US2019171099A1PendingUtilityA1
Polymerizable composition comprising an oxime sulfonate as thermal curing agent
Est. expiryJan 28, 2031(~4.5 yrs left)· nominal 20-yr term from priority
C07D 295/04C07D 213/78C07C 309/73C07C 309/67C07D 213/59C07D 291/02C07D 277/54C07D 265/32C07C 327/58C07C 309/30C07D 327/06C08F 220/10C07C 2602/42C07C 2601/14G03F 7/322G03F 7/031G03F 7/029G02B 5/201C07D 309/08C07D 307/10C07D 279/12C07C 327/60C07C 309/00G02B 5/223G03F 7/028G03F 7/032G03F 7/027G03F 7/0045G03F 7/0007H10P 76/00
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Claims
Abstract
The present invention also relates to the use of the this composition, to novel oxime sulfonates and the use of the oxime sulfonates as thermal curing promoter.
Claims
exact text as granted — not AI-modified1 - 44 . (canceled)
45 : An oxime sulfonate compound of the formula I,
QA a B b C c (I)
where
a is 0, 1, 2, 3, 4 or 6;
b is 0, 1, 2, 3, 4 or 6; and
c is 0, 1, 2, 3, 4 or 6;
where the sum of a+b+c is 2, 3, 4 or 6
where
A is a group
B is a group
C is a group
where
# denotes the point of attachment to Q;
X is S, SO 2 or NR 14 ;
Q if a is 2, b is 0 and c is 0
is a divalent linker, which is selected from L-C 1 -C 30 -alkylene-L,
L-C 2 -C 30 -alkenylene-L, L-C 3 -C 16 -cycloalkylene-L, L-heterocycloalkylene-L, L-C 6 -C 20 -arylene-L, L-heteroarylene-L, L-C 1 -C 30 -alkylene-L 2 -L,
L-C 2 -C 30 -alkenylene-L 2 -L,
L-C 3 -C 16 -cycloalkylene-L 1 -C 3 -C 16 -cycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -heterocycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -C 6 -C 20 -arylene-L
L-C 3 -C 16 -cycloalkylene-L 1 -heteroarylene-L,
L-C 6 -C 20 -arylene-L 1 -C 6 -C 20 -arylene-L,
L-C 6 -C 20 -arylene-L 1 -heteroarylene-L,
L-heteroarylene-L 1 -heteroarylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -C 3 -C 16 -cycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -heterocycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -C 6 -C 20 -arylene-L
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -heteroarylene-L,
L-C 6 -C 20 -arylene-L 1 -L 3 -L 1 -C 6 -C 20 -arylene-L,
L-C 6 -C 20 -arylene-L 1 -L 3 -L 1 -heteroarylene-L,
L-heteroarylene-L 1 -L 3 -L 1 -heteroarylene-L,
where each alkylene and each alkenylene may be interrupted by one or more identical or different nonadjacent groups L 4 , and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arylene and each heteroarylene may carry one or more identical or different radicals R Qc ,
where
L is independently of one another selected from a single bond, C(S)O, C(S)NR 12 ;
L 1 is independently of one another a single bond, O, S, NR 14 , CO, OC(O), C(O)O, C(S)O, OC(S), C(O)NR 10 , NR 10 C(O), C(S)NR 12 , NR 12 C(S) or NR 10 SO 2 ;
L 2 is C 3 -C 20 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene or heteroarylene,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more CO and/or may be substituted by one or more identical or different radicals R L2b ,
where arylene and heteroarylene may be substituted by one or more identical or different radicals R L2c , where
R L2b is independently of one another selected from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 or phenyl;
R L2 c has one of the meanings indicated for R L2b ;
L 3 is selected from C 1 -C 30 -alkylene, C 2 -C 30 -alkenylene, C 3 -C 20 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene and heteroarylene,
where alkylene and alkenylene may be interrupted by one or more identical or different O, S, NR 6 and CO and/or may carry one or more identical or different radicals R L3a ,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more CO, and/or may be substituted by one or more identical or different radicals R L3b ,
where arylene and heterarylene may be substituted by one or more identical or different radicals R L3c , where
R L3 a is independently of one another selected from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 10 -cycloalkyl, heterocyclyl, heteroaryl, phenyl and naphthyl, where the five last-mentioned radicals may be substituted by one or more identical or different radicals R 3aa , where
R 3aa has one of the meanings indicated for R L2b ;
R L3b has one of the meanings indicated for R L2b ;
R L3 c has one of the meanings indicated for R L2 c;
L 4 is independently of one another selected from O, S, NR 6 , CO, C(O)O, OC(O), C(O)NR 10 , NR 10 C(O), C(S)NR 12 , NR 12 C(S), NR 10 SO 2 , C 3 -C 20 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, and heteroarylene,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more CO, and/or may be substituted by one or more identical or different radicals R L4b ,
where arylene and heteroarylene may be substituted by one or more identical or different radicals R L4c , where
R L4b has one of the meanings indicated for R L2b ; and
R L4c has one of the meanings indicated for R L2c ;
R Qa is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 ,
C 3 -C 10 -cycloalkyl which may be interrupted by one or two CO groups, heterocyclyl which may be interrupted by one or two CO groups, heteroaryl, phenyl and naphthyl, where the five last-mentioned radicals may be substituted by one or more identical or different radicals R Qaa , where
R Qaa is independently of one another selected from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;
R Qb is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, heteroaryl, phenyl and naphthyl, where the three last-mentioned radicals may be substituted by one or more identical or different radicals R Qba ,
where
R Qba has one of the meanings indicated for R Qaa ;
R Qc is independently of one another selected from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , phenyl, C 3 -C 10 -cycloalkyl and heterocyclyl, where in the two last-mentioned radicals one or two CH 2 groups may be replaced by CO;
Q if b is 2, a is 0 and c is 0,
is a divalent linker, which is selected from
L 5 -C 1 -C 30 -alkylene-L 5 , L 5 -C 2 -C 30 -alkenylene-L 5 , L-C 3 -C 16 -cycloalkylene-L 5 , L 5 -heterocycloalkylene-L 5 , L 5 -C 6 -C 20 -arylene-L 5 , L 5 -heteroarylene-L 5 ,
L 5 -C 1 -C 30 -alkylene-L 6 -L 5 , L 5 -C 2 -C 30 -alkenylene-L 6 -L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -C 3 -C 16 -cycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -heterocycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 1 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -heteroarylene-L 5 ,
L 5 -C 6 -C 20 -arylene-L 7 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 6 -C 20 -arylene-L 7 -heteroarylene-L 5 ,
L 5 -heteroarylene-L 7 -heteroarylene-L 5
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -C 3 -C 16 -cycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -heterocycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -heteroarylene-L 5 ,
L 5 -C 6 -C 20 -arylene-L 7 -L 8 -L 7 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 6 -C 20 -arylene-L 7 -L 8 -L 7 -heteroarylene-L 5 ,
L 5 -heteroarylene-L 7 -L 8 -L 7 -heteroarylene-L 5 ,
where each alkylene and each alkenylene may be interrupted by one or more identical or different groups L 9 , and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arylene radicand heteroarylene may carry one or more identical or different radicals R Qc , where
L 5 independently of one another is a single bond, S, O, NR 6 , CO, C(O)O, OC(O), NR 10 CO or CONR 10 ;
L 6 has one of the meanings indicated for L 2 ;
L 7 has one of the meanings indicated for L 1 ;
L 8 has one of the meanings indicated for L 3 ;
L 9 has one of the meanings indicated for L 4 ;
or
Q if c is 2, a is 0 and b is 0.
is a divalent linker, which is selected from C 1 -C 30 -alkylene, C 2 -C 30 -alkenylene, C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, heteroarylene, C 1 -C 30 -alkylene-L 10 , C 2 -C 30 -alkenylene-L 10 ,
C 3 -C 16 -cycloalkylene-L 11 -C 3 -C 16 -cycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -heterocycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -C 6 -C 20 -arylene,
C 3 -C 16 -cycloalkylene-L 11 -heteroarylene,
C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene,
C 6 -C 20 -arylene-L 1 -heteroarylene, heteroarylene-L 1 -heteroarylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -C 3 -C 16 -cycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -C 6 -C 20 -arylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -heterocycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -heteroarylene,
C 6 -C 20 -arylene-L 11 -L 12 -L 11 -C 6 -C 20 -arylene,
C 6 -C 20 -arylene-L 11 -L 12 -L 11 -heteroaylene,
heteroarylene-L 11 -L 12 -L 11 -heteroarylene,
where each alkylene and each alkenylene may be interrupted by one or more identical or different groups L 13 , and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arylene and each heteroarylene may carry one or more identical or different radicals R Qc ,
where
L 10 has one of the meanings indicated for L 2
L 11 has one of the meanings indicated for L 1 ;
L 12 has one the meanings indicated for L 3 ;
L 13 has one of the meanings indicated for L 4 ;
or
Q if two of the indices a, b or c are each 1 and the remaining index is 0, the sum of a+b+c being 2,
is a divalent linker, which is selected from C 1 -C 30 -alkylene, C 2 -C 30 -alkenylene, C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, heteroarylene, C 1 -C 30 -alkylene-L 10 , C 2 -C 30 -alkenylene-L 10 ,
C 3 -C 16 -cycloalkylene-L 11 -C 3 -C 16 -cycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -heterocycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -C 6 -C 20 -arylene,
C 3 -C 16 -cycloalkylene-L 11 -heteroarylene,
C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene,
C 6 -C 20 -arylene-L 11 -heteroarylene, heteroarylene-L 11 -heteroarylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -C 3 -C 16 -cycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -C 6 -C 20 -arylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -heterocycloalkylene,
C 3 -C 6 -cycloalkylene-L 11 -L 12 -L 11 -heteroarylene,
C 6 -C 20 -arylene-L 11 -L 12 -L 11 -C 6 -C 20 -arylene,
C 6 -C 20 -arylene-L 11 -L 12 -L 11 -heteroaylene,
heteroarylene-L 11 -L 12 -L 11 -heteroarylene,
where each alkylene and each alkenylene may be interrupted by one or more identical or different groups L 13 , and/or may carry one or more identical or different radicals R Qb ;
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arylene and each heteroarylene may carry one or more identical or different radicals R Qc ,
where
L 10 has one of the meanings indicated for L 2
L 11 has one of the meanings indicated for L 1 ;
L 12 has one the meanings indicated for L 3 ;
L 13 has one of the meanings indicated for L 4 ;
or
Q if the sum of a+b+c=3,
is a trivalent linker, which is selected from C 1 -C 30 -alkanetriyl, C 2 -C 30 -alkenetriyl, C 3 -C 16 -cycloalkanetriyl, heterocycloalkanetriyl, C 6 -C 20 -arenetriyl, heteroarenetriyl, C 1 -C 30 -alkanetriyl-L 14 -L 15 , C 2 -C 30 -alkenetriyl-L 14 -L 15 , C 1 -C 30 -alkylene-L 14 -L 16 , C 2 -C 30 -alkenetriyl-L 14 -L 15 , C 2 -C 30 -alkenylene-L 14 -L 16 , C 3 -C 16 -cycloalkanetriyl-L 14 -L 11 -C 3 -C 16 -cycloalkylene, C 3 -C 16 -cycloalkanetriyl-L 14 -L 15 -C 6 -C 20 -arylene, C 6 -C 20 -arenetriyl-L 14 -L 15 -C 6 -C 20 -arylene, and C 6 -C 20 -arylene-L 14 -L 15 -C 3 -C 16 -cycloalkanetriyl
where each alkanetriyl, each alkylene, each alkenetriyl and each alkenylene may be interrupted by one or more identical or different groups L 17 and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkanetriyl, each cycloalkylene, each heterocycloalkanetriyl and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arenetriyl, each arylene, each heteroarenetriyl and each heteroarylene may carry one or more identical or different radicals R Qc , where
L 14 has one of the meanings indicated for L 1 ;
L 15 has one of the meanings indicated for L 2 ;
L 16 is C 6 -C 20 -arenetriyl, heteroarenetriyl, C 3 -C 20 -cycloalkanetriyl and heterocycloalkanetriyl, where cycloalkanetriyl and heterocycloalkanetriyl may be interrupted by one or more CO, and/or may be substituted by one or more identical or different radicals R L6b ,
where arenetriyl and heteroarenetriyl may be substituted by one or more identical or different radicals R L16c , where
R L16b has one of the meanings indicated for R L2b ;
R L16c has one of the meanings indicated for R L2c ;
L 17 has one of the meanings indicated for L 4 ;
Q if the sum of a+b+c=4,
is a tetravalent linker, which is selected from C 1 -C 30 -alkanetetrayl which may be interrupted by one or more identical or different groups L 18 and/or may carry one or more identical or different radicals R Qa ;
where
L 18 has one of the meanings given for L 17 ;
Q if the sum of a+b+c=6
is a hexavalent linker which is selected from C 2 -C 30 -alkanehexayl which may be interrupted by one or more identical or different groups L 19 and/or may carry one or more identical or different radicals R Qa ;
where
L 19 has one of the meanings given for L 17 ;
R 1 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl, heteroaryl, C 1 -C 20 -alkanoyl, C 3 -C 20 -cycloalkanoyl, C 2 -C 20 -alkenoyl, C 6 -C 20 -aroyl, CSNR 12 R 13 , C(O)OR 9 or CSOR 9 ,
where C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 1a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 1b , where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or different radicals R 1c ,
where C 1 -C 20 -alkanoyl and C 2 -C 20 -alkenoyl may carry one or more identical or different radicals R 1a ,
where C 3 -C 20 -cycloalkanoyl may carry one or more identical or different radicals R 1b ,
where C 6 -C 20 -aroyl may carry one or more identical or different radicals R 1d , where
R 1a is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 1aa ,
where
R 1aa is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -alkyl which may be interrupted by one or more groups selected from CO, O, S, C(O)O, OC(O), C(O)S and SC(O), C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;
R 1b is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 1 -C 12 -alkyl, C 1 -C 12 -hydroxyalkyl, C 1 -C 12 -haloalkyl, C 2 -C 12 -alkenyl, heteroaryl and C 6 -C 10 -aryl where the two last-mentioned radicals may carry one or more identical or different radicals R 1ba , where
R 1ba has one of the meanings indicated for R 1aa ;
R 1c is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl where the two last-mentioned radicals may be interrupted by one or two C═O groups and where phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl may carry one or more identical or different radicals R 1ca , where
R 1ca has one of the meanings indicated for R 1aa ;
R 1d is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, C 6 -C 10 -aryl and heteroaryl where the four last-mentioned radicals may carry one or more radicals R 1da , where R 1da has one of the meanings indicated for R 1aa ;
or
if b is 2, 3, 4 or 6 and/or c is 2, 3, 4 or 6, two radicals R 1 together can be a divalent bridging group having 1 to 20 atoms between the flanking bonds,
or
if b is 2, 3, 4 or 6, at least one group-X 1 may be bound to a carbon atom or nitrogen atom of Q via a divalent bridging group having 1 to 10 atoms between the flanking bonds,
R 2 is hydrogen, SR 4 , OR 5 , NR 1 R 14 , COR 8 , SO 2 R 4 , COOR 9 , CONR 10 R 11 , SO 2 NR 10 R 11 , PO(OR 9 ) 2 , CN, C 1 -C 16 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl, heteroaryl, C 1 -C 20 -alkanoyl, C 2 -C 20 -alkenoyl, C 3 -C 20 -cycloalkanoyl, C 6 -C 20 -aroyl or a group R 2a ,
where C 1 -C 16 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 2a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 2b ,
where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or different radicals R 2c ,
where C 1 -C 20 -alkanoyl and C 2 -C 20 -alkenoyl may carry one or more identical or different radicals R 2a ,
where C 3 -C 20 -cycloalkanoyl may carry one or more identical or different radicals R 2b ,
where C 6 -C 20 -aroyl may carry one or more identical or different radicals R 2d ,
where
R 2a is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 2aa ,
where
R 2a is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -alkyl which may be interrupted by one or more groups selected from CO, O, S, C(O)O, OC(O), C(O)S and SC(O), C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, phenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;
R 2b has one of the meanings indicated for R 1b ;
R 2c has one of the meanings indicated for R 1c ;
R 2d has one of the meanings indicated for R 1d ;
E is selected from
where
# is the point of attachment to the remainder of the molecule;
d is 0, 1, 2, 3 or 4;
e is 0, 1, or 2;
f is 0, 1, or 2;
g is 0, 1, 2, 3 or 4;
R 2e has one of the meanings indicated for R 2c ;
R 2f is C 1 -C 20 -alkylene-COO − , C 2 -C 20 -alkenylene-COO − , C 2 -C 20 -alkynylene-COO − , C 3 -C 20 -cycloalkylene-COO − , heterocycloalkylene-COO − , C 6 -C 20 -arylene-COO − , heteroarylene-COO − , C 1 -C 20 -alkylene-S(O 2 )O − , C 2 -C 20 -alkenylene-S(O 2 )O − , C 2 -C 20 -alkynylene-S(O 2 )O − , C 3 -C 20 -cycloalkylene-S(O 2 )O − , heterocycloalkylene-S(O 2 )O − , C 6 -C 2 O-arylene-S(O 2 )O − , heteroarylene-S(O 2 )O − , C 1 -C 20 -alkylene-OS(O 2 )O − , C 2 -C 20 -alkenylene-OS(O 2 )O − , C 2 -C 20 -alkynylene-OS(O 2 )O − , C 3 -C 20 -cycloalkylene-OS(O 2 )O − , heterocycloalkylene-OS(O 2 )O − , C 6 -C 20 -arylene-OS(O 2 )O— or heteroarylene-OS(O 2 )O −
where each alkylene, each alkenyle and each alkynyle may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 2a ,
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or two groups CO and/or may carry one or more identical or different radicals R 2b ,
where each arylene and each heteroarylene may carry one or more radicals R 2c ,
An − is Cl − , Br − , l − , SCN − , BF 4 − , PF 6 − , ClO 4 − , SbF 6 − , AsF 6 − , C 1 -C 20 -alkyl-COO − , C 1 -C 20 -alkyl-S(O) 2 O − , C 1 -C 20 -alkyl-OS(O) 2 O − , C 6 -C 20 -aryl-COO − , C 6 -C 20 -aryl-S(O) 2 O − or C 6 -C 20 -aryl-OS(O) 2 O − , where the aryl moiety of the three last-mentioned radicals may be substituted by 1, 2, 3 or 4 identical or different C 1 -C 20 -alkyl;
or
—R 2 together with —X—R 1 may be X—(C 1 -C 20 -alkylene)-Y, X—(C 2 -C 20 -alkenylene)-Y, X—(C 3 -C 20 -cycloalkylene)-Y, X-(heterocycloalkylene)-Y, X-(o-phenylene)-Y, X-(o-xylylene)-Y, X-(o-phenylene-C 1 -C 12 -alkylene)-Y, X—(C 1 -C 12 -alkylene-o-phenylene)-Y, X—(O—C 1 -C 20 -alkylene)-Y, X—(S—C 1 -C 20 -alkylene)-Y or X—(N(R 6 )—C 1 -C 20 -alkylene)-Y, Y being attached to the oxime carbon atom carrying X
where each alkylene and alkenylene may comprise one or more identical or different groups selected from O, S, NR 6 and CO and/or may be substituted by one or more radicals R 2g ,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more groups CO and/or may be optionally substituted by one or more identical or different radicals R 2h ,
where each phenylene and the phenylene moiety of o-xylylene may be substituted by one or more identical or different radicals R 2h ,
where
Y is O, S, NR 14 , CO, SC(O), OC(O), C(O)O, NR 10 C(O), C(O)NR 10 , NR 10 SO 2 or a single bond;
R 2g is independently of one another selected from F, Cl, Br, I, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , heteroaryl and C 6 -C 10 -aryl where the two-last-mentioned radicals may carry one or more radicals R 2ga , where R 2ga is phenoxy or has one of the meanings indicated for R 1aa ;
R 2h is independently of one another selected from F, Cl, Br, I, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, heteroaryl and C 6 -C 10 -aryl where the two last-mentioned radicals may carry one or more radicals R 2ha , where R 2h has one of the meanings indicated for R 1aa ;
or if X is S, —R 2 together with —S—R 1 may be S—C(S)—NR 12 —C(O) or S—C(═NOR 15 )—C(O)—NR 12 —C(O), where R 15 is hydrogen or phenylsulfonyl where the phenyl moiety may be substituted by C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,
or if a is 2, 3, 4 or 6 and/or c is 2, 3, 4 or 6, two radicals R 2 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds;
R 3 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl or heteroaryl,
where C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 3a , where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 3b , where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or radicals R 3c ,
where
R 3a has one of the meanings indicated for R 2a ;
R 3b has one of the meanings indicated for R 1b ;
R 3c has one of the meanings indicated for R 1c ;
or
—X—R 1 and R 3 may together form a divalent radical selected from
X—(C 1 -C 20 -alkylene)-Z, X—(C 2 -C 20 -alkenylene)-Z, X—(C 3 -C 20 -cycloalkylene)-Z, X-(heterocycloalkylene)-Z, X-(o-phenylene)-Z,
X-(o-xylylene)-Z, X—(C 0 -C 12 -alkylene-heteroarylene-C 0 -C 12 -alkylene)-Z;
X-(o-phenylene-C 1 -C 12 -alkylene)-Z,
X—(C 1 -C 12 -alkylene-o-phenylene)-Z and S—C(S)—NR 12 —C(O),
where Z is attached to the sulfur atom of the sulfonate group, where each alkylene and each alkenylene may be interrupted by one or more identical or different groups selected from O, S, NR 6 and CO and/or may be substituted by one or more radicals R 3g ,
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more groups CO and/or may be optionally substituted by one or more identical or different radicals R 3h ,
where each phenylene and the phenylene moiety of o-xylylene may be substituted by one or more identical or different radicals R 3h , where
R 3g has one of the meanings indicated for R 2g ;
R 3h has one of the meanings indicated for R 2h ; and
Z is O, S, NR 14 , CO, OC(O), SC(O), C(O)O, NR 10 C(O), C(O)NR 10 , NR 10 (SO 2 ) or a single bond;
R 4 is selected independently of one another from hydrogen, C 1 -C 20 -alkyl, C 2 -C 12 -alkenyl,
C 3 -C 10 -cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or more C═O groups,
C 1 -C 20 -alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C 1 -C 8 -alkyl)- and CO, and/or may carry one or more identical or different radicals R 4a ,
C 2 -C 12 -alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C 1 -C 8 -alkyl)-,
—(CH 2 CH 2 O) m H, with m being 1-20,
—(CH 2 CH 2 O) n (CO)—(C 1 -C 8 -alkyl), with n being 1-20, C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C 1 -C 6 -alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C 1 -C 6 -alkyl, OH or C 1 -C 6 -alkoxy,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R 4c ,
or phenyl or naphthyl which forms a 5- or 6-membered ring with the phenyl ring to which the SR 4 is attached via a single bond, C 1 -C 4 -alkylene, O, S, NR 6 or CO,
where
R 4a is selected independently of one another from F, Cl, Br, I, C 3 -C 10 -cycloalkyl, heterocyclyl, phenyl, OH, SH, CN, C 3 -C 6 -alkenoxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO)O(C 1 -C 8 -alkyl), O(CO)—(C 1 -C 8 -alkyl), O(CO)-phenyl, (CO)OH and (CO)O(C 1 -C 8 -alkyl);
R 4c is selected independently of one another from F, Cl, Br, I, C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -alkoxy, phenyl-C 1 -C 3 -alkoxy, phenoxy, C 1 -C 12 -alkylsulfanyl, phenylsulfanyl, —(CO)O(C 1 -C 8 -alkyl), (CO)N(C 1 -C 8 -alkyl) 2 and phenyl;
R 5 is selected independently of one another from hydrogen, C 1 -C 20 -alkyl, C 2 -C 12 -alkenyl,
C 3 -C 10 -cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or two C═O groups,
C 1 -C 20 -alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C 1 -C 8 -alkyl)- and CO, and/or may carry one or more identical or different radicals R 5a ,
C 2 -C 12 -alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C 1 -C 8 -alkyl)-,
—(CH 2 CH 2 O) m H, with m being 1-20,
—(CH 2 CH 2 O) n (CO)—(C 1 -C 8 -alkyl), with n being 1-20,
C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C 1 -C 6 -alkoxy,
C 2 -C 8 -alkanoyl, which is interrupted by one or more identical or different groups selected from —O— and —S— and may be substituted by one or more identical or different radicals selected from hydroxyaminylene (═N—OH), F, Cl, Br, I, OH and C 1 -C 6 -alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C 1 -C 6 -alkyl, OH or C 1 -C 6 -alkoxy, phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R 5c ,
or phenyl or naphthyl which forms a 5- or 6-membered ring with the phenyl ring to which the OR 5 is attached via a single bond, C 1 -C 4 -alkylene, O, S, NR 6 or CO,
where
R 5a has one of the meanings indicated for R 4a ;
R 5c has one of the meanings indicated for R 4c ;
R 6 , R 10 and R 12 are selected independently of one another from hydrogen, OR 5 , C 1 -C 20 -alkyl, C 2 -C 12 -alkenyl,
C 3 -C 10 -cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or two C═O groups,
C 1 -C 20 -alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C 1 -C 8 -alkyl)- and CO, and/or may carry one or more identical or different radicals R 6a ,
C 2 -C 12 -alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C 1 -C 8 -alkyl)-,
—(CH 2 CH 2 O) o H, with o being 1-20,
—(CH 2 CH 2 O) p (CO)—(C 1 -C 8 -alkyl), with p being 1-20,
C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C 1 -C 6 -alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C 1 -C 6 -alkyl, —OH or C 1 -C 6 -alkoxy, phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R 6c ,
where
R 6a has one of the meanings indicated for R 4a ;
R 6c has one of the meanings indicated for R 4c ;
or
two radicals R 6 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds;
or
two radicals R 10 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds;
or
two radicals R 12 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds;
R 7 , R 11 and R 13 are independently of one another selected from OR 5 , C 1 -C 20 -alkyl, C 2 -C 12 -alkenyl,
C 3 -C 10 -cycloalkyl, heterocyclyl, where in the two last-mentioned radicals one or two CH 2 groups may be replaced by a C═O group,
C 1 -C 20 -alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C 1 -C 8 -alkyl)- and CO, and/or may carry one or more identical or different radicals R 7a ,
C 2 -C 12 -alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C 1 -C 8 -alkyl)-,
—(CH 2 CH 2 O) q H, with q being 1-20,
—(CH 2 CH 2 O) r (CO)—(C 1 -C 8 -alkyl), with r being 1-20,
C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C 1 -C 6 -alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C 1 -C 6 -alkyl, OH or C 1 -C 6 -alkoxy, phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R 7c ,
where
R 7a has one of the meanings indicated for R 4a ;
R 7c has one of the meanings indicated for R 4c ;
or
R 6 and R 7 together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which may have a further heteroatom or heteroatomic group selected from the group consisting of CO, O, S and N(C 1 -C 8 -alkyl) as ring member and which may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl;
or
R 10 and R 11 together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which may have a further heteroatom or heteroatomic group selected from the group consisting of CO, O, S and N(C 1 -C 8 -alkyl) as ring member and which may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl;
or
R 12 and R 13 together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which may have a further heteroatom or heteroatomic group selected from the group consisting of CO, O, S and N(C 1 -C 8 -alkyl) as ring member and which may carry 1, 2, 3 or 4 C 1 -C 4 -alkyl;
R 8 is independently of one another selected from hydrogen, C 1 -C 20 -alkyl, C 2 -C 12 -alkenyl,
C 3 -C 10 -cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or more C═O groups,
C 1 -C 20 -alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C 1 -C 8 -alkyl)- and CO, and/or may carry one or more identical or different radicals R 8a ,
C 2 -C 12 -alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C 1 -C 8 -alkyl)-,
—(CH 2 CH 2 O) s H, with s being 1-20,
—(CH 2 CH 2 O) t (CO)—(C 1 -C 8 -alkyl), with t being 1-20,
C 6 -C 20 -aryl and heteroaryl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R 8c ,
where
R 8a has one of the meanings indicated for R 4a ;
R 8c has one of the meanings indicated for R 4c ;
R 9 is independently of one another selected from hydrogen, C 1 -C 20 -alkyl, C 2 -C 12 -alkenyl, C 3 -C 10 -cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or more C═O groups,
C 1 -C 20 -alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C 1 -C 8 -alkyl)- and CO, and/or may carry one or more identical or different radicals R 9a ,
C 2 -C 12 -alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C 1 -C 8 -alkyl)-,
—(CH 2 CH 2 O) u H, with u being 1-20,
—(CH 2 CH 2 O) v (CO)—(C 1 -C 8 -alkyl), with v being 1-20,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R 9c ,
where
R 9a has one of the meanings indicated for R 4a ;
R 9c has one of the meanings indicated for R 4c ;
R 14 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl,
C 6 -C 20 -aryl, heteroaryl, C 1 -C 20 -alkanoyl, C 2 -C 20 -alkenoyl, C 3 -C 20 -cycloalkanoyl, C 6 -C 20 -aroyl, CSNR 12 R 13 or CSOR 9 ,
where C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected —O—, —S—, —N(R 6 )— and CO and/or may carry one or more identical or different radicals R 14a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R 14b ,
where C 6 -C 20 -aryl, heteroaryl may carry one or more identical or radicals R 14c ,
where C 1 -C 20 -alkanoyl, C 2 -C 20 -alkenoyl may carry one or more identical or different radicals R 14a ,
where C 3 -C 20 -cycloalkanoyl may carry one or more identical or different radicals R 14b ,
where C 6 -C 20 -aroyl may carry one or more identical or different radicals R 14d ,
where
R 14a has one of the meanings indicated for R 2a ,
R 14b has one of the meanings indicated for R 1b ,
R 14c has one of the meanings indicated for R 1c ;
R 14d has one of the meanings indicated for R 1d ;
or
R 1 together with R 14 may be a divalent bridging group having 1 to 20 atoms between the flanking bonds;
or two radicals R 14 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds.
46 : The compound of formula I according to claim 45 ,
where X is S or NR 14 ; Q if a is 2, b is 0 and c is 0
is a divalent linker, which is selected from L-C 1 -C 30 -alkylene-L,
L-C 2 -C 30 -alkenylene-L, L-C 3 -C 16 -cycloalkylene-L, L-heterocycloalkylene-L, L-C 6 -C 20 -arylene-L, L-heteroarylene-L, L-C 1 -C 30 -alkylene-L 2 -L,
L-C 2 -C 30 -alkenylene-L 2 -L,
L-C 3 -C 16 -cycloalkylene-L 1 -C 3 -C 16 -cycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -heterocycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -C 6 -C 20 -arylene-L
L-C 3 -C 16 -cycloalkylene-L 1 -heteroarylene-L,
L-C 6 -C 20 -arylene-L 1 -C 6 -C 20 -arylene-L,
L-C 6 -C 20 -arylene-L 1 -heteroarylene-L,
L-heteroarylene-L 1 -heteroarylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -C 3 -C 16 -cycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -heterocycloalkylene-L,
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -C 6 -C 20 -arylene-L
L-C 3 -C 16 -cycloalkylene-L 1 -L 3 -L 1 -heteroarylene-L,
L-C 6 -C 20 -arylene-L 1 -L 3 -L 1 -C 6 -C 20 -arylene-L,
L-C 6 -C 20 -arylene-L 1 -L 3 -L 1 -heteroarylene-L,
L-heteroarylene-L 1 -L 3 -L 1 -heteroarylene-L,
where each alkylene and each alkenylene may be interrupted by one or more identical or different nonadjacent groups L 4 , and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arylene and each heteroarylene may carry one or more identical or different radicals R Qc ,
where
L is independently of one another selected from a single bond, C(S)O, C(S)NR 12 ;
L 1 is independently of one another a single bond, O, S, NR 14 , CO, OC(O), C(O)O, C(S)O, OC(S), C(O)NR 10 , NR 10 C(O), C(S)NR 12 , NR 12 C(S) or NR 10 SO 2 ;
L 2 is C 3 -C 20 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene or heteroarylene,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more CO and/or may be substituted by one or more identical or different radicals R L2b ,
where arylene and heteroarylene may be substituted by one or more identical or different radicals R L2c , where
R L2b is independently of one another selected from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 or phenyl;
R L2c has one of the meanings indicated for R L2b ;
L 3 is selected from C 1 -C 30 -alkylene, C 2 -C 30 -alkenylene, C 3 -C 20 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene and heteroarylene,
where alkylene and alkenylene may be interrupted by one or more identical or different O, S, NR 6 and CO and/or may carry one or more identical or different radicals R L3a ,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more CO, and/or may be substituted by one or more identical or different radicals R L3b ,
where arylene and heterarylene may be substituted by one or more identical or different radicals R L3c , where
R L3a is independently of one another selected from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 10 -cycloalkyl, heterocyclyl, heteroaryl, phenyl and naphthyl, where the five last-mentioned radicals may be substituted by one or more identical or different radicals R 3aa , where
R 3aa has one of the meanings indicated for R L2b ;
R L3b has one of the meanings indicated for R L2b ;
R L3c has one of the meanings indicated for R L2c ;
L 4 is independently of one another selected from O, S, NR 6 , CO, C(O)O, OC(O), C(O)NR 10 , NR 10 C(O), C(S)NR 12 , NR 12 C(S), NR 10 SO 2 , C 3 -C 20 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, and heteroarylene, where cycloalkylene and heterocycloalkylene may be interrupted by one or more CO, and/or may be substituted by one or more identical or different radicals R L4b ,
where arylene and heteroarylene may be substituted by one or more identical or different radicals R L4c , where
R L4b has one of the meanings indicated for R L2b ; and
R L4c has one of the meanings indicated for R L2c ;
R Qa is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 ,
C 3 -C 10 -cycloalkyl which may be interrupted by one or two CO groups, heterocyclyl which may be interrupted by one or two CO groups, heteroaryl, phenyl and naphthyl, where the five last-mentioned radicals may be substituted by one or more identical or different radicals R Qaa , where
R Qaa is independently of one another selected from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;
R Qb is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, heteroaryl, phenyl and naphthyl, where the three last-mentioned radicals may be substituted by one or more identical or different radicals R Qba , where
R Qba has one of the meanings indicated for R Qaa ;
R Qc is independently of one another selected from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , phenyl, C 3 -C 10 -cycloalkyl and heterocyclyl, where in the two last-mentioned radicals one or two CH 2 groups may be replaced by CO;
Q if b is 2, a is 0 and c is 0,
is a divalent linker, which is selected from
L 5 -C 1 -C 30 -alkylene-L 5 , L-C 2 -C 30 -alkenylene-L 5 , L 5 -C 3 -C 16 -cycloalkylene-L 5 , L 5 -heterocycloalkylene-L 5 , L 5 -C 6 -C 20 -arylene-L 5 , L 5 -heteroarylene-L 5 ,
L 5 -C 1 -C 30 -alkylene-L 6 -L 5 , L 5 -C 2 -C 30 -alkenylene-L 6 -L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -C 3 -C 16 -cycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -heterocycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -heteroarylene-L 5 ,
L 5 -C 6 -C 20 -arylene-L 7 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 6 -C 20 -arylene-L 7 -heteroarylene-L 5 ,
L 5 -heteroarylene-L 7 -heteroarylene-L 5
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -C 3 -C 16 -cycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -heterocycloalkylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 3 -C 16 -cycloalkylene-L 7 -L 8 -L 7 -heteroarylene-L 5 ,
L-C 6 -C 20 -arylene-L 7 -L 8 -L 7 -C 6 -C 20 -arylene-L 5 ,
L 5 -C 6 -C 20 -arylene-L 7 -L 8 -L 7 -heteroarylene-L 5 ,
L 5 -heteroarylene-L 7 -L 8 -L 7 -heteroarylene-L 5 ,
where each alkylene and each alkenylene may be interrupted by one or more identical or different groups L 9 , and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arylene radicand heteroarylene may carry one or more identical or different radicals R Qc , where
L 5 independently of one another is a single bond, S, O, NR 6 , CO, C(O)O, OC(O), NR 10 CO or CONR 10 ;
L 6 has one of the meanings indicated for L 2 ;
L 7 has one of the meanings indicated for L 1 ;
L 8 has one of the meanings indicated for L 3 ;
L 9 has one of the meanings indicated for L 4 ;
or Q if c is 2, a is 0 and b is 0.
is a divalent linker, which is selected from C 1 -C 30 -alkylene, C 2 -C 30 -alkenylene,
C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, heteroarylene, C 1 -C 30 -alkylene-L 10 , C 2 -C 30 -alkenylene-L 10 ,
C 3 -C 16 -cycloalkylene-L 11 -C 3 -C 16 -cycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -heterocycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -C 6 -C 20 -arylene,
C 3 -C 16 -cycloalkylene-L 11 -heteroarylene,
C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene,
C 6 -C 20 -arylene-L 11 -heteroarylene, heteroarylene-L 11 -heteroarylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -C 3 -C 16 -cycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -C 6 -C 20 -arylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -heterocycloalkylene,
C 3 -C 16 -cycloalkylene-L 11 -L 12 -L 11 -heteroarylene,
C 6 -C 20 -arylene-L 11 -L 12 -L 11 -C 6 -C 20 -arylene,
C 6 -C 20 -arylene-L 11 -L 12 -L 11 -heteroaylene,
heteroarylene-L 11 -L 12 -L 11 -heteroarylene,
where each alkylene and each alkenylene may be interrupted by one or more identical or different groups L 13 , and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arylene and each heteroarylene may carry one or more identical or different radicals R Qc ,
where
L 10 has one of the meanings indicated for L 2
L 11 has one of the meanings indicated for L 1 ;
L 12 has one the meanings indicated for L 3 ;
L 13 has one of the meanings indicated for L 4 ;
or Q if the sum of a+b+c=3,
is a trivalent linker, which is selected from C 1 -C 30 -alkanetriyl, C 2 -C 30 -alkenetriyl, C 3 -C 16 -cycloalkanetriyl, heterocycloalkanetriyl, C 6 -C 20 -arenetriyl, heteroarenetriyl, C 1 -C 30 -alkanetriyl-L 14 -L 15 , C 2 -C 30 -alkenetriyl-L 14 -L 15 , C 1 -C 30 -alkylene-L 14 -L 16 , C 2 -C 30 -alkenetriyl-L 14 -L 15 , C 2 -C 30 -alkenylene-L 14 -L 16 , C 3 -C 16 -cycloalkanetriyl-L 14 -L 11 -C 3 -C 16 -cycloalkylene, C 3 -C 16 -cycloalkanetriyl-L 14 -L 15 -C 6 -C 20 -arylene, C 6 -C 20 -arenetriyl-L 14 -L 15 -C 6 -C 20 -arylene, and C 6 -C 20 -arylene-L 14 -L 15 -C 3 -C 16 -cycloalkanetriyl
where each alkanetriyl, each alkylene, each alkenetriyl and each alkenylene may be interrupted by one or more identical or different groups L 17 and/or may carry one or more identical or different radicals R Qa ;
where each cycloalkanetriyl, each cycloalkylene, each heterocycloalkanetriyl and each heterocycloalkylene may be interrupted by one or more CO groups and/or may carry one or more identical or different radicals R Qb ,
where each arenetriyl, each arylene, each heteroarenetriyl and each heteroarylene may carry one or more identical or different radicals R Qc , where
L 14 has one of the meanings indicated for L 1 ;
L 15 has one of the meanings indicated for L 2 ;
L 16 is C 6 -C 20 -arenetriyl, heteroarenetriyl, C 3 -C 20 -cycloalkanetriyl and heterocycloalkanetriyl, where cycloalkanetriyl and heterocycloalkanetriyl may be interrupted by one or more CO, and/or may be substituted by one or more identical or different radicals R L16b ,
where arenetriyl and heteroarenetriyl may be substituted by one or more identical or different radicals R L16c , where
R L16b has one of the meanings indicated for R L2b ;
R L16c has one of the meanings indicated for R L2c ;
L 17 has one of the meanings indicated for L 4 ;
Q if the sum of a+b+c=4,
is a tetravalent linker, which is selected from C 1 -C 30 -alkanetetrayl which may be interrupted by one or more identical or different groups L 18 and/or may carry one or more identical or different radicals R Qa ;
where
L 18 has one of the meanings given for L 17 ;
Q if the sum of a+b+c=6
is a hexavalent linker which is selected from C 2 -C 30 -alkanehexayl which may be interrupted by one or more identical or different groups L 19 and/or may carry one or more identical or different radicals R Qa ;
where
L 19 has one of the meanings given for L 17 ;
R 1 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl, heteroaryl, C 1 -C 20 -alkanoyl, C 3 -C 20 -cycloalkanoyl, C 2 -C 20 -alkenoyl, C 6 -C 20 -aroyl, CSNR 12 R 13 , C(O)OR 9 or CSOR 9 ,
where C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 1a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 1b ,
where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or different radicals R 1c ,
where C 1 -C 20 -alkanoyl and C 2 -C 20 -alkenoyl may carry one or more identical or different radicals R 1a ,
where C 3 -C 20 -cycloalkanoyl may carry one or more identical or different radicals R 1b ,
where C 6 -C 20 -aroyl may carry one or more identical or different radicals R 1d ,
where
R 1a is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 1aa ,
where
R 1aa is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;
R 1b is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 1 -C 12 -alkyl, C 1 -C 12 -hydroxyalkyl, C 1 -C 12 -haloalkyl, C 2 -C 12 -alkenyl, heteroaryl and C 6 -C 10 -aryl where the two last-mentioned radicals may carry one or more identical or different radicals
R 1ba , where
R 1ba has one of the meanings indicated for R 1aa ;
R 1c is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl where the two last-mentioned radicals may be interrupted by one or two C═O groups and where phenyl, heteroaryl, heterocyclyl and C 3 -C 10 -cycloalkyl may carry one or more identical or different radicals R 1ca , where
R 1c a has one of the meanings indicated for R 1aa ;
R 1d is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, C 6 -C 10 -aryl and heteroaryl where the four last-mentioned radicals may carry one or more radicals R 1da , where R 1da has one of the meanings indicated for R 1aa ;
or
if b is 2, 3, 4 or 6 and/or c is 2, 3, 4 or 6, two radicals R 1 together can be a divalent bridging group having 1 to 20 atoms between the flanking bonds, or
if b is 2, 3, 4 or 6, at least one group-X—R 1 may be bound to a carbon atom or nitrogen atom of Q via a divalent bridging group having 1 to 10 atoms between the flanking bonds,
R 2 is hydrogen, SR 4 , OR 5 , NR 1 R 14 , COR 8 , SO 2 R 4 , COOR 9 , CONR 10 R 11 , SO 2 NR 10 R 11 , PO(OR 9 ) 2 , CN, C 1 -C 16 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl, heteroaryl, C 1 -C 20 -alkanoyl, C 2 -C 20 -alkenoyl, C 3 -C 20 -cycloalkanoyl, C 6 -C 20 -aroyl or a group E,
where C 1 -C 16 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 2a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 2b ,
where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or different radicals R 2c ,
where C 1 -C 20 -alkanoyl and C 2 -C 20 -alkenoyl may carry one or more identical or different radicals R 2a ,
where C 3 -C 20 -cycloalkanoyl may carry one or more identical or different radicals R 2b ,
where C 6 -C 20 -aroyl may carry one or more identical or different radicals R 2d ,
where
R 2a is selected independently of one another from F, Cl, Br, I, CN, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 3 -C 20 -cycloalkyl which may be interrupted by one or more CO groups, heterocyclyl which may be interrupted by one or more CO groups, heteroaryl and C 6 -C 10 -aryl where the four last-mentioned radicals may carry one or more identical or different radicals R 2aa ,
where
R 2a is selected independently of one another from C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C 12 -hydroxyalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ;
R 2b has one of the meanings indicated for R 1b ;
R 2c has one of the meanings indicated for R 1c ;
R 2d has one of the meanings indicated for R 1d ;
E is selected from
where
# is the point of attachment to the remainder of the molecule;
d is 0, 1, 2, 3 or 4;
e is 0, 1, or 2;
f is 0, 1, or 2;
g is 0, 1, 2, 3 or 4;
R 2e has one of the meanings indicated for R 2c ;
R 2f is C 1 -C 20 -alkylene-COO − , C 2 -C 20 -alkenylene-COO − , C 2 -C 20 -alkynylene-COO − , C 3 -C 20 -cycloalkylene-COO − , heterocycloalkylene-COO − , C 6 -C 20 -arylene-COO − , heteroarylene-COO − , C 1 -C 20 -alkylene-S(O 2 )O—, C 2 -C 20 -alkenylene-S(O 2 )O − , C 2 -C 20 -alkynylene-S(O 2 )O − , C 3 -C 20 -cycloalkylene-S(O 2 )O − , heterocycloalkylene-S(O 2 )O − , C 6 -C 20 -arylene-S(O 2 )O − , heteroarylene-S(O 2 )O − , C 1 -C 20 -alkylene-OS(O 2 )O − , C 2 -C 20 -alkenylene-OS(O 2 )O − , C 2 -C 20 -alkynylene-OS(O 2 )O − , C 3 -C 20 -cycloalkylene-OS(O 2 )O − , heterocycloalkylene-OS(O 2 )O − , C 6 -C 20 -arylene-OS(O 2 )O— or heteroarylene-OS(O 2 )O −
where each alkylene, each alkenyle and each alkynyle may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 2a , where each cycloalkylene and each heterocycloalkylene may be interrupted by one or two groups CO and/or may carry one or more identical or different radicals R 2b ,
where each arylene and each heteroarylene may carry one or more radicals R 2c ,
An − is Cl − , Br − , I − , SCN − , BF 4 − , PF 6 − , ClO 4 − , SbF 6 − , AsF 6 − , C 1 -C 20 -alkyl-COO − , C 1 -C 20 -alkyl-S(O) 2 O—, C 1 -C 20 -alkyl-OS(O) 2 O—, C 6 -C 20 -aryl-COO − , C 6 -C 20 -aryl-S(O) 2 O— or C 6 -C 20 -aryl-OS(O) 2 O—, where the aryl moiety of the three last-mentioned radicals may be substituted by 1, 2, 3 or 4 identical or different C 1 -C 20 -alkyl;
or
—R 2 together with —X—R 1 may be X—(C 1 -C 20 -alkylene)-Y, X—(C 2 -C 20 -alkenylene)-Y, X—(C 3 -C 20 -cycloalkylene)-Y, X-(heterocycloalkylene)-Y, X-(o-phenylene)-Y, X-(o-xylylene)-Y, X-(o-phenylene-C 1 -C 12 -alkylene)-Y, X—(C 1 -C 12 -alkylene-o-phenylene)-Y, X—(O—C 1 -C 20 -alkylene)-Y, X—(S—C 1 -C 20 -alkylene)-Y or X—(N(R 6 )—C 1 -C 20 -alkylene)-Y, Y being attached to the oxime carbon atom carrying X
where each alkylene and alkenylene may comprise one or more identical or different groups selected from O, S, NR 6 and CO and/or may be substituted by one or more radicals R 2g ,
where cycloalkylene and heterocycloalkylene may be interrupted by one or more groups CO and/or may be optionally substituted by one or more identical or different radicals R 2h ,
where each phenylene and the phenylene moiety of o-xylylene may be substituted by one or more identical or different radicals R 2h ,
where
Y is O, S, NR 14 , CO, SC(O), OC(O), C(O)O, NR 10 C(O), C(O)NR 10 , NR 10 SO 2 or a single bond;
R 2g is independently of one another selected from F, Cl, Br, I, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , heteroaryl and C 6 -C 10 -aryl where the two-last-mentioned radicals may carry one or more radicals R 2ga , where R 2ga has one of the meanings indicated for R 1aa ;
R 2h is independently of one another selected from F, Cl, Br, I, SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 , C 1 -C 12 -alkyl, C 1 -C 12 -haloalkyl, heteroaryl and C 6 -C 10 -aryl where the two last-mentioned radicals may carry one or more radicals R 2ha , where R 2ha has one of the meanings indicated for R 1aa ;
or if X is S, —R 2 together with —S—R 1 may be S—C(S)—NR 12 —C(O),
or
if a is 2, 3, 4 or 6 and/or c is 2, 3, 4 or 6, two radicals R 2 together may be a divalent bridging group having 1 to 20 atoms between the flanking bonds;
R 3 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 20 -cycloalkyl, heterocyclyl, C 6 -C 20 -aryl or heteroaryl,
where C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl and C 2 -C 20 -alkynyl may be interrupted by one or more identical or different groups selected from —O—, —S—, —N(R 6 )— and CO, and/or may carry one or more identical or different radicals R 3a ,
where C 3 -C 20 -cycloalkyl and heterocyclyl may be interrupted by one or more CO groups, and/or may carry one or more identical or different radicals R 3b ,
where C 6 -C 20 -aryl and heteroaryl may carry one or more identical or radicals R 3c ,
where
R 3a has one of the meanings indicated for R 2a ;
R 3b has one of the meanings indicated for R 1b ;
R 3c has one of the meanings indicated for R 1c ;
or
—X—R 1 and R 3 may together form a divalent radical selected from
X—(C 1 -C 20 -alkylene)-Z, X—(C 2 -C 20 -alkenylene)-Z, X—(C 3 -C 20 -cycloalkylene)-Z, X-(heterocycloalkylene)-Z, X-(o-phenylene)-Z,
X-(o-xylylene)-Z, X—(C 0 -C 12 -alkylene-heteroarylene-C 0 -C 12 -alkylene)-Z;
X-(o-phenylene-C 1 -C 12 -alkylene)-Z,
X—(C 1 -C 12 -alkylene-o-phenylene)-Z and S—C(S)—NR 12 —C(O),
where Z is attached to the sulfur atom of the sulfonate group, where each alkylene and each alkenylene may be interrupted by one or more identical or different groups selected from O, S, NR 6 and CO and/or may be substituted by one or more radicals R 3g ,
where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more groups CO and/or may be optionally substituted by one or more identical or different radicals R 3h ,
where each phenylene and the phenylene moiety of o-xylylene may be substituted by one or more identical or different radicals R 3h , where
R 3g has one of the meanings indicated for R 2g ;
R 3h has one of the meanings indicated for R 2h ; and
Z is O, S, NR 14 , CO, OC(O), SC(O), C(O)O, NR 10 C(O), C(O)NR 10 , NR 10 (SO 2 ) or a single bond;
R 5 is selected independently of one another from hydrogen, C 1 -C 20 -alkyl, C 2 -C 12 -alkenyl,
C 3 -C 10 -cycloalkyl, heterocyclyl, where the two last-mentioned radicals may be interrupted by one or two C═O groups,
C 1 -C 20 -alkyl which is interrupted by one or more identical or different groups selected from —O—, —S—, —N(C 1 -C 8 -alkyl)- and CO, and/or may carry one or more identical or different radicals R 5a ,
C 2 -C 12 -alkenyl which is interrupted by one or more identical or different groups selected from —O—, —S—, and —N(C 1 -C 8 -alkyl)-,
—(CH 2 CH 2 O) m H, with m being 1-20,
—(CH 2 CH 2 O) n (CO)—(C 1 -C 8 -alkyl), with n being 1-20,
C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl, where the two-last mentioned radicals may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, OH or C 1 -C 6 -alkoxy,
benzoyl which may be substituted by one or more identical or different radicals selected from F, Cl, Br, I, C 1 -C 6 -alkyl, OH or C 1 -C 6 -alkoxy,
phenyl and naphthyl, where the two last-mentioned radicals may be substituted by one or more identical or different radicals R 5c ,
or phenyl or naphthyl which forms a 5- or 6-membered ring with the phenyl ring to which the OR 5 is attached via a single bond, C 1 -C 4 -alkylene, O, S, NR 6 or CO,
where
R 5a has one of the meanings indicated for R 4a ;
R 5c has one of the meanings indicated for R 4c .
47 : The compound of formula I according to claim 45 , where
X is S or NR 14 and R 14 is C 1 -C 12 -alkyl, which may be interrupted by one or more O, S, NR 6 or CO and/or may be substituted by one or more identical or different radicals R 14a selected from CN, COR 8 , COOR 9 , CONR 10 R 11 , phenyl and C 3 -C 8 -cycloalkyl which may interrupted by one or two CO groups and where the two last-mentioned radicals may be substituted by one or more identical or different radicals selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ; C 2 -C 12 -alkenyl, which may be interrupted by one or more O, S, NR 6 or CO and/or may be substituted by one or more identical or different radicals R 14a selected from CN, COR 8 , COOR 9 , CONR 10 R 11 , phenyl and C 3 -C 8 -cycloalkyl which may interrupted by one or two CO groups and where the two last-mentioned radicals may be substituted by one or more identical or different radicals selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 and CONR 10 R 11 ; C 3 -C 12 -cycloalkyl, which may be interrupted by one or more CO and/or may be substituted by one or more identical or different radicals R 14b selected from C 1 -C 8 -alkyl, CN, COR 8 , COOR 9 , CONR 10 R 11 ; phenyl, which may be substituted by one or more identical or different radicals R 14c selected from C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 and phenyl, or two radicals R 14 together may be a divalent bridging group having 1 to 10 atoms between the flanking bonds, where R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 are as defined in claim 45 .
48 : The compound of formula I according to claim 45 , where R 1 is CSNR 12 R 13 ; C(O)OR 9 , CSOR 9 ; C 3 -C 12 -alkyl; C 3 -C 12 -cycloalkyl; C 2 -C 12 -alkenyl; C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, where the two last-mentioned radicals are interrupted by one or more identical or different groups selected from O, S, NR 6 or CO and/or which are substituted by one, two or three identical or different radicals R 1a ,
C 3 -C 12 -cycloalkyl, which may be interrupted by one or two CO group(s) and/or which may be substituted by one, two or three radicals R 1b , heterocyclyl, which may be interrupted by one or two CO group(s) and/or which may be substituted by one, two or three radicals R 1b , phenyl, naphthyl or heteraryl, where the three last-mentioned radicals may be substituted by one or more identical or different radicals R 1c , C 6 -C 10 -aroyl, which may be substituted by one or more identical or different radicals R 1d , where R 1a , R 1b , R 1c , R 1d , R 6 , R 9 , R 12 , R 13 are as defined in claim 45 .
49 : The compound of formula I according to claim 45 , where R 2 is COR 8 , COOR 9 , CONR 10 R 11 ,
C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, where the 2 last-mentioned radicals may be substituted by one or more identical or different radicals R 2a , C 3 -C 12 -cycloalkyl, which may be substituted by one or more identical or different radicals R 2b , C 6 -C 10 -aryl, which may be substituted by one or more identical or different radicals R 2c ; 5- or 6-membered heteroaryl comprising besides carbon atoms one, two or three heteroatoms selected from N, O and S and which may be substituted by one or more radicals R 2c ; or pyridinium of the formula
where # is the point of attachment to the remainder of the molecule and R 2f is C 1 -C 12 -alkylene-COO − , C 1 -C 12 -alkylene-S(O) 2 O— or C 1 -C 12 -alkylene-OS(O) 2 O—, where R 2a , R 2b , R 2c , R 8 , R 9 , R 10 and R 11 are as defined in claim 45 .
50 : The compound of formula I according to claim 45 , where —X—R 1 together with R 2 are —X—(C 1 -C 8 -alkylene)-O—C(O)—, —X—(C 3 -C 6 -cycloalkylene)-O—C(O)—, —X-(o-phenylene)-O—C(O)—, —X—(C 1 -C 8 -alkylene)-S—C(O)—, —X—(C 1 -C 8 -alkylene)-NR 10 —C(O)—, —X—(C 3 -C 6 -cycloalkylene)-NR 10 —C(O)—, or —X-(o-phenylene)-NR 10 —C(O)—, where each alkylene moiety may be substituted by one or more identical or different radicals R 2g , each cycloalkylene moiety may be substituted by one or more identical or different radicals R 2h and o-phenylene may be substituted by one or more identical or different radicals R 2h , where R 10 , R 2g , R 2h and X are as defined in claim 1 , or
—X—R 1 together with R 2 are —S—C(S)—NR 12 —C(O)—, where R 12 is as defined in claim 45 .
51 : The compound of formula I according to claim 45 , in which X is NR 14 , R 1 and R 14 together with the nitrogen atom to which they are bound form a 5-, 6- or 7-membered saturated or unsaturated heterocycle which may comprise a further heteroatom or heteroatomic group selected from O, S, NH, N(C 1 -C 8 -alkyl) and CO and which may carry 1, 2, 3 or 4 substituents independently of one another selected from halogen, cyano, C 1 -C 4 -alkyl, nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy.
52 : The compound of formula I according to claim 45 s, where R 3 is selected from C 2 -C 12 -alkyl, C 2 -C 12 -alkenyl, naphthyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl, where the phenyl moiety is substituted by one or more radicals selected from F, Cl, Br, I, C 1 -C 4 -alkoxycarbonylsulfanyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkyl, phenoxy, phenyl and cyano, C 1 -C 6 -haloalkyl, C 2 -C 12 -alkyl which is substituted by C 1 -C 4 -alkoxycarbonyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -cycloalkyl-C 1 -C 12 -alkyl, heteroaryl, heterocyclyl, and C 6 -C 10 -aryl, where
each cycloalkyl and heterocyclyl may be interrupted by one or two CO and/or may be substituted by one or more C 1 -C 12 -alkyl and where aryl may be substituted by one or more identical or different radicals selected from C 1 -C 12 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 12 -alkenyl, F, Cl, Br, I, CN, NO 2 , SR 4 , OR 5 , NR 6 R 7 , COR 8 , COOR 9 , CONR 10 R 11 or phenyl, where R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are as defined in claim 45 .
53 : The compound of formula I according to claim 45 , where a is 2 and b is 0 and c is 0, and Q is L-C 1 -C 30 -alkylene-L, L-C 3 -C 16 -cycloalkylene-L, L-heterocycloalkylene-L, L-C 6 -C 20 -arylene-L, L-C 1 -C 30 -alkylene-L 2 -L, L-C 3 -C 16 -cycloalkylene-L 1 -C 3 -C 16 -cycloalkylene-L or L-C 6 -C 20 -arylene-L 1 -C 6 -C 20 -arylene-L, where each alkylene may be interrupted by one or more identical or different non-adjacent phenylene, OC(O), C(O)O, O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO,
and where L is a single bond, C(S)O or C(S)NR 12 ; L 1 is a single bond, O or S; and L 2 is C 3 -C 20 -cycloalkylene, heterocycloalkylene or C 6 -C 20 -arylene.
54 : The compound of formula I according to claim 45 , where b is 2 and a is 0 and c is 0, and Q is L 5 -C 1 -C 30 -alkylene-L 5 , L 5 -C 3 -C 16 -cycloalkylene-L 5 , L 5 -heterocycloalkylene-L 5 , L 5 -C 6 -C 20 -arylene-L 5 , L 5 -C 3 -C 16 -cycloalkylene-L 7 -C 3 -C 16 -cycloalkylene-L 5 or L 5 -C 6 -C 20 -arylene-L 7 -C 6 -C 20 -arylene-L 5 , where alkylene may be interrupted by one or more identical or different non-adjacent O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, where L 5 is a single bond, S, O, NR 6 , CO, C(O)O, OC(O), NR 10 C(O) or CONR 10 , L 7 is a single bond, O or S and R 6 and R 10 are as defined in claim 45 .
55 : The compound of formula I according to claim 45 , where c is 2, a is 0 and b is 0 and Q is a divalent linker selected from C 1 -C 30 -alkylene, C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, C 3 -C 16 -cycloalkylene-L 11 -C 3 -C 3 -C 16 -cycloalkylene, C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene, where alkylene may be interrupted by one or more identical or different non-adjacent O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, and where L 11 is a single bond, O or S.
56 : The compound of formula I according to claim 45 , where two of the indices a, b and c are 1, and the remaining index is 0, Q is a divalent linker, which is selected from C 1 -C 30 -alkylene, C 3 -C 16 -cycloalkylene, heterocycloalkylene, C 6 -C 20 -arylene, C 3 -C 16 -cycloalkylene-L 11 -C 3 -C 16 -cycloalkylene, C 6 -C 20 -arylene-L 11 -C 6 -C 20 -arylene, where alkylene may be interrupted by one or more identical or different non-adjacent phenylene, C(O)O, OC(O); O or S, where each cycloalkylene and each heterocycloalkylene may be interrupted by one or more CO, and where L 11 is a single bond, O or S.
57 : The compound of formula I according to claim 45 , where the sum of a+b+c is 3, Q is a trivalent linker, which is selected from C 1 -C 30 -alkanetriyl, C 3 -C 16 -cycloalkanetriyl, C 6 -C 20 -arenetriyl, C 1 -C 30 -alkanetriyl-L 14 -L 15 , C 1 -C 3 O-alkylene-L 14 -L 16 , C 6 -C 20 -arenetriyl-L 14 -L 5 -C 6 -C 20 -arylene, and C 6 -C 2 O-arylene-L 14 -L 15 -C 3 -C 16 -cycloalkanetriyl where each alkanetriyl and each alkylene may be interrupted by one or more identical or different non-adjacent groups selected from O, S, CO and C(O)O and/or may carry one or more identical or different radicals R Qa , where R Qa is as defined in claim 45 ;
where each cycloalkanetriyl may be interrupted by one or more CO groups, where L 14 is a single bond, O or S, L 15 is C 3 -C 20 -cycloalkylene, heterocycloalkylene or C 6 -C 20 -arylene and where L 16 is arenetriyl.
58 : The compound according to claim 45 , where the compound of formula I is selected from compounds of the formulae IA, IB and IC
where
Q, X, R 1 R 2 and R 3 are as defined in claim 1 or 2 ;
a is 2, 3 or 4;
b is 2 or 3; and
c is 2 or 3.
59 : The compound according to claim 58 , being the compound of the formula IA, where
a is 2, X is S, N(C 1 -C 6 -alkyl), N(C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl), N(benzyl), N(phenethyl), N(C 2 -C 6 -alkenyl) or N(C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl); each R 2 is independently selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl or morpholinoamide; each R 3 is independently selected from the group consisting of C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms 1 or 2 heteroatoms or heteroatomic groups selected from O, S, SO and SO 2 , thienyl, phenyl or benzyl where each of the two last mentioned radicals may be unsubstituted or may carry one, two, three, four or five radicals independently of one another selected fluorine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -fluoroalkyl, C 1 -C 4 -alkoxycarbonyl and C 2 -C 6 -alkenyl; Q is phenylene, phenylen-S-phenylene, or C 1 -C 10 -alkylene which may be interrupted by one, two, three or four non-adjacent groups selected from phenylene, O and S.
60 : The compound according to claim 58 , being the compound of the formula IA, where
a is 3; X is S; each R 2 is independently selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl or morpholinoamide; each R 3 is independently selected from the group consisting of C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms 1 or 2 heteroatoms or heteroatomic groups selected from O, S, SO and SO 2 , thienyl, phenyl or benzyl where each of the two last mentioned radicals may be unsubstituted or may carry one, two, three, four or five radicals independently of one another selected fluorine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -fluoroalkyl, C 1 -C 4 -alkoxycarbonyl and C 2 -C 6 -alkenyl; Q is C 1 -C 20 -alkanetriyl, which may be interrupted by 3, 4, 5, 6, 7, 8, or 9 identical or different groups selected from O, S, NR 6 , CO, C(O)O.
61 : The compound according to claim 58 , being the compound of the formula IA, where
a is 4; X is S; each R 2 is independently selected from the group consisting of C 1 -C 4 -alkyl or C 1 -C 4 -alkoxycarbonyl; each R 3 is independently selected from the group consisting of C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms 1 or 2 heteroatoms or heteroatomic groups selected from O, S, SO and SO 2 , thienyl, phenyl or benzyl where each of the two last mentioned radicals may be unsubstituted or may carry one, two, three, four or five radicals independently of one another selected fluorine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -fluoroalkyl, C 1 -C 4 -alkoxycarbonyl and C 2 -C 6 -alkenyl; Q is C 1 -C 20 -alkanetetrayl, which may be interrupted by 3, 4, 5, 6, 7, 8, or 9 identical or different groups selected from O, S, NR 6 , CO and C(O)O.
62 : The compound according to claim 58 , being the compound of the formula IB, where
b is 2; X is S; each R 1 is independently selected from the group consisting of C 1 -C 6 -alkyl, mercapto-C 3 -C 6 -alkyl, mercapto-C 3 -C 6 -alkyl-S—C 1 -C 2 -alkyl, C 2 -C 4 -alkenyl, benzyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl; phenyl; phenyl which is substituted by one or two C 1 -C 4 -alkyl or C 2 -C 4 -alkenyl; and Q is C 1 -C 10 -alkylene which may be interrupted by one, two, three or four more non-adjacent atoms selected from O and S.
63 : The compound according to claim 58 , being the compound of the formula IC, where
c is 2; X is S; each R 1 is independently selected from the group consisting of C 1 -C 6 -alkyl, C 3 -C 8 -alkenyl, mercapto-C 3 -C 6 -alkyl, mercapto-C 3 -C 6 -alkyl-S—C 1 -C 2 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 2 -alkyl, C 2 -C 4 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 2 -alkyl, phenyl-C 1 -C 4 -alkylsulfanyl-C 1 -C 4 -alkyl-O—C 1 -C 4 -alkyl, phenethylsulfanyl-C 1 -C 4 -alkyl-O—C 1 -C 2 -alkyl, phenyl, phenethyl or benzyl where each phenyl moiety in the five last mentioned radicals may be substituted by one, two or three radicals selected from nitro, C 2 -C 4 -alkenyl and C 1 -C 4 -alkyl; each R 2 is independently selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 4 -alkoxycarbonyl, morpholinoamide or C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl; and Q is C 1 -C 10 -alkylene which may be interrupted by one, two, three or four non-adjacent groups selected from O, S, phenylene and naphthylene.
64 : The compound according to claim 45 , being the compound of formula ID,
where
Q is a divalent linker selected from is phenylene, phenylen-S-phenylene, or C 1 -C 10 -alkylene which may be interrupted by one, two, three or four non-adjacent groups selected from phenylene, O and S;
each X is S;
R 1 is C 3 -C 6 -alkyl, mercapto-C 3 -C 6 -alkyl, mercapto-C 3 -C 6 -alkyl-S—C 1 -C 2 -alkyl, C 2 -C 4 -alkenyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 2 -alkyl, benzylsulfanyl-C 1 -C 4 -alkyl-O—C 1 -C 4 -alkyl, phenethylsulfanyl-C 1 -C 4 -alkyl-O—C 1 -C 4 -alkyl, phenyl or benzyl where phenyl and the phenyl moiety of benzyl may be substituted by one, two or three radicals selected from nitro and C 1 -C 4 -alkyl, benzyl which is substituted by C 1 -C 4 -alkanoyl-S—C 1 -C 2 -alkyl;
each R 2 is independently of each other selected from independently selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 4 -alkoxycarbonyl, morpholinoamide or C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxycarbonyl; and
R 3 is C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, 5- or 6-membered saturated heterocyclyl comprising besides carbon atoms 1 or 2 heteroatoms or heteroatomic groups selected from O, S, SO and SO 2 , thienyl, phenyl or benzyl where each of the two last mentioned radicals may be unsubstituted or may carry one, two, three, four or five radicals independently of one another selected fluorine, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -fluoroalkyl, C 1 -C 4 -alkoxycarbonyl and C 2 -C 6 -alkenyl.Join the waitlist — get patent alerts
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