Mesotrione
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Mesotrione
structure -
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CAS No:
104206-82-8
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Formula:
C14H13NO7S
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Chemical Name:
Mesotrione
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Synonyms:
1,3-Cyclohexanedione,2-[4-(methylsulfonyl)-2-nitrobenzoyl]-;2-[4-(Methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione;Mesotrione;ZA 1296;Callisto;Tenacity (herbicide);Tenacity;Xiaohuangcaotong;435270-61-4;207996-81-4
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CAS No:
Description
Mesotrione is an aromatic ketone that is cyclohexa-1,3-dione in which one of the hydrogens at position 2 is substituted by a 4-(methanesulfonyl)-2-nitrobenzoyl group. It has a role as a herbicide, an EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor, a xenobiotic, an environmental contaminant and a carotenoid biosynthesis inhibitor. It is a sulfone, a C-nitro compound, an aromatic ketone and a beta-triketone. It derives from a benzophenone.
Mesotrione Basic Attributes
339.32
339.32
600-533-4
48TR68G21T
DTXSID7032424
Pale yellow solid|Opaque solid
2930909059
Characteristics
139.55000
-0.70
Light yellow crystalline powder
1.5±0.1 g/cm3
157-159 °C
643.3±55.0 °C at 760 mmHg
342.9±31.5 °C
1.583
Solubility in g/L at 20 deg c): in acetonitrile 117.0, acetone 93.3, 1,2-dichloroethane 66.3, ethyl acetate 18.6, methanol 4.6, toluene 3.1, xylene 1.6, n-heptane <0.5
0-6°C
<5.69X10-3 mPa /<4.27X10-8 mm Hg)/ at 20 deg C
Faint pleasant odor
Henry's Law constant: <1.2X10-10 atm-cu m/mol at 20 °C (est)
pKa = 3.12 at 20 °C; 0.6503 (associated) and 0.3404 (dissociated)
175.66 Ų [M+H]+ [CCS Type: TW]|177.77 Ų [M-H]-
Hydroxyl radical reaction rate constant = 7.3X10-12 cu cm/molec-sec at 25 °C (est)
Safety Information
UN 3077
50/53
60-61
N
Stable to hydrolysis (pH 4-9).
P273-P501
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.|Do not reuse product containers. Dispose of product containers, waste containers, and residues according to local, state, and federal health and environmental regulations|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.
Strong oxidizing agents
USEPA; Mesotrione Preliminary Work Plan, Registration Review: Initial Docket, Case Number 7256, Docket Number EPA-HQ-OPP-2013-0779 (June 2014). This document summarizes the Environmental Protection Agency's current position on the mesotrione registration review case.[Available from, as of September 19, 2014: http://www.noticeandcomment.com/June-2014-Mesotrione-Preliminary-Work-Plan-Registration-Review-Initial-Docket-Case-Number-7256-fn-142964.aspx]|European Commission; Standing Committee on the Food Chain and Animal Health for Mesotrione (104206-82-8) SANCO/1416/2001 (April 2003).
|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H361 (43.56%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P260, P273, P281, P308+P313, P314, P391, P405, and P501|Aggregated GHS information provided by 225 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Chemical-resistant gloves.|Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place., The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Wear self contained breathing apparatus for fire fighting if necessary.|Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.|Control spill at its source and contain to prevent from spreading, contaminating soil, or entering sewage and drainage systems or any body of water. Clean up immediately. Solid; Sweep up material and place in compatible disposal container. Liquid: Cover entire spill with absorbing material and place into compatible disposal container. Scrub area with hard water detergent. Pick up wash liquid with additional absorbent and place in container. Seal container and arrange disposition.
Long-sleeved shirt and long pants. Shoes plus socks.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.
It is a mild eye irritant, but is not a dermal irritant or a dermal sensitizer.
Toxicity
IDENTIFICATION AND USE: Mesotrione is a pale yellow solid with a faint pleasant odor. Mesotrione is an herbicide used on field corn, seed corn, sweet corn, yellow popcorn, and grain sorghum. 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. HUMAN EXPOSURE AND TOXICITY: Limited information is available on the effects of exposure to mesotrione on humans. Administration of mesotrione to volunteers resulted in an increase in plasma tyrosine concentrations, which reached a maximum of approximately 300 nmol/mL following a dose of 4 mg/kg body weight. Concentrations returned to background levels within 2 days of dosing. Urinary excretion of tyrosine metabolites was increased during the 24 hr immediately following a dose of 4 mg/kg, but returned to background levels during the following 24 hr period. Thus, the minimal and transient effects of mesotrione minimize the likelihood of a clinical effect in the event of systemic exposure occurring during occupational use. Mesotrione is not likely to be carcinogenic to humans. ANIMAL STUDIES: In animals, mesotrione is a mild eye irritant, but is not a dermal irritant or a dermal sensitizer. In subchronic and chronic oral studies, ocular lesions, liver and kidney effects, and/or body weight decrements were the major adverse effects seen in rat, mouse, and dog. Plasma tyrosine levels were increased in rat, mouse and dog in the chronic and reproduction studies. The ocular, liver and kidney effects are believed to be mediated by high tyrosine levels in the blood caused by inhibition of the enzyme 4-hydroxyphenylpyruvate dioxygenase. No evidence of neuropathology was found in acute and sub-chronic neurotoxicity studies in rat. However, sciatic nerve demyelination in the chronic rat study was associated with increased plasma tyrosine concentration. Increased incidence of thyroid adenomas in female rats only at the highest dose level in the 2 year rat study was also associated with increased plasma tyrosine concentration. Reduced/delayed ossification in rat, rabbit and mouse developmental studies were noted in the absence of overt maternal toxicity. ECOTOXICITY STUDIES: Antioxidative stress systems, saturation changes of lipid membranes, and the capacity of bacteria to degrade mesotrione were examined. The results showed that Escherichia coli DH5-alpha was able to tolerate high doses of the herbicide (10 times field rate), and completely degraded mesotrione after 3 hr of exposure. Growth rates in the presence of mesotrione were lower than in the control, prior to the period of degradation, showing toxic effects of this herbicide on bacterial cells. Changes in the saturation of the membrane lipids reduced the damage caused by reactive oxygen species and possibly hindered the entry of xenobiotics in the cell, while activating glutathione-S-transferase enzyme.
... A range of acute, subchronic and reproduction studies in the rat involving administration of different doses of mesotrione, with or without co-administration of dietary L-tyrosine and a developmental study in the rabbit utilising both mesotrione and tyrosine were used to elucidate the role of tyrosine in the pathogenesis of effects. ...The incidence and/or severity of the changes correlated with plasma tyrosine concentrations but not with concentrations of mesotrione.
LD50 Rat dermal >2000 mg/kg|LD50 Rat oral >5000 mg/kg
/FIELD STUDIES/ Population /of Pardosa spp /SRP: wolf spiders/ (all life stages)/ in test plots mirrored that in control plots. Application rate 0.150 kg as/ha. No long term adverse effects seen. /From table/|/OTHER TOXICITY INFORMATION/ Antioxidative stress systems, saturation changes of lipid membranes, and the capacity of bacteria to degrade mesotrione were examined. Escherichia coli DH5-alpha was chosen as a non-environmental strain, which is already a model bacterium for studying metabolism and adaptation. The results showed that this bacterium was able to tolerate high doses of the herbicide (10x field rate), and completely degraded mesotrione after 3 hr of exposure, as determined by a High Performance Liquid Chromatography. Growth rates in the presence of mesotrione were lower than in the control, prior to the period of degradation, showing toxic effects of this herbicide on bacterial cells. Changes in the saturation of the membrane lipids reduced the damage caused by reactive oxygen species and possibly hindered the entry of xenobiotics in the cell, while activating glutathione-S-transferase enzyme in the antioxidant system and in the metabolizing process of the herbicide. Considering that E. coli DH5-alpha is a non-environmental strain and it had no previous contact with mesotrione, the defense system found in this strain could be considered non-specific. This bacterium system response may be a general adaptation mechanism by which bacterial strains resist to damage from the presence of herbicides in agricultural soils.
Mesotriones'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 measured in 19 soils from the US and Europe ranging from 15 to 390(2,3), indicate that mesotrione is expected to have very high to moderate mobility in soil(SRC). Mesotrione is a weak acid with a pKa of 3.12(4) which indicates mesotrione will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5). The anionic form of mesotrione is a resonance enol-tautomer of the undissociated keto-tautomer(2). The Koc is inversely correlated with pH; as the pH increases, the Koc decreases(2,3). Volatilization of mesotrione from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of <1.2X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, <4.27X10-8 mm Hg(6), and water solubility, 160 mg/L(6). Mesotrione is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. The direct photolysis half-life on soil surfaces has been estimated to be 24 days at a latitude of 37-50 deg north(4). Degradation studies in active versus sterilized soils have demonstrated that biodegradation is the major degradation pathway in soils(3). Aerobic laboratory studies in 17 soils at 20-25 °C have observed dissipation half-lives ranging from 6-27 days(4,6); a half-life of 30 days was approximated for aerobic soil at 10 °C(4). One anaerobic test at 20 °C had a half-life of 4 days(4). Field dissipation studies at 6 sites (1 French, 3 German, 2 Italian) found half-lives of 3-7 days(4,6). Soil degradation was found to be related to soil pH, with half-lives decreasing with increasing soil pH(2,4).|AQUATIC FATE: Based on a classification scheme(1), Koc values measured in 19 soils from the US and Europe ranging from 15 to 390(2,3), indicate that mesotrione is not expected to adsorb to suspended solids and sediment(SRC). In water-sediment distribution tests, mesotrione was predominantly found in the water phase (>82%) with a maximum of 3.8% partitioning to sediment(4). Mesotrione is a weak acid with a pKa of 3.12(4) which indicates mesotrione will primarily exist in anion form in the environment and the anionic form of mesotrione is a resonance enol-tautomer of the undissociated keto-tautomer(2). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of <1.2X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, <4.27X10-8 mm Hg(6), and water solubility, 160 mg/L(6). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow of 0.90 at pH 5(4) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. Mesotrione is stable to hydrolysis at pH 4-9(4). Mesotrione is susceptible to direct photolysis in water with estimated half-lives of 81-97 days under summer conditions at 40-50 deg N latitude(4). The presence of organic matter in natural waters may increase the photodegradation rate by an order of magnitude due to sensitized photo-oxidation(9). Degradation studies in active versus sterilized soil-water systems have demonstrated that biodegradation is the major degradation pathway(3). Laboratory dissipation studies in water and water-sediment systems have observed mesotrione half-lives of 3.9-6.6 days(4).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mesotrione, which has a vapor pressure of <4.27X10-8 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase mesotrione may be removed from the air by wet and dry deposition(SRC). Mesotrione absorbs at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
In aqueous hydrolysis studies, very little degradation of mesotrione occurred after 30 days in the pH range 4-9 at both 25 °C and 50 °C(1); therefore, mesotrione is considered to be hydrolytically stable(1). Mesotrione absorbs at wavelengths >290 nm in water(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). In water at wavelengths >290 nm, mesotrione has measurable quantum yields of <4.6X10-6 to 1.3X10-4 over the pH range of 4-9(1). The photostability half-life of mesotrione in water at summer conditions at approximately 40-50 deg N latitude in northern Europe is estimated as 81-97 days(1). The reaction rate constant for the direct photolysis of mesotrione in water irradiated at 365 nm with a black light lamp was 1X10-5/sec(2) which corresponds to a half-life of about 19 hours(SRC). Using simulated sunlight irradiation, the reaction rate constant for the photolysis of mesotrione in water was 3.3X10-7/sec(2) which corresponds to a half-life of about 24 days(SRC). Addition of natural organic matter from the Suwannee River to the aqueous solutions irradiated by the simulated sunlight increased the reaction constant by approximately an order of magnitude(2); this faster photodegradation was due to sensitized photo-oxidation(2). Photodegradation products included MNBA (4-(methylsulfonyl)-2-nitrobenzoic acid)(2).
An estimated BCF of 3 was calculated for mesotrione(SRC), using a measured log Kow range of 0.90 at pH 5 to <-1.0 at pH 9(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).
Koc values for mesotrione were measured in 15 soils from the US and Europe and ranged from 15 to 390(1). Koc values of 22.4 to 183.9 were measured in four different loam soils(2). According to a classification scheme(3), these Koc values suggest that mesotrione is expected to have very high to moderate mobility in soil. Mesotrione is a weak acid with a pKa of 3.12 at 20 °C(4) which indicates mesotrione will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5). The anionic form of mesotrione is a resonance enol-tautomer of the undissociated keto-tautomer(1). The measured Koc values were determined in soils with pH values ranging from 4.6 to 7.7 with the Koc inversely correlated with pH(1,2); as the pH increases, the Koc decreases(1,2).
The Henry's Law constant for mesotrione is estimated as <1.2X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, <4.27X10-8 mm Hg(1), and water solubility, 160 mg/L in unbuffered water(1). This Henry's Law constant indicates that mesotrione is expected to be essentially nonvolatile from water surfaces(2). In addition, a pKa of 3.12 indicates mesotrione will exist primarily in the anionic enol-tautomer form(3) at pH values of 5 to 9 and therefore volatilization from water or moist soil surfaces is not expected to be an important fate process. Mesotrione is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure.
Occupational exposure to mesotrione may occur through inhalation and dermal contact with this compound at workplaces where mesotrione is produced or used(SRC). Based on the proposed use patterns, short-term dermal and inhalation exposures are expected for private applicators (farmers treating their own crops) and commercial applicators(1). The general population may be exposed to mesotrione via inhalation of ambient air and dermal contact with residues of mesotrione in the vicinity of areas where mesotrione is applied as a herbicide(SRC).
Drug Information
Approximately 70% /mestrione was absorbed/ within 72 hours. /Mestrione was/ widely distributed, highest residues in liver and kidney at 72 hours. No evidence of accumulation. 65-70% excreted within 72 hours, mainly via urine (55%)|NTBC (2-(2-nitro-4-fluoromethylbenzoyl)-1,3-cyclohexanedione) and mesotrione (2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione) are inhibitors of 4-hydroxyphenyl pyruvate dioxygenase (HPPD). NTBC has been successfully used as a treatment for hereditary tyrosinaemia type 1 (HT-1), while mesotrione has been developed as an herbicide. The pharmacokinetics of the two compounds were investigated in healthy male volunteers following single oral administration. The aim of the NTBC study was to assess the bioequivalence of two different formulations and to determine the extent of the induced tyrosinaemia. The mesotrione study was performed to determine the magnitude and duration of the effect on tyrosine catabolism. Additionally, the urinary excretion of unchanged mesotrione was measured to assess the importance of this route of clearance and to help develop a strategy for monitoring occupational exposure. ... A total of 28 volunteers participated in two separate studies with the compounds. In the first study, the relative bioavailability of NTBC from liquid and capsule formulations was compared and the effect on plasma tyrosine concentrations measured. In the second study the pharmacokinetics of mesotrione were determined at three doses. Plasma tyrosine concentrations were monitored and the urinary excretion of mesotrione and tyrosine metabolites was measured. Both compounds were well tolerated at the dose levels studied. Peak plasma concentrations of NTBC were rapidly attained following a single oral dose of 1 mg x kg(-1) body weight of either formulation and the half-life in plasma was approximately 54 hr. There were no statistical differences in mean (+/- s.d.) AUC(0,infinity) (capsule 602 +/- 154 vs solution 602 +/- 146 ug x ml(-1) hr) or t1/2 (capsule 55 +/- 13 vs solution 54 +/- 8 hr) and these parameters supported the bioequivalence of the two formulations. Mesotrione was also rapidly absorbed, with a significant proportion of the dose eliminated unchanged in urine. The plasma half-life was approximately 1 hr and was independent of dose and AUC(0,infinity) and Cmax increased linearly with dose. Following administration of 1 mg NTBC x kg(-1) in either formulation, the concentrations of tyrosine in plasma increased to approximately 1100 nmol x ml(-1). Concentrations were still approximately 8 times those of background at 14 days after dosing, but had returned to background levels within 2 months of the second dose. Administration of mesotrione resulted in an increase in tyrosine concentrations which reached a maximum of approximately 300 nmol x ml(-1) following a dose of 4 mg x kg(-1) body weight. Concentrations returned to those of background within 2 days of dosing. Urinary excretion of tyrosine metabolites was increased during the 24 hr immediately following a dose of 4 mg mesotrione x kg(-1), but returned to background levels during the following 24 hr period. ...
Limited metabolism, up to 5% metabolized by hydroxylation.|The metabolic fate of [(14)C]-2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione (mesotrione) has been determined in the male and female rat and mouse following a single oral dose of either 1 or 100 mg/kg, in rat given 14 consecutive oral doses of 1 mg/kg, and in the surgically prepared, bile duct-cannulated rat following a single oral dose of 50 mg/kg. ...Mesotrione was extensively absorbed and rapidly excreted via urine in both rat and mouse. ...The major metabolic pathway was hydroxylation of the aromatic ring.
... The plasma half-life was approximately 1 hr ...
Mechanistic studies show that the toxic effects of /mesotrione/ are largely attributable to increased plasma tyrosine levels following 4-hydroxyphenyl pyruvate dioxygenase (HPPD) inhibition. Tyrosine levels are increased to a greater extent in rats (particularly males) due to differences in the activity of enzymes in the tyrosine catabolic pathway. Studies show that the mouse is more predictive of the response in humans. Human volunteer study (single oral dose) shows a NOAEL of 0.5 mg/kg bw.
/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 TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) 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/
/HUMAN EXPOSURE STUDIES/ ... Mesotrione (2-(4-methylsulphonyl-2-nitrobenzoyl)-1,3-cyclohexanedione) inhibits 4-hydroxyphenyl pyruvate dioxygenase (HPPD). ... The mesotrione study was performed to determine the magnitude and duration of the effect on tyrosine catabolism. Additionally, the urinary excretion of unchanged mesotrione was measured to assess the importance of this route of clearance and to help develop a strategy for monitoring occupational exposure. /Three groups, each consisting of six male volunteers between 19 and 53 years, were given a single oral dose of either 0.1, 0.5 or 4 mg mesotrione/kg./ ... Plasma tyrosine concentrations were monitored and the urinary excretion of mesotrione and tyrosine metabolites was measured. ... Administration of mesotrione resulted in an increase in tyrosine concentrations, which reached a maximum of approximately 300 nmol/mL following a dose of 4 mg/kg body weight. Concentrations returned to those of background within 2 days of dosing. Urinary excretion of tyrosine metabolites was increased during the 24 hr immediately following a dose of 4 mg mesotrione/kg, but returned to background levels during the following 24 hr period. ... /The/ minimal and transient effects of mesotrione minimize the likelihood of a clinical effect in the event of systemic exposure occurring during occupational use.|/OTHER TOXICITY INFORMATION/ Mechanistic studies show that the toxic effects of /mesotrione/ are largely attributable to increased plasma tyrosine levels following 4-hydroxyphenyl pyruvate dioxygenase (HPPD) inhibition. Tyrosine levels are increased to a greater extent in rats (particularly males) due to differences in the activity of enzymes in the tyrosine catabolic pathway. Studies show that the mouse is more predictive of the response in humans. Human volunteer study (single oral dose) shows a NOAEL of 0.5 mg/kg bw.
(2-nitro-4-(methylsullfonyl))benzoylcyclohexane-1,3-dione
Mesotrione Use and Manufacturing
Mesotrione is prepared by reaction of 3-methylmercaptonitrobenzene with acetyl chloride in the presence of aluminum trichloride yielding the corresponding ketone, which is oxidized with sodium oxychloride giving the corresponding 4-methylsulfonyl compound, which in turn is condensed with cyclohexane-1,3-dione to give the corresponding enol ester. The latter is rearranged to the desired product with potassium cyanide in the presence of triethylamine.|Preparation: C. G. Carter, European Patent Office 186118 (1986 to Stauffer); idem, United States of America 5006158 (1991 to ICI).
Herbicide.
A review of total mesotrione usage data for the last 5 years indicates that the primary use site is corn, accounting for approximately 98% of both total pounds applied and total acres treated. Field corn represents the highest percent crop treated in terms of acres grown and acres treated at 20.2%. Usage data is not available for mesotrione use in non-agricultural sites.
Formulation Type(s): Granular, water dispersible granules, emulsifiable concentrate, soluble concentrate, solution-ready to use, pressurized liquid, and soluble concentrate/solid.|Suspension concentrate.|Premix Partners: Atrazine; Glyphosate; S-Metolachlor; Nicosulfuron; Rimsulfuron; Terbuthylazine.|Callisto Herbicide (Syngenta Crop Protection, LLC): Active ingredient: mesotrione 40.0%.|For more Formulations/Preparations (Complete) data for MESOTRIONE (28 total), please visit the HSDB record page.
Callisto Herbicide is effective in controlling broadleaf weeds in field corn. It will replace atrazine and isoxaflutole herbicides. Mesotrione is a new class of herbicide and if used in Resistance Management Programs it can mitigate the increase in resistant biotypes.|The manufacturing impurity 1-cyano-6-(methylsulfonyl)-7-nitro-9H-xanthen-9-one is considered to be of toxicological concern and must remain below 0.0002% (w/w) in the technical product.|Triketone herbicide for use in maize; inhibits p-hydroxyphenylpyruvate dioxygenase (HPPD). Synthetic mimic of leptospermone, a natural herbicide produced by the bottlebrush plant, Callistemon citrinus Stapf.
... High-pressure liquid chromatography fluorescence detector (HPLC/FLD), is available to enforce the tolerance expression.|HPLC determination in crops, soil, water.
Agrochemicals -> Herbicides|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)
Mesotrione has known environmental transformation products that include 2-amino-4-methylsulfonylbenzoic acid and 4-methylsulfonyl-2-nitrobenzoic acid.|Mesotrione has known environmental transformation products that include AMBA and MNBA.
Computed Properties
Molecular Weight:339.32
XLogP3:0.7
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:339.04127293
Monoisotopic Mass:339.04127293
Topological Polar Surface Area:140
Heavy Atom Count:23
Complexity:627
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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