Patent EA-000417-B1 (EA)
Title: O-benzyl oxime derivatives and its possible isomers and mixtures thereof
Inventor: ZIEGLER HUGO
IPC: A01N43/80
Filed: 1996-06-14
Abstract: 1. O-benzyl oxime derivatives of the general formula I   and its possible isomers and isomer mixtures, in which a) X is an N atom and Y is an oxygen atom or NH, or b) X is CH and in which furthermore R1 is C1-C4 alkyl; R2 is hydrogen, C1-C6 alkyl or cyclopropyl; R3 is Ci-C6 alkoxy which is unsubstituted or substituted by 1 to 5 halogen atoms, substituted or unsubstituted aryloxy, C1-C6 alkylthio which is unsubstituted or substituted by 1 to 5 halogen atoms, substituted or unsubstituted arylthio, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted heteroarylthio, substituted or unsubstituted aralkyl, substituted or unsubstituted biphenyl, substituted or unsubstituted C2-C4 alkynylphenyl, substituted or unsubstituted heteroarylmethyl; and R4 is C1-C6 alkyl; C1-C6 haloalkyl having 1 to 5 halogen atoms; C1-C4 alkoxy- C1-C2 alkyl; C2-C6 alkenyl which is unsubstituted or substituted by 1 to 3 halogen atoms; C2-C6 alkynyl; C3-C6 cycloalkyl- C1-C4 alkyl which is unsubstituted or substituted by 1 to 4 halogen atoms; where R3 has a meaning other than dichlorobenzyl when, simultaneously, R1 is methyl, R2 is hydrogen, X is CH, Y is oxygen and R4 is C1-C4 alkyl. 2. A compound according to Claim 1, in which R3 is C1-C6 alkoxy; C1-C4 aloalkoxy; substituted or unsubstituted phenoxy; C1-C6 alkylthio which is unsubstituted or substituted by 1 to 3 substituents selected from halogen, C1-C4 alkyl, C1-C4 alkoxy, CF3 and substituted phenylthio; or is unsubstituted or in each case halo-substituted pyridyloxy, pyrimidinyloxy, quinolyloxy, quinazolinyloxy or quinoxazolinyl; or an unsubsrituted or C1-C4 alkyl- or halogcn-substituted benzothiazolykhio, benzoxazolylthio, imidazolylthio or tetrazolylthio radical; or a diphenyl, C2-C4 alkynylphenyl, benzyl or naphthylmethyl, which is unsubstituted or substituted by 1 to 3 substituents selected from halogen, C1-C4 alkyl. C1-C4 alkoxy, CF3 and CN; R4 is C1-C4 alkyl; C1-C4 haloalkyl; unsubstituted or halo-substituted C2-C4 alkenyl; C3-C4 a1kynyl; unsubstituted or halo-substituted cyclopropylmcthyl; while X, Y, R1 and R2 are as defined for formula I. 3. A compound according to Claim 2, in which R1 is methyl and R2 is hydrogen, methyl or cyclopropyl,while X, Y, R3 and R4 are as defined. 4. A compound according to Claim 1, in which: X is CH or N, Y is oxygen, R1 is methyl or :ethyl, R2 is methyl or cyclopropyl, and in which R3 and R4 are as defined for formula I. 5. A compound accordind to alaim 1, in which: X is nitrogen, Y is NH, R1 is methyl, ethyl or isopropyl, R2 is methyl or cyclopropyl, and in which R3 and R4 are as defined for formula I. 6. A compound according to Claim 1, in which: R1 is methyl, R2 is methyl, R4 is C1-C6 alkyl, while X, Y and R3 are as defined for formula I. 7. A compound according to Claim 1, in which: R1 is methyl, R2 is methyl R3 is substituted or unsubstituted C1-C6 alkoxy or substituted or unsubstituted C1-C6 alkylthio, while X, Y and R4 are as defined for formula I. 8. A compound according to Claim 1, in which: R1 is methyl, R2 is methyl, R3 is substituted or unsubstituted aryloxy or substituted or unsubstituted arylthio, while X, Y and R4 are as de fined for formula 9. A compound according to Claim 1, in which: R1 is methyl, R2 is methyl, R3 is substituted or unsubstituted heteroaryloxy or substituted or unsubstituted hetcroarylthio, while X, Y and R4 are as defined for formula I. 10. A compound according to Claim 1, in which:R1 is methyl, R2 is methyl, R3 is substituted or unsubstituted benzyl or substituted or unsubstituted hetcroarylmeyl, while X, Y and R4 are as defined: for formula I. 11. A compound according to Claim 1, in which: R1 is methyl R2 is methyl R3 is substituted or unsubstituted biphenyl or substituted or unsubstituted C2-C4 alkynylphenyl, while X, Y and R4 are as defined for formula I. 12. A compound according to Claim 11, in which R4 is methyl, ethyl or allyl, R3 is an unsubstituted or substituted C2-C4 alkynylphenyl group in which the possible substituent is located on the alkynyl group and is selected from C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl (especially CF3) C1-C4 haloalkoxy (especially OCF3), C1-C4 alkylthio. halogen, nitro, cyano, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, nnsubstituted or substituted phenyl (where the phenyl substituents are selected from C1-C4 alkyl, C1-C4 alkoxy, hydroxyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkylthio, halogen, nitro and cyano); C1-C4 hydroxyalkyl, which can be 0-acylated(C1-C4) or O-alkylated(C1-C4); C1 -C5 alkoxycarbonyl; carbamoyl, N-( C1-C4 alkyl)carbamoyl; N,N-di(C1-C4alkyl)carbamoyl; N- C1-C4alkyl-N- C1-C4aIkoxycarbamoyl; unsubstituted or halogen-substituted cyclopropylmethoxycarbonyl,. unsubstituted, C1-C4alkoxy-substituted or halogen-substituted C2-C5alkenyl, and a five- or six-membered heteroaryl ring which is unsubstituted or substituted by halogen, cyano, hydroxyl, and also alkyl, alkenyl, alkoxy, alkenyloxy or alkynyloxy each having not more than 4 carbon atoms. 13. A compound according to Claim 12, in which R3 is an unsubstituted or substituted ethynylphenyl group, the possible subsiituent on the ethynyl group being selected from C1-C4alkyl; C1-C4alkoxy; C1-C2 haloalkyI; C1-C2 haloalkoxy; fluorine, chlorine, bromine, iodine; nitro;cyano; phenyl, which is unsubstituted or substituted up to three times (where the phenyl substituents are selected from C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl, C1-C4haloalkoxy, hydroxyl, halogen, nitro, and cyano); C1-C4hydroxyalkyl, which can be O- alkylated (C1-C4); C1-C4alkoxycarbonyl, N-methyl-N-methoxycarbamoyl and unsubstituted or substituted C2-C5 alkenyl, whose possible substituents are selected from halogen and C1-C2 alkoxy. 14. A compound according to 11, in which R3 is a substituted ethynylphenyl group, the sudstituent on the ethynyl group being a five- or six-membered heteroaryl ring which is unsubstituted or substituted up to three times by halogen, cyano, C1-C4alkyl, C1-C4alkoxy or hydroxyl. 15. A compound according to Claim 14, in which the heteroaryl ring is selected from pyridine pyrimidine, pyrazine, pyridazine, triazine, (iso)thiazolc, (iso)oxazole, pyrrole, pyrazole, imidazole, triazole and thiophene, and which is unsubstituted or substituted by up to three substituents selected from methyl, ethyl, isopropyl, CN, halogen, mcthoxy and hydroxyl. 16. A compound according to Claim 13, in which the substituent on the ethynyl group is selected from C1-C4alkyl, C1-C4alkoxy; C1-C2haloalkyl; C1-C2 haloalkoxy; chlorine, bromine, iodine; nitro; cyano; C1-C4 hydroxyalkyl, which can be O- C1-C4alkylated; C1-C4alkoxycarbonyl; N-methyl-N-methoxycarbamoyl and unsubstituted or substituted C2-C5alkenyl, whose possible substituents are selected from halogen and methoxy. 17 A compound according to Claim 12, in which R3 is an unsubstituted or substituted 3- or 4-(C2-C4 alkynyl)phenyl group. 18. A compound according to Claim 1, in which the X=C double bond has the E configuration. 19. A compound according to Claim 11, in which R4 is methyl and R3 is 4-ethynylphenyl. 20. A compound according to Claim 14, in which R4 is methyl and R3 is 4-(pyrazinylethynyl)phenyl. 21. A compound according to Claim 14, in which R4 is methyl and R3 is 4-(pyridylethynyl)phenyl. 22. A compound according to Claim 21, in which R3 is 4-(3'-pyridylethynyl)phenyl. 23. A compound according to Claim 14, in which R4 is methyl and R3 is 4-(5-pyrimidinylethynyl)phenyl.