Carboxamide derivatives as pesticidal compounds

Abstract

Disclosed are compounds of formula (I) which possess pesticidal, especially nematicidal properties wherein in the structural elements have the meaning as indicated in the description. ##STR00001##

Claims

1. A compound of formula (I) ##STR00204## or a salt, N-oxide, metal complex or metalloid complex thereof, wherein B.sup.1 and B.sup.2 are C—X or N, wherein at least one of B.sup.1 or B.sup.2 is N, n is 0, 1, 2, 3 or 4, limited by the number of available positions in the ring to which a substituent X can be connected, each X is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF.sub.5, —CHO, —OCHO, —NHCHO, —COOH, —CONH.sub.2, —CONH(OH), —OCONH.sub.2, (hydroxyimino)-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-alkylamino, di-(C.sub.1-C.sub.8-alkyl)amino, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyloxy, C.sub.2-C.sub.8-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-alkynyloxy, C.sub.3-C.sub.8-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyl, C.sub.1-C.sub.8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.8-alkyl), —CON(C.sub.1-C.sub.8-alkyl).sub.2, —CONH(OC.sub.1-C.sub.8-alkyl), —CON(C.sub.1-C.sub.8-alkyl)(C.sub.1-C.sub.8-alkyl), C.sub.1-C.sub.8-alkoxycarbonyl, C.sub.1-C.sub.8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyloxy, C.sub.1-C.sub.8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonylamino, C.sub.1-C.sub.8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.8-alkyl), —OCON(C.sub.1-C.sub.8-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.8-alkyl), —OCO(OC.sub.1-C.sub.8-alkyl), —S—C.sub.1-C.sub.8-alkyl, —S—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.8-alkyl, —S(O)—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.8-alkyl, —S(O).sub.2—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, (C.sub.1-C.sub.6-alkoxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.2-C.sub.6-alkenyloxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.3-C.sub.6-alkynyloxyimino)-C.sub.1-C.sub.6-alkyl, (benzyloxyimino)-C.sub.1-C.sub.6-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino, m is 0, 1, 2, 3, 4 or 5, and each Y is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF.sub.5, —CHO, —OCHO, —NHCHO, —COOH, —CONH.sub.2, —CONH(OH), —OCONH.sub.2, (hydroxyimino)-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-alkylamino, di-(C.sub.1-C.sub.8-alkyl)amino, wherein both alkyl residues may form a 4- to 7-membered heterocycle incorporating the nitrogen bonded to the phenyl system of the compound, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyloxy, C.sub.2-C.sub.8-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-alkynyloxy, C.sub.3-C.sub.8-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyl, C.sub.1-C.sub.8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.8-alkyl), —CON(C.sub.1-C.sub.8-alkyl).sub.2, —CONH(OC.sub.1-C.sub.8-alkyl), —CON(C.sub.1-C.sub.8-alkyl)(C.sub.1-C.sub.8-alkyl), C.sub.1-C.sub.8-alkoxycarbonyl, C.sub.1-C.sub.8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyloxy, C.sub.1-C.sub.8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonylamino, C.sub.1-C.sub.8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.8-alkyl), —OCON(C.sub.1-C.sub.8-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.8-alkyl), —OCO(OC.sub.1-C.sub.8-alkyl), —S—C.sub.1-C.sub.8-alkyl, —S—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.8-alkyl, —S(O)—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.8-alkyl, —S(O).sub.2—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —CH.sub.2—S—C.sub.1-C.sub.8-alkyl, —CH.sub.2—S(O)—C.sub.1-C.sub.8-alkyl, —CH.sub.2—S(O).sub.2—C.sub.1-C.sub.8-alkyl, (C.sub.1-C.sub.6-alkoxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.2-C.sub.6-alkenyloxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.3-C.sub.6-alkynyloxyimino)-C.sub.1-C.sub.6-alkyl, (benzyloxyimino)-C.sub.1-C.sub.6-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino, or m is 2, 3, 4 or 5, and at least two substituents Y are vicinal and, together with the carbon atoms to which they are bonded, form an annellated 5- or 6-membered carbocycle or a 5- or 6-membered heterocycle with one or two heteroatoms selected from the group consisting of oxygen and nitrogen, whereat two oxygen atoms are not directly connected, the carbocycle or heterocycle being independently substituted by 0 to 4 halogen atoms, 0 to 2 oxo-groups, 0 to 8 C.sub.1-C.sub.8-alkyl, 0 to 8 C.sub.1-C.sub.8-alkoxy or 0 to 4 C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, and the remaining substituents Y are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF.sub.5, —CHO, —OCHO, —NHCHO, —COOH, —CONH.sub.2, —CONH(OH), —OCONH.sub.2, (hydroxyimino)-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-alkylamino, di-(C.sub.1-C.sub.8-alkyl)amino, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyloxy, C.sub.2-C.sub.8-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-alkynyloxy, C.sub.3-C.sub.8-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyl, C.sub.1-C.sub.8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.8-alkyl), —CON(C.sub.1-C.sub.8-alkyl).sub.2, —CONH(OC.sub.1-C.sub.8-alkyl), —CON(OC.sub.1-C.sub.8-alkyl)(C.sub.1-C.sub.8-alkyl), C.sub.1-C.sub.8-alkoxycarbonyl, C.sub.1-C.sub.8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyloxy, C.sub.1-C.sub.8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonylamino, C.sub.1-C.sub.8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.8-alkyl), —OCON(C.sub.1-C.sub.8-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.8-alkyl), —OCO(OC.sub.1-C.sub.8-alkyl), —S—C.sub.1-C.sub.8-alkyl, —S—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.8-alkyl, —S(O)—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.8-alkyl, —S(O).sub.2—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —CH.sub.2—S—C.sub.1-C.sub.8-alkyl, —CH.sub.2—S(O)—C.sub.1-C.sub.8-alkyl, —CH.sub.2—S(O).sub.2—C.sub.1-C.sub.8-alkyl, (C.sub.1-C.sub.6-alkoxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.2-C.sub.6-alkenyloxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.3-C.sub.6-alkynyloxyimino)-C.sub.1-C.sub.6-alkyl, (benzyloxyimino)-C.sub.1-C.sub.6-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —SH, —CHO, —OCHO, —NHCHO, —COOH, —CONH.sub.2, —CONH(OH), —OCONH.sub.2, a (hydroxyimino)-C.sub.1-C.sub.6-alkyl group, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylamino, di-(C.sub.1-C.sub.6-alkyl)amino, C.sub.1-C.sub.6-alkoxy, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halogenocycloalkyl-C.sub.1-C.sub.6-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.6-alkyl), —CON(C.sub.1-C.sub.6-alkyl).sub.2, —CONH(OC.sub.1-C.sub.6-alkyl), —CON(OC.sub.1-C.sub.6-alkyl)(C.sub.1-C.sub.6-alkyl), C.sub.1-C.sub.6-alkoxycarbonyl, a C.sub.1-C.sub.6-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C.sub.1-C.sub.6-alkyl, —OC(O)—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C.sub.1-C.sub.6-alkyl, —NHC(O)—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.6-alkyl), —OCON(C.sub.1-C.sub.6-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.6-alkyl), OCO(OC.sub.1-C.sub.6-alkyl), —S—C.sub.1-C.sub.6-alkyl, —S—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.6-alkyl, —S(O)—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.6-alkyl, —S(O).sub.2—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, benzyl, benzyloxy, —S-benzyl, —S(O)-benzyl, —S(O).sub.2-benzyl, benzylamino, phenoxy, —S-phenyl, —S(O)-phenyl, —S(O).sub.2-phenyl, phenylamino, phenylcarbonylamino and phenyl, with the proviso that R.sup.1 is fluorine and/or R.sup.2 is fluorine, R.sup.5 is selected from the group consisting of hydrogen, cyano, —CHO, —OH, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.6-alkyl, —CONH(C.sub.1-C.sub.6-alkyl), C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.6-alkyl, cyano-C.sub.1-C.sub.6-alkyl, amino-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylamino-C.sub.1-C.sub.6-alkyl, di-(C.sub.1-C.sub.6-alkyl)amino-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-benzyloxycarbonyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkylcarbonyl, —S—C.sub.1-C.sub.6-alkyl, S—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.6-alkyl, and S(O).sub.2—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, A is a phenyl group of the formula (A1) ##STR00205## wherein o is 0, 1, 2, 3, 4 or 5, and each R is independently selected from the group consisting of halogen, nitro, —OH, NH.sub.2, SH, SF.sub.5, CHO, OCHO, NHCHO, COOH, cyano, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-halogenoalkyl having 1 to 9 halogen atoms, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.6-cycloalkyl, —S—C.sub.1-C.sub.8-alkyl, —S—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkoxy-C.sub.2-C.sub.8-alkenyl, C.sub.1-C.sub.8-alkoxycarbonyl, C.sub.1-C.sub.8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyloxy, C.sub.1-C.sub.8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.8-alkyl, —S(O)—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.8-alkyl, —S(O).sub.2—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylsulfonamide, —NH(C.sub.1-C.sub.8-alkyl), N(C.sub.1-C.sub.8-alkyl).sub.2, phenyl (optionally substituted by C.sub.1-C.sub.6-alkoxy) and phenoxy, or two R bonded to adjacent carbon atoms are taken together to form —O(CH.sub.2).sub.pO—, wherein p is 1 or 2, or A is a heterocycle of the formula (Het-1) ##STR00206## wherein R.sup.6 and R.sup.7 may be the same or different and are selected from the group consisting of hydrogen, halogen, amino, nitro, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.8 is selected from the group consisting of hydrogen, halogen, nitro, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-2) ##STR00207## wherein R.sup.9 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.10 and R.sup.11 may be the same or different and are selected from the group consisting of hydrogen, halogen, amino, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-3) ##STR00208## wherein R.sup.12 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.13 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-4) ##STR00209## wherein R.sup.14 and R.sup.15 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, phenyl optionally substituted by halogen or C.sub.1-C.sub.4-alkyl and pyridyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.16 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-5) ##STR00210## wherein R.sup.17 and R.sup.18 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyloxy and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.19 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 atoms, or A is a heterocycle of the formula (Het-6) ##STR00211## wherein R.sup.20 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.21 and R.sup.23 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalky having 1 to 5 halogen atoms, and R.sup.22 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, hydroxyl-C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—N(C.sub.1-C.sub.4-alkyl).sub.2, C.sub.1-C.sub.6-alkylcarbonyl, —S(O).sub.2-phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and benzoyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-7) ##STR00212## wherein R.sup.24 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, hydroxy-C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—N(C.sub.1-C.sub.4-alkyl).sub.2, C.sub.1-C.sub.6-alkylcarbonyl, —S(O).sub.2-phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and benzoyl (optionally substituted by halogen or a C.sub.1-C.sub.4-alkyl), and R.sup.25, R.sup.26 and R.sup.27 may be the same or different and are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-alkylcarbonyl, or A is a heterocycle of the formula (Het-8) ##STR00213## wherein R.sup.28 is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl, and R.sup.29 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-9) ##STR00214## wherein R.sup.30 is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl, and R.sup.31 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-10) ##STR00215## wherein R.sup.32 is selected from the group consisting of hydrogen, halogen, amino, cyano, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.33 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.5-halogenoalkoxy having 1 to 9 halogen atoms, amino, substituted or unsubstituted C.sub.1-C.sub.5-alkylamino and substituted or unsubstituted di-(C.sub.1-C.sub.5-alkyl)-amino, or A is a heterocycle of the formula (Het-11) ##STR00216## wherein R.sup.34 is selected from the group consisting of hydrogen, halogen, amino, cyano, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.35 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-12) ##STR00217## wherein R.sup.36 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, aminocarbonyl and aminocarbonyl-C.sub.1-C.sub.4-alkyl, and R.sup.37 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and R.sup.38 is selected from the group consisting of hydrogen, phenyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O)—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.2—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkylthio-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkoxy-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-13) ##STR00218## wherein R.sup.39 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 atoms, aminocarbonyl and aminocarbonyl-C.sub.1-C.sub.4-alkyl, and R.sup.40 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkylS(O)—C.sub.1-C.sub.4-alkyl, and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and R.sup.41 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O)—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.2—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkylthio-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl or nitro), or A is a heterocycle of the formula (Het-14) ##STR00219## wherein R.sup.42 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, aminocarbonyl and aminocarbonyl-C.sub.1-C.sub.4-alkyl, and R.sup.43 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.44 is selected from the group consisting of hydrogen, phenyl, benzyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O)—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.2—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkylthio-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogeno alkoxy-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-15) ##STR00220## wherein R.sup.45 and R.sup.46 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-16) ##STR00221## wherein R.sup.47 and R.sup.48 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, phenyl (optionally substituted by halogen or a C.sub.1-C.sub.4-alkyl), and heterocyclyl like pyridyl, pyrimidinyl and thiadiazolyl (each optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-17) ##STR00222## wherein R.sup.49 and R.sup.50 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-18) ##STR00223## wherein R.sup.51 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-19) ##STR00224## wherein R.sup.52 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.53 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-20) ##STR00225## wherein R.sup.54 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-21) ##STR00226## wherein R.sup.55 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, and R.sup.56, R.sup.57 and R.sup.58, which may be the same or different, are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-22) ##STR00227## wherein R.sup.59 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4 alkoxy, —S—C.sub.1-C.sub.5-alkyl, S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.2-C.sub.5-alkenyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, phenyloxy (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and —S-phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.60, R.sup.61 and R.sup.62, which may the same or different, are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, N-morpholine optionally substituted by halogen or C.sub.1-C.sub.4-alkyl, and thienyl (optionally substituted by halogen or a C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-23) ##STR00228## wherein R.sup.63, R.sup.64, R.sup.65 and R.sup.66, which may be the same or different, are selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-24) ##STR00229## wherein R.sup.67 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.68 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-alkoxycarbonyl, benzyl (optionally substituted by 1 to 3 halogen atoms), benzyloxycarbonyl (optionally substituted by 1 to 3 halogen atoms), and heterocyclyl like pyridyl and pyrimidinyl (each optionally substituted by halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms), or A is a heterocycle of the formula (Het-25) ##STR00230## wherein R.sup.69 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, and R.sup.70 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and benzyl, or A is a heterocycle of the formula (Het-26) ##STR00231## wherein X.sup.1 is selected from the group consisting of sulphur, —SO—, —SO.sub.2— and —CH.sub.2—, and R.sup.71 is selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.72 and R.sup.73 may be the same or different and are selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-27) ##STR00232## wherein R.sup.74 is selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-28) ##STR00233## wherein R.sup.75 is selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-29) ##STR00234## wherein R.sup.76 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms.

2. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1, wherein B.sup.1, B.sup.2 are C—X or N, wherein at least one of B.sup.1 or B.sup.2 is N, n is 1 or 2, limited by the number of available positions in the ring to which a substituent X can be connected, each X is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyloxy, C.sub.2-C.sub.4-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.4-alkynyloxy, C.sub.3-C.sub.4-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.4-alkyl), —CON(C.sub.1-C.sub.4-alkyl).sub.2, —CONH(OC.sub.1-C.sub.4-alkyl), —CON(OC.sub.1-C.sub.4-alkyl)(C.sub.1-C.sub.4-alkyl), C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyloxy, C.sub.1-C.sub.4-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonylamino, C.sub.1-C.sub.4-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.4-alkyl), —OCON(C.sub.1-C.sub.4-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.4-alkyl), —OCO(OC.sub.1-C.sub.4-alkyl), —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, (C.sub.1-C.sub.4-alkoxyimino)-C.sub.1-C.sub.4-alkyl, (C.sub.2-C.sub.6-alkenyloxyimino)-C.sub.1-C.sub.4-alkyl, (C.sub.3-C.sub.6-alkynyloxyimino)-C.sub.1-C.sub.4-alkyl, (benzyloxyimino)-C.sub.1-C.sub.6-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, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, wherein both alkyl residues may form a 4- to 7-membered heterocycle incorporating the nitrogen bonded to the phenyl system of the compound, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyloxy, C.sub.2-C.sub.4-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.4-alkynyloxy, C.sub.3-C.sub.4-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.4-alkyl), —CON(C.sub.1-C.sub.4-alkyl).sub.2, —CONH(OC.sub.1-C.sub.4-alkyl), —CON(OC.sub.1-C.sub.4-alkyl)(C.sub.1-C.sub.4-alkyl), C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyloxy, C.sub.1-C.sub.4-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonylamino, C.sub.1-C.sub.4-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.4-alkyl), —OCON(C.sub.1-C.sub.4-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.4-alkyl), —OCO(OC.sub.1-C.sub.4-alkyl), —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —CH.sub.2—S—C.sub.1-C.sub.4-alkyl, —CH.sub.2—S(O)—C.sub.1-C.sub.4-alkyl, —CH.sub.2—S(O).sub.2—C.sub.1-C.sub.4-alkyl, (C.sub.1-C.sub.4-alkoxyimino)-C.sub.1-C.sub.4-alkyl, (C.sub.2-C.sub.6-alkenyloxyimino)-C.sub.1-C.sub.4-alkyl, (C.sub.3-C.sub.6-alkynyloxyimino)-C.sub.1-C.sub.4-alkyl, (benzyloxyimino)-C.sub.1-C.sub.6-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino, or m is 2, 3 or 4 and at least two substituents Y are vicinal and, together with the carbon atoms to which they are bonded, form an annellated 5- or 6-membered carbocycle or a 5- or 6-membered heterocycle with one or two heteroatoms selected from the group consisting of oxygen and nitrogen, whereat two oxygen atoms are not directly connected, the carbocycle or heterocycle being independently substituted by 0 to 2 halogen atoms, 0 to 2 oxo-groups, 0 to 4 C.sub.1-C.sub.4-alkyl, 0 to 4 C.sub.1-C.sub.4-alkoxy or 0 to 2 C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and the remaining substituents Y are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyloxy, C.sub.2-C.sub.4-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.4-alkynyloxy, C.sub.3-C.sub.4-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.4-alkyl), —CON(C.sub.1-C.sub.4-alkyl).sub.2, —CONH(OC.sub.1-C.sub.4-alkyl), —CON(OC.sub.1-C.sub.4-alkyl)(C.sub.1-C.sub.4-alkyl), C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyloxy, C.sub.1-C.sub.4-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonylamino, C.sub.1-C.sub.4-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.4-alkyl), —OCON(C.sub.1-C.sub.4-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.4-alkyl), —OCO(OC.sub.1-C.sub.4-alkyl), —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —CH.sub.2—S—C.sub.1-C.sub.4-alkyl, —CH.sub.2—S(O)—C.sub.1-C.sub.4-alkyl, —CH.sub.2—S(O).sub.2—C.sub.1-C.sub.4-alkyl, (C.sub.1-C.sub.4-alkoxyimino)-C.sub.1-C.sub.4-alkyl, (C.sub.2-C.sub.6-alkenyloxyimino)-C.sub.1-C.sub.4-alkyl, (C.sub.3-C.sub.6-alkynyloxyimino)-C.sub.1-C.sub.4-alkyl, (benzyloxyimino)-C.sub.1-C.sub.6-alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —CHO, —COOH, —CONH.sub.2, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyloxy, C.sub.2-C.sub.4-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.4-alkynyloxy, C.sub.3-C.sub.4-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.6-halogenocycloalkyl-C.sub.1-C.sub.3-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.4-alkyl), —CON(C.sub.1-C.sub.4-alkyl).sub.2, —CONH(OC.sub.1-C.sub.4-alkyl), —CON(OC.sub.1-C.sub.4-alkyl)(C.sub.1-C.sub.4-alkyl), C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C.sub.1-C.sub.4-alkyl, —OC(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C.sub.1-C.sub.4-alkyl, —NHC(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.4-alkyl), —OCON(C.sub.1-C.sub.4-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.4-alkyl), OCO(OC.sub.1-C.sub.4-alkyl), —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, benzyl, benzyloxy, —S-benzyl, —S(O)-benzyl, —S(O).sub.2-benzyl, benzylamino, phenoxy, —S-phenyl, —S(O)-phenyl, —S(O).sub.2-phenyl, phenylamino, phenylcarbonylamino and phenyl, with the proviso that R.sup.1 is fluorine and/or R.sup.2 is fluorine, R.sup.5 is selected from the group consisting of hydrogen, —CHO, —OH, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, cyano-C.sub.1-C.sub.4-alkyl, amino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylamino-C.sub.1-C.sub.4-alkyl, di-(C.sub.1-C.sub.4-alkyl)amino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxycarbonyl, benzyloxycarbonyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkylcarbonyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, A is a phenyl group of formula (A1) ##STR00235## wherein o is 0, 1 or 2, and each R is independently selected from the group consisting of halogen, nitro, —OH, CHO, OCHO, NHCHO, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.6-cycloalkyl, —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkenyl, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylcarbonyloxy, C.sub.1-C.sub.4-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylsulfonamide, —NH(C.sub.1-C.sub.4-alkyl), N(C.sub.1-C.sub.4-alkyl).sub.2, phenyl (optionally substituted by C.sub.1-C.sub.4-alkoxy) and phenoxy, or two R bonded to adjacent carbon atoms are taken together to form O(CH.sub.2).sub.pO—, wherein p is 1 or 2, or A is a heterocycle of the formula (Het-1) ##STR00236## wherein R.sup.6 and R.sup.7 may be the same or different and are selected from the group consisting of hydrogen, halogen, nitro, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.8 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-2) ##STR00237## wherein R.sup.9 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.10 and R.sup.11 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, phenyl optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-4) ##STR00238## wherein R.sup.14 and R.sup.15 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and pyridyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.16 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-5) ##STR00239## wherein R.sup.17 and R.sup.18 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyloxy and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.19 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 atoms, or A is a heterocycle of the formula (Het-6) ##STR00240## wherein R.sup.20 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.21 and R.sup.23 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalky having 1 to 5 halogen atoms, and R.sup.22 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-7) ##STR00241## wherein R.sup.24 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkylcarbonyl, and benzoyl (optionally substituted by halogen or a C.sub.1-C.sub.4-alkyl), and R.sup.25, R.sup.26 and R.sup.27 may be the same or different and are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-alkylcarbonyl, or A is a heterocycle of the formula (Het-9) ##STR00242## wherein R.sup.30 is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl, and R.sup.31 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-10) ##STR00243## wherein R.sup.32 is selected from the group consisting of hydrogen, halogen, amino, cyano, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.33 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.5-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, substituted or unsubstituted C.sub.1-C.sub.5-alkylamino and substituted or unsubstituted di-(C.sub.1-C.sub.5-alkyl)-amino, or A is a heterocycle of the formula (Het-11) ##STR00244## wherein R.sup.34 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.35 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-12) ##STR00245## wherein R.sup.36 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl and —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.37 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and R.sup.38 is selected from the group consisting of phenyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O)—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.2—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkylthio-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkoxy-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-13) ##STR00246## wherein R.sup.39 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 atoms, aminocarbonyl and aminocarbonyl-C.sub.1-C.sub.4-alkyl, and R.sup.40 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and R.sup.41 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O)—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.2—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkylthio-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms and phenyl optionally substituted by halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl or nitro, or A is a heterocycle of the formula (Het-14) ##STR00247## wherein R.sup.42 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, aminocarbonyl and aminocarbonyl-C.sub.1-C.sub.4-alkyl, and R.sup.43 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.44 is selected from the group consisting of phenyl, benzyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylthio-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O)—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-S(O).sub.2—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkylthio-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkoxy-C.sub.1-C.sub.4-alkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-15) ##STR00248## wherein R.sup.45 and R.sup.46 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-16) ##STR00249## wherein R.sup.47 and R.sup.48 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, phenyl (optionally substituted by halogen or a C.sub.1-C.sub.4-alkyl), or heterocyclyl like pyridyl, pyrimidinyl and thiadiazolyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-17) ##STR00250## wherein R.sup.49 and R.sup.50 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-19) ##STR00251## wherein R.sup.52 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.53 is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-20) ##STR00252## wherein R.sup.54 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-21) ##STR00253## wherein R.sup.55 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, and R.sup.56, R.sup.57 and R.sup.58, which may be the same or different, are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-22) ##STR00254## wherein R.sup.59 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4 alkoxy, —S—C.sub.1-C.sub.5-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.2-C.sub.5-alkenyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, phenyloxy (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and —S-phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.60, R.sup.61 and R.sup.62, which may the same or different, are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, N-morpholine (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and thienyl (optionally substituted by halogen or a C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-23) ##STR00255## wherein R.sup.63, R.sup.64, R.sup.65 and R.sup.66, which may be the same or different, are selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-24) ##STR00256## wherein R.sup.67 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.68 is selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-alkoxycarbonyl, benzyl (optionally substituted by 1 to 3 halogen atoms), benzyloxycarbonyl (optionally substituted by 1 to 3 halogen atoms) and heterocyclyl like pyrimidinyl, (optionally substituted by halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms), or A is a heterocycle of the formula (Het-25) ##STR00257## wherein R.sup.69 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.70 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and benzyl, or A is a heterocycle of the formula (Het-26) ##STR00258## wherein X.sup.1 is selected from the group consisting of sulphur, —SO—, and —SO.sub.2—, and R.sup.71 is selected from the group consisting of C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.72 and R.sup.73 may be the same or different and are selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-29) ##STR00259## wherein R.sup.76 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms.

3. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1 or 2, wherein B.sup.1, B.sup.2 are C—X or N, wherein at least one of B.sup.1 or B.sup.2 is N, n is 1, X is selected from the group consisting of hydrogen, halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, m is 0, 1, 2 or 3, and each Y is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, wherein both alkyl residues may form a 4- to 7-membered heterocycle incorporating the nitrogen bonded to the phenyl system of the compound, C.sub.1-C.sub.4-alkylcarbonylamino, —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or m is 2 or 3, and at least two substituents Y are vicinal and, together with the phenyl ring to which they are bonded, form a structure which is selected from: ##STR00260## ##STR00261## and the remaining substituent Y is selected from the group consisting of hydrogen, halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, 41ydroxyl, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.4-alkoxycarbonyl, —OC(O)—C.sub.1-C.sub.4-alkyl, —NHC(O)—C.sub.1-C.sub.4-alkyl, and phenyl, with the proviso that R.sup.1 is fluorine and/or R.sup.2 is fluorine, R.sup.3 and R.sup.4 are the same or different and are selected from the group consisting of hydrogen, —COOH, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogeno alkyl C.sub.1-C.sub.4-alkoxy, 41ydroxyl-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.3-alkyl, —CONH(C.sub.1-C.sub.4-alkyl), C.sub.1-C.sub.4-alkoxycarbonyl, —OC(O)—C.sub.1-C.sub.4-alkyl, and phenyl, R.sup.5 is selected from the group consisting of hydrogen, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkylcarbonyl, and C.sub.1-C.sub.4-alkoxycarbonyl, A is a phenyl group of formula (A1) ##STR00262## wherein o is 0, 1 or 2, and each R is independently selected from the group consisting of halogen, nitro, —OH, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1C.sub.1-C.sub.4-alkoxycarbonyl, —NH(C.sub.1-C.sub.4-alkyl), phenyl (optionally substituted by C.sub.1-C.sub.4-alkoxy) and phenoxy, or A is a heterocycle of the formula (Het-1) ##STR00263## wherein R.sup.6 and R.sup.7 may be the same or different and are selected from the group consisting of hydrogen, halogen, nitro, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.8 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-2) ##STR00264## wherein R.sup.9 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.10 and R.sup.11 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and phenyl optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-4) ##STR00265## wherein R.sup.14 and R.sup.15 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and pyridyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.16 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, or A is a heterocycle of the formula (Het-5) ##STR00266## wherein R.sup.17 and R.sup.18 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyloxy and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.19 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 atoms, or A is a heterocycle of the formula (Het-6) ##STR00267## wherein R.sup.20 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and R.sup.21 and R.sup.23 may be the same or different and are selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalky having 1 to 5 halogen atoms, and R.sup.22 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, and C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, or A represents a heterocycle of the formula (Het-10) ##STR00268## wherein R.sup.32 is selected from the group consisting of hydrogen, halogen, amino, cyano, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.33 is selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.5-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, substituted or unsubstituted C.sub.1-C.sub.5-alkylamino and substituted or unsubstituted di-(C.sub.1-C.sub.5-alkyl)-amino, or A represents a heterocycle of the formula (Het-21) ##STR00269## wherein R.sup.55 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, and R.sup.56, R.sup.57 and R.sup.58, which may be the same or different, are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl and —S(O).sub.2—C.sub.1-C.sub.4-alkyl, or A is a heterocycle of the formula (Het-22) ##STR00270## wherein R.sup.59 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4 alkoxy, —S—C.sub.1-C.sub.5-alkyl, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, —S—C.sub.2-C.sub.5-alkenyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, phenyloxy (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and —S-phenyl (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl), and R.sup.60, R.sup.61 and R.sup.62, which may the same or different, are selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, —S—C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, N-morpholine (optionally substituted by halogen or C.sub.1-C.sub.4-alkyl) and thienyl (optionally substituted by halogen or a C.sub.1-C.sub.4-alkyl), or A is a heterocycle of the formula (Het-29) ##STR00271## wherein R.sup.76 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms.

4. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1 or 2, wherein B.sup.1 is N, B.sup.2 is CH, n is 1, X is selected from the group consisting of hydrogen, halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, and C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, m is 0, 1 or 2, and each Y is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.1-C.sub.4-alkylamino, di-(C.sub.1-C.sub.4-alkyl)amino, wherein both alkyl residues may form a 4- to 7-membered heterocycle incorporating the nitrogen bonded to the phenyl system of the compound, C.sub.1-C.sub.4-alkylcarbonylamino, —S—C.sub.1-C.sub.4-alkyl, —S—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.4-alkyl, —S(O)—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.4-alkyl, and —S(O).sub.2—C.sub.1-C.sub.4-halogenoalkyl having 1 to 5 halogen atoms, or m is 2 or 3, and at least two substituents Y are vicinal and, together with the phenyl ring to which they are bonded, form a structure which is selected from: ##STR00272## ##STR00273## and the remaining substituent Y is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, i-propyl, n-propyl, n-butyl, s-butyl, t-butyl, i-butyl, methoxy, ethoxy, isopropoxy, n-propoxy, trifluoromethyl and difluoromethyl, R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, methyl, ethyl, methoxy, ethoxy and fluorine, with the proviso that R.sup.1 is fluorine and/or R.sup.2 is fluorine, R.sup.3 and R.sup.4 are the same or different and are selected from the group consisting of hydrogen, methyl and ethyl, R.sup.5 is hydrogen, A is selected from: ##STR00274## or A is selected from: ##STR00275##

5. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1 or 2, wherein B.sup.1 is N, B.sup.2 is CH, n is 1, X is selected from the group consisting of hydrogen and chlorine, m is 0, 1 or 2, and each Y is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, i-propyl, n-propyl, n-butyl, s-butyl, t-butyl, i-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, n-propoxy, trifluoromethoxy, difluoromethoxy, methylamino, dimethylamino, pyrrolidino, N-methyl-piperazino, morpholino, methylcarbonylamino, methylsulfonyl, methylsulfinyl, methylsulfanyl, trifluoromethylsulfonyl, trifluoromethylsulfinyl or trifluoromethylsulfanyl, or m is 2 or 3, and at least two substituents Y are vicinal and, together with the phenyl ring to which they are bonded, form a structure which is selected from: ##STR00276## and the remaining substituent Y is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, methyl, ethyl, i-propyl, n-propyl, n-butyl, s-butyl, t-butyl, i-butyl, methoxy, ethoxy, isopropoxy, n-propoxy, trifluoromethyl and difluoromethyl, R.sup.1 and R.sup.2 are independently hydrogen, methyl or fluorine, with the proviso that R.sup.1 is fluorine and/or R.sup.2 is fluorine, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, and A is ##STR00277## or ##STR00278## or ##STR00279##

6. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1 or 2 which is represented by formula (I-1) ##STR00280## and wherein R.sup.1, R.sup.2, X, Y, n, m and A are as defined in claim 1 or in claim 2.

7. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1 or 2, wherein the phenyl ring bearing the substituent Ym is in para-position.

8. The compound of formula (INT-a) ##STR00281## or a salt, N-oxide, metal complex or metalloid complex thereof, wherein R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —SH, —CHO, —OCHO, —NHCHO, —COOH, —CONH.sub.2, —CONH(OH), —OCONH.sub.2, a (hydroxyimino)-C.sub.1-C.sub.6-alkyl group, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylamino, di-(C.sub.1-C.sub.6-alkyl)amino, C.sub.1-C.sub.6-alkoxy, hydroxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halogenocycloalkyl-C.sub.1-C.sub.6-alkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.6-alkyl), —CON(C.sub.1-C.sub.6-alkyl).sub.2, —CONH(OC.sub.1-C.sub.6-alkyl), —CON(OC.sub.1-C.sub.6-alkyl)(C.sub.1-C.sub.6-alkyl), C.sub.1-C.sub.6-alkoxycarbonyl, a C.sub.1-C.sub.6-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C.sub.1-C.sub.6-alkyl, —OC(O)—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C.sub.1-C.sub.6-alkyl, —NHC(O)—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.6-alkyl), —OCON(C.sub.1-C.sub.6-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.6-alkyl), OCO(OC.sub.1-C.sub.6-alkyl), —S—C.sub.1-C.sub.6-alkyl, —S—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.6-alkyl, —S(O)—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.6-alkyl, —S(O).sub.2—C.sub.1-C.sub.6-halogenoalkyl having 1 to 5 halogen atoms, benzyl, benzyloxy, —S-benzyl, —S(O)-benzyl, —S(O).sub.2-benzyl, benzylamino, phenoxy, —S-phenyl, —S(O)-phenyl, —S(O).sub.2-phenyl, phenylamino, phenylcarbonylamino and phenyl, with the proviso that R.sup.1 is fluorine and/or R.sup.2 is fluorine, Y is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF.sub.5, —CHO, —OCHO, —NHCHO, —COOH, —CONH.sub.2, —CONH(OH), —OCONH.sub.2, (hydroxyimino)-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-alkylamino, di-(C.sub.1-C.sub.8-alkyl)amino, wherein both alkyl residues may form a 4- to 7-membered heterocycle incorporating the nitrogen bonded to the phenyl system of the compound, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-halogenoalkoxy having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyloxy, C.sub.2-C.sub.8-halogenoalkenyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-alkynyloxy, C.sub.3-C.sub.8-halogenoalkynyloxy having 1 to 5 halogen atoms, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halogenocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyl, C.sub.1-C.sub.8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C.sub.1-C.sub.8-alkyl), —CON(C.sub.1-C.sub.8-alkyl).sub.2, —CONH(OC.sub.1-C.sub.8-alkyl), —CON(OC.sub.1-C.sub.8-alkyl)(C.sub.1-C.sub.8-alkyl), C.sub.1-C.sub.8-alkoxycarbonyl, C.sub.1-C.sub.8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonyloxy, C.sub.1-C.sub.8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkylcarbonylamino, C.sub.1-C.sub.8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C.sub.1-C.sub.8-alkyl), —OCON(C.sub.1-C.sub.8-alkyl).sub.2, —OCONH(OC.sub.1-C.sub.8-alkyl), —OCO(OC.sub.1-C.sub.8-alkyl), —S—C.sub.1-C.sub.8-alkyl, —S—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C.sub.1-C.sub.8-alkyl, —S(O)—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —S(O).sub.2—C.sub.1-C.sub.8-alkyl, —S(O).sub.2—C.sub.1-C.sub.8-halogenoalkyl having 1 to 5 halogen atoms, —CH.sub.2—S—C.sub.1-C.sub.8-alkyl, —CH.sub.2—S(O)—C.sub.1-C.sub.8-alkyl, —CH.sub.2—S(O).sub.2—C.sub.1-C.sub.8-alkyl, (C.sub.1-C.sub.6-alkoxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.2-C.sub.6-alkenyloxyimino)-C.sub.1-C.sub.6-alkyl, (C.sub.3-C.sub.6-alkynyloxyimino)-C.sub.1-C.sub.6-alkyl, (benzyloxyimino)-C.sub.1-C.sub.6-alkyl, benzyloxy, —S-benzyl, benzyl amino, phenoxy, —S-phenyl and phenylamino, and m is 0, 1, 2, 3, 4 or 5.

9. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 8, wherein the phenyl ring bearing the substituent Ym is in para-position.

10. The compound or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 8 or 9 which is represented by formula (INT-1) ##STR00282##

11. A formulation comprising at least one compound of formula (I) or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1.

12. The formulation according to claim 11 which further comprises at least one extender and/or at least one surfactant.

13. The formulation according to claim 11 or 12, wherein the compound of the formula (I), or a salt, N-oxide, metal complex or metalloid complex thereof, is present in a mixture with at least one other active compound.

14. A method for controlling an animal pest, wherein a compound of formula (I) or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1, or a formulation according to claim 11 is allowed to act on the animal pest and/or their habitat.

15. The method according to claim 14, wherein the animal pest comprises a nematode or is a nematode.

16. A method for protecting a seed and/or a germinating plant from attack by a pest, particularly a nematode, comprising the step of contacting the seed with a compound of formula (I) or a salt, N-oxide, metal complex or metalloid complex thereof according to claim 1, or with a formulation according to claim 11.

17. A seed obtained by a method according to claim 16.

Description

PREPARATION EXAMPLES

(1) .sup.1H-NMR Data

(2) .sup.1H-NMR-data were determined with a Bruker Avance 400 (Method M1) equipped with a flow cell (60 μl volume) or with a Bruker AVIII 400 equipped with 1.7 mm cryo-CPTCI probe head or with a Bruker AVII 600 (600.13 MHz) equipped with a 5 mm cyroTCI probe head or with a Bruker AVIII 600 (601.6 MHz) equipped with a 5 mm cryo CPMNP probe head with tetramethylsilane as reference (0.0) and the solvents CD.sub.3CN, CDCl.sub.3 or D.sub.6-DMSO.

(3) NMR-data of selected examples are listed in classic format (chemical shift S, multiplicity, number of hydrogen atoms) or as NMR-peak-lists.

(4) The NMR spectra of steps 1 to 5 of preparation 1 have been measured on a Varian 400 MHz Mercury Plus.

(5) Preparation 1:

(6) Step 1:

Synthesis of ethyl (5-bromo-3-chloropyridin-2-yl)-(cyano)acetate

(7) ##STR00141##

(8) To a suspension of NaH (4.0 g, 1.5 eq.) in DMF (45 ml) at 0° C., ethyl cyanoacetate (10.6 ml, 1.5 eq.) was added and stirred at room temperature for 30 minutes. Then 5-bromo-2,3-dichloropyridine (15.0 g, 1.0 eq.) in DMF (30 ml) was added to the reaction mixture at room temperature and stirred at 80° C. for 4 hours. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified over silica gel (100-200 mesh) column chromatography by eluting with 5% EtOAc/pet ether, this yielded 10.0 g (49.8%).

(9) .sup.1H-NMR (400 MHz, CDCl.sub.3); δ 1.3 (t, 3H), 4.3 (q, 2H), 5.3 (s, 1H), 8.0 (s, 1H), 8.6 (s, 1H).

(10) Step 2:

Synthesis of (5-bromo-3-chloropyridin-2-yl)acetonitrile

(11) ##STR00142##

(12) To a solution of ethyl (5-bromo-3-chloropyridin-2-yl)(cyano)acetate (10.0 g, 1.0 eq.) in DMSO (30 ml) and water (5 ml) at room temperature, NaCl (636 mg, 0.33 eq) was added and the reaction mixture was stirred at 170° C. for one hour. After completion of reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified over silica gel (100-200 mesh) column chromatography by eluting with 3% EtOAc/pet ether to yield 7.0 g (91.8%).

(13) .sup.1H-NMR (400 MHz, CDCl.sub.3); δ 4 (s, 2H) 7.9 (s, 1H), 8.6 (s, 1H).

(14) Step 3:

Synthesis of tert-butyl [2-(5-bromo-3-chloropyridin-2-yl)ethyl]carbamate

(15) ##STR00143##

(16) The solution of (5-bromo-3-chloropyridin-2-yl)acetonitrile (2×3.5 g, 1.0 eq.) in methanol (2×28 ml) at 0° C., BOC anhydride (2×3.5 ml, 1.1 eq.), NiCl.sub.2.6H.sub.2O (2×1.08 g, 0.3 eq.), NaBH.sub.4 (2×1.72 g, 3.0 eq.) were added and the reaction mixture was stirred at room temperature for 30 minutes. After completion of reaction the reaction mixture was concentrated under reduced pressure, the residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified over silica gel (100-200 mesh) column chromatography by eluting with 10% EtOAc/pet ether to to yield 5.0 g (49.2%).

(17) .sup.1H-NMR (400 MHz, CDCl.sub.3); δ 1.4 (s, 9H), 3.1 (m, 2H), 3.6 (m, 2H), 5.1 (br, 1H), 7.8 (s, 1H), 8.5 (s, 1H).

(18) Step 4:

Synthesis of 2-(5-bromo-3-chloropyridin-2-yl)ethanamine hydrochloride

(19) ##STR00144##

(20) The solution of tert-butyl [2-(5-bromo-3-chloropyridin-2-yl)ethyl]carbamate (5.0 g, 1.0 eq.) in methanol (30 ml) at room temperature, methanolic HCl (50 ml) was added and the reaction mixture was stirred at 70° C. for one hour. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by ethyl acetate washings to yield 3.0 g (74%).

(21) .sup.1H-NMR (400 MHz, D.sub.6-DMSO); δ: 3.2 (m, 4H), 8.2 (br, 2H), 8.4 (s, 1H), 8.6 (s, 1H).

(22) Step 5:

Synthesis of N-[2-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-(trifluoromethyl)benzamide

(23) ##STR00145##

(24) To a solution of 2-(5-bromo-3-chloropyridin-2-yl)ethanamine hydrochloride (3.0 g, 1.0 eq.) in THF (30 ml) at room temperature, TEA (4.6 ml, 3.0 eq.), 2-trifluoromethyl benzoic acid (2.3 g, 1.1 eq.), EDC.HCl (3.16 g, 1.5 eq.) were added and stirred for 15 minutes. Then HOBT (2.23 g, 1.5 eq.) was added to the reaction mixture and continued the reaction at same temperature for four hours. After completion of reaction, the reaction mixture was diluted with 2N HCl and extracted with ethyl acetate. The combined organic layers were washed with Na.sub.2CO.sub.3 solution, brine, dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure to yield 3.0 g, (68.2%).

(25) .sup.1H-NMR (400 MHz, CDCl.sub.3); δ 3.2 (m, 2H), 4 (m, 2H), 6.6 (br, 1H), 7.5-7.6 (m, 3H), 7.7 (m, 1H), 7.8 (s, 1H), 8.4 (s, 1H).

(26) Step 6:

Synthesis of N-{2-[3-chloro-5-(4-chlorophenyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide (expl. 1)

(27) ##STR00146##

(28) 114 mg (0.28 mmol) N-[2-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-(trifluoromethyl)benzamide (from step 5) and 43.8 mg (0.28 mmol) (4-chlorophenyl)boronic acid were dissolved in 3 mL dioxane. Thereafter, 20.7 mg (0.02 mmol) dichloro-bis(tricyclohexylphosphine) palladium-(II) and 182.5 mg (0.56 mmol) cesium carbonate in 0.5 mL water were added and treated in a sealed microwave vial in a Biotage microwave oven (Initiator) at 100° C. for 20 minutes. The reaction mixture was filtered over a silica gel sodium sulfate cartridge, the solvents were evaporated and the crude product was purified by silica gel chromatography (cyclohexane/ethyl acetate gradient) to afford 103 mg (79.9%) of the title compound as off-white solid.

(29) LC-MS (M+H).sup.+=439.0

(30) .sup.1H-NMR (400 MHz, d6-DMSO); δ 8.85 (d, 1H), 8.63 (t, NH), 8.25 (d, 1H), 7.84 (d, 2H), 7.77-7.61 (m, 3H), 7.58 (d, 2H), 7.53 (d, 1H), 3.69-3.64 (qu, 2H), 3.19-3.15 (t, 2H).

(31) Preparation 2:

(32) Step 1:

Synthesis of 2-(5-bromo-3-chloropyridin-2-yl)-2,2-difluoroethanamine was performed in analogy to WO 2013/064460 A1 (referred as intermediate IIa-14 and IIa-151

(33) ##STR00147##

(34) .sup.1H-NMR (400 MHz, d6-DMSO); δ 8.78 (d, J=1.6 Hz, 1H), 8.52 (d, J=2.0 Hz, 1H), 3.37 (t, J=14.8 Hz, 2H), 1.72 (s, 2H).

(35) Step 2a:

Synthesis of N-[2-(5-bromo-3-chloropyridin-2-yl)-2,2-difluoroethyl]-2-(trifluoromethyl)benzamide

(36) ##STR00148##

(37) To a solution of 2-(5-bromo-3-chloropyridin-2-yl)-2,2-difluoroethanamine (2.56 g, 1.03 eq.) in dichloromethane (50 ml) at room temperature, TEA (3.38 ml, 3.0 eq.) and 2-trifluoromethyl benzoic acid chloride (1.68 g, 1.0 eq.) were added and stirred overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with dichloromethane. The solvent of the combined organic layers was evaporated under reduced pressure. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate) to yield 2.86 g (68.5%) as off-white solid.

(38) LC-MS (M+H).sup.+=442.9; 444.9

(39) .sup.1H-NMR (400 MHz, d6-DMSO); δ 8.97 (t, 1H, NH), 8.80 (d, 1H), 8.56 (d, 1H), 7.77-7.63 (m, 3H), 7.45 (d, 1H), 4.28-4.19 (m, 2H).

(40) Step 2b:

Synthesis of 2-[3-chloro-5-(4-fluorophenyl)-2-pyridyl]-2,2-difluoro-ethanamine (expl. INT-1)

(41) ##STR00149##

(42) 42 mg (0.3 mmol) (4-fluorophenyl)boronic acid and 100 mg (0.3 mmol) 2-(5-bromo-3-chloro-2-pyridyl)-2,2-difluoro-ethanamine from step 1 were dissolved in 4.6 mL dioxane followed by addition of 195.5 mg (0.6 mmol) cesium carbonate in 0.58 mL water and 22.14 mg (0.03 mmol) dichloro-bis(tricyclohexylphosphine)-palladium-(II) catalyst. The reaction mixture was kept under stirring in a closed vial for 16 h at 100° C. The reaction mixture was filtered via a silica gel/sodium sulfate cartridge, solvents have been evaporated under reduced pressure and the remaining yellow-coloured solid was purified by MPLC on silicagel (solvent gradient cyclohexane/ethylacetate) to afford 69 mg the title compound as colorless crystalline solid (yield: 77%).

(43) LC-MS (M+H).sup.+=287.0

(44) .sup.1H-NMR (400 MHz, d6-DMSO); δ 8.93 (s, 1H), 8.41 (s, 1H), 7.94-7.90 (dd, 2H), 7.39 (t, 2H), 3.45-3.37 (dd, 2H), 3.33 (m, 2H, NH.sub.2).

(45) Step 3:

Synthesis of N-{2-[3-chloro-5-(4-chlorophenyl)pyridin-2-yl]-2,2-difluoroethyl}-2-(trifluoromethyl)-benzamide (expl. 2)

(46) ##STR00150##

(47) 100 mg (0.22 mmol) N-[2-(5-bromo-3-chloropyridin-2-yl)-2,2-difluoroethy]-2-(trifluoromethyl)-benzamide (from step 2a) and 35.2 mg (0.22 mmol) (4-chlorophenyl)boronic acid were dissolved in 3 mL dioxane. Thereafter, 16.6 mg (0.02 mmol) dichlorobis(tricyclohexylphosphine) palladium(II) and 146.6 mg (0.45 mmol) cesium carbonate in 0.44 mL water were added and treated in a sealed microwave vial in a Biotage microwave oven (Initiator) at 100° C. for 20 minutes. The reaction mixture was filtered over a silica gel sodium sulfate cartridge, the solvents were evaporated and the crude product was purified by preparative HPLC to afford 35 mg (32%) of the title compound as off-white solid.

(48) For LC-MS (M+H).sup.+ and .sup.1H-NMR see example table (example 2).

(49) Preparation 3:

(50) Step 1:

Synthesis of ethyl 2-(3-chloro-5-nitropyridin-2-yl)-2-cyanopropanoate

(51) ##STR00151##

(52) To a solution of 2,3-dichloro-5-nitropyridine (90 g, 466 mmol) in 500 ml of dimethylformamide, 60 g of ethyl 2-cyanopropanoate (472 mmol) and 150 g of potassium carbonate were added. The resulting reaction mixture was stirred overnight at 60° C. After cooling down, 2.0 L of water were added and the reaction mixture was extracted with ethyl acetate (3×300 ml). The combined organic layers were washed with water (200 ml), brine (200 ml), dried over anhydrous sodium sulphate and concentrated. This afforded 105 g of the title compound (80%), which was used in the next steep without purification.

(53) Step 2:

Synthesis of 2-(3-chloro-5-nitropyridin-2-yl)propanenitrile

(54) ##STR00152##

(55) A suspension of 105 g of ethyl 2-(3-chloro-5-nitropyridin-2-yl)-2-cyanopropanoate (371 mmol), LiCl (100 g) in dimethylsulfoxide (600 ml) and water (80 ml) were heated at 120° C. overnight. The reaction mixture was then cooled down, diluted with water (3000 ml) and extracted with ethyl acetate (5×300 ml). The combined organic layers were washed with water (2×500 ml), brine (200 ml), dried over anhydrous sodium sulphate and concentrated. The crude product was dissolved in ethanol (500 ml) and charcoal (70 g) was added. The resulting mixture was refluxed overnight under stirring. Then reaction mixture was filtered and concentrated. This afforded 55 g of the title compound (70%).

(56) Step 3:

Synthesis 2-(5-amino-3-chloropyridin-2-yl)propanenitrile

(57) ##STR00153##

(58) To a solution of 55 g of 2-(3-chloro-5-nitropyridin-2-yl)propanenitrile (260 mmol) in mixture of ethanol and water (700 and 5 ml) powdered Fe (146 g, 2.600 mol), NH.sub.4Cl (4.5 g) and HCl (10 N, 5 ml) were added. The reaction mixture was stirred for one hour and then refluxed overnight under stirring. On the next day suspension was filtered through a silica pad and the filtrate was concentrated. The residue was dissolved in ethyl acetate (800 ml) and the solution was washed with saturated NaHCO.sub.3, water, brine and dried over anhydrous sodium sulphate. Concentration afforded 35 g of the title compound as a crude material which was used in the next step without further purification.

(59) Step 4:

Synthesis 2-(5-bromo-3-chloropyridin-2-yl)propanenitrile

(60) ##STR00154##

(61) A mixture of CuBr.sub.2 (53 g, 237 mmol) and t-BuONO (30 g 291 mmol) in acetonitrile (500 ml) was cooled to −5° C. A solution of 35 g of 2-(5-amino-3-chloropyridin-2-yl)propanenitrile (193 mmol) in acetonitrile was added drop by drop under stirring over 40 min. The reaction mixture was stirred overnight at room temperature and then evaporated. The residue was dissolved in ethyl acetate (800 ml) and 400 ml of saturated aqueous NH.sub.4Cl solution were added. The organic layer was separated, washed with water, brine dried over anhydrous sodium sulphate. Evaporation afforded 43 g of the title compound as a crude material which was used in the next step without further purification.

(62) Step 5:

Synthesis 2-(5-bromo-3-chloropyridin-2-yl)-2-fluoropropanenitrile

(63) ##STR00155##

(64) A solution of 43 g of crude 2-(5-bromo-3-chloropyridin-2-yl)propanenitrile and 61 g of NFSI (N-fluorobenzenesulfonimide) (193 mmol) in tetrahydrofuran (1000 ml) was cooled to −20° C. and 29.4 g of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (193 mmol) were added dropwise under stirring. When addition was completed, the reaction mixture was gradually warmed to room temperature during 2 hours. Then the reaction mixture was cooled down to −20° C. again and NFSI (20 g) and DBU (10 g) were added as previously. Then the reaction mixture was stirred for one hour and 1 L of ether was added. The resulting reaction mixture was filtered through a silica pad and the filtrate was concentrated. The crude material obtained was purified by column on silica to afford 14.5 g of the title compound as a pure material (55 mmol, 31%).

(65) Step 6:

Synthesis 2-(5-bromo-3-chloropyridin-2-yl)-2-fluoropropan-1-amine hydrochloride

(66) ##STR00156##

(67) To a solution of 14.5 g of 2-(5-bromo-3-chloropyridin-2-yl)-2-fluoropropanenitrile (55 mmol) in THF (250 ml) at −60° C. a solution of LiAlH.sub.4 (2.3 g 60.5 mmol) in THF (300 ml) was added dropwise. The resulting reaction mixture was stirred at the same temperature for one hour. Then a solution of HCl in 1,4-dioxane (10%, 200 ml) was added at −40° C. dropwise under stirring. The resulting solution was evaporated and the residue obtained was purified by chromatography on silica. The material obtained after chromatography column was re-purified by trituration with acetone. This afforded 6.17 g of the title compound (20.3 mmol, 36%).

(68) LC-MS (M+H-HCl).sup.+=267.0

(69) .sup.1H-NMR (400 MHz, d6-DMSO); δ 8.69 (s, 1H), 8.44 (s, 1H), 3.72-3.65 (dd, 1H), 3.43-3.36 (t, 1H), 1.81 (d, 3H).

(70) Step 7:

Synthesis of N-[2-(5-bromo-3-chloropyridin-2-yl)-2-fluoropropyl]-2-(trifluoromethyl) benzamide

(71) ##STR00157##

(72) To a solution of 2-(5-bromo-3-chloropyridin-2-yl)-2-fluoropropan-1-amine hydrochloride (3.0 g, 1.0 eq.) in dichloromethane (50 ml) at room temperature, N—N-diisopropylethylamine (5.2 ml, 3.0 eq.) was added. Then 2-(trifluoromethyl) benzoyl chloride (2.5 g, 1.2 eq.) was added dropwise. After completion of the reaction, the reaction mixture was diluted with water. After dichloromethane extraction, the organic phase was washed with brine and dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure and this afforded 4.6 g of the title compound (97% yield).

(73) LC-MS (M+H).sup.+=439.0; 440.9

(74) .sup.1H-NMR (400 MHz, d6-DMSO); δ 8.49 (d, 1H), 7.93 (d, 1H), 7.74-7.48 (m, 4H), 6.42 (s, NH), 4.29-4.14 (m, 2H), 1.90 (d, 3H).

(75) Step 8:

Synthesis of N-{2-[3-chloro-5-(4-fluorophenyl)pyridin-2-yl]-2-fluoropropyl}-2-(trifluoromethyl) benzamide (expl. 21)

(76) ##STR00158##

(77) 38.5 mg (0.27 mmol) of 4-(fluorophenyl)boronic acid and 120 mg (0.25 mmol) of of N-[2-(5-bromo-3-chloropyridin-2-yl)-2-fluoropropyl]-2-(trifluoromethyl)benzamide from the previous step were dissolved in 3 mL of dioxane followed by addition 0.28 mmol of sodium carbonate (in an aqueous solution), 10.21 mg (0.01 mmol) of 1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) catalyst. The reaction mixture was kept under stirring in a closed vial for 3 h at 80° C. To the reaction mixture was added ethyl acetate. Then the reaction mixture was filtered through a celite layer. The celite was washed with ethyl acetate. The reaction mixture was then dried over anhydrous sodium sulphate. The residue obtained was purified by MPLC on silicagel (solvent gradient cyclohexane/ethylacetate) to afford 53.3 mg the title compound (example 21) (yield: 44%).

(78) For LC-MS (M+H).sup.+ and .sup.1H-NMR see example table (example 21).

(79) According to the methods described above, the following compounds of general formula (I) have been prepared.

(80) Compounds of Formula (I-1)

(81) ##STR00159##

(82) R.sup.1, R.sup.2, X, Y, n, m and A are as defined by each individual structure.

(83) TABLE-US-00001 TABLE 1 logP .sup.1) (M + H).sup.+ Example no. Formula (HCOOH) (LC/MS) .sup.1H-NMR 1 0 3.97.sup.[a] 439.0 DMSO 8.85 (d, 1H), 8.63 (t, NH), 8.25 (d, 1H), 7.84 (d, 2H), 7.77-7.61 (m, 3H), 7.58 (d, 2H), 7.53 (d, 1H), 3.69-3.64 (qu, 2H), 3.19- 3.15 (t, 2H). 2 4.17.sup.[a] 475.0 NMR peak list 3 4.17.sup.[a] 475.1 NMR peak list 4 3.78.sup.[a] 507.1 NMR peak list 5 3.75.sup.[a] 441.0 NMR peak list 6 3.94.sup.[a] 505.1 NMR peak list 7 3.68.sup.[a] 471.1 NMR peak list 8 3.53.sup.[a] 485.1 NMR peak list 9 4.00.sup.[a] 455.1 NMR peak list 10 4.17.sup.[a] 509.1 NMR peak list 11 0 4.64.sup.[a] 509.0 511.0 NMR peak list 12 3.89.sup.[a] 477.1 NMR peak list 13 3.73.sup.[a] 459.1 NMR peak list 14 3.84.sup.[a] 477.1 NMR peak list 15 4.57.sup.[a] 509.0 511.0 NMR peak list 16 4.00.sup.[a] 475.1 NMR peak list 17 4.09.sup.[a] 484.1 NMR peak list 18 3.44.sup.[a] 456.0 NMR peak list 19 3.51.sup.[a] 460.8 NMR peak list 20 3.83.sup.[a] 471.9 473.9 NMR peak list 21 0 3.96.sup.[a] 455.0 NMR peak list 22 2.15.sup.[a] 452.0 NMR peak list 23 3.92.sup.[a] 437.0 NMR peak list 24 3.74.sup.[a] 459.1 NMR peak list 25 4.18.sup.[a] 521.1 NMR peak list 26 3.29.sup.[a] 460.1 NMR peak list 27 4.38.sup.[a] 470.9 NMR peak list 28 3.38.sup.[a] 438.0 NMR peak list 29 4.35.sup.[a] 451.0 NMR peak list 30 4.83.sup.[a] 510.1 NMR peak list 31 0 1.78.sup.[a] 3.39.sup.[b] 539.0 NMR peak list 32 3.59.sup.[a] 526.0 NMR peak list 33 2.65.sup.[a] 519.1 NMR peak list 34 4.19.sup.[a] 526.9 NMR peak list 35 4.10.sup.[a] 487.0 NMR peak list 36 3.39.sup.[a] 470.0 NMR peak list 37 3.29.sup.[a] 466.0 NMR peak list 38 2.70.sup.[a] 498.0 NMR peak list 39 4.65.sup.[a] 540.9 NMR peak list
Intermediates of Formula (INT-a)

(84) ##STR00199##

(85) R.sup.1, R.sup.2, X, Y, n and m are as defined by each individual structure.

(86) TABLE-US-00002 TABLE 2 logP .sup.1) (M + H).sup.+ Example no. Formula (HCOOH) (LC/MS) .sup.1H-NMR INT-1 00 1.18.sup.[a] 2.61.sup.[b] 287.0 .sup.1H-NMR (400 MHz, d6- DMSO); δ 8.93 (s, 1H), 8.41 (s, 1H), 7.94-7.90 (dd, 2H), 7.39 (t, 2H), 3.45- 3.37 (dd, 2H), 3.33 (m, 2H, NH.sub.2). .sup.1) Measurement of LogP values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods: .sup.[a]logP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). .sup.[b]logP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

(87) Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.

(88) In table 1, (M+H).sup.+ or (M−H).sup.− means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy by electrospray ionization (ESI+ or −).

(89) NMR Peak List of Example Compounds:

(90) .sup.1H-NMR-data were determined with a Bruker Avance 400 (Method M1) equipped with a flow cell (60 μl volume) or with a Bruker AVIII 400 equipped with 1.7 mm cryo-CPTCI probe head or with a Bruker AVII 600 (600.13 MHz) equipped with a 5 mm cyroTCI probe head or with a Bruker AVIII 600 (601.6 MHz) equipped with a 5 mm cryo CPMNP probe head with tetramethylsilane as reference (0.0) and the solvents CD.sub.3CN, CDCl.sub.3 or D.sub.6-DMSO.

(91) .sup.1H-NMR data of selected examples are written in form of .sup.1H-NMR-peak lists. To each signal peak are listed the δ-value in ppm and the signal intensity in round brackets. Between the δ-value—signal intensity pairs are semicolons as delimiters.

(92) The peak list of an example has therefore the form:

(93) δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i); . . . ; δ.sub.n (intensity.sub.n)

(94) Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

(95) For calibrating chemical shift for .sup.1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.

(96) The .sup.1H-NMR peak lists are similar to classical .sup.1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

(97) Additionally they can show like classical .sup.1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.

(98) To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown in our 1H-NMR peak lists and have usually on average a high intensity.

(99) The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).

(100) Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via “side-products-fingerprints”.

(101) An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical .sup.1H-NMR interpretation.

(102) Further details of NMR-data description with peak lists you find in the publication “Citation of NMR Peaklist Data within Patent Applications” of the Research Disclosure Database Number 564025.

(103) Patent Applications” of the Research Disclosure Database Number 564025.

(104) TABLE-US-00003 TABLE 3 NMR Peaklist of examples from Table 1 Example 2: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.012 (2.3); 8.997 (5.1); 8.987 (10.3); 8.982 (11.8); 8.476 (9.5); 8.471 (9.7); 8.317 (1.3); 7.927 (1.5); 7.920 (13.4); 7.916 (4.9); 7.904 (4.7); 7.899 (15.7); 7.781 (4.5); 7.762 (6.3); 7.752 (2.2); 7.732 (5.1); 7.714 (3.7); 7.669 (3.7); 7.650 (4.7); 7.631 (3.5); 7.624 (16.0); 7.620 (5.3); 7.608 (4.3); 7.603 (13.7); 7.484 (5.3); 7.465 (4.6); 7.446 (0.3); 4.352 (1.9); 4.336 (2.0); 4.314 (4.6); 4.299 (4.4); 4.277 (2.3); 4.261 (2.2); 3.327 (478.7); 2.676 (1.8); 2.671 (2.6); 2.667 (2.0); 2.542 (0.6); 2.524 (5.2); 2.520 (8.3); 2.511 (138.6); 2.507 (293.7); 2.502 (397.7); 2.498 (296.6); 2.493 (149.3); 2.338 (0.9); 2.333 (1.9); 2.329 (2.6); 2.324 (2.0); 2.075 (0.6); 0.008 (0.5); 0.000 (19.2); −0.008 (0.8) Example 3: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.014 (13.8); 9.009 (14.7); 8.988 (3.0); 8.523 (12.4); 8.519 (12.6); 7.989 (11.4); 7.869 (0.6); 7.866 (0.7); 7.859 (3.4); 7.854 (3.6); 7.846 (6.6); 7.841 (4.0); 7.837 (4.4); 7.832 (4.0); 7.826 (1.0); 7.821 (0.7); 7.784 (6.1); 7.765 (8.3); 7.755 (3.0); 7.736 (6.8); 7.717 (4.8); 7.672 (4.8); 7.653 (6.2); 7.634 (2.3); 7.598 (1.1); 7.577 (14.5); 7.573 (9.0); 7.567 (14.8); 7.564 (16.0); 7.553 (1.2); 7.488 (7.2); 7.469 (6.3); 4.356 (2.7); 4.341 (2.8); 4.319 (6.3); 4.303 (6.0); 4.281 (3.1); 4.266 (2.9); 3.328 (168.0); 2.676 (0.9); 2.671 (1.2); 2.667 (0.9); 2.542 (65.1); 2.525 (3.5); 2.511 (72.9); 2.507 (145.5); 2.502 (192.0); 2.498 (143.4); 2.494 (73.0); 2.368 (0.3); 2.334 (0.9); 2.329 (1.3); 2.325 (1.0); 1.259 (0.3); 1.234 (0.7); 0.008 (0.6); 0.000 (16.6); −0.008 (0.7) Example 4: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.012 (2.6); 8.997 (5.5); 8.980 (12.6); 8.975 (11.4); 8.457 (10.8); 8.452 (10.7); 7.966 (1.7); 7.958 (14.7); 7.954 (5.2); 7.941 (5.2); 7.936 (16.0); 7.929 (1.8); 7.783 (5.2); 7.764 (7.1); 7.753 (2.5); 7.734 (5.9); 7.715 (4.1); 7.670 (4.1); 7.651 (5.3); 7.632 (1.9); 7.549 (5.4); 7.486 (6.2); 7.468 (5.4); 7.365 (12.4); 7.355 (14.1); 7.333 (13.3); 7.180 (5.6); 4.355 (2.2); 4.340 (2.3); 4.318 (5.2); 4.302 (5.0); 4.280 (2.6); 4.265 (2.4); 3.329 (193.1); 2.676 (0.9); 2.671 (1.2); 2.667 (0.9); 2.541 (71.0); 2.524 (3.5); 2.511 (72.3); 2.507 (143.7); 2.502 (188.2); 2.498 (138.5); 2.494 (68.9); 2.333 (0.9); 2.329 (1.2); 2.324 (0.9); 1.259 (0.4); 1.234 (0.7); 0.008 (0.6); 0.000 (17.9); −0.008 (0.7) Example 5: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.012 (3.3); 8.997 (6.9); 8.980 (16.0); 8.975 (14.5); 8.804 (0.6); 8.799 (0.6); 8.566 (0.6); 8.444 (13.5); 8.440 (13.3); 7.872 (13.7); 7.854 (15.5); 7.783 (6.9); 7.763 (9.6); 7.755 (3.9); 7.735 (7.7); 7.716 (5.4); 7.670 (5.6); 7.651 (7.3); 7.631 (2.7); 7.570 (5.4); 7.553 (14.9); 7.534 (12.6); 7.520 (8.3); 7.509 (2.8); 7.503 (7.0); 7.488 (9.4); 7.469 (7.0); 7.448 (0.5); 7.428 (0.4); 6.937 (0.4); 6.916 (0.4); 4.359 (3.1); 4.344 (3.3); 4.322 (7.2); 4.306 (6.9); 4.284 (3.7); 4.269 (3.4); 4.243 (0.5); 4.228 (0.5); 3.968 (0.4); 3.500 (0.4); 3.481 (0.5); 3.470 (0.3); 3.427 (0.6); 3.414 (0.8); 3.396 (0.8); 3.326 (407.9); 3.188 (0.4); 2.711 (0.5); 2.675 (2.9); 2.671 (3.7); 2.541 (93.5); 2.506 (451.1); 2.502 (569.2); 2.497 (433.4); 2.368 (0.5); 2.333 (2.8); 2.328 (3.6); 1.299 (0.4); 1.258 (0.5); 1.235 (1.4); 0.000 (45.4) Example 5: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.036 (0.4); 9.016 (3.3); 9.000 (6.9); 8.980 (14.7); 8.975 (14.7); 8.443 (13.7); 8.439 (14.1); 8.318 (0.7); 7.875 (10.6); 7.872 (14.5); 7.854 (16.0); 7.782 (6.7); 7.763 (9.5); 7.755 (3.8); 7.735 (7.7); 7.716 (5.4); 7.670 (5.5); 7.651 (7.2); 7.631 (2.8); 7.574 (3.7); 7.570 (5.7); 7.566 (3.0); 7.553 (15.8); 7.534 (13.2); 7.524 (5.3); 7.520 (8.7); 7.509 (2.8); 7.503 (7.5); 7.489 (9.1); 7.470 (7.9); 4.360 (3.0); 4.345 (3.1); 4.323 (7.0); 4.307 (6.8); 4.286 (3.6); 4.270 (3.5); 3.331 (190.8); 2.676 (0.9); 2.672 (1.3); 2.667 (1.0); 2.525 (3.5); 2.507 (143.9); 2.503 (189.0); 2.498 (143.7); 2.334 (0.9); 2.329 (1.3); 2.325 (1.0); 0.146 (1.1); 0.008 (9.5); 0.000 (222.2); −0.008 (12.3); −0.150 (1.1) Example 6: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.004 (0.7); 8.988 (1.6); 8.982 (3.3); 8.977 (3.3); 8.468 (2.9); 8.463 (2.9); 8.028 (3.1); 8.022 (3.3); 7.879 (1.5); 7.874 (1.4); 7.858 (1.6); 7.852 (1.5); 7.784 (1.4); 7.764 (1.9); 7.752 (0.7); 7.734 (1.7); 7.716 (1.1); 7.671 (1.1); 7.652 (1.4); 7.633 (0.5); 7.486 (1.7); 7.468 (1.4); 7.316 (2.7); 7.294 (2.5); 4.345 (0.6); 4.329 (0.6); 4.308 (1.4); 4.292 (1.3); 4.270 (0.7); 4.255 (0.7); 3.932 (16.0); 3.888 (0.7); 3.384 (0.3); 3.335 (333.2); 2.676 (0.6); 2.671 (0.8); 2.667 (0.6); 2.542 (48.9); 2.525 (2.1); 2.511 (47.0); 2.507 (95.3); 2.502 (126.6); 2.498 (93.9); 2.493 (47.0); 2.333 (0.6); 2.329 (0.8); 2.324 (0.6); 1.235 (0.3); 0.000 (2.3) Example 7: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 8.997 (0.5); 8.981 (1.1); 8.966 (0.6); 8.941 (2.3); 8.936 (2.3); 8.383 (2.3); 8.379 (2.3); 7.846 (3.2); 7.841 (1.1); 7.828 (1.1); 7.823 (3.5); 7.816 (0.4); 7.782 (1.1); 7.762 (1.5); 7.752 (0.5); 7.733 (1.3); 7.714 (0.9); 7.669 (0.9); 7.650 (1.2); 7.631 (0.4); 7.485 (1.3); 7.466 (1.1); 7.113 (0.4); 7.106 (3.5); 7.101 (1.1); 7.089 (1.1); 7.084 (3.4); 7.076 (0.3); 4.346 (0.5); 4.330 (0.5); 4.309 (1.1); 4.293 (1.1); 4.271 (0.6); 4.255 (0.5); 3.828 (16.0); 3.334 (278.1); 2.676 (0.6); 2.671 (0.8); 2.667 (0.6); 2.541 (16.1); 2.524 (2.2); 2.511 (47.1); 2.507 (95.8); 2.502 (127.1); 2.498 (93.3); 2.493 (45.7); 2.333 (0.6); 2.329 (0.8); 2.324 (0.6); 0.000 (1.9) Example 8: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 8.998 (1.0); 8.983 (2.1); 8.967 (1.1); 8.925 (4.0); 8.920 (4.2); 8.377 (4.0); 8.372 (4.1); 7.783 (2.1); 7.763 (2.9); 7.752 (1.0); 7.733 (2.4); 7.715 (1.7); 7.670 (1.7); 7.650 (2.2); 7.632 (0.8); 7.513 (4.2); 7.509 (4.6); 7.484 (2.5); 7.465 (2.1); 7.399 (2.2); 7.395 (2.1); 7.379 (2.4); 7.374 (2.4); 7.089 (4.3); 7.069 (3.9); 6.114 (16.0); 4.341 (0.9); 4.325 (1.0); 4.304 (2.1); 4.288 (2.0); 4.266 (1.1); 4.251 (1.0); 3.330 (162.5); 2.675 (0.6); 2.671 (0.8); 2.667 (0.6); 2.541 (25.4); 2.506 (92.9); 2.502 (121.6); 2.498 (92.6); 2.333 (0.6); 2.329 (0.8); 2.325 (0.6); 1.235 (0.4); 0.000 (6.6) Example 9: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.023 (0.7); 9.008 (1.5); 8.993 (0.7); 8.643 (3.1); 8.638 (3.3); 8.179 (3.2); 8.175 (3.3); 7.783 (1.6); 7.764 (2.1); 7.750 (0.7); 7.731 (1.8); 7.712 (1.2); 7.671 (1.3); 7.652 (1.6); 7.633 (0.6); 7.485 (1.9); 7.467 (1.6); 7.392 (1.0); 7.386 (1.3); 7.373 (4.7); 7.361 (0.9); 7.357 (0.9); 7.338 (1.6); 7.332 (1.5); 7.324 (3.2); 7.319 (3.0); 7.307 (0.6); 4.375 (0.7); 4.359 (0.7); 4.338 (1.6); 4.322 (1.6); 4.300 (0.8); 4.285 (0.8); 3.392 (0.4); 3.332 (361.5); 2.675 (0.8); 2.671 (1.1); 2.667 (0.8); 2.541 (17.9); 2.524 (3.0); 2.506 (129.9); 2.502 (171.9); 2.497 (129.4); 2.333 (0.8); 2.329 (1.1); 2.324 (0.8); 2.261 (16.0); 1.235 (0.4); 0.000 (2.5) Example 10: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.063 (14.6); 9.058 (14.8); 9.025 (3.7); 9.010 (7.6); 8.994 (3.8); 8.605 (15.0); 8.600 (14.8); 8.233 (12.5); 8.194 (6.7); 8.174 (7.3); 7.879 (5.4); 7.859 (8.7); 7.807 (6.4); 7.787 (16.0); 7.767 (13.5); 7.756 (4.2); 7.736 (8.4); 7.718 (6.0); 7.673 (5.9); 7.654 (7.5); 7.635 (2.9); 7.494 (8.7); 7.475 (7.6); 4.366 (3.3); 4.350 (3.5); 4.329 (7.6); 4.313 (7.4); 4.291 (4.0); 4.276 (3.6); 3.413 (0.5); 3.399 (0.5); 3.331 (303.9); 2.676 (1.2); 2.672 (1.5); 2.667 (1.1); 2.542 (44.2); 2.507 (180.9); 2.503 (229.6); 2.498 (173.9); 2.334 (1.2); 2.330 (1.5); 2.325 (1.1); 1.299 (0.3); 1.259 (0.5); 1.234 (1.0); 0.008 (0.8); 0.000 (14.5) Example 11: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.053 (6.2); 9.048 (6.4); 9.025 (1.5); 9.010 (3.1); 8.994 (1.5); 8.592 (6.3); 8.587 (6.3); 8.008 (15.3); 8.003 (16.0); 7.787 (3.1); 7.767 (4.3); 7.759 (4.6); 7.755 (8.2); 7.751 (4.1); 7.737 (3.5); 7.718 (2.4); 7.674 (2.4); 7.654 (3.1); 7.636 (1.2); 7.488 (3.6); 7.469 (3.1); 4.352 (1.3); 4.337 (1.4); 4.315 (3.1); 4.300 (2.9); 4.278 (1.5); 4.262 (1.4); 3.331 (112.4); 2.676 (0.4); 2.672 (0.5); 2.667 (0.4); 2.542 (54.2); 2.525 (1.4); 2.512 (29.4); 2.507 (59.2); 2.503 (78.5); 2.498 (58.0); 2.494 (28.6); 2.334 (0.4); 2.329 (0.5); 2.325 (0.4); 1.233 (0.4); 0.000 (5.1) Example 12: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.061 (14.8); 9.057 (14.9); 9.025 (3.6); 9.009 (7.4); 8.994 (3.6); 8.569 (14.9); 8.564 (14.6); 7.785 (7.4); 7.765 (10.8); 7.756 (4.9); 7.738 (16.0); 7.723 (12.6); 7.718 (14.5); 7.707 (2.0); 7.673 (6.1); 7.654 (7.7); 7.635 (2.9); 7.484 (8.9); 7.466 (7.8); 7.431 (2.0); 7.426 (3.2); 7.421 (1.9); 7.408 (4.1); 7.403 (6.4); 7.398 (3.7); 7.385 (2.2); 7.380 (3.3); 4.353 (3.3); 4.337 (3.4); 4.316 (7.8); 4.300 (7.4); 4.278 (3.9); 4.262 (3.6); 3.331 (201.9); 2.676 (0.7); 2.672 (1.0); 2.667 (0.7); 2.542 (56.9); 2.525 (3.0); 2.511 (63.7); 2.507 (122.4); 2.503 (158.4); 2.498 (117.2); 2.368 (0.4); 2.334 (0.8); 2.330 (1.1); 2.325 (0.8); 1.258 (0.4); 1.233 (0.8); 0.000 (9.0); −0.008 (0.4) Example 13: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.027 (4.1); 9.012 (8.1); 8.996 (3.8); 8.841 (16.0); 8.731 (0.9); 8.726 (0.9); 8.349 (15.0); 8.300 (0.9); 8.295 (0.9); 7.858 (0.9); 7.854 (0.9); 7.783 (8.3); 7.764 (11.5); 7.750 (4.0); 7.743 (4.6); 7.738 (5.5); 7.732 (10.1); 7.723 (8.8); 7.719 (9.7); 7.714 (7.8); 7.704 (4.8); 7.699 (4.7); 7.671 (6.8); 7.652 (8.6); 7.633 (3.3); 7.614 (1.0); 7.609 (1.2); 7.605 (1.6); 7.594 (1.9); 7.590 (2.0); 7.581 (2.3); 7.576 (4.5); 7.572 (4.2); 7.562 (3.4); 7.558 (4.6); 7.555 (5.3); 7.550 (3.2); 7.541 (3.0); 7.537 (2.7); 7.481 (9.8); 7.462 (8.6); 7.445 (6.3); 7.424 (5.2); 7.418 (7.6); 7.413 (8.4); 7.394 (13.1); 7.375 (5.0); 7.373 (4.7); 4.367 (3.8); 4.351 (3.8); 4.330 (8.7); 4.314 (8.3); 4.293 (4.4); 4.277 (4.0); 3.416 (0.4); 3.400 (0.4); 3.331 (276.3); 2.997 (0.4); 2.712 (1.4); 2.676 (1.0); 2.672 (1.4); 2.667 (1.1); 2.542 (314.5); 2.525 (3.9); 2.511 (78.9); 2.507 (156.3); 2.502 (204.1); 2.498 (149.9); 2.494 (74.3); 2.368 (1.4); 2.334 (1.0); 2.329 (1.3); 2.325 (1.0); 1.258 (0.4); 1.234 (0.7); 0.008 (0.5); 0.000 (13.0); −0.009 (0.5) Example 14: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.011 (13.8); 9.006 (16.0); 8.987 (3.0); 8.509 (12.3); 8.504 (12.1); 8.101 (2.7); 8.096 (2.8); 8.082 (3.0); 8.076 (3.3); 8.071 (3.1); 8.066 (2.9); 8.052 (2.7); 8.046 (2.7); 7.784 (8.7); 7.776 (3.6); 7.765 (12.0); 7.756 (4.7); 7.735 (7.1); 7.717 (5.0); 7.672 (5.1); 7.663 (3.7); 7.653 (6.7); 7.642 (5.6); 7.637 (5.2); 7.620 (3.0); 7.616 (5.2); 7.594 (2.2); 7.485 (7.4); 7.466 (6.4); 4.351 (2.8); 4.336 (2.8); 4.314 (6.4); 4.298 (6.1); 4.276 (3.2); 4.261 (3.0); 3.331 (234.5); 2.712 (0.4); 2.676 (0.9); 2.672 (1.2); 2.667 (0.9); 2.542 (99.0); 2.525 (3.3); 2.507 (139.2); 2.503 (180.3); 2.498 (132.2); 2.368 (0.4); 2.334 (0.9); 2.329 (1.2); 2.325 (0.9); 1.259 (0.3); 1.234 (0.8); 0.008 (0.4); 0.000 (10.6); −0.008 (0.4) Example 15: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.038 (2.3); 9.022 (4.8); 9.007 (2.3); 8.730 (10.3); 8.725 (10.3); 8.317 (0.4); 8.300 (10.6); 8.295 (10.2); 7.860 (9.3); 7.855 (9.7); 7.785 (4.7); 7.765 (6.3); 7.745 (2.0); 7.728 (5.3); 7.709 (3.8); 7.672 (3.9); 7.652 (4.8); 7.635 (3.7); 7.630 (2.6); 7.614 (11.2); 7.609 (12.7); 7.605 (16.0); 7.584 (2.4); 7.475 (5.6); 7.456 (4.8); 6.918 (0.4); 4.374 (2.2); 4.358 (2.2); 4.336 (4.9); 4.321 (4.8); 4.299 (2.6); 4.283 (2.2); 3.966 (0.4); 3.713 (0.4); 3.602 (0.4); 3.581 (0.4); 3.562 (0.4); 3.514 (0.5); 3.501 (0.6); 3.481 (0.6); 3.468 (0.7); 3.450 (0.5); 3.424 (0.9); 3.410 (1.7); 3.395 (1.9); 3.328 (1214.5); 3.189 (0.4); 2.711 (0.9); 2.697 (0.3); 2.675 (4.9); 2.671 (6.6); 2.666 (4.9); 2.646 (0.5); 2.636 (0.4); 2.631 (0.5); 2.625 (0.5); 2.621 (0.5); 2.615 (0.5); 2.604 (0.6); 2.541 (186.3); 2.524 (21.6); 2.510 (396.7); 2.506 (771.2); 2.502 (999.6); 2.497 (728.5); 2.493 (357.4); 2.423 (0.5); 2.408 (0.4); 2.367 (0.8); 2.333 (4.7); 2.328 (6.4); 2.324 (4.7); 2.288 (0.5); 1.299 (0.7); 1.258 (1.0); 1.235 (2.5); 1.056 (0.4); 1.041 (0.4); 0.854 (0.3); 0.008 (2.1); 0.000 (54.0); −0.008 (2.0) Example 16: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.040 (3.2); 9.025 (6.9); 9.009 (3.3); 8.732 (13.8); 8.728 (14.6); 8.300 (1.4); 8.295 (1.5); 8.286 (13.3); 8.282 (13.5); 7.859 (1.2); 7.854 (1.2); 7.786 (6.8); 7.767 (9.3); 7.748 (3.0); 7.730 (7.6); 7.711 (5.5); 7.683 (0.8); 7.672 (11.3); 7.667 (6.1); 7.654 (12.0); 7.650 (11.7); 7.635 (3.0); 7.614 (1.4); 7.609 (1.6); 7.605 (2.1); 7.584 (0.7); 7.578 (4.0); 7.572 (3.3); 7.567 (4.0); 7.563 (4.9); 7.555 (10.7); 7.550 (4.2); 7.546 (2.1); 7.538 (10.4); 7.531 (14.1); 7.523 (16.0); 7.513 (8.3); 7.510 (5.9); 7.496 (1.4); 7.491 (1.0); 7.480 (7.9); 7.461 (6.9); 4.382 (2.9); 4.366 (3.0); 4.344 (6.7); 4.329 (6.6); 4.307 (3.5); 4.291 (3.2); 3.413 (0.3); 3.329 (170.9); 2.711 (0.3); 2.676 (0.8); 2.671 (1.1); 2.667 (0.8); 2.542 (80.2); 2.524 (2.8); 2.511 (60.7); 2.507 (122.5); 2.502 (162.2); 2.498 (119.9); 2.493 (59.6); 2.368 (0.4); 2.333 (0.8); 2.329 (1.1); 2.324 (0.8); 1.235 (0.7); 0.008 (0.5); 0.000 (16.0); −0.008 (0.6) Example 17: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 8.980 (0.4); 8.964 (0.7); 8.949 (0.4); 8.901 (1.4); 8.896 (1.4); 8.296 (1.4); 8.291 (1.4); 7.782 (0.7); 7.762 (1.0); 7.750 (0.5); 7.743 (1.9); 7.732 (1.0); 7.726 (0.8); 7.720 (2.1); 7.713 (0.8); 7.668 (0.6); 7.649 (0.7); 7.487 (0.8); 7.468 (0.7); 6.837 (1.8); 6.814 (1.8); 4.298 (0.7); 4.283 (0.7); 4.261 (0.3); 4.246 (0.3); 3.342 (146.2); 2.983 (16.0); 2.526 (0.6); 2.512 (14.0); 2.508 (28.1); 2.503 (37.1); 2.499 (27.5); 2.494 (13.7); 2.075 (0.4); 0.008 (1.5); 0.000 (42.1); −0.009 (1.7) Example 18: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.756 (3.7); 8.745 (3.5); 8.595 (5.9); 8.592 (6.3); 7.915 (9.7); 7.894 (3.9); 7.561 (3.7); 7.554 (5.4); 7.549 (5.7); 7.541 (7.9); 7.532 (7.1); 7.520 (5.4); 7.262 (40.5); 7.222 (0.9); 7.214 (4.9); 7.193 (8.9); 7.171 (4.3); 6.660 (1.3); 6.647 (2.1); 4.383 (0.9); 4.368 (0.9); 4.348 (1.7); 4.332 (2.2); 4.315 (0.9); 4.296 (1.8); 4.280 (1.9); 4.274 (1.9); 4.258 (1.7); 4.239 (2.6); 4.223 (2.6); 4.204 (1.0); 4.189 (0.8); 1.956 (15.9); 1.903 (16.0); 1.843 (0.7); 1.557 (42.0); 1.254 (0.6); 0.000 (38.8) Example 19: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.266 (2.5); 9.251 (5.2); 9.235 (2.5); 9.027 (8.2); 9.022 (10.0); 8.973 (10.4); 8.967 (9.5); 8.962 (11.3); 8.958 (10.9); 8.471 (10.9); 8.466 (10.9); 8.317 (2.5); 7.965 (0.8); 7.957 (7.4); 7.952 (3.4); 7.944 (8.3); 7.935 (8.9); 7.927 (3.5); 7.921 (8.1); 7.914 (0.9); 7.426 (0.8); 7.419 (8.4); 7.414 (2.8); 7.396 (16.0); 7.379 (2.6); 7.374 (7.9); 7.366 (0.8); 4.441 (2.4); 4.426 (2.4); 4.404 (5.6); 4.388 (5.4); 4.366 (2.8); 4.350 (2.6); 3.345 (246.7); 2.678 (0.6); 2.673 (0.8); 2.669 (0.6); 2.527 (1.9); 2.513 (46.8); 2.509 (95.8); 2.504 (126.3); 2.500 (92.7); 2.496 (46.2); 2.335 (0.6); 2.331 (0.8); 2.327 (0.6); 2.076 (0.7); 0.146 (0.6); 0.008 (4.6); 0.000 (138.5); −0.009 (5.3); −0.150 (0.6) Example 20: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.608 (0.4); 8.604 (0.5); 7.931 (0.5); 7.926 (0.5); 7.493 (1.3); 7.484 (1.4); 7.265 (17.7); 1.955 (1.2); 1.901 (1.2); 1.638 (6.8); 1.626 (16.0); 0.008 (0.5); 0.000 (15.0) Example 21: .sup.1H-NMR (601.6 MHz, CDCl.sub.3): δ = 8.602 (5.8); 8.599 (5.7); 7.908 (6.2); 7.905 (6.1); 7.771 (1.5); 7.688 (3.3); 7.675 (3.9); 7.588 (1.3); 7.576 (3.5); 7.563 (2.9); 7.554 (0.8); 7.549 (4.9); 7.545 (2.6); 7.540 (7.4); 7.534 (5.9); 7.526 (7.9); 7.516 (5.2); 7.503 (2.8); 7.294 (0.5); 7.289 (0.6); 7.283 (0.6); 7.279 (1.0); 7.274 (0.7); 7.268 (0.9); 7.263 (11.5); 7.208 (0.6); 7.203 (4.9); 7.200 (1.7); 7.189 (8.9); 7.178 (1.7); 7.175 (4.4); 7.170 (0.5); 6.788 (1.0); 6.783 (1.0); 6.774 (1.0); 6.768 (1.0); 6.607 (1.1); 6.597 (1.9); 6.588 (1.1); 4.361 (1.0); 4.351 (1.0); 4.338 (1.6); 4.327 (2.4); 4.317 (1.0); 4.304 (1.6); 4.293 (1.5); 4.259 (1.5); 4.249 (1.6); 4.235 (2.3); 4.224 (2.3); 4.211 (1.1); 4.201 (1.0); 1.946 (16.0); 1.911 (16.0); 1.885 (0.7); 1.849 (0.6); 1.643 (2.5); 1.265 (0.6); 1.254 (1.1); 0.005 (2.4); 0.000 (45.7); −0.005 (2.1) Example 22: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.719 (2.6); 8.714 (2.7); 8.636 (3.0); 8.632 (3.2); 8.219 (0.5); 7.936 (3.3); 7.932 (3.4); 7.785 (1.8); 7.779 (1.8); 7.765 (1.8); 7.759 (1.9); 7.690 (1.7); 7.671 (2.1); 7.596 (0.6); 7.581 (1.7); 7.562 (1.8); 7.542 (1.6); 7.524 (4.5); 7.505 (1.7); 7.307 (2.6); 7.287 (2.6); 7.263 (25.1); 7.162 (0.4); 7.156 (0.4); 7.079 (0.7); 7.058 (0.4); 6.560 (0.6); 6.547 (1.1); 6.532 (0.6); 5.302 (1.7); 4.381 (0.5); 4.365 (0.5); 4.346 (0.9); 4.330 (1.3); 4.315 (0.5); 4.295 (0.9); 4.280 (0.9); 4.271 (0.9); 4.255 (0.9); 4.234 (1.2); 4.219 (1.2); 4.199 (0.5); 4.183 (0.4); 2.654 (0.4); 2.637 (16.0); 2.629 (3.0); 2.497 (3.6); 2.101 (0.4); 2.064 (0.4); 2.057 (0.4); 2.047 (0.5); 2.006 (0.4); 1.959 (8.8); 1.905 (8.7); 0.000 (22.7) Example 23: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.646 (5.4); 8.641 (5.4); 7.951 (6.1); 7.946 (5.9); 7.691 (2.7); 7.672 (3.6); 7.593 (1.0); 7.577 (7.6); 7.572 (3.1); 7.559 (10.8); 7.539 (2.7); 7.521 (9.4); 7.499 (8.7); 7.480 (4.5); 7.468 (2.1); 7.464 (3.4); 7.461 (1.9); 7.453 (1.1); 7.447 (3.2); 7.439 (0.6); 7.428 (0.8); 7.262 (118.1); 6.998 (0.7); 6.585 (1.6); 4.375 (0.8); 4.360 (0.8); 4.340 (1.7); 4.325 (2.3); 4.310 (0.8); 4.290 (1.8); 4.279 (2.0); 4.275 (2.0); 4.264 (1.7); 4.243 (2.2); 4.227 (2.2); 4.207 (0.8); 4.192 (0.7); 1.963 (16.0); 1.910 (16.0); 1.573 (163.5); 1.426 (7.2); 1.413 (1.0); 1.264 (0.5); 1.254 (0.5); 1.248 (0.5); 1.107 (2.9); 0.146 (0.5); 0.000 (114.9); −0.008 (4.1); −0.150 (0.5) Example 24: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.014 (2.6); 8.999 (5.4); 8.983 (2.8); 8.970 (11.0); 8.966 (10.9); 8.450 (11.1); 8.445 (10.8); 8.318 (1.1); 7.953 (7.7); 7.948 (3.6); 7.940 (8.7); 7.931 (9.1); 7.923 (3.8); 7.917 (8.1); 7.910 (0.9); 7.783 (5.4); 7.763 (7.4); 7.753 (2.6); 7.734 (6.1); 7.716 (4.3); 7.670 (4.3); 7.651 (5.4); 7.632 (2.0); 7.487 (6.4); 7.468 (5.6); 7.421 (1.0); 7.413 (8.4); 7.408 (2.9); 7.391 (16.0); 7.374 (2.9); 7.369 (7.7); 7.361 (0.8); 4.354 (2.4); 4.338 (2.5); 4.316 (5.4); 4.301 (5.3); 4.279 (2.8); 4.263 (2.6); 3.330 (164.2); 3.307 (0.6); 2.676 (1.1); 2.672 (1.4); 2.667 (1.1); 2.525 (4.4); 2.511 (81.7); 2.507 (159.1); 2.503 (205.4); 2.498 (150.6); 2.334 (1.0); 2.329 (1.3); 2.325 (1.0); 0.008 (2.1); 0.000 (54.6); −0.008 (2.1) Example 25: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.022 (3.3); 9.007 (7.0); 8.987 (14.9); 8.982 (14.4); 8.477 (14.1); 8.472 (14.1); 8.316 (3.5); 8.017 (14.8); 8.013 (15.2); 7.784 (6.6); 7.763 (15.0); 7.758 (8.6); 7.742 (9.7); 7.737 (14.8); 7.717 (5.3); 7.672 (5.3); 7.653 (6.7); 7.634 (2.5); 7.607 (16.0); 7.586 (12.5); 7.486 (7.8); 7.467 (6.8); 4.354 (2.9); 4.338 (2.9); 4.316 (6.6); 4.301 (6.4); 4.279 (3.3); 4.263 (3.1); 3.415 (0.4); 3.396 (0.7); 3.344 (778.5); 3.320 (4.2); 2.677 (1.0); 2.673 (1.3); 2.669 (1.0); 2.526 (3.6); 2.513 (74.3); 2.508 (150.5); 2.504 (198.5); 2.499 (145.7); 2.495 (72.1); 2.335 (0.9); 2.331 (1.3); 2.326 (0.9); 0.008 (2.0); 0.000 (61.4); −0.008 (2.3) Example 26: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 9.187 (2.8); 9.172 (5.8); 9.156 (2.8); 8.972 (11.0); 8.967 (11.0); 8.807 (6.0); 8.797 (6.1); 8.460 (11.5); 8.456 (11.2); 8.318 (0.5); 7.955 (11.9); 7.941 (9.9); 7.933 (16.0); 7.925 (5.3); 7.920 (8.6); 7.805 (5.3); 7.793 (5.3); 7.786 (4.5); 7.774 (4.2); 7.417 (8.4); 7.395 (16.0); 7.372 (7.8); 4.386 (2.5); 4.370 (2.6); 4.348 (5.8); 4.333 (5.6); 4.311 (3.0); 4.295 (2.8); 3.330 (144.5); 2.676 (1.1); 2.672 (1.4); 2.667 (1.1); 2.507 (170.5); 2.503 (216.4); 2.498 (161.4); 2.334 (1.1); 2.329 (1.5); 2.325 (1.1); 2.076 (0.4); 0.008 (2.3); 0.000 (51.6); −0.008 (2.8) Example 27: .sup.1H-NMR (601.6 MHz, CDCl.sub.3): δ = 19.953 (0.7); 8.615 (6.1); 8.612 (6.0); 7.916 (6.9); 7.913 (6.7); 7.687 (3.5); 7.675 (3.9); 7.588 (1.3); 7.576 (3.5); 7.563 (2.9); 7.537 (2.6); 7.520 (5.2); 7.509 (7.8); 7.495 (14.7); 7.478 (14.3); 7.464 (5.2); 7.434 (0.7); 7.263 (112.6); 7.087 (0.6); 6.548 (1.7); 5.302 (0.7); 4.351 (1.1); 4.340 (0.9); 4.328 (1.5); 4.318 (2.3); 4.307 (1.1); 4.294 (1.5); 4.284 (1.6); 4.259 (1.6); 4.248 (1.7); 4.234 (2.3); 4.224 (2.2); 4.211 (1.1); 4.201 (0.9); 1.945 (16.0); 1.910 (15.9); 1.597 (17.0); 1.591 (19.7); 1.584 (25.4); 1.578 (30.5); 1.575 (22.7); 1.254 (1.0); 0.000 (86.7); −0.100 (0.5) Example 28: .sup.1H-NMR (601.6 MHz, CDCl.sub.3): δ = 19.949 (0.6); 8.753 (3.0); 8.745 (2.8); 8.634 (4.8); 8.491 (0.5); 7.962 (5.1); 7.959 (5.2); 7.905 (2.7); 7.893 (2.9); 7.572 (4.9); 7.559 (7.0); 7.546 (2.5); 7.541 (2.4); 7.532 (2.0); 7.512 (3.1); 7.501 (6.1); 7.488 (3.7); 7.465 (2.4); 7.453 (2.8); 7.441 (1.0); 7.263 (49.5); 6.688 (1.5); 4.368 (0.7); 4.359 (0.7); 4.345 (1.1); 4.335 (1.5); 4.324 (0.7); 4.311 (1.1); 4.299 (1.1); 4.267 (1.2); 4.256 (1.2); 4.244 (1.9); 4.234 (1.7); 4.222 (0.9); 4.211 (0.8); 1.954 (10.9); 1.919 (10.8); 1.886 (1.1); 1.851 (1.0); 1.604 (16.0); 1.595 (20.2); 1.589 (20.9); 1.587 (21.6); 1.584 (19.8); 1.253 (1.1); 0.069 (2.7); 0.000 (42.7) Example 29: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.626 (3.5); 8.621 (3.6); 7.927 (3.9); 7.922 (3.8); 7.688 (1.8); 7.670 (2.3); 7.590 (0.6); 7.574 (1.9); 7.567 (0.9); 7.555 (2.0); 7.536 (1.7); 7.518 (4.8); 7.500 (1.8); 7.474 (4.7); 7.454 (6.1); 7.309 (4.9); 7.289 (3.8); 7.262 (47.0); 6.605 (0.6); 6.590 (1.1); 6.578 (0.6); 4.365 (0.5); 4.349 (0.5); 4.330 (1.1); 4.315 (1.4); 4.299 (0.5); 4.280 (1.1); 4.271 (1.2); 4.265 (1.2); 4.256 (1.1); 4.235 (1.4); 4.219 (1.4); 4.200 (0.5); 4.184 (0.5); 2.432 (0.4); 2.416 (16.0); 1.956 (10.1); 1.902 (10.1); 1.575 (31.7); 0.008 (1.6); 0.000 (43.9); −0.008 (1.8) Example 30: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 8.974 (1.9); 8.959 (4.1); 8.943 (1.9); 8.892 (7.2); 8.888 (7.5); 8.317 (0.5); 8.278 (7.4); 8.273 (7.4); 7.781 (3.7); 7.761 (5.2); 7.749 (2.0); 7.736 (10.3); 7.732 (7.8); 7.714 (12.6); 7.667 (3.0); 7.648 (3.8); 7.629 (1.4); 7.486 (4.4); 7.468 (4.0); 6.662 (9.2); 6.640 (9.0); 4.331 (1.6); 4.316 (1.6); 4.294 (3.6); 4.279 (3.5); 4.257 (1.8); 4.241 (1.7); 3.327 (205.1); 3.316 (7.1); 3.299 (15.4); 3.283 (6.0); 3.254 (0.4); 3.236 (0.5); 2.983 (0.6); 2.676 (1.1); 2.671 (1.6); 2.667 (1.2); 2.662 (0.6); 2.524 (4.3); 2.511 (84.9); 2.506 (172.8); 2.502 (230.6); 2.497 (172.0); 2.493 (86.4); 2.333 (1.1); 2.329 (1.6); 2.324 (1.2); 2.075 (1.4); 2.010 (0.6); 1.995 (6.0); 1.986 (7.1); 1.979 (16.0); 1.971 (7.1); 1.962 (5.9); 1.948 (1.0); 1.251 (3.7); 1.233 (0.9); 0.146 (1.1); 0.008 (8.6); 0.000 (258.3); −0.009 (10.6); −0.150 (1.2) Example 31: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 8.985 (1.1); 8.970 (2.2); 8.954 (1.1); 8.915 (3.7); 8.911 (3.8); 8.332 (3.8); 8.327 (3.8); 8.317 (0.7); 7.780 (2.2); 7.760 (3.7); 7.754 (5.3); 7.732 (7.2); 7.712 (1.8); 7.667 (1.7); 7.648 (2.2); 7.628 (0.8); 7.484 (2.5); 7.466 (2.2); 7.071 (4.5); 7.049 (4.3); 4.337 (0.9); 4.321 (1.0); 4.300 (2.0); 4.284 (1.9); 4.262 (1.1); 4.247 (1.0); 3.327 (285.7); 3.263 (4.4); 3.251 (6.0); 3.238 (4.7); 2.671 (2.2); 2.506 (242.1); 2.502 (316.4); 2.498 (246.3); 2.465 (5.7); 2.453 (6.8); 2.441 (4.8); 2.329 (2.1); 2.227 (16.0); 2.075 (0.7); 0.146 (1.2); 0.008 (9.8); 0.000 (239.2); −0.150 (1.2) Example 32: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ = 8.990 (2.4); 8.975 (5.1); 8.959 (2.4); 8.925 (9.4); 8.921 (9.7); 8.344 (9.7); 8.340 (9.7); 8.313 (2.1); 7.779 (14.8); 7.761 (10.5); 7.757 (14.0); 7.732 (5.2); 7.714 (3.6); 7.669 (3.9); 7.650 (4.7); 7.631 (1.6); 7.485 (5.4); 7.467 (4.7); 7.087 (11.5); 7.064 (10.9); 6.543 (0.4); 4.340 (2.1); 4.324 (2.2); 4.303 (4.6); 4.287 (4.4); 4.265 (2.4); 4.250 (2.2); 3.947 (2.2); 3.768 (12.4); 3.756 (16.0); 3.743 (13.7); 3.560 (1.3); 3.361 (5408.7); 3.278 (2.0); 3.231 (12.7); 3.218 (15.6); 3.206 (11.7); 3.168 (0.4); 3.149 (0.4); 2.678 (3.7); 2.673 (5.2); 2.669 (3.9); 2.527 (12.9); 2.522 (20.2); 2.513 (283.3); 2.509 (586.5); 2.504 (782.5); 2.500 (579.1); 2.495 (287.2); 2.335 (3.7); 2.331 (5.2); 2.326 (3.8); 1.262 (0.7); 1.069 (11.0); 0.146 (2.3); 0.008 (17.5); 0.000 (568.5); −0.009 (22.4); −0.150 (2.5) Example 33: 1H-NMR (400.0 MHz, d6-DMSO): =9.056 (10.9); 9.034 (2.9); 9.018 (5.7); 9.003 (2.8); 8.572 (10.9); 8.318 (0.5); 8.160 (9.1); 8.139 (15.9); 8.087 (16.0); 8.067 (9.7); 8.056 (4.4); 8.045 (3.7); 8.024 (0.8); 7.784 (5.4); 7.765 (7.5); 7.736 (6.1); 7.717 (4.3); 7.672 (4.4); 7.653 (5.6); 7.634 (2.1); 7.489 (6.4); 7.471 (5.6); 4.367 (2.4); 4.352 (2.6); 4.330 (5.3); 4.315 (5.1); 4.293 (2.8); 4.278 (2.6); 4.038 (0.5); 4.020 (0.5); 3.332 (218.9); 3.299 (45.9); 3.289 (10.5); 2.671 (1.9); 2.503 (284.3); 2.330 (1.9); 1.990 (1.9); 1.193 (0.6); 1.175 (1.0); 1.158 (0.5); 0.000 (34.2) Example 34: 1H-NMR (400.0 MHz, d6-DMSO): =9.046 (15.5); 9.041 (16.0); 9.028 (3.8); 9.013 (7.5); 8.997 (3.6); 8.600 (15.9); 8.596 (15.5); 8.318 (0.8); 8.273 (10.8); 8.256 (10.3); 8.251 (8.5); 8.245 (5.3); 7.785 (7.4); 7.766 (10.1); 7.754 (3.5); 7.743 (5.1); 7.736 (9.6); 7.717 (12.8); 7.705 (1.7); 7.693 (4.3); 7.673 (5.9); 7.654 (7.5); 7.635 (2.8); 7.492 (8.8); 7.474 (7.6); 4.361 (3.2); 4.345 (3.3); 4.323 (7.5); 4.307 (7.2); 4.285 (3.8); 4.270 (3.5); 3.331 (126.5); 2.677 (0.9); 2.672 (1.3); 2.668 (0.9); 2.664 (0.5); 2.526 (3.1); 2.512 (71.9); 2.508 (146.0); 2.503 (191.4); 2.499 (139.5); 2.495 (68.0); 2.335 (0.9); 2.330 (1.3); 2.326 (0.9); 1.990 (1.1); 1.398 (3.1); 1.234 (2.5); 1.194 (0.3); 1.176 (0.6); 0.146 (0.7); 0.008 (5.2); 0.000 (152.8); −0.009 (5.7); −0.150 (0.7) Example 35: 1H-NMR (400.0 MHz, d6-DMSO): =9.006 (2.6); 8.990 (5.5); 8.971 (11.9); 8.967 (11.3); 8.430 (10.8); 8.425 (10.9); 8.318 (0.7); 7.837 (14.2); 7.816 (16.0); 7.782 (5.1); 7.762 (7.0); 7.752 (2.5); 7.733 (5.8); 7.714 (4.2); 7.669 (4.2); 7.650 (5.3); 7.631 (2.0); 7.486 (6.2); 7.467 (5.4); 7.416 (15.8); 7.394 (14.6); 4.349 (2.3); 4.334 (2.3); 4.312 (5.1); 4.297 (5.0); 4.275 (2.6); 4.259 (2.4); 4.038 (0.4); 4.020 (0.4); 3.332 (182.1); 2.712 (0.4); 2.676 (1.4); 2.672 (1.9); 2.667 (1.4); 2.566 (0.6); 2.538 (71.1); 2.525 (5.4); 2.507 (214.8); 2.503 (279.3); 2.498 (207.1); 2.361 (0.4); 2.334 (1.3); 2.329 (1.8); 2.325 (1.4); 1.989 (1.7); 1.398 (2.4); 1.193 (0.5); 1.175 (0.9); 1.157 (0.5); 0.146 (0.8); 0.008 (6.2); 0.000 (171.7); −0.008 (7.4); −0.150 (0.8) Example 36: 1H-NMR (400.0 MHz, d6-DMSO): =8.976 (0.6); 8.961 (1.2); 8.945 (0.6); 8.865 (2.3); 8.860 (2.4); 8.249 (2.4); 8.245 (2.4); 7.781 (1.2); 7.762 (1.6); 7.749 (0.5); 7.731 (1.3); 7.713 (0.9); 7.667 (1.3); 7.660 (3.3); 7.644 (1.6); 7.639 (3.4); 7.631 (0.8); 7.485 (1.4); 7.466 (1.2); 6.662 (3.3); 6.640 (3.3); 6.182 (0.3); 6.169 (1.1); 6.157 (1.0); 6.144 (0.3); 4.330 (0.5); 4.315 (0.5); 4.293 (1.2); 4.277 (1.1); 4.255 (0.6); 4.240 (0.6); 3.937 (2.3); 3.334 (52.0); 2.738 (6.2); 2.726 (6.2); 2.525 (0.7); 2.512 (14.5); 2.507 (29.9); 2.503 (39.5); 2.498 (28.9); 2.494 (14.2); 1.069 (16.0); 0.008 (0.8); 0.000 (25.4); −0.009 (1.0) Example 37: 1H-NMR (400.0 MHz, d6-DMSO): =9.056 (8.3); 9.052 (8.6); 9.028 (2.1); 9.013 (4.3); 8.997 (2.0); 8.568 (8.6); 8.564 (8.5); 8.317 (0.4); 8.103 (7.9); 8.082 (16.0); 8.039 (16.0); 8.018 (8.1); 7.781 (4.2); 7.762 (5.8); 7.753 (2.1); 7.733 (4.7); 7.715 (3.3); 7.670 (3.3); 7.651 (4.2); 7.632 (1.6); 7.485 (5.0); 7.466 (4.3); 4.359 (1.8); 4.343 (1.9); 4.322 (4.2); 4.306 (4.0); 4.284 (2.1); 4.269 (2.0); 4.038 (0.4); 4.020 (0.4); 3.332 (190.7); 2.676 (0.8); 2.672 (1.1); 2.668 (0.8); 2.525 (2.7); 2.507 (120.4); 2.503 (157.4); 2.498 (117.3); 2.334 (0.8); 2.330 (1.0); 2.325 (0.8); 1.989 (1.6); 1.193 (0.4); 1.175 (0.9); 1.157 (0.4); 0.008 (1.9); 0.000 (55.8); −0.008 (2.4) Example 38: 1H-NMR (400.0 MHz, d6-DMSO): =10.158 (3.6); 9.003 (1.0); 8.987 (2.1); 8.972 (1.1); 8.952 (3.8); 8.949 (3.9); 8.393 (3.8); 8.389 (3.8); 7.840 (3.6); 7.818 (5.9); 7.782 (2.0); 7.761 (3.3); 7.751 (6.3); 7.730 (5.0); 7.715 (1.8); 7.669 (1.6); 7.650 (2.2); 7.631 (1.0); 7.484 (2.4); 7.466 (2.1); 4.346 (0.9); 4.331 (1.0); 4.309 (2.0); 4.294 (1.9); 4.272 (1.1); 4.256 (1.0); 4.038 (0.4); 4.020 (0.4); 3.334 (72.1); 2.672 (0.5); 2.503 (70.3); 2.329 (0.5); 2.082 (16.0); 2.056 (0.7); 1.989 (1.6); 1.193 (0.4); 1.175 (0.8); 1.157 (0.4); 0.000 (19.7) Example 39: 1H-NMR (400.0 MHz, d6-DMSO): =9.057 (0.3); 9.036 (10.4); 9.031 (11.4); 9.013 (5.1); 8.998 (2.4); 8.540 (10.2); 8.535 (9.9); 8.318 (0.4); 8.040 (12.0); 8.019 (16.0); 7.936 (0.5); 7.931 (0.4); 7.915 (0.4); 7.894 (13.5); 7.874 (10.4); 7.851 (0.4); 7.783 (4.8); 7.763 (6.6); 7.754 (2.4); 7.734 (5.4); 7.716 (3.8); 7.671 (3.9); 7.652 (5.0); 7.633 (1.9); 7.487 (5.6); 7.468 (4.9); 4.363 (2.1); 4.347 (2.2); 4.326 (4.8); 4.310 (4.6); 4.288 (2.5); 4.273 (2.3); 3.385 (0.4); 3.335 (340.1); 2.677 (0.9); 2.672 (1.2); 2.668 (0.9); 2.525 (3.6); 2.512 (72.9); 2.508 (140.6); 2.503 (180.0); 2.499 (131.9); 2.334 (0.9); 2.330 (1.2); 2.325 (0.9); 1.398 (0.6); 1.311 (3.1); 0.008 (2.8); 0.000 (66.7); −0.008 (2.7)

Biological Examples

In Vitro Assay with Nippostrongylus brasiliensis (NIPOBR)

(105) Adult Nippostrongylus brasiliensis were washed with saline buffer containing 100 U/ml penicillin, 0.1 mg/ml streptomycin and 2.5 μg/ml amphotericin B. Test compounds were dissolved in DMSO and worms were incubated in medium in a final concentration of 10 μg/ml (10 ppm) respectively 1 μg/ml (1 ppm). An aliquot of the medium was used to determine the acetylcholine esterase activity in comparison to a negative control. The principle of measuring acetylcholine esterase as readout for anthelmintic activity was described in Rapson et al (1986) and Rapson et al (1987).

(106) For the following examples, activity (reduction of AChE compared to negative control) was 60% or higher at 10 ppm: 1, 3, 4, 5, 7, 8, 11, 12, 14, 15, 16, 18, 24

(107) For the following examples, activity (reduction of AChE compared to negative control) was 60% or higher at 1 ppm: 1, 2, 3, 4, 5, 7, 8, 10, 11, 12, 13, 14, 15, 16, 24

(108) In Vitro Assay with Cooperia curticei (COOPCU)

(109) Solvent: Dimethyl Sulfoxide

(110) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with “Ringer's solution” to the desired concentration.

(111) Approximately 40 nematode larvae (Cooperia curticei) are transferred into a test tube containing the compound solution.

(112) After 5 days percentage of larval mortality is recorded. 100% efficacy means all larvae are killed; 0% efficacy means no larvae are killed.

(113) In this test for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 24, 30, 31, 32

(114) In Vitro Assay with Haemonchus contortus (HAEMCO)

(115) Solvent: Dimethyl Sulfoxide

(116) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with “Ringer's solution” to the desired concentration.

(117) Approximately 40 larvae of the red stomach worm (Haemonchus contortus) are transferred into a test tube containing compound solution.

(118) After 5 days percentage of larval mortality are recorded. 100% efficacy means all larvae are killed, 0% efficacy means no larvae are killed.

(119) In this test for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 24, 31

(120) In this test for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 20 ppm: 30

(121) Meloidogyne incognita (MELGIN) Assay

(122) Solvent: 125.0 parts by weight of acetone

(123) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water to the desired concentration.

(124) Vessels are filled with sand, a solution of the active ingredient, a suspension containing eggs and larvae of the southern root-knot nematode (Meloidogyne incognita) and salad seeds. The salad seeds germinate and the seedlings grow. Galls develop in the roots.

(125) After 14 days the nematicidal activity is determined on the basis of the percentage of gall formation. 100% means no galls were found and 0% means the number of galls found on the roots of the treated plants was equal to that in untreated control plants.

(126) In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 ppm: 1, 4, 7, 8, 9, 14, 18, 21, 24, 26

(127) In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 20 ppm: 5, 6, 11, 15, 19

(128) In Vivo Efficacy Test

(129) Haemonchus contortus/Trichostrongylus Colubriformis/Gerbil

(130) Gerbils, experimentally infected with Haemonchus and/or Trichostrongylus, were treated once during late prepatency. Test compounds were formulated as solutions or suspensions and applied parenterally or orally.

(131) Efficacy was determined per group as reduction of worm count in stomach and small intestine, respectively, after necropsy compared to worm count in an infected and placebo-treated control group.

(132) The following examples were tested and had an activity of 75% or higher at the given treatment (see table 4):

(133) TABLE-US-00004 TABLE 4 Treatment Haemonchus Trichostrongylus 20 mg/kg intraperitoneally 12, 14 14 10 mg/kg intraperitoneally 24 24 20 mg/kg subcutaneous 24 24 50 mg/kg orally  1

Formulation Examples

(134) An example for a formulation according to the present invention is the following:

(135) TABLE-US-00005 8 mg compound of Example 14 0.2 mL diethylene glycol monoethyl ether 0.2 mL Polyoxyl 35 Castor Oil 1.6 mL physiological sodium chloride solution

(136) An example for a preparation of such a formulation is as follows. The compound of the present invention was dissolved in 1 part diethylene glycol monoethyl ether and mixed with 1 part Polyoxyl 35 Castor Oil and 8 parts physiological sodium chloride solution.

(137) Such a formulation is suitable for oral or parenteral application.

(138) Formulations of other compounds of the present invention can be prepared in an analogue way and show analogue or identical compositions.

Comparative Example

In Vitro Assay with Haemonchus contortus (HAEMCO)

(139) Solvent: Dimethyl Sulfoxide

(140) To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with “Ringer's solution” to the desired concentration.

(141) Approximately 40 larvae of the red stomach worm (Haemonchus contortus) are transferred into a test tube containing compound solution.

(142) After 5 days percentage of larval mortality are recorded. 100% efficacy means all larvae are killed, 0% efficacy means no larvae are killed.

(143) In this test, for example, the following compound from the preparation example show a superior level of activity compared to the prior state of the art: see table 5

(144) TABLE-US-00006 TABLE 5 Substance Structure Object Concentration % Efficacy dat Ex.-No. 1-49 Known from WO2012/118139 01 HAEMCO  20 ppm   4 ppm 0.8 ppm 80 60 60 5dat 5dat 5dat Ex.-No. 1 From table 1 02 HAEMCO  20 ppm   4 ppm 0.8 ppm 100 100 100 5dat 5dat 5dat Ex.-No. 24 From table 1 03 HAEMCO  20 ppm   4 ppm 0.8 ppm 100 100 100 5dat 5dat 5dat