Malononitrile compounds

A compound of formula I

• wherein X is S(═O)n and n=0, 1 or 2,
• R1 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl,
• phenyl or a 5- to 6-membered heteraromatic ring system which may contain 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which heteroaromatic ring is bonded to the X atom via a carbon atom of the ring, and which phenyl or which heteraromatic ring may be bonded via a C1-C10-alkyl group thus forming an aryl-C1-C10-alkyl or hetaryl-C1-C10-alkyl moiety,
• wherein phenyl or the heteroaromatic ring may be fused to a ring selected from the group consisting of phenyl and a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which may contain 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur,
• wherein the hydrogen atoms in the above groups R1 may be partially or in total be replaced by any combination of groups R5;
• A is —NRb2, —C(=G)GRb, —C(=G)NRb2, —C(═NORb)Rb, C(=G)[N═SRb2], —C(=G)NRb—NRb2, wherein two groups Rb together may form a C2-C6-alkandiyl, C2-C6-alkenediyl or C1-C3-alkyl-G-C1-C3-alkyl bridge which may be substituted by 1 to 5 groups R2,
• phenyl or a 3- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteroaromatic ring which may contain 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur,
• wherein phenyl, the heterocyclic ring, or the heteroaromatic ring may be fused to a ring selected from the group consisting of phenyl and a 5- to 6-membered saturated, partially unsaturated or aromatic heterocyclic ring which may contain 1 to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur,
• wherein phenyl or the 5- to 6-membered heteroaromatic ring or the respective fused ring systems may be unsubstituted or substituted by any combination of 1 to 6 groups R2;
• B is a saturated or partially unsaturated hydrocarbon chain with one to 3 carbon chain atoms, wherein the hydrogen atoms of this chain may all or in part be replaced with any combination of groups selected from R3;
• D is a saturated or partially unsaturated hydrocarbon chain with one to 5 carbon chain atoms or C3-C6-cycloalkyl, wherein the hydrogen atoms of this chain or of this cycloalkyl may all or in part be replaced with any combination of groups selected from R4;
• R2 is halogen, cyano, nitro, hydroxy, mercapto, amino, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, C3-C6-halocycloalkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-haloalkoxy, C2-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, C3-C6-cycloalkyloxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkyloxy, C3-C6-halocycloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkylthio, C3-C6-halocycloalkylthio, C1-C6-alkylsulfinyl, C2-C6-alkenylsulfinyl, C3-C6-alkynylsulfinyl, C1-C6-haloalkylsulfinyl, C2-C6-haloalkenylsulfinyl, C3-C6-haloalkynylsulfinyl, C1-C6-alkylsulfonyl, C2-C6-alkenylsulfonyl, C3-C6-alkynylsulfonyl, C1-C6-haloalkylsulfonyl, C2-C6-haloalkenylsulfonyl, C3-C6-haloalkynylsulfonyl, C1-C6-alkylamino, C2-C6-alkenylamino, C2-C6-alkynylamino, di(C1-C6-alkyl)amino, di(C2-C6-alkenyl)amino, di(C2-C6-alkynyl)amino, tri(C1-C10)alkylsilyl, or
• phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteraromatic ring system which may contain 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl and which heteroaromatic ring may be bonded via an oxygen or a sulfur atom or a C1-C4-alkyl-group,
• wherein the above groups R2 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from Ra, or
• R2 is —C(=G)Rb, —C(=G)ORb, —C(=G)NRb2, —C(=G)[N═SRb2], —C(═NORb)Rb, —C(═NORb)NRb2, —C(═NNRb2)Rb, —OC(=G)-OC(=G)ORb, N═SRb2, —NRbC(=G)Rb, —N[C(=G)Rb]2, —NRbC(=G)ORb, —C(=G)NRb—NRb2, —C(=G)NRb—NRb[C(=G)Rb], —NRb—C(=G)NRb2, —NRb—NRbC(=G)Rb, —NRb—N[C(=G)Rb]2, —N[(C=G)Rb]—NRb2, —NRb—NRb[(C=G)GRb], —NRb[(C=G)NRb2, —NRb[C═NRb]Rb, —NRb(C═NRb)NRb2, —O—NRb2, —O—NRb(C=G)Rb, —SO2NRb2, —NRbSO2Rb, —S(═O)Rb, —S(═O)2Rb, —SO2ORb, or —OSO2Rb;
• R3 is halogen, cyano, amino, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-haloalkoxy, C2-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, or
• phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteraromatic ring system which may contain 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl or which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom, or
• 2 groups R3 together with the carbon atom of the hydrocarbon chain may form a 3- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen,
• wherein the above groups R3 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from Ra, or
• R4 is halogen, cyano, amino, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-haloalkoxy, C2-C6-haloalkenyloxy, C3-C6-haloalkynyloxy, C1-C6-alkoxycarbonyl, C1-C6-alkenyloxycarbonyl, C1-C6-alkylamino, di(C1-C6-alkyl)amino, tri(C1-C10)alkylsilyl, or
• phenyl or a 5- to 7-membered saturated or partially unsaturated heterocyclic ring which may contain 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen or a 5- to 6-membered heteraromatic ring system which may contain 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which phenyl and which heterocyclic or heteroaromatic ring may be bonded via an oxygen or a sulfur atom,
• wherein the above groups R4 are unsubstituted, or the hydrogen atoms in these groups may all or in part be replaced with any combination of groups selected from Ra, or
• the moiety R4-D-X—R1 together may form a saturated or unsaturated ring of formula α
• which may have 5 to 7 ring members and besides sulfur 1 to 2 further heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and which ring may be substituted with 1 to 5 groups selected from Ra, or
• the moiety R4-D-X—R1 together may form a group of formula β wherein x is 1 to 5,
• containing a saturated or unsaturated ring which may have 5 to 7 ring members and besides sulfur 1 to 2 further heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and which ring may be substituted with 1 to 5 groups selected from Ra;
• R5 is a group R3;
• G is oxygen or sulfur;
• Ra is each independently halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, C3-C8-halocycloalkenyl, phenoxy, ORi, SRi, S(═O)Ri, S(═O)2Ri, NRiRj, —S(═O)2NRiR, C(═O)Ri, C(═O)ORi, C(═O)NRiRj, C(═NORi)Rj, —NRiC(=G)Rj, —N[C(=G)Ri]2, —NRiC(=G)ORj, —C(=G)NRi—NRj2, —NRiSO2Rj, SiRiyRj3-y (y is 0 to 3), or
• phenyl or a 5- to 6-membered heteraromatic ring which may contain 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, wherein the carbon atoms in phenyl or in the heteroaromatic ring may be substituted with 1 to 5 halogens;
• Ri, Rj are each independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, or C3-C6-halocycloalkenyl;
• Rb is each independently C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, C3-C8-halocycloalkenyl, C3-C6-cycloalkyl-C1-C4-alkyl, or C3-C8-halocycloalkyl-C1-C4-alkyl, or
• phenyl or a 5- to 6-membered heteraromatic ring which may contain 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which heteroaromatic ring may be bound via a C1-C4-alkyl-moiety, and wherein the carbon atoms in phenyl or in the heteroaromatic ring may be substituted with 1 to 3 groups Ra;
• or the enantiomers or diastereomers or salts or N-oxides thereof.