Aminocyclopyrachlor

213.62102

213.62

1312995-182-4

O19K7667GO

DTXSID0074683

Granules

2933599020

89.83000

1.21790

1.635g/cm3

432.3ºC at 760 mmHg

215.3ºC

1.7

In water at 20 °C: 2810 mg/L (in Milli-Q water), 3130 mg/L (pH 4), 4200 mg/L (pH 7), 3870 mg/L (pH 9)

Do not contaminate water, other pesticides, fertilizer, food or feed in storage. Store in original container. Store in a cool, dry place. Keep out of the reach of children. /DuPont Method 50SG Herbicide/

3.7X10-8 mm Hg at 25 °C

Henry's Law constant = 3.47X10-12 atm-cu m/mol at 20 °C

pKa = 4.65 at 20 °C|pKa (estimated) = 2.71 (acid), 17.86 (amino function), 1.48 and 1.96 (ring nitrogens)

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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.

H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|Aggregated GHS information provided by 156 companies from 1 notifications to the ECHA C&L Inventory.

Personal Protective Equipment (PPE): Mixers and loaders must wear: Long-sleeved shirt and long pants. Shoes plus socks. Applicators: After the product has been diluted in accordance with label directions for use, shirt, pants, socks, and shoes are sufficient Personal Protective Equipment (PPE). /DuPont Method 50SG Herbicide/|Wear protective eyewear to prevent contact with this substance. /DuPont Method 50SG Herbicide/

In the event of fire, wear self-contained breathing apparatus. Wear full protective equipment. Evacuate personnel and keep upwind of fire. If area is heavily exposed to fire and if conditions permit, let fire burn itself out since water may increase the area contaminated. Do not allow run-off from fire fighting to enter drains or water courses. In the event of fire, cool tanks with water spray. /DuPont Method 50SG Herbicide/|Suitable extinguishing media: Water spray, foam, dry chemical, carbon dioxide (CO2). /DuPont Method 50SG Herbicide/|Not a fire or explosion hazard. /DuPont Method 50SG Herbicide/

Do not contaminate water when disposing of equipment washwaters or rinsate. /DuPont Method 50SG Herbicide/|Safeguards (Personnel): Evacuate personnel, thoroughly ventilate area, use self-contained breathing apparatus. Wear personal protective equipment.. /DuPont Method 50SG Herbicide/|Spill Cleanup: Sweep up and shovel into suitable containers for disposal. /DuPont Method 50SG Herbicide/|Accidental Release Measures: Prevent material from entering sewers, waterways, or low areas. Follow applicable Federal, State/Provincial and Local laws/regulations. /DuPont Method 50SG Herbicide/

Wash thoroughly with soap and water after handling and 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. /DuPont Method 50SG 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. /DuPont Method 50SG Herbicide/|Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry. /DuPont Method 50SG Herbicide/|Do not enter terrestrial/non-crop treated areas without protective clothing until sprays have dried. /DuPont Method 50SG Herbicide/

LD50 Rat dermal >5000 mg/kg /Technical/|LD50 Rat oral >5000 mg/kg /Technical/|LD50 Rat dermal >5000 mg/kg /Aminocyclopyrachlor-methyl technical/

/AQUATIC SPECIES/ A 90-day chronic toxicity test was submitted that evaluated the effects of the acid on the earlylife stage of rainbow trout under flow-through conditions. Measured test concentrations were between 0.69 and 11 mg a.e./L. There were no treatment-related effects on hatching success, time to hatch, post-hatch survival, time to swim-up, or growth at any treatment level. The 90-day LC/EC50 for all endpoints was >11 mg a.e./L, and the NOAEC and LOAEC were 11 and >11 mg a.e./L, respectively. /Aminocyclopyrachlor-acid/

Aminocyclopyrachlor'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). In August 2010, EPA conditionally registered the active ingredient aminocyclopyrachlor for pesticide applications(2); in August 2011, the EPA issued a Stop Sale, Use or Removal Order for the herbicide Imprelis (which contains the active ingredient aminocyclopyrachlor) which may be causing injury to certain species of evergreen trees, particularly Norway spruce and white pine(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an observed Koc range of 9 to 67(2) indicates that aminocyclopyrachlor is expected to have very high to high mobility in soil(SRC). The pKa of aminocyclopyrachlor is 4.65(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of aminocyclopyrachlor from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.47X10-12 atm-cu m/mole(3). Aminocyclopyrachlor is slowly photolyzed on soil (half-life of 129 days)(3). Aerobic soil metabolism tests had half-life ranges of 114-433 in three different soils(3). Aminocyclopyrachlor half-lives ranged from 22 to 126 days in terrestrial field dissipation studies conducted in the continental United States and Canada(3).|AQUATIC FATE: Based on a classification scheme(1), an observed Koc range of 9 to 67(2), indicates that aminocyclopyrachlor is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 3.47X10-12 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -2.48 at pH 7(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The major route of environmental degradation of aminocyclopyrachlor in water is aqueous photolysis with a half-life of l.2 days in shallow, clear, and well-lit natural (pH 6.2) water bodies and 7.8 days in pH 4 buffer solution(4); the photolysis degradation products included 5-chloro-2-cyclopropyl-pyrimidin-4-ylamine, 4-cyano-2-cyclopropy1-1H-imidazole-5-carboxylic acid and cyclopropanecarboxylic acid(4). Aminocyclopyrachlor is stable to hydrolysis at environmental conditions(4). Aerobic aquatic metabolism tests had observed aminocyclopyrachlor half-lives greater than 100 days(4) with metabolites that included CO2 and 5-chloro-2-cyclopropyl-pyrimidin-4-ylamine(4); anaerobic metabolism tests had observed half-lives greater than 120 days (calculated half-life 1733 days)(4).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), aminocyclopyrachlor, which has a vapor pressure of 3.7X10-8 mm Hg at 25 °C(2) will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase aminocyclopyrachlor is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 5 days(SRC), calculated from its rate constant of 3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase aminocyclopyrachlor may be removed from the air by wet or dry deposition(SRC).

The rate constant for the vapor-phase reaction of aminocyclopyrachlor with photochemically-produced hydroxyl radicals has been estimated as 3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Aminocyclopyrachlor degrades via photolysis with a half-life of 1.2 days in well-lit natural water bodies (pH 6.2) and 7.8 days in pH 4 buffer(2); it is slowly photolyzed on soil (half-life of 129 days)(2); the photolysis degradation products included 5-chloro-2-cyclopropyl-pyrimidin-4-ylamine, 4-cyano-2-cyclopropy1-1H-imidazole-5-carboxylic acid and cyclopropanecarboxylic acid(2). Aminocyclopyrachlor is stable to hydrolysis at pH 4,7, and 9(2); no hydrolysis was observed at 50 °C over duration greater than 5 days(2).

An estimated BCF of 3.1 was calculated in fish for aminocyclopyrachlor(SRC), using a log Kow of -2.48 at pH 7(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).

In sorption-desorption studies using 14 soils from Brazil, aminocyclopyrachlor had Koc values ranging from 9 to 67(1). A Koc range of 2 to 26 was observed in test soils(2). According to a classification scheme(3), these Koc values suggest that aminocyclopyrachlor is expected to have very high to high in soil. In terrestrial field studies, aminocyclopyrachlor was detected at soil depths of 70 - 90 cm at 365 days, indicating that leaching of residues into groundwater may occur(4). The pKa of aminocyclopyrachlor is 4.65(2), indicating that this compound will exist partially 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).

The Henry's Law constant for aminocyclopyrachlor is 3.47X10-12 atm-cu m/mole at 20 °C(1). This Henry's Law constant indicates that aminocyclopyrachlor is expected to be essentially nonvolatile from water surfaces(2).

Occupational handler exposure to aminocyclopyrachlor may occur dermally and by inhalation(1).

4 rats per sex per group with surgically implanted jugular vein cannulas received a single oral gavage dose of (14)C-DPX-MAT28 /aminocyclopyrachlor/ at 25 and 500 mg/kg and were placed in metabolism cages. Serial blood samples were collected pre-treatment and at 5, 15, and 30 minutes, and 1, 2, 4, 8, 12, 24, and 30 hours post-dosing from the jugular vein cannula. Plasma contained quantifiable concentrations of (14)C residues for up to 30 hours post-treatment. Group mean plasma half-lives were nearly identical for males (5.6 hours) and females (5.7 hours) at both 25 and 500 mg/kg. Group mean peak plasma concentrations (Cmax) were 3.8 ug.equiv/g for males and 5.0 ug.equiv/g for females at 25 mg/kg and 57.3 ug.equiv/g for males and 61.6 ?g.equiv/g for females at 500 mg/kg (a 12 to 15 fold increase in Cmax with the 20-fold increase in dose). Times to peak plasma concentrations (Tmax) were 0.5 hours (males) and 0.4 hours (females) at 25 mg/kg and 0.6 hours (males) to 1.0 hours (females) at 500 mg/kg. Group mean area under the curve values (AUCINF) for plasma were 7.0 hr*ug/g for males and 9.0 hr*ug/g for females at 25 mg/kg and 151 hr*ug/g for males and 168 hr*ug/g for females at 500 mg/kg (21.5 (males) and 18 (females) fold increases over the low dose values). Group mean Cmax values for red blood cells were 1.3 ug.equiv/g for males and 2.0 ug.equiv/g for females at 25 mg/kg and 27.2 ug.equiv/g for males and 28.7 ug.equiv/g for females at 500 mg/kg. Group mean Tmax values for RBCs were 0.5 hour (males) and 0.3 hour (females) at 25 mg/kg and 0.6 hour for males and 1.0 hour for females at the high dose.|3 rats per sex received a single oral gavage dose of (14)C-DPX-MAT28 /aminocyclopyrachlor/ at 500 mg/kg. Rats were sacrificed 30 minutes post-treatment and whole blood was collected and separated into plasma and erythrocytes. Additionally, 1 rat per sex was used for collection of control plasma. The only identifiable component in plasma was DPX-MAT28 at group mean concentrations of 219 uM for males and 251 uM for females. No biotransformation was indicated. DPX-MAT28 circulated in plasma and was excreted in the urine and feces as intact parent chemical|One rat per sex received a single oral gavage dose of (14)C-DPX-MAT28 /aminocyclopyrachlor/ at 25 mg/kg. Animals were placed in glass metabolism units for collection of (14)C exhaled volatiles and (14)CO2 for 48 hours (at 24-hour intervals). Urine and feces were also collected at 24-hour intervals over dry ice for 168 hours. Urine, feces, tissues, carcass, cage wash, and residual feed were analyzed (LSC, HPLC, mass spectrometry (MS)) to determine preliminary material balance and tissue distribution (urine and feces were analyzed for metabolites). Radioactivity was not detected in respired breath during 48 hours after a single 25 mg/kg dose. Excretion of radioactivity occurred in both urine and feces with the majority eliminated during the first 24 hours after dosing. During 168 hours post-treatment, 36.3% (male) and 55.8% (female) of administered dose was excreted in urine and 32.1% (male) and 51.7% (female) was eliminated in feces (24 hour values were 35.9% (male) and 53.7% (female) in urine and 31.1% (male) and 48.0% (female) in feces). The overall material balance was 69.9% (male) and 107.9% (female) after 168 hours. (14)C residues in tissues were generally below the limit of quantification except the male carcass contained 0.039% of administered dose. DPX-MAT28 was the only component identified in urine (35.9% (males) and 53.7% (females) of administered dose) and feces (31.1% (males) and 48.0% (females) of dose).

1 male and 1 female rat received a single oral gavage dose of (14)C-DPX-KJM44 /aminocyclopyrachlor methyl/ at 25 mg/kg. Animals were placed in glass metabolism units for collection of 14C exhaled volatiles and (14)CO2 for 48 hours (at 24-hour intervals). Urine and feces were also collected at 24-hour intervals over dry ice for 168 hours. Radioactivity was quantified in urine, feces, tissues, carcass, cage wash, and residual feed and urine and feces were also analyzed for metabolites (LSC, HPLC, mass spectrometry (MS)). Radioactivity was not detected in respired breath during 48 hours after a single 25 mg/kg dose. Urine was the main route of excretion of radioactivity with 80.4% (male) and 79.3% (female) of administered dose detected during 168 hours post-dosing (most (78.8% for both sexes) was excreted during the first 24 hours after dosing). 6.67% (male) and 3.06% (female) of administered radioactivity was found in feces during 168 hours with the majority excreted during 48 hours post-treatment (5.6% (male) and 2.8% (female)). Radioactivity detected in cage wash and residual food was 2.0% and 0.1% for the male and female, respectively. The overall material balance was 89.2% (male) and 82.6% (female) after 168 hours. 14C residues in tissues were generally below the limit of quantification except male and female carcasses contained 0.144% and 0.121% of administered dose, respectively, and the male gastrointestinal tract and contents contained 0.009% of dose combined. DPX-MAT28 /aminocyclopyrachlor/ was the only metabolite identified in urine (78.8% of administered dose for both sexes) and feces (4.57% (males) and 1.72% (females) of dose). /Aminocyclopyrachlor-methyl/

4 rats per sex per group with surgically implanted jugular vein cannulas received a single oral gavage dose of (14)C-DPX-MAT28 /aminocyclopyrachlor/ at 25 and 500 mg/kg and were placed in metabolism cages. Serial blood samples were collected pre-treatment and at 5, 15, and 30 minutes, and 1, 2, 4, 8, 12, 24, and 30 hours post-dosing from the jugular vein cannula. ... Group mean plasma half-lives were nearly identical for males (5.6 hours) and females (5.7 hours) at both 25 and 500 mg/kg.

/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/|Skin decontamination. Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other herbicides/|For more Antidote and Emergency Treatment (Complete) data for Aminocyclopyrachlor (7 total), please visit the HSDB record page.

/GENOTOXICITY/ In a mammalian cell cytogenetics assay (chromosome aberration), lymphocyte cultures were prepared from human peripheral blood and exposed to DPX-MAT28 (/aminocyclopyrachlor/ 92.2% a.i.) in DMSO at concentrations of 0, 267, 534, 1068, or 2136 ug/mL for either 4 hours followed by a 16 hour recovery period (+/-S9) or for 20 hours with no recovery period (-S9). The S9 fraction was derived from the livers of male rats induced with Aroclor 1254. Cyclophosphamide and mitomycin C served as the positive controls in the presence and absence of S9, respectively. DPX-MAT28 was tested up to the limit dose (2136 ug/mL, 10mM). No precipitation of the test material was observed at any concentration (+/-S9). No substantial decreases in mitotic index were observed at any concentration after 4 (+/-S9) or 20 hrs (-S9) of treatment; therefore, concentrations of 0, 534, 1068, and 2136 ug/mL were selected for evaluation of chromosomal aberrations in each assay. No significant increases in the mean percentage of cells with structural or numerical abortions or in aberrations per cell were observed after treatment for 4 hrs (+/-S9) or 20 hrs (-S9). The positive controls induced the appropriate response in the presence and absence of S9. There was no evidence of chromosome aberrations induced over background in the presence or absence of S9-activation.

6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid

Ortho MAT28S RTU (The Scotts Company): Aminocyclopyrachlor 0.0045%.|Ortho MAT28N RTU (The Scotts Company): Aminocyclopyrachlor 0.01%.|Ortho MAT28NS Conc (The Scotts Company): Aminocyclopyrachlor 0.25%.|Ortho MAT28N Combo RTU (The Scotts Company): Aminocyclopyrachlor 0.01%; Quinclorac 0.1%; Dicamba 0.044%.|For more Formulations/Preparations (Complete) data for Aminocyclopyrachlor (20 total), please visit the HSDB record page.

In August 2010, EPA conditionally registered the active ingredient aminocyclopyrachlor for pesticide applications. In August 2011, the EPA issued a Stop Sale, Use or Removal Order for the herbicide Imprelis (which contains the active ingredient aminocyclopyrachlor) which may be causing injury to certain species of evergreen trees, particularly Norway spruce and white pine.

Analytical methods have been developed for the detection and quantitation of a new herbicide active ingredient, aminocyclopyrachlor, and its analogue aminocyclopyrachlor methyl in environmental samples. The analytes were purified from soil extracts and water samples using solid phase extraction based on mixed-mode cation exchange/reverse phase retention. Analyte identification and quantitative analyses were performed by high performance liquid chromatography coupled to tandem mass spectrometry by an electrospray ionization source. External standards prepared in neat solvents were used for quantitation, providing acceptable accuracy, with no matrix effects observed during method validation. The method limits of quantitation (LOQ) were 0.10 ng/mL (ppb, parts-per-billion) in water and 1.0 ng/g in soil for both compounds. The limit of detection (LOD) in water was estimated to be 20 ng/L (ppt, parts-per-trillion) for aminocyclopyrachlor and 1 ng/L for aminocyclopyrachlor methyl, while LODs in soil were 100 ng/kg and 10 ng/kg for aminocyclopyrachlor and aminocyclopyrachlor methyl, respectively. The stability of both compounds in various solvents was evaluated as part of method development. Tandem mass spectrometry experiments were also conducted to investigate the gas-phase fragmentation of aminocyclopyrachlor and its methyl analogue, and the results are reported. A statistical analysis of method validation data generated at two laboratories by multiple chemists authenticates the ruggedness and good reproducibility of the analytical procedures tested.|A prototype multiresidue method based on fast extraction and dilution of samples followed by flow injection mass spectrometric analysis is proposed here for high-throughput chemical screening in complex matrices. The method was tested for sulfonylurea herbicides (triflusulfuron methyl, azimsulfuron, chlorimuron ethyl, sulfometuron methyl, chlorsulfuron, and flupyrsulfuron methyl), carbamate insecticides (oxamyl and methomyl), pyrimidine carboxylic acid herbicides (aminocyclopyrachlor and aminocyclopyrachlor methyl), and anthranilic diamide insecticides (chlorantraniliprole and cyantraniliprole). Lemon and pecan were used as representative high-water and low-water content matrices, respectively, and a sample extraction procedure was designed for each commodity type. Matrix-matched external standards were used for calibration, yielding linear responses with correlation coefficients (r) consistently >0.99. The limits of detection (LOD) were estimated to be between 0.01 and 0.03 mg/kg for all analytes, allowing execution of recovery tests with samples fortified at =0.05 mg/kg. Average analyte recoveries obtained during method validation for lemon and pecan ranged from 75 to 118% with standard deviations between 3 and 21%. Representative food processed fractions were also tested, that is, soybean oil and corn meal, yielding individual analyte average recoveries ranging from 62 to 114% with standard deviations between 4 and 18%. An intralaboratory blind test was also performed; the method excelled with 0 false positives and 0 false negatives in 240 residue measurements (20 samples X 12 analytes). The daily throughput of the fast extraction and dilution (FED) procedure is estimated at 72 samples/chemist, whereas the flow injection mass spectrometry (FI-MS) throughput could be as high as 4.3 sample injections/min, making very efficient use of mass spectrometers with negligible instrumental analysis time compared to the sample homogenization, preparation, and data processing steps.|Adequate analytical methods for enforcement purposes are available to monitor residues of aminocyclopyrachlor in grass commodities, milk, meat and meat byproducts. The analytical methods for both grass commodities and ruminant commodities use an LC/MS/MS system operating with an electrospray interface (ESI) in positive ion mode with limits of quantitation (LOQ) of 0.01 ppm.