Patent GB-811861-A (GB)
Title: Improvements in or relating to thio-carbaminates, bisthio-carbaminates and bisdithio-carbaminates, methods of producing such substances and to compositions containing such substances for treating plants
IPC: C07D295/21
Filed: 1956-03-27
Abstract: The invention comprises thiocarbaminates, bis-thiocarbaminates and bis-dithiocarbaminates of the formul : <FORM:0811861/IV (b)/1> and <FORM:0811861/IV (b)/2> in which R1 and R2 represent hydrogen and/or alkyl groups or form, together with the nitrogen atom, a ring of not more than 6 atoms, R3 represents a bivalent, if desired substituted, alkylene, aralkylene or arylene group, R5 represents a bivalent alkylene, aralkylene or arylene group or, together with the two nitrogen atoms and the two groups R2 forms a ring of not more than 6 atoms, or, together with one nitrogen atom and the group R2 attached to this atom, a ring of not more than 6 atoms, X represents an NH2 or substituted NH2 group, an OH group or an OH group in which the hydrogen atom is replaced by a cation, or an alkyl, aralkyl or aryl group, and Z represents an oxygen or sulphur atom.  R1 and R2 are preferably C1-4 alkyl groups, particularly methyl ethyl or isopropyl groups; R3 and R5 are preferably phenylene or C1-4 alkylene groups, particularly methylene, ethylene, isopropylene, propylene or butylene groups; X is preferably an OH group or a C1-6 alkoxy group, particularly a methoxy or ethoxy group.  Compounds of the first general formula and of the second general formula in which Z represents oxygen, are obtained by reacting a compound <FORM:0811861/IV (b)/3> where Me is a metal cation and Alk is an alkylene group, with a compound <FORM:0811861/IV (b)/4> or <FORM:0811861/IV (b)/5> respectively.  Compounds of the second general formula in which Z represents sulphur are obtained by reacting a compound <FORM:0811861/IV (b)/6> wherein Me is a metal cation, with a compound <FORM:0811861/IV (b)/7> wherein Hlg is a halogen atom.  The examples describe the preparation of di-sodium-S:S1-bis - (carboxymethyl) - ethylene bis - dithiocarbaminate and N:N - dimethylthiocarbamyl-glycolic acid. Reference is also made to products of the formul : <FORM:0811861/IV (b)/8> <FORM:0811861/IV (b)/9> <FORM:0811861/IV (b)/100> <FORM:0811861/IV (b)/111> to the corresponding free acids; to S:S1-bis-(carboxymethyl) - ethylene - bis - dithiocarbaminate; and to other salts and esters of such compounds.  A starting material of the formula: <FORM:0811861/IV (b)/122> is prepared by adding chloroacetamide to the solution of the compound <FORM:0811861/IV (b)/133> obtained by reacting sodium glycolate with carbon disulphide and caustic potash.ALSO:Pesticidal and plant growth stimulating compositions comprise thiocarbaminates, bisthiocarbaminates and bis-dithio-carbaminates of the formulae <FORM:0811861/I/1> and <FORM:0811861/I/2> in which R1 and R2 represent hydrogen and/or alkyl groups or form, together with the nitrogen atom, a ring of not more than 6 atoms, R3 represents a bivalent, if desired substituted, alkylene, aralkylene or arylene group, R5 represents a bivalent alkylene, aralkylene or arylene group, or, together with the two nitrogen atoms and the two groups R2, forms a ring of not more than 6 atoms, or, together with one nitrogen atom and the group R2 attached to this atom, a ring of not more than 6 atoms, X represents an NH2 or substituted NH2 group, an OH group or an OH group in which the hydrogen atom is replaced by a cation (e.g. sodium) or an alkyl, aralkyl group, and Z represents an oxygen or sulphur atom, together with a liquid or solid inert carrier material, preferably water.ALSO:Pesticidal and plant growth stimulating compositions comprise thiocarbaminates, bis-thiocarbaminates and bis-dithio-carbaminates of the formul :  <FORM:0811861/VI/1> and <FORM:0811861/VI/2> in which R1 and R2 represent hydrogen and/or alkyl groups or form, together with the nitrogen atom, a ring of not more than 6 atoms, R3 represents a bivalent, if desired substituted, alkylene, aralkylene or arylene group, R5 represents a bivalent alkylene, aralkylene or arylene group, or, together with the two nitrogen atoms and the two groups R2 forms a ring of not more than 6 atoms, or, together with one nitrogen atom and the group R2 attached to this atom, a ring of not more than 6 atoms, X represents an NH2 or substituted NH2 group, an OH group or an OH group in which the hydrogen atom is replaced by a cation (e.g. sodium) or an alkyl, aralkyl or aryl group, and Z represents an oxygen or sulphur atom, together with a liquid or solid inert carrier material, preferably water.