Prodiamine
Chemical compound
From Wikipedia, the free encyclopedia
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).
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| Names | |
|---|---|
| Preferred IUPAC name
2,6-Dinitro-N1,N1-dipropyl-4-(trifluoromethyl)benzene-1,3-diamine | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.044.914 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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: | |
  | |
| 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).
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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]