Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to novel pyridazine compounds of formula I. Moreover, the invention relates to processes and intermediates for preparing pyridazines of formula I, and also to active compound combinations comprising them, to compositions comprising them and to their use for protecting growing plants from attack or infestation by invertebrate pests.
• the invention relates to methods of applying such compounds.
• the invention also relates to seed comprising such compounds.
• Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property.
• There is an ongoing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes.
• WO 2009/027393, WO 2010/034737, WO 2010/034738, and WO 2010/112177 describe derivatives of N-arylamides derived from pyrazole carboxylic acids and pyrimidine or pyridine amines.
• WO 2016/128298, WO 2017/137337, WO 2017/137319, WO 2017/137338, WO 2017/137339, and WO 2017/186536 describe derivatives of N-arylamides derived from imidazole carboxylic acids and pyridine amines. These compounds are dscribed as useful for combating invertebrate pests.
• the present invention relates to novel pyridazine compounds of formula i
• R P1 , R P2 , and R P3 are independently of each other H, CN, halogen, CrC 4 -alkyl, CrC 3 -haloalkyl, CrC 4 -alkoxy, CrC 3 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 3 -haloalkylthio, Ci-C 4 -aikylsulfinyl, CrCs-haloalkylsulfiny!, Ci-C 4 -aIkyIsulfonyl, CrC 3 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 - Ce-halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, or Ci-C 4 -alkoxy-CrC 4 - alkyl;
• T is S, O, or NR 1b , wherein R 1b is H, Ci-Cio-alkyl, Ci-C 4 -haloalkyl, C 3 -Cio-cycloalkyl, C 3 -Cio-cycloalkylmethyl, C3-C10- halocycloalkyl, C 2 -Ci 0 -alkenyl, C 2 -Cio-haloalkenyl, C 2 -Cio-alkynyl, CrCio-alkoxy-Ci-C 4 - a!ky!, OR a , 3- to 10-membered heterocyclyl, 3- to 10-mem bered heterocyclyI-CrC 4 -alkyl, aryl, hetaryl, aryl-Ci-C4-alkyl, or hetaryl-CrC4-alkyl, wherein the cyclic moieties are unsubstituted or substituted with one or more
• R 1 is H, CN, CrCio-alkyl, CrCio-haloalkyl, C 3 -Cio-cycloalkyl, C 3 -Cio-halocycloalkyl, C1-C4- alkoxy-Ci-C 4 -alkyl, C 2 -Cio-alkenyl, C 2 -Cio-haloalkenyl, C2-Ci 0 -alkynyl, C 3 -Cio-haloalkynyl, CrCs-alkylene-CN, OR a , CrCs-alkylene-OR 3 , C(Y)R b , Ci-C5-alkylene-C(Y)R b , C(Y)OR c , Ci-C 5 -alkylene-C(Y)OR c , S(0) 2 R d , NR e R f , Ci-C 5 -alkylene-NR e R f ,
• heterocyclyl hetaryl, aryl-Ci-Cs-alkyl, C3-Cio-cycloalkyl-Ci-C 5 -alkyl, 3- to 10-membered heterocyclyl-CrCs-alkyl, or hetaryl-CrCs-alkyl, wherein the cyclic moieties are
• R 2 is H, CN, CrCio-alkyl, C2-Cio-alkenyl, C 2 -Cio-alkynyl, U-C 3 -Cio-cycloalkyl, L 1 -(3- to 6- membered heterocyclyl), L 1 -aryl, or L 1 -heteroaryl, which heterocyclyl groups contain one or more, same or different heteroatoms O, N, S(0) m or NR 3A , which cyclic groups may contain one or more groups CO, and wherein the groups are unsubstituted or substituted with one or more, same or different substituents R x ; wherein
• L 1 is a direct bond, Ci-C 8 -alkylene, C 2 -C 8 -alkenylene, C 2 -C 8 -alkynylene, or C 3 -Ce- cycloalkylene, wherein the C-atoms are unsubstituted or substituted with one or more, same or different substituents R x ;
• R 3 is H, halogen, CN, Ci-Cio-alkyl, CrCio-haloalkyl, CrCio-alkoxy, or CrCio-haloalkoxy;
• L 2 is CrCe-alkylene, C 2 -C e -alkenylene, C 2 -C 8 -alkynylene, or Ca-Ce-cycloalkylene, wherein the C-atoms are unsubstituted or substituted with one or more, same or different substituents R x ;
• R 4a , R 4b and R 4c are independently of each other H, halogen, CN, NO 2 , CrCio-alkyl, C 2 -C 10 - alkenyl, or C 2 -Cio-alkynyl, wherein the C-atoms are unsubstituted or substituted with one or more, same or different substituents R x ;
• A is a 3- to 12-membered non-aromatic carbo- or heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidised, and which carbo- or heterocycles are unsubstituted or substituted with one or more, same or different substituents Ri and/or R';
• D is a direct bond, Ci-Ce-alkylene, C 2 -C 6 -alkenyiene, or C 2 -C 6 -aikynylene, which carbon chains are unsubstituted or substituted with one or more, same or different substituents
• E is a non-aromatic 3- to 12-membered carbo- or heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidised, and which carbo- or heterocycles are unsubstituted or substituted with one or more, same or different substituents R n and/or R';
• R 4d is CrC-rhaloalkyl or C 3 -C 6 -cycloalkyl, which may each be halogenated;
• G is CrCe-a!kylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynyIene, C 3 -C 6 -cycloalkylene, or Cs-Ce- cycloalkenylene, wherein the C-atoms are unsubstituted or substituted with one or more, same or different substituents RP;
• R 4e is H, CrCe-alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -aIkynyl, Cs-Ce-cycloalkyl, Cs-Ce-cycIoalken l, or a 3- to 6-membered heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidised, which groups are unsubstituted or substituted with one or more, same or different substituents R r and/or R 1 ;
• Q is a direct bond, CrCe-alkylene, C 2 -Ce-alkenylene, or C 2 -C 8 -alkynylene, which carbon chains are unsubstituted or substituted with one or more, same or different substituents R r ; or
• Q and R 4e together form a 3- to 6-membered carbocyclic ring, or a 4- to 6-membered
• heterocycle with a direct bond to the imidazole which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and which rings are unsubstituted or substituted with one or more, same or different substituents R r and/or R 1 ;
• M is O, S, NR M , NOR M , or NSR M ;
• R M is a group mentioned for R 4® , or wherein
• R M and Q together form a 4- to 6-membered unsaturated, non-aromatic N-containing
• heterocycle which heterocycle may contain an additional heteroatom O, or S, wherein S may be oxidized, and which ring is unsubstituted or substituted with one or more, same or different substituents R r ;
• R 4 s is H, CrCe-alkyl, CrCe-alkyl-X, Cs-C B -cycloaikyl, or Cs-Ce-cycloalkyl-X;
• R 4f is CrCe-alkyl, CrCe-alkyl-X, Cs-Ce-cycloalkyl, or C 3 -C 6 -cycloalkyl-X; wherein the C1-C6- alkyl or Ca-Ce-cycloalkyl groups are unsubstituted or substituted with one or more, same or different substituents R ⁇ ; wherein
• X is O, S, NH or NR';
• R 4 9 and R 4f together with the carbon atom to which they are bonded form a 3- to 8-membered, saturated or unsaturated carbo- or heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and wherein the carbo- or heterocycles are unsubstituted or substituted with one or more, same or different substituents R‘ and/or R 1 ;
• W is CrCe-alkylene, Cs-Ce-cydoalkylene, Cs-Ce-heterocycloalkylene, C 2 -C 8 -alkenylene, C 3 - Ce-cycloalkenylene, C 3 -Ce-heterocycloalkenylene, or C 2 -C 8 -alkynylene, wherein W is unsubstituted or substituted with one or more, same or different substituents R‘ and/or R 1 ;
• V is O, S or NR 1a , wherein
• R 1a is H, CrCio-alkyl, Ci-C4-haloalkyl, Ca-Cio-cyctoalkyl, Ca-Cio-cycIoalkylmethyl, C 3 -C 10 - halocycloalkyl, C 2 -Cio-alkenyl, C 2 -Cio-haloalkenyl, C2-Cio-alkynyl, CrCio-alkoxy-Ci-C4- alkyl, OR a , 3- to 10-membered heterocyclyl, 3- to 10-mem bered heterocyciyl-CrC4-alkyl, aryl, hetaryl, aryl-CrC4-alkyl, or hetaryl-Ci-C4-alkyl, wherein the cyclic moieties are unsubstituted or substituted with one or more, same or different substituents R aa ; or wherein
• R 1a and R 4 a together with the carbon atom to which R 4 s is bonded and the nitrogen atom to
• R 1a is bonded as well as the nitrogen atom between said carbon atom and said nitrogen atom form a 4- to 8-membered heterocycle, which contains the two nitrogen atoms as heteroatoms, and may further contain one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and wherein the heterocycle is unsubstituted or substituted with one or more, same or different substituents R‘ and/or R 1 ; or R 4 is
• R 4h , R 4i are independently of each other CN; Ci-Ce-alkyl, Ci-Ce-alkenyl, or C 2 -Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A1 ;
• heterocyclyl-Ci-C 4 -alkyl which heterocyclyl group contains one or more, same or different heteroatoms O, N, S(0) m or NR 3A , which cyclic groups may contain one or more, same or different groups C(G A )R 2A , and wherein the C-atoms of these groups are unsubstituted or substituted by one or more, same or different substituents R M ;
• aryl or hetaryl which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R A5 ; or
• G A is O, N-CN, or N-OR 2A ;
• R 2A is H; Ci-Ce-aikyi, C 2 -Ce-alkenyl, or C 2 -C 8 -alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• heterocyclyl-CrC 4 -alkyl which heterocyclyl group contains one or more, same or different heteroatoms O or S(0) m , and wherein the C-atoms of these groups are unsubstituted or substituted by one or more, same or different substituents R M ;
• aryl or hetaryl which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R A6 ; or
• R 3A is H; CrC 6 -alkyl, Ca-Ce-aikenyl, or Ca-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ; or
• R 4A is H; Ci-Ce-alkyl, Ca-Ce-alkenyl, or Cs-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 4 i is H; Ci-Ce-alkyl, C 2 -Ce-alkenyl, or C2-Ce-aIkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• heterocyclyl group contains one or more, same or different heteroatoms O, N, S(0) m or NR 4aB , which cyclic groups may contain one or more groups CO, and wherein the C-atoms of these groups are unsubstituted or substituted by one or more, same or different substituents R M ; or
• R 2B , R 3B , R 4B are independently of each other H; CrCe-alkyl, C 2 -Ce-alkenyl, or C 2 -Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• aryl or hetaryl which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R A6 ; or
• R 3aB is H; CrCe-alkyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• aryl or hetaryl which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R A6 ; or
• R 4aB is H; CrC 4 -alkyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents selected from halogen or Ci-C 4 -alkoxy;
• R 5B is CrCe-alkyl, C 2 -Ce-alkenyl, or C 2 -C 8 -alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents selected from halogen or C 1 -C 4 - alkoxy; or
• R 6B is CrCe-alkyl, C 2 -Ce-aIkenyl, or C2-Ce-alkynyi, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 41 is H; CrCe-alkyl, C2-Ce-alkenyl, or C2-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• heterocyclyl group contains one or more, same or different heteroatoms O, or S(0) m , and which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R M ;
• aryl or hetaryl which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R A6 ; or
• # are the bonds to the carbon atom of the C(T 1 ) moiety of the C(T 1 )R 41 group; and wherein L A and L B are independently from each other O, or S(0) m ; and
• a 1 is C2-C 4 -alkylene, wherein the C-atoms are unsubstituted or substituted with one or more, same or different substituents R 4C ;
• R 1C is H; CrCe-alkyl, C2-Ce-alkenyl, or C2-C8-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 2C is H; CrCe-alkyl, C2-Ce-aIkenyi, or C 2 -C 8 -alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 3C is H; CrCe-alkyl, C 2 -Ce-alkenyl, or C2-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 4C is halogen; CrCe-alkyl, C 2 -Ce-alkenyl, or C2-C 8 -alkyn I, which aliphatic groups are
• two R 4C bonded to the same carbon atom form a C 2 -C 4 -alkylene chain, which chain is unsubstituted or substituted by one or more, same or different substituents R M ; or two R 4C bonded to the same carbon atom form a Ci-C 4 -alkenylene chain with the double bond of the chain being attached to said carbon atom, which chain is unsubstituted or substituted by one or more, same or different substituents R M ;
• R 4m is H; CrCe-alkyl, C 2 -C 8 -alkenyl, or C2-C8-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• aryl or hetaryl which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R A6 ; or
• R 4n is H; CrCe-alkyl, C 2 -C 0 -alkenyl, or C2-C 8 -aIkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 40 is H; CrCe-alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, CrC 4 -alkoxy, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A2 ; C3-Ce-cycIoalkyI, or 3- to 8-membered heterocyelyl, which heterocyclyl group contains one or more, same or different heteroatoms O, N, S(0) m or NR 3A , which cyclic groups may contain one or more groups CO, and which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R M ;
• aryi-Ci-C 4 -alkyl or hetaryl-CrC 4 -alkyl wherein the C-atoms of these groups are unsubstituted or substituted by one or more, same or different substituents R A7 ; or R 4n and R 40 together with the nitrogen atom to which they are bonded form a 3- to 8-membered heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and wherein the heterocycle is unsubstituted or substituted with one or more, same or different substituents R M ;
• R 4 P is H; CrCe-alkyl, C 2 -C 8 -alkenyl, or C 2 -Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 4( i is H; CrCe-alkyl, C 2 -C 8 -alkenyl, or C 2 -Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 4r is H; CrCe-alkyl, C 2 -C 8 -alkenyl, or C 2 -Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• aryl, hetaryl, aryl-CrC 4 -aIkyl or hetaryl-CrC 4 -alkyl which groups are unsubstituted or substituted by one or more, same or different substituents R A6 ;
• R 4s is aryl or hetaryl, which cyclic groups are unsubstituted or substituted by one or more, same or different substituents R 1D ;
• R 1D is CN, NO2, halogen, NR 2D R 3D ; Ci-C 4 -alkyl, Ci-C4-alkoxy-CrC 4 -alkyl, CrC4-halogenalkyl, CrC 4 -alkoxy, CrC 4 -haloalkoxy, Ci-C 4 -alkyl-S(0) m -, CrC 4 -haloalkyl-S(0) m -, carboxy; or aryl, or hetaryl, which groups are unsubstituted or substituted with one or more, same or different substituents R A6 ; or
• heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and which heterocycle is unsubstituted or substituted with one or more, same or different
• R 2D is H; Ci-C 4 -alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C3-Ce-cycloalkyl, which groups are
• R 3D is H; CrC4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or Cs-Ce-cycloalkyl, which groups are
• R 2D and R 3D together with the nitrogen atom to which they are bonded form a 3- to 8-membered heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and which heterocycle is unsubstituted or substituted with one or more, same or different substituents R A6 ;
• R 4t is H; CN; CrCe-alkyl, C2-C8-alkenyl, or C2-Ce-alkynyl, which aliphatic groups are
• aryl, hetaryl, aryl-Ci-C4-alkyl, or hetaryl-CrC 4 -alkyl which groups are unsubstituted or substituted by one or more, same or different substituents R A6 ;
• R 4u is H; Ci-C 4 -alkyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ; or
• R 4t and R 4u together with the carbon atom to which they are bonded form a 3- to 8-membered carbocyclic or heterocyclic ring, which heterocyclic ring contains one or more, same or different heteroatoms O, N, S(0) m , or NR 1F , which cyclic groups may contain one or more, same or different groups CO, and wherein the carbocyclic or heterocyclic ring is unsubstituted or substituted with one or more, same or different substituents R A3 ; or
• R 4t and R 4u together are C 2 -C 6 -alkenyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 4v is H; S(0) n R 1E , OR 2E , or N(R 3E )(R 4E ),
• R 4t and/or R 4u is H » or CrCe-alkyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 , R 4v is S(0) n R 1E , OR 2E , or N(R 3E )(R 4E );
• R 1E is CrCe-alkyl, Ca-Ce-alkenyl, or Ca-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A9 ;
• Cs-Ce-cycloalkenyl Cs-Ce-cycloalkeny l-C 1 -C4-al kyl , 3- to 8-membered heterocyclyl, or 3- to 8-mem bered heterocyclyl-Ci-C4-alkyl, which heterocyclyl group contains one or more, same or different heteroatoms O, N, S(0) m , or NR 1F , which cyclic groups may contain one or more, same or different groups CO, and wherein the C-atoms of these groups are unsubstituted or substituted by one or more, same or different substituents R A4 ; or aryl, hetaryl, aryl-CrC 4 -alkyl, or hetaryl-CrC 4 -alkyl, which groups are unsubstituted or substituted by one or more, same or different substituents R A6 ;
• R 2E is H; CrCe-alkyl, Cs-Ca-alkenyl, or C3-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A9 ;
• R 3E is H; CrCe-alkyl, Cs-Ca-a!kenyl, or Cs-Ce-a!kynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 4E is H; CrCe-alkyl, C 3 -C 8 -alkenyl, or Ca-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ; or
• R 3E and R 4E together with the nitrogen atom to which they are bonded form a 3- to 9-membered heterocycle, which heterocyclyl group contains one or more, same or different
• heteroatoms O, N, S(0) m , or NR 1F which cyclic groups may contain one or more, same or different groups CO, and wherein the C-atoms of these groups are unsubstituted or substituted by one or more, same or different substituents R A8 ; or
• R 5E and R 6E are independently of each other H; Ci-Ce-alkyl, C 3 -Ca-alkenyl, or Cs-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 5E and R 6E together with the nitrogen atom to which they are bonded form a 3- to 8-membered heterocyclic ring, which heterocyclic ring contains one or more, same or different heteroatoms O, or S(0) m , and which heterocycle is unsubstituted or substituted with one or more, same or different substituents R A1 °;
• R 7E is H; CrCe-alkyl, Ca-Ce-alkenyl, or C3-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• Cs-Ce-cycloalkenyl Cs-Ce-cycloalkenyl-C 1 -C 4 -alkyl , 3- to 8-membered heterocyclyl, or 3- to 8-membered heterocyclyl-CrC 4 -alkyl, which heterocyclyl group contains one or more, same or different heteroatoms O, N, S(0) m , or NR 1F , which cyclic groups may contain one or more, same or different groups CO, and wherein the C-atoms of these groups are unsubstituted or substituted by one or more, same or different substituents R M ; or aryl, hetaryl, aryl-CrC 4 -alkyl, or hetaryl-Ci-C4-alkyl, which groups are unsubstituted or substituted by one or more, same or different substituents R Ae ;
• R 8E is H; CrCe-alkyl, Cs-Ce-alkenyl, or C 3 -C8-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 9E is Ci-Ce-alkyl, Ca-Ce-alkenyl, or Cs-Ce-alkynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R 1 F is H; CrCe-alkyl, Ca-Ce-alkenyl, or Cs-Ce-aikynyl, which aliphatic groups are unsubstituted or substituted by one or more, same or different substituents R A3 ;
• R a , R b , R c are independently of each other H, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 3 -Ce-cycloalkyl, C 3 - Ce-cycloalkylmethyl, Cs-Ce-halocycloalkyl, C 3 -C 6 -cycloalkenyl, Cs-Ce-cycloalkenylmethyl, C 3 -C 6 -halocycloalkenyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, Ci-C 4 -alkoxy-Cr C 4 -alkyl, 3- to 6-mem bered heterocyclyl, 3- to 6-membered heterocyclyl-CrC 4 -alkyl, aryl, hetaryl, aryl-CrC 4 -alkyl, or hetaryl-
• R d is H, CrC 4 -alkoxy, CrC4-alkyl, CrC4-haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl,
• R e ,R f are independently of each other H, CrC 4 -alkyl, CrC 4 -haloalkyl, Cs-Ce-cycloalkyl, Cs-Ce- cycloalkylmethyl, Cs-Ce-halocycloalkyl, Cs-Ce-cycloalkenyl, Cs-Ce-cycloalkenylmethyl, C 3 - Ce-halocycloalkenyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -alkynyl, CrC 4 -alkoxy-Ci-C 4 - alkyl, CrC 4 -alkylcarbonyl, CrC 4 -haloalkylcarbonyl, CrC 4 -alkylsulfonyl, Ci-C 4 - haloalkylsulfonyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl
• R e and R f together with the nitrogen atom to which they are bonded form a 5- or 6-membered, saturated or unsaturated heterocycle, which may contain a further heteroatom O, S, or N, wherein S may be oxidized, and wherein the heterocycles are unsubstituted or substituted with one or more, same or different substituents R aa ;
• R9,R h are independently of each other H, CrC 4 -alkyl, Ci-C 4 -haloalkyl, l_-C3-Ce-cycloalkyl, L-C3- Ce-halocycloalkyl, L-Ca-Ce-cycloalkenyl, L-Cs-Ce-halocycloalkenyl, C2-C 4 -alkenyl, C 2 -C 4 - ha!oalkenyl, C2-C 4 -alkynyl, CrC 4 -alkoxy-Ci-C 4 -alkyl, 3- to 6-membered heterocyclyl, 3- to 6-membered heterocyclyl-CrC 4 -alkyl, aryl, hetaryl, aryl-CrC 4 -alkyl, or hetaryl-CrC 4 -alkyl, wherein the cyclic moieties are unsubstituted or substituted with one or more, same
• R' is H, CN, CrC 4 -alkyl, CrC 4 -haloalkyl, L-Cs-Ce-cycloalkyl, L-Cs-Ce-halocycloalkyl, L-C 3 -C 6 - cycloalkenyl, L-Cs-Ce-halocycloalkenyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C 2 -C 4 -alkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, aryl, or aryl-CrC 4 -alkyl, wherein the aryl rings are unsubstituted or substituted with one or more, same or different substituents R aa ;
• Ri bonded to C is halogen, OH, CN, NO2, Ci-Cio-alkyl, CrCio-haloalkyl, CrCio-alkoxy, Cr Cio-haloalkoxy, S(0) m R k , Cs-Ce-cycloalkyl, or 3- to 6-membered heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, which Ri groups are unsubstituted or substituted with one or more, same or different substituents R m and/or R', and wherein two groups Ri connected to the same or adjacent ring atoms may together form a 3- to 6-membered carbo- or heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidised, which cycles are unsubstituted or substituted with one or more, same or different substituents R m and/or R 1 ;
• R k is H, CrC 4 -alkyl, Ci-C 4 -haloalkyl, or Cs-Ce-cycloalkyl, which cycle is unsubstituted or substituted with one or more, same or different substituents R 1 ;
• R 1 bonded to N is CrC 4 -alkyl, Cr -haloalk l, Ci-C 4 -alkylcarbonyl, CrC 4 -haloalkylcarbonyl, or CrC 4 -alkoxycarbonyl;
• R m bonded to C is halogen, OH, CN, NO2, CrC 4 -alkyl, Ci-C 4 -haloalkyl, Ca-Ce-cycloalkyl, Cr C 4 -alkoxy, CrC 4 -haloalkoxy, or S(0) m R k ;
• R 10 is H, Ci-C 4 -alkyl, CrC 4 -haloalkyl, C 3 -Ce-cycloalkyl, or Ci-C 4 -alkoxy;
• R° bonded to C is Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 3 -Ce-cycloalkyl, CrC -alkoxy, CrC - alkylcarbonyl, Ci-C 4 -haloalkylcarbonyI, or Ci-C 4 -alkoxycarbonyl;
• RP is halogen, CN, NO 2 , Ci-C 2 -alkyl, CrC 2 -haloalkyl, C 3 -C 6 -cycloalkyl, CrC 4 -alkoxy, or Cr C2-haloalkoxy, or two groups RP can together form a 3- to 6-membered carbo- or heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidised, which carbo- or heterocycle is unsubstituted or substituted with one or more, same or different substituents R ;
• R q is halogen, CN, NO2, CrC 4 -alkyl, Ci-C 4 -haloalkyl, C3-Ce-cycfoaIkyl, CrC 4 -alkoxy, or Cr C 4 -haloalkoxy;
• R r bonded to C is halogen, CN, NO 2 , CrC 2 -alkyl, CrC 2 -haloalkyl, Ci-C -alkoxy, C 1 -C 2 - haloalkoxy, or S(0) m R k ; or two groups R r together form a 3- to 6-membered carbo- or heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and which carbo- or heterocycles are unsubstituted or substituted with R s ;
• R s is halogen, CN, NO2, CrC 2 -alkyl, CrC2-haloalkyl, Cs-Ce-cycloalk l, Ci-C 4 -alkoxy, or Cr C 2 -haloalkoxy;
• R v is CrC 4 -alkyl, CrC 4 -haloalkyl, Cs-Ce-cycloalkyl, or C 3 -Ce-halocycloalkyl;
• R w is H, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ca-Ce-cycloalkyl, C 3 -Ce-halocycloal ky I , CrC 4 -alkoxy, or CrC 4 -haloalkoxy;
• R x is halogen, CN, N0 2 , Ci-C 4 -alkyl, CrC 4 -haloalkyl, CrC 4 -alkoxy, Ci-C 4 -haloalkoxy,
• R y is halogen, CN, NO2, CrC 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, CrC4-haIoalkoxy,
• R aa is halogen, CN, NO2, CrC 4 -alkyl, Ci-C -haloalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -haloalkoxy;
• R A1 is CN, halogen, Ci-C 4 -alkoxy, Ci-C 4 -alkyl-S(0) m -, C(0)R 2A , C(0)NR 2A R 3A , or C(G A )R 2A ;
• R A2 is CN, halogen, OH, CrC 4 -alkoxy, Ci-C 4 -alkoxycarbonyl, or Ci-C 4 -alkyl-S(0) m -;
• R A3 is CN, halogen, CrC 4 -aikoxy, or Ci-C 4 -alkyl-S(0) m -;
• R M is CN, halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, or Ci-C 4 -alkoxy;
• R A5 is CN, NO2, halogen, oxime ether, acylamido, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkyl-S(0) m -, Ci-C 4 -haloalkyl-S(0)m-; or
• R Z1 is CN, NO2, halogen, Ci-C 4 -aikyl, Ci-C 4 -haloalkyl, CrC 4 -alkoxy, Ci-C 4 -haloalkoxy, C1-C4- alkyl-S(0) m -, CrC 4 -haloalkyl-S(0) m -, hetaryloxy, or aryloxy;
• R A6 is CN, NO2, halogen, CrC 4 -alkyl, CrC 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, C1-C4- alkyl-S(0) m -, or Ci-C4-haloalkyl-S(0) m -;
• R A7 is CN, NO2, halogen, Ci-C4-alkyl, C r C 4 -haloalkyl, OH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Cr C4-alkyl-S(0)m-, or Ci-C 4 -haloalkyl-S(0) m -;
• R A8 is H, CN, N0 2I Ci-C 4 -alkyl, Gs-Ce-cyc!oaikyl, CrC 5 -haloalkyl, Ci-C 4 -alkoxy, C1-C4- haloalkoxy, Cs-Ce-halogencycloalkyi, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, cyano-CrC 4 -alkyl, C3-C6- cycloal kyl-C 1 -C 4 -al ky I , C2-C 6 -alkenyl, Ca-Ce-alkynyl, Ci-C 4 -alkyl-S(0) m -, C1-C4- alkylcarbonyl, C1 -Ce-haloalkylcarbonyl , CrCe-a!koxycarbonyl, C Ce-alkyfaminocarbonyl, di-(CrC 6 )-
• R Z2 is CN, N0 2I halogen, CrC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 4 -alkoxy, C1-C4- haloalkyl, Ci-C 6 -haloalkoxy, or Ci-C 4 -aikylthio;
• R A9 is CN, halogen, Ci-C 4 -alkoxy, Ci-C 4 -alkyl-S(0)m-, C(0)OR 2A , C(0)NR 2A R 3A , or C(G A )R 2A ;
• R A1 ° is Ci-C 2 -alkyl, CrC 2 -haloaikyi, Ci-C 2 -alkoxy;
• Y is O or S
• n 0, 1 or 2;
• the present invention relates to a composition and to an agricultural composition for combating animal pests comprising at least one compound of formula I.
• the present invention relates to a method for combating or controlling invertebrate pests and to a method for protecting growing plants form attack or infestation by invertebrate pests.
• the present invention relates to seed comprising a compound of formula I, and in yet another aspect, the present invention relates to the use of the compounds of formula I for protecting growing plants from attack or infestation by invertebrate pests.
• the present invention relates to compounds of formula I, wherein T is O, S or NR 1b . These compounds correspond to formula 1.1 , formula I.2 and formula 1.3, respectively.
• the compounds according to the invention can be prepared analogously to the synthesis routes described in WO 2009/027393 and WO 2010/034737 or according to standard processes of organic chemistry.
• Compounds of formula 1.1 wherein T is O, can be prepared e.g. by reacting activated imidazole carboxylic add derivatives of formula il with a 4-aminopyridazine of formula III (e.g. Houben-Weyl:“Methoden der organ. Chemie” [Methods of Organic Chemistry], Georg-Thieme- Verlag, Stutgart, New York 1985, Volume E5, pp. 941-1045).
• a 4-aminopyridazine of formula III e.g. Houben-Weyl:“Methoden der organ. Chemie” [Methods of Organic Chemistry], Georg-Thieme- Verlag, Stutgart, New York 1985, Volume E5, pp. 941-1045).
• Compounds of formula 1.1 wherein R 1 is different from hydrogen can also be prepared by alkylating the amides 1.1 , in which R 1 is hydrogen, using suitable alkylating agents in the presence of bases.
• the alkylation can be effected under standard conditions known from literature.
• X is a suitable leaving group such as halogen, Ns, p-nitrophenoxy, pentafluorophenoxy or the like.
• Activated imidazole carboxylic acid derivatives of formula II are preferably halides, activated esters, anhydrides, or azides, e.g. chlorides, fluorides, bromides, para-nitrophenyl esters, pentafluorophenyl esters, N-hydroxysuccinimides, or hydroxybenzotriazol-1-yl esters.
• the introduction of groups R 2 , R 3 and R 4 into the imidazole compounds of formula II may be effected by generally known methods of organic chemistry. For example, the introduction of sulfur bonded R 4 groups in formula I.A(v) compounds as defined in further detail below can be achieved analogously to the synthesis routes described in WO 2016/128298.
• R 4 groups as defined herein can be achieved analogously to the synthesis routes described in WO 2017/137337, WO 2017/137319, WO 2017/137338, WO 2017/137339, or WO 2017/186536.
• imidazole carboxylic acid derivatives of formula II may comprise any one of the following groups as R 4
• the following activated imidazole carboxylic acid derivatives of formula II are preferably used in the above described syntheses of the imidazole compounds of formula 1.1. It is to be understood that the substituent R 3 and the group -COX may be present in two different positions. Accordingly, the following compounds of formula II, namely the compounds of formulae ll(iiia)-1 to ll(viii)-1 and the compounds of formula ll(iiia)-2 to li(viii)-2, are relevant for the present application. It is to be understood that the compounds of formula ll(iiia)-1 to ll(viii)-1 are preferred over the compounds of formula ll(iiia)-2 to ll(viii)-2.
• the activated imidazole carboxylic acid derivatives of formula II including the activated imidazole carboxylic acid derivatives of formulae ll(iiia)-1 , ll(iiib)-1 , ll(iiic)-1 , ll(iiid)-1 , ll(iva)-1 , ll(ivb)-1 , ll(va)-1 , II(vb)-1 , ll(vc)-1 , ll(via)-1 , ll(vib)-1 , ll(vic)-1 , ll(vid)-1 , ll(vii)-1 and ll(viii)-1 as well as the activated imidazole carboxylic acid derivatives of formulae ll(iiia)-2, ll(iiib)-2, ll(iiic)-2, ll(iiid)-2, ll(iva)-2, ll(ivb)-2, ll(va)-2, ll(vb)-2
• the activated imidazole carboxylic acid derivatives of formulae ll(ivb)-1 and ll(ivb)-2 can be prepared by methods known in the art starting from commercially available precursors.
• the carbon nitrogen double bond of group (ivb) may be established by a reaction, which is analogous to an imine formation, starting from an aldehyde or ketone substituted by R 4 ⁇ and R 4f and a suitable imidazole carboxylic acid derivative (see WO 2013/072882, J. Org.
• the V-W-bond of group (ivb) may be established by a substitution reaction, starting from an oxime, thioxime or hydrazine substituted by R 4 s and R 4f and a suitable imidazole carboxylic acid derivative, which contains a leaving group at the W substituent (see J. Med. Chem, 28(7), p. 896 (1985)).
• the imidazole carboxylic acid derivative may be converted to an activated imidazole carboxylic acid derivative of formula ll(ivb)-1 or ll(ib)-2.
• Compounds of formula I.2, wherein T is S can be prepared e.g. by reacting compounds of formula 1.1 with 2, 4-bis(4-methoxyphenyl)-1 , 3, 2, 4-dithiadiphosphentane-2, 4-disulfide or PSs according to the method described in Synthesis 2003, p. 1929.
• N-oxides of the compounds of formula I can be prepared by oxidation of compounds I according to standard methods of preparing heteroaromatic N-oxides, e.g. by the method described in Journal of Organometallic Chemistry 1989, 370, 17-31. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds I can advantageously be prepared from other compounds I by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like.
• reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by
• intemediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration.
• radicals attached to the backbone of formula I may contain one or more centers of chirality.
• the compounds of formula I are present in the form of different
• the present invention relates to every possible stereoisomer of the formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
• the compounds of formula I may also be present in the form of different tautomers depending e.g. on the selection of the radical R 4 .
• the present invention relates to every possible tautomer of the formula I.
• the compounds of formula I may be present in the form of different geometric isomers depending e.g. on the selection of R 4 . If geometric isomers are possible, the present invention relates to both, the E- and Z-isomers of the compounds of formula I.
• the compounds of formula I may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
• the present invention relates to amorphous and crystalline compounds of formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.
• Salts of the compounds of the formula I are preferably veterinary and/or agriculturally acceptable salts, preferably agriculturally acceptable salts. They can be formed in a customary manner, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality.
• Veterinary and/or agriculturally useful salts of the compounds of formula I encompass especially the acid addition salts of those acids whose cations and anion, respectively, have no adverse effect on the pesticidal action of the compounds of formula I.
• Anions of useful aid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of CrC4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of formula I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
• N-oxide includes any compound of formula I, which has at least one tertiary nitrogen atom that is oxidized to an N-Oxide moiety.
• the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
• the prefix C n - C m indicates in each case the possible number of carbon atoms in the group.
• halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine and bromine.
• alkyl as used herein and in the alkyl moieties of alkylamino, alkylcarbonyl, alkylthio, alkylsulfinyl, slkylsulfonyl and alkoxyaikyl denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms.
• alkyl group examples include methyl, ethyl, n-propyl, iso-propyl, n-buty!, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1-methylbutyI, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1 ,1- dimethylpropyl, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methy!pentyl, 3-methylpentyl, 4- methy I pentyl, 1 ,1 -dimethyl-butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl-butyl, 2,2-dimethylbutyl, 2,3- dimethylbutyi, 3,3-dimethyl-butyl, 1-ethyibutyI, 2-ethylbutyl, 1 ,1
• haloalkyl as used herein and in the haloalkyl moieties of haloalkylcarbonyl, hafoalkoxycarbonyf, haloalkylthio, haloalkylsulfonyl, haloalkylsulfinyl, haloalkoxy and
• haloalkoxyalkyl denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.
• Preferred haloalkyl moieties are selected from Ci-C4-haloalkyl, more preferably from Cr C3-haloalkyl or CrC2-haloalkyl, in particular from Ci-C2-fluoroalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroeth l, and the like.
• alkoxy denotes in each case a straight-chain or branched alkyl group which is bonded via an oxygen atom and has usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms.
• alkoxy group examples are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert- butyloxy, and the like.
• alkoxyaikyl refers to alkyl usually comprising 1 to 10, frequently 1 to 4, preferably 1 to 2 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 4, preferably 1 or 2 carbon atoms as defined above. Examples are CH2OCH3,
• haloalkoxy denotes in each case a straight-chain or branched alkoxy group having from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
• Preferred haloalkoxy moieties include C1-C4- haloalkoxy, in particular Ci-C2-fluoroalkoxy, such as fluoromethoxy, difluoromethoxy,
• haloalkylthio refers to an alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
• haloalkylsulfinyi refers to an alkylsulfinyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
• haloalkylsulfonyl refers to an alkylsulfonyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
• haloaikylcarbonyl refers to an alkylcarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
• alkoxycarbonyl refers to an alkylcarbonyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.
• haioa!koxycarbonyl refers to an alkoxycarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
• alkenyl denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. vinyl, ally!
• haloalkenyl refers to an alkenyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms.
• alkynyl denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. ethynyl, propargyl (2-propyn-1-yl), 1-propyn-1-yl, 1-methylprop-2-yn-1-yl), 2-butyn-1-yl, 3-butyn-1-yl, 1- pentyn-1-y(, 3-pentyn-1-yl, 4-pentyn-l-yl, 1 -methylbut-2-yn- 1 -yl, 1 -ethylprop-2-yn- 1 -yl and the like.
• haloalkynyl refers to an alkynyi group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms.
• cycloaiky as used herein and in the cycloalkyl moieties of cycloalkylalkyl, cycloalkoxy and cycloalkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 or from 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl or cyclopropyl, cyclobutyl, cyclopentyi and cyclohexyl.
• hafocycloalkyl as used herein and in the halocycloalkyl moieties of halocycloalkoxy and halocycloalkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 C atoms or 3 to 8 C atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine.
• Examples are 1- and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3, 3- tetrafluorocyclopropyl, 1- and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2- trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 1-,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3- , 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5- dichlorocyclopentyl and the like.
• cycloalkoxy refers to a cycloalkyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.
• halocycloalkoxy refers to a halocycloalkyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.
• cycloalkylthio refers to a cycloalkyl group as defined above, which is bonded via a sulfur atom to the remainder of the molecule.
• halocycloalkylthio refers to a halocycloalkyl group as defined above, which is bonded via a sulfur atom to the remainder of the molecule.
• cycloalkylsulfonyl refers to a cycloalkyl group which is bonded via the sulfur atom of the sulfonyl group to the remainder of the molecule.
• cycloalkenyl as used herein and in the cycloalkenyl moieties of cycloalkenylalkyl, cycloalkenyloxy and cycloalkenylthio denotes in each case a monocyclic singly unsaturated non-aromatic radical having usually from 3 to 10, e.g. 3 or 4 or from 5 to 10 carbon atoms, preferably from 3- to 8 carbon atoms, more preferably from 3 to 6 carbon atoms.
• cycloalkenyl group may be bonded to the remainder of the molecule via a carbon atom, which froms the double bond, or via a carbon atom, which forms a single bond, preferably via a carbon atom, which forms a double bond.
• exemplary cycloalkenyl groups include cyclopropen- 1-yl, cyclohexen-1-yl, cyclohepten-1-yl or cycloocten-1-yl.
• halocycloalkenyl as used herein and in the halocycloalkenyl moieties of
• halocycloalkenyloxy and halocycloalkenylthio denotes in each case a monocyclic singly un saturated non-aromatic radical having usually from 3 to 10, e.g. 3 or 4 or from 5 to 10 carbon atoms, preferably from 3- to 8 carbon atoms, more preferably from 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine.
• the halocycloalkenyl group may be bonded to the remainder of the molecule via a carbon atom, which forms the double bond, or via a carbon atom, which forms a single bond, preferably via a carbon atom, which forms a double bond.
• Examples are 3,3,- difluorocyclopropen-1 -yl and 3,3-dichlorocyc!opropen-1 -yi.
• cycloalkenyloxy refers to a cycloalkenyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.
• halocycloalkenyloxy refers to a halocycloalkenyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.
• cycloalkenytthio refers to a cycloalkenyl group as defined above, which is bonded via a sulfur atom to the remainder of the molecule.
• halocycloalkenylthio refers to a halocycloalkenyl group as defined above, which is bonded via a sulfur atom to the remainder of the molecule.
• “carbocycle” or“carbocyclyl” includes in general a 3- to 12-membered, preferably a 3- to 8-mem bered or a 5- to 8-membered, more preferably a 5- or 6-membered mono-cyclic, non-aromatic ring comprising 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms.
• the term“carbocycle” covers cycloalkyl and cycloalkenyl groups as defined above.
• heterocycloalkyl includes in general 3- to 8-membered, in particular 6-membered monocyclic saturated heterocyclic non-aromatic radicals.
• the heterocyclic non-aromatic radicals usually comprise 1 , 2, or 3 heteroatoms selected from N, O and S as ring members, where S- atoms as ring members may be present as S, SO or SO2.
• heterocycloalkenyl includes in general 3- to 8-membered, in particular 6-membered monocyclic singly unsaturated heterocyclic non-aromatic radicals.
• the heterocyclic nonaromatic radicals usually comprise 1 , 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2.
• heterocycle or “heterocyclyi” includes in general 3- to 12-membered, preferably 3- to 8-membered or 5- to 8-membered, more preferably 5- or 6-membered, in particular 6 membered monocyclic heterocyclic non-aromatic radicals.
• the heterocyclic non-aromatic radicals usually comprise 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2.
• Examples of 5- or 6-membered heterocyclic radicals comprise saturated or unsaturated, nonaromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxide (S- oxothietan l), thietanyl-S-dioxide (S-dioxothiethanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1 ,3-dioxolanyl, thio!anyl, S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxod i hydroth ienyl , S-dioxodihydro-thienyl, oxazolidinyl, oxazolinyl, thiazolin
• aryl includes mono-, bi- or tricyclic aromatic radicals having usually from 6 to 14, preferably 6, 10 or 14 carbon atoms.
• exemplary aryl groups include phenyl, naphthyl and anthracenyl. Phenyl is preferred as aryl group.
• heteroaryl includes monocyclic 5- or 6-mem bered heteroaromatic radicals comprising as ring members 1 , 2, 3 or 4 heteroatoms selected from N, O and S. Examples of 5- or 6-mem bered heteroaromatic radicals comprising as ring members 1 , 2, 3 or 4 heteroatoms selected from N, O and S. Examples of 5- or 6-mem bered heteroaromatic radicals comprising as ring members 1 , 2, 3 or 4 heteroatoms selected from N, O and S. Examples of 5- or
• 6-mem bered heteroaromatic radicals include pyridyl, i.e. 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e.
• 5-isothiazolyl pyrazolyl, i.e. 1-, 3-, 4- or 5-pyrazolyl, i.e. 1-, 2-, 4- or 5-imidazolyl, oxadiazolyl, e.g. 2- or 5-[1 ,3,4]oxadiazolyl, 4- or 5-(1 ,2,3-oxadiazol)yl, 3- or 5-(1 ,2,4-oxadiazol)yl, 2- or 5-(1 ,3,4-thiadiazol)yl, thiadiazolyl, e.g.
• heteroaromatic radicals comprising as ring members 1 , 2 or 3 heteroatoms selected from N, O and S, wherein a 5- or 6-membered heteroaromatic ring is fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical.
• Examples of a 5- or 6- mem bered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzo-thienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, quinolinyl, isoquinolinyl, purinyl, 1 ,8- naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.
• These fused hetaryl radicals may be bonded to the remainder of the molecule via any ring atom of 5- or 6- membered heteroaromatic ring or via a carbon atom of the fused phenyl moiety.
• heterocyclyloxy refers to heterocyclyl, hetaryl and aryl as defined above and phenyl, which are bonded via an oxygen atom to the remainder of the molecule.
• heterocyclylsulfonyl refers to heterocyclyl, hetaryl and aryl as defined above, and phenyl, respectively, which are bonded via the sulfur atom of a sulfonyl group to the remainder of the molecule.
• arylalkoxy and“phenylalkoxy” refer to arylalkyl as defined above and phenylalkyl, respectively, which are bonded via an oxygen atom to the remainder of the molecule.
• alkylene refers to alkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl and alkynyl as defined above, respectively, which are bonded to the remainder of the molecule, via two atoms, preferably via two carbon atoms, of the respective group, so that they represent a linker between two moieties of the molecule.
• cyclic moiety can refer to any cyclic groups, which are present in the compounds of formula I, and which are defined above, e.g. cycloalkyl, cycloalkenyl, carbocycle,
• heterocycloalkyl heterocycloalkenyl, heterocycle, aryl, hetaryl and the like.
• aliphatic can refer to any non-aromatic hydrocarbon group, wherein the constituent carbon atoms can be straight-chain, branched-chain, or cyclic and/or wherein heteroatoms can be bond to the carbon chain. Furthermore, these aliphatic groups can be substituted by one or more, same or different substituents.
• carboxy refers to any carboxyl groups, which are bonded via the carbon atom of the carboxyl group (-COOH) to the remainder of the molecule.
• the invention relates to compounds of formula I, wherein T is O, i.e.
• the present invention relates to compounds of formula I, wherein the imidazole ring is bonded to the pyridazine ring via an amide group in the 5-position of the imidazole ring. Such compounds correspond to compounds of formula I.A.
• the present invention relates to compounds of formula I, wherein the imidazole ring is bonded to the pyridazine ring via an amide group in the 4-position of the imidazole ring. Such compounds correspond to compounds of formula I.B.
• Compounds of formula LA are particularly preferred according to the present invention.
• the compounds of formula I may be present in three tautomeric forms T-A, T-B, or T-C, if R 1 is H. This is illustrated for the compounds of formula I.A below. The same considerations also apply to the compounds of formula I.B.
• R 1 is different from H
• the compounds of formula I may be present in three isomeric forms ISO-A, ISO-B, or ISO-C. This is illustrated for the compounds of formula LA below. The same considerations also apply to the compounds of formula I.B.
• the compounds of formula I are present in the form of the structural isomer ISO-A.
• the compounds of formula I may also be present in the form of the structural isomers ISO-B, or ISO-C, or in the form of mixtures thereof.
• the structural isomer ISO-A only throughout the
• Isomer ISO-C can be obtained by alkylation of compounds I, wherein R 1 is hydrogen.
• the reaction can be performed by analogy to known N-alkylation of pyridazines.
• N-alkylation of pyridazines is known in literature and can be found in e.g., J. Chem. Soc., Perkin Trans., vol. 1 , p. 401 (1988), and J. Org. Chem., vol. 46, p. 2467 (1981).
• the following compound I. A may be used as starting material.
• T is O and the imdiazole ring is bonded to the remainder of the molecule in 5-position, corresponding to formula 1.1.A, or in 4- position, corresponding to formula 1.1.B, with the compounds of formula 1.1. A being preferred.
• R P1 , R pz and R P3 are H. These compounds correspond to formula l * .
• R P1 , R pz and R P3 are H and the imdiazole ring is bonded to the remainder of the molecule in 5-position, corresponding to formula .A, or in 4-position, corresponding to formula P.B, with the compounds of formula .A being preferred.
• R P1 , R P2 and R P3 are H and T is O.
• Such compounds correspond to compounds of formula .1.
• R P1 , R P2 and R P3 are H, the imidazole ring is either bonded in 4- or 5-position, and T is O.
• R P1 , R P2 and R P3 are H, the imidazole ring is either bonded in 4- or 5-position, and T is O.
• the present invention relates to compounds of formula I, wherein R 4 is any one of the groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii).
• R 4 is any one of the groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii), and R P1 , R P2 and R P3 are H.
• R 4 is any one of the groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii),
• R P1 , R P2 and R P3 are H, and the imdiazole ring is bonded to the remainder of the molecule in 5-position, corresponding to formula l*.A(i), G.L( ⁇ ), l*.A(iiia), I*. A(iiib), .A(iiic), I*. A(iiid), I*.
• R 4 is any one of the groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii), R P1 , R P2 and R P3 are H, and T is O.
• R 4 is any one of the groups (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii), R P1 , R P2 and R P3 are H, the imidazole ring is either bonded in 4- or 5-position, preferably in the 5-position, and T is O.
• the present invention relates to compounds of formula I, wherein R 4 is any one of the groups (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii), wherein T is O, and wherein the imidazole ring is bonded to the remainder of the molecule in position 5.
• the present invention relates to compounds of formula 1.1. Apia).
• the present invention relates to compounds of formula l.i .A(iiib), I.i .A(iiic), or I.I .A(iiid),
• the present invention relates to compounds of formula l.i .A(iva) or l.i .A(ivb).
• the present invention relates to compounds of formula
• the present invention relates to compounds of formula M .A(via), I. A(vib), M .A(vic), or 1.1.A(vid),
• the present invention relates to compounds of formula l.1.A(vii), or l.i .A(viii).
• a compounds are those of formula 1.1.A(iiia), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula IM .A(iiia).
• a compounds are those of formula U .A(iiib), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula IM .A(iiib).
• a compounds are those of formula 1.1.A(iiic), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula I * .1.A(iiic).
• a compounds are those of formula 1.1.A(iiid), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula I * .1.A(iiid).
• a compounds are those of formula l.i .A(iva), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula l * .1.A(iva).
• a compounds are those of formula M .A(ivb), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula l * .1.A(ivb).
• a compounds are those of formula l.i .A(va), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula IM .A(va).
• a compounds are those of formula l.1.A(vb), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula l*.1.A(vb).
• a compounds are those of formula l.i .A(vc), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula l*.1.A(vc).
• a compounds are those of formula l.1.A(via), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula IM .A(via).
• a compounds are those of formula l. A(vib), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula .lA(vib).
• a compounds are those of formula l.lA(vic), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula IM .A(vic).
• a compounds are those of formula 1.1.A(vid), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula IM .A(vid).
• 1.1.A compounds are those of formula 1.1.A(vii), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula IM .A(vii).
• a compounds are those of formula 1.1.A(viii), wherein R P1 , R P2 and R P3 are H. Such compounds are compounds of formula l * .1.A(viii).
• the present invention relates to compounds of formula I, wherein R 1 is H, CrC2-alkyl, Cs-Cs-cydoalkyl, or CrC 2 -alkoxy-Ci-C2-alkyl.
• R 1 is H, or C1-C2- aikyl.
• the present invention relates to compounds of formula I, wherein R 2 and R 3 are independently of each other H, halogen, CN, CrC4-alkyI, CrC4 ⁇ haloalkyl, C 3 -C 4 - cycloalkyl, or benzyl.
• R 2 is Ci-C 2 -alkyl, CrC 2 -haioalkyl, C 3 -cycloa(kyl, or benzyl, more preferably, R 2 is C r C 2 -alkyl, or CrC 2 -haloalkyl.
• R 3 is H, halogen, CrC 2 -alkyl, or Ci-C 2 -haloalkyl, more preferably, R 3 is H.
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , CH 2 CH 3 , benzyl, or halomethyl
• R 3 is H, Br, or Cl.
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3I or halomethyl
• R 3 is H.
• the present invention relates to compounds of formula I, wherein R 1 is H, CH 3 or CH2CH3.
• the present invention relates to compounds of formula I, wherein R 2 is CH 3 , or halomethyl, more preferably CH 3> or fluoromethyl.
• the present invention relates to compounds of formula I, wherein R 3 is H.
• R 1 , R 2 and R 3 are also preferred in connection with the above described preferred compounds, in particular the G compounds, the 1.1 compounds, the .1 compounds, the I. A compounds, the G.L compounds, the 1.1.
• R 4 is preferably any one of the options (i), (ii), (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii).
• the present invention relates to compounds of formula I, in particular to the compounds, the 1.1 compounds, the .1 compounds, the I. A compounds, the .A compounds, the 1.1.A compounds, the .1.A compounds as defined above, wherein R 4 is any one of the options (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid),
• R 4u , R 4v , A, D, E, G, M, Q, T 1 , V, W, Y and m are as defined above.
• R 4a is CN, C 2 -C 6 -alkyf, Ci-C 2 -haloalkyl, CrC 2 -alkoxy-Ci-C 2 -alkyl, or C 3 -C6-cyclcalkyl,
• R 4c is H or CH 3 .
• R 4a is H, F, CN, Ci-C 2 -alkyl, or halomethyl
• A is a cycloalkyl ring, preferably a cyclohexyl, a cyclopentyl, or a cyclobutyl ring, or a tetrahydropyrane, or tetrahydrofurane ring, which rings may be substituted as indicated above.
• R 4a is CN, Ci-C 2 -alkyl, Ci-C2-haloalkyl, or cyclopropyl, wherein the C-atoms may be
• R 4b is H, CN, Ci-C 2 -alkyl, or CrC 2 -haloalkyl, wherein the C-atoms may be substituted as indicated above;
• D is a direct bond, or CrC 4 -alkylene
• E is a non-aromatic heterocyclic group, wherein the heterocycle may be substituted as indicated above, and wherein a phenyl group may be optionally annealed to the heterocycle.
• G is an a-branched C 2 -C 3 -alkylene, preferably CH(CH 3 ), or CH(CH 3 )CH 2 ;
• n 0, or 1 ;
• R 4d is CrC 2 -haloalkyl, or C-C 3 H 5 , wherein the C-atoms may be halogenated.
• Q is a direct bond, or an a-branched or straight chain CrCe-alkylene, C 2 -C8-alkenylene, or C 2 -Ce-alkynylene, which carbon chains can be substituted or unsubstituted as indicated above;
• R 4e is H, or CH 3 ; or
• G and R 4e together form a 4- to 6-mem bered carbocyclic ring or a 4- to 6-membered
• heterocyclic ring which contains O or S as heteroatom, and which groups may be substituted as indicated above;
• M is O, S, NOCH 3I or NSCH 3 ;
• R M is a group mentioned for R 4® , or wherein
• R M and G together form a 4- to 6-membered unsaturated, non-aromatic N-containing
• heterocycle which heterocycle may contain an additional heteroatom O, or S, wherein S may be oxidized, and which ring is unsubstituted or substituted as indicated above.
• W is an a-branched or straight chain Ci-Ce-alkylene, Cs-Ce-cycloalkylene, or C 3 -C 0 - heterocycloalkylene, wherein W is substituted as indicated above;
• V is O, or S; R 4 9 is H, CrC4-alkyl, or Cs-Ce-cycloalkyl;
• R 4f is H, Ci-C4-alkyl, or Cs-Ce-cycloalkyl; or
• R 4 9 and R 4f together with the carbon atom to which they are bonded form a 3- to 8- membered, saturated or unsaturated carbo- or heterocycle, which heterocycle contains one or more, same or different heteroatoms N, O, or S, wherein S may be oxidized, and wherein the carbo- or heterocycles are unsubstituted or substituted as indicated above.
• R 4h is methyl, ethyl, n-butyl, n-pentyl, n-propyl, iso-propyl, ally!, 3,3-dimethylallyl, propargyi, cyclohexyl, tetrahydro-pyranyl, tetrahydro-thiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]- bicycloheptanyl, methoxyethyl, methox propyl, ethoxyethyl, ethylthioethyl,
• n 0, 1 , or 2, preferably 0, or 2, particularly preferrably 0.
• R 4i is methyl, ethyl, propyl, iso-propyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3- cyanopropyl, cyclohexyl, 3,3,3-trifluoro-propyl, 3-fluoro-propyl, 2-methylsulfanylethyl, 2-
• R 4 i and R 4k together with the nitrogen atom to which they are bonded form a 5-or 8- membered heterocycle, which heterocycle contains the nitrogen atom as heteroatom, and may further contain one or two, same or different heteroatoms N or O, and which rings are substituted as indicated above;
• R 4 ' is H, methyl, ethyl, iso-propyl, 1 -cyano-1 -methylethyl, or cyclopropyl;
• T 1 is O, N-OR 1G , N-NR 2C R 3C , or a cycle of formula T 11 as indicated above, and wherein the substituents are defined as indicated above;
• R 4m is methyl or ethyl
• R 4n is H, methyl, ethyl, methylsulfonyl, or cyclopropylsulfonyl;
• R 4 ° is H, methyl, ethyl, iso-propyl, iso-butyl, tert.-butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbony I methyl , ethoxycarbonylmethyl, cyclopropyl, 1-cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyrid in-3-yl, phenylmethyl, or 1 -phenyl-2-hydroxyethyl; or
• R 4n and R 4 ° together are (CFhH (CH2)4, (CH2)3, or (CFb ⁇ OiChk ;
• Y is O or S
• R 4 P is H, Ci-C 6 -alkyl, C3-C6-alkenyl, or Cs-Ce-alkyrt l, which are unsubstituted or substituted as indicated above, or C 3 -C 6 -cycloalkyl, Ci-C 6 -alkylcarbonyl, Ci-C 6 -alkoxycarbonyl, aryl-Ci-C 4 -alkyl, or aryl-Ci-C 4 -alkoxy, which are unsubstituted or substituted as indicated above; and R 4 ⁇ is H, CrCs-alkyl, Ca-Ce-alkenyl, or C3-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or C 3 -Ce-cycloalkyl, Ci-C 6 -alkylcarbonyl, CrCe-a!koxycarbonyf, aryl-Ci-C 4 -alkyl, or ary
• R 4r is H, CrC 4 -alkyl, Cs-Ce-alkenyl, or C3-C6-alkynyl, which are unsubstituted or substituted as indicated above, or C3-Ce-cycloalkyl, or C3-Ce-cycloalkyl-CrC 4 -alkyl, which are unsubstituted or substituted as indicated above, or aryl, hetaryl, arylalkyl, or
• hetarylalkyl which are unsubstituted or substituted as indicated above.
• R 4s is 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methy(-5-[(2,2,2- trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2- trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3- chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1 -methyl-1 H- pyrrol-2-yl, 3-fury!, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3- [(cyclopropylmethyl)sutfanyl]phenyl,
• R 4t is H, methyl, trifluorom ethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3- pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl, or benzyl;
• R 4u is H, or methyl
• R 4t and R 4u together are vinyl, prop-1-en-2-yl, (1 £)-prop-1-en-1-yl, (1 )-prop-1-en-1-yl, or cyclopropyl;
• R 4v is H, S(0) m R 1E , OR 2E , or N(R 3E )(R 4E ), wherein if R 4t and/or R 4u is H, or CrCe-alkyl, R 4v is S(0) m R 1E , OR 2E , or N(R 3E )(R 4E );
• R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3- chlorophenyl, or 4-chloro-phenyl;
• R 3E and R 4E together with the nitrogen atom to which they are bonded form a 5-me bered heterocycle, which heterocyclyl group contains one or two N-atoms, which cyclic groups may contain one group CO, and wherein the C-atoms are substituted with trifluoromethyl, methyl, or cyclopropyl.
• R 4 groups (iiia), (iiib), (iiic), (iiid), (iva), (ivb), (va), (vb), (vc), (via), (vib), (vie), (vid), (vii), or (viii), which are relevant for the compounds of formula I, in particular to the I* compounds, the 1.1 compounds, the IM compounds, the LA compounds, the .A compounds, the 1.1. A compounds, the I * .1. A compounds as defined above, it is further preferred that R 1 , R 2 , and R 3 correspond to the preferred options provided above.
• R 1 is H, CHa, or C2H5, preferably H, or CH3;
• R 2 is CH3, CH2CH3, benzyl, or halomethyl
• R 3 is H, Br, or Cl
• R 1 is H, CH3, or C2H5, preferably H, or CH 3 ;
• R 2 is CH 3 , or halomethyl
• R 3 is H.
• One preferred embodiment relates to compounds of formula P.A(iiia), wherein
• R 1 is H, CH3, or C2H5, preferably H, or CH3;
• R 2 is CH3, or halomethyl
• R 3 is H
• R 4a , R 4b and R 4c is C3-C4-cycloalkenyl, Cs-C ⁇ halocycloalkenyl, OR a , or SR a , wherein R a is C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycIoaIkenyl; and
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .A(iiib), wherein
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or halomethyl
• R 3 is H
• R 4a is as defined above;
• A is a C 3 -C4-cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .A(iiic), wherein
• R 1 is H, CH 3I or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or halomethyl
• R 3 is H
• R 4a and R 4b are as defined above;
• E is a C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l * .A(iiid), wherein
• R 1 is H, CH 3I or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3> or halomethyl
• R 3 is H
• R 4d is CrC2-haloalkyl, or c-C 3 H 5 , wherein the C-atoms may be halogenated;
• G is a C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula P.A(iva), wherein
• R 1 is H, CH 3I or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CHs, or halomethyl
• R 3 is H
• R 4® is H, or CH 3 ;
• Q is a direct bond, or an «-branched or straight chain CrCs-alkylene, C 2 -C 8 -alkenylene, or C 2 -Ce-alkynylene, which carbon chains can be substituted or unsubstituted as indicated above;
• M is O, S, NOCH 3 , or NSCH 3 ;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .A(ivb), wherein
• R 1 is H, CH 3J or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CHs, or halomethyl
• R 3 is H
• R 4f is H, CrC 4 -aIkyI, or C 3 -Ce-cycloalkyl
• R 4 9 is H, Ci-C 4 -alkyl, or Cs-Ce-cycloalkyl
• V is O, or S
• W is an «-branched or straight chain Ci-C 8 -alkylene, C 3 -C 8 -cycloalkylene, or C 3 -C 8 - heterocycloalkylene, wherein W is substituted as indicated above;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l*,A(va), wherein
• R 1 is H, or CHs, preferably CHs
• R 2 is CH 3 ;
• R 3 is H, chlorine, or bromine, preferably H
• R 4h is methyl, ethyl, n-butyl, n-pentyl, n-propyl, iso-propyl, ally!, 3,3-dimethyIallyI, propargyl, cyclohexyl, tetrahydro-pyranyl, tetrahydro-thiopyranyl, 3-oxetanyl, 5-oxa-[3.3,0]- bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl,
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l * .A(vb), wherein
• R 1 is H, methyl, ethyl, or cyclopropyl
• R 2 is CHs
• R 3 is H, chlorine, or bromine, preferably H
• R 4i is methyl, ethyl, propyl, iso-propyl, cyclopentyl, sec-butyl, al!yl, 3-methoxy propyl, 3- cyanopropyl, cyclohexyl, 3, 3, 3-trif I uoro-propy 1 , 3-fluoro-propyl, 2-methylsulfanylethyl, 2- [(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran-
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l * .A(vc), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 and R 4k together with the nitrogen atom to which they are bonded form a 5-or 6- membered heterocycle, which heterocycle contains the nitrogen atom as heteroatom;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l * .A(via), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 ' is H, methyl, ethyl, iso-propyl, 1 -cyano-1 -methylethyl, or cyclopropyl;
• T 1 is as defined above;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .A(vib), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4m is methyl, or ethyl
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l * A(vic), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H;
• R 4n is H, methyl, ethyl, methylsulfonyl, or cyclopropylsulfonyl;
• R 40 is H, methyl, ethyl, iso-propyl, iso-butyl, tert. -butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyi, ethoxycarbony I methyl, cyclopropyl, 1 -cyanocyclopropyl, cyclopentyi, cyclopropyl methyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl, or 1 -phenyl-2-hydroxyethyl; or
• R 4n and R 40 together are (CH 2 )5, (CH2)4, (CH2)3, or (CH 2 ) 2 0(CH2)2;
• Y is O, or S
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula r.A(vid), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 P is H, CrCe-alkyl, Ca-Ce-alkenyl, or C3-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or Cs-Ce-cycloalkyl, CrCe-alkylcarbonyl, CrCe-alkoxycarbonyl, aryl-CrC4-alkyl, or aryl-Ci-C4-alkoxy, which are unsubstituted or substituted as indicated above;
• R 4( i is H, CrCe-alkyl, Ca-Ce-alkenyl, or Cs-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or Cs-Ce-cycloalk l, CrCe-alkylcarbonyl, CrCe-alkoxycarbonyl, aryl-Ci-C 4 -alkyl, or aryl-Ci-C 4 -alkoxy, which are unsubstituted or substituted as indicated above; and
• R 4r is H, Ci-C4-alkyl, Ca-Ce-alkenyl, or Cs-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or Cs-Ce-cycloalk l, or C 3 -C8-cycloalkyl-Ci-C4-alkyl, which are unsubstituted or substituted as indicated above, or aryl, hetaryl, arylalkyl, or
• hetarylalkyl which are unsubstituted or substituted as indicated above;
• Y is O, or S
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula G.A(n ⁇ ), wherein
• R 1 is H, methyl, ethyl, preferably methyl and ethyl;
• R 2 is CH 3 ;
• R 3 is H, chlorine, bromine, preferably H
• R 4s is 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2- trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2- trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3- chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1 -methyl-1 H- pyrrol-2-yl, 3-fury I, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3- [(cyclopropylmethyl)sulfanyl]phenyl, 3-(meth
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula G.L(n ⁇ ), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3
• R 3 is H
• R 4t is H, methyl, triffuoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3- pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl, or benzyl;
• R 4u is H, or methyl
• R 4t and R 4u together are vinyl, prop-1-en-2-yl, (1 £)-prop-1-en-1-yl, (1 )-prop-1-en-1-yl, or cyclopropyl;
• R 4v is H, S(0) m R 1E , OR 2E , or N(R 3E )(R 4E ), wherein if R 4t and/or R 4u is H, or CrCe-alkyl, R 4v is S(0) m R 1E , OR 2E , or N(R 3E )(R 4E );
• R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2- methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, or 2- pyrimidyl;
• R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3- chlorophenyl, or 4-chloro-phenyl;
• R 3E and R 4E together with the nitrogen atom to which they are bonded form a 5-mem bered heterocycle, which heterocyclyl group contains one or two N-atoms, which cyclic groups may contain one group CO, and wherein the C-atoms are substituted with trifluoromethyi, methyl, or cyclopropyl;
• T is O, S or NR 1b .
• Another preferred embodiment refers to compounds of formula .B(iiia), wherein
• R 1 is H, CH 3J or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or ha!omethyl
• R 3 is H
• R 4a , R 4b and R 4c is Cs-C ⁇ cycloalkenyl, C 3 -C4-halocycloal kenyl , OR a , or SR a , wherein R a is C 3 -C 4 -cycloal kenyl, or C 3 -C 4 -halocycloalkenyl; and
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .B(iiib), wherein
• R 1 is H, CHs, or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or halomethyl
• R 3 is H
• R 4a is as defined above;
• A is a C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group
• T is O, S or NR 1b .
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CHs, or halomethyl
• R 3 is H
• R 4a and R 4b are as defined above;
• E is a C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .B(iiid), wherein
• R 1 is H, CHs, or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or halomethyl
• R 3 is H
• R 4d is Ci-C 2 -haloalkyl, or C-C 3 H 5 , wherein the C-atoms may be halogenated;
• G is a C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .B(iva), wherein
• R 1 is H, CH 3I or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CHs, or halomethyl
• R 3 is H
• R 4e is H, or CH 3 ;
• Q is a df ' rect bond, or an «-branched or straight chain CrCe-alky!ene, C 2 -C 8 -alkenylene, or C 2 -Ce-alkynylene, which carbon chains can be substituted or unsubstituted as indicated above;
• M is O, S, NOCH 3 , or NSCH 3 ;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .B(ivb), wherein
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or haiomethyi
• R 3 is H
• R 4f is H, CrC4-alkyl, or C 3 -C 6 -cycloalkyl
• R 4 a is H, Ci-C 4 -alkyl, or C3-C 6 -cycloalkyl
• V is O, or S
• W is an a-branched or straight chain CrCe-alkylene, C3-C8-cycloalkylene, or Ca-Cs- heterocycloalkylene, wherein W is substituted as indicated above;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l*.B(va), wherein
• R 1 is H, or CH 3 , preferably CH3;
• R 2 is CH 3 ;
• R 3 is H, chlorine, or bromine, preferably H
• R 4h is methyl, ethyl, n-butyl, n-pentyl, n-propyl, iso-propyl, ally!, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydro-pyranyl, tetrahydro-thiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]- bicycloheptan l, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl,
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l*.B(vb), wherein
• R 1 is H, methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H, chlorine, or bromine, preferably H
• R 4 ' is methyl, ethyl, propyl, iso-propyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3- cyanopropyl, cyclohexyl, 3,3,3-trifluoro-propyl, 3-fluoro-propyl, 2-methylsulfanylethyl, 2- [(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran- 3-yl, tetrahydro-2H-pyran-4yl, tetrahydro-2H-thiopyran-4-yi, phenyl, 3- methylsulfanylphenyl, 4-chlorophenyl, 4-fluorophenyl, 2,5-difluorophenyl, 2,4- difluorophenyl, 3,5-difluorophen
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula l * .B(vc), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 and R 4k together with the nitrogen atom to which they are bonded form a 5-or 6- membered heterocycle, which heterocycle contains the nitrogen atom as heteroatom;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula r.B(via), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 41 is H, methyl, ethyl, iso-propyl, 1 -cyano-1 -methylethyl, or cyclopropyl;
• T 1 is as defined above;
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .B(vib), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4m is methyl, or ethyl
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .B(vic), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4n is H, methyl, ethyl, methylsulfonyl, or cyclopropylsulfonyl;
• R 40 is H, methyl, ethyl, iso-propyl, iso-butyl, tert.-butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonyl methyl , ethoxycarbonylmethyl, cyclopropyl, 1 -cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl, or 1 -phenyl-2-hydroxyethyl; or
• R 4n and R 4 ° together are (ChfeK (CH2)4, (CH2) 3 , or (CH2)20(CH2)2;
• Y is O, or S
• T is O, S or NR 1b ,
• Another preferred embodiment relates to compounds of formula r.B(vid), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 P is H, CrCe-alkyl, Cs-Ce-alkenyl, or C 3 -C 6 -alkynyl, which are unsubstituted or substituted as indicated above, or C 3 -C 6 -cycloaikyl, CrCe-alkylcarbonyl, CrCe-alkoxycarbonyl, aryl-Ci-C4-alkyl, or aryl-CrC4-alkoxy, which are unsubstituted or substituted as indicated above;
• R 4 is H, CrCe-alkyl, Ca-Ce-alkenyl, or Ca-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or Cs-Ce-cycloalkyl, CrCe-alkylcarbonyl, Ci-C 6 -alkoxycarbonyl, aryl-CrC4-alkyl, or aryl-CrC4-alkoxy, which are unsubstituted or substituted as indicated above; and
• R 4r is H, CrC4-alkyl, Cs-Ce-alkeny!, or Cs-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or C 3 -Ce-cycloalkyl, or C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl, which are unsubstituted or substituted as indicated above, or aryl, hetaryl, arylalkyl, or hetarylalkyl, which are unsubstituted or substituted as indicated above;
• Y is O, or S
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula P.B(vii), wherein
• R 1 is H, methyl, ethyl, preferably methyl and ethyl;
• R 2 is CH 3 ;
• R 3 is H, chlorine, bromine, preferably H
• R 4s is 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2- trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2- trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3- chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1 -methyl-1 H- pyrrol-2-yl, 3-fury I, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3- [(cyclopropylmethyl)sulfanyl]phenyl, 3-(meth
• T is O, S or NR 1b .
• Another preferred embodiment relates to compounds of formula .B(n ⁇ ), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CHs
• R 3 is H
• R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3- pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl, or benzyl;
• R 4u is H, or methyl; or R 4t and R 4u together are vinyl, prop-1 -en-2-yl, (1 £)-prop-1-en-1-yl, (1 )-prop-1-en-1-yl, or cyclopropyl;
• R 4v is H, S(0) m R 1E , OR 2E , or N(R 3E )(R 4E ), wherein if R 4t and/or R 4u is H, or CrCe-alkyl, R 4v is S(0) m R 1E , OR 2E , or N(R 3E )(R 4E );
• R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2- methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, or 2- pyrimidyl;
• R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3- chlorophenyl, or 4-chloro-phenyl;
• R 3E and R 4E together with the nitrogen atom to which they are bonded form a 5-membered heterocycle, which heterocyclyl group contains one or two N-atoms, which cyclic groups may contain one group CO, and wherein the C-atoms are substituted with trifluoromethyl, methyl, or cyclopropyl;
• T is O, S or NR 1b .
• More preferred embodiments relate to compounds of formula IM .A(iiia), wherein
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CHs, or halomethyl
• R 3 is H
• R 4a , R 4b and R 4c is C3-C4-cycloalkenyl, C3-C4-halocycloalkenyl, OR ® , or SR a , wherein R a is C3-C4-cycloalkenyl, or C 3 -C4-halocycloalkenyl.
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CHs, or halomethyl
• R 3 is H
• R 4a is as defined above;
• A is a C 3 -C4-cycloalkenyl, or C 3 -C4-halocycloalkenyl group.
• R 1 is H, CHs, or C2H5, preferably H, or CH 3 ;
• R 2 is CHs, or halomethyl
• R 3 is H
• E is a C 3 -C4-cycloalkenyl, or C3-C4-halocycloalkenyl group.
• R 1 is H, CHs, or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or halomethyl
• R 3 is H
• R 4d is Ci-C2-haloalkyl, or C-C3H5, wherein the C-atoms may be halogenated;
• G is a C 3 -C4-cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group.
• R 1 is H, CH 3I or C2H5, preferably H, or CH 3 ;
• R 2 is CH3, or halomethyl
• R 3 is H;
• R 4e is H, or CH 3 ;
• Q is a direct bond, or an a-branched or straight chain C Ce-alkylene, C2-Ce-alkenyiene, or Cz-Ce-alkynylene, which carbon chains can be substituted or unsubstituted as indicated above;
• M is O, S, NOCHs, or NSCH 3 .
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3J or halomethyl
• R 3 is H
• R 4f is H, Ci-C4-alkyl, or Ca-Ce-cycloalkyl
• R 4 9 is H, Ci-C 4 -alkyl, or Cs-Ce-cyc!oaikyl;
• V is O, or S
• W is an a-branched or straight chain Ci-C 8 -alkylene, Ca-Ce-cycloalkylene, or C 3 -C 8 - heterocycloalkylene, wherein W is substituted as indicated above.
• R 1 is H, or CH 3 , preferably CH 3 ;
• R 2 is CH 3 ;
• R 3 is H, chlorine, or bromine, preferably H
• R 4h is methyl, ethyl, n-butyl, n-pentyl, n-propyl, iso-propyl, ally!, 3,3-dimethylaIlyI, propargyl, cyclohexyl, tetrahydro-pyranyl, tetrahydro-thiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]- bicycloheptanyl, methoxyethyl, methoxypropyl, ethoxyethyl, ethylthioethyl,
• hydroxycarbonyl-methyl carbamoyl-methyl, N-methylcarbamoyl-methyl, N-c- propylcarbamoyl-methyl, N , N-dimethylcarbamoyl-methyl, 2-methoximino-propyl, cyclopropylmethyl, phenyl, 4-methylphenyl, 2-nitrophenyl, 3-methyIthiophenyl, 4-chloro- phenyl, 4-fluoro-phenyl, 4-tert.-butyl-phenyl, 4-methoxy-phenyl, 4-nitrophenyl, 4- dimethylamino-phenyl, 2-fluoro-phenyl, 2-methoxy-phenyl, 2-dimethylaminosulfonyl- phenyl, 2-dimethylaminocarbamoyl-phenyl, 3-nitrophenyl, 3-trifluoromethyl-phenyl, 3- chloro-phenyl, 2,5-dichloro-phenyl,
• R 1 is H, methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H, chlorine, or bromine, preferably H
• R 4i is methyl, ethyl, propyl, iso-propyl, cyclopentyl, sec-butyl, ally!, 3-methoxypropyl, 3- cyanopropyl, cyclohexyl, 3,3,3-trifluoro-propyl, 3-f!uoro-propyI, 2-methylsulfanylethyl, 2- [(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran-
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3
• R 3 is H
• R 4 i and R 4k together with the nitrogen atom to which they are bonded form a 5-or 6- membered heterocycle, which heterocycle contains the nitrogen atom as heteroatom.
• R 4 i and R 4k together with the nitrogen atom to which they are bonded form a 5-or 6- membered heterocycle, which heterocycle contains the nitrogen atom as heteroatom.
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 41 is H, methyl, ethyl, iso-propyl, 1 -cyano-1 -methylethyl, or cyclopropyl;
• T 1 is as defined above. Further more preferred embodiments relate to compounds of formula IM .A(vib), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R2 is CH 3
• R 3 is H
• R 4m is methyl, or ethyl.
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4n is H, methyl, ethyl, methylsulfonyl, or cyclopropylsulfonyl;
• R4° j S H methyl, ethyl, iso-propyl, iso-butyl, tert.-butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyl, ethoxycarbony I methyl , cyclopropyl, 1 -cyanocyclopropyl , cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl, or 1 -phenyl-2-hydroxyethyl; or
• R 4n and R 40 together are (CH 2 )5, (CH2) 4 , (CH2)3, or (CH2)20(CH2)2;
• Y is O, or S.
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 P is H, CrCe-alkyl, Cs-Ce-alkenyl, or Cs-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or C 3 -C 6 -cycloalkyl, CrCe-alkylcarbonyl, Ci-C 6 -alkoxycarbonyl, aryl-CrC4-alkyl, or aryl-Ci-C 4 -alkoxy, which are unsubstituted or substituted as indicated above;
• R 4 P is H, CrCe-alkyl, C 3 -C 6 -alkenyl, or Cs-Ce-alkyn l, which are unsubstituted or substituted as indicated above, or C 3 -C 6 -cycloalkyl, Ci-C 6 -alkylcarbonyl, C 1 -C 6 -al koxycarbonyl , aryl-Ci-C4-alkyl, or aryl-Ci-C 4 -alkoxy, which are unsubstituted or substituted as indicated above;
• R 4r is H, Ci-C 4 -alkyl, Cs-Ce-alkenyl, or Cs-Ce-alkynyl, which are unsubstituted or substituted as indicated above, or C 3 -C 8 -cycloalkyl, or C 3 -Ce-cycloalky l-C 1 -C 4 -al kyl , which are unsubstituted or substituted as indicated above, or aryl, hetaryl, arylalkyl, or
• hetarylalkyl which are unsubstituted or substituted as indicated above;
• Y is O, or S.
• R 1 is H, methyl, ethyl, preferably methyl and ethyl;
• R 2 is CH 3 ;
• R 3 is H, chlorine, bromine, preferably H
• R 4s is 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2- trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2- trifluoroethyl)sulfinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3- chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1 -methyl-1 H- pyrrol-2-yl, 3-furyl, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)suifanyl]phenyl, 3- [(cyclopropylmethyl)sulfanyl]phenyl, 3-(meth
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichiorophenyi, 2-pyridinyl, 3- pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl, or benzyl;
• R 4u is H, or methyl
• R 4t and R 4u together are vinyl, prop-1-en-2-yl, (1 £)-prop-1-en-1-yl, (1 )-prop-1-en-1-yl, or cyclopropyl;
• R 4v is H, S(0) m R 1E , OR 2E , or N(R 3E )(R 4E ), wherein if R 4t and/or R 4u is H, or CrCe-alkyl, R 4v is S(0) m R 1E , OR 2E , or N(R 3E )(R 4E );
• R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, 2,2-dimethylpropyl, 2- methoxy-2-oxoethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, or 2- pyrimidyl;
• R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropylmethyl, benzyl, 3- chlorophenyl, or 4-chloro-phenyl;
• R 3E and R 4E together with the nitrogen atom to which they are bonded form a 5-membered heterocycle, which heterocyclyl group contains one or two N-atoms, which cyclic groups may contain one group CO, and wherein the C-atoms are substituted with trifluoromethyl, methyl, or cyclopropyl.
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH3;
• R 2 is CH3, or halomethyl
• R 3 is H
• R 4a , R 4b and R 4c is C3-C 4 -cycloalkenyl, C 3 -C 4 -halocycloalkenyl, OR a , or SR a , wherein R a is C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl.
• R 1 is H, CH 3J or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 , or halomethyl
• R 3 is H
• R 4a is as defined above;
• A is a C 3 -C4-cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group.
• R 1 is H, CHs, or C 2 H 5 , preferably H, or CH3;
• R 2 is CH 3 , or halomethyl
• R 3 is H
• E is a C 3 -C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group.
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3I or halomethyl
• R 3 is H
• R 4d is Ci-C 2 -haloalkyl, or C-C 3 H 5 , wherein the C-atoms may be halogenated;
• G is a C3-C 4 -cycloalkenyl, or C 3 -C 4 -halocycloalkenyl group.
• R 1 is H, CH 3 , or C 2 H 5 , preferably H, or CH 3 ;
• R 2 is CH 3 or halomethyl
• R 3 is H
• R 4e is H, or CH3;
• Q is a direct bond, or an a-branched or straight chain CrCe-alkylene, C 2 -C 8 -alkenylene, or C 2 -C 8 -alkynylene, which carbon chains can be substituted or unsubstituted as indicated above;
• M is O, S, NOCH 3 , or NSCH 3 .
• Further more preferred embodiments relate to compounds of formula IM .B(ivb), wherein
• R 1 is H, CHa, or G 2 H 5 , preferably H, or Chh;
• R 2 is CH3, or halomethyl
• R 3 is H
• R 4f is H, CrC 4 -alkyl, or Cs-Ce-cycloalkyl
• R 4 9 is H, CrC 4 -alkyl, or Cs-Ce-cycloalkyl
• V is O, or S
• W is an «-branched or straight chain CrCe-alkylene, Ca-Ce-cycloalkylene, or C3-C8- heterocycloa!kylene, wherein W is substituted as indicated above.
• R 1 is H, or CH 3 , preferably Ch ;
• R 2 is CH 3 ;
• R 3 is H, chlorine, or bromine, preferably H
• R 4h is methyl, ethyl, n-butyl, n-pentyl, n-propyl, iso-propyl, allyl, 3,3-dimethylallyl, propargyl, cyclohexyl, tetrahydro-pyranyl, tetrahydro-thiopyranyl, 3-oxetanyl, 5-oxa-[3.3.0]- bicycloheptanyl, methoxyethyl, methoxypropy!, ethoxyethyl, ethylthioeth l,
• R 1 is H, methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H, chlorine, or bromine, preferably H
• R 4i is methyl, ethyl, propyl, iso-propyl, cyclopentyl, sec-butyl, allyl, 3-methoxypropyl, 3- cyanopropyl, cyclohexyl, 3, 3, 3-trif I uoro-propyl , 3-fluoro-propyl, 2-methylsulfanylethyl, 2- [(2,2,2-trifluoroethyl)sulfanyl]ethyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl, tetrahydrofuran- 3-yl, tetrahydro-2H-pyran-4yl, tetrahydro-2H-thiopyran-4-yl, phenyl, 3- methylsulfanylphenyl, 4-chlorophenyl, 4-fluorophenyl, 2,5-difluorophenyl, 2,4- difluorophenyl, 3,5-difluor
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 i and R 4k together with the nitrogen atom to which they are bonded form a 5-or 6- membered heterocycle, which heterocycle contains the nitrogen atom as heteroatom.
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 41 is H, methyl, ethyl, iso-propyl, 1 -cyano-1 -methylethyl, or cyclopropyl;
• T 1 is as defined above.
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4m is methyl, or ethyl. Further more preferred embodiments relate to compounds of formula IM .B(vic), wherein
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4n is H, methyl, ethyl, methylsulfonyl, or cyclopropylsulfonyl;
• R 40 is H, methyl, ethyl, iso-propyl, iso-butyl, tert. -butyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, 2-methoxyethyl, cyanomethyl, methoxycarbonylmethyl , ethoxycarbonylmethyl, cyclopropyl, 1 -cyanocyclopropyl, cyclopentyl, cyclopropylmethyl, methoxy, ethoxy, phenyl, pyridin-3-yl, phenylmethyl, or 1-phenyl-2-hydroxyethyl; or
• R 4n and R 40 together are (Chfejs, (CFb (CH2)3, or (OH 2 )2q(OH2)2;
• Y is O, or S.
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4 P is H, CrCe-alkyl, C 3 -C 6 -alkenyl, or C3-C6-alkynyl, which are unsubstituted or substituted as indicated above, or Cs-Ce-cycloalkyl, Ci-Ce-alkylcarbonyl, Ci-Ce-alkoxycarbonyl, aryl-Ci-C 4 -aikyI, or aryl-Ci-C4-alkoxy, which are unsubstituted or substituted as indicated above;
• R 4 P is H, Ci-C 6 -alkyl, Cs-Ce-alkenyl, or C 3 -C 6 -alkynyl, which are unsubstituted or substituted as indicated above, or Cs-Ce-cycloalkyl, CrCe-alkylcarbonyl, Ci-Ce-alkoxycarbonyl, aryl-CrC4-alkyl, or aryl-Ci-C4-alkoxy, which are unsubstituted or substituted as indicated above;
• R 4r is H, CrC4-alkyl, C3-C6-alkenyl, or C3-C6-alkynyl, which are unsubstituted or substituted as indicated above, or C 3 -C 8 -cycloalkyl, or C3-C 8 -cycloalkyl-Ci-C4-alkyl, which are unsubstituted or substituted as indicated above, or aryl, hetaryl, arylalkyl, or
• hetarylalkyl which are unsubstituted or substituted as indicated above;
• Y is O, or S.
• R 1 is H, methyl, ethyl, preferably methyl and ethyl;
• R 2 is CH 3 ;
• R 3 is H, chlorine, bromine, preferably H
• R 4s is 3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl, 2-fluoro-4-methyl-5-[(2,2,2- trifluoroethyl)sulfanyl]phenyl, 3-(methylsulfanyl)phenyl, pyrimidin-2-yl, 3-[(2,2,2- trifiuoroethyl)suifinyl]phenyl, phenyl, pyridin-3-yl, 3,5-dimethylphenyl, 2-chlorophenyl, 3- chlorophenyl, 4-chiorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 1 -methyl-1 H- pyrrol-2-yl, 3-fury I, 2,5-dimethyl-3-thienyl, 3-[(trifluoromethyl)sulfanyl]phenyl, 3- [(cyclopropylmethyl)sulfanyl]phenyl, 3-(
• R 1 is methyl, ethyl, or cyclopropyl
• R 2 is CH 3 ;
• R 3 is H
• R 4t is H, methyl, trifluoromethyl, trichloromethyl, isopropyl, isobutyl, isopentyl, phenyl, 2- chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,4-dichlorophenyl, 2-pyridinyl, 3- pyridinyl, 4-pyridinyl, 4-chloropyridin-3-yl, 2-pyrimidyl, or benzyl;
• R 4u is H, or methyl
• R 4t and R 4u together are vinyl, prop-1 -en-2-yl, (1 £)-prop-1-en-1-yl, (1 )-prop-1-en-1-yl, or cyclopropyl;
• R 4v is H, S(0) m R 1E , OR 2E , or N(R 3E )(R 4E ), wherein if R 4 ⁇ and/or R 4u is H, or CrCe-alkyl, R 4v is S(0) m R 1E , OR 2E , or N(R 3E )(R 4E );
• R 1E is methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopropyl methyl, 2,2-dimethylpropyl, 2- m ethoxy-2-oxoethy I , phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, or 2- pyrimidyl;
• R 2E is H, methyl, ethyl, 2,2,2-trifluoroethyl, isopropyl, cyclopropyl methyl, benzyl, 3- chlorophenyl, or 4-chloro-phenyl; R 3E and R 4E together with the nitrogen atom to which they are bonded form a 5-membered heterocycle, which heterocyclyl group contains one or two N-atoms, which cyclic groups may contain one group CO, and wherein the C-atoms are substituted with trifluorom ethyl, methyl, or cyclopropyl.
• R 1 is H, methyl, or ethyl
• R 2 is CH 3 ;
• R 3 is H
• R 4n , R 40 is methyl
• R 4s is phenyl
• R 4t and R 4u together are cyclopropyl
• R 4v is H
• Y is O.
• Table 1 Compounds of the formula IM .A(iiia), .1 A(iiib), .1 A(iiic), IM .A(iiid), .1 A(iva), or .1 A(ivb), wherein R 1 is H, R 3 is H, and the combination of R 2 and R 4 for a compound corresponds in each case to one row of Table A.
• Table 2 Compounds of the formula IM .A(iiia), l*.1 A(iiib), I*.1. A(iiic), .1 A(iiid), IM .A(iva), or G.1 A(ivb), wherein R 1 is CH 3 , R 3 is H, and the combination of R 2 and R 4 for a compound corresponds in each case to one row of Table A.
• Table 3 Compounds of the formula IM .A(iiia), l*.1 A(iiib), l*.1.A(iiic), l * .1 A(iiid), IM .A(iva), or IM .A(ivb), wherein R 1 is CH2CH3, R 3 is H, and the combination of R 2 and R 4 for a compound corresponds in each case to one row of Table A.
• # in each case designates the bond to the imidazole moiety.
• Table 4 Compounds of the formula G.1.A(va), in which R 1 is H, R 2 is CH 3 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 5 Compounds of the formula P.1.A(va), in which R 1 is CH 3 , R 2 is CH 3 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 6 Compounds of the formula .i .A(va), in which R 1 is CH 2 CH 3 , R 2 is CH 3 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B,
• Table 7 Compounds of the formula IM .A(va), in which R 1 is H, R 2 is GH 2 CH 3 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 8 Compounds of the formula IM .A(va), in which R 1 is GH 3 , R 2 is CH 2 GH 3 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 9 Compounds of the formula IM .A(va), in which R 1 is CH2CH 3 , R 2 is CH 2 GH 3 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 10 Compounds of the formula l * .1.A(va), in which R 1 is H, R 2 is GhfeCeHs, R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B
• Table 11 Compounds of the formula IM .A(va), in which R 1 is GH 3 , R 2 is CH 2 G 6 H 5 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B,
• Table 12 Compounds of the formula IM .A(va), in which R 1 is CH2CH3, R 2 is CH 2 C 6 H 5 , R 3 is H, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 13 Compounds of the formula l*.1.A(va), in which R 1 is H, R 2 is GH 3 , R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 14 Compounds of the formula IM .A(va), in which R 1 is GH 3 , R 2 is GH 3 , R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B
• Table 15 Compounds of the formula l * .1.A(va), in which R 1 is CH2CH 3 , R 2 is CH 3 , R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 16 Compounds of the formula .1.A(va), in which R 1 is H, R 2 is CH 2 CH 3 , R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 17 Compounds of the formula l*.1.(va), in which R 1 is CH 3 , R 2 is CH 2 CH 3 , R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B
• Table 18 Compounds of the formula IM .A(va), in which R 1 is CH 2 GH 3 , R 2 is CH 2 CH 3 , R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 19 Compounds of the formula l*.1.A(va), in which R 1 is H, R 2 is CH 2 C 6 H 5 , R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 20 Compounds of the formula .i .A(va), in which R 1 is CH 3 , R 2 is CH2C6H5, R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 21 Compounds of the formula IM .A(va), in which R 1 is CH2CH 3 , R 2 is ChkCeHs, R 3 is Br, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 22 Compounds of the formula .1.A(va), in which R 1 is H, R 2 is CH 3 , R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B
• Table 23 Compounds of the formula IM .A(va), in which R 1 is CH 3 , R 2 is CH 3 , R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 24 Compounds of the formula l * .1.A(va), in which R 1 is CH2CH3, R 2 is CH3, R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 25 Compounds of the formula IM .A(va), in which R 1 is H, R 2 is CH2CH3, R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 26 Compounds of the formula IM .A(va), in which R 1 is CH 3 , R 2 is CH2CH3, R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 27 Compounds of the formula IM .A(va), in which R 1 is CH2CH3, R 2 is CH2CH3, R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B
• Table 28 Compounds of the formula IM .A(va), in which R 1 is H, R 2 is CH2C6H5, R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 29 Compounds of the formula IM .A(va), in which R 1 is CH3, R 2 is CH2C6H5, R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.
• Table 30 Compounds of the formula IM .A(va), in which R 1 is CH2CH3, R 2 is CH2C6H5, R 3 is Cl, and the combination of m and R 4h for a compound corresponds in each case to one row of Table B.

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• 2019
  • 2019-01-10 WO PCT/EP2019/050537 patent/WO2019137995A1/fr active Application Filing

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