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Prodiamine

Prodiamine
Names
Preferred IUPAC name
2,6-Dinitro-N1,N1-dipropyl-4-(trifluoromethyl)benzene-1,3-diamine
Other names
  • Prodiamina (Polish)
  • BRN 2181386
  • USB 3153
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.044.914 Edit this at Wikidata
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
Appearance Yellow powder[1]
Density 1410 kg/m3[1]
Melting point 124–125 °C (255–257 °F; 397–398 K)[2]
Boiling point N/A, degrades at 240°C[1]
0.013 mg/L[1]
Solubility in acetone 226 g/L[1]
Solubility in benzene 74 g/L[1]
Solubility in ethanol 7 g/L[1]
Solubility in xylene 35.4 g/L[1]
Vapor pressure 0.0033 mPa[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Skin & eye irritant[1]
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
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).

Prodiamine is a preëmergent herbicide of the dinitroaniline class. Prodiamine is used with crops such as soybeans, alfalfa, cotton, and ornamental crops. Prodiamine inhibits the formation of microtubules,[3] making it a Group D (Aus), K1 (global) or 3 (numeric).

Prodiamine was developed by Sandoz AG and marketed beginning in 1987.[4] Prodiamine can be obtained starting from 2,4-dichlorobenzotrifluoride.[5] It is normally sold formulated as dispersible granules or liquid concentrate. It is not registered in the United Kingdom or European Union,[1] though it is used in Australia, sold under the "Spartan" and "Barricade" trademarks.[6][7]

Prodiamine is surface applied, and requires no soil incorporation.[8]

Toxicity and environmental behaviour

Prodiamine is practically non-toxic to mammals, with an oral LD50 of over 5000 mg/kg (tested on rats). No observable effect exists for rats fed up to 6 mg/kg/day. For birds, the LD50 is over 2250 mg/kg, for bees, over 100 micrograms per bee, and for earthworms over 1000 mg/kg.[1] These values are not tested beyond there, as they already show the acute toxicity not to be a concern.

Prodiamine has moderate aquatic toxicity, with a 96-hour LC50 of 0.829 mg/L for rainbow trout, and a NOEL of 12 μg/L over 21 days. It has a similar acute toxicity to daphnia, though a higher NOEL of 23 μg/L. The LC50 is better for crustaceans, at 2.1 mg/L. Prodiamine is highly toxic to algae, halting growth at 3 μg/L.[1]

In soil, prodiamine has a half-life of 60 to 80 days by most estimates, except the EPA which states 120 days. It is non-mobile in soil, and unlikely to bioaccumulate.[1]

References

  1. ^ a b c d e f g h i j k l m n Hertfordshire, University of. "Prodiamine (Ref: SAN 745H)". sitem.herts.ac.uk. Pesticide Properties Database.
  2. ^ 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): 5179–5183. doi:10.1016/j.bmcl.2010.07.003. PMC 2922421. PMID 20675138.
  3. ^ "Herbicide Mode-Of-Action Summary". Purdue University.
  4. ^ Entry on Prodiamin. at: Römpp Online. Georg Thieme Verlag, retrieved 8 June 2020.
  5. ^ Thomas A. Unger (1996). Pesticide Synthesis Handbook. p. 877. ISBN 978-0-8155-1401-5.
  6. ^ "Spartan Herbicide (Prodiamine)". Specialist Sales. 25 February 2024.
  7. ^ "Barricade Herbicide". Specialist Sales. 18 April 2023.
  8. ^ "Trifluralin vs Prodiamine: A Comparison for Weed Control". POMAIS Agriculture. 24 October 2024.
  • Prodiamine in the Pesticide Properties DataBase (PPDB)

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