NOVEL HETEROARYL-SUBSTITUTED AMINOALKYL AZOLE COMPOUNDS AS PESTICIDES

Abstract

The present invention relates to novel heteroaryl-substituted aminoalkyl azole compounds of the general formula (I), in which the structural elements Y, Q.sup.1, Q.sup.2, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the meaning given in the description, to formulations and compositions comprising such compounds and for their use in the control of animal pests including arthropods and insects in plant protection and to their use for control of ectoparasites on animals.

##STR00001##

Claims

1. A compound of formula (I) ##STR00280## in which Q.sup.1 and Q.sup.2 are independently CR.sup.5 or N, provided at least one of Q.sup.1 and Q.sup.2 is N; Y is a direct bond or optionally substituted CH.sub.2; R.sup.1 is hydrogen; in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkylC.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6 alkynyl; or phenyl-C.sub.1-C.sub.6alkyl, in which phenyl is optionally substituted with one to five substituents, each independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —Si(CH.sub.3).sub.3, —SF.sub.5, —NH.sub.2, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl; R.sup.2 is a heteroaromatic bicyclic system containing 9-10 ring members including 1-4 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with 0-4 substituents X, and 0-2 substituents Z and 0-1 substitutents Z.sup.1; X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2, —SF.sub.5, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.3-C.sub.6cyloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.6cycloalkylthio, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, heterocyclylsulfanyl, heterocyclylsulfinyl, heterocyclylsulfonyl, heteroarylsulfanyl, heteroarylsulfinyl, heteroarylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S-phenylsulfinimidoyl, S-heterocyclylsulfinimidoyl, S-heteroarylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S-phenylsulfonimidoyl, S-heterocyclylsulfonimidoyl, S-heteroarylsulfonimidoyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(heterocyclyl), —SO.sub.2N(C.sub.1-C.sub.4alkyl)(heterocyclyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl)(heterocyclyl), —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl, tri(C.sub.1-C.sub.4alkyl)silyl; and 3-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with up to 4 substituents selected independently from the group consisting of fluorine, chlorine, bromine and C.sub.1-C.sub.3 alkyl; Z is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2, —SF.sub.5, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.6cycloalkylthio, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl, tri(C.sub.1-C.sub.4alkyl)silyl; and 3-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with up to 4 substituents selected independently from the group consisting of fluorine, chlorine, bromine and C.sub.1-C.sub.3alkyl; Z.sup.1 is hydrogen, or in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.2-C.sub.3haloalkyl, or C.sub.1-C.sub.4 alkoxy; R.sup.3 is hydrogen or optionally substituted C.sub.1-C.sub.6 alkyl; R.sup.4 is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is optionally substituted with one to three substituents selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CO.sub.2—C.sub.1-C.sub.6alkyl, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —NH.sub.2, —SF.sub.5; and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CONH(C.sub.3-C.sub.6cycloalkylalkyl), CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkylalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2—C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —C(═NOC.sub.1-C.sub.6alkyl)H and —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl; and 3-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with up to 4 substituents selected independently from the group consisting of fluorine, chlorine, bromine and C.sub.1-C.sub.3alkyl, or one of the substituents may optionally be selected from the following substructures S1-S24, in which the bond to the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is marked with a # and Z.sup.4 is CO or SO.sub.2 and Y.sup.4 is independently selected from CO or SO.sub.2: ##STR00281## ##STR00282## R.sup.41 is a heterocyclic ring which is selected from the group consisting of 3- to 10-membered saturated or partially unsaturated heterocyclyl, 5-membered heteroaryl, 6-membered heteroaryl, 9-membered heteroaryl and 10-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, 5-C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)—SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)—SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —NHCS—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CS—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CS—C.sub.1-C.sub.6alkyl, —NHCS—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CS-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C.sub.1-C.sub.6alkyl), —CSN(C.sub.1-C.sub.6alkyl).sub.2, —CSNH(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.3-C.sub.6cycloalkyl).sub.2, —CSNH-phenyl, —CSN(C.sub.1-C.sub.6alkyl)phenyl, —CSN(C.sub.3-C.sub.6cycloalkyl)phenyl, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; R.sup.42 is hydrogen, hydroxy; or in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, phenyl-C.sub.1-C.sub.6alkyl, naphthyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy-, C.sub.1-C.sub.6 haloalkoxy; or phenyl, wherein the phenyl is optionally substituted by one to three substituents independently selected from the group consisting of halogen, —CN, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylthio, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, and C.sub.1-C.sub.6 haloalkylsulfonyl; R.sup.43 is in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, phenyl-C.sub.1-C.sub.6alkyl, naphthyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxy-, C.sub.1-C.sub.6 haloalkoxy; or phenyl, wherein the phenyl is optionally substituted by one to three substituents independently selected from the group consisting of halogen, —CN, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylthio, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, and C.sub.1-C.sub.6 haloalkylsulfonyl; R.sup.44 is in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, phenyl-C.sub.1-C.sub.6alkyl, naphthyl-C.sub.1-C.sub.6alkyl; R.sup.45 is hydrogen or in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, phenyl-C.sub.1-C.sub.6alkyl, naphthyl-C.sub.1-C.sub.6 alkyl; or R.sup.41 and R.sup.42 together with the nitrogen atom to which they are attached, represent a monocyclic or polycyclic optionally substituted 3- to 12-membered saturated or partially unsaturated heterocyclyl which may contain further heteroatoms; R.sup.5 is —NH.sub.2, hydrogen, halogen, —CN, or in each case optionally substituted C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.3-C.sub.4halocycloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, —CH—(C.sub.1-C.sub.3alkoxy).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.3-C.sub.6cycloalkyl, —C(═NOC.sub.1-C.sub.4alkyl)H, or —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl.

2. The compound according to claim 1, in which Q.sup.1 and Q.sup.2 are independently CR.sup.5 or N, provided at least one of Q.sup.1 and Q.sup.2 is N; Y is a direct bond; R.sup.1 is hydrogen; in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkylC.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6 alkynyl; or phenyl-C.sub.1-C.sub.6alkyl, in which phenyl is optionally substituted with one to five substituents, each independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —Si(CH.sub.3).sub.3, —SF.sub.5, —NH.sub.2, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl; R.sup.2 is selected from one of the following bicyclic heterocycles T1-T70, in which the bond to the N atom is marked with a #; ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## wherein n is an integer from 0 to 4; m is an integer from 0 to 2; X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.6cycloalkylthio, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CONHSO.sub.2(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —CON(C.sub.1-C.sub.4alkyl)SO.sub.2(C.sub.1-C.sub.4alkyl), —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and 4-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N and O and optionally substituted with 1-2 substituents selected from the group consisting of methyl and ethyl; Z is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.6cycloalkylthio, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CONHSO.sub.2(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —CON(C.sub.1-C.sub.4alkyl)SO.sub.2(C.sub.1-C.sub.4alkyl), —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; Z.sup.1 is hydrogen, or in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, or C.sub.2-C.sub.3 haloalkyl; R.sup.3 is hydrogen or optionally substituted C.sub.1-C.sub.6 alkyl; R.sup.4 is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl, wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is optionally substituted with one to three substituents selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —SO.sub.2NH.sub.2, —NO.sub.2, —NH.sub.2, —SF.sub.5, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.6cycloalkylthio, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CONHSO.sub.2(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CONH(C.sub.3-C.sub.6cycloalkylalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkylalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —CON(C.sub.1-C.sub.4alkyl)SO.sub.2(C.sub.1-C.sub.4alkyl), —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and 3-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O and S and optionally substituted with up to 4 substituents selected independently from the group consisting of fluorine, chlorine, bromine and C.sub.1-C.sub.3alkyl; or one of the substituents may optionally be selected from the following substructures S1-S24, in which the bond to the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is marked with a # and Z.sup.4 is CO or SO.sub.2 and Y.sup.4 is independently selected from CO or SO.sub.2: ##STR00290## ##STR00291## R.sup.41 is a heterocyclic ring which is selected from the group consisting of 4- to 10-membered saturated or partially unsaturated heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and —CO.sub.2—C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkoxy, C.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfinyl, C.sub.1-C.sub.4haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.4alkyl, —NHCO—C.sub.3-C.sub.4cycloalkyl, —N(C.sub.1-C.sub.4alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(CO—C.sub.1-C.sub.4alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.4alkyl), —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.4alkyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)-SO.sub.2—C.sub.1-C.sub.4alkyl, —CON(C.sub.1-C.sub.4alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.4haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —NHSO.sub.2—C.sub.1-C.sub.4alkyl, —NHSO.sub.2—C.sub.1-C.sub.4haloalkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2—C.sub.1-C.sub.4alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-C.sub.1-C.sub.4alkyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.4alkyl), —SO.sub.2N(C.sub.1-C.sub.4alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; R.sup.42 is hydrogen, hydroxy; and C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl, naphthyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy-, C.sub.1-C.sub.4haloalkoxy; R.sup.43 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl, naphthyl-C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy-, C.sub.1-C.sub.4 haloalkoxy; R.sup.44 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl, naphthyl-C.sub.1-C.sub.4 alkyl; R.sup.45 is hydrogen and C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6haloalkenyl, C.sub.2-C.sub.6alkynyl, C.sub.2-C.sub.6haloalkynyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl, naphthyl-C.sub.1-C.sub.4 alkyl; or R.sup.41 and R.sup.42 together with the nitrogen atom to which they are attached, represent a monocyclic, spirocyclic or bridged polycyclic 4- to 12-membered saturated or partially unsaturated heterocyclyl which may contain up to two further heteroatoms selected from the group of oxygen, nitrogen and sulfur and which is optionally substituted with one to three substituents selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, and —NH.sub.2; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkoxy, C.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.4haloalkylthio, C.sub.1-C.sub.4haloalkylsulfinyl, C.sub.1-C.sub.4haloalkylsulfonyl, —NHSO.sub.2—C.sub.1-C.sub.4alkyl, —NHCO.sub.2-C.sub.1-C.sub.4alkyl, —OCONH—C.sub.1-C.sub.4alkyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —NHCO—C.sub.1-C.sub.4cycloalkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cycloalkyl, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —SO.sub.2NH(C.sub.1-C.sub.4alkyl); R.sup.5 is hydrogen, halogen, CN, or in each case optionally substituted C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.3-C.sub.4halocycloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, —CH—(C.sub.1-C.sub.3alkoxy).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —C(═NOC.sub.1-C.sub.4alkyl)H, or —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl.

3. The compound according to claim 1, in which Q.sup.1 is N; Q.sup.2 is CR.sup.5; Y is a direct bond; R.sup.1 is hydrogen; C.sub.1-C.sub.6alkyl, optionally substituted with a substituent selected from the group of —CN, methoxy, ethoxy, methylthio and methylsulfonyl; or C.sub.1-C.sub.6haloalkyl; C.sub.3-C.sub.6cycloalkylC.sub.1-C.sub.6alkyl; C.sub.2-C.sub.6alkenyl; C.sub.2-C.sub.6alkynyl; or C.sub.2-C.sub.6 haloalkenyl; R.sup.2 is selected from one of the following bicyclic heterocycles T1-T21, T23-T30, T32-T39, T41, T42, T68-T70, in which the bond to the N atom is marked with a #; ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## wherein n is an integer from 0 to 4; m is an integer from 0 to 2; X is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2, SF.sub.5 and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, cycloalkylthio, cycloalkylsulfinyl, cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, phenylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CONHSO.sub.2(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —CON(C.sub.1-C.sub.4alkyl)SO.sub.2(C.sub.1-C.sub.4alkyl), —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and 4-6 membered heterocyclyl containing 1-2 oxygen atoms and optionally substituted with 1-2 substituents selected from the group consisting of methyl and ethyl; Z is selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CONHSO.sub.2(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —CON(C.sub.1-C.sub.4alkyl)SO.sub.2(C.sub.1-C.sub.4alkyl), —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; Z.sup.1 is selected from the group consisting of hydrogen and C.sub.1-C.sub.6 alkyl; R.sup.3 is hydrogen or C.sub.1-C.sub.6 alkyl; R.sup.4 is pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl, wherein the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is optionally substituted with one to three substituents selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —SO.sub.2NH.sub.2, —NO.sub.2, —NH.sub.2, —SF.sub.5, and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.3-C.sub.6halocycloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NHCO—C.sub.1-C.sub.4alkyl, NHCO—C.sub.3-C.sub.6cycloalkyl, —NHSO.sub.2(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.3-C.sub.6cyclolkyl, —N(C.sub.1-C.sub.4alkyl)SO.sub.2C.sub.1-C.sub.4alkyl, —N(SO.sub.2C.sub.1-C.sub.4alkyl).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CONH(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CONHSO.sub.2(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —CON(C.sub.1-C.sub.4alkyl)(C.sub.3-C.sub.6cycloalkyl), —CONH(C.sub.3-C.sub.6cycloalkylalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkylalkyl), —CON(C.sub.1-C.sub.4alkyl)-phenyl, —CON(C.sub.1-C.sub.4alkyl)SO.sub.2(C.sub.1-C.sub.4alkyl); and 3-6 membered heterocyclyl containing 1-2 heteroatoms selected from the group consisting of N, O, and S and optionally substituted with up to 4 substituents selected independently from the group consisting of fluorine, chlorine, bromine, methyl and ethyl; or one of the substituents may optionally be selected from the following substructures S1, S2, S3, S4, S5, S16 and S17, in which the bond to the pyridine, pyrimidine, pyrazine, pyridazine or 5-membered heteroaryl is marked with a # and Z.sup.4 is CO: ##STR00297## R.sup.41 is a heterocyclic ring which is selected from the group consisting of 4- to 8-membered saturated or partially unsaturated heterocyclyl, 5-membered heteroaryl and 6-membered heteroaryl, each of which is optionally substituted by one to two substituents independently selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and —CO.sub.2—C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.4cycloalkylsulfanyl, C.sub.3-C.sub.4cycloalkylsulfinyl, C.sub.3-C.sub.4cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.3alkyl), —N(C.sub.1-C.sub.3alkyl).sub.2, —NHCO—C.sub.1-C.sub.3alkyl, —N(C.sub.1-C.sub.3alkyl)CO—C.sub.1-C.sub.3alkyl, —N(C.sub.3-C.sub.4cycloalkyl)CO—C.sub.1-C.sub.3alkyl, —NHCO—C.sub.3-C.sub.4cycloalkyl, —N(C.sub.1-C.sub.3alkyl)CO—(C.sub.3-C.sub.4cycloalkyl), —N(C.sub.3-C.sub.4cycloalkyl)CO—(C.sub.3-C.sub.4cycloalkyl), —CONH(C.sub.1-C.sub.3alkyl), —CON(C.sub.1-C.sub.3alkyl).sub.2, —CONH(C.sub.3-C.sub.4cycloalkyl), —CON(C.sub.1-C.sub.3alkyl)(C.sub.3-C.sub.4cycloalkyl), —CON(C.sub.3-C.sub.4cycloalkyl).sub.2, —NHSO.sub.2—C.sub.1-C.sub.3alkyl, —NHSO.sub.2—C.sub.1-C.sub.3haloalkyl, —N(C.sub.1-C.sub.3alkyl)SO.sub.2—C.sub.1-C.sub.3alkyl, —N(C.sub.3-C.sub.4cycloalkyl)SO.sub.2—C.sub.1-C.sub.3alkyl, —NHSO.sub.2—C.sub.3-C.sub.4cycloalkyl, —N(C.sub.1-C.sub.3alkyl)SO.sub.2—(C.sub.3-C.sub.4cycloalkyl), —N(C.sub.3-C.sub.4cycloalkyl)SO.sub.2—(C.sub.3-C.sub.4cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.3alkyl), —SO.sub.2N(C.sub.1-C.sub.3alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.3alkyl)(C.sub.3-C.sub.4cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.4cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.4cycloalkyl).sub.2; R.sup.42 is hydrogen, hydroxy; and C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4haloalkenyl, C.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.4cycloalkyl, C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl, phenyl-C.sub.1-C.sub.2alky, C.sub.1-C.sub.3alkoxy; R.sup.43 is C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4haloalkenyl, C.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.4cycloalkyl, C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl, phenyl-C.sub.1-C.sub.2alkyl, C.sub.1-C.sub.3alkoxy; R.sup.44 is C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4haloalkenyl, C.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.4cycloalkyl, C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl, phenyl-C.sub.1-C.sub.2alkyl; R.sup.45 is hydrogen and C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4haloalkenyl, C.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.4cycloalkyl, C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl, phenyl-C.sub.1-C.sub.2alkyl; or R.sup.41 and R.sup.42 together with the nitrogen atom to which they are attached, represent a monocyclic, spirocyclic or bridged polycyclic 4- to 8-membered saturated heterocyclyl which may contain up to one further heteroatom selected from the group of oxygen, nitrogen and sulfur and which is optionally substituted with one to three substituents selected from the group consisting of halogen, ═O (oxo), ═S (thiono), hydroxy, and —CN; and —CO.sub.2—C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3alkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.4cycloalkylsulfanyl, C.sub.3-C.sub.4cycloalkylsulfinyl, C.sub.3-C.sub.4cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NHCO—C.sub.1-C.sub.3alkyl, —N(C.sub.1-C.sub.3alkyl)CO—C.sub.1-C.sub.3alkyl, —NHCO—C.sub.1-C.sub.3cycloalkyl, —N(C.sub.1-C.sub.3alkyl)CO—C.sub.3-C.sub.4cycloalkyl, —CO.sub.2C.sub.1-C.sub.3alkyl, —CONH(C.sub.1-C.sub.3alkyl), —CONH(C.sub.3-C.sub.4cycloalkyl), and —CON(C.sub.1-C.sub.3alkyl).sub.2; R.sup.5 is hydrogen, halogen, CN, or in each case optionally substituted C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.3-C.sub.4halocycloalkyl, C.sub.1-C.sub.3alkoxy, or C.sub.1-C.sub.3haloalkoxy.

4. The compound according to claim 1, in which Q.sup.1 is N; Q.sup.2 is CR.sup.5; Y is a direct bond; R.sup.1 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthioethyl, methylsulfonylethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropylmethyl, cyclobutylmethyl, 2-propen-1-yl, 3-methyl-but-2-en-1-yl, 3,3-difluoro-prop-2-en-1-yl, 3,3-dichloro-prop-2-en-1-yl or 2-propyn-1-yl; R.sup.2 is selected from one of the following bicyclic heterocycles T1, T2, T3, T7 or T8, in which the bond to the N atom is marked with a #; ##STR00298## wherein n is an integer from 0 to 2; and m is an integer from 0 to 1; and X is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, —CN, —NO.sub.2, —SF.sub.5, methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, cyclobutyl, oxacyclobutyl, cyclopentyl, oxacyclopent-2-yl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, and trifluoromethylsulfonyl; cyclopropylthio, cyclopropylsulfinyl, cylopropylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, and Z is selected from the group consisting of hydrogen, fluorine, chlorine, bromine; methyl, ethyl and cyclopropyl; Z.sup.1 is selected from the group consisting of hydrogen and methyl; R.sup.3 is hydrogen or methyl; R.sup.4 is thiazol, pyridine, pyrazine, pyridazine or pyrimidine, wherein the thiazol, pyridine, pyrazine, pyridazine or pyrimidine is optionally substituted with one to three substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, —CN, —NO.sub.2, —CONH.sub.2, —SO.sub.2NH.sub.2, methyl, ethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, cyclopropyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl morpholinylcarbonyl, dimethylmorpholinylcarbonyl, piperidinylcarbonyl, pyrrolidinylcarbonyl, azetidinylcarbonyl, azepanylcarbonyl, oxazepanylcarbonyl, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-cyclopropylmethyl, N-methylcarbamoyl, morpholinylsulfonyl, dimethylmorpholinylsulfonyl, piperidinylsulfonyl, pyrrolidinylsulfonyl, azetidinylsulfonyl, azepanylsulfonyl, and oxazepanylsulfonyl; oxetanyl, tetrahydrofuranyl, pyranyl R.sup.5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy or difluoromethyl.

5. The compound according to claim 1, in which Q.sup.1 is N; Q.sup.2 is CR.sup.5; Y is a direct bond; R.sup.1 is hydrogen; R.sup.2 is selected from one of the following bicyclic heterocycles T1, T2 and T7 in which the bond to the N atom is marked with a # ##STR00299## wherein n is an integer of 0-2; and X is independently selected from the group consisting of hydrogen, chlorine, bromine, —CN, —SF.sub.5, trifluoromethyl, trifluoromethoxy, difluoromethoxy, methyl, isopropyl, tert-butyl, cyclopropyl, methylthio, ethylthio, cyclopropylthio and phenylsulfonyl; R.sup.3 is methyl; R.sup.4 is thiazol, pyridine, pyrazine, pyridazine or pyrimidine, wherein the thiazol, pyridine, pyrazine, pyridazine or pyrimidine is unsubstituted or is substituted with one substituent selected from the group consisting of fluorine, chlorine, bromine, —CN, —NH.sub.2, —CONH.sub.2, —SO.sub.2NH.sub.2, methyl, trifluoromethyl, methoxy, ethoxy, morpholin-4-ylcarbonyl, dimethylmorpholin-4-ylcarbonyl, pyrrolidine-1-ylcarbonyl, N-ethylcarbamoyl, N,N-diethylcarbamoyl, (N-cyclopropylmethyl,N-methyl)carbamoyl and oxetanyl or said thiazol, pyridine, pyrazine, pyridazine or pyrimidine optionally carries a second substituent selected from fluorine, chlorine and bromine; R.sup.5 is hydrogen, methyl, methoxy or cyclopropyl.

6. The compound according to claim 1, comprising a structure according to formula (I′). ##STR00300##

7. The compound according to claim 1, comprising a structure according to formula (I″). ##STR00301##

8. The compound according to claim 1, in which Q.sup.1 represents N or CR.sup.5 and Q.sup.2 represents N.

9. The compound according to claim 1, in which Q.sup.1 represents N and Q.sup.2 represents CR.sup.5.

10. The compound of formula (k). ##STR00302##

11. A formulation, comprising at least one compound of formula (I) according to claim 1.

12. The formulation according to claim 11, wherein the compound of formula (I) is in a mixture with at least one further active compound.

13. A method for controlling a pest, optionally an animal pest, comprising allowing a compound of formula (I) according to claim 1 or a formulation thereof to act on the pest and/or a habitat thereof, wherein methods for treatment of an animal body by surgery or therapy and methods practised on an animal body are excluded.

14. A method for protecting seed and/or a germinating plant from a pest, optionally an animal pest, comprising contacting said seed with a compound of formula (I) according to claim 1 or with a formulation thereof.

15. Seed obtained by a method according to claim 14.

Description

PREPARATION EXAMPLES

Intermediate 1A

6-Chloro-5-(trifluoromethyl)-1,3-benzoxazole-2(3H)-thione

[0537] ##STR00054##

[0538] 2-Amino-5-chloro-4-(trifluoromethyl)phenol (1.00 g, 4.73 mmol) was dissolved in pyridine (10 mL) and potassium O-ethyl carbonodithioate (1.14 g, 7.09 mmol) was added. The mixture was heated to 120° C. for 2 h. After cooling to RT, the mixture was poured into water and acidified with 1M hydrochloric acid against universal indicator paper. The mixture was extracted with MTBE, the organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate 10:1) to give 826 mg (100% purity, 69% yield) of intermediate 1A.

[0539] LC-MS (Method 1): R.sub.t=1.82 min; MS (ESIneg): m/z=252 [M−H].sup.−

[0540] .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 2.096 (0.64), 2.558 (14.33), 7.560 (16.00), 8.037 (13.36).

Intermediate 2A

2,6-dichloro-5-(trifluoromethyl)-1,3-benzoxazole

[0541] ##STR00055##

[0542] 6-chloro-5-(trifluoromethyl)-1,3-benzoxazole-2(3H)-thione (intermediate 1A, 820 mg, 3.23 mmol) was dissolved in thionyl chloride (6.0 mL, 82 mmol) and DMF (600 μL, 7.8 mmol) was added. The mixture was heated to 70° C. and stirred for 15 min until the evolution of gas ceased. The reaction mixture was poured into saturated aqueous sodium carbonate solution and extracted with three portions of MTBE. The organic extract was washed with brine, passed through a Macherey & Nagel MN 616 WA filter and evaporated. The crude product was triturated with cyclohexane and dried under vacuum. 468 mg (94% purity, 53% yield of intermediate 2A were obtained as a light-red solid.

[0543] .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 7.452 (0.87), 7.808 (0.58), 8.336 (16.00), 8.372 (13.50).

Intermediate 3A

N.SUP.2.-[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]-L-alaninamide

[0544] ##STR00056##

[0545] 2,6-Dichloro-5-(trifluoromethyl)-1,3-benzoxazole (intermediate 2A, 480 mg, 1.87 mmol), DIPEA (980 μl, 5.6 mmol) and L-alaninamide hydrochloride (1:1) (257 mg, 2.06 mmol) were dissolved in THF (5.0 mL). The mixture was heated over night to 65° C. with stirring. After cooling to RT, it was poured into water and extracted with three portions of ethyl acetate The combined organic extracts were dried over Chromabond PTL (30 mL cartridge) and evaporated. The oily residue was triturated with dichloromethane to form a precipitate that was filtered and washed with two portions of dichloromethane. The filtrate was evaporated and triturated once more with dichloromethane to yield a second crop of the product. The precipitates were combined to give 450 mg (100% purity, 78% yield) of intermediate 3A.

[0546] LC-MS (Method 1): R.sub.t=1.48 min; MS (ESIpos): m/z=308 [M+H].sup.+

[0547] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.378 (16.00), 1.390 (15.94), 2.509 (10.70), 4.223 (0.64), 4.235 (2.59), 4.247 (3.82), 4.259 (2.51), 4.271 (0.61), 7.129 (4.62), 7.571 (4.60), 7.677 (12.43), 7.864 (10.42), 8.677 (3.99), 8.689 (3.84).

Example I-001

6-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)-1,3-benzoxazol-2-amine

[0548] ##STR00057##

[0549] N.sup.2-[6-Chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]-L-alaninamide (intermediate 3A, 445 mg, 1.45 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (480 μl, 3.6 mmol) were dissolved in dichloromethane (5.0 mL) and heated to reflux for 90 min. The solvent was distilled, the residue was taken up into a mixture of 1,4-dioxane (5.0 mL) and acetic acid (1.0 ml, 17 mmol). and 2-hydrazinylpyrimidine (319 mg, 2.89 mmol) was added. This mixture was heated to 60° C. for 3 h, then cooled, poured into saturated aqueous sodium carbonate solution and extracted with three portions of MTBE. The organic extract was washed with brine, passed through a Macherey & Nagel MN 616 WA filter and evaporated. The crude product solidified upon evaporation. It was first triturated with acetonitrile and eventually purified by preparative HPLC (RP C-18 phase with a gradient of water, acetonitrile with 0.1% ammonia) to give 364 mg (100% purity, 61% yield) of the title compound.

[0550] LC-MS (Method 1): R.sub.t=1.72 min; MS (ESIpos): m/z=410 [M+H].sup.+

[0551] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.665 (14.88), 1.677 (14.84), 5.770 (4.10), 5.899 (0.58), 5.911 (2.43), 5.923 (3.32), 5.935 (2.32), 5.946 (0.57), 7.543 (12.13), 7.656 (4.10), 7.664 (8.18), 7.672 (4.27), 7.836 (9.88), 8.192 (13.15), 8.995 (16.00), 9.003 (15.71), 9.250 (4.43), 9.263 (4.24).

##STR00058##

TABLE-US-00005 TABLE 1 Example Structure NMR Peaklist.sup.[1] LC-MS.sup.[1] I-002 [00059] embedded image .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 1.653 (13.39), 1.664 (13.33), 2.089 (0.89), 5.767 (6.85), 5.864 (0.50), 5.875 (1.98), 5.887 (2.37), 5.900 (1.92), 5.912 (0.49), 6.946 (1.65), 6.952 (1.80), 6.954 (1.94), 6.960 (2.44), 6.965 (1.82), 6.967 (2.30, 6.974 (2.22), 7.045 (0.53), 7.046 (0.52), 7.058 (4.51), 7.060 (6.06), 7.066 (8.34), 7.073 (0.58), 7.291 (4.35), LC-MS (Method 1): R.sub.t = 1.16 min; MS (ESIpos): m/z = 308 [M + H].sup.+ 7.304 (4.17), 7.666 (4.20), 7.674 (8.06), 7.682 (4.22). I-003 [00060] embedded image .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 1.231 (0.49), 1.667 (15.28), 1.679 (15.16), 5.901 (0.57), 5.913 (2.40), 5.925 (3.20), 5.937 (2.39), 5.949 (0.59), 7.334 (2.88), 7.348 (3.34), 7.418 (5.93), 7.420 (5.76), 7.525 (4.96), 7.538 (4.28), 7.665 (4.17), 7.673 (8.25), 7.681 (4.31), 8.182 (13.61), 9.004 (15.97), 9.012 (16.00), 9.084 (4.47), 9.097 LC-MS (Method 1): R.sub.t = 1.56 min; MS (ESIpos): m/z = 376 [M + H].sup.+ (4.33). I-004 [00061] embedded image .sup.1H-NMR (400 MHz, DMSO-d.sup.6) δ [ppm]: 1.104 (1.96), 1.676 (15.79), 16.93 (16.00), 3.074 (0.62), 3.566 (0.83), 5.982 (0.76), 5.998 (2.57), 6.016 (3.75), 6.034 (2.59), 7.070 (2.56), 7.090 (5.32), 7.110 (3.21), 7.342 (5.25), 7.362 (4.62), 7.559 (4.76), 7.579 (4.46), 7.627 (3.35), 7.639 (6.38), 7.651 (3.61), 8.175 (6.31), 8.961 (10.70), 8.973 (10.73), LC-MS (Method 1): R.sub.t = 1.56 min; MS (ESIpos): m/z = 376 [M + H].sup.+ 9.150 (4.63), 9.170 (4.60). I-005 [00062] embedded image .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 1.672 (15.37), 1.684 (15.18), 5.935 (0.54), 5.946 (2.22), 5.959 (3.23), 5.971 (2.18), 5.982 (0.53), 7.618 (6.12), 7.668 (4.28), 7.676 (8.47), 7.684 (4.39), 7.797 (6.17), 8.186 (14.31), 9.011 (16.00), 9.019 (15.75), 9.593 (4.45), 9.606 (4.24). LC-MS (Method 1): R.sub.t = 1.87 min; MS (ESIpos): m/z = 444 [M + H].sup.+ I-006 [00063] embedded image .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 1.666 (14.80), 1.677 (14.80), 5.932 (1.56), 7.443 (6.25), 7.445 (6.33), 7.487 (6.44), 7.663 (4.32), 7.671 (8.48), 7.679 (4.37), 8.186 (13.36), 9.003 (16.00), 9.011 (16.00), 9.423 (2.11). LC-MS (Method 1): R.sub.t = 1.79 min; MS (ESIpos): m/z = 410 [M + H].sup.+ I-007 [00064] embedded image .sup.1H-NMR (400 MHz, DMSO-d.sup.6) δ [ppm]: 1.635 (8.54), 1.652 (8.65), 2.322 (16.00), 5.844 (1.27), 5.862 (1.81), 5.881 (1.28), 7.270 (4.99), 7.351 (5.05), 7.646 (1.86), 7.658 (3.79), 7.670 (2.00), 8.155 (4.44), 8.779 (2.23), 8.799 (2.18), 8.983 (6.63), 8.995 (6.62). LC-MS (Method 1): Rt = 1.62 min; MS (ESIpos): m/z = 400 [M + H].sup.+ I-008 [00065] embedded image .sup.1H-NMR (400 MHz, DMSO-d.sup.6) δ [ppm]: 1.652 (15.82), 1.669 (16.00), 2.075 (1.89), 5.992 (0.57), 6.009 (2.28), 6.027 (3.47), 6.044 (2.30), 6.062 (0.60), 7.206 (12.03), 7.676 (4.03), 7.689 (8.05), 7.701 (4.30), 7.953 (12.25), 8.171 (12.12), 8.970 (4.26), 8.988 (4.23), 9.014 (15.44), 9.027 (15.30). LC-MS (Method 1): R.sub.t = 1.77 min; MS (ESIpos): m/z = 292 [M + H].sup.+ I-009 [00066] embedded image .sup.1H-NMR (400 MHz, DMSO-d.sup.6) δ [ppm]: 1.658 (15.74), 1.675 (16.00), 5.991 (0.58), 6.008 (2.44), 6.025 (3.66), 6.044 (2.48), 6.061 (0.61), 6.954 (2.55), 6.966 (4.65), 6.972 (5.63), 6.986 (6.24), 6.989 (5.21), 7.118 (3.14), 7.137 (4.67), 7.156 (2.05), 7.591 (4.89), 7.609 (3.71), 7.612 (3.96), 7.686 (3.72), 7.698 (7.55), 7.710 (3.99), 8.148 (10.36), 8.645 LC-MS (Method 3): R.sub.t = 0.65 min; MS (ESIpos): m/z = 324 [M + H].sup.+ (4.24), 8.664 (4.17), 9.032 (13.91), 9.044 (13.94). I-010 [00067] embedded image .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 1.649 (16.00), 1.660 (15.99), 2.078 (1.52), 5.874 (0.54), 5.866 (2.23), 5.898 (3.16), 5.910 (2.20), 5.921 (0.56), 7.271 (7.04), 7.274 (9.19), 7.288 (9.51), 7.290 (6.90), 7.653 (3.97), 7.661 (7.70), 7.669 (3.96), 8.171 (13.88), 8.991 (15.73), 8.999 (15.41), 9.250 (3.90), 9.263 (3.74). LC-MS (MCW-FT- MS-M1): R.sub.t = 1.72 min; MS (ESIpos): m/z = 420 [M + H].sup.+ I-011 [00068] embedded image .sup.1H-NMR (600 MHz, DMSO-d.sup.6) δ [ppm]: 1.637 (6.15), 1.649 (6.08), 2.074 (1.79), 2.321 (16.00), 5.893 (1.01), 5.906 (1.22), 5.917 (1.00), 7.544 (5.06), 7.598 (1.70), 7.606 (3.35), 7.614 (1.73), 7.823 (4.05), 8.947 (6.55), 8.955 (6.37), 9.198 (1.74), 9.211 (1.70). LC-MS (Method 1): R.sub.t = 1.74 min; MS (ESIpos): m/z = 424 [M + H].sup.+ I-12 [00069] embedded image .sup.1H-NMR (500 MHz, DMSO-d.sup.6) δ [ppm]: −0.006 (0.82), 0.006 (0.62), 1.645 (6.01), 1.659 (6.01), 2.316 (16.00), 5.926 (0.96), 5.940 (1.32), 5.955 (0.93), 7.606 (4.17), 7.1616 (3.53), 7.625 (1.80), 7.789 (2.51), 8.960 (6.60), 8.969 (6.46), 9.531 (1.73), 9.547 (1.67). LC-MS (Method 1): R.sub.t = 1.89 min; MS (ESIpos): m/z = 458 [M + H].sup.+ I-13 [00070] embedded image .sup.1H-NMR (400 MHz, DMSO-d.sup.6) δ [ppm]: 1.106 (2.66), 1.157 (0.71), 1.175 (1.42), 1.193 (0.73), 1.643 (15.79), 1.660 (16.00), 1.989 (2.63), 3.077 (0.79), 4.021 (0.63), 4.039 (0.62), 5.755 (4.87), 5.861 (0.57), 5.878 (2.44), 5.896 (3.51), 5.914 (2.45), 5.932 (0.61), 7.152 (4.64), 7.156 (5.57), 7.181 (5.33), 7.186 (3.70), 7.647 (3.59), 7.659 (7.38), 7.671 (3.87), 8.167 (9.27), 8.987 (13.21), 8.999 (13.23), 9.240 (4.39), 9.259 LC-MS (Method 1): R.sub.t = 1.68 min; MS (ESIpos): m/z = 376 [M + H].sup.+ (4.30). I-14 [00071] embedded image .sup.1H-NMR (400 MHz, DMSO-d.sup.6) δ [ppm]: −0.008 (0.53), 0.008 (0.67), 1.639 (6.14), 1.656 (6.28), 2.318 (16.00), 5.898 (1.00), 5.917 (1.32), 5.935 (1.01), 7.444 (2.89), 7.474 (2.75), 7.601 (1.78), 7.613 (3.55), 7.625 (1.88), 8.954 (6.76), 8.966 (6.67), 9.363 (1.79), 9.383 (1.78). LC-MS (Method 3): R.sub.t = 0.94 min; MS (ESIpos): m/z = 424 [M + H].sup.+ I-15 [00072] embedded image .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.397 (4.67), 1.640 (15.80), 1.657 (16.00), 5.889 (1.42), 5.906 (2.09), 5.922 (1.44), 7.472 (9.38), 7.917 (5.87), 7.939 (6.86), 8.180 (9.52), 8.218 (4.39), 8.225 (4.57), 8.240 (3.94), 8.246 (4.08), 8.629 (4.81), 8.635 (4.67), 9.386 (2.60), 9.401 (2.23). LC-MS (Method 1): R.sub.t = 2.36 min; MS (ESIpos): m/z = 443 [M + H].sup.+ I-16 [00073] embedded image .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.162 (0.73), 1.177 (1.46), 1.191 (0.74), 1.362 (0.42), 1.377 (0.43), 1.397 (1.70), 1.649 (14.79), 1.663 (14.70), 1.991 (2.74), 4.025 (0.64), 4.039 (0.63), 5.863 (0.56), 5.877 (2.27), 5.891 (3.03), 5.906 (2.23), 5.92 (0.55), 7.339 (14.12), 7.645 (4.19), 7.655 (8.20), 7.664 (4.28), 7.720 (13.52), 8.173 (13.09), 8.982 (16.00), 8.992 (15.69), 9.065 (3.93), 9.081 (3.78). LC-MS (Method 1): R.sub.t = 1.65 min; MS (ESIpos): m/z = 376 [M + H].sup.+ I-17 [00074] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.177 (0.83), 1.648 (16.00), 1.659 (15.89), 1.991 (1.56), 5.758 (3.56), 5.975 (0.44), 5.987 (1.72), 5.998 (2.58), 6.010 (1.67), 6.021 (0.42), 7.578 (13.08), 7.841 (10.72), 8.101 (6.05), 8.116 (6.42), 8.256 (13.89), 8.584 (4.27), 8.588 (4.24), 8.598 (4.04), 8.602 (4.02), 9.053 (6.27), 9.057 (5.97), 9.265 (3.02), 9.278 (2.81). LC-MS (Method 1): R.sub.t = 2.02 min; MS (ESIpos): m/z = 434 [M + H].sup.+ I-18 [00075] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.107 (1.09), 1.166 (0.72), 1.178 (1.44), 1.189 (0.72), 1.655 (14.29), 1.667 (14.24), 1.992 (2.78), 4.026 (0.66), 4.038 (0.66), 5.758 (5.11), 5.988 (0.51), 5.999 (1.98), 6.011 (2.94), 6.023 (1.95), 6.035 (0.48), 7.483 (16.00), 81.06 (5.22), 8.120 (5.55), 8.256 (11.45), 8.589 (3.64), 8.593 (3.69), 8.604 (3.47), 8.607 (3.50), 9.061 (5.51), 9.064 (5.57), 9.440 (3.65), 9.453 (3.51). LC-MS (Method 1): R.sub.t = 2.09 min; MS (ESIpos): m/z = 434 [M + H].sup.+ I-019 [00076] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.594 (0.45), 1.606 (0.48), 1.625 (6.43), 1.636 (6.42), 2.192 (0.67), 2.332 (16.00), 3.582 (2.29), 5.974 (1.07), 5.986 (1.42), 5.998 (1.06), 7.589 (5.33), 7.842 (4.47), 8.037 (2.46), 8.051 (2.60), 8.541 (1.79), 8.545 (1.79), 8.555 (1.71), 8.559 (1.72), 9.021 (2.46), 9.024 (2.49), 9.250 (1.89), 9.264 (1.85). LC-MS (Method 4): R.sub.t = 3.47 min; MS (ESIpos): m/z = 448 [M + H].sup.+ I-020 [00077] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.632 (6.22), 1.643 (6.20), 1.653 (0.49), 2.332 (16.00), 5.985 (0.99), 5.997 (1.38), 6.010 (1.03), 7.484 (3.42), 7.493 (3.13), 8.042 (2.33), 8.056 (2.48), 8.546 (1.76), 8.549 (1.82), 8.560 (1.67), 8.564 (1.74), 9.029 (2.28), 9.032 (2.38), 9.421 (1.84), 9.433 (1.77). LC-MS (Method 3): R.sub.t = 1.12 min; MS (ESIpos): m/z = 448 [M + H].sup.+ I-021 [00078] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.640 (6.09), 1.651 (6.11), 1.660 (0.40), 2.079 (0.66), 2.332 (16.00), 6.012 (0.96), 6.024 (1.37), 6.036 (0.96), 7.613 (2.54), 7.841 (2.56), 8.048 (2.36), 8.063 (2.50), 8.552 (1.76), 8.556 (1.80), 8.567 (1.66), 8.570 (1.72), 9.034 (2.27), 9.037 (2.33), 9.585 (1.86), 9.599 (1.77). LC-MS (Method 3): R.sub.t = 1.15 min; MS (ESIpos): m/z = 482 [M + H].sup.+ I-022 [00079] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.664 (6.05), 1.676 (6.08), 2.361 (16.00), 5.172 (1.01), 5.185 (1.24), 5.197 (0.99), 7.333 (4.02), 7.779 (4.00), 8.773 (2.38), 8.776 (2.44), 8.917 (2.32), 8.919 (2.29), 9.119 (1.87), 9.133 (1.79). LC-MS (Method 1): Rt = 2.22 min; MS (ESIpos): m/z = 525 [M + H].sup.+ I-023 [00080] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.664 (5.73), 1.675 (5.72), 2.359 (16.00), 5.166 90.98), 5.179 (1.16), 5.191 (0.96), 7.259 (2.14), 7.485 (2.43), 8.789 (2.09), 8.792 (2.18), 8.907 (2.01), 8.909 (1.98), 9.269 (1.68), 9.282 (1.60). LC-MS (Method 1): Rt = 2.32 min; MS (ESIPos): m/z = 525 [M + H].sup.+ I-024 [00081] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.671 (5.91), 1.682 (5.87), 2.075 (0.98), 2.357 (16.00), 5.185 (1.03), 5.198 (1.33), 5.210 (1.00), 7.624 (5.27), 8.766 (2.20), 8.769 (2.25), 8.870 (2.09), 8.872 (2.02), 9.397 (1.64), 9.410 (1.56). LC-MS (Method 1): Rt = 2.33 min; MS (ESIpos): m/z = 559 [M + H].sup.+ I-025 [00082] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.643 (6.14), 1.655 (6.09), 2.337 (16.00), 5.992 (1.02), 6.003 (1.22), 6.016 (1.01), 7.545 (5.20), 7.832 (4.10), 8.060 (1.80), 8.074 (1.90), 8.467 (1.16), 8.471 (1.16), 8.481 (1.11), 8.485 (1.08), 8.958 (1.78), 9.247 (1.80), 9.260 (1.72). LC-MS (Method 1): R.sub.t = 2.38 min; MS (ESIpos): m/z = 491 [M + H].sup.+ I-026 [00083] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: −0.021 (0.91), 1.232 (1.78), 1.657 (16.00), 1.668 (15.89), 2.427 (0.46), 2.657 (0.41), 3.353 (0.50), 6.033 (2.02), 7.614 (6.83), 7.834 (7.01), 8.111 (5.75), 8.125 (6.13), 8.253 (12.11), 8.593 (4.11), 8.596 (4.08), 8.607 (3.91), 8.611 (3.89), 9.062 (6.37), 9.065 (6.16), 9.605 (3.20). LC-MS (Method 1): R.sub.t = 2.17 min; MS (ESIpos): m/z = 468 [M + H].sup.+ I-027 [00084] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: −0.021 (1.84), 0.005 (1.42), 1.230 (3.69), 1.672 (16.00), 1.684 (15.95), 6.002 (0.51), 6.013 (2.00), 6.025 (2.97), 6.037 (1.98), 6.048 (0.48), 7.443 (7.19), 7.476 (6.79), 8.119 (4.71), 8.133 (5.04), 8.247 (14.16), 8.511 (3.01), 8.515 (3.09), 8.526 (2.87), 8.529 (2.91), 8.991 (4.89), 9.430 (3.76), 9.442 (3.62). LC-MS (Method 1): R.sub.t = 2.41 min; MS (ESIpos): m/z = 477 [M + H].sup.+ I-028 [00085] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) .Math. [ppm]: 1.649 (6.04 ), 1.661 (5.97), 2.338 (16.00), 6.005 (0.92), 6.017 (1.22), 6.029 (0.91), 7.456 (2.76), 7.478 (2.63), 8.066 (1.81), 8.080 (1.91), 8.471 (1.16), 8.475 (1.16), 8.485 (1.11), 8.489 (1.08), 8.959 (1.80), 9.413 (1.78), 9.426 (1.68). LC-MS (Method 1): R.sub.t = 2.48 min; MS (ESIpos): m/z = 491 [M + H].sup.+ I-029 [00086] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.656 (5.96), 1.667 (5.97), 2.076 (1.21), 2.336 (16.00), 6.027 (0.78), 6.040 (1.11), 6.052 (0.76), 7.608 (2.30), 7.806 (2.37), 8.070 (1.78), 8.084 (1.88), 8.473 (1.16), 8.477 (1.15), 8.488 (1.08), 8.492 (1.07), 8.956 (1.73), 9.570 (1.43), 9.583 (1.37). LC-MS (Method 1): R.sub.t = 2.52 Min; MS (ESIpos): m/z = 525 [M + H].sup.+ I-30 [00087] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.005 (0.67), 1.168 (2.53), 1.180 (5.24), 1.191 (2.60), 1.397 (2.41), 1.683 (16.00), 1.695 (15.93), 1.994 (9.92), 4.016 (0.77), 4.029 (2.33), 4.040 (2.29), 4.052 (0.75), 6.028 (0.55), 6.039 (2.29), 6.051 (3.40), 6.063 (2.28), 6.074 (0.57), 7.604 (6.33), 7.795 (6.52), 8.125 (4.81), 8.140 (5.13), 8.248 (14.42), 8.514 (3.07), 8.518 (3.14), 8.528 (2.90), 8.532 (2.92), 8.983 (4.95), 9.592 (4.74), 9.604 (4.53). LC-MS (Method 1): Rt = 2.45 min; MS (ESIpos): m/z = 511 [M + H].sup.+ I-031 [00088] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.671 (16.00), 1.682 (15.97), 5.991 (0.66), 6.003 (2.58), 6.015 (3.73), 6.027 (2.57), 6.039 (0.67), 7.530 (12.17), 7.828 (10.25), 8.115 (4.99), 8.129 (5.31), 8.249 (12.43), 8.507 (3.37), 8.511 (3.49), 8.522 (3.24), 8.525 (3.25), 8.988 (6.01), 9.265 (4.71), 9.278 (4.58). LC-MS (Method 1): R.sub.t = 2.34 min; MS (ESIpos): m/z = 477 [M + H].sup.+ I-032 [00089] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.397 (0.63), 1.649 (15.96), 1.660 (16.00), 5.907 (0.60), 5.919 (2.49), 5.930 (3.70), 5.942 (2.42), 5.954 (0.60), 7.609 (7.05), 7.820 (7.31), 7.929 (6.44), 7.943 (7.06), 8.180 (13.41), 8.228 (4.26), 8.232 (4.16), 8.242 (3.86), 8.246 (3.77), 8.632 (6.49), 8.636 (6.26), 9.558 (4.69), 9.570 (4.55). LC-MS (Method 1): R.sub.t = 2.40 min; MS (ESIpos): m/z = 477 [M + H].sup.+ I-033 [00090] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.165 (1.10), 1.177 (2.22), 1.189 (1.11), 1.640 (6.09), 1.652 (6.06), 1.991 (4.19), 3.324 (16.00), 4.026 (0.99), 4.038 (0.98), 5.885 (0.95), 5.897 (1.32), 5.909 (0.95), 7.565 (4.88), 7.828 (3.73), 7.918 (2.42), 7.932 (2.67), 8.183 (5.28), 8.219 (1.67), 8.223 (1.68), 8.233 (1.50), 8.238 (1.54), 8.625 (2.36), 8.629 (2.33), 9.224 (1.75), 9.237 (1.68). LC-MS (Method 1): R.sub.t = 2.28 min; MS (ESIpos): m/z = 443 [M + H].sup.+ I-034 [00091] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.666 (15.96), 1.678 (16.00), 5.907 (0.58), 5.918 (2.33), 5.930 (3.43), 5.942 (2.30), 5.954 (0.58), 7.453 (7.55), 7.556 (7.61), 7.658 (3.74), 7.666 (7.45), 7.674 (3.88), 8.176 (12.70), 9.000 (14.34), 9.008 (14.18), 9.393 (4.31), 9.406 (4.16). LC-MS (Method 1): R.sub.t = 1.81 min; MS (ESIpos): m/z = 454 [M + H].sup.+

TABLE-US-00006 TABLE 2 Intermediates according to structure (b) Interme- diate Structure Analytics/NMR Peaklist.sup.[1] (b)-001 [00092] embedded image .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (0.93), 0.008 (0.93), 3.371 (16.00), 7.377 (0.67), 7.479 (0.64), 7.483 (0.67), 7.489 (0.95), 7.836 (1.33), 7.840 (1.37), 7.858 (1.74), 7.861 (1.77), 8.007 (2.58), 8.028 (2.03), 8.220 (2.53). (b)-002 [00093] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 2.423 (11.11), 2.497 (11.78), 2.500 (16.00), 2.503 (12.44), 2.511 (2.22), 2.515 (2.00), 2.605 (0.89), 2.616 (0.67), 2.652 (11.33), 7.636 (4.67), 7.650 (10.00), 7.663 (6.00), 7.794 (10.00), 7.807 (8.44), 8.117 (9.78), 8.131 (9.33). (b)-003 [00094] embedded image .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 2.428 (0.64), 2.580 (0.64), 2.617 (0.45), 2.657 (0.76), 3.327 (0.52), 3.391 (0.53), 8.222 (16.00), 8.640 (15.98). (b)-004 [00095] .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (1.11), 8.060 (15.98), 8.240 (16.00). (b)-005 [00096] .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 2.463 (16.00), 7.832 (4.23), 8.023 (5.39). (b)-006 [00097] embedded image .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (1.68), 0.008 (2.29), 1.231 (1.27), 1.249 (0.65), 1.266 (0.92), 1.283 (0.47), 2.525 (1.16), 3.149 (1.08), 3.154 (1.26), 3.626 (0.84), 7.872 (15.12), 7.875 (16.00), 8.045 (16.00), 8.048 (15.41). (b)-007 [00098] .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (1.32), 0.008 (1.33), 1.232 (0.52), 2.712 (0.43), 5.755 (3.73), 7.161 (0.61), 7.166 (0.65), 7.334 (0.45), 7.339 (0.44), 7.779 (14.75), 7.783 (16.00), 7.934 (15.74), 7.938 (15.24). (b)-008 [00099] embedded image GC-MS (Method 5) R.sup.1 = 4.11 min; MS (ESI) m/z = 300.9 [M.sup.+]. (b)-009 [00100] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 8.144 (16.00), 8.270 (15.79). (b)-010 [00101] .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (0.41), 0.008 (0.49), 1.107 (16.00), 3.077 (4.56), 3.162 (0.75), 7.965 (2.95), 7.967 (3.14), 8.301 (2.00), 8.305 (2.04). (b)-011 [00102] embedded image GC-MS (method 9) Rt = 4.80 min; MS (EI) m/z = 229 [M].sup.+. (b)-012 [00103] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 4.298 (0.44), 4.371 (0.47), 4.381 (0.43), 7.595 (0.96), 7.837 (0.82), 8.227 (16.00), 8.416 (15.80). (b)-013 [00104] GC-MS (method 9) Rt = 5.36 min; MS (EI) m/z = 227 [M].sup.+. (b)-014 [00105] embedded image GC-MS (method 9) Rt = 5.86 min; MS (EI) m/z = 233 [M].sup.+. (b)-015 [00106] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.331 (16.00), 7.580 (1.03), 7.583 (1.03), 7.714 (1.07), 7.717 (0.99). (b)-016 [00107] LC-MS (method 1): Rt = 2.35 min; MS (ESIpos): m/z = 260 [M + H].sup.+ (b)-017 [00108] embedded image LC-MS (method 1): Rt = 2.29 min; MS (ESIpos): m/z = 248 [M + H].sup.+ (b)-018 [00109] GC-MS (method 9) Rt = 3.17 min; MS (EI) m/z = 271 [M].sup.+. (b)-019 [00110] GC-MS (method 9) Rt = 3.92 min; MS (EI) m/z = 313 [M].sup.+. (b)-020 [00111] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.194 (0.45), 3.147 (2.46), 8.098 (9.29), 8.324 (16.00). (b)-021 [00112] embedded image .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.010 (0.91), 0.006 (1.04), 1.396 (4.42), 1.987 (0.48), 2.327 (0.50), 2.365 (0.70), 2.669 (0.51), 2.709 (0.72), 7.615 (6.00), 7.619 (2.47), 7.632 (15.79), 7.636 (8.19), 7.652 (11.27), 7.688 (3.67), 7.691 (6.53), 7.694 (3.77), 7.704 (2.59), 7.709 (7.97), 7.715 (1.76), 7.725 (1.61), 7.728 (2.45), 8.074 (11.05), 8.077 (16.00), 8.082 (3.74), 8.095 (12.80), 8.103 (1.41), 8.191 (12.89), 8.195 (12.82), 8.391 (12.99), 8.395 (12.18).

TABLE-US-00007 TABLE 3 (k) [00113] embedded image Intermediate Structure LC-MS.sup.[1] (k)-001 [00114] HPLC-MS (method 2) R.sub.t = 0.94 min; MS (ESIpos): m/z = 206 [M + H].sup.+ (k)-002 [00115] HPLC-MS (method 2) R.sub.t = 1.24 min; MS (ESIpos): m/z = 274 [M + H].sup.+ (k)-003 [00116] HPLC-MS (method 2) R.sub.t = 1.29 min; MS (ESIpos): m/z = 274 [M + H].sup.+ (k)-004 [00117] embedded image HPLC-MS (method 1) R.sub.t = 1.64 min; MS (ESIpos): m/z = 342 [M + H].sup.+ (k)-005 [00118] HPLC-MS (method 1) R.sub.t = 1.55 min; MS (ESIpos): m/z = 308 [M + H].sup.+ (k)-006 [00119] HPLC-MS (method 1) R.sub.t = 1.35 min; MS (ESIpos): m/z = 298 [M + H].sup.+ (k)-007 [00120] HPLC-MS (method 1) R.sub.t = 1.50 min; MS (ESIpos): m/z = 290 [M + H].sup.+ (k)-008 [00121] embedded image HPLC-MS (method 1) R.sub.t = 0.98 min, MS (ESIpos): m/z = 222 [M + H].sup.+ (k)-009 [00122] HPLC-MS (method 2) R.sub.t = 1.36 min; MS (ESIpos): m/z = 321 [M + H].sup.+ (k)-010 [00123] HPLC-MS (method 1) R.sub.t = 1.48 min; MS (ESIpos): m/z = 308 [M + H].sup.+ (k)-011 [00124] HPLC-MS (method 1) R.sub.t = 1.40 min; MS (ESIpos): m/z = 274 [M + H].sup.+ (k)-012 [00125] embedded image HPLC-MS (method 2) R.sub.t = 1.36 min; MS (ESIpos): m/z = 321 [M + H].sup.+ (k)-013 [00126] HPLC-MS (method 1) R.sub.t = 1.40 min; MS (ESIpos): m/z = 274 [M + H].sup.+ (k)-014 [00127] HPLC-MS (method 3): R.sub.t = 0.83 min; MS (ESIpos): m/z = 352 [M + H].sup.+ (k)-015 [00128] HPLC-MS (method 3): R.sub.t = 0.72 min; MS (ESIpos): m/z = 274 [M + H].sup.+ (k)-016 [00129] embedded image HPLC-MS (method 1) R.sub.t = 1.51 min; MS (ESIpos): m/z = 280 [M + H].sup.+ (k)-017 [00130] HPLC-MS (method 1) R.sub.t = 1.14 min; MS (ESIpos): m/z = 265 [M + H].sup.+ (k)-018 [00131] HPLC-MS (method 1) R.sub.t = 1.54 min; MS (ESIpos): m/z = 308 [M + H].sup.+ (k)-019 [00132] HPLC-MS (method 1) R.sub.t = 1.64 min; MS (ESIpos): m/z = 282 [M + H].sup.+ (k)-020 [00133] embedded image HPLC-MS (method 7) R.sub.t = 0.98 min; MS (ESIneg): m/z = 284 [M − H].sup.− (k)-021 [00134] HPLC-MS (method 1) R.sub.t = 1.74 min; MS (ESIpos): m/z = 296 [M + H].sup.+ (k)-022 [00135] HPLC-MS (method 1) R.sub.t = 1.56 min; MS (ESIpos): m/z = 312 [M + H].sup.+ (k)-023 [00136] HPLC-MS (method 1) R.sub.t = 1.48 min; MS (ESIpos): m/z = 300 [M + H].sup.+ (k)-024 [00137] embedded image HPLC-MS (method 1) R.sub.t = 1.59 min; MS (ESIpos): m/z = 324 [M + H].sup.+ (k)-025 [00138] HPLC-MS (method 1) R.sub.t = 1.66 min; MS (ESIpos): m/z = 366 [M + H].sup.+ (k)-026 [00139] HPLC-MS (method 1) R.sub.t = 1.53 min; MS (ESIpos): m/z = 324 [M + H].sup.+ (k)-027 [00140] HPLC-MS (method 1) R.sub.t = 1.41 min; MS (ESIpos): m/z = 380 [M + H].sup.+ (k)-28 [00141] embedded image LC-MS (method 7): R.sub.t = 0.90 min; MS (ESIneg): m/z = 306 [M − H].sup.− (k)-29 [00142] LC-MS (method 1): R.sub.t = 1.24 min; MS (ESIpos): m/z = 352 [M + H].sup.+ (k)-30 [00143] LC-MS (method 1): R.sub.t = 1.23 min; MS (ESIpos): m/z = 352 [M + H].sup.+ (k)-31 [00144] LC-MS (method 1): R.sub.t = 1.22 min; MS (ESIpos): m/z = 308 [M + H].sup.+ (k)-32 [00145] embedded image LC-MS (method 1): R.sub.t = 1.22 min; MS (ESIpos): m/z = 308 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.350 (15.92), 1.361 (16.00), 4.150 (1.31), 4.162 (1.94), 4.174 (1.26), 6.943 (2.36), 7.059 (1.44), 7.072 (1.39), 7.293 (2.36), 7.848 (8.53), 9.272 (7.46).

Synthesis of Intermediates According to Formulas (t), (u), (v)

Intermediate 4A

Ethyl {[4-chloro-5-(trifluoromethyl)pyridin-2-yl]carbamothioyl}carbamate

[0552] ##STR00146##

[0553] 4-Chloro-5-(trifluoromethyl)pyridin-2-amine (1.80 g, 9.16 mmol) was dissolved in 1,4-dioxane (20 mL), ethyl carbonisothiocyanatidate (1.3 mL, 11 mmol) was added and the mixture was stirred at 95° C. for 4 h. The solvent was removed by distillation and the residue was purified by flash chromatography on silica gel (eluent: gradient of cyclohexane with 0-60% dichloromethane). 3.00 g (98% purity, 97% yield) of the title compound were obtained.

[0554] LC-MS (method 1): R.sub.t=2.22 min; MS (ESIpos): m/z=328 [M+H].sup.+

[0555] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.261 (7.79), 1.273 (16.00), 1.285 (7.76), 1.398 (0.86), 4.229 (2.44), 4.240 (7.51), 4.252 (7.45), 4.264 (2.36), 8.828 (5.86), 9.049 (2.65), 11.941 (1.34), 12.450 (1.50).

Intermediate 5A, (t)-005

7-Chloro-6-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine

[0556] ##STR00147##

[0557] DIPEA (7.8 ml, 45 mmol) was added to a suspension of hydroxyl amine hydrochloride (3.13 g, 45.0 mmol) in a mixture of ethanol and methanol (1:1, 91 mL). This mixture was stirred at room temperature for 30 min, then ethyl {[4-chloro-5-(trifluoromethyl)pyridin-2-yl]carbamothioyl}carbamate (intermediate 4A, 2.95 g, 9.00 mmol) was added and the mixture was heated slowly to reflux. After 90 min at reflux, the solvents were distilled and the residue was mixed with water (100 mL). The solid precipitate was isolated by suction and dried under vacuum to give 2.11 g (94% purity, 93% yield) of the title compound.

[0558] Analytic data see table 4.

TABLE-US-00008 TABLE 4 Intermediates according to structure (t) (t) [00148] embedded image Interme- diate Structure Analytics/NMR (Peaklist.sup.[1] (t)-001 [00149] LC-MS (method 1): R.sub.t = 1.21 min; MS (ESIpos): m/z = 237 [M + H].sup.+ (t)-002 [00150] LC-MS (method 1): R.sub.t = 1.31 min; MS (ESIpos): m/z = 281 [M + H].sup.+ (t)-003 [00151] LC-MS (method 1): R.sub.t = 1.27 min; MS (ESIpos): m/z = 281 [M + H].sup.+ (t)-004 [00152] embedded image LC-MS (method 1): R.sub.t = 1.28 min; MS (ESIpos): m/z = 237 [M + H].sup.+ (t)-005 [00153] LC-MS (method 1): R.sub.t = 1.28 min; MS (ESIpos): m/z = 237 [M + H].sup.+ .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.030 (0.51), 1.043 (0.46), 1.257 (0.63), 6.511 (14.27), 7.782 (16.00), 9.194 (14.47).

Intermediate 6A, (u)-005

Ethyl N-[7-chloro-6-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-DL-alaninate

[0559] ##STR00154##

[0560] 7-Chloro-6-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine (intermediate 5A, 473 mg, 2.00 mmol) was dissolved in DMF (20 mL), cesium carbonate (2.61 g, 8.00 mmol) and (rac) ethyl 2-bromopropanoate were added and the mixture was heated to 60° C. for 16 h. The mixture was filtered and the filtrate was charged upon a prep HPLC device and chromatographed (RP C-18 10 μm, acetonitrile/water+0.1% TFA 10:90->95:5) 336 mg (100% purity, 50% yield) of the title compound were isolated.

[0561] Analytical data see table 5.

TABLE-US-00009 TABLE 5 Intermediates according to structure (u) (u) [00155] embedded image Interme- diate Structure Analytics/NMR Peaklist.sup.[1] (u)-001 [00156] LC-MS (method 7): R.sub.t = 1.26 min; MS (ESIpos): m/z = 337 [M + H].sup.+ (u)-002 [00157] LC-MS (method 1): R.sub.t = 1.88 min; MS (ESIpos): m/z = 381 [M + H].sup.+ (u)-003 [00158] LC-MS (method 1): R.sub.t = 1.91 min; MS (ESIpos): m/z = 381 [M + H].sup.+ (u)-004 [00159] embedded image LC-MS (method 1): R.sub.t = 1.85 min; MS (ESIpos): m/z = 337 [M + H].sup.+ (u)-005 [00160] LC-MS (method 3): R.sub.t = 0.93 min; MS (ESIpos): m/z = 337 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.106 (2.02), 1.148 (4.32), 1.165 (9.03), 1.183 (4.50), 1.196 (1.01), 1.204 (0.47), 1.214 (0.50), 1.370 (0.40), 1.411 (6.27), 1.430 (6.22), 1.441 (0.85), 3.077 (0.56), 3.353 (16.00), 4.038 (0.63), 4.048 (0.65), 4.056 (0.70), 4.065 (1.83), 4.070 (0.81), 4.083 (1.92), 4.088 (1.96), 4.101 (0.81), 4.105 (1.87), 4.115 (0.70), 4.123 (0.74), 4.132 (0.65), 4.275 (0.70), 4.293 (0.96), 4.312 (0.64), 7.557 (0.89), 7.577 (0.84), 7.881 (2.08), 9.309 (2.55).

Intermediate 7A, (v)-005

N-[7-chloro-6-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-DL-alanine

[0562] ##STR00161##

[0563] Ethyl N-[7-chloro-6-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-DL-alaninate (336 mg, 998 μmol) was dissolved in ethanol (20 mL), an aqueous solution of lithium hydroxide (3.0 ml, 1.0 M, 3.0 mmol) was added and the mixture was stirred at room temperature for 30 min. The solution was acidified with 1 M hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to give 324 mg (97% purity, quant) of the title compound.

[0564] Analytical data see table 6.

TABLE-US-00010 TABLE 6 Intermediates according to structure (v) (v) [00162] embedded image Interme- diate Structure Analytics/NMR Peaklist.sup.[1] (v)-001 [00163] LC-MS (method 7): R.sub.t = 1.00 min; MS (ESIneg): m/z = 307 [M − H].sup.− (v)-002 [00164] LC-MS (method 1): R.sub.t = 1.43 min; MS (ESIpos): m/z = 353 [M + H].sup.+ (v)-003 [00165] LC-MS (method 1): R.sub.t = 1.42 min; MS (ESIpos): m/z = 353 [M + H].sup.+ (v)-004 [00166] embedded image LC-MS (method 1): R.sub.t = 1.39 min; MS (ESIpos): m/z = 309 [M + H].sup.+ (v)-005 [00167] LC-MS (method 1): R.sub.t = 1.39 min; MS (ESIpos): m/z = 309 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.164 (4.03), 1.176 (8.04), 1.188 (4.16), 1.206 (0.51), 1.218 (0.66), 1.229 (2.15), 1.240 (2.09), 1.392 (0.60), 1.405 (0.99), 1.414 (15.92), 1.427 (16.00), 1.909 (0.81), 1.987 (15.42), 4.014 (1.28), 4.026 (3.86), 4.038 (4.00), 4.049 (1.46), 4.221 (1.23), 4.232 (1.71), 4.243 (1.21), 7.385 (1.22), 7.396 (1.20), 7.859 (9.46), 9.294 (8.70).

Intermediate 8A, (k)-32

N.SUP.2.-[7-chloro-6-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-DL-alaninamide

[0565] ##STR00168##

[0566] N-[7-chloro-6-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-DL-alanine (309 mg, 1.00 mmol) was dissolved in DMF (5.5 mL). Ammonium chloride (107 mg, 2.00 mmol), HATU (570 mg, 1.50 mmol) and eventually DIPEA (520 μL, 3.0 mmol) were added and the mixture was stirred at ambient temperature. The crude mixture was directly charged upon a preparative HPLC device and chromatographed (RP C-18 10 μm acetonitrile/water+0.1% TFA 10:90->95:5) to give 230 mg (100% purity, 75% yield) of the title compound.

[0567] Analytical data see table 3.

Synthesis of Starting Materials According to Structure (f)

[0568] Most compounds according to structure (f) (see scheme 3) are commercially available or described in the literature.

##STR00169##

[0569] In some cases these intermediates had to be prepared. Procedures are given in the following.

Intermediate 9A

2-Chloro-6-nitro-4-(pentafluoro-lambda.SUP.6.-sulfanyl)phenol

[0570] ##STR00170##

[0571] 2-Chloro-4-(pentafluoro-lambda.sup.6-sulfanyl)phenol (910 mg, 3.57 mmol) was dissolved in glacial acetic acid (16 mL). The mixture was heated to 50° C. and sodium nitrite (493 mg, 7.15 mmol) was added. The mixture was heated to 60° C. over night. After cooling to RT, the mixture was diluted with water and extracted with ethyl acetate. The organic extract was filtered, dried and evaporated. The crude material (1.15 g, 88% purity, 94% yield) was used directly in the next step.

[0572] LC-MS (method 1): R.sub.t=1.89 min; MS (ESIneg): m/z=300 [M−H].sup.−

[0573] .sup.1H NMR (600 MHz, DMSO-d6) δ [ppm]: 1.236 (0.46), 2.380 (0.64), 2.569 (1.94), 4.406 (1.58), 7.105 (0.64), 7.120 (0.68), 7.697 (0.77), 7.702 (0.65), 7.712 (0.58), 7.717 (0.61), 7.889 (1.18), 7.894 (1.14), 7.982 (1.99), 8.076 (1.59), 8.081 (1.57), 8.312 (9.48), 8.315 (10.32), 8.317 (12.80), 8.319 (11.45), 8.358 (16.00), 8.363 (13.49), 8.513 (1.36), 8.518 (1.34).

Intermediate 10A

2-Amino-6-chloro-4-(pentafluoro-lambda.SUP.6.-sulfanyl)phenol

[0574] ##STR00171##

[0575] 2-Chloro-6-nitro-4-(pentafluoro-lambda.sup.6-sulfanyl)phenol (intermediate 9A, 910 mg, 3.04 mmol) was dissolved in ethanol (10 mL) and hydrogenated for 4 h in the presence of Raney-Nickel (17.8 mg, 304 μmot) at ambient pressure and room temperature. The catalyst was then filtered off and the filtrate was evaporated. The crude product was eventually purified by preparative HPLC (RP C-18 phase with a gradient of water, acetonitrile with 0.1% ammonia) to give 655 mg (80% yield) of the title compound.

[0576] LC-MS (method 1): R.sub.t=1.71 min; MS (ESIneg): m/z=268 [M−H].sup.−

[0577] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 2.140 (0.42), 3.722 (1.55), 7.013 (13.72), 7.018 (14.76), 7.091 (16.00), 7.095 (13.83).

Intermediate 11A

Cyclopropanethiol

[0578] ##STR00172##

[0579] To a solution of Cyclopropyl magnesium bromide (1.00 M, 700 mL, 1.00 eq) in THF was added sulfur (22.5 g, 700 mmol, 1.00 eq) at 0° C. in portions slowly. The mixture was stirred at 50° C. for 3 hr. Then lithium aluminium hydride (13.3 g, 350 mmol, 0.50 eq) was added at 0° C. in portions. The mixture was stirred at 65° C. for 1 hr. The mixture was quenched by addition H.sub.2O (100 mL) slowly at 0° C. 400 mL of 5% sulfuric acid were added and the mixture was extracted with MTBE (3×150 mL) and the combined organic phase were dried over sodium sulfate, filtered and the crude product (51.9 g) was used in the next step without further purification.

Intermediate 12A

4-Chloro-5-(cyclopropylsulfanyl)-2-nitrophenol

[0580] ##STR00173##

[0581] To a solution of intermediate 11A (51.9 g, 700 mmol) in MTBE (450 ml), sodium hydride (25.1 g, 626 mmol, 60% in mineral oil, 2.00 eq) was added. The mixture was stirred at 0° C. for 30 min. Then a solution of 4-chloro-5-fluoro-2-nitrophenol (60.0 g, 313 mmol) in THF (120 mL) was added drop-wise at 0° C. The mixture was stirred at 45° C. for 11.5 hr. The reaction mixture was quenched by addition of water (500 mL), then extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (200 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by recrystallization from MTBE (100 mL) at 25° C. to give the title compound (60.0 g, 244 mmol, 78% yield) as yellow solid.

[0582] .sup.1H NMR: (400 MHz, DMSO-d.sub.6) δ 11.35 (br s, 1H), 7.99 (s, 1H), 7.39 (s, 1H), 2.31-2.25 (m, 1H), 1.26-1.19 (m, 2H), 0.74-0.66 (m, 2H).

Intermediate 13A

4-Chloro-5-(cyclopropylsulfonyl)-2-nitrophenol

[0583] ##STR00174##

[0584] To a solution of intermediate 12A (40.0 g, 163 mmol, 1.00 eq) in methanol (300 mL) and water (100 mL), potassium peroxomonosulfate (Oxon®, 500 g, 814 mmol) was added slowly at 0° C. The mixture was stirred at 25° C. for 16 h. The reaction mixture was quenched by addition of saturated sodium sulfite solution (600 mL), then it was filtered and the filtrate was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (200 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The crude product title compound (40.0 g, 144 mmol, 89% yield) was obtained as a yellow solid and used in the next step without further purification.

Intermediate 14A

2-Amino-4-chloro-5-(cyclopropylsulfonyl)phenol

[0585] ##STR00175##

[0586] To a solution of intermediate 13A (40.0 g, 144 mmol) in ethanol (400 mL), tin(II)chloride dihydrate (97.5 g, 432 mmol) was added. The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, and aqueous sodium hydrogen carbonate was added to adjust the pH to 8-9. The mixture was then extracted with ethyl acetate (3×200 mL). The combined organic layers were concentrated in vacuo. The crude product was triturated with dichloromethane (100 mL) at 25° C. for 30 min, then filtered and the filter cake was obtained as product. (14.00 g, 33.7 mmol, 39% yield, 99% purity) as grey solid.

[0587] .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ=9.93 (s, 1H), 7.17 (s, 1H), 6.74 (s, 1H), 5.77 (s, 2H), 3.03-2.80 (m, 1H), 1.01 (d, J=6.4 Hz, 4H)

Intermediate 15A

2-amino-4-chloro-5-(cyclopropylsulfanyl)phenol

[0588] ##STR00176##

[0589] To a solution of 12A (20.0 g, 81.4 mmol, 1.00 eq) in EtOH (200 mL) tin(II)chloride dihydrate (55.1 g, 244 mmol) was added. The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature and aqueous sodium hydrogen carbonate was added to adjust the system pH to 8-9. The mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were concentrated in vacuo. The mixture was cooled to room temperature and then filtered, and the filtrate was concentrated under reduce pressure with rotary-evaporator. The crude product was triturated with dichloromethane (100 mL) at 25° C. for 30 min, then filtered and the filter cake was obtained as product (10.0 g, 45.9 mmol, 56% yield, 99.0% purity) as grey solid.

[0590] .sup.1H NMR (400 MHz, DMSO-d6) δ 9.43 (br s, 1H), 6.95-6.91 (m, 1H), 6.66 (s, 1H), 4.80 (br s, 2H), 2.12 (tt, J=4.3, 7.4 Hz, 1H), 1.00-0.94 (m, 2H), 0.59-0.53 (m, 2H)

Intermediate 16A

4-Chloro-5-(methylsulfanyl)-2-nitrophenol

[0591] ##STR00177##

[0592] To a solution of 4-chloro-5-fluoro-2-nitrophenol (30.0 g, 157 mmol) in methanol (300 mL), sodium methylsulfide (110 g, 313 mmol, 100 mL) was slowly added at 0° C. The mixture was stirred at 80° C. for 3 h. The reaction mixture was concentrated under reduced pressure to give crude product. The crude product was purified by re-crystallization from dichloromethane (100 mL) at 25° C. to give the title compound (40.0 g, crude) as red solid which was used in the next step without further purification.

[0593] .sup.1H NMR: (400 MHz, DMSO-d6) δ 7.71 (s, 1H), 6.17 (s, 1H), 2.33 (s, 3H).

Intermediate 17A

4-Chloro-5-(methylsulfonyl)-2-nitrophenol

[0594] ##STR00178##

[0595] To a solution of 4-chloro-5-(methylsulfanyl)-2-nitrophenol (intermediate 16A, 20.0 g, 91.1 mmol) in methanol (300 mL) and water (100 mL), potassium peroxomonosulfate (Oxone®, 140 g, 228 mmol) was slowly added at 0° C. The mixture was stirred at 25° C. for 16 h. The reaction mixture was quenched by addition of saturated sodium sulfite solution (300 mL). Then it was filtered, and the filtrate was extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine (200 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude title compound (15.0 g, 59.6 mmol, 66% yield) which was used in the next step without further purification.

[0596] .sup.1H NMR: δ 10.44 (s, 1H), 8.32 (s, 1H), 8.04 (s, 1H), 3.32 (s, 3H).

Intermediate 18A

2-Amino-4-chloro-5-(methylsulfonyl)phenol

[0597] ##STR00179##

[0598] To a solution of 4-chloro-5-(methylsulfonyl)-2-nitrophenol (intermediate 17A, 15.0 g, 59.6 mmol) in ethanol (150 mL), tin(II)chloride dihydrate (40.4 g, 179 mmol) was added. The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, and aqueous sodium hydrogen carbonate was added to adjust the system pH to 8-9. Then it was extracted with ethyl acetate (3×50.0 mL). The combined organic layers were concentrated under vacuum. The crude product was triturated with DCM (30.0 mL) and MeOH (5.00 mL) at 25° C. for 30 min. The title compound (5.00 g, 24.4 mmol, 41% yield, 96.5% purity) was obtained as grey solid.

[0599] .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.97 (br s, 1H), 7.26 (s, 1H), 6.72 (s, 1H), 5.78 (s, 2H), 3.17 (s, 3H).

Intermediate 19A

2-Amino-4-chloro-5-(methylsulfanyl)phenol

[0600] ##STR00180##

[0601] To a solution of 4-Chloro-5-(methylsulfanyl)-2-nitrophenol (20.0 g, 91.1 mmol) in ethanol (200 mL), tin(II)chloride dihydrate (61.6 g, 273 mmol) was added. The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, and aqueous sodium hydrogen carbonate was added to adjust the system pH to 8-9. Then it was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over anhydrous sodium sulfate and then evaporated. The crude product was triturated with ethanol (20.0 mL) at 62° C. for 30 min, then cooled to 25° C. The title compound precipitated as a white solid (5.00 g, 25.6 mmol, 28% yield, 97.0% purity).

[0602] .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.42 (br s, 1H), 6.69 (s, 1H), 6.66 (s, 1H), 4.83 (br s, 2H), 2.31 (s, 3H)

Intermediate 20A

4-Chloro-5-(ethylsulfanyl)-2-nitrophenol

[0603] ##STR00181##

[0604] To a solution of 4-chloro-5-fluoro-2-nitrophenol (30.0 g, 157 mmol) in methanol (300 mL), sodium ethylsulfide (43.9 g, 522 mmol) was slowly added at 0° C. The mixture was stirred at 80° C. for 12 h. The reaction mixture was concentrated under reduced pressure to give the crude product. The crude product was purified by triturated with dichloromethane (100 mL) at 25° C. to give the title compound (50.0 g, crude) as red solid which was used in the next step without further purification.

[0605] .sup.1H NMR: (400 MHz, DMSO-d.sub.6) δ 7.71 (s, 1H), 6.24 (s, 1H), 3.44 (q, J=6.9 Hz, 2H), 1.27 (t, J=7.3 Hz, 3H).

Intermediate 21A

4-Chloro-5-(ethylsulfonyl)-2-nitrophenol

[0606] ##STR00182##

[0607] To a solution of 4-chloro-5-(ethylsulfanyl)-2-nitrophenol (intermediate 20A, 30.0 g, 129 mmol) in methanol (300 mL) and water (100 mL), potassium peroxomonosulfate (Oxone®, 197 g, 321 mmol) was slowly added at 0° C. The mixture was stirred at 25° C. for 16 h. The reaction mixture was quenched by addition of saturated sodium sulfite solution (300 mL). Then it was filtered, and the filtrate was extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine (200 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the title compound (30 g, crude) which was used in the next step without further purification.

[0608] .sup.1H NMR: δ 8.17 (s, 1H), 7.67 (s, 1H), 3.51 (q, J=7.4 Hz, 2H), 1.15 (t, J=7.4 Hz, 3H).

Intermediate 22A

2-Amino-4-chloro-5-(ethylsulfonyl)phenol

[0609] ##STR00183##

[0610] To a solution of 4-chloro-5-(ethylsulfonyl)-2-nitrophenol (intermediate 21A, 30.0 g, 113 mmol) in ethanol (300 mL), tin(II)chloride dihydrate (76.4 g, 339 mmol) was added. The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, and aqueous sodium hydrogen carbonate was added to adjust the system pH to 8-9. Then it was extracted with ethyl acetate (3×50.0 mL). The combined organic layers were concentrated under vacuum. The crude product was purified by preparative HPLC (RP-18 column, water-acetonitrile gradient with 0.1% conc hydrochloric acid) to obtain the title compound (5.00 g, 24.4 mmol, 41% yield, 97% purity) as grey solid.

[0611] .sup.1HNMR (400 MHz, DMSO-d6) δ 9.94 (br s, 1H), 7.23 (s, 1H), 6.73 (s, 1H), 5.78 (s, 2H), 3.28 (q, J=7.4 Hz, 2H), 1.07 (t, J=7.4 Hz, 3H).

Intermediate 23A

2-Amino-4-chloro-5-(ethylsulfanyl)phenol

[0612] ##STR00184##

[0613] To a solution of 4-Chloro-5-(ethylsulfanyl)-2-nitrophenol (intermediate 20A, 20.0 g, 85.6 mmol) in ethanol (200 mL), tin(II)chloride dihydrate (57.9 g, 257 mmol) was added. The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, and aqueous sodium hydrogen carbonate was added to adjust the system pH to 8-9. Then it was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over anhydrous sodium sulfate and then evaporated. The crude product was triturated with dichloromethane (50.0 mL) at 25° C. for 30 min, then cooled to 25° C. and eventually filtered. The filter cake contained the title compound (7.00 g, 33.7 mmol, 39% yield, 98.0% purity) as a grey solid.

[0614] .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 9.41 (br s, 1H), 6.78 (s, 1H), 6.67 (s, 1H), 4.93 (br s, 2H), 2.73 (q, J=7.3 Hz, 2H), 1.14 (t, J=7.3 Hz, 3H).

Intermediate 24A

2-Chloro-4-cyclopropyl-6-nitrophenol

[0615] ##STR00185##

[0616] 2-Chloro-4-cyclopropylphenol (1.53 g, 9.07 mmol) was dissolved in glacial acetic acid (23 mL) at RT, sodium nitrite (1.25 g, 18.1 mmol) was added in small portions over 2 h. The reaction was concentrated under vacuum, the residue was diluted with ethyl acetate, washed with water (50 mL) and brine (50 mL), dried over sodium sulfate filtered and evaporated. The crude material was purified over silica gel (cyclohexane-ethyl acetate gradient) to provide 794 mg (88% purity, 36% yield) of the title compound.

[0617] LC-MS (method 1): R.sub.t=1.99 min; MS (ESIneg): m/z=212 [M−H].sup.−

[0618] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.700 (4.18), 0.708 (14.97), 0.711 (12.32), 0.716 (13.12), 0.719 (13.99), 0.727 (4.89), 0.743 (0.42), 0.841 (1.05), 0.844 (1.23), 0.849 (1.21), 0.859 (0.79), 0.903 (0.44), 0.917 (0.56), 0.928 (4.68), 0.936 (11.66), 0.939 (11.92), 0.942 (5.63), 0.950 (11.90), 0.953 (11.42), 0.961 (3.88), 1.003 (0.77), 1.007 (0.74), 1.017 (0.80), 1.021 (0.71), 1.959 (1.83), 1.967 (3.63), 1.973 (3.86), 1.981 (6.84), 1.990 (3.73), 1.995 (3.30), 2.004 (1.54), 2.039 (0.44), 6.032 (0.49), 7.282 (0.97), 7.285 (1.12), 7.322 (1.06), 7.326 (0.92), 7.371 (0.58), 7.374 (0.55), 7.525 (15.03), 7.529 (16.00), 7.622 (15.85), 7.626 (14.44), 10.735 (2.00).

Intermediate 25A

2-Amino-6-chloro-4-cyclopropylphenol

[0619] ##STR00186##

[0620] 2-Chloro-4-cyclopropyl-6-nitrophenol (intermediate 24A, 1.43 g, 6.71 mmol) was dissolved in ethanol (130 mL) and hydrogenated at room temperature and ambient pressure in the presence of Raney-nickel (17.8 mg, 304 μmol) for 2.5 h. The catalyst was removed by filtration over a pad of celite and the crude product was chromatographed over silica gel (cyclohexane-ethyl acetate gradient) to give 1.07 g (100% purity, 87% yield) of the title compound.

[0621] LC-MS (method 1): R.sub.t=1.39 min; MS (ESIpos): m/z=184 [M+H].sup.+

[0622] .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 0.467 (3.75), 0.478 (11.44), 0.483 (10.51), 0.490 (11.45), 0.495 (11.06), 0.506 (4.42), 0.782 (4.19), 0.792 (9.75), 0.797 (10.71), 0.803 (5.13), 0.808 (4.54), 0.813 (10.60), 0.818 (10.28), 0.829 (3.92), 1.157 (1.64), 1.175 (3.36), 1.192 (1.70), 1.655 (1.40), 1.668 (2.78), 1.677 (2.86), 1.681 (1.76), 1.689 (5.21), 1.698 (1.74), 1.702 (2.71), 1.710 (2.56), 1.723 (1.21), 1.988 (5.79), 4.002 (0.44), 4.021 (1.33), 4.038 (1.34), 4.056 (0.44), 4.798 (0.65), 6.251 (9.22), 6.257 (14.40), 6.274 (16.00), 6.279 (10.34).

[0623] In analogy to intermediates 32A and 33A, the following intermediates were synthesized:

Intermediate 26A

4-(Benzenesulfonyl)-2-chloro-6-nitrophenol

[0624] ##STR00187##

[0625] LC-MS (method 1): R.sub.t=1.48 min; MS (ESIneg): m/z=312 [M−H].sup.−

[0626] .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 2.384 (0.53), 2.423 (0.75), 2.612 (0.56), 2.652 (0.68), 7.561 (5.26), 7.573 (15.32), 7.577 (16.00), 7.582 (13.79), 7.586 (11.90), 7.608 (5.96), 7.620 (7.49), 7.632 (2.11), 7.864 (14.21), 7.877 (13.41), 8.129 (11.27), 8.133 (10.96).

Intermediate 27A

2-Amino-4-(benzenesulfonyl)-6-chlorophenol

[0627] ##STR00188##

[0628] LC-MS method 1): R.sub.t=1.38 min; MS (ESIpos): m/z=284 [M+H].sup.+

[0629] .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.042 (3.54), 1.056 (7.00), 1.070 (3.52), 3.420 (2.62), 3.434 (5.21), 3.448 (5.19), 3.462 (2.69), 3.851 (0.43), 6.663 (8.68), 6.668 (8.73), 6.969 (7.71), 6.975 (7.28), 7.310 (0.42), 7.462 (0.47), 7.491 (1.40), 7.498 (2.13), 7.508 (8.37), 7.523 (16.00), 7.533 (3.25), 7.546 (0.87), 7.574 (0.56), 7.587 (0.67), 7.728 (8.01), 7.732 (7.15), 7.744 (7.36), 7.747 (6.13).

Synthesis of Carboxylic Acid Derivatives

Example I-120

tert-Butyl 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H-1,2,4-triazol-1-yl}pyridine-3-carboxylate

[0630] ##STR00189##

[0631] N.sup.2-[6-Chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]-L-alaninamide (intermediate 3A, 500 mg, 1.63 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (540 μl, 4.1 mmol) were dissolved in dichloromethane (10.0 mL) and heated to reflux for 30 min. The solvent was distilled, the residue was taken up into a mixture of 1,4-dioxane (10.0 mL) and acetic acid (2.0 ml, 34 mmol) and tert-butyl 6-hydrazinylpyridine-3-carboxylate (CAS RN 163213-19-2, 680 mg, 3.25 mmol) was added. This mixture was heated to 60° C. for 1 h, then cooled, poured into saturated aqueous sodium carbonate solution and basified with 1M sodium hydroxide and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, evaporated and eventually purified by preparative HPLC (RP C-18 phase with a gradient of water, acetonitrile with 0.1% ammonia) to give 760 mg (100% purity, 92% yield) of the title compound. Analytical data see table 7.

Example I-121

6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H-1,2,4-triazol-1-yl}pyridine-3-carboxylic acid

[0632] ##STR00190##

[0633] tert-Butyl 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H-1,2,4-triazol-1-yl}pyridine-3-carboxylate (intermediate 16A, 760 mg, 100% purity, 1.49 mmol) was dissolved in 1,4-dioxane (1.0 mL) and cooled to 0° C., 4 M hydrochloric acid in 1,4-dioxane (7.4 mL, 30 mmol) and 1 M aqueous hydrochloric acid (1.5 mL, 1.5 mmol) were added slowly and stirring was maintained over night. Then the mixture was poured into water. The precipitate was filtered and dried under vacuum to give 542 mg (98% purity, 78% yield) of the title compound. For analytical data, see table 7.

Example I-110

6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H-1,2,4-triazol-1-yl}-N-ethylpyridine-3-carboxamide

[0634] ##STR00191##

[0635] 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H-1,2,4-triazol-1-yl}pyridine-3-carboxylic acid (intermediate 17A, 120 mg, 265 μmot) was dissolved in DMF (2.4 mL). The mixture was cooled to 0° C. on an ice bath, then HATU (151 mg, 398 μmot) and ethanamine (2 M in THF, 400 μl, 800 μmot) were added. The mixture was stirred at ambient temperature over night. Then another portion of HATU (151 mg, 398 μmot) and ethanamine (2 M in THF, 400 μl, 800 μmot) were added, the mixture was heated to 60° C. on a heating block for 5 h. The mixture was poured into water and extracted with ethyl acetate. The organic extract was dried over a Chromabond PTL cartridge, evaporated and the crude product was purified by preparative HPLC (RP C-18 phase with a gradient of water, acetonitrile with 0.1% ammonia) to give 49.0 mg (100% purity, 39% yield) of the title compound. For analytical data, see table 7.

Example I-56

6-Chloro-N-[(1S)-1-{1-[5-(oxetan-3-yl)pyrimidin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]-5-(trifluoromethyl)-1,3-benzoxazol-2-amine

[0636] ##STR00192##

[0637] N-{(1S)-1-[1-(5-bromopyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-amine (example I-62, 50.0 mg, 102 μmot) and) Ir(4′,6′-dF5-CF3-ppy)2(4,4′-dtbbpy)PF6) (CAS RN 870987-63-6, 2.30 mg, 2.1 μmot) were put into a 5 mL microwave vial which was then sealed (vial A). In another 5 mL vial, werden nickel(II)chloride dimethoxyethane complex (1.1 mg, 5.1 μmot) and 4,4′-di-tert-butyl-2,2′-bipyridine (1.4 mg, 5.1 μmot) were dissolved in 1,2-dimethoxyethane (2.0 mL) and stirred for 5 min. The solution was transferred to vial A, tris-trimethylsilane (25 mg, 102 μmot), 2,6-dimethylpyridine (36 μl, 310 μmot and 3-bromooxetane (63 mg, 460 μmot) were added. The vial was placed in a Blue Box with one 34 W Kessil light and the mixture was irradiated over night. Then, the vial was opened and the reaction mixture was diluted with a 1:1 mixture of water and conc. Sodium hydrogen carbonate. It was extracted with 3 portions of ethyl acetate, the combined extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated. The crude product was purified by preparative HPLC (RP-C18, water acetonitrile gradient) to give the title compound (11.0 mg, 22% yield). For analytics, see table 7.

TABLE-US-00011 TABLE 7 Structure IUPAC-Name LC-MS (method): Retention time; Mass found Example .sup.1H-NMR I-035 [00193] embedded image N-{(1S)-1-[1-(5-bromo-1,3-thiazol-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7-chloro- 5-(trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 3): R.sub.t = 1.18 min; MS (ESIpos): m/z = 492.9 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.656 (6.16), 1.668 (6.31), 1.681 (16.00), 1.692 (15.90), 2.072 (15.27), 5.941 (0.91), 5.953 (1.39), 5.965 (0.89), 5.981 (0.58), 5.993 (2.24), 6.004 (3.42), 6.016 (2.24), 6.027 (0.53), 7.554 (11.03), 7.653 (4.88), 7.761 (6.00), 7.766 (9.21), 7.788 (11.22), 7.794 (7.50), 8.210 (4.59), 8.226 (11.92), 9.584 (1.50), 9.596 (1.44), 9.685 (4.00), 9.697 (3.85). I-036 [00194] embedded image 7-chloro-N-{(1S)-1-[1-(5-chloropyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 1): R.sub.t = 1.99 min; MS (ESIpos): m/z = 444 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.661 (9.02), 1.672 (9.03), 5.873 (1.44), 5.885 (2.10), 5.897 (1.42), 7.424 (4.21), 7.484 (4.22), 8.204 (7.29), 9.140 (16.00), 9.406 (2.69), 9.419 (2.60). I-037 [00195] embedded image 7-chloro-N-{(1S)-1-[1-(4-ethoxypyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 1): R.sub.t = 2.10 min; MS (ESIpos): m/z = 454 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.338 (7.74), 1.350 (16.00), 1.362 (7.88), 1.679 (12.18), 1.690 (12.15), 3.645 (1.83), 4.426 (1.08), 4.432 (1.03), 4.439 (1.18), 4.444 (3.09), 4.449 (1.48), 4.456 (3.17), 4.461 (3.21), 4.467 (1.44), 4.473 (3.09), 4.478 (1.19), 4.485 (1.01), 4.490 (1.05), 5.930 (0.44), 5.942 (1.85), 5.954 (2.75), 5.966 (1.86), 5.977 (0.45), 7.038 (5.58), 7.047 (5.70), 7.438 (6.00), 7.481 (5.97), 8.147 (9.93), 8.653 (5.47), 8.662 (5.40), 9.407 (3.60), 9.420 (3.49). I-038 [00196] embedded image 7-chloro-N-{(1S)-1-[1-(4-methyl-1,3-thiazol-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}- 5-(trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 3): R.sub.t = 1.21 min; MS (ESIpos): m/z = 429 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.230 (0.67), 1.665 (8.84), 1.677 (8.85), 2.078 (0.71), 2.258 (16.00), 5.875 (1.43), 5.887 (2.13), 5.899 (1.41), 7.290 (4.81), 7.499 (4.47), 7.552 (4.62), 8.192 (6.60), 9.424 (2.49), 9.437 (2.42). I-039 [00197] embedded image 7-chloro-N-{(1S)-1-[1-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 1): R.sub.t = 1.96 min; MS (ESIpos): m/z = 410 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.683 (16.00), 1.694 (15.99), 2.091 (2.57), 2.559 (8.53), 3.693 (0.41), 5.860 (0.64), 5.871 (2.56), 5.883 (3.84), 5.895 (2.53), 5.906 (0.63), 7.441 (8.69), 7.471 (8.58), 8.276 (12.15), 8.660 (6.67), 8.796 (7.29), 8.800 (6.64), 9.213 (9.66), 9.432 (4.85), 9.444 (4.70). I-040 [00198] embedded image 7-Chlor-N-{(1S)-1-[1-(5-methylpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.90 min; MS (ESIpos): m/z = 424 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.652 (8.67), 1.664 (8.62), 2.354 (16.00), 5.856 (1.31), 5.868 (1.82), 5.880 (1.27), 7.431 (3.68), 7.465 (3.63), 8.138 (6.99), 8.827 (10.12), 9.338 (2.22), 9.351 (2.14). I-041 [00199] embedded image 5-{5-[(1S)-1-{[7-Chlor-5-(trifluormethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H- 1,2,4-triazol-1-yl}pyrazin-2-carbonitril LC-MS (method 1): R.sub.t = 2.07 min; MS (ESIpos): m/z = 435 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.653 (15.59), 1.665 (16.00), 2.069 (0.48), 5.743 (0.64), 5.911 (0.57), 5.923 (2.41), 5.935 (3.63), 5.947 (2.54), 5.958 (0.71), 7.459 (7.28), 7.477 (7.01), 8.357 (12.52), 9.228 (7.65), 9.230 (8.21), 9.376 (7.72), 9.378 (7.97), 9.425 (4.27), 9.437 (4.21). I-042 [00200] embedded image 2-{5-[(1S)-1-{[7-Chlor-5-(trifluormethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H- 1,2,4-triazol-1-yl}pyrimidin-5-carbonitril LC-MS (method 3): R.sub.t = 0.94 min; MS (ESIpos): m/z = 435 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (1.61), 0.008 (1.71), 1.656 (8.00), 1.673 (8.06), 2.524 (0.55), 5.961 (1.27), 5.979 (1.81), 5.997 (1.27), 7.469 (3.62), 7.489 (3.42), 8.267 (6.50), 9.432 (2.33), 9.451 (2.23), 9.490 (16.00). I-043 [00201] embedded image 7-Chlor-N-{(1S)-1-[1-(5-methoxypyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.88 min; MS (ESIpos): m/z = 440 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.646 (5.36), 1.658 (5.38), 3.961 (16.00), 5.747 (0.83), 5.759 (1.14), 5.772 (0.81), 7.406 (2.22), 7.407 (2.27), 7.460 (2.27), 8.116 (4.53 ), 8.701 (10.56), 9.309 (1.46), 9.322 (1.41). I-044 [00202] embedded image N-{(1S)-1-[1-(5-Brompyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7-chlor-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.03 min; MS (ESIpos): m/z = 488 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.665 (10.62), 1.677 (10.54), 5.859 (0.44), 5.871 (1.70), 5.883 (2.52), 5.895 (1.67), 5.906 (0.42), 7.410 (5.29), 7.469 (5.28), 8.196 (7.72), 9.188 (16.00), 9.370 (3.09), 9.383 (2.98). I-045 [00203] embedded image 7-Chlor-N-{(1S)-1-[1-(5-fluorpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.89 min; MS (ESIpos): m/z = 428 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.658 (9.04), 1.670 (9.11), 5.830 (1.40), 5.842 (2.01), 5.855 (1.39), 7.433 (3.86), 7.482 (3.78), 8.184 (8.02), 9.116 (16.00), 9.393 (2.53), 9.406 (2.42). I-046 [00204] embedded image 7-Chlor-N-{(1S)-1-[1-(6-chlorpyridazin-3-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.10 min; MS (ESIpos): m/z = 444 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.690 (16.00), 1.701 (15.83), 5.838 (0.80), 5.849 (2.74), 5.861 (4.04), 5.872 (2.69), 5.883 (0.72), 7.437 (9.14), 7.482 (8.94), 8.247 (3.97), 8.262 (8.45), 8.288 (8.31), 8.303 (4.17), 8.320 (10.92), 9.459 (4.95), 9.472 (4.79). I-047 [00205] embedded image 7-Chlor-N-{(1S)-1-[1-(pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.96 min; MS (ESIpos): m/z = 410 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO -d6) δ [ppm]: −0.006 (3.89), 1.671 (16.00), 1.682 (15.99), 6.104 (0.59), 6.116 (2.42), 6.128 (3.53), 6.140 (2.40), 6.151 (0.61), 7.479 (7.59), 7.491 (8.01), 8.012 (4.84), 8.013 (4.80), 8.021 (5.04), 8.023 (4.92), 8.272 (13.19), 9.042 (7.29), 9.051 (7.12), 9.210 (8.55), 9.464 (4.56), 9.476 (4.38). I-048 [00206] embedded image 7-Chlor-N-{(rac)-1-[1-(pyrimidin-2-yl)-3-(trifluormethyl)-1H-1,2,4-triazol-5- yl]ethyl}-5-(trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.18 min; MS (ESIpos): m/z = 478 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.724 (16.00), 1.735 (15.74), 1.875 (0.68), 1.887 (0.67), 2.074 (7.35), 5.960 (0.66), 5.973 (2.70), 5.984 (3.95), 5.996 (2.47), 6.007 (0.59), 7.415 (7.87), 7.480 (7.82), 7.757 (3.81), 7.765 (7.46), 7.774 (3.82), 8.728 (0.55), 8.736 (0.54), 9.049 (14.30), 9.057 (14.12), 9.469 (4.61), 9.482 (4.45). I-049 [00207] embedded image (6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridin-3-yl)[(2R,6S)-2,6-dimethylmorpholin-4- yl]methanone LC-MS (method 7): R.sub.t = 1.35 min; MS (ESIpos): m/z = 550 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.985 (1.95), 1.164 (5.98), 1.176 (9.65), 1.188 (4.89), 1.238 (0.56), 1.288 (0.43), 1.298 (0.45), 1.399 (3.50), 1.665 (15.36), 1.676 (15.09), 1.908 (0.67), 1.986 (16.00), 2.039 (0.86), 2.069 (2.41), 2.422 (0.71), 2.571 (0.44), 2.652 (0.56), 2.869 (0.44), 3.324 (0.98), 3.441 (0.58), 3.573 (2.05), 4.014 (1.21), 4.025 (3.78), 4.037 (3.75), 4.049 (1.23), 4.387 (0.60), 5.987 (0.54), 5.998 (2.12), 6.010 (2.94), 6.022 (2.10), 6.033 (0.53), 7.6563 (12.88), 7.577 (0.42), 7.810 (10.30), 7.959 (4.71), 7.973 (5.51), 8.133 (4.33), 8.136 (4.36), 8.147 (3.59), 8.150 (3.78), 8.188 (14.26), 8.572 (5.96), 8.575 (5.93), 9.190 (3.55), 9.204 (3.49). I-050 [00208] embedded image 7-Chlor-N-{(1S)-1-[1-(1,3-thiazol-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 1.12 min; MS (ESIpos): m/z = 415 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.602 (4.89), 1.643 (15.89), 1.655 (16.00), 3.570 (3.29), 5.911 (1.19), 5.922 (3.53), 5.933 (3.54), 5.944 (1.21), 7.456 (5.19), 7.485 (4.99), 7.770 (5.85), 7.776 (8.81), 7.797 (8.72), 7.803 (5.97), 8.203 (11.40). I-051 [00209] embedded image 7-Chlor-N-{(1S)-1-[1-(4-methoxypyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxaozl-2-amin LC-MS (method 1): R.sub.t = 1.96 min; MS (ESIpos): m/z = 440 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.677 (6.13), 1.694 (6.20), 1.989 (0.45), 4.030 (16.00), 5.967 (0.98), 5.985 (1.44), 6.003 (0.99), 7.064 (2.71), 7.079 (2.82), 7.453 (2.86), 7.480 (2.74), 8.148 (4.04), 8.657 (2.80), 8.671 (2.78), 9.401 (1.90), 9.421 (1.85). I-052 [00210] embedded image 2-{5-[(1S)-1-{[7-Chlor-5-(trifluormethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H- 1,2,4-triazol-1-yl}isonicotinonitril LC-MS (method 1): R.sub.t = 2.11 min; MS (ESIpos): m/z = 434 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.651 (15.86), 1.668 (16.00), 1.906 (0.63), 1.920 (0.61), 1.934 (1.04), 1.977 (0.99), 2.075 (5.61), 5.919 (1.65), 5.936 (2.52), 5.954 (1.67), 5.970 (0.42), 7.469 (8.25), 7.480 (7.66), 7.979 (4.81), 7.982 (5.03), 7.992 (5.10), 7.995 (5.33), 8.240 (13.85), 8.350 (7.83), 8.785 (6.13), 8.787 (5.92), 9.798 (6.06), 8.800 (5.85), 9.401 (2.97), 9.419 (2.92). I-053 [00211] embedded image 7-Bromo-N-{(1S)-1-[3-methyl-1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.85 min; MS (ESIpos): m/z = 468 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.644 (8.41), 1.655 (8.54), 2.321 (16.00), 5.906 (1.50), 5.918 (2.14), 5.929 (1.52), 7.460 (4.62), 7.554 (4.67), 7.617 (3.40), 7.625 (2.16), 8.962 (6.38), 8.970 (6.52), 9.376 (2.55), 9.388 (2.54). I-054 [00212] embedded image 7-Brom-N-{(1S)-1-[1-(5-chlorpyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.34 min; MS (ESIpos): m/z = 487 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.638 (15.77), 1.655 (16.00), 5.883 (1.40), 5.900 (2.10), 5.916 (1.41), 7.488 (6.21), 7.555 (6.02), 7.919 (5.87), 7.941 (6.88), 8.177 (9.82), 8.217 (4.20), 8.223 (4.32), 8.239 (3.72), 8.245 (3.88), 8.630 (4.55), 8.636 (4.61), 9.387 (2.58), 9.402 (2.56). I-055 [00213] embedded image 6-[5-[(1S)-1-{[7-Brom-5-(trifluormethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H- 1,2,4-triazol-1-yl}nicotinonitril LC-MS (Method 1): R.sub.t = 2.09 min; MS (ESIpos): m/z = 478 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.646 (15.70), 1.663 (16..00), 5.986 (1.77), 6.003 (2.61), 6.018 (1.78), 7.499 (7.20), 7.560 (7.20), 8.101 (5.70), 8.123 (6.34), 8.249 (9.12), 8.581 (4.00), 8.586 (4.06), 8.603 (3.78), 8.608 (3.79), 9.059 (5.16), 9.063 (5.10), 9.431 (3.26), 9.446 (3.19). I-056 [00214] embedded image 6-Chlor-N-[(1S)-1-{1-[5-(oxetan-3-yl)pyrimidin-2-yl]-1H-1,2,4-triazol-5- yl}ethyl]-5-(trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.68 min; MS (ESIpos): m/z = 466 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.660 (9.60), 1.671 (9.78), 1.679 (1.97), 1.691 (1.62), 1.699 (1.01), 1.710 (0.86), 4.381 (0.41), 4.393 (1.19), 4.406 (2.00), 4.419 (1.37), 4.432 (0.55), 4.681 (2.14), 4.692 (4.12), 4.697 (2.45), 4.702 (2.52), 4.707 (4.09), 4.718 (2.17), 4.939 (4.16), 4.949 (4.41), 4.953 (4.29), 4.963 (3.56), 5.880 (1.03), 5.891 (1.52), 5.903 (1.03), 7.415 (0.63), 7.516 (8.03), 7.637 (0.69), 7.821 (7.55), 8.171 (8.21), 8.178 (0.93), 8.186 (1.26), 8.955 (1.33), 8.962 (1.30, 9.043 (16.00), 9.215 (1.55), 9.227 (1.53). I-057 [00215] embedded image 5-{5-[(1S)-1-{[6-Chlor-5-(trifluormethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H- 1,2,4-triazol-1-yl}pyrazin-2-carbonitril LC-MS (method 3): R.sub.t = 1.02 min; MS (ESIpos): m/z = 435 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.178 (0.64), 1.398 (0.88), 1.654 (16.00), 1.666 (15.98), 1.990 (1.16), 2.074 (1.17), 5.902 (0.63), 5.914 (2.57), 5.925 (3.69), 5.937 (2.53), 5.949 (0.61), 7.552 (12.67), 7.834 (10.41), 8.360 (13.38), 9.227 (8.54), 9.229 (8.27), 9.258 (4.59), 9.271 (4.37), 9.377 (8.84), 9.379 (8.29). I-058 [00216] embedded image 6-Chlor-N-{(1S)-1-[1-(5-methoxypyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.82 min; MS (ESIpos): m/z = 440 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.638 (5.30), 1.655 (5.36), 3.959 (16.00), 5.731 (0.84), 5.750 (1.13), 5.768 (0.82), 7.507 (4.15), 7.814 (2.67), 8.126 (3.79), 8.705 (9.91), 9.168 (1.56), 9.187 (1.51). I-0159 [00217] embedded image 6-Chlor-N-{(1)S-1-[1-(5-chlorpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.94 min; MS (ESIpos): m/z = 444 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.659 (9.44), 1.671 (9.45), 5.857 (1.48), 5.869 (2.11), 5.881 (1.46), 7.507 (7.29), 7.815 (6.04), 8.195 (7.39), 9.124 (16.00), 9.196 (2.59), 9.209 (2.50). I-060 [00218] embedded image 6-Chlor-N-{(1S)-1-[1-(5-methylpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.84 min; MS (ESIpos): m/z = 424 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.651 (8.39), 1.662 (8.45), 2.352 (16.00), 5.847 (1.35), 5.859 (1.94), 5.871 (1.33), 7.524 (6.16), 7.804 (5.15), 8.141 (6.04), 8.824 (10.43), 9.166 (2.42), 9.179 (2.35). I-061 [00219] embedded image 6-Chlor-N-{(1S)-1-[1-(5-fluorpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.81 min; MS (ESIpos): m/z = 428 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.656 (9.85), 1.668 (9.84), 3.635 (1.39), 5.816 (1.49), 5.828 (2.08), 5.840 (1.46), 7.516 (7.58), 7.812 (6.17), 8.175 (7.89), 9.098 (16.00), 9.181 (2.48), 9.194 (2.38). I-062 [00220] embedded image N-{(1S)-1-[1-(5-Brompyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-6-chlor-5- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 1.02 min; MS (ESIpos): m/z = 488 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.165 (1.92), 1.177 (3.95), 1.189 (1.97), 1.657 (8.22), 1.669 (8.22), 1.991 (7.45), 4.014 (0.60), 4.026 (1.79), 4.038 (1.76), 4.049 (0.59), 5.857 (1.31), 5.869 (1.84), 5.881 (1.29), 7.508 (6.50), 7.829 (5.52), 8.205 (7.05), 9.194 (16.00), 9.234 (2.44), 9.247 (2.32). I-063 [00221] embedded image 7-Chlor-5-isopropyl-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}- 1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 0.97 min; MS (ESIpos): m/z = 384 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.152 (15.94), 1.154 (15.70), 1.163 (16.00), 1.165 (15.54), 1.646 (10.66), 1.657 (10.63), 2.077 (0.75), 2.841 (0.64), 2.852 (1.58), 2.864 (2.09), 2.876 (1.52), 2.887 (0.60), 3.959 (0.48), 5.857 (1.57), 5.870 (2.22), 5.882 (1.55), 6.909 (5.87), 6.924 (5.90), 7.667 (2.77), 7.676 (5.43), 7.683 (2.83), 8.150 (9.01), 8.954 (2.78), 8.967 (2.66), 9.009 (10.57), 9.017 (10.30). I-064 [00222] embedded image 2-(5-{(1S)-1-[(7-Chlor-5-isopropyl-1,3-benzoxazol-2-yl)amino]ethyl}-1H-1,2,4- triazol-1-yl)isonicotinonitril LC-MS (method 7): R.sub.t = 1.45 min; MS (ESIpos): m/z = 408 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.153 (15.66), 1.169 (16.00), 1.628 (9.28), 1.645 (9.33), 2.074 (0.83), 2.831 (0.57), 2.848 (1.43), 2.865 (1.89), 2.882 (1.37), 2.899 (0.53), 5.860 (1.43), 5.878 (2.03), 5.896 (1.43), 6.911 (4.44), 6.914 (5.12), 6.946 (5.22), 6.949 (4.35), 7.991 (2.76 ), 7.995 (2.83), 8.004 (2.91), 8.007 (2.96), 8.216 (6.81), 8.341 (3.94), 8.810 (3.43), 8.811 (3.43), 8.822 (3.38), 8.824 (3.36), 8.969 (2.61), 8.989 (2.52). I-065 [00223] embedded image 7-Chlor-5-cyclopropyl-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5- yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 0.90 min; MS (ESIpos): m/z = 382 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 0.612 (1.76), 0.623 (5.50), 0.628 (5.47), 0.636 (5.83), 0.640 (5.56), 0.651 (2.30), 8.62 (2.02), 0.872 (5.16), 0.877 (5.16), 0.883 (2.75), 0.893 (5.45), 0.898 (5.16), 0.909 (1.81), 1.633 (15.83), 1.650 (16.00), 1.868 (0.81), 1.880 (1.62), 1.889 (1.77), 1.901 (3.06), 1.914 (1.65), 1.922 (1.54), 1.935 (0.73), 5.754 (6.17), 5.826 (0.55), 5.844 (2.37), 5.862 (3.35), 5.880 (2.36), 5.898 (0.57), 6.728 (7.71), 6.732 (8.25), 6.789 (8.34), 6.792 (7.43), 7.651 (4.00), 7.663 (8.12), 7.675 (4.26), 8.147 (10.78), 8.937 (4.26), 8.957 (4.16), 8.993 (14.60), 9.005 (14.60). I-066 [00224] embedded image 7-Chlor-5-isopropyl-N-{(1S)-1-[1-(pyrimidin-4-yl)-1H-1,2,4-triazol-5-yl]ethyl}- 1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.04 min; MS (ESIpos): m/z = 384 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: −0.007 (0.69), 1.140 (16.00), 1.151 (15.99), 1.646 (7.38), 1.657 (7.30), 2.071 (4.65), 2.830 (0.43), 2.842 (1.07), 2.854 (1.42), 2.865 (1.03), 6.071 (1.08), 6.083 (1.53), 6.095 (1.05), 6.911 (3.53), 6.913 (3.64), 6.978 (3.77), 6.980 (3.44), 8.010 (2.16), 8.011 (2.11), 8.019 (2.20), 8.021 (2.15), 8.246 (6.44), 9.037 (1.96), 9.043 (3.79), 9.052 (4.30), 9.223 (3.72), 9.224 (3.67). I-067 [00225] embedded image 7-Chlor-5-cyclopropyl-N-{(1S)-1-[1-(3-fluorpyridin-2-yl)-1H-1,2,4-triazol-5- yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.90 min; MS (EISpos): m/z = 399 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.644 (6.94), 0.651 (7.32), 9.901 (6.04), 0.904 (6.21), 0.915 (6.56), 0.918 (6.23), 1.627 (15.82), 1.638 (16.00), 1.904 (0.88), 1.913 (1.75), 1.918 (2.05), 1.927 (3.15), 1.935 (2.05), 1.941 (1.72), 1.949 (0.87), 2.075 (1.24), 5.188 (0.69), 5.200 (2.57), 5.212 (3.89), 5.224 (2.66), 5.236 (0.77), 6.710 (9.16), 6.766 (9.02), 6.768 (9.15), 7.698 (1.61), 7.705 (2.71), 7.711 (3.48), 7.719 (3.02), 7.725 (1.90), 8.094 (2.44), 8.108 (4.32), 8.124 (2.33), 8.194 (11.59), 8.417 (4.92), 8.425 (4.86), 8.860 (4.52), 8.872 (4.49). I-068 [00226] embedded image N-{(1S)-1-[1-(5-Brompyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7-chlor-5- isopropyl-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 1.12 min; MS (ESIneg): m/z = 460 [M − H].sup.− .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.162 (13.45), 1.166 (13.74), 1.174 (13.81), 1.178 (13.13), 1.204 (0.40), 1.646 (10.40), 1.657 (10.33), 2.850 (0.70), 2.861 (1.66), 2.872 (2.17), 2.884 (1.58), 2.895 (0.64), 3.665 (0.44), 5.797 (0.43), 5.809 (1.63), 5.821 (2.40), 5.833 (1.60), 5.844 (0.40), 6.890 (6.11), 6.908 (6.02), 8.170 (7.68), 8.930 (2.87), 8.943 (2.77), 9.197 (16.00). I-069 [00227] embedded image 7-Chlor-5-(pentafluor-lambda.sup.6-sulfanyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H- 1,2,4-triazol-5-yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.90 min; MS (ESIpos): m/z = 468 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (1.22), 0.008 (1.17), 1.660 (14.13), 1.677 (14.13), 2.525 (0.86), 5.891 (0.48), 5.909 (2.13), 5.927 (2.97), 5.945 (2.13), 5.962 (0.49), 7.50 (10.93), 7.55 (8.82), 7.661 (9.45), 7.674 (4.95), 7.685 (8.22), 7.690 (6.16 ), 8.176 (9.15), 8.991 (16.00), 9.003 (15.76), 9.464 (3.89), 9.484 (3.77). I-070 [00228] embedded image 7-Chlor-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (triflourmethoxy)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.83 min; MS (ESIpos): m/z = 426 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.655 (16.00), 1.667 (15.93), 2.852 (0.41), 2.916 (0.70), 3.091 (0.50), 5.885 (0.57), 5.896 (2.42), 5.908 (3.43), 5.920 (2.36), 5.932 (0.60), 7.124 (5.06), 7.158 (5.37), 7.649 (3.82), 7.657 (7.57), 7.665 (3.95), 8.161 (12.54), 8.989 (14.51), 8.998 (14.28), 9.285 (4.18), 9.298 (4.06). I-071 [00229] embedded image N-{(1S)-1-[1-(5-Brompyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7-chlor-5- (difluormethoxy)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.86 min; MS (ESIpos): m/z = 486 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.647 (9.52), 1.658 (9.57), 2.071 (1.55), 5.837 (1.49), 5.849 (2.22), 5.860 (1.49), 6.899 (3.65), 6.903 (4.31), 6.943 (4.46), 6.947 (3.93), 7.024 (1.91), 7.147 (3.82), 7.271 (1.84), 8.182 (7.75), 9.185 (16.00), 9.196 (2.85), 9.209 (2.63). I-072 [00230] embedded image 5-Chlor-6-(cyclopropylsulfanyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol- 5-yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.76 min; MS (ESIpos): m/z = 414 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.588 (1.86), 0.595 (5.86), 0.605 (6.13), 0.612 (3.15), 0.622 (1.88), 1.114 (1.57), 1.121 (5.47), 1.125 (5.94), 1.133 (6.58), 1.136 (5.78), 1.143 (2.02), 1.166 (0.86), 1.179 (0.80), 1.363 (1.26), 1.375 (1.27), 1.420 (0.45), 1.438 (0.42), 1.466 (0.92), 1.478 (0.91), 1.503 (0.72), 1.514 (1.04), 1.522 (1.15), 1.653 (16.00), 1.664 (15.89), 2.261 (0.92), 2.268 (1.74), 2.273 (2.08), 2.281 (3.40), 2.288 (2.06), 2.293 (2.01), 2.300 (1.21), 2.311 (0.56), 3.131 (0.58), 3.310 (0.89), 3.464 (0.97), 3.907 (2.04), 4.162 (0.56), 4.172 (0.52), 4.211 (0.50), 4.223 (0.56), 4.236 (0.48), 5.212 (0.44), 5.861 (0.58), 5.872 (2.30), 5.885 (3.16), 5.897 (2.23), 5.909 (0.54), 6.759 (0.42), 7.184 (13.79), 7.209 (0.41), 7.282 (0.87), 7.335 (1.04), 7.353 (0.76), 7.542 (13.43), 7.574 (0.86), 7.595 (1.16), 7.603 (0.96), 7.653 (4.29), 7.661 (7.89), 7.669 (4.07), 8.170 (13.66), 8.348 (0.76), 8.356 (0.72), 8.884 (4.02), 8.897 (3.85), 8.989 (15.08), 8.998 (14.91), 10.010 (0.47). I-073 [00231] embedded image 5-Chor-6-(ethylsulfanoyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5- yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.70 min; MS (ESIpos): m/z = 402 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.196 (7.65), 1.208 (16.00), 1.221 (8.07), 1.646 (11.71), 1.658 (11.63), 2.939 (2.50), 2.951 (7.57), 2.963 (7.54), 2.975 (2.51), 5.858 (0.44), 5.870 (1.77), 5.882 (2.42), 5.894 (1.71), 5.905 (0.40), 7.203 (9.76), 7.438 (9.90), 7.650 (2.77), 7.658 (5.51), 7.666 (2.84), 8.166 (9.82), 8.928 (3.16), 8.941 (3.01), 8.988 (10.59), 8.996 (10.46). I-074 [00232] embedded image 7-Chlor-5-(difluormethoxy)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5- yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.62 min; MS (ESIpos): m/z = 408 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.517 (0.45), 1.655 (16.00), 1.666 (15.98), 5.873 (0.60), 5.885 (2.38), 5.897 (3.56), 5.908 (2.39), 5.920 (0.58), 6.918 (7.55), 6.934 (7.60), 7.022 (2.53), 7.145 (5.12), 7.269 (2.49), 7.650 (3.45), 7.658 (6.88), 7.666 (3.56), 8.156 (11.38), 8.991 (13.34), 8.992 (9.58), 8.999 (13.15), 9.179 (4.11), 9.192 (3.98). I-075 [00233] embedded image 5-tert-Butyl-7-chlor-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}- 1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.97 min; MS (ESIpos): m/z = 398 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.246 (16.00), 1.645 (2.09), 1.656 (2.06), 5.870 (0.43), 7.012 (1.07), 7.015 (1.12), 7.064 (1.15), 7.067 (1.03), 7.669 (0.51), 7.677 (1.00), 7.685 (0.52), 8.149 (1.77), 8.958 (0.52), 8.971 (0.50), 9.011 (1.94), 9.019 (1.91). I-076 [00234] embedded image 5-Chlor-6-(methylsulfanyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5- yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.58 min; MS (ESIpos): m/z = 388 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.646 (6.19), 1.657 (6.13), 2.466 (16.00), 2.492 (0.62), 3.831 (0.71), 5.863 (0.91), 5.875 (1.20), 5.887 (0.87), 7.191 (5.59), 7.339 (5.14), 7.649 (1.62), 7.657 (3.22), 7.665 (1.67), 8.165 (5.36), 8.887 (1.58), 8.901 (1.52), 8.986 (6.21), 8.994 (6.11). I-077 [00235] embedded image 6-(5-[(1S)-1-[(5-tert-Butyl-7-chlor-1,3-benzoxazol-2-yl)amino]ethyl}-1H-1,2,4- triazol-1-yl)nicotinonitril LC-MS (method 1): R.sub.t = 2.25 min; MS (ESIpos): m/z = 422 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.243 (16.00), 1.629 (2.14), 1.641 (2.13), 5.968 (0.49), 7.020 (1.08), 7.022 (1.11), 7.102 (1.14), 7.104 (1.06), 8.105 (0.85), 8.119 (0.90), 8.231 (1.80), 8.591 (0.54), 8.595 (0.54), 8.606 (0.51), 8.609 (0.52), 9.014 (0.66), 9.027 (0.63), 9.079 (0.85), 9.083 (0.82). I-078 [00236] embedded image N-{(1S)-1-[1-(5-Brompyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7-chlor-5- (trifluormethoxy)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.08 min; MS (ESIpos): m/z = 504 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.649 (9.48), 1.660 (9.37), 3.676 (1.43), 5.849 (1.49), 5.861 (2.16), 5.873 (1.43), 7.104 (3.24), 7.167 (3.43), 8.187 (7.48), 9.183 (16.00), 9.299 (2.62), 9.312 (2.52). I-079 [00237] embedded image 7-Chlor-N-{(1S)-1-[1-(5-chlorpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethoxy)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.05 min; MS (ESIpos): m/z = 460 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.650 (8.12), 1.662 (8.05), 3.649 (1.62), 3.676 (1.45), 3.716 (0.67), 5.851 (1.22), 5.863 (1.71), 5.875 (1.18), 7.109 (2.41), 7.111 (2.46), 7.169 (2.55), 7.171 (2.32), 8.189 (6.78 ), 9.126 (16.00), 9.301 (2.08), 9.314 (1.99). I-080 [00238] embedded image 7-Chlor-5-(phenylsulfonyl)-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5- yl]ethyl}-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.62 min; MS (ESIpos): m/z = 482 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.648 (15.36), 1.660 (15.14), 2.074 (0.48), 5.884 (0.55), 5.896 (2.34), 5.908 (3.36), 5.920 (2.29), 5.931 (0.53), 7.587 (4.18), 7.592 (8.36), 7.594 (8.85), 7.599 (8.85), 7.613 (5.83), 7.652 (4.82), 7.656 (9.39), 7.659 (11.10), 7.665 (3.60), 7.668 (4.86), 7.677 (4.52), 7.690 (1.61), 7.980 (6.60), 7.982 (8.33), 7.995 (7.52), 8.148 (13.27), 8.988 (16.00), 8.996 (15.59), 9.441 (4.36), 9.454 (4.15). I-081 [00239] embedded image 6-Chlor-N-{(1S)-1-[1-(5-fluorpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethoxy)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.86 min; MS (ESIpos): m/z = 444 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.644 (9.63), 1.656 (9.58), 5.796 (1.48), 5.808 (2.06), 5.820 (1.44), 7.266 (3.82), 7.762 (7.96), 8.168 (7.85), 9.094 (16.00), 9.114 (2.55), 9.127 (2.44). I-082 [00240] embedded image 6-Chlor-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluormethoxy)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 1.77 min; MS (ESIpos): m/z = 426 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.652 (16.00), 1.663 (15.95), 2.069 (1.50), 5.874 (0.63), 5.886 (2.51), 5.898 (3.53), 5.910 (2.45), 5.922 (0.61), 7.275 (6.87), 7.641 (3.87), 7.649 (7.57), 7.657 (3.91), 7.753 (12.48), 8.161 (12.33), 8.980 (14.62), 8.988 (14.41), 9.110 (4.40), 9.123 (4.24). I-083 [00241] embedded image N-{(1S)-1-[1-(5-Brompyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7-chlor-5- (pentafluor-lambda.sup.6-sulfanyl)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.13 min; MS (ESIpos): m/z = 546 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.663 (9.93), 1.675 (9.93), 5.855 (0.41), 5.867 (1.60), 5.879 (2.35), 5.891 (1.58), 5.902 (0.40), 7.611 (4.56), 7.614 (4.77), 7.679 (4.93), 7.682 (4.55), 8.197 (7.48), 9.187 (16.00), 9.451 (2.90), 9.464 (2.81). I-084 [00242] embedded image 7-Chlor-2-({1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}amino)-1,3- benzoxazol-5-carbonitril LC-MS (method 1): R.sub.t = 1.42 min; MS (ESIpos): m/z = 367 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.452 (0.47), 1.464 (0.48), 1.661 (15.38), 1.673 (15.29), 5.900 (0.56), 5.912 (2.30), 5.924 (3.23), 5.936 (2.26), 5.947 (0.55), 7.586 (7.64), 7.588 (7.93), 7.656 (4.18), 7.664 (8.32), 7.672 (4.50), 7.678 (7.98), 7.680 (7.83), 8.180 (13.72), 8.995 (16.00), 9.003 (15.76), 9.452 (4.24), 9.465 (4.07). I-085 [00243] embedded image N-{(1S)-1-[1-(5-Brompyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-6-chlor-5 (trifluormethoxy)-1,3-benzoxazol-2-amin LC-MS (method 1): R.sub.t = 2.02 min; MS (ESIpos): m/z = 504 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.646 (8.16), 1.658 (8.10), 3.264 (0.48), 5.838 (1.27), 5.850 (1.71), 5.862 (1.27), 7.247 (3.02), 7.248 (2.92), 7.765 (6.58), 8.187 (6.80), 9.129 (2.20), 9.142 (2.15), 9.179 (16.00). I-086 [00244] embedded image 5-Chlor-N-[(1S)-1-{3-methyl-1-[5-(trifluormethyl)pyridin-2-yl]-1H-1,2,4- triazol-5-yl}ethyl]-7-(trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 1.28 min; MS (ESIpoz): m/z = 491 [M + H].sup.+ .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.636 (5.76), 1.650 (5.72), 2.336 (16.00), 5.997 (0.86), 6.011 (1.16), 6.026 (0.83), 7.336 (2.16), 7.338 (2.20), 7.519 (2.16), 7.522 (2.05), 8.063 (1.75), 8.080 (1.88), 8.468 (1.14), 8.472 (1.13), 8.485 (1.06), 8.490 (1.03), 8.946 (1.75), 8.947 (1.74), 8.949 (1.72), 8.950 (1.71), 9.425 (1.59), 9.441 (1.52). I-087 [00245] embedded image 5-Chlor-7-(trifluormethyl)-N-[(1S)-1-{1-[5-(trifluormethyl)pyridin-2-yl]-1H- 1,2,4-triazol-5-yl}ethyl]-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 1.24 min; MS (ESIpos): m/z = 477 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.657 (16.00), 1.669 (15.81), 6.010 (1.91), 6.021 (1.91), 7.338 (5.79), 7.340 (5.95), 7.512 (5.76), 7.515 (5.60), 8.117 (4.75), 8.131 (5.04), 8.239 (14.00), 8.511 (3.12), 8.515 (3.14), 8.525 (2.93), 8.529 (2.91), 8.978 (4.99), 9.454 (3.53). I-088 [00246] embedded image 6-{5-[(1S)-1-{[5-Chlor-7-(trifluormethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-1H- 1,2,4-triazol-1-yl}nicotinonitril LC-MS (method 3): R.sub.t = 1.09 min; MS (ESIpos): m/z = 434 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.640 (16.00), 1.651 (15.98), 1.920 (0.40), 5.988 (1.49), 5.999 (2.19), 6.010 (1.48), 7.344 (5.99), 7.346 (6.31), 7.538 (5.93), 7.541 (5.92), 8.100 (6.02), 8.114 (6.40), 8.247 (13.65), 8.589 (4.26), 8.593 (4.37), 8.603 (4.04), 8.607 (4.17), 9.056 (6.02), 9.059 (6.07), 9.462 (2.70), 9.472 (2.47). I-089 [00247] embedded image 5-Chlor-N-{(1S)-1-[3-methyl-1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 0.95 min; MS (ESIpos): m/z = 424 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: −0.008 (0.58), 0.008 (0.69), 1.175 (0.56), 1.625 (5.83), 1.643 (5.88), 1.989 (1.04), 2.075 (0.41), 2.315 (16.00), 5.890 (0.94), 5.908 (1.22), 5.926 (0.94), 7.336 (2.14), 7.339 (2.25), 7.493 (2.08), 7.497 (1.97), 7.602 (1.87), 7.614 (3.74), 7.626 (1.98), 8.955 (7.27), 8.967 (7.07), 9.386 (1.67), 9.406 (1.62). I-090 [00248] embedded image 5-Chlor-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7- (trifluormethyl)-1,3-benzoxazol-2-amin LC-MS (method 3): R.sub.t = 0.93 min; MS (ESIpos): m/z = 410 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.652 (16.00), 1.664 (15.90), 2.078 (0.63), 5.758 (2.50), 5.898 (0.62), 5.910 (2.45), 5.922 (3.54), 5.934 (2.40), 5.945 (0.61), 7.338 (6.26), 7.340 (6.43), 7.489 (6.05), 7.491 (5.86), 7.656 (4.04), 7.664 (7.81), 7.672 (4.13), 8.169 (12.75), 8.996 (14.79), 9.004 (14.70), 9.414 (4.50), 9.426 (4.30). I-091 [00249] embedded image 6-{5-[(1S)-1-{[5-Chlor-7-(trifluormethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-3- methyl-1H-1,2,4-triazol-1-yl)nicotinonitril LC-MS (method 3): R.sub.t = 1.12 min; MS (ESIpos): m/z = 448 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.618 (6.24), 1.630 (6.20), 1.919 (0.45), 1.928 (0.48), 2.329 (16.00), 2.657 (0.63), 5.977 (0.89), 5.898 (1.29), 6.001 (0.89), 7.344 (2.33), 7.347 (2.41), 7.545 (2.36), 7.548 (2.29), 8.037 (2.35), 8.051 (2.51), 8.546 (1.76), 8.550 (1.78), 8.561 (1.66), 8.565 (1.73), 9.026 (2.30), 9.029 (2.34), 9.443 (1.55), 9.456 (1.51). I-092 [00250] embedded image 8-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-6- (trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine LC-MS (method 7): R.sub.t = 1.05 min; MS (ESIpos): m/z = 410 [M + H].sup.+ .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.033 (0.49), 1.045 (0.44), 1.630 (12.36), 1.643 (12.26), 2.519 (0.62), 3.568 (1.23), 5.754 (0.71), 5.854 (1.02), 5.868 (1.50), 5.882 (0.98), 7.628 (4.15), 7.638 (8.01), 7.647 (4.20), 7.854 (1.22), 7.870 (1.19), 7.979 (5.40), 7.981 (5.25 ), 8.111 (11.37), 8.985 (16.00), 8.995 (15.39), 9.101 (4.66). I-093 [00251] embedded image N-{(1S)-1-[1-(5-bromopyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-8-chloro-6- (trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine LC-MS (method 1): R.sub.t = 1.75 min; MS (ESIpos): m/z = 488 [M + H].sup.+ .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: −0.120 (0.80), −0.007 (8.39), 0.007 (6.71), 0.117 (0.82), 1.422 (0.55), 1.436 (0.57), 1.631 (6.12), 1.645 (6.06), 2.731 (0.67), 2.891 (0.84), 3.634 (1.35), 3.935 (1.93), 5.817 (0.46), 5.831 (0.69), 5.844 (0.48), 7.880 (0.53), 7.897 (0.50), 7.986 (2.88), 7.989 (2.80), 8.141 (6.18), 9.104 (2.44), 9.183 (16.00). I-094 [00252] embedded image 6-bromo-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7- (trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine LC-MS (method 8): R.sub.t = 0.83 min; MS (ESIpos): m/z = 456 [M + H].sup.+ .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.106 (16.00), 1.616 (4.42), 1.630 (4.41), 3.077 (5.23), 3.169 (0.43), 5.753 (0.85), 5.852 (0.53), 7.625 (1.29), 7.634 (2.50), 7.644 (1.28), 7.857 (2.68), 8.098 (4.03), 8.980 (4.90), 8.990 (4.75), 9.122 (2.72). I-095 [00253] embedded image 6-bromo-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-8- (trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine LC-MS (method 1): R.sub.t = 1.50 min; MS (ESIpos): m/z = 454 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.619 (15.53), 1.631 (15.40), 3.933 (2.57), 5.744 (2.14), 5.848 (1.44), 5.860 (1.44), 7.620 (4.18), 7.628 (8.33), 7.636 (4.30), 7.821 (0.66), 7.985 (5.57), 8.088 (12.93), 8.975 (16.00), 8.983 (15.87), 9.095 (5.31). I-096 [00254] embedded image 6-chloro-N-{(1S)-1-[1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-7- (trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine LC-MS (method 1): R.sub.t = 1.48 min; MS (ESIpos): m/z = 410 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.624 (15.09), 1.635 (14.98), 5.848 (1.06), 5.859 (1.56), 5.870 (1.04), 7.624 (4.12), 7.632 (8.27), 7.640 (4.30), 7.680 (1.07), 7.692 (1.05), 7.859 (8.27), 8.096 (12.33), 8.980 (16.00), 8.988 (15.64), 9.073 (8.18). I-097 [00255] embedded image 7-chloro-N-{(1S)-1-[1-(pyrimdin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-6- (trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine LC-MS (method 7): R.sub.t = 1.07 min; MS (ESIpos): m/z = 410 [M + H].sup.+ .sup.1H-NMR (400 MHz, DMSO-d6) δ [ppm]: 1.413 (0.79), 1.431 (0.80), 1.613 (13.67), 1.630 (13.35), 2.368 (0.56), 2.711 (0.51), 5.827 (1.40), 5.844 (1.90), 5.863 (1.28), 7.623 (4.40), 7.635 (8.50), 7.647 (4.45), 7.731 (7.60), 7.761 (1.70), 7.895 (0.43), 8.105 (10.20), 8.980 (16.00), 8.992 (15.36), 9.104 (6.91), 9.299 (0.41). I-098 [00256] embedded image 6-{5-[(1S)-1-{[6-chloro-4-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}-N-(cyanomethyl)-N-methylpyridine-3-carboxamide LC-MS (method 7): R.sub.t = 1.25 min; MS (ESIpos): m/z = 505 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.164 (1.40), 1.175 (2.78), 1.187 (1.44), 1.663 (10.79), 1.674 (10.72), 1.986 (5.41), 2.691 (0.60), 3.071 (16.00), 3.252 (0.46), 3.256 (0.51), 3.263 (0.50), 4.013 (0.44), 4.025 (1.24), 4.037 (1.26), 4.049 (0.42), 4.585 (5.93), 5.744 (9.41), 5.980 (0.43), 5.991 (1.73), 6.003 (2.53), 6.016 (1.80), 6.027 (0.46), 7.570 (7.90), 7.811 (6.35), 7.985 (2.59), 7.999 (2.92), 8.198 (8.63), 8.228 (1.00), 8.669 (1.74), 9.197 (2.19), 9.211 (2.20). I-099 [00257] embedded image (6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridin-3-yl)(morpholin-4-yl)methanone LC-MS (method 7): R.sub.t = 1.23 min; MS (ESIpos): m/z = 522 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.107 (1.86), 1.664 (16.00), 1.675 (15.91), 2.070 (2.61), 2.424 (0.40), 3.078 (0.64), 3.371 (1.13), 5.970 (0.65), 5.981 (2.63), 5.994 (3.82), 6.005 (2.60), 6.017 (0.64), 7.574 (12.56), 7.814 (9.68), 7.957 (5.94), 7.971 (6.82), 8.147 (4.14), 8.150 (4.11), 8.161 (3.61), 8.165 (3.58), 8.188 (12.45), 8.582 (6.87), 8.585 (6.68), 9.188 (3.22), 9.201 (3.08). I-100 [00258] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-3- cyclopropyl-1H-1,2,4-triazol-1-yl}pyridine-3-carbonitrile LC-MS (method 1): R.sub.t = 2.31 min; MS (ESIpos): m/z = 474 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.804 (0.73), 0.814 (1.39), 0.819 (1.59), 0.823 (2.06), 0.831 (2.73), 0.838 (1.57), 0.875 (1.65), 0.882 (2.78), 0.890 (2.07), 0.896 (1.52), 0.900 (1.57), 0.908 (0.96), 0.941 (0.76), 0.946 (0.69), 0.956 (2.09), 0.961 (2.30), 0.970 (4.70), 0.975 (3.24), 0.982 (4.62), 0.989 (1.88), 0.994 (1.71), 1.004 (0.47), 1.009 (0.48), 1.614 (16.00), 1.626 (15.88), 2.020 (0.96), 2.028 (1.85), 2.034 (2.10), 2.042 (3.42), 2.050 (1.98), 2.056 (1.68), 2.064 (0.81), 5.939 (0.71), 5.951 (2.72), 5.963 (3.78), 5.975 (2.74), 5.986 (0.66), 7.577 (12.58), 7.822 (9.48), 8.020 (6.10), 8.034 (6.44), 8.524 (4.16), 8.527 (4.29), 8.538 (3.98), 8.542 (4.06), 8.992 (6.09), 8.995 (6.02), 9.177 (3.47), 9.190 (3.31). I-101 [00259] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]-3- methoxy-1H-1,2,4-triazol-1-yl}pyridine-3-carbonitrile LC-MS (method 1): R.sub.t = 2.17 min; MS (ESIpos): m/z = 464 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.627 (6.47), 1.639 (6.43), 3.953 (16.00), 5.959 (1.07), 5.971 (1.59), 5.983 (1.08), 7.592 (5.06), 7.839 (3.81), 7.982 (2.61), 7.996 (2.72), 8.533 (1.56), 8.536 (1.66), 8.547 (1.50), 8.5551 (1.62), 8.999 (2.41), 9.002 (2.47), 9.232 (1.33), 9.245 (1.27). I-102 [00260] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}-N,N-diethylpyridine-3-carboxamide LC-MS (method 7): R.sub.t = 1.35 min; MS (ESIpos): m/z = 508 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.039 (3.33), 1.155 (3.36), 1.235 (0.44), 1.249 (0.71), 1.261 (0.77), 1.274 (0.50), 1.665 (16.00), 1.676 (15.96), 2.423 (0.49), 2.652 (0.45), 3.187 (2.01), 3.462 (1.92), 5.969 (0.69), 5.980 (2.70), 5.993 (3.78), 6.004 (2.57), 6.016 (0.65), 7.575 (12.54), 7.808 (10.22), 7.930 (5.94), 7.944 (6.85), 8.093 (4.24), 8.097 (4.20), 8.107 (3.53), 8.111 (3.47), 8.184 (12.55), 8.501 (6.96), 8.504 (6.43), 9.163 (3.86), 9.176 (3.68). I-103 [00261] embedded image (6-{5-[(1S)-1-{[6-chloro-5-(trifluroomethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridin-3-yl)(pyrrolidin-1-yl)methanone LC-MS (method 7): R.sub.t = 1.29 min; MS (ESIpos): m/z = 506 [M + H].sup.+ .sup.1H-NMR (500 MHz, DMSO-d6) δ [ppm]: 1.232 (1.16), 1.247 (5.63), 1.261 (6.41), 1.275 (3.52), 1.642 (0.69), 1.662 (13.21), 1.676 (13.07), 1.776 (1.70), 1.789 (2.74), 1.797 (2.96), 1.810 (2.32), 1.833 (0.78), 1.856 (2.40), 1.862 (2.36), 1.868 (2.88), 1.876 (2.72), 1.890 (1.58), 2.560 (1.47), 2.690 (0.60), 3.130 (0.54), 3.139 (0.54), 3.145 (0.54), 3.154 (0.52), 3.324 (2.00), 3.337 (4.50), 3.350 (4.50), 3.63 (2.25), 3.369 (1.56), 3.383 (1.19), 3.488 (16.00), 3.502 (7.71), 3.604 (0.64), 3.617 (0.68), 3.624 (0.67), 3.630 (0.60), 3.638 (0.52), 5.976 (0.51), 5.990 (2.20), 6.005 (2.93), 6.020 (2.11), 6.033 (0.50), 7.592 (11.72), 7.820 (9.92), 7.930 (5.24), 7.947 (5.80), 8.198 (12.98), 8.219 (4.06), 8.223 (4.03), 8.235 (3.47), 8.240 (3.54), 8.638 (5.76), 8.642 (5.51), 9.183 (4.04), 9.199 (3.86). I-104 [00262] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridine-3-carboxamide LC-MS (method 1): R.sub.t = 1.62 min; MS (ESIpos): m/z = 452 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.234 (0.58), 1.664 (16.00), 1.675 (15.92), 5.988 (0.67), 5.999 (2.62), 6.012 (3.74), 6.023 (2.60), 6.035 (0.67), 7.570 (12.64), 7.683 (2.80), 7.814 (9.38), 7.997 (6.03), 8.011 (6.35 ), 8.195 (12.47), 8.237 (2.89), 8.486 (4.06), 8.490 (4.07), 8.500 (3.78), 8.504 (3.84), 8.983 (6.66), 8.986 (6.55), 9.215 (3.44), 9.227 (3.21). I-105 [00263] embedded image 2-{5-[(1S)-1-{[6-chloro-5-(trifluoromethoxy)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}-1,3-thiazole-5-carbonitrile LC-MS (method 1): R.sub.t = 2.16 min; MS (ESIpos): m/z = 456 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.645 (16.00), 1.656 (15.99), 5.881 (0.62), 5.892 (2.62), 5.904 (3.95), 5.916 (2.61), 5.927 (0.61), 7.387 (6.77), 7.810 (12.61), 8.317 (13.15), 8.664 (13.86), 9.261 (3.61), 9.274 (3.49). I-106 [00264] embedded image 6-{5-[(1S)-1-{[7-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}-N,N-diethylpyridine-3-carboxamide LC-MS (method 7): R.sub.t = 1.39 min; MS (ESIpos): mz = 508 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.039 (3.70), 1.155 (3.92), 1.637 (0.65), 1.648 (0.80), 1.671 (15.77), 1.683 (16.00), 2.345 (1.30), 2.424 (0.46), 2.652 (0.76), 3.192 (2.24), 3.457 (2.74), 5.984 (0.64), 5.996 (2.59), 6.008 (3.79), 6.020 (2.61), 6.032 (0.82), 7.462 (7.77), 7.481 (8.20), 7.940 (5.67), 7.954 (6.72), 8.100 (4.31), 8.104 (4.41), 8.114 (3.74), 8.117 (3.83), 8.186 (12.12), 8.448 (0.53), 8.509 (6.58), 8.512 (6.50), 9.341 (3.38), 9.353 (3.42). I-107 [00265] embedded image (6-{5-[(1S)-1-{[7-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridin-3-yl)[(2R,6S)-2,6-dimethylmorpholin-4- yl]methanone LC-MS (method 7): R.sub.t = 1.39 min; MS (ESIpos): m/z = 550 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.984 (2.38), 1.165 (4.70), 1.177 (6.58), 1.188 (3.31), 1.235 (0.47), 1.250 (0.53), 1.262 (0.53), 1.640 (0.65), 1.651 (0.83), 1.672 (16.00), 1.684 (15.70), 1.988 (10.15), 2.344 (1.20), 2.424 (0.47), 2.734 (9.19), 2.892 (10.76), 3.46 (0.66), 3.567 (2.49), 3.578 (2.64), 4.014 (1.54), 4.026 (3.23), 4.038 (3.28), 4.050 (1.78), 4.165 (2.08), 4.380 (0.98), 6.004 (0.55), 6.016 (2.11), 6.028 (3.10), 6.040 (2.09), 6.051 (0.53), 7.466 (11.69), 7.954 (1.54), 7.968 (5.28), 7.983 (6.12), 8.140 (4.31), 8.143 (4.41), 8.154 (3.71), 8.158 (3.80), 8.189 (13.33), 8.586 (6.47), 8.590 (6.50), 9.37 (3.04), 9.386 (2.93). I-108 [00266] embedded image (6-{5-[(1S)-1-{[7-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridin-3-yl)(morpholin-4-yl)methanone LC-MS (method 7): R.sub.t = 1.26 min; MS (ESIpos): m/z = 522 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.638 (0.65), 1.648 (0.86), 1.668 (16.00), 1.679 (15.78), 2.340 (1.23), 2.691 (2.85), 2.732 (3.51), 2.890 (3.96), 3.392 (1.31), 5.982 (0.61), 5.994 (2.54), 6.006 (3.69), 6.018 (2.50), 6.029 (0.58), 7.466 (8.16), 7.475 (8.34), 7.964 (5.62), 7.978 (6.45), 8.152 (4.18), 8.155 (4.32), 8.166 (3.66), 8.169 (3.76), 8.185 (12.55), 8.464 (0.50), 8.593 (6.42), 8.597 (6.53), 9.362 (3.62), 9.375 (3.50). I-109 [00267] embedded image N-{(1S)-1-[1-(5-amnopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-6-chloro-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 10: R.sub.t = 1.73 min; MS (ESIpos): m/z = 424 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.165 (2.67), 1.177 (5.39), 1.189 (2.74), 1.398 (1.68), 1.591 (16.00), 1.603 (15.91), 1.989 (10.26), 2.087 (0.81), 4.015 (0.82), 4.027 (2.45), 4.039 (2.43), 4.051 (0.81), 5.666 (13.07), 5.682 (1.77), 5.693 (2.28), 5.705 (1.53), 5.747 (0.52), 6.743 (0.50), 6.757 (0.65), 7.143 (3.95), 7.148 (3.86), 7.158 (4.27), 7.162 (4.14), 7.454 (6.66), 7.468 (6.04), 7.602 (13.11), 7.788 (6.84), 7.795 (10.87), 8.004 (13.30), 9.083 (2.63), 9.094 (2.06), 9.277 (0.76). I-110 [00268] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}-N-ethylpyridine-3-carboxamide LC-MS (method 1): R.sub.1 = 1.86 min; MS (ESIpos): m/z = 480 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.141 (4.59), 1.153 (9.47), 1.165 (4.63), 1.664 (7.27), 1.675 (7.24), 3.307 (1.15), 3.319 (4.46), 3.328 (16.00), 3.340 (3.40), 3.352 (0.97), 5.988 (1.12), 6.000 (1.58), 6.012 (1.14), 7.564 (5.78), 7.180 (4.59), 7.990 (2.63), 8.005 (2.78), 8.193 (5.88), 8.455 (1.80), 8.458 (1.85), 8.469 (1.69), 8.472 (1.73), 8.727 (0.83), 8.736 (1.55), 8.745 (0.81), 8.941 (2.86), 8.945 (2.87), 9.204 (2.15), 9.217 (2.05). I-111 [00269] embedded image 6-chloro-N-{(1S)-1-[1-(3-fluoropyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 1): R.sub.t = 1.88 min; MS (ESIpos): m/z = 427 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.654 (16.00), 1.665 (15.84), 2.072 (2.49), 5.248 (0.71), 5.260 (2.66), 5.272 (3.90), 5.283 (2.60), 5.295 (0.67), 7.448 (11.05), 7.679 (1.69), 7.686 (2.80), 7.693 (3.44), 7.700 (3.02), 7.707 (1.85), 7.777 (9.04), 8.082 (2.34), 8.096 (4.07), 8.112 (2.15), 8.211 (10.80), 8.406 (4.74), 8.413 (4.66), 9.113 (4.47), 9.126 (4.34). I-112 [00270] embedded image 6-{5-[(1S)-1-{[7-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridine-3-sulfonamide LC-MS (method 1): R.sub.t = 1.79 min; MS (ESIpos): m/z = 488 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.676 (16.00), 1.687 (15.85), 2.072 (0.60), 3.570 (3.35), 3.643 (3.24), 5.982 (0.64), 5.994 (2.53), 6.006 (3.73), 6.018 (2.47), 6.029 (0.62), 7.466 (8.05), 7.482 (8.58), 7.731 (15.43), 8.126 (6.00), 8.140 (6.55), 8.226 (12.27), 8.457 (4.06), 8.461 (3.95), 8.471 (3.71), 8.475 (3.62), 8.906 (6.63), 8.910 (6.56), 9.401 (4.72), 9.414 (4.54). I-113 [00271] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}-N-(cyclopropylmethyl)-N-methyylpyridine-3-carboxamide LC-MS (method 7): R.sub.t = 1.38 min; MS (ESIpos): m/z = 520 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 0.045 (1.18), 0.297 (1.34), 0.441 (1.23), 0.512 (1.34), 0.935 (0.53), 1.070 (0.52), 1.665 (16.00), 1.677 (15.83), 2.967 (2.55), 3.081 (3.18), 3.369 (1.61), 5.990 (1.64), 6.002 (2.37), 6.014 (1.62), 7.575 (9.47), 7.809 (10.73), 7.840 (0.42), 7.940 (5.56), 7.954 (6.42), 8.131 (1.58), 8.18 (13.70), 8.549 (2.74), 9.179 (4.30), 9.193 (4.11). I-114 [00272] embedded image 7-chloro-N-{(1S)-1-[1-(3-fluoropyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 7): R.sub.t = 1.32 min; MS (ESIpos): m/z = 427 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.654 (16.00), 1.666 (15.90), 3.261 (0.43), 3.270 (0.95), 3.333 (0.41), 3.338 (0.52), 5.246 (0.62), 5.258 (2.54), 5.269 (3.77), 5.281 (2.47), 5.293 (0.56), 7.348 (6.78), 7.469 (6.91), 7.684 (1.59), 7.691 (2.58), 7.698 (3.32), 7.705 (2.80), 7.712 (1.73), 7.838 (0.58), 8.089 (2.08), 8.104 (3.61), 8.119 (1.88), 8.207 (12.31), 8.406 (4.25), 8.414 (4.16), 9.284 (4.21), 9.296 (4.02). I-115 [00273] embedded image 6-chloro-N-{(1S)-1-[1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 1): R.sub.t = 2.07 min; MS (ESIpos): m/z = 409 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.651 (8.43), 1.663 (8.35), 3.571 (16.00), 5.959 (1.24), 5.971 (1.75), 5.983 (1.26), 7.493 (1.35), 7.502 (1.49), 7.506 (1.47), 7.514 (1.45), 7.574 (6.51), 7.807 (5.03), 7.897 (2.43), 7.910 (2.83), 8.090 (1.14), 8.093 (1.21), 8.103 (1.74), 8.106 (1.82), 8.116 (0.99), 8.119 (1.01), 8.147 (6.52), 8.531 (1.66), 8.533 (1.73), 8.539 (1.71), 8.541 (1.68), 9.175 (2.11), 9.188 (2.05). I-116 [00274] embedded image 7-chloro-N-{(1S)-1-[1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 1): R.sub.t = 2.15 min; MS (ESIpos): m/z = 409 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.656 (16.00), 1.668 (15.82), 3.328 (0.41), 3.570 (13.84), 5.982 (1.95), 7.459 (7.58), 7.474 (7.92), 7.498 (2.85), 7.506 (3.17), 7.510 (3.15), 7.518 (2.98), 7.902 (4.70), 7.916 (5.46), 8.094 (2.18), 8.097 (2.15), 8.108 (3.60), 8.120 (1.90), 8.123 (1.79), 8.146 (11.47), 8.542 (3.72), 8.550 (3.65), 9.352 (2.75). I-117 [00275] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethoxy)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridine-3-carbonitrile LC-MS (method 1): R.sub.t = 2.08 min; MS (ESIpos): m/z = 450 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.643 (16.00), 1.655 (15.78), 5.967 (0.65), 5.978 (2.59), 5.990 (3.71), 6.002 (2.51), 6.014 (0.63), 7.328 (7.42), 7.778 (11.53), 8.097 (5.78), 8.111 (6.16), 8.243 (11.94), 8.577 (4.02), 8.580 (3.79), 8.591 (3.85), 8.594 (3.61), 9.046 (6.50), 9.049 (5.84), 9.170 (4.68), 9.183 (4.49). I-118 [00276] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridine-3-sulfonamide LC-MS (method 1): R.sub.t = 1.73 min; MS (ESIpos): m/z = 488 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.671 (16.00), 1.683 (15.88), 5.966 (0.61), 5.978 (2.55), 5.990 (3.68), 6.002 (2.52), 6.013 (0.62), 7.580 (12.86), 7.731 (14.69), 7.819 (10.31), 8.120 (6.08), 8.134 (6.61), 8.226 (13.21), 8.452 (4.13), 8.456 (4.17), 8.467 (3.77), 8.471 (3.84), 8.894 (6.40), 8.898 (6.35), 9.226 (4.62), 9.239 (4.44). I-119 [00277] embedded image 7-chloro-N-{(1S)-1-[1-(4-chloropyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5- (trifluoromethyl)-1,3-benzoxazol-2-amine LC-MS (method 1): R.sub.t = 2.09 min; MS (ESIpos): m/z = 443 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.663 (16.00), 1.674 (15.82), 1.911 (4.05), 1.915 (0.95), 1.933 (0.85), 1.977 (0.70), 2.565 (0.48), 2.735 (8.57), 2.893 (9.75), 3.600 (1.73), 5.364 (0.61), 5.375 (2.48), 5.387 (3.63), 5.399 (2.44), 5.410 (0.59), 7.485 (8.16), 7.493 (7.58), 7.764 (4.17), 7.767 (4.52), 7.773 (4.33), 7.776 (4.55), 7.903 (7.64), 7.906 (7.52), 7.955 (1.42), 8.251 (12.92), 8.578 (7.17), 8.587 (6.87), 9.323 (4.05), 9.336 (3.93). I-120 [00278] embedded image tert-Butyl 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2- yl]amino}ethyl]-1H-1,2,4-triazol-1-yl}pyridine-3-carboxylate LC-MS (method 1): R.sub.t = 2.52 min; MS (ESIpos): m/z = 509 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.398 (1.04), 1.527 (1.76), 1.552 (16.00), 1.665 (2.26), 1.676 (2.24), 1.908 (1.81), 1.944 (0.53), 1.975 (0.52), 1.986 (0.73), 5.745 (1.05), 6.013 (0.52), 7.568 (1.76), 7.816 (1.33), 8.006 (0.88), 8.020 (0.92), 8.218 (1.70), 8.469 (0.57), 8.473 (0.57), 8.483 (0.53), 8.487 (0.53), 8.878 (0.91), 8.882 (0.88), 9.157 (0.45), 9.170 (0.44). I-121 [00279] embedded image 6-{5-[(1S)-1-{[6-chloro-5-(trifluoromethyl)-1,3-benzoxazol-2-yl]amino}ethyl]- 1H-1,2,4-triazol-1-yl}pyridine-3-carboxylic acid LC-MS (method 8): R.sub.t = 0.96 min; MS (ESIpos): m/z = 453 [M + H].sup.+ .sup.1H-NMR (600 MHz, DMSO-d6) δ [ppm]: 1.166 (0.94), 1.178 (1.88), 1.190 (0.96), 1.232 (0.41), 1.499 (0.54), 1.511 (0.56), 1.665 (16.00), 1.677 (15.81), 1.990 (3.60), 4.028 (0.90), 4.039 (0.87), 6.002 (0.70), 6.014 (2.61), 6.026 (3.78), 6.038 (2.55), 6.049 (0.68), 7.65 (11.86), 7.814 (9.25), 8.027 (6.07), 8.041 (6.23), 8.213 (11.67), 8.520 (4.18), 8.524 (4.02), 8.535 (3.99), 8.538 (3.79), 8.984 (6.80), 8.987 (6.67), 9.204 (3.43), 9.217 (3.25), 13.572 (1.15).

Biological Examples

[0638] Boophilus microplus—Injection Test (BOOPMI Injection)

[0639] Solvent: dimethyl sulfoxide

[0640] 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 solvent to the desired concentration.

[0641] Five adult engorged female ticks (Boophilus microplus) are injected with 1 μL compound solution into the abdomen. The ticks are transferred into replica plates and incubated in a climate chamber.

[0642] After 7 days egg deposition of fertile eggs is monitored. Eggs where fertility is not visible are stored in a climate chamber till hatching after about 42 days. An efficacy of 100% means all eggs are infertile; 0% means all eggs are fertile.

[0643] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 μg/animal: I-001, I-005, I-006, I-010, I-011, I-012, I-014, I-015, I-016, I-017, I-018, I-019, I-021, I-026, I-027, I-030, I-032, I-034, I-036, I-039, I-045, I-047, I-051, I-052, I-053, I-054, I-055, I-056, I-062, I-063, I-065, I-066, I-067, I-068, I-073, I-075, I-076, I-077, I-084, I-089, I-090, I-091, I-092, I-094.

[0644] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 20 μg/animal I-008, I-050, I-064.

[0645] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 4 μg/animal: I-001, I-005, I-006, I-011, I-012, I-014, I-017, I-018, I-021, I-026, I-027, I-034, I-036, I-039, I-040, I-044, I-045, I-047, I-052, I-053, I-062, I-065, I-066, I-067, I-068, I-069, I-075, I-076, I-077, I-084, I-089, I-094.

[0646] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 4 μg/animal I-015, I-030, I-035, I-038, I-050, I-055, I-056, I-057, I-063, I-074, I-079, I-090.

[0647] Rhipicephalus microplus—In-Vitro Contact Tests Larval Cattle Tick (Strain Parkhurst, Resistant Against Synthetic Pyrethroids) (BOOPMI Contact)

[0648] 9 mg compound is solved in 1 ml acetone and diluted with acetone to the desired concentration. 250 μL of the test solution is filled in 25 ml glass test tubes and homogeneously distributed on the inner walls by rotation and tilting on a shaking device (2 h at 30 rpm). With a compound concentration of 900 ppm, an inner surface of 44.7 cm.sup.2 and a homogeneous distribution, a dose of 5 μg/cm.sup.2 is achieved.

[0649] After the solvent has evaporated, each test tube is filled with 20-50 cattle tick larvae (Rhipicephalus microplus), closed with a perforated lid and incubated in a horizontal position at 85% relative humidity and 27° C. in an incubator. After 48 hours efficacy is determined. The larvae are patted on the ground of the tubes and negative geotactic behaviour is recorded. Larvae that climb back to the top of the vial in a manner comparable to untreated control larvae are marked as alive, larvae not climbing back up comparable to untreated control larvae but are moving uncoordinatedly or only twitching their legs are marked as moribund, tick larvae remaining on the bottom and not moving at all are counted as dead.

[0650] A compound shows a good efficacy against Rhipicephalus microplus, if at a compound concentration of 5 μg/cm.sup.2 an efficacy of at least 80% is monitored. An efficacy of 100% means all larvae are dead or moribund; 0% means no larvae are dead or moribund.

[0651] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-001, I-005, I-006, I-007, I-013, I-014, I-015, I-016, I-017, I-019, I-020, I-026, I-027, I-029, I-033, I-036, I-044, I-047, I-049, I-054, I-055, I-057, I-058, I-059, I-060, I-061, I-062, I-073, I-080, I-082, I-083, I-085, I-087, I-088, I-090, I-092, I-093, I-097.

[0652] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-034, I-039, I-040, I-042, I-066, I-072, I-076, I-081, I-086, I-091, I-096.

[0653] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-008, I-011, I-018, I-021, I-037, I-041, I-045, I-046, I-051, I-056, I-068, I-069, I-084, I-095.

[0654] Ctenocephalides felis—In-Vitro Contact Tests Adult Cat Flea

[0655] 9 mg compound is solved in 1 ml acetone and diluted with acetone to the desired concentration. 250 of the test solution is filled in 25 ml glass test tubes and homogeneously distributed on the inner walls by rotation and tilting on a shaking device (2 h at 30 rpm). With a compound concentration of 900 ppm, an inner surface of 44.7 cm.sup.2 and a homogeneous distribution, a dose of 5 μg/cm.sup.2 is achieved.

[0656] After the solvent has evaporated, each test tube is filled with 5-10 adult cat fleas (Ctenocephalides felis), closed with a perforated lid and incubated in a lying position at room temperature and relative humidity. After 48 hours efficacy is determined. The fleas are patted on the ground of the tubes and are incubated on a heating plate at 45-50° C. for at most 5 minutes Immotile or uncoordinated moving fleas, which are not able to escape the heat by climbing upwards, are marked as dead or moribund.

[0657] A compound shows a good efficacy against Ctenocephalides felis, if at a compound concentration of 5 μg/cm.sup.2 an efficacy of at least 80% is monitored. An efficacy of 100% means all fleas are dead or moribund; 0% means no fleas are dead or moribund.

[0658] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-001, I-005, I-006, I-017, I-019, I-040, I-045, I-052, I-057, I-058, I-059, I-060, I-061, I-062, I-065, I-074, I-079, I-081, I-082, I-084, I-085, I-093, I-094, I-096, I-097, I-098.

[0659] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-042, I-049, I-070, I-071, I-092.

[0660] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-014, I-036, I-083.

[0661] Ctenocephalides felis—Oral Test (CTECFE)

[0662] Solvent: dimethyl sulfoxide

[0663] 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 cattle blood to the desired concentration.

[0664] Approximately 20 adult unfed cat fleas (Ctenocephalides felis) are placed in flea chambers. The blood chamber, sealed with parafilm on the bottom, are filled with cattle blood supplied with compound solution and placed on the gauze covered top of the flea chamber, so that the fleas are able to suck the blood. The blood chamber is heated to 37° C. whereas the flea chamber is kept at room temperature.

[0665] After 2 days mortality in % is determined. 100% means all the fleas have been killed; 0% means none of the fleas have been killed.

[0666] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 ppm: I-001, I-005, I-006, I-007, I-010, I-011, I-012, I-014, I-026, I-034, I-035, I-036, I-039, I-040, I-044, I-045, I-048, I-053, I-056, I-057, I-065, I-069, I-070, I-071, I-072, I-074, I-076, I-078, I-079, I-092, I-093, I-094, I-095, I-096.

[0667] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 ppm: I-013, I-033, I-041, I-050, I-073.

[0668] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 100 ppm: I-067, I-075.

[0669] Rhipicephalus sanguineus—In-Vitro Contact Tests with Adult Brown Dog Ticks (RHIPSA Contact)

[0670] 9 mg compound is solved in 1 ml acetone and diluted with acetone to the desired concentration. 250 μl_, of the test solution is filled in 25 ml glass test tubes and homogeneously distributed on the inner walls by rotation and tilting on a shaking device (2 h at 30 rpm). With a compound concentration of 900 ppm, an inner surface of 44.7 cm.sup.2 and a homogeneous distribution, a dose of 5 μg/cm.sup.2 is achieved.

[0671] After the solvent has evaporated, each test tube is filled with 5-10 adult brown dog ticks (Rhipicephalus sanguineus), closed with a perforated lid and incubated in a lying position at room temperature and relative humidity. After 48 hours efficacy is determined. The ticks are patted on the ground of the tubes and are incubated on a heating plate at 45-50° C. for at most 5 minutes Immotile or uncoordinated moving ticks, which are not able to escape the heat by climbing upwards, are marked as dead or moribund.

[0672] A compound shows a good efficacy against Rhipicephalus sanguineus, if at a compound concentration of 5 μg/cm.sup.2 an efficacy of at least 80% is monitored. An efficacy of 100% means all ticks are dead or moribund; 0% means no ticks are dead or moribund.

[0673] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-001, I-034, I-036, I-039, I-040, I-045, I-047, I-049, I-055, I-059, I-062, I-065, I-081, I-082, I-083, I-085, I-090, I-096.

[0674] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-011, I-031, I-060, I-061, I-066, I-067, I-084, I-097.

[0675] Diabrotica balteata—Spray Test

[0676] Solvent: 78.0 parts by weight of acetone [0677] 1.5 parts by weight of dimethylformamide

[0678] Emulsifier: alkylarylpolyglycol ether

[0679] 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, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0680] Soaked wheat seeds (Triticum aestivum) are placed in a multiple well plate filled with agar and some water and are incubated for 1 day to germinate (5 seeds per well). The germinated wheat seeds are sprayed with a test solution containing the desired concentration of the active ingredient. Afterwards each unit is infected with 10-20 larvae of the banded cucumber beetle (Diabrotica balteata).

[0681] After 7 days efficacy in % is determined. 100% means all the seedlings have grown up like in the untreated, uninfected control; 0% means none of the seedlings have grown.

[0682] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha (=160 μg/well): I-001, I-005, I-006, I-010, I-011, I-013, I-014, I-015, I-016, I-017, I-018, I-019, I-021, I-026, I-039, I-045, I-047, I-052, I-053, I-055, I-062, I-064, I-065, I-066, I-084, I-088, I-090.

[0683] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 500 g/ha (=160 μg/well): I-003, I-009, I-034, I-063, I-067.

[0684] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 g/ha: I-011, I-014, I-016, I-017, I-018, I-019, I-021, I-034, I-035, I-036, I-039, I-040, I-041, I-044, I-045, I-047, I-055, I-058, I-059, I-060, I-061, I-062, I-063, I-064, I-065, I-069, I-070, I-071, I-078, I-079, I-081, I-082, I-085, I-094, I-098, I-100, I-101, I-102, I-103.

[0685] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 100 g/ha: I-010, I-049, I-083.

[0686] Meloidogyne incognita—Test

[0687] Solvent: 125.0 parts by weight of acetone

[0688] 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.

[0689] 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.

[0690] After 14 days the nematicidal activity is determined based on 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.

[0691] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 20 ppm: I-046, I-087, I-088, I-091.

[0692] Myzus persicae—Oral Test

[0693] Solvent: 100 parts by weight acetone

[0694] 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.

[0695] 50 μl compound solution is filled in microtiter plates and 150 μl IPL41 insect medium (33%+15% sugar) is added to obtain a total volume of 200 μl per well. Afterwards the plates are sealed with parafilm through which a mixed population of the green peach aphid (Myzus persicae) can suck on the compound preparation.

[0696] After 5 days mortality in % is determined. 100% means all aphids have been killed and 0% means none of the aphids have been killed.

[0697] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 4 ppm: I-001, I-061, I-082.

[0698] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 4 ppm: I-005, I-006, I-011, I-017, I-037, I-059, I-060, I-081, I-086, I-100.

[0699] Myzus persicae—Spray Test

[0700] Solvent: 78.0 parts by weight acetone [0701] 1.5 parts by weight dimethylformamide

[0702] Emulsifier: alkylarylpolyglycol ether

[0703] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0704] Chinese cabbage (Brassica pekinensis) leaf disks infected with all instars of the green peach aphid (Myzus persicae), are sprayed with a preparation of the active ingredient of the desired concentration.

[0705] After 5 days mortality in % is determined. 100% means all aphids have been killed and 0% means none of the aphids have been killed.

[0706] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-013.

[0707] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500 g/ha: I-091.

[0708] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 g/ha: I-081, I-085, I-092, I-093.

[0709] Nezara viridula—Spray Test

[0710] Solvent: 78.0 parts by weight of acetone [0711] 1.5 parts by weight of dimethylformamide

[0712] Emulsifier: alkylarylpolyglycol ether

[0713] 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, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0714] Barley plants (Hordeum vulgare) are sprayed with a test solution containing the desired concentration of the active ingredient and are infested with larvae of the southern green stink bug (Nezara viridula).

[0715] After 4 days, mortality in % is determined. 100% means all the stink bugs have been killed; 0% means none of the stink bugs have been killed.

[0716] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-017.

[0717] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 g/ha: I-085.

[0718] Nilaparvata lugens—Spray Test

[0719] Solvent: 78.0 parts by weight of acetone [0720] 1.5 parts by weight of dimethylformamide

[0721] Emulsifier: alkylarylpolyglycol ether

[0722] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0723] Rice plants (Oryza sativa) are sprayed with a preparation of the active ingredient of the desired concentration and the plants are infested with the brown planthopper (Nilaparvata lugens).

[0724] After 4 days mortality in % is determined. 100% means all planthoppers have been killed and 0% means none of the planthoppers have been killed.

[0725] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-007, I-009.

[0726] Spodoptera frugiperda—Spray Test

[0727] Solvent: 78.0 parts by weight acetone [0728] 1.5 parts by weight dimethylformamide

[0729] Emulsifier: alkylarylpolyglycol ether

[0730] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0731] Maize (Zea mays) leaf sections are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf sections are infested with fall armyworm larvae (Spodoptera frugiperda).

[0732] After 7 days mortality in % is determined. 100% means all caterpillars have been killed and 0% means none of the caterpillars have been killed.

[0733] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-001, I-005, I-006, I-010, I-011, I-012, I-014, I-015, I-016, I-017, I-018, I-019, I-026, I-027, I-032, I-033, I-034, I-039, I-045, I-047, I-052, I-054, I-055, I-062, I-090.

[0734] In this test, for example, the following compounds from the preparation examples showed good activity of 83% at an application rate of 500 g/ha: I-088.

[0735] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 g/ha: I-001, I-005, I-006, I-017, I-018, I-026, I-034, I-036, I-043, I-044, I-045, I-047, I-049, I-055, I-057, I-059, I-061, I-062, I-069, I-070, I-081, I-082, I-083, I-085, I-098, I-100, I-102.

[0736] In this test, for example, the following compounds from the preparation examples showed good activity of 83% at an application rate of 100 g/ha: I-058, I-060.

[0737] Tetranychus urticae—Spray Test OP-Resistant

[0738] Solvent: 78.0 parts by weight acetone [0739] 1.5 parts by weight dimethylformamide

[0740] Emulsifier: alkylarylpolyglycol ether

[0741] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

[0742] French bean (Phaseolus vulgaris) leaf disks infected with all instars of the two spotted spidermite (Tetranychus urticae) are sprayed with a preparation of the active ingredient of the desired concentration.

[0743] After 6 days mortality in % is determined. 100% means all spider mites have been killed and 0% means none of the spider mites have been killed.

[0744] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500 g/ha: I-016, I-067.

[0745] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 g/ha: I-085.

[0746] Aedes aegypti Test (AEDSAE Surface Treatment & Contact Assay)

[0747] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

[0748] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/mL/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Aedes aegypti strain MONHEIM are placed onto the dried surface. The exposure time is 30 minutes.

[0749] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.

[0750] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-001, I-005, I-017, I-059, I-061, I-081.

[0751] The following examples showed in this test efficacy of 85-100% at a surface concentration of 4 mg/m.sup.2: I-001, I-006, I-017, I-059, I-061, I-081.

[0752] Culex quinquefasciatus Test (CULXFA Surface Treatment & Contact Assay)

[0753] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

[0754] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/mL/RME 2 000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Culex quinquefasciatus strain P00 are placed onto the dried surface. The exposure time is 30 minutes.

[0755] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.

[0756] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-001, I-005.

[0757] The following examples showed in this test efficacy of 90-100% at a surface concentration of 4 mg/m.sup.2: I-001.

[0758] Anopheles funestus Test (ANPHFU Surface Treatment & Contact Assay)

[0759] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

[0760] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/mL/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Anopheles funestus strain FUMOZ-R (Hunt et al., Med. Vet. Entomol. 2005 September; 19(3): 271-275) are placed onto the dried surface. The exposure time is 30 minutes.

[0761] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.

[0762] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-005, I-017, I-059, I-081.

[0763] The following examples showed in this test efficacy of 85-100% at a surface concentration of 4 mg/m.sup.2: I-017, I-059, I-061, I-081.

[0764] Musca domestica Test (MUSCDO Surface Treatment & Contact Assay)

[0765] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)

[0766] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/mL/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult flies of the species Musca domestica strain WHO-N are placed onto the dried surface. The exposure time is 30 minutes.

[0767] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.

[0768] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-001, I-017, I-081.

[0769] The following examples showed in this test efficacy of 90-100% at a surface concentration of 4 mg/m.sup.2: I-017, I-059, I-061, I-081.

NOVEL HETEROARYL-SUBSTITUTED AMINOALKYL AZOLE COMPOUNDS AS PESTICIDES

Inventors

Cpc classification

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C07D401/14

CHEMISTRY; METALLURGY

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A01N43/653

HUMAN NECESSITIES

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A01N43/76

HUMAN NECESSITIES

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C07D417/14

CHEMISTRY; METALLURGY

Classification Explorer

C07D403/14

CHEMISTRY; METALLURGY

Classification Explorer

A01N43/78

HUMAN NECESSITIES

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C07D413/14

CHEMISTRY; METALLURGY

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A01N43/90

HUMAN NECESSITIES

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C07D471/04

CHEMISTRY; METALLURGY

International classification

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C07D413/14

CHEMISTRY; METALLURGY

Classification Explorer

A01N43/653

HUMAN NECESSITIES

Classification Explorer

A01N43/76

HUMAN NECESSITIES

Classification Explorer

A01N43/78

HUMAN NECESSITIES

Classification Explorer

A01N43/90

HUMAN NECESSITIES

Classification Explorer

C07D403/14

CHEMISTRY; METALLURGY

Classification Explorer

C07D417/14

CHEMISTRY; METALLURGY

Classification Explorer

C07D471/04

CHEMISTRY; METALLURGY

Abstract

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Description