Imazamox
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Imazamox
structure -
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CAS No:
114311-32-9
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Formula:
C15H19N3O4
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Chemical Name:
Imazamox
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Synonyms:
3-Pyridinecarboxylic acid,2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-(methoxymethyl)-;2-[4,5-Dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-(methoxymethyl)-3-pyridinecarboxylic acid;CL 299263;Imazamox;AC 299263;Raptor;Raptor (herbicide);Pulsar;(±)-Imazamox;5-Methoxymethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) nicotinic acid;Sweeper;Sweeper 70DG;2-[4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-methoxymethylnicotinic acid;Pulsar (herbicide);Pulsar 40;Global;(R,S)-Imazamox;182636-13-1
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CAS No:
Description
Off-White SolidImazamox (2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5- (methoxymethyl)-3-pyridinecarboxylic acid) is a systemic herbicide that moves throughout the plant tissue and prevents plants from producing a necessary enzyme, acetolactate synthase (ALS), which is not found in animals. Susceptible plants will stop growing soon after treatment, but plant death and decomposition will occur over several weeks.
2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid is a pyridinemonocarboxylic acid that is nicotinic acid which is substituted substituted at position 5 by a methoxymethyl group and at position 2 by a 4,5-dihydro-1H-imidazol-2-yl group, that in turn is substituted by isopropyl, methyl, and oxo groups at positions 4, 4, and 5, respectively. It is a pyridinemonocarboxylic acid, an ether, an imidazolone and a member of imidazolines.
Characteristics
101
0.73 (pH 5 & 6, corrected)
1.39 g/cm3 @ Temp: 20 °C
166 °C
1.603
Hexane 0.0006; methanol 6.68; acetonitrile 1.85; toluene 0.21; acetone 2.93; dichloromethane 14.3; ethyl acetate 1.02 (all g/100 mL)
0-6°C
1.26X10-11 mm Hg at 25 deg C (est)
LD50 (technical grade) orally in rats: >5000 mg/kg; dermally in rabbits: >4000 mg/kg; LC50 by inhalation in rats: >6.3 mg/l (Glover)
Odorless
Henry's Law constant = 9.15X10-19 atm-cu m/mol at 25 °C (est)
pKa1 = 2.3; pKa2 = 3.3|pKa = 2.3, 3.3 and 10.8; the active ingredient will exist primarily in the singly ionized form in the pH range 5-9
Partition coefficient (octanol/water): 0.004 (pH 7)|Hydroxyl radical reaction rate constant = 2.13X10-11 cu cm/mole-sec at 25 °C (est)
Product is not a corrosive hazard
Safety Information
UN30779/PG3
3
50/53
60-61
N
Stable under recommended storage conditions.
P273-P501
H410
SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product; Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging; Dispose of as unused product.
Strong oxidizing agents
|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H361 (11.18%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|Aggregated GHS information provided by 322 companies from 4 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).|Skin protection; Handle with 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).
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Wear self contained breathing apparatus for fire fighting if necessary.
Carbon oxides, nitrogen oxides (NOx)
Personal precautions, protective equipment and emergency procedures; Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.|Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Provide appropriate exhaust ventilation at places where dust is formed.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
It is not a /significant/ skin or eye irritant or a skin sensitizer.
SOIL: Water quality data compiled from the USGS National Water Information System (NWIS) reports soil monitoring data for imazamox. One routine sample was reported for Oct 22, 2014, imazamox was not detected, LOD = 31.1 ng/L(1).
Toxicity
IDENTIFICATION AND USE: Imazamox is off-white powdered solid. It is a herbicide applied post-emergence in soybean. HUMAN STUDIES: In an in vitro study, human embryonic stem cells were treated with imazamox at a concentration of 0, 1, 10 or 100 umol/L, incubation did not induce cytotoxicity. ANIMAL STUDIES: In the acute toxicity studies, the substance has low acute toxicity when administered orally, dermally or by inhalation to rats. It is not a significant skin or eye irritant or a skin sensitizer. Imazamox showed no short-term and long-term toxicity after oral exposure to rats, mice and dogs up to the limit top dose level tested in each study. Based on available genotoxicity studies imazamox is unlikely to be genotoxic. The substance showed no carcinogenic potential in both species. In the multigeneration toxicity study, fertility and overall reproductive performance was not impaired. In developmental toxicity studies maternal toxicity in rats and in rabbits was observed. No developmental toxicity was observed in rats whereas agenesis of the intermediate lobe of lung and cervical hemivertebra was observed in rabbits. ECOTOXICITY STUDIES: Imazamox is practically nontoxic to avian species, finfish, aquatic invertebrates, and honeybees following acute exposure.
LD50 Rat oral >5000 mg/kg bw|LD50 Rabbit dermal >4000 mg/kg bw
/AQUATIC SPECIES/ The highest concentrations of herbicides measured in flowing surface waters are often only present for short periods of time. These herbicide pulses can reach concentrations that would affect aquatic plants if present over a long time. The aim of this study was to assess the effect of a 3-hr herbicide pulse relative to the effects of long-term (4 and 7 days) exposure of six herbicides with different sites of action and different K(ow) on the growth of the floating macrophyte Lemna minor. The herbicides were the two photosynthetic inhibitors: diquat and terbuthylazine, the inhibitors of acetolactate syntase (ALS), imazamox and metsulfuron-methyl and the microtubule assembly inhibitors propyzamide and pendimethalin. The log K(ow) ranged from -4.6 to 5.2. For imazamox, metsulfuron-methyl, propyzamide and pendimethalin a 3-hr pulse induced the effect on area-specific growth as did a 4-day exposure at an approximate 10-fold higher concentration.|/PLANTS/ Alterations on growth, amino acids metabolism and some antioxidant enzyme activities as result of imazamox treatment were examined in determinate and indeterminate nodules, formed by Phaseolus vulgaris and Vicia sativa, respectively. Young seedlings of both legumes were inoculated with their respective microsymbionts and grown under controlled conditions. At vegetative growth, plants were treated with imazamox (250 uM) in the nutrient solution and harvested 7 days after. Imazamox was mainly accumulated in V. sativa where concentrations were more than six fold higher than those detected in P. vulgaris. Nodule dry weight and total nitrogen content were reduced by the herbicide treatment: the highest decrease of nodule biomass (50%) and nitrogen content (40%) were registered in V. sativa and P. vulgaris, respectively. The concentration of branched-chain amino acids (BCAA) did not change in neither determinate nor indeterminate nodules even though the acetohydroxyacid synthase activity decreased in root and nodules of both symbioses with the herbicide application. Based on this last result and taking into account that total free amino acids increased in roots but not in nodules of common vetch, a possible BCAA translocation from root to nodule could occur. Our results suggest that the maintenance of BCAA balance in nodule become a priority for the plant in such conditions. The involvement of activities glutathione-S-transferase, guaiacol peroxidase and superoxide dismutase in the response of the symbioses to imazamox are also discussed.|/OTHER TOXICITY INFORMATION/ ...Imazamox is practically nontoxic to avian species, finfish, aquatic invertebrates, and honeybees following acute exposure.
Imazamox's production may result in its release to the environment through various waste streams; its use as a broad-spectrum herbicide for post-emergence control of broadleaf weeds and grass (1,2) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 5 to 143(2) indicate that imazamox is expected to have very high mobility in soil(SRC). The pKa values of imazamox have been reported as 2.3, 3.3 and 10.8(3), indicating that this compound will exist entirely in anion form in the environment and anions generally do not adsorb as strongly to soils containing organic carbon and clay as their neutral counterparts(4). Volatilization of imazamox is not expected to be an important fate process(SRC) because this chemical expected to exist as an anion in the environment and anions do not volatilize. Imazamox is primarily degraded by microbes in soil under aerobic conditions(2,3); essentially no degradation occurs under anaerobic conditions(2). Imazamox is considered moderately persistent with half-lives ranging between 15 to 142 days(2,3); its limited persistence will restrict leaching of imazamox into groundwater(2).|TERRESTRIAL FATE: In a field study with 5 soils, terrestrial dissipation half-lives ranged between 15 and 130 days(1). Leaching was found to be very limited in field studies(2).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 5 to 143(2) indicate that imazamox is not expected to adsorb to suspended solids and sediment(SRC). The pKa values of imazamox have been reported as 2.3, 3.3 and 10.8(3) indicating imazamox will exist 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(SRC). According to a classification scheme(4), an estimated BCF of 3.2(SRC), from its log Kow of 0.73(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Photodegradation can be rapid with a half-life of 6.8 hours observed in laboratory studies(2,3); this rate is only applicable at the surface of the water with rates decreasing with water depth. Imazamox is stable to hydrolysis at pH 5, 7 and 9(2). Imazamox is considered moderately persistent in soil with half-lives ranging between 15 to 142 days(2,3).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), imazamox, which has an estimated vapor pressure of 1.26X10-11 mm Hg at 25 °C determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase imazamox may be removed from the air by wet and dry deposition(SRC). Imazamox photolytically decays with reported half-lives of 6.8 hours (or 0.3 days)(5,6) and 78 minutes (or 3 days)(7) for primary degradation in aqueous media. Direct aqueous photolysis results in several stable degradates(7). Photolysis in soil is a slower process with a half-life of 65 days(6). The rate of photodegradation decreases in the presence of Cu(II) and Ca(II) salts which form stable complexes with imazamox(7).
The rate constant for the vapor-phase reaction of imazamox with photochemically-produced hydroxyl radicals has been estimated as 2.13X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). However, this is not expected to be an important fate process as this chemical does not exist in the vapor phase in the ambient atmosphere. Imazamox is stable to hydrolysis at environmentally relevant pH values(3,5). No degradation was observed at 25 °C and pH values of 4, 5, 7, and 9 and a hydrolysis half-life of 192 days was reported for pH 9 at 25 °C(4,5). Imazamox photolytically decays with reported half-lives of 6.8 hours(or 0.3 days )(3,4) and 78 minutes (or 3 days)(6) for primary degradation in aqueous media. Direct aqueous photolysis results in several stable degradates, one was completely degraded after 100 hours while the remaining persist(6). Photolysis in soil is a slower process with a half-life of 65 days(4). The rate of photodegradation decreases in the presence of Cu(II) and Ca(II) salts which form stable complexes with imazamox(6).
Imazamox concentrations in whole and edible bluegill fish tissue were below the quantification limit, and the BCF for inedible tissue was less than 1X the concentration tested(1). An estimated BCF of 3.2 was calculated in fish for imazamox(SRC), using a log Kow of 0.73(2) and a regression-derived equation(3). According to a classification scheme(4), this BCF data suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The experimental Koc of imazamox ranges from 5 to 143, tested in soils with 0.29 to 2.59% organic carbon(1). According to a classification scheme(2), these Koc values suggest that imazamox is expected to have very high mobility in soil. The pKa values of imazamox have been reported as 2.3, 3.3 and 10.8(3), indicating that this compound will exist entirely in anion form in the environment and anions generally do not adsorb as strongly to soils containing organic carbon and clay than their neutral counterparts(4). While imazamox is considered very mobile, the terminal soil metabolite is moderately mobile to immobile, with Koc values ranging between 331 to 1924(5). Leaching of imazamox in field studies was very limited(5). Imazamox is generally weakly bound to soil, but adsorption increases as organic matter and clay content increase and decreasing pH can increase binding due to ionization(3). Adsorption is irreversible and increases with time and as soil becomes drier(3). Imazamox remains in the top 30 cm (12 inches) of soil and field studies suggest little potential for movement with surface water(3).
The Henry's Law constant for imazamox is estimated as 9.15X10-19 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that imazamox is expected to be essentially nonvolatile from water surfaces(2). The pKa values of imazamox have been reported as 2.3, 3.3, and 10.8(3). These values indicate imazamox will exist entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from moist soil is not expected to be an important fate process(2). Imazamox is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.26X10-11 mm Hg(SRC), determined from a fragment constant method(4).
GROUND WATER: Water quality data compiled from the Retrieval (STORET) Data Warehouse and the USGS National Water Information System (NWIS) reports ground water monitoring data for imazamox. USGS Water Science Center monitoring sites in the US as well as monitoring sites in the Minnesota Department of Agriculture - Pesticide Monitoring program and Arizona Dept of Environmental Quality report data for imazamox. Select data from the 2012 to 2017 monitoring years follows(1).[Table#6631]|SURFACE WATER: Water quality data compiled from the Retrieval (STORET) Data Warehouse and the USGS National Water Information System (NWIS) reports surface water monitoring data for imazamox. USGS Water Science Center monitoring sites in the US and the Minnesota Department of Agriculture - Pesticide Monitoring report data for imazamox. Select data from the 2012 to 2017 monitoring years follows(1).[Table#6632]
In FDA total diet studies analyzing foods as part of the pesticide monitoring program during the fiscal year 2014, imazamox was detected in 3% of food items examined at concentrations of 0.0001-0.005 ppm, in FY2013 imazamox was detected in 2% (0.0001-0.0007 ppm)(1). For fiscal years 2009 through 2012 imazamox was not listed in the reports(1). Imazamox was not listed in the FDA total diet study Market Baskets 2004 to 2005(2).
Occupational exposure to imazamox may occur through inhalation of dust and dermal contact with this compound at workplaces where imazamox is produced or used. Monitoring data indicate that the general population may be exposed to imazamox via ingestion of food and drinking water contaminated with this compound and dermal contact with surface waters containing this compound, especially in areas where it has been applied.(SRC)
Drug Information
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.)
Plant absorption: Absorption occurs through both the foliage and roots.|Rapidly excreted primarily in the urine following iv admin /to rats/, and in the urine and feces following oral admin, mainly as unchanged parent.|Forty-four Sprague Dawley rats (5/sex/group) were dosed with (14)C-/imazamox/ by a single intravenous (iv) dose at 10 mg/kg or a single oral gavage dose according to the following regiments: (1) 10 mg/kg body weight; (2) 14-day preconditioning with 10 mg/kg non-radiolabelled /imazamox/, followed by 10 mg/kg (14)C-/imazamox/; or (3) 1000 mg/kg body weight. The elimination patterns indicated that the radioactive residue were rapidly cleared from the body (ca. 95%) excreted in urine and recovered within 12 hours after dosing for all dose groups. Approximately, 74-75% of the radioactivity was absorbed via oral administration at 10 mg/kg dose and 74.4-74.5% excreted in urine and 18.7- 24.0% in feces. Much higher proportion of the dose was excreted in feces following oral dose (18.7- 24.0%) compared to iv injection (1.9-2.7%), most likely due to incomplete absorption. Three components accounted for ca. 99% of the total urinary radioactivity (98.2%, parent; 0.6%, 5- hydroxymethyl-nicotinic acid metabolite; and 0.4%, 5-carboxy-nicotinic acid metabolite) and ca. 89% of the extractable radioactivity in the feces (76.4%, parent; 9.6%, 5-hydroxymethyl-nicotinic acid metabolite; and 2.5%, 5-carboxy-nicotinic acid metabolite). The radioactive residues in the tissues were low (< 0.007%), and no (14)C-residues were detected in the expired air.|In rats, imazamox was rapidly absorbed, and the oral absorption was approximately 75% of the administered dose. Urine was the major route of excretion (>74%).
Imazamox is a racemic mixture. No information on chiral conversion in the mammalian metabolism or toxicity of specific enantiomer is available. However, information available in the fate and behaviour and residues section indicated that chiral conversion does not occur and exposure would be only to the racemic mixture.|Forty-four Sprague Dawley rats (5/sex/group) were dosed with (14)C-/imazamox/ ...Three components accounted for ca. 99% of the total urinary radioactivity (98.2%, parent; 0.6%, 5- hydroxymethyl-nicotinic acid metabolite; and 0.4%, 5-carboxy-nicotinic acid metabolite) and ca. 89% of the extractable radioactivity in the feces (76.4%, parent; 9.6%, 5-hydroxymethyl-nicotinic acid metabolite; and 2.5%, 5-carboxy-nicotinic acid metabolite). The radioactive residues in the tissues were low (<0.007%), and no (14)C-residues were detected in the expired air.|(14)C-(15)N-labelled/unlabelled imazamox mix was incubated with dog, rabbit, rat, mouse or human liver microsomes in the presence of a nicotinamide adenine dinucleotide phosphate (NADPH)-generating system. With 90% recovered radioactivity and above, only the parent molecule was detected in all test systems by high-performance liquid chromatographic analysis in fresh samples after the incubation. Under the conditions of the study, imazamox was not metabolized by liver microsomes of dogs, rabbits, rats, mice or humans. No unique human metabolite was detected. Under the conditions of the study, the positive control, testosterone, was metabolized by the microsome samples originating from different species.|In rats, imazamox was rapidly absorbed, and the oral absorption was approximately 75% of the administered dose. Urine was the major route of excretion (>74%). Most of the elimination occurred within the first 24 hours after dosing, as unchanged parent compound. Smaller amounts of the test substance were excreted through faeces (>19% in animals receiving 10 mg/kg bw and approximately 10-20% in animals receiving 1000 mg/kg bw). Only trace amounts of tissue residue were detected. Imazamox appears not to be metabolized. Trace levels of imazamox-related compounds detected in the urine and faeces were attributed to the presence of impurities in the dosing solution, not to rat metabolism.
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/|Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an iv with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/PREGNANCY AND HUMAN REPRODUCTION/ In an in vitro study, human embryonic stem cells (WA09) were treated with imazamox at a concentration of 0, 1, 10 or 100 umol/L. Metabolomic changes were assessed by liquid chromatographic-mass spectrometric analysis. According to the authors, incubation did not induce cytotoxicity. Data were analysed with models to predict developmental toxicity, which were set up with data from (1) pharmaceutical agents or (2) selected pesticides from the USEPA's Toxicity Reference Database (ToxRefDB). ...
imazamox
Imazamox Use and Manufacturing
The first preparation method uses propionaldehyde as the starting material, and forms a series of reactions with formaldehyde condensation, ring closure, halogenation, methoxylation and the like to obtain methoxazone smoke. Preparation method 2: Methoxypropanal, diethyl oxalate, and methyl isopropyl ketone are used as starting materials to prepare methimifen smoke through the following series of reactions.
Herbicide.
Raptor Herbicide Technical (BASF Corporation): Active ingredient: imazamox 97.4%.|Raptor Herbicide (BASF Corporation): Active ingredient: imazamox 12.1%.|Raptor DG Herbicide (BASF Corporation): Active ingredient: imazamox 70%.|Clearcast Herbicide (BASF Corporation): Active ingredient: imazamox 12.1%.|For more Formulations/Preparations (Complete) data for Imazamox (10 total), please visit the HSDB record page.
Imazamox is a selective broad-spectrum herbicide with contact and residual activities, used post-emergence for the control of broadleaf and grass weeds in soya beans and other vegetables grown in rotation with sugar beet and other crops. It inhibits acetolactate synthase.
... this study aimed to develop a simple and efficient method for determination of imidazolinones (imazamox, imazapic, imazapyr, imazaquin and imazethapyr) residues in soil, using an extraction with aqueous ammonium acetate solution (0.5 M) and clean-up with dispersive solid phase extraction employing PSA, followed by UHPLC-MS/MS analysis. Satisfactory values of accuracy (70-93%) and RSD (=17%) were achieved, as well as lower limit of quantification (5.0 ug kg(-1)). Considering the matrix and compounds complexity, the developed and validated method proved to be an excellent tool for rapid analysis (20 min), with reliability for application in real samples with wide pH range. In the analysis of 22 real samples, the method allowed the quantification of imazapic (5.84 and 12.1 ug kg(-1)), imazapyr (5.3 ug kg(-1)) and imazethapyr (24.0 and 37.7 ug kg(-1)) in three samples.|Imazamox is extracted from soybean seed with acidic aqueous methanol and cleaned up via solvent partitioning and solid phase extraction techniques. Imazamox is determined by HPLC equipped with a UV detector. The detection sensitivity of this method is 50 ppb. Imazamox and its metabolites are extracted from soil using 0.5 N NaOH. Following precipitation and filtration, the extract is fractionated by differential elution. To separate imazamox from its metabolite, each fraction is analyzed by HPLC on a reverse phase column. Level of quantification is 5 ppb.|OBJECTIVE: To develop a method based on liquid chromatography and ultraviolet absorption detection for simultaneous determination of imazamox and its metabolites in plants. Sample preparation was based on ultrasound-assisted extraction (70 W power and duty cycle of 0.7 s/s for 10 min) with subsequent filtration of the extracts and clean-up and concentration prior to chromatographic separation and detection at 240 nm. The chromatographic analysis was completed in 30 min using a Luna HILIC column. Identification and confirmatory analysis of the presence of imazamox and its metabolites in extracts from treated plants was performed by LC-TOF/MS in high resolution mode for precursor ions. The metabolites were quantified using a surrogate approach based on an imazamox standard. The method was validated by analysing wheat samples treated with 200 g per hectare of active ingredient imazamox. The linear dynamic range of the calibration curve was within 0.27-600 ug/mL, with a correlation coefficient of 0.998 and precision--studied at 0.1 and 2 ug/mL--of 2.9% and 5.0% for repeatability, and 4.7% and 6.9% for reproducibility, respectively. The analytical characteristics of the method make it recommendable for evaluating the metabolism of imazamox in plants.|The photodecomposition of imazamox, a herbicide of the imidazolinone family, was investigated in pure water. The main photoproducts from the photolysis were followed over time by liquid chromatography mass spectrometry and structures were proposed from exact mass determinations obtained by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. The method comprised exact mass determination with better than 0.2 ppm mass accuracy and a corresponding structural visualization taking care of respective isotopes with an adapted van Krevelen diagram that enabled a systematic approach to the characterisation of the elementary composition of each photoproduct. By taking advantage of the high resolving power of FT-ICR MS to make precise formula assignments, the derived 2D van Krevelen diagram (O/C; H/C; m/z) enabled one to structurally differentiate the formed photoproducts and to propose a degradation pathway for imazamox.|For more Analytic Laboratory Methods (Complete) data for Imazamox (9 total), please visit the HSDB record page.
Agrochemicals -> Herbicides|Environmental transformation -> Pesticides (parent, predecessor)
Imazamox has known environmental transformation products that include CL 312622 and CL 354825.
Computed Properties
Molecular Weight:305.33
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:305.13755610
Monoisotopic Mass:305.13755610
Topological Polar Surface Area:101
Heavy Atom Count:22
Complexity:491
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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