Linuron

Chemical compound
Linuron
Identifiers
  • 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea
CAS Number
  • 330-55-2
PubChem CID
  • 9502
ChemSpider
  • 9130
UNII
  • 01XP1SU59O
CompTox Dashboard (EPA)
  • DTXSID2024163 Edit this at Wikidata
ECHA InfoCard100.005.779 Edit this at Wikidata
Chemical and physical data
FormulaC9H10Cl2N2O2
Molar mass249.09 g·mol−1
3D model (JSmol)
  • Interactive image
  • CN(C(=O)NC1=CC(=C(C=C1)Cl)Cl)OC
InChI
  • InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)
  • Key:XKJMBINCVNINCA-UHFFFAOYSA-N

Linuron (3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea) is a phenylurea herbicide[1] that is used to control the growth of grass and weeds for the purpose of supporting the growth of crops like soybeans.[2][3]

Pharmacology

Mechanism of action

Linuron acts via inhibition of photosystem II, which is necessary for photosynthetic electron transport in plants.[2][3]

Effects in animals

Linuron has been found to produce reproductive toxicity in animals by acting as an androgen receptor (AR) antagonist, and for this reason, is considered to be an endocrine disruptor.[2][4] Consequently, in January 2017, the Standing Committee on Plants, Animals, Food and Feed (SCoPAFF) of the European Commission DG "Health and food safety" decided to not renew its regulatory approval.[5] Sales are expected to cease by June 2017.[5]

See also

References

  1. ^ Maier-Bode H, Härtel K (1981). "Linuron and monolinuron". Residue Reviews. Reviews of Environmental Contamination and Toxicology. 77: 1–364. doi:10.1007/978-1-4612-5874-2_1. ISBN 978-1-4612-5876-6. PMID 7017855.
  2. ^ a b c Mercurio S (30 August 2016). Understanding Toxicology. Jones & Bartlett Learning. pp. 705–. ISBN 978-1-284-12761-4.
  3. ^ a b Roberts TR (1998). Metabolic Pathways of Agrochemicals. Royal Society of Chemistry. pp. 744–. ISBN 978-0-85404-494-8.
  4. ^ "Peer review of the pesticide risk assessment of the active substance linuron". EFSA Journal. 14 (7). July 2016. doi:10.2903/j.efsa.2016.4518.
  5. ^ a b Curtis M. "Linuron fails to gain renewed approval". fginsight.com. Briefing Media Ltd. Retrieved 24 May 2017.
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Anilides/anilinesAromatic acidsArsenicals
HPPD inhbitors
OrganophosphorusPhenoxy
Auxins
ACCase inhibitors
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Pyrimidinediones
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PyridinesQuaternary
Photosystem I inhibitors
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ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids