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Sulfentrazone

Sulfentrazone structure

Sulfentrazone 

structure
  • CAS No:

    122836-35-5

  • Formula:

    C11H10Cl2F2N4O3S

  • Chemical Name:

    Sulfentrazone

  • Synonyms:

    Methanesulfonamide,N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]-;N-[2,4-Dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide;F 6285;Sulfentrazone;Authority;Authority 75DF;Capaz;Boral;Blanket;Spartan;Dismiss;2′,4′-Dichloro-5′-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)methanesulfonanilide;111991-58-3

  • Categories:

    Organic Chemistry  >  Amides

Description

Solid


Solid


Sulfentrazone is a member of the class of triazoles that is 5-oxo-1,2,4-triazole which is substituted at positions 1, 3, and 4 by 2,4-dichloro-5-[(methylsulfonyl)amino]phenyl, methyl, and difluoromethyl groups, respectively. A protoporphyrinogen oxidase inhibitor, it is used as a herbicide to control broad-leaved weeds in soya and tobacco crops. Not approved for use within the European Union. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor, a herbicide and an agrochemical. It is a sulfonamide, a dichlorobenzene, an organofluorine compound and a member of triazoles.

Sulfentrazone Basic Attributes

387.19

387.19

602-896-4

7TY7WT1599

DTXSID6032645

Tan solid

Characteristics

90.5

0.99 @ pH 7

Solid

1.21 g/cm3 @ Temp: 20 °C

121-123 °C

468.2±55.0 °C at 760 mmHg

237.0±31.5 °C

1.646

In water, 110 mg/l (pH 6) at 25 deg C; 780 mg/l (pH 7) at 25 deg C; 16000 mg/l (pH 7.5) at 25 deg C

0-6°C

9.75X10-10 mm Hg @ 25 deg C

Faint sulfur-like

pKa = 6.56

173.63 Ų [M+H]+ [CCS Type: TW]

Safety Information

UN3077 (solid); UN3082(liquid)

P260, P261, P271, P273, P304+P312, P304+P340, P312, P314, P391, P501

H332

|Warning|H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]|P260, P261, P271, P273, P304+P312, P304+P340, P312, P314, P391, and P501|Aggregated GHS information provided by 127 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

LD50 Rat oral 2855 mg/kg|LD50 Rabbit percutaneous >2000 mg/kg|LC50 Rat inhalation >4.14 mg/L/4 hr|LD50 Rat dermal >2000 mg/kg

Sulfentrazone's production may result in its release to the environment through various waste streams; it's use as a herbicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Sulfentrazone has high mobility in soil based on an average Koc of 43 (and Kd < 1) with a strong potential to leach into groundwater and move offsite to surface water(1). A groundwater monitoring study in North Carolina determined sulfentrazone leaches substantially to groundwater in areas with sandy soil(1). Volatilization losses from soil are negligible(2). Direct photolysis of sulfentrazone in aqueous solutions is rapid (half-life of 1 to 12 hours)(3), therefore, photodecomposition on soil surfaces exposed to sunlight may be possible. Based on laboratory tests, loss of sulfentrazone in soil appears to be primarily by microbial degradation(2). An aerobic half-life of 1.5 years and anaerobic half-life of 9 years has been reported(1). The field dissipation half-life is reported to range from 110 to 280 days(2).|AQUATIC FATE: Based on an average Koc of 43 (and Kd < 1), sulfentrazone is not expected to adsorb to suspended solids and sediment(1). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 6.37X10-13 atm-cu m/mole(SRC), derived from its vapor pressure, 9.75X10-10 mm Hg(3), and water solubility, 780 mg/l(3). According to a classification scheme(4), an estimated BCF of 3.1(SRC), from an experimental log Kow(1) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Direct photolysis of buffered aqueous solutions exposed to simulated sunlight occurs rapidly with half-lives of about 1 hour at pH 6 and pH 7, and 12 hours at pH 5(6). Sulfentrazone is stable to hydrolysis and biodegradation(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfentrazone, which has a vapor pressure of 9.75X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase sulfentrazone may be removed from the air by wet and dry deposition(SRC).

The aqueous photolysis of radiolabeled sulfentrazone was studied in sterile pH 5, 7 and 9 buffers(1). Quartz tubes containing the buffers were exposed to continuous illumination from a filtered xenon lamp with output set equivalent to summer irradiation at 40 deg N latitude(1). At pH 7 and 9, sulfentrazone had photolysis half-lives of about 1 hour; photolysis at pH 5 was somewhat slower with a half-life of about 12 hours(1). Whole molecule photolysis involved de-chlorination, and in some cases, replacement of the halogen(s) with hydroxyl groups(1).|The rate constant for the vapor-phase reaction of sulfentrazone with photochemically-produced hydroxyl radicals has been estimated as 2.45X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Sulfentrazone is not susceptible to aqueous hydrolysis(2).

An estimated BCF of 3.1 was calculated for sulfentrazone(SRC), using an experimental log Kow of 0.99 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).

Sulfentrazone has a reported average Koc of 43 (and Kd < 1) and a high mobility in soil(1). Sulfentrazone has also been reported to be moderately mobile in soil with a mobility greater than alachlor, but less than metribuzin(2). The compound showed a strong potential to leach into groundwater and move offsite to surface water; a groundwater monitoring study in North Carolina determined sulfentrazone leaches substantially to groundwater in areas with sandy soil(1).

The Henry's Law constant for sulfentrazone is estimated as 6.37X10-13 atm-cu m/mole(SRC) derived from its vapor pressure, 9.75X10-10 mm Hg(1), and water solubility, 780 mg/l(1). This Henry's Law constant indicates that sulfentrazone is expected to be essentially nonvolatile from water surfaces(2). Sulfentrazone is reported to have negligible volatilization losses from soil(3).

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

Drug Information

A metabolism study in rats resulted in the admin dose & nearly all radioactivity excreted in the urine, indicating nearly complete absorption. most of the test article was eliminated by urine & feces within 72 hr, & appeared to be independent of dose & sex.|Mode of action: Herbicide absorbed by the roots & foliage, with translocation primarily in the apoplasm, & limited movement in the phloem.

In soya beans, over 95% of the parent sulfentrazone is metabolized to the non-polar, hydroxymethyl analogue within 12 hr. This analogue is also rapidly converted, over the same time period, to three polar metabolites, two of which are glycosidic derivatives & one a non-glycoside metabolite.

Mode of action: Herbicide absorbed by the roots & foliage, with translocation primarily in the apoplasm, & limited movement in the phloem. Acts through the inhibition of protoporphyrinogen oxidase in the chlorophyll biosynthesis pathway, leading to the subsequent build-up of toxic intermediates.

FP 846

Sulfentrazone Use and Manufacturing

Uses

Herbicide.

USEPA/OPP Pesticide Code 129081; Trade Names: F6285(Herbicide), FMC 97285, Sulfentrazone(F6285) 4F Herbicide, Sulfentrazone(F6285) 75DF Herbicide.|92.2% technical; 39.6% flowable liquid end-use; 75.0% water dispersible granule end-use|AUTHORITY premix of sulfentrazone + chlorimuron-ethyl at 56.3% + 9.4%, DG; CANOPY XL premix of sulfentrazone + chlorimuron-ethyl at 56.3% + 9.4%

Agrochemicals -> Herbicides

Computed Properties

Molecular Weight:387.2
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:385.9818731
Monoisotopic Mass:385.9818731
Topological Polar Surface Area:90.5
Heavy Atom Count:23
Complexity:613
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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