Oxime sulfonates and the use thereof as latent acids

A compound of the formula I, II or III

• R1 is C1-C18alkylsulfonyl, C1-C10haloalkylsulfonyl,
• C2-C12alkenylsulfonyl, C2-C12alkynylsulfonyl, C3-C30cycloalkylsulfonyl, C1-C18alkylsulfonyl interrupted by one or more O or C1-C10haloalkylsulfonyl interrupted by one or more O;
• wherein the groups C1-C18alkylsulfonyl, C1-C10haloalkylsulfonyl, C2-C12alkenylsulfonyl, C2-C12alkynylsulfonyl, C3-C30cycloalkylsulfonyl, interrupted C1-C18alkylsulfonyl and interrupted C1-C10haloalkylsulfonyl optionally are substituted by one or more C3-C30cycloalkyl, C4-C30cycloalkenyl, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or are substituted by NO2, CN, Ar2, (CO)R7, (CO)OR′3, (CO)NR4R5, O(CO)R7, O(CO)OR′3, O(CO)NR4R6, NR6(CO)R7, NR6(CO)OR′3, OR′3, NR4R5, SR6, SOR7, SO2R7 and/or OSO2R7;
• or R1 is camphorylsulfonyl, phenyl-C1-C3alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl or heteroarylsulfonyl,
• wherein the groups camphorylsulfonyl, phenyl-C1-C3alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl and heteroarylsulfonyl optionally are substituted by one or more C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR6 CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6 CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or are substituted by halogen, NO2, CN, Ar2, (CO)R7, (CO)OR′3, (CO)NR4R5, O(CO)R7, O(CO)OR′3, O(CO)NR4R6, NR6(CO)R7, NR6(CO)OR′3, OR′3, NR4R6, SR6, SOR7, SO2R7 and/or OSO2R7;
• wherein all radicals R1 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;
• R′1, is phenylenedisulfonyl, naphthylenedisulfonyl,
• diphenylenedisulfonyl or oxydiphenylenedisulfonyl,
• wherein the groups phenylenedisulfonyl, naphthylenedisulfonyl,
• diphenylenedisulfonyl and oxydiphenylenedisulfonyl optionally are substituted by one or more C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or are substituted by halogen, NO2, CN, Ar2, (CO)R2, (CO)OR′3, (CO)NR4R5, O(CO)R7, O(CO)OR′3, O(CO)NR4R5, NR6(CO)R2, NR6(CO)OR′3, OR′3, NR4R5, SR6, SOR7, SO2R7 and/or OSO2R7;
• or R′1 is C1-C12alkylenedisulfonyl or C1-C10haloalkylenedisulfonyl;
• wherein all radicals R′1, 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;
• R2 is CN, C1-C10haloalkyl or C1-C10haloalkyl which is substituted by 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, SOR2, SO2R2, OSO2R7, and/or a group of formula IV
• Ar1 is phenyl, biphenylyl, fluorenyl, naphthyl, anthryl, phenanthryl or heteroaryl, wherein the groups phenyl, biphenylyl, fluorenyl, naphthyl, anthryl, phenanthryl and heteroaryl optionally are substituted by one or more C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or are substituted by a group of formula IV
• 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 and/or OSO2R7;
• optionally the substituents C1-C18alkyl, C2-C12alkenyl, (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 C1-C18alkyl, C2-C12alkenyl, R3, R4, R6, R6 and/or R7, with further substituents on the phenyl, biphenylyl, naphthyl, anthryl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, biphenylyl, naphthyl, anthryl, phenanthryl, or heteroaryl ring;
• 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;
• Ar1 is phenylene, biphenylene, naphthylene,
• heteroarylene, oxydiphenylene or
• wherein the groups phenylene, biphenylene, naphthylene,
• heteroarylene, oxydiphenylene and
• optionally are substituted by one or more C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or are substituted by a group of formula IV
• or are substituted by 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 and/or OSO2R7,
• optionally the substituents C1-C18alkyl, C2-C12alkenyl, (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 C1-C18alkyl, C2-C12alkenyl, R3, R4, R5, R6 and/or R7, with further substituents on the phenylene, biphenylene, naphthylene,
• heteroarylene,
• or oxydiphenylene ring or with one of the carbon atoms of the phenylene, biphenylene, naphthylene,
• heteroarylene,
• or oxydiphenylene ring;
• or Ar′1 is —Ar″1—X1—Y1—X1—Ar″1—;
• wherein all radicals Ar′1 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,
• Ar″1 is phenylene, biphenylene, naphthylene, heteroarylene;
• wherein the groups phenylene, biphenylene, naphthylene, heteroarylene optionally are substituted by one or more C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or are substituted by 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 and/or OSO2R7,
• optionally the substituents C1-C18alkyl, C2-C12alkenyl, (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 C1-C18alkyl, C2-C12alkenyl, R3, R4, R5, R6 and/or R7, with further substituents on the phenylene, biphenylene, naphthylene, heteroarylene ring or with one of the carbon atoms of the phenylene, biphenylene, naphthylene, heteroarylene ring;
• wherein all radicals A″1 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;
• X1 is a direct bond, O, S, NR6, CO, O(CO), S(CO), NR6(CO), SO, SO2, or OSO2;
• or X1 is C1-C18alkylene or phenylene wherein these radicals are unsubstituted or substituted by one or more C1-C18alkyl, C1-C4haloalkyl, halogen, OR3 and/or SR6;
• Y1 is C1-C18alkylene which optionally is substituted by OR3, SR6, halogen, phenyl and/or a group of formula IV
• or Y1 is C2-C18alkylene which is interrupted by one or more O, S, NR5, CO SO and/or SO2 and which optionally is substituted by a group of formula IV
• R′3 is hydrogen, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl;
• or R′3 is C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or R′3 is phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl or phenanthrylsulfonyl;
• wherein the groups phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl and phenanthrylsulfonyl optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, NR4R5, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy and/or benzoyloxy;
• R3 is C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl;
• all of which optionally are substituted by a group of formula IV
• or R3 is C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or R3 is phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthryl sulfonyl or phenanthrylsulfonyl;
• wherein the groups phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl and phenanthrylsulfonyl optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, NR4R5, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy, benzoyloxy and/or a group of formula IV
• or R3 is hydrogen;
• R4 and R5 independently of each other are hydrogen, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or R4 and R5 independently of each other are phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl or phenanthrylsulfonyl;
• wherein the groups phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl and phenanthrylsulfonyl optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, C1-C18alkylamino, C1-C18dialkylamino, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy, and/or by benzoyloxy;
• 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, NR8 or CO;
• R6 is hydrogen, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR8, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR8, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR8, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR8, CO, SO and/or SO2;
• or R6 is phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl or phenanthrylsulfonyl;
• wherein the groups phenyl, naphthyl, C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthrylsulfonyl and phenanthrylsulfonyl optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, NR4R6, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy and/or by benzoyloxy;
• R7 is hydrogen, C3-C30cycloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C2-C18alkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenyl which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• or R7 is phenyl, or naphthyl both of which optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, NR4R6, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy and/or by benzoyloxy;
• R8 is C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl or phenyl-C1-C3alkyl;
• Ar2 is phenyl, biphenylyl or naphthyl,
• wherein the groups phenyl, biphenylyl and naphthyl optionally are substituted by one or more OH, C1-C18alkyl, C1-C10haloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, NR4R5, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy and/or by benzoyloxy;
• A1, A2 and A3 independently of each other are hydrogen, halogen, CN, C1-C18alkyl, C1-C18alkyl which is substituted by OR3;
• or A1, A2 and A3 independently of each other are C1-C10haloalkyl, (CO)R7, (CO)OR3, or (CO)NR4R5;
• D2 is a direct bond, O, (CO)O, (CO)S, (CO)NR6, SO2, OSO2, Ar′2, C1-C18alkylene;
• or A3 and D2 together with the ethylenically unsaturated double bond to which they are attached form C3-C30cycloalkenyl which optionally is interrupted by one or more O, S, N, NR6, CO, SO and/or SO2;
• or A2 and D2 together with the carbon of the ethylenically unsaturated double bond to which they are attached form C3-C30cycloalkyl which optionally is interrupted by one or more O, S, N, NR6, CO, SO and/or SO2;
• D3 and D4 independently of each other are a direct bond, O, S, NR6, CO, O(CO), (CO)O, (CO)S, (CO)NR6, SO, SO2, OSO2, Ar′2,
• C1-C18alkylene, C3-C30cycloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, C2-C18alkylene which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C3-C30cycloalkylene which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C4-C30cycloalkenylene which is interrupted by one or more O, S, NR6, CO, SO and/or SO2, C2-C12alkenylene which is interrupted by one or more O, S, NR6, CO, SO and/or SO2;
• wherein the groups C1-C18alkylene, C3-C30cycloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, interrupted C2-C18alkylene, interrupted C3-C30cycloalkylene interrupted C4-C30cycloalkenylene and interrupted C2-C12alkenylene optionally are substituted by one or more Ar2, OH, halogen, NO2, CN, C1-C18alkoxy, phenoxy, NR4R5, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy, and/or by benzoyloxy;
• wherein all radicals D3 and O4 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;
• Ar′2 is phenylene, biphenylene, naphthylene or heteroarylene;
• wherein the groups phenylene, biphenylene, naphthylene and heteroarylene optionally are substituted by one or more OH, C1-C18alkyl, C1-C10haloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, NR4R5, C1-C12alkylthio, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyloxy and/or by benzoyloxy;
• R2a has one of the meanings given for R2;
• provided that at least one of the radicals R2, R3, Ar1 or Ar1′ comprises a group of the formula IV.