IE37629L - Herbicidal triazines. - Google Patents

Abstract

1435585 6-Amino-s-triazin-2,4[1H,3H]-dione derivatives E I DU PONT DE NEMOURS & CO 23 May 1973 [24 May 1972 5 April 1973 (2)] 24677/73 Headings A5E E1C5J E1C5P E1C5M E1C14A E1C15D3 E1A3B ElA3Cand E1A5B3 Novel compounds have the Formula I wherein R 1 is selected from (a) alkyl of 2 to 8 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 4 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms, cycloalkylmethyl of 4 to 9 carbon atoms, cycloalkenylmethyl of 6 to 9 carbon atoms, bicycloalkyl or bicycloalkenyl of 7 to 10 carbon atoms and bicycloalkylmethyl or bicycloalkenylmethyl of 8 to 11 carbon atoms, trimethylcyclohexyl and tetramethylcyclohexyl; (b) the above alkyl groups substituted with one methoxy, ethoxy, methylthio or ethylthio group; (c) the above cycloalkyl groups substituted with one alkyl group of 2 to 4 carbon atoms, 1 or 2 methyl groups, 1 or 2 chlorine or bromine atoms, one methoxy or one ethoxy group; and (d) a group of Formula wherein Q is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of alkylthio of 1 or 2 carbon atoms, nitro or a trifluoromethyl group; Y is hydrogen, chlorine or methyl; and Z is hydrogen or chlorine; R 2 is hydrogen, alkyl of 1 to 3 carbon atoms or a cation selected from Na<SP>+</SP>, Li<SP>+</SP>, K<SP>+</SP>, (Ca/2)<SP>+</SP>, ammonium and dimethylammonium; R 2 is hydrogen, methyl or ethyl; R 4 is alkyl of 1 to 4 carbon atoms, alkenyl of 3 or 4 carbon atoms, alkynyl of 3 or 4 carbon atoms, or methoxy; and X is oxygen or sulphur; provided that when X is sulphur, neither R 2 nor R 3 is hydrogen. The compounds of Formula I are prepared, for example, by reaction of a corresponding 6- methylthio compound with an amine of Formula R 3 R 4 NH or, in the case of a 4-thio derivative, by reaction of P 2 S 5 with the corresponding 2,4-dione derivative. The compounds of Formula I in which R 2 is alkyl [=R<SP>1</SP> 2 ] are also obtained by cyclization, in the presence of a base (an alkali metal C 1-4 alkoxide), of a compound of Formula CH 3 O-CO-NR<SP>1</SP> 2 -C(NR 3 R 4 )=N-CX-NHR 1 These latter starting materials are themselves obtained by reacting methoxycarbonyl-cyanamide with an alkylating agent of Formula R<SP>1</SP> 2 -Q [Q = chloride, bromide, iodide or -O-SO 2 OR<SP>1</SP> 2 ] to form N-methoxycarbonyl-N-alkylcyanamide, reacting the latter with an amine of Formula R 3 R 4 NH to form a compound of Formula CH 3 O-CO-NR<SP>1</SP> 2 -C(NR 3 R 4 )=NH and then reacting this intermediate with an isocyanate or isothiocyanate of Formula R 1 NCX. The compounds of Formula I are herbicides. [GB1435585A]