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,^[3] making it a Group D (Aus), K1 (global) or 3 (numeric).

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 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]