Oryzalin

Oryzalin
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 4-(Dipropylamino)-3,5-dinitrobenzenesulfonamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.038.873
Chemical and physical data
FormulaC12H18N4O6S
Molar mass346.36 g·mol−1
3D model (JSmol)
Melting point137 to 139 °C (279 to 282 °F)
SMILES
  • CCCN(CCC)c1c([N+](=O)[O-])cc(S(N)(=O)=O)cc1[N+](=O)[O-]
InChI
  • InChI=1S/C12H18N4O6S/c1-3-5-14(6-4-2)12-10(15(17)18)7-9(23(13,21)22)8-11(12)16(19)20/h7-8H,3-6H2,1-2H3,(H2,13,21,22) ☒N
  • Key:UNAHYJYOSSSJHH-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Oryzalin is a herbicide of the dinitroaniline class. It acts through the disruption (depolymerization) of microtubules, thus blocking anisotropic growth of plant cells.[1] It can also be used to induce polyploidy in plants as an alternative to colchicine.[2]

Oryzalin's mode of action is inhibition of microtubule assembly, so its HRAC classification is Group D (Australia), Group K1 (global) or Group 3 (numeric).[3]

Roughly 250,000 pounds (110 t) was used in the US in 2019, down from about 750,000 pounds (340 t) in 2010, and 1,000,000 pounds (450 t) in 1995 (by USGS estimates).[4]

References

  1. ^ Taiz L, Zeiger E (2010). Plant Physiology (5th ed.). Sinauer Associates. pp. 433–434. ISBN 978-0-87893-866-7.
  2. ^ Klíma M, Vyvadilová M, Kucera V (January 2008). "Chromosome doubling effects of selected antimitotic agents in Brassica napus microspore culture" (PDF). Czech Journal of Genetics and Plant Breeding. 44 (1): 30–36. doi:10.17221/1328-CJGPB.
  3. ^ "Classification of Herbicides According to Site of Action". www.weedscience.org. WSSA. Retrieved 3 July 2025.
  4. ^ "Pesticide Use Maps - Oryzalin". water.usgs.gov. USGS. Retrieved 15 August 2025.
  • Oryzalin in the Pesticide Properties DataBase (PPDB)
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