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Home > Encyclopedia > Fluthiacet-methyl

Fluthiacet-methyl

Fluthiacet-methyl structure

Fluthiacet-methyl 

structure
  • CAS No:

    117337-19-6

  • Formula:

    C15H15ClFN3O3S2

  • Chemical Name:

    Fluthiacet-methyl

  • Synonyms:

    Acetic acid,2-[[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]thio]-,methyl ester;Acetic acid,[[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]thio]-,methyl ester;1H,3H-[1,3,4]Thiadiazolo[3,4-a]pyridazine,acetic acid deriv.;Methyl 2-[[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]thio]acetamide;Fluthiacet-methyl;KIH 9201;Action;CGA 248757;Blizzard;Appeal;Cadet;177602-28-7

Description

Fluthiacet-methyl is a methyl ester resulting from the formal condensation of the carboxy group of fluthiacet with methanol. A proherbicide for fluthiacet, it is used for the control of broad-leaved weeds in crops such as maize and soya. It has a role as an agrochemical, an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor and a proherbicide. It is an organic sulfide, a methyl ester, a member of monochlorobenzenes, a member of monofluorobenzenes and a thiadiazolopyridazine. It derives from a fluthiacet.

Fluthiacet-methyl Basic Attributes

403.87900

403.88

601-473-1

7C989JK2XB

DTXSID2032556

White powder|Ivory powder

2930909056

Characteristics

119.13000

2.79510

White powder

1.57 g/cm3

106 °C

503.5ºC at 760 mmHg

258.3ºC

1.69

2.10e-06 M|In methanol 4.41, acetone 101, toluene 84, n-octanol 1.86, acetonitrile 68.7, ethyl acetate 73.5, dichloromethane 9 (all in g/L at 25 °C); in n-hexane 0.232 g/L at 20 °C.|In water 0.85 (distilled), 0.78 (pH 5 and 7) mg/L at 25 °C.

0-6ºC

2.9E-10mmHg at 25°C

Odorless

Henry's Law constant= 2.1X10-9 atm-cu m/mole at 25 °C /Estimated/

Hydroxyl radical reaction rate constant= 3.4X10-11 cu cm/molecule-sec at 25 °C /Estimated/

Safety Information

In water, DT50 484.8 days (pH 5), 17.7 days (pH 7), 0.2 days (pH 9). In light, DT50 4.92 days.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P273, P280, P305+P351+P338, P337+P313, P391, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Long-sleeved shirt and long pants. Shoes plus socks. Waterproof gloves.

/To extinguish fire use/ dry chemical powder, foam, carbon dioxide or dry sand.

Toxicity

LD50 Rat oral >5000 mg/kg|LC50 Rat inhalation (nose only) >5.048 mg/L air/4 hr|LD50 Rabbit dermal >2000 mg/kg

Fluthiacet-methyl'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: Based on a classification scheme(1), an estimated Koc value of 2,700(SRC), determined from a log Kow of 3.77(2) and a regression-derived equation(3), indicates that fluthiacet-methyl is expected to have slight mobility in soil(SRC). Volatilization of fluthiacet-methyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 3.31X10-9 mm Hg(2), and water solubility, 0.86 mg/L(2). Fluthiacet-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.31X10-9 mm Hg(2). A photolysis half-life on soil of 21 days has been reported(2).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,700(SRC), determined from a log Kow of 3.77(2) and a regression-derived equation(3), indicates that fluthiacet-methyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 3.31X10-9 mm Hg(2), and water solubility, 0.86 mg/L(2). According to a classification scheme(4), an estimated BCF of 160(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A hydrolysis half-life of 18 days (pH 7) has been reported(2).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluthiacet-methyl, which has a vapor pressure of 3.31X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase. Particulate-phase fluthiacet-methyl may be removed from the air by wet and dry deposition(SRC). A half-life in light of 4.92 days has been reported(2).|Stability in water DT50 484.8 days (pH 5), 17.7 days (pH 7), 0.2 days (pH 9). In light DT50 of 4.92 days.

A hydrolysis half-life of 18 days at pH 7 and a photolysis on soil half-life of 21 days have been reported for fluthiacet-methyl(2).

An estimated BCF of 160 was calculated for fluthiacet-methyl(SRC), using a log Kow of 3.77(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered physically or chemically once released into the environment.

The Koc of fluthiacet-methyl is estimated as 2,700(SRC), using a log Kow of 3.77(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that fluthiacet-methyl is expected to have slight mobility in soil.

The Henry's Law constant for fluthiacet-methyl is estimated as 2.1X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 3.31X10-9 mm Hg(1), and water solubility, 0.85 mg/L(1). This Henry's Law constant indicates that fluthiacet-methyl is expected to be essentially nonvolatile from water surfaces(2). Fluthiacet-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

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

Drug Information

...Fluthiacet-methyl was absorbed rapidly at both the low and high dose for both male and female rats. Repeated oral dosing had no effect on extent of absorption. Tissue levels of 14C-fluthiacet-methyl derived radioactivity in the single and repeated low dose groups did not exceed 0.018 ppm for any tissue. At the single high dose, female rats showed higher levels of 14C-fluthiacet-methyl derived radioactivity in tissues than males except for muscle, brain, fat and plasma. Excretion in males was predominantly in feces for all dose groups, with between 67-87% of administered radioactivity excreted by this route. In females, the percentage of administered radioactivity in urine across all dose groups (40-48%) was approximately equivalent to the percent excreted in feces (39-52%). The greater fecal excretion in males was based on a greater percentage excretion in bile for males (37%) vs. females (19%).

/SRP:/ 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/|/SRP:/ 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/

Fluthiacet-methyl Use and Manufacturing

Methods of Manufacturing

Fluthiacet-methyl is produced by reaction of 1-[(2-fluoro-4-chloro-5-thiomethylacetate)phenylthiocarbamoyl]-2-methoxycarbonylhexahydropyridazine with methanolic potassium hydroxide, followed by treatment with trichloromethyl chloroformate.

Uses

For fluthiacet-methyl (USEPA/OPP Pesticide Code: 108803) ACTIVE products with label matches. /SRP: 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./|Herbicide; Cotton defoliant, broadleaf weed control in field corn or soybeans.

Trade names: Action, Appeal|Emulsifiable concentrate, wettable powder.

Preparation:M. Yamaguchi et al., EP 273417; eidem, US 4906279 (1988,1990 both to Kumiai Chem Ind)|Fluthiacet-methyl, which inhibits protoporphyrinogen oxidase, is a selective contact herbicide used post--emergence for the control of broad-leaved weeds in maize and soya beans.

Product and residue analysis by glc with NPD.

Computed Properties

Molecular Weight:403.9
XLogP3:3.9
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:5
Exact Mass:403.0227396
Monoisotopic Mass:403.0227396
Topological Polar Surface Area:113
Heavy Atom Count:25
Complexity:568
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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