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Ethofumesat

Ethofumesate

HCID 33360
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
26225-79-6
Standard-SMILES
CCOC1Oc2ccc(OS(C)(=O)=O)cc2C1(C)C
InChIKey
IRCMYGHHKLLGHV-UHFFFAOYSA-N
Summenformel
C13H18O5S
Durchschnittliche Molmasse
286,35 g/mol
Monoisotopische Masse
286,08749468

Überblick

2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate is a methanesulfonate ester that is methanesulfonic acid in which the hydrogen of the hydroxy group has been replaced by a 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl group. It is a methanesulfonate ester, an ether and a member of 1-benzofurans.

Namen und Bezeichner

Bevorzugter Name
Ethofumesate
IUPAC
(2-ethoxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate
Lokaler Name
Ethofumesat
Englischer Name
Ethofumesate
Summenformel
C13H18O5S
Molmasse
286.34

Namen und Synonyme

ETHOFUMESATE26225-79-6ProgressTramatNortron (new)2-Ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonateDTXSID8034580NC 8438CR 14658BURAKOSATKEMIRON PLUS5-Benzofuranol, 2-Ethoxy-2,3-dihydro-3,3-dimethyl-, methanesulfonate
Weitere Namen anzeigen
ETOFUMESATEnc8438NortonNORTRONcr14658ETHOSATETHOSIN
3051U1Z8KVDTXCID6014580CHEBI:83768RefChem:592706CHEBI:81990247-525-3(2-ethoxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonateNortran

Datenbank-Bezeichner

CAS
26225-79-6
PubChem CID
33360
DTXSID
DTXSID8034580
ChEMBL
CHEMBL2133153
ChEBI
CHEBI:83768
UNII

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,7
Polarare Oberfläche (TPSA)
70,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
19
Formalladung
0
Komplexität
411

Experimentelle und physikochemische Eigenschaften

Pesticides · 6 Einträge

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Herbicides, Other

Pesticides -> Herbicides -> Benzofuranyl alkylsulfonate herbicides

Environmental transformation -> Pesticides (parent, predecessor)

Herbicides

LogP · 2 Einträge

log Kow = 2.7

2.7

OdorMild, aromatic odor
Density1.29 at 20 °C
Color/FormWhite crystaline solid
Solubility · 2 Einträge

>600 mg/L in acetone, dichloromethane, dimethyl sulfoxide, ethyl acetate; 300-600 g/L in toluene and p-xylene; 120-150 g/L in methanol; 60-76 g/L in ethanol; 25-30 g/L in isopropanol; 4.67 g/L in hexane

In water, 50 mg/L at 25 °C

Flash PointNon-combustibile
Human DrugsPharmaceuticals

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Warning

H400 (46%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

Regulation (EC) No 1107/2009 (amended)

Ethofumesate is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

02/37/EC, Reg. (EU) 2016/1426, Reg. (EU) 2016/950, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012

Ethofumesate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 5-Benzofuranol, 2-ethoxy-2,3-dihydro-3,3-dimethyl-, methanesulfonate, (.+-.)-: Environment tier I assessment
Hazards SummaryMay cause irritation; [MSDSonline] Slightly irritating in rabbit eye; Not sensitizing in guinea pig testing; No adverse effects in 90-day feeding study of rats at 20,000 ppm; [IUCLID: Ethofumesate - 2000]
Special Reports · 1 Eintrag

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Ethofumesate EPA 738-R-05-010 September 2005. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of June 26, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]

FIFRA Requirements

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites/In animals the/ major metabolite is the lactone or free acid form of the respective 2-oxo compound.
MeSH Pharmacological ClassificationPesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

Verwendung und Herstellung

Uses · 6 Einträge

Used as systemic herbicide for control of annual broad-leaved and grass weeds in beets, vegetables, tobacco, pastures, turf, and other crops; Also used as silvicide (kills trees and forests); [HSDB]

Farming (Pesticides) [Category: Industry]

For Ethofumesate (USEPA/OPP Pesticide Code: 110601) 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, silvicide.

Selective systemic herbicide ... used pre- and/or post-emergence in sugar and other beet crops, turf, ryegrass and the other pasture grasses, at 0.3-2.0 kg/ha. It is effective in controlling a wide range of important grasses and broad-leaved weeds, with a good persistence of activity in the soil. In beet crops, 1.0-2.0 kg/ha can be used, but ethofumesate is normally recommended at 0.2-2.0 kg/ha in tank-mixtures or co-formulations with other residual or contact herbicides for use in beet.

Herbicide; For control of annual broadleaf and grass weeds in beets, green beans, grass seed crops,onions,peas,spinach grown for seed, sunflower,strawberries, tobacco, and turf.

Methods of Manufacturing · 2 Einträge

Ethofumesate is made by first reacting 2-methylpropionaldehyde and morpholine. That product is reacted with p-benzoquinone to give 2,3-dihydro-3,3-dimethyl-2-morpholinobenzofuran-5-ol. That compound can be reacted with mesyl chloride (methanesulfonyl chloride) to give ethofumesate.

... P.S. Gates et al., US patent 3,689,507 (1972 to Fisons)

Zugehörige Reaktionen

7
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 67252
HRID 67252als Eduktuspto-grants-1982_08
Reaktionsgleichung von HRID 236691
HRID 236691als Eduktuspto-grants-1979_06
Reaktionsgleichung von HRID 615953
HRID 615953als Eduktuspto-grants-1978_02
Reaktionsgleichung von HRID 807965
HRID 807965als EduktTest data from https://doi.org/10.1039/C8SC04228D
Reaktionsgleichung von HRID 1112121
HRID 1112121als Eduktuspto-grants-1978_10
Reaktionsgleichung von HRID 1578504
HRID 1578504als Eduktuspto-grants-1976_02
Reaktionsgleichung von HRID 2072311
HRID 2072311als Eduktuspto-grants-1977_09

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
3051U1Z8KV
EC Number
247-525-3
Nikkaji
J3.065.123E
Melting Point · 2 Einträge

70-72 °C

MP: 69-71 °C (technical grades)

Vapor Pressure · 2 Einträge

0.0000049 [mmHg]

4.9X10-6 mm Hg at 25 °C

Physical DescriptionWhite solid; [Merck Index] Colorless solid; [MSDSonline]
Stability/Shelf Life · 2 Einträge

Relatively stable in water.

Stable to hydrolysis in water at pH 7 and 9. At pH 5.0, DT50 940 day, forming the hydroxy analogue. Phototransformed in water, DT50 31 hr. Degraded in air, DT50 4.1 hr.

Physikochemische Eigenschaften

Schmelzpunkt
70 · 70-72°
Siedepunkt
364.85 °C · 364.85°C
Dichte
1.3165 · 1.3165 (rough estimate)
Brechungsindex
1.506 · 1.5060 (estimate)
Flammpunkt
100 °C · 100 °C
storage temp.
0 · 0-6°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
Farbe
Pale Beige
Wasserlöslichkeit
50.34 mg/L · 50.34mg/L(25 ºC)
Merck
13 · 13,3778
BRN
5759730 · 5759730
Henry's Law Constant
2.7 · 2.7×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Major Application
agricultureenvironmental
InChI
1S/C13H18O5S/c1-5-16-12-13(2,3)10-8-9(18-19(4,14)15)6-7-11(10)17-12/h6-8,12H,5H2,1-4H3
InChIKey
IRCMYGHHKLLGHV-UHFFFAOYSA-N
SMILES
CCOC1Oc2ccc(OS(C)(=O)=O)cc2C1(C)C
LogP
2.7 · 2.700
CAS Datenbank
26225 · 26225-79-6(CAS DataBase Reference)
NIST chemische Informationen
Ethofumesate(26225-79-6)
EPA chemische Informationen
Ethofumesate (26225-79-6)
· 4 Einträge

Tolerances are established for combined residues of the herbicide ethofumesate (2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate) and its metabolites 2-hydroxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate and 2,3-dihydro-3,3-dimethyl-2-oxo-5-benzofuranyl methanesulfonate (both calculated as the parent compound) in or on the following raw agricultural commodities: beet, sugar, roots; beet, sugar, tops; cattle, fat; cattle, meat byproducts; cattle, meat; goat, fat; goat, meat byproducts; goat, meat; grass, straw; hog, fat; hog, meat byproducts; hog, meat; horse, fat; horse, meat byproducts; horse, meat; sheep, fat; sheep, meat byproducts; and sheep, meat.

Tolerances are established for combined residues of the herbicide ethofumesate (2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate; CAS Reg. No. 26225-79-6) and its metabolites 2-hydroxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate and 2,3-dihydro-3,3-dimethyl-2-oxo-5-benzofuranyl methanesulfonate, (both calculated as the parent compound) in or on the following processed feeds when present therein as a result of application of the herbicide to the growing crops: sugar beet molasses.

The Agency has completed its assessment of the dietary, occupational, residential, and ecological risks associated with the use of pesticide products containing the active ingredient ethofumesate. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient ethofumesate, the Agency has sufficient information on the human health and ecological effects of ethofumesate to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that ethofumesate containing products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk mitigation measures outlined in this document are adopted; and (iii) label amendments are made to reflect these measures.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Ethofumesate is found on List B. Case No: 2265; Pesticide type: Herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): 2-Ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate; Data Call-in (DCI) Date(s): 06/19/91, 01/04/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Hazard Classes and Categories · 3 Einträge

Aquatic Acute 1 (46%)

Hazardous to the aquatic environment (acute) - category 1

Aquatic Acute 1

Sicherheit und Schutzausrüstung

Storage Conditions · 2 Einträge

Do not store near food feed or fertilizer.Flowable formulation non-combustible can be stored down to 15 °F.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

Cleanup Methods · 2 Einträge

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.

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.

Disposal Methods · 2 Einträge

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.

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.

Preventive Measures · 5 Einträge

Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.

Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.

Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.

Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

For more Preventive Measures (Complete) data for ETHOFUMESATE (6 total), please visit the HSDB record page.

Allowable Tolerances · 2 Einträge

Tolerances are established for combined residues of the herbicide ethofumesate (2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate) and its metabolites 2-hydroxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate and 2,3-dihydro-3,3-dimethyl-2-oxo-5-benzofuranyl methanesulfonate (both calculated as the parent compound) in or on the following raw agricultural commodities: beet, sugar, roots, 0.1 ppm; beet, sugar, tops, 1.00 ppm; cattle, fat, 0.05 ppm; cattle, meat byproducts, 0.05 ppm; cattle, meat, 0.05 ppm; goat, fat, 0.05 ppm; goat, meat byproducts, 0.05 ppm; goat, meat, 0.05 ppm; grass, straw, 1 ppm; hog, fat, 0.05 ppm; hog, meat byproducts, 0.05 ppm; hog, meat, 0.05 ppm; horse, fat, 0.05 ppm; horse, meat byproducts, 0.05 ppm; horse, meat, 0.05 ppm; sheep, fat, 0.05 ppm; sheep, meat byproducts, 0.05 ppm; and sheep, meat, 0.05 ppm.

Tolerances are established for combined residues of the herbicide ethofumesate (2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate; CAS Reg. No. 26225-79-6) and its metabolites 2-hydroxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate and 2,3-dihydro-3,3-dimethyl-2-oxo-5-benzofuranyl methanesulfonate, (both calculated as the parent compound) in or on the following processed feeds when present therein as a result of application of the herbicide to the growing crops: sugar beet molasses, 0.5 ppm.

Personal Protective Equipment (PPE) · 3 Einträge

Chemical-resistant gloves. long-sleeved shirt and long pants. Protectice eyewear. Shoes plus socks.

...Respiratory protection (minimum standard is a filtering facepiece respirator with NPF of 12) and clothing (overalls and rubber gloves) to prevent skin contact. ...and goggles... .

Wear appropriate chemical protective gloves, boots, and goggles. /Organochlorine pesticide, solid or liquid, NOS/

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

LC50 Cyprinus carpio (Common Carp) 10.92 mg/L/96 hr /Conditions of bioassay not specified in source examined/

LC50 Anas platyrhynchos (Mallard duck) diet >10000 ppm/8 days

LD50 Apis mellifera (Honey bee, adult) topical >50 ug/bee

LC50 Colinus virginianus (Bobwhite quail) diet >5000 ppm/8 days

For more Ecotoxicity Values (Complete) data for ETHOFUMESATE (12 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 55-500 measured in 10 soils(2), indicates that ethofumesate is expected to have moderate to high mobility in soil(SRC). Volatilization of ethofumesate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4.9X10-6 mm Hg(3), and water solubility, 50 mg/L(4). Ethofumesate is not expected to volatilize from dry soil surfaces(SRC) based on its vapor pressure(3). The photodegradation half-life of ethofumesate was reported as 165 hours on soil surfaces, and its biodegradation half-life was reported to range from 83 to 253 days under aerobic conditions(5).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 55-500(2), indicate that ethofumesate 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 3.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4.9X10-6 mm Hg(4), and water solubility, 50 mg/L(5). According to a classification scheme(6), an estimated BCF of 24(SRC), from a log Kow of 2.7(5) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The photodegradation half-life of ethofumesate was reported as 28 to 31 hours in aqueous solution(8). Ethofumesate is stable to hydrolysis at pH 5, 7, and 9(8). The 50% dissipation time (DT50) of ethofumesate in a sediment/water microcosm was reported as 125 days(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethofumesate, which has a vapor pressure of 4.9X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase ethofumesate 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 7 hours(SRC), calculated from its rate constant of 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase ethofumesate will be removed from the atmosphere by wet and dry deposition. The photodegradation half-life of ethofumesate was reported as 28 to 31 hours in aqueous solution(4), suggesting direct photolysis in the atmosphere is possible(SRC).

Acute Toxicity LinkChemical: ETHOFUMESATE
Soil Adsorption/Mobility · 1 Eintrag

The Koc value of ethofumesate measured in 10 different soils ranged from 55 to 500, with a mean value of 213(1). According to a classification scheme(2), these Koc values suggest that ethofumesate is expected to have high to moderate mobility in soil(SRC).

Human Toxicity Excerpts · 2 Einträge

/CASE REPORTS/ In one case an employee developed a headache when he worked in the smell of the technical material. There were two cases of contamination with the spray dilution of an emulsifiable concentrate formulation of ethofumesate plus another product; in one of these cases no toxic effects were seen, in the other there was transient weakness and light-headedness, possibly caused by the solvent. In the final case, eye contamination with an emulsifiable concentrate formulation of ethofumesate may have produced a corneal ulcer; again this may have been a solvent effect.

/OTHER TOXICITY INFORMATION: GENOTOXICITY/ A study of cytogenetic changes in Yugoslavian pesticide applicators was conducted. The cohort consisted of 27 male growers, mean age 39 years, in the Yugoslavian vineyard industry. They applied pesticide mixtures that contained herbicides such as ethofumesate and 2,4-D, fungicides such as triadimefon, vinclozolin, and cineb, and the insecticide diazinon. Controls consisted of 15 male school teachers from a nearby town, mean age 42.31 yr, and 20 males, mean age 38.9 yr, from Belgrade University. All subjects were nonsmokers. Blood samples were collected from the subjects before the start of the spraying season, after 1 month of spraying, and at the end of the spraying season. The lymphocytes were harvested from the samples and scored for chromosome aberrations, sister chromatid exchanges (SCEs), and micronuclei. During the prespraying season, the mean frequency of unstable chromosome aberrations was slightly, but significantly higher in the vineyard workers than in both control groups. The mean frequency of micronucleated cells was similar in all three groups. No significant differences in mean SCE frequency between the three groups was seen, although there were significant individual differences among subjects in all groups. The incidence of chromosomal aberrations and micronucleated cells was increased in the vineyard workers 1 mo after the start of the spraying season compared to the prespraying season. Only the increase in micronucleated cells was statistically significant. No increase in SCE frequency was seen. At the end of the spraying season, the incidence of unstable chromosome aberrations and binucleated cells in the vineyard workers was significantly increased compared to the prespraying period. The micronuclei frequency was significantly correlated with the chromosome aberration frequency and the frequency of both endpoints was significantly higher than in the controls. The SCE frequency was not significantly increased in the exposed workers. The authors conclude that environmental exposure to pesticide mixtures causes cytogenetic changes indicative of a genetic hazard in the lymphocytes of exposed sprayers.

Artificial Pollution Sources · 1 Eintrag

Ethofumesate's production may result in its release to the environment through various waste streams; it's use as an herbicide(1) will result in its direct release to the environment(SRC). Ethofumesate is currently registered for use on sugar beets, garden beets, table beets, carrots and various turf uses, including grass seed, sod and ornamental turf(1). It is also registered for use in seed production of Swiss Chard and spinach(1).

Environmental Biodegradation · 1 Eintrag

AEROBIC: The microbial dissipation half-life of ethofumesate in soils under aerobic conditions was reported to range from 83 to 253 days(1). The 50% dissipation time (DT50) of ethofumesate in a sediment/water microcosm was reported as 125 days(2). The half-life of ethofumesate in soil at 22 to 25 °C was reported as 45 days(3).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 24 was calculated for ethofumesate(SRC), using a log Kow of 2.7(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).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for ethofumesate is estimated as 3.7X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 4.9X10-6 mm Hg(1), and water solubility, 50 mg/L(2). This Henry's Law constant indicates that ethofumesate is expected to be essentially nonvolatile from water surfaces(3). Ethofumesate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to be an important environmental fate process(SRC). Ethofumesate is not expected to volatilize from dry soil surfaces(SRC) based on its vapor pressure(1).

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Twenty Sprague-Dawley rats (10 male, 10 female) were fed 0, 1000, 5000, or 20000 ppm ethofumesate for 90 days. Decreased body weight gain and reduced food intake /observed in/ females at 20,000 ppm. Increased liver and kidney weight in both sexes at 20,000 ppm. No treatment-related deaths or clinical signs of reaction to treatment.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ /In/ a carcinogenicity study... Ethofumesate, 90.8% /was/ fed in the diet to Syrian hamsters, 50/sex/test group, 100/sex in control, at 0, 80, 400 or 2000 ppm; exposure began 1 week before mating of parents, continued through gestation, lactation and lifespan (84-98 weeks; sacrificed when group reached 60% mortality. NOEL = 400 ppm (increased liver weight without histopathological finding) ... Use of hamsters is justified on basis they are less susceptible to disease, are sensitive to carcinogens and are acceptable by FIFRA.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ /Beagle dogs fed daily 0, 800, 4000, or 20,000 ppm for 104 weeks./ Reduction in red blood cell counts at 12 weeks and 50 weeks at 4000 and 20,000 ppm. Decrease in hemoglobin at 50 weeks for doses of 4000 and 20,000 ppm. Increased alkaline phosphates, from 12 weeks, at 4000 and 20,000 ppm. Increase in glutamic pyruvic transaminase at weeks 12 and 102 at doses of 4000 and 20,000 ppm. At termination, liver weight increase in both sexes at 20,000 ppm. No associated histopathological change.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Ethofumesate technical (purity = 92.5%) was fed in the diet for 2 years to CFHB Wistar rats (40/sex/group) at 0 (60/sex), 8, 40, 200, 1000 or 5000 ppm (60/sex), equivalent to 0.5, 2.2, 10.5, 55 or 300 mg/kg during the first 6 weeks. No adverse effect. NOEL = 1000 ppm (55-83% mortality in 5000 ppm males; chronic nephritis, especially in males was a major cause of death; murine respiratory disease was observed in "every" rat; body weights were depressed 6% in males and 12% in females at termination--5000 ppm; hematology and clinical chemistry parameters were marginal-- no electrolytes, cholesterol at 12 months only; 5/sex control and 5000 ppm only were analyzed at 12 months with no 18 month sampling; histopathology - no spinal cord; increased liver weights with no histopathological findings and no observable effects on clinical chemistry). No oncogenic effect was reported. The increase in liver weight with no accompanying histopathological findings was ... considered to be due to enzyme induction and of questionable biological significance.

For more Non-Human Toxicity Excerpts (Complete) data for ETHOFUMESATE (12 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of ethofumesate with photochemically-produced hydroxyl radicals has been estimated as 5.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Ethofumesate is stable to hydrolysis at pH 5, 7, and 9(2). The photodegradation half-life of ethofumesate was reported as 28 to 31 hours in aqueous solution and 165 hours in soil(2). The hydrolysis half-life of ethofumesate was reported as 940 days at pH 9(3).

Regulatorische Informationen

FIFRA Requirements · 4 Einträge

Tolerances are established for combined residues of the herbicide ethofumesate (2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate) and its metabolites 2-hydroxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate and 2,3-dihydro-3,3-dimethyl-2-oxo-5-benzofuranyl methanesulfonate (both calculated as the parent compound) in or on the following raw agricultural commodities: beet, sugar, roots; beet, sugar, tops; cattle, fat; cattle, meat byproducts; cattle, meat; goat, fat; goat, meat byproducts; goat, meat; grass, straw; hog, fat; hog, meat byproducts; hog, meat; horse, fat; horse, meat byproducts; horse, meat; sheep, fat; sheep, meat byproducts; and sheep, meat.

Tolerances are established for combined residues of the herbicide ethofumesate (2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate; CAS Reg. No. 26225-79-6) and its metabolites 2-hydroxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate and 2,3-dihydro-3,3-dimethyl-2-oxo-5-benzofuranyl methanesulfonate, (both calculated as the parent compound) in or on the following processed feeds when present therein as a result of application of the herbicide to the growing crops: sugar beet molasses.

The Agency has completed its assessment of the dietary, occupational, residential, and ecological risks associated with the use of pesticide products containing the active ingredient ethofumesate. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient ethofumesate, the Agency has sufficient information on the human health and ecological effects of ethofumesate to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that ethofumesate containing products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk mitigation measures outlined in this document are adopted; and (iii) label amendments are made to reflect these measures.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Ethofumesate is found on List B. Case No: 2265; Pesticide type: Herbicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): 2-Ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate; Data Call-in (DCI) Date(s): 06/19/91, 01/04/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Sicherheitsdaten

wgk
2
ridadr
UN 3077 9/PG 3
hs_code
29329990
RTECS-Nr.
DF7716500
risk_code
51/53
Toxizität
LD50 orally in rats: 1130 mg/kg (PB85-143766)
hazard_code
N
safety_code
61
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
26225-79-6(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
Formulations/Preparations · 5 Einträge

Selected products: Betanal Progress; ...Tramat; Ethosat; Ethosin; Keeper; Kubist; ...Kemiron; Legclene; Aran; Boxer; Darby; MSS Thor; Salute; Stapler; Stemat. ...Discontinued products: Atlas Thor; Fumat; MSS Ethosan; Primasan.

Selected products- Mixtures: Betanal Tandem (+phenmedipham); ...Betamix Progress (+desmedipham +phenmedipham); Betanal Progress OF (+desmedipham +phenmedipham); Betanal Quattro (+desmedipham +metamitron +phenmedipham); Betanal Trio (+metamitron +phenmedipham); Leyclene (+bromoxynil +ioxynil) (as salts); Progress (+desmedipham +phenmedipham); Spectron (+chloridazon); Beetup Pro (+desmedipham +phenmedipham); Beetup Trio (+desmedipham +phenmedipham); Betasana Trio (+desmedipham +phenmedipham); Betosip Combi (+phenmedipham); Bettix Triple (+desmedipham +metamitron +phenmedipham); Contatto (+desmedipham +phenmedipham); Goalpost (+phenmedipham); Goldpost (+phenmedipham); Gremlin (+chloridazon); Kontakt Twin (+phenmedipham); MagicTandem (+phenmedipham); Magnum (+chloridazon); Powertwin (+phenmedipham); Saherb (+desmedipham +phenmedipham +trifluralin); Synbetan D Forte (+desmedipham); Synbetan P Forte (+phenmedipham); Torero (+metamitron); Twin (+phenmedipham). Discontinued products- Mixtures: Medimat 2 (+phenmedipham); Tandem (+phenmedipham).

Trade names: Norton, Progress, and Prograss

Formulation types include flowable concentrate, emulsifiable concentrate, and granular products

... suspension concentrate

Use Classification · 5 Einträge

Pharmaceuticals

Pesticides -> Herbicides -> Benzofuranyl alkylsulfonate herbicides

Environmental transformation -> Pesticides (parent, predecessor)

Herbicides

HERBICIDES

Anwendungen

VerwendenEthofumesate is a herbicide.

Anbieter83 Anbieter

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