RU2002126272A - ASOLES DERIVATIVES AS THERAPEUTIC AGENTS AGAINST FUNGAL INFECTIONS - Google Patents

Claims (23)

1. The compound of formula IA

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ and R _{2 are} independently selected from the group consisting of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl and (8) C ₁ -C ₄ alkoxy; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; R _{3 is} selected from the group consisting of a C ₁ -C ₄ alkyl group, halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, cyano, carboxyl and SO ₂ R ′ where R ′ is hydrogen, alkyl or aryl; X ₁ , X ₂ , Y ₁ , Y ₂ and Z are independently selected from the group consisting of halogen, nitro, cyano, amino, sulfonyl, aryl or substituted aryl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxyl or protected carboxyl. 2. The compound of formula IB

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ and R _{2 are} independently selected from the group consisting of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl and (8) C ₁ -C ₄ alkoxy; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ', where R' represents hydrogen, alkyl or aryl; R ₃ selected from the group consisting of C ₁ -C ₄ alkyl group, halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, cyano, carboxyl and SO ₂ R ', where R' represents hydrogen, alkyl or aryl ; R ₄ selected from the group consisting of hydrogen, unsubstituted or substituted C ₁ -C ₄ alkyl groups; B is selected from oxygen and sulfur atoms; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl. 3. The compound of formula II

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and (8 ) C ₁ -C ₄ alkoxy; R ₄ selected from the group consisting of hydrogen, unsubstituted or substituted C ₁ -C ₄ alkyl group, R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents, each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ -C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino , (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (s) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl), which may be substituted with 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted with 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy (E) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxy, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxy, (l) tetrafluoropropyl and (m) tetrafluoroethoxy; B is selected from oxygen and sulfur atoms; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl. 4. The compound of formula III

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted with 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, ( 2) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro, (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl; R ₁ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and (8 ) C ₁ -C ₄ alkoxy; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl; X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; B is selected from oxygen and sulfur atoms. 5. A compound selected from the group consisting of 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (4-chlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 1), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (4-chlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 2), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2,4-dinitrophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 3), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2,4-dinitrophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 4), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- [ 4- (1-phenylpiperazinyl) phenyl] -3- (2H, 4H) -1,2,4-triazolone (compound No. 5), 2 - {[1R28 / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (1-phenylpiperazinyl) phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 6), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3,4-dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 7), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3,4-dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 8), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3-trifluoromethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 9), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3-trifluoromethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 10), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 11), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 12), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (4-methoxyphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 13), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (4-methoxyphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 14), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3-chloro-4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 15), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3-chloro-4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 16), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3-chloro-4-methylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 17),) 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3-chloro-4-methylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 18),) 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2,4-dimethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 19), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2,4-dimethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 20), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (5-chloro-2-methylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 21), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (5-chloro-2-methylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 22), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3,4-dimethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 23), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3,4-dimethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 24), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 25), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 26), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2-methoxy-5-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 27), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2-methoxy-5-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 28), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3,5-dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 29), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (3,5-dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 30), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2-ethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 31), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2-ethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 32), 2 - {[1R2R / 1S2S] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2,4-dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 33), 2 - {[1R2S / 1S2R] -2- (2,4-Difluorophenyl) -2-hydroxy-1-methyl-3- (1H-1,2,4-triazol-1-yl) propyl} -4- { 4- [4- (2,4-dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 34), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2-methoxyphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 35), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 36), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3,4- dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 37), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2,4- diaminophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 38), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-methylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (Compound No. 39) 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2,4- dinitrophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 40), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-methoxyphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 41), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2-methoxyphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 42), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 43), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-hydroxyphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 44), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- [4- [1-phenylpiperazinyl] phenyl} - 3- (2H, 4H) -1,2,4-triazolone (compound No. 45), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-chlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -5-methyl-1,2,4-triazolone (compound No. 46), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-chlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 47), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (5-chloro- 2-methylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 48), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3-chloro- 4-methylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 49), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2,4- dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 50), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3-trifluoromethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 51), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2,4- difluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 52), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3-chloro- 4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 53), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2,4- dimethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 54), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3,4- difluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 55), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3,4- dimethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 56), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3-chlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 57), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2-chloro- 4-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 58), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2-methoxy- 5-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 59), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2-ethylphenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 60), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (3,5- dichlorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 61), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (2-fluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 62), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (1,2, 3-trifluorophenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 63), 3- {4- [4- (p-Tolylaminothiocarbonylamino) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 64), 3- {4- [4- (Isopropylaminothiocarbonylamino) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2-ol ( connection No. 65), 3- {4- [4- (4-Chlorophenylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 66), 3- {4- [4- (4-Chlorophenylthioureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 67), 3- {4- [4- (1-Naphthylthioureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 68), 3- {4- [4- (1-Naphthylthioureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 69), 3- {4- [4- (4-Trifluoromethylphenylthioureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 70), 3- {4- [4- (4-Methoxyphenylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 71), 3- {4- [4- (2,4-Dichlorophenylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propane- 2-ol (compound No. 72), 3- {4- [4- (4-Chlorophenyl-N-ethylureurido) piperazinyl] phenoxy) -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) propane- 3-amino-2-ol (compound No. 73), 3- {4- [4- (4-Chlorophenyl-N-ethylureureido) piperazinyl] phenoxy) -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) -2- ethoxy-3-propylamine (compound No. 74), 3- {4- [4-N- (4-Chlorophenyl) -N- (methylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl ) -2-methoxypropane (compound No. 75), 3- {4- [4- (4-Aminophenylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 76), [1R2R / 1S2S] 1- {4- [4- (4-Chlorophenylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1-methyl-3- (1H-1,2,4- triazolyl) -propan-2-ol (compound No. 77), [1R2S / 1S2R] 1- {4- [4- (4-Chlorophenylureido) piperazinyl] phenoxy} 2- (2,4-difluorophenyl) -1-methyl-3- (1H-1,2,4-triazolyl ) -propan-2-ol (compound No. 78), 1- {4- [4- (4-Trifluoromethylphenylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1-methyl-3- (1H-1,2,4-triazol-1-yl) - propan-2-ol (compound No. 79), 3- {4- [4- (Phenylureido) piperazinyl] phenoxy} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -propan-2- ol (compound No. 80), 2- (2,4-Difluorophenyl) -3- {4- (thioureidophenyl) N-methyl-N-phenyl} -1- (1H-1,2,4-triazolyl) propan-3-amino-2-ol (compound No. 81) 2- (2,4-Difluorophenyl) -3- {4- (isopropylthioureido) N-methyl-N-phenyl} -1- (1H-1,2,4-triazolyl) propan-3-amino-2-ol (unit number 82) 3- {N- [4- (p-Tolylthioureido) phenyl] -N-methyl} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) propan-3- amino-2-ol (compound No. 83), 3- {N- [4- (p-Fluorophenylureido) phenyl] N-methyl} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) propan-3- amino-2-ol (compound No. 84), 3- {N- [4- (p-Nitrophenylureido) phenyl] -N-methyl} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) propan-3- amino-2-ol (compound No. 85), 3- {N- [4- (p-Chlorophenylureido) phenyl] N methyl} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) propane-3- amino-2-ol (compound No. 86), 3- {N- [4- (Carboxymethyl) phenylureido) phenyl] -N-methyl} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) propan-3 amino-2-ol (compound No. 87), 3- {N- [4- (2-Methoxy-2-oxoethyl) phenylureido) phenyl] -N-methyl} -2- (2,4-difluorophenyl) -1- (1H-1,2,4- triazolyl) -propan-3-amino-2-ol (compound No. 88), 3- {N- [4- (p-Chlorophenylthioureido) phenylureido) phenyl] N-methyl} -2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazolyl) propane -3-amino-2-ol (compound No. 89), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (isopropylthioureido) -1 -piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 90), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-chlorophenylureido) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 91), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4-chlorophenylthioureido) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 92), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4- (2 -methoxy-2-oxoethyl) phenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 93), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4- (carboxyethyl ) -phenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 94), 2- [2- (2,4-Difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propyl] -4- {4- [4- (4- (2 -hydroxyethyl) phenyl) -1-piperazinyl] phenyl} -3- (2H, 4H) -1,2,4-triazolone (compound No. 95). 6. A pharmaceutical composition comprising a compound of claims 1-5 and a pharmaceutically acceptable carrier. 7. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound according to claims 1-5 or a physiologically acceptable acid addition salt thereof and a pharmaceutically acceptable carrier for treating a fungal infection. 8. A method of treating or preventing a fungal infection in animals, comprising administering to said animal a compound of formula IA

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ and R _{2 are} independently selected from the group consisting of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl and (8) C ₁ -C ₄ alkoxy; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; R _{3 is} selected from the group consisting of a C ₁ -C ₄ alkyl group, halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, cyano, carboxyl and SO ₂ R ', where R' is hydrogen, alkyl or aryl ; X ₁ , X ₂ , Y ₁ , Y ₂ and Z are independently selected from the group consisting of halogen, nitro, cyano, amino, sulfonyl, aryl or substituted aryl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxyl or protected carboxyl. 9. A method of treating or preventing a fungal infection in an animal, comprising administering to said animal a compound of formula IB

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ and R _{2 are} independently selected from the group consisting of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl and (8) C ₁ -C ₄ alkoxy; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; R _{3 is} selected from the group consisting of a C ₁ -C ₄ alkyl group, halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, cyano, carboxyl and SO ₂ R ', where R' is hydrogen, alkyl or aryl ; R ₄ selected from the group consisting of hydrogen, unsubstituted or substituted C ₁ -C ₄ alkyl groups; B is selected from oxygen and sulfur atoms; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl. 10. A method of treating or preventing a fungal infection in an animal, comprising administering to said animal a compound of formula II

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and (8 ) C ₁ -C ₄ alkoxy; R ₄ selected from the group consisting of hydrogen, unsubstituted or substituted C ₁ -C ₄ alkyl groups; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ -C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino , (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl), which may be substituted with 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted with 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl; B is selected from oxygen and sulfur atoms; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl. 11. A method of treating or preventing a fungal infection in an animal, comprising administering to said animal a compound of formula III

and its pharmaceutically acceptable salts, enantiomers, diastereomers, N-oxides, prodrugs or metabolites, where R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted with 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, ( 2) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro, (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl; R ₁ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and (8 ) C ₁ -C ₄ alkoxy; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl; X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; B is selected from oxygen and sulfur atoms. 12. A method of treating or preventing a fungal infection in an animal, comprising the step of administering to said animal a pharmaceutical composition according to claim 6 or 7. 13. The method of obtaining the compounds of formula IA

where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ and R _{2 are} independently selected from the group consisting of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl and (8) C ₁ -C ₄ alkoxy; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; R _{3 is} selected from the group consisting of a C ₁ -C ₄ alkyl group, halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, cyano, carboxyl and SO ₂ R where R is hydrogen, alkyl or aryl; X ₁ , X ₂ , Y ₁ , Y ₂ and Z are independently selected from the group consisting of halogen, nitro, cyano, amino, sulfonyl, aryl or substituted aryl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxyl or protected carboxyl, comprising the interaction of 1- [2- (2,4-disubstituted phenyl) -2,3-epoxy derivative of 1,2,4-triazole of formula IV

where X, R and R ₁ are as previously defined, with triazol-3-one derivatives of formula V

where R ₂ , R ₃ , X ₁ , X ₂ , Y, Y ₁ , Y ₂ and Z are as defined above, in the presence of sodium hydride to obtain the desired compound of formula IA. 14. The method of obtaining the compounds of formula IA

where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted with 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ and R _{2 are} independently selected from the group consisting of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl and (8) C ₁ -C ₄ alkoxy; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; R _{3 is} selected from the group consisting of a C ₁ -C ₄ alkyl group, halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, cyano, carboxyl and SO ₂ R ', where R' is hydrogen, alkyl or aryl ; X ₁ , X ₂ , Y ₁ , Y ₂ and Z are independently selected from the group consisting of halogen, nitro, cyano, amino, sulfonyl, aryl or substituted aryl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxyl or protected carboxyl, comprising the interaction of an epoxy derivative of formula VI

with 1,2,4-triazole to give a compound of formula IA. 15. The method of obtaining the compounds of formula IB

where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ and R _{2 are} independently selected from the group consisting of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl and (8) C ₁ -C ₄ alkoxy; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; R _{3 is} selected from the group consisting of a C ₁ -C ₄ alkyl group, halogen, hydroxy, C ₁ -C ₄ alkoxy, nitro, amino, cyano, carboxyl and SO ₂ R ', where R' is hydrogen, alkyl or aryl ; R ₄ selected from the group consisting of hydrogen, unsubstituted or substituted C ₁ -C ₄ alkyl groups; B is selected from oxygen and sulfur atoms; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl, comprising the interaction of the compounds of formula ID

where X, R, R ₁ , R ₂ , R ₃ and Y have the same meanings as defined above, with a compound of formula R ₅ —N = C = B, where R ₅ and B are as previously defined to form a compound of formula IC

which, by reaction with R ₄ Z, is converted into a compound of formula IB, wherein X, R, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , Y and B have the same meanings as previously defined; Z represents any halogen atom. 16. The method of obtaining the compounds of formula II

where X is selected from the group consisting of CH ₂ , CO, CS, SO ₂ and —N = N—; R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (2 ) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro , (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl ; R ₁ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and (8 ) C ₁ -C ₄ alkoxy; R ₄ selected from the group consisting of hydrogen, unsubstituted or substituted C ₁ -C ₄ alkyl groups; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; B is selected from oxygen and sulfur atoms, comprising reacting a compound of formula VII

with a compound R ₅ —N = C = B, where R, R ₁ , R ₅ , X and Y are as defined above, to give a compound of formula VIII

and then reacting a compound of formula VIII with R ₄ Z, where R _{4 is} selected from the group consisting of hydrogen, an unsubstituted or substituted C ₁ -C ₄ alkyl group, and Z is any halogen atom to produce a compound of formula II. 17. A method of obtaining a compound of formula III

where R is selected from the group consisting of (1) C ₁ -C ₄ alkyl unsubstituted or substituted with 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, ( 2) C ₁ -C ₄ alkoxy, (3) halogen, (4) formyl, (5) carboxyl, (6) C ₁ -C ₄ acyloxy, (7) phenyl or substituted phenyl, (8) hydroxy, (9) nitro, (10) amino, (11) furyl, (12) triazolyl, (13) thienyl, (14) piperazinyl, (15) morpholinyl, (16) thiomorpholinyl, (17) imidazolyl, (18) oxazolyl and (19) triazolonyl; R ₁ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and (8 ) C ₁ -C ₄ alkoxy; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl; X is selected from the group consisting of CH ₂ , CO, CS, OS ₂ and —N = N—; Y represents a phenyl group unsubstituted or substituted by substituents, each of which is independently selected from the group consisting of (1) halogen, (2) nitro, (3) amino, (4) cyano, (5) carboxyl or protected carboxyl, ( 6) hydroxy, (7) C ₁ -C ₄ alkoxy and (8) SO ₂ R ′, where R ′ represents hydrogen, alkyl or aryl; B is selected from oxygen and sulfur atoms, comprising reacting a compound of formula IX

with a compound of formula B = C = NR ₅ to give the desired compound of Formula III. 18. The method of obtaining the compounds of formula IA, where X = CH ₂ , R = F, R ₁ = H, Y = C ₆ H ₄ -, R ₃ = H

where R ₂ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ - C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and ( 8) C ₁ -C ₄ alkoxy; X ₁ , X ₂ , Y ₁ , Y ₂ and Z are independently selected from the group consisting of halogen, nitro, cyano, amino, sulfonyl, aryl or substituted aryl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxyl or protected carboxyl, comprising the interaction of triazol-3-one derivatives of formula V, where R ₃ = H, Y = C ₆ H ₄ -

where R ₂ , X ₁ , X ₂ , Y ₁ , Y ₂ and Z are as defined above, with a compound of formula IV, where R = F, R ₁ = H, X = CH ₂

in the presence of sodium hydride. 19. The method of obtaining derivatives of triazol-3-one of the formula V, where R ₃ = N, Y = C ₆ H ₄ -

comprising the interaction of substituted phenylpiperazine of formula XIV

where X ₁ , X ₂ , Y ₁ , Y ₂ and Z are independently selected from the group consisting of halogen, nitro, cyano, amino, sulfonyl, aryl or substituted aryl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxyl or protected carboxyl, with 4-chloronitrobenzene to form the corresponding nitroaryl compound of formula XV

which, by catalytic reduction, is converted into an aniline derivative of the formula XVI

then acylation of the compound of formula XVI with phenylchloroformate to form the phenylcarbamate derivative of formula XVII

the interaction of the carbamate derivative of formula XVII with hydrazine hydrate to obtain a derivative of semicarbazide of the formula XVIII

and cyclizing the compound of formula XVIII with formamidine derivatives to form triazol-3-one derivatives of formula V. 20. A method of obtaining a compound of Formula IA, where X = CH ₂ , R = F, R ₁ = CH ₃ , Y = C ₆ H ₄ -, R ₃ = H

where R ₂ selected from the group consisting of (1) hydrogen, (2) C ₁ -C ₄ alkyl group, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ - C ₄ alkoxy and amino, (3) nitro, (4) amino, (5) cyano, (6) carboxyl or protected carboxyl, (7) SO ₂ R ', where R' represents hydrogen, alkyl or aryl, and ( 8) C ₁ -C ₄ alkoxy; X ₁ , X ₂ , Y ₁ , Y ₂ and Z are independently selected from the group consisting of halogen, nitro, cyano, amino, sulfonyl, aryl or substituted aryl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, carboxyl or protected carboxyl, comprising the interaction of 1,3-difluorobenzene of the formula X

with racemic (±) 2-chloropropionyl chloride of the formula XIX

with the formation of the compound (±) 2-chloro-2-methyl-2 ’, 4’-difluoro-acetophenone of the formula XX

from which upon condensation with an intermediate compound of the formula V, where R ₃ = H, Y = C ₆ H ₄ and R ₂ , X ₁ , X ₂ , Y ₁ , Y ₂ and Z are as defined above

in the presence of sodium hydride, a compound of formula XXI is formed

which is then epoxidized with trimethylsulfoxonium iodide (TMSI) in DMSO to give an epoxy derivative of formula VI, where X = CH ₂ , R = F, R ₁ = CH ₃ , Y = C ₆ H ₄ -, R ₃ = H

from which, when condensed with 1,2,4-triazole, a compound of formula IA is formed. 21. The method of obtaining compounds of formula II, where X = CH ₂ , R = F, R ₁ = H, Y = C ₆ H ₄ -

where R ₄ selected from the group consisting of hydrogen, unsubstituted or substituted C ₁ -C ₄ alkyl groups; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl unsubstituted or substituted by 1-3 substituents each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ - C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl ), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl; B is selected from oxygen and sulfur atoms, comprising the interaction of 2- (2,4-difluorophenyl) -3- (1H-1,2,4-triazolyl) -1- [4- (piperazinyl) phenoxy] propan-2-ol of formula VII, where X = CH ₂ , R = F, R ₁ = H, Y = C ₆ H ₄ -

with a compound of formula B = C = NR ₅ to form a compound of formula VIII, where X = CH ₂ , R = F, R ₁ = H, Y = C ₆ H ₄ -

where R ₅ and B are as previously defined, then reacting a compound of formula VIII with R ₄ Z, where R _{4 is} selected from the group consisting of hydrogen, an unsubstituted or substituted C ₁ -C ₄ alkyl group, in the presence of sodium hydride to form the desired compound of formula II. 22. The method of obtaining the compounds of Formula II, where X = CH ₂ , R = F, R ₁ = CH ₃ , R ₄ = H, Y = C ₆ H ₄ -

where R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents, each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each independently selected from a group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f ) C ₁ -C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, ( n) amino, (o) furyl, (p) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl), which may be substituted by 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alko B, (e) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxy, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxy, (l) tetrafluoropropyl and (m) tetrafluoroethoxy; B is selected from oxygen and sulfur atoms, comprising treating 2,4-difluoro-α-methyl-phenacyl chloride of formula XXII

1-acetyl-4-hydroxyphenylpiperazine of the formula XXIII

with the formation of 2- [4- (4-acetylpiperazine) phenoxy] -2-methyl-2 ’, 4’-difluoroacetophenone of the formula XXIV

from which, when treated with trimethylsulfoxonium iodide, the corresponding epoxide of formula XXV is formed

which then interacts with 1,2,4-triazole to give a compound of formula XXVI

from which, by hydrolysis, a compound of formula VII is obtained, where X = CH ₂ , R = F, R ₁ = CH ₃ , Y = C ₆ H ₄

and by reacting a compound of formula VII with R ₅ —N═C═B, a compound of formula II is obtained. 23. The method of obtaining the compounds of formula III, where X = CH ₂ , R = F, R ₁ = H, Y = C ₆ H ₄ -

where B is selected from oxygen and sulfur atoms; R _{5 is} selected from the group of (1) hydrogen, (2) a C ₁ -C ₄ alkyl group unsubstituted or substituted by 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy, and amino, (3) phenyl unsubstituted or substituted by 1-3 substituents, each independently selected from the group consisting of (a) C ₁ -C ₄ alkyl, unsubstituted or substituted by 1-3 substituents, each independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) C ₁ -C ₄ alkoxy, (c) halogen, (d) formyl, (e) carboxyl, (f) C ₁ -C ₄ acyloxy, (g) C ₁ -C ₄ alkoxycarbonylamino, (h) phenyloxy or naphthyloxycarbonylamino, (i) semicarbazido, (j) formamido, (k) thioformamido, (l) hydroxy, (m) nitro, (n) amino, ( o) furyl, (r) triazolyl, (q) thienyl, (r) oxazolyl, (s) imidazolyl, (t) CF ₂ and (u) OCF ₃ , (4) naphthyl or naphthyl (C ₁ -C ₄ alkyl) which may be substituted with 1-6 substituents selected from (a) C ₁ -C ₄ alkyl, unsubstituted or substituted with 1-3 substituents, each of which is independently selected from the group consisting of halogen, hydroxy, C ₁ -C ₄ alkoxy and amino, (b) halogen, (c) (C ₁ -C ₄ alkyl) halo, (d) C ₁ -C ₄ alkoxy, ( f) hydroxy, (f) amino, (g) carboxyl, (h) trifluoromethoxyl, (i) trifluoromethyl, (j) tetrafluoroethyl, (k) tetrafluoroethoxyl, (l) tetrafluoropropyl, and (m) tetrafluoropropoxyl, including 1- [2 - (2,4-difluorophenyl) -2,3-epoxypropyl] -1H-1,2,4-triazole of formula IV, where R = F, X = CH ₂ , R ₁ = H

with N-methyl-4-nitroaniline of formula XXVII to give 2- (2,4-difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) -1-propylamino-1N, methyl 4-nitrobenzene of the formula XXVIII

from which, upon reduction, 2- (2,4-difluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) -1-propylamino-1H-methyl-4-aniline of formula IX is obtained where X = CH ₂ , R = F, R ₁ = H, Y = C ₆ H ₄ -

which, by reacting with B = C = NR _{5, is} converted into a compound of formula III.