Prodiamine

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, making it a Group D, K1 or 3.
Prodiamine was developed by Sandoz AG and marketed beginning in 1987. Prodiamine can be obtained starting from 2,4-dichlorobenzotrifluoride. It is normally sold formulated as dispersible granules or liquid concentrate. It is not registered in the United Kingdom or European Union, though it is used in Australia, sold under the "Spartan" and "Barricade" trademarks.
Prodiamine is surface applied, and requires no soil incorporation.

Toxicity and environmental behaviour

Prodiamine is practically non-toxic to mammals, with an oral LD₅₀ of over 5000 mg/kg. 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. 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.
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.