Patent CA-2041615-A1 (CA)
Title: Pyrimidine derivatives
Inventor: HIRATSUKA MITSUNORI
IPC: C07D309/06
Filed: 1991-05-01
Abstract: ABSTRACT OF THE DISCLOSURE          A pyrimidine derivative having the formula,                   (1) wherein A is C3-C8 cycloalkyl C1-C6 alkyl, C3-C8 cycloalkyl C1-C6 alkyl substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxy-carbonyl and halogen,  C3-C6 oxacycloalkyl C3-C6 oxacycloalkyl substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6  alkoxycarbonyl and halogen, C3-C6 oxacycloalkyl C1-C6 alkyl, C3-C6 oxacyclo-alkyl C1-C6 alkyl substituted with at least one member selected from the group consisting of C1-4 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl and halogen, C3-C5 dioxacycloalkyl, C3-C5 dioxacycloalkyl substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl and halogen, C2-C5 dioxa-cycloalkyl C1-C6 alkyl or C2-C5 dioxacycloalkyl C1-C6 alkyl substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl and halogen; each of R1 and R2, which may be the same or differnt, is C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkoxy or halogen;         X is oxygen or sulfur;         Z is nitrogen or CY4; each of Y1, Y2 and Y3, which may be the same or different, is hydrogen, halogen, C1-C6 alkyl or C1-C6 alkoxy; and Y4 is hydrogen, hydroxyl, mercapto, nitro, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C1-C6 alkoxy, halo C3-C6 alkenyloxy, halo C3-C6 alkynyloxy, C1-C6 alkoxy C1-C6 alkyl, C3-C6 alkenyloxy C1-C6 alkyl, C3-C5 alkynyloxy C1-C6 alkyl, cyano, formyl, carboxyl, C1-C6 alkoxycarbonyl, C3-C6 alkenyloxycarbonyl, C3-C6 alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl and halogen, phenoxy, phenoxy substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl and halogen, benzyloxy, benzyloxy substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-4 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxy-carbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl and halogen,               , wherein each of R5 and R6, which may be the same or different, is hydrogen, C1-C6 alkyl, C3-C6 alkenyl or C3-C6 alkynyl,             , wherein R5 and R6 are as defined above,            , wherein R7 is C1-C6 alkyl, C3-C6 alkenyl or C3-C6 alkynyl and m is an integer of 0, 1 or 2, and X is as defined above,          , wherein R7 and X are as defined above, or          , wherein R7 and m are as defined above, and n is an integer from 1 to 4 is prepared by (A)       a method which comprises reacting a compound having the formula,   wherein A, X, Z, Y1, Y2 and Y3 are as defined above, with a compound having the formula,         , wherein each of R1 and R2 are as defined above; W is halogen or             , wherein R8 is C1-C6 alkyl, benzyl or benzyl substituted with at least one member selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halogen or nitro; and m is an integer of 0, 1 or 2; (B)       a method which comprises the steps of (i)       reacting a carboxylic acid derivative having the formula,   wherein X, z, Y1, Y2, Y3, R1 and R2 are as defined above, with an acid-halogenating agent or an active esterifying agent to obtain a reaction product; and (ii)      reacting the reaction product with an alcohol derivative having the formula, HO-A wherein A is as defined above; or (C)       a method which comprises reacting an unesterified pyrimidine derivative having the formula,   wherein X, Z, Y1, Y2, Y3, R1 and R2 are as defined above, with a halide having the formula, W3-A, wherein A is as defined above, and W3 is halogen.  The pyrimidine derivative can be incorporated as an active ingredient into a herbicidal composition together with an inert carrier or a diluent.  The herbicidal composition shows a high herbicidal activity.