Halogenated oxime derivatives and the use thereof

A compound of the formula I

• wherein
• R1 is C1-C10haloalkylsulfonyl;
• R2 is C1-C10haloalkyl;
• Ar1 is phenyl, biphenylyl, fluorenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl, all of which are optionally substituted by one or more C1-C18alkyl, C1-C8haloalkyl, phenyl-C1-C3-alkyl, halogen, —NO2, —CN, —Ar2, —(CO)R7, —(CO)OR3, —(CO)NR4R5, —O(CO)R7, —O(CO)OR3, —O(CO)NR4R5, —NR6(CO)R7, —NR6(CO)OR3, —OR3, —NR4R5, —SR6, —SOR7, —SO2R7, —OSO2R7,C3-C30cycloalkyl;
• or by
• C3-C30cycloalkyl which is interrupted by one or more —O—, —S—, —NR6—, —O(CO)—, or —NR6(CO)—;
• optionally the substituents —(CO)R7, —(CO)OR3, —(CO)NR4R5, —O(CO)R7, —O(CO)OR3, —O(CO)NR4R5, —NR6(CO)R7, —NR6(CO)OR3, —OR3, —NR4R5, —SR6, —SOR7, —SO2R7 and/or —OSO2R7 form 5-, 6- or 7-membered rings, via the radicals R3, R4, R5, R6 and/or R7, with further substituents on the phenyl, biphenylyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring;
• or optionally the substituents C1-C18alkyl form alkylene bridges from one carbon atom of the phenyl, biphenylyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring to another carbon atom of said ring;
• said alkylene bridges optionally being condensed with further phenyl rings;
• wherein all radicals Ar1 optionally additionally are substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid;
• X is —F;
• R3 is phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or is C2-C18alkyl which is interrupted by one or more —O—;
• or is C3-C30cycloalkyl which is interrupted by one or more —O—, —S—, —NR23—, —O(CO)— or —NR23(CO)—;
• or R3 is C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
• all of which optionally are substituted by one or more —Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, —NO2, —CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio phenylthiocarbonyl, —NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsufonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C 18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R3 is hydrogen;
• R4 and R5 independently of each other are phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or are C2-C18alkyl which is interrupted by one or more —O—;
• or are C3-C30cycloalkyl which is interrupted by one or more —O—, —S—, —NR6—, —O(CO)—, or —NR6(CO)—;
• or are C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
• all of which optionally are substituted by one or more —Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, —NO2, —CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenyithiocarbonyl, —NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R4 and R5 independently of each other are hydrogen;
• or R4 and R5, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring which optionally is interrupted by one or more —O—, —NR6— or —CO—;
• R6 is phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or is C2-C18alkyl which is interrupted by one or more —O—;
• or is C3-C30cycloalkyl which is interrupted by one or more —O—, —S—, —NR6—, —O(CO)—, or NR6(CO)—;
• or is C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
• all of which optionally is substituted by one or more —Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, —NO2, —CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenyithiocarbonyl, —NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R6 is hydrogen;
• R7 is phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or is C2-C18alkyl which is interrupted by one or more —O—;
• or is C3-C30cycloalkyl which is interrupted by one or more —O—, —S—, —NR6—, —O(CO)—, or NR6(CO)—;
• all of which optionally are substituted by one or more —Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, —NO2, —CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenyithiocarbonyl, —NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R7 is hydrogen;
• and
• Ar2 is phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl, all of which optionally are substituted by one or more C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl;
• C3-C30cycloalkyl which is interrupted by one or more —O—, —S—, —NR6-, —O(CO)—, or —NR6(CO)—;
• or is substituted by halogen, —NO2, —CN, phenyl, —(CO)R7 , —(CO)OR3, —(CO)NR4R5, —O(CO)R7, —O(CO)OR3, —O(CO)NR4R5, —NR6(CO)R7 , —NR6(CO)OR3, —OR3, —NR4R5, —SR6, —SOR7, —SO2R7 and/or —OSO02R7, optionally the substituents —(CO)R7, —(CO)OR3, —(CO)NR4R5, —O(CO)R7, —O(CO)OR3, —O(CO)NR4R5, —NR6(CO)R7, —NR6(CO)OR3 , —OR3, —NR4R5, —SR6, —SOR7, —SO2R7 and/or —OSO2R7 form 5-, 6- or 7-membered rings, via the radicals R3, R4, R5, R6 and/or R7, with further substituents on the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring.