Patent EA-000435-B1 (EA)
Title: Triazoline and isoxazoline bis-oxime derivatives
Inventor: ZIEGLER HUGO
IPC: C07C281/06
Filed: 1996-06-21
Abstract: 1. A bis-oxime derivative of the formula I   in which   W is oxygen or sulfur, and the other are substituents defined as follows: R1 = hydrogen, C1-C4-alkyl; cyclopropyl; R2 = hydrogen, C1-C6-alkyl; halo(C1-C6)alkyl; C2-C6-alkoxyalkyl; C3-C6-cycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; cyano; C1-C6-alkoxycarbonyl; C1-C6-alkyl-S(O)n; substituted or unsubstituted aryl- S(O)n; C1-C6-alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted heteroaryloxy; unsubstituted or mono- to trimethyl-substituted heterocyclyl; substituted or unsubstituted aryl-C1-C6-alkyl, substituted or unsubstituted heteroaryl-C1-C6-alkyl; R3 = hydrogen; C1-C6 alkyl; C1-C6-haloalkyl having 1 to 5 halogen atoms; C1-C4-alkoxy-C1-C2-alkyl; unsubstituted or mono- to trihalo-substituted C2-C6-alkenyl; C2-C6-alkynyl; unsubstituted or mono- to tetrahalo-substituted C3-C6- cycloalkyl-C1-C4-alkyl; n = 0 to 2; R8 = H, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl; X = OR5, SR5, NR6R7, halogen (especially Cl); R6, R7 = independently of one another H, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkynyl; R5 = C1-C4 alkyl, C1-C3 haloalkyl. 2. A compound according to Claim 1, wherein R8 is methyl and X is methoxy, R2; is as defined with the exception of halo (C1-C6)alkyl and R1, R3, n and W are as defined. 3. A compound according to Claim 1, wherein: R1 is hydrogen, methyl, ethyl or cyclopropyl; R2 is a phenyl group which carries an unsubstituted or substituted ethynyl group whose possible substituents are: C1-C4-alkyl, C1-C4-hydroxyalkyl, halogen, C1-C4-haloalkyl, cyano, C1-C5-alkoxycarbonyl or cyclopropylmethoxycarbonyl; C2-C5-alkenyl which is unsusbtituted or substituted by C2-C4-alkoxy and/or halogen; N-methyl-N-methoxycarbamoyl; unsubstituted or substituted phenyl (the substituents being selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, CF3, CN, halogen and OCF3); unsubstituted or substituted, five- to six-membered heteroaryl whose substituents can be halogen, cyano, methyl, methoxy. hydroxyl; and R3 is methyl, ethyl or allyl. 4. A compound according to Claim 2, wherein R1 is hydrogen, methyl, ethyl or cyclopropyl, R2 is hydrogen, methyl, ethyl, cyclopropyl, cyano, methoxycarbonyl, -S(O)n C1-C4-alkyl or C1-C5-alkoxy, or is a naphthyl, biphenyl, phenoxyphenyl or phenyltniophenyl ring system each of which can be unsubstituted or substituted by from one to three substituents selected from the group consisting of halogen and C1-C2 alkyl; or is a phenyl radical attached directly or via oxygen, S(0)n or CH2, which is unsubstituted or is substituted by not more than three substituents selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, halogen, CF3, OCF3, C2-C4-alkynyl, NO2, -S(O)n-C1-C4-alkyl and a cyclopropylmethoxy group which is unsubstituted or substituted in the ring by one or two halogen atoms; or is a pyridine or pyrimidine ring which is attached directly or via oxygen or CH2; or is a thiazoline or oxazoline ring which is unsubstituted or is mono- or disubstituted, identically or differently, by methyl or halogen; while R3 and n are as defined for formula I. 5. A compound according to Claim 2, wherein R1 and R3 are methyl and R2 is methyl, cyano, pyridine or is phenyl attached directly or via oxygen, S(O)n or CH2, which is unsubstituted or substituted by not more than three substituents selected from the group consisting of methyl, methylthio, methoxy, fluorine, chlorine, bromine, CF3, OCF3, propyn-2-yl, NO2 and cyano; or is a thiazole ring or a naphthyl, biphenyl or phenoxyphenyl ring system which is unsubstituted or is substituted in each case up to twice, identically or differently, by methyl and/or halogen; while A and n are as defined for formula I. 6. A compound according to Claim 1, wherein R1, R2 and R3 are methyl and A denotes the ring systems indicated.