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Prodiamine

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Prodiamine
Names
Preferred IUPAC name 2,6-Dinitro-N,N-dipropyl-4-(trifluoromethyl)benzene-1,3-diamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.044.914 Edit this at Wikidata
EC Number
  • 249-421-3
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H17F3N4O4/c1-3-5-18(6-4-2)11-9(19(21)22)7-8(13(14,15)16)10(17)12(11)20(23)24/h7H,3-6,17H2,1-2H3Key: RSVPPPHXAASNOL-UHFFFAOYSA-N
SMILES
  • CCCN(CCC)C1=C(C=C(C(=C1(=O))N)C(F)(F)F)(=O)
Properties
Chemical formula C13H17F3N4O4
Molar mass 350.298 g·mol
Melting point 124–125 °C (255–257 °F; 397–398 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H332, H410
Precautionary statements P261, P271, P273, P304+P312, P304+P340, P312, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Prodiamine is a preemergent herbicide of the dinitroaniline class. Prodiamine is used with crops such as soybeans, alfalfa, cotton, and ornamental crops. Prodiamine inhibits the formation of microtubules.

Prodiamine was developed by Sandoz AG and marketed beginning in 1987.

Prodiamine can be obtained starting from 2,4-dichlorobenzotrifluoride.

References

  1. Endeshaw, Molla M; Li, Catherine; Leon, Jessica de; Yao, Ni; Latibeaudiere, Kirk; Premalatha, Kokku; Morrissette, Naomi; Werbovetz, Karl A (2010). "Synthesis and evaluation of oryzalin analogs against Toxoplasma gondii". Bioorganic & Medicinal Chemistry Letters. 20 (17): 5179. doi:10.1016/j.bmcl.2010.07.003. PMC 2922421. PMID 20675138.
  2. "Herbicide Mode-Of-Action Summary". Purdue University.
  3. Entry on Prodiamin. at: Römpp Online. Georg Thieme Verlag, retrieved 8 June 2020.
  4. Thomas A. Unger (1996). Pesticide Synthesis Handbook. p. 877. ISBN 978-0-8155-1401-5.
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