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
CAS Number	29091-21-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82032
ChEMBL	ChEMBL1223140
ChemSpider	31719
ECHA InfoCard	100.044.914
EC Number	249-421-3
KEGG	C18884
PubChem CID	34469
UNII	IJI5J414Q6
CompTox Dashboard (EPA)	DTXSID1034210
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,3-6,17H2,1-2H3 Key: RSVPPPHXAASNOL-UHFFFAOYSA-N
SMILES CCCN(CCC)C1=C(C=C(C(=C1[N+](=O)[O-])N)C(F)(F)F)[N+](=O)[O-]
Properties
Chemical formula	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]
Solubility in water	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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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, ^[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. 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. 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.

External links

• Prodiamine in the Pesticide Properties DataBase (PPDB)