Oryzalin

Oryzalin
Names
	IUPAC name 4-(Dipropylamino)-3,5-dinitrobenzenesulfonamide
Identifiers
CAS Number	19044-88-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	27326;
ECHA InfoCard	100.038.873
KEGG	C18877;
PubChem CID	29393;
UNII	662E385DWH;
CompTox Dashboard (EPA)	DTXSID8024238 ;
	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) Key: UNAHYJYOSSSJHH-UHFFFAOYSA-N ;
	SMILES CCCN(CCC)c1c([N+](=O)[O-])cc(S(N)(=O)=O)cc1[N+](=O)[O-];
Properties
Chemical formula	C12H18N4O6S
Molar mass	346.36 g·mol−1
Melting point	137–129 °C (279–264 °F; 410–402 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Oryzalin is an 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]

Research

Oryzalin has been studied for its potential use as an antiparasitic agent, particularly against Leishmania.^[5]^[6]

References

↑ Taiz L, Zeiger E (2010). Plant Physiology (5th ed.). Sinauer Associates. pp. 433–434. ISBN 978-0-87893-866-7.
↑ 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.
↑ "Classification of Herbicides According to Site of Action". www.weedscience.org. WSSA. Retrieved 3 July 2025.
↑ "Pesticide Use Maps - Oryzalin". water.usgs.gov. USGS. Retrieved 15 August 2025.
↑ Chan, Marion Man-Ying; Triemer, Richard E.; Fong, Dunne (1991). "Effect of the anti-microtubule drug oryzalin on growth and differentiation of the parasitic protozoan Leishmania mexicana". Differentiation. 46 (1): 15–21. doi:10.1111/j.1432-0436.1991.tb00861.x. PMID 2044859.
↑ Lopes, Rui M.; Corvo, M. Luísa; Eleutério, Carla V.; Carvalheiro, Manuela C.; Scoulica, Effie; Cruz, M. Eugénia M. (2012). "Formulation of oryzalin (ORZ) liposomes: In vitro studies and in vivo fate". European Journal of Pharmaceutics and Biopharmaceutics. 82 (2): 281–290. doi:10.1016/j.ejpb.2012.06.013. PMID 22771930.

External links

Oryzalin in the Pesticide Properties DataBase (PPDB)

[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.

[5] Chan, Marion Man-Ying; Triemer, Richard E.; Fong, Dunne (1991). "Effect of the anti-microtubule drug oryzalin on growth and differentiation of the parasitic protozoan Leishmania mexicana". Differentiation. 46 (1): 15–21. doi:10.1111/j.1432-0436.1991.tb00861.x. PMID 2044859.

[6] Lopes, Rui M.; Corvo, M. Luísa; Eleutério, Carla V.; Carvalheiro, Manuela C.; Scoulica, Effie; Cruz, M. Eugénia M. (2012). "Formulation of oryzalin (ORZ) liposomes: In vitro studies and in vivo fate". European Journal of Pharmaceutics and Biopharmaceutics. 82 (2): 281–290. doi:10.1016/j.ejpb.2012.06.013. PMID 22771930.

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