Patent GB-1056290-A (GB)
Title: Dicycloalkyl ureas
IPC: C07C275/26
Filed: 1964-05-04
Abstract: The invention comprises urea derivatives of the formula R1-NH-CO-NH-(CH2)t-R2, in which t is 0 or 1 and, when t is 0, R1 and R2 are different cycloalkyl groups of 5-8 carbon atoms or different bicycloalkyl groups of 7 or 8 carbon atoms and, when t is 1, R1 and R2 are identical or different cycloalkyl groups of 5-8 carbon atoms or bicycloalkyl groups of 7 or 8 carbon atoms.  In any event, the cycloalkyl or bicycloalkyl groups may be substituted by one or two halogen atoms or by one or two methyl groups or by one halogen atom and one methyl group.  The compounds may be prepared by reacting an appropriate isocyanate or urea derivative with an appropriate amine. Examples are given in which (1) cyclohexyl isocyanate and 2-methylcyclohexylamine yield 1-(2 - methyl - cyclohexyl) - 3 - cyclohexyl urea, (2) cyclohexyl isocyanate and hexahydro-benzylamine yield 1-cyclohexyl-3-cyclohexyl-methyl urea, (3) cyclopentyl urea and 2-methyl-cyclohexylamine yield 1 - cyclopentyl - 3 - (2-methylcyclohexyl) urea, (4) cyclopentyl urea and cyclooctylamine yield 1 - cyclopentyl - 3-cyclooctyl urea, (5) cyclohexyl isocyanate and 4 - amino - 1,3 - dimethyl - cyclohexane yield 1 - cylcohexyl - 3 - (1,3 - dimethylcyclohexyl) urea, (6) cyclohexyl isocyanate and 3-methyl-cyclohexylamine yield 1 - cyclohexyl - 3 - (3-methylcyclohexyl) urea, (7) cyclopentyl urea and hexahydrobenzylamine yield 1-(cyclohexyl-methyl) -3-cyclopentyl urea. Other specified products include 1-(3-bromocyclohexyl)-3-cycloheptyl urea, 1-(2-iodocyclohexyl)-3-(2-methyl-cyclohexyl) urea, 1 - (2 - norbornylmethyl) - 3-cyclohexyl urea, 1-(bicyclooctyl)-3-cyclohexyl urea, 1-(dichlorocyclopentyl)-3-cyclooctyl urea and 1-(2-methylcyclohexyl)-3-(2-fluorocyclohexyl) urea.  The products are useful as selective weed-killers (see Division A5).  Reference has been directed by the Comptroller to Specification 812,120.ALSO:As selective weed-killers, use is made of urea derivatives of the formula R1-NH-CO-NH-(CH2)t-R2, in which t is 0 or 1 and, when t is 0, R1 and R2 are different cycloalkyl groups of 5-8 carbon atoms or different bicycloakyl groups of 7 or 8 carbon atoms and, when t is 1, R1 and R2 are identical or different cycloalkyl groups of 5-8 carbon atoms or bicycloalkyl groups of 7 or 8 carbon atoms.  In any event, the cycloalkyl or bicycloalkyl groups may be substituted by one or two halogen atoms or by one or two methyl groups or by one halogen atom and one methyl group (see Division C2).  Specified products include 1-(2-methyl-cyclohexyl)-3-cyclohexyl urea, 1-cyclohexyl-3-cyclohexylmethyl urea, 1-cyclopentyl-3-(2-methylcyclohexyl) urea, 1-cyclopentyl-3-cyclohexyl) urea, 1-(cyclohexylmethyl)-3-cyclocyclohexyl) urea, 1-cyclohexyl-3-(3-methylcyclohexyl) urea, 1-(cyclohexylmethyl)3-3cyclopentyl urea, 1-(3-bromocyclohexyl)-3-cycloheptyl urea, 1-(2-idocyclohexyl)-3-(2-methylcyclohexyl) urea, 1-(2-norbornylmethyl)-3-cyclohexyl urea, 1-(bicyclooctyl)-3-cyclohexyl urea, 1-(dichloro-cyclopentyl)-3-cyclooctyl urea and 1-(2-methylcyclohexyl)-3-(2-fluorocyclohexyl) urea.  The products may be formulated as solid compositions or solutions or emulsions with the aid of diluents.  The diluents may be inert solids, anionic, cationic or non-ionic surface-active agents, mineral oils or water-solvents, a number of each of which are specified.  The compositions may contain also plant nutrients, fertilizers, insecticides, fungicides, nematocides and other herbicides and a number of suitable insecticides, fungicides and herbicides are also specified.  Examples of herbicidal compositions and of their use are given.  Reference has been directed by the Comptroller to Specification 812,120.