Compounds for use in anthelminthic treatment

A compound of formula (I-1)

• wherein
• X1 is selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, and C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
• X2 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, and C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
• m is 1, 2, or 3;
• each Y is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkylamino, di-(C1-C4-alkyl)amino, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C1-C4-alkyl, —S—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C1-C4-alkyl, —S(O)—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)2—C1-C4-alkyl, —S(O)2—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkylcarbonylamino;
• and
• A is selected from the group consisting of
• in which
• # depicts the bond which connects A to the rest of the molecule;
• and salts, solvates, solvates of the salts, N-oxides, metal complexes or metalloid complexes thereof.

A method for the control, treatment, or prevention of infections with helminths, comprising administering an effective amount of a compound of formula (I), or a salt, a solvate, a solvate of a salt, an N-oxide, a metal complex, or a metalloid complex thereof, to an animal or human in need thereof

• wherein
• R1 is selected from the group consisting of hydrogen, —CHO, —OH, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 5 halogen atoms, C3-C4-alkenyl, C3-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C3-alkyl, cyano-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di-(C1-C4-alkyl)amino-C1-C4-alkyl, C1-C4-alkylcarbonyl, C1-C4-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C1-C4-alkoxycarbonyl, benzyloxycarbonyl, C1-C4-alkoxy-C1-C4-alkylcarbonyl, —S(O)2—C1-C4-alkyl, and —S(O)2—C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
• n is 0, 1, 2, or 3;
• each X is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF5, —CHO, —OCHO, —NHCHO, —COOH, —CONH2, —CONH(OH), —OCONH2, (hydroxyimino)-C1-C6-alkyl, C1-C8-alkyl, C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-(C1-C8-alkyl)amino, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C2-C8-alkenyloxy, C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, C3-C8-alkynyloxy, C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, C3-C8-cycloalkyl, C3-C8-halogenocycloalkyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C1-C8-alkyl), —CON(C1-C8-alkyl)2, —CONH(OC1-C8-alkyl), —CON(OC1-C8-alkyl)(C1-C8-alkyl), C1-C8-alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C1-C8-alkyl), —OCON(C1-C8-alkyl)2, —OCONH(OC1-C8-alkyl), —OCO(OC1-C8-alkyl), —S—C1-C8-alkyl, —S—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C1-C8-alkyl, —S(O)—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)2—C1-C8-alkyl, —S(O)2—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, (C1-C6-alkoxyimino)-C1-C6-alkyl, (C2-C6-alkenyloxyimino)-C1-C6-alkyl, (C3-C6-alkynyloxyimino)-C1-C6-alkyl, (benzyloxyimino)-C1-C6-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl, and phenylamino;
• m is 0, 1, 2, 3, or 4;
• and
• each Y is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF5, —CHO, —OCHO, —NHCHO, —COOH, —CONH2, —CONH(OH), —OCONH2, (hydroxyimino)-C1-C6-alkyl, C1-C8-alkyl, C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-(C1-C8-alkyl)amino, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C2-C8-alkenyloxy, C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, C3-C8-alkynyloxy, C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, C3-C8-cycloalkyl, C3-C8-halogenocycloalkyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C1-C8-alkyl), —CON(C1-C8-alkyl)2, —CONH(OC1-C8-alkyl), —CON(OC1-C8-alkyl)(C1-C8-alkyl), C1-C8-alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C1-C8-alkyl), —OCON(C1-C8-alkyl)2, —OCONH(OC1-C8-alkyl), —OCO(OC1-C8-alkyl), —S—C1-C8-alkyl, —S—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C1-C8-alkyl, —S(O)—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)2—C1-C8-alkyl, —S(O)2—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, —CH2—S—C1-C8-alkyl, —CH2—S(O)—C1-C8-alkyl, —CH2—S(O)2—C1-C8-alkyl, (C1-C6-alkoxyimino)-C1-C6-alkyl, (C2-C6-alkenyloxyimino)-C1-C6-alkyl, and (C3-C6-alkynyloxyimino)-C1-C6-alkyl;
• wherein two Y may additionally be selected from —O—C1-C3-alkoxy and —O—C1-C3-halogenalkoxy having 1 to 5 halogen atoms, with each oxy function being the connecting atom of the individual Y, thereby forming an annelated 5-, 6- or 7-membered ring with the phenyl moiety that they are connected to;
• or
• each Y is independently selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-halogenoalkyl having 1 to 5 halogen atoms, and a 4 to 7 membered heterocyclic ring system with 1 to 3 heteroatoms, but not O—O, O—S or 3 heteroatoms in a row, independently substituted by oxo, thiono or 1 to 12 substituents Z independently selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —SH, —CHO, —COOH, —CONH2, —CONH(OH), —OCONH2, (hydroxyimino)-C1-C6-alkyl, C1-C6-alkyl, alkyl, C1-C6-halogenoalkyl having 1 to 5 halogen atoms, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, C1-C6-alkoxy, C1-C6-halogenoalkoxy having 1 to 5 halogen atoms, C2-C6-alkenyloxy, C2-C6-halogenoalkenyloxy having 1 to 5 halogen atoms, C3-C6-alkynyloxy, C3-C6-halogenoalkynyloxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 5 halogen atoms, C1-C6-alkylcarbonyl, C1-C6-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C1-C6-alkyl), —CON(C1-C6-alkyl)2, —CONH(OC1-C6-alkyl), —CON(OC1-C6-alkyl)(C1-C6-alkyl), C1-C6-alkoxycarbonyl, C1-C6-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C6-alkylcarbonyloxy, C1-C6-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C6-alkylcarbonylamino, C1-C6-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C1-C6-alkyl), —OCON(C1-C6-alkyl)2, —OCONH(OC1-C6-alkyl), —OCO(OC1-C6-alkyl), —S—C1-C6-alkyl, —S—C1-C6-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C1-C6-alkyl, —S(O)—C1-C6-halogenoalkyl having 1 to 5 halogen atoms, —S(O)2—C1-C6-alkyl, and —S(O)2—C1-C6-halogenoalkyl having 1 to 5 halogen atoms;
• and
• A represents a phenyl group of the formula (A1)
• in which
• # depicts the bond which connects A to the rest of the molecule;
• o is 0, 1, 2, 3, 4, or 5;
• and
• each R is independently selected from the group consisting of halogen, nitro, —OH, NH2, SH, SF5, CHO, OCHO, NHCHO, COOH, cyano, C1-C8-alkyl, C1-C8-halogenoalkyl having 1 to 9 halogen atoms, C2-C8-alkenyl, C2-C8-alkynyl, C3-C6-cycloalkyl, —S—C1-C8-alkyl, —S—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C1-C8-alkoxy-C2-C8-alkenyl, C1-C8-alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, —S(O)—C1-C8-alkyl, —S(O)—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)2—C1-C8-alkyl, —S(O)2—C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C1-C8-alkylsulfonamide, —NH(C1-C8-alkyl), N(C1-C8-alkyl)2, phenyl (optionally substituted by C1-C6-alkoxy) and phenoxy;
• wherein two R bonded to adjacent carbon atoms may together represent —O(CH2)pO—, wherein p represents 1 or 2;
• A represents a heterocycle of the formula (Het-1)
• in which
• # depicts the bond which connects A to the rest of the molecule;
• R11 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4 alkoxy, —S—C1-C5-alkyl, S(O)—C1-C4-alkyl, —S(O)2—C1-C4-alkyl, —S—C2-C5-alkenyl, —S—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms;
• and
• R12, R13, and R14, which may be the same or be different, are selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, —S—C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C1-C4-alkyl, and —S(O)2—C1-C4-alkyl;
• A represents a heterocycle of the formula (Het-2)
• in which
• # depicts the bond which connects A to the rest of the molecule;
• and
• R21 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, and C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
• or
• A represents a heterocycle of the formula (Het-3)
• in which
• # depicts the bond which connects A to the rest of the molecule;
• R31 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4 alkoxy, —S—C1-C5-alkyl, S(O)—C1-C4-alkyl, —S(O)2—C1-C4-alkyl, —S—C2-C5-alkenyl, —S—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms;
• and
• R32, R33, and R34, which may be the same or be different, are selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, —S—C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C1-C4-alkyl, and —S(O)2—C1-C4-alkyl;
• and salts, solvates, solvates of the salts, N-oxides, metal complexes or metalloid complexes thereof.