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Penoxsulam

Penoxsulam structure

Penoxsulam 

structure
  • CAS No:

    219714-96-2

  • Formula:

    C16H14F5N5O5S

  • Chemical Name:

    Penoxsulam

  • Synonyms:

    Benzenesulfonamide,2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)-;2-(2,2-Difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide;Penoxsulam;Granite;DASH 001;Ricer 240SC;Granite SC;Grasp;Grasp (benzenesulfonamide);Grasp EC;Clipper;Clipper (benzenesulfonamide);Clipper 20OD;Ricer;Granite (herbicide);Viper;Rainbow 25OD

  • Categories:

    Agrochemicals  >  Herbicides

Description

Penoxsulam is a member of triazolopyrimidines.

Penoxsulam Basic Attributes

483.37

483.37

1806241-263-5

784ELC1SCZ

DTXSID0034803

Off-white|Tan solid

Characteristics

125

-0.354

1.61 at 20 deg C

223-224 °C

1.588

In water (mg/L at 20 deg C): 5.7 mg/L at pH 5; 408 mg/L at pH 7; 1460 at pH 9

0-6°C

9.55X10-11 mPa /SRC: 7.2X10-16 mm Hg/ at 25 deg C

LD50 (mg/kg): >5000 orally in rats; >5000 dermally in rabbits; LC50 (8 day) in bobwhite quail, mallard duck (ppm): >4411, >4310; LC50 (96 hr) in rainbow trout, bluegill sunfish, common carp (mg/l): >102, >103, >101 (Larelle)

Musty

Henry's Law constant = 1.1X10-18 atm-cu m/mole at 25 °C (est)

pKa = 5.1

Safety Information

UN 3077 9 / PGIII

3

50/53

61

N

Thermally stable at typical use temperatures. /Grasp SC Herbicide/

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.|Waste resulting from the use of this product must be disposed of on site or at an approved waste disposal facility. /Grasp SC Herbicide/|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential users/|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential users/

Avoid contact with oxidizing materials.

|Warning|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 250 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Applicators and other handlers must wear: Long-sleeved shirt and long pants. Shoes plus socks. /Grasp SC Herbicide/|... Restricted entry interval (REI) of 12 hours. 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. Chemical-resistant gloves made of any waterproof material. Shoes plus socks. /Grasp SC Herbicide/

Special Protective Equipment for Firefighters. Wear positive-pressure self-contained breathing apparatus (SCBA) and protective fire fighting clothing (includes fire fighting helment, coat, trousers, boots, and gloves). If protective equipment is not available or not used, fight fire from a protected location or safe distance. /Grasp SC Herbicide/|Keep people away. Isolate fire and deny unnecessary entry. To extinguish combustible residues of this product use water fog, carbon dioxide, dry chemical or foam. Contain fire water run-off if possible. Fire water run-off, if not contained, may cause environmental damage. /Grasp SC Herbicide/

Do not contaminate water when disposing of equipment washwater or rinsate. /Grasp SC Herbicide/|ACCIDENTAL RELEASE MEASURES. ... Contain spilled material if possible. Small spills: Absorb with materials such as: Clay. Dirt. Sand. Zorb-all. Collect in suitable and properly labeled containers. /Grasp SC Herbicide/|If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

Use this product only in accordance with its labelling and with the Worker Protection Standard, 40 CFR part 170. /Grasp SC Herbicide/|Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. /Grasp SC Herbicide/|Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Grasp SC 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. /Grasp SC Herbicide/|For more Preventive Measures (Complete) data for Penoxsulam (23 total), please visit the HSDB record page.

Toxicity

LC50 Rat inhalation > 2 mg/kg/4 hr|LD50 Rabbit dermal > 5,000 mg/kg|LD50 Rat oral > 5,000 mg/kg

Penoxsulam'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), a Koc value of 30(SRC), using a log Kow of -0.35(2) and a regression-derived equation(3), indicates that penoxsulam is expected to have very high mobility in soil(SRC). The pKa of penoxsulam is 5.1(2), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of penoxsulam from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-18 atm-cu m/mole(SRC), based upon its vapor pressure, 7.2X10-16 mm Hg(2), and water solubility, 408 mg/L(2). Penoxsulam is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). In soil penoxsulam is expected to biodegrade rapidly based on reported aerobic half-lives of 22 to 58 days at 20 °C and an anaerobic half-life of 6.6 days also at 20 °C(2). Penoxsulam is rapidly photodegraded from soil with half-lives of 5.2 to 12.8 days(5).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 30(SRC), using a log Kow of -0.35(2) and a regression-derived equation(3), indicates that penoxsulam is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.1X10-18 atm-cu m/mole(SRC), derived from its vapor pressure, 7.2X10-16 mm Hg(2), and water solubility, 408 mg/L(2). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Aqueous biodegradation of penoxsulam is expected based on reported anaerobic half-lives of 2 to 13 days in simulated flooded rice field conditions(2). Penoxsulam is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Penoxsulam is rapidly photodegraded from water with half-lives of 2.9 to 26.5 days(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), penoxsulam, which has a vapor pressure of 7.2X10-16 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase penoxsulam may be removed from the air by wet or dry deposition(SRC).

Penoxsulam is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Penoxsulam is rapidly photodegraded from soil with half-lives of 5.2 to 12.8 days and from water with half-lives of 2.9 to 26.5 days(2).

An estimated BCF of 3 was calculated in fish for penoxsulam(SRC), using a log Kow of -0.35(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). Penoxsulam is reported to be rapidly excreted with low potential to bioaccumulate(1).

The Koc of penoxsulam is estimated as 30(SRC), using a log Kow of -0.35(1) and a regression-derived equation(2). According to a classification scheme(3), this Koc value suggests that penoxsulam is expected to have very high mobility in soil. Kd values of penoxsulam have been reported to range from 0.14 to 5.05(3). The pKa of penoxsulam is 5.1(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

The Henry's Law constant for penoxsulam is estimated as 1.1X10-18 atm-cu m/mole(SRC) derived from its vapor pressure, 7.2X10-16 mm Hg(1), and water solubility, 408 mg/L(1). This Henry's Law constant indicates that penoxsulam is expected to be essentially nonvolatile from water surfaces and moist soil(2). Penoxsulam is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Penoxsulam residual was not detected (detection limit 0.002 mg/kg) in harvested rice grain(1).

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

Drug Information

All dosing was by gavage with labeled penoxsulam (XDE-638) (97.5% purity of unlabeled penoxsulam, triazole label purity > 99%, phenyl ring label purity 98.4%) in 0.5% Methocel suspension. Generally, groups of 4 rats/sex were used in each of 8 tests using triazole-labeled 14C-XDE-638. One additional set of 4 males was tested using phenyl-labeled 14C-XDE-638 to assess the extent of cleavage between triazole and phenyl moieties. Rats fitted with jugular vein cannulae were used primarily to determine the time course of residue concentrations in plasma, urine, and feces after single dosing with either 5 or 250 mg/kg penoxsulam. These rats were sacrificed on day 7 (as were the phenyl-labeled males), and tissue residues were determined at that time. Time to maximal plasma concentration (Cmax) was about 0.5 hr and 2 hr for both sexes at 5 and 250 mg/kg, respectively. Time to half of maximal concentration of radiolabel (1/2 Cmax) at 5 and 250 mg/kg were determined to be 2.6 hr and 3.0 hr for males, respectively, and 2.9 hr and 5.6 hr for females, respectively. Thus four sets of males and females were sacrificed following single oral dosing to achieve approximately Cmax and 1/2 Cmax plasma levels at the two dose levels, and to obtain tissue and excreta samples at early stages of exposure. Radiolabel was measured in each of 24 tissues at each sacrifice time. Quantities of major metabolites were assessed in pooled plasma at various intervals, and in liver and kidney tissue at sacrifice times. Three rats/sex were fitted with bile duct cannulae, and bile was collected at intervals over 24 hr to assess biliary excretion rate and metabolite analysis. Four additional rats/sex were dosed daily for 15 days with 5 mg/kg/day prior to treatment with triazole labeled 14C-XDE-638 on day 16. These rats were evaluated for residues in excreta and for tissue levels of metabolites, which were found to be comparable to non-pre-treated rats. Metabolite separation was by HPLC using C-18 stationary phase and a gradient program sufficient to separate most major peaks for detection by UV (254 nm) and by 14C-detector. Metabolite identification was by retention time and negative ion LC/MS. Estimated total absorption after 5 mg/kg was about 85% for either sex). Absorption was much lower after 250 mg/kg (17% in males, 32% in females). Unless otherwise stated, results below derive from single-dose administration of 5 mg/kg triazole-labeled penoxsulam. A comparison of distribution patterns of urinary and fecal metabolites following phenyl- or triazole-label indicated that most (at least 90%) of penoxsulam residues remained intact between the two labeled rings. Parent compound was the most abundant urinary residue, constituting about 31% and 19% of administered dose in urine samples of males dosed with triazole- or phenyl-labeled 14C, respectively. Females consistently excreted much larger percentages of label in urine than did males. In the 7-day urine collection in females, 66% of administered dose was parent penoxsulam. The most abundant fecal metabolite in either sex in the 7-day collection was an uncharacterized 'Metabolite Y,' comprising 14% to 19% of administered dose in males and 6% in females. Parent penoxsulam constituted 12% to 15% of administered label in feces of males and 3% in females. About 88% of 24-hr fecal label in males represented absorbed penoxsulam, based on percentage of label excreted in the bile. As expected, considering the proportionally higher excretion of label in females via the urine, females excreted much less in 24-hr bile collections than did males (14% of administered dose in females vs. 56% of administered dose in males). The largest single provisionally identified component of bile was the glutathione product of 5-hydroxy- or 8-hydroxy-penoxsulam (18% of administered penoxsulam). Two glucuronide products of hydroxylated penoxsulam (position of hydroxylation product unknown in either case) appeared to account together for about 15% of administered label in bile. Tissue concentration evaluations during times of 1/2 Cmax plasma concentrations revealed relatively high initial liver residue concentrations, whereas other tissues (except for 'GI/Ingesta') had much lower levels. Radiolabel in liver and in all other tissues were very low by day 7. Parent penoxsulam was much more abundant than any other residues in plasma, liver, and kidneys. Comparative concentrations of penoxsulam in ug-equivalents/g tissue at the time of plasma 1/2 Cmax for these tissues in males and females, respectively, were 10 and 9 for plasma, 44 and 50 for liver, and 3 and 4 for kidney. Originally, this study was unacceptable but upgradeable with identification of 'Metabolite Y,' which constituted up to 19% of fecal residues|In a metabolism study in rats, (14)C-penoxsulam was rapidly and nearly completely absorbed at the low dose of 5.0 mg/kg, but at the high dose of 250 mg/kg, there was evidence that absorption was largely incomplete (i.e. absorption was saturated). Both gender and dose affected the excretion pattern. At the low dose, the major route of excretion of radioactivity was via the feces in males and via the urine in females. At the high dose, radioactivity was predominantly excreted via the feces in both sexes. A significant enterohepatic circulation was observed, particularly in males. Most (>90%) of the administered dose was excreted within 36-48 hours. There was negligible radioactivity in tissues at 7 days and no evidence of accumulation in any tissue/organ. Although numerous metabolites were revealed in the urine, feces and bile, nearly all were <1% of the administered dose. Parent compound and a 2-hydroxyphenyl derivative were the major compounds in urine and feces.

All dosing was by gavage with labeled penoxsulam (XDE-638) (97.5% purity of unlabeled penoxsulam, triazole label purity > 99%, phenyl ring label purity 98.4%) in 0.5% Methocel suspension. Generally, groups of 4 rats/sex were used in each of 8 tests using triazole-labeled 14C-XDE-638. One additional set of 4 males was tested using phenyl-labeled 14C-XDE-638 to assess the extent of cleavage between triazole and phenyl moieties. Rats fitted with jugular vein cannulae were used primarily to determine the time course of residue concentrations in plasma, urine, and feces after single dosing with either 5 or 250 mg/kg penoxsulam. ... Quantities of major metabolites were assessed in pooled plasma at various intervals, and in liver and kidney tissue at sacrifice times. Three rats/sex were fitted with bile duct cannulae, and bile was collected at intervals over 24 hr to assess biliary excretion rate and metabolite analysis. Four additional rats/sex were dosed daily for 15 days with 5 mg/kg/day prior to treatment with triazole labeled 14C-XDE-638 on day 16. These rats were evaluated for residues in excreta and for tissue levels of metabolites, which were found to be comparable to non-pre-treated rats. Metabolite separation was by HPLC using C-18 stationary phase and a gradient program sufficient to separate most major peaks for detection by UV (254 nm) and by 14C-detector. Metabolite identification was by retention time and negative ion LC/MS. ... A comparison of distribution patterns of urinary and fecal metabolites following phenyl- or triazole-label indicated that most (at least 90%) of penoxsulam residues remained intact between the two labeled rings. Parent compound was the most abundant urinary residue, constituting about 31% and 19% of administered dose in urine samples of males dosed with triazole- or phenyl-labeled 14C, respectively. ... The most abundant fecal metabolite in either sex in the 7-day collection was an uncharacterized 'Metabolite Y,' comprising 14% to 19% of administered dose in males and 6% in females. Parent penoxsulam constituted 12% to 15% of administered label in feces of males and 3% in females. ... The largest single provisionally identified component of bile was the glutathione product of 5-hydroxy- or 8-hydroxy-penoxsulam (18% of administered penoxsulam). Two glucuronide products of hydroxylated penoxsulam (position of hydroxylation product unknown in either case) appeared to account together for about 15% of administered label in bile. ...

Sulfonamide herbicides ... inhibit the enzyme acetolactate synthase (ALS)... /Sulfonamides/

/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/

penoxsulam

Penoxsulam Use and Manufacturing

Methods of Manufacturing

Penoxsulam can be prepared by reaction of 2-amino-5,8-dimethoxy-1,2,4-triazole with 2- (2,2-difluoroethyl)-6-trifluoromethylbenzenesulfonyl chloride in the presence of a base.

Uses

Herbicide.

Granule; oil dispersion; suspension concentrate (= flowable concentrate)|PREMIX PARTNERS: Cyhalofop-butyl; Triclopyr.|Turf Fertilizer Plus Penoxsulam Weed Control (Lebanon Seaboard Corporation) 0.03% Penoxsulam|Penoxsulam Technical (Dow Agrosciences LLC.) 98% Penoxsulam|For more Formulations/Preparations (Complete) data for Penoxsulam (28 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies penoxsulam as unlikely to present an acute hazard in normal use; Main Use: herbicide.

Method: Abraxis 515565; Procedure: colorimetric immunoassay; Analyte: penoxsulam; Matrix: water (groundwater, surface water, well water); Detection Limit: 0.17 ppb.|Determination of residues in soil or water by lc/ms/ms.

Agrochemicals -> Herbicides|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Penoxsulam has known environmental transformation products that include Penoxsulam metabolite 5-OH, Penoxsulam metabolite BSA, Penoxsulam metabolite BST, Penoxsulam metabolite BSTCA, and Penoxsulam metabolite SFA.

Computed Properties

Molecular Weight:483.4
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:14
Rotatable Bond Count:8
Exact Mass:483.06358055
Monoisotopic Mass:483.06358055
Topological Polar Surface Area:125
Heavy Atom Count:32
Complexity:727
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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