Decahydro-1,4-methanonaphthalen carboxamides

A compound of formula (Ic)

• Wherein
• X is a single or double bond;
• Y is O, S, N(R11) or (CR12R13)(CR14R15)m(CR16R17)n;
• m is 0 or 1;
• n is 0 or 1;
• R1 is hydrogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, CH2C≡CR8, CH2CR9a═CHR9b, CH═C═CH2 or COR10;
• R2 and R3 are each, independently, hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy or C1-4 haloalkoxy;
• R4, R5, R6, R7, R5a and R5b are each, independently, hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, hydroxymethyl, C1-4 alkoxymethyl, C(O)CH3 or C(O)OCH3;
• R8, R9a and R9b are each, independently, hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkylene;
• and R10 is hydrogen, C1-6 alkyl, C1-6 haloalkyl, C1-4 alkoxy(C1-4) alkylene, C1-4 alkyl-S— (C1-4) alkylene, C1-4 alkoxy or aryl;
• R11 is hydrogen, C1-4 alkyl, benzyl wherein the phenyl group is optionally substituted with up to three substituents, each independently selected from halogen, C1-4 alkyl, C1-4 haloalkyl and C1-4 alkoxy, formyl, C(O)C1-4 alkyl optionally substituted by halogen or C1-4 alkoxy, C(═O)O—C1-6 alkyl optionally substituted by halogen, C1-4 alkoxy or cyano or C1-4 alkoxy(C1-4)alkylene;
• R12, R13, R14, R15, R16 and R17 are each, independently, hydrogen, halogen, hydroxy, C1-6 alkyl, C2-6 alkenyl both optionally substituted by halogen, hydroxy, C1-4 alkoxy, ═O, aryl or O—C(O)—C1-4 alkyl or a 3-7 membered carboxylic ring itself optionally substituted by up to three methyl groups, a 3-7 membered saturated ring optionally substituted by up to three methyl groups and optionally containing one heteroatom selected from nitrogen and oxygen or C1-4 alkoxy;
• or R12 and R13 together with the carbon atom to which they are attached form the group C═O or a 3-5 membered carbocyclic ring optionally substituted by up to three methyl groups and optionally with up to 2 heteroatoms each independently selected from O and N;
• or R12 and R13 together form a C1-6 alkylidene optionally substituted by up to three methyl groups or a C3-6 cycloalkylidene group optionally substituted by up to three methyl groups;
• A represents one of the radicals A1 to A18 below
• R18 represents hydrogen, cyano, halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio comprising in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C1-C4-alkyl,
• R19 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio,
• R20 represents hydrogen, C1-C4-alkyl, hydroxy-C1-C4-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkylthio-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl comprising in each case 1 to 5 halogen atoms, or phenyl,
• R21 and R22 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R23 represents halogen, cyano or C1-C4-alkyl, or C1-C4-haloalkyl or C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms,
• R24 and R25 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R26 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R27 represents halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio comprising in each case 1 to 5 halogen atoms,
• R28 represents halogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkylthio or C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms,
• R29 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl,
• R30 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R31 represents C1-C4-alkyl,
• Q1 represents S sulphur, SO, SO2 or CH2,
• p represents 0, 1 or 2, wherein R31 represents identical or different radicals if p represents 2,
• R32 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R33 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R34 and R35 independently of one another represent hydrogen, halogen, amino, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R36 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R37 and R38 independently of one another represent hydrogen, halogen, amino, nitro, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R39 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R40 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R41 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R42 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R43 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R44 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R45 represents hydrogen or C1-C4-alkyl,
• R46 represents halogen or C1-C4-alkyl,
• R47 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R48 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R49 represents halogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkylthio or C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms,
• R50 represents C1-C4-alkyl.

A method for producing compound according to formula (Ia) or (Ib) according to the following reaction schemes.

• Wherein
• X is a single or double bond;
• Y is O, S, N(R11) or (CR12R13)(CR14R15)m(CR16R17)n;
• m is 0 or 1;
• n is 0 or 1;
• R1 is hydrogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, CH2C≡CR8, CH2CR9a═CHR9b, CH═C═CH2 or COR10;
• R2 and R3 are each, independently, hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy or C1-4 haloalkoxy;
• R4, R5, R6, R7, R5a and R5b are each, independently, hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, hydroxymethyl, C1-4 alkoxymethyl, C(O)CH3 or C(O)OCH3;
• R8, R9a and R9b are each, independently, hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkylene;
• and R10 is hydrogen, C1-6 alkyl, C1-6 haloalkyl, C1-4alkoxy(C1-4) alkylene, C1-4 alkyl-S— (C1-4) alkylene, C1-4 alkoxy or aryl;
• R11 is hydrogen, C1-4 alkyl, benzyl wherein the phenyl group is optionally substituted with up to three substituents, each independently selected from halogen, C1-4 alkyl, C1-4 haloalkyl and C1-4 alkoxy, formyl, C(O)C1-4 alkyl optionally substituted by halogen or C1-4 alkoxy, C(═O)O—C1-6 alkyl optionally substituted by halogen, C1-4 alkoxy or cyano or C1-4 alkoxy(C1-4)alkylene;
• R12, R13, R14, R15, R16 and R17 are each, independently, hydrogen, halogen, hydroxy, C1-6 alkyl, C2-6 alkenyl both optionally substituted by halogen, hydroxy, C1-4 alkoxy, ═O, aryl or O—C(O)—C1-4 alkyl or a 3-7 membered carboxylic ring itself optionally substituted by up to three methyl groups, a 3-7 membered saturated ring optionally substituted by up to three methyl groups and optionally containing one heteroatom selected from nitrogen and oxygen or C1-4 alkoxy;
• or R12 and R13 together with the carbon atom to which they are attached form the group C═O or a 3-5 membered carbocyclic ring optionally substituted by up to three methyl groups and optionally with up to 2 heteroatoms each independently selected from O and N;
• or R12 and R13 together form a C1-6 alkylidene optionally substituted by up to three methyl groups or a C3-6 cycloalkylidene group optionally substituted by up to three methyl groups;
• A represents one of the radicals A1 to A18 below
• R18 represents hydrogen, cyano, halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio comprising in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C1-C4-alkyl,
• R19 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylthio,
• R20 represents hydrogen, C1-C4-alkyl, hydroxy-C1-C4-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkylthio-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl comprising in each case 1 to 5 halogen atoms, or phenyl,
• R21 and R22 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R23 represents halogen, cyano or C1-C4-alkyl, or C1-C4-haloalkyl or C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms,
• R24 and R25 independently of one another represent hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R26 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R27 represents halogen, hydroxyl, cyano, C1-C6-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio comprising in each case 1 to 5 halogen atoms,
• R28 represents halogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkylthio or C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms,
• R29 represents hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl,
• R30 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R31 represents C1-C4-alkyl,
• Q1 represents S sulphur, SO, SO2 or CH2,
• p represents 0, 1 or 2, wherein R31 represents identical or different radicals if p represents 2,
• R32 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R33 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R34 and R35 independently of one another represent hydrogen, halogen, amino, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R36 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R37 and R38 independently of one another represent hydrogen, halogen, amino, nitro, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R39 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R40 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R41 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R42 represents hydrogen, halogen, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, cyano, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R43 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R44 represents halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R45 represents hydrogen or C1-C4-alkyl,
• R46 represents halogen or C1-C4-alkyl,
• R47 represents C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R48 represents hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl comprising 1 to 5 halogen atoms,
• R49 represents halogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkyl, C1-C4-haloalkylthio or C1-C4-haloalkoxy comprising in each case 1 to 5 halogen atoms,
• R50 represents C1-C4-alkyl.