Patent GB-927347-A (GB)
Title: Process for the production of new triazine derivatives and their use as herbicides
IPC: A01N43/70
Filed: 1959-11-03
Abstract: The invention comprises compounds of the formula: <FORM:0927347/IV(a)/1> wherein X and Y represent oxygen or sulphur, R1 and R2 represent C1-6 alkyl, C1-6 alkenyl or C1-6 alkoxyalkyl radicals, R3 and R5 represent hydrogen or C1-6 alkyl or C1-6 alkenyl radicals, R4 represents hydrogen or a C1-6 alkyl, C1-6 alkenyl or C1-6 alkoxyalkyl radical, and "alk" represents a C1-6 alkylene radical.  The compounds are prepared (1) by reacting a 2-halogen-4:6-diamino-s-triazine of the formula: <FORM:0927347/IV(a)/2> wherein "Hal" represents chlorine or bromine, with an alkali metal compound of an alcohol or of a mercaptan of the formula HX-alk-Y-R1; (2) by reacting a triazine derivative of the formula:  <FORM:0927347/IV(a)/3> wherein "Hal" represents chlorine or bromine, with an amine of the formula HNR4R5 in the presence of an acid binding agent; (3) by reacting a triazine derivative of the formula:  <FORM:0927347/IV(a)/4> wherein "Hal" represents chlorine or bromine, with an amine of the formula HNR2R3 in the presence of an acid binding agent; (4) By reacting a 2-(R1-Y-alk-X-substituted)-4:6-dichloro-(or dibromo-)-s-triazine with two molecules of an amine of the formula HNR2R3 or HNR4R5 in the presence of an acid binding agent; and (5) by reacting an alkali metal salt of a 2-mercapto-4:6-diamino-s-triazine of the formula: <FORM:0927347/IV(a)/5> with a reactive ester (e.g. a halide or an alkali metal salt of an acid sulphuric acid ester or aryl sulphonic acid ester) of a compound of the formula HO-alk-Y-R1.  Specification 927,348 is referred to.ALSO:Agents for the inhibition of plant growth, in particular weed killers, comprise as the active ingredient triazine derivatives of the formula:-  <FORM:0927347/I/1> wherein X and Y represent oxygen or sulphur, R1 and R2 represent C1-6 alkyl, C1-6 alkenyl or C1-6 alkoxyalkyl radicals, R3 and R5 represent hydrogen or C1-6 alkyl or C1-6 alkenyl radicals, R4 represents hydrogen or a C1-6 alkyl, C1-6 alkenyl or C1-6 alkoxyalkyl radical, and "Alk" represents a C1-6 alkylene radical, together with suitable carriers and distributing agents, including fertilisers such as ammonium sulphate or urea, and plant growth accelerators such as 3-amino-1, 2, 4-triazole.  Carriers also include compounds having a phytotoxic action such as high boiling mineral oil fractions; inert solvents such as alcohols, water, ketones, cyclic and chlorinated hydrocarbons, animal and vegetable oils; emulsifying, dispersing and surface active agents such as quaternary ammonium compounds, soaps, soft soaps, alkali metal salts of aliphatic long chained sulphuric acid monoesters, of aliphatic-aromatic sulphonic acids or of long-chain alkoxy acetic acids, polyethylene glycol ethers of fatty alcohols or of alkyl phenols, polycondensation products of ethylene oxide and sulphite waste liquors; solid materials such as talcum, diatomaceous earth, kaolin, bentonite, calcium carbonate, tricalcium phosphate, sand, sawdust and ground cork; other herbicides such as salts of a , a -dichloropropionic acid.  The above agents or their active ingredients may be applied to arable land or plants growing thereon in quantities ranging from 0,25 to 20 lbs. per acre, in order to inhibit the growth of undersirable plants.  Such inhibition may take the form of herbicidal effects, defoliation (e.g. of cotton plants), desiccation (e.g. of potato plants), blossom thinning and prolongation of harvesting periods and storing propensities. Specification 927,348 is referred to.ALSO:Agents for the inhibition of plant growth, in particular weed killers, comprise as the active ingredient triazine derivatives of the formula <FORM:0927347/VI/1> wherein X and Y represents oxygen or sulphur, R1 and R2 represent C1-6 alkyl  C1-6 alkenyl or C1-6 alkoxyalkyl radicals, R3 and R5 represent hydrogen or C1-6 alkyl or C1-6 alkenyl radicals, R4 represents hydrogen or a C1-6 alkel, C1-6 alkenyl or C1-6 alkoxyalkyl radical, and "Alk" represents a C1-6 alkylene radical, together with suitable carriers and distributing agents, including fertilisers such as ammonium sulphate or urea, and plant growth accelerators such as 3-amino-1, 2, 4-triazole.  Carriers also include compounds having a phytotoxic action such as coal tar oils, high boiling mineral oil fractions, inert solvents such as alcohols, water, ketones, cyclic and chlorinated hydrocarbons e.g. ethanol, isopropanol acetone, butanone, cyclohexanone, diacetone alcohol, benzene, toluene xylene, tetrachloroethane or ethylene chloride, animal and vegetable oils; emulsifying, dispersing and surface active agents such as quaternary ammonium compounds, soaps, soft soaps, alkali metal salts of aliphatic long chained sulphuric acid monoesters, of aliphatic-aromatic sulphonic acids or of long-chain alkoxy acetic acids, polyethylene glycol ethers of fatty alcohols or of alkyl phenols, polycondensation products of ethylene oxide and sulphite waste liquors; solid materials such as talcum, diatomaceous earth, kaolin, bentonite, calcium carbonate, tricalcium phosphate, sand, sawdust and ground cork; other herbicides such as salts of a ,a -dichloropropionic acid.  The above agents or their active ingredients may be applied to arable land or to plants growing therein in quantities ranging from 0.25 to 20 lb. per acre, in order to inhibit the growth of undesirable plants.  Such inhibition may take the form of herbicidal effects, defoliation (e.g. of cotton plants), desiccation (e.g. of potato plants), blossom thinning and prolongation of harvesting periods and storing propensities. Specification 927,348 is referred to.