NOMENCLATURE
dicamba
Common name dicamba
IUPAC name 3,6-dichloro-o-anisic acid; 3,6-dichloro-2-methoxybenzoic acid
Chemical Abstracts name 3,6-dichloro-2-methoxybenzoic acid
CAS RN [1918–00–9]; [7600–50–2] 5-hydroxy derivative
PHYSICAL CHEMISTRY
dicamba
Mol. wt. 221.0 M.f. C8H6Cl2O3 Form Pure a.i. (992 g/kg) is a white granular solid. Tech. is a light cream to tan solid, composed of granules, lumps and flakes. M.p. 114–116 °C B.p. >200 °C V.p. 1.67 mPa (25 °C, calc.) Kow logP = –0.55 (pH 5.0), –1.88 (pH 6.8), –1.9 (pH 8.9) (OECD 105) Henry 1.0 × 10-4 Pa m3 mol-1 S.g./density 1.488 (25 °C) Solubility In water 6.6 (pH 1.8), >250 (pH 4.1, 6.8, 8.2) (all in g/l, 25 °C). In methanol, ethyl acetate and acetone >500, dichloromethane 340, toluene 180, hexane 2.8, octanol 490 (all in g/l, 25 °C). Stability Resistant to oxidation and hydrolysis under normal conditions. Stable in acids and alkalis. Decomposes at c. 200 °C. Aqueous photolysis DT50 14–50 d. pKa 1.97
APPLICATIONS
Biochemistry Synthetic auxin (acting like indolylacetic acid).
Mode of action Selective systemic herbicide, absorbed by the leaves and roots, with ready translocation throughout the plant via both the symplastic and apoplastic systems. Acts as an auxin-like growth regulator.
Uses Control of annual and perennial broad-leaved weeds and brush species in cereals, maize, sorghum, sugar cane, asparagus, perennial seed grasses, turf, pastures, rangeland and non-crop land. Used in combinations with many other herbicides. Phytotoxicity Most legumes are sensitive.
Formulation types GR; SL.
Compatibility Precipitation of the free acid from water may occur if the dimethylammonium salt is combined with lime sulfur, heavy-metal salts, or strongly acidic materials.
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