Glufosinate-Ammonium

HCID 53597CAS 73777-50-1

Grundinformationen

Standard-SMILES
CP(=O)(O)CCC(N)C(=O)[O-].[NH4+]
InChIKey
ZBMRKNMTMPPMMK-UHFFFAOYSA-N
Summenformel
C5H15N2O4P
Durchschnittliche Molmasse
198,16 g/mol
Monoisotopische Masse
198,07694359

Überblick

Glufosinate-Ammonium is a synthetic organophosphate glutamine synthetase inhibitor and neurotoxin that is used as a pesticide. It is characterized as a highly soluble and volatile white to light yellow crystalline solid with a slightly pungent odor, and exposure occurs by inhalation, ingestion, or contact.

Namen und Bezeichner

Bevorzugter Name
Glufosinate-Ammonium
IUPAC
azanium 2-amino-4-[hydroxy(methyl)phosphoryl]butanoate

Namen und Synonyme

Glufosinate-ammoniumLiberty77182-82-2GLUFOSINATE AMMONIUMFinaleIgniteDashBasta LSGluphosinate ammoniumBusterIgnite ISC HerbicideAmmonium glufusinate
Weitere Namen anzeigen
Basta F1Liberty (pesticide)Finale 14SLCaswell No. 580IUNII-LBR207X9DFLBR207X9DFHOE 00661Glufosinate Monoammonium Salt

Datenbank-Bezeichner

CAS
73777-50-1、77182-82-2
PubChem CID
53597
DTXSID
DTXSID1024120
UNII
LBR207X9DF
EC Number
278-636-5

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
104 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
3
Schwere Atome
12

Experimentelle und physikochemische Eigenschaften

Pesticides · 3 Einträge

Pesticide -> EPA IRIS

Pesticides -> Herbicides, Other

Pesticide

LogPlog Kow < 0.1 (pH 7, 22 °C)
OdorSlightly pungent odor
Density1.4 g/ml at 20 °C
Color/FormWhite to light yellow crystalline powder
Solubility · 3 Einträge

Water solubility 1370 g/l (+/- 11%)

In organic solvents at 20 °C, g/100 ml: acetone = 0.016, toluene = 0.014, n-hexane = 0.02, ethanol = 0.065, ethyl acetate = 0.014

In water, 1,370 g/l @ 22 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Danger

H302+H312+H332 (66.8%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P203, P260, P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P308+P316, P317, P318, P319, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Hazard Traits - Reproductive Toxicity

Council Directive (EEC) No 414/1991 (Repealed by Reg. EC No 1107/2009 (amended))

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

REACH registered substance: Ammonium 2-amino-4-(hydroxymethylphosphinyl)butyrate (EC: 278-636-5)

Glufosinate-ammonium: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryMay cause irritation; Effects in high-dose animal studies include convulsions; [MSDSonline] Not a teratogen in animal studies, but may have effect on glutamate receptors in brain after fetal exposure; [REPROTOX]
FIFRA Requirements · 3 Einträge

Tolerances are established for residues of the herbicide glufosinate ammonium (butonic acid, 2-amino-4-(hydroxymethylphosphinyl)-, monoammonium salt) and its metabolite, 3-methylphosphinico-propionic acid, expressed as 2-amino-4-(hydroxmethylphosphinyl)butanoic acid equivalents, in or on the following food commodities: almond, hulls; apple; banana; banana, pulp; cattle, fat; cattle, meat; cattle, meat byproducts; egg; goat, fat; goat, meat; goat, meat byproducts; grape; hog, fat; hog, meat; hog, meat byproducts; horse, fat; horse, meat; horse, meat byproducts; milk; nut, tree group; potato; potato chips; potato granules and flakes; poultry, fat; poultry, meat; poultry, meat byproducts; sheep, fat; sheep, meat; and sheep, meat byproducts.

Tolerances are established for the combined residues of glufosinate ammonium (butonic acid, 2-amino-4-(hydroxymethylphosphinyl)-, monoammonium salt) and its metabolites, 2-acetamido-4methylphosphinico-butanoic acid and 3-methylphosphinico-propionic acid, expressed as 2-amino-4-(hydroxymethylphosphinyl)butanoic acid equivalents, in or on the following food commodities derived from transgenic canola, transgenic field corn, transgenic soybeans and transgenic sugar beets that are tolerant to the herbicide glufosinate ammonium as follows: aspirated grain fractions; beet, sugar, molasses; beet, sugar, roots; beet, sugar, tops (leaves); canola, meal; canola, seed; corn, field, forage; corn, field, grain; corn, field, stover; soybean, hulls; and soybean.

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128850; Tpye of Pesticide: conventional-herbicide; Use Site: food use, ornamentals, turf, etc.; Year: 1993.

Hazard Classes and Categories · 4 Einträge

Acute Tox. 4 (100%)

Reproductive toxicity - category 1B

Acute toxicity (Oral) - Category 4

Repr. 1B

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Allowable Tolerances · 2 Einträge

Tolerances are established for residues of the herbicide glufosinate ammonium (butonic acid, 2-amino-4-(hydroxymethylphosphinyl)-, monoammonium salt) and its metabolite, 3-methylphosphinico-propionic acid, expressed as 2-amino-4-(hydroxmethylphosphinyl)butanoic acid equivalents, in or on the following food commodities: almond, hulls: 0.50 ppm; apple: 0.05 ppm; banana: 0.03 ppm; banana, pulp: 0.20 ppm; cattle, fat: 0.05 ppm; cattle, meat: 0.05 ppm; cattle, meat byproducts: 0.10 ppm; egg: 0.05 ppm; goat, fat: 0.05 ppm; goat, meat: 0.05 ppm; goat, meat byproducts: 0.10 ppm; grape: 0.05 ppm; hog, fat: 0.05 ppm; hog, meat: 0.05 ppm; hog, meat byproducts: 0.10 ppm; horse, fat: 0.05 ppm; horse, meat: 0.05 ppm; horse, meat byproducts: 0.10 ppm; milk: 0.02 ppm; nut, tree group: 0.10 ppm; potato: 0.80 ppm; potato chips: 1.60 ppm; potato granules and flakes: 2.00 ppm; poultry, fat: 0.05 ppm; poultry, meat: 0.05 ppm; poultry, meat byproducts: 0.10 ppm; sheep, fat: 0.05 ppm; sheep, meat: 0.05 ppm; and sheep, meat byproducts: 0.10 ppm.

Tolerances are established for the combined residues of glufosinate ammonium (butonic acid, 2-amino-4-(hydroxymethylphosphinyl)-, monoammonium salt) and its metabolites, 2-acetamido-4methylphosphinico-butanoic acid and 3-methylphosphinico-propionic acid, expressed as 2-amino-4-(hydroxymethylphosphinyl)butanoic acid equivalents, in or on the following food commodities derived from transgenic canola, transgenic field corn, transgenic soybeans and transgenic sugar beets that are tolerant to the herbicide glufosinate ammonium as follows: aspirated grain fractions: 25.0 ppm; beet, sugar, molasses: 5.0 ppm; beet, sugar, roots: 0.9 ppm; beet, sugar, tops (leaves): 1.5 ppm; canola, meal: 1.1 ppm; canola, seed: 0.4 ppm; corn, field, forage: 4.0 ppm; corn, field, grain: 0.2 ppm; corn, field, stover: 6.0 ppm; soybean, hulls: 5.0 ppm; and soybean: 2.0 ppm.

Toxikologische Informationen

Target OrgansUrinary
Health EffectsSeizures; muscle weakness (post-status epileptic myopathy); convulsions; and even death. (T10)
Ecotoxicity Values · 5 Einträge

LC50 Japanese quail >5000 mg/kg (8 day dietary)

LC50 Rainbow trout 710 mg/l (96 hr) /Conditions of bioassay not specified./

LC50 Bluegill >1000 mg/l (96 hr) /Conditions of bioassay not specified./

LC50 Carp >1000 mg/l (96 hr) /Conditions of bioassay not specified./

LC50 Golden orfe >1000 mg/l (96 hr) /Conditions of bioassay not specified./

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an observed Koc range of 9.6 to 1,229 (recommended avg of 430)(2) indicates that glufosinate-ammonium can have low to high mobility in soil(SRC). Field studies have indicated that glufosinate-ammonium rarely leaches below 10-15 cm in soil(3,4), presumably because of rapid microbial degradation(3). Microbial degradation occurs rapidly in soil with transformation to 3-methylphosphinyl-propionic acid and 2-methylphosphinyl-acetic acid and ultimately to carbon dioxide(4-6). The aerobic half-life in soil is typically 3-11 days(2,4-6) with an anaerobic half-life of 5-10 days(2). Field dissipation half-lives 6-20 days (avg 13 days) are reported(2). A laboratory batch and in situ microcosm study(7) demonstrated that glufosinate-ammonium can be persistent and transported in an aquifer with relatively low clay content and little labile organic carbon.

AQUATIC FATE: Based on a classification scheme(1), an observed Koc range of 9.6 to 1,229 (recommended avg of 430)(2) indicates that glufosinate-ammonium can have low to high adsorption to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.4X10-14 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from a log Kow of <0.10(4), and a regression-derived equation(6) suggests the potential for bioconcentration in aquatic organisms is low(SRC). The aqueous hydrolysis rate of glufosinate-ammonium is reported to be <0.0023/day at 25 °C and pH 5,7 and 9(2) which corresponds to a half-life of greater than 300 days(SRC). The aqueous photolysis rate of glufosinate-ammonium is also reported to be <0.0023/day(2) which corresponds to a half-life of greater than 300 days(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), glufosinate-ammonium, which has an estimated vapor pressure of 9.1X10-12 mm Hg at 25 °C(SRC), determinded from a fragment constant method(2), is expected to exist solely in particulate phase in the ambient atmosphere. Particulate-phase glufosinate-ammonium may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity SummaryGlufosinate irreversibly inhibits the enzyme glutamine synthetase, which decreases ammonia detoxification. Increased ammonia levels lead to impairment of photorespiration and photosynthesis in plants. (T10)

Regulatorische Informationen

FIFRA Requirements · 3 Einträge

Tolerances are established for residues of the herbicide glufosinate ammonium (butonic acid, 2-amino-4-(hydroxymethylphosphinyl)-, monoammonium salt) and its metabolite, 3-methylphosphinico-propionic acid, expressed as 2-amino-4-(hydroxmethylphosphinyl)butanoic acid equivalents, in or on the following food commodities: almond, hulls; apple; banana; banana, pulp; cattle, fat; cattle, meat; cattle, meat byproducts; egg; goat, fat; goat, meat; goat, meat byproducts; grape; hog, fat; hog, meat; hog, meat byproducts; horse, fat; horse, meat; horse, meat byproducts; milk; nut, tree group; potato; potato chips; potato granules and flakes; poultry, fat; poultry, meat; poultry, meat byproducts; sheep, fat; sheep, meat; and sheep, meat byproducts.

Tolerances are established for the combined residues of glufosinate ammonium (butonic acid, 2-amino-4-(hydroxymethylphosphinyl)-, monoammonium salt) and its metabolites, 2-acetamido-4methylphosphinico-butanoic acid and 3-methylphosphinico-propionic acid, expressed as 2-amino-4-(hydroxymethylphosphinyl)butanoic acid equivalents, in or on the following food commodities derived from transgenic canola, transgenic field corn, transgenic soybeans and transgenic sugar beets that are tolerant to the herbicide glufosinate ammonium as follows: aspirated grain fractions; beet, sugar, molasses; beet, sugar, roots; beet, sugar, tops (leaves); canola, meal; canola, seed; corn, field, forage; corn, field, grain; corn, field, stover; soybean, hulls; and soybean.

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128850; Tpye of Pesticide: conventional-herbicide; Use Site: food use, ornamentals, turf, etc.; Year: 1993.

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

...Glufosinate ammonium is a structural analogue of glutamate & acts in plants by inhibition of glutamine synthetase leading to a complete breakdown of ammonia metab. Owing to the structural analogy of glufosinate ammonium to glutamate, its effect on various glutamate-utilizing systems needed to be investigated in mammals. Although in laboratory animals glufosinate ammonium causes an inhibition of glutamine synthetase activity in different tissues, this inhibition led to slight increases of glutamate and ammonia levels at high sublethal and lethal doses only. After oral admin for 28 days, glufosinate ammonium had no effect on glutathione & carbohydrate metab & no effect on biosynthesis of non-essential amino acids in rats & dogs. Glufosinate ammonium does not interfere with various neurotransmitter receptors in vitro & does not influence the catecholamine neurotransmitter tissue concn after iv application. The results of these studies show that ... in mammals the inhibition of glutamine synthetase activity in various tissues does not lead to a breakdown of ammonia metab. The mammalian metab ... compensates for this inhibition of glutamine synthetase activity by various other metabolic pathways ...

Biological Half-Life...A 65-yr-old male ingested BASTA, which contains 20% w/v of glufosinate ammonium... The changes in serum glufosinate concn exhibited T-1/2 alpha of 1.84 and T-1/2 beta of 9.59 hr. /BASTA/
Metabolism/Metabolites · 2 Einträge

The principal metabolite in urine & feces is 3-[hydroxy(methyl)phosphinoyl]propionic acid.

In plants, degradation of glufosinate-ammonium involves deamination, decarboxylation, & finally beta-oxidation to carbon dioxide.

Verwendung und Herstellung

Uses · 5 Einträge

Used as broad spectrum post-emergence herbicide for grapes, orchards, plantations, ornamentals, and non-cropland; Also used as crop desiccant; [HSDB]

Farming (Pesticides) [Category: Industry]

For Glufosinate-ammonium (USEPA/OPP Pesticide Code: 128850) 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 that can be applied post-emergence in noncrop areas and as a directed spray in field-grown and container nursery stock. It is nonselective and controls a broad spectrum and annual and perennial grass and broadleaf weeds.

Herbicide for a wide spectrum of annual, perennial broadleaf weeds and grasses in grapes, orchards, plantations, and ornamentals; along drains, canals, noncropland, and for desiccation of agricultural crops.

Formulations/Preparations · 4 Einträge

USEPA/OPP Pesticide Code 128850; Trade Names: HOE 039866, Basta, Ignite ISC Herbicide, HOE 00661.

Aqueous solution

Soluble concentrate

BASTA

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