Patent GB-973888-A (GB)
Title: New triazine derivatives,compositions containing same,and processes for their production
IPC: A01N43/70
Filed: 1961-02-20
Abstract: Plants are treated with a triazine derivative of the formula <FORM:0973888/C1/1> in which Hal represents chlorine, bromine or fluorine, R1 represents hydrogen or an alkyl radical having from 1 to 5 carbon atoms or an alkenyl radical having from 2 to 4 carbon atoms, R2 represents hydrogen or an alkyl radical having from 1 to 5 carbon atoms, an alkenyl radical having from 2 to 4 carbon atoms or an alkoxyalkyl radical having a total of at most 8 carbon atoms, and X represents chlorine, bromine or fluorine or an <FORM:0973888/C1/2> radical in which R3 is an alkyl radical having from 1 to 5 carbon atoms, an alkenyl radical having from 2 to 4 carbon atoms or an alkoxyalkyl radical having a total of at most 8 carbon atoms, or the acyl radical of a saturated or unsaturated fatty acid having from 2 to 5 carbon atoms, and R4 is a radical corresponding to the definition for R2 (see Division C2). The triazine derivative may be applied in the form of a solution, emulsion, suspension or dust.  The liquid medium may be water or an organic liquid having a b.p. of 100-150 DEG  C.  An emulsifying agent may be present.  A dust may contain talcum, diatomaceous earth, kaolin, bentonite, calcium carbonate, tricalcium phosphate, sand, sawdust, or cork powder. 3-amino-1,2,4-triazole or a salt of a ,a -dichloropropionic acid may also be present to enhance the activity.ALSO:The invention comprises triazine derivatives of the general formula <FORM:0973888/C1/1> in which Hal represents chlorine, bromine or fluorine, R1 represents hydrogen or an alkyl radical having from 1 to 5 carbon atoms or an alkenyl radical having from 2 to 4 carbon atoms, R2 represents hydrogen or an alkyl radical having from 1 to 5 carbon atoms, an alkenyl radical having from 2 to 4 carbon atoms or an alkoxyalkyl radical having a total of at most 8 carbon atoms, and X represents chlorine, bromine or fluorine or an -N <FORM:0973888/C1/2> radical in which R3 is an alkyl radical having from 1 to 5 carbon atoms, an alkenyl radical having from 2 to 4 carbon atoms or an alkoxyalkyl radical having a total of at most 8 carbon atoms, or the acyl radical of a saturated or unsaturated fatty acid having from 2 to 5 carbon atoms, and R4 is a radical corresponding to the definition for R2. The compounds wherein X is halogen or an amide group may be prepared by reacting, in an inert solvent, a cyanuric trihalide with one or two mols of an alkali metal salt of an acid amide of the general formula R2NHCOR1 in which R1 and R2 have the meanings given above; in producing the diamido compounds, one mol each of two different amide salts may be used.  The compounds wherein X is an amino group may be prepared by reacting a cyanuric acid trihalide successively, and in any order, with one mol of an alkali metal salt of an acid amide as defined above and, in the presence of an acid binding agent, with one mol of an amine of the general formula R31R4NH in which R31 is an alkyl radical having from 1 to 5 carbon atoms, an alkenyl radical having from 2 to 4 carbon atoms or an alkoxyalkyl radical having a total of at most 8 carbon atoms, and R4 has the meaning given above. The compounds wherein X is an amino group may also be prepared by reacting a compound of the general formula <FORM:0973888/C1/3> in which Hal, R31 and R4 have the meanings given above, with one mol of an alkali metal salt of an acid amide, as defined above, in an organic solvent.  The monoamido-triazines may further be prepared by monoacylating a compound of the general formula <FORM:0973888/C1/4> in which X1 is chlorine, bromine or fluorine, or a <FORM:0973888/C1/5> radical, and all the other symbols have the meanings given above. Acylation can be achieved by (a) heating such a compound, in an inert organic solvent, with an anhydride or halide of an acid of the general formula R1COOH in which R1 has the meaning given above or (b) reacting such a triazine compound with an aliphatic ketene containing from 2 to 4 carbon atoms, particularly carbomethylene, in the presence of a small amount of a mineral acid. The starting triazine compounds used in these latter monoacylation processes may be obtained by reacting a cyanuric halide, in the presence of an acid binding agent, with one or two equivalents of an appropriate aliphatic amine and, where two equivalents are used, one equivalent of each of two different, suitable amines may be employed; several of these triazine derivatives are exemplified, most of which are known compounds. Many compounds of the invention are exemplified, typical examples being 2, 4-dichloro-6-(N-formyl-methylamino-1, 3, 5-triazine, 2, 4-dichloro-6-(N-acetyl-allylamino)-1, 3, 5-triazine, 2, 4-difluoro-6-(N-acetyl-ethylamino)-1, 3, 5-triazine, 2-fluoro-4, 6-bis-(N-acetyl-ethylamino)-1, 3, 5-triazine, 2-chloro-4, 6-bis-(N-n-butyryl-methylamino)-1, 3, 5-triazine, 2-chloro-4, 6-bis-(N-crotonyl-ethylamino)-1, 3, 5-triazine, 2-chloro-4, 6-bis-[N-acetyl-(g -methoxypropylamino)]-1,3,5-triazine, 2-fluoro-4-ethylamino(N-acetyl-ethylamino)-1, 3, 5-triazine, 2-chloro-4-diethylamino-6-(N-acetyl-ethylamino)-1, 3, 5-triazine, 2-chloro-4-diethylamino-6-(N-acetyl-ethylamino)-1, 3, 5-triazine, 2-chloro-4-allylamino-6-(N-acetyl-allylamino)-1, 3, 5-triazine and 2-chloro-4-(g -methoxy propylamino)-6-[N - acetyl - (g  - methoxypropylamino)]-1, 3, 5-triazine.  The compounds of the invention are useful as herbicidal agents and, also, for inhibiting plant growth in other ways (see Division A5) and for accelerating plant growth (see Division C1).ALSO:Compositions for weed control and other plant growth inhibiting effects, e.g. defoliation, comprise as active ingredient a triazine derivative of the formula <FORM:0973888/A5-A6/1> in which Hal represents chlorine, bromine, or fluorine, R1 represents hydrogen or an alkyl radical having from 1 to 5 carbon atoms or alkenyl radical having from 2 to 4 carbon atoms, R2 represents hydrogen or an alkyl radical having from 1 to 5 carbon atoms, an alkenyl radical having from 2 to 4 carbon atoms or an alkoxyalkyl radical having a total of at most 8 carbon atoms, and X represents chlorine, bromine or fluorine or an <FORM:0973888/A5-A6/2> radical in which R3 is an alkyl radical having from 1 to 5 carbon atoms, an alkenyl radical having from 2 to 4 carbon atoms or an alkoxyalkyl radical having a total of at most 8 carbon atoms, or the acyl radical of a saturated or unsaturated fatty acid having from 2 to 5 carbon atoms, and R4 is a radical corresponding to the definition for R2.  The compositions may be used in the form of solutions, emulsions, suspensions or dusts, wherein the active ingredients are admixed with conventional carriers and/or emulsifying or dispersing agents. The compositions may also contain substances having bactericidal or fungicidal properties.  For accelerating the action of the active ingredients, a substance such as 3-amino-1,2,4-triazole may be added and, for broadening the spectrum of herbicidal activity, substances such as salts of a ,a -dichloropropionic acid may be incorporated in the compositions. Fertilizers, e.g. ammonium sulphate or urea, may also be present.  In examples illustrating the herbicidal compositions, the following active ingredients are specified:-2 - chloro - 4 - isopropylamino - 6 - (N - acetyl - ethylamino) - 1,3,5 - triazine, 2 - bromo - 4 - ethylamino - 6 - (N - acetyl - ethylamino) - 1,3,5 - triazine, 2 - chloro - 4 - ethylamino - 6 - (N - acetyl - ethylamino) - 1,3,5 - triazine, 2 - chloro - 4 - ethylamino - 6 - (N - propionyl - ethylamino) 1,3,5 - triazine, 2,4 - dichloro - 6 - (N - formyl - methylamino) - 1,3,5 - triazine, 2 - chloro - 4 - methylamino - 6 - (N - acetyl - methylamino) 1,3,5 - triazine and 2 - chloro - 4,6 - bis - (N - acetyl - ethylamino) - 1,3,5 - triazine.  (For the preparation of the triazine derivatives see Division C2).