GB1129797A — Phosphorus-containing pyrimidine derivatives and biologically active compositions containing them

USPTO Abstract

1,129,797. Phosphorus-containing pyrimidine derivatives. IMPERIAL CHEMICAL INDUSTRIES Ltd. 15 March, 1967 [31 March, 1966 (2)], Nos. 14266/66 and 14267/66. Heading C2C. [Also in Division A5] The invention comprises pyrimidine derivatives having the formula or a salt thereof (e.g. hydrochloride), wherein either (a) X is O or S, R 1 is H, R 2 is H, alkyl, alkenyl, aryl (which may be substituted), cycloalkyl, lower acyl containing up to 6 carbon atoms or nitrogen-containing heterocyclic radical, R 4 and R 5 are H, alkyl, alkenyl or substituted or unsubstituted aryl, and R 6 is alkyl, alkenyl or aryl, provided that R 1 , R 2 and R 5 are not all hydrogen; or (b) X is O or S, R 1 and R 2 are alkyl or alkenyl or together with the N atom form a substituted or unsubstituted heterocyclic radical e.g. piperidino or morpholino, R 4 is an unsubstituted or substituted aryl radical, R 5 is H or a substituted or unsubstituted alkyl or alkenyl radical and R 2 is a substituted or unsubstituted alkyl or alkenyl radical. The invention also includes as novel compounds those of the above formula in which (1) NR 1 R 2 is NH 2 , R 4 is CH 3 , R 5 is H and O-P(X)(OR 6 ) 2 is OP(S)(OCH 3 ) 2 ; (2) NR 1 R 2 is NH 2 , R 4 is phenyl, R 5 is H and O-P(X)(OR 6 ) 2 is OP(O)(OC 4 H 9n ) 2 ; and (3) NR 1 R 2 is NH 2 , R 4 is nC 3 H 7 , R 5 is H and O-P(X)(OR 6 ) 2 is OP(S)(OC 2 H 5 ) 2 . The compounds may be obtained by reacting if necessary in the presence of a diluent, a compound of the formula wherein R 7 is H or an alkali metal with a halogen derivative of the formula Y-P(X)(OR 6 ) 2 wherein Y is halogen, e.g. Cl or Br. When R 7 is hydrogen the reaction may be carried out in the presence of an acid binding agent. Several examples are given and the products have biologically-active properties being useful as active ingredients in pesticidal, fungicidal and veterinary compositions.