N-arylamidine-substituted trifluoroethyl sulfide derivatives as acaricides and insecticides

Abstract

The present invention relates to novel N-arylamide-substituted trifluoroethyl sulfide derivatives of the formula (I) ##STR00001## in which X.sup.1, X.sup.2, X.sup.3, X.sup.4, R.sup.1, R.sup.2, R.sup.3, n have the meanings given in the descriptionto their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation.

Claims

1. An N-arylamidine-substituted trifluoroethyl sulfide derivative of formula (I) ##STR00533## in which n represents the number 0, 1 or 2, X.sup.1, X.sup.2, X.sup.3, X.sup.4 independently of one another represent hydrogen, halogen, hydroxy, amino, OCN, SCN, SF.sub.5, trialkylsilyl, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxycarbonylalkyl, alkoxyalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkoxy, haloalkoxy, cyanoalkoxy, hydroxycarbonylalkoxy, alkoxycarbonylalkoxy, alkoxyalkoxy, alkylhydroxyimino, alkoxyimino, alkylalkoxyimino, haloalkylalkoxyimino, alkylthio, haloalkylthio, alkoxyalkylthio, alkylthioalkyl, alkylsulfinyl, haloalkylsulfinyl, alkoxyalkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, haloalkylsulfonyl, alkoxyalkylsulfonyl, alkylsulfonylalkyl, alkylsulfonyloxy, alkylcarbonyl, haloalkylcarbonyl, carboxyl, alkylcarbonyloxy, alkoxycarbonyl, haloalkoxycarbonyl, alkoxycarbonylalkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, cycloalkylaminocarbonyl, alkyl sulfonylamino, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfoximino, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, or represent optionally substituted phenylalkyl, phenoxy, phenylalkyloxy, phenoxyalkyl, phenylthio, phenylthioalkyl, phenylsulfinyl, phenylsulfonyl, hetarylalkyl, hetaryloxy, hetarylalkyloxy, hetarylthio, hetarylsulfinyl, hetarylsulfonyl, or represent optionally substituted saturated or unsaturated cycloalkylalkyl, cycloalkyloxy, cycloalkylalkoxy, cycloalkylthio, cycloalkylalkylthio, cycloalkylsulfinyl, cycloalkylalkylsulfinyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl, or represent NR.sup.4R.sup.5, where R.sup.4 and R.sup.5 independently of one another represent hydrogen, cyano, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, acyl, alkoxycarbonyl, or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached may form an optionally substituted saturated or unsaturated five- to eight-membered ring which is optionally interrupted by heteroatoms from the group consisting of O, S and N, or represent a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N, or X.sup.2 and X.sup.3 or X.sup.3 and X.sup.4, form, together with the carbon atoms to which they are attached, a 5- or 6-membered ring which is optionally substituted and optionally interrupted by heteroatoms from the group consisting of O, S, N and CO, R.sup.3 represents alkoxyalkul, cyanoalkyl, alkylthioalkyl, haloalkenyl, alkynyl, haloalkynyl, or represent a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcabonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N, or represents a 3- to 6-membered aromatic ring which contains one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkyl sulfinyl, alkylsulfonyl, alkyl sulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcabonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N, R.sup.1 and R.sup.2 independently of one another represent hydrogen, cyano, alkyl, haloalkyl, alkoxy, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, represent optionally substituted alkylcarbonyl, alkoxycarbonyl, arylcarbonyl, hetarylcarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, alkylsulfinyl, haloalkylsulfinyl, arylsulfinyl, arylalkylsulfinyl, hetarylsulfinyl, hetarylalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, arylsulfonyl, arylalkylsulfonyl, hetarylsulfonyl, hetarylalkylsulfonyl, or represent a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once or twice by CO, SO or SO.sub.2 and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N, or represent (CH.sub.2).sub.mR.sup.6, O(CH.sub.2).sub.mR.sup.6, (CH.sub.2).sub.mOR.sup.6, where R.sup.6 represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once or twice by CO and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N, where m represents the number 1, 2, 3 or 4, or R.sup.1 and R.sup.2 may also form, together with the nitrogen atom to which they are attached, a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may optionally contain one or more further heteroatoms from the group consisting of sulfur, oxygen (where oxygen atoms must not be directly adjacent to one another) and nitrogen and/or optionally at least one carbonyl group, or R.sup.1 and R.sup.3 together with the atoms to which they are attached represent one of the following groups, ##STR00534## each of which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, where the arrow points to the remainder of the molecule, and/or a diastereomer, enantiomer, rotamer, tautomer and/or salt thereof.

2. The compound as claimed in claim 1, where n represents the number 0, 1 or 2, X.sup.1, X.sup.2, X.sup.3, X.sup.4 independently of one another represent hydrogen, halogen, hydroxy, amino, OCN, SCN, SF.sub.5, tri-(C.sub.1-C.sub.6)-alkylsilyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, hydroxycarbonyl-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-cyanoalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-cyanoalkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-cyanoalkoxy, (C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.7)-alkylhydroxyimino, (C.sub.1-C.sub.7)-alkoxyimino, (C.sub.1-C.sub.6)-alkyl-(C.sub.1-C.sub.7)-alkoxyimino, (C.sub.1-C.sub.6)-haloalkyl-(C.sub.1-C.sub.7)-alkoxyimino, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.1-C.sub.7)-haloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy, (C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.1-C.sub.7)-haloalkoxycarbonyl, (C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aminocarbonyl, (C.sub.1-C.sub.7)-alkylaminocarbonyl, di-(C.sub.1-C.sub.7)-alkylaminocarbonyl, (C.sub.1-C.sub.7)-alkenylaminocarbonyl, di-(C.sub.1-C.sub.7)-alkenylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)-alkylsulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)-alkylaminosulfonyl, di-(C.sub.1-C.sub.6)-alkylaminosulfonyl, (C.sub.1-C.sub.6)-alkylsulfoximino, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, or represent phenyl-(C.sub.1-C.sub.6)-alkyl, phenoxy, phenyl-(C.sub.1-C.sub.4)-alkyloxy, phenoxy-(C.sub.1-C.sub.4)-alkyl, phenylthio, phenylthio-(C.sub.1-C.sub.4)-alkyl, phenylsulfinyl, phenylsulfonyl, hetaryl-(C.sub.1-C.sub.6)-alkyl, hetaryloxy, hetaryl-(C.sub.1-C.sub.4)-alkyloxy, hetarylthio, hetarylsulfinyl, hetarylsulfonyl, optionally saturated or unsaturated (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylthio, (C.sub.3-C.sub.8)-cycloalkylsulfinyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.3-C.sub.8)-cycloalkylsulfonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylsulfonyl, substituted by optionally saturated or unsaturated (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy optionally substituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, (C.sub.1-C.sub.7)-alkylcarbonylamino, (C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy, aminocarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.3-C.sub.8)-cycloalkylamino, (C.sub.1-C.sub.6)-alkylsulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)-alkylaminosulfonyl and di-(C.sub.1-C.sub.6)-alkylaminosulfonyl and optionally interrupted by one or two heteroatoms from the group consisting of O, S and N, or represent NR.sup.4R.sup.5, where R.sup.4 and R.sup.5 independently of one another represent hydrogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-(C .sub.1-C.sub.6)-thioalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-cyanoalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)- haloalkynyl, (C.sub.2-C.sub.8)-cyanoalkynyl, acyl, (C.sub.1-C.sub.7)-alkoxycarbonyl, or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached may form a saturated or unsaturated five- to seven-membered ring which is optionally substituted by identical or different substituents from the group consisting of halogen, cyano, hydroxy, amino, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy or by (C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl optionally substituted by identical or different substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkyl and optionally interrupted by heteroatoms from the group consisting of O, S and N and is optionally interrupted by heteroatoms from the group consisting of O, S and N, or represent (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.3-C.sub.8)-cycloalkenyl, phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, pyrazolyl or triazolyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, or by (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy, optionally substituted by halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkyl and optionally interrupted by heteroatoms from the group consisting of O, S and N, or X.sup.2 and X.sup.3 or X.sup.3 and X.sup.4 may form the following 5- or 6-membered rings which are optionally substituted by identical or different substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, ##STR00535## or X.sup.2 and X.sup.3 or X.sup.3 and X.sup.4 may form the following fused rings which are optionally mono- or polysubstituted by identical or different substituents, where the substituents independently of one another may be selected from the group consisting of hydrogen, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfonyl, amino, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino and (C.sub.3-C.sub.8)-cycloalkylamino, ##STR00536## R.sup.3 represents (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, or represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, (C.sub.1-C.sub.7)-alkylcarbonylamino, (C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy, aminocarbonyl, (C.sub.1-C.sub.7)-arylaminocarbonyl, di-(C.sub.1-C.sub.6)alkyl-aminocarbonyl, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.3-C.sub.6)-cycloalkylamino, (C.sub.1-C.sub.6)-alkyl sulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)-alkylaminosulfonyl and di-(C.sub.1-C.sub.6)-alkylaminosulfonyl, or substituted by (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy optionally substituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy and optionally interrupted by heteroatoms from the group consisting of O, S and N, or represents a 3- to 6-membered aromatic ring which contains one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)- haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkyl sulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylthio, (C .sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, (C.sub.1-C.sub.7)-alkylcarbonylamino, (C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy, aminocarbonyl, (C.sub.1-C.sub.7)-arylaminocarbonyl, di-(C.sub.1-C.sub.6)alkyl-aminocarbonyl, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.3-C.sub.6)-cycloalkylamino, (C.sub.1-C.sub.6)-alkylsulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)-alkylaminosulfonyl and di-(C.sub.1-C.sub.6)-alkylaminosulfonyl, or substituted by (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy optionally substituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy and optionally interrupted by heteroatoms from the group consisting of O, S and N, R.sup.1 and R.sup.2 independently of one another represent hydrogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-cyanoalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-cyanoalkynyl, represent (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.7)-alkoxycarbonyl, arylcarbonyl, hetarylcarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfinyl, arylsulfinyl, aryl-(C.sub.1-C.sub.6)-alkylsulfinyl, hetarylsulfinyl, hetaryl-(C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, arylsulfonyl, aryl-(C.sub.1-C.sub.6)-alkylsulfonyl, hetarylsulfonyl, hetaryl-(C.sub.1-C.sub.6)-alkylsulfonyl optionally substituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, or represent a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N, which may optionally be interrupted one or twice by CO, SO or SO.sub.2 and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, (C.sub.1-C.sub.7)-alkylcarbonylamino, (C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy, aminocarbonyl, (C.sub.1-C.sub.7)-arylaminocarbonyl, di-(C.sub.1-C.sub.7)-alkylaminocarbonyl, aminothiocarbonyl, (C.sub.1-C.sub.7)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.7)-alkylaminothiocarbonyl, (C.sub.3-C.sub.8)-cycloalkylamino, (C.sub.1-C.sub.6)-alkyl sulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)-alkylaminosulfonyl and di-(C.sub.1-C.sub.6)-alkylaminosulfonyl, or by (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy optionally interrupted by heteroatoms from the group consisting of O, S and N, or represent (CH.sub.2).sub.mR.sup.6, O(CH.sub.2).sub.mR.sup.6, (CH.sub.2).sub.mOR.sup.6, where R.sup.6 represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once or twice by CO and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)alkylamino, (C.sub.1-C.sub.7)-alkylcabonylamino, (C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy, aminocarbonyl, (C.sub.1-C.sub.7)-alkylaminocarbonyl, di-(C.sub.1-C.sub.7)-alkylaminocarbonyl, aminothiocarbonyl, (C.sub.1-C.sub.7)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.7)alkylaminothiocarbonyl, (C.sub.3-C.sub.8)-cycloalkylamino, (C.sub.1-C.sub.6)-alkyl sulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)-alkylaminosulfonyl or di-(C.sub.1-C.sub.6)-alkylaminosulfonyl, or by identical or different substituents from the group consisting of (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl and (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy optionally substituted by halogen, cyano, nitro, hydroxy, amino, carboxy, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, (C.sub.1-C.sub.7)-alkylcabonylamino, (C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy, aminocarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.3-C.sub.8)-cycloalkylamino, (C.sub.1-C.sub.6)-alkyl sulfonylamino, aminosulfonyl, (C.sub.1-C.sub.6)-alkylaminosulfonyl or di-(C.sub.1-C.sub.6)-alkylaminosulfonyl and optionally interrupted by heteroatoms from the group consisting of O, S and N, where m represents the number 1, 2 or 3, or R.sup.1 and R.sup.2 together with the atoms to which they are attached may form a saturated or unsaturated 4- to 8-membered ring which is optionally mono- or polysubstituted by (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, halogen, (C.sub.1-C.sub.4)-haloalkyl and which may optionally contain one or two further heteroatoms from the group consisting of sulfur, oxygen and nitrogen (where oxygen atoms must not be directly adjacent to one another) and/or at least one carbonyl group, or R.sup.1 and R.sup.3 together with the atoms to which they are attached represent one of the following groups, ##STR00537## each of which may optionally be mono- or distributed by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methycyclopropyl, where the arrow point to the remainder of the molecule.

3. The compound as claimed in claim 1, where n represents the number 0 or 1, X.sup.1, X.sup.2, X.sup.3, X.sup.4 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, aminothiocarbonyl, or represent phenyl-(C.sub.1-C.sub.4)-alkyl, phenoxy, hetaryl-(C.sub.1-C.sub.4)-alkyl, hetaryloxy, optionally saturated or unsaturated (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkyloxy, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.4)-alkoxy, optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or by optionally saturated or unsaturated (C.sub.3-C.sub.6)-cycloalkyl which is optionally interrupted by a heteroatom from the group consisting of O, S and N, or represent (C.sub.3-C.sub.6)-cycloalkyl, phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, pyrazolyl, triazolyl or tetrazolyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.3-C.sub.6)-cycloalkyl, or X.sup.2 and X.sup.3 or X.sup.3 and X.sup.4 may form the following 5- or 6-membered ring which are optionally mono- to tetrasubstituted by fluorine or (C.sub.1-C.sub.4)-alkyl, ##STR00538## or X.sup.2 and X.sup.3 or X.sup.3 and X.sup.4 may form the fused rings below which are optionally monosubstituted or two by identical or different substituents, where the substituents independently of one another may be selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, (C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, ##STR00539## R.sup.3 represents (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-cyanoalkyl, or represents a 3- to 6-membered saturated or partially saturated or ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N and which is optionally mono- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, or substituted by (C.sub.3-C.sub.6)-cycloalkyl, or represents a 3- to 6-membered aromatic ring which contains one to two heteroatoms from the group consisting of O, S and N and which is optionally mono- or trisubstituted by identical or different sub stituents from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, or substituted by (C.sub.3-C.sub.6)-cyclalkyl, R.sup.1 and R.sup.2 independently of one another represent hydrogen, cyano, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-hydroxyalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, represent (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.5)-alkoxycarbonyl, arylcarbonyl, thiophenylcarbonyl, pyridylcarbonyl, pyrimidylcarbonyl, thiazolylcarbonyl, pyrazolylcarbonyl, (C.sub.1-C.sub.4)-alkylsulfinyl, (C.sub.1-C.sub.4)-haloalkylsulfinyl, arylsulfinyl, aryl-(C.sub.1-C.sub.4)-alkylsulfinyl, hetarylsulfinyl, hetaryl-(C.sub.1-C.sub.4)-alkylsulfinyl, (C.sub.1-C.sub.4)-alkylsulfonyl, (C.sub.1-C.sub.4)-haloalkylsulfonyl, arylsulfonyl, aryl-(C.sub.1-C.sub.4)-alkylsulfonyl, hetarylsulfonyl, hetaryl-(C.sub.1-C.sub.4)-alkylsulfonyl optionally mono- to trisubstituted independently of one another by substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylsulfinyl, (C.sub.1-C.sub.4)-alkylsulfonyl, (C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, or represents a 3- to 6-membered saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once or twice by CO and which is optionally mono- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, or represents (CH.sub.2).sub.mR.sup.6, (CH.sub.2).sub.mOR.sup.6, where R.sup.6 represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once or twice by CO and which is optionally mono- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, where m represents the number 1 or 2, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached may form a saturated or unsaturated 3- to 6-membered ring which is optionally mono- or tetrasubstituted by fluorine, chlorine, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkyl and which may optionally contain a further heteroatom from the group consisting of sulfur, oxygen and nitrogen and/or at least one carbonyl group, or R.sup.1 and R.sup.3 together with the atoms to which they are attached represent one of the following groups, ##STR00540## each of which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, where the arrow points to the remainder of the molecule.

4. The compound as claimed in claim 1, where n represents the number 0 or 1, X.sup.1 and X.sup.3 represent hydrogen, X.sup.2 and X.sup.4 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, OCH.sub.2CF.sub.3, R.sup.2 represents hydrogen, methyl or ethyl, R.sup.1 and R.sup.3 together with the atoms to which they are attached represent one of the following groups, ##STR00541## each of which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, where the arrow points to the remainder of the molecule.

5. A compound of formula (I) ##STR00542## where n represents the number 0 or 1, X.sup.1 and X.sup.3 represent hydrogen, X.sup.2 and X.sup.4 independently of one another represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, OCH.sub.2CF.sub.3, aminothiocarbonyl, or phenylmethyl, phenoxy, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl, pyrazolylmethyl, pyridyloxy, pyrimidyloxy, thiazolyloxy, pyrazolyloxy, cyclopropylmethyl, cyclopropylmethoxy, optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifloromethoxy, difluoromethoxy or cyclopropyl, or represents (C.sub.3-C.sub.6)-cycloalkyl, phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, pyrazolyl, triazolyl or tetrazolyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy or by cyclopropyl, optionally X.sup.2 and X.sup.4 represent the following combinations X.sup.2/X.sup.4: F/F, Cl/Cl, F/Cl, Cl/F, Br/Br, Br/Cl, Cl/Br, Br/F, F/Br, methyl/methyl, methyl/F, F/methyl, methyl/Cl, Cl/methyl, methyl/Br, Br/methyl, ethyl/ethyl, ethyl/F, F/ethyl, ethyl/Cl, Cl/ethyl, ethyl/Br, Br/ethyl, methoxy/methyl, methyl/methoxy, methyl/H, ethyl/H, chlorine/H, bromine/H, fluorine/H, methoxy/H, H/chlorine, H/fluorine, H/bromine, H/methyl, H/methoxy, H/ethyl R.sup.3 represents hydrogen, ethyl, propyl, cyano, trifluoromethyl, difluoromethyl, dichloromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, (2,2,2)-trifluoroethyl, 2-chloro-(2,2)-difluoroethyl, (2,2)-dichloro-2-fluoroethyl, (2,2,2)-trichloroethyl, pentafluoroethyl, methoxymethyl, methoxyethyl, cyanomethyl, allyl, butenyl, or represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N and which may optionally be mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, optionally the following rings are explicitly mentioned: cyclopropyl, phenyl, pyridyl, pyrimidyl, thiazolyl, pyrazolyl and thienyl which may optionally be substituted by the substituents mentioned, R.sup.1 represents cyano, cyanomethyl, methylcarbonyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, methoxycarbonyl, ethoxycarbonyl, represents arylcarbonyl, pyridylcarbonyl, pyrimidylcarbonyl, thiazolylcarbonyl, pyrazolylcarbonyl, methylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, allyl, butenyl, methoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methylamino, dimethylamino, or represents oxetanyl, thietanyl, trimethylenesulfonyl, trimethylenesulfinyl, oxanyl or thianyl which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl which are optionally mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, R.sup.2 represents hydrogen, methyl or ethyl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached may form a saturated or unsaturated 3- to 6-membered ring which is optionally mono-, di-, tri- or tetrasubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl and which contains one or two further heteroatoms from the group consisting of sulfur and nitrogen, or together with the nitrogen atom to which they are attached may form a saturated or unsaturated 4-membered ring which is optionally mono-, di-, tri- or tetrasubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl and which optionally contains one further heteroatom from the group consisting of oxygen, sulfur and nitrogen, optionally the following rings are explicitly mentioned, ##STR00543## in which the nitrogen atom to which R.sup.1 and R.sup.2 are attached represent the cycle and the arrow points to the remainder of the molecule, which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl and/or a diastereomer, enantiomer, rotamer, tautomer and/or salt thereof.

6. A compound, of formula (I) ##STR00544## where n represents the number 0 or 1, X.sup.1 and X.sup.3 represent hydrogen, X.sup.2 and X.sup.4 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, OCH.sub.2CF.sub.3, aminothiocarbonyl, or phenylmethyl, phenoxy, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl, pyrazolylmethyl, pyridyloxy, pyrimidyloxy, thiazolyloxy, pyrazolyloxy, cyclopropylmethyl, cyclopropylmethoxy, optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifloromethoxy, difluoromethoxy or cyclopropyl, or represents (C.sub.3-C.sub.6)-cycloalkyl, phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, pyrazolyl, triazolyl or tetrazolyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy or by cyclopropyl, optionally, X.sup.2 and X.sup.4 represent the following combinations X.sup.2/X.sup.4: F/F, Cl/Cl, F/Cl, Cl/F, Br/Br, Br/Cl, Cl/Br, Br/F, F/Br, methyl/methyl, methyl/F, F/methyl, methyl/Cl, Cl/methyl, methyl/Br, Br/methyl, ethyl/ethyl, ethyl/F, F/ethyl, ethyl/Cl, Cl/ethyl, ethyl/Br, Br/ethyl, methoxy/methyl, methyl/methoxy, methyl/H, ethyl/H, chlorine/H, bromine/H, fluorine/H, methoxy/H, H/chlorine, H/fluorine, H/bromine, H/methyl, H/methoxy, H/ethyl, R.sup.3 represents methoxymethyl, methoxyethyl, cyanomethyl, allyl, butenyl, oxolanyl, pentandienyl, butadienyl, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, pyrrolyl, furanyl, thiazolyl, pyrazolyl or thienyl which may optionally be mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, or represents aryl, in particular phenyl, which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, R.sup.1 and R.sup.2 independently of one another represent hydrogen, cyano, methyl, ethyl, propyl, butyl, sec-butyl, isopropyl, tert-butyl, (2,2,2)-trifluoroethyl, (2,2)-difluoromethyl, methoxy, ethoxy, cyanomethyl, methoxymethyl, methoxyethyl, allyl, butenyl, propynyl, methylcarbonyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, methoxycarbonyl, ethoxycarbonyl, represent arylcarbonyl, pyridylcarbonyl, pyrimidylcarbonyl, thiazolylcarbonyl, pyrazolylcarbonyl, methylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, allyl, butenyl, methoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methylamino, dimethylamino, or represent a 3- to 6-membered saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once, twice or three times by CO and which may optionally be mono- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, optionally the following rings are explicitly mentioned: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, oxetane, phenyl, thienyl and pyridyl which may optionally be substituted by the substituents mentioned, or represent (CH.sub.2).sub.mR.sup.6, where R.sup.6 represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, may optionally be interrupted once or twice by CO and which may optionally be mono-, di- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, where m represents the number 1, optionally the following R.sup.6 are explicitly mentioned: cyclopropyl, phenyl and pyridyl which may optionally be substituted by the substituents mentioned, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached may form a saturated or unsaturated 3- to 6-membered ring which is optionally mono-, di-, tri- or tetrasubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, which may optionally contain one or two further heteroatoms from the group consisting of sulfur, oxygen and nitrogen (where oxygen atoms must not be directly adjacent to one another) and/or at least one CH2 group is replaced by a carbonyl group, optionally the following rings are explicitly mentioned: ##STR00545## in which the nitrogen atom to which R.sup.1 and R.sup.2 are attached represent the cycle and the arrow points to the remainder of the molecule, which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl and/or a diastereomer, enantiomer, rotamer, tautomer and/or salt thereof.

7. A compound, of formula (I) ##STR00546## where n represents the number 0 or 1, X.sup.1 and X.sup.3 represent hydrogen, X.sup.2 and X.sup.4 represent the following combinations X.sup.2/X.sup.4: vinyl/H, H/vinyl, ethynyl/H, H/ethynyl, methoxy/H, H/methoxy, ethoxy/H, H/ethoxy, aminothiocarbonyl/H, H/aminothiocarbonyl, vinyl/methyl, methyl/vinyl, ethynyl/methyl, methyl/ethynyl, methoxy/methyl, methyl/methoxy, ethoxy/methyl, methyl/ethoxy, aminothiocarbonyl/methyl, methyl/aminothiocarbonyl, vinyl/F, F/vinyl, ethynyl/F, F/ethynyl, methoxy/F, F/methoxy, ethoxy/F, F/ethoxy, aminothiocarbonyl/F, F/aminothiocarbonyl, vinyl/Cl, Cl/vinyl, ethynyl/Cl, Cl/ethynyl, methoxy/Cl, Cl/methoxy, ethoxy/Cl, Cl/ethoxy, aminothiocarbonyl/Cl, Cl/aminothiocarbonyl, R.sup.3 represents hydrogen, ethyl, propyl, cyano, trifluoromethyl, difluoromethyl, dichloromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl, (2,2,2)-trifluoroethyl, 2-chloro-(2,2)-difluoroethyl, (2,2)-dichloro-2-fluoroethyl, (2,2,2)-trichloroethyl, pentafluoroethyl, methoxymethyl, methoxyethyl, cyanomethyl, allyl, butenyl, or represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N and which may optionally be mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl optionally the following rings are explicitly mentioned: cyclopropyl, phenyl, pyridyl, pyrimidyl, thiazolyl, pyrazolyl and thienyl which may optionally be substituted by the substituents mentioned, R.sup.1 and R.sup.2 independently of one another represent hydrogen, cyano, methyl, ethyl, propyl, butyl, sec-butyl, isopropyl, tert-butyl, (2,2,2)-trifluoroethyl, (2,2)-difluoromethyl, methoxy, ethoxy, cyanomethyl, methoxymethyl, methoxyethyl, allyl, butenyl, propynyl, methylcarbonyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, methoxycarbonyl, ethoxycarbonyl, represent arylcarbonyl, pyridylcarbonyl, pyrimidylcarbonyl, thiazolylcarbonyl, pyrazolylcarbonyl, methylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl optionally mono- or disubstituted independently of one another by fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, allyl, butenyl, methoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, methylamino, dimethylamino, or represent a 3- to 6-membered saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once, twice or three times by CO and which may optionally be mono- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, optionally the following rings are explicitly mentioned: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, oxetane, phenyl, thienyl and pyridyl which may optionally be substituted by the substituents mentioned, or represent (CH.sub.2).sub.mR.sup.6, where R.sup.6 represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, may optionally be interrupted once or twice by CO and which may optionally be mono-, di- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, where m represents the number 1, optionally the following R.sup.6 are explicitly mentioned: cyclopropyl, phenyl and pyridyl which may optionally be substituted by the substituents mentioned, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached may form a saturated or unsaturated 3- to 6-membered ring which is optionally mono-, di-, tri- or tetrasubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, which may optionally contain one or two further heteroatoms from the group consisting of sulfur, oxygen and nitrogen (where oxygen atoms must not be directly adjacent to one another) and/or at least one CH2 group is replaced by a carbonyl group, optionally the following rings are explicitly mentioned: ##STR00547## in which the nitrogen atom to which R.sup.1 and R.sup.2 are attached represent the cycle and the arrow points to the remainder of the molecule, which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl, difluoromethyl, R.sup.1 and R.sup.3 together with the atoms to which they are attached may form a saturated or unsaturated 5- to 6-membered ring and/or one which is optionally mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyano, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, (C.sub.3-C.sub.4)-alkanediyl, (C.sub.3-C.sub.4)-alkenediyl, butanedienyl (where butanedienyl may optionally be mono- or disubstituted by methyl, fluorine, chlorine, bromine, methoxy or trifluoromethyl and/or may optionally be interrupted by at least one oxygen or/and nitrogen atom) and which may optionally contain a further sulfur or oxygen or nitrogen atom and/or a carbonyl group, optionally R.sup.1 and R.sup.3 together with the atoms to which they are attached represent the following group, ##STR00548## each of which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, where the arrow points to the remainder of the molecule and/or a diastereomer, enantiomer, rotamer, tautomer and/or salt thereof.

8. An N-arylamidine-substituted trifluoroethyl sulfide derivative of formula (I) ##STR00549## in which n represents the number 0 or 1, X.sup.1 and X.sup.3 represent hydrogen, X.sup.2 and X.sup.4 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, OCH.sub.2CF.sub.3, aminothiocarbonyl, or phenylmethyl, phenoxy, pyridylmethyl, pyrimidylmethyl, thiazolylmethyl, pyrazolylmethyl, pyridyloxy, pyrimidyloxy, thiazolyloxy, pyrazolyloxy, cyclopropylmethyl, cyclopropylmethoxy, optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifloromethoxy, difluoromethoxy or cyclopropyl, or represents (C.sub.3-C.sub.6)-cycloalkyl, phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, oxadiazolyl, pyrazolyl, triazolyl or tetrazolyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy or by cyclopropyl, R.sup.1 and R.sup.3 together with the atoms to which they are attached form a saturated or unsaturated 5- to 6-membered ring and/or one which is optionally mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyano, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, (C.sub.3-C.sub.4)-alkanediyl, (C.sub.3-C.sub.4)-alkenediyl, butanedienyl (where butanedienyl may optionally be mono- or disubstituted by methyl, fluorine, chlorine, bromine, methoxy or trifluoromethyl and/or may optionally be interrupted by at least one oxygen or/and nitrogen atom) and which may optionally contain a further sulfur or oxygen or nitrogen atom and/or a carbonyl group, optionally R.sup.1 and R.sup.3 together with the atoms to which they are attached represent the following group, ##STR00550## each of which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, where the arrow points to the remainder of the molecule, R.sup.2 represents cyano, (2,2,2)-trifluoroethyl, (2,2)-difluoromethyl, 2-chloro-(2,2)-difluoroethyl, (2,2)-dichloro-2-fluoroethyl, (2,2,2)-trichloroethyl, pentafluoroethyl, 2-chlorotetrafluoroethyl, allyl, butenyl, propynyl, methylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, trifluoromethylsulfonyl, or represent a 3- to 6-membered saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once, twice or three times by CO and which may optionally be mono- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, or represent (CH.sub.2).sub.mR.sup.6, where R.sup.6 represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to two heteroatoms from the group consisting of O, S and N, may optionally be interrupted once or twice by CO and which may optionally be mono-, di- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl, where m represents the number 1 and/or a diastereomer, enantiomer, rotamer, tautomer and/or salt thereof.

9. An active compound composition comprising at least one compound as claimed in claim 1 and at least one further active compound selected from the group consisting of (1) alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chloropyrifos, chloropyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion; (2) chlordane, endosulfan; ethiprole, fipronil; (3) acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)-(1R) isomers), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer), prallethrin, pyrethrine (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomers)], tralomethrin, transfluthrin; DDT; methoxychlor; (4) acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine; (5) spinetoram and spinosad; (6) abamectin, emamectin benzoate, lepimectin and milbemectin; (7) hydroprene, kinoprene and methoprene; or fenoxycarb; or pyriproxyfen; (8) methyl bromide and other alkyl halides; or chloropicrin; or sulfuryl fluoride; or borax; or tartar emetic; (9) pymetrozine; or flonicamid; (10) clofentezine, hexythiazox and diflovidazin; or etoxazole; (11) Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1; (12) diafenthiuron; or azocyclotin, cyhexatin and fenbutatin oxide; or propargite; or tetradifon; (13) chlorfenapyr, DNOC and sulfluramid; (14) bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium; (15) bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron; (16) Buprofezin; (17) Cyromazine; (18) chromafenozide, halofenozide, methoxyfenozide and tebufenozide; (19) amitraz; (20) hydramethylnone; or acequinocyl; or fluacrypyrim; (21) fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or rotenone (Derris); (22) indoxacarb; or metaflumizone; (23) spirodiclofen, spiromesifen and spirotetramat; (24) aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanide; (25) Cyenopyrafen; (28) chlorantraniliprole and flubendiamide; amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, cyantraniliprole, cyflumetofen, dicofol, diflovidazin, fluensulfone, flufenerim, flufiprole, fluopyram fufenozide, imidaclothiz, iprodione, meperfluthrin, pyridalyl, pyrifluquinazon, tetramethylfluthrin and iodomethane; and 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide, 4-{[(6-bromopyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, 4-{[(6-fluoropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one, 4-{[(2-chloro-1,3-thiazol-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, 4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, flupyradifurone, 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one, 4-{[(5,6-dichloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one, 4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one, 4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one, 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H), {[1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-.sup.4-sulfanylidene}cyanamide and its diastereomers {[(1R)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-.sup.4-sulfanylidene}cyanamide (A) and {[(1 S)-1-(6-chloropyridin-3-yl)ethyl](methyl)oxido-.sup.4-sulfanylidene}cyanamide (B) and also sulfoxaflor and its diastereomers [(R)-methyl(oxido){(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-.sup.4-sulfanylidene]cyanamide (A1) and [(S)-methyl(oxido){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-.sup.4-sulfanylidene]cyanamide (A2), identified as diastereomer group A, [(R)-methyl(oxido){(1S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-.sup.4-sulfanylidene]cyanamide (B1) and [(S)-methyl(oxido) {(1R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-.sup.4-sulfanylidene]cyanamide (B2), identified as diastereomer group B and 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one, 3-(4-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine [(3 S,4aR,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-6,12-dihydroxy-4,12b-dimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromen-4-yl]methylcyclopropanecarboxylate, 2-cyano-3-(difluoromethoxy)-N,N-dimethylbenzenesulfonamide, 2-cyano-3-(difluoromethoxy)-N-methylbenzenesulfonamide, 2-cyano-3-(difluoromethoxy)-N-ethylbenzenesulfonamide, 4-(difluoromethoxy)-N-ethyl-N-methyl-1,2-benzothiazole-3-amine 1,1-dioxide, N-[1-(2,3-dimethylphenyl)-2-(3,5-dimethylphenyl)ethyl]-4,5-dihydro-1,3-thiazole-2-amine, {1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4-piperidin]-1 (2H)-yl}(2-chloropyridin-4-yl)methanone, 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate, 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine, (2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,3-trifluoropropyl)malononitrile, (2,2,3,3,4,4,5,5-octafluoropentyl)(3,3,4,4,4-pentafluorobutyl)malononitrile, 8-[2-(cyclopropylmethoxy)-4-(trifluoromethyl)phenoxy]-3-[6-(trifluoromethyl)pyridazin-3-yl]-3-azabicyclo[3.2.1]octane, flometoquin, PF1364 (CAS Reg. No. 1204776-60-2), 5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile, 5-[5-(2-chloropyridin-4-yl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl)}benzamide, 4-{[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-chloropyridin-3-yl)methyl](ethyl)amino}-1,3-oxazol-2(5H)-one, 4-{[(6-chloropyridin-3-yl)methyl](methyl)amino}-1,3-oxazol-2(5H)-one, NNI-0711, 1-acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)-3-isobutylphenyl]-N-isobutyryl-3,5-dimethyl-1H-pyrazole-4-carboxamide, methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate, methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate, methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate, methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-diethylhydrazinecarboxylate, methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate, (5RS,7RS;5RS,7SR)-1-(6-chloro-3-pyridylmethyl)-1,2,3,5,6,7-hexahydro-7-methyl-8-nitro-5-propoxyimidazo[1,2-a]pyridine, 2-{6-[2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine, 2-{6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}pyrimidine, 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide, 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide, N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-1H-tetrazol-1-yl]methyl}-1H-pyrazole-5-carboxamide, N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl)-1H-pyrazole-5-carboxamide, (1E)-N-[(6-chloropyridin-3-yl)methyl]-N-cyano-N-(2,2-difluoroethyl)ethanimidamide, N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide and methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethyl-1-methylhydrazinecarboxylate, and/or at least one further active compound selected from the group consisting of (1) (1.1) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole (113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.11) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin (67306-00-7), (1.18) fenpropimorph (67306-03-0), (1.19) fluquinconazole (136426-54-5), (1.20) flurprimidol (56425-91-3), (1.21) flusilazole (85509-19-9), (1.22) flutriafol (76674-21-0), (1.23) furconazole (112839-33-5), (1.24) furconazole-cis (112839-32-4), (1.25) hexaconazole (79983-71-4), (1.26) imazalil (60534-80-7), (1.27) imazalil sulfate (58594-72-2), (1.28) imibenconazole (86598-92-7), (1.29) ipconazole (125225-28-7), (1.30) metconazole (125116-23-6), (1.31) myclobutanil (88671-89-0), (1.32) naftifin (65472-88-0), (1.33) nuarimol (63284-71-9), (1.34) oxpoconazole (174212-12-5), (1.35) paclobutrazole (76738-62-0), (1.36) pefurazoate (101903-30-4), (1.37) penconazole (66246-88-6), (1.38) piperalin (3478-94-2), (1.39) prochloraz (67747-09-5), (1.40) propiconazole (60207-90-1), (1.41) prothioconazole (178928-70-6), (1.42) pyributicarb (88678-67-5), (1.43) pyrifenox (88283-41-4), (1.44) quinconazole (103970-75-8), (1.45) simeconazole (149508-90-7), (1.46) spiroxamine (118134-30-8), (1.47) tebuconazole (107534-96-3), (1.48) terbinafin (91161-71-6), (1.49) tetraconazole (112281-77-3), (1.50) triadimefon (43121-43-3), (1.51) triadimenol (89482-17-7), (1.52) tridemorph (81412-43-3), (1.53) triflumizole (68694-11-1), (1.54) triforine (26644-46-2), (1.55) triticonazole (131983-72-7), (1.56) uniconazole (83657-22-1), (1.57) uniconazole-p (83657-17-4), (1.58) viniconazole (77174-66-4), (1.59) voriconazole (137234-62-9), (1.60) 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol (129586-32-9), (1.61) methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate (110323-95-0), (1.62) N-{5-(difluoromethyl)-2-methyl-4-[3-(trimethyl silyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide, (1.63) N-ethyl-N-methyl-N-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide and (1.64) O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]1H-imidazole-1-carbothioate (111226-71-2); (2) (2.1) bixafen (581809-46-3), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram (24691-80-3), (2.6) fluopyram (658066-35-4), (2.7) flutolanil (66332-96-5), (2.8) fluxapyroxad (907204-31-3), (2.9) furametpyr (123572-88-3), (2.10) furmecyclox (60568-05-0), (2.11) isopyrazam mixture of the syn-epimeric racemate 1RS,4SR,9RS and the anti-empimeric racemate 1RS,4SR,9SR (881685-58-1), (2.12) isopyrazam (anti-epimeric racemate), (2.13) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18) mepronil (55814-41-0), (2.19) oxycarboxin (5259-88-1), (2.20) penflufen (494793-67-8), (2.21) penthiopyrad (183675-82-3), (2.22) sedaxane (874967-67-6), (2.23) thifluzamid (130000-40-7), (2.24) 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (2.25) 3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide, (2.27) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (1092400-95-7), (2.28) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4-amine (1210070-84-0), (2.29) N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.30) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and (2.31) N-[(1R,4S)-9-(dichloromethylene-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide; (3) (3.1) ametoctradin (865318-97-4), (3.2) amisulbrom (348635-87-0), (3.3) azoxystrobin (131860-33-8), (3.4) cyazofamid (120116-88-3), (3.5) coumethoxystrobin (850881-30-0), (3.6) coumoxystrobin (850881-70-8), (3.5) dimoxystrobin (141600-52-4), (3.6) enestroburin (238410-11-2), (3.9) famoxadone (131807-57-3) (3.10) fenamidone (161326-34-7), (3.11) fenoxystrobin (918162-02-4), (3.12) fluoxastrobin (361377-29-9), (3.13) kresoxim-methyl (143390-89-0), (3.14) metominostrobin (133408-50-1), (3.15) orysastrobin (189892-69-1), (3.16) picoxystrobin (117428-22-5), (3.17) pyraclostrobin (175013-18-0), (3.18) pyrametostrobin (915410-70-7), (3.19) pyraoxystrobin (862588-11-2), (3.20) pyribencarb (799247-52-2), (3.21) triclopyricarb (902760-40-1), (3.22) trifloxystrobin (141517-21-7), (3.23) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide, (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene)}amino)oxy]methyl}phenyl)ethanamide, (3.25) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide (158169-73-4), (3.26) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide (326896-28-0), (3.27) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, (3.28) 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide (119899-14-8), (3.29) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (3.30) methyl (2E)-2-{2-[({cyclopropyl [(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyprop-2-enoate (149601-03-6), (3.31) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide (226551-21-9), (3.32) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (173662-97-0) and (3.33) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (394657-24-0); (4) (4.1) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9), (4.5) ethaboxam (162650-77-3), (4.6) fluopicolid (239110-15-7), (4.7) fuberidazole (3878-19-1), (4.8) pencycuron (66063-05-6), (4.9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11) thiophanate (23564-06-9), (4.12) zoxamide (156052-68-5), (4.13) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine (214706-53-3) and (4.14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine (1002756-87-7); (5) (5.1) Bordeaux mixture (8011-63-0), (5.2) captafol (2425-06-1), (5.3) captan (133-06-2), (5.4) chlorothalonil (1897-45-6), (5.5) copper preparations such as copper hydroxide (20427-59-2), (5.6) copper naphthenate (1338-02-9), (5.7) copper oxide (1317-39-1), (5.8) copper oxychloride (1332-40-7), (5.9) copper sulfate (7758-98-7), (5.10) dichlofluanid (1085-98-9), (5.11) dithianon (3347-22-6), (5.12) dodine (2439-10-3), (5.13) dodine free base, (5.14) ferbam (14484-64-1), (5.15) fluorofolpet (719-96-0), (5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5.18) guazatine acetate, (5.19) iminoctadine (13516-27-3), (5.20) iminoctadine albesilate (169202-06-6), (5.21) iminoctadine triacetate (57520-17-9), (5.22) mancopper (53988-93-5), (5.23) mancozeb (8018-01-7), (5.24) maneb (12427-38-2), (5.25) metiram (9006-42-2), (5.26) zinc metiram (9006-42-2), (5.27) copper-oxine (10380-28-6), (5.28) propamidine (104-32-5), (5.29) propineb (12071-83-9), (5.30) sulfur and sulfur preparations such as, for example, calcium polysulfide (7704-34-9), (5.31) thiram (137-26-8), (5.32) tolylfluanid (731-27-1), (5.33) zineb (12122-67-7) and (5.34) ziram (137-30-4); (6) (6.1) acibenzolar-S-methyl (135158-54-2), (6.2) isotianil (224049-04-1), (6.3) probenazole (27605-76-1) and (6.4) tiadinil (223580-51-6); (7) (7.1) andoprim (23951-85-1), (7.2) blasticidin-S(2079-00-7), (7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980-18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7), (7.7) pyrimethanil (53112-28-0) and (7.8) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline (861647-32-7); (8) (8.1) fentin acetate (900-95-8), (8.2) fentin chloride (639-58-7), (8.3) fentin hydroxide (76-87-9) and (8.4) silthiofam (175217-20-6); (9) (9.1) benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3) flumorph (211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (11113-80-7), (9.7) polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8) and (9.9) valifenalate (283159-94-4; 283159-90-0); (10) (10.1) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos (26087-47-8), (10.8) isoprothiolane (50512-35-1), (10.9) propamocarb (25606-41-1), (10.10) propamocarb hydrochloride (25606-41-1), (10.11) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18-6), (10.13) quintozene (82-68-8), (10.14) tecnazene (117-18-0) and (10.15) tolclofos-methyl (57018-04-9); (11) (11.1) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (11.4) fthalide (27355-22-2), (11.5) pyroquilon (57369-32-1), (11.6) tricyclazole (41814-78-2) and (11.7) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate (851524-22-6); (12) (12.1) benalaxyl (71626-11-4), (12.2) benalaxyl-M (kiralaxyl) (98243-83-5), (12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7), (12.8) hymexazole (10004-44-1), (12.9) metalaxyl (57837-19-1), (12.10) metalaxyl-M (mefenoxam) (70630-17-0), (12.11) ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3) and (12.13) oxolinic acid (14698-29-4); (13) (13.1) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341-86-1), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7) and (13.7) vinclozolin (50471-44-8); (14) (14.1) binapacryl (485-31-4), (14.2) dinocap (131-72-6), (14.3) ferimzone (89269-64-7), (14.4) fluazinam (79622-59-6) and (14.5) meptyldinocap (131-72-6); (15) (15.1) benthiazole (21564-17-0), (15.2) bethoxazine (163269-30-5), (15.3) capsimycin (70694-08-5), (15.4) carvone (99-49-0), (15.5) chinomethionat (2439-01-2), (15.6) pyriofenone (chlazafenone) (688046-61-9), (15.7) cufraneb (11096-18-7), (15.8) cyflufenamid (180409-60-3), (15.9) cymoxanil (57966-95-7), (15.10) cyprosulfamide (221667-31-8), (15.11) dazomet (533-74-4), (15.12) debacarb (62732-91-6), (15.13) dichlorophen (97-23-4), (15.14) diclomezine (62865-36-5), (15.15) difenzoquat (49866-87-7), (15.16) difenzoquat methylsulfate (43222-48-6), (15.17) diphenylamine (122-39-4), (15.18) EcoMate, (15.19) fenpyrazamine (473798-59-3), (15.20) flumetover (154025-04-4), (15.21) fluoromid (41205-21-4), (15.22) flusulfamide (106917-52-6), (15.23) flutianil (304900-25-2), (15.24) fosetyl-aluminum (39148-24-8), (15.25) fosetyl-calcium, (15.26) fosetyl-sodium (39148-16-8), (15.27) hexachlorobenzene (118-74-1), (15.28) irumamycin (81604-73-1), (15.29) methasulfocarb (66952-49-6), (15.30) methyl isothiocyanate (556-61-6), (15.31) metrafenone (220899-03-6), (15.32) mildiomycin (67527-71-3), (15.33) natamycin (7681-93-8), (15.34) nickel dimethyldithiocarbamate (15521-65-0), (15.35) nitrothal-isopropyl (10552-74-6), (15.36) octhilinone (26530-20-1), (15.37) oxamocarb (917242-12-7), (15.38) oxyfenthiin (34407-87-9), (15.39) pentachlorophenol and its salts (87-86-5), (15.40) phenothrin, (15.41) phosphoric acid and its salts (13598-36-2), (15.42) propamocarb-fosetylate, (15.43) propanosine-sodium (88498-02-6), (15.44) proquinazid (189278-12-4), (15.45) pyrimorph (868390-90-3), (15.45e) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one (1231776-28-5), (15.45z) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one (1231776-29-6), (15.46) pyrrolnitrin (1018-71-9), (15.47) tebufloquin (376645-78-2), (15.48) tecloftalam (76280-91-6), (15.49) tolnifanide (304911-98-6), (15.50) triazoxide (72459-58-6), (15.51) trichlamide (70193-21-4), (15.52) zarilamid (84527-51-5), (15.53) (3 S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate (517875-34-2), (15.54) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (1003319-79-6), (15.55) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (1003319-80-9), (15.56) 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (1003318-67-9), (15.57) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate (111227-17-9), (15.58) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine (13108-52-6), (15.59) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one (221451-58-7), (15.60) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c]dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.61) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (1003316-53-7), (15.62) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5 S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (1003316-54-8), (15.63) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4, 5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (1003316-51-5), (15.64) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.65) 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine, (15.66) 2-phenylphenol and its salts (90-43-7), (15.67) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (861647-85-0), (15.68) 3,4,5-trichloropyridine-2,6-dicarbonitrile (17824-85-0), (15.69) 3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (15.71) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (15.72) 5-amino-1,3,4-thiadiazole-2-thiole, (15.73) 5-chloro-N-phenyl-N-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide (134-31-6), (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine (1174376-11-4), (15.75) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine (1174376-25-0), (15.76) 5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.77) ethyl-(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, (15.78) N-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (15.79) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (15.80) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (15.81) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide, (15.82) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide, (15.83) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide, (15.84) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.85) N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.86) N-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide, (15.87) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide (922514-49-6), (15.88) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide (922514-07-6), (15.89) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide (922514-48-5), (15.90) pentyl-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}) carbamate, (15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol (134-31-6), (15.93) quinolin-8-ol sulfate (2:1) (134-31-6) and (15.94) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}) carbamate; (16) (16.1) 1-methyl-3-(trifluoromethyl)-N-[2-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.2) N-(4-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (16.3) N-(2,4-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (16.4) 3-(difluoromethyl)-1-methyl-N-[4-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.5) N-(2,5-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (16.6) 3-(difluoromethyl)-1-methyl-N-[4-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.7) 5-fluoro-1,3-dimethyl-N-[4-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.8) 2-chloro-N-[4-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide, (16.9) 3-(difluoromethyl)-N-[4-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (16.10) N-[4-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.11) 3-(difluoromethyl)-N-(4-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide, (16.12) N-(4-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.13) 2-chloro-N-(4-ethynylbiphenyl-2-yl)pyridine-3-carboxamide, (16.14) 2-chloro-N-[4-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide, (16.15) 4-(difluoromethyl)-2-methyl-N-[4-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide, (16.16) 5-fluoro-N-[4-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.17) 2-chloro-N-[4-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide, (16.18) 3-(difluoromethyl)-N-[4-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (16.19) 5-fluoro-N-[4-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (16.20) 2-chloro-N-[4-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide, (16.21) (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, (16.22) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methyl sulfonyl)valinamide (220706-93-4), (16.23) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid and (16.24) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyri din-2-yl}carbamate.

10. An agrochemical composition, comprising at least one compound as claimed in claim 1 and one or more extenders and/or surfactants.

11. A process for preparing an agrochemical composition, comprising mixing a compound as claimed in claim 1 with one or more extenders and/or surfactants.

12. A method for controlling one or more animal pests selected from the group consisting of insects, arachnids, helminths, nematodes and molluses, comprising allowing a compound as claimed in claim 1 to act on said animal pest and/or a habitat thereof.

13. The compound as claimed in claim 4, wherein X.sup.2 and X.sup.4 represent the following combinations X.sup.2/X.sup.4: F/F, Cl/Cl, F/Cl, Cl/F, Br/Br, Br/Cl, Cl/Br, Br/F, F/Br, methyl/methyl, methyl/F, F/methyl, methyl/Cl, Cl/methyl, methyl/Br, Br/methyl, ethyl/ethyl, ethyl/F, F/ethyl, ethyl/Cl, Cl/ethyl, ethyl/Br or Br/ethyl.

14. The compound as claimed in claim 8, wherein R.sup.2 represents a ring selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, oxetane, phenyl, thienyl and pyridyl, which may optionally be mono- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl.

15. The compound as claimed in claim 8, wherein R.sup.2 represents (CH.sub.2).sub.mR.sup.6, where R.sup.6 represents a ring selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl and pyridyl, which may optionally be mono-, di- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, ethynyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy and cyclopropyl.

16. The compound as claimed in claim 8, wherein X.sup.2 and X.sup.4 represent the following combinations X.sup.2/X.sup.4: F/F, Cl/Cl, F/Cl, Cl/F, Br/Br, Br/Cl, Cl/Br, Br/F, F/Br, methyl/methyl, methyl/F, F/methyl, methyl/Cl, Cl/methyl, methyl/Br, Br/methyl, ethyl/ethyl, ethyl/F, F/ethyl, ethyl/Cl, Cl/ethyl, ethyl/Br, Br/ethyl, methoxy/methyl, methyl/methoxy, methyl/H, ethyl/H, chlorine/H, bromine/H, fluorine/H, methoxy/H, H/chlorine, H/fluorine, H/bromine, H/methyl, H/methoxy or H/ethyl.

17. The compound as claimed in claim 8, wherein R.sup.1 and R.sup.3 together with the atoms to which they are attached represent the following group, ##STR00551## each of which may optionally be mono- or disubstituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, trifluoromethyl, difluoromethyl, cyclopropyl, chlorocyclopropyl, fluorocyclopropyl, cyanocyclopropyl, methylcyclopropyl, where the arrow points to the remainder of the molecule.

18. An agrochemical composition, comprising at least one compound as claimed in claim 8 and one or more extenders and/or surfactants.

19. A process for preparing an agrochemical composition, comprising mixing a compound as claimed in claim 8 with one or more extenders and/or surfactants.

20. A method for controlling one or more animal pests selected from the group consisting of insects, arachnids, helminths, nematodes and molluses, comprising allowing a compound as claimed in claim 8 to act on said animal pest and/or a habitat thereof.

Description

ILLUSTRATION OF THE PROCESSES AND INTERMEDIATES

(1) The Preparation and Use Examples which follow illustrate the invention without limiting it.

Preparation Example 1

2,2,2-Trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-N,N-dimethylethanimidamide (Ib-01)

Step 1: 2,2,2-Trifluoro-N-(2-fluoro-4-methylphenyl)acetamide (VI-1)

(2) ##STR00031##

(3) At 0 C., 27.5 g of 2-fluoro-4-methylaniline are initially charged in 300 ml of dichloromethane, 26.7 g of triethylamine are added and 50.8 g of trifluoroacetic anhydride are then added dropwise. The mixture is stirred at 0 C. for another 2 h and then concentrated by rotary evaporation. The residue is taken up in water and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered and the solvent is removed under reduced pressure. This gives 49.0 g (100% of theory) of the trifluoroacetamide (VI-1).

(4) log P(HCOOH): 2.40

Step 2: 4-Fluoro-2-methyl-5-[(trifluoroacetyl)amino]benzenesulfonyl chloride (V-1)

(5) ##STR00032##

(6) 258 g of chlorosulfonic acid are initially charged, and 49 g of 2,2,2-trifluoro-N-(2-fluoro-4-methylphenyl)acetamide (VI-1) are added a little at a time at room temperature. The mixture is stirred at room temperature for another 16 h. With stirring, the mixture is added to ice and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered and the solvent is removed under reduced pressure. This gives 70.8 g of the chlorosulfonyl (V-1). The crude product is immediately reacted further.

Step 3: N,N-[Disulfanediylbis(6-fluoro-4-methylbenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-1)

(7) ##STR00033##

(8) 298.8 g of sodium iodide are dissolved in 1000 ml of trifluoroacetic acid, and 70.8 g of 4-fluoro-2-methyl-5-Ktrifluoroacetyl)aminoThenzenesulfonyl chloride (V-1) are added at room temperature. The mixture is stirred at room temperature for 16 h and the solvent is then removed under reduced pressure. The residue is triturated with water and filtered off with suction. This gives 62.3 g (86% of theory) of the disulfide (IV-1) as a solid.

(9) log P(HCOOH): 4.41

Step 4: 2,2,2-Trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}acetamide (III-1)

(10) ##STR00034##

(11) 3.4 g of N,N-[disulfanediylbis(6-fluoro-4-methylbenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-1) are dissolved in 150 ml of N,N-dimethylformamide, and 1.86 g of potassium carbonate, 3.11 g of 1,1,1-trifluoroiodoethane (XVI-1), 2.39 g of Rongalite and a few drops of water are added. The reaction mixture is stirred at room temperature for 16 h. Most of the N,N-dimethylformamide is distilled off under reduced pressure. The residue is taken up in water and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered, and the solvent is then removed under reduced pressure. This gives 4.48 g (90% of theory) of the thioether (III-1).

(12) log P(HCOOH): 3.31

Step 5: 2,2,2-Trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}ethanimidoyl chloride (II-1)

(13) ##STR00035##

(14) 1 g of 2,2,2-trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}acetamide (III-1), 1.51 g of triethylamine and 4.01 g of diphenyl chlorophosphate in 20 ml of acetonitrile are heated under reflux for 16 h. After cooling, ethyl acetate is added and the precipitated solid is filtered off and discarded. The filtrate is adsorbed on silica gel and chromatographed using cyclohexane/ethyl acetate (98/2). Removal of the solvent affords 1 g of the imidoyl chloride (II-1).

Step 6: 2,2,2-Trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N-dimethylethanimidamide (Ia-01)

(15) ##STR00036##

(16) 0.77 g of dimethylamine (2 M in THF) is initially charged in 40 ml of acetonitrile, and 1 g of 2,2,2-trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}ethanimidoyl chloride (II-1) dissolved in 10 ml of acetonitrile is added dropwise at room temperature. The reaction mixture is stirred at room temperature for 16 h and the solvent is then removed under reduced pressure. The residue is taken up in water and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered, and the solvent is then removed under reduced pressure. This gives 0.36 g (35% of theory) of the amidine (Ia-01).

(17) log P(HCOOH): 4.48

Step 7: 2,2,2-Trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-N,N-dimethylethanimidamide (Ib-01)

(18) ##STR00037##

(19) 0.36 g of 2,2,2-trifluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N-dimethylethanimidamide (Ia-01) is dissolved in 30 ml of dichloromethane, and 0.21 g of meta-chloroperbenzoic acid is added at room temperature. The reaction mixture is stirred at room temperature for another 16 h and then made alkaline using sodium carbonate solution. Excess meta-chloroperbenzoic acid is reduced with sodium thiosulfate. After phase separation, the solvent is removed under reduced pressure. The residue is chromatographed with cyclohexane/acetone (9/1). This gives 0.31 g (79% of theory) of the amidine (Ib-01).

(20) log P(HCOOH): 3.15

Preparation Example 2

5-Amino-4-fluoro-2-methylbenzenethiol (XI-1)

Step 1: S-(5-Acetamido-4-fluoro-2-methylphenyl)ethanethioate (XII-1)

(21) ##STR00038##

(22) 99.3 g of 5-acetamido-4-fluoro-2-methylbenzenesulfonyl chloride (XV-1) are suspended in 700 ml of glacial acetic acid, 0.9 g of iodine and 38.7 g of red phosphorus are added, and the mixture is stirred at reflux for 5 h. After cooling, the solid is filtered off and the filtrate is concentrated by rotary evaporation. The residue is triturated with water and filtered off with suction. This gives 57.6 g (67% of theory) of the thioate (XII-1) as a solid.

(23) log P(HCOOH): 1.78

Step 2: 5-Amino-4-fluoro-2-methylbenzenethiol (XI-1)

(24) ##STR00039##

(25) 57.4 g of S-(5-acetamido-4-fluoro-2-methylphenyl)ethanethioate (XII-1) are dissolved in 750 ml of water and 96.6 g of potassium hydroxide. The reaction mixture is boiled at reflux for 16 hours. After cooling, the solution is adjusted to pH 2-3 using hydrochloric acid, and the precipitated solid is filtered off with suction. This gives 35.8 g (94% of theory) of the thiol (XI-1) as a solid.

(26) log P(HCOOH): 3.70

(27) Chiral Oxidation of (III) to (XVII)

Example 1

Synthesis of 2,2,2-trifluoro-N-{4-fluoro-2-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}acetamide

(28) ##STR00040##

(29) In a three-necked flask, 500 mg (1.49 mmol) of 2,2,2-trifluoro-N-{4-fluoro-2-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}acetamide were dissolved in 5 g of chloroform and cooled to 15 C. A solution of 15.82 mg (0.06 mmol) of vanadium acetylacetonate and 29.84 mg (0.089 mmol) of (S)(2,4-di-tert-butyl-6-{(E)-[(1-hydroxy-3,3-dimethylbutan-2-yl)imino]-methyl}phenol 1 g of chloroform was added to this mixture. After 5 minutes, a solution of 225.5 mg (1.79 mmol) of 30% strength H.sub.2O.sub.2 and 300 mg buffer solution pH 7 (KH.sub.2PO.sub.4/Na.sub.2HPO.sub.4) was metered in over 20 minutes. The progress of the reaction was monitored by HPLC. After a reaction time of 2 h, 100 mg of thiosulfate solution were added and most of the chloroform was evaporated under reduced pressure. 5 g of cyclohexane were added to the residue and the precipitated solid was filtered off.

(30) This gave 1-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole (91.24% pure by HPLC) as a beige solid. The enantiomeric excess was determined by HPLC on a chiral phase (Daicel Chiracel OJ-RH 150) with a ratio of 25.90:74.10.

(31) Chiral Oxidation of (Ia) to (Ib)

Example 1

Synthesis of N-{2,4-dichloro-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-2,2,2-trifluoroethanimidamide

(32) ##STR00041##

(33) In a three-necked flask, 1 g (2.69 mmol) of N-{2,4-dichloro-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroethanimidamide was dissolved in 10 ml of chloroform and cooled to 15 C. A solution of 29 mg (0.10 mmol) of vanadium acetylacetonate and 54 mg (0.16 mmol) of (S)(2,4-di-tert-butyl-6-{(E)-[(1-hydroxy-3,3-dimethylbutan-2-yl)imino]-methyl}phenol in 2 ml of chloroform was added to this mixture. A solution of 367 mg (3.23 mmol) of 30% strength H.sub.2O.sub.2 and 750 mg buffer solution pH 7 (KH.sub.2PO.sub.4/Na.sub.2HPO.sub.4) was metered in over 4 hours. The progress of the reaction was monitored by TLC. After a reaction time of 2 h, 128 mg of thiosulfate solution (1M) were added and the mixture was stirred overnight. The phases were separated and most of the chloroform (except for about 3 ml) was evaporated under reduced pressure. Cyclohexane was added to the residue and the precipitated solid was filtered off.

(34) This gave 980 mg of N-{2,4-dichloro-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-2,2,2-trifluoroethanimidamide (purity by HPLC >99%) as a solid. The enantiomeric excess was determined by HPLC on a chiral phase (Daicel Chiracel OD-RH 150) with a ratio of 89.63:10.37.

Preparation Example 3

N-{4-Chloro-3-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-2,2,2-trifluoroethanimidamide (Ib-108)

Step 1: 1,1-Disulfanediylbis(2-chloro-5-nitrobenzene)

(35) ##STR00042##

(36) With vigorous stirring, 236.1 g (1.02 mol) of chlorosulfonic acid are added to 52.0 g (203.1 mmol) of 2-chloro-5-nitrobenzenesulfonyl chloride, and the mixture is stirred at room temperature overnight. After addition of 40% strength aqueous sodium bisulfite solution, the solid formed is filtered off with suction, washed with water and dried on a clay disk overnight. This gives 36.1 g (100% pure, 94% of theory) of the title compound as a gray-brown solid.

(37) log P(HCOOH): 5.03; log P(neutral): 5.01; 1H-NMR (D6-DMSO, 400 MHz) ppm 8.40 (d, 2H), 8.18-8.16 (m, 2H), 7.91 (d, 2H); GC-MS: EI mass (m/z): 376 (2Cl) [M]+

Step 2: 3,3-Disulfanediylbis(4-chloroaniline)

(38) ##STR00043##

(39) 8.00 g (21.2 mmol) of 1,1-disulfanediylbis(2-chloro-5-nitrobenzene) are dissolved in 150 ml of THF, 1.6 g of Raney nickel are added and the mixture is stirred at 50 C. under a hydrogen atmosphere (20 bar) for 72 h. Using THF, the reaction mixture is filtered through kieselguhr, and the filtrate is freed from the solvent under reduced pressure. This gives 6.64 g (90% pure, 89% of theory) of a mixture of 1,1-disulfanediylbis(2-chloro-5-nitrobenzene) and 5-amino-2-chlorobenzenethiol which is alkylated without further purification.

1,1-Disulfanediylbis (2-chloro-5-nitrobenzene)

(40) log P(HCOOH): 3.31; log P(neutral): 3.35; 1H-NMR (D6-DMSO 400 MHz) ppm 7.10 (d, 2H), 6.73 (d, 2H), 6.47-6.44 (m, 2H), 5.51 (broad, 4H); GC-MS: EI mass (m/z): 316 (2Cl) [M]+

5-Amino-2-chlorobenzenethiol

(41) log P(HCOOH): 1.64; log P(neutral): not measurable; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.01 (d, 1H), 6.54 (d, 1H), 6.35-6.32 (m, 1H), 5.28 (broad, 3H); GC-MS: EI mass (m/z): 159 (1Cl) [M]+

Step 3: 4-Chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]aniline

(42) ##STR00044##

(43) 6.40 g of a mixture of disulfanediylbis(2-chloro-5-nitrobenzene) and 5-amino-2-chlorobenzenethiol (about 20 mmol) are initially charged in 100 ml of N,N-dimethylformamide, and 7.02 g (40.3 mmol) of sodium dithionite, 5.58 g (40.3 mmol) of potassium carbonate and 5.49 g (40.3 mmol) of Rongalit are added and the mixture is cooled to 0 C. 9.32 g of 1,1,1-trifluoro-2-iodoethane are added dropwise at 0 C. The reaction mixture is stirred at room temperature overnight. Most of the solvent is removed under reduced pressure, water is added to the residue and the mixture is extracted with ethyl acetate. The combined organic phases are washed successively with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel by means of MPLC using the mobile phase cyclohexane/ethyl acetate gives 4.70 g (98% pure, 47% of theory) of the title compound as a yellow liquid.

(44) log P(HCOOH): 2.64; log P(neutral): 2.69; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.09 (d, 1H), 6.78 (d, 1H), 6.49-6.46 (m, 1H), 5.37 (broad, 2H), 3.90 (q, 2H); GC-MS: EI mass (m/z): 241 (1Cl) [M]+

Step 4: N-{4-Chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide

(45) ##STR00045##

(46) 1.00 g (4.14 mmol) of 4-chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]aniline is initially charged in 14 ml of dichloromethane, and 0.50 g (4.97 mmol) of triethylamine is added at 0 C. 0.96 g (4.55 mmol) of trifluoroacetic anhydride is added dropwise at 0 C. The reaction mixture is stirred at room temperature overnight, then washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel by means of MPLC using the mobile phase cyclohexane/ethyl acetate gives 1.00 g (99% pure, 71% of theory) of the title compound as a colorless solid.

(47) log P(HCOOH): 3.46; log P(neutral): 3.41; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.43 (s, 1H), 7.91 (d, 1H), 7.63-7.69 (m, 1H), 7.56-7.58 (m, 1H), 4.05 (q, 2H); 1H-NMR (CDCl.sub.3, 400 MHz) ppm 7.85 (broad, 1H), 7.82 (d, 1H), 7.52-7.45 (m, 2H), 3.53 (q, 2H); GC-MS: EI mass (m/z): 337 (1Cl) [M]+

Step 5: N-{4-Chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroethanimidoyl chloride

(48) ##STR00046##

(49) 880 mg (2.61 mmol) of N-{4-chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide are initially charged in 17 ml of acetonitrile, 1.32 g (13.03 mmol) of triethylamine and 3.50 g (13.03 mmol) of diphenyl chlorophosphate are added at room temperature and the mixture is heated at reflux overnight. After cooling, ethyl acetate is added and the mixture is filtered and concentrated. The residue is directly subjected to purification by column chromatography on silica gel by MPLC using the mobile phase cyclohexane/ethyl acetate. This gives 640 mg (93% pure, 64% of theory) of the title compound as a yellow oil.

(50) log P(HCOOH): 4.77; log P(neutral): 4.73; 1H-NMR (CDCl.sub.3, 400 MHz) ppm 7.51 (d, 1H), 7.24 (d, 1H), 7.02-7.00 (m, 1H), 3.51 (q, 2H); GC-MS: EI mass (m/z): 355 (2Cl) [M]+

Step 6: N-{4-Chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroethanimidamide (Ia-204)

(51) ##STR00047##

(52) 210 mg (0.59 mmol) of N-{4-chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroethanimidoyl chloride are initially charged in 5 ml of acetonitrile, and a solution of 241 mg (3.54 mmol) of 25% strength aqueous ammonia solution in 5 ml of acetonitrile is added. The reaction mixture is stirred at room temperature overnight and then concentrated. The residue is extracted with water and ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel by means of MPLC using the mobile phase cyclohexane/ethyl acetate gives 120 mg (100% pure, 60% of theory) of the title compound as a yellow oil.

(53) log P(HCOOH): 3.10; log P(neutral): 3.10; 1H-NMR (D6-DMSO 400 MHz) ppm 7.42 (d, 1H), 7.26 (broad, 2H), 7.05 (d, 1H), 6.75-6.72 (m, 1H), 4.13 (q, 2H)

Step 7: N-{4-Chloro-3-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-2,2,2-trifluoroethanimidamide (Ib-108)

(54) ##STR00048##

(55) 90 mg (0.27 mmol) of N-{4-chloro-3-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroethanimidamide are dissolved in 6 ml of dichloromethane, and 68 mg (0.29 mmol) of meta-chloroperbenzoic acid are added at 0 C. After two hours of stirring at 0 C., another 23 mg (0.13 mmol) are added. The reaction mixture is stirred at room temperature overnight and then diluted with dichloromethane and washed successively with 40% strength sodium bisulfite solution and saturated aqueous sodium bicarbonate. The organic phase is dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel by means of MPLC using the mobile phase cyclohexane/ethyl acetate gives 90 mg (95% pure, 91% of theory) of the title compound as a beige solid.

(56) log P(HCOOH): 2.25; log P(neutral): 2.21; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.57 (d, 1H), 7.42 (broad, 2H), 7.30 (d, 1H), 7.10-7.07 (m, 1H), 4.22-4.04 (m, 2H)

Preparation Example 4

N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N-methyl-4-(trifluoromethyl)benzenecarboximidamide (Ia-250)

Step 1: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-4-(trifluoromethyl)benzamide

(57) ##STR00049##

(58) 1.00 g (4.18 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline is initially charged in 25 ml of dichloromethane, 0.47 g (4.60 mmol) of triethylamine is added and the mixture is cooled to 0 C. 0.96 g (4.60 mmol) of 4-(trifluoromethyl)benzoyl chloride in 25 ml of dichloromethane is added dropwise at 0 C. The reaction mixture is stirred at room temperature overnight. 0.17 g (0.84 mmol) of 4-(trifluoromethyl)benzoyl chloride is added, and the mixture is stirred at room temperature for a further 3 h. The reaction mixture is diluted with dichloromethane, washed successively with semisaturated aqueous ammonium chloride solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. The residue is triturated with petroleum ether, filtered off with suction and dried. This gives 1.69 g (95% pure, 93% of theory) of the title compound as a colorless solid.

(59) log P(HCOOH): 4.20; log P(neutral): 4.17; 1H-NMR (D6-DMSO, 400 MHz) ppm 10.40 (s, 1H), 8.17 (d, 2H), 7.93 (d, 2H), 7.82 (d, 1H), 7.31 (d, 1H), 3.89 (q, 2H), 2.42 (s, 3H); 1H-NMR (CD.sub.3CN, 400 MHz) ppm 8.70 (broad, 1H), 8.12 (d, 1H), 8.08 (d, 2H), 7.84 (d, 2H), 7.17 (d, 1H), 3.57 (q, 2H), 2.46 (s, 3H); GC-MS: EI mass (m/z): 411 [M]+

Step 2: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-4-(trifluoromethyl)benzenecarboximidoyl chloride

(60) ##STR00050##

(61) 1.00 g (2.43 mmol) of N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-4-(trifluoromethyl)benzamide is initially charged in 20 ml of dichloromethane, 0.51 g (2.43 mmol) of phosphorus pentachloride is added and the mixture is stirred at room temperature overnight. Another 0.51 g (2.43 mmol) of phosphorus pentachloride is added and the mixture is stirred at room temperature overnight. A further 0.51 g (2.43 mmol) of phosphorus pentachloride is added, and the reaction mixture is stirred at room temperature for 3 h and then filtered through silica gel and concentrated. This gives 0.91 g (74% pure, 65% of theory) of the title compound as a yellow oil which is directly reacted further.

(62) 1H-NMR (CD.sub.3CN, 400 MHz) ppm 8.32 (d, 2H), 7.86 (d, 2H), 7.32 (d, 1H), 7.21 (d, 1H), 3.58 (q, 2H), 2.47 (s, 3H); GC-MS: EI mass (m/z): 429 (1Cl) [M]+

Step 3: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N-methyl-4-(trifluoromethyl)benzenecarboximidamide

(63) ##STR00051##

(64) 150 mg (4.65 mmol) of methylamine (2M in THF) are initially charged in 25 ml of acetonitrile, 400 mg (0.93 mmol) of N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-4-(trifluoromethyl)benzenecarboximidoyl chloride in 25 ml of acetonitrile are added at 0 C. and the mixture is stirred at room temperature overnight and then concentrated. The residue is purified by column chromatography on silica gel by MPLC using the mobile phase cyclohexane/ethyl acetate. This gives 220 mg (99% pure, 56% of theory) of the title compound as a yellow solid.

(65) log P(HCOOH): 1.96; log P(neutral): 4.08; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.64 (d, 2H), 7.46 (d, 1H), 7.39 (d, 2H), 6.88 (d, 1H), 7.76 (d, 1H), 3.53 (q, 2H), 2.89 (d, 3H), 2.20 (s, 3H); GC-MS: EI mass (m/z): 424 [M]+

Preparation Example 5

5-Chloro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N-dimethylthiophene-2-carboximidamide (Ia-149)

Step 1: 5-Chloro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N-dimethylthiophene-2-carboximidamide

(66) ##STR00052##

(67) 743 mg (4.85 mmol) of phosphoryl chloride are added to 200 mg (0.84 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 206 mg (1.09 mmol) of 5-chloro-N,N-dimethylthiophene-2-carboxamide, and the mixture is heated at reflux overnight. After cooling, the reaction mixture is poured into water, made alkaline with potassium carbonate and extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel by means of MPLC using the mobile phase cyclohexane/ethyl acetate gives 165 mg (92% pure, 44% of theory) of the title compound as a red-brown oil.

(68) log P(HCOOH): 2.11; log P(neutral): 4.89; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.00 (d, 1H), 7.93 (d, 1H), 6.87-6.84 (m, 2H), 3.68 (q, 2H), 2.97 (broad, 6H), 2.23 (s, 3H)

Preparation Example 6

N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N,1-trimethyl-1H-pyrrole-2-carboximidamide (Ia-162)

Step 1: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N,1-trimethyl-1H-pyrrole-2-carboximidamide

(69) ##STR00053##

(70) 743 mg (4.85 mmol) of phosphoryl chloride are added to 200 mg (0.84 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 165 mg (1.09 mmol) of N,N,1-trimethyl-1H-pyrrole-2-carboxamide, and the mixture is heated at reflux overnight. After cooling, the reaction mixture is poured into water, made alkaline with potassium carbonate and extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel by means of MPLC using the mobile phase cyclohexane/ethyl acetate gives 177 mg (99% pure, 56% of theory) of the title compound as a yellow oil.

(71) log P(HCOOH): 1.67; log P(neutral): 4.11; 1H-NMR (D6-DMSO, 400 MHz) ppm 6.88 (d, 1H), 6.70-6.68 (m, 1H), 6.64 (d, 1H), 5.91-5.89 (m, 2H), 3.59 (q, 2H), 3.39 (s, 3H), 3.05 (broad, 3H), 2.77 (broad, 3H), 2.21 (s, 3H)

Preparation Example 7

N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N-dimethylfuran-2-carboximidamide (Ia-166)

Step 1: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N,N-dimethylfuran-2-carboximidamide

(72) ##STR00054##

(73) 743 mg (4.85 mmol) of phosphoryl chloride are added to 200 mg (0.84 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 139 mg (1.09 mmol) of N,N-dimethyl-2-furanamide, and the mixture is heated at reflux overnight. After cooling, the reaction mixture is poured into water, made alkaline with potassium carbonate and extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel by means of MPLC using the mobile phase cyclohexane/ethyl acetate gives 64 mg (98% pure, 21% of theory) of the title compound as a yellow oil.

(74) log P(HCOOH): 1.57; log P(neutral): 3.94; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.69-7.67 (m, 1H), 6.91 (d, 1H), 6.76 (d, 1H), 6.43-6.40 (m, 1H), 6.25 (d, 1H), 3.69 (q, 2H), 2.94 (s, 6H), 2.24 (s, 3H)

Preparation Example 8

2-Methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline

Step 1: 5-Acetamido-4-methoxy-2-methylbenzenesulfonyl chloride

(75) ##STR00055##

(76) A little at a time, 19.5 g (108.8 mmol) of N-(2-methoxy-4-methylphenyl)acetamide [CAS-RN 89345-81-3] are added to 150 g (1287 mmol) of chlorosulfonic acid, and the mixture is stirred at 80 C. for another 4 h. After cooling, the mixture is added to ice-water and the solid obtained is filtered off with suction, giving 25.4 g of product (84.1% of theory, purity 100% according to 1H-NMR).

(77) 1H-NMR (D6-DMSO) ppm: 9.04 (s, 1H), 8.14 (s, 1H), 6.80 (s, 1H), 3.80 (s, 3H), 2.48 (s, 3H), 2.04 (s, 3H)

Step 2: N,N-[Disulfanediylbis(6-methoxy-4-methylbenzene-3,1-diyl)]diacetamide

(78) ##STR00056##

(79) 25.3 g (91.1 mmol) of 5-acetamido-4-methoxy-2-methylbenzenesulfonyl chloride and 14.6 g (261.4 mmol) of iron powder in 400 ml of ethanol and 36.7 g of concentrated hydrochloric acid are heated under reflux for 12 h. After removal of the solvent under reduced pressure, the residue is triturated with water and filtered off with suction, giving 9.4 g of crude product (49.1% of theory, purity 86.4% according to LC/MS) as a light-brown solid.

(80) log P(HCOOH): 2.73

Step 3: N-{2-Methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}acetamide

(81) ##STR00057##

(82) 9.4 g (22.35 mmol) of N,N-[disulfanediylbis(6-methoxy-4-methylbenzene-3,1-diyl)]diacetamide are initially charged in 60 ml of dimethylformamide, 6.5 g of sodium dithionite, 15.9 g of potassium carbonate and 5.45 g of sodium bisphosphate and 40 ml of water are added and the mixture is then stirred at 60 C. for 3 h. After cooling, 12.5 g (59.54 mmol) of 1,1,1-trifluoro-2-iodoethane are added and the mixture is stirred at 75 C. for a further 12 h. After removal of the solvent under reduced pressure, the residue that remains is acidified with concentrated hydrochloric acid and the precipitate formed is filtered off with suction. This leaves 5.3 g of product (80.8% of theory, purity >95% according to 1H-NMR).

(83) 1H-NMR (D6-DMSO) ppm: 9.15 (s, 1H), 8.14 (s, 1H), 6.98 (s, 1H), 3.83 (s, 3H), 3.69-3.61 (q, 2H), 2.40 (s, 3H), 2.06 (s, 3H)

Step 4: 2-Methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline

(84) ##STR00058##

(85) 5.3 g (22.35 mmol) of N-{2-methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}acetamide in 125 ml of 5 molar hydrochloric acid are stirred under reflux for 18 h. The reaction mixture is made alkaline with aqueous sodium hydroxide solution and extracted with dichloromethane. The organic phase is separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 3.6 g of product as a dark-orange oil (79.3% of theory, purity 96.8% according to LC/MS).

(86) 1H-NMR (D6-DMSO) ppm: 6.83 (s, 1H), 6.72 (s, 1H), 4.64 (broad, 2H), 3.75 (s, 3H), 3.64-3.56 (q, 2H), 2.30 (s, 3H)

Preparation Example 9

3-[(2,2,2-Trifluoroethyl)sulfanyl]aniline

(87) ##STR00059##

(88) 6.5 g (51.92 mmol) of 3-aminobenzenethiol are initially charged in 200 ml of acetonitrile, 13.7 g of potassium carbonate, 1.6 g of solid sodium hydroxide, 1 ml of dimethyl sulfoxide and 13 g (61.93 mmol) of 1,1,1-trifluoro-2-iodoethane are added and the mixture is stirred at 45 C. for 18 h. The reaction mixture is diluted with 250 ml of water and extracted with dichloromethane. The organic phase is separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 9.5 g of product as a brown oil (88.3% of theory, purity 97.9% according to LC/MS).

(89) 1H-NMR (D6-DMSO) ppm: 7.00-6.97 (m, 1H), 6.61 (m, 1H), 6.59 (m, 1H), 6.47-6.45 (m, 1H), 5.19 (broad, 2H), 3.88-3.80 (q, 2H)

(90) log P(HCOOH): 2.01

Preparation Example 10

N-(2,2-Difluoroethyl)cyclopropanecarboxamide (XXIV-1)

(91) ##STR00060##

(92) 14.4 g (137.75 mmol) of cyclopropanecarbonyl chloride are dissolved in 300 ml of anhydrous tetrahydrofuran. After the addition of 1 g of triethylamine, a solution of 16.8 g (207.24 mmol) of 2,2-difluoroethanamine in 50 ml of anhydrous tetrahydrofuran is added dropwise. After the end of the addition, the mixture is stirred at room temperature for another 18 h and subsequently at 40 C. for another 1 h. The mixture is diluted with 200 ml of water and extracted with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves a residue of 18.9 g of product (92% of theory, purity 100% according to 1H-NMR) as a white solid.

(93) 1H-NMR (D6-DMSO) ppm: 8.46 (t, 1H), 5.99 (tt, 1H), 3.54-3.43 (m, 2H), 1.65-1.59 (m, 1H), 0.70-0.60 (m, 4H)

Preparation Example 11

1-Fluorocyclopropanecarboxamide (XXIV-2)

(94) ##STR00061##

(95) A little at a time, 600 mg (4.9 mmol) of 1-fluorocyclopropanecarbonyl chloride [CAS-RN 149961-53-5] are added to 15 g of ammonium hydroxide (28-30% by weight strength solution of NH.sub.3 in water), and the mixture is stirred at room temperature for another 18 h. The resulting precipitate is filtered off with suction, giving 470 mg of product (93.1% of theory, purity 100% according to 1H-NMR) as a white solid.

(96) 1H-NMR (D6-DMSO) ppm: 7.80 (broad, 1H), 7.58 (broad, 1H), 1.29-1.12 (m, 4H)

Preparation Example 12

(4-Chlorophenyl)(4,4-difluoropiperidin-1-yl)methanone (XXIV-3)

(97) ##STR00062##

(98) 470 mg (2.98 mmol) of 4,4-difluoropiperidinium chloride are initially charged in 35 ml of anhydrous toluene. After the addition of 1.4 g of triethylamine, 690 mg (3.94 mmol) of 4-chlorobenzoyl chloride are added a little at a time, and the mixture is stirred at 100 C. for a further 18 h. The reaction mixture is diluted with 250 ml of water and the organic phase is separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 480 mg of product as an orange oil (62% of theory, purity 88% according to LC/MS).

(99) 1H-NMR (D6-DMSO) ppm: 7.54-7.49 (m, 4H), 3.70 (m, 2H), 3.39 (m, 2H), 2.03 (m, 4H)

Preparation Example 13

N-{2-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}cyclopropanecarboxamide (XXIV-4)

(100) ##STR00063##

(101) 550 mg (2.11 mmol) of 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine are initially charged in 20 ml of anhydrous dichloromethane. After the addition of 1 g of triethylamine, 270 mg (2.58 mmol) of cyclopropanecarbonyl chloride, dissolved in 5 ml of anhydrous dichloromethane, are added dropwise, and the mixture is then stirred at 50 C. for another 12 h. The reaction mixture is diluted with 50 ml of water and the organic phase is separated off, dried over magnesium sulfate and freed from the solvent under reduced pressure. This gives 450 mg of product as an orange solid (73% of theory, purity 87.1% according to LC/MS).

(102) 1H-NMR (D6-DMSO) ppm: 8.89 (d, 1H), 8.41 (d, 1H), 8.17 (t, 1H), 3.53-3.48 (m, 2H), 3.11 (t, 2H), 1.51-1.46 (m, 1H), 0.63-0.59 (m, 4H)

Preparation Example 14

1-Fluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-cyclopropanecarboximidamide (Ib-19)

Step 1: 1-Fluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}cyclopropanecarboximidamide (Ia-27)

(103) ##STR00064##

(104) 1.4 g (9.13 mmol) of phosphoryl chloride are added to 400 mg (1.67 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 470 mg (4.56 mmol) of 1-fluorocyclopropanecarboxamide, and the mixture is stirred at 95 C. for 18 h. The residue that remains after rotary evaporation is stirred with water, made alkaline with solid potassium carbonate and extracted with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 380 mg of product (70.1% of theory, purity 88.8% according to LC/MS) as residue.

(105) log P(HCOOH): 1.2

Step 2: 1-Fluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}cyclopropanecarboximidamide (Ib-19)

(106) ##STR00065##

(107) At 0-4 C., 310 mg (0.96 mmol) of 1-fluoro-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}cyclopropanecarboximidamide (Ia-27) are initially charged in 30 ml of trichloromethane. After the addition of 335 mg of buffer solution pH 7 (KH2PO4/Na2HPO4) and 65 mg of benzyltriethylammonium chloride, 230 mg (70% strength, 1.03 mmol) of m-chloroperbenzoic acid are added a little at a time at 0-4 C. and the reaction mixture is stirred at room temperature for 24 h. A 33% strength aqueous sodium bisulfite solution is added, and the mixture is then extracted twice with dichloromethane. The combined organic phases are washed with water, dried over sodium sulfate and filtered. After removal of the solvent under reduced pressure, the residue is purified by column chromatography using MPLC on RP(C-18) with water/acetonitrile. This gives 42 mg of product (12.9% of theory, purity 98.1% according to LC/MS).

Preparation Example 15

2,2,2-Trifluoro-N-{2-methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}ethanimidamide (Ia-236)

(108) ##STR00066##

(109) 2.5 g (16.3 mmol) of phosphoryl chloride are added to 300 mg (1.19 mmol) of 2-methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 400 mg (3.54 mmol) of trifluoroacetamide, and the mixture is stirred at 95 C. for 18 h. The residue that remains after rotary evaporation is stirred with water, made alkaline with solid potassium carbonate and extracted with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 61.3 mg of product (14.1% of theory, purity >95% according to 1H-NMR) as residue.

Preparation Example 16

N-[(4-Chlorophenyl)(morpholin-4-yl)methylene]-2-methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-268)

(110) ##STR00067##

(111) 2.5 g (16.3 mmol) of phosphoryl chloride are added to 300 mg (1.19 mmol) of 2-methoxy-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 360 mg (1.60 mmol) of (4-chlorophenyl)(morpholin-4-yl)methanone, and the mixture is stirred at 95 C. for 18 h. The residue that remains after rotary evaporation is stirred with water, made alkaline with solid potassium carbonate and extracted with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 247 mg of product (40.9% of theory, purity 90.9% according to LC/MS) as residue.

Preparation Example 17

N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-N-methylpyridine-3-carboximidamide (Ib-28)

Step 1: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N-methylpyridine-3-carboximidamide (Ia-61)

(112) ##STR00068##

(113) 1.5 g (9.78 mmol) of phosphoryl chloride are added to 400 mg (1.67 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 450 mg (3.31 mmol) of N-methylnicotinamide, and the mixture is stirred at 95 C. for 18 h. The residue that remains after rotary evaporation is stirred with water, made alkaline with solid potassium carbonate and extracted with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 550 mg of product (92.1% of theory, purity 92.9% according to LC/MS) as residue.

Step 2: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-N-methylpyridine-3-carboximidamide (Ib-28)

(114) ##STR00069##

(115) At 0-4 C., 460 mg (1.29 mmol) of N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N-methylpyridine-3-carboximidamide (Ia-61) are initially charged in 40 ml of trichloromethane. After the addition of 460 mg of buffer solution pH 7 (KH.sub.2PO.sub.4/Na.sub.2HPO.sub.4) and 90 mg of benzyltriethylammonium chloride, 320 mg (70%, 0.261 mmol) of m-chloroperbenzoic acid are added a little at a time at 0-4 C. and the reaction mixture is stirred at RT for 24 h. A 33% strength aqueous sodium bisulfite solution is added, and the mixture is then extracted twice with dichloromethane. The combined organic phases are washed with water, dried over sodium sulfate and filtered. After removal of the solvent under reduced pressure, the residue is purified by column chromatography using MPLC on RP(C-18) with water/acetonitrile. This gives 145 mg of product (30.2% of theory, purity 98.7% according to HPLC).

Preparation Example 18

N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}pyrazine-2-carboximidamide (Ib-62)

Step 1: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}pyrazine-2-carboximidamide (Ia-117)

(116) ##STR00070##

(117) 2 g (13.04 mmol) of phosphoryl chloride are added to 300 mg (1.25 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 190 mg (1.54 mmol) of pyrazinecarboxamide, and the mixture is stirred at 95 C. for 18 h. The residue that remains after rotary evaporation is stirred with water, made alkaline with solid potassium carbonate and extracted with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 365 mg of product (84.5% of theory, purity 91.2% according to LC/MS) as residue.

(118) log P(HCOOH): 1.24

Step 2: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}pyrazine-2-carboximidamide (Ib-62)

(119) ##STR00071##

(120) At 0-4 C., 305 mg (0.89 mmol) of N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}pyrazine-2-carboximidamide (Ia-117) are initially charged in 30 ml of trichloromethane. After the addition of 320 mg of buffer solution pH 7 (KH.sub.2PO.sub.4/Na.sub.2HPO.sub.4) and 60 mg of benzyltriethylammonium chloride, 225 mg (70%, 1.04 mmol) of m-chloroperbenzoic acid are added a little at a time at 0-4 C. and the reaction mixture is stirred at RT for 24 h. A 33% strength aqueous bisulfite solution is added, and the mixture is then extracted twice with dichloromethane. The combined organic phases are washed with water, dried over sodium sulfate and filtered. After removal of the solvent under reduced pressure, the residue is adsorbed on RP(C-18) material. Purification by column chromatography using MPLC on RP(C-18) with water/acetonitrile gives 55 mg (17.2% of theory, purity 100% according to LC/MS) of product as a light-beige solid.

(121) log P(HCOOH): 0.84 log P(neutral): 1.77

Preparation Example 19

2-Fluoro-4-methyl-N-[1-(2,2,2-trifluoroethyl)pyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline (Ib-115)

Step 1: N-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N-(2,2,2-trifluoroethyl)cyclopropanecarboximidamide (Ia-145) and 2-fluoro-4-methyl-N-[1-(2,2,2-trifluoroethyl)pyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-189)

(122) ##STR00072##

(123) 1.5 g (9.78 mmol) of phosphoryl chloride are added to 300 mg (1.25 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 430 mg (2.57 mmol) of N-(2,2,2-trifluoroethyl)cyclopropanecarboxamide, and the mixture is stirred at 95 C. for 18 h. The residue that remains after rotary evaporation is stirred with water, made alkaline with solid potassium carbonate and extracted with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves 630 mg of crude product as an about 3:1 mixture of the isomers described above as residue.

(124) Purification by column chromatography using MPLC on RP(C-18) with water/acetonitrile gives 239.8 mg (49.2% of theory, purity 80% according to 1H-NMR) of N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-N-(2,2,2 trifluoroethyl)cyclopropanecarboximidamide (Ia-145)

(125) ##STR00073##

(126) 13C-NMR (D6-DMSO) ppm: 161.0, 153.5, 137.0, 133.9, 128.1, 127.2, 117.5, 41.0, 35.6, 19.6, 11.6, 6.2

(127) log P(HCOOH): 1.99 log P(neutral): 4.12

(128) and 72.4 mg (14.9% of theory, purity 100% according to HPLC) of 2-fluoro-4-methyl-N-[1-(2,2,2-trifluoroethyl)pyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-189).

(129) ##STR00074##

(130) 1H-NMR (D6-DMSO) ppm: 7.09-7.01 (m, 2H), 4.28-4.21 (q, 2H), 3.89-3.81 (q, 2H), 3.51-3.47 (t, 2H), 2.36-2.30 (t, 2H), 2.32 (s, 3H), 1.98-1.90 (m, 2H).

(131) log P(HCOOH): 2.32 log P(neutral): 4.37

Step 2: 2-Fluoro-4-methyl-N-[1-(2,2,2-trifluoroethyl)pyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline (Ib-115)

(132) ##STR00075##

(133) At 0-4 C., 900 mg (2.32 mmol) of 2-fluoro-4-methyl-N-[1-(2,2,2-trifluoroethyl)pyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-189) are initially charged in 40 ml of trichloromethane. After the addition of 850 mg of buffer solution pH 7 (KH.sub.2PO.sub.4/Na.sub.2HPO.sub.4) and 160 mg of benzyltriethylammonium chloride, 600 mg (77%, 2.68 mmol) of m-chloroperbenzoic acid are added a little at a time at 0-4 C. and the reaction mixture is stirred at RT for 24 h. A 33% strength aqueous sodium bisulfite solution is added, and the mixture is then extracted twice with dichloromethane. The combined organic phases are washed with water, dried over sodium sulfate and filtered. After removal of the solvent under reduced pressure, the residue is purified by column chromatography using MPLC on RP(C-18) with water/acetonitrile. This gives 70 mg of product (7.5% of theory, purity 95.2% according to LC/MS).

(134) 13C-NMR (D6-DMSO) ppm: 164.2, 155.6, 138.3, 136.0, 129.8, 125.1, 124.2, 119.9, 117.9, 56.8, 49.5, 44.4, 27.0, 19.5, 16.4

Preparation Example 20

2,4-Dimethyl-N-[1,3-oxazolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline

Step 1: 1-(2-Chloroethyl)-3-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}urea

(135) ##STR00076##

(136) A little at a time, 1.45 g (6.16 mmol) of 2,4-dimethyl-5[(2,2,2-trifluoroethyl)sulfanyl]aniline are added to a solution of 700 mg (6.63 mmol) of 2-chloroethyl isocyanate in 50 ml of tert-butyl methyl ether and a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and subsequently stirred at room temperature for another 18 h. Under reduced pressure, almost all of the solvent is removed from the mixture, and the resulting white solid is filtered off with suction. This leaves 2.00 g of product (88.5% of theory, purity 94.4% according to LC/MS).

(137) 1H-NMR (D6-DMSO) ppm: 8.01 (s, 1H), 7.83 (s, 1H), 7.04 (s, 1H), 6.83 (t, 1H), 3.77-3.69 (q, 2H), 3.68-3.65 (m, 2H), 3.45-3.40 (m, 2H), 2.30 (s, 3H), 2.14 (s, 3H).

Step 2: 2,4-Dimethyl-N-[1,3-oxazolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline

(138) ##STR00077##

(139) 900 mg (2.64 mmol) of 1-(2-chloroethyl)-3-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}urea in a mixture of 15 ml of water and 20 ml of propionitrile with 4 g of potassium carbonate are heated under reflux for 18 h. Under reduced pressure, the mixture is freed from the solvent and the slurry of solids that remains is acidified with dilute hydrochloric acid. The mixture is then allowed to stand for 18 h, and the beige precipitate is then filtered off with suction. This gives 560 mg of crude product. Purification by column chromatography using a Biotage Isolera One and ethyl acetate/cyclohexane 2:1 v/v as mobile phase gives 130 mg of product (16.2% of theory, purity according to LC/MS 81.5%).

(140) log P(HCOOH): 1.36

Preparation Example 21

2-Fluoro-4-methyl-N-[1,3-thiazinan-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-279)

Step 1: 2-Fluoro-4-methyl-N-[(1,3-thiazinan-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]anilinium chloride (Ia-278)

(141) ##STR00078##

(142) A little at a time, 1.61 g (6.72 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline are added to a solution of 1 g (7.37 mmol) of 3-chloropropyl isocyanate in 30 ml of tert-butyl methyl ether and a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and subsequently stirred at room temperature for another 18 h. Under reduced pressure, the mixture is freed from the solvent. The residue that remains is a light-beige oil which slowly crystallizes. This leaves 2.3 g of product (91.3% of theory, purity 95% according to LC/MS).

(143) 13C-NMR (D6-DMSO) ppm: 166.0 (broad), 156.1, 142.1, 131.7, 129.4, 126.1, 120.6, 118.6, 41.3, 34.9, 26.6, 20.6

(144) log P(HCOOH): 1.34

Step 2: 2-Fluoro-4-methyl-N-[1,3-thiazinan-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-279)

(145) ##STR00079##

(146) 2.2 g (5.87 mmol) of 2-fluoro-4-methyl-N-[1,3-thiazinan-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]anilinium chloride (Ia-278) are dissolved in 50 ml of water and made alkaline with ammonium hydroxide (28-30% by weight solution of NH.sub.3 in water). The mixture is extracted repeatedly with dichloromethane. The combined organic phases are separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. This leaves a residue of 1.56 g of product (68.3% of theory, purity 100% according to 1H-NMR) as shiny amber crystals.

Preparation Example 22

2-Fluoro-4-methyl-N-[1,3-thiazolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline

Step 1: 1-(2-Chloroethyl)-3-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}thiourea

(147) ##STR00080##

(148) A little at a time, 1.9 g (7.94 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline are added to a solution of 1 g (8.22 mmol) of 2-chloroethyl isothiocyanate in 50 ml of tert-butyl methyl ether and a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and subsequently stirred at room temperature for another 18 h. Under reduced pressure, almost all of the solvent is removed from the mixture, and the resulting white solid is filtered off with suction. This leaves 2.88 g of product (97.1% of theory, purity 100% according to 1H-NMR).

(149) 1H-NMR (D6-DMSO) ppm: 7.68-7.67 (m, 1H), 7.43-7.40 (m, 1H), 4.03-3.93 (m, 4H), 3.61 (t, 2H), 2.41 (s, 3H).

Step 2: 2-Fluoro-4-methyl-N-[1,3-thiazolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-238)

(150) ##STR00081##

(151) 2.75 g (7.62 mmol) of 1-(2-chloroethyl)-3-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}urea in a mixture of 3 ml of water and 100 ml of propionitrile with 2 g of potassium carbonate, 3.5 g of cesium carbonate, 0.1 g of sodium hydroxide and 0.1 g of potassium iodide are heated under reflux for 48 h. Under reduced pressure, the mixture is freed from the solvent and the slurry of solids that remains is neutralized with dilute hydrochloric acid. The mixture is extracted repeatedly with dichloromethane. The combined organic phases are separated off, dried over magnesium sulfate and freed from the solvent under reduced pressure. This gives 2.38 g of a brown oil as a crude product. Purification by column chromatography using a Biotage Isolera One using a 50 g Snap cartridge and ethyl acetate/cyclohexane 1:1 v/v as mobile phase gives 590 mg of product (23.9% of theory, purity according to LC/MS 92.9%).

(152) 13C-NMR (D6-DMSO) ppm: 163.3, 153.7, 134.8, 126.9 (broad), 126.9, 126.0, 117.0, 45.0 (broad), 35.5, 29.8, 19.4

Step 3: 2-Fluoro-4-methyl-N-[1,3-thiazolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline

(153) ##STR00082##

(154) At 0-4 C., 99 mg (0.305 mmol) of 2-fluoro-4-methyl-N-[1,3-thiazolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (Ia-238) are initially charged in 10 ml of trichloromethane. After the addition of 120 mg of buffer solution pH 7 (KH.sub.2PO.sub.4/Na.sub.2HPO.sub.4) and 20 mg of benzyltriethylammonium chloride, 80 mg (70%, 0.357 mmol) of m-chloroperbenzoic acid are added a little at a time at 0-4 C. and the reaction mixture is stirred at RT for 24 h. A 33% strength aqueous sodium bisulfite solution is added, and the mixture is then extracted twice with dichloromethane. The combined organic phases are washed with water, dried over sodium sulfate and filtered. After removal of the solvent under reduced pressure, the residue is purified by column chromatography using MPLC on RP(C-18) with water/acetonitrile. This gives 15 mg of product (14.4% of theory, purity 100% according to LC/MS).

(155) 13C-NMR (D6-DMSO) ppm: 165.3, 157.5, 137.2, 131.5, 125.6, 120.6, 119.5, 58.5, 46.4, 31.3

(156) log P(HCOOH): 0.80

Preparation Example 23

2-Fluoro-4-methyl-N-[(2E)-1-phenylpyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline (Ib-55)

Step 1: 2-Fluoro-4-methyl-N-[(2E)-1-phenylpyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline

(157) ##STR00083##

(158) 150 mg (0.63 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline and 202 mg (1.25 mmol) of N-phenyl-2-pyrrolidinone are initially charged. 0.29 ml (3.14 mmol) of phosphoryl chloride is slowly added dropwise and the reaction mixture is stirred at 100 C. for 2 h. After cooling, the mixture is poured into ice-water, the pH is adjusted to 8-9 using aqueous sodium hydroxide solution and the mixture is extracted three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is taken up in acetonitrile, adsorbed onto RP(C-18) and purified by MPLC on RP(C-18) using water/acetonitrile. Two fractions are isolated: 89 mg (98% pure, 37% of theory) and 65 mg (98% pure, 27% of theory) of the title compound.

(159) log P(HCOOH): 1.83; log P(neutral): 4.92; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.85 (d, 2H), 7.36 (dd, 2H), 7.12-7.09 (m, 3H), 3.92-3.84 (m, 4H), 2H under the DMSO peak, 2.33 (s, 3H), 2.05-1.97 (m, 2H)

Step 2: 2-Fluoro-4-methyl-N-[(2E)-1-phenylpyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline (Ib-55)

(160) ##STR00084##

(161) At 0-4 C., 89 g (0.23 mmol) of 2-fluoro-4-methyl-N-[(2E)-1-phenylpyrrolidin-2-ylidene]-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline are initially charged in 3 ml of dichloromethane, 69 mg (0.28 mmol) of meta-chloroperbenzoic acid (70%) are added and the reaction mixture is stirred at room temperature for another 2 h. A 33% strength sodium thiosulfate solution (peroxide test carried out) and a saturated sodium bicarbonate solution are then added, and the mixture is extracted twice with dichloromethane. The combined organic phases are washed with a saturated sodium carbonate solution, dried over sodium sulfate and filtered, and the solvent is removed under reduced pressure. The residue comprises 98 mg (94% pure, 99% of theory) of the title compound as a brown oil.

(162) log P(HCOOH): 1.27; log P(neutral): 3.47; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.86 (d, 2H), 7.37 (m, 3H), 7.22 (d, 1H), 7.09 (dd, 1H), 4.14-4.02 (m, 2H), 3.73 (dd, 2H), 2.67-2.57 (m, 2H), 2.33 (s, 3H), 2.07-1.99 (m, 2H)

Preparation Example 24

2-({2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (Ib-71)

Step 1.a: 1-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-3-(2,2,2-trifluoroethyl)thiourea known from JP 2011-42611 (example 250)

(163) ##STR00085##

(164) 1.00 g (4.18 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline is initially charged in 5 ml of dichloromethane, and 0.006 ml (0.042 mmol) of triethylamine is added. After the addition of 0.59 g (4.18 mmol) of 1,1,1-trifluoro-2-isothiocyanatoethane, the reaction mixture is stirred at room temperature overnight. The solvent is removed under reduced pressure, the residue is triturated with a little toluene and the insoluble fraction is filtered off with suction and dried. This gives 0.31 g (100% pure, 20% of theory) of the title compound as a white solid. Under reduced pressure, the filtrate is freed from the solvent. The residue of 1.30 g comprises the title compound in a purity of 77%.

(165) log P(HCOOH): 3.32; log P(neutral): 3.24; 1H-NMR (D6-DMSO, 400 MHz) ppm 9.62 (bs, 1H), 8.34 (bs, 1H), 7.76 (d, 1H), 7.26 (d, 1H), 4.46-4.40 (m, 2H), 3.87 (q, 2H), 2.38 (s, 3H)

Step 2.a: 2-({2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (Ia-175)

(166) ##STR00086##

(167) 75 mg (97% pure, 0.19 mmol) of 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-3-(2,2,2-trifluoroethyl)thiourea and 27 mg (0.19 mmol) of bromoacetic acid are initially charged in 2 ml of toluene, and the mixture is stirred at reflux for 6 h. After cooling, a saturated sodium chloride solution is added to the reaction mixture and the organic phase is separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. The residue is applied to RP(C-18) material and purified by means of MPLC on RP(C-18) using water/acetonitrile. 18 mg (100% pure, 23% of theory) of the title compound are isolated as a white solid.

(168) log P(HCOOH): 4.09; log P(neutral): 3.99; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.27 (d, 1H), 7.21 (d, 1H), 4.58 (q, 2H), 4.24 (s, 2H), 3.87 (q, 2H), 2.39 (s, 3H)

Step 3.a: 2-({2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (Ib-71)

(169) ##STR00087##

(170) At 0-4 C., 136 g (0.32 mmol) of 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one are initially charged in 3 ml of dichloromethane, 84 mg (0.32 mmol) of meta-chloroperbenzoic acid (70%) are added and the reaction mixture is stirred at room temperature for another 2 h. A 33% strength sodium thiosulfate solution (peroxide test carried out) and a saturated sodium bicarbonate solution are then added, and the mixture is extracted twice with dichloromethane. The combined organic phases are washed with a saturated sodium carbonate solution, dried over sodium sulfate and filtered, and the solvent is removed under reduced pressure. The residue comprises 136 mg (100% pure, 96% of theory) of the title compound as a lightly colored oil which, over time, crystallizes to give a white solid.

(171) log P(HCOOH): 2.93; log P(neutral): 2.87; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.51 (d, 1H), 7.38 (d, 1H), 4.62-4.57 (m, 2H), 4.26-4.14 (m, 3H), 4.04-3.94 (m, 1H), 2.36 (s, 3H)

(172) Alternatively, synthesis can be carried out as follows:

Step 1.b: 2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline

(173) ##STR00088##

(174) At 0-4 C., 5.00 g (0.21 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline are initially charged in 100 ml of dichloromethane, 6.18 g (0.25 mmol) of meta-chloroperbenzoic acid are added and the reaction mixture is stirred at room temperature for 2 h. A 33% strength sodium thiosulfate solution is then added (peroxide test carried out), and the mixture is extracted twice with dichloromethane. The combined organic phases are washed with a saturated sodium carbonate solution, dried over sodium sulfate and filtered, and the solvent is removed under reduced pressure. The residue comprises 5.10 g (90% pure, 86% of theory) of the title compound as a brown oil.

(175) log P(HCOOH): 1.77; log P(neutral): 1.72; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.26 (d, 1H), 7.02 (d, 1H), 5.45 (bs, 2H), 4.08-3.95 (m, 1H), 3.88-3.75 (m, 1H), 2.19 (s, 3H)

Step 2.b: 1-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(2,2,2-trifluoroethyl)thiourea

(176) ##STR00089##

(177) 1.00 g (3.53 mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (90% pure) is initially charged in 5 ml of dichloromethane, and 0.005 ml (0.035 mmol) of triethylamine is added. After the addition of 0.50 g (3.53 mmol) of 1,1,1-trifluoro-2-isothiocyanatoethane, the reaction mixture is stirred at room temperature overnight. The insoluble fraction is filtered off with suction and dried. This gives 0.60 g (100% pure, 43% of theory) of the title compound as a white solid. Under reduced pressure, the filtrate is freed from the solvent. The residue of 0.81 g comprises the title compound in a purity of 54%.

(178) log P(HCOOH): 2.34; log P(neutral): 2.30; 1H-NMR (D6-DMSO, 400 MHz) ppm 9.75 (bs, 1H), 8.50 (bs, 1H), 8.12 (bd, 1H), 7.36 (d, 1H), 4.52-4.40 (m, 1H), 4.21-4.15 (m, 1H), 4.05-3.95 (m, 1H), 2.36 (s, 3H)

Step 3.c: 2-({2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (Ib-71)

(179) ##STR00090##

(180) 200 mg (0.51 mmol) of 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(2,2,2-trifluoroethyl)thiourea and 70 mg (0.51 mmol) of bromoacetic acid are initially charged in 2 ml of toluene, and the mixture is stirred at reflux for 6 h. A saturated sodium chloride solution is added to the reaction mixture and the organic phase is separated off, dried over sodium sulfate and freed from the solvent under reduced pressure. The residue is applied to RP(C-18) material and purified by means of MPLC on RP(C-18) using water/acetonitrile. 63 mg (97% pure, 28% of theory) of the title compound are isolated as a white solid.

Preparation Example 25

Synthesis of 3,4-dimethyl-5-(methylsulfanyl)-1,2,4-thiadiazol-4-ium methylsulfate

(181) ##STR00091##

Step 1: 3,4-Dimethyl-1,2,4-thiadiazol-5(4H)-one

(182) ##STR00092##

(183) At 0 C., 6.13 g (27.6 mmol) of phosphorus pentasulfide are added to a solution of 1.80 g (13.80 mmol) of 3,4-dimethyl-1,2,4-thiadiazol-5(4H)-one (crude, prepared according to J. Chem. Soc. Perkin Trans. 1 1983, 4, 687-691) in xylene, and the mixture is then heated at 100 C. for 4 h. After aqueous work-up and chromatographic purification, 0.60 g (30% of theory) of the title compound is obtained.

Step 2: 3,4-Dimethyl-5-(methylsulfanyl)-1,2,4-thiadiazol-4-ium methylsulfate

(184) ##STR00093##

(185) With stirring, 0.62 g (4.52 mmol) of dimethyl sulfate is added to a solution of 0.60 g (4.10 mmol) of 3,4-dimethyl-1,2,4-thiadiazole-5(4H)-thione in acetonitrile, and the mixture is stirred at reflux for 5 h. After cooling, the solvent is removed under reduced pressure and the residue obtained (1.50 g) is reacted further crude.

Preparation Example 26

N-(3,4-Dimethyl-1,2,4-thiadiazol-5(4H)-ylidene)-2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulfinyl]aniline (Ib-173)

Step 1: N-(3,4-Dimethyl-1,2,4-thiadiazol-5(4H)-ylidene)-2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline

(186) The preparation processes described above can be used to give the compounds of the formula (I)for example the following compounds of the formula (I):

(187) TABLE-US-00001 Ex n R.sup.1 R.sup.2 R.sup.3 X.sup.1 X.sup.2 X.sup.3 X.sup.4 log P Ia-01 0 CH.sub.3 CH.sub.3 CF.sub.3 H F H CH.sub.3 4.48.sup.[a]; 4.5.sup.[b] Ia-02 0 propyl H CF.sub.3 H F H CH.sub.3 4.45.sup.[a]; 4.43.sup.[b] Ia-03 0 H H CHF.sub.2 H F H CH.sub.3 2.2.sup.[c] Ia-04 0 pyridin-2-ylmethyl H CF.sub.3 H F H CH.sub.3 3.68.sup.[a] Ia-05 0 propan-2-yl H CF.sub.3 H F H CH.sub.3 4.51.sup.[a]; 4.52.sup.[b] Ia-06 0 H H PD-F-heptyl H F H CH.sub.3 Ia-07 0 H H CF.sub.3 H CH.sub.3 H CH.sub.3 3.36.sup.[a]; 3.4.sup.[b] Ia-08 0 pyridin-2-ylmethyl pyridin-2-ylmethyl CF.sub.3 H F H CH.sub.3 Ia-09 0 CH.sub.3 H CF.sub.3 H CH.sub.3 H F 3.72.sup.[a]; 3.69.sup.[b] Ia-10 0 CH.sub.3 CH.sub.3 DD-F-hexyl H F H CH.sub.3 Ia-11 0 methylsulfonyl H CF.sub.3 H F H CH.sub.3 3.05.sup.[a] Ia-12 0 CH.sub.3 H CF.sub.3 H CH.sub.3 H CH.sub.3 3.95.sup.[a]; 4.01.sup.[b] Ia-13 0 CH.sub.3 H CF.sub.3 H F H CH.sub.3 3.7.sup.[a]; 3.71.sup.[b] Ia-14 0 H H CF.sub.3 H Cl H Cl Ia-15 0 CH.sub.3 H CF.sub.3 H Cl H Cl 4.2.sup.[a]; 4.2.sup.[b] Ia-16 0 (trifluoromethyl)sulfonyl H CF.sub.3 H F H CH.sub.3 Ia-17 0 H H CF.sub.3 H CH.sub.3 H F 3.16.sup.[a]; 3.14.sup.[b] Ia-18 0 ethyl H CF.sub.3 H F H CH.sub.3 4.12.sup.[a]; 4.12.sup.[b] Ia-19 0 CH.sub.3 H CF.sub.3 H H H CF.sub.3 Ia-20 0 CH.sub.3 H CF.sub.3 H Cl H CH.sub.3 Ia-21 0 H H CF.sub.3 H F H CH.sub.3 3.13.sup.[a]; 3.17.sup.[a]; 3.12.sup.[b] Ia-22 0 H H DD-F-hexyl H F H CH.sub.3 Ia-23 0 CH.sub.3 CH.sub.3 CF.sub.3 H CH.sub.3 H CH.sub.3 4.87.sup.[a]; 4.87.sup.[b] Ia-24 0 CH.sub.3 CH.sub.3 CF.sub.3 H CH.sub.3 H F 4.53.sup.[a]; 4.47.sup.[b] Ia-25 0 H H CF.sub.3 H H H CF.sub.3 Ia-26 0 Cpr H CF.sub.3 H F H CH.sub.3 4.03.sup.[a]; 4.02.sup.[b] Ib-01 1 CH.sub.3 CH.sub.3 CF.sub.3 H F H CH.sub.3 Ib-02 1 ethyl H CF.sub.3 H F H CH.sub.3 Ib-03 1 propan-2-yl H CF.sub.3 H F H CH.sub.3 Ib-04 1 CH.sub.3 H CF.sub.3 H CH.sub.3 H CH.sub.3 3.15.sup.[a]; 3.09.sup.[b] Ib-05 1 CH.sub.3 H CF.sub.3 H CH.sub.3 H F 2.86.sup.[a]; 2.79.sup.[b] Ib-06 1 propyl H CF.sub.3 H F H CH.sub.3 3.24.sup.[a]; 3.17.sup.[b] Ib-07 1 CH.sub.3 H CF.sub.3 H F H CH.sub.3 2.64.sup.[a]; 2.61.sup.[b] Ib-08 1 Cpr H CF.sub.3 H F H CH.sub.3 2.68.sup.[a]; 2.67.sup.[b] Ib-09 1 CH.sub.3 CH.sub.3 CF.sub.3 H CH.sub.3 H CH.sub.3 3.23.sup.[a]; 3.19.sup.[b] Ib-10 1 CH.sub.3 H CF.sub.3 H H H CF.sub.3 2.52.sup.[a]; 2.49.sup.[b] lb-11 1 H H CF.sub.3 H F H CH.sub.3 2.77.sup.[a]; 2.71.sup.[b] Ib-12 1 H H CF.sub.3 H CH.sub.3 H CH.sub.3 3.36.sup.[a]; 3.3.sup.[b] Ib-13 1 H H CF.sub.3 H CH.sub.3 H F Ib-14 1 H H CF.sub.3 H Cl H Cl 2.05.sup.[a]; 2.02.sup.[b] Ib-15 1 CH.sub.3 CH.sub.3 CF.sub.3 H CH.sub.3 H F 2.17.sup.[a]; 2.14.sup.[b] Ib-16 1 H H CF.sub.3 H H H CF.sub.3 2.2.sup.[a]; 2.19.sup.[b]
Abbreviations:

(188) PD-F-heptyl=pentadecafluoroheptyl; DD-F-hexyl=1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl; CHF.sub.2=difluoromethyl; Cpr=cyclopropyl; Cl=chlorine; F=fluorine.

(189) The log P values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using reversed-phase columns (C18) by the following methods:

(190) .sup.[a] The LC-MS determination in the acidic range is carried out at pH 2.7 using 0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) as mobile phases; linear gradient from 10% acetonitrile to 95% acetonitrile. Also referred to as log P(HCOOH).

(191) .sup.[b] The LC-MS determination in the neutral range is carried out at pH 7.8 using 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as mobile phases; linear gradient from 10% acetonitrile to 95% acetonitrile. Also referred to as log P(neutral).

(192) .sup.[c] The determination in the acidic range is carried out at pH 2.3 using 0.1% aqueous phosphoric acid and acetonitrile as mobile phases; linear gradient from 10% acetonitrile to 95% acetonitrile.

(193) Calibration is carried out using unbranched alkan-2-ones (having from 3 to 16 carbon atoms) with known log P values (the log P values are determined by the retention times using linear interpolation between two successive alkanones).

(194) The lambda-max values were determined in the maxima of the chromatographic signals using the UV spectra from 200 nm to 400 nm.

(195) NMR Data of Selected Examples

(196) The NMR data for selected examples are listed either in conventional form (6 values, number of hydrogen atoms, multiplet splitting) or as NMR peak lists.

(197) NMR peak list method:

(198) When the 1H NMR data for selected examples are noted in the form of 1H NMR peak lists, first the value in ppm and then the signal intensity is listed for each signal peak, separated by a space. The value-signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.

(199) The peak list for one example therefore takes the form of:

(200) .sub.1 intensity.sub.1; .sub.2 intensity.sub.2; . . . ; .sub.i intensity.sub.i; . . . ; .sub.n intensity.sub.n

(201) The solvent in which the NMR spectrum was recorded is listed in square brackets after the number of the example and before the NMR peak list or the conventional NMR interpretation list.

(202) TABLE-US-00002 Example number 1H-NMR data Ia-01 1H-NMR (D6-DMSO): 7.12 (d, 1H), 7.07 (d, 1H), 3.84-3.92 (m, 2H), 2.98 (broad, 6H), 2.33 (s, 3H) Ia-02 1H-NMR (CDCl3): 7.03-7.09 (m, 1H), 6.91-6.93 (m, 1H), 5.29 (broad, 1H), 3.28-3.38 (m, 4H), 2.42 (s, 3H), 1.69 (broad, 2H), 1.01 (broad, 2H), 0.83-0.88 (m, 1H) Ia-03 1H-NMR (D6-DMSO): 7.11-7.14 (m, 1H), 7.06-7.04 (m, 1H), 6.92-6.98 (broad, 2H), 6.30 (tt, 1H), 3.83-3.91 (q, 2H), 2.34 (s, 3H) Ia-05 [CDCl.sub.3] 7.26 45.31; 7.09 0.35; 7.03 0.72; 6.93 0.95; 6.91 0.85; 5.09 0.50; 4.13 0.50; 3.30 1.93; 3.28 1.82; 2.42 16.00; 1.57 44.22; 1.43 0.36; 1.33 0.54; 1.29 4.62; 1.28 4.60; 1.26 1.33; 1.25 1.06; 1.25 1.27; 1.23 0.74; 1.08 0.47; 0.01 0.72; 0.00 24.21; 0.01 0.77 Ia-07 1H-NMR (D6-DMSO): 7.10 (s, 1H), 6.98 (broad, 2H), 6.85 (s, 1H), 3.87 (q, 2H), 2.30 (s, 3H), 1.98 (s, 3H) Ia-09 [DMSO-D.sub.6] 7.09 3.30; 7.07 3.26; 6.87 0.35; 6.85 0.33; 4.06 0.56; 4.04 1.74; 4.02 1.77; 4.00 0.62; 3.92 0.37; 3.86 1.00; 3.35 143.04; 3.34 312.18; 2.79 0.68; 2.78 0.62; 2.74 0.37; 2.73 0.35; 2.68 0.56; 2.67 0.68; 2.67 0.49; 2.54 0.38; 2.53 0.96; 2.51 54.21; 2.50 72.95; 2.34 0.46; 2.33 0.64; 2.33 0.79; 2.33 0.64; 2.32 0.46; 2.07 1.95; 2.04 0.35; 2.01 16.00; 1.99 8.08; 1.36 0.69; 1.24 0.46; 1.19 2.26; 1.17 4.49; 1.16 2.17; 0.88 0.50; 0.86 0.36; 0.00 9.11 Ia-12 [DMSO-D.sub.6] 7.01 4.28; 4.03 0.82; 4.02 0.83; 3.79 0.35; 3.37 0.42; 3.34 331.71; 3.33 0.37; 3.32 2.34; 2.79 0.50; 2.62 0.35; 2.61 0.48; 2.61 0.35; 2.52 0.66; 2.52 0.84; 2.52 0.90; 2.51 23.83; 2.51 51.40; 2.50 70.93; 2.50 51.33; 2.50 23.51; 2.44 0.53; 2.39 0.35; 2.39 0.53; 2.38 0.38; 2.36 0.58; 2.33 0.49; 2.31 0.74; 2.28 16.00; 2.19 0.55; 1.99 3.80; 1.97 7.19; 1.19 0.93; 1.17 1.84; 1.16 0.90; 0.01 0.74; 0.00 23.54; 0.01 0.71 Ia-13 [CDCl.sub.3] 7.26 51.97; 7.09 0.34; 7.04 0.43; 6.93 0.64; 6.92 0.56; 3.73 0.51; 3.72 0.51; 3.49 0.37; 3.30 1.06; 3.29 1.10; 3.29 0.94; 3.28 0.80; 3.01 1.54; 2.42 16.00; 2.36 0.92; 1.57 10.32; 1.26 0.76; 1.25 1.28; 1.23 0.63; 0.01 0.86; 0.00 28.20; 0.01 0.93 Ia-14 1H-NMR (D6-DMSO): 7.67 (s, 1H), 7.15 (s, 1H), 4.16 (q, 2H) Ia-15 1H-NMR (D6-DMSO): 8.30 (broad, 1H), 7.61 (s, 1H), 7.20 (s, 1H), 4.14 (q, 2H), 2.62 (broad, 3H) Ia-17 1H-NMR (D6-DMSO): 7.15 (d, 1H), 7.10 (broad, 2H), 6.92 (d, 1H), 3.90 (q, 2H), 2.01 (s, 3H) Ia-18 [CDCl.sub.3] 7.26 18.05; 7.26 0.39; 7.25 0.35; 7.24 0.34; 7.04 0.64; 6.94 0.46; 6.93 1.00; 6.92 0.76; 6.91 0.76; 6.84 0.35; 6.82 0.33; 5.26 0.47; 3.45 1.08; 3.41 0.41; 3.39 0.32; 3.30 1.56; 3.28 1.39; 2.47 0.74; 2.42 16.00; 1.58 15.92; 1.29 1.95; 1.26 0.51; 1.25 0.43; 1.25 0.48; 1.09 0.37; 0.00 9.63; 0.01 0.33 Ia-19 1H-NMR (CDCl3): 7.58 (d, 1H), 7.13 (s, 1H), 6.85 (d, 1H), 5.31 (broad, 1H), 3.45 (q, 2H), 2.93 (broad, 3H) Ia-21 1H-NMR (D6-DMSO): 7.17 (d, 1H), 7.09 (d, 1H), 3.91 (q, 2H), 2.34 (s, 3H) Ia-23 1H-NMR (D6-DMSO): 7.02 (s, 1H), 6.79 (s, 1H), 3.83 (q, 2H), 2.87 (broad, 6H), 2.28 (s, 3H), 1.96 (s, 3H) Ia-24 1H-NMR (D6-DMSO): 7.09 (d, 1H), 6.86 (broad, 1H), 3.89 (q, 2H), 2.90 (broad, 3H), 2.00 (s, 3H) Ia-25 1H-NMR (CDCl3): 7.72 (d, 1H), 7.24 (m, 1H), 6.96-6.99 (m, 1H), 4.98 (broad, 2H), 3.48 (q, 2H) Ia-26 [CDCl.sub.3] 7.26 29.38; 6.94 1.54; 6.92 1.55; 3.73 0.38; 3.72 0.38; 3.49 0.34; 3.33 0.70; 3.32 0.83; 2.47 0.43; 2.42 16.00; 1.57 6.79; 1.26 0.58; 1.25 1.07; 1.23 0.54; 0.48 0.53; 0.43 0.39; 0.01 0.45; 0.00 15.80; 0.01 0.53

(203) TABLE-US-00003 Example number 1H-NMR data Ib-01 1H-NMR (D6-DMSO): 7.29 (d, 1H), 7.23 (d, 1H), 4.02-4.14 (m, 2H), 3.01 (broad, 6H), 2.31 (s, 3H) Ib-02 1H-NMR (D6-DMSO): 8.30 (broad, 1H), 7.29 (d, 1H), 7.22 (d, 1H), 4.08-4.14 (m, 2H), 3.99 (broad, 2H), 2.31 (s, 3H), 1.11 (broad, 3H) Ib-03 1H-NMR (D6-DMSO): 8.02 (broad, 1H), 7.28 (d, 1H), 7.21 (d, 1H), 4.08-4.14 (m, 2H), 3.96-4.00 (m, 1H), 2.31 (s, 3H), 1.12-1.17 (broad, 6H) Ib-04 1H-NMR (D6-DMSO): 8.01 (broad, 1H), 7.00-7.20 (m, 2H), 3.70-4.10 (m, 2H), 2.80 (broad, 3H), 2.27 (s, 3H), 2.07 (s, 3H) Ib-05 [DMSO-D.sub.6] 7.76 0.68; 7.75 0.68; 7.48 0.42; 7.46 0.41; 7.27 5.26; 7.26 5.26; 7.09 0.34; 7.02 0.49; 4.32 0.34; 4.30 0.38; 4.27 0.47; 4.26 0.80; 4.24 1.46; 4.22 2.04; 4.20 1.69; 4.18 0.75; 3.35 821.56; 3.34 2.15; 3.33 2.32; 3.17 0.58; 3.16 0.56; 2.81 0.80; 2.73 0.36; 2.62 0.57; 2.62 1.01; 2.62 1.31; 2.61 0.98; 2.61 0.52; 2.54 1.16; 2.52 3.60; 2.52 4.50; 2.52 5.20; 2.51 63.77; 2.51 130.55; 2.50 175.10; 2.50 122.46; 2.50 53.43; 2.48 0.53; 2.39 0.67; 2.39 1.11; 2.39 1.41; 2.38 1.11; 2.38 0.73; 2.37 6.18; 2.33 0.38; 2.31 0.37; 2.27 4.25; 2.11 16.00; 2.09 5.30; 2.08 1.22; 2.02 0.44; 1.91 0.99; 1.23 0.51; 1.14 1.46; 0.01 0.51; 0.00 12.92 Ib-06 1H-NMR (D6-DMSO): 7.28 (d, 1H), 7.22 (d, 1H), 4.10-4.14 (m, 1H), 3.90-4.09 (m, 1H), 3.10-3.30 (broad, 2H), 2.31 (s, 3H), 1.51-1.56 (broad, 2H), 0.84-0.91 (broad, 3H) Ib-07 1H-NMR (D6-DMSO): 7.30 (d, 1H), 7.22 (d, 1H), 3.99-4.15 (m, 2H), 2.66-2.73 (broad, 3H), 2.31 (s, 3H) Ib-08 [DMSO-D.sub.6] 8.43 0.75; 7.39 0.32; 7.22 1.80; 7.20 1.79; 4.37 0.45; 4.13 0.35; 4.11 0.82; 4.09 0.84; 4.07 0.47; 4.05 0.32; 4.03 0.53; 4.02 0.49; 3.45 0.50; 3.44 0.51; 3.44 0.56; 3.43 0.58; 3.43 0.36; 3.42 0.38; 3.40 0.48; 3.40 0.57; 3.39 1.02; 3.38 1.14; 3.35 1478.79; 3.33 18.72; 2.62 0.34; 2.62 0.79; 2.62 1.07; 2.61 0.78; 2.61 0.36; 2.54 0.67; 2.52 1.59; 2.52 2.06; 2.52 2.16; 2.51 57.91; 2.51 127.88; 2.50 173.56; 2.50 123.42; 2.50 53.41; 2.39 0.33; 2.39 0.75; 2.39 1.04; 2.38 0.74; 2.38 0.33; 2.31 16.00; 2.08 2.40; 1.99 1.93; 1.23 0.45; 1.19 0.50; 1.17 1.09; 1.16 0.49; 1.07 0.79; 1.05 1.55; 1.04 0.73; 0.42 0.41; 0.41 0.44; 0.01 0.39; 0.00 13.49; 0.01 0.41 Ib-09 1H-NMR (D6-DMSO): 7.12 (s, 1H), 7.03 (s, 1H), 4.03-4.07 (m, 2H), 2.91 (broad, 6H), 2.27 (s, 3H), 2.07 (s, 3H) Ib-10 1H-NMR (CDCl3): 7.63-7.71 (m, 2H), 7.07 (d, 1H), 5.63 (broad, 1H), 3.25-3.58 (m, 2H), 2.94 (d, 3H) Ib-11 1H-NMR (D6-DMSO): 7.37 (d, 1H), 7.28 (d, 1H), 4.03-4.10 (m, 2H), 2.34 (s, 3H) Ib-12 1H-NMR (D6-DMSO): 7.19 (s, 1H), 7.17 (s, 1H), 3.96-4.04 (m, 2H), 2.30 (s, 3H), 2.07 (s, 3H) Ib-13 1H-NMR (D6-DMSO): 7.31 (d, 1H), 7.10 (d, 1H), 4.23-4.29 (m, 1H), 4.13-4.18 (m, 1H), 2.10 (s, 3H) Ib-14 1H-NMR (D6-DMSO): 7.87 (s, 1H), 7.54 (broad, 2H), 7.33 (s, 1H), 4.10-4.18 (m, 2H) Ib-15 1H-NMR (D6-DMSO): 7.27 (d, 1H), 6.98 (d, 1H), 4.23 (m, 2H), 2.94 (broad, 6H), 2.09 (s, 3H)

(204) TABLE-US-00004 Example number Structure Analytical data Ia-27 1H-NMR (D6-DMSO): 7.11-7.08 (m, 1H), 7.04-7.02 (m, 1H), 6.68 (broad, 2H), 3.89-3.81 (q, 2H), 2.33 (s, 3H), 1.37-1.30 (m, 4H) Ia-28 1H-NMR (D6-DMSO): 7.87 (s, 1H), 7.60-7.27 (broad, 2H), 7.10 (s, 1H), 4.15 (q, 2H) Ia-29 1H-NMR (D6-DMSO): 7.10-7.07 (m, 1H), 7.00-6.98 (m, 1H), 6.60 (broad, 2H), 5.03 (m, 1H), 3.88-3.80 (q, 2H), 2.32 (s, 3H), 2.05- 1.98 (m, 1H), 1.72-1.63 (m, 1H) Ia-30 1H-NMR (D6-DMSO): 7.37 (s, 1H), 7.26 (broad, 2H), 6.99 (s, 1H), 4.00-3.92 (q, 2H), 2.32 (s, 3H) Ia-31 logP (HCOOH) = 4.73, logP(neutral) = 4.67 Ia-32 00 1H-NMR (D6-DMSO): 7.82 (s, 1H), 7.12 (s, 1H), 4.14 (q, 2H), 3.00 (s, 6H) Ia-33 01 1H-NMR (D6-DMSO): 7.06-7.03 (m, 1H), 6.94-6.92 (m, 1H), 6.37 (broad, 2H), 4.93-4.76 (m, 1H), 3.86-3.78 (q, 2H), 2.31 (s, 3H), 2.09-2.05 (m, 1H), 1.42-1.24 (m, 2H) Ia-34 02 1H-NMR (D6-DMSO): 7.03 (s, 1H), 6.76 (s, 1H), 5.99 (broad, 2H), 3.86-3.78 (q, 2H), 2.29 (s, 3H), 1.91 (s, 3H), 1.59-1.55 (m, 2H), 1.29- 1.26 (m, 2H) Ia-35 03 1H-NMR (D6-DMSO): 7.48 (d, 1H), 7.20 (d, 1H), 4.05 (q, 2H), 3.01 (s, 6H) Ia-36 04 1H-NMR (D6-DMSO): 7.29 (m, 1H), 6.94 (m, 1H), 6.32 (broad, 2H), 3.97-3.89 (q, 2H), 2.29 (s, 3H), 1.60 (m, 2H), 1.28 (m, 2H) Ia-37 05 1H-NMR (D6-DMSO): 8.22 (broad, 1H), 7.82 (s, 1H), 7.16 (s, 1H), 4.13 (q, 2H), 2.65 (bs, 3H) Ia-38 06 1H-NMR (D6-DMSO): 7.37 (s, 1H), 7.32 (broad, 2H), 7.00 (s, 1H), 4.01-3.93 (q, 2H), 2.31 (s, 3H) Ia-39 07 1H-NMR (D6-DMSO): 7.01 (m, 2H), 3.84 (q, 2H), 3.38- 3.32 (m, 2H), 2.88 (s, 3H), 2.30 (s, 3H), 2.25 (t, 2H), 1.88 (q, 2H) Ia-40 08 1H-NMR (D6-DMSO): 9.12-9.11 (m, 1H), 8.68-8.67 (m, 1H), 8.32- 8.28 (m, 1H), 7.50-7.47 (m, 1H), 7.17-7.12 (m, 2H), 6.79 (broad, 2H), 3.93-3.85 (q, 2H), 2.36 (s, 3H) Ia-41 09 logP (HCOOH) = 4.62 Ia-42 0 1H-NMR (D6-DMSO): 9.32 (m, 1H), 9.00-8.98 (m, 1H), 8.27- 8.26 (m, 1H), 7.19-7.16 (m, 2H), 7.05-6.98 (broad, 2H), 3.93- 3.85 (q, 2H), 2.37 (s, 3H) Ia-43 1H-NMR (D6-DMSO): 8.32 (bs, 1H), 7.58 (d, 1H), 7.22- 7.20 (m, 1H), 4.05 (q, 2H), 2.80-2.60 (broad,3H) - peaks of the main isomer Ia-44 1H-NMR (D6-DMSO): 7.42-7.35 (m, 2H), 7.28-7.24 (m, 2H), 7.08- 7.06 (m, 1H), 6.88-6.83 (m, 2H), 3.65-3.57 (q, 2H), 2.86-2.85 (d, 3H), 2.21 (s, 3H) Ia-45 LogP (HCOOH) = 4.82, logP(neutral) = 4.71 Ia-46 1H-NMR (D6-DMSO): 8.94 (m, 1H), 8.37-8.34 (m, 1H), 7.63- 7.61 (m, 1H), 7.17-7.12 (m, 2H), 6.86 (broad, 2H), 3.92-3.84 (q, 2H), 2.36 (s, 3H) Ia-47 1H-NMR (D6-DMSO): 7.35 (broad, 2H), 7.17-7.15 (m, 1H), 7.06- 7.04 (m, 1H), 3.92-3.85 (q, 2H), 2.35 (s, 3H) Ia-48 1H-NMR (D6-DMSO): 7.34 (m, 1H), 6.99 (s, 1H), 6.84 (broad, 2H), 6.31 (t, 1H), 3.99-3.91 (q, 2H), 2.30 (s, 3H) Ia-49 1H-NMR (D6-DMSO): 8.63-8.64 (m, 1H), 8.34-8.32 (m, 1H), 7.98- 7.94 (m, 1H), 7.59-7.55 (m, 1H), 7.36 (s, 1H), 7.02 (s, 1H), 6.60 (broad, 2H), 4.05-3.98 (q, 2H), 2.05 (s, 3H) Ia-50 1H-NMR (D6-DMSO): 7.51-6.74 (m, 6H), 3.64-3.56 (q, 2H), 2.98 (s, 3H), 2.89 (s, 3H), 2.18 (s, 3H) Ia-51 1H-NMR (D6-DMSO): 7.10 (d, 1H), 7.04 (d, 1H), 3.86 (q, 2H), 3.40- 3.36 (m, 4H), 2.32 (s, 3H), 1.15-1.11 (m, 6H) Ia-52 0 1H-NMR (D6-DMSO): 8.32 (bs, 1H), 7.49-7.44 (m, 1H), 7.32- 7.21 (m, 1H), 4.04 (q, 2H), 2.70 (bs, 3H) Ia-53 1H-NMR (D6-DMSO): 7.29 (s, 1H), 6.90 (s, 1H), 4.04-3.98 (q, 2H), 2.92 (broad, 6H), 1.98 (s, 3H) Ia-54 1H-NMR (D6-DMSO): 8.86 (broad, 1H), 7.13-7.05 (broad, 2H), 4.77 (broad, 2H), 4.60 (broad, 2H), 4.40 (broad, 1H), 3.85 (broad, 2H), 2.33 (s, 3H) Ia-55 1H-NMR (D6-DMSO): 7.08-7.04 (m, 2H), 6.23 (tt, 1H), 3.87- 3.77 (m, 4H), 3.48-3.46 (t, 2H), 2.31 (s, 3H), 2.32-2.29 (t, 2H); 1.94- 1.90 (m, 2H) Ia-56 1H-NMR (D6-DMSO): 7.37 (s, 1H), 7.27 (broad, 2H), 7.03 (s, 1H), 4.03-3.95 (q, 2H), 2.31 (s, 3H) Ia-57 1H-NMR (D6-DMSO): 7.62 (s, 1H), 7.17 (s, 1H), 4.17-4.12 (m, 2H), 3.00 (s, 6H) Ia-58 1H-NMR (D6-DMSO): 7.10-7.07 (m, 1H), 7.00-6.98 (m, 1H), 6.42 (broad, 2H), 3.88-3.80 (q, 2H), 2.32 (s, 3H), 1.57 (m, 2H), 1.29 (m, 2H) Ia-59 1H-NMR (D6-DMSO): 8.46-8.44 (m, 1H), 8.32-8.31 (m, 1H), 7.60- 7.58 (m, 1H), 7.33-7.30 (m, 1H), 6.83-6.80 (m, 2H), 3.69- 3.61 (q, 2H), 3.01 (s, 3H), 2.93 (s, 3H), 2.17 (s, 3H) Ia-60 1H-NMR (D6-DMSO): 7.37-7.32 (m, 3H), 7.19-7.17 (m, 2H), 6.88- 6.85 (m, 1H), 6.80-6.78 (m, 1H), 3.64-3.56 (q, 2H), 2.86-2.85 (d, 3H), 2.21 (s, 3H) Ia-61 1H-NMR (D6-DMSO): 8.47-8.46 (m, 1H), 8.36 (m, 1H), 7.57- 7.55 (m, 1H), 7.51-7.48 (m, 1H), 7.30-7.27 (m, 1H), 6.89- 6.83 (m, 2H), 3.70-3.62 (q, 2H), 2.89-2.88 (d, 3H), 2.20 (s, 3H) Ia-62 0 1H-NMR (D6-DMSO): 7.54 (s, 1H), 7.02 (broad, 1H), 4.11 (q, 2H), 3.28 (t, 2H), 2.96 (s, 3H), 2.08 (t, 2H), 1.77-1.71 (m, 2H), 1.62- 1.56 (m, 2H) Ia-63 1H-NMR (D6-DMSO): 8.65-8.64 (m, 1H), 8.31-8.29 (m, 1H), 7.98- 7.94 (m, 1H), 7.59-7.56 (m, 1H), 7.17-7.14 (m, 2H), 6.80 (broad, 2H), 3.93-3.85 (q, 2H), 2.36 (s, 3H) Ia-64 1H-NMR (D6-DMSO): 8.46-8.45 (m, 1H), 8.37 (s, 1H), 7.57- 7.55 (m, 1H), 7.49-7.48 (broad, 1H), 7.30-7.27 (m, 1H), 7.13 (s, 1H), 6.78 (s, 1H), 3.73-3.65 (q, 2H), 2.90-2.88 (d, 3H), 2.17 (s, 3H) Ia-65 1H-NMR (D6-DMSO): 7.10 (s, 1H), 6.98 (broad, 2H), 6.83 (s, 1H), 3.89-3.81 (q, 2H), 2.31 (s, 3H), 1.98 (s, 3H) Ia-66 1H-NMR (D6-DMSO): 9.14 (m, 1H), 8.67-8.66 (m, 1H), 8.33- 8.30 (m, 1H), 7.50-7.46 (m, 1H), 7.10 (s, 1H), 6.91 (s, 1H), 6.41 (broad, 2H), 3.89-3.81 (q, 2H), 2.33 (s, 3H), 2.04 (s, 3H) Ia-67 1H-NMR (D6-DMSO): 7.09-7.06 (m, 1H), 6.94-6.92 (m, 1H), 6.53 (broad, 2H), 3.86-3.78 (m, 2H), 2.67 (m, 1H), 2.33 (s, 3H), 1.96- 1.90 (m, 1H), 1.76-1.70 (m, 1H) Ia-68 1H-NMR (D6-DMSO): 7.53 (s, 1H), 7.10 (s, 1H), 4.11 (q, 2H), 3.39 (t, 2H), 2.90 (s, 3H), 2.26 (t, 2H), 1.90 (q, 2H) Ia-69 1H-NMR (D6-DMSO): 8.33 (broad, 1H), 7.50-7.24 (m, 4H), 6.88- 6.85 (m, 1H), 6.76-6.73 (m, 1H), 3.49-3.45 (q, 2H), 2.89-2.88 (d, 3H), 2.18 (s, 3H) Ia-70 1H-NMR (D6-DMSO): 7.36 (s, 1H), 7.22 (broad, 2H), 6.92 (s, 1H), 4.07-3.99 (q, 2H), 1.98 (s, 3H) Ia-71 1H-NMR (D6-DMSO): 7.35-7.32 (m, 2H), 7.19-7.16 (m, 2H), 7.09 (s, 1H), 6.70 (s, 1H), 3.68-3.60 (q, 2H), 2.90 (broad, 6H), 2.15 (s, 3H) Ia-72 0 1H-NMR (D6-DMSO): 8.55-8.54 (m, 1H), 8.04-7.96 (m, 2H), 7.72 (m, 1H), 7.60-7.57 (m, 1H), 7.37 (m, 1H), 6.93-6.90 (m, 1H), 3.63 (q, 2H), 2.83-2.81 (d, 3H), 2.24 (s, 3H) Ia-73 1H-NMR (D6-DMSO): 8.69-8.68 (m, 2H), 7.90-7.89 (m, 2H), 7.17- 7.11 (m, 2H), 6.85 (broad, 2H), 3.93-3.85 (q, 2H), 2.36 (s, 3H) Ia-74 1H-NMR (D6-DMSO): 7.27 (s, 1H), 6.84 (s, 1H), 6.21 (broad, 2H), 4.04-3.94 (q, 2H), 1.93 (s, 3H), 1.30-1.15 (m, 4H) Ia-75 1H-NMR (D6-DMSO): 7.09-7.06 (m, 1H), 6.94-6.92 (m, 1H), 6.65 (broad, 2H), 3.85-3.77 (q, 2H), 2.68-2.62 (m, 1H), 2.33 (s, 3H), 2.17-2.14 (m, 1H), 1.91-1.87 (m, 1H) Ia-76 1H-NMR (D6-DMSO): 7.36 (m, 1H), 7.15 (broad, 2H), 6.95 (s, 1H), 4.08-4.00 (q, 2H), 1.99 (s, 3H) Ia-77 1H-NMR (D6-DMSO): 7.33(d, 1H), 6.99 (d, 1H), 6.64-6.61 (m, 1H), 4.15-4.07 (m, 2H), 2.92 (s, 6H) Ia-78 1H-NMR (D6-DMSO): 7.85 (d, 2H), 7.36 (dd, 2H), 7.12- 7.09 (m, 3H), 3.92-3.84 (m, 4H), 2H under the DMSO peak, 2.33 (s, 3H), 2.05-1.97 (m, 2H) Ia-79 1H-NMR (D6-DMSO): 7.05-7.01 (m, 2H), 6.10 (broad, 2H), 3.88- 3.80 (q, 2H), 2.32 (s, 3H), 2.31 (s, 3H), 2.30 (s, 3H), 1.74 (m, 1H), 1.17 (m, 2H) Ia-80 1H-NMR (D6-DMSO): 8.49-8.48 (m, 2H), 7.51-7.49 (m, 1H), 7.15- 7.14 (m, 2H), 6.87-6.85 (m, 2H), 3.69-3.61 (q, 2H), 2.88-2.87 (d, 3H), 2.20 (s, 3H) Ia-81 1H-NMR (D6-DMSO): 8.95-8.96 (m, 1H), 8.36-8.39 (m, 1H), 7.61- 7.63 (m, 1H), 7.10 (s, 1H), 6.91 (s, 1H), 6.49 (broad, 2H), 3.81- 3.89 (q, 2H), 2.32 (s, 3H), 2.03 (s, 3H) Ia-82 0 1H-NMR (D6-DMSO): 7.09-7.06 (m, 1H), 7.01-6.99 (m, 1H), 6.19 (broad, 2H), 3.95 (s, 2H), 3.88-3.80 (q, 2H), 3.33 (s, 3H), 2.32 (s, 3H) Ia-83 1H-NMR (D6-DMSO): 8.64-8.63 (m, 1H), 8.30-8.28 (m, 1H), 7.98- 7.93 (m, 1H), 7.58-7.55 (m, 1H), 7.33-7.29 (m, 1H), 7.13- 7.11 (m, 1H), 7.02 (s, 1H), 6.84-6.82 (m, 1H), 6.64 (broad, 2H), 4.04- 3.96 (q, 2H) Ia-84 1H-NMR (D6-DMSO): 7.40-7.17 (m, 4H), 6.87-6.84 (m, 1H), 6.77- 6.75 (m, 1H), 3.59-3.46 (m, 2H), 3.14 (broad, 3H), 2.71 (broad, 3H), 2.17 (s, 3H) Ia-85 1H-NMR (D6-DMSO): 8.33 (broad, 1H), 7.11-7.06 (m, 2H), 3.83 (q, 2H), 2.33 (s, 3H), 1.34 (broad, 3H), 0.76 (broad, 2H), 0.57 (broad, 2H) Ia-86 1H-NMR (D6-DMSO): 9.27-9.25 (m, 1H), 8.58-8.56 (m, 1H), 8.03- 8.01 (m, 1H), 7.18-7.14 (m, 2H), 7.01 (broad, 2H), 3.93-3.85 (q, 2H), 2.37 (s, 3H) Ia-87 1H-NMR (D6-DMSO): 8.00 (broad, 1H), 7.28 (s, 1H), 6.95 (broad, 1H), 4.09-4.01 (q, 2H), 2.68-2.67 (broad, 3H), 2.00 (s, 3H) Ia-88 1H-NMR (D6-DMSO): 7.53 (s, 1H), 7.102 (s, 1H), 4.12 (q, 2H), 3.39 (dd, 2H), 2.90 (s, 3H), 2.26 (dd, 2H), 1.90 (m, 2H) Ia-89 logP (HCOOH) = 5.15, logP(neutral) = 5.15 Ia-90 1H-NMR (D6-DMSO): 7.03 (d, 1H), 6.93 (d, 1H), 3.84 (q, 2H), 3.25 (t, 2H), 2.94 (s, 3H), 2.30 (s, 3H), 2.10 (t, 2H), 1.76-1.70 (m, 2H), 1.60-1.54 (m, 2H) Ia-91 1H-NMR (D6-DMSO): 8.44-8.43 (m, 1H), 8.32 (m, 1H), 7.51- 7.48 (m, 1H), 7.28-7.21 (m, 2H), 6.89 (s, 1H), 6.41 (broad, 1H), 3.47- 3.39 (q, 2H), 2.88 (broad, 3H), 2.17 (s, 3H), 2.07 (s, 3H) Ia-92 0 1H-NMR (D6-DMSO): 7.04-7.01 (m, 1H), 6.93-6.91 (m, 1H), 6.12 (broad, 2H), 3.86-3.78 (q, 2H), 2.31 (s, 3H), 1.52 (m, 1H), 0.88- 0.84 (m, 2H), 0.72-0.71 (m, 2H) Ia-93 1H-NMR (D6-DMSO): 7.10-7.07 (m, 2H), 3.87-3.79 (q, 2H), 3.11 (broad, 6H), 2.34 (s, 3H), 1.69-1.68 (m, 1H), 0.68-0.66 (m, 2H), 0.33 (m, 2H) Ia-94 1H-NMR (D6-DMSO): 7.10-7.07 (m, 1H), 6.98-6.96 (m, 1H), 6.15 (broad, 2H), 3.88-3.81 (q, 2H), 3.12-3.08 (m, 1H), 2.33 (s, 3H), 2.37-1.71 (m, 6H) Ia-95 1H-NMR (D6-DMSO): 8.69-8.67 (m, 2H), 7.92-7.91 (m, 2H), 7.11 (s, 1H), 6.90 (s, 1H), 6.47 (broad, 2H), 3.89-3.81 (q, 2H), 2.32 (s, 3H), 2.02 (s, 3H) Ia-96 logP (HCOOH) = 4.37, logP(neutral) = 4.37 Ia-97 1H-NMR (D6-DMSO): 8.20 (bs, 1H), 7.48 (d, 1H), 7.32- 7.17 (m, 1H), 3.98 (q, 2H), 2.90-2.50 (broad, 3H) Ia-98 1H-NMR (D6-DMSO): 8.64-8.63 (m, 1H), 8.35-8.33 (m, 1H), 7.98- 7.93 (m, 1H), 7.58-7.54 (m, 1H), 7.11 (s, 1H), 6.94 (s, 1H), 6.41 (broad, 2H), 3.89-3.82 (q, 2H), 2.33 (s, 3H), 2.03 (s, 3H) Ia-99 1H-NMR (D6-DMSO): 7.09-7.02 (m, 2H), 6.22 (broad, 2H), 4.40- 4.36 (t, 1H), 3.97-3.92 (m, 1H), 3.88-3.80 (q, 2H), 3.76-3.72 (m, 1H), 2.33 (s, 3H), 2.23-2.16 (m, 1H), 2.06-1.98 (m, 1H), 1.89-1.77 (m, 2H) Ia-100 1H-NMR (D6-DMSO): 7.25-7.21 (m, 1H), 7.07-7.05 (m, 1H), 6.83 (m, 1H), 6.65-6.63 (m, 1H), 6.18 (broad, 2H), 4.00-3.92 (q, 2H), 1.55 (m, 2H), 1.26 (m, 2H) Ia-101 1H-NMR (D6-DMSO): 8.69-8.67 (m, 2H), 7.91-7.89 (m, 2H), 7.32- 7.29 (m, 1H), 7.12-7.10 (m, 1H), 6.98 (s, 1H), 6.79-6.77 (m, 1H), 6.65 (broad, 2H), 4.04-3.96 (q, 2H) Ia-102 0 1H-NMR (D6-DMSO): 7.24 (s, 1H), 6.79 (s, 1H), 5.95 (broad, 2H), 4.00-3.92 (q, 2H), 1.93 (s, 3H), 1.51 (broad, 1H), 0.89-0.86 (m, 2H), 0.73-0.70 (m, 2H) Ia-103 1H-NMR (D6-DMSO): 7.54 (bs, 1H), 7.02 (bs, 1H), 4.11 (q, 2H), 3.33 (dd, 2H), 2.96 (s, 3H), 2.08 (dd, 2H), 1.74 (m, 2H), 1.58 (m, 2H) Ia-104 1H-NMR (D6-DMSO): 9.12 (s, 1H), 8.67-8.66 (m, 1H), 8.31- 8.29 (m, 1H), 7.50-7.46 (m, 1H), 7.32-7.28 (m, 1H), 7.12- 7.10 (m, 1H), 6.99 (s, 1H), 6.80-6.78 (m, 1H), 6.66-6.59 (broad, 2H), 4.04-3.96 (q, 2H) Ia-105 1H-NMR (D6-DMSO): 7.33 (bs, 1H), 7.20 (bs, 1H), 3.92 (q, 2H), 3.66 (bs, 2H), 3.34 (m, 2H), 3.13 (bs, 3H), 2.33 (bs, 3H), 2.16 (bs, 3H), 2.02-1.95 (m, 2H) Ia-106 1H-NMR (D6-DMSO): 7.05(m, 1H), 6.88 (m, 1H), 3.75 (q, 2H), 2.98 (s, 3H), 2.87 (s, 3H), 2.33 (s, 3H), 1.83 (m, 2H), 0.95-0.93 (m, 7H) Ia-107 1H-NMR (D6-DMSO): 8.94-8.93 (m, 1H), 8.41-8.34 (m, 2H), 7.82- 7.80 (m, 1H), 7.63-7.61 (m, 1H), 7.32-7.28 (m, 1H), 6.99 (s, 1H), 6.68-6.65 (broad, 2H), 4.00 (q, 2H) Ia-108 1H-NMR (D6-DMSO): 7.15-7.09 (m, 2H), 3.89-3.81 (q, 2H), 2.61 (m, 1H), 2.33 (s, 3H), 1.45 (m, 1H), 0.84-0.80 (m, 3H), 0.69- 0.61 (m, 4H), 0.50 (m, 2H) Ia-109 1H-NMR (D6-DMSO): 7.48 (d, 1H), 7.15 (d, 1H), 4.00 (q, 2H), 2.98 (s, 6H) Ia-110 1H-NMR (D6-DMSO): 7.18 (d, 1H), 7.04-6.97 (m, 2H), 3.83 (q, 2H), 3.15 (m, 2H), 2.31 (s, 3H), 1.35 (m, 1H), 0.99 (t, 3H), 0.79- 0.77 (m, 2H), 0.60-0.57 (m, 2H) Ia-111 1H-NMR (D6-DMSO): 7.40 (broad, 2H), 7.18-7.15 (m, 1H), 7.07- 7.05 (m, 1H), 3.93-3.85 (q, 2H), 2.35 (s, 3H) Ia-112 0 1H-NMR (D6-DMSO): 7.14-7.12 (m, 1H), 7.06-7.04 (m, 1H), 6.75 (broad, 2H), 4.18 (s, 2H), 3.90-3.82 (q, 2H), 2.34 (s, 3H) Ia-113 1H-NMR (D6-DMSO): 8.15 (s, 1H), 7.33 (bs, 1H), 7.21 (d, 1H), 3.94 (q, 2H), 3.49 (broad, 2H), 3.19 (broad, 3H), 2.34 (s, 3H), 2.24- 2.06 (m, 5H), 1.78 (broad, 2H), 1.61 (broad, 2H) Ia-114 1H-NMR (D6-DMSO): 8.44-8.42 (m, 1H), 8.31-8.30 (m, 1H), 7.60- 7.58 (m, 1H), 7.32-7.29 (m, 1H), 6.96-6.92 (m, 1H), 6.79- 6.77 (m, 1H), 6.60-6.59 (m, 1H), 6.41-6.38 (m, 1H), 3.79-3.71 (q, 2H), 3.00 (broad, 3H); 2.92 (broad, 3H) Ia-115 1H-NMR (D6-DMSO): 7.36-7.28 (broad, 2H), 7.17-7.15 (m, 1H), 7.09-7.06 (s, 1H), 3.94-3.86 (q, 2H), 2.34 (s, 3H) Ia-116 1H-NMR (D6-DMSO): 8.04-8.01 (m, 2H), 7.29-7.25 (m, 2H), 7.14- 7.09 (m, 2H), 6.61 (broad, 2H), 3.87 (q, 2H), 2.36 (s, 3H) Ia-117 1H-NMR (D6-DMSO): 9.45-9.44 (m, 1H), 8.83-8.82 (m, 1H), 8.72- 8.71 (m, 1H), 7.20-7.16 (m, 2H), 6.98-6.92 (broad, 2H), 3.93-3.85 (q, 2H), 2.37 (s, 3H) Ia-118 1H-NMR (D6-DMSO): 7.11-7.08 (m, 1H), 7.01-6.99 (m, 1H), 6.26 (broad, 2H), 3.90-3.82 (q, 2H), 2.32 (s, 3H), 1.66-1.56 (m, 4H) Ia-119 1H-NMR (D6-DMSO): 7.77-7.75 (m, 2H), 7.36-7.34 (m, 2H), 6.83 (d, 1H), 6.74 (d, 1H), 3.57 (q, 2H), 3.10 (broad, 3H), 2.73 (broad, 3H), 2.17 (s, 3H) Ia-120 1H-NMR (D6-DMSO): 7.35-7.29 (m, 1H), 7.12-7.07 (m, 1H), 7.02- 7.01 (m, 1H), 7.00-6.93 (m, 1H), 6.84-6.78 (m, 2H), 3.60 (q, 2H), 3.07 (broad, 3H), 2.73 (broad, 3H), 2.17 (s, 3H) Ia-121 1H-NMR (D6-DMSO): 7.76 (s, 1H), 7.48-7.33 (broad, 2H), 7.13 (s, 1H), 4.20-4.12 (m, 2H) Ia-122 0 1H-NMR (D6-DMSO): 7.09 (s,1H), 6.90 (broad, 2H), 6.84 (s, 1H), 3.90-3.82 (q, 2H), 2.31 (s, 3H), 1.99 (s, 3H) Ia-123 1H-NMR (D6-DMSO): 7.56 (s, 1H), 7.04 (s, 1H), 6.53 (broad, 2H), 4.13-4.05 (q, 2H), 1.62-1.59 (m, 2H), 1.31-1.28 (m, 2H) Ia-124 1H-NMR (D6-DMSO): 7.78 (s, 1H), 7.57-7.33 (broad, 1H), 7.12 (s, 1H), 4.19-4.11 (2H) Ia-125 1H-NMR (D6-DMSO): 7.63 (s, 1H), 7.09 (s, 1H), 7.02- 6.97 (broad, 2H), 6.34 (t, 1H), 4.16-4.09 (q, 2H) Ia-126 1H-NMR (D6-DMSO): 7.40-7.39 (m, 1H), 7.33-7.27 (m, 1H), 7.16- 7.11 (m, 1H), 7.02-6.97 (m, 2H), 6.87-6.82 (t, 2H), 3.64-3.56 (q, 2H), 2.87-2.86 (m, 3H), 2.21 (s, 3H) Ia-127 1H-NMR (D6-DMSO): 7.10 (s, 1H), 7.05 (broad, 2H), 6.84 (s, 1H), 3.90-3.82 (q, 2H), 2.31 (s, 3H), 1.96 (s, 3H) Ia-128 1H-NMR (D6-DMSO): 7.19-7.16 (m, 2H), 7.13-7.08 (m, 2H), 6.82 (d, 1H), 6.72 (d, 1H), 3.58 (q, 2H), 3.01 (broad, 3H), 2.72 (broad, 3H), 2.17 (s, 3H) Ia-129 logP (HCOOH) = 4.2, logP(neutral) = 4.2 Ia-130 1H-NMR (D6-DMSO): 9.33 (m, 1H), 9.01-9.00 (m, 1H), 8.28- 8.27 (m, 1H), 7.66 (s, 1H), 7.21 (s, 1H), 7.12-7.00 (broad, 2H), 4.16- 4.08 (q, 2H) Ia-131 1H-NMR (D6-DMSO): 7.77-7.75 (m, 2H), 7.36-7.34 (m, 2H), 6.83 (d, 1H), 6.74 (d, 1H), 3.58 (q, 2H), 3.10 (broad, 3H), 2.70 (broad, 3H), 2.17 (s, 3H) Ia-132 00 1H-NMR (D6-DMSO): 7.11-7.10 (m, 1H), 7.07-7.01 (m, 1H), 6.49 (broad, 2H), 3.88-3.83 (q, 2H), 3.65 (s, 2H), 2.33 (s, 3H) Ia-133 01 1H-NMR (D6-DMSO, 400 MHz): 7.58 (d, 1H), 7.18 (d, 1H), 4.06 (q, 2H), 3.01 (s, 6H) Ia-134 02 1H-NMR (D6-DMSO): 8.66-8.65 (m, 1H), 8.32-8.30 (m, 1H), 8.00- 7.95 (m, 1H), 7.64 (s, 1H), 7.60-7.57 (m, 1H), 7.20 (s, 1H), 6.95 (broad, 2H), 4.16-4.08 (m, 2H) Ia-135 03 1H-NMR (D6-DMSO): 8.95 (broad, 1H), 8.38-8.32 (m, 1H), 7.64 (m, 2H), 7.19 (s, 1H), 6.94 (broad, 2H), 4.15-4.08 (q, 2H) Ia-136 04 1H-NMR (D6-DMSO): 8.47-8.45 (m, 1H), 8.35(s, 1H), 7.56- 7.54 (m, 1H), 7.39-7.38 (m, 1H), 7.31-7.27 (m, 1H), 7.15 (s, 1H), 6.54 (broad, 1H), 3.71-3.64 (q, 2H), 2.89-2.88 (d, 3H), 2.08 (s, 3H). Ia-138 05 1H-NMR (D6-DMSO): 7.20-7.16 (m, 2H), 4.79 (q, 2H), 3.83 (q, 2H), 2.35 (s, 3H), 2.10 (s, 3H), 2.03 (s, 3H) Ia-139 06 1H-NMR (D6-DMSO): 7.52 (s, 1H), 6.98 (s, 1H), 6.24- 6.15 (broad, 2H), 4.11-4.03 (q, 2H), 1.51 (m, 1H), 0.92-0.88 (m, 2H), 0.76-0.71 (m, 2H) Ia-140 07 1H-NMR (D6-DMSO): 7.58 (s, 1H), 6.95 (s, 1H), 6.70 (broad, 2H), 4.07-4.00 (m, 2H), 2.17-2.14 (m, 1H), 1.95-1.93 (m, 1H) Ia-141 08 1H-NMR (D6-DMSO): 9.13 (m, 1H), 8.69 (m, 1H), 8.32 (m, 1H), 7.64 (s, 1H), 7.49 (m, 1H), 7.18 (s, 1H), 6.89 (broad, 2H), 4.16- 4.08 (broad, 2H) Ia-143 09 logP (HCOOH) = 1.37, logP(neutral) = 3.25 Ia-144 0 1H-NMR (D6-DMSO): 7.34-7.33 (m, 1H), 7.23-7.20 (m, 2H), 7.12- 7.07 (m, 2H), 6.85 (d, 1H), 6.77 (d, 1H), 3.58 (q, 2H), 2.86- 2.85 (m, 3H), 2.21 (s, 3H) Ia-145 1H-NMR (D6-DMSO): 7.09-7.07 (m, 1H), 6.99-6.98 (m, 1H), 6.72 (broad, 1H), 3.85-3.79 (m, 4H), 2.33 (s, 3H), 1.41 (broad, 1H), 0.85-0.83 (m, 2H), 0.68-0.65 (m, 2H) Ia-146 1H-NMR (D6-DMSO): 8.50-8.49 (m, 1H), 8.41 (s, 1H), 7.71 (broad, 1H), 7.50-7.58 (m, 1H), 7.52-7.48 (m, 1H), 7.34- 7.30 (m, 1H), 6.95 (broad, 1H), 3.96-3.88 (q, 2H), 2.92-2.90 (d, 3H) Ia-147 1H-NMR (D6-DMSO): 7.36-7.30 (m, 1H), 7.17-7.08 (m, 3H), 6.83 (d, 1H), 6.73 (d, 1H), 3.55 (q, 2H), 3.13 (broad, 3H), 2.76 (broad, 3H), 2.17 (s, 3H) Ia-148 1H-NMR (D6-DMSO): 8.46-8.45 (m, 1H), 8.03 (s, 1H), 7.64- 7.63 (q, 1H), 6.90-6.94 (m, 2H), 3.72-3.64 (q, 2H), 2.89 (d, 3H), 2.22 (s, 3H) Ia-149 1H-NMR (D6-DMSO): 7.00 (m, 1H), 6.94-6.91 (d, 1H), 6.86- 6.84 (m, 2H), 3.68 (q, 2H), 2.97 (s, 6H), 2.23 (s, 3H) Ia-150 1H-NMR (D6-DMSO): 8.24-8.23 (m, 1H), 7.76 (broad, 1H), 7.66- 7.63 (m, 1H), 7.45-7.43 (m, 1H), 6.90-6.87 (m, 2H), 6.03- 5.97 (m, 1H), 5.32-5.28 (m, 1H), 5.16-5.13 (m, 1H), 4.02 (broad, 2H), 3.72-3.64 (q, 2H), 2.22 (s, 3H) Ia-151 1H-NMR (D6-DMSO): 8.90 (m, 1H), 8.67 (m, 2H), 7.89- 7.88 (m, 1H), 7.67-7.66 (m, 1H), 7.46-7.45 (m, 1H), 7.22- 7.19 (m, 1H), 3.89-3.73 (m, 4H), 2.30 (s, 3H), 1.38-1.35 (t, 3H) Ia-152 1H-NMR (D6-DMSO): 8.25-8.20 (m, 2H), 7.73 (broad, 1H), 7.66- 7.61 (m, 1H), 7.48-7.46 (m, 1H), 6.94 (broad, 1H), 3.97-3.89 (q, 2H), 2.91-2.90 (d, 3H) Ia-153 1H-NMR (D6-DMSO): 8.58 (t, 1H), 7.60 (m, 1H), 7.10 (m, 1H), 4.10-3.87 (m, 4H), 1.38 (m, 1H), 0.88 (m, 2H), 0.71 (m, 2H) Ia-155 0 1H-NMR (D6-DMSO): 7.96 (bs, 1H), 7.48 (d, 1H), 7.33 (bs, 2H), 6.51 (d, 1H), 3.90-3.70 (m, 2H) Ia-156 1H-NMR (D6-DMSO): 7.54 (s, 1H), 6.98 (s, 1H), 6.10 (broad, 2H), 4.10-4.02 (q, 2H), 2.14 (m, 1H), 1.84-1.15 (m, 10H) Ia-158 1H-NMR (D6-DMSO): 8.21-8.18 (m, 1H), 7.65-7.58 (m, 2H), 7.43- 7.41 (m, 1H), 6.90-6.87 (m, 2H), 3.73-3.66 (q, 2H), 2.22 (s, 3H), 2.92 (m, 1H), 0.74-0.67 (m, 2H), 0.60-0.56 (m, 2H) Ia-159 1H-NMR (D6-DMSO): 8.84 (m, 1H), 8.21-8.19 (m, 1H), 8.02- 8.00 (m, 1H), 7.61-7.59 (m, 1H), 7.29-7.26 (m, 2H), 3.76-3.69 (q, 2H), 2.84 (broad, 3H), 2.30 (s, 3H) Ia-160 1H-NMR (D6-DMSO): 8.57 (m, 1H), 7.96-7.94 (m, 1H), 7.86- 7.84 (m, 1H), 6.91-6.88 (m, 2H), 3.65-3.57 (q, 2H), 3.15 (broad, 3H), 2.80 (broad, 3H), 2.18 (s, 3H) Ia-161 1H-NMR (D6-DMSO): 7.08-7.05 (m, 1H), 6.98 (m, 1H), 6.20 (broad, 2H), 3.87-3.79 (q, 2H), 2.33 (s, 3H), 2.30 (m, 1H), 1.84- 1.52 (m, 8H) Ia-162 1H-NMR (D6-DMSO): 6.88 (d, 1H), 6.70-6.69 (m, 1H), 6.63 (d, 1H), 5.91-5.89 (m, 2H), 3.58 (q, 2H), 3.39 (s, 3H), 3.05 (broad, 3H), 2.77 (broad, 3H), 2.21 (s, 3H) Ia-163 1H-NMR (D6-DMSO): 7.05-6.99 (m, 2H), 6.24 (broad, 1H), 3.86- 3.78 (q, 2H), 2.65-2.64 (d, 3H), 2.31 (s, 3H) 1.35 (m, 1H), 0.79- 0.75 (m, 2H), 0.62-0.57 (m, 2H) Ia-165 logP (HCOOH) = 1.68, logP(neutral) = 3.49 Ia-166 1H-NMR (D6-DMSO): 7.68 (m, 1H), 6.91 (d, 1H), 6.75 (d, 1H), 6.42-6.41 (m, 1H), 6.25-6.24 (m, 1H), 3.69 (q, 2H), 2.94 (s, 6H), 2.24 (s, 3H) Ia-167 0 1H-NMR (D6-DMSO): 8.42-8.40 (m, 1H), 8.29 (m, 1H), 7.59- 7.56 (m, 1H), 7.30-7.27 (m, 1H), 6.83 (s, 1H) 2.04 (s, 3H), 6.42 (s, 1H), 2.13 (s, 3H), 3.51-3.43 (q, 2H), 2.92 (broad, 6H) Ia-168 1H-NMR (D6-DMSO): 8.35-8.33 (m, 1H), 7.76 (m, 1H), 7.54- 7.52 (m, 1H), 7.25 (m, 1H), 7.07 (m, 2H), 3.74 (q, 2H), 3.07 (d, 3H), 2.27 (s, 3H) Ia-169 1H-NMR (D6-DMSO): 7.05-7.02 (m, 1H), 6.93-6.91 (m, 1H), 5.90 (broad, 2H), 3.85-3.77 (q, 2H), 2.3 (s, 3H), 2.16-2.10 (m, 1H), 1.83-1.15 (m, 10H) Ia-171 1H-NMR (D6-DMSO): 8.73 (broad, 1H), 7.32-7.25 (broad, 5H), 7.08-7.05 (m, 1H), 6.96-6.94 (m, 1H), 4.48 (broad, 2H) 3.78 (q, 2H), 2.32 (s, 3H) Ia-172 1H-NMR (D6-DMSO): 8.70 (m, 2H), 7.90-7.87 (m, 2H), 7.64 (m, 1H), 7.18 (s, 1H), 6.94 (broad, 2H), 4.15-4.08 (q, 2H) Ia-173 1H-NMR (D6-DMSO): 7.60 (s, 1H), 7.06 (s, 1H), 6.63- 6.54 (broad, 2H), 4.14-4.07 (q, 2H), 3.67 (s, 2H) Ia-175 1H-NMR (D6-DMSO): 7.27 (d, 1H), 7.21 (d, 1H), 4.58 (q, 2H), 4.24 (s, 2H), 3.87 (q, 2H), 2.39 (s, 3H) Ia-176 1H-NMR (D6-DMSO): 7.31-7.29 (m, 2H), 7.14-7.08 (m, 3H), 6.89 (s, 1H), 6.36 (s, 1H), 3.41-3.33 (q, 2H), 2.85 (broad, 3H), 2.18 (s, 3H), 2.07 (s, 3H) Ia-177 1H-NMR (D6-DMSO): 7.59-7.58 (m, 1H), 7.43 (s, 1H), 7.40- 7.27 (m, 3H), 7.08-7.06 (m, 1H), 6.88 (s, 1H), 3.90-3.82 (q, 2H), 2.88- 2.87 (d, 3H) Ia-178 1H-NMR (D6-DMSO): 7.73 (m, 1H), 7.03-6.93 (m, 3H), 6.19- 5.87 (m, 3H), 3.80-3.71 (m, 3H), 2.32 (s, 3H), 1.80-1.78 (d, 3H), 1.48 (m, 2H), 1.03-1.02 (d, 3H), 0.81 (t, 3H) Ia-180 0 1H-NMR (D6-DMSO): 7.07-7.04 (m, 2H), 3.80 (q, 2H), 3.18 (broad, 4H), 2.33 (s, 3H), 1.84 (broad, 4H) Ia-181 1H-NMR (D6-DMSO): 7.76 (m, 1H), 7.65-7.64 (m, 1H), 7.15- 7.08 (m, 3H), 6.68 (broad, 2H), 3.92-3.84 (q, 2H), 2.35 (s, 3H) Ia-182 1H-NMR (D6-DMSO): 7.59-7.56 (m, 1H), 6.98-6.95 (m, 2H), 6.87 (d, 1H), 6.77 (d, 1H), 3.63 (q, 2H), 2.96 (s, 6H), 2.20 (s, 3H) Ia-183 1H-NMR (D6-DMSO): 8.46-8.45 (m, 1H), 8.36 (s, 1H), 7.57- 7.55 (m, 1H), 7.33-7.27 (m, 2H), 7.01-6.97 (m, 1H), 6.84- 6.82 (m, 1H), 6.64 (s, 1H), 6.44-6.42 (m, 1H), 3.79-3.71 (q, 2H), 2.87- 2.86 (d, 3H) Ia-184 1H-NMR (D6-DMSO): 8.48 (broad, 1H), 7.11-7.01 (m, 2H), 4.90 (broad, 1H), 3.79 (q, 2H), 3.50 (broad, 2H), 3.18 (broad, 2H), 2.34 (s, 3H) Ia-185 1H-NMR (D6-DMSO): 7.25-7.21 (m, 1H), 6.96-6.90 (m, 2H), 6.84- 6.81 (m, 2H), 6.60 (d, 1H), 3.73 (s, 3H), 3.50-3.37 (m, 2H), 3.10 (broad, 3H), 2.69 (broad, 3H), 2.17 (s, 3H) Ia-186 1H-NMR (D6-DMSO): 7.06-7.02 (m, 2H), 6.84-6.80 (m, 3H), 6.70 (d, 1H), 3.68 (s, 3H), 3.54 (q, 2H), 2.91 (broad, 6H), 2.17 (s, 3H) Ia-187 1H-NMR (D6-DMSO): 7.14 (s, 1H), 7.00 (s, 1H), 3.92 (s, 2H), 3.82 (q, 2H), 2.71 (septet, 1H), 2.33 (s, 3H), 2.06 (s, 3H), 1.00- 0.90 (m, 4H) Ia-188 1H-NMR (D6-DMSO): 7.28-7.25 (m, 2H), 6.32 (tt, 1H), 4.21- 4.12 (m, 4H), 3.87 (q, 2H), 2.38 (s, 3H) Ia-189 1H-NMR (D6-DMSO) 7.09-7.01 (m, 2H), 4.24 (q, 2H), 3.85 (q, 2H), 3.49 (t, 2H), 2.33 (t, 3H), 2.32 (s, 3H), 1.98-1.90 (m, 2H) Ia-190 0 1H-NMR (D6-DMSO): 9.49 (m, 1H), 8.81 (m, 1H), 8.71 (m, 1H), 7.13 (s, 1H), 6.98 (s, 1H), 6.53 (broad, 2H), 3.86 (q, 2H), 2.33 (s, 3H), 2.06 (s, 3H) Ia-191 1H-NMR (D6-DMSO): 8.15 (d, 2H), 7.72 (d, 2H), 7.14 (d, 2H), 3.95- 3.85 (m, 2 2H), 2.54 (m, 2H), 2.34 (s, 3H), 2.04 (m, 2H) Ia-192 1H-NMR (D6-DMSO): 7.67 (d, 1H), 7.36 (d, 1H), 4.59 (q, 2H), 4.27 (s, 2H), 4.06 (q, 2H) Ia-193 1H-NMR (D6-DMSO): 7.30-7.25 (m, 3H), 7.13-7.11 (m, 2H), 6.81- 6.78 (m, 1H), 6.73-6.71 (m, 1H), 3.54 (q, 2H), 3.08 (broad, 3H), 2.75 (broad, 3H), 2.16 (s, 3H) Ia-194 1H-NMR (D6-DMSO): 7.51 (d, 1H), 7.19 (d, 1H), 6.85 (dd, 1H), 4.57 (q, 2H), 4.21 (s, 2H), 4.12 (q, 2H) Ia-195 1H-NMR (D6-DMSO): 7.27 (d, 1H), 7.09 (d, 1H), 6.79 (dd, 1H), 4.57 (q, 2H), 4.18 (s, 2H), 3.94 (q, 2H), 2.35 (s, 3H) Ia-196 1H-NMR (D6-DMSO): 7.76 (s, 1H), 7.35 (s, 1H), 4.13 (q, 2H), 4.02 (s, 2H), 2.71 (septet, 1H), 1.02-0.94 (m, 4H) Ia-197 1H-NMR (D6-DMSO): 7.25-7.20 (m, 2H), 3.98 (s, 2H), 3.87 (q, 2H), 2.74-2.60 (m, 1H), 2.40 (s, 3H), 1.00-0.87 (m, 4H) Ia-198 1H-NMR (D6-DMSO): 9.30 (broad, 1H), 7.85 (s, 1H), 7.75 (s, 1H), 4.21 (q, 2H), 2.87 (s, 3H), 1.20 (m, 2H), 1.05 (m, 2H) Ia-199 1H-NMR (D6-DMSO): 8.47-8.46 (m, 1H), 8.37-8.36 (m, 1H), 7.66- 7.63 (m, 1H), 7.37 (s, 1H), 7.35-7.31(m, 1H), 6.92 (s, 1H), 3.92 (q, 2H), 3.08 (broad, 3H), 2.85 (broad, 3H) Ia-200 0 1H-NMR (D6-DMSO): 8.87 (s, 1H), 8.38 (m, 1H), 7.04-7.02 (m, 1H), 6.94 (s, 1H), 6.33 (broad, 1H), 3.79 (q, 2H), 3.63-3.58 (m, 2H), 3.23 (t, 2H), 2.31 (s, 3H), 1.34 (m, 1H), 0.76-0.72 (m, 2H), 0.60- 0.55 (m, 2H) Ia-201 1H-NMR (D6-DMSO): 7.10-7.05 (m, 2H), 5.14-5.06 (m, 1H), 3.89- 3.81 (q, 2H), 3.51-3.49 (m, 2H), 2.32 (s, 3H), 2.30-2.28 (m, 2H), 1.98- 1.89 (m, 2H), 1.38-1.36 (broad, 3H) Ia-202 1H-NMR (D6-DMSO): 7.59 (s, 1H), 7.05 (s, 1H), 4.10 (q, 2H), 3.70 (s, 2H), 3.08 (broad, 6H) Ia-203 1H-NMR (D6-DMSO): 7.66 (d, 1H) 7.55-7.41 (m, 4H), 6.87- 6.83 (m, 2H), 3.56 (q, 2H), 2.89 (d, 3H), 2.19 (s, 3H) Ia-204 1H-NMR (D6-DMSO): 7.42 (d, 1H), 7.26 (broad, 2H), 7.05 (d, 1H), 6.75-6.72 (m, 1H), 4.13 (q, 2H) Ia-205 1H-NMR (D6-DMSO): 7.35 (s, 1H), 7.31-7.27 (m, 3H), 7.18- 7.16 (m, 2H), 6.81 (s, 1H), 3.82 (q, 2H), 3.10 (broad, 3H), 2.82 (d, 3H) Ia-206 1H-NMR (D6-DMSO): 7.09-7.06 (m, 1H), 7.01-6.99 (m, 1H), 6.47- 6.44 (m, 1H), 3.85 (q, 2H), 2.65-2.59 (m, 2H), 2.33 (s, 3H), 1.41 (m, 1H), 1.27 (d, 3H), 0.96-0.61 (m, 4H) Ia-207 1H-NMR (D6-DMSO): 7.45-6.76 (m, 6H), 3.86 (q, 2H), 3.17 (broad, 3H), 2.73 (broad, 3H) Ia-208 1H-NMR (D6-DMSO): 9.45 (s, 1H), 8.84 (m, 1H), 8.74-8.73 (m, 1H), 7.66 (s, 1H), 7.23 (s, 1H), 7.03 (broad, 2H), 4.12 (q, 2H) Ia-209 1H-NMR (D6-DMSO): 7.61 (broad, 1H), 7.11 (broad, 1H), 6.20 (broad, 2H), 4.10 (q, 2H), 3.14 (m, 1H), 2.32-1.78 (m, 6H) Ia-210 0 1H-NMR (D6-DMSO): 7.65 (s, 1H), 7.15 (broad, 2H), 7.10 (s, 1H), 4.15 (q, 2H) Ia-211 1H-NMR (D6-DMSO): 7.39-7.35 (m, 3H), 7.21-7.19 (m, 2H), 6.85 (s, 1H), 3.86 (q, 2H), 3.07 (broad, 3H), 2.79 (broad, 3H) Ia-212 1H-NMR (D6-DMSO): 7.63 (d, 1H), 7.54-7.46 (m, 2H), 7.42 (d, 1H), 6.83-6.78 (m, 2H), 3.56 (q, 2H), 3.11 (broad, 3H), 2.76 (broad, 3H), 2.16 (s, 3H) Ia-213 1H-NMR (D6-DMSO): 7.20 (d, 1H), 7.10 (broad, 2H), 6.96 (d, 1H), 6.69-6.67 (m, 1H), 3.97 (q, 2H), 2.31 (s, 3H) Ia-214 1H-NMR (D6-DMSO): 8.56-8.55 (m, 1H), 7.69-7.68 (m, 2H), 7.38- 7.22 (m, 3H), 6.93 (s, 1H), 3.48 (broad, 2H), 2.77 (broad, 3H), 2.22 (s, 3H), 2.06 (s, 3H) Ia-215 1H-NMR (D6-DMSO): 7.99 (d, 2H), 7.51 (d, 2H), 7.14-7.09 (m, 2H), 6.65 (broad, 2H), 3.87 (q, 2H), 2.35 (s, 3H) Ia-216 1H-NMR (D6-DMSO): 7.10-7.07 (m, 1H), 6.94-6.92 (m, 1H), 3.83 (q, 2H), 3.52 (q, 2H), 3.04 (broad, 6H), 2.32 (s, 3H) Ia-217 1H-NMR (D6-DMSO): 8.05 (broad, 1H), 7.32 (d, 1H), 7.03 (broad, 1H), 6.65 (broad, 1H), 4.09 (q, 2H), 2.70 (broad, 3H) Ia-218 1H-NMR (D6-DMSO): 7.57 (d, 1H), 7.49 (broad, 1H), 7.17 (d, 1H), 7.05-6.99 (m, 2H), 3. Ia-219 1H-NMR (D6-DMSO): 7.58 (s, 1H), 7.07 (s, 1H), 6.40 (broad, 2H), 3.93 (q, 2H), 1.75-1.61 (m, 4H) Ia-220 0 1H-NMR (D6-DMSO): 8.49-8.47 (m, 1H), 8.39 (m, 1H), 7.65 (t, 1H), 7.59-7.57 (m, 1H), 7.42 (s, 1H), 7.37-7.29 (m, 1H), 6.90 (s, 1H), 3.90 (q, 2H), 3.43-3.38 (m, 2H), 1.23 (t, 3H) Ia-221 1H-NMR (D6-DMSO): 7.36-7.34 (m, 2H), 7.20-7.18 (m, 2H), 6.87- 6.84 (m, 1H), 6.82-6.80 (m, 1H), 3.66-3.58 (m, 8H), 3.30 (broad, 2H), 2.19 (s, 3H) Ia-222 1H-NMR (D6-DMSO): 7.10 (d, 1H), 6.89 (broad, 1H), 6.55 (d, 1H), 3.93 (q, 2H), 2.87 (broad, 6H), 2.29 (s, 3H) Ia-223 1H-NMR (D6-DMSO): 8.30 (d, 2H), 8.21 (d, 2H), 7.17-7.13 (m, 2H), 6.89 (broad, 2H), 3.89 (q, 2H), 2.37 (s, 3H) Ia-224 1H-NMR (D6-DMSO): 8.43-8.42 (m, 1H), 8.31 (m, 1H), 7.52- 7.50 (m, 1H), 7.27-7.20 (m, 2H), 6.89 (s, 1H), 6.39 (s, 1H), 3.45- 3.33 (m, 4H), 2.17 (s, 3H), 2.07 (s, 3H), 1.22 (t, 3H) Ia-225 1H-NMR (D6-DMSO): 7.07-7.04 (m, 1H), 6.95-6.94 (m, 1H), 5.95 (broad, 2H), 3.82 (q, 2H), 2.32 (s, 3H), 1.14 (d, 6H) Ia-226 1H-NMR (D6-DMSO): 7.90 (broad, 1H), 7.09 (d, 1H), 6.89 (broad, 1H), 6.58 (broad, 1H), 4.03 (q, 2H) 2.76 (broad, 3H), 2.29 (s, 3H) Ia-227 1H-NMR (D6-DMSO): 8.15 (m, 1H), 7.68-7.65 (m, 1H), 7.42- 7.40 (m, 1H), 6.86 (s, 1H), 6.45 (s, 1H), 3.52 (q, 2H), 2.92 (broad, 6H), 2.16 (s, 3H), 2.04 (s, 3H) Ia-228 1H-NMR (D6-DMSO): 7.05-6.95 (m, 2H), 6.26 (broad, 1H), 3.80 (q, 2H), 3.09-3.01 (m, 2H), 2.32 (s, 3H), 2.22-0.60 (m, 15H) Ia-229 1H-NMR (D6-DMSO): 8.32-8.27 (m, 1H), 7.82 (broad, 1H), 7.65 (m, 1H), 7.48-7.46 (m, 2H), 7.02 (broad, 1H), 3.97 (q, 2H), 2.83 (m, 1H), 0.69-0.61 (m, 4H) Ia-230 0 1H-NMR (D6-DMSO): 7.40-7.23 (m, 4H), 6.89-6.86 (m, 1H), 6.81- 6.79 (m,1H), 3.65-3.49 (m, 8H), 3.02-3.00 (m, 2H), 2.18 (s, 3H) Ia-231 1H-NMR (D6-DMSO): 7.32-7.30 (m, 2H), 7.14-7.12 (m, 2H), 6.83 (s, 1H), 6.39 (s, 1H), 3.44 (q, 2H), 2.89 (broad, 6H), 2.15 (s, 3H), 2.04 (s, 3H) Ia-232 1H-NMR (D6-DMSO): 8.14 (m, 1H), 7.55-7.53 (m, 1H), 7.38- 7.37 (m, 2H), 6.91 (s, 1H), 6.47 (s, 1H), 3.50 (q, 2H), 2.87 (m, 1H), 2.19 (s, 3H), 2.08 (s, 3H), 0.71 (m, 2H), 0.58 (m, 2H) Ia-233 1H-NMR (D6-DMSO): 7.26 (broad, 1H), 7.09-7.06 (m, 1H), 6.97- 6.95 (m, 1H), 3.84 (q, 2H), 3.14 (q, 2H), 2.77 (d, 3H), 2.32 (s, 3H) Ia-234 1H-NMR (D6-DMSO): 9.50-9.49 (m, 1H), 8.83-8.82 (m, 1H), 8.72 (s, 1H), 7.37 (s, 1H), 7.07 (s, 1H), 6.75 (broad, 2H), 4.03 (q, 2H), 2.08 (s, 3H) Ia-235 1H-NMR (D6-DMSO): 8.88 (s, 1H), 8.39 (m, 1H), 7.54 (s, 1H), 7.05 (s, 1H), 6.53 (broad, 1H), 4.07 (q, 2H), 3.64-3.59 (m, 2H), 3.27 (t, 2H), 1.35-1.30 (m, 1H), 0.79-0.76 (m, 2H), 0.60-0.59 (m, 2H) Ia-236 1H-NMR (D6-DMSO): 6.96-6.92 (m, 4H), 3.75 (q, 2H), 3.73 (s, 3H), 2.39 (s, 3H) Ia-237 1H-NMR (D6-DMSO): 8.23-8.22 (m, 1H), 7.73-7.70 (m, 1H), 7.49- 7.47 (m, 1H), 7.42 (s, 1H), 6.95 (s, 1H), 3.94 (q, 2H), 3.10 (broad, 3H), 2.83 (broad, 3H) Ia-238 1H-NMR (D6-DMSO): 7.78 (broad, 1H), 7.12-7.07 (m, 2H), 3.83- 3.75 (m, 2H), 3.55 (broad, 2H), 3.29 (t, 2H), 2.33 (s, 3H) Ia-239 1H-NMR (D6-DMSO): 8.46-8.45 (m, 2H), 7.19 (broad, 1H), 7.11 (m, 2H), 6.90 (s, 1H), 6.42 (broad, 1H), 3.44 (q, 2H), 2.87 (broad, 3H), 2.17 (s, 3H), 2.07 (s, 3H) Ia-240 00 1H-NMR (D6-DMSO): 7.28-7.22 (m, 3H), 7.10-7.08 (m, 2H), 6.81 (s, 1H), 6.37 (s, 1H), 3.36 (q, 2H), 2.90 (broad, 6H), 2.13 (s, 3H), 2.05 (s, 3H) Ia-241 01 1H-NMR (D6-DMSO): 7.01 (s, 1H), 6.89 (t, 1H), 6.63 (s, 1H), 4.10- 4.02 (m, 2H), 3.77 (q, 2H), 2.50 (m, 1H), 2.29 (s, 3H), 1.92 (s, 3H), 1.67-1.63 (m, 6H), 1.36-1.35 (m, 2H) Ia-242 02 1H-NMR (D6-DMSO): 7.65 (d, 2H), 7.38 (d, 2H), 6.84 (d ,1H), 6.73 (d, 1H), 3.53 (q, 2H), 3.11 (broad, 3H), 2.73 (broad, 3H), 2.17 (s, 3H) Ia-243 03 1H-NMR (D6-DMSO): 7.65 (s, 1H), 7.20 (s, 1H), 7.03-7.01 (m, 1H), 4.36 (t, 2H), 3.80 (q, 2H), 3.50 (broad, 2H), 2.31 (s, 3H) Ia-244 04 1H-NMR (D6-DMSO): 8.04 (s, 1H), 7.95 (s, 1H), 6.63 (s, 1H), 4.32 (q, 2H), 1.88 (s, 2H), 1.41-1.34 (m, 1H), 0.83-0.67 (m, 4H) Ia-245 05 1H-NMR (D6-DMSO): 7.68-7.60 (m, 2H), 7.54-7.49 (m, 1H), 7.40 (d, 1H), 6.85 (d, 1H), 6.66 (d, 1H), 3.55-3.43 (m, 2H), 3.12 (broad, 3H), 2.63 (broad, 3H), 2.17 (s, 3H) Ia-247 06 1H-NMR (D6-DMSO): 7.09-7.04 (m, 2H), 6.40-6.39 (m, 1H), 4.60- 4.55 (m, 1H), 3.84 (q, 2H), 3.49-2.04 (m, 6H), 1.37-1.36 (m, 1H), 0.86-0.83 (m, 2H), 0.65-0.61 (m, 2H) Ia-248 07 1H-NMR (D6-DMSO): 8.56-8.55 (m, 1H), 7.79-7.75 (m, 2H), 7.47 (s, 1H), 7.42-7.39 (m, 2H), 6.86 (s, 1H), 3.89 (q, 2H), 2.81 (d, 3H) Ia-249 08 1H-NMR (D6-DMSO): 7.74-7.72 (m, 1H), 7.50-7.48 (m, 1H), 6.61 (s, 1H), 4.08 (q, 2H), 2.44 (s, 3H), 1.91 (s, 3H), 1.46-1.40 (m, 1H), 0.82-0.68 (m, 4H) Ia-250 09 1H-NMR (D6-DMSO): 7.64 (d, 2H), 7.46 (d, 1H), 7.39 (d, 2H), 6.88 (d, 1H), 7.76 (d, 1H), 3.53 (q, 2H), 2.89 (d, 3H), 2.20 (s, 3H). Ia-251 0 logP (HCOOH) = 2.23 Ia-252 1H-NMR (D6-DMSO): 7.29-7.27 (m, 2H), 7.10-7.08 (m, 2H), 6.59 (m, 2H), 3.60 (s, 3H), 3.46 (q, 2H), 2.87 (broad, 6H), 2.22 (s, 3H) Ia-253 1H-NMR (D6-DMSO): 7.59 (s, 1H), 7.14 (s, 1H), 6.85 (broad, 1H), 6.20 (tt, 1H), 4.11 (q, 2H), 3.57-3.47 (m, 2H), 1.34 (m, 1H), 0.86- 0.82 (m, 2H), 0.69-0.64 (m, 2H) Ia-254 1H-NMR (D6-DMSO): 7.58 (s, 1H), 7.27 (broad, 1H), 6.96 (s, 1H), 4.14-4.02 (m, 4H), 2.46-2.44 (m, 1H), 1.67-1.63 (m, 6H), 1.39- 1.38 (m, 2H) Ia-255 1H-NMR (D6-DMSO): 6.87 (s, 1H), 6.81 (s, 1H), 5.98 (broad, 2H), 3.72 (q, 2H), 3.69 (s, 3H), 2.37 (s, 3H), 1.57-1.54 (m, 2H), 1.27- 1.24 (m, 2H) Ia-256 1H-NMR (D6-DMSO): 7.58 (s, 1H), 7.23 (broad, 1H), 7.04 (s, 1H), 6.23 (tt, 1H), 4.12 (q, 2H), 3.62-3.52 (m, 2H), 2.45-2.41 (m, 1H), 1.68-1.60 (m, 6H), 1.39-1.37 (m, 2H) Ia-257 1H-NMR (D6-DMSO): 7.00 (s, 1H), 6.79 (broad, 1H), 6.68 (s, 1H), 6.16 (tt, 1H), 3.78 (q, 2H), 3.57 (m, 2H), 2.49 (m, 1H), 2.28 (s, 3H), 1.93 (s, 3H), 1.68-1.61 (m, 6H), 1.35-1.34 (m, 2H) Ia-258 1H-NMR (D6-DMSO): 7.56 (s, 1H), 7.05 (s, 1H), 6.32 (broad, 2H), 4.09 (q, 2H), 3.98-3.96 (m, 2H), 3.33 (s, 3H) Ia-259 1H-NMR (D6-DMSO): 7.55 (s, 1H), 7.34 (broad, 1H), 6.99 (s, 1H), 4.14-4.02 (m, 4H), 3.26-3.17 (m, 1H), 2.12-1.56 (m, 6H) Ia-260 1H-NMR (D6-DMSO): 9.30-9.29 (m, 1H), 8.97-8.96 (m, 1H), 8.26- 8.25 (m, 1H), 7.01 (s, 1H), 6.96 (s, 1H), 6.60 (broad, 2H), 3.75 (q, 2H), 3.73 (s, 3H), 2.42 (s, 3H) Ia-261 0 1H-NMR (D6-DMSO): 7.22 (t, 1H), 7.06-7.03 (m, 1H), 6.90- 6.88 (m, 1H), 4.10-4.01 (m, 2H), 3.82 (q, 2H), 3.20-3.16 (m, 1H), 2.32 (s, 3H), 2.11-2.06 (m, 2H), 1.79-1.59 (m, 4H) Ia-262 1H-NMR (D6-DMSO): 7.56 (s, 1H), 7.06 (s, 1H), 6.26 (broad, 2H), 4.39 (m, 1H), 4.09 (q, 2H), 3.98-3.92 (m, 1H), 3.77-3.75 (m, 1H), 2.17-2.08 (m, 2H), 1.92-1.86 (m, 2H) Ia-263 1H-NMR (D6-DMSO): 7.94 (d, 2H), 7.13-7.07 (m, 2H), 6.97 (d, 2H), 6.44 (broad, 2H), 3.86 (q, 2H), 3.81 (s, 3H), 2.35 (s, 3H) Ia-264 1H-NMR (D6-DMSO): 8.59 (s, 1H), 7.88-7.82 (m, 3H), 7.48 (s, 1H), 6.91 (s, 1H), 3.87 (q, 2H), 2.93 (d, 3H) Ia-265 1H-NMR (D6-DMSO): 7.34-7.01 (m, 5H), 6.89 (s, 1H), 6.41 (s, 1H), 3.39 (q, 2H), 2.86 (broad, 3H), 2.18 (s, 3H), 2.07 (s, 3H) Ia-266 1H-NMR (D6-DMSO): 8.03-7.99 (m, 2H), 7.62 (s, 1H), 7.53- 7.51 (m, 2H), 7.15 (s, 1H), 6.75 (broad, 2H), 4.13 (q, 2H) Ia-267 1H-NMR (D6-DMSO): 7.02 (t, 1H), 6.98 (s, 1H), 6.63 (s, 1H), 4.11- 4.02 (m, 2H), 3.78 (q, 2H), 3.14 (m, 1H), 2.28 (s, 3H), 2.12- 2.04 (m, 2H), 1.91 (s, 3H), 1.75-1.59 (m, 4H) Ia-268 1H-NMR (D6-DMSO): 7.30-7.28 (m, 2H), 7.14-7.11 (m, 2H), 6.64- 6.62 (m, 2H), 3.63 (m, 6H), 3.59 (s, 3H), 3.48 (q, 2H), 3.34- 3.29 (broad, 2H), 2.23 (s, 3H) Ia-269 1H-NMR (D6-DMSO): 8.48-8.46 (m, 1H), 8.40-8.39 (m, 1H), 7.67- 7.65 (m, 1H), 7.33-7.30 (m, 1H), 6.90-6.83 (m, 2H), 3.66 (q, 2H), 3.59-3.49 (m, 4H), 2.18 (s, 3H), 2.15-2.06 (m, 4H) Ia-270 1H-NMR (D6-DMSO): 7.37-7.35 (m, 2H), 7.25-7.23(m, 2H), 6.87- 6.82 (m, 2H), 3.61 (q, 2H), 3.47 (m, 4H), 2.19(s, 3H), 2.03 (m, 4H) Ia-271 0 1H-NMR (D6-DMSO): 8.14 (m, 1H), 8.02 (m, 1H), 7.86- 7.83 (m, 2H), 7.23-7.22 (m, 1H), 7.15-7.14 (m, 1H), 4.26- 4.18 (m, 2H), 1.52 (m, 1H), 1.28 (m, 2H), 0.85-0.83 (m, 2H) Ia-272 1H-NMR (D6-DMSO): 7.17 (s, 1H), 7.00 (s, 1H), 4.59 (q, 2H), 4.18 (s, 2H), 3.81 (q, 2H), 2.33 (s, 3H), 2.04 (s, 3H) Ia-273 1H-NMR (D6-DMSO): 7.26-7.23 (m, 2H), 4.09 (s, 2H), 3.87 (q, 2H), 3.17 (s, 3H), 2.37 (s, 3H) Ia-274 1H-NMR (D6-DMSO): 7.44 (m, 1H), 7.39-7.37 (m, 2H), 7.28- 7.26 (m, 2H), 6.92 (s, 1H), 3.90-3.83 (q, 2H), 3.60 (m, 4H), 2.06 (m, 4H) Ia-275 1H-NMR (D6-DMSO): 7.47 (s, 1H), 7.20 (s, 1H), 4.60 (q, 2H), 4.25 (s, 2H), 3.94 (q, 2H), 2.35 (s, 3H) Ia-276 1H-NMR (D6-DMSO): 7.24-7.19 (m, 2H), 6.72 (s, 1H), 4.93 (q, 2H), 3.86 (q, 2H), 2.36 (s, 3H), 1.52-1.44 (m, 4H) Ia-277 1H-NMR (D6-DMSO): 7.24-7.19 (m, 2H), 3.86 (q, 2H), 3.44 (s, 3H), 2.36 (s, 6H) Ia-278 1H-NMR (D6-DMSO): 7.65-7.64 (m, 1H), 7.42-7.40 (m, 1H), 4.02- 3.96 (q, 2H), 3.45 (t, 2H), 3.41 (broad, 1H), 3.27 (t, 2H), 2.41 (s, 3H), 2.09-2.05 (m, 2H) Ia-279 1H-NMR (D6-DMSO): 7.55 (broad, 1H), 7.05 (s, 1H), 7.02 (s, 1H), 3.83-3.75 (q, 2H), 3.26-3.23 (m, 2H), 2.97-2.94 (m, 2H), 2.31 (s, 3H), 1.96-1.90 (m, 2H).

(205) TABLE-US-00005 Example number Structure Analytical data Ib-17 1H-NMR (D6-DMSO): 7.87 (s, 1H), 7.54 (broad, 2H), 7.33 (s, 1H), 4.18-4.10 (m, 2H) Ib-18 0 1H-NMR (D6-DMSO): 8.10 (s, 1H), 7.80-7.30 (broad, 1H), 7.29 (s, 1H), 4.16-4.05 (m, 2H) Ib-19 1H-NMR (D6-DMSO): 7.29-7.27 (m, 1H), 7.18-7.15 (m, 1H), 6.74 (broad, 2H), 4.06-3.98 (m, 2H), 2.30 (s, 3H), 1.39-1.29 (m, 4H) Ib-20 1H-NMR (D6-DMSO): 7.27 (d, 1H), 7.14 (d, 1H), 4.09-3.98 (m, 2H), 3.34-3.33 (m, 2H), 2.90 (s, 3H), 2.38-2.22 (m, 5H), 1.93- 1.88 (m, 2H) Ib-21 logP (HCOOH) = 3.32, logP (neutral = 3.32) Ib-22 1H-NMR (D6-DMSO): 7.27- 7.24 (m, 1H), 7.19-7.16 (m, 1H), 6.57 (broad, 2H), 4.05-3.97 (m, 2H), 2.31 (s, 3H), 1.57 (m, 2H), 1.31-1.28 (m, 2H) Ib-23 1H-NMR (D6-DMSO): 7.28 (d, 1H), 7.21 (d, 1H), 4.14-3.98 (m, 2H), 3.48-3.43 (m, 2H), 2.97 (s, 3H), 2.31 (s, 3H), 1.15 (t, 3H) Ib-24 1H-NMR (D6-DMSO): 8.41 (broad, 1H), 8.04 (s, 1H), 7.27 (s, 1H), 4.25-4.02 (m, 2H), 2.66 (broad, 3H) Ib-25 1H-NMR (D6-DMSO): 8.03 (s, 1H), 7.22 (s, 1H), 4.23-4.05 (m, 2H), 3.03 (broad, 3H) and 3H under the DMSO peak Ib-26 1H-NMR (D6-DMSO): 7.83 (s, 1H), 7.25 (s, 1H), 4.16-4.12 (m, 1H), 4.27-4.21 (m, 1H), 3.04 (s, 6H) Ib-27 1H-NMR (D6-DMSO): 7.41 (m, 1H), 7.23 (m, 1H), 6.53 (broad, 2H), 4.06-3-97 (m, 2H), 2.29 (s, 3H), 1.62-1.59 (m, 2H), 1.32-1.29 (m, 2H) Ib-28 0 1H-NMR (D6-DMSO): 8.50- 8.49 (m, 1H), 8.38 (broad, 1H), 7.66-7.60 (m, 2H), 7.34-7.31 (m, 1H), 7.16-7.14 (m, 1H), 6.96- 6.93 (m, 1H), 3.97-3.88 (m, 1H), 3.76-3.70 (m, 1H), 2.91-2.90 (d, 3H), 2.20 (s, 3H) Ib-29 1H-NMR (D6-DMSO): 8.40 (s, broad, 1H), 7.28 (d, 1H), 7.21 (d, 1H), 4.15-4.06 (m, 1H), 4.00- 3.94 (m, 1H), 3.08 (s, broad, 2H ), 2.31 (s, 3H), l.09 (s, broad, 1H), 0.46-0.44 (m, 2H), 0.22 (s, broad, 2H) Ib-30 1H-NMR (D6-DMSO): 8.12 (d, 2H), 7.73 (d, 2H), 7.41 (d, 1H), 7.26 (d, 1H), 4.15-4.05 (m, 2H), 3.96 (t, 2H), 2.69-2.50 (m, 4H), 2.34 (s, 3H), 2.09-2.02 (m, 2H) Ib-31 1H-NMR (D6-DMSO): 7.50 (s, 1H), 7.40 (broad, 2H), 7.28 (s, 1H), 4.10-4.02 (q, 2H), 2.32 (s, 3H) Ib-32 1H-NMR (D6-DMSO): 7.68 (d, 1H), 7.32 (d, 1H), 4.28-4.10 (m, 2H), 3.05 (s, 6H) Ib-33 1H-NMR (D6-DMSO): 7.33- 7.31 (m, 1H), 7.19-7.16 (m, 1H), 6.26 (tt, 1H), 4.12-3.98 (m, 2H), 3.87-3.78 (dt, 2H), 3.52-3.48 (m, 2H), 2.35 (m, 2H), 2.30 (s, 3H), 1.98-1.90 (m, 2H) Ib-34 1H-NMR (D6-DMSO): 7.27 (d, 1H), 7.21 (d, 1H), 4.15-3.98 (m, 2H), 3.45-3.40 (m, 4H), 2.30 (s, 3H), 1.18-1.14 (m, 6H) Ib-35 1H-NMR (D6-DMSO): 7.51 (s, 1H), 7.45 (broad, 2H), 7.29 (s, 1H), 4.11-4.01 (m, 2H), 2.32 (s, 3H) Ib-36 1H-NMR (D6-DMSO): 8.48 (s, 1H), 7.30 (d, 1H), 7.21 (d, 1H), 4.15-3.95 (m, 2H), 2.31 (s, 3H), 1.33-1.24 (m, 3H), 0.77 (s, 2H), 0.57 (s, 2H) Ib-37 1H-NMR (D6-DMSO): 7.52 (broad, 1H), 7.37-7.35 (m, 2H), 7.22-7.20 (m, 2H), 7.06-7.04 (m, 1H), 6.97-6.95 (m, 1H), 3.92- 3.83 (m, 1H), 3.64-3.58 (m, 1H), 2.89-2.88 (d, 3H), 2.20 (s, 3H) Ib-38 0 1H-NMR (D6-DMSO): 7.50 (broad, 2H), 7.34-7.32 (m, 1H), 7.28-7.25 (m, 1H), 4.21-4.02 (m, 2H), 2.34 (s, 3H) Ib-39 1H-NMR (D6-DMSO): 7.26- 7.25 (m, 1H), 7.13-7.11 (m, 1H), 6.45 (broad, 1H), 4.05-3.96 (m, 2H), 2.29 (s, 3H), 2.21-2.18 (m, 1H), 1.87-1.84 (m, 1H), 0.81- 0.80 (m, 2H), 0.66-0.54 (m, 4H), 0.44 (m, 2H) Ib-40 1H-NMR (D6-DMSO): 7.34- 7.32 (m, 1H), 7.29-7.26 (m, 1H), 7.23 (broad, 2H), 4.13-4.01 (m, 2H), 2.34 (s, 3H) Ib-41 1H-NMR (D6-DMSO): 8.48 (bs, 1H), 7.68 (d, 1H), 7.32 (d, 1H), 4.28-4.05 (m, 2H), 2.72 (bs, 3H) Ib-42 1H-NMR (D6-DMSO): 7.55 (broad, 2H), 7.35-7.33 (m, 1H), 7.29-7.26 (m, 1H), 4.12- 4.01 (m, 2H), 2.34 (s, 3H) Ib-43 1H-NMR (D6-DMSO): 8.22- 8.20 (m, 1H), 7.44-7.41 (m, 1H), 6.49 (tt, 1H), 4.21-3.93 (m, 2H), 2.36 (s, 3H) Ib-44 1H-NMR (D6-DMSO): 7.87 (s, 1H), 7.54 (broad, 2H), 7.33 (s, 1H), 4.18-4.10 (m, 2H) Ib-45 1H-NMR (D6-DMSO): 8.66- 8.65 (m, 1H), 8.33-8.31 (m, 1H), 8.00-7.95 (m, 1H), 7.60-7.57 (m, 1H), 7.46-7.44 (m, H), 7.27-7.24 (m, 1H), 6.95 (broad, 2H), 4.11- 4.03 (q, 2H), 2.35 (s, 3H) Ib-46 1H-NMR (D6-DMSO): 7.28- 7.26 (m, 1H), 7.15-7.12 (m, 1H), 6.30 (broad, 1H), 4.02 (m, 2H), 3.19 (m, 2H), 2.29 (s, 3H), 1.90 (m, 1H), 1.08 (t, 3H), 0.85-0.81 (m, 2H), 0.64-0.62 (m, 2H) Ib-47 1H-NMR (D6-DMSO): 8.48- 8.46 (m, 1H), 8.32 (broad, 1H), 7.65 (broad, 1H), 7.36-7.33 (m, 1H), 7.07-7.05 (m, 1H), 6.93- 6.90 (m, 1H), 3.92-3.83 (m, 1H), 3.68-3.61 (m, 1H), 3.13 (broad, 3H), 2.81 (broad, 3H), 2.16 (s, 3H) Ib-48 0 1H-NMR (D6-DMSO): 8.96- 8.95 (m, 1H), 8.38-8.35 (m, 1H), 7.65-7.63 (m, 1H), 7.43- 7.41 (m, 1H), 7.27-7.24 (m, 1H), 7.00 (broad, 2H), 4.10- 4.02 (q, 2H), 2.35 (s, 3H) Ib-49 logP (HCOOH) = 3.22, logP (neutral) = 3.12 Ib-50 1H-NMR (D6-DMSO): 7.40 (s, 1H), 7.25-7.19 (m, 2H), 4.11-4.08 (m, 1H), 4.00-3.97 (m, 1H), 2.30 (s, 3H), 1.42 (s, 9H) Ib-51 1H-NMR (D6-DMSO): 7.24- 7.22 (m, 1H), 7.11-7.08 (m, 1H), 4.11-3.92 (m, 2H), 3.08 (s, 6H), 2.30 (s, 3H), 1.66 (m, 1H), 0.68-0.63 (m, 2H), 0.32- 0.30 (m, 1H), 0.23-0.21 (m, 1H) Ib-52 1H-NMR (D6-DMSO): 7.20 (d, 1H), 7.13 (d, 1H), 4.09-3.97 (m, 2H), 3.32 (s, 3H), 3.28 (t, 2H), 2.22 (s, 3H), 2.20-2.05 (m, 2H), 1.78-1.72 (m, 2H), 1.62-1.56 (m, 2H) Ib-53 1H-NMR (D6-DMSO): 7.15- 7.12 (m, 1H), 6.94-6.92 (m, 1H), 4.06-3.88 (m, 2H), 2.32 (s, 3H), 1.55 (m, 1H), 0.88- 0.84 (m, 2H), 0.74 (m, 2H) Ib-54 1H-NMR (D6-DMSO): 8.97 (broad, 1H), 7.30-7.22 (m, 2H), 4.77 (broad, 2H), 4.59 (broad, 3H), 4.19-4.07 (m, 1H), 3.97 (broad, 1H), 2.32 (s, 3H) Ib-55 1H-NMR (D6-DMSO): 7.86 (d, 2H), 7.37 (m, 3H), 7.22 (d, 1H), 7.09 (dd, 1H), 4.14-4.02 (m, 2H), 3.73 (dd, 2H), 2.67- 2.57 (m, 2H), 2.33 (s, 3H), 2.07-1.99 (m, 2H) Ib-56 1H-NMR (D6-DMSO): 2.30 (s, 3H), 2.62 (broad, 3H), 4.17- 3.95 (m, 2H), 7.28 (beit, 1H), 7.44 (s, 1H), 8.22 (broad, 1H) Ib-57 1H-NMR (D6-DMSO): 8.32 (s, 1H), 7.40-7.36 (broad, 1H), 7.29 (s, 1H), 4.19-4.14 (m, 2H) Ib-58 0 1H-NMR (D6-DMSO): 8.56- 8.55 (m, 1H), 7.77-7.73 (m, 1H), 7.69 (broad, 1H), 7.41- 7.38 (m, 2H), 7.10-7.08 (m, 1H), 7.02-6.99 (m, 1H), 3.97- 3.91 (m, 1H), 3.73-3.67 (m, 1H), 2.84-2.83 (d, 3H), 2.23 (s, 3H) Ib-59 1H-NMR (D6-DMSO): 7.78 (d, 1H), 7.32 (d, 1H), 4.20- 4.06 (m, 2H), 3.05 (s, 3H) Ib-60 1H-NMR (D6-DMSO): 7.29- 7.12 (m, 4H), 6.97 (d, 1H), 6.93 (d, 1H), 3.88-3.79 (m, 1H), 3.62-3.50 (m, 1H), 3.11 (broad, 3H), 2.79-2.77 (broad, 3H), 2.17 (s, 3H) Ib-61 1H-NMR (D6-DMSO): 7.81- 7.79 (m, 2H), 7.46 (broad, 1H), 7.29 (broad, 1H), 6.98 (d, 1H), 6.94 (d, 1H), 3.88-3.79 (m, 1H), 3.63-3.52 (m, 1H), 3.14 (broad, 3H), 2.76 (broad, 3H), 2.16 (s, 3H) Ib-62 1H-NMR (D6-DMSO): 9.46- 9.45 (m, 1H), 8.84 (m, 1H), 8.74-8.73 (m, 1H), 7.48-7.46 (m, 1H), 7.29-7.26 (m, 1H), 7.12 (broad, 2H), 4.12-4.04 (m, 2H), 2.36 (s, 3H) Ib-63 1H-NMR (D6-DMSO): 9.13 (s, 1H), 8.70-8.69 (m, 1H), 8.32- 8.30 (m, 1H), 7.52-7.49 (m, 1H), 7.43-7.41 (m, 1H), 7.26-7.23 (m, 1H), 6.94 (broad, 2H), 4.11-4.03 (m, 2H), 2.35 (s, 3H) Ib-64 1H-NMR (D6-DMSO): 7.84 (m, 1H), 7.35 (m, 1H), 6.85 (broad, 2H), 4.16-4.08 (m, 2H), 1.65 (m, 2H), 1.37 (m, 2H) Ib-65 1H-NMR (D6-DMSO): 9.34 (m, 1H), 9.01-9.00 (m, 1H), 8.28- 8.27 (m, 1H), 7.47-7.45 (m, 1H), 7.29-7.25 (m, 1H), 7.16 (broad, 2H), 4.12-4.01 (m, 2H), 2.36 (s, 3H) Ib-66 1H-NMR (D6-DMSO): 7.38- 7.33 (m, 1H), 7.15-7.10 (m, 1H), 7.03 (broad, 2H), 6.98- 6.92 (m, 2H), 3.89-3.82 (m, 1H), 3.61-3.55 (m, 1H), 3.12 (broad, 3H), 2.83 (broad, 3H), 2.17 (s, 3H) Ib-67 1H-NMR (D6-DMSO): 7.56- 7.54 (m, 1H), 7.36-7.30 (m, 1H), 7.19-6.95 (m, 5H), 3.94- 3.85 (m, 1H), 3.70-3.64 (m, 1H), 2.89-2.88 (m, 3H), 2.21 (s, 3H) Ib-68 0 1H-NMR (D6-DMSO): 7.99 (s, 1H), 7.63 (broad, 2H), 7.32 (s, 1H), 4.18-4.06 (m, 2H) Ib-69 1H-NMR (D6-DMSO): 9.35 (m, 1H), 9.03-9.02 (m, 1H), 8.32- 8.28 (m, 1H), 7.87 (s, 1H), 7.41 (s, 1H), 7.08 (broad, 2H), 4.19- 4.11 (m, 2H) Ib-71 1H-NMR (D6-DMSO): 7.51 (d, 1H), 7.38 (d, 1H), 4.62-4.57 (m, 2H), 4.26-4.14 (m, 3H), 4.04- 3.94 (m, 1H), 2.36 (s, 3H) Ib-72 1H-NMR (D6-DMSO): 7.29- 7.27 (m, 1H), 7.21-7.18 (m, 1H), 6.42 (broad, 2H), 4.07-3.99 (m, 2H), 2.32 (s, 3H), 1.68-1.59 (m, 4H) Ib-73 1H-NMR (D6-DMSO): 7.3-6.93 (m, 6H), 3.88-3.79 (m, 1H), 3.58-3.47 (m, 1H), 3.10 (broad, 3H), 2.78 (broad, 3H), 2.17 (s, 3H) Ib-74 1H-NMR (D6-DMSO): 8.87 (broad, 1H), 7.33-7.16 (m, 7H), 4.47 (broad, 2H), 4.12-4.06 (m, 1H), 3.90 (broad, 1H), 2.30 (s, 3H) Ib-75 1H-NMR (D6-DMSO): 8.49 (m, 1H), 8.09 (m, 1H), 7.90- 7.88 (m, 1H), 7.03-6.96 (m, 2H), 3.90-3.84 (m, 1H), 3.56- 3.50 (m, 1H), 3.17 (broad, 3H), 2.80 (broad, 3H), 2.17 (s, 3H) Ib-76 1H-NMR (D6-DMSO): 7.57- 7.56 (q, 1H) 7.40-7.38 (m, 1H), 7.31-7.27 (m, 2H), 7.13-7.08 (m, 2H), 6.98-6.95 (m, 1H), 3.92-3.83 (m, 1H), 3.70-3.63 (m, 1H), 2.89-2.87 (d, 3H), 2.21 (s, 3H) Ib-77 1H-NMR (D6-DMSO): 7.81- 7.79 (m, 2H), 7.46 (broad, 1H), 7.29 (broad, 1H), 6.98 (d, 1H), 6.94 (d, 1H), 3.88-3.79 (m, 1H), 3.63-3.52 (m, 1H), 3.14 (broad, 3H), 2.75 (broad, 3H), 2.16 (2.3H) Ib-78 1H-NMR (D6-DMSO): 8.49 (broad, 1H), 7.78 (d, 1H), 7.33 (d, 1H), 4.24-4.02 (m, 2H), 2.73 (broad, 3H) Ib-79 00 1H-NMR (D6-DMSO): 7.11 (s, 1H), 7.08 (s, 1H), 6.19 (broad, 2H), 4.00-3.92 (m, 2H), 2.27 (s, 3H), 2.00 (s, 3H), 1.58 (m, 2H), 1.30-1.29 (m, 2H) Ib-80 01 1H-NMR (D6-DMSO): 7.8 (s, 1H), 7.30 (s, 1H), 7.15 (broad, 2H), 6.40 (t, 1H), 4.18-4.10 (m, 2H) Ib-81 02 1H-NMR (D6-DMSO): 7.61- 7.60 (m, 1H),7.04-6.97 (m, 4H), 3.92-3.86 (m, 1H), 3.65-3.52 (m, 1H), 3.02 (s, 6H), 2.20 (s, 3H) Ib-82 03 1H-NMR (D6-DMSO): 6.96- 6.91 (m, 2H), 6.70 (broad, 1H), 5.90 (broad, 2H), 3.83-3.74 (m, 2H), 3.18 (s, 6H), 2.21 (broad, 6H) Ib-83 04 1H-NMR (D6-DMSO): 7.78 (s, 1H), 7.26 (m, 1H), 7.01 (broad, 1H), 4.22-4.01 (m, 4H), 1.40- 1.38 (m, 1H), 0.96-0.86 (m, 2H), 0.78-0.71 (m, 2H) Ib-84 05 1H-NMR (D6-DMSO): 8.50- 8.48 (m, 1H), 8.38 (m, 1H), 7.65-7.59 (m, 2H), 7.33-7.30 (m, 1H), 7.15-7.13 (m, 1H), 6.95-6.92 (m, 1H), 3.97-3.88 (m, 1H), 3.79-3.70 (m, 1H), 3.44-3.37 (m, 2H), 2.20 (s, 3H), 1.22 (t, 3H) Ib-85 06 1H-NMR (D6-DMSO): 7.52- 7.51 (m, 1H), 7.3 (broad, 2H), 7.18 (s, 1H), 4.16-4.02 (m, 2H), 2.10 (s, 3H) Ib-86 07 logP (HCOOH) = 3.04, logP (neutral) = 3.05 Ib-87 08 1H-NMR (D6-DMSO): 7.35- 6.92 (m, 6H), 3.85-3.79 (m, 1H), 3.58-3.51 (m, 1H), 3.16 (broad, 3H), 2.79 (broad, 3H), 2.16 (s, 3H) Ib-88 09 1H-NMR (D6-DMSO): 8.22 (m, 1H), 7.80 (m, 1H), 7.66 (m, 1H), 7.48-7.46 (m, 1H), 7.20-7.21 (m, 1H), 7.01-6.98 (m, 1H), 4.05- 3.93 (m, 1H), 3.80 (m, 1H), 2.93 (m, 1H), 2.22 (s, 3H), 0.73 (m, 2H), 0.59 (m, 2H) Ib-89 0 1H-NMR (D6-DMSO): 8.28-8.27 (m, 1H), 7.90 (broad, 1H), 7.67- 7.64 (m, 2H), 7.50-7.48 (m, 1H), 7.03 (s, 1H), 4.17-4.05 (m, 1H), 3.89-3.80 (m, 1H), 2.92-2.91 (d, 3H) Ib-90 1H-NMR (D6-DMSO): 8.09 (broad, 1H), 7.44 (s, 1H), 7.12 (broad, 1H), 4.18-4.05 (m, 2H), 2.68-2.63 (broad, 3H), 2.11 (s, 3H) Ib-91 1H-NMR (D6-DMSO): 9.01 (broad, 1H), 7.38 (d, 1H), 7.24 (d, 1H), 4.58-4.57 (m, 2H), 4.35 (broad, 3H), 4.16-4.09 (m, 1H), 3.93 (broad, 1H), 2.32 (s, 3H) Ib-92 1H-NMR (D6-DMSO): 8.60 (s, 1H), 7.84-7.81 (m, 3H), 7.13- 7.11 (m, 1H), 7.02-6.99 (m, 1H), 3.97-3.88 (m, 1H), 3.67-3.61 (m, 1H), 2.94-2.93 (d, 3H), 2.21 (s, 3H) Ib-93 1H-NMR (D6-DMSO): 8.46-8.45 (m, 1H) 8.32 (broad, 1H), 7.58- 7.56 (m, 1H), 7.37-7.29 (m, 2H), 6.99 (s, 1H), 6.66 (s, 1H), 3.74- 3.68 (m, 2H), 2.91-2.90 (d, 3H), 2.17 (s, 3H), 2.15 (s, 3H) Ib-94 1H-NMR (D6-DMSO): 8.98- 8.97 (m, 1H), 8.40-8.37 (m, 1H), 7.71-7.68 (m, 1H), 7.40- 7.38 (m, 1H), 7.26-7.24 (m, 1H), 4.06-3.96 (m, 2H), 2.33 (s, 3H), 2.16 (s, 3H) Ib-95 1H-NMR (D6-DMSO): 8.53- 8.51 (m, 1H), 8.41 (m, 1H), 7.85 (q, 1H), 7.63 (s, 1H), 7.62-7.59 (m, 1H), 7.36-7.33 (m, 1H), 7.00 (s, 1H), 4.12-4.00 (m, 1H), 3.86- 3.75 (m, 1H), 2.93-2.92 (d, 3H) Ib-96 1H-NMR (D6-DMSO): 7.29 (d, 1H), 7.21 (d, 1H), 4.15-3.99 (m, 2H), 3.41 (broad, 4H), 2.31 (s, 3H), 1.86 (broad, 4H) Ib-97 1H-NMR (D6-DMSO): 8.52- 8.50 (m, 1H), 7.65-7.64 (q, 1H), 7.19-7.12 (m, 3H), 6.97-6.95 (m, 1H), 3.96-3.87 (m, 1H), 3.74-3.68 (m, 1H), 2.90-2.89 (d, 3H), 2.20 (s, 3H) Ib-98 1H-NMR (D6-DMSO): 8.44- 8.43 (m, 1H), 8.32-8.29 (m, 1H), 7.60 (m, 1H), 7.35-7.31 (m, 1H), 6.94 (s, 1H), 6.66 (s, 1H), 3.70- 3.64 (m, 1H), 3.30-3.24 (m, 1H), 2.96 (broad, 6H), 2.14 (s, 3H), 2.13 (s, 3H) Ib-99 0 1H-NMR (D6-DMSO): 7.30- 7.25 (m, 1H), 7.09 (m, 1H), 6.65 (broad, 2H), 4.07-4.02 (m, 2H), 2.97-2.93 (m, 1H), 2.33 (s, 3H), 2.22-1.71 (m, 6H) Ib-100 1H-NMR (D6-DMSO): 7.35- 7.15 (m, 4H), 6.98-6.96 (m, 2H), 6.61 (s, 1H), 3.69-3.63 (m, 1H), 3.22-3.17 (m, 1H), 2.88 (broad, 3H), 2.17 (s, 3H), 2.16 (s, 3H) Ib-101 1H-NMR (D6-DMSO): 8.98 (broad, 1H), 7.72-7.70 (m, 2H), 7.52-7.51 (broad, 1H), 7.21- 7.19 (m, 3H), 4.56 (broad, 2H), 4.13-4.06 (m, 1H), 3.93-3.90 (m, 1H), 2.28 (s, 3H) Ib-102 1H-NMR (D6-DMSO): 8.66- 8.64 (m, 1H), 8.37-8.32 (m, 1H), 7.99-7.95 (m, 1H), 7.59-7.56 (m, 1H), 7.27 (s, 1H), 7.19 (s, 1H), 6.60 (broad, 2H), 4.05-3.97 (m, 2H), 2.31 (s, 3H), 2.13 (s, 3H) Ib-103 1H-NMR (D6-DMSO): 8.50- 8.49 (m, 1H), 8.36 (s, 1H), 7.58- 7.57 (m, 2H), 7.34-7.30 (m, 2H), 6.68 (broad, 1H), 3.91-3.82 (m, 1H), 3.59-3.53 (m, 1H), 2.92- 2.91 (d, 3H), 2.20 (s, 3H) Ib-104 1H-NMR (D6-DMSO): 8.16- 8.14 (m, 2H), 7.78-7.77 (broad, 1H), 7.23-7.21 (m, 1H), 7.03- 7.00 (m, 1H), 4.02-3.93 (m, 1H), 3.84-3.77 (m, 1H), 2.91-2.90 (d, 3H), 2.23 (s, 3H) Ib-105 1H-NMR (D6-DMSO): 7.46- 6.94 (m, 6H), 3.85-3.74 (m, 1H), 3.54-3.48 (m, 1H), 3.17 (broad, 3H), 2.74 (broad, 3H), 2.15 (s, 3H) Ib-106 1H-NMR (D6-DMSO): 7.29- 7.27 (m, 1H), 7.20-7.17 (m, 1H), 6.84 (broad, 1H), 4.11- 3.64 (m, 4H), 2.30 (s, 3H), 1.44-1.41 (m, 1H), 0.91-0.84 (m, 2H), 0.72-0.69 (m, 2H) Ib-107 1H-NMR (D6-DMSO): 7.52- 6.95 (m, 7H), 3.82-3.72 (m, 2H), 2.91-2.90 (d, 3H), 2.18 (s, 3H) Ib-108 1H-NMR (D6-DMSO): 7.57 (d, 1H), 7.42 (broad, 2H), 7.30 (d, 1H), 7.10-7.07 (m, 1H), 4.22-4.04 (m, 2H) Ib-109 0 1H-NMR (D6-DMSO): 8.57- 8.55 (m, 1H), 7.91 (broad, 1H), 7.82-7.77 (m, 1H), 7.66 (s, 1H), 7.44-7.41 (m, 2H), 6.96 (s, 1H), 4.10-4.01 (m, 1H), 3.87-3.78 (m, 1H), 2.84-2.83 (d, 3H) Ib-110 1H-NMR (D6-DMSO): 8.14 (broad, 1H), 7.48 (d, 1H), 7.22 (d, 1H), 7.03-7.00 (m, 1H), 4.25-4.01 (m, 2H), 3.67 (broad, 3H) Ib-111 1H-NMR (D6-DMSO): 7.31- 7.29 (m, 2H), 7.25 (broad, 2H), 6.98-6.95 (m, 1H), 4.09-4.00 (m, 2H), 2.33 (s, 3H) Ib-112 1H-NMR (D6-DMSO): 7.09 (m, 2H), 5.17-5.13 (m, 1H), 4.03-3.93 (m, 2H), 3.51- 3.45 (m, 1H), 3.32-3.30 (m, 1H), 2.43-2.07 (m, 2H), 2.27 (s, 3H), 2.06 (s, 3H), 1.95- 1.88 (m, 2H), 1.40-1.38 (d, 3H) Ib-113 1H-NMR (D6-DMSO): 7.70- 7.61 (m, 2H), 7.57 (s, 1H), 7.53-7.44 (m, 2H), 7.12 (d, 1H), 7.65 (d, 1H), 3.87-3.77 (m, 1H), 3.66-3.54 (m, 1H), 2.90 (d, 3H), 2.19 (s, 3H) Ib-114 1H-NMR (D6-DMSO): 7.65 (d, 2H), 7.54 (t, 1H), 7.39 (broad, 1H), 7.04 (broad, 1H), 6.92 (d, 1H), 3.83-3.70 (m, 2H), 3.14 (broad, 3H), 3.28 (broad, 3H), 2.16 (s, 3H) Ib-115 1H-NMR (D6-DMSO): 7.31- 7.29 (m, 1H), 7.20-7.17 (m, 1H), 4.27 (q, 2H), 4.12-4.00 (m, 2H), 3.52 (t, 2H), 2.47- 2.25 (m, 2H), 2.31 (s, 3H), 2.00-1.92 (m, 2H) Ib-116 1H-NMR (D6-DMSO): 7.57 (d, 1H), 7.37 (d, 1H), 6.33 (tt, 1H), 4.25-4.13 (m, 5H), 4.01-3.89 (m, 2H), 2.36 (s, 3H) Ib-117 1H-NMR (D6-DMSO): 7.62- 7.56 (m, 2H), 7.50-7.48 (m, 1H), 4.60 (q, 2H), 4.27-4.00 (m, 4H) Ib-118 1H-NMR (D6-DMSO): 8.00 (d, 2H), 7.53 (d, 2H), 7.39 (d, 1H), 7.23 (d, 1H), 6.80 (broad, 2H), 4.06 (q, 2H), 2.34 (s, 3H) Ib-119 0 1H-NMR (D6-DMSO): 8.23 (broad, 1H), 7.73-7.72 (broad, 1H), 7.62 (s, 1H), 7.52-7.50 (m, 1H), 6.97 (s, 1H), 4.14- 4.02 (m, 1H), 3.82-3.70 (m, 1H), 3.00 (broad, 6H) Ib-120 1H-NMR (D6-DMSO): 7.86 (d, 1H), 7.53 (d, 1H), 4.60 (q, 2H), 4.36-4.24 (m, 3H), 4.17-4.06 (m, 1H) Ib-121 1H-NMR (D6-DMSO): 7.81 (d, 1H), 7.56 (dd, 1H), 7.47 (d, 1H), 4.61 (q, 2H), 4.31- 4.07 (m, 4H) Ib-122 1H-NMR (D6-DMSO): 7.96 (s, 1H), 7.51 (s, 1H), 4.36- 4.24 (m, 1H), 4.14-4.00 (m, 3H), 2.75-2.70 (m, 1H), 1.02-0.92 (m, 4H) Ib-123 1H-NMR (D6-DMSO): 8.50- 8.49 (m, 1H), 8.36 (m, 1H), 7.67-7.64 (m, 1H), 7.60 (s, 1H), 7.39-7.36 (m, 1H), 6.96 (s, 1H), 4.05-3.96 (m, 1H), 3.78-3.66 (m, 1H), 3.05 (broad, 6H) Ib-124 1H-NMR (D6-DMSO): 7.69 (broad, 2H), 7.54 (broad, 1H), 7.27 (broad, 1H), 6.97-6.14 (m, 2H), 3.84-3.70 (m, 1H), 3.43-3.30 (m, 1H), 3.15 (broad, 3H), 2.77 (broad, 3H), 2.16 (s, 3H) Ib-125 1H-NMR (D6-DMSO): 8.02 (broad, 1H), 7.22-7.17 (m, 2H), 6.89 (broad, 1H), 4.12- 4.06 (m, 1H), 3.92 (broad, 1H), 2.76 (broad, 3H), 2.30 (s, 3H) Ib-126 1H-NMR (D6-DMSO): 7.27 (m, 3H), 7.12 (broad, 2H), 6.92 (s, 1H), 6.62 (s, 1H), 3.50 (m, 2H), 2.93 (broad, 6H), 2.16 (s, 3H), 2.13 (s, 3H) Ib-127 1H-NMR (D6-DMSO): 7.57 (s, 1H), 7.34-7.30 (m, 3H), 7.16 (m, 2H), 6.86 (s, 1H), 3.97-3.85 (m, 1H), 3.61-3.49 (m, 1H), 3.05 (broad, 6H) Ib-128 1H-NMR (D6-DMSO): 7.86 (s, 1H), 7.44 (d, 1H), 7.13 (d, 1H), 4.10-3.98 (m, 2H), 3.05 (bs, 3H), 2.95 (bs, 3H), 2.30 (s, 3H) Ib-129 0 1H-NMR (D6-DMSO): 7.78 (s, 1H), 7.34 (s, 1H), 6.95 (broad, 1H), 6.21 (tt, 1H), 4.22- 4.07 (m, 2H), 3.59-3.52 (m, 2H), 1.37 (m, 1H), 0.90-0.87 (m, 2H), 0.73-0.71 (m, 2H) Ib-130 1H-NMR (D6-DMSO): 8.88 (s, 1H), 8.39 (m, 1H), 7.73 (s, 1H), 7.27 (s, 1H), 6.66 (m, 1H), 4.21-4.05 (m, 2H), 3.68- 3.59 (m, 2H), 2.50 (m, 2H), 1.34 (m, 1H), 0.82-0.81 (m, 2H), 0.68-0.66 (m, 2H) Ib-131 1H-NMR (D6-DMSO): 7.73- 7.72 (m, 1H), 7.45 (m, 1H), 4.19-3.97 (m, 2H), 2.40 (s, 3H), 1.93-1.19 (m, 10H) Ib-132 1H-NMR (D6-DMSO): 7.35- 7.33 (m, 1H), 7.19-7.16 (m, 1H), 6.75 (broad, 1H), 6.15 (tt, 1H), 4.11-3.96 (m, 2H), 3.60-3.50 (m, 2H), 2.31 (s, 3H), 1.40 (broad, 1H), 0.90- 0.82 (m, 2H), 0.73-0.67 (m, 2H) Ib-133 1H-NMR (D6-DMSO): 8.15 (broad, 1H), 7.70 (broad, 1H), 7.48-7.46 (m, 1H), 6.96 (s, 1H), 6.63 (s, 1H), 3.77-3.71 (m, 1H), 3.35-3.26 (m, 1H), 2.96 (broad, 6H), 2.15 (s, 3H), 2.13 (s, 3H) Ib-134 1H-NMR (D6-DMSO): 7.53 (d, 1H), 7.36 (d, 1H), 4.22- 4.10 (m, 3H), 4.04-3.92 (m, 1H), 3.19 (s, 3H), 2.35 (s, 3H) Ib-135 1H-NMR (D6-DMSO): 7.50 (d, 1H), 7.35 (d, 1H), 4.28- 4.12 (m, 1H), 4.02-3.91 (m, 3H), 2.75-2.55 (m, 1H), 2.35 (s, 3H), 1.01-0.88 (m, 4H)- peaks of the main isomer- Ib-136 1H-NMR (D6-DMSO): 8.15 (broad, 1H), 7.60-7.44 (m, 3H), 7.01 (s, 1H), 6.70 (s, 1H), 3.79 (m, 2H), 2.90 (m, 1H), 2.19 (s, 3H), 2.16 (s, 3H), 0.72 (m, 2H), 0.58 (m, 2H) Ib-137 1H-NMR (D6-DMSO): 7.90- 7.86 (m, 1H), 7.65-7.63 (m, 1H), 6.66 (s, 1H), 4.30-4.16 (m, 2H), 1.95 (d, 2H), 1.41 (m, 1H), 0.81-0.70 (m, 4H) Ib-138 1H-NMR (D6-DMSO): 7.90 (s, 1H), 7.41 (s, 1H), 6.41 (broad, 2H), 4.10-3.97 (m, 2H), 2.04 (s, 3H), 1.64-1.58 (m, 2H), 1.32-1.29 (m, 2H) Ib-139 0 1H-NMR (D6-DMSO): 7.44 (d, 1H), 7.37 (d, 1H), 7.08 (dd, 1H), 4.58 (q, 2H), 4.23- 4.11 (m, 3H), 4.00-3.88 (m, 1H), 2.35 (s, 3H) Ib-140 1H-NMR (D6-DMSO): 7.77 (broad, 1H), 7.64 (s, 1H), 7.43- 7.41 (m, 1H), 7.34-7.30 (m, 2H), 7.09-7.07 (m, 1H), 6.97 (s, 1H), 4.08-3.96 (m, 1H), 3.81-3.70 (m, 1H), 2.90 (d, 3H) Ib-141 1H-NMR (D6-DMSO): 7.34 (s, 1H), 7.26 (s, 1H), 4.61 (q, 2H), 4.20 (s, 2H), 4.19-4.07 (m, 1H), 3.91-3.79 (m, 1H), 2.31 (s, 3H), 2.14 (s, 3H) Ib-142 1H-NMR (D6-DMSO): 7.13 (t, 1H), 7.07 (s, 1H), 6.92 (s, 1H), 4.15-3.88 (m, 4H), 3.16- 3.12 (m, 1H), 2.26 (s, 3H), 2.17-2.05 (m, 2H), 2.00 (s, 3H), 1.80-1.60 (m, 4H) Ib-143 1H-NMR (D6-DMSO): 7.40- 7.38 (m, 2H), 7.29 (broad, 2H), 7.10-7.08 (m, 1H), 6.98-6.95 (m, 1H), 3.94-3.82 (m, 1H), 3.61-3.48 (m, 1H), 3.31 (broad, 4H), 2.18 (s, 3H), 2.06 (broad, 4H) Ib-144 1H-NMR (D6-DMSO): 8.62 (broad, 1H), 7.99 (broad, 1H), 7.91-7.87 (m, 2H), 7.67 (s, 1H), 6.98 (s, 1H), 4.15-4.03 (m, 1H), 3.79-3.68 (m, 1H), 2.96-2.95 (d, 3H) Ib-145 1H-NMR (D6-DMSO): 7.68 (d, 2H), 7.63 (d, 1H), 7.42 (d, 2H), 7.02-7.96 (m, 2H), 3.90- 3.79 (m, 1H), 3.52-3.40 (m, 1H), 2.91 (d, 3H), 2.20 (s, 3H) Ib-146 1H-NMR (D6-DMSO): 7.66 (d, 1H), 7.45 (d, 1H), 7.21 (dd, 1H), 4.59 (q, 2H), 4.30- 4.21 (m, 3H), 4.14-4.04 (m, 1H) Ib-147 1H-NMR (D6-DMSO): 7.47- 7.20 (m, 4H), 6.94 (s, 1H), 6.80-6.76 (m, 1H), 3.64-3.51 (m, 1H), 3.19 (broad, 3H), 3.06-2.97 (m, 1H), 2.74 (broad, 3H), 2.21 (d, 3H), 2.13 (s, 3H) Ib-148 1H-NMR (D6-DMSO): 7.70- 7.43 (m, 5H), 7.00-6.95 (m, 2H), 3.90-3.70 (m, 1H), 3.47-3.24 (m, 1H), 2.89 (d, 3H), 2.16 (s, 3H) Ib-149 0 1H-NMR (D6-DMSO): 7.73- 7.72 (broad, 1H), 7.63 (s, 1H), 7.40-7.38 (m, 2H), 7.22-7.20 (m, 2H), 6.89 (s, 1H), 4.05- 3.96 (m, 1H), 3.73-3.66 (m, 1H), 2.91-2.90 (d, 3H) Ib-150 1H-NMR (D6-DMSO): 8.52- 8.51 (m, 1H), 8.40 (m, 1H), 7.85 (t, 1H), 7.63 (s, 1H), 7.61- 7.58 (m, 1H), 7.35-7.32 (m, 1H), 6.97 (s, 1H), 4.11-4.00 (m, 1H), 3.83-3.76 (m, 1H), 3.43 (m, 2H), 1.25 (t, 3H) Ib-151 1H-NMR (D6-DMSO): 8.33 (broad, 1H), 7.98 (broad, 1H), 7.72 (broad, 1H), 7.66 (s, 1H), 7.50-7.48 (m, 1H), 7.13 (broad, 1H), 4.16-4.07 (m, 1H), 3.96- 3.88 (m, 1H), 2.77 (broad, 1H), 0.66-0.62 (m, 4H) Ib-152 1H-NMR (D6-DMSO): 8.55- 8.53 (m, 2H), 7.85-7.84 (m, 1H), 7.64 (s, 1H), 7.19-7.18 (m, 2H), 6.97 (s, 1H), 4.09- 4.00 (m, 1H), 3.83-3.74 (m, 1H), 2.92-2.90 (d, 3H) Ib-153 1H-NMR (D6-DMSO): 9.50 (s, 1H), 8.84-8.83 (m, 1H), 8.74-8.73 (m, 1H), 7.51 (s, 1H), 7.30 (s, 1H), 6.95 (broad, 2H), 4.16-4.02 (m, 2H), 2.18 (s, 3H) Ib-154 1H-NMR (D6-DMSO): 7.36- 7.34 (m, 2H), 7.15 (broad, 2H), 6.93 (s, 1H), 6.60 (s, 1H), 3.67- 3.60 (m, 1H), 3.21-3.14 (m, 1H), 2.94 (broad, 6H), 2.14 (s, 6H) Ib-155 1H-NMR (D6-DMSO): 7.09 (s, 1H), 6.99 (t, 1H), 6.93 (s, 1H), 4.13-3.84 (m, 4H), 2.49 (m, 1H), 2.26 (s, 3H), 2.00 (s, 3H), 1.68-1.67 (broad, 6H), 1.38-1.37 (broad, 2H) Ib-156 1H-NMR (D6-DMSO): 7.32 (s, 1H), 7.24 (s, 1H), 4.14- 4.05 (m, 1H), 3.94 (s, 2H), 3.91-3.82 (m, 1H), 2.73 (septet, 1H), 2.31 (s, 3H), 2.15 (s, 3H), 1.02-0.90 (m, 4H) Ib-157 1H-NMR (D6-DMSO): 7.45- 6.96 (m, 6H), 3.86-3.47 (m, 8H), 3.03 (m, 2H), 2.16 (s, 3H) Ib-158 1H-NMR (D6-DMSO): 7.54 (d, 1H), 7.27 (d, 1H), 4.82 (q, 2H), 4.17-4.07 (m, 1H), 4.02-3.93 (m, 1H), 2.32 (s, 3H), 2.12 (s, 3H), 2.05 (s, 3H) Ib-159 0 1H-NMR (D6-DMSO): 7.34 (s, 1H), 7.24 (s, 1H), 4.14-4.05 (m, 3H), 3.87-3.81 (m, 1H), 3.20 (s, 3H), 2.31 (s, 3H), 2.15 (s, 3H) Ib-160 1H-NMR (D6-DMSO): 7.10- 7.09 (m, 2H), 6.25-6.23 (m, 1H), 5.10-5.00 (m, 1H), 4.03-3.87 (m, 2H), 2.26 (s, 3H), 2.05 (s, 3H), 1.36-1.33 (m, 1H), 1.29- 1.28 (d, 3H), 1.01-0.96 (m, 1H), 0.82-0.76 (m, 1H), 0.68-0.61 (m, 2H) Ib-161 logP (HCOOH) = 1.28, logP (neutral) = 2.95 Ib-162 1H-NMR (D6-DMSO): 7.91- 7.89 (m, 2H), 7.72-7.70 (m, 1H), 7.57-7.53 (m, 1H), 6.94- 6.84 (m, 2H), 3.84-3.72 (m, 1H), 3.69 (s, 3H), 3.44-3.32 (m, 1H), 2.95 (broad, 6H), 2.17 (s, 3H) Ib-163 1H-NMR (D6-DMSO): 8.87 (m, 1H), 8.38 (m, 1H), 7.28- 7.26 (m, 1H), 7.14-7.12 (m, 1H), 6.45 (m, 1H), 4.10-3.93 (m, 2H), 3.63-3.60 (m, 2H), 3.25 (t, 2H), 2.29 (s, 3H), l.36 (m, 1H), 0.78-0.75 (m, 2H), 0.63-0.61 (m, 2H) Ib-165 1H-NMR (D6-DMSO): 8.30 (s, 1H), 7.89-7.88 (m, 1H), 6.69 (s, 1H), 4.43-4.29 (m, 2H), 1.94-1.91 (d, 2H), 1.39 (m, 1H), 0.81-0.74 (m, 4H) Ib-166 1H-NMR (D6-DMSO): 7.35 (broad, 1H), 7.17-7.13 (m, 2H), 4.12-3.98 (m, 4H), 3.21-3.16 (m, 1H), 2.30 (s, 3H), 2.16- 2.09 (m, 2H), 1.84-1.61 (m, 4H) Ib-167 1H-NMR (D6-DMSO): 7.74 (s, 1H), 7.50 (broad, 1H), 7.12 (s, 1H), 4.24-4.07 (m, 4H), 3.23-3.14 (m, 1H), 2.18-1.59 (m, 6H) Ib-168 1H-NMR (D6-DMSO): 7.51 (d, 1H), 7.38 (d, 1H), 4.62- 4.57 (m, 2H), 4.26-4.14 (m, 3H), 4.04-3.94 (m, 1H), 2.36 (s, 3H) Ib-169 1H-NMR (D6-DMSO): 7.31- 7.29 (m, 1H), 7.20-7.17 (m, 1H), 5.14-5.10 (m, 1H), 4.12-4.01 (m, 2H), 3.55-3.49 (m, 2H), 2.47-2.28 (m, 2H), 2.30 (s, 3H), 1.96-1.92 (m, 2H), 1.39-1.38 (d, 3H) Ib-170 0 1H-NMR (D6-DMSO): 9.51 (d, 1H), 8.83-8.82 (d, 1H), 8.73 (s, 1H), 7.30 (s, 1H), 7.21 (s, 1H), 6.75 (broad, 2H), 4.06-3.97 (m, 2H), 2.32 (s, 3H), 2.15 (s, 3H) Ib-171 1H-NMR (D6-DMSO): 7.51 (d, 1H), 7.38 (d, 1H), 4.62- 4.57 (m, 2H), 4.26-4.14 (m, 3H), 4.04-3.94 (m, 1H), 2.36 (s, 3H) Ib-172 1H-NMR (D6-DMSO): 7.55 (d, 1H), 7.31 (d, 1H), 6.76 (s, 1H). 4.96 (q, 2H), 4.18-3.95 (m, 2H), 2.33 (s, 3H), 1.52- 1.45 (m, 4H) Ib-173 1H-NMR (D6-DMSO): 7.37 (s, 1H), 7.22 (s, 1H), 4.12- 4.06 (m, 1H), 3.89-3.82 (m, 2H), 3.47 (s, 3H), 2.37 (s, 3H), 2.29 (s, 3H), 2.20 (s, 3H) Ib-174 1H-NMR (D6-DMSO): 7.55 (d, 1H), 7.53 (d, 1H), 4.19-4.13 (m, 1H), 4.00-3.93 (m, 1H), 3.45 (s, 3H), 2.38 (s, 3H), 2.33 (s, 3H)

(206) The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and their relative intensities may be shown in comparison to the most intense signal in the spectrum.

(207) The lists of the 1H NMR peaks are similar to the conventional 1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

(208) In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds, which likewise form part of the subject-matter of the invention, and/or peaks of impurities.

(209) In the reporting of compound signals in the delta range of solvents and/or water, our lists of 1H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-d.sub.6 and the peak of water, which usually have a high intensity on average.

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

(211) Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in this case to identify reproduction of our preparation process with reference to by-product fingerprints.

(212) An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 1H NMR interpretation.

(213) If, as a result of the -value being rounded to two digits after the comma, there are signals having the same -value, their intensities after addition give the same image that would also be observed in the printout of a classic NMR in the region of this -value.

(214) The preparation processes described above can be used to obtain the compounds of the formula (II), for example the following compounds of the formula (II):

N-{2-Chloro-4-fluoro-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroethanimidoyl chloride (II-4)

(215) ##STR00495##

(216) GC-MS: EI mass (m/z): 373 (2Cl) [M].sup.+

(217) The preparation processes described above can be used to obtain the compounds of the formula (III), for example the following compounds of the formula (III):

2,2,2-Trifluoro-N-{4-fluoro-2-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-acetamide (III-4)

(218) ##STR00496##

(219) log P(HCOOH): 3.16; log P(neutral): 3.1; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.05 (s, 1H), 7.59 (d, 1H), 7.31 (d, 1H), 3.96 (q, 2H), 2.17 (s, 3H)

N-{4-Bromo-2-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide (III-5)

(220) ##STR00497##

(221) log P(HCOOH): 3.78; 1H-NMR (D6-DMSO, 400 MHz) ppm 4.17-4.24 (m, 2H), 7.79 (s, 1H), 8.01 (s, 1H), 11.45 (s, 1H)

N-{2,4-Dibromo-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide (III-6)

(222) ##STR00498##

(223) log P(HCOOH): 3.81; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.21 (s, 1H), 7.90 (s, 1H), 7.56 (s, 1H), 3.99 (q, 2H)

N-{2-Chloro-4-fluoro-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide (III-7)

(224) ##STR00499##

(225) log P(HCOOH): 3.33; log P(neutral): 3.11; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.39 (s, 1H), 7.85 (d, 1H), 7.76 (d, 1H), 4.08 (q, 2H)

N-{4-Chloro-2-fluoro-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide (III-8)

(226) ##STR00500##

(227) log P(HCOOH): 3.34; log P(neutral): 3.14; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.47 (bs, 1H), 7.85 (d, 1H), 7.76 (d, 1H), 4.09 (q, 2H)

N-{4-Bromo-2-chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide (III-9)

(228) ##STR00501##

(229) log P(HCOOH): 3.46; log P(neutral): 3.11; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.46 (s, 1H), 7.87 (d, 1H), 7.82 (d, 1H), 4.11 (q, 2H)

(230) The preparation processes described above can be used to obtain the compounds of the formula (IV), for example the following compounds of the formula (IV):

N,N-[Disulfanediylbis(4-fluoro-6-methylbenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-2)

(231) ##STR00502##

(232) log P(HCOOH): 4.0; log P(neutral): 3.92; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.04 (s, 2H), 7.62 (d, 2H), 7.32 (d, 2H), 2.19 (s, 6H)

N,N-[Disulfanediylbis(4-bromo-6-chlorobenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-3)

(233) ##STR00503##

(234) log P(HCOOH): 5.42

N,N-[Disulfanediylbis(4,6-dibromobenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-4)

(235) ##STR00504##

(236) log P(HCOOH): 5.62; log P(neutral): 4.49; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.38 (s, 2H), 8.18 (s, 2H), 7.77 (d, 2H)

N,N-[Disulfanediylbis(6-chloro-4-fluorobenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-5)

(237) ##STR00505##

(238) log P(HCOOH): 4.45; log P(neutral): 3.81; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.37 (s, 2H), 7.88 (d, 2H), 7.80 (d, 2H)

N,N-[Disulfanediylbis(4-chloro-6-fluorobenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-6)

(239) ##STR00506##

(240) log P(HCOOH): 4.60; log P(neutral): 3.82; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.44 (s, 2H), 7.95 (d, 2H), 7.83 (d, 2H)

N,N-[Disulfanediylbis(4-bromo-6-fluorobenzene-3,1-diyl)]bis(2,2,2-trifluoroacetamide) (IV-7)

(241) ##STR00507##

(242) log P(HCOOH): 4.76; log P(neutral): 4.02; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.44 (s, 2H), 7.95-7.89 (m, 4H)

(243) The preparation processes described above can be used to obtain the compounds of the formula (V), for example the following compounds of the formula (V):

2-Fluoro-4-methyl-5-[(trifluoroacetyl)amino]benzenesulfonyl chloride (V-2)

(244) ##STR00508##

(245) 1H-NMR (D6-DMSO, 400 MHz) ppm 10.98 (s, 1H), 7.48 (d, 1H), 7.12 (d, 1H), 2.15 (s, 3H)

2,4-Dibromo-5-[(trifluoroacetyl)amino]benzenesulfonyl chloride (V-3)

(246) ##STR00509##

(247) 1H-NMR (D6-DMSO, 400 MHz) ppm 9.20 (bs, 1H), 8.56 (s, 1H), 8.36 (s, 1H)

4-Chloro-2-fluoro-5-[(trifluoroacetyl)amino]benzenesulfonyl chloride (V-4)

(248) ##STR00510##

(249) 1H-NMR (D6-DMSO, 400 MHz) ppm 11.30 (s, 1H), 7.72-7.67 (m, 1H), 7.59-7.55 (d, 1H)

2-Bromo-4-fluoro-5-[(trifluoroacetyl)amino]benzenesulfonyl chloride (V-5)

(250) ##STR00511##

(251) 1H-NMR (D6-DMSO, 400 MHz) ppm 9.38 (bs, 1H), 8.00-7.97 (m, 1H), 7.68 (d, 1H)

(252) The preparation processes described above can be used to obtain the compounds of the formula (VI), for example the following compounds of the formula (VI):

2,2,2-Trifluoro-N-(4-fluoro-2-methylphenyl)acetamide (VI-2)

(253) ##STR00512##

(254) log P(HCOOH): 2.2; log P(neutral): 2.19; 1H-NMR (D6-DMSO, 400 MHz) ppm 10.97 (s, 1H), 7.28-7.30 (m, 1H), 7.19-7.21 (m, 1H), 7.08-7.11 (m, 1H), 2.18 (s, 3H)

N-(4-Bromo-2-chlorophenyl)-2,2,2-trifluoroacetamide (VI-3)

(255) ##STR00513##

(256) log P(HCOOH): 3.01; log P(neutral): 2.81; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.35 (s, 1H), 7.92 (d, 1H), 7.65 (dd, 1H), 7.45 (d, 1H)

N-(2,4-Dibromophenyl)-2,2,2-trifluoroacetamide (VI-4)

(257) ##STR00514##

(258) log P(HCOOH): 3.10; log P(neutral): 2.89; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.36 (s, 1H), 8.04 (d, 1H), 7.69 (dd, 1H), 7.43 (d, 1H)

N-(2-Chloro-4-fluorophenyl)-2,2,2-trifluoroacetamide (VI-5)

(259) ##STR00515##

(260) log P(HCOOH): 2.46; log P(neutral): 2.31; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.29 (s, 1H), 7.64 (dd, 1H), 7.53 (dd, 1H), 7.35-7.30 (m, 1H)

N-(4-Chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide (VI-6)

(261) ##STR00516##

(262) log P(HCOOH): 2.53; log P(neutral): 2.40; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.29 (s, 1H), 7.62 (dd, 1H), 7.55 (dd, 1H), 7.37 (dd, 1H)

N-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroacetamide (VI-7)

(263) ##STR00517##

(264) log P(HCOOH): 2.73; log P(neutral): 2.51; 1H-NMR (D6-DMSO, 400 MHz) ppm 11.36 (s, 1H), 7.74 (d, 1H), 7.52-7.46 (m, 2H)

(265) The preparation processes described above can be used to obtain the compounds of the formula (X), for example the following compounds of the formula (X):

4-Chloro-2-fluoro-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (X-6)

(266) ##STR00518##

(267) 11.0 g (30.9 mmol) of N-{4-chloro-2-fluoro-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-2,2,2-trifluoroacetamide in 150 ml of dioxane are added carefully to a solution of 10.3 ml (186 mmol) of sulfuric acid (96% strength) in 100 ml of water. The reaction mixture is then heated under reflux overnight. After cooling, the solution is adjusted to pH 7 using a saturated sodium bicarbonate solution and a little sodium carbonate and extracted three times with ethyl acetate. The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue comprises 8.27 g (96% pure, 99% of theory) of the title compound as a black oil/solid mixture.

(268) log P(HCOOH): 3.02; log P(neutral): 3.00; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.27 (d, 1H), 7.04 (d, 1H), 5.46 (bs, 2H), 3.85 (q, 2H)

2-Chloro-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (X-7)

(269) ##STR00519##

(270) log P(HCOOH): 3.00; log P(neutral): 2.95; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.16 (d, 1H), 6.89 (d, 1H), 6.68-6.65 (m, 1H), 5.48 (broad, 2H), 3.89 (q, 2H); GC-MS: EI mass (m/z): 241 (1Cl) [M]+

2-Fluoro-5-[(2,2,2-trifluoroethyl)sulfanyl]aniline (X-8)

(271) ##STR00520##

(272) log P(HCOOH): 2.57; log P(neutral): 2.53; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.01-6.97 (m, 1H), 6.92-6.89 (m, 1H), 6.69-6.64 (m, 1H), 5.31 (broad, 2H), 3.82 (q, 2H); GC-MS: EI mass (m/z): 225 [M]+

(273) The preparation processes described above can be used to obtain the compounds of the formula (XXI), for example the following compounds of the formula (XXI):

1,1-Disulfanediylbis(4-chloro-3-nitrobenzene) (XXI-2)

(274) ##STR00521##

(275) log P(HCOOH): 4.58; log P(neutral): 4.58; 1H-NMR (D6-DMSO, 400 MHz) ppm 8.29 (d, 2H), 7.89-7.86 (m, 2H), 7.81 (d, 2H); GC-MS: EI mass (m/z): 376 (2Cl) [M]+

1,1-Disulfanediylbis(4-fluoro-3-nitrobenzene) (XXI-3)

(276) ##STR00522##

(277) log P(HCOOH): 3.83; log P(neutral): 3.79; 1H-NMR (D6-DMSO, 400 MHz) ppm 8.32-8.29 (m, 2H), 8.03-7.97 (m, 2H), 7.69-7.63 (m, 2H); GC-MS: EI mass (m/z): 344 [M]+

1,1-Disulfanediylbis(2,4-dichloro-5-nitrobenzene) (XXI-4)

(278) ##STR00523##

(279) log P(HCOOH): 5.69; log P(neutral): 5.64; 1H-NMR (D6-DMSO, 400 MHz) ppm 8.33 (s, 2H), 8.21 (s, 2H)

(280) The preparation processes described above can be used to obtain the compounds of the formula (XXII), for example the following compounds of the formula (XXII):

3,3-Disulfanediylbis(6-chloroaniline) (XXII-2)

(281) ##STR00524##

(282) log P(HCOOH): 3.84; log P(neutral): 3.83; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.18 (d, 2H), 6.94 (d, 2H), 6.65-6.62 (m, 2H), 5.59 (broad, 4H); GC-MS: EI mass (m/z): 316 (2Cl) [M]+

3,3-Disulfanediylbis(6-fluoroaniline) (XXII-3)

(283) ##STR00525##

(284) log P(HCOOH): 2.98; log P(neutral): 2.97; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.02-6.95 (m, 2H), 6.95-6.82 (m, 2H), 6.62-6.57 (m, 2H), 5.40 (broad, 4H); GC-MS: EI mass (m/z): 284 [M]+

3,3-Disulfanediylbis(4,6-dichloroaniline) (XXII-4)

(285) ##STR00526##

(286) log P(HCOOH): 5.14; log P(neutral): 4.95; 1H-NMR (D6-DMSO, 400 MHz) ppm 7.41 (s, 2H), 6.95 (s, 2H), 5.78 (broad, 4H); GC-MS: EI mass (m/z): 386 (4Cl) [M]+

(287) The preparation processes described above can be used to obtain the compounds of the formula (XXIV), for example the following compounds of the formula (XXIV):

1-Chloro-2-fluorocyclopropanecarboxamide (XXIV-1)

(288) ##STR00527##

(289) 1H-NMR (D6-DMSO) ppm: 7.84 (broad, 1H), 7.75 (broad, 1H), 5.05-4.86 (m, 1H), 1.89-1.81 (m, 1H), 1.69-1.60 (m, 1H)

N-(2,2,2-Trifluoroethyl)cyclopentanecarboxamide (XXIV-2)

(290) ##STR00528##

(291) 1H-NMR (D6-DMSO) ppm: 8.43 (broad, 1H), 3.92-3.83 (m, 2H), 3.08-3.07 (m, 1H), 2.67-2.59 (m, 1H), 1.79-1.49 (m, 7H)

N-(2,2-Difluoroethyl)cyclopentanecarboxamide (XXIV-3)

(292) ##STR00529##

(293) 1H-NMR (D6-DMSO) ppm: 8.18 (t, 1H), 5.97 (tt, 1H), 3.50-3.40 (m, 2H), 3.08-3.06 (m, 1H), 2.64-2.57 (m, 1H), 1.78-1.45 (m, 7H)

N-(1,1,1-Trifluoropropan-2-yl)cyclopropanecarboxamide (XXIV-4)

(294) ##STR00530##

(295) 1H-NMR (D6-DMSO) ppm: 8.62-8.60 (d, 1H), 4.62-4.55 (m, 1H), 1.63-1.59 (m, 1H), 1.24-1.23 (d, 3H), 0.72-0.70 (m, 4H)

(3-Pyridyl)(4,4-difluoropiperidin-1-yl)methanone (XXIV-5)

(296) ##STR00531##

(297) 1H-NMR (D6-DMSO) ppm: 8.67-8.66 (m, 2H), 7.90-7.87 (m, 1H), 7.51-7.48 (m, 1H), 3.73 (m, 2H), 3.42 (m, 2H), 2.06 (m, 4H)

(2-Chlorophenyl)(4,4-difluoropiperidin-1-yl)methanone (XXIV-6)

(298) ##STR00532##

(299) 1H-NMR (D6-DMSO) ppm: 7.56-7.53 (m, 1H), 7.49-7.41 (m, 3H), 3.90-3.84 (m, 1H), 3.70-3.64 (m, 1H), 3.34-3.22 (m, 2H), 2.15-1.90 (m, 4H)

Use Examples

Phaedon Test (PHAECO Spray Treatment)

(300) Solvents: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide

(301) Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

(302) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. Disks of Chinese cabbage leaves (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

(303) After 7 days, the effect in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

(304) In this test, for example, the following compounds from the Preparation Examples show an efficacy of 100% at an application rate of 500 g/ha: Ia-02, Ia-04, Ia-05, Ia-13, Ia-14, Ia-15, Ia-18, Ia-19,

(305) Ib-02, Ib-10, Ib-11, Ib-14, Ib-16

(306) Tetranychus Test, OP-Resistant (TETRUR Spray Treatment)

(307) Solvents: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide

(308) Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

(309) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. Disks of bean leaves (Phaseolus vulgaris) which are infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

(310) After 6 days, the effect in % is determined. 100% here means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed.

(311) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 500 g/ha: Ia-09, Ia-17, Ib-04, Ib-05

(312) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 500 g/ha: Ia-02, Ia-03, Ia-05, Ia-07, Ia-12, Ia-13, Ia-15, Ia-18,

(313) Ia-23, Ia-26, Ib-02, Ib-03, Ib-06, Ib-07, Ib-08, Ib-09, Ib-12, Ib-13, Ib-15

(314) Meloidogyne incognita Test (MELGIN)

(315) Solvents: 80.0 parts by weight of acetone

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

(317) Containers are filled with sand, solution of active compound, Meloidogyne incognita egg/larvae suspension and lettuce seeds. The lettuce seeds germinate and the plants develop. On the roots, galls are formed.

(318) After 14 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls have been found; 0% means that the number of galls on the treated plants corresponds to the untreated control.

(319) In this test, for example, the following compound from the Preparation Examples shows an efficacy of 90% at an application rate of 20 ppm: Ia-07

(320) In this test, for example, the following compound from the Preparation Examples shows an efficacy of 100% at an application rate of 20 ppm: Ib-02

(321) Lucilia cuprina (48 h)

(322) Solvent: dimethyl sulfoxide

(323) 10 mg of active compound are dissolved in 0.5 ml of dimethyl sulfoxide. To prepare a suitable formulation, the active compound solution is diluted with water to the concentration desired in each case. About 20 Lucilia cuprina larvae are introduced into a test tube which contains about 1 cm.sup.3 of horse meat and 0.5 ml of the preparation of active compound to be tested. After 48 hours, the efficacy of the active compound preparation is determined as % larvae mortality.

(324) In this test, for example, the following compounds of the Preparation Examples show an effect of 100% at an application rate of 100 ppm: Ia-21, Ib-11

(325) Boophilus microplus Test (BOOPMI Injection)

(326) Solvent: dimethyl sulfoxide

(327) To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent, and the concentrate is diluted with solvent to the desired concentration. The solution of active compound is injected into the abdomen (Boophilus microplus), and the animals are transferred into dishes and kept in a climatized room. The activity is assessed by laying of fertile eggs.

(328) After 7 days, the effect in % is determined. 100% means that none of the ticks has laid any fertile eggs.

(329) In this test, for example, the following compound from the Preparation Examples shows an efficacy of 80% at an application rate of 20 g/animal: Ia-04

(330) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 20 g/animal: Ia-01, Ia-21, Ia-22, Ib-01, Ib-10, Ib-11, Ib-14, Ib-16

(331) Unless indicated otherwise, the test solution in the examples below was prepared as follows:

(332) 1 part by weight of active compound is mixed with the stated amounts of a solvent and emulsifier mixture (3 parts by weight of dimethylformamide as solvent and 1 part by weight of polyoxyethylene alkyl phenyl ether as emulsifier) and the solution is diluted with water to the desired concentration.

(333) Spider Mite Test (Tetranychus urticae)

(334) 50 to 100 adult spider mites are placed onto the leaves of a kidney bean plant at the two-leaf stage growing in a pot having a diameter of 6 cm.

(335) After one day, using a paint spray gun, the plant is sprayed with a sufficient amount of the active compound preparation of the desired concentration and placed in a greenhouse. After 7 days, the acaricidal effect is determined. 100% here means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed.

(336) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an active compound concentration of 100 ppm:

(337) Ia-21, Ia-01, Ib-11, Ib-01, Ia-06, Ia-14, Ia-15, Ib-14, Ia-20, Ia-25, Ia-19, Ib-16 and Ib-10

(338) Cucrbit Leaf Beetle Test (Aulacophora femoralis)

(339) Cucumber leaves are dipped into the test solution of the appropriate concentration and then air-dried. The leaves are then inserted into a plastic dish filled with sterile soil and five Aulacophora femoralis larvae at the second larval stage. The dishes are placed in a climatized room at 25 C.

(340) After 7 days, the effect in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

(341) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an active compound concentration of 500 ppm:

(342) Ia-21, Ib-11, Ib-01, Ib-14, Ib-16 and Ib-10

(343) Boophilus microplusDip Test (BOOPMI Dip)

(344) Test animals: cattle ticks (Boophilus microplus) Parkhurst strain, SP-resistant

(345) Solvent: dimethyl sulfoxide

(346) 10 mg of active compound are dissolved in 0.5 ml of dimethyl sulfoxide. To prepare a suitable formulation, the active compound solution is diluted with water to the concentration desired in each case.

(347) This active compound preparation is pipetted into tubes. 8-10 adult engorged female cattle ticks (Boophilus microplus) are transferred into a further tube with holes. The tube is immersed into the active compound formulation, and all ticks are completely wetted. After the liquid has run out, the ticks are transferred on filter disks into plastic dishes and stored in a climate-controlled room.

(348) The activity is assessed after 7 days by laying of fertile eggs. Eggs whose fertility is not visible from the outside are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. An efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all eggs are fertile.

(349) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 ppm: Ia-189, Ib-115, Ib-33

(350) Boophilus microplusInjection Test (BOOPMI inj)

(351) Solvent: dimethyl sulfoxide

(352) To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent, and the concentrate is diluted with solvent to the desired concentration.

(353) 1 l of the active compound solution is injected into the abdomen of 5 engorged adult female cattle ticks (Boophilus microplus). The animals are transferred into dishes and kept in a climate-controlled room.

(354) The activity is assessed after 7 days by laying of fertile eggs. Eggs whose fertility is not visible from the outside are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. An efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all eggs are fertile.

(355) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 20 g/animal: Ia-01, Ia-115, Ia-116, Ia-118, Ia-120, Ia-13, Ia-189, Ia-206, Ia-21, Ia-22, Ia-27, Ia-34, Ia-39, Ia-44, Ia-50, Ia-66, Ia-80, Ib-01, Ib-02, Ib-03, Ib-07, Ib-10, Ib-108, Ib-11, Ib-115, Ib-12, Ib-14, Ib-14, Ib-16, Ib-17, Ib-18, Ib-19, Ib-20, Ib-33, Ib-35, Ib-38, Ib-40, Ib-47, Ib-48, Ib-58, Ib-59, Ib-68, Ib-85

(356) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 20 g/animal: Ib-44

(357) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 20 g/animal: Ia-04, Ib-24, Ib-89

(358) Cooperia curticei Test (COOPCU)

(359) Solvent: dimethyl sulfoxide

(360) To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with Ringer solution to the desired concentration.

(361) Vessels containing the active compound preparation of the desired concentration are populated with about 40 nematode larvae (Cooperia curticei).

(362) After 5 days, the kill in % is determined. 100% means that all of the larvae have been killed; 0% means that none of the larvae have been killed.

(363) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 ppm: Ia-220

(364) Lucilia cuprina Test (LUCICU)

(365) Solvent: dimethyl sulfoxide

(366) To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.

(367) About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) are transferred into a test vessel containing minced horsemeat and the active compound preparation of the desired concentration.

(368) After 2 days, the kill in % is determined. 100% means that all larvae have been killed; 0% means that no larvae have been killed.

(369) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 ppm: Ia-21, Ib-11

(370) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 100 ppm: Ia-13

(371) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 100 ppm: Ib-02

(372) Myzus persicaeSpray Test (MYZUPE)

(373) Solvents: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide

(374) Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

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

(376) disks of Chinese cabbage leaves (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.

(377) After 6 days, the effect in % is determined. 100% here means that all of the aphids have been killed; 0% means that none of the aphids have been killed.

(378) In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g/ha, an effect of 100%: Ia-206, Ia-228, Ib-44

(379) In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g/ha, an effect of 90%: Ia-34, Ia-116, Ib-123

(380) In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 100 g/ha, an effect of 80%: Ib-42

(381) Phaedon cochleariaeSpray Test (PHAECO)

(382) Solvents: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide

(383) Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

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

(385) disks of Chinese cabbage leaves (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

(386) After 7 days, the effect in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.

(387) In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g/ha, an effect of 100%: Ia-02, Ia-04, Ia-05, Ia-13, Ia-14, Ia-15, Ia-18, Ia-19, Ia-27, Ia-28, Ia-29, Ia-31, Ia-35, Ia-36, Ia-38, Ia-45, Ia-78, Ia-79, Ia-115, Ia-118, Ia-121, Ia-135, Ia-139, Ia-149, Ia-162, Ia-191, Ia-202, Ia-209, Ia-229, Ib-02, Ib-10, Ib-11, Ib-14, Ib-16, Ib-17, Ib-20, Ib-20, Ib-27, Ib-39, Ib-43, Ib-44, Ib-56, Ib-57, Ib-68, Ib-78, Ib-83, Ib-101, Ib-110, Ib-111, Ib-115

(388) In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g/ha, an effect of 83%: Ia-33, Ia-92, Ia-130, Ia-134, Ia-171, Ia-204, Ia-207, Ia-210, Ib-18, Ib-30, Ib-108, Ib-137, Ib-143

(389) Tetranychus urticaeSpray Test, OP-Resistant (TETRUR)

(390) Solvents: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide

(391) Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

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

(393) disks of bean leaves (Phaseolus vulgaris) which are infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

(394) After 6 days, the effect in % is determined. 100% here means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed.

(395) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 500 g/ha: Ia-01, Ia-02, Ia-03, Ia-04, Ia-05, Ia-06, Ia-07, Ia-08, Ia-11, Ia-12, Ia-13, Ia-14, Ia-15, Ia-16, Ia-18, Ia-19, Ia-20, Ia-21, Ia-22, Ia-23, Ia-25, Ia-26, Ia-27, Ia-28, Ia-29, Ia-30, Ia-31, Ia-32, Ia-33, Ia-34, Ia-35, Ia-36, Ia-37, Ia-38, Ia-39, Ia-40, Ia-41, Ia-42, Ia-43, Ia-44, Ia-46, Ia-47, Ia-48, Ia-49, Ia-50, Ia-51, Ia-52, Ia-53, Ia-54, Ia-55, Ia-56, Ia-57, Ia-60, Ia-61, Ia-64, Ia-65, Ia-66, Ia-67, Ia-69, Ia-70, Ia-71, Ia-72, Ia-73, Ia-74, Ia-75, Ia-76, Ia-77, Ia-78, Ia-79, Ia-80, Ia-81, Ia-82, Ia-83, Ia-84, Ia-85, Ia-86, Ia-87, Ia-89, Ia-93, Ia-94, Ia-95, Ia-96, Ia-97, Ia-98, Ia-99, Ia-100, Ia-115, Ia-116, Ia-119, Ia-120, Ia-121, Ia-122, Ia-123, Ia-124, Ia-125, Ia-126, Ia-127, Ia-129, Ia-130, Ia-131, Ia-132, Ia-133, Ia-134, Ia-135, Ia-136, Ia-138, Ia-139, Ia-140, Ia-141, Ia-141, Ia-143, Ia-144, Ia-145, Ia-146, Ia-147, Ia-148, Ia-150, Ia-151, Ia-152, Ia-153, Ia-156, Ia-158, Ia-161, Ia-162, Ia-163, Ia-165, Ia-166, Ia-187, Ia-188, Ia-189, Ia-191, Ia-193, Ia-194, Ia-195, Ia-197, Ia-201, Ia-202, Ia-203, Ia-205, Ia-206, Ia-207, Ia-208, Ia-209, Ia-210, Ia-211, Ia-213, Ia-214, Ia-217, Ia-221, Ia-222, Ia-224, Ia-225, Ia-226, Ia-227, Ia-230, Ia-233, Ia-234, Ia-236, Ia-238, Ia-239, Ia-242, Ia-247, Ia-249, Ia-272, Ia-275, Ia-276, Ib-02, Ib-03, Ib-06, Ib-07, Ib-08, Ib-09, Ib-10, Ib-11, Ib-12, Ib-13, Ib-14, Ib-15, Ib-16, Ib-17, Ib-19, Ib-20, Ib-21, Ib-22, Ib-24, Ib-25, Ib-26, Ib-27, Ib-28, Ib-29, Ib-30, Ib-31, Ib-32, Ib-33, Ib-34, Ib-35, Ib-36, Ib-37, Ib-38, Ib-39, Ib-40, Ib-42, Ib-43, Ib-45, Ib-46, Ib-47, Ib-48, Ib-49, Ib-50, Ib-51, Ib-52, Ib-53, Ib-56, Ib-57, Ib-58, Ib-59, Ib-61, Ib-62, Ib-63, Ib-64, Ib-65, Ib-68, Ib-69, Ib-71, Ib-72, Ib-75, Ib-76, Ib-78, Ib-79, Ib-80, Ib-81, Ib-82, Ib-83, Ib-84, Ib-85, Ib-86, Ib-87, Ib-88, Ib-89, Ib-90, Ib-92, Ib-93, Ib-94, Ib-95, Ib-97, Ib-98, Ib-99, Ib-100, Ib-108, Ib-109, Ib-110, Ib-112, Ib-113, Ib-114, Ib-115, Ib-117, Ib-118, Ib-119, Ib-120, Ib-121, Ib-123, Ib-125, Ib-126, Ib-127, Ib-129, Ib-130, Ib-131, Ib-132, Ib-135, Ib-137, Ib-138, Ib-139, Ib-140, Ib-141, Ib-148, Ib-151, Ib-160, Ib-169, Ib-174

(396) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 500 g/ha: Ia-59, Ia-62, Ia-63, Ia-68, Ia-83, Ia-88, Ia-91, Ia-92, Ia-101, Ia-102, Ia-103, Ia-104, Ia-105, Ia-106, Ia-107, Ia-117, Ia-118, Ia-128, Ia-149, Ia-155, Ia-159, Ia-160, Ia-167, Ia-168, Ia-169, Ia-171, Ia-172, Ia-173, Ia-175, Ia-176, Ia-177, Ia-178, Ia-180, Ia-190, Ia-192, Ia-196, Ia-204, Ia-205, Ia-212, Ia-215, Ia-216, Ia-218, Ia-219, Ia-220, Ia-223, Ia-228, Ia-229, Ia-231, Ia-232, Ia-235, Ia-237, Ia-240, Ia-241, Ia-243, Ia-244, Ia-245, Ia-248, Ia-250, Ia-251, Ia-252, Ia-253, Ia-254, Ia-255, Ia-256, Ia-257, Ia-258, Ia-259, Ia-260, Ia-261, Ia-262, Ia-263, Ia-264, Ia-265, Ia-266, Ia-267, Ia-268, Ia-269, Ia-270, Ia-278, Ib-01, Ib-23, Ib-41, Ib-54, Ib-60, Ib-66, Ib-67, Ib-73, Ib-74, Ib-77, Ib-91, Ib-96, Ib-101, Ib-102, Ib-103, Ib-104, Ib-111, Ib-116, Ib-122, Ib-124, Ib-128, Ib-133, Ib-134, Ib-136, Ib-142, Ib-143, Ib-144, Ib-145, Ib-146, Ib-147, Ib-149, Ib-150, Ib-152, Ib-153, Ib-154, Ib-155, Ib-156, Ib-157, Ib-158, Ib-166, Ib-167, Ib-172

(397) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 500 g/ha: Ia-09, Ia-17, Ia-45, Ia-90, Ia-108, Ia-109, Ib-04, Ib-05, Ib-18

(398) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 100 g/ha: Ia-58

(399) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 100 g/ha: Ia-181

(400) Tetranychus urticaeSpray Test, OP-Resistant (TETRUR)

(401) Solvents: 7 parts by weight of dimethylformamide

(402) Emulsifier: 2 part by weight of alkylaryl polyglycol ether

(403) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. If the addition of ammonium salts or/and penetrants is required, these are in each case added in a concentration of 1000 ppm to the solution of the preparation.

(404) Bean plants (Phaseolus vulgaris) which are heavily infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are treated by spraying with the active compound preparation of the desired concentration.

(405) After 7 days, the effect in % is determined. 100% here means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed.

(406) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 90% at an application rate of 100 ppm: Ib-44

(407) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 100% at an application rate of 20 ppm: Ib-168

(408) In this test, for example, the following compounds of the Preparation Examples show an efficacy of 80% at an application rate of 20 ppm: Ib-159.