Glufosinate ammonium

Names

[ Name ]:
Glufosinate ammonium

[Synonym ]:
Glufosinate Ammonium
2-Amino-4-(hydroxymethylphosphinyl)butyric acid ammonium salt
2-Amino-4-(hydroxymethylphosphinyl)butanoic acid, monoammonium salt
DL-Phosphinothricin, monoammonium salt
2-Amino-4-(hydroxymethylphosphinyl)butanoic acid monoammonium salt
2-Amino-4-[hydroxy(methyl)phosphoryl]butanoic acid ammoniate (1:1)
Glufosinate ammonium salt
Ammonium (3-amino-3-carboxypropyl)methylphosphinate
ammonium (2RS)-2-amino-4-(methylphosphinato)butyric acid
Monoammonium 2-amino-4-(hydroxymethylphosphinyl)butanoate
Ammonium 2-amino-4-(hydroxymethylphosphinyl)butyrate
Basta
Monoammonium 4-[hydroxy(methyl)phosphinoyl]-DL-homoalaninate
2-Amino-4-[hydroxy(methyl)phosphoryl]butanoic acid ammoniate
QVYZ2PQO&1 &&(DL) Form NH4 Salt
Ammonium (DL-homoalanine-4-yl)methylphosphinate
Glufosinate-ammonium
MFCD00055562
Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, ammonium salt
Ammonium 2-amino-4-[hydroxy(methyl)phosphoryl]butanoate
glufosinate-ammonum
EINECS 278-636-5

Biological Activity

[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].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

Glufosinate ammonium (1-100 μM; 12DIV) disrupts cell-cell adhesion in differentiated V-SVZ neural stem cells (NSCs)[2]. Glufosinate ammonium (1-100 μM; 12DIV) significantly decreases Celsr2 gene expression at 100 μM[2]. Glufosinate ammonium impairs ependymal cell capability to synthetize cilia[2]. RT-PCR[2] Cell Line: Ependymal cells Concentration: 1, 3, 10, 100 μM Incubation Time: During 12DIV (NSCs-to-ependymal cells time point) Result: Significantly decreased Celsr2 gene expression at 100 μM.

[In Vivo]

Glufosinate ammonium (10-250 mg/kg; gavage; Daily; on days 6-15 of gestation) indicates maternal toxicity in the groups given 50 or 250 mg/kg in Wistar rats[3]. The Elimination of Glufosinate ammonium (oral intubation) in the blood takes place with a half-life of less than 4 hours in male and female rats[3].

[References]

[1]. Áy Z, et al. The effect of high concentrations of glufosinate ammonium on the yield components of transgenic spring wheat (Triticum aestivum L.) constitutively expressing the bar gene. ScientificWorldJournal. 2012;2012:657945.

[2]. Feat-Vetel J, et al. Multiple effects of the herbicide glufosinate-ammonium and its main metabolite on neural stem cells from the subventricular zone of newborn mice. Neurotoxicology. 2018 Dec;69:152-163.

[3]. Ebert E, et al. Summary of safety evaluation toxicity studies of glufosinate ammonium. Food Chem Toxicol. 1990 May;28(5):339-49.

Chemical & Physical Properties

[ Boiling Point ]:
519.1ºC at 760 mmHg

[ Melting Point ]:
210°C

[ Molecular Formula ]:
C₅H₁₅N₂O₄P

[ Molecular Weight ]:
215.18800

[ Flash Point ]:
100 °C

[ Exact Mass ]:
215.10300

[ PSA ]:
116.09000

[ LogP ]:
0.24480

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EK7713600

CHEMICAL NAME :: Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, monoammonium salt

CAS REGISTRY NUMBER :: 77182-82-2

LAST UPDATED :: 199710

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C5-H11-N-O4-P.H4-N

MOLECULAR WEIGHT :: 198.19

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1600 uL/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - other changes

REFERENCE :: JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988- Volume(issue)/page/year: 7,47,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1850 mg/kg

TOXIC EFFECTS :: Behavioral - coma Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - other changes

REFERENCE :: VHTODE Veterinary and Human Toxicology. (American College of Veterinary and Comparative Toxicology, Publication Office, Comparative Toxicology, Manhattan, KS 66506) V.19- 1977- Volume(issue)/page/year: 36,17,1994

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1620 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C154,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85JFAN "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc. of Chemistry, 1983-86 Volume(issue)/page/year: A810,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 83 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 28,339,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 61 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 28,339,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 416 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,458,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 82 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 28,339,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 88 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 28,339,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,458,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18200 mg/kg/13W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes in urine composition Kidney, Ureter, Bladder - changes in bladder weight

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 28,339,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 13978 mg/kg/13W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - changes in potassium Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 28,339,1990

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302 + H312 + H332-H360Fd-H373

[ Precautionary Statements ]:
P201-P260-P280-P301 + P312 + P330-P308 + P313

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
53-45

[ RIDADR ]:
2588

[ RTECS ]:
EK7713600

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2931901917

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2931900090

[ Summary ]:
2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

Articles

A review of methods for the analysis of orphan and difficult pesticides: glyphosate, glufosinate, quaternary ammonium and phenoxy acid herbicides, and dithiocarbamate and phthalimide fungicides.

J. AOAC Int. 97(4) , 965-77, (2014)

This article reviews the chromatography/MS methodologies for analysis of pesticide residues of orphan and difficult chemical classes in a variety of sample matrixes including water, urine, blood, and ...

Repression of flowering under a noninductive photoperiod by the HDA9-AGL19-FT module in Arabidopsis.

New Phytol. 206(1) , 281-94, (2015)

Posttranslational acetylation of histones is reversibly regulated by histone deacetylases (HDACs). Despite the evident significance of HDACs in Arabidopsis development, the biological roles and underl...

Role of glutamate receptors and nitric oxide on the effects of glufosinate ammonium, an organophosphate pesticide, on in vivo dopamine release in rat striatum.

Toxicology 311(3) , 154-61, (2013)

The purpose of the present work was to assess the possible role of glutamatergic receptors and nitric oxide (NO) production on effects of glufosinate ammonium (GLA), an organophosphate pesticide struc...