >5000 mg/kg|LD50 Mouse oral (female) 2430 mg/kg|LD50 Mouse oral (male) 2570 mg/kg|For more Non-Human Toxicity Values (Complete) data for Clethodim (6 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ /In a/ Mallard duck chronic exposure reproductive toxicity /study/ ...no effects on growth or reproduction /were found up to 833 ppm (the highest concentration tested). /technical Clethodim/

Clethodim'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), an estimated Koc value of 8000(SRC), determined from a structure estimation method(2), indicates that clethodim is expected to be immobile in soil(SRC). Volatilization of clethodim from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Clethodim is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation half-lives of 1 to 3 days using 5 unspecified soils under aerobic conditions(5) suggest that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8000(SRC), determined from a structure estimation method(2), indicates that clethodim is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 280(SRC), from an estimated log Kow of 4.21(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Clethodim hydrolysis is pH dependent with degradation of 37%, 7%, and 0% reported at pH 5, pH 6, and pH 7, respectively, after 20 hours incubation(8). Biodegradation half-lives of 1 to 3 days using 5 unspecified soils under aerobic conditions(9) suggest that biodegradation is an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), clethodim, which has an estimated vapor pressure of 2.7X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Clethodim contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Clethodim hydrolysis in 50 mM buffer at 21 °C is pH dependent with degradation of 37%, 7%, and 0% at pH 5, pH 6, and pH 7, respectively, after 20 hours incubation(1). Hydrolysis half-lives of 28, 300, and 310 days have been reported at pH 5, 7, and 9, respectively(2). Clethodim contains chromophores that absorb at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC). Aqueous photolysis half-lives in sterile buffers, pH 5, and at pH 7 ranged from 1.7 to 9.6 days without a photosensitizer, 0.5 to 1.2 days with a photosensitizer(2).

An estimated BCF of 280 was calculated in fish for clethodim(SRC), using an estimated log Kow of 4.21(1) and a regression-derived equation(2). Using a modeling approach based on the quantitative structure-activity relationship (QSAR), a log BCF of 1.84, corresponding to a BCF of 70, was calculated(3). According to a classification scheme(4), these estimated BCF values suggest the potential for bioconcentration in aquatic organisms is high to moderate(SRC), provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of clethodim can be estimated to be 8000(SRC). According to a classification scheme(2), this estimated Koc value suggests that clethodim is expected to be immobile in soil. Freundlich adsorption coefficients (Kd) of 0.08 to 1.6 in five soil types have been reported(3).

The Henry's Law constant for clethodim is estimated as 1.2X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that clethodim is expected to be essentially nonvolatile from water and moist soil surfaces(2). Clethodim is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-9 mm Hg(SRC), determined from a fragment constant method(3).

A single lactating goat received (propyl-1-(14)C)-clethodim at 1.16 mg/kg bw per day in alfalfa diet, in three equal daily doses of 14.2 mg for three days and then a single dose of 14.2 mg on the fourth day, for a total of 10 doses. One female goat served as control. The treated goat was sacrificed 4 hrs after the final dose. ... Milk contained only 0.14%; the peak concentration (0.035 ppm) was attained after the sixth dose....

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

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.)

A single lactating goat received (propyl-1-(14)C)-clethodim at 1.16 mg/kg bw per day in alfalfa diet, in three equal daily doses of 14.2 mg for three days and then a single dose of 14.2 mg on the fourth day, for a total of 10 doses. One female goat served as control. The treated goat was sacrificed 4 hrs after the final dose. Clethodim was rapidly absorbed: the peak blood radiocarbon concentration (0.273 ppm) was achieved within the first hour after the initial dose. The mean amount of radiolabel recovered in the urine represented 56% of the administered dose and that in the feces, 34%. The total amount of radiolabel found in the milk, blood and tissues represented less than 1% of the amount administered. ... The tissues contained 0.37% and the blood, 0.22% of the dose. The highest residual tissue concentrations were detected in the liver and kidney.|Groups of 8-10 white Leghorn laying hens were given (cyclohexene-4,6-(14)C)-clethodim at 0, 2.1 or 51.3 mg/kg bw per day for five consecutive days and were sacrificed about 4 hrs after the final treatment. Radioanalysis showed that 78% of the low dose and 85% of the high dose of administered radioactivity was excreted in the feces; 1.9% of the low dose and 4.2% of the high dose were found in the tissues. The radiolabel was distributed in the tissues in the following order of decreasing concentration: gastrointestinal tract > kidney > liver. In eggs, 0.1% of the low dose and 0.3% of the high dose were found; the levels were highest in egg whites, intermediate in shells and lowest in yolks.|Male and female Crl:CD(SD)BR rats were given single oral doses of [propyl-1-(14)C]-clethodim at 4.4 or 468 mg/kg bw or unlabelled test material at 4.5 mg/kg bw per day for 14 consecutive days before treatment with a single radiolabeled dose of 4.8 mg/kg bw. Elimination was rapid: 94-98% of the administered dose was excreted within 48 hrs after treatment. The principal route of excretion was the urine (87-93%), and a smaller percentage (9-17%) of the radioactivity was eliminated in the feces. The mean amount of radioactivity excreted in expired air as carbon dioxide represented 0.5-1% of the administered dose. Although the elimination patterns were similar in all groups, the rate of elimination was somewhat faster in animals that were administered the single low dose of 4.4 mg/kg bw (98% eliminated within 40 hrs) than in those given the single high dose of 468 mg/kg bw (98% within 50 hrs). No differences in elimination rate were seen for animals of either sex administered repeated low doses of clethodim. Seven days after treatment, the total amount of radiolabel recovered from organs and tissues was less than 1% of the administered dose. The highest residual tissue concentrations were found in the adrenals, kidney and liver. There were no significant dose-related or sex-specific differences in tissue distribution, when expressed as a proportion of the dose administered, and there was no evidence of bioaccumulation.

... A lactating goat received (propyl-1-(14)C)-clethodim / at 1.16 mg/kg bw per day in alfalfa diet, in three equal daily doses of 14.2 mg for three days and then a single dose of 14.2 mg on the fourth day, for a total of 10 doses. One female goat served as control. The treated goat was sacrificed 4 hrs after the final dose. / ... hind- and forequarter muscle, peritoneal and subcutaneous fat, liver, kidneys, heart and blood were collected to allow characterization of metabolites. The major urinary metabolite was clethodim sulfoxide, which accounted for 67% of the urinary radiocarbon. Other urinary radiolabelled components were identified as clethodim (3-27%) and demethyl sulfoxide (12-18%), S-methyl (7-13%), imine sulfoxide (1.5-2.8%), sulfone (1.5-2.2%) and 5-hydroxy sulfoxide (0-3%). In the milk, about half of the radiocarbon could be extracted into organic solvents and occurred in clethodim, clethodim sulfoxide and clethodim demethyl sulfoxide; the other half of the radiocarbon was water soluble and was shown to be (14)C-lactose. In blood and tissues, the maximal extractable radiocarbon residues accounted for 77-95% of the radiolabel and were identified as clethodim and the sulfoxide, demethyl sulfoxide, imine sulfoxide, sulfone and 5-hydroxy sulfone. The proposed metabolic pathway in goats was essentially the same as that proposed for rats.|Two groups of eight white Leghorn laying hens were given daily doses of (cyclohexene-4,6-(14)C)-clethodim at 2.1 or 51.3 mg/kg bw per day by capsule for five consecutive days. The hens were sacrificed about 4 hrs after the final dose, and tissues were collected for analysis. Two major metabolites, clethodim sulfone and clethodim sulfoxide, were identified in tissues and eggs. Clethodim sulfone accounted for up to 57% of tissue levels of radiolabel, whereas clethodim sulfoxide accounted for 10-31%. Clethodim sulfoxide was the principal metabolite in egg white (26-82%) and yolk (25-37%); parent clethodim was detected in significantly smaller amounts in both tissues and eggs. The proposed metabolic pathway in chickens was different from and considered to be simpler than that observed in rats and goats, since none of the imine, 5-hydroxy or S-methyl analogues was detected in chickens.|... A group of male rats /Crl:CD(SD)BR/ were given a single oral dose of 450 mg/kg bw radiolabeled compound to ensure a sufficiently large quantity of labeled metabolites. Urine and feces were collected and analyzed for the parent compound and its metabolites. The metabolic profiles of males and females in all dose groups were remarkably similar. Nine urinary metabolites were identified and characterized. The major metabolite was clethodim sulfoxide (representing 65-75% of the administered dose), and smaller amounts were found of the imine sulfoxide (6-13%), the sulfone (1-3%), the 5-hydroxy sulfoxide/sulfone (0.5-1.5%) and the oxazole sulfone (0-5%). The primary fecal metabolites, which accounted for more than 1% of the radiolabel, were identified as clethodim sulfoxide and the imine sulfoxide. Minor (present as < 1% of the dose) urinary and fecal metabolites were the oxazole sulfoxide, the demethyl sulfoxide and the aromatic sulfone. Other minor fecal metabolites were clethodim sulfone, the trione sulfoxide and c-olefins. Parent clethodim accounted for about 1% of the administered dose.|The proposed metabolic pathways for clethodim in rats ... is postulated that once clethodim has been absorbed it can be: oxidized to clethodim sulfoxide (dominant process); converted to the S-methyl via a sulfonium cation intermediate; cleaved at the oxime N-O bond to generate imine or hydroxylated at the 5 position.

... Fatty acid synthesis inhibitor.

/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/

2-((1E)-N-(((2E)-3-chloro-2-propen-1-yl)oxy)propanimidoyl)-5-(2-(ethylsulfanyl)propyl)-3-hydroxy-2-cyclohexen-1-one

Accounted for 1.4% of herbicide usage in Canada 1996-1998

Emulsifiable concentrate|Section 2EC Herbicide (Winfield Solutions, LLC) Clethodim 26.4%|Aceto Clethodim 2 EC (Aceto Agricultural Chemicals Corp.) Clethodim 26.4%|Tapout (Helena Chemical Co.) Clethodim 12.6%|For more Formulations/Preparations (Complete) data for Clethodim (42 total), please visit the HSDB record page.

Adequate enforcement methodology (GC/FPD-S) is available to enforce the tolerance expression.|Analysis by HPLC

Agrochemicals -> Herbicides|Herbicides

Clethodim has known environmental transformation products that include clethodim oxazole sulfone, clethodim sulfone, and clethodim sulfoxide.