Preparation of 4-substituted di:nitroaniline derivatives used as cell division inhibitors in herbicides

摘要

Preparation of 4-substituted dinitroaniline derivatives of formula (I) comprises: (i) denitrating a 4-substituted phenol in slight excess of nitrating agent with a quantity of protons and catalyst comprising transition metals of column IV-XII of the periodic table (preferably soluble ions of Fe<3+>, Fe<2+>, Zn<2+> or Cu<2+>); (ii) alkylating using monohaloalkyl containing at least 3C (optionally cyclic and/or containing at least one unsaturation), monohaloalkyl containing at least 2C and optionally comprising a saturated cycle or at least one unsaturation or (RO)nR'X (preferably chloromethyl polymethoxyethers or chloromethyl polyethoxyethers, ethylene oxides, propylene oxides or compounds of formula (II)); and (iii) aminating with a primary or secondary amine. R1 = tert.-butyl, sulphonamido, CF3, methylsulphonyl or isopropyl; and R2, R3 = 1-6C alkyl, cycloalkyl, haloalkyl or alkanyl;