Dicyano Alkanoic Acid Amides for Combating Animal Pests

A dicyano alkanoic acid amide of formula I

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof.

A process for the preparation of a dicyano alkanoic acid amide compound of formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof;
• wherein the process comprises:
• reacting compounds (II) with compound (III) in the presence of a base to give compounds (I),
• wherein X, R1, R2, R3, R4, R5 and R6 are as defined above for compounds of formula I and Z1 represents a halogen atom, methanesulfonyl, trifluoromethanesulfonyl or toluenesulfonyl.

A method for combating insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a dicyano alkanoic acid amide compound of formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof.

A method for the control of insects, acarids or nematodes by contacting the insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of a dicyano alkanoic acid amide compound of formula I

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10 haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof, or compositions comprising at least one compound thereof.

A method of protecting growing plants from attack or infestation by insects, acarids or nematodes by applying to the foliage of the plants, or to the soil or water in which they are growing, a pesticidally effective amount of a dicyano alkanoic acid amide compound of formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof, or compositions comprising at least one compound thereof.

A method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a dicyano alkanoic acid amide compound of formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof, their enantiomers or veterinarily acceptable salts, or compositions comprising at least one compound thereof.

A method for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites wherein the method comprises a parasiticidally effective amount of a dicyano alkanoic acid amide compound of formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof, or their enantiomers or veterinary acceptable salts.

A veterinary composition comprising a parasiticidally active amount of a compound of formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof and a veterinary acceptable carrier.

An agricultural composition comprising a pesticidally active amount of a compound of formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof and an agriculturally acceptable carrier.

A method for the protection of seeds from soil insects and of the seedlings'roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one dicyano alkanoic acid amide compound of the formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or salts thereof, or a composition comprising at least one compound thereof.

A seed comprising a dicyano alkanoic acid amide compound of the formula I:

• wherein
• R1 is hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, or C3-C10-haloalkynyl;
• R2 is hydrogen, cyano, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C10-alkoxy, or C1-C10-haloalkoxy;
• R3 and R4 each independently are hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C4-C6-cycloalkenyl, C4-C6-halocycloalkenyl, or
• R3 and R4 together can be C2-C10-alkylene, C2-C10-haloalkylene, C4-C10-alkenylene or C4-C10-haloalkenylene;
• X is oxygen or sulfur;
• R5 and R6 each independently are hydrogen, C1-C10-alkyl, which is unsubstituted or substituted with 1 to 3 substituents each independently selected from the group of cyano, nitro, hydroxy, NR7R8, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and phenyl, wherein phenyl is unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-haloalkenyloxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, R7R8N—C(═O)—, phenylcarbonyl, benzylcarbonyl or phenyl wherein phenylcarbonyl, benzylcarbonyl and phenyl are unsubstituted or substituted with 1 to 5 substituents Ra;
• or
• R5 and R6 each independently are a saturated, partially unsaturated or unsaturated 5- to 6-membered heterocyclic radical which may contain 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur and which radical may be bonded via a carbonyl (C(═O)) linkage, and which radical is unsubstituted or substituted with any combination of 1 to 4 groups Ra;
• Ra is halogen, cyano, nitro, C1-C10-alkyl, C1-C10-haloalkyl, C3-C10-cycloalkyl, C3-C10-halocycloalkyl, C2-C10-alkenyl, C2-C10-haloalkenyl, C2-C10-alkynyl, C3-C10-haloalkynyl, C1-C10-alkoxy, C1-C10-haloalkoxy, C1-C10-alkylthio, C1-C10-haloalkylthio, C1-C10-alkylsulfinyl, C1-C10-haloalkylsulfinyl, C1-C10-alkylsulfonyl, C1-C10-haloalkylsulfonyl, hydroxy, NR7R8, C1-C10-alkoxycarbonyl, C1-C10-haloalkoxycarbonyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl or R7R8N—C(═O)—;
• R7, R8 are each independently hydrogen, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkylcarbonyl, C1-C10-haloalkylcarbonyl, benzyl, phenyl, phenylcarbonyl, C1-C10-alkylsulfonyl, or C1-C10-haloalkylsulfonyl;
• or the enantiomers or diastereomers or agriculturally useful salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.