Oxime ester photoinitiators

A compound of formula I, II, III or IV,

• wherein
• R1 is hydrogen, C1-C20alkyl, C1-C6alkyl-C3-C6cycloalkyl, C3-C20cycloalkyl, C2-C12alkenyl, wherein C3-C20cycloalkyl or C2-C12alkenyl is uninterrupted or interrupted by one or more O, S, CO, NR10 or COOR4;
• or
• R1 is C1-C20alkyl which is unsubstituted or substituted by one or more halogen, OR4, SR9, NR10R11, COOR4CONR10R11, CN, PO(OR3a)2, S(O)m—R3a,
• C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4, SR9, NR10R11, PO(OR3a)2 or S(O)m—R3a;
• or
• R1 is C2-C20alkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO, SO2, phenylene, naphthylene or NR10, wherein the interrupted C2-C20alkyl is unsubstituted or substituted by one or more halogen, C3-C8cycloalkyl, OH, SH, OR4, SR9, COOR4, O(CO)—R3a, CONR10R11, NR10R11, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4, SR9 or NR10R11;
• or
• R1 is C6-C20aryl or C3-C20heteroaryl each of which is unsubstituted or substituted by one or more C1-C20alkyl, phenyl, halogen, C1-C4haloalkyl, CN, NO2, OR4, SR9, NR10R11, COOR4, (CO)—R3a, (CO)NR10R11, PO(OR3a)2, S(O)m—R3a or group
• or by one or more C2-C20alkyl which is interrupted by one or more O, S, or NR10;
• or by one or more C1-C20alkyl which is unsubstituted or substituted by one or more halogen, COOR4, CONR10R11, phenyl, C3-C8cycloalkyl, C3-C20heteroaryl, C6-C20aryloxycarbonyl, C3-C20heteroaryloxycarbonyl, OR4, SR9 or NR10R11;
• or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR4, SR9 or NR10R11;
• R1 is C2-C20alkanoyl or benzoyl which is unsubstituted or substituted by one or more C1-C6alkyl, phenyl, OR4, SR9 or NR10R11;
• or
• R1 is C2-C12alkoxycarbonyl optionally interrupted by one or more —O— and/or optionally substituted by one or more hydroxyl groups;
• or
• R1 is phenoxycarbonyl which is unsubstituted or substituted by C1-C6alkyl, halogen, phenyl, OR4, SR9 or NR10R11;
• or
• R1 is CN, (CO)—R3a, COOR4, CONR10R11, NO2, PO(OR3a)2 or S(O)m—R3a;
• R1′ is C1-C20alkylene, C1-C20alkylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or NR8, wherein the C1-C20alkylene and interrupted C1-C20alkylene is unsubstituted or substituted by halogen or OR4, or
• R1′ is C2-C20alkenylene, C2-C20alkenylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or by NR10, wherein the C2-C20alkenylene and interrupted C2-C20alkenylene is unsubstituted or substituted by halogen or OR4, or
• R1′ is C5-C8cycloalkylene, C5-C8cycloalkenylene,
• wherein the groups CyH2y and CzH2z are uninterrupted or interrupted by one or more O, S or by NR10;
• R1a is hydrogen, C1-C20alkyl, CN, (CO)—R3a, COOR4a, CONR10aR11a, NO2, PO(OR3a)2 or S(O)m—R3a;
• or
• R1a is C1-C20alkyl substituted by one or more halogen, OR4a, SR9a, NR10aR11a, CN, COOR4a, CONR10aR11a, PO(OR3a)2, S(O)m—R3a, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4a, SR9a NR10aR11a, PO(OR3a)2 or S(O)m—R3a;
• or
• R1a is C1-C20alkyl interrupted by one or more O, S, NR10a CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)R3a, COOR4a, CONR10aR11a, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4a, SR9a or NR10aR11a;
• or
• R1a is C2-C12alkenyl or C3-C20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10a or COOR4a;
• or
• R1a is C6-C20aryl or C3-C20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—R3a CONR10aR11a, PO(OR3a)2 or S(O)m—R3a;
• or by one or more C1-C20alkyl which is unsubstituted or substituted by one or more halogen, COOR4a, CONR10aR11a, phenyl, C3-C8cycloalkyl, C3-C20heteroaryl, OR4a, SR9a or NR10aR11a;
• or by one or more C2-C20alkyl which is interrupted by one or more O, S or NR10a;
• or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR4a, SR9a or NR10aR11a;
• R2 is hydrogen, C1-C20alkyl or C1-C6alkyl-C3-C6-cycloalkyl which is unsubstituted or substituted by one or more halogen, OR4, SR9, COOR4CONR10R11, NR10R11, PO(OR3a)2;
• COR3a, or
• R2 is C2-C20alkyl or C1-C6alkyl-C3-C6-cycloalkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), SO, SO2, phenylene, naphthylene or NR10, wherein the interrupted C2-C20alkyl is unsubstituted or substituted by one or more halogen, OR4, SR9, COOR4, CONR10R11, NR10R11;
• or
• R2 is C2-C4hydroxyalkyl, C2-C10alkoxyalkyl, C3-C5alkenyl, C3-C8cycloalkyl, phenyl-C1-C3alkyl, C2-C8alkanoyl, C3-C12alkenoyl, benzoyl;
• or
• R2 is C6-C20aryl or C3-C20heteroaryl each of which is unsubstituted or substituted by one or more C1-C12alkyl, C1-C4haloalkyl, phenyl, halogen, CN, NO2, OR4, SR9, NR10R11, (CO)—R3a, or by C2-C20alkyl which is interrupted by one or more O, S, or NR10, or each of which is substituted by one or more C1-C20alkyl which is unsubstituted or substituted by one or more halogen, COOR4, CONR10R11, phenyl, C3-C8cycloalkyl, C3-C20heteroaryl, C6-C20aryloxycarbonyl, C3-C20heteroaryloxycarbonyl, OR4, SR9 or NR10R11;
• or
• R2 is a group
• R2′ is C1-C20alkylene, C1-C20alkylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or NR8, wherein the C1-C20alkylene and interrupted C1-C20alkylene is unsubstituted or substituted by halogen or OR4, or
• R2′ is C2-C20alkenylene, C2-C20alkenylene which is interrupted by one or more O, S, (CO)O, O(CO), phenylene, naphthylene or by NR10, wherein the C2-C20alkenylene and interrupted C2-C20alkenylene is unsubstituted or substituted by halogen or OR4, or
• R2′ is C5-C8cycloalkylene, C5-C8cycloalkenylene,
• wherein the groups CyH2y and CzH2z are uninterrupted or interrupted by one or more O, S or by NR10;
• R3 is hydrogen or C1-C20alkyl;
• or
• R3 is C1-C20alkyl substituted by one or more halogen, OR4, SR9, NR10R11, CN, COOR4, CONR10R11, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4, SR9 or NR10R11;
• or
• R3 is C1-C20alkyl interrupted by one or more O, S, NR10, CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—R3a, COOR4, CONR10R11 C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4, SR9 or NR10R11;
• or
• R3 is C2-C12alkenyl or C3-C20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10 or COOR4;
• or
• R3 is C6-C20aryl or C3-C20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4, SR9, NR10R11, COOR4, (CO)—R3a or SO2—R3a;
• or
• R3 is C1-C20alkoxy, which is unsubstituted or substituted by one or more C1-C10alkyl, C1-C4haloalkyl, halogen, phenyl, C1-C20alkylphenyl or C1-C8alkoxyphenyl;
• or
• R3 is C1-C20alkoxy, which is interrupted by one or more O, S, NR10, CO, SO or SO2;
• or
• R3 is C6-C20aryloxy or C3-C20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4, SR9, NR10R11, COOR4, (CO)—R3a or SO2—R3a;
• R3a is hydrogen or C1-C20alkyl;
• or
• R3a is C1-C20alkyl substituted by one or more halogen, OR4a, SR9a, NR10aR11a, CN, COOR4a, CONR10aR11a, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4a, SR9a or NR10aR11a;
• or
• R3a is C1-C20alkyl interrupted by one or more O, S, NR10a CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—(C1-C8alkyl), COOR4a, CONR10aR11a, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4a, SR9a or NR10aR11a;
• or
• R3a is C2-C12alkenyl or C3-C20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10a or COOR4a;
• or
• R3a is C6-C20aryl or C3-C20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—(C1-C8alkyl) or SO2—(C1-C4haloalkyl);
• or
• R3a is C1-C20alkoxy, which is unsubstituted or substituted by one or more C1-C10alkyl, C1-C4haloalkyl, halogen, phenyl, C1-C20alkylphenyl or C1-C8alkoxyphenyl;
• or
• R3a is C1-C20alkoxy, which is interrupted by one or more O, S, NR10a CO, SO or SO2;
• or
• R3a is C6-C20aryloxy or C3-C20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—(C1-C8alkyl) or SO2—(C1-C4haloalkyl);
• or
• R3a is a group
• R3b is hydrogen or C1-C20alkyl;
• or
• R3b is C1-C20alkyl substituted by one or more halogen, OR4a, SR9a, NR10aR11a, CN, COOR4a, CONR10aR11a, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4a, SR9a or NR10aR11a;
• or
• R3b is C1-C20alkyl interrupted by one or more O, S, NR10a CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—(C1-C8alkyl), COOR4a, CONR10aR11a, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4a, SR9a or NR10aR11a;
• or
• R3b is C2-C12alkenyl or C3-C20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10a or COOR4a;
• or
• R3b is C6-C20aryl or C3-C20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—(C1-C8alkyl) or SO2—(C1-C4haloalkyl);
• or
• R3b is C1-C20alkoxy, which is unsubstituted or substituted by one or more C1-C10alkyl, C1-C4haloalkyl, halogen, phenyl, C1-C20alkylphenyl or C1-C8alkoxyphenyl;
• or
• R3b is C1-C20alkoxy, which is interrupted by one or more O, S, NR10a CO, SO or SO2;
• or
• R3b is C6-C20aryloxy or C3-C20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—(C1-C8alkyl) or SO2—(C1-C4haloalkyl);
• R4 is hydrogen, (CO)—R3a, COOR4a, CONR10R11, S(O)m—R3a or PO(OR3a)2;
• or
• R4 is C1-C20alkyl, which is substituted by one or more halogen, OR4a, SR9a, NR10aR11a CN, COOR4a, CONR10aR11a, PO(OR3a)2, S(O)m—R3a, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4a, SR9a NR10aR11a PO(OR3a)2 or S(O)m—R3a;
• or
• R4 is C1-C20alkyl interrupted by one or more O, S, NR10a, CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—R3a, COOR4a, CONR10aR11a, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4a, SR9a or NR10aR11a;
• or
• R4 is C2-C12alkenyl or C3-C20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10a or COOR4a;
• or
• R4 is C6-C20aryl, which is substituted by one or more halogen, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—R3a, CONR10aR11a, PO(OR3a)2, S(O)m—R3a or group
• or by one or more C1-C20alkyl which is unsubstituted or substituted by one or more halogen, COOR4a, CONR10aR11a, phenyl, C3-C8cycloalkyl, C3-C20heteroaryl, OR4a, SR9a or NR10aR11a;
• or by one or more C2-C20alkyl which is interrupted by one or more O, S or NR10a;
• or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR4a, SR9a or NR10aR11a;
• or
• R4 is C3-C20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—R3a, CONR10aR11a, PO(OR3a)2, S(O)m—R3a or group
• or by one or more C1-C20alkyl which is unsubstituted or substituted by one or more halogen, COOR4a, CONR10aR11a, phenyl, C3-C8cycloalkyl, C3-C20heteroaryl, OR4a, SR9a or NR10aR11a;
• or by one or more C2-C20alkyl which is interrupted by one or more O, S or NR10a;
• or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR4a, SR9a or NR10aR11a;
• or
• R4 together with one of the carbon atom of R1 forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C1-C20alkyl, OR4a, SR9a, NR10aR11a (CO)—R3a, NO2, halogen, C1-C4haloalkyl, CN, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl,
• or C3-C20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• R4′ is —(CO)—, —(CO)O—, —(CO)N—, —S(O)m—, —PO(O)2—, or —OP(O)2;
• R4a is hydrogen, C1-C20alkyl, (CO)O(C1-C8alkyl) or CON(C1-C8alkyl)2;
• or
• R4a is C1-C20alkyl substituted by one or more halogen, OH, SH, CN, C3-C8alkenoxy, OCH2CH2CN, OCH2CH2(CO)O(C1-C8alkyl), O(CO)—(C1-C8alkyl), O(CO)—(C2-C4)alkenyl, O(CO)-phenyl, (CO)OH, (CO)O(C1-C8alkyl), C3-C8cycloalkyl, SO2—(C1-C4haloalkyl), O(C1-C4haloalkyl), phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl or C3-C8cycloalkyl which is interrupted by one or more O;
• or
• R4a is C2-C20alkyl interrupted by one or more O, S, N(C1-C8alkyl), CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)(C1-C8alkyl), (CO)O(C1-C8alkyl), (CO)N(C1-C8alkyl)2, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, C1-C8alkoxy, C1-C8alkylsulfanyl or N(C1-C8alkyl)2;
• or
• R4a is C2-C12alkenyl, (CO)O(C1-C8alkenyl) or C3-C8cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, N(C1-C8alkyl) or COO(C1-C8alkyl);
• or
• R4a is C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, CN, NO2, OH, C1-C8alkyl, C1-C4haloalkyl, C1-C8alkoxy, phenyl-C1-C3alkyloxy, phenoxy, C1-C8alkylsulfanyl, phenylsulfanyl, N(C1-C8alkyl)2, diphenylamino, (CO)O(C1-C8alkyl), (CO)—C1-C8alkyl or (CO)N(C1-C8)2, phenyl or benzoyl;
• or
• R4a is C1-C20alkanoyl, C3-C12alkenoyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl, OH, C1-C8alkoxy, phenoxy, C1-C8alkylsulfanyl, phenylsulfanyl, N(C1-C8alkyl)2 or diphenylamino;
• R5, R6, R7 and R8 independently of each other are hydrogen, C1-C20alkyl, C6-C20aryl, C1-C20alkoxy, C6-C20arylC1-C20alkyl, hydroxyC1-C20alkyl, hydroxyC1-C20alkoxyC1-C20alkyl, C3-C10cycloalkyl, amino, CN, NO2, hydroxy,
• (CO)—R3a, OR4a or COOR4;
• R9 is hydrogen or C1-C20alkyl;
• or
• R9 is C1-C20alkyl substituted by one or more halogen, OR4a, SR9a, NR10aR11a, CN, COOR4a CONR10aR11a, PO(OR3a)2, S(O)m—R3a, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4a, SR9a NR10aR11a, PO(OR3a)2 or S(O)m—R3a;
• or
• R9 is C1-C20alkyl interrupted by one or more O, S, NR10a CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—R3a, COOR4a, CONR10aR11a, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4a, SR9a or NR10aR11a;
• or
• R9 is C2-C12alkenyl or C3-C20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10a or COOR4a;
• or
• R9 is C6-C20aryl or C3-C20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—R3a CONR10aR11a, PO(OR3a)2, S(O)m—R3a or group
• or by one or more C1-C20alkyl which is unsubstituted or substituted by one or more halogen, COOR4a, CONR10aR11a, phenyl, C3-C8cycloalkyl, C3-C20heteroaryl, OR4a, SR9a or NR10aR11a;
• or by one or more C2-C20alkyl which is interrupted by one or more O, S or NR10a;
• or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR4a, SR9a or NR10aR11a;
• or
• R9 together with one of the carbon atom of R1 forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C1-C20alkyl, OR4a, SR9a, NR10aR11a (CO)—R3a, NO2, halogen, C1-C4haloalkyl, CN, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl,
• or C3-C20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• R9a is hydrogen or C1-C20alkyl;
• or
• R9a is C1-C20alkyl substituted by one or more halogen, OH, SH, CN, C3-C8alkenoxy, OCH2CH2CN, OCH2CH2(CO)O(C1-C8alkyl), O(CO)—(C1-C8alkyl), O(CO)—(C2-C4)alkenyl, O(CO)-phenyl, (CO)OH, (CO)O(C1-C8alkyl), C3-C8cycloalkyl, SO2—(C1-C4haloalkyl), O(C1-C4haloalkyl), phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl or C3-C8cycloalkyl which is interrupted by one or more O;
• or
• R9a is C2-C20alkyl interrupted by one or more O, S, N(C1-C8alkyl), CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)(C1-C8alkyl), (CO)O(C1-C8alkyl), (CO)N(C1-C8alkyl)2, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, C1-C8alkoxy, C1-C8alkylsulfanyl or N(C1-C8alkyl)2;
• or
• R9a is C2-C12alkenyl or C3-C8cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, N(C1-C8alkyl) or COO(C1-C8alkyl);
• or
• R9a is C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, CN, NO2, OH, C1-C8alkyl, C1-C4haloalkyl, C1-C8alkoxy, phenyl-C1-C3alkyloxy, phenoxy, C1-C8alkylsulfanyl, phenylsulfanyl, N(C1-C8alkyl)2, diphenylamino, (CO)O(C1-C8alkyl), (CO)—C1-C8alkyl or (CO)N(C1-C8)2, phenyl or benzoyl;
• or
• R9a is C1-C20alkanoyl, C3-C12alkenoyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl, OH, C1-C8alkoxy, phenoxy, C1-C8alkylsulfanyl, phenylsulfanyl, N(C1-C8alkyl)2 or diphenylamino;
• R10 and R11 independently of each other are hydrogen, C1-C20alkyl, S(O)m—R3a, O(CO)—R3a(CO)—R3a or CONR10aR11a;
• or
• R10 and R11 independently of each other are C1-C20alkyl substituted by one or more halogen, OR4a, SR9a, NR10aR11a, CN, COOR4a, CONR10aR11a, PO(OR3a)2, S(O)m—R3a, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4a, SR9a, NR10aR11a PO(OR3a)2 or S(O)m—R3a;
• or
• R10 and R11 independently of each other are C1-C20alkyl interrupted by one or more O, S, NR10a CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—R3a, COOR4a, CONR10aR11a, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4a, SR9a or NR10aR11a;
• or
• R10 and R11 independently of each other are C2-C12alkenyl or C3-C20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10a or COOR4a;
• or
• R10 and R11 independently of each other are C6-C20aryl or C3-C20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, CN, NO2, OR4a, SR9a, NR10aR11a, COOR4a, (CO)—R3a CONR10aR11a, PO(OR3a)2, S(O)m—R3a or group
• or by one or more C1-C20alkyl which is unsubstituted or substituted by one or more halogen, COOR4a, CONR10aR11a, phenyl, C3-C8cycloalkyl, C3-C20heteroaryl, OR4a, SR9a or NR10aR11a;
• or by one or more C2-C20alkyl which is interrupted by one or more O, S or NR10a;
• or by one or more phenyl, naphthyl, benzoyl or naphthoyl, each of which is unsubstituted or substituted by OR4a, SR9a or NR10aR11a;
• or
• R10 and R11 independently of each other are C1-C20alkoxy, which is unsubstituted or substituted by one or more halogen, phenyl, C1-C8alkylphenyl or C1-C8alkoxyphenyl;
• or
• R10 and R11 independently of each other are C1-C20alkoxy, which is interrupted by one or more O, S, NR10a CO, SO or SO2;
• or
• R10 and R11 independently of each other are C6-C20aryloxy or C3-C20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C1-C8alkyl, C1-C4haloalkyl, phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4a, SR9a, NR10aR11a COOR4a, (CO)—R3a or SO2—R3a;
• or
• R10 together with one of the carbon atom of R1 forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C1-C20alkyl, OR4a, SR9a, NR10aR11a (CO)—R3a, NO2, halogen, C1-C4-haloalkyl, CN, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl,
• or C3-C20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• or
• R10 and R11 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR10a and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C1-C20alkyl, OR4a, SR9a, NR10aR11a (CO)—R3a, NO2, halogen, C1-C4-haloalkyl, CN, phenyl,
• or C3-C20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10a;
• R10a and R11a independently of each other are hydrogen, C1-C20alkyl, S(O)m—(C1-C8alkyl), O(CO)(C1-C8alkyl), (CO)(C1-C8alkyl), (CO)O(C1-C8alkyl) or CON(C1-C8alkyl)2;
• or
• R10a and R11a independently of each other are C1-C20alkyl substituted by one or more halogen, OH, SH, CN, C3-C8alkenoxy, OCH2CH2CN, OCH2CH2(CO)O(C1-C8alkyl), O(CO)—(C1-C8alkyl), O(CO)—(C2-C4)alkenyl, O(CO)-phenyl, (CO)OH, (CO)O(C1-C8alkyl), C3-C8cycloalkyl, SO2—(C1-C4haloalkyl), O(C1-C4haloalkyl), phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl or C3-C8cycloalkyl which is interrupted by one or more O;
• or
• R10a and R11a independently of each other are C2-C20alkyl interrupted by one or more O, S, N(C1-C8alkyl), CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)(C1-C8alkyl), (CO)O(C1-C8alkyl), (CO)N(C1-C8alkyl)2, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, C1-C8alkoxy, C1-C8alkylsulfanyl or N(C1-C8alkyl)2;
• or
• R10a and R11a independently of each other are C2-C12alkenyl or C3-C8cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, N(C1-C8alkyl) or COO(C1-C8alkyl);
• or
• R10a and R11a independently of each other are C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, CN, NO2, OH, C1-C8alkyl, C1-C4haloalkyl, C1-C8alkoxy, phenyl-C1-C3alkyloxy, phenoxy, C1-C8alkylsulfanyl, phenylsulfanyl, N(C1-C8alkyl)2, diphenylamino, (CO)O(C1-C8alkyl), (CO)—C1-C8alkyl or (CO)N(C1-C8alkyl)2, phenyl or benzoyl;
• or
• R10a and R11a independently of each other are C1-C20alkanoyl, C3-C12alkenoyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl, OH, C1-C8alkoxy, phenoxy, C1-C8alkylsulfanyl, phenylsulfanyl, N(C1-C8alkyl)2 or diphenylamino;
• or
• R10a and R11a independently of each other are C1-C20alkoxy, which is unsubstituted or substituted by one or more halogen, phenyl, C1-C8alkylphenyl or C1-C8alkoxyphenyl;
• or
• R10a and R11a independently of each other are C1-C20alkoxy, which is interrupted by one or more O, S, N(C1-C8alkyl), CO, SO or SO2;
• or
• R10a and R11a independently of each other are C6-C20aryloxy or C3-C20heteroaryloxy, each of which is unsubstituted or substituted by one or more halogen, C1-C8alkyl, C1-C4haloalkyl, phenyl, C1-C8alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, C1-C8alkoxy, C1-C8alkylsulfanyl, N(C1-C8alkyl)2, CO(OC1-C8alkyl), (CO)—(C1-C8alkyl) or SO2—(C1-C8alkyl);
• or
• R10a and R11a together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or N(C1-C8alkyl), and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C1-C8alkyl, C1-C8alkoxy, C1-C8alkylsulfanyl, N(C1-C8alkyl)2, NO2, halogen, C1-C4haloalkyl, CN, phenyl or C3-C20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or N(C1-C8alkyl);
• R12 and R13 independently of each other are hydrogen, C1-C12alkyl optionally substituted by one or more halogen, phenyl, CN, —OH, —SH, C1-C4alkoxy, (CO)OH or (CO)O(C1-C4alkyl);
• or
• R12 and R13 are phenyl optionally substituted by one or more C1-C6alkyl, halogen, CN, OR4, SR9 or NR10R11;
• or
• R12 and R13 are halogen, CN, OR4, SR9, SOR9, SO2R9 or NR10R11, wherein the substituents OR4, SR9 or NR10R11 optionally form 5- or 6-membered rings via the radicals R4, R9, R10 and/or R11 with one of the carbon atoms of the phenyl, naphthyl, benzoyl or naphthoyl group or that of the substituent R3a;
• or
• R2 and R13 together are a group
• wherein R14, R15, R16 and R17 independently of one another are hydrogen, C1-C12alkyl optionally substituted by one or more halogen, phenyl, CN, —OH, —SH, C1-C4alkoxy, (CO)OH or (CO)O(C1-C4alkyl);
• or R14, R15, R16 and R17 are phenyl optionally substituted by one or more C1-C6alkyl, halogen, CN, OR4, SR9 or NR10R11;
• or R14, R15, R16 and R17 are halogen, CN, OR4, SR9 or NR10R11;
• or
• R12 and R13 together are a group
• wherein R18 and R19 independently of each other are hydrogen, C1-C12alkyl optionally substituted by one or more halogen, phenyl, CN, —OH, —SH, C1-C4-alkoxy, (CO)OH or (CO)O(C1-C4alkyl);
• or
• R18 and R19 are phenyl optionally substituted by one or more C1-C6alkyl, halogen, CN, OR4, SR9 or NR10R11;
• M is a direct bond or a divalent linking group C1-C20alkylene or C1-C20alkylene substituted by one or more halogen, OR4, SR9, NR10R11, CN, COOR4, CONR10R11, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4, SR9 or NR10R11;
• or
• M is C1-C20alkylene interrupted by one or more O, S, NR10, CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—R3a, COOR4, CONR10R11, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4, SR9 or NR10R11;
• or
• M is C2-C12alkenylene or C3-C20cycloalkylene, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10 or COOR4;
• or
• M is C6-C20arylene or C3-C20heteroarylene, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4, SR9, NR10R11, COOR4, (CO)—R3a or SO2—R3a;
• M′ is a direct bond or a divalent linking group selected from C1-C20alkylene or C1-C20alkylene substituted by one or more halogen, OR4, SR9, NR10R11, CN, COOR4, CONR10R11, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4, SR9 or NR10R11;
• or
• M′ is C1-C20alkylene interrupted by one or more O, S, NR10, CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—R3a, COOR4, CONR10R11, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4, SR9 or NR10R11;
• or
• M′ is C2-C12alkenylene or C3-C20cycloalkylene, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10 or COOR4;
• or
• M′ is C6-C20arylene or C3-C20heteroarylene, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4, SR9, NR10R11, COOR4, (CO)—R3a or SO2—R3a;
• M″ is a direct bond or a divalent linking group selected from C1-C20alkylene or C1-C20alkylene substituted by one or more halogen, OR4, SR9, NR10R11, CN, COOR4, CONR10R11, C3-C8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR10;
• or by one or more C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, each of which is unsubstituted or substituted by one or more halogen, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, C1-C4haloalkyl, CN, NO2, OR4, SR9 or NR10R11;
• or
• M″ is C1-C20alkylene interrupted by one or more O, S, NR10, CO, SO or SO2, which is unsubstituted or substituted by C3-C8cycloalkyl, OH, SH, O(CO)—R3a, COOR4, CONR10R11, C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl, wherein C6-C20aryl, C3-C20heteroaryl, C6-C20aroyl or C3-C20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C1-C8alkyl, OR4, SR9 or NR10R11;
• or
• M″ is C2-C12alkenylene or C3-C20cycloalkylene, each of which is uninterrupted or interrupted by one or more O, S, CO, NR10 or COOR4;
• or
• M″ is C6-C20arylene or C3-C20heteroarylene, each of which is unsubstituted or substituted by one or more halogen, C1-C20alkyl, C1-C4haloalkyl, phenyl, C1-C20alkylphenyl, C1-C8alkoxyphenyl, CN, NO2, OR4, SR9, NR10R11, COOR4, (CO)—R3a or SO2—R3a;
• m is 1 or 2;
• Q is CO or a direct bond;
• and
• x, y and z independently of each other are an integer 1, 2, 3 or 4.