OXIME ESTER PHOTOINITIATORS

Abstract

Compounds of the formulae (I) or (II)

##STR00001##

wherein X is

##STR00002## A is O, S, NR.sub.5 or CR.sub.16R.sub.17; R.sub.1 is for example hydrogen or C.sub.1-C.sub.20alkyl R.sub.2 is for example hydrogen, C.sub.1-C.sub.20alkyl or C.sub.6-C.sub.20aryl R.sub.5 for example is C.sub.1-C.sub.20alkyl; R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 for example independently of each other are hydrogen. C.sub.1-C.sub.20alkyl, halogen, CN or NO.sub.2; Ar.sub.1 is for example unsubstituted or substituted C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl, C.sub.3-C.sub.20heteroarylcarbonyl or

##STR00003## or Ar.sub.1 is

##STR00004## Ar.sub.2 is for example phenylene,

##STR00005##

all of which are unsubstituted or substituted M is for example unsubstituted or substituted C.sub.1-C.sub.20alkylene Y is a direct bond, O, S, NR.sub.5 or CO; Z.sub.1 is for example O or S; Z.sub.2 is a direct bond, O, S or NR.sub.5; and Q is CO or a direct bond.

Claims

1. Compounds of formulae (I) or (II) ##STR00191## wherein X is ##STR00192## A is O, S, NR.sub.5 or CR.sub.16R.sub.17; R.sub.1 is selected from: hydrogen, or C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, of which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; or or R.sub.1 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.1 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted, or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; R.sub.1 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a or SO.sub.2R.sub.1a; R.sub.1 is C.sub.1-C.sub.20alkoxy, which is unsubstituted, or substituted by one or more C.sub.1-C.sub.10alkyl, C.sub.1-C.sub.4haloalkyl, halogen, phenyl, C.sub.1-C.sub.20alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; R.sub.1 is C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2; R.sub.1 is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a or SO.sub.2R.sub.1a; or R.sub.1 is R.sub.1a, and R.sub.1a is selected from hydrogen, or C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, CN, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.1a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted, or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.1a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5a or COOR.sub.3a; R.sub.1a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)(C.sub.1-C.sub.8alkyl), benzoyl or SO.sub.2(C.sub.1-C.sub.4haloalkyl); R.sub.1a is C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more C.sub.1-C.sub.10alkyl, C.sub.1-C.sub.4haloalkyl, halogen, phenyl, C.sub.1-C.sub.20alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; R.sub.1a is C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2; or R.sub.1a is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted,or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)(C.sub.1-C.sub.8alkyl), SO.sub.2(C.sub.1-C.sub.4haloalkyl), benzoyl, or ##STR00193## which benzoyl or ##STR00194## is unsubstituted, or substituted by ##STR00195## R.sub.2 is selected from hydrogen, CN, (CO)R.sub.1a, (CO)OR.sub.3, CONR.sub.5R.sub.6, NO.sub.2, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.2 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00196## C.sub.3-C.sub.8cycloalkyl which is unintenupted or interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.2 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.2 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted, or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; R.sub.2 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a(CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00197## C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5R.sub.6, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by one or more OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; or R.sub.2 is R.sub.2a, and R.sub.2a is selected from hydrogen, CN, (CO)R.sub.1a, (CO)OR.sub.3a, CONR.sub.5aR.sub.6a, NO.sub.2, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.2a is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, CN, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstitutotor substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.2a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted, or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.2a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted, or interrupted by one or more O, S, CO, NR.sub.5a or COOR.sub.3a; or R.sub.2a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)R.sub.1a(CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5aR.sub.6a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5a, phenyl, naphthyl, benzoyl and naphthoyl, each of which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted, or substituted by one or more OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.3 is selected from hydrogen, (CO)R.sub.1a, (CO)OR.sub.3a, CONR.sub.5R.sub.6, C.sub.1-C.sub.20alkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, CN, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.3 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted, or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.3 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted, or interrupted by one or more O, S, CO, NR.sub.5a or COOR.sub.3a; R.sub.3 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)R.sub.1a(CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00198## C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5aR.sub.6a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5a; phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted, or substituted by one or more OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.3 together with one of the carbon atoms of R.sub.2 or M forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted, or interrupted by O, S or NR.sub.5a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted, or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, (CO)R.sub.1a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00199## or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5a; or R.sub.3 is R.sub.3a, and R.sub.3a is selected from hydrogen, (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; R.sub.3a is C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.2-C.sub.4)alkenyl, O(CO)phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl and C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; R.sub.3a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; R.sub.3a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl is uninterrupted, or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); or R.sub.3a is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)C.sub.1-C.sub.8alkyl or (CO)N(C.sub.1-C.sub.8).sub.2, phenyl or benzoyl; or R.sub.3a is C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl, which C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; R.sub.4 is selected from hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, CN, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.4 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted, or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.4 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted, or interrupted by one or more O, S, CO, NR.sub.5a or COOR.sub.3a; R.sub.4 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)R.sub.1a(CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00200## C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5aR.sub.6a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5a, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted, or substituted by OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.4 together with one of the carbon atoms of R.sub.2 or M forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted, or interrupted by O, S or NR.sub.5a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, (CO)R.sub.1a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00201## or C.sub.3-C.sub.20cyclalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5a; or R.sub.4 is R.sub.4a, and R.sub.4a is selected from hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.2-C.sub.4)alkenyl, O(CO)phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl and C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; R.sub.4a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; R.sub.4a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl is uninterrupted, or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); R.sub.4a is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)C.sub.1-C.sub.8alkyl, (CO)N(C.sub.1-C.sub.8).sub.2, phenyl or benzoyl; or R.sub.4a is C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl, which C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; R.sub.5 and R.sub.6 independently of each other are hydrogen, S(O).sub.mR.sub.1a, O(CO)R.sub.1a, (CO)R.sub.1a or CONR.sub.5aR.sub.6a; R.sub.5 and R.sub.6 independently of each other are C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, CN, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.3-C.sub.8cycloalkyl, which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, of which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.5 and R.sub.6 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted, or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.5 and R.sub.6 independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5a or COOR.sub.3a; R.sub.5 and R.sub.6 independently of each other are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)R.sub.1a(CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00202## C.sub.1-C.sub.20alkyl, which is unsubstituted or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5aR.sub.6a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5a, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted, or substituted by OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.5 and R.sub.6 independently of each other are C.sub.1-C.sub.20alkoxy, which is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; R.sub.5 and R.sub.6 independently of each other are C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2; R.sub.5 and R.sub.6 independently of each other are C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)R.sub.1a or SO.sub.2R.sub.1a; R.sub.5 together with one of the carbon atoms of R.sub.2 or M forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted, or interrupted by O, S or NR.sub.5a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted, or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, (CO)R.sub.1a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00203## or C.sub.3-C.sub.20cyclalkyl, which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5a; R.sub.5 and R.sub.6 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 NR.sub.5a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted, or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, (CO)R.sub.1a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, ##STR00204## or C.sub.3-C.sub.20cyclalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5a; or R.sub.5 and R.sub.6 is R.sub.5a and R.sub.6a, and R.sub.5a and R.sub.6a are independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, S(O).sub.m(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), (CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; R.sub.5a and R.sub.6a independently of each other are C.sub.1-C.sub.20alkyl substituted by one or more halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.2-C.sub.4)alkenyl, O(CO)phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8eycloalkyl, SO.sub.2(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.3-C.sub.8cycloalkyl or C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sub.5a and R.sub.6a independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; R.sub.5a and R.sub.6a independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); R.sub.5a and R.sub.6a independently of each other are C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)C.sub.1-C.sub.8alkyl, (CO)N(C.sub.1-C.sub.8alkyl).sub.2, phenyl or benzoyl; R.sub.5a and R.sub.6a independently of each other are C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl, which C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; R.sub.5a and R.sub.6a independently of each other are C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sub.5a and R.sub.6a independently of each other are C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2; R.sub.5a and R.sub.6a independently of each other are C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, CO(OC.sub.1-C.sub.8alkyl), (CO)(C.sub.1-C.sub.8alkyl) or SO.sub.2(C.sub.1-C.sub.8alkyl); or R.sub.5a and R.sub.6a 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(C.sub.1-C.sub.8alkyl), and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, NO.sub.2, halogen, C.sub.1-C.sub.4haloalkyl, CN, phenyl or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or N(C.sub.1-C.sub.8alkyl); R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, halogen, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00205## wherein the substituents OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6 optionally form 5- or 6-membered ring via the radicals R.sub.3, R.sub.4, R.sub.5 or R.sub.6 with further substituents on the group X; or R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are C.sub.1-C.sub.20alkyl substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; or R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a(CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00206## C.sub.1-C.sub.20alkyl, which is unsubstituted or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5R.sub.6, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted, or substituted by OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; or R.sub.8 and R.sub.9, R.sub.9 and R.sub.10, or R.sub.10 and R.sub.11 are ##STR00207## R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, halogen, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00208## wherein the substituents OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6 optionally form a 5- or 6-membered ring via the radicals R.sub.3, R.sub.4, R.sub.5 or R.sub.6 with further substituents on the group X; or R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of each other are C.sub.1-C.sub.20alkyl substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of each other are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a(CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00209## C.sub.1-C.sub.20alkyl, which is unsubstituted or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5R.sub.6, phenyl, C.sub.3-C.sub.8cycloallcyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.16 and R.sub.17 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.16 and R.sub.17 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.16 and R.sub.17 independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; R.sub.16 and R.sub.17 independently of each other are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a or SO.sub.2R.sub.1a; or R.sub.16 and R.sub.17 together with the carbon 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 NR.sub.5a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, (CO)R.sub.1a, NO.sub.2, halogen, C.sub.1-C.sub.4haloalkyl, CN, phenyl or C.sub.3-C.sub.20cyclalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5a; Ar.sub.1 is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl, C.sub.3-C.sub.20heteroarylcarbonyl or ##STR00210## which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl, C.sub.3-C.sub.20heteroarylcarbonyl or ##STR00211## is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, COOR.sub.3, (CO)R.sub.1a, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00212## OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, wherein the substituents OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6 optionally form 5- or 6-membered rings via the radicals R.sub.3, R.sub.4, R.sub.5 or R.sub.6 with further substituents on the phenyl ring, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sub.3, CONR.sub.5R.sub.6, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5, C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; or Ar.sub.1 is ##STR00213## Ar.sub.2 is phenylene, naphthylene, phenylenecarbonyl, naphthylenecarbonyl, ##STR00214## which phenylene, naphthylene, phenylenecarbonyl, naphthylenecarbonyl, ##STR00215## is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, COOR.sub.3, (CO)R.sub.1a, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00216## OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sub.3, CONR.sub.5R.sub.6, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6, C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; M is C.sub.1-C.sub.20alkylene which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR3, SR4 or NR5R6; M is C.sub.2-C.sub.20alkylene interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which C.sub.1-C.sub.20alkylene or C.sub.2-C.sub.20alkylene is unsubstituted or substituted by one or more substituents selected from the group consisting of C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; M is C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene, which C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; or M is C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene, which C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a or SO.sub.2R.sub.1a; Y is a direct bond, O, S, NR.sub.5 or CO; Z.sub.1 is O, S, CO or CR.sub.16(R.sub.17); Z.sub.2 is a direct bond, O, S or NR.sub.5; m is 1 or 2; and Q is CO or a direct bond.

2. Compounds of the formulae (I) or (II) according to claim 1, wherein X is ##STR00217## A is O, S, NR.sub.5 or CR.sub.16R.sub.17; R.sub.1 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, (CO)OR.sub.3, C.sub.3-C.sub.8cycloalkyl or C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sub.1 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more OH, O(CO)R.sub.1a or (CO)OR.sub.3; or R.sub.1 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl; or R.sub.1 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen or C.sub.1-C.sub.20alkyl; or R.sub.1 is C.sub.1-C.sub.20alkoxy, C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy; R.sub.1a is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl interrupted by one or more O, C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl, C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)(C.sub.1-C.sub.8alkyl) or benzoyl; or R.sub.1a is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by benzoyl, or ##STR00218## which benzoyl or ##STR00219## is unsubstituted or substituted by ##STR00220## R.sub.2 is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, (CO)OR.sub.3, ##STR00221## or C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O; or R.sub.2 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, O(CO)R.sub.1a or (CO)OR.sub.3; or R.sub.2 is C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl or C.sub.6-C.sub.20aryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, NO.sub.2, OR.sub.3, SR.sub.4, COOR.sub.3, (CO)R.sub.1a or ##STR00222## R.sub.2a is hydrogen, (CO)R.sub.1a, (CO)OR.sub.3a, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sub.3a, SR.sub.4a or C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O; R.sub.3 is hydrogen, (CO)R.sub.1a, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O; or R.sub.3 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH or (CO)OR.sub.3a; or R.sub.3 is C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl or C.sub.6-C.sub.20aryl, which C.sub.6-C.sub.20aryl is unsubstituted or substituted by one or more halogen or C.sub.1-C.sub.20alkyl; R.sub.3a is C.sub.1-C.sub.20alkyl; R.sub.4 is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more OR.sub.3a, (CO)OR.sub.3a, C.sub.3-C.sub.8cycloalkyl or C.sub.6-C.sub.20aryl; or R.sub.4 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more OH or (CO)OR.sub.3a; or R.sub.4 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl; or R.sub.4 is C.sub.6-C.sub.20aryl which is unsubstituted or substituted by one or more halogen or C.sub.2-C.sub.20alkyl which is uninterrupted or interrupted by one or more O; R.sub.4a is C.sub.1-C.sub.20alkyl; R.sub.5 and R.sub.6 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sub.3a, SR.sub.4a, (CO)OR.sub.3a, C.sub.3-C.sub.8cycloalkyl or C.sub.6-C.sub.20aryl; or R.sub.5 and R.sub.6 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by OH or SH; or R.sub.5 and R.sub.6 independently of each other are C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl or C.sub.6-C.sub.20aryl; or R.sub.5 and R.sub.6 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 NR.sub.5a; R.sub.5a and R.sub.6a independently of each other are hydrogen or C.sub.1-C.sub.20alkyl; R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a; or R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are C.sub.1-C.sub.20alkyl substituted by one or more halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, (CO)OR.sub.3, C.sub.6-C.sub.20aryl or C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O; or R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O; or R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a or ##STR00223## or R.sub.8 and R.sub.9, R.sub.9 and R.sub.10, or R.sub.10 and R.sub.11 are ##STR00224## R.sub.12, R.sub.13, R.sub.14 and R.sub.15 independently of each other are hydrogen or C.sub.1-C.sub.20alkyl; Ar.sub.1 is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl, C.sub.3-C.sub.20heteroarylcarbonyl or ##STR00225## which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl, C.sub.3-C.sub.20heteroarylcarbonyl or ##STR00226## is unsubstituted or substituted by one or more halogen, COOR.sub.3, (CO)R.sub.1a, ##STR00227## OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl or phenyl; or Ar.sub.1 is ##STR00228## Ar.sub.2 is phenylene, naphthylene, ##STR00229## which phenylene, naphthylene, ##STR00230## is unsubstituted or substituted by one or more halogen, COOR.sub.3, (CO)R.sub.1a, ##STR00231## OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl, phenyl or C.sub.2-C.sub.20alkyl which is interrupted by one or more O; M is C.sub.1-C.sub.20alkylene, C.sub.2-C.sub.20alkylene interrupted by one or more O or S, C.sub.2-C.sub.12alkenylene, C.sub.3-C.sub.20cycloalkylene or C.sub.6-C.sub.20arylene; Y is a direct bond, O, S, NR.sub.5 or CO; Z.sub.1 is O, S, CO or CR.sub.16(R.sub.17); Z.sub.2 is a direct bond, O, S or NR.sub.5; and Q is CO or a direct bond.

3. Compounds of the formula (I) or (II) according to claim 1, wherein X is ##STR00232## A is O, S or NR.sub.5; R.sub.1 is C.sub.1-C.sub.20alkyl, C.sub.6-C.sub.20aryl or C.sub.1-C.sub.20alkoxy; R.sub.1a is C.sub.1-C.sub.20alkyl or C.sub.6-C.sub.20aryl; R.sub.2 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by halogen, SR.sub.4, NR.sub.5R.sub.6, (CO)OR.sub.3 or C.sub.3-C.sub.8cycloalkyl; or R.sub.2 is C.sub.6-C.sub.20aryl which is unsubstituted or substituted by C.sub.1-C.sub.20alkyl; R.sub.3 is C.sub.1-C.sub.20alkyl or R.sub.3 together with one of the carbon atoms of R.sub.2 forms a 5- or 6-membered, preferably 6-membered, saturated ring; R.sub.4 is C.sub.6-C.sub.20aryl; R.sub.5 and R.sub.6 independently of each other are O(CO)R.sub.1a, (CO)R.sub.1a or C.sub.1-C.sub.20alkyl; R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, halogen, NO.sub.2, OR.sub.3, (CO)R.sub.1a or C.sub.6-C.sub.20aryl; or R.sub.8 and R.sub.9 are ##STR00233## R.sub.12, R.sub.13, R.sub.14 and R.sub.15 are hydrogen or C.sub.1-C.sub.4alkyl, preferably hydrogen; R.sub.16 and R.sub.17 are hydrogen; or R.sub.16 and R.sub.17 together with the carbon atom to which they are attached form a 5- or 6-membered saturated ring; Ar.sub.1 is C.sub.6-C.sub.20aryl or ##STR00234## Ar.sub.2 is ##STR00235## M is C.sub.2-C.sub.20alkylene interrupted by S; Y is a direct bond; Z.sub.1 is O, S or CR.sub.16(R.sub.17); and Z.sub.2 is O or S.

4. A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable compound and (b) as photoinitiator, at least one compound of the formula I or II as defined in claim 1.

5. A photopolymerizable composition according to claim 4, wherein the component (a) is a resin obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of an epoxy resin and an unsaturated monocarboxylic acid.

6. A photopolymerizable composition according to claim 4, further comprising at least one photoinitiator (c) and other additives (d).

7. A photopolymerizable composition according to claim 6 wherein the additive (d) is selected from a pigment, or a mixture of pigments, or a dye, or a mixture of dyes, or a mixture of one or more pigments with one or more dyes.

8. A photopolymerizable composition according to claim 6 wherein the additive (d) is a dispersant or a mixture of dispersants.

9. A photopolymerizable composition according to claim 4, comprising 0.05 to 25% by weight of the photoinitiator (b), based on the composition.

10. A photopolymerizable composition according to claim 4, further comprising a photosensitizer selected from the group consisting of benzophenone, benzophenone derivatives, thioxanthone, thioxanthone derivatives, anthraquinone, anthraquinone derivatives, coumarin and coumarine derivatives.

11. A photopolymerizable composition according to claim 6, further comprising a binder polymer (e).

12. A process for the preparation of a compound of the formula I or II as defined in claim 1 by reacting the corresponding oxime compound of the formula (1A) or (IIA) ##STR00236## wherein X, Ar.sub.1, M and R.sub.2 are as defined in claim 1, with an acyl halide of the formula III or an anhydride of the formula IV ##STR00237## wherein Hal is a halogen, in particular Cl, and R.sub.14 is as defined in claim 20, in the presence of a base or a mixture of bases.

13. A process for the photopolymerization of compounds containing ethylenically unsaturated double bonds, the process comprising irradiating a composition according to claim 4 with electromagnetic radiation in the range from 150 to 600 nm, or with an electron beam or with X-rays.

14. A process according to claim 13 for producing pigmented and non-pigmented paints, varnishes, powder coatings, printing inks, printing plates, adhesives, dental compositions, gel coats, photoresists for electronics, for encapsulating electrical and electronic components, for producing magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etch masks, colour proofing systems, glass fibre cable coatings, screen printing stencils, for producing three-dimensional objects, image recording materials, microelectronic circuits, decolorizing materials, bank/pixel definition layers for OLED, sealants for LCD and OLED, insulation/passivation layers for LCD and OLED, insulation for metal wiring/transparent conductive films for touch panel, coatings for touch panel, decorative inks for touch panel, protective films for touch panel or etching resists for touch panel.

15. A substrate coated on at least one surface with a composition according to claim 4.

16. A process for the photographic production of relief images comprising providing the coated substrate according to claim 15, subjecting the substrate to imagewise exposure, and removing unexposed portions with a developer.

17. A color filter comprising red, green and blue picture elements and optionally a black matrix, each of the elements including a photosensitive resin and a pigment on a transparent substrate, and a transparent electrode either on the surface of the substrate or on the surface of the picture elements, wherein said photosensitive resin comprises a polyfunctional acrylate monomer, an organic polymer binder and a photopolymerization initiator of formula I or II as defined in claim 1.

18.-19. (canceled)

20. Compounds of formula (IA) or (IIA) ##STR00238## wherein X is ##STR00239## R.sub.2 is C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00240## C.sub.3-C.sub.8cycloalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.2 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted, or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; R.sub.2 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; R.sub.2 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a(CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00241## C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5R.sub.6, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted, or substituted by one or more OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; or R.sub.2 is R.sub.2a, and R.sub.2a is selected from hydrogen, CN, (CO)R.sub.1a, (CO)OR.sub.3a, CONR.sub.5aR.sub.6a, NO.sub.2, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.2a is C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, CN, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2 or S(O).sub.mR.sub.1a; R.sub.2a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sub.5a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted, or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3a, (CO)NR.sub.5aR.sub.6a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; R.sub.2a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted, or interrupted by one or more O, S, CO, NR.sub.5a or COOR.sub.3a; or R.sub.2a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sub.3a, SR.sub.4a, NR.sub.5aR.sub.6a, COOR.sub.3a, (CO)R.sub.1a(CO)NR.sub.5aR.sub.6a, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, C.sub.1-C.sub.20alkyl which is unsubstituted, or substituted by one or more halogen, COOR.sub.3a, CONR.sub.5aR.sub.6a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5a, phenyl, naphthyl, benzoyl and naphthoyl, each of which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted, or substituted by one or more OR.sub.3a, SR.sub.4a or NR.sub.5aR.sub.6a; Ar.sub.1 is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl, C.sub.3-C.sub.20heteroarylcarbonyl or ##STR00242## which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl, C.sub.3-C.sub.20heteroarylcarbonyl or ##STR00243## is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, COOR.sub.3, (CO)R.sub.1a, (CO)NR.sub.5R.sub.6, PO(OR.sub.1a).sub.2, S(O).sub.mR.sub.1a, ##STR00244## OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, wherein the substituents OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6 optionally form 5- or 6-membered rings via the radicals R.sub.3, R.sub.4, R.sub.5 or R.sub.6 with further substituents on the phenyl ring, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sub.3, CONR.sub.5R.sub.6, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sub.5, C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; or Ar.sub.1 is ##STR00245## and M is C.sub.1-C.sub.20alkylene which is unsubstituted, or substituted by one or more substituents selected from the group consisting of halogen, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, CN, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.3-C.sub.8cycloalkyl which is uninterrupted, or interrupted by one or more O, S, CO or NR.sub.5, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR3, SR4 or NR5R6; M is C.sub.2-C.sub.20alkylene interrupted by one or more O, S, NR.sub.5, CO, SO or SO.sub.2, which C.sub.1-C.sub.20alkylene or C.sub.2-C.sub.20alkylene is unsubstituted or substituted by one or more substituents selected from the group consisting of C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sub.1a, (CO)OR.sub.3, (CO)NR.sub.5R.sub.6, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sub.3, SR.sub.4 or NR.sub.5R.sub.6; M is C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene, which C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene is uninterrupted, or interrupted by one or more O, S, CO, NR.sub.5 or COOR.sub.3; or M is C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene, which C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene is unsubstituted, or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sub.3, SR.sub.4, NR.sub.5R.sub.6, COOR.sub.3, (CO)R.sub.1a or SO.sub.2R.sub.1a.

21. The photopolymerizable composition according to claim 11, wherein the binder is a-copolymer of methacrylate and methacrylic acid.

Description

SYNTHESIS EXAMPLES

Example 1

Preparation of OE-1

[0629] ##STR00105##

[0630] 1.1: Preparation of IM-1:

##STR00106##

[0631] To 7.36 g of aluminum chloride in dichloromethan (50 mL) are added 9.31 g of diphenyl sulfide in portions at 0 C. Then, 5.56 g of chloroacetyl cholide is added at 0 C. and stirred for 2 hours at room temperature. To the reaction mixture, 7.33 g of aluminum chloride and 5.59 g of n-butyryl chloride are added to the mixture at 0 C., and then the mixture is stirred overnight. After the reaction mixture is poured onto ice water, the organic layer is extracted with dichloromethane. The solution is dried over MgSO.sub.4, concentrated, and the residue is purified by column chromatography, giving 10.35 g of IM1 as white powder.

[0632] 1.2: Preparation of IM-2

##STR00107##

[0633] To 1.0 g of the diketone (IM-1) in 30 ml of acetone, 1.11 g of potassium carbonate and 0.73 g of salicylaldehyde are added and stirred under reflux for 3 hours. The reaction miture is allowed to warm to room temperature, water is added and acidified by adding aq. HCl. The precipitate is collected by filtration and dried to give 1.0 g of IM-2.

[0634] 1.3: Preparation of IM-3

##STR00108##

[0635] To 1.0 g of IM-2 in CH.sub.3(CO)OC.sub.2H.sub.5 (AcOEt) (10 ml), 0.35 g of hydroxyl ammonium chloride and 5 ml of pyridine are added. The mixture is stirred under reflux for 3 hours. The reaction mixture is allowed to warm to room temperature and then is poured into water. The organic layer is extracted with AcOEt and dried over MgSO.sub.4. After concentration, the crude product is purified by column chromatography, giving 283 mg of IM-3 as pale yellow solid.

[0636] 1.4: Preparation of OE-1

[0637] To 283 mg of IM-3 in AcOEt (14 ml), 78.5 mg of acetyl chloride and 111 mg of triethyl amine are added and stirred for 3 hours at room temperature. The reaction mixture is poured into water and extracted with AcOEt. After concentration, the crude product is purified by column chromatography, giving 226 mg of OE-1 as pale yellow solid.

Example 2

Preparation of OE-2

[0638] OE-2 is prepared according to the method as described in example 1 except using the corresponding acid chloride. The structure and physical data are collected in the following table 1.

Example 3

Preparation of OE-3

[0639] OS-3 is prepared according to the method as described in example 1 except using the corresponding acid chloride and 2-hydroxy-1-naphthaldehyde instead of salicylaldehyde. The structure and physical data are collected in the following table 1.

Example 4

Preparation of OE-4

[0640] OE-4 is prepared according to the method as described in example 1 except using diphenylether instead of diphenylsulfide. The structure and physical data are collected in the following table 1.

Example 5

Preparation of OE-5

[0641] ##STR00109##

[0642] 5.1: Preparation of IM-4

##STR00110##

[0643] To 2.95 g of aluminum chloride in dichloromethan (20 mL) are added 5.59 g of diphenyl sulfide in portions at 0 C. Then, 3.42 g of 2-methoxybenzoyl choride is added at 0 C. and stirred for 2 hours at room temperature. After the reaction mixture is poured onto ice water, the organic layer is extracted with dichloromethane. The solution is dried over MgSO.sub.4, concentrated, and the residue is purified by column chromatography, giving 2.80 g of IM-4 as yellow solid.

[0644] 5.2: Preparation of IM-6

##STR00111##

[0645] To 1.00 g of diketone (IM-4) in 13 ml of acetone, 0.46 g of potassium carbonate and 0.46 g of 2-chloroacetophenone are added, and stirred under reflux overnight. After the reaction mixture is allowed to warm to room temperature, water is added, extracted by ethyl acetate and dried over Mg.sub.2SO.sub.4. The organic layer is evaporated, giving 1.0 g of IM-5. IM-5 is converted to IM-6 by means of Friedel-Crafts acetylation.

[0646] 5.3: Preparation of OE-5

[0647] IM-6 is converted to OE-5 according to the method as described in example 1.4. The corresponding physical data are collected in the following table 1.

Examples 6-11

Preparation of OE6-OE11

[0648] The compounds OE6-OE11 are prepared according to the method as described in example 1. The structures and physical data are collected in table 1.

Examples 12-31, 33-73

Preparation of OE12-OE31 and OE33-OE73

[0649] The oxime ester compounds OE12-OE31 and OE33-OE73 are prepared according to the method as described in example 1 using the corresponding ketone for oximation followed by a esterification.

Exampie 32

Preparation of OE32

[0650] The compound OE32 is prepared according to the method as described in example 1 via diketone (IM-7) and oxime (IM-8). The crude product is purified by recrystallization from CH.sub.3COOC.sub.2H.sub.5 (AcOEt)/hexane, giving OE32 as a mixture of EZ (93:7) isomers.

##STR00112## ##STR00113##

[0651] .sup.1H-NMR data

[0652] IM-7(CDCl.sub.3):0.88-0.98(d, 2H), 1.50-1.75(m, 3H), 2.80-2.88(t, 2H), 7.28-8.06 (m, 13H),

[0653] IM-8(DMSO-d6):0.78-0.92(m, 6H), 1.20-1.60(m,3H), 2.42-2.76(m, 2H), 7.34-8.02 (m, 13H),10.68-11.30(two singlet, 1H)

Example 74-75

[0654] A mixture of oxime EZ isomers (IM-8) is purified by colomun chromatography, giving a single component of oxime isomer E(IM-9) and Z(IM-10). OE74 and OE75 are prepared via conventional esterification manner from IM-9 and IM-10, respectively:

##STR00114##

[0655] .sup.1H-NMR data

[0656] IM-9:(DMSO-d6) 0.84-0.92(m, 6H), 1.30-1.60(m,3H), 2.64-2.76(m, 2H), 7.34-7.98 (m, 13H),11.30(s, 1H)

[0657] IM-10:(DMSO-d6) 0.78-0.84(m, 6H), 1.20-1.38(m,3H), 2.42-2.54(m, 2H), 7.34-8.02 (m, 13H), 10.68(s, 1H)

[0658] The oxime ester compounds (OE) are formed in E/Z isomeric mixtures. Only in single cases a differentiation and separation of said forms is indicated.

TABLE-US-00001 TABLE 1 Oxime Ester Structure .sup.1H NMR in CDCl.sub.3 OE-1 [00115] 0.96-1.02(t, 3H), 1.54- 1.66( m, 2H), 2.50(s, 3H), 2.78-2.86(t, 2H), 7.28-7.32 (d, 1H), 7.32-7.36(d, 2H), 7.46-7.50(d, 2H), 7.52(s, 1H), 7.68-7.74(m, 3H), 7.95- 7.99(d, 2H) OE-2 [00116] 0.84-0.90( t, 3H), 1.22- 1.42(m, 8H), 1.54-1.60(m, 2H), 2.71 (s, 3H), 2.82-2.87(t, 2H), 7.31-7.40 (m, 3H), 7.48- 7.56(m, 4H), 7.62-7.66(d, 1H) 7.72-7.76(d, 3H), 7.98- 7.82(d, 2H) OE-3 [00117] 2.29 (s, 3H), 2.42 (s, 3H), 7.38-7.42(d, 2H), 7.52-7.56 (d, 2H), 7.55-7.77(m, 3H), 7.76-7.80(d, 2H), 7.92-7.95(d, 1H), 7.97-7.80(d, 1H), 8.04(s, 1H), 8.03-.07(d, 2H), 8.19- 8.22(d, 1H) OE-4 [00118] 2.29 (s, 3H), 2.42 (s, 3H), 7.13-7.19 (m, 4H), 7.55-7.60 (t, 1H), 7.65-7.70(t, 1H), 7.74- 7.78(d, 1H), 7.80-7.85(d, 2H), 7.92-7.96(d, 1H), 7.97- 7.81(d, 1H) 8.07(s, 1H), 8.16- 8.23( m, 3H). OE-5 [00119] 2.28 (s, 3H), 2.39 (s, 3H), 7.31-7.42 (m, 7H), 7.46-7.50 (d, 2H), 7.52-7.58(m, 2H), 7.64-7.72(m, 4H), 7.87- 7.91(d, 2H) OE6 [00120] 0.96-1.06(t, 3H), 1.60- 1.68(m, 2H), 2.28(s, 3H), 2.80-2.88(t, 2H), 7.36- 7.52(m, 6H), 7.72-7.76(d, 2H), 7.84-7.94(m, 5H) OE7 [00121] 0.96-1.06(t, 3H), 1.60- 1.68(m, 2H), 2.28(s, 3H), 2.80-2.88(t, 2H), 7.36- 7.52(m, 6H), 7.72-7.76(d, 2H), 7.84-7.94(m, 5H) OE8 [00122] 1.22-1.27(t, 3H), 2.3(s, 3H), 2.56-2.62(t, 2H), 3.14-3.20(t, 2H), 4.10-4.18(q, 2H), 7.32- 7.4(m, 3H), 7.48-7.53(m, 3H), 7.56(s, 1H), 7.62-7.66(d, 1H), 7.72-7.76(m, 3H), 7.99- 8.20(d, 2H) OE9 [00123] 0.82-0.92(t, 3H), 1.20- 1.44(m, 8H), 1.52-1.62(m, 2H), 2.66(s, 3H), 2.80-2.90(t, 2H), 4.03(s, 3H), 6.94-6.98(d, 1H), 7.21-7.31(m, 2H), 7.34- 7.39(d, 2H), 7.48-7.52(d, 2H), 7.56(s, 1H), 7.70-7.74(d, 2H), 7.82-7.86(d, 2H) OE10 [00124] 0.98-1.06(t, 3H), 1.25-1.30(t, 3H), 1.58-1.68(m, 2H), 2.53- 2.59(q, 2H), 2.82-2.86( t, 2H), 7.32-7.40(m, 3H), 7.49- 7.56(m, 3H), 7.55(s, 1H), 7.63-7.66(d, 1H), 7.72- 7.76(m, 3H), 7.98-8.02(d, 2H) OE11 [00125] 1.04-1.08(t, 3H), 1.70- 1.98(m, 2H), 2.94-3.02(q, 2H), 7.31-7.37(t, 1H), 7.37- 7.41(d, 2H), 7.48-7.56(m, 6H), 760-7.66(t, 2H), 7.72- 7.75(t, 1H), 7.81-7.85(d, 2H), 7.99-7.82(d, 2H), 8.10-8.14(d, 2H) OE12 [00126] 0.86-0.92( t, 3H), 1.22- 1.62(m, 12H), 2.27 (s, 3H), 2.82-2.87(t, 2H), 3.12-3.20 (q, 2H), 7.31-8.10(m, 12H) OE13 [00127] 0.82-0.94( t, 3H), 1.20- 1.42(m, 8H), 1.50-1.60(m, 2H), 2.27 (s, 3H), 2.80-2.90(t, 2H), 7.18-7.82 (m, 17H) OE14 [00128] 0.88(t, 9H), 0.84-0.94( d, 3H), 1.08-1.36(m, 2H), 1.82- 1.96(m, 1H), 2.27 (s, 3H), 270-2.92(m, 2H), 7.32-806 (m, 13H) OE15 [00129] 0.98-1.04(t, 3H), 1.58- 1.68(m, 2H), 2.278s, 3H), 2.80-2.89(t, 2H), 4.4(s, 3H), 6.95-8.08m, 12H) OE16 [00130] 2.27(s, 3H) 7.19-8.22(m, 17H) OE17 [00131] 2.28(s, 3H), 2.41(s, 3H), 4.04(s, 3H), 7.75-8.08(m, 12H) OE18 [00132] 2.12(s, 3H), 2.28(s, 3H), 7.19- 8.22(m, 17H) OE19 [00133] 2.30(s, 3H), 2.48(s, 3H), 4.07(s, 2H), 7.33-8.29(m, 11H) OE20 [00134] 0.82(t, 9H), 0.90-0.99( m, 4H), 1.10-1.35(m, 2H), 2.08 (s 3H), 2.52-2.88(m, 2H), 7.32- 8.06 (m, 13H) OE21 [00135] 1.05-1.20(t, 2H), 1.50- 1.70(m, 6H), 1.75- 1.86(m, 3H), 2.27(s, 3H) 2.80- 2.89( t, 2H), 7.32-8.02m, 13H) OE22 [00136] 0.84-0.92(t, 3H), 1.20- 1.44(m, 8H), 1.50- 1.60(m, 2H), 2.27(s, 3H), 2.66(s, 3H), 2.80-2.90(t, 2H), 7.30-8.10(m, 12H) OE23 [00137] 0.82-0.92(t, 3H), 1.22- 1.40(m, 8H), 1.52- 1.62(m, 2H), 2.27(s, 3H), 2.49(s, 3H), 2.63(s, 3H), 2.80-2.90(t, 2H), 7.28- 8.06(m, 11H) OE24 [00138] 0.92-0.98(t, 3H), 1.35- 1.46(m, 2H), 1.52- 1.60(m, 2H) 2.27(s, 3H), 2.65(s, 3H), 2.80-2.88(t, 2H), 7.32-8.06(m, 12H) OE25 [00139] 0.92-0.98(t, 3H), 1.36- 1.46(m, 2H), 1.52- 1.60(m, 2H), 2.27(s, 3H), 2.49(s, 3H), 2.63(s, 3H), 2.82- 7.28-8.06(m, 11H) OE26 [00140] 2.28(s, 3H), 2.41(s, 3H), 2.66(s, 3H), 2.80-2.90(t, 2H), 7.32-8.06(m, 12H) OE27 [00141] 0.96-1.04(t, 3H), 1.48- 1.56(, 2H), 1.78-1.86(m, 2H), 2.28(s, 3H), 2.41(s, 3H), 4.00- 4.06(t, 2H), 6.94-7.98(m, 12H) OE28 [00142] 1.18-1.24(t, 3H), 2.28(s, 3H), 2.49(s, 3H), 2.63(s, 3H), 2.82- 2.90(t, 2H), 7.38-8.04(m, 11H) OE29 [00143] 0.92-0.98( d, 6H), 1.26-1.32 (d, 6H), 1.42-1.50(m, 2H), 1.60-1.70 (m, 1H), 2.27 (s, 3H), 2.80-2.88(m, 2H), 2.98- 3.08(m, 1H), 7.36-8.01 (m, 12H) OE30 [00144] 2.28(s, 3H), 2.41(s, 3H), 2.64(s, 3H), 7.08-8.04(m, 11H) OE31 [00145] 0.84-0.92(t, 3H), 1.22- 1.40(m, 8H), 1.52- 1.62(m, 2H), 2.27(s, 3H), 2.80-2.88(t, 2H), 7.20- 8.02(m, 12H) OE32 [00146] 0.82-0.98( d, 6H), 1.36-- 1.70(m, 3H), 2.05-2.27 (m, 3H), 2.66-2.86(m, 2H), 7.31- 8.06 (m, 13H), OE33 [00147] 0.82-0.90(t, 3H), 1.20- 1.40(m, 12H), 1.50- 1.60(m, 2H), 2.27(s, 3H), 2.80-2.90(t, 2H), 7.31- 8.02(m, 13H) OE34 [00148] 2.28(s, 3H), 2.41(s, 3H), 7.20- 8.01(m, 14H) OE35 [00149] 1.39(s, 9H), 1.55(s, 9H), 2.28(s, 3H), 2.41(s, 3H), 2.64(s, 3H), 7.36-8.06(m, 11H) OE36 [00150] 0.84-0.98(m, 2H), 1.08- 1.38(m, 4H), 1.40-1.50(m, 2H), 1.60-1.78(m, 5H), 2.27 (s, 3H), 2.80-2.88(m, 2H), 7.31-8.01 (m, 13H) OE37 [00151] 0.82-0.92(t, 3H), 1.18- 1.38(m, 16H), 1.50- 1.60(m, 2H), 2.27(s, 3H), 2.80-2.90(t, 2H), 7.31- 8.02(m, 13H) OE38 [00152] 0.84-0.98( m, 2H), 1.08- 1.38(m, 4H), 1.40-1.50(m, 2H), 1.60-1.78(m, 5H), 2.27 (s, 3H), 2.80-2.88(m, 2H), 7.20-7.81 (m, 12H) OE39 [00153] 0.94-0.98( d, 6H), 1.40- 1.50(m. 2H), 1.60-1.70(m, 1H), 2.27 (s, 3H), 2.80- 2.88(m, 2H), 7.21-8.02 (m, 12H), OE40 [00154] 0.84-0.98( m, 2H), 1.08- 1.38(m, 4H), 1.40-1.50(m, 2H), 1.4(s, 9H), 1.60-1.78(m, 5H), 2.27(s, 3H), 2.80- 2.88(m, 2H), 7.31-8.00 (m, 12H) OE41 [00155] 0.94-0.98( d, 6H), 1.39(s, 9H), 1.40-1.50(m, 2H), 1.60-1.70(m, 1H), 2.27 (s, 3H), 2.80-2.88(m, 2H), 7.32- 8.01 (m, 12H) OE42 [00156] 0.64-0.74(t, 3H), 1.35(s, 6H), 1.66-1.74(q, 2H), 2.28(s, 3H), 2.41(s, 3H), 7.35-8.02(m, 12H) OE43 [00157] 0.64-0.74(t, 3H), 1.08- 1.20(m, 2H), 1.34(s, 6H), 1.50- 1.88(m, 11H), 2.27(s, 3H), 2.80-2.90(t, 2H), 7.36- 8.02(m, 12H) OE44 [00158] 0.94-0.98( d, 6H), 1.39(s, 9H), 1.40-1.50(m, 2H), 1.54(s, 9H), 1.60-1.70(m, 1H), 2.27 (s, 3H), 2.80-2.88(m, 2H), 7.32-8.01 (m, 11H) OE45 [00159] 0.94-0.98( d, 6H), 1.40- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.27 (s, 3H), 2.66(s, 3H), 2.80-2.88(m, 2H), 7.31-8.06 (m, 12H) OE46 [00160] 1.28-1.36(d, 6H), 2.27(s, 3H), 2.41(s, 3H), 2.98- 3.08(m, 1H), 7.34-8.00(m, 12H) OE47 [00161] 1.05-1.20(t, 2H), 1.50- 1.70(m, 6H), 1.75- 1.86(m, 3H), 2.27(s, 3H), 2.49(s, 3H), 2.80-2.89( t, 2H), 7.32-8.10m, 12H) OE48 [00162] 0.84-0.98( m, 2H), 1.08- 1.38(m, 4H), 1.40-1.50(m, 2H), 1.60-1.78(m, 5H), 2.27 (s, 3H), 2.48(s, 3H), 2.80- 2.88(m, 2H), 7.34-8.05 (m, 12H) OE49 [00163] 0.94-0.98( d, 6H), 1.40- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.27 (s, 3H), 2.48(s, 3H), 2.80-2.88(m, 2H), 7.34-8.05 (m, 12H) OE50 [00164] 2.27(s, 3H), 2.41(s, 3H), 2.50(s, 3H), 2.51(s, 3H), 7.30- 8.02(m, 11H) OE51 [00165] 0.73(s, 9H), 1.05-1.20(t, 2H), 1.45(s, 6H), 1.75-1.86(m, 3H) 1.50-1.70(m, 6H), ,2.27(s, 3H) 2.80-2.89( t, 2H), 7.32- 8.10m, 12H) OE52 [00166] 0.73(s, 9H), 1.45(s, 6H), 1.82(s, 2H), 2.30(s, 3H) 2.43 (s, 3H), 7.40-8.06(m, 12H) OE53 [00167] 0.94-0.98( d, 6H), 1.40- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.29 (s, 3H), 2.63(s, 3H), 2.80-2.88(m, 2H), 7.25-8.08 (m, 12H) OE54 [00168] 0.84-0.98(m, 2H), 1.08- 1.38(m, 4H), 1.40-1.50(m, 2H), 1.60-1.78(m, 5H), 2.29 (s, 3H), 2.63(s, 3H), 2.80- 2.88(m, 2H), 7.25-8.08 (m, 12H) OE55 [00169] 1.05-1.20(t, 2H), 1.50- 1.70(m, 6H), 1.75- 1.86(m, 3H), 2.27(s, 3H), 2.66(s, 3H), 2.80-2.89( t, 2H), 7.32-8.08m, 12H) OE56 [00170] 1.16-1.22(d, 3H), 1.90(s, 3H), 2.28(s, 3H), 2.30(s, 3H), 3.07-3.30(m, 2H), 4.80- 4.95(m, 1H), 7.32-8.04(m, 13H) OE57 [00171] 2.02-2.16(m, 2H), 2.27(s, 3H), 3.30-3.06(m, 2H), 3.58- 3.64(t, 2H), 7.32-8.04(m, 13H) OE58 [00172] 0.94-0.98( d, 6H), 1.40- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.27(s, 3H), 2.80- 2.88(m, 2H), 4.10(s, 3H), 7.15-7.88 (m, 13H) OE59 [00173] 0.82-1.80(m, 17H), 2.26 (s, 3H). 2.78-2.86(t, 2H), 3.40- 3.50(q, 4H), 6.75-7.96 (m, 12H) OE60 [00174] 0.84-0.98( m, 2H), 1.08- 1.38(m, 4H), 1.40-1.50(m, 2H), 1.60-1.78(m, 5H), 2.27 (s, 3H), 2.80-2.88(m, 2H), 7.34-8.70 (m, 12H) OE61 [00175] 0.94-0.98( d, 6H), 1.40- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.29 (s, 3H), 2.90-3.00(t, 2H), 7.24-8.78(m, 11H) OE62 [00176] 0.94-0.98( d, 6H), 1.40- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.29 (s, 3H), 2.90-3.00(t, 2H), 7.32-8.92 (m, 11H) OE63 [00177] 0.82-0.92(t, 3H), 1.18-1.43(t, 3H), 1.50-1.62(m, 2H), 2.82- 2.90(t, 2H), 4.33-4.40(q, 2H), 7.32-8.04 (m, 13H) OE64 [00178] 2.01(s, 3H), 4.16(s, 2H), 7.28-8.04(m, 18H) OE65 [00179] 2.27(s, 3H), 3.05-3.10(t, 2H), 4.30-4.35(t, 2H), 6.98-8.35 (m, 12H) OE66 [00180] 2.27(s, 3H), 3.05-3.10(t, 2H), 4.30-4.35(t, 2H), 6.98-8.35 (m, 12H) OE67 [00181] 0.94-0.98( d, 6H), 1.40- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.27(s, 3H), 2.80- 2.88(m, 2H), 3.87(s, 3H), 7.34-8.44 (m, 13H) OE68 [00182] 1.82-1.98(m, 4H), 2.28(s, 6H), 2.64-2.74(t, 4H), 2.92- 3.00(t, 4H), 7.30-8.04 (m, 26H OE69 [00183] 0.85-1.02(m, 6H), 1.36- 1.72(m, 3H), 2.06-2.18(m, 8H), 2.29(s, 3H), 2.70-2.92(m, 2H), 7.28-8.40(m, 11H) OE70 [00184] 0.85-1.02(m, 6H), 1.36- 1.42(m, 3H) 2.29(s, 3H), 2.70-2.92(m, 2H), 4.08(s, 2H), 7.28-8.30(m, 11H OE71 [00185] 0.85-1.20(m, 2H), 1.50- 1.70(m, 6H), 1.75- 1.86(m, 3H), 2.29(s, 3H), 2.70-2.92(m, 2H), 4.08(s, 2H), 7.28-8.30(m, 11H) OE72 [00186] 0.85-0.98(m, 2H), 1.08- 1.38(m, 4H), 1.40-1.50(m, 2H), 1.60-1.78(m, 5H), 2.27(s, 3H), 2.80-2.88(m, 2H), 4.08(s, 2H), 7.28-8.30(m, 11H) OE73 [00187] 0.85-1.02(m, 6H), 1.36- 1.42(m, 3H), 2.29(s, 3H), 2.70-2.92(m, 2H), 4.08(s, 2H), 7.28-8.22 (m, 13H) OE74 [00188] 0.92-0.98( d, 6H), 1.42- 1.50(m, 2H), 1.60-1.70(m, 1H), 2.27 (s, 3H), 2.80- 2.88(m, 2H), 7.31-8.02 (m, 13H) OE75 [00189] 0.82-0.86(d, 6H), 1.32- 1.50(m, 3H), 2.05(s, 3H), 2.66-2.72(t, 2H), 7.31- 8.06(m, 13H)

APPLICATION EXAMPLES

[0659] Preparation of Poly(benzylmethacrylate-co-methacrylic acid)

[0660] 24 g of benzylmethacrylate, 6 g of methacrylic acid and 0.525 g of azobisisobutyronitrile (AIBN) are dissolved in 90 ml of propylene glycol 1-monomethyl ether 2-acetate (PGMEA). The resulting reaction mixture is placed in a preheated oil bath at 80 C. After stirring for 5 hours at 80 C. under nitrogen, the resulting viscous solution is cooled to room temperature and used without further purification. The solid content is about 25%.

[0661] Sensitivity Test A

[0662] A photocurable composition for a sensitivity test is prepared by mixing the following components:

TABLE-US-00002 100.0 parts by weight of copolymer of benzylmethacrylate and methacrylic acid (benzylmethacrylate: methacrylic acid = 80:20 by weight) 25% propylene glycol 1-monomethyl ether 2-acetate (PGMEA) solution, prepared in above example 25.0 parts by weight of dipentaerythritol hexaacrylate ((DPHA), provided by SIGMA-ALDRICH), 1.0 parts by weight of the photoinitiator (PI), and 75.0 parts by weight of PGMEA

[0663] All operations are carried out under yellow light. The compositions are applied to an aluminum plate using an electric applicator with a wire wound bar. The solvent is removed by heating at 80 C. for 10 minutes in a convection oven. The thickness of the dry film is approximately 2 m. A standardized test negative film with 21 steps of different optical density (Stouffer step wedge) is placed with an air gap of around 300 m between the film and the resist. A glass plate is placed over the negative film to fix the masks with 21 steps. Exposure is carried out using a 250 W super high pressure mercury lamp (USHIO, USH-250BY) at a distance of 20 cm. A total exposure dose measured by an optical power meter (USHIO, UNIMETER UIT-150-A with UVD-S365 detector) on the glass plate is 250 mJ/cm.sup.2. After exposure, the exposed film is developed with an alkaline solution (5% aqueous solution of DL-A4, Yokohama Yushi) for 120 sec. at 28 C. by using a spray type developer (AD-1200, Takizawa Sangyo). The sensitivity of the initiator used is characterized by indicating the highest number of the step remained (i.e. polymerized) after developing. The higher the number of steps, the more sensitive is the initiator tested. The results are listed in table 2.

TABLE-US-00003 TABLE 2 Photo sensitivity Example No. PI No. of steps A1 OE-1 17 A2 OE-2 17 A3 OE-3 17 A5 OE-5 14 A6 OE-6 16 A7 OE-7 16 A8 OE-8 16 A9 OE9 16 A10 OE10 15 A11 OE12 16 A12 OE13 15 A13 OE14 16 A14 OE15 16 A15 OE16 13 A16 OE17 16 A17 OE18 15 A18 OE19 18 A19 OE20 16 A20 OE21 17 Comparative OE-R1 12 example 1

[0664] OE-R1 is

##STR00190##

as disclosed in WO04/050653, Example 6.

[0665] As shown in table 2, the compounds according to the invention show higher photosensitivity than the comparative compound.

[0666] Sensitivity Test B

[0667] A photocurable composition for a sensitivity test is prepared by mixing the following components:

TABLE-US-00004 88.6 parts by weight solvent (PGMEA) 86.1 parts by weight alkaline developable binder, 29.0% solution (Ripoxy SPC-1000, provided by Showa Highpolymer) 25.3 parts by weight multifunctional acrylate (DPHA, provided by SIGMA-ALDRICH) 1.0 parts by weight photoinitiator (PI)

[0668] All operations are carried out under yellow light. The compositions are applied to a silicon wafer using a spincoater. The solvent is removed by heating at 80 C. for 10 minutes in a convection oven. The thickness of the dry film is approximately 2 m. A standardized test negative film with 30 steps of different optical density (FUJIFILM imaging Systems, Gray step chart) is placed with an air gap of around 300 m between the film and the resist. A silicon wafer is placed over the negative film to fix the masks with 30 steps. Exposure is carried out using a 250 W super high pressure mercury lamp (USHIO, USH-250BY) at a distance of 20 cm. A total exposure dose measured by an optical power meter (USHIO, UNIMETER UIT-150-A with UVD-S365 detector) on the silicon wafer is 150 mJ/cm.sup.2. After exposure, the exposed film is developed with an alkaline solution (5% aqueous solution of DL-A4, Yokohama Yushi) for 60 sec. at 28 C. by using a spray type developer (AD-1200, Takizawa Sangyo). The necessary UV dose is corresponded to UV dose of full curing (i.e. the pattern is not dissolved with the alkaline solution) after developing. The smaller the value of the dose, the more sensitive is the tested initiator. The results are listed in table 3.

TABLE-US-00005 TABLE 3 Necessary UV dose for full cure Example No. PI [mJ/cm.sup.2] B1 OE2 15.3 B2 OE3 17.6 B3 OE12 17.6 B4 OE13 24.3 B5 OE14 12.8 B6 OE15 15.4 B7 OE18 15.4 B8 OE19 9.0 B9 OE21 10.6 B10 OE22 20.7 B11 OE23 20.7 B12 OE24 15.4 B13 OE25 12.8 B14 OE26 12.8 B15 OE27 10.6 B16 OE29 7.5 B17 OE30 12.8 B18 OE31 15.4 B19 OE32 9.0 B20 OE33 15.4 B21 OE34 15.4 B22 OE35 10.6 B23 OE36 9.0 B24 OE37 15.4 B25 OE38 12.8 B26 OE39 12.8 B27 OE40 10.6 B28 OE41 10.6 B29 OE42 12.8 B30 OE43 10.6 B31 OE44 10.6 B32 OE45 9.0 B33 OE46 17.6 B34 OE47 7.5 B35 OE48 10.6 B36 OE49 7.5 B37 OE50 17.6 B38 OE51 10.6 B39 OE52 20.7 B40 OE53 7.5 B41 OE54 9.0 B42 OE55 10.6 B43 OE57 17.6 B44 OE58 15.4 B45 OE60 10.6 B46 OE62 15.4 B47 OE65 9.0 B48 OE66 12.8 B49 OE67 20.7 B50 OE68 29.3 B51 OE69 7.5 B52 OE70 7.5 Comparative OE-R1 55.7 example 2

[0669] OE-R1 is Example 6 as disclosed in WO04/050653.

[0670] As shown in table 3, the compounds according to the invention show higher photosensitivity than the comparative compound.