Preparation of substituted guanidine derivatives

A process for preparing substituted guanidine compounds of the formula I, ##STR7## where the substituents have the following meanings independently of one another:

• R.sup.1 H,
• C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl;
• R.sup.2 C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl,
• --(C.sub.1 -C.sub.20 -alkylene)--COOR.sup.3,
• --(C.sub.1 -C.sub.20 -alkylene)--CONR.sup.4 R.sup.5, --(C.sub.1 -C.sub.20 -alkylene)--CN,
• --(C.sub.1 -C.sub.20 -alkylene)--SO.sub.2 R.sup.6,
• --[(CH.sub.2).sub.m --X--].sub.p --[(CH.sub.2).sub.n --Y--].sub.q --[(CH.sub.2).sub.o ].sub.r --Z;
• m, n, o
• 0 to 10;
• p, q, r
• 0 to 50,000;
• X O, NH;
• Y N--[(CH.sub.2).sub.m --X--].sub.p --[(CH.sub.2).sub.n --Y--].sub.q --[(CH.sub.2).sub.o ].sub.r --Z;
• Z OH, NH.sub.2 ;
• R.sup.3 H, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.6 -C.sub.18 -aryl
• Na, K, Li, Ca, Mg, N(R.sup.7).sub.4 ;
• R.sup.4 and R.sup.5 independently of one another
• H, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.6 -C.sub.18 -aryl;
• R.sup.6 OR.sup.8, N(R.sup.9).sub.2 ;
• R.sup.7 H, C.sub.1 -C.sub.20 -alkyl;
• R.sup.8 H, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.6 -C.sub.18 -aryl,
• Na, K, Li, Ca, Mg, N(R.sup.7).sub.4 ;
• R.sup.9 H, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.10 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.6 -C.sub.18 -aryl;
• which comprises
• a) reacting calcium cyanamide with an alcohol of the formula R.sup.10 -OH to give an isourea compound of the formula II, ##STR8## where R.sup.10 can be C.sub.1 -C.sub.20 -alkyl, b) reacting the substituted isourea II with a primary or secondary amine of the formula III, ##STR9## where the substituents R.sup.1 and R.sup.2 have the abovementioned meanings, to give guanidine compounds of the formula I.