Substituted ureas and herbicidal compositions containing them

Abstract

The invention comprises N-(nortricyclyl-3) ureas of the formula <FORM:1071507/C2/1> in which R1 denotes an unsubstituted or substituted aliphatic hydrocarbon radical and R11 and R111 denote hydrogen atoms or unsubstituted or substituted hydrocarbon or alkoxy radicals or, together with the nitrogen atom to which they are attached, form an unsubstituted or substituted heterocyclic radical containing 5 or 6 ring members. When at least one of the radical R11 and R111 is an alkoxy radical, R1 may also denote hydrogen. R1 may be an alkyl or cycloalkyl radical and R11 and R111 may be alkyl, alkenyl, alkynyl or cycloalkyl radicals. The compounds may be prepared by reacting nortricyclyl-3-isocyanate or nortricyclyl-3-carbamic acid esters with amines, or by reacting nortricyclyl amines with isocyanates or carbamic acid chlorides. Examples are given. The products are useful as herbicides (see Division A5). Nortricyclyl - 3 - isocyanate, for use as an intermediate, is prepared by treating N-nortricyclyl carbamic acid ethyl ester with diphenylmethane-4,41-diisocyanate and a polyphenylmethyl polyisocyanate (such as is obtained by condensing aniline and formaldehyde and phosgenating the product).ALSO:As herbicides, use is made of N-(nortricyclyl)-3 ureas of the formula <FORM:1071507/A5-A6/1> in which R\sv denotes hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical containing 5 or 6 ring members (see atoms or unsubstituted or substituted hydrocarbon or alkoxy radicals or, together with the nitrogen atom to which they are attached, form an unsubstituted or substituted heterocyclic radical containing 5 or 6 ring members (see Division C2). R\sv may be an alkyl or cycloalkyl radical and R\yF and R\yG may be alkyl, alkenyl, alkynyl or cycloalkyl radicals. The compounds may be formulated as solutions, emulsions, suspensions, powders, pastes or granulates with the aid of solid or liquid diluents and, optionally, of emulsifying or dispersing agents, a number of solid or liquid diluents, emulsifying agents and dispersing agents being specified. Comparative experimental results are given.

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    US-3454393-AJuly 08, 1969Bayer AgNortricyclic-3-ureas and their herbicidal compositions and methods of use