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glyphosate
Sign in to saveAlso known as Phosphonomethylglycine, N-(phosphonomethyl)glycine
Glyphosate (IUPAC name: '''N-(phosphonomethyl)glycine') is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). Glyphosate-based herbicides (GBHs) are used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. American agricultural company Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup''. Monsanto's last commercially relevant United States patent expired in 2000.
OverviewAI-generated
Glyphosate is a chemical compound with the formula C₃H₈NO₅P. Its IUPAC name is (carboxymethylazaniumyl)methyl-hydroxyphosphinate. The substance has a mass of 169.014 and a density of 1.704. It melts at 184.5 and decomposes at 187.
Chemical properties include a charge of 0, an xlogp of -4.7, and a tpsa of 114. The molecule contains three hydrogen bond donors and five hydrogen bond acceptors. A PubChem entry lists its weight as 169.07.
Glyphosate is the subject of 6610 PubMed records. It is referenced by 496 other encyclopedia articles.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C3H8NO5P
- Molecular weight
- 169.07 g/mol
- IUPAC name
- (carboxymethylazaniumyl)methyl-hydroxyphosphinate
- SMILES
- C(C(=O)O)[NH2+]CP(=O)(O)[O-]
- InChIKey
- XDDAORKBJWWYJS-UHFFFAOYSA-N
- XLogP
- -4.7
- Polar surface area
- 114 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
6,610 papers- The impact and toxicity of glyphosate and glyphosate-based herbicides on health and immunity.Journal of immunotoxicology · 2020
- Evolution of Glyphosate-Resistant Weeds.Reviews of environmental contamination and toxicology · 2021
- Glyphosate contamination in European rivers not from herbicide application?Water research · 2024
- Glyphosate Herbicide: Reproductive Outcomes and Multigenerational Effects.Frontiers in endocrinology · 2021
- Biomonitoring Equivalents for glyphosate.Regulatory toxicology and pharmacology : RTP · 2023
via PubMed
~58 min read
Encyclopedic overview
52 sectionsContents
- Discovery
- Chemistry
- Synthesis
- Impurities
- Formulations
- Mode of action
- Uses
- Genetically modified crops
- Environmental fate
- Residues in food products
- Toxicity
- Glyphosate alone
- Humans
- Cancer
- Other mammals
- Aquatic and marine animals
- Antimicrobial activity
- Soil biota
- Endocrine disruption
- Effect on plant health
- Glyphosate-based formulations
- Human
- Aquatic fauna
- Genetic damage
- Government and organization positions
- European Food Safety Authority
- International Agency for Research on Cancer
- Reviews of the EFSA and IARC reports
- US Environmental Protection Agency
- Monsanto response and campaign
- California Office of Environmental Health Hazard Assessment
- European Chemicals Agency
- Effects of use
- Emergence of resistant weeds
- Palmer amaranth
- ''Conyza'' species
- Ryegrass
- Johnson grass
- Monarch butterfly populations
- Legal status
- Europe
- European Union
- National level regulation
- Other countries
- Legal cases
- Lawsuits claiming liability for cancer
- Advertising controversies
- Trade dumping allegations
- Misinformation
- See also
- References
- External links
Glyphosate (IUPAC name: '''N-(phosphonomethyl)glycine') is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). Glyphosate-based herbicides (GBHs) are used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. American agricultural company Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup''. Monsanto's last commercially relevant United States patent expired in 2000.
Farmers quickly adopted glyphosate for agricultural weed control, especially after Monsanto introduced glyphosate-resistant Roundup Ready crops, enabling farmers to kill weeds without killing their crops. In 2007, glyphosate was the most used herbicide in the United States' agricultural sector and the second-most used (after 2,4-D) in home and garden, government and industry, and commercial applications. From the late 1970s to 2016, there was a 100-fold increase in the frequency and volume of application of GBHs worldwide, with further increases expected in the future.
Excerpted from Wikipedia’s “glyphosate” article, available under the CC BY-SA 4.0 licence.