Prodiamine

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.[2]

Prodiamine
Names
Preferred IUPAC name
2,6-Dinitro-N1,N1-dipropyl-4-(trifluoromethyl)benzene-1,3-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.044.914
EC Number
  • 249-421-3
KEGG
UNII
  • 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,3-6,17H2,1-2H3
    Key: RSVPPPHXAASNOL-UHFFFAOYSA-N
  • CCCN(CCC)C1=C(C=C(C(=C1[N+](=O)[O-])N)C(F)(F)F)[N+](=O)[O-]
Properties
C13H17F3N4O4
Molar mass 350.298 g·mol−1
Melting point 124–125 °C (255–257 °F; 397–398 K)[1]
Hazards
GHS labelling:
Warning
H332, H410
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 [77 °F], 100 kPa).
Infobox references

Prodiamine was developed by Sandoz AG and marketed beginning in 1987.[3]

Prodiamine can be obtained from 2,4-dichlorobenzotrifluoride by reaction with nitric acid in the presence of sulfuric acid, dipropylamine, and ammonia.[4]

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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