Patent EP-0469711-A1 (EP)
Inventor: HIRATSUKA MITSUNORI
IPC: C07D239/60
Filed: 1991-06-24
Abstract: A pyrimidine derivative has the formula,
     wherein each of R 1  and R 2 , which may be the same or different, is C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkoxy or halogen;
     R 3  is hydrogen, C 1 -C 6  alkyl, phenyl or phenyl substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl, nitro and halogen;   each of R 4  and R 5 , which may be the same or different, is hydrogen, C 1 -C 6  alkyl, halo C 1 -C 6  alkyl, phenyl, phenyl substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl, nitro and halogen, benzyl, pyridyl, pyridyl substituted with at least one member selected from the group consisting of Ci-C 6  alkyl, Ci-C 6  alkoxy, halo Ci-C 6  alkyl, Ci-C 6  alkoxycarbonyl, nitro and halogen, quinolinyl, quinolinyl substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl, nitro and halogen, C 1 -C 6  alkylcarbonyl, C 1 -C 6  alkoxycarbonyl, and
     wherein A 1  is C 4 -C 7  alkylene, C 4 -C 7  alkylene substituted with C 1 -C 6  alkyl, a group of the formula, -(CH 2 ) q -A 2- (CH 2 ) r -,  
wherein A 2  is S, O,
     wherein R 9  is hydrogen, C 1 -C 6  alkyl, q and r are integers and satisfy the criteria, 3 ≦ q + r ≦ 6, q ≧ 1, r ≧ 1, or a group of the formula,  
-(CR 2 ) q -A 2 -(CH 2 ) r -,  
substituted with C 1 -C 6  alkyl wherein q, r and A 2  are as defined above; or a group of the formula,
     wherein A is C 2 -C 4  alkylene or C 2 -C 4  alkylene substituted with C 1 -C 6  alkyl, or a group of the formula,
     wherein A is as defined above;   X is oxygen or sulfur;   Z is nitrogen or CY 4   ;     each of Y 1 , Y 2  and Y 3 , which may be the same or different, is hydrogen, halogen, C 1 -C 6  alkyl or C 1 -C 6  alkoxy; and   Y 4  is hydrogen, hydroxyl, mercapto, nitro, halogen, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 3 -C 6  alkenyloxy, C 3 -C 6  alkynyloxy, halo C 1 -C 6  alkyl, halo C 2 -C 6  alkenyl, halo C 2 -C 6  alkynyl, halo C 1 -C 6  alkoxy, halo C 3 -C 6  alkenyloxy, halo C 3 -C 6  alkynyloxy, C 1 -C 6  alkoxy C 1 -C 6  alkyl, C 3 -C 6  alkenyloxy C 1 -C 6  alkyl,C 3 -C 6  alkynyloxy C 1 -C 6  alkyl, cyano, formyl, carboxyl, C 1 -C 6  alkoxycarbonyl, C 3 -C 6  alkenyloxycarbonyl, C 3 -C 6  alkynyloxycarbonyl, phenyl, phenyl substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl and halogen, phenoxy, phenoxy substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl and halogen, phenylthio, phenylthio substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl and halogen, benzyloxy, benzyloxy substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl and halogen, benzylthio, benzylthio substituted with at least one member selected from the group consisting of C 1 -C 6  alkyl, C 1 -C 6  alkoxy, halo C 1 -C 6  alkyl, C 1 -C 6  alkoxycarbonyl and halogen,
         wherein each of R 8  and R 6 , which may be the same or different, is hydrogen, C 1 -C 6  alkyl, C 3 -C 6  alkenyl or C 3 -C 6  alkynyl,
         wherein R 8  and R 6  are as defined above,
         wherein R 7  is C 1 -C 6  alkyl, C 3 -C 6  alkenyl or C 3 -C 6  alkynyl and m is an integer of 0, 1 or 2,
         wherein X 1  is oxygen or sulfur, and R 7  is as defined above, or
         wherein R 7  and m are as defined above, and n is an integer from 1 to 4.