ES466117A1 - Procedure for preparing herbicides based on diurethans. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

A method of preparing new cycloalkanecarboxanilide derivatives of the formula **(See formula)** where X represents an O, S, SO, SO2 or -NR3 moiety; Y represents a fluorine, chlorine or bromine atom, a cyano, nitro group, C (R3) = NOR3 or C (O) R3, or the group -Zp-alcohol, in which the portion of alcohol contains 1 to 6 atoms carbon and can be substituted by one or more fluorine, chlorine or bromine atoms, and Z represents an O, S, SO or SO2 group; R1 an alcohol group of from 1 to 6 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, or an aryl group of 6 to 10 carbon atoms, each optionally substituted by one or more fluorine atoms, chlorine or bromine, or represents an alkynyl group of from 3 to 4 carbon atoms, an alkoxyalkoxy group in which each alcohol group contains 1 to 6 carbon atoms, a cycloalkoxy group having 3 to 7 carbon atoms in the ring, an aralkoyl group of from 7 to 9 carbon atoms optionally substituted on the ring by one or two fluorine, chlorine or bromine atoms, or by an alcohol group of from 1 to 4 carbon atoms, a group of formula (see formula), or, when X represents the group NR3, R1 can represent the group (see formula), or, when X represents the group SO2, R1 can also represent the group (see formula); R2 represents an alcohol group of 1 to 6 carbon atoms, a fluorine, chlorine or bromine atom, an alkoxy or alcoholyl group in which the alcohol portion contains 1 to 6 carbon atoms, with the proviso that when Y represents a NO2 group and X represents an O- radical, R1 does not represent a methyl group; R3, R4 and R5 each independently represent a hydrogen atom or an alcohol or cycloalkoxy group of up to 6 carbon atoms, and R5 can also represent an alkoxy group of up to 6 carbon atoms; when X represents the group NR3, then R1 and R3 together can form part of a heterocyclic ring, such as **(See formula)** when R1 represents the group NR4R5, then R4 and R5 together may form part of a heterocyclic ring as shown above for R1 and R3 taken together; R6 represents an alcohol group of from 1 to 6 carbon atoms or an aryl or aralcohyl group of from 6 to 10 carbon atoms, optionally substituted by one or more fluorine, chlorine or bromine atoms; m is 2 or 3; n is 1 or 2; and p is 0 6 or 1, a process comprising reacting a 3,4-disubstituted aniline of the formula **(See formula)** with a cycloalkane carboxylic acid chloride of the formula **(See formula)** where X, Y, R1, R2 and n have the meanings defined above, in the presence of a base. (Machine-translation by Google Translate, not legally binding)