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Home > Encyclopedia > Sethoxydim

Sethoxydim

Sethoxydim structure

Sethoxydim 

structure
  • CAS No:

    74051-80-2

  • Formula:

    C17H29NO3S

  • Chemical Name:

    Sethoxydim

  • Synonyms:

    2-Cyclohexen-1-one,2-[1-(ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-;2-[1-(Ethoxyimino)butyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one;BAS 9052;NP 55;Cyethoxydim;Poast;BAS 90520H;Sethoxydim;ARD 34/02;Nabu;Alloxol S;Expand;BASF 9052;Nabu S;Expand Plus;Fervinal;Grasidim;Poast Plus;Fervinal plus;Sertin;Segment;2-(1-(Ethoxyimino)butyl)-5-(2-(ethylthio)propyl)-3-hydroxycyclohex-2-enone;73468-19-6;74433-80-0;77107-41-6

  • Categories:

    Agrochemicals  >  Herbicides

Description

Oily, amber liquid. Odorless. Flammable. Commercial product is available as an emulsifiable concen- trate.


Sethoxydim is an oily odorless liquid. Non corrosive. Used as an herbicide.


Sethoxydim is an oily odorless liquid. Non corrosive. Used as an herbicide.|Sethoxydim is an organic hydroxy compound.

Sethoxydim Basic Attributes

327.48

327.48

277-682-3

1189NNQ8F6

DTXSID9024304|DTXSID7058466

Oily liquid

29309090

Characteristics

80.7

1.65 at pH 7; 4.51 at pH 5

Oily odorless liquid

1.043 g/mL at 25 deg C

<25 °C

>90 deg C at pressure 3X10-5 mm Hg

215ºC

1.534

soluble in most common organic solvents including acetone, benzene, ethyl acetate, hexane and methanol at >1 Kg/Kg.

2-8°C

1.6X10-7 mm Hg at 20-25 deg C

Oral-Rat LD50: 3200 mg/kg; Oral-Mouse LD50: 5600 mg/kg

Combustion produces toxic nitrogen oxide and sulfur oxide gas

Odorless

Henry's Law constant = 2.2X10-11 atm-cu m/mole at 25 °C (est)

Hydroxy radical reaction rate constant = 1.5X10-10 cu cm/molec-sec at 25 °C (est)|Ozone reaction rate constant = 1.1X10-17 cu cm/molec-sec at 25 °C (est)

Slightly water soluble.

Hydrocarbons, Aliphatic Unsaturated

A cyclohexene, oxime derivative. This compound is incompatible with organic and inorganic copper compounds. Oximes chemically similar to, but more reactive than an amide. Incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Also incompatible with strongly oxidizing acids, peroxides, and hydroperoxides.

Safety Information

NONH for all modes of transport

2

GW7191000

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

The commercial product is stable for at least 2 yr under normal storage conditions. At 10 mg/L, 12 hr/day illumination with xenon lamp, DT50 is 5.5 days (pH 8.7, 25 deg C).

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.

Incompatible with organic and inorganic copper compounds.

California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Sethoxydim (74051-80-2) as of April 18, 2005.

Chemical-resistant apron when cleaning equipment, mixing, or loading. Chemical-resistant footwear plus socks. Chemical-resistant gloves. Chemical resistant headgear for overhead exposure. Coveralls over short sleeved shirt and short pants.

SEDIMENT: Ten sampling sites on the Sarno and Volturno Rivers in the Campania region, Italy were studied from July 1, 1988 through June 30 , 1989(1). Three of four Sarno River sites tested positive, at concentrations of 26 ng/g (very polluted), 13 ng/g (agricultural area), and 64 ng/g (mouth of the Sarno River(1). One of six Vulturno River sites tested positive, with a concentration of 130 ng/g in a sample from the Regi Lagni mouth; all concentrations reported in ng/g dry weight(1).

Toxicity

moderately toxic

LD50 Rat oral 3200-3500 mg/kg|LD50 Rat dermal >5000 mg/kg|LD50 Rat (male) oral 3125 mg/kg|LD50 Rat (female) oral 2676 mg/kg|For more Non-Human Toxicity Values (Complete) data for SETHOXYDIM (8 total), please visit the HSDB record page.

Sethoxydim'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 190(SRC), determined from a log Kow of 1.65(2) and a regression-derived equation(3), indicates that sethoxydim is expected to have moderate mobility in soil(SRC). Volatilization of sethoxydim from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Sethoxydim is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.6X10-7 mm Hg(5). Based on a reported half-lives of 4 weeks in clay and 2 weeks in sandy loam(6), biodegradation may be an important factor in the environmental fate of sethoxydim in soil(SRC).|TERRESTRIAL FATE: Field dissipation studies of sethoxydim were conducted on three different types of soils in Minnesota, Sandy loam from Westport, MN, silt loam from Rochester MN and clay loam from Waseca, MN. Sethoxydim was applied to corn corps at the rate of 0.3 kg/hr. Applications were made in June 1989 and June 1990. 37%, 51%, and 29% of the initial concentration of 100 ug/kg of sethoxydim to soil was found in sandy loam, silt loam, and clay loam, respectively, 29 days after treatment in 1989 while in 1990 86%, 52% ,and 24%, respectively, of sethoxydim remained in the same soils 21 days after treatment(1). Most of the compound was found at depths of 0-15 cm. 173 days after application trace amounts of the compound were detected(1).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 190(SRC), determined from a log Kow of 1.65(2)and a regression-derived equation(3), indicates that sethoxydim 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 2.2X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 11(SRC), from its known log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis may be an important factor in the environmental fate of sethoxydim which had reported half-lives of 1.6, 45, and 438 days at pH 3, 6, and 9, respectively(7). Based on a reported half-life of 4 weeks in clay and 2 weeks in sandy loam(8), biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sethoxydim, which has a vapor pressure of 1.6X10-7 mm Hg at 20-25 deg(2), will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase sethoxydim 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 1 day(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The rate constant for the vapor-phase reaction of sethoxydim with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). Particulate-phase sethoxydim may be removed from the air by wet and dry deposition(SRC). Sethoxydim has been shown to be stable to light(5).

The rate constant for the vapor-phase reaction of sethoxydim with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of sethoxydim with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Sethoxydim has reported half-lives in water of 1.6, 45 and 438 days at pH 3, 6, and 9, respectively(3). Sethoxydim has been shown to be stable to light(4). At 10 mg/L, the half-life is 5.5 days when illuminated for 12 hours/day with a xenon lamp at 25 deg and pH 8.7(4).

An estimated BCF of 11 was calculated for sethoxydim(SRC), using a log Kow of 1.65(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.

100.00 L/kg|The Koc of sethoxydim is estimated as 190(SRC), using a log Kow of 1.65(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that sethoxydim is expected to have moderate mobility in soil. Soil studies of sethoxydim have found little evidence of soil leaching. In a field study, the majority of sethoxydim was found in the first 15 cm of soil; samples were taken at day 0, 7, 21,73 and 138(4).

The Henry's Law constant for sethoxydim is estimated as 2.2X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that sethoxydim is expected to be essentially nonvolatile from moist soil(SRC) and water surfaces(2). Sethoxydim is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.6X10-7 mm Hg(3).

Occupational exposure to sethoxydim may occur through dermal contact with this compound at workplaces where sethoxydim is produced or used. (SRC)

Drug Information

In rats, following oral administration, 78.5% is eliminated in the urine and 20.1% in the feces within 48 hr.|In a rat metabolism study, excretion was extremely rapid and tissue accumulation was negligible.

In soya beans, the parent molecule is oxidised, structurally rearranged, and conjugated. Transformation to metabolites is very rapid.

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/|Ingestions of these herbicides are likely to be followed by vomiting and diarrhea due to the irritant properties. ... Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum hydroxide antacids may be useful in neutralizing the irritant actions of most acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if spontaneous diarrhea has not already commenced. Dehydration and electrolyte disturbances may be severe enough to require intravenous fluids. There are no specific antidotes for poisoning by these herbicides. ... If large amounts of herbicide have been ingested and the patient is seen within an hour of the ingestion, gastrointestinal decontamination should be considered. /Other Herbicides/|If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balence and administer intravenous infusions of glucose, normal saline, Ringers solution, or Ringers lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. Supportive measures are ordinarily sufficient for successful management of excessive exposure to these herbicides. If the patients condition deteriorates in spite of good supportive care, the operation of an alternative or additional toxicant should be suspected. /Other Herbicides/

sethoxydim

Sethoxydim Use and Manufacturing

Methods of Manufacturing

Sethoxydim is produced by reaction of ethylmercaptan with crotonal, followed by reaction with acetone, dimethylmalonate, hydrolysis reagents, butyryl chloride, and hydroxyethylamine.

Uses

Herbicide.

Emulsifiable concentrate|Selected products: Nabu; Poast; Checkmate; Conclude G; Fervinal; Grasidim; Manifest G; Prestige; Torpedo; Ultima 160; Vantage. Mixtures: Conclude Ultra (+acifluorfen-sodium+ bentazone-sodium); Rezult (+bentazone-sodium).

Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Inhibits mitosis. ...Selective systemic herbicide, absorbed predominantly by the foliage, and, to a lesser extent, by the roots. Translocated rapidly both acropetally and basipetally.

Product analysis by hplc with u.v. detection ... Residues determined by hplc.

Agrochemicals -> Herbicides

Computed Properties

Molecular Weight:327.5
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:9
Exact Mass:327.18681496
Monoisotopic Mass:327.18681496
Topological Polar Surface Area:84.2
Heavy Atom Count:22
Complexity:432
Undefined Atom Stereocenter Count:2
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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