Glufosinate-ammonium
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Glufosinate-ammonium
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CAS No:
77182-82-2
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Formula:
C5H12NO4P.H3N
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Chemical Name:
Glufosinate-ammonium
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Synonyms:
Butanoic acid,2-amino-4-(hydroxymethylphosphinyl)-,ammonium salt (1:1);Butanoic acid,2-amino-4-(hydroxymethylphosphinyl)-,monoammonium salt;Basta;HOE 00661;Glufosinate-ammonium;HOE 39866;Ammonium glufosinate;Finale;Finale 14SL;Basta LS;Ignite;Glufosinate monoammonium salt;Liberty;Liberty (pesticide);Dash;Basta Fl;Buster;Basta 150SL;BASTA 15;Ignite 280;Glufosinate ammonium salt;Liberty 280SL;106917-54-8;118336-14-4;82785-28-2
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CAS No:
Description
Glufosinate ammonium, a phosphinic acid analogue of glutamic acid, is an herbicide which is converted by plant cells into PT (L-phosphinothricin). Glufosinate ammonium exerts neurotoxic activity[1][2].
Glufosinate-ammonium Basic Attributes
215.18800
215.10300
278-636-5
DTXSID1024120
White to light yellow crystalline powder
2931901917
Characteristics
116.09000
log Kow < 0.1 (pH 7, 22 °C)
1.4 g/cm3 @ Temp: 20 °C
215 °C
519.1ºC at 760 mmHg
267.7ºC
Soluble in water
0-6ºC
LD50 in male, female mice, male, female rats (mg/kg): 431, 416, 2000, 1620 orally (Langelüddeke)
Slightly pungent odor
pKa1 = <2; pKa2 = 2.9; pKa3 = 9.8
135.4 Ų [M-H]-
Aqueous hydrolysis rate <0.0023/day at 25 °C and pH 5,7,9
Non-corrosive
Safety Information
III
6.1(b)
UN 2588
1
R22
53-45
EK7713600
Xn
Stable. Incompatible with strong oxidizing agents.
P201-P260-P280-P301 + P312 + P330-P308 + P313
H302 + H312 + H332-H360Fd-H373
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.
|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P314, P322, P330, P363, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P307+P311, P308+P313, P312, P314, P321, P322, P330, P363, P391, P405, and P501|Aggregated GHS information provided by 142 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P330, P333+P313, P363, P403+P233, P405, and P501
Toxicity
LD50 Rat (male) oral 2000 mg/kg|LD50 Rat (female) oral 1620 mg/kg|LD50 Mouse (male) oral 431 mg/kg|LD50 Mouse (female) oral 416 mg/kg|For more Non-Human Toxicity Values (Complete) data for GLUFOSINATE-AMMONIUM (11 total), please visit the HSDB record page.
Glufosinate-ammonium'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 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).
The rate constant for the vapor-phase reaction of glufosinate-ammonium with photochemically-produced hydroxyl radicals has been estimated as 3.07X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 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).
An estimated BCF of <3.2 was calculated for glufosinate-ammonium (SRC), using a log Kow of <0.1 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).
426.58 L/kg|Glufosinate-ammonium has observed Koc values ranging from 9.6 in sand to 1,229 in volcanic ash(1); the average recommended Koc is 430(1). According to a classification scheme(2), this Koc range suggests that glufosinate-ammonium can have high to low mobility in soil.|Field studies have indicated that glufosinate-ammonium rarely leaches below 10-15 cm in soil(1,2), presumably because of rapid microbial degradation(1).
The Henry's Law constant for glufosinate-ammonium is estimated as 4.4X10-14 atm-cu m/mole(1). This Henry's Law constant indicates that glufosinate-ammonium is expected to be essentially nonvolatile from water surfaces(2).
Occupational exposure to glufosinate-ammonium may occur through inhalation of dust and dermal contact with this compound at workplaces where glufosinate-ammonium is produced or used. (SRC)
Drug Information
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)
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.
...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/
...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 ...
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/|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/|BASTA is a herbicide containing glufosinate-ammonium 18.5% and a surface-active agent. There were 6 fatalities in 34 cases of glufosinate-ammonium poisoning reported by the Japan Poison Information Center. To evaluate efficacy in the removal of glufosinate ammonium from the blood, 2 bottles were prepared containing 600 mL of heparinized bovine blood with 1 mL or 3 mL of BASTA. Direct hemoperfusion or hemodialysis was performed for 2 hours at a flow rate of 50 mL/min. The final glufosinate ammonium concn of the blood bottle containing 1 mL of BASTA decreased to 96.9% of the initial concn after direct hemoperfusion and to 0.5% after hemodialysis. The final glufosinate ammonium concn of the bottle containing 3 mL of BASTA decreased to 62.2% after direct hemoperfusion and to 0.9% after hemodialysis. Hemodialysis is more effective than direct hemoperfusion for removal of glufosinate ammonium from blood.
/HUMAN EXPOSURE STUDIES/ ... In acute oral BASTA poisoning, patients develop a variety of clinical signs, including disturbed consciousness, convulsions, & apnea. These effects are suspected to be due to the effects of glufosinate on the CNS. ... A 60-yr-old man ingested 500 mL of BASTA herbicide ... He developed not only unconsciousness, respiratory distress, & convulsions but also an incr in urine output (7885 mL/d), elevated serum sodium (167 mEq/L), elevated plasma osmolality (332 mOsm/kg), & a decr in both urine osmolality (200 mOsm/kg) & urine specific gravity (1.003), which suggested the development of diabetes insipidus. The plasma level of antidiuretic hormone remained within the normal range (1.3 pg/mL), despite high plasma osmolality. The admin of desmopressin was successful in normalizing urine volume, specific gravity, & osmolality. Serum sodium corrected gradually within 48 hrs. /BASTA/|/CASE REPORTS/ ...A 65-yr-old male ingested BASTA, which contains 20% w/v of glufosinate ammonium, about 300 ml, more than the estimated human toxic dose. Four and a half hours after ingestion, he showed speech ataxia and systemic tremor. He was prophylactically intubated before the occurrence of serious respiratory failure. After 5 days of artificial ventilation he was extubated and discharged without any sequelae. We studied the serial change of serum glufosinate concn every 3-6 hr and assessed the urinary excretion of glufosinate every 24 hr. The absorbed amount of glufosinate was estimated from the cumulative excreted in urine. ... The changes in serum glufosinate concn exhibited T1/2alpha of 1.84 and T1/2beta of 9.59 hr. The apparent distribution volume at beta-phase and the total body clearance were 1.44 l/kg and 86.6 ml/min, respectively. Renal clearance was estimated to be 77.9 ml/min... /BASTA/|/CASE REPORTS/ ...A 69-yr-old female was admitted to the emergency department after taking 500 ml of BASTA. On arrival she was conscious, and gut decontamination, hemodialysis and hemoperfusion were performed. However, 8-1/2 hrs after ingestion, general convulsions occurred. Her serum CK increased to a peak of 24,900 IU/L on the third day of admission. An 87-yr-old male was admitted to the emergency department 3-1/2 hrs after taking 200 ml of BASTA and receiving gastric lavage at a local emergency room. On arrival he was conscious, and serial activated charcoal and hemodialysis was performed. Blood concn of glufosinate ammonium after hemodialysis decreased from 1.56 ug/ml to 0.68 ug/ml. Thirty hours after admission he had general convulsions. Glufosinate ammonium was not detected in the cerebrospinal fluid 6 hr after the convulsions. His serum CK increased to a peak of 17,870 IU/L on the 5th day of admission. /BASTA/|/CASE REPORTS/ ... A case of a 64-yr-old man who ingested glufosinate ... /was reported/. The patient suffered mental disturbances and hematological changes together with GI effects shortly after ingesting the poison, and later developed generalized convulsions, impaired respiration and circulatory failure. During recovery he exhibited loss of short-term memory (retrograde and anterograde amnesia). Neurotoxicity is a characteristic of glufosinate poisoning, although the mechanism is not clear. From the analysis of clinical symptoms of previously published cases, glufosinate toxicity appears to arise both from the active ingredient and the surfactant in the formulation. /PHOSPHINOTHRICIN/|For more Human Toxicity Excerpts (Complete) data for GLUFOSINATE-AMMONIUM (6 total), please visit the HSDB record page.
2-amino-4-methylphosphinobutyric acid
Glufosinate-ammonium Use and Manufacturing
Organophosphorus herbicide, glutamine synthesis inhibitor, non-selective contact herbicide. It has a certain systemic effect and can be used for weeding in orchards, vineyards, and non-arable land. It can also be used for potato fields to control annual or perennial dicotyledons, gramineous weeds and sedges, such as S. sylvestris, crabgrass, barnyard grass, etc. Setaria, wild wheat, wild corn, orchardgrass, fescue, serrata, fluffy grass, ryegrass, reed, bluegrass, wild oats, bromegrass, porcini, lamella, small wild sesame, solanum, Chrysanthemum, creeping grass, cut bentgrass, grass, field forget-me-not, bermudagrass, amaranth, etc. The amount used depends on the crop and weeds, and the amount used per hectare is 1 to 2 kg or more, such as raspberries and ferns for preventing forests and alpine pastures. The usage amount is 1.5-20kg/hm2. Used in orchards, vineyards, non-arable land, potato fields, etc. to prevent and control annual and perennial dicotyledonous and gramineous weeds, such as sagegrass, crabgrass, barnyard, wild barley, ryegrass, setaria, golden foxtail, Wild wheat, wild corn, perennial gramineous weeds and sedges, such as duck buds, tricornis, fescue, etc.
USEPA/OPP Pesticide Code 128850; Trade Names: HOE 039866, Basta, Ignite ISC Herbicide, HOE 00661.|Aqueous solution|Soluble concentrate|BASTA
Pesticide or Metabolite (M) Common Name: Glufosinate-ammonium; Commodity: Almond hulls, almond meat; Method Source: Hoechst-Celanese; Method ID: HRAV-5A; Method Date: 4/20/89; Instrument: GC/FPD; Estimated LOQ (ppm): 0.05. /From table/|Pesticide or Metabolite (M) Common Name: Glufosinate-ammonium; Commodity: Canola seed, sugarbeet roots; Method Source: Aventis Crop Science; Method ID: BK/01/99; Method Date: 5/20/2000; Instrument: GC/FPD; Estimated LOQ (ppm): 0.05. /From table/
Agrochemicals -> Herbicides
Computed Properties
Molecular Weight:198.16
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:198.07694396
Monoisotopic Mass:198.07694396
Topological Polar Surface Area:104
Heavy Atom Count:12
Complexity:187
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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Latest News on Glufosinate-ammonium
- BASF to stop production of glufosinate-ammonium at Knapsack and Frankfurt sites in Germany by the end of 2024
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