Novel Pyrazole Derivatives

Abstract

The present invention relates to novel pyrazole derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for controlling harmful microorganisms in crop protection and in the protection of materials. Further, the present invention also relates to certain intermediates useful for producing said novel pyrazole derivatives.

Claims

1. Compound of formula (I) ##STR00024## And/or one or more tautomers and/or salts thereof, wherein R.sup.1 is H, CH.sub.3, F, Cl, Br, or C.sub.1-C.sub.4 alkoxy, R.sup.2 is methyl or ethyl, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a 5- to 7-membered carbocyclic ring, optionally substituted with up to 5 independently selected substituents R.sup.Q1; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q1 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, Q.sup.2 is a 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R.sup.Q2; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q2 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein each R.sup.N is independently selected from the group consisting of cyano, 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 alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.2-C.sub.6 alkoxyalkyl, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminoalkyl and C.sub.3-C.sub.6 dialkylaminoalkyl, C.sub.1-C.sub.6 aminoalkyl, benzyl, SO.sub.2R.sup.S, wherein each R.sup.C is independently selected from the group consisting of H and C.sub.1-C.sub.4 alkyl, wherein R.sup.1N and R.sup.2N each are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein each R.sup.S is independently selected from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, and C.sub.3-C.sub.6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, provided that at least one substituent R.sup.Q2 is C.sub.3-C.sub.7 alkenylalkoxy or C.sub.3-C.sub.7 alkynylalkoxy.

2. Compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein R.sup.1 is H, CH.sub.3, F, Cl, Br, or OCH.sub.3, R.sup.2 is methyl or ethyl, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a 5- to 7-membered fully saturated carbocyclic ring or a fully unsaturated 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R.sup.Q1; or a 5- to 7-membered fully saturated heterocyclic ring or a fully unsaturated 5- or 6-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein the heterocyclic ring is optionally substituted with up to 3 substituents R.sup.Q1 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CHNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, Q.sup.2 is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R.sup.Q2; or is a fully unsaturated or a fully saturated 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q2 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CHNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein each R.sup.N is independently selected from the group consisting of cyano, 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 alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.2-C.sub.6 alkoxyalkyl, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminoalkyl and C.sub.3-C.sub.6 dialkylaminoalkyl, C.sub.1-C.sub.6 aminoalkyl, benzyl, SO.sub.2R.sup.S, wherein R.sup.1N and R.sup.2N each are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein each R.sup.S is independently selected from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, and C.sub.3-C.sub.6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, provided that at least one substituent R.sup.Q2 is C.sub.3-C.sub.7 alkenylalkoxy or C.sub.3-C.sub.7 alkynylalkoxy.

3. Compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein R.sup.1 is H, CH.sub.3, F, Cl or Br, R.sup.2 is CH.sub.3, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a ring selected from the group consisting of phenyl, 5- or 6-membered heteroaromatic rings, 5- to 7-membered fully saturated heterocyclic rings, and 5- to 7-membered fully saturated carbocyclic rings, wherein Q.sup.1 is optionally substituted with up to 5 substituents R.sup.Q1; wherein each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CHNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, Q.sup.2 is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic or heterocyclic ring, optionally substituted with up to 5 substituents R.sup.Q2; wherein each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CHNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein R.sup.1N and R.sup.2N are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, provided that at least one substituent R.sup.Q2 is C.sub.3-C.sub.7 alkenylalkoxy or C.sub.3-C.sub.7 alkynylalkoxy.

4. Compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein R.sup.1 is CH.sub.3 or Cl, R.sup.2 is CH.sub.3, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a ring selected from the group consisting of phenyl, 5- or 6-membered heteroaromatic rings, 5- to 7-membered fully saturated heterocyclic rings, and 5- or 6-membered fully saturated carbocyclic rings, wherein Q.sup.1 is optionally substituted with up to 5 substituents R.sup.Q1; wherein each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.1-C.sub.4 alkanoylamino, SF.sub.5, SCN, isonitrile, CHNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, Q.sup.2 is a ring selected from the group consisting of phenyl, 5-membered heteroaromatic rings and 6-membered heteroaromatic rings, wherein Q.sup.2 is optionally substituted with up to 5 substituents R.sup.Q2; wherein each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.4 alkenylalkoxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.1-C.sub.4 alkanoylamino, SF.sub.5, SCN, isonitrile, CHNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein R.sup.1N and R.sup.2N are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, provided that at least one substituent R.sup.Q2 is C.sub.3-C.sub.7 alkenylalkoxy or C.sub.3-C.sub.7 alkynylalkoxy.

5. Compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein R.sup.1 is CH.sub.3 or Cl, R.sup.2 is CH.sub.3, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a ring selected from the group consisting of phenyl, 5- or 6-membered heteroaromatic rings, 5- to 7-membered fully saturated heterocyclic rings, and 5- or 6-membered fully saturated carbocyclic rings, wherein Q.sup.1 is optionally substituted with up to 5 substituents R.sup.Q1; wherein each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.1-C.sub.4 alkanoylamino, SF.sub.5, SCN, isonitrile, CHNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein R.sup.1N and R.sup.2N are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein optionally substituted phenyl is phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, Q.sup.2 is a ring selected from the group consisting of phenyl or pyridinyl, wherein Q.sup.2 is optionally substituted with one or more substituents R.sup.Q2; wherein each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, 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.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, provided that at least one substituent R.sup.Q2 is propargyloxy or allyloxy.

6. Compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein R.sup.1 is CH.sub.3 or Cl, R.sup.2 is CH.sub.3, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a ring selected from the group consisting of phenyl, furanyl, pyridinyl, piperidinyl, azepanyl and morpholinyl, wherein Q.sup.1 is optionally substituted with up to 5 substituents R.sup.Q1; wherein each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.1-C.sub.4 alkanoylamino, SF.sub.5, SCN, isonitrile, NR.sup.1NR.sup.2N, wherein R.sup.1N and R.sup.2N are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, provided that at least one of the substituents R.sup.Q1 is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, 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.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, Q.sup.2 is a phenyl ring substituted with one, two, three or four substituents R.sup.Q2; wherein each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, 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.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, provided that one, two or three substituents R.sup.Q2 are propargyloxy or allyloxy.

7. Compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein R.sup.1 is CH.sub.3 or Cl, R.sup.2 is CH.sub.3, X is NH or O, Q.sup.1 is a phenyl or a furanyl ring, wherein Q.sup.1 is optionally substituted with one or more substituents R.sup.Q1 selected from the group consisting of F, Cl, Br, I, cyano, nitro, amino, hydroxy, 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.3-C.sub.6 alkenylalkoxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, Q.sup.2 is a phenyl ring substituted with one, two, three or four substituents R.sup.Q2; wherein each R.sup.Q2 is independently selected from the group consisting of F, Cl, Br, I, cyano, hydroxy, 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.3-C.sub.6 alkenylalkoxy, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, provided that one, two or three substituents R.sup.Q2 are propargyloxy or allyloxy.

8. Compound of formula (I) according to claim 1, and/or one or more tautomers and/or salts thereof, wherein R.sup.1 is CH.sub.3 or Cl, R.sup.2 is CH.sub.3, X is NH or O, Q.sup.1 is a phenyl ring substituted with one or more substituents R.sup.Q1 selected from the group consisting of F, Cl, Br, I, cyano, nitro, amino, hydroxy, 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 alkenylalkoxy, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.6 alkynyloxy, Q.sup.2 is a phenyl ring substituted with one, two, three or four substituents R.sup.Q2; wherein each R.sup.Q2 is independently selected from the group consisting of F, Cl, Br, I, cyano, hydroxy, 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 alkenylalkoxy, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.6 alkynyloxy, provided that one, two or three substituents R.sup.Q2 are propargyloxy or allyloxy.

9. Composition comprising (a) a fungicidally effective amount of a compound as defined in claim 1, and one or more further constituents selected from the group consisting of groups (b) and (c): (b) agrochemically acceptable adjuvants, optionally selected from the group consisting of surfactants, liquid diluents and solid diluents, and (c) other pesticidally active ingredients.

10. Method for controlling one or more plant diseases caused by fungal plant pathogens, comprising (i) providing a compound of the formula (I) as defined in claim 1, and (ii) applying to the plant, to a portion of the plant or to plant seeds a fungicidally effective amount the compound provided in (i).

11. A product comprising a compound of the formula (I) as defined in claim 1 for controlling fungi, optionally for controlling fungi in plants or plant seeds.

12. Method for producing a compound of formula (I) as defined in claim 1, comprising: (i) providing a compound of formula (Z-ix) ##STR00025## (ii) providing a compound of formula (Z-x)
R.sup.2NHNH.sub.2 (Z-x) (iii) reacting compounds (Z-ix) and (Z-x), thereby obtaining a compound of formula (I).

13. Compound of formula (Z-ix) ##STR00026## and/or one or more tautomers, solvates and/or salts thereof, wherein R.sup.1 is H, CH.sub.3, F, Cl, Br, or C.sub.1-C.sub.4 alkoxy, R.sup.2 is methyl or ethyl, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a 5- to 7-membered carbocyclic ring, optionally substituted with up to 5 independently selected substituents R.sup.Q1; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q1 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, Q.sup.2 is a 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R.sup.Q2; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q2 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein each R.sup.N is independently selected from the group consisting of cyano, 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 alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.2-C.sub.6 alkoxyalkyl, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminoalkyl and C.sub.3-C.sub.6 dialkylaminoalkyl, C.sub.1-C.sub.6 aminoalkyl, benzyl, SO.sub.2R.sup.S, wherein each R.sup.C is independently selected from the group consisting of H and C.sub.1-C.sub.4 alkyl, wherein R.sup.1N and R.sup.2N each are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein each R.sup.S is independently selected from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, and C.sub.3-C.sub.6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, provided that at least one substituent R.sup.Q2 is C.sub.3-C.sub.7 alkenylalkoxy or C.sub.3-C.sub.7 alkynylalkoxy.

14. Compound of formula (Z-ii)
Q.sup.2-NCS (Z-ii) Wherein R.sup.1 is H, CH.sub.3, F, Cl, Br, or C.sub.1-C.sub.4 alkoxy, R.sup.2 is methyl or ethyl, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a 5- to 7-membered carbocyclic ring, optionally substituted with up to 5 independently selected substituents R.sup.Q1; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q1 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, Q.sup.2 is a 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R.sup.Q2; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q2 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein each R.sup.N is independently selected from the group consisting of cyano, 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 alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.2-C.sub.6 alkoxyalkyl, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminoalkyl and C.sub.3-C.sub.6 dialkylaminoalkyl, C.sub.1-C.sub.6 aminoalkyl, benzyl, SO.sub.2R.sup.S, wherein each R.sup.C is independently selected from the group consisting of H and C.sub.1-C.sub.4 alkyl, wherein R.sup.1N and R.sup.2N each are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein each R.sup.S is independently selected from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, and C.sub.3-C.sub.6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, provided that at least one substituent R.sup.Q2 is C.sub.3-C.sub.7 alkenylalkoxy or C.sub.3-C.sub.7 alkynylalkoxy.

15. Compound of formula (Z-i)
Q.sup.2-NH.sub.2 (Z-i) Wherein R.sup.1 is H, CH.sub.3, F, Cl, Br, or C.sub.1-C.sub.4 alkoxy, R.sup.2 is methyl or ethyl, X is a structure element selected from the group consisting of NH, N(CH.sub.3), O, S, CH.sub.2, CH(OH), and CH(CH.sub.3), Q.sup.1 is a 5- to 7-membered carbocyclic ring, optionally substituted with up to 5 independently selected substituents R.sup.Q1; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q1 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, Q.sup.2 is a 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R.sup.Q2; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(O) and C(S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(O).sub.2, wherein the heterocyclic ring is optionally substituted with up to 5 substituents R.sup.Q2 on carbon atom heterocyclic ring members and optionally substituted with substituents R.sup.N on nitrogen atom heterocyclic ring members, if present, each R.sup.Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 haloalkyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.3-C.sub.6 heterocyclyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 haloalkoxy, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.7 alkenylalkoxy, C.sub.2-C.sub.6 alkenyloxy, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.7 alkynylalkoxy, C.sub.3-C.sub.7 alkynyloxy, C.sub.3-C.sub.7 cycloalkoxy, C.sub.3-C.sub.6 halocycloalkoxy, C.sub.3-C.sub.6 heterocyclyloxy, C.sub.1-C.sub.3 alkylthio, C.sub.1-C.sub.3 haloalkylthio, C.sub.1-C.sub.3 alkylsulfinyl, C.sub.1-C.sub.3 haloalkylsulfinyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 haloalkylsulfonyl, C.sub.1-C.sub.2 alkylsulfonyloxy, C.sub.1-C.sub.2 haloalkylsulfonyloxy, C.sub.4-C.sub.7 alkylcycloalkyl, C.sub.4-C.sub.6 cycloalkylalkyl, C.sub.2-C.sub.3 alkylcarbonyl, C.sub.2-C.sub.3 alkylcarbonyloxy, C.sub.1-C.sub.4 alkanoylamino, C.sub.2-C.sub.3 alkylcarbonylamino, (C.sub.1-C.sub.6 alkoxy)iminocarbonyl, tri(C.sub.1-C.sub.4-alkyl)silyl, SCF.sub.3, SF.sub.5, SCN, isonitrile, CR.sup.CNOC.sub.1-C.sub.4 alkyl, NR.sup.1NR.sup.2N and optionally substituted phenyl, wherein each R.sup.N is independently selected from the group consisting of cyano, 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 alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy, C.sub.2-C.sub.6 alkoxyalkyl, C.sub.2-C.sub.6 alkylcarbonyl, C.sub.2-C.sub.6 alkoxycarbonyl, C.sub.2-C.sub.6 alkylaminoalkyl and C.sub.3-C.sub.6 dialkylaminoalkyl, C.sub.1-C.sub.6 aminoalkyl, benzyl, SO.sub.2R.sup.S, wherein each R.sup.C is independently selected from the group consisting of H and C.sub.1-C.sub.4 alkyl, wherein R.sup.1N and R.sup.2N each are independently selected from C.sub.1-C.sub.4 alkyl and C.sub.3-C.sub.6 cycloalkyl, wherein each R.sup.S is independently selected from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, and C.sub.3-C.sub.6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, 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)-alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.1-C.sub.4 alkoxy, provided that at least one substituent R.sup.Q2 is C.sub.3-C.sub.7 alkenylalkoxy or C.sub.3-C.sub.7 alkynylalkoxy.

Description

EXAMPLES

Log P Values

[0275] Measurement of Log P values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods:

[.sup.a] Log P value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
[.sup.b] Log P value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
[.sup.c] Log P value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0276] Calibration was done with straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.

NMR-Peak Lists

[0277] .sup.1H-NMR data of selected examples are written in form of .sup.1H-NMR-peak lists. To each signal peak are listed the -value in ppm and the signal intensity in round brackets. Between the -valuesignal intensity pairs are semicolons as delimiters.

[0278] The peak list of an example has therefore the form:

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

[0279] Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

[0280] For calibrating chemical shift for .sup.1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.

[0281] The .sup.1H-NMR peak lists are similar to classical .sup.1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

[0282] Additionally they can show like classical .sup.1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.

[0283] To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown in our .sup.1H-NMR peak lists and have usually on average a high intensity.

[0284] The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).

[0285] Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via side-products-fingerprints.

[0286] An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical .sup.1H-NMR interpretation.

[0287] Further details of NMR-data description with peak lists you find in the publication Citation of NMR Peaklist Data within Patent Applications of the Research Disclosure Database Number 564025.

Synthesis Example 1

Preparation of 4-[4-(Allyloxy)-2-fluorophenyl]-N-[2,4-difluoro-6-(prop-2-yn-1-yloxy)phenyl]-1,3-dimethyl-1H-pyrazol-5-amine (compound I-22)

Example 1.1Step 1

1-(2-fluoro-4-methoxyphenyl)acetone (Z-iv-2)

[0288] ##STR00011##

[0289] 1-Bromo-2-fluoro-4-methoxybenzene (3.00 g, 14.6 mmol) was dissolved in acetone (30.0 mL) in a dry reaction tube. Cesium carbonate (9.54 g, 29.2 mmol) was added. The mixture was degassed with argon for 5 minutes, then [Pd(cinnamyl)Cl.sub.2].sub.2 (CAS-RN 12131-44-11, 114 mg, 0.21 mmol) and MorDalPhos (CAS-RN 1237588-12-3, 0.41 g, 0.87 mmol) were added, the tube was sealed and the mixture was heated to 90 C. in a stirring block for 18 h. After that, the mixture was diluted with conc ammonium chloride, extracted with ethyl acetate and the organic phase was dried over sodium sulphate, filtered and eventually evaporated. The crude product was purified by flash chromatography over silica gel. Yield: 2.28 g (81% of theory).

Example 1.2Step 2

1-(2-fluoro-4-hydroxyphenyl)acetone

[0290] ##STR00012##

[0291] The product from Step 1 (2.34 g, 12.8 mmol) was dissolved in acetic acid (47 mL). Cone hydrobromic acid (14.5 mL) was added and the mixture was stirred under reflux for 5 h. The reaction was then cooled to room temperature, diluted with ice-water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography over silica gel to give 1.80 g (82% of theory) of 1-(2-fluoro-4-hydroxyphenyl)acetone.

[0292] log P[.sup.a]=1.13.

Example 1.3Step 3

1-[4-(allyloxy)-2-fluorophenyl]acetone (Z-iv-1)

[0293] ##STR00013##

[0294] The product from Step 2 (1.80 g, 10.7 mmol) was dissolved in DMF (20.0 mL), potassium carbonate (2.22 g, 16.0 mmol) was added and then allyl bromide (1.11 mL, 12.8 mmol) were added slowly under stirring. The reaction mixture was stirred for 16 h at ambient temperature. Water was then added, the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography over silica gel to give 1.61 g (72% of theory) of the desired product.

Example 1.4Step 4

3,5-difluoro-2-isothiocyanatophenyl prop-2-yn-1-yl ether (Z-ii-03)

[0295] ##STR00014##

[0296] 2,4-Difluoro-6-(prop-2-yn-1-yloxy)aniline (1.00 g, 5.46 mmol) was dissolved in dichloromethane (10.0 mL), sodium hydrogen carbonate (1.61 g, 19.1 mmol) was added and the mixture was cooled to 0 C. Thiophosgene (0.55 mL, 5.46 mmol) was added dropwise, the reaction was then stirred for 2 h and finally partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate, filtered and evaporated. Yield: 1.23 g (quant.).

[0297] log P (pH 2.3)=3.72

Example 1.5Step 5

4-[4-(Allyloxy)-2-fluorophenyl]-N-[2,4-difluoro-6-(prop-2-yn-1-yloxy)phenyl]-1,3-dimethyl-1H-pyrazol-5-amine (compound I-22)

[0298] ##STR00015##

[0299] Sodium hydride (60% in paraffine, 0.05 g, 1.24 mmol) was suspended under argon in THF (2.0 mL). The product from Example 1.3Step 3 (0.24 g, 1.15 mmol) was dissolved in THF (3.0 mL) and was then added dropwise at 0 C. to the suspension of sodium hydride. Stirring was maintained for 1 h at 0 C., then a solution of the product from Example 1.4Step 4 (0.20 g, 0.88 mmol) in THF (3.0 mL) was added and the reaction was stirred for further 1 h at 0 C. After that, acetic acid (0.18 mL, 3.10 mmol) and methyl hydrazine (0.06 mL, 1.10 mmol) were added and the reaction was stirred at reflux for 2 h. Conc. ammonium chloride was added followed by extraction with ethyl acetate. The combined organic phases were washed with water and brine, dried, concentrated and purified via companion to afford the product in a yield of 0.22 g (54% of theory).

Preparation Examples

[0300] The compounds according to formula (I) of the invention listed in the following table were obtained in analogy to the examples above and to the general description of the processes of preparing the compounds of the formula (I).

[0301] The following compounds I-01 to I-67 of the formula (I) (R.sup.1=methyl, R.sup.2=methyl) were synthesised, and are preferred compounds of formula (I) according to the present invention:

TABLE-US-00002 Ex N.sup.o X Q.sup.1 Q.sup.2 LogP I-01 NH 2-chloro-4-fluorophenyl 2,4-difluoro-6-(prop-2-yn-1- 3.26.sup.[a]; yloxy)phenyl 3.10.sup.[c] I-02 NH 2-chloro-4-fluorophenyl 4-(allyloxy)-2,6-difluorophenyl 3.54.sup.[a]; 3.40.sup.[c] I-03 NH 2-chloro-4-fluorophenyl 2,6-difluoro-4-(prop-2-yn-1- 3.09.sup.[a]; yloxy)phenyl 2.90.sup.[c] I-04 N(CH.sub.3) 2-chloro-4-fluorophenyl 4-(allyloxy)-2,6-difluorophenyl 4.40.sup.[a] I-05 NH 2,4-dichlorophenyl 2,4-difluoro-6-(prop-2-yn-1- 3.69.sup.[a] yloxy)phenyl I-06 NH 2-fluorophenyl 2,6-difluoro-4-(prop-2-yn-1- 2.78.sup.[a] yloxy)phenyl I-07 NH 2-fluorophenyl 2,4-difluoro-6-(prop-2-yn-1- 2.96.sup.[a] yloxy)phenyl I-08 NH 2,4-dichlorophenyl 4-(allyloxy)-2,6-difluorophenyl 3.97.sup.[a] I-09 NH 2,4-dichlorophenyl 2,6-difluoro-4-(prop-2-yn-1- 3.44.sup.[a] yloxy)phenyl I-10 NH 3,5-dimethoxyphenyl 2,6-difluoro-4-(prop-2-yn-1- 2.73.sup.[a] yloxy)phenyl I-11 NH 3,5-dimethoxyphenyl 4-(allyloxy)-2,6-difluorophenyl 3.11.sup.[a] I-12 NH 3,5-dimethoxyphenyl 2,4-difluoro-6-(prop-2-yn-1- 2.85.sup.[a] yloxy)phenyl I-13 NH 2-fluorophenyl 4-(allyloxy)-2,6-difluorophenyl 3.22.sup.[a] I-14 NH 2,4-difluorophenyl 2,6-difluoro-4-(prop-2-yn-1- 2.90.sup.[a] yloxy)phenyl I-15 NH 2,4-difluorophenyl 4-(allyloxy)-2,6-difluorophenyl 3.33.sup.[a] I-16 NH 2,4-difluorophenyl 2,4-difluoro-6-(prop-2-yn-1- 3.07.sup.[a] yloxy)phenyl I-17 NH 2-fluoro-4-methoxyphenyl 2,6-difluoro-4-(prop-2-yn-1- 2.74.sup.[a] yloxy)phenyl I-18 NH 2-fluoro-4-methoxyphenyl 4-(allyloxy)-2,6-difluorophenyl 3.11.sup.[a] I-19 NH 2-fluoro-4-methoxyphenyl 2,4-difluoro-6-(prop-2-yn-1- 2.86.sup.[a] yloxy)phenyl I-20 NH 6-chloropyridin-3-yl 2,6-difluoro-4-(prop-2-yn-1- 2.56.sup.[a]; yloxy)phenyl 2.54.sup.[b] I-21 NH 6-chloropyridin-3-yl 4-(allyloxy)-2,6-difluorophenyl 2.95.sup.[a]; 2.92.sup.[b] I-22 NH 4-(allyloxy)-2-fluorophenyl 2,4-difluoro-6-(prop-2-yn-1- 3.30.sup.[a] yloxy)phenyl I-23 NH 4-(allyloxy)-2-fluorophenyl 4-(allyloxy)-2,6-difluorophenyl 3.62.sup.[a] I-24 NH 4-(allyloxy)-2-fluorophenyl 2,6-difluoro-4-(prop-2-yn-1- 3.17.sup.[a] yloxy)phenyl I-25 NH 6-chloropyridin-3-yl 2,4-difluoro-6-(prop-2-yn-1- 2.69.sup.[a]; yloxy)phenyl 2.63.sup.[b] I-26 NH 2-fluoro-4-(prop-2-yn-1- 2,4-difluoro-6-(prop-2-yn-1- 2.88.sup.[a] yloxy)phenyl yloxy)phenyl I-27 NH 2-fluoro-4-(prop-2-yn-1- 2,6-difluoro-4-(prop-2-yn-1- 2.77.sup.[a] yloxy)phenyl yloxy)phenyl I-28 NH 2-fluoro-4-(prop-2-yn-1- 4-(allyloxy)-2,6-difluorophenyl 3.13.sup.[a] yloxy)phenyl I-29 NH 2-chloro-4-fluorophenyl 2-fluoro-4-(prop-2-yn-1- 3.25.sup.[a]; yloxy)phenyl 3.22.sup.[b] I-30 NH 2-chloro-4-fluorophenyl 4-(allyloxy)phenyl 3.51.sup.[a]; 3.52.sup.[b] I-31 NH 2-chloro-4-fluorophenyl 4-(prop-2-yn-1-yloxy)phenyl 3.09.sup.[a]; 3.06.sup.[b] I-32 NH 2-chloro-4-fluorophenyl 2-chloro-4-(prop-2-yn-1- 3.65.sup.[a]; yloxy)phenyl 3.59.sup.[b] I-33 NH 2-chloro-4-fluorophenyl 2,5-difluoro-4-(prop-2-yn-1- 3.33.sup.[a]; yloxy)phenyl 3.23.sup.[b]; 3.20.sup.[c] I-34 NH 2-chloro-4-fluorophenyl 4-(allyloxy)-2,5-difluorophenyl 3.74.sup.[a]; 3.66.sup.[b]; 3.60.sup.[c] I-35 NH 2-chloro-4-fluorophenyl 4-(allyloxy)-3-fluorophenyl 3.61.sup.[a]; 3.56.sup.[b]; 3.50.sup.[c] I-36 NH 2-chloro-4-fluorophenyl 3-fluoro-4-(prop-2-yn-1- 3.17.sup.[a]; yloxy)phenyl 3.14.sup.[b]; 3.10.sup.[c] I-37 NH 2-chloro-4-fluorophenyl 5-(allyloxy)-2-fluorophenyl 3.78.sup.[a]; 3.73.sup.[b]; 3.70.sup.[c] I-38 NH 2-chloro-4-fluorophenyl 2-fluoro-5-(prop-2-yn-1- 3.33.sup.[a]; yloxy)phenyl 3.27.sup.[b]; 3.20.sup.[c] I-39 NH 2,4-dichlorophenyl 2,5-difluoro-4-(prop-2-yn-1- 3.70.sup.[a]; yloxy)phenyl 3.62.sup.[b]; 3.60.sup.[c] I-40 NH 2,4-dichlorophenyl 2-chloro-4-(prop-2-yn-1- 4.13.sup.[a]; yloxy)phenyl 4.06.sup.[b]; 4.00.sup.[c] I-41 NH 2-chloro-4-fluorophenyl 4-(allyloxy)-2-chlorophenyl 4.23.sup.[a]; 4.20.sup.[b] I-42 NH 2-bromo-4-fluorophenyl 2,4-difluoro-6-(prop-2-yn-1- 3.33.sup.[a]; yloxy)phenyl 3.32.sup.[b] I-43 NH 2-bromo-4-fluorophenyl 2-(prop-2-yn-1-yloxy)phenyl 3.60.sup.[a] I-44 NH 2-bromo-4-fluorophenyl 2-(allyloxy)-5-fluorophenyl 4.08.sup.[a] I-45 NH 2-bromo-4-fluorophenyl 5-fluoro-2-(prop-2-yn-1- 3.64.sup.[a] yloxy)phenyl I-46 NH 2-bromo-4-fluorophenyl 2-(allyloxy)-4-methylphenyl 4.39.sup.[a] I-47 NH 2-bromo-4-fluorophenyl 4-methyl-2-(prop-2-yn-1- 3.87.sup.[a] yloxy)phenyl I-48 NH 2-chloro-4-fluorophenyl 2-(allyloxy)phenyl 3.99.sup.[a] I-49 NH 2-chloro-4-fluorophenyl 2-(prop-2-yn-1-yloxy)phenyl 3.53.sup.[a] I-50 NH 2-chloro-4-fluorophenyl 2-(allyloxy)-5-fluorophenyl 4.01.sup.[a] I-51 NH 2-chloro-4-fluorophenyl 5-fluoro-2-(prop-2-yn-1- 3.58.sup.[a] yloxy)phenyl I-52 NH 2-chloro-4-fluorophenyl 2-(allyloxy)-4-methylphenyl 4.32.sup.[a] I-53 NH 2-chloro-4-fluorophenyl 4-methyl-2-(prop-2-yn-1- 3.83.sup.[a] yloxy)phenyl I-54 NH 2,4-dichlorophenyl 2-(allyloxy)phenyl 4.49.sup.[a] I-55 NH 2,4-dichlorophenyl 2-(prop-2-yn-1-yloxy)phenyl 3.96.sup.[a] I-56 NH 2,4-dichlorophenyl 2-(allyloxy)-5-fluorophenyl 4.49.sup.[a] I-57 NH 2,4-dichlorophenyl 2-(allyloxy)-4-methylphenyl 4.85.sup.[a] I-58 NH 2,4-dichlorophenyl 4-methyl-2-(prop-2-yn-1- 4.30.sup.[a] yloxy)phenyl I-59 NH 2,4,6-trifluorophenyl 2,4-difluoro-6-(prop-2-yn-1- 3.10.sup.[a] yloxy)phenyl I-60 NH 4-chloro-2,6-difluorophenyl 2,4-difluoro-6-(prop-2-yn-1- 3.49.sup.[a] yloxy)phenyl I-61 NH 2,6-difluoro-4-methoxyphenyl 2,4-difluoro-6-(prop-2-yn-1- 3.00.sup.[a] yloxy)phenyl I-62 NH 2,6-difluoro-4-methoxyphenyl 2,6-difluoro-4-(prop-2-yn-1- 2.85.sup.[a] yloxy)phenyl I-63 NH 2,6-difluoro-4-(prop-2-yn-1- 2,4-difluoro-6-(prop-2-yn-1- 2.99.sup.[a] yloxy)phenyl yloxy)phenyl I-64 NH 2-chloro-4-fluorophenyl 2-chloro-6-(prop-2-yn-1- 3.56.sup.[a] yloxy)phenyl I-65 NH 2-chloro-4-fluorophenyl 2-(allyloxy)-6-chlorophenyl 4.06.sup.[a] I-66 NH 2,4-dichlorophenyl 2-chloro-6-(prop-2-yn-1- 3.99.sup.[a] yloxy)phenyl I-67 NH 2,4-difluorophenyl 2-chloro-6-(prop-2-yn-1- 3.26.sup.[a] yloxy)phenyl

NMR Peak Lists for Active Ingredients According to Formula (I)

Example I-01

[0302] .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO):

[0303] =7.208 (1.4); 7.203 (1.4); 7.193 (1.5); 7.188 (1.4); 7.060 (1.1); 7.049 (1.2); 7.046 (1.6); 7.035 (1.6); 7.028 (2.4); 6.984 (0.9); 6.979 (0.8); 6.970 (1.5); 6.965 (1.4); 6.956 (0.7); 6.951 (0.6); 6.595 (0.9); 6.578 (0.9); 6.527 (0.5); 6.522 (0.5); 6.508 (0.9); 6.493 (0.6); 6.489 (0.5); 4.730 (1.8); 4.727 (2.0); 4.719 (1.9); 4.715 (1.9); 3.660 (1.6); 3.656 (3.9); 3.652 (16.0); 3.636 (0.5); 3.330 (16.6); 2.524 (0.4); 2.521 (0.5); 2.518 (0.5); 2.509 (12.5); 2.506 (28.6); 2.503 (41.1); 2.500 (31.7); 2.497 (16.2); 1.883 (14.5); 1.872 (0.7); 0.005 (1.8); 0.000 (62.3); 0.006 (3.0)

Example I-02

[0304] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0305] =7.375 (2.4); 7.192 (1.5); 7.186 (1.6); 7.170 (1.6); 7.163 (1.6); 7.081 (0.9); 7.065 (1.1); 7.060 (1.7); 7.044 (1.6); 7.016 (1.2); 7.009 (1.0); 6.995 (1.8); 6.988 (1.6); 6.973 (0.7); 6.967 (0.6); 6.432 (0.5); 6.421 (3.7); 6.395 (3.6); 6.384 (0.5); 5.953 (0.4); 5.940 (0.7); 5.926 (0.7); 5.913 (0.9); 5.909 (0.5); 5.900 (0.5); 5.896 (0.9); 5.883 (0.8); 5.870 (0.9); 5.857 (0.4); 5.301 (1.5); 5.297 (1.6); 5.293 (0.6); 5.258 (1.8); 5.254 (2.9); 5.250 (2.0); 5.227 (1.5); 5.223 (1.4); 4.431 (2.4); 4.427 (2.5); 4.422 (1.9); 4.418 (2.4); 4.414 (2.3); 3.659 (16.0); 3.326 (24.0); 2.525 (0.8); 2.511 (17.0); 2.507 (34.1); 2.502 (45.0); 2.498 (33.3); 2.493 (16.5); 1.879 (15.6); 0.008 (2.6); 0.000 (68.9); 0.009 (2.8)

Example I-03

[0306] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0307] =7.417 (2.4); 7.197 (1.6); 7.191 (1.7); 7.175 (1.7); 7.169 (1.6); 7.086 (0.9); 7.069 (1.1); 7.064 (1.7); 7.048 (1.6); 7.019 (1.2); 7.012 (1.0); 6.998 (1.8); 6.991 (1.6); 6.977 (0.7); 6.970 (0.6); 6.490 (0.5); 6.479 (3.7); 6.453 (3.7); 6.442 (0.5); 4.663 (5.2); 4.657 (5.3); 3.662 (16.0); 3.580 (1.5); 3.574 (3.4); 3.569 (1.5); 3.327 (24.5); 2.713 (0.4); 2.701 (0.4); 2.525 (0.6); 2.511 (14.0); 2.507 (28.7); 2.502 (38.2); 2.498 (28.2); 2.493 (13.9); 1.989 (0.4); 1.888 (15.6); 1.596 (0.6); 0.008 (2.0); 0.000 (57.6); 0.009 (2.2)

Example I-04

[0308] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0309] =7.369 (1.4); 7.363 (1.5); 7.347 (1.4); 7.341 (1.4); 7.123 (0.5); 7.117 (0.4); 7.102 (1.6); 7.096 (1.5); 7.080 (2.7); 7.075 (1.6); 7.063 (2.1); 7.059 (0.8); 7.042 (0.6); 6.553 (0.6); 6.543 (3.3); 6.516 (3.3); 6.507 (0.6); 6.000 (0.3); 5.987 (0.8); 5.974 (0.7); 5.960 (0.9); 5.957 (0.5); 5.947 (0.4); 5.944 (1.0); 5.930 (0.8); 5.917 (0.9); 5.904 (0.4); 5.363 (0.5); 5.359 (1.5); 5.355 (1.6); 5.351 (0.6); 5.320 (0.5); 5.316 (1.3); 5.311 (1.4); 5.307 (0.6); 5.275 (1.5); 5.271 (1.5); 5.249 (1.4); 5.245 (1.4); 4.499 (1.9); 4.496 (3.3); 4.492 (2.1); 4.486 (2.0); 4.483 (3.2); 4.479 (1.9); 3.645 (15.5); 3.326 (35.9); 3.099 (8.6); 2.671 (0.4); 2.667 (0.3); 2.524 (1.0); 2.511 (24.3); 2.507 (51.0); 2.502 (68.5); 2.497 (50.0); 2.493 (24.2); 2.329 (0.4); 2.300 (0.4); 1.839 (16.0); 0.000 (4.8)

Example I-05

[0310] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0311] =11.852 (0.5); 7.577 (0.5); 7.572 (0.5); 7.388 (0.3); 7.379 (3.3); 7.374 (3.5); 7.368 (0.4); 7.273 (0.4); 7.183 (1.7); 7.178 (1.6); 7.163 (2.2); 7.157 (2.2); 7.082 (2.4); 7.036 (3.6); 7.015 (2.7); 6.619 (0.7); 6.613 (1.1); 6.608 (0.9); 6.592 (0.8); 6.586 (1.1); 6.546 (0.7); 6.539 (0.6); 6.523 (0.8); 6.517 (1.1); 6.512 (0.7); 6.495 (0.7); 6.489 (0.6); 4.734 (2.4); 4.728 (4.2); 4.722 (2.4); 3.819 (1.6); 3.664 (1.5); 3.659 (3.2); 3.652 (2.2); 3.646 (16.0); 3.509 (0.9); 3.338 (42.4); 3.336 (41.4); 3.331 (49.7); 2.707 (0.8); 2.695 (0.8); 2.676 (0.4); 2.671 (0.6); 2.667 (0.4); 2.525 (1.6); 2.511 (31.0); 2.507 (62.8); 2.502 (82.6); 2.498 (60.2); 2.493 (29.7); 2.334 (0.4); 2.329 (0.5); 2.325 (0.4); 1.909 (0.4); 1.891 (15.7); 1.604 (1.8); 1.397 (14.7); 1.235 (0.4); 1.040 (1.2); 0.008 (2.2); 0.000 (61.5); 0.009 (2.3)

Example I-06

[0312] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0313] =7.469 (2.2); 7.146 (0.3); 7.142 (0.4); 7.133 (0.4); 7.128 (0.9); 7.123 (0.7); 7.108 (1.0); 7.103 (0.6); 7.095 (0.5); 7.090 (0.5); 7.057 (0.5); 7.053 (0.6); 7.038 (1.4); 7.034 (1.3); 7.019 (1.0); 7.015 (0.8); 6.986 (1.3); 6.983 (1.5); 6.967 (1.7); 6.965 (1.9); 6.953 (1.2); 6.950 (1.2); 6.946 (0.9); 6.928 (1.3); 6.907 (0.8); 6.482 (0.5); 6.470 (3.6); 6.444 (3.6); 6.432 (0.5); 4.639 (5.6); 4.633 (5.7); 3.653 (16.0); 3.600 (1.5); 3.594 (3.4); 3.588 (1.5); 3.339 (34.7); 3.336 (39.0); 3.332 (44.8); 2.671 (0.4); 2.525 (1.0); 2.511 (22.4); 2.507 (45.3); 2.502 (59.7); 2.498 (43.8); 2.493 (21.7); 2.329 (0.4); 1.962 (11.2); 1.235 (0.5); 0.008 (2.0); 0.000 (60.1); 0.009 (2.3)

Example I-07

[0314] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0315] =7.150 (0.6); 7.145 (0.6); 7.131 (1.3); 7.128 (1.2); 7.126 (1.2); 7.112 (3.8); 7.098 (0.8); 7.094 (0.7); 7.045 (0.7); 7.042 (0.7); 7.027 (1.6); 7.023 (1.6); 7.007 (1.2); 6.974 (1.4); 6.963 (1.8); 6.945 (2.8); 6.927 (1.8); 6.614 (1.3); 6.588 (1.3); 6.506 (0.8); 6.500 (0.7); 6.483 (0.9); 6.478 (1.4); 6.472 (0.8); 6.455 (0.8); 6.449 (0.7); 4.743 (5.8); 4.738 (5.8); 3.805 (0.9); 3.665 (1.7); 3.659 (3.5); 3.653 (2.0); 3.642 (16.0); 3.425 (0.3); 3.338 (12.8); 3.334 (15.1); 2.932 (0.3); 2.507 (16.1); 2.503 (19.9); 1.958 (12.2); 1.587 (0.7); 1.068 (0.6); 0.008 (1.0); 0.000 (19.6); 0.008 (1.0)

Example I-08

[0316] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0317] =7.437 (2.7); 7.348 (3.5); 7.342 (3.7); 7.202 (1.8); 7.197 (1.7); 7.181 (2.3); 7.176 (2.3); 7.045 (3.2); 7.025 (2.5); 6.433 (0.5); 6.422 (3.8); 6.396 (3.7); 6.386 (0.6); 5.966 (0.4); 5.953 (0.8); 5.940 (0.8); 5.927 (0.9); 5.923 (0.5); 5.914 (0.5); 5.910 (1.0); 5.897 (0.9); 5.883 (1.0); 5.870 (0.5); 5.318 (1.6); 5.314 (1.7); 5.310 (0.7); 5.274 (2.0); 5.270 (3.1); 5.267 (2.1); 5.244 (1.5); 5.240 (1.4); 4.433 (1.7); 4.429 (1.9); 4.425 (2.2); 4.420 (2.2); 4.416 (1.9); 4.413 (1.7); 3.659 (16.0); 3.332 (16.0); 2.525 (0.4); 2.512 (9.5); 2.507 (19.1); 2.503 (25.0); 2.498 (18.2); 2.494 (8.9); 1.886 (15.8); 1.397 (2.4); 0.008 (0.7); 0.000 (22.0); 0.009 (0.9)

Example I-09

[0318] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0319] =7.576 (0.5); 7.571 (0.5); 7.465 (2.6); 7.388 (0.3); 7.382 (0.3); 7.366 (3.5); 7.361 (3.8); 7.273 (0.6); 7.252 (0.4); 7.213 (1.7); 7.207 (1.6); 7.192 (2.2); 7.187 (2.2); 7.055 (3.2); 7.034 (2.5); 6.498 (0.5); 6.486 (3.7); 6.461 (3.7); 6.450 (0.5); 4.659 (5.1); 4.653 (5.3); 3.658 (16.0); 3.595 (1.5); 3.589 (3.5); 3.583 (1.6); 3.510 (1.5); 3.331 (28.4); 2.708 (1.1); 2.696 (1.1); 2.525 (0.7); 2.520 (1.1); 2.511 (15.5); 2.507 (31.9); 2.503 (42.5); 2.498 (31.2); 2.494 (15.6); 1.989 (1.3); 1.896 (15.7); 1.604 (3.0); 1.585 (0.5); 1.397 (6.1); 1.193 (0.4); 1.175 (0.7); 1.157 (0.3); 0.008 (1.0); 0.000 (31.7); 0.009 (1.2)

Example I-10

[0320] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0321] =7.400 (1.1); 6.614 (1.6); 6.588 (1.6); 6.329 (2.9); 6.323 (3.1); 6.234 (0.9); 6.229 (1.5); 6.223 (0.8); 4.678 (2.6); 4.673 (2.6); 3.635 (16.0); 3.626 (7.5); 3.602 (0.4); 3.568 (0.7); 3.562 (1.5); 3.557 (0.7); 3.325 (7.9); 2.506 (12.6); 2.502 (15.8); 2.497 (11.7); 2.131 (6.4); 1.989 (1.1); 1.909 (0.8); 1.175 (0.6); 0.008 (0.7); 0.000 (13.7); 0.008 (0.8)

Example I-11

[0322] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0323] =7.352 (1.0); 6.549 (1.5); 6.523 (1.5); 6.309 (2.7); 6.303 (3.1); 6.224 (0.9); 6.219 (1.5); 6.213 (0.7); 5.966 (0.3); 5.939 (0.4); 5.922 (0.4); 5.909 (0.4); 5.896 (0.4); 5.334 (0.7); 5.330 (0.7); 5.291 (0.6); 5.287 (0.6); 5.239 (0.7); 5.235 (0.7); 5.213 (0.6); 5.209 (0.6); 4.435 (0.9); 4.432 (1.5); 4.428 (1.0); 4.422 (0.9); 4.419 (1.5); 4.415 (0.9); 3.638 (16.0); 3.623 (6.7); 3.325 (8.9); 2.511 (5.7); 2.506 (11.7); 2.502 (15.6); 2.497 (11.6); 2.493 (5.8); 2.116 (6.5); 1.989 (1.2); 1.909 (0.6); 1.398 (1.0); 1.193 (0.3); 1.175 (0.7); 1.157 (0.3); 0.008 (0.5); 0.000 (14.8); 0.009 (0.6)

Example I-12

[0324] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0325] =7.100 (0.9); 7.094 (0.9); 6.742 (0.4); 6.737 (0.4); 6.721 (0.3); 6.716 (0.4); 6.710 (0.4); 6.619 (0.3); 6.613 (0.6); 6.313 (2.9); 6.307 (3.2); 6.216 (0.9); 6.210 (1.5); 6.204 (0.7); 5.756 (0.4); 4.756 (2.2); 4.750 (2.3); 3.637 (0.9); 3.631 (2.4); 3.625 (16.0); 3.601 (6.4); 3.327 (2.3); 2.511 (3.5); 2.506 (7.3); 2.502 (9.8); 2.497 (7.2); 2.493 (3.6); 2.127 (6.3); 1.909 (0.4); 0.008 (0.4); 0.000 (11.5); 0.009 (0.4)

Example I-13

[0326] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0327] =7.422 (2.4); 7.149 (0.4); 7.144 (0.4); 7.135 (0.4); 7.130 (0.9); 7.125 (0.8); 7.110 (1.1); 7.105 (0.6); 7.097 (0.5); 7.092 (0.5); 7.055 (0.6); 7.051 (0.6); 7.036 (1.4); 7.032 (1.4); 7.017 (1.1); 7.013 (0.9); 6.980 (1.6); 6.961 (2.0); 6.951 (1.2); 6.945 (0.9); 6.943 (0.9); 6.927 (1.4); 6.905 (0.9); 6.429 (0.5); 6.417 (3.7); 6.391 (3.7); 6.380 (0.5); 5.952 (0.3); 5.939 (0.7); 5.926 (0.7); 5.913 (0.8); 5.900 (0.5); 5.896 (0.9); 5.883 (0.8); 5.870 (0.9); 5.857 (0.4); 5.308 (1.5); 5.304 (1.6); 5.265 (1.3); 5.261 (1.4); 5.245 (1.6); 5.241 (1.5); 5.219 (1.4); 5.215 (1.4); 4.397 (3.5); 4.384 (3.4); 3.650 (16.0); 3.329 (57.1); 2.676 (0.4); 2.671 (0.5); 2.667 (0.4); 2.506 (59.7); 2.502 (76.7); 2.498 (56.3); 2.333 (0.4); 2.329 (0.5); 2.325 (0.4); 1.954 (12.0); 0.146 (0.3); 0.008 (3.0); 0.000 (72.5); 0.008 (2.9); 0.150 (0.3)

Example I-14

[0328] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0329] =7.502 (1.6); 7.083 (0.4); 7.062 (0.9); 7.045 (0.9); 7.041 (0.6); 7.023 (0.5); 6.972 (0.5); 6.966 (0.5); 6.948 (0.8); 6.941 (0.8); 6.923 (0.5); 6.917 (0.5); 6.886 (0.5); 6.880 (0.4); 6.865 (0.9); 6.859 (0.7); 6.843 (0.4); 6.837 (0.3); 6.503 (2.5); 6.478 (2.5); 6.466 (0.3); 4.667 (3.8); 4.661 (3.8); 3.652 (10.5); 3.573 (1.0); 3.567 (2.2); 3.561 (1.0); 3.327 (17.2); 2.525 (0.4); 2.520 (0.6); 2.511 (8.9); 2.507 (18.3); 2.502 (24.7); 2.498 (18.5); 2.493 (9.3); 1.989 (0.5); 1.943 (7.9); 1.398 (16.0); 0.008 (0.7); 0.000 (22.0); 0.009 (0.8)

Example I-15

[0330] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0331] =7.463 (2.8); 7.074 (0.6); 7.053 (1.4); 7.036 (1.4); 7.014 (0.7); 6.970 (0.7); 6.964 (0.8); 6.946 (1.3); 6.939 (1.4); 6.922 (0.7); 6.915 (0.8); 6.880 (0.8); 6.874 (0.7); 6.859 (1.4); 6.853 (1.2); 6.838 (0.7); 6.832 (0.6); 6.458 (0.6); 6.446 (3.9); 6.420 (3.8); 6.409 (0.6); 5.954 (0.3); 5.941 (0.7); 5.928 (0.7); 5.915 (0.8); 5.911 (0.5); 5.898 (0.9); 5.885 (0.8); 5.872 (0.9); 5.859 (0.4); 5.304 (1.5); 5.300 (1.7); 5.261 (1.4); 5.257 (1.6); 5.252 (1.4); 5.249 (1.8); 5.245 (1.6); 5.223 (1.5); 5.219 (1.5); 4.430 (3.7); 4.417 (3.7); 3.650 (16.0); 3.328 (26.3); 2.507 (30.2); 2.502 (39.7); 2.498 (30.6); 1.934 (13.2); 0.008 (1.4); 0.000 (30.9)

Example I-16

[0332] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0333] =7.155 (2.3); 7.151 (2.3); 7.056 (0.6); 7.038 (0.8); 7.034 (1.4); 7.017 (1.4); 7.013 (0.9); 6.996 (1.3); 6.990 (0.8); 6.972 (1.2); 6.966 (1.3); 6.948 (0.7); 6.941 (0.7); 6.855 (0.7); 6.849 (0.7); 6.833 (1.2); 6.827 (1.2); 6.812 (0.6); 6.806 (0.5); 6.654 (0.7); 6.649 (1.1); 6.644 (0.9); 6.627 (0.8); 6.623 (1.1); 6.617 (0.8); 6.543 (0.7); 6.536 (0.6); 6.520 (0.8); 6.514 (1.2); 6.508 (0.7); 6.492 (0.7); 6.485 (0.6); 4.762 (5.3); 4.756 (5.5); 4.038 (0.9); 4.020 (0.9); 3.676 (1.5); 3.670 (3.4); 3.664 (1.5); 3.639 (16.0); 3.506 (0.7); 3.327 (30.9); 2.671 (0.3); 2.525 (0.8); 2.520 (1.2); 2.511 (17.9); 2.507 (36.6); 2.502 (49.3); 2.498 (36.8); 2.493 (18.4); 2.329 (0.3); 1.989 (4.1); 1.937 (10.8); 1.908 (2.8); 1.398 (3.8); 1.193 (1.1); 1.175 (2.2); 1.157 (1.1); 0.008 (1.3); 0.000 (41.3); 0.009 (1.5)

Example I-17

[0334] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0335] =7.387 (2.2); 6.941 (0.9); 6.920 (1.8); 6.899 (1.0); 6.580 (3.0); 6.555 (3.1); 6.510 (0.4); 6.497 (3.2); 6.472 (3.2); 6.459 (0.4); 4.652 (4.9); 4.646 (5.0); 3.678 (16.0); 3.636 (13.0); 3.577 (1.3); 3.571 (2.7); 3.565 (1.2); 3.329 (9.1); 2.507 (13.1); 2.502 (17.4); 2.498 (13.1); 1.939 (10.4); 0.008 (0.6); 0.000 (15.4); 0.008 (0.6)

Example I-18

[0336] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0337] =7.355 (2.3); 6.925 (0.9); 6.904 (1.8); 6.883 (1.1); 6.566 (3.5); 6.541 (2.6); 6.535 (0.9); 6.445 (0.4); 6.433 (3.3); 6.407 (3.2); 6.395 (0.5); 5.950 (0.6); 5.937 (0.6); 5.924 (0.7); 5.920 (0.5); 5.907 (0.8); 5.894 (0.7); 5.881 (0.8); 5.868 (0.4); 5.315 (1.3); 5.311 (1.4); 5.271 (1.2); 5.267 (1.3); 5.245 (1.3); 5.241 (1.3); 5.218 (1.3); 5.215 (1.3); 4.411 (3.1); 4.398 (3.0); 3.673 (16.0); 3.637 (13.0); 3.329 (9.9); 2.524 (0.3); 2.507 (13.8); 2.502 (18.4); 2.498 (14.1); 1.928 (10.6); 1.909 (0.5); 0.008 (0.6); 0.000 (16.5); 0.008 (0.7)

Example I-19

[0338] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0339] =7.020 (2.3); 7.016 (2.3); 6.932 (1.1); 6.910 (2.2); 6.889 (1.3); 6.649 (0.8); 6.644 (1.1); 6.622 (0.8); 6.617 (1.1); 6.612 (1.0); 6.606 (1.4); 6.600 (1.6); 6.577 (1.1); 6.571 (1.6); 6.555 (1.7); 6.549 (1.3); 6.534 (2.0); 6.528 (1.8); 6.512 (0.8); 6.506 (1.2); 6.500 (0.8); 6.484 (0.7); 6.477 (0.6); 5.757 (0.5); 4.753 (4.9); 4.747 (5.0); 3.683 (16.0); 3.668 (1.9); 3.662 (3.2); 3.656 (1.7); 3.624 (12.9); 3.330 (14.0); 2.507 (15.3); 2.502 (19.9); 2.498 (15.6); 1.935 (9.7); 1.910 (0.8); 0.008 (0.8); 0.000 (15.0)

Example I-20

[0340] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0341] =8.176 (2.6); 8.170 (2.8); 7.595 (2.5); 7.588 (2.5); 7.582 (1.7); 7.567 (1.9); 7.561 (1.9); 7.341 (3.1); 7.320 (2.6); 6.634 (0.5); 6.621 (3.8); 6.595 (3.8); 6.582 (0.5); 5.757 (3.4); 4.692 (5.8); 4.686 (6.0); 3.633 (16.0); 3.571 (1.5); 3.565 (3.4); 3.559 (1.5); 3.328 (52.1); 2.671 (0.4); 2.667 (0.3); 2.524 (1.0); 2.507 (48.9); 2.502 (64.6); 2.498 (48.9); 2.329 (0.4); 2.325 (0.3); 2.116 (15.5); 1.989 (0.6); 1.909 (0.4); 0.008 (2.2); 0.000 (60.1); 0.008 (2.6)

Example I-21

[0342] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0343] =8.135 (2.5); 8.129 (2.6); 7.559 (2.4); 7.555 (3.0); 7.548 (1.8); 7.534 (2.0); 7.528 (2.0); 7.321 (2.9); 7.319 (2.9); 7.300 (2.5); 7.299 (2.5); 6.568 (0.5); 6.556 (3.8); 6.530 (3.7); 6.518 (0.5); 5.979 (0.4); 5.966 (0.8); 5.953 (0.7); 5.940 (0.9); 5.936 (0.5); 5.926 (0.5); 5.923 (1.0); 5.910 (0.8); 5.896 (0.9); 5.883 (0.5); 5.757 (2.3); 5.334 (0.5); 5.330 (1.5); 5.326 (1.7); 5.322 (0.6); 5.291 (0.5); 5.287 (1.4); 5.283 (1.5); 5.279 (0.6); 5.257 (0.7); 5.254 (1.6); 5.250 (1.5); 5.228 (1.4); 5.224 (1.4); 4.451 (2.0); 4.448 (3.4); 4.444 (2.2); 4.438 (2.1); 4.435 (3.4); 4.431 (2.0); 3.636 (16.0); 3.327 (60.3); 2.676 (0.4); 2.671 (0.5); 2.667 (0.4); 2.525 (1.2); 2.520 (1.8); 2.511 (27.5); 2.507 (56.3); 2.502 (75.0); 2.498 (55.5); 2.493 (27.6); 2.334 (0.4); 2.329 (0.5); 2.325 (0.4); 2.098 (15.6); 1.909 (0.4); 0.146 (0.4); 0.008 (2.8); 0.000 (83.2); 0.009 (2.9); 0.150 (0.4)

Example I-22

[0344] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0345] =7.035 (2.8); 7.032 (2.7); 6.915 (1.4); 6.893 (2.8); 6.872 (1.6); 6.641 (1.0); 6.637 (1.3); 6.610 (2.8); 6.604 (2.7); 6.580 (1.4); 6.574 (2.0); 6.562 (2.2); 6.555 (1.5); 6.541 (1.7); 6.534 (1.5); 6.521 (0.8); 6.515 (0.7); 6.498 (1.0); 6.493 (1.4); 6.487 (0.9); 6.470 (0.8); 6.464 (0.7); 6.027 (0.4); 6.014 (0.8); 6.000 (0.8); 5.987 (1.0); 5.984 (0.6); 5.974 (0.6); 5.970 (1.0); 5.957 (0.9); 5.944 (1.0); 5.931 (0.5); 5.359 (1.7); 5.355 (1.8); 5.316 (1.5); 5.312 (1.6); 5.265 (1.8); 5.261 (1.7); 5.238 (1.7); 5.235 (1.6); 4.749 (6.0); 4.743 (6.0); 4.505 (4.0); 4.492 (3.9); 3.670 (1.7); 3.664 (3.5); 3.658 (1.7); 3.626 (16.0); 3.332 (22.9); 2.507 (20.7); 2.503 (26.6); 2.498 (20.0); 2.142 (0.6); 1.933 (12.4); 1.909 (0.5); 0.008 (2.1); 0.000 (44.2)

Example I-23

[0346] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0347] =7.372 (2.6); 6.915 (1.0); 6.892 (2.2); 6.878 (0.5); 6.871 (1.4); 6.580 (2.2); 6.573 (4.9); 6.556 (1.9); 6.552 (2.1); 6.545 (2.1); 6.539 (1.1); 6.448 (0.5); 6.426 (4.0); 6.400 (3.7); 6.388 (0.5); 6.021 (0.5); 6.008 (0.9); 5.995 (0.9); 5.990 (0.4); 5.982 (1.1); 5.978 (0.7); 5.969 (0.8); 5.965 (1.2); 5.961 (0.7); 5.952 (1.1); 5.948 (1.1); 5.939 (1.3); 5.935 (1.0); 5.930 (0.5); 5.926 (0.8); 5.922 (1.1); 5.918 (0.7); 5.913 (0.4); 5.909 (0.7); 5.905 (1.1); 5.900 (0.3); 5.892 (0.9); 5.887 (0.3); 5.878 (1.0); 5.866 (0.5); 5.761 (0.6); 5.754 (2.2); 5.365 (1.2); 5.361 (2.0); 5.357 (1.8); 5.353 (0.7); 5.322 (2.2); 5.318 (3.6); 5.314 (3.3); 5.310 (1.2); 5.279 (1.2); 5.275 (2.0); 5.270 (2.0); 5.266 (1.4); 5.264 (1.5); 5.260 (2.2); 5.256 (2.0); 5.252 (1.2); 5.246 (1.6); 5.242 (2.6); 5.238 (2.6); 5.234 (2.3); 5.229 (1.8); 5.226 (1.1); 5.219 (1.2); 5.216 (1.9); 5.212 (1.5); 5.208 (0.6); 4.486 (3.3); 4.482 (4.3); 4.478 (3.2); 4.473 (3.1); 4.469 (3.7); 4.407 (3.3); 4.403 (4.4); 4.399 (3.3); 4.394 (3.1); 4.390 (3.7); 4.387 (2.0); 3.648 (5.0); 3.640 (16.0); 3.385 (40.0); 3.366 (35.4); 3.357 (45.4); 2.514 (14.9); 2.509 (21.5); 2.505 (23.9); 2.500 (15.8); 2.496 (7.1); 1.929 (12.8); 1.920 (2.0); 1.911 (6.4); 0.008 (7.9); 0.000 (31.5); 0.009 (1.2)

Example I-24

[0348] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0349] =7.399 (2.7); 6.930 (1.0); 6.908 (2.2); 6.887 (1.4); 6.588 (4.4); 6.562 (3.0); 6.556 (1.1); 6.504 (0.5); 6.492 (4.0); 6.466 (4.0); 6.454 (0.5); 6.029 (0.4); 6.016 (0.8); 6.003 (0.8); 5.989 (0.9); 5.976 (0.5); 5.973 (0.9); 5.959 (0.9); 5.946 (0.9); 5.933 (0.5); 5.369 (1.6); 5.365 (1.7); 5.326 (1.4); 5.322 (1.4); 5.266 (1.7); 5.263 (1.6); 5.240 (1.6); 5.236 (1.5); 4.643 (6.1); 4.637 (6.2); 4.491 (3.7); 4.478 (3.7); 3.637 (16.0); 3.573 (1.6); 3.568 (3.5); 3.562 (1.6); 3.331 (37.2); 2.525 (0.6); 2.507 (25.9); 2.503 (33.8); 2.498 (25.2); 1.989 (0.5); 1.939 (13.1); 1.398 (2.5); 0.008 (2.0); 0.000 (48.9); 0.008 (2.0)

Example I-25

[0350] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0351] =8.369 (2.8); 8.364 (2.8); 7.819 (1.8); 7.812 (1.8); 7.798 (2.0); 7.792 (2.0); 7.484 (3.0); 7.464 (2.7); 6.836 (0.8); 6.829 (1.1); 6.826 (1.0); 6.809 (0.8); 6.802 (1.2); 6.786 (0.8); 6.780 (0.6); 6.763 (1.1); 6.760 (1.2); 6.737 (0.8); 6.730 (0.6); 6.590 (3.6); 5.756 (6.4); 4.800 (5.5); 4.794 (5.7); 3.639 (1.5); 3.633 (3.3); 3.628 (1.5); 3.569 (16.0); 3.328 (27.9); 2.506 (30.4); 2.502 (39.9); 2.498 (30.2); 2.206 (15.5); 1.989 (0.9); 1.909 (0.7); 1.175 (0.5); 0.008 (1.8); 0.000 (44.3); 0.008 (2.0)

Example I-26

[0352] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0353] =7.037 (2.5); 7.033 (2.5); 6.953 (1.4); 6.932 (2.8); 6.910 (1.6); 6.669 (1.5); 6.663 (1.7); 6.640 (2.2); 6.634 (2.7); 6.616 (0.9); 6.607 (2.8); 6.601 (1.7); 6.586 (1.6); 6.579 (1.4); 6.530 (0.8); 6.524 (0.7); 6.508 (0.9); 6.502 (1.3); 6.495 (0.8); 6.479 (0.8); 6.473 (0.7); 5.757 (1.0); 4.749 (5.9); 4.743 (6.0); 4.733 (6.4); 4.727 (6.3); 3.665 (1.7); 3.659 (3.7); 3.653 (1.7); 3.623 (16.0); 3.584 (1.7); 3.578 (3.7); 3.572 (1.6); 3.338 (20.5); 2.520 (0.5); 2.512 (7.3); 2.507 (14.9); 2.503 (19.7); 2.498 (14.2); 2.494 (6.9); 1.940 (11.3); 0.000 (3.1)

Example I-27

[0354] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0355] =7.396 (2.6); 6.973 (1.3); 6.952 (2.5); 6.940 (0.4); 6.929 (1.3); 6.658 (1.2); 6.652 (1.9); 6.637 (1.6); 6.634 (1.8); 6.628 (1.8); 6.622 (1.8); 6.617 (2.3); 6.611 (1.1); 6.516 (0.5); 6.503 (4.0); 6.478 (3.9); 6.465 (0.5); 4.721 (6.1); 4.715 (6.2); 4.650 (6.1); 4.644 (6.3); 3.631 (16.0); 3.579 (1.7); 3.573 (4.2); 3.565 (4.1); 3.559 (1.7); 3.329 (43.4); 2.671 (0.4); 2.525 (0.8); 2.511 (20.2); 2.507 (41.1); 2.502 (54.2); 2.498 (39.8); 2.493 (19.8); 2.329 (0.4); 1.989 (0.7); 1.947 (12.5); 1.908 (0.5); 1.398 (9.1); 1.175 (0.4); 0.000 (6.6)

Example I-28

[0356] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0357] =7.365 (2.5); 6.952 (1.2); 6.931 (2.3); 6.915 (0.4); 6.908 (1.1); 6.639 (1.2); 6.633 (1.9); 6.622 (1.6); 6.619 (1.7); 6.609 (1.5); 6.602 (3.4); 6.595 (1.1); 6.447 (0.5); 6.435 (3.9); 6.409 (3.9); 6.397 (0.5); 5.969 (0.4); 5.956 (0.8); 5.943 (0.8); 5.930 (1.0); 5.926 (0.6); 5.917 (0.5); 5.913 (1.0); 5.900 (0.9); 5.887 (1.0); 5.873 (0.5); 5.330 (0.6); 5.326 (1.7); 5.322 (1.8); 5.318 (0.7); 5.287 (0.5); 5.283 (1.5); 5.279 (1.6); 5.275 (0.7); 5.253 (0.7); 5.250 (1.7); 5.246 (1.7); 5.227 (0.7); 5.224 (1.6); 5.220 (1.6); 4.712 (6.0); 4.706 (6.2); 4.412 (2.2); 4.408 (3.8); 4.405 (2.4); 4.399 (2.3); 4.395 (3.6); 4.392 (2.2); 3.632 (16.0); 3.585 (1.7); 3.579 (3.8); 3.573 (1.7); 3.330 (45.5); 2.671 (0.4); 2.524 (0.8); 2.520 (1.3); 2.511 (19.4); 2.507 (40.0); 2.502 (53.3); 2.498 (39.2); 2.493 (19.4); 2.329 (0.4); 2.183 (0.4); 1.989 (0.9); 1.935 (12.6); 1.909 (2.5); 1.355 (3.3); 1.193 (0.4); 1.175 (0.6); 1.169 (1.1); 0.008 (0.4); 0.000 (13.4); 0.009 (0.5)

Example I-29

[0358] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0359] =7.451 (2.6); 7.449 (2.6); 7.367 (1.6); 7.361 (1.7); 7.345 (1.7); 7.338 (1.7); 7.229 (1.2); 7.213 (1.4); 7.208 (2.0); 7.192 (1.8); 7.142 (1.1); 7.135 (1.0); 7.121 (1.8); 7.114 (1.6); 7.099 (0.7); 7.093 (0.7); 6.767 (1.5); 6.760 (1.5); 6.734 (1.5); 6.727 (1.5); 6.492 (1.0); 6.487 (0.9); 6.470 (1.3); 6.464 (1.3); 6.371 (1.6); 6.347 (2.0); 6.324 (1.2); 5.757 (1.7); 4.640 (6.1); 4.634 (6.2); 3.582 (16.0); 3.526 (1.6); 3.521 (3.6); 3.515 (1.6); 3.331 (46.3); 2.525 (0.6); 2.511 (15.6); 2.507 (31.1); 2.503 (40.8); 2.498 (30.2); 2.494 (15.3); 2.006 (15.5); 0.008 (0.5); 0.000 (15.1); 0.008 (0.6)

Example I-30

[0360] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0361] =8.317 (0.4); 7.489 (3.7); 7.463 (0.4); 7.408 (1.5); 7.402 (1.6); 7.386 (1.6); 7.379 (1.5); 7.199 (0.9); 7.182 (1.2); 7.177 (2.2); 7.161 (2.0); 7.149 (1.3); 7.142 (1.2); 7.128 (1.8); 7.121 (1.6); 7.106 (0.6); 7.100 (0.6); 6.675 (0.4); 6.666 (3.9); 6.661 (1.5); 6.649 (1.4); 6.644 (4.8); 6.635 (0.9); 6.612 (0.5); 6.446 (0.5); 6.437 (4.8); 6.420 (1.3); 6.415 (4.2); 6.017 (0.3); 6.004 (0.7); 5.991 (0.7); 5.978 (0.8); 5.974 (0.5); 5.965 (0.5); 5.961 (0.9); 5.948 (0.8); 5.935 (0.9); 5.922 (0.4); 5.757 (0.5); 5.344 (0.5); 5.340 (1.4); 5.336 (1.6); 5.332 (0.7); 5.297 (1.3); 5.293 (1.4); 5.288 (0.6); 5.212 (1.4); 5.208 (1.4); 5.186 (1.3); 5.182 (1.3); 4.392 (3.5); 4.389 (2.3); 4.383 (2.2); 4.379 (3.4); 3.853 (0.4); 3.836 (0.4); 3.536 (15.5); 3.329 (61.0); 2.675 (0.3); 2.671 (0.5); 2.667 (0.4); 2.524 (1.5); 2.511 (28.5); 2.507 (57.1); 2.502 (75.3); 2.498 (56.6); 2.333 (0.4); 2.329 (0.5); 2.325 (0.4); 2.044 (0.4); 2.008 (16.0); 1.252 (0.5); 1.235 (1.2); 1.218 (0.5); 0.146 (0.5); 0.008 (4.4); 0.000 (113.6); 0.008 (5.4); 0.020 (0.4); 0.150 (0.5)

Example I-31

[0362] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0363] =7.541 (4.0); 7.415 (1.6); 7.409 (1.7); 7.393 (1.6); 7.386 (1.6); 7.208 (1.0); 7.191 (1.2); 7.186 (2.2); 7.170 (2.1); 7.156 (1.3); 7.150 (1.2); 7.135 (1.8); 7.128 (1.6); 7.114 (0.6); 7.107 (0.6); 6.719 (0.4); 6.710 (4.3); 6.705 (1.5); 6.693 (1.6); 6.688 (5.1); 6.679 (0.5); 6.458 (0.5); 6.450 (5.1); 6.444 (1.7); 6.433 (1.5); 6.427 (4.4); 6.419 (0.4); 5.757 (3.3); 4.605 (6.4); 4.600 (6.5); 3.920 (0.4); 3.818 (0.5); 3.539 (16.0); 3.491 (1.6); 3.485 (3.4); 3.479 (1.6); 3.332 (74.2); 2.672 (0.3); 2.525 (0.9); 2.511 (19.3); 2.507 (38.3); 2.502 (49.9); 2.498 (37.2); 2.494 (18.9); 2.183 (0.7); 2.012 (15.4); 1.039 (0.4); 0.008 (0.9); 0.000 (23.2); 0.008 (1.0)

Example I-32

[0364] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0365] =7.397 (1.6); 7.391 (1.7); 7.375 (1.7); 7.368 (1.6); 7.283 (1.3); 7.266 (1.5); 7.261 (1.9); 7.245 (1.8); 7.203 (4.1); 7.160 (1.1); 7.154 (1.0); 7.139 (1.8); 7.133 (1.6); 7.118 (0.8); 7.111 (0.7); 6.936 (3.4); 6.929 (3.6); 6.669 (1.6); 6.662 (1.5); 6.647 (1.8); 6.640 (1.7); 6.312 (3.5); 6.290 (3.2); 5.756 (2.3); 4.659 (6.2); 4.653 (6.2); 3.571 (16.0); 3.529 (1.7); 3.523 (3.6); 3.518 (1.6); 3.331 (51.8); 2.525 (0.9); 2.511 (18.5); 2.507 (36.7); 2.503 (47.7); 2.498 (34.9); 2.494 (17.3); 2.028 (15.6); 0.008 (0.3); 0.000 (9.1); 0.008 (0.3)

Example I-33

[0366] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0367] =7.754 (2.5); 7.403 (1.6); 7.396 (1.6); 7.381 (1.7); 7.374 (1.6); 7.259 (1.2); 7.243 (1.4); 7.237 (1.9); 7.221 (1.8); 7.171 (1.1); 7.164 (1.0); 7.149 (1.7); 7.143 (1.6); 7.128 (0.7); 7.122 (0.7); 7.073 (1.2); 7.054 (1.2); 7.042 (1.2); 7.022 (1.2); 6.240 (1.2); 6.220 (1.3); 6.209 (1.3); 6.188 (1.3); 5.757 (4.3); 4.713 (6.0); 4.707 (6.1); 3.627 (0.4); 3.614 (16.0); 3.573 (1.6); 3.567 (3.4); 3.561 (1.6); 3.344 (0.9); 3.332 (46.4); 3.315 (0.4); 2.525 (0.9); 2.512 (16.6); 2.507 (33.0); 2.503 (43.3); 2.498 (32.0); 2.494 (16.3); 2.021 (15.5); 1.397 (0.5); 0.000 (1.6)

Example I-34

[0368] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0369] =7.688 (2.4); 7.394 (1.6); 7.387 (1.7); 7.372 (1.7); 7.365 (1.7); 7.249 (1.2); 7.233 (1.3); 7.227 (2.0); 7.211 (1.8); 7.162 (1.1); 7.156 (1.0); 7.141 (1.7); 7.134 (1.6); 7.120 (0.7); 7.113 (0.7); 6.998 (1.2); 6.979 (1.2); 6.967 (1.2); 6.947 (1.2); 6.242 (1.2); 6.221 (1.3); 6.210 (1.3); 6.190 (1.3); 5.986 (0.4); 5.972 (0.8); 5.959 (0.7); 5.946 (0.9); 5.943 (0.6); 5.932 (0.5); 5.929 (1.0); 5.916 (0.8); 5.903 (0.9); 5.889 (0.5); 5.758 (3.2); 5.336 (0.5); 5.332 (1.5); 5.328 (1.7); 5.324 (0.7); 5.293 (0.5); 5.289 (1.3); 5.285 (1.5); 5.281 (0.6); 5.241 (1.5); 5.237 (1.5); 5.215 (1.4); 5.211 (1.4); 4.472 (3.4); 4.459 (3.4); 3.648 (0.3); 3.612 (16.0); 3.367 (0.7); 3.331 (33.0); 2.548 (0.5); 2.543 (0.8); 2.539 (0.8); 2.534 (0.5); 2.512 (15.4); 2.507 (31.6); 2.503 (42.2); 2.498 (31.5); 2.494 (16.3); 2.050 (0.3); 2.014 (15.5); 1.235 (0.7); 0.000 (1.6)

Example I-35

[0370] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0371] =7.760 (3.5); 7.429 (1.5); 7.422 (1.6); 7.406 (1.6); 7.400 (1.5); 7.220 (0.9); 7.203 (1.1); 7.198 (2.2); 7.182 (2.0); 7.170 (1.3); 7.164 (1.1); 7.149 (1.7); 7.143 (1.5); 7.128 (0.6); 7.121 (0.5); 6.874 (1.3); 6.851 (2.2); 6.828 (1.4); 6.317 (1.4); 6.311 (1.6); 6.284 (1.3); 6.277 (1.7); 6.239 (1.1); 6.237 (1.3); 6.233 (1.1); 6.217 (1.1); 6.215 (1.2); 6.211 (1.0); 6.008 (0.4); 5.995 (0.8); 5.982 (0.7); 5.968 (0.9); 5.965 (0.6); 5.955 (0.5); 5.952 (1.0); 5.938 (0.8); 5.925 (0.9); 5.912 (0.4); 5.757 (2.5); 5.340 (0.6); 5.336 (1.6); 5.332 (1.7); 5.328 (0.7); 5.297 (0.5); 5.293 (1.4); 5.289 (1.4); 5.285 (0.6); 5.225 (1.5); 5.221 (1.5); 5.199 (1.4); 5.195 (1.4); 4.441 (3.6); 4.427 (3.6); 3.561 (16.0); 3.331 (40.5); 2.525 (0.7); 2.511 (15.3); 2.507 (30.5); 2.503 (40.0); 2.498 (29.7); 2.018 (15.6); 1.397 (0.4); 0.146 (0.7); 0.008 (6.2); 0.000 (129.2); 0.009 (6.7); 0.150 (0.7)

Example I-36

[0372] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0373] =7.818 (3.6); 7.435 (1.5); 7.428 (1.6); 7.413 (1.6); 7.406 (1.6); 7.228 (0.9); 7.212 (1.2); 7.207 (2.1); 7.191 (2.0); 7.177 (1.3); 7.170 (1.1); 7.155 (1.7); 7.149 (1.5); 7.134 (0.6); 7.128 (0.5); 6.947 (1.3); 6.924 (2.3); 6.901 (1.4); 6.322 (1.3); 6.315 (1.6); 6.289 (1.2); 6.282 (1.7); 6.260 (1.3); 6.254 (1.0); 6.238 (1.2); 6.234 (1.0); 5.757 (4.0); 4.661 (6.2); 4.655 (6.4); 3.564 (16.0); 3.535 (1.6); 3.529 (3.3); 3.523 (1.6); 3.332 (69.8); 2.672 (0.3); 2.525 (0.9); 2.511 (20.5); 2.507 (40.8); 2.503 (53.7); 2.498 (39.8); 2.329 (0.3); 2.021 (15.4); 1.398 (0.4); 0.146 (0.9); 0.022 (0.5); 0.008 (7.8); 0.000 (164.2); 0.009 (8.6); 0.150 (0.9)

Example I-37

[0374] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0375] =7.743 (2.4); 7.740 (2.4); 7.426 (1.6); 7.420 (1.7); 7.404 (1.7); 7.397 (1.7); 7.293 (1.3); 7.278 (1.4); 7.272 (1.9); 7.256 (1.8); 7.189 (1.1); 7.182 (1.0); 7.168 (1.8); 7.161 (1.6); 7.146 (0.8); 7.140 (0.7); 6.945 (1.5); 6.923 (1.6); 6.917 (1.6); 6.895 (1.6); 6.187 (0.8); 6.179 (1.5); 6.171 (0.9); 6.164 (0.8); 6.157 (1.3); 6.148 (0.8); 5.967 (0.4); 5.954 (0.8); 5.941 (0.7); 5.927 (0.9); 5.924 (0.5); 5.915 (0.5); 5.911 (1.0); 5.897 (0.8); 5.884 (1.0); 5.871 (0.5); 5.856 (1.5); 5.849 (1.5); 5.838 (1.5); 5.830 (1.4); 5.757 (2.6); 5.298 (0.6); 5.294 (1.6); 5.290 (1.7); 5.286 (0.7); 5.251 (1.4); 5.247 (1.5); 5.243 (0.6); 5.201 (1.6); 5.197 (1.5); 5.174 (1.5); 5.170 (1.4); 4.321 (3.5); 4.317 (2.4); 4.311 (2.3); 4.308 (3.5); 3.593 (16.0); 3.330 (46.4); 2.525 (0.7); 2.511 (17.8); 2.507 (35.9); 2.503 (47.1); 2.498 (34.9); 2.494 (17.6); 2.047 (15.9); 1.235 (0.4); 0.146 (0.4); 0.008 (3.5); 0.000 (89.7); 0.009 (4.0); 0.150 (0.4)

Example I-38

[0376] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0377] =7.767 (2.4); 7.763 (2.4); 7.424 (1.6); 7.418 (1.7); 7.402 (1.7); 7.396 (1.6); 7.296 (1.3); 7.280 (1.4); 7.275 (1.9); 7.259 (1.8); 7.189 (1.1); 7.183 (1.0); 7.168 (1.7); 7.161 (1.6); 7.147 (0.7); 7.140 (0.7); 6.982 (1.5); 6.960 (1.6); 6.954 (1.6); 6.932 (1.6); 6.246 (0.8); 6.238 (1.5); 6.230 (0.9); 6.224 (0.8); 6.216 (1.3); 6.208 (0.7); 5.893 (1.5); 5.885 (1.5); 5.874 (1.5); 5.867 (1.4); 5.757 (3.7); 4.559 (4.2); 3.590 (16.0); 3.520 (1.6); 3.515 (3.4); 3.509 (1.6); 3.332 (66.9); 2.525 (0.9); 2.512 (17.8); 2.507 (36.2); 2.503 (47.7); 2.498 (34.9); 2.494 (17.2); 2.044 (15.8); 1.398 (0.5); 0.146 (0.5); 0.008 (3.4); 0.000 (92.0); 0.008 (3.7); 0.150 (0.5)

Example I-39

[0378] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0379] =7.783 (2.8); 7.570 (3.3); 7.564 (3.5); 7.362 (1.7); 7.356 (1.6); 7.341 (2.2); 7.335 (2.2); 7.230 (3.9); 7.210 (2.9); 7.083 (1.2); 7.063 (1.3); 7.052 (1.3); 7.032 (1.2); 6.239 (1.3); 6.218 (1.3); 6.207 (1.3); 6.187 (1.3); 5.758 (4.3); 4.715 (6.0); 4.710 (6.2); 3.613 (16.0); 3.578 (1.6); 3.572 (3.2); 3.567 (1.6); 3.332 (39.1); 2.508 (31.7); 2.503 (41.5); 2.499 (31.5); 2.027 (15.6); 1.397 (0.4); 0.008 (1.2); 0.000 (32.9)

Example I-40

[0380] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0381] =7.566 (3.3); 7.560 (3.6); 7.351 (1.6); 7.346 (1.5); 7.330 (2.3); 7.325 (2.3); 7.253 (4.1); 7.237 (4.7); 7.233 (4.0); 6.944 (3.3); 6.937 (3.5); 6.673 (1.6); 6.666 (1.5); 6.651 (1.8); 6.644 (1.7); 6.307 (3.3); 6.284 (3.0); 5.757 (2.2); 4.661 (6.2); 4.655 (6.4); 3.569 (16.0); 3.533 (1.7); 3.528 (3.4); 3.522 (1.7); 3.333 (96.3); 2.672 (0.5); 2.507 (57.5); 2.503 (73.6); 2.499 (56.2); 2.330 (0.5); 2.035 (15.7); 1.397 (0.9); 1.235 (0.5); 0.008 (0.9); 0.000 (20.6)

Example I-41

[0382] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0383] =7.389 (1.5); 7.383 (1.6); 7.367 (1.6); 7.361 (1.5); 7.273 (1.3); 7.257 (1.5); 7.252 (2.0); 7.236 (1.8); 7.155 (4.6); 7.147 (1.3); 7.132 (2.1); 7.126 (1.7); 7.111 (0.8); 7.104 (0.7); 6.870 (3.0); 6.863 (3.2); 6.833 (0.4); 6.826 (0.4); 6.632 (1.4); 6.625 (1.4); 6.610 (1.6); 6.603 (1.7); 6.312 (3.2); 6.290 (2.9); 5.993 (0.3); 5.980 (0.7); 5.967 (0.7); 5.954 (0.8); 5.951 (0.5); 5.937 (0.8); 5.924 (0.7); 5.911 (0.8); 5.898 (0.4); 5.757 (1.8); 5.331 (1.4); 5.327 (1.5); 5.288 (1.3); 5.284 (1.3); 5.223 (1.5); 5.220 (1.4); 5.197 (1.4); 5.193 (1.4); 4.427 (3.4); 4.414 (3.3); 3.878 (0.5); 3.860 (0.5); 3.570 (15.3); 3.330 (23.9); 2.507 (28.6); 2.503 (36.6); 2.498 (27.5); 2.022 (16.0); 1.245 (0.5); 1.227 (1.1); 1.210 (0.5); 0.007 (2.0); 0.000 (43.0)

Example I-42

[0384] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0385] =7.370 (1.3); 7.364 (1.4); 7.349 (1.4); 7.343 (1.4); 7.067 (0.5); 7.046 (2.0); 7.035 (1.4); 7.029 (2.9); 7.014 (1.5); 7.008 (1.4); 6.993 (0.4); 6.987 (0.4); 6.957 (2.4); 6.596 (1.0); 6.569 (1.0); 6.542 (0.7); 6.536 (0.6); 6.519 (0.8); 6.515 (1.0); 6.509 (0.7); 6.493 (0.7); 6.486 (0.6); 5.757 (0.9); 4.724 (2.4); 4.718 (4.4); 4.712 (2.6); 3.825 (0.4); 3.653 (16.0); 3.510 (0.7); 3.330 (38.5); 2.715 (0.5); 2.704 (0.5); 2.672 (0.4); 2.525 (0.9); 2.507 (42.3); 2.502 (56.7); 2.498 (43.6); 2.329 (0.4); 2.183 (0.4); 1.877 (13.8); 1.601 (1.4); 1.235 (0.7); 0.000 (2.2)

Example I-43

[0386] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0387] =7.341 (1.5); 7.334 (1.6); 7.320 (1.6); 7.313 (1.5); 7.259 (9.6); 7.110 (1.3); 7.095 (1.4); 7.089 (1.8); 7.074 (1.7); 6.955 (1.0); 6.949 (0.9); 6.935 (1.4); 6.928 (1.3); 6.913 (1.7); 6.908 (1.7); 6.893 (1.7); 6.889 (1.7); 6.812 (0.5); 6.808 (0.5); 6.793 (1.4); 6.789 (1.3); 6.774 (1.2); 6.770 (1.0); 6.757 (1.2); 6.752 (1.4); 6.737 (1.4); 6.733 (1.5); 6.718 (0.6); 6.714 (0.5); 6.383 (1.6); 6.379 (1.7); 6.364 (1.4); 6.359 (1.4); 5.702 (1.8); 5.296 (1.6); 4.704 (6.1); 4.698 (6.1); 3.681 (16.0); 2.492 (1.7); 2.486 (3.4); 2.480 (1.6); 2.170 (15.9); 2.001 (2.9); 1.595 (1.1); 0.000 (0.3)

Example I-44

[0388] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0389] =7.351 (1.5); 7.344 (1.5); 7.330 (1.5); 7.323 (1.5); 7.260 (13.6); 7.134 (1.3); 7.119 (1.4); 7.112 (1.7); 7.097 (1.7); 6.985 (0.9); 6.979 (0.9); 6.965 (1.3); 6.958 (1.3); 6.944 (0.7); 6.937 (0.7); 6.691 (1.3); 6.678 (1.3); 6.668 (1.4); 6.656 (1.4); 6.388 (0.8); 6.380 (0.8); 6.366 (1.2); 6.359 (1.3); 6.345 (0.7); 6.337 (0.7); 6.091 (1.5); 6.084 (1.4); 6.066 (1.5); 6.058 (1.4); 6.046 (0.4); 6.032 (0.7); 6.019 (0.7); 6.006 (0.8); 6.003 (0.5); 5.993 (0.5); 5.989 (0.8); 5.976 (0.8); 5.963 (0.8); 5.950 (0.4); 5.832 (1.6); 5.368 (0.5); 5.364 (1.3); 5.360 (1.4); 5.356 (0.6); 5.324 (0.5); 5.321 (1.2); 5.317 (1.2); 5.313 (0.5); 5.297 (0.5); 5.279 (1.4); 5.276 (1.4); 5.253 (1.3); 5.249 (1.3); 4.512 (2.2); 4.508 (2.2); 4.503 (1.4); 4.499 (2.2); 4.495 (2.1); 3.706 (16.0); 2.172 (16.0); 2.003 (0.4); 1.567 (4.9); 0.000 (0.5)

Example I-45

[0390] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0391] =7.352 (1.5); 7.346 (1.6); 7.332 (1.6); 7.325 (1.5); 7.261 (6.7); 7.133 (1.3); 7.118 (1.4); 7.111 (1.8); 7.096 (1.7); 6.985 (1.0); 6.979 (1.0); 6.965 (1.3); 6.959 (1.3); 6.944 (0.8); 6.937 (0.7); 6.835 (1.3); 6.823 (1.4); 6.813 (1.5); 6.801 (1.4); 6.417 (0.8); 6.410 (0.9); 6.397 (1.1); 6.395 (1.0); 6.389 (1.1); 6.375 (0.8); 6.367 (0.8); 6.114 (1.5); 6.107 (1.4); 6.089 (1.6); 6.082 (1.4); 5.794 (1.5); 5.296 (1.3); 4.666 (5.2); 4.660 (5.1); 3.699 (16.0); 2.480 (1.7); 2.474 (3.5); 2.468 (1.7); 2.170 (15.9); 2.001 (3.1); 1.615 (0.6)

Example I-46

[0392] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0393] =7.339 (1.6); 7.332 (1.6); 7.318 (1.6); 7.311 (1.5); 7.259 (7.5); 7.107 (1.3); 7.092 (1.4); 7.086 (1.8); 7.071 (1.7); 6.953 (1.0); 6.947 (1.0); 6.933 (1.4); 6.926 (1.3); 6.912 (0.8); 6.905 (0.7); 6.602 (2.0); 6.599 (2.2); 6.559 (1.0); 6.538 (1.1); 6.249 (2.7); 6.229 (2.4); 6.067 (0.4); 6.054 (0.8); 6.041 (0.7); 6.027 (0.9); 6.024 (0.5); 6.014 (0.5); 6.011 (0.9); 5.997 (0.8); 5.984 (0.9); 5.971 (0.4); 5.623 (1.9); 5.376 (0.5); 5.372 (1.4); 5.368 (1.4); 5.364 (0.5); 5.333 (0.5); 5.329 (1.2); 5.325 (1.2); 5.321 (0.5); 5.295 (1.5); 5.276 (0.6); 5.273 (1.5); 5.269 (1.5); 5.266 (0.6); 5.250 (0.5); 5.246 (1.4); 5.243 (1.4); 5.239 (0.5); 4.537 (0.8); 4.533 (1.5); 4.530 (1.5); 4.526 (1.6); 4.523 (1.5); 4.520 (1.6); 4.517 (1.5); 4.513 (1.4); 4.510 (0.8); 3.676 (16.0); 2.218 (11.4); 2.165 (15.8); 2.000 (1.7); 1.641 (0.5)

Example I-47

[0394] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0395] =7.341 (1.5); 7.335 (1.6); 7.321 (1.5); 7.314 (1.5); 7.259 (7.8); 7.106 (1.3); 7.091 (1.4); 7.085 (1.7); 7.070 (1.7); 6.955 (1.0); 6.948 (0.9); 6.934 (1.4); 6.928 (1.3); 6.913 (0.7); 6.907 (0.7); 6.717 (2.2); 6.713 (2.2); 6.606 (1.0); 6.586 (1.2); 6.274 (2.8); 6.254 (2.5); 5.569 (2.0); 5.296 (1.7); 4.681 (6.1); 4.675 (6.1); 3.665 (16.0); 2.487 (1.7); 2.481 (3.4); 2.475 (1.6); 2.327 (0.4); 2.237 (11.7); 2.163 (15.8); 2.001 (2.2); 1.611 (1.0)

Example I-48

[0396] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0397] =7.259 (11.5); 7.155 (1.5); 7.148 (1.5); 7.133 (1.5); 7.127 (1.5); 7.117 (1.4); 7.101 (1.4); 7.095 (1.7); 7.080 (1.6); 6.911 (1.0); 6.904 (0.9); 6.891 (1.3); 6.884 (1.2); 6.869 (0.8); 6.863 (0.8); 6.794 (1.0); 6.789 (0.8); 6.776 (1.5); 6.770 (1.9); 6.765 (0.4); 6.760 (0.5); 6.746 (1.4); 6.741 (1.2); 6.729 (2.6); 6.724 (2.5); 6.711 (1.4); 6.706 (1.1); 6.692 (0.4); 6.345 (1.6); 6.340 (1.6); 6.328 (0.9); 6.326 (1.0); 6.322 (1.4); 6.070 (0.4); 6.057 (0.7); 6.044 (0.7); 6.031 (0.8); 6.027 (0.5); 6.018 (0.5); 6.014 (0.9); 6.001 (0.8); 5.988 (0.9); 5.974 (0.4); 5.759 (1.8); 5.381 (0.5); 5.377 (1.4); 5.373 (1.4); 5.369 (0.5); 5.338 (0.5); 5.334 (1.2); 5.330 (1.2); 5.326 (0.5); 5.296 (0.4); 5.286 (0.6); 5.283 (1.5); 5.280 (1.5); 5.276 (0.5); 5.260 (0.5); 5.257 (1.4); 5.253 (1.3); 5.250 (0.5); 4.556 (1.7); 4.545 (1.7); 3.690 (16.0); 2.181 (15.9); 2.001 (0.4); 1.584 (1.7); 0.000 (0.4)

Example I-49

[0398] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0399] =7.259 (4.3); 7.156 (1.5); 7.149 (1.6); 7.134 (1.5); 7.128 (1.6); 7.114 (1.4); 7.098 (1.4); 7.092 (1.7); 7.077 (1.6); 6.916 (1.3); 6.912 (1.5); 6.910 (1.3); 6.903 (1.0); 6.897 (1.8); 6.893 (1.9); 6.889 (1.6); 6.883 (1.3); 6.868 (0.8); 6.861 (0.8); 6.810 (0.5); 6.807 (0.5); 6.791 (1.4); 6.788 (1.4); 6.773 (1.2); 6.769 (1.0); 6.758 (1.3); 6.753 (1.5); 6.739 (1.4); 6.734 (1.5); 6.720 (0.6); 6.715 (0.5); 6.367 (1.6); 6.362 (1.7); 6.347 (1.4); 6.343 (1.5); 5.706 (1.9); 5.293 (1.1); 4.707 (6.2); 4.701 (6.2); 3.680 (16.0); 2.494 (1.7); 2.488 (3.6); 2.482 (1.7); 2.178 (15.9); 1.998 (2.7)

Example I-50

[0400] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0401] =7.260 (6.4); 7.167 (1.5); 7.160 (1.6); 7.145 (1.5); 7.138 (2.1); 7.122 (1.4); 7.116 (1.7); 7.100 (1.6); 6.940 (1.0); 6.933 (0.9); 6.920 (1.3); 6.913 (1.2); 6.899 (0.8); 6.892 (0.7); 6.695 (1.3); 6.683 (1.3); 6.673 (1.4); 6.661 (1.4); 6.389 (0.9); 6.382 (0.9); 6.368 (1.2); 6.361 (1.2); 6.347 (0.8); 6.339 (0.8); 6.075 (1.5); 6.068 (1.5); 6.050 (1.6); 6.046 (0.6); 6.043 (1.5); 6.033 (0.8); 6.020 (0.7); 6.007 (0.8); 6.003 (0.5); 5.993 (0.5); 5.990 (0.9); 5.977 (0.8); 5.963 (0.9); 5.950 (0.4); 5.834 (1.5); 5.367 (0.5); 5.364 (1.3); 5.360 (1.4); 5.356 (0.6); 5.324 (0.5); 5.320 (1.2); 5.317 (1.2); 5.313 (0.5); 5.296 (0.3); 5.285 (0.6); 5.282 (1.5); 5.279 (1.4); 5.275 (0.5); 5.259 (0.6); 5.256 (1.4); 5.252 (1.3); 5.249 (0.5); 4.514 (1.8); 4.502 (1.8); 3.705 (16.0); 2.182 (15.9); 2.001 (0.4); 1.615 (0.6)

Example I-51

[0402] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0403] =7.260 (9.0); 7.169 (1.5); 7.163 (1.5); 7.148 (1.5); 7.141 (1.5); 7.135 (1.4); 7.120 (1.4); 7.114 (1.7); 7.098 (1.6); 6.940 (1.0); 6.933 (0.9); 6.920 (1.3); 6.913 (1.2); 6.898 (0.8); 6.892 (0.7); 6.839 (1.3); 6.826 (1.4); 6.817 (1.5); 6.804 (1.4); 6.419 (0.9); 6.412 (0.9); 6.399 (1.1); 6.397 (1.1); 6.391 (1.1); 6.390 (1.1); 6.377 (0.8); 6.369 (0.8); 6.095 (1.5); 6.087 (1.4); 6.070 (1.6); 6.062 (1.4); 5.793 (1.4); 5.297 (1.1); 4.670 (5.6); 4.664 (5.6); 3.699 (16.0); 2.484 (1.7); 2.478 (3.6); 2.472 (1.7); 2.179 (15.9); 1.592 (1.0); 1.256 (1.8); 0.000 (0.3)

Example I-52

[0404] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0405] =7.258 (4.9); 7.154 (1.5); 7.147 (1.6); 7.132 (1.5); 7.126 (1.6); 7.112 (1.4); 7.097 (1.5); 7.091 (1.7); 7.075 (1.6); 6.909 (1.0); 6.902 (1.0); 6.888 (1.3); 6.882 (1.2); 6.867 (0.9); 6.860 (0.8); 6.607 (1.9); 6.604 (2.2); 6.558 (1.0); 6.556 (1.0); 6.538 (1.1); 6.536 (1.1); 6.236 (2.7); 6.216 (2.4); 6.066 (0.4); 6.053 (0.8); 6.040 (0.8); 6.027 (0.9); 6.023 (0.5); 6.014 (0.5); 6.010 (0.9); 5.997 (0.9); 5.984 (0.9); 5.971 (0.5); 5.628 (1.9); 5.375 (0.5); 5.371 (1.4); 5.368 (1.5); 5.364 (0.6); 5.332 (0.5); 5.328 (1.2); 5.324 (1.3); 5.320 (0.5); 5.292 (1.3); 5.278 (0.6); 5.275 (1.5); 5.271 (1.6); 5.268 (0.7); 5.252 (0.6); 5.248 (1.4); 5.245 (1.4); 5.241 (0.6); 4.532 (1.6); 4.522 (1.5); 3.675 (16.0); 2.220 (11.3); 2.175 (15.8)

Example I-53

[0406] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0407] =7.259 (6.0); 7.157 (1.5); 7.150 (1.5); 7.135 (1.5); 7.129 (1.5); 7.110 (1.3); 7.094 (1.4); 7.088 (1.7); 7.073 (1.6); 6.910 (0.9); 6.903 (0.9); 6.889 (1.4); 6.883 (1.3); 6.868 (0.8); 6.862 (0.7); 6.721 (2.3); 6.718 (2.4); 6.605 (1.1); 6.585 (1.3); 6.257 (2.8); 6.237 (2.5); 5.571 (2.2); 5.295 (2.2); 4.685 (6.2); 4.679 (6.1); 3.665 (15.9); 2.489 (1.6); 2.483 (3.3); 2.477 (1.6); 2.238 (12.4); 2.172 (16.0); 2.000 (1.3); 1.627 (0.4)

Example I-54

[0408] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0409] =7.411 (3.0); 7.405 (3.1); 7.258 (7.2); 7.157 (1.4); 7.152 (1.3); 7.137 (2.3); 7.131 (2.2); 7.074 (3.8); 7.054 (2.3); 6.798 (1.0); 6.793 (0.8); 6.791 (0.8); 6.780 (1.4); 6.774 (1.9); 6.759 (0.6); 6.746 (1.4); 6.741 (1.2); 6.733 (1.8); 6.729 (2.2); 6.727 (2.4); 6.722 (1.2); 6.715 (1.3); 6.710 (1.1); 6.696 (0.4); 6.331 (1.6); 6.325 (1.4); 6.314 (0.8); 6.312 (1.0); 6.307 (1.4); 6.074 (0.4); 6.061 (0.7); 6.048 (0.7); 6.035 (0.8); 6.031 (0.5); 6.021 (0.5); 6.018 (0.9); 6.005 (0.8); 5.991 (0.9); 5.978 (0.4); 5.768 (2.0); 5.386 (0.5); 5.382 (1.4); 5.378 (1.4); 5.374 (0.6); 5.342 (0.5); 5.339 (1.2); 5.335 (1.3); 5.331 (0.5); 5.295 (1.1); 5.292 (0.7); 5.288 (1.5); 5.285 (1.5); 5.281 (0.6); 5.265 (0.5); 5.262 (1.4); 5.258 (1.3); 5.255 (0.5); 4.561 (2.0); 4.548 (1.9); 3.686 (16.0); 2.185 (16.0); 1.604 (0.5)

Example I-55

[0410] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0411] =7.412 (3.0); 7.407 (3.1); 7.259 (8.6); 7.157 (1.6); 7.151 (1.5); 7.136 (2.4); 7.131 (2.4); 7.070 (3.8); 7.050 (2.3); 6.920 (1.3); 6.916 (1.2); 6.900 (1.7); 6.896 (1.7); 6.810 (0.4); 6.807 (0.5); 6.792 (1.4); 6.788 (1.3); 6.773 (1.3); 6.769 (1.1); 6.763 (1.4); 6.758 (1.5); 6.744 (1.4); 6.739 (1.6); 6.725 (0.6); 6.720 (0.5); 6.353 (1.6); 6.348 (1.7); 6.333 (1.3); 6.329 (1.5); 5.713 (1.9); 5.295 (2.1); 4.714 (6.1); 4.708 (6.1); 4.337 (0.3); 3.678 (15.9); 2.496 (1.8); 2.490 (3.8); 2.485 (1.7); 2.182 (16.0); 2.000 (0.8); 1.601 (0.5)

Example I-56

[0412] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0413] =7.423 (3.1); 7.418 (3.2); 7.259 (7.8); 7.188 (1.5); 7.182 (1.4); 7.167 (2.3); 7.162 (2.2); 7.094 (3.7); 7.074 (2.4); 6.700 (1.3); 6.687 (1.3); 6.678 (1.4); 6.665 (1.4); 6.395 (0.9); 6.388 (0.9); 6.374 (1.2); 6.367 (1.2); 6.352 (0.8); 6.345 (0.8); 6.061 (1.6); 6.053 (1.5); 6.036 (1.9); 6.028 (1.5); 6.024 (0.8); 6.011 (0.8); 6.007 (0.5); 5.997 (0.5); 5.994 (0.9); 5.981 (0.8); 5.967 (0.9); 5.954 (0.5); 5.842 (1.6); 5.372 (0.5); 5.369 (1.4); 5.365 (1.4); 5.361 (0.6); 5.329 (0.5); 5.326 (1.2); 5.322 (1.3); 5.318 (0.5); 5.296 (1.8); 5.290 (0.6); 5.287 (1.5); 5.284 (1.5); 5.281 (0.6); 5.264 (0.6); 5.261 (1.4); 5.258 (1.4); 5.254 (0.5); 4.519 (2.1); 4.506 (2.0); 3.701 (16.0); 2.186 (16.0); 2.001 (0.5); 1.589 (0.8)

Example I-57

[0414] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0415] =7.409 (3.1); 7.404 (3.2); 7.258 (7.8); 7.155 (1.4); 7.150 (1.4); 7.135 (2.3); 7.129 (2.2); 7.069 (3.8); 7.048 (2.4); 6.611 (2.1); 6.607 (2.3); 6.556 (1.1); 6.536 (1.2); 6.221 (2.8); 6.201 (2.5); 6.071 (0.4); 6.058 (0.7); 6.045 (0.7); 6.032 (0.8); 6.028 (0.5); 6.018 (0.5); 6.015 (0.9); 6.002 (0.9); 5.989 (0.9); 5.975 (0.5); 5.634 (2.2); 5.381 (0.5); 5.377 (1.4); 5.373 (1.4); 5.369 (0.6); 5.338 (0.5); 5.334 (1.2); 5.330 (1.3); 5.326 (0.6); 5.295 (1.7); 5.284 (0.6); 5.281 (1.5); 5.277 (1.5); 5.274 (0.7); 5.258 (0.6); 5.255 (1.4); 5.251 (1.4); 5.248 (0.6); 4.539 (1.9); 4.526 (1.9); 4.330 (0.6); 3.672 (16.0); 2.309 (0.8); 2.222 (11.8); 2.193 (0.5); 2.179 (16.0); 2.130 (0.3); 2.000 (0.4); 1.609 (0.5)

Example I-58

[0416] .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

[0417] =7.412 (3.1); 7.406 (3.2); 7.259 (8.0); 7.155 (1.5); 7.150 (1.4); 7.135 (2.3); 7.129 (2.3); 7.066 (3.8); 7.045 (2.4); 6.724 (2.1); 6.720 (2.2); 6.603 (1.0); 6.583 (1.1); 6.243 (2.8); 6.223 (2.5); 5.581 (2.1); 5.295 (3.0); 4.691 (6.2); 4.685 (6.2); 4.628 (0.4); 4.622 (0.4); 4.321 (0.6); 3.663 (16.0); 2.492 (1.7); 2.486 (3.6); 2.480 (1.7); 2.329 (0.7); 2.240 (11.6); 2.176 (15.9); 2.000 (1.6); 1.603 (0.6)

Example I-59

[0418] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0419] =7.279 (2.6); 6.900 (2.0); 6.881 (2.3); 6.877 (2.3); 6.858 (1.9); 6.633 (0.8); 6.627 (1.1); 6.622 (0.9); 6.606 (0.8); 6.600 (1.1); 6.595 (0.9); 6.568 (0.7); 6.561 (0.6); 6.545 (0.9); 6.540 (1.1); 6.534 (0.7); 6.518 (0.7); 6.511 (0.6); 4.727 (5.2); 4.721 (5.3); 3.665 (16.0); 3.648 (1.7); 3.642 (3.6); 3.636 (1.6); 3.331 (19.4); 2.525 (0.7); 2.512 (15.2); 2.507 (30.8); 2.503 (40.4); 2.498 (29.4); 2.494 (14.3); 1.899 (0.4); 1.874 (12.6); 1.859 (0.4); 1.235 (0.3); 0.008 (0.9); 0.000 (25.0); 0.008 (1.0)

Example I-60

[0420] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0421] =7.329 (2.7); 7.182 (0.3); 7.071 (0.4); 7.059 (4.4); 7.042 (4.2); 7.030 (0.5); 6.633 (0.7); 6.627 (1.1); 6.623 (0.9); 6.606 (0.8); 6.601 (1.1); 6.567 (0.7); 6.560 (0.6); 6.544 (0.9); 6.539 (1.1); 6.533 (0.7); 6.517 (0.8); 6.510 (0.6); 4.729 (5.2); 4.723 (5.3); 3.661 (16.0); 3.649 (1.9); 3.643 (3.8); 3.637 (1.6); 3.327 (36.9); 2.676 (0.4); 2.671 (0.6); 2.667 (0.4); 2.541 (0.4); 2.525 (1.6); 2.520 (2.4); 2.511 (33.9); 2.507 (68.3); 2.502 (89.8); 2.498 (66.2); 2.493 (32.8); 2.333 (0.4); 2.329 (0.6); 2.324 (0.4); 2.300 (1.3); 1.881 (12.5); 1.235 (0.4); 0.008 (2.0); 0.000 (59.5); 0.009 (2.2)

Example I-61

[0422] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0423] =7.124 (2.0); 7.121 (2.0); 6.607 (0.6); 6.601 (0.8); 6.597 (0.7); 6.580 (0.6); 6.575 (0.8); 6.570 (0.7); 6.535 (0.6); 6.529 (0.5); 6.512 (0.7); 6.507 (0.9); 6.501 (0.6); 6.485 (0.6); 6.478 (0.6); 6.467 (0.4); 6.456 (3.1); 6.433 (3.1); 6.422 (0.4); 5.757 (1.8); 4.711 (4.2); 4.706 (4.3); 3.686 (16.0); 3.651 (12.6); 3.642 (1.6); 3.636 (3.0); 3.630 (1.3); 3.326 (44.3); 2.676 (0.5); 2.671 (0.7); 2.667 (0.5); 2.541 (1.0); 2.524 (1.6); 2.520 (2.4); 2.511 (34.5); 2.507 (71.5); 2.502 (95.7); 2.497 (71.0); 2.493 (35.4); 2.333 (0.5); 2.329 (0.6); 2.324 (0.5); 1.868 (10.1); 0.008 (2.1); 0.000 (67.8); 0.009 (2.6)

Example I-62

[0424] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0425] =7.555 (2.9); 6.481 (3.9); 6.457 (6.7); 6.436 (4.0); 5.757 (0.3); 4.653 (5.6); 4.647 (5.6); 3.766 (0.4); 3.677 (16.0); 3.662 (14.1); 3.598 (1.7); 3.593 (3.0); 3.377 (14.1); 2.540 (1.7); 2.502 (48.5); 1.876 (12.2); 0.000 (15.1)

Example I-63

[0426] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0427] =11.650 (0.6); 7.144 (2.9); 6.795 (0.5); 6.772 (0.5); 6.753 (0.4); 6.729 (0.4); 6.594 (1.3); 6.572 (0.9); 6.567 (1.3); 6.536 (0.4); 6.525 (1.3); 6.516 (4.6); 6.494 (4.9); 6.483 (0.7); 6.474 (1.1); 6.468 (0.7); 5.757 (1.1); 4.854 (0.9); 4.848 (1.0); 4.844 (0.7); 4.837 (0.7); 4.754 (5.9); 4.749 (6.0); 4.707 (5.7); 4.701 (5.7); 3.783 (0.7); 3.761 (1.5); 3.706 (0.5); 3.653 (16.0); 3.640 (2.9); 3.634 (4.6); 3.630 (3.3); 3.624 (4.2); 3.619 (1.9); 3.571 (0.4); 3.561 (0.4); 3.331 (10.9); 2.507 (25.2); 2.503 (32.7); 2.498 (24.3); 2.211 (1.8); 1.873 (13.7); 1.235 (0.4); 1.192 (0.9); 0.008 (1.7); 0.000 (43.7); 0.008 (2.0)

Example I-64

[0428] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0429] =7.183 (1.6); 7.177 (1.6); 7.161 (1.6); 7.154 (1.6); 7.096 (1.4); 7.080 (1.5); 7.074 (1.9); 7.058 (1.7); 7.025 (3.8); 6.943 (1.0); 6.936 (1.0); 6.922 (1.8); 6.915 (1.6); 6.900 (0.8); 6.894 (0.7); 6.763 (0.8); 6.754 (1.0); 6.747 (1.3); 6.738 (2.8); 6.732 (1.3); 6.720 (7.8); 6.712 (2.1); 6.704 (1.7); 4.668 (2.2); 4.662 (2.5); 4.656 (2.5); 4.650 (2.2); 3.664 (16.0); 3.620 (1.6); 3.614 (3.2); 3.608 (1.5); 3.331 (29.7); 2.525 (0.9); 2.507 (35.8); 2.502 (46.9); 2.498 (34.3); 2.494 (17.0); 1.905 (16.0); 1.234 (0.5); 0.000 (0.7)

Example I-65

[0430] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0431] =7.179 (1.6); 7.173 (1.7); 7.157 (1.6); 7.150 (1.6); 7.087 (1.4); 7.071 (1.5); 7.065 (1.9); 7.049 (1.7); 6.954 (3.8); 6.947 (1.5); 6.940 (1.1); 6.925 (1.8); 6.918 (1.6); 6.904 (0.8); 6.897 (0.7); 6.714 (0.7); 6.709 (0.9); 6.695 (2.7); 6.690 (4.5); 6.671 (3.6); 6.661 (0.5); 6.652 (1.6); 6.643 (2.3); 6.637 (2.0); 6.624 (1.0); 6.618 (0.9); 5.935 (0.6); 5.922 (0.6); 5.909 (0.7); 5.905 (0.5); 5.896 (0.4); 5.892 (0.8); 5.879 (0.6); 5.865 (0.8); 5.853 (0.4); 5.758 (0.7); 5.303 (1.4); 5.299 (1.5); 5.260 (1.2); 5.256 (1.3); 5.226 (1.5); 5.222 (1.5); 5.199 (1.4); 5.195 (1.4); 4.376 (3.0); 4.364 (3.0); 3.688 (0.7); 3.673 (15.9); 3.638 (0.5); 3.332 (19.2); 2.525 (0.6); 2.512 (12.4); 2.507 (25.2); 2.503 (33.2); 2.499 (24.6); 2.494 (12.6); 1.944 (0.3); 1.933 (0.6); 1.921 (1.4); 1.906 (16.0); 1.234 (0.4); 1.190 (0.5); 0.000 (0.5)

Example I-66

[0432] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0433] =7.353 (3.3); 7.348 (3.5); 7.138 (1.4); 7.133 (1.3); 7.117 (2.6); 7.112 (2.6); 7.073 (7.1); 7.053 (2.4); 6.775 (0.8); 6.765 (1.1); 6.760 (1.4); 6.750 (2.7); 6.739 (1.6); 6.729 (8.2); 6.720 (2.3); 6.714 (2.0); 5.757 (1.0); 4.671 (2.1); 4.665 (2.5); 4.659 (2.4); 4.654 (2.2); 3.777 (0.4); 3.657 (15.9); 3.631 (0.4); 3.617 (1.5); 3.611 (3.2); 3.605 (1.5); 3.331 (23.8); 2.525 (0.7); 2.507 (32.0); 2.503 (41.9); 2.498 (30.8); 1.989 (1.3); 1.914 (16.0); 1.298 (0.3); 1.259 (0.5); 1.235 (0.6); 1.193 (0.4); 1.175 (0.7); 1.157 (0.3); 0.000 (0.5)

Example I-67

[0434] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0435] =7.195 (3.7); 7.075 (0.7); 7.058 (0.9); 7.054 (1.5); 7.037 (1.5); 7.033 (1.0); 7.015 (0.8); 6.975 (0.8); 6.968 (0.8); 6.950 (1.3); 6.944 (1.3); 6.926 (0.8); 6.919 (0.8); 6.818 (1.3); 6.806 (2.5); 6.794 (2.5); 6.784 (0.6); 6.777 (1.3); 6.771 (1.2); 6.755 (0.6); 6.750 (0.6); 6.728 (0.3); 6.715 (0.4); 6.707 (4.9); 6.706 (4.9); 6.695 (4.9); 4.712 (5.5); 4.706 (5.5); 3.794 (0.3); 3.686 (0.5); 3.647 (16.0); 3.638 (2.1); 3.632 (3.4); 3.626 (1.6); 3.443 (0.3); 3.331 (23.1); 2.525 (0.7); 2.511 (15.5); 2.507 (31.3); 2.503 (41.2); 2.498 (30.3); 1.951 (10.4); 1.846 (0.5); 1.259 (0.4); 1.235 (0.7)

[0436] The following intermediates were synthesised according to the examples and methods described above

Intermediates According to the Formula (Z-ix):

[0437] ##STR00016##

TABLE-US-00003 Ex N.sup.o R.sup.1 Q.sup.1 Q.sup.2 LogP Z-ix-01 methyl 2-chloro-4- 4-(allyloxy)-2,6- 4.55.sup.[a] fluorophenyl difluorophenyl Z-ix-01 methyl 2-chloro-4- 2,6-difluoro-4-(prop-2- 4.13.sup.[a] fluorophenyl yn-1-yloxy)phenyl Z-ix-03 methyl 2-chloro-4- 2,4-difluoro-6- 3.65.sup.[a] fluorophenyl (prop-2-yn-1- yloxy)phenyl

NMR Peak Lists of Intermediates According to the Formula (Z-ix)

Example Z-ix-01

[0438] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0439] =14.097 (3.6); 8.545 (0.4); 8.317 (3.0); 7.736 (0.4); 7.679 (0.3); 7.664 (0.4); 7.658 (0.4); 7.643 (0.4); 7.594 (0.3); 7.578 (0.8); 7.571 (0.8); 7.551 (1.1); 7.534 (1.2); 7.528 (1.2); 7.512 (1.2); 7.471 (0.4); 7.465 (0.4); 7.436 (1.4); 7.429 (1.3); 7.414 (1.3); 7.407 (1.3); 7.380 (1.3); 7.370 (1.8); 7.364 (1.6); 7.358 (1.9); 7.353 (3.3); 7.349 (2.8); 7.331 (2.8); 7.323 (1.7); 7.317 (1.5); 7.300 (1.6); 7.296 (1.8); 7.279 (1.6); 7.244 (0.6); 7.217 (3.0); 7.211 (2.7); 7.195 (3.8); 7.189 (3.5); 7.179 (3.0); 7.164 (1.5); 7.158 (1.5); 7.137 (1.1); 7.129 (2.5); 7.122 (2.2); 7.115 (1.7); 7.106 (2.2); 7.099 (2.3); 7.088 (0.9); 7.061 (0.8); 7.051 (2.6); 7.045 (2.6); 7.041 (1.4); 7.033 (1.1); 7.023 (1.1); 7.013 (1.8); 7.007 (1.4); 7.002 (2.1); 6.992 (2.4); 6.985 (2.1); 6.980 (1.3); 6.971 (1.2); 6.964 (1.1); 6.870 (0.6); 6.669 (3.2); 6.646 (3.3); 6.582 (1.3); 6.576 (1.2); 6.550 (1.3); 6.544 (1.2); 6.069 (0.7); 6.057 (1.3); 6.044 (1.4); 6.030 (1.3); 6.014 (1.4); 6.001 (1.4); 5.988 (1.2); 5.975 (0.5); 5.450 (0.5); 5.436 (1.6); 5.432 (1.6); 5.415 (1.6); 5.411 (1.7); 5.393 (1.5); 5.389 (1.4); 5.372 (1.3); 5.289 (1.8); 5.285 (1.7); 5.263 (1.7); 5.259 (1.6); 5.252 (1.5); 5.248 (1.5); 5.225 (1.1); 4.733 (0.4); 4.721 (0.4); 4.655 (0.7); 4.641 (0.8); 4.629 (0.4); 4.572 (3.4); 4.559 (3.4); 4.532 (2.9); 4.519 (2.8); 3.920 (7.4); 3.492 (0.4); 3.474 (0.4); 3.325 (181.2); 3.211 (0.4); 2.942 (1.3); 2.696 (0.5); 2.675 (5.9); 2.671 (7.8); 2.666 (5.7); 2.603 (0.8); 2.506 (898.8); 2.502 (1142.4); 2.497 (846.3); 2.392 (0.4); 2.378 (0.4); 2.359 (0.4); 2.333 (5.7); 2.328 (7.5); 2.324 (5.6); 2.282 (0.6); 2.267 (0.4); 2.225 (2.9); 2.182 (15.5); 2.073 (0.9); 2.061 (1.0); 2.021 (0.4); 1.621 (15.6); 1.603 (1.7); 1.589 (11.6); 1.491 (13.3); 1.486 (16.0); 1.457 (0.4); 1.388 (0.4); 1.355 (5.6); 1.330 (0.5); 1.262 (2.7); 1.235 (6.8); 1.169 (0.9); 1.148 (1.0); 1.117 (0.4); 1.102 (0.4); 1.080 (0.4); 1.065 (0.4); 1.036 (0.4); 0.980 (0.5); 0.931 (0.3); 0.915 (0.3); 0.854 (2.2); 0.837 (1.8); 0.817 (1.0); 0.146 (6.2); 0.036 (0.9); 0.008 (66.4); 0.000 (1332.6); 0.008 (81.7); 0.056 (1.2); 0.095 (0.5); 0.120 (0.4); 0.132 (0.4); 0.150 (6.5)

Example Z-ix-02

[0440] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0441] =14.136 (3.6); 8.316 (3.5); 7.641 (0.4); 7.619 (0.5); 7.615 (0.5); 7.579 (0.4); 7.534 (0.4); 7.497 (0.4); 7.476 (0.3); 7.470 (0.4); 7.426 (0.4); 7.414 (0.3); 7.407 (0.4); 7.358 (1.3); 7.337 (1.5); 7.331 (1.4); 7.310 (1.6); 7.299 (1.4); 7.293 (1.3); 7.263 (0.4); 7.246 (0.4); 7.220 (3.2); 7.213 (2.0); 7.202 (2.0); 7.198 (3.5); 7.190 (2.1); 7.181 (2.0); 7.175 (0.7); 7.169 (0.7); 7.161 (0.6); 7.150 (1.0); 7.144 (1.2); 7.129 (1.6); 7.123 (1.6); 7.107 (2.4); 7.064 (0.3); 7.039 (0.5); 7.025 (1.2); 7.018 (1.3); 7.011 (0.5); 7.003 (2.1); 6.997 (2.1); 6.982 (1.0); 6.975 (1.0); 6.869 (0.6); 6.713 (3.5); 6.690 (3.5); 6.659 (0.4); 6.643 (1.0); 6.609 (0.7); 4.983 (0.5); 4.977 (0.6); 4.935 (0.4); 4.903 (1.1); 4.897 (1.2); 4.871 (0.6); 4.855 (0.4); 4.819 (5.9); 4.813 (6.0); 4.785 (0.4); 4.751 (6.3); 4.745 (6.3); 4.707 (0.4); 4.695 (0.5); 4.688 (0.5); 3.919 (0.9); 3.692 (0.5); 3.647 (0.5); 3.635 (0.8); 3.624 (1.7); 3.618 (3.7); 3.612 (1.7); 3.602 (0.4); 3.595 (0.4); 3.586 (0.4); 3.559 (0.4); 3.553 (0.4); 3.539 (1.9); 3.534 (3.9); 3.528 (1.9); 3.477 (0.4); 3.458 (0.3); 3.447 (0.4); 3.440 (0.4); 3.433 (0.4); 3.403 (0.5); 3.323 (567.6); 2.875 (0.3); 2.843 (0.4); 2.760 (0.5); 2.750 (0.4); 2.729 (0.5); 2.718 (0.6); 2.701 (0.6); 2.680 (3.2); 2.675 (6.4); 2.671 (8.7); 2.666 (6.6); 2.662 (3.3); 2.647 (0.7); 2.641 (0.8); 2.604 (1.1); 2.524 (23.0); 2.519 (34.3); 2.511 (447.5); 2.506 (925.7); 2.502 (1237.3); 2.497 (900.2); 2.493 (434.2); 2.338 (2.2); 2.333 (5.3); 2.328 (7.5); 2.324 (5.5); 2.319 (2.4); 2.245 (0.5); 2.227 (2.5); 2.182 (2.2); 2.090 (0.3); 2.073 (0.4); 2.061 (0.4); 1.902 (10.4); 1.606 (8.8); 1.489 (16.0); 1.475 (0.7); 1.355 (6.0); 1.296 (0.3); 1.262 (1.4); 1.235 (5.1); 1.207 (1.9); 1.192 (2.0); 1.169 (1.4); 1.165 (1.2); 1.150 (1.1); 1.126 (0.5); 1.111 (0.3); 0.980 (0.5); 0.935 (0.4); 0.868 (0.6); 0.853 (1.7); 0.835 (1.2); 0.810 (0.7); 0.146 (7.9); 0.138 (0.5); 0.063 (0.5); 0.054 (0.7); 0.035 (1.0); 0.026 (1.3); 0.008 (60.4); 0.000 (1802.7); 0.009 (64.8); 0.025 (1.8); 0.032 (0.8); 0.041 (0.5); 0.049 (0.4); 0.150 (7.7)

Example Z-ix-03

[0442] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0443] =8.317 (9.5); 7.609 (0.4); 7.594 (0.4); 7.426 (0.3); 7.413 (0.4); 7.409 (0.4); 7.379 (0.4); 7.367 (2.1); 7.349 (2.5); 7.345 (2.6); 7.328 (2.5); 7.310 (0.4); 7.288 (0.5); 7.245 (0.4); 7.223 (0.4); 7.201 (0.5); 7.179 (0.8); 7.172 (0.7); 7.146 (0.8); 7.126 (2.3); 7.120 (2.7); 7.103 (2.2); 7.096 (2.4); 7.045 (0.4); 7.011 (1.4); 7.005 (1.3); 6.990 (2.4); 6.983 (2.2); 6.968 (1.2); 6.962 (1.1); 6.762 (0.4); 6.737 (0.5); 5.030 (2.7); 5.024 (2.7); 4.893 (0.4); 4.863 (0.7); 4.858 (0.7); 4.849 (0.9); 4.844 (1.0); 4.826 (0.4); 4.484 (0.4); 3.919 (0.6); 3.756 (0.6); 3.750 (1.2); 3.744 (0.6); 3.629 (0.4); 3.460 (0.4); 3.324 (120.9); 2.675 (3.9); 2.671 (5.2); 2.666 (3.9); 2.506 (599.2); 2.502 (767.7); 2.497 (568.3); 2.332 (3.7); 2.328 (5.1); 2.324 (3.8); 2.309 (0.5); 2.267 (0.4); 2.222 (0.4); 2.182 (1.5); 2.001 (0.8); 1.602 (1.7); 1.574 (16.0); 1.511 (0.4); 1.489 (0.6); 1.482 (0.7); 1.355 (2.6); 1.283 (1.4); 1.262 (3.1); 1.235 (5.3); 1.194 (1.1); 1.168 (1.0); 1.147 (0.7); 1.101 (0.6); 1.080 (0.4); 0.911 (0.4); 0.898 (0.4); 0.853 (2.0); 0.836 (1.4); 0.813 (0.8); 0.146 (4.3); 0.034 (0.4); 0.008 (41.5); 0.000 (912.8); 0.008 (44.1); 0.066 (0.4); 0.150 (4.4)

Intermediates According to the Formula (Z-iv):

[0444] ##STR00017##

TABLE-US-00004 Ex N.sup.o R.sup.1 Q.sup.1 LogP Z-iv-01 methyl 4-(allyloxy)-2-fluorophenyl 2.60.sup.[a] Z-iv-02 methyl 2-fluoro-4-methoxyphenyl 1.95.sup.[a] Z-iv-03 methyl 2-fluoro-4-(prop-2-yn-1-yloxy)phenyl 2.16.sup.[a] Z-iv-04 methyl 2,6-difluoro-4-(prop-2-yn-1-yloxy)phenyl 2.39.sup.[a]

[0445] The compounds Z-iv-01 to Z-iv-04 are preferred compounds of formula (Z-iv) in the context of the present invention.

NMR Peak Lists of Intermediates According to the Formula (Z-iv)

Example Z-iv-01

[0446] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0447] =7.157 (1.0); 7.135 (2.0); 7.113 (1.1); 6.825 (1.1); 6.819 (1.3); 6.795 (1.1); 6.789 (1.4); 6.760 (1.3); 6.754 (1.1); 6.739 (1.1); 6.733 (1.0); 6.060 (0.6); 6.046 (0.7); 6.033 (0.7); 6.030 (0.4); 6.020 (0.4); 6.016 (0.8); 6.003 (0.7); 5.990 (0.8); 5.977 (0.4); 5.422 (0.4); 5.418 (1.3); 5.414 (1.4); 5.410 (0.5); 5.379 (0.4); 5.375 (1.2); 5.371 (1.2); 5.366 (0.5); 5.283 (0.5); 5.279 (1.2); 5.275 (1.2); 5.256 (0.5); 5.253 (1.1); 5.249 (1.2); 4.576 (1.7); 4.572 (3.1); 4.569 (1.9); 4.563 (1.8); 4.559 (3.0); 4.555 (1.8); 3.729 (5.5); 3.327 (82.5); 2.675 (0.4); 2.671 (0.6); 2.666 (0.4); 2.524 (1.4); 2.519 (2.2); 2.511 (30.8); 2.506 (63.0); 2.502 (83.8); 2.497 (61.9); 2.493 (30.9); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4); 2.141 (16.0); 0.146 (0.5); 0.008 (3.8); 0.000 (110.0); 0.009 (4.6); 0.150 (0.5)

Example Z-iv-02

[0448] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0449] =7.165 (1.1); 7.144 (2.2); 7.122 (1.2); 6.810 (1.3); 6.804 (1.5); 6.780 (1.3); 6.774 (1.5); 6.746 (1.6); 6.740 (1.3); 6.725 (1.4); 6.719 (1.2); 3.821 (0.4); 3.751 (16.0); 3.731 (6.9); 3.331 (6.4); 2.506 (8.2); 2.503 (9.6); 2.140 (14.0); 1.989 (0.4); 0.002 (6.1); 0.000 (8.8)

Example Z-iv-03

[0450] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0451] =7.184 (1.0); 7.163 (2.0); 7.141 (1.1); 6.870 (1.2); 6.864 (1.3); 6.840 (1.1); 6.834 (1.4); 6.794 (1.3); 6.788 (1.1); 6.773 (1.1); 6.767 (1.0); 4.812 (5.6); 4.806 (5.7); 3.748 (5.4); 3.602 (1.3); 3.596 (3.0); 3.590 (1.3); 3.328 (59.4); 2.671 (0.3); 2.524 (0.8); 2.519 (1.3); 2.511 (19.3); 2.506 (39.7); 2.502 (52.8); 2.497 (38.8); 2.493 (19.0); 2.329 (0.3); 2.150 (16.0); 0.008 (1.0); 0.000 (31.9); 0.009 (1.1)

Example Z-iv-04

[0452] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0453] =6.804 (0.6); 6.795 (3.6); 6.771 (3.6); 6.762 (0.6); 4.853 (5.7); 4.847 (5.8); 3.782 (6.3); 3.645 (1.5); 3.639 (3.1); 3.633 (1.5); 3.332 (55.0); 2.507 (30.0); 2.502 (38.4); 2.498 (28.9); 2.210 (16.0); 0.007 (2.6); 0.000 (50.4)

Intermediates According to the Formula (Z-ii):

[0454]
Q.sup.2-NCS (Z-ii)

TABLE-US-00005 Ex N.sup.o Q.sup.2 LogP Z-ii-01 4-(allyloxy)-2,6-difluorophenyl 4.54.sup.[a] Z-ii-02 2,6-difluoro-4-(prop-2-yn-1-yloxy)phenyl 3.86.sup.[a] Z-ii-03 2,4-difluoro-6-(prop-2-yn-1-yloxy)phenyl 3.68.sup.[a] Z-ii-04 4-(prop-2-yn-1-yloxy)phenyl 3.42.sup.[a]; 3.41.sup.[b] Z-ii-05 4-(allyloxy)phenyl 4.06.sup.[a]; 4.09.sup.[b] Z-ii-06 4-(allyloxy)-3-fluorophenyl 4.06.sup.[a] Z-ii-07 5-(allyloxy)-2-fluorophenyl 4.30.sup.[a] Z-ii-08 2-fluoro-5-(prop-2-yn-1-yloxy)phenyl 3.62.sup.[a] Z-ii-09 2,5-difluoro-4-(prop-2-yn-1-yloxy)phenyl 3.64.sup.[a] Z-ii-10 4-(allyloxy)-2,5-difluorophenyl 4.24.sup.[a] Z-ii-11 3-fluoro-4-(prop-2-yn-1-yloxy)phenyl 3.47.sup.[a] Z-ii-12 2-chloro-4-(prop-2-yn-1-yloxy)phenyl 3.99.sup.[a]; 3.96.sup.[b] Z-ii-13 4-(allyloxy)-2-chlorophenyl 4.72.sup.[a]; 4.72.sup.[b] Z-ii-14 2-chloro-6-(prop-2-yn-1-yloxy)phenyl 3.86.sup.[a] Z-ii-15 2-(allyloxy)-6-chlorophenyl Z-ii-16 2-(allyloxy)-5-fluorophenyl 4.24.sup.[a] Z-ii-17 5-fluoro-2-(prop-2-yn-1-yloxy)phenyl 3.62.sup.[a] Z-ii-18 4-methyl-2-(prop-2-yn-1-yloxy)phenyl 3.82.sup.[a] Z-ii-19 2-(allyloxy)-5-cyanophenyl 3.71.sup.[a] Z-ii-20 5-cyano-2-(prop-2-yn-1-yloxy)phenyl 3.13.sup.[a]

NMR Peak Lists of Intermediates According to the Formula (Z-ii)

Example Z-ii-01

[0455] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0456] =7.060 (0.4); 7.036 (2.0); 7.028 (6.6); 7.023 (16.0); 6.999 (15.5); 6.994 (6.9); 6.986 (1.9); 6.054 (1.3); 6.040 (2.8); 6.027 (2.7); 6.014 (3.2); 6.011 (2.0); 6.000 (1.7); 5.997 (3.4); 5.984 (3.0); 5.971 (3.4); 5.957 (1.6); 5.756 (4.0); 5.436 (1.9); 5.432 (5.5); 5.428 (5.9); 5.424 (2.4); 5.393 (1.7); 5.389 (4.8); 5.385 (5.1); 5.381 (2.1); 5.313 (2.1); 5.310 (5.4); 5.306 (5.5); 5.287 (2.0); 5.284 (5.0); 5.280 (5.2); 4.750 (0.3); 4.737 (0.3); 4.638 (7.2); 4.634 (12.9); 4.631 (8.3); 4.624 (7.5); 4.621 (12.6); 4.617 (7.9); 3.563 (1.7); 2.676 (0.5); 2.671 (0.7); 2.667 (0.5); 2.525 (1.8); 2.511 (39.8); 2.507 (82.3); 2.502 (110.5); 2.498 (82.2); 2.494 (41.5); 2.334 (0.5); 2.329 (0.7); 2.325 (0.5); 0.146 (0.7); 0.008 (5.2); 0.000 (152.9); 0.009 (6.6); 0.150 (0.7)

Example Z-ii-02

[0457] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0458] =7.074 (1.3); 7.066 (4.4); 7.062 (10.3); 7.037 (10.0); 7.033 (4.6); 7.025 (1.2); 5.030 (0.4); 5.024 (0.4); 4.902 (15.8); 4.896 (16.0); 3.689 (3.7); 3.683 (7.6); 3.677 (3.7); 3.638 (0.5); 3.635 (0.5); 3.619 (0.5); 2.525 (0.6); 2.521 (1.0); 2.512 (15.2); 2.508 (31.2); 2.503 (41.5); 2.499 (30.5); 2.494 (15.1); 1.209 (1.3); 1.193 (1.5); 1.172 (0.7); 1.156 (0.5); 0.008 (2.2); 0.000 (63.2); 0.009 (2.5)

Example Z-ii-03

[0459] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0460] =7.177 (1.7); 7.171 (2.1); 7.154 (2.1); 7.152 (2.2); 7.148 (2.7); 7.145 (2.8); 7.129 (1.7); 7.121 (3.4); 7.116 (2.9); 7.109 (1.9); 7.094 (2.5); 7.089 (2.9); 7.083 (1.9); 5.756 (0.9); 5.030 (15.7); 5.024 (16.0); 3.756 (3.7); 3.750 (8.0); 3.744 (3.7); 3.500 (2.0); 2.676 (0.4); 2.671 (0.6); 2.667 (0.4); 2.525 (1.5); 2.520 (2.3); 2.511 (32.5); 2.507 (67.8); 2.502 (91.0); 2.498 (67.3); 2.493 (33.5); 2.333 (0.4); 2.329 (0.6); 2.324 (0.4); 0.146 (0.6); 0.008 (4.6); 0.000 (135.1); 0.009 (5.5); 0.150 (0.6)

Example Z-ii-04

[0461] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0462] =7.439 (1.1); 7.431 (11.3); 7.425 (3.7); 7.413 (3.9); 7.408 (12.5); 7.400 (1.2); 7.062 (1.3); 7.054 (12.6); 7.048 (4.0); 7.037 (3.7); 7.031 (11.1); 7.023 (1.0); 4.846 (15.9); 4.840 (16.0); 3.615 (3.8); 3.609 (7.7); 3.603 (3.7); 3.395 (13.0); 2.672 (0.4); 2.525 (1.1); 2.507 (50.6); 2.502 (65.5); 2.498 (48.7); 2.333 (0.3); 2.329 (0.4); 0.000 (0.6)

Example Z-ii-05

[0463] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0464] =7.407 (1.3); 7.398 (14.1); 7.393 (4.6); 7.388 (1.9); 7.381 (4.8); 7.375 (16.0); 7.367 (2.3); 7.024 (1.6); 7.016 (16.0); 7.010 (4.9); 6.999 (4.4); 6.993 (14.2); 6.984 (1.6); 6.982 (1.6); 6.976 (0.5); 6.965 (0.4); 6.959 (1.1); 6.072 (1.1); 6.059 (2.3); 6.046 (2.3); 6.033 (2.6); 6.029 (1.5); 6.019 (1.4); 6.016 (2.8); 6.003 (2.6); 5.989 (2.8); 5.976 (1.4); 5.419 (1.7); 5.414 (4.8); 5.410 (5.0); 5.406 (1.9); 5.375 (1.5); 5.371 (4.2); 5.367 (4.3); 5.363 (1.7); 5.288 (1.8); 5.284 (4.5); 5.281 (4.5); 5.277 (1.9); 5.262 (1.7); 5.258 (4.2); 5.254 (4.2); 5.251 (1.8); 4.605 (6.3); 4.601 (11.0); 4.598 (6.8); 4.592 (6.6); 4.588 (10.8); 4.584 (6.5); 4.067 (0.3); 4.049 (1.1); 4.032 (1.1); 4.014 (0.4); 3.332 (38.3); 2.526 (0.7); 2.521 (1.0); 2.512 (14.5); 2.508 (29.6); 2.503 (39.3); 2.499 (29.2); 2.494 (14.7); 1.397 (2.5); 1.337 (1.2); 1.319 (2.4); 1.302 (1.1); 0.008 (0.8); 0.000 (23.5); 0.009 (0.9)

Example Z-ii-06

[0465] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0466] =7.511 (6.3); 7.506 (6.7); 7.482 (6.5); 7.476 (7.0); 7.283 (3.1); 7.281 (3.1); 7.277 (3.2); 7.259 (8.4); 7.254 (9.0); 7.240 (9.5); 7.218 (10.8); 7.196 (4.2); 6.975 (0.4); 6.966 (0.6); 6.960 (0.5); 6.954 (0.4); 6.081 (1.5); 6.067 (3.1); 6.054 (3.1); 6.041 (3.6); 6.038 (2.6); 6.024 (4.0); 6.011 (3.6); 5.998 (3.8); 5.985 (1.8); 5.432 (6.6); 5.428 (7.2); 5.389 (5.8); 5.385 (6.3); 5.309 (6.6); 5.306 (6.9); 5.283 (6.4); 5.280 (6.5); 4.685 (16.0); 4.671 (15.8); 4.594 (0.5); 4.580 (0.5); 4.111 (0.5); 4.093 (0.5); 3.422 (10.6); 2.677 (0.3); 2.673 (0.5); 2.668 (0.4); 2.508 (53.9); 2.504 (71.0); 2.499 (54.5); 2.330 (0.5); 1.384 (0.5); 1.366 (1.1); 1.359 (0.4); 1.349 (0.6); 1.341 (0.7); 1.335 (0.4); 1.324 (0.4); 1.316 (0.5); 1.299 (1.3); 1.259 (1.5); 1.233 (2.1); 0.146 (0.4); 0.007 (3.1); 0.000 (81.0); 0.008 (4.4); 0.150 (0.4)

Example Z-ii-07

[0467] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0468] =7.368 (7.0); 7.355 (0.4); 7.345 (13.2); 7.321 (7.8); 7.115 (6.5); 7.107 (7.5); 7.099 (6.9); 7.091 (7.5); 6.995 (4.4); 6.985 (5.8); 6.977 (4.2); 6.972 (4.3); 6.962 (5.0); 6.954 (3.5); 6.057 (1.5); 6.044 (3.2); 6.031 (3.3); 6.018 (3.7); 6.014 (2.3); 6.004 (2.1); 6.001 (4.1); 5.988 (3.7); 5.974 (4.0); 5.961 (2.0); 5.417 (2.4); 5.413 (6.8); 5.408 (7.3); 5.404 (3.2); 5.374 (2.1); 5.369 (5.9); 5.365 (6.4); 5.361 (2.7); 5.287 (2.7); 5.284 (6.6); 5.280 (6.7); 5.276 (3.2); 5.261 (2.6); 5.257 (6.2); 5.253 (6.4); 5.250 (3.0); 4.571 (9.2); 4.567 (16.0); 4.563 (10.5); 4.557 (10.0); 4.554 (16.0); 4.550 (10.2); 4.528 (0.3); 4.524 (0.4); 3.749 (0.4); 3.745 (0.4); 3.701 (2.3); 2.527 (0.6); 2.513 (15.6); 2.509 (32.1); 2.505 (43.3); 2.500 (33.6); 2.496 (17.9)

Example Z-ii-08

[0469] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0470] =7.406 (3.8); 7.383 (7.2); 7.359 (4.2); 7.157 (3.6); 7.149 (4.1); 7.142 (3.7); 7.134 (4.0); 7.036 (2.5); 7.028 (2.8); 7.026 (3.2); 7.018 (2.3); 7.013 (2.2); 7.005 (2.5); 7.003 (2.7); 6.995 (1.9); 5.757 (0.4); 4.820 (15.8); 4.814 (16.0); 3.662 (1.5); 3.638 (0.6); 3.622 (3.8); 3.616 (8.0); 3.610 (3.8); 2.526 (0.4); 2.522 (0.6); 2.513 (8.9); 2.508 (18.3); 2.504 (24.5); 2.499 (18.2); 2.495 (9.0)

Example Z-ii-09

[0471] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0472] =7.633 (3.5); 7.614 (3.6); 7.605 (3.6); 7.586 (3.5); 7.477 (3.4); 7.458 (3.5); 7.448 (3.5); 7.429 (3.4); 4.972 (15.9); 4.966 (16.0); 3.720 (4.0); 3.714 (8.4); 3.708 (3.9); 3.328 (25.1); 2.526 (0.7); 2.512 (14.2); 2.508 (28.6); 2.503 (37.8); 2.499 (28.1); 2.495 (14.1); 1.398 (1.5); 0.008 (1.6); 0.000 (44.2); 0.009 (1.8)

Example Z-ii-10

[0473] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0474] =7.601 (6.5); 7.582 (6.6); 7.572 (6.6); 7.554 (6.5); 7.436 (6.1); 7.417 (6.3); 7.407 (6.2); 7.388 (6.1); 6.077 (1.6); 6.063 (3.4); 6.050 (3.2); 6.037 (3.9); 6.034 (2.4); 6.023 (2.3); 6.020 (4.3); 6.007 (3.7); 5.994 (4.2); 5.980 (2.1); 5.452 (2.6); 5.448 (7.1); 5.444 (7.4); 5.440 (2.9); 5.409 (2.3); 5.405 (6.2); 5.401 (6.4); 5.397 (2.5); 5.327 (6.9); 5.324 (6.9); 5.301 (6.4); 5.298 (6.5); 4.701 (9.6); 4.698 (16.0); 4.695 (10.2); 4.688 (9.9); 4.685 (15.7); 4.682 (9.8); 3.329 (39.8); 2.673 (0.4); 2.526 (1.0); 2.513 (22.1); 2.508 (44.8); 2.504 (59.2); 2.499 (43.9); 2.495 (22.0); 2.331 (0.4); 1.398 (1.3); 1.341 (0.3); 0.008 (2.4); 0.000 (67.0); 0.009 (2.7)

Example Z-ii-11

[0475] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0476] =7.535 (3.3); 7.530 (3.5); 7.506 (3.7); 7.500 (3.9); 7.328 (1.7); 7.322 (1.4); 7.305 (6.9); 7.299 (11.2); 7.278 (5.5); 7.256 (2.0); 4.945 (15.7); 4.939 (16.0); 3.676 (3.7); 3.670 (7.6); 3.664 (3.7); 3.532 (1.6); 2.526 (0.4); 2.508 (19.4); 2.504 (25.9); 2.499 (19.7); 0.008 (1.3); 0.000 (33.1); 0.008 (1.6)

Example Z-ii-12

[0477] .sup.1H-NMR (400.0 MHz, d6-DMSO):

[0478] =7.539 (8.4); 7.516 (9.3); 7.307 (8.3); 7.300 (8.7); 7.050 (5.0); 7.043 (4.7); 7.028 (4.6); 7.021 (4.4); 4.895 (15.8); 4.889 (16.0); 3.657 (3.7); 3.651 (7.9); 3.645 (3.7); 3.330 (28.0); 2.526 (0.6); 2.521 (0.9); 2.512 (13.4); 2.508 (27.6); 2.503 (36.7); 2.499 (27.0); 2.494 (13.4); 1.397 (1.0); 0.008 (2.2); 0.000 (59.6); 0.009 (2.4)

Example Z-ii-13

[0479] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0480] =7.506 (14.6); 7.495 (2.5); 7.484 (15.9); 7.473 (2.5); 7.273 (0.4); 7.261 (14.2); 7.254 (15.1); 7.222 (2.0); 7.215 (2.2); 7.014 (8.5); 7.007 (8.1); 6.991 (7.8); 6.984 (7.6); 6.979 (1.8); 6.972 (1.3); 6.957 (1.1); 6.950 (1.1); 6.061 (1.6); 6.048 (3.2); 6.035 (3.2); 6.022 (3.6); 6.018 (2.3); 6.008 (2.1); 6.005 (4.0); 5.992 (3.7); 5.978 (3.9); 5.965 (1.9); 5.424 (2.4); 5.420 (6.6); 5.416 (7.0); 5.412 (2.9); 5.381 (2.1); 5.377 (5.8); 5.373 (6.1); 5.369 (2.5); 5.297 (6.7); 5.294 (6.8); 5.271 (6.2); 5.267 (6.4); 4.641 (9.0); 4.638 (16.0); 4.635 (10.3); 4.628 (9.5); 4.625 (15.8); 4.621 (9.7); 4.609 (0.4); 4.099 (0.9); 4.082 (3.0); 4.064 (3.0); 4.047 (0.9); 3.330 (57.6); 2.677 (0.5); 2.672 (0.6); 2.668 (0.5); 2.526 (1.5); 2.512 (34.5); 2.508 (70.6); 2.503 (94.1); 2.499 (70.3); 2.495 (35.9); 2.335 (0.4); 2.330 (0.6); 2.326 (0.5); 1.398 (1.7); 1.333 (3.0); 1.316 (6.2); 1.299 (3.0); 0.146 (0.7); 0.008 (5.4); 0.000 (148.3); 0.008 (6.7); 0.150 (0.7)

Example Z-ii-14

[0481] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0482] =7.386 (3.4); 7.366 (7.2); 7.345 (6.1); 7.240 (7.1); 7.229 (7.4); 7.227 (4.9); 7.220 (4.3); 7.218 (4.6); 7.209 (5.0); 7.206 (4.1); 5.008 (15.9); 5.002 (16.0); 3.713 (4.2); 3.707 (8.9); 3.702 (4.0); 3.331 (23.3); 2.672 (0.4); 2.525 (1.0); 2.512 (20.9); 2.508 (41.7); 2.503 (54.2); 2.499 (39.4); 2.495 (19.5); 2.330 (0.3); 1.397 (1.0); 0.146 (0.4); 0.008 (3.8); 0.000 (89.9); 0.009 (3.6); 0.150 (0.4)

Example Z-ii-16

[0483] .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

[0484] =7.260 (3.6); 6.946 (2.3); 6.936 (2.8); 6.920 (2.8); 6.915 (5.2); 6.910 (3.6); 6.906 (6.6); 6.890 (4.9); 6.880 (6.6); 6.861 (9.0); 6.845 (14.8); 6.836 (7.1); 6.830 (5.3); 6.818 (8.6); 6.808 (6.3); 6.123 (1.6); 6.106 (3.2); 6.088 (2.9); 6.070 (3.8); 6.065 (2.3); 6.054 (2.2); 6.048 (4.2); 6.031 (3.6); 6.013 (4.4); 5.996 (2.3); 5.541 (2.6); 5.536 (6.4); 5.531 (6.8); 5.526 (3.1); 5.483 (2.2); 5.478 (5.3); 5.473 (5.6); 5.468 (2.5); 5.359 (2.8); 5.354 (7.0); 5.350 (7.1); 5.345 (3.1); 5.323 (2.6); 5.319 (6.4); 5.314 (6.6); 5.310 (2.9); 4.600 (9.0); 4.595 (16.0); 4.590 (10.0); 4.584 (9.8); 4.578 (16.0); 4.573 (9.4); 1.561 (7.2); 1.264 (1.1); 0.903 (0.4); 0.881 (1.2); 0.858 (0.5); 0.000 (3.4)

Example Z-ii-17

[0485] .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

[0486] =7.262 (2.8); 7.048 (2.0); 7.032 (2.2); 7.018 (4.4); 7.002 (4.3); 6.974 (2.5); 6.964 (2.9); 6.948 (2.6); 6.944 (1.5); 6.938 (3.0); 6.934 (1.8); 6.918 (1.1); 6.908 (1.6); 6.875 (3.5); 6.865 (2.9); 6.847 (3.6); 6.837 (2.9); 5.300 (0.6); 4.774 (15.7); 4.766 (16.0); 2.576 (3.8); 2.568 (7.7); 2.560 (3.9); 1.559 (5.4); 0.000 (2.6)

Example Z-ii-18

[0487] .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

[0488] =7.259 (1.2); 7.027 (2.8); 7.000 (3.4); 6.861 (3.1); 6.757 (1.7); 6.754 (1.7); 6.730 (1.4); 6.727 (1.4); 5.298 (0.5); 4.774 (8.1); 4.766 (8.2); 2.569 (2.1); 2.561 (4.2); 2.553 (2.1); 2.354 (16.0); 1.562 (2.5); 0.000 (1.0)

Example Z-ii-19

[0489] .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

[0490] =7.522 (7.5); 7.515 (8.2); 7.493 (8.4); 7.486 (9.2); 7.358 (15.3); 7.351 (14.1); 7.266 (6.7); 6.986 (14.1); 6.957 (12.7); 6.128 (1.5); 6.111 (3.2); 6.093 (3.0); 6.076 (3.8); 6.071 (2.3); 6.059 (2.3); 6.054 (4.2); 6.036 (3.7); 6.018 (4.4); 6.001 (2.3); 5.567 (2.9); 5.562 (6.4); 5.558 (6.6); 5.553 (3.2); 5.510 (2.4); 5.505 (5.3); 5.501 (5.3); 5.496 (2.6); 5.417 (3.1); 5.413 (7.1); 5.409 (6.9); 5.405 (3.1); 5.382 (2.8); 5.378 (6.4); 5.373 (6.3); 5.369 (2.8); 4.713 (9.3); 4.708 (16.0); 4.703 (9.9); 4.696 (10.1); 4.691 (15.8); 4.686 (9.1); 1.588 (3.5); 0.000 (5.8)

Example Z-ii-20

[0491] .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

[0492] =7.557 (3.9); 7.551 (4.2); 7.529 (4.5); 7.522 (4.9); 7.385 (7.7); 7.378 (7.2); 7.270 (1.9); 7.165 (7.6); 7.136 (6.6); 4.889 (15.9); 4.881 (16.0); 2.647 (4.1); 2.639 (8.4); 2.631 (4.1); 1.609 (4.3); 0.000 (1.5)

Biological Examples

Biological Example 1: In Vivo Preventive Test on Puccinia recondita (Brown Rust on Wheat)

[0493]

TABLE-US-00006 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0494] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0495] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0496] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20 C. and at 100% relative humidity and then for 10 days at 20 C. and at 70-80% relative humidity.

[0497] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0498] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-04.

Biological Example 2: In Vivo Preventive Test on Septoria tritici (Leaf Spot on Wheat)

[0499]

TABLE-US-00007 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0500] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0501] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0502] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18 C. and at 100% relative humidity and then for 21 days at 20 C. and at 90% relative humidity.

[0503] The test is evaluated 24 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0504] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-04.

Biological Example 3: In Vivo Preventive Test on Sphaerotheca Fuliginea (Powdery Mildew on Cucurbits)

[0505]

TABLE-US-00008 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0506] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0507] The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0508] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants are incubated for 72 hours at 18 C. and at 100% relative humidity and then for 12 days at 20 C. and at 70-80% relative humidity.

[0509] The test is evaluated 15 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0510] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03.

Biological Example 4: In Vivo Preventive Test on Uromyces Appendiculatus (Bean Rust)

[0511]

TABLE-US-00009 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0512] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0513] The young plants of bean are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0514] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants are incubated for 24 hours at 20 C. and at 100% relative humidity and then for 10 days at 20 C. and at 70-80% relative humidity.

[0515] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0516] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03.

Biological Example 5: In Vivo Preventive Test on Venturia inaequalis (Apples)

[0517]

TABLE-US-00010 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0518] 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 water to the desired concentration.

[0519] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 100%.

[0520] The plants are then placed in a greenhouse at approximately 21 C. and a relative atmospheric humidity of approximately 90%.

[0521] The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0522] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 250 ppm of active ingredient: I-01; I-02; I-03.

Biological Example B1: In Vivo Preventive Test on Botrytis Cinerea (Grey Mould)

[0523]

TABLE-US-00011 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0524] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0525] The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0526] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The contaminated gherkin plants are incubated for 4 to 5 days at 17 C. and at 90% relative humidity.

[0527] The test is evaluated 4 to 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0528] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-03; I-42

[0529] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-05

[0530] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-07; I-19; I-26; I-64

Biological Example B2: In Vivo Preventive Test on Puccinia recondita (Brown Rust on Wheat)

[0531]

TABLE-US-00012 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0532] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0533] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0534] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20 C. and at 100% relative humidity and then for 10 days at 20 C. and at 70-80% relative humidity.

[0535] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0536] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-14; I-19; I-31; I-52; I-56; I-62; I-63; I-65

[0537] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-02; I-03; I-04; I-06; I-08; I-09; I-16; I-29; I-30; I-41; I-45; I-47; I-49; I-50; I-51; I-53; I-57; I-58; I-64; I-66; I-67

[0538] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-05; I-32; I-42; I-59; I-60; I-61

Biological Example B3: In Vivo Preventive Test on Septoria tritici (Leaf Spot on Wheat)

[0539]

TABLE-US-00013 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0540] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0541] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0542] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18 C. and at 100% relative humidity and then for 21 days at 20 C. and at 90% relative humidity.

[0543] The test is evaluated 24 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0544] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-17; I-18; I-24; I-25; I-28; I-44; I-45; I-46; I-50; I-55; I-56

[0545] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-04; I-05; I-06; I-07; I-08; I-09; I-13; I-14; I-15; I-16; I-19; I-22; I-23; I-26; I-29; I-30; I-31; I-32; I-33; I-34; I-35; I-36; I-37; I-38; I-39; I-40; I-41; I- 42; I-43; I-47; I-48; I-49; I-51; I-52; I-53; I-54; I-57; I-58; I-59; I-60; I-61; I-62; I-63; I-64; I-65; I-66; I-67

Biological Example B4: In Vivo Preventive Test on Sphaerotheca fuliginea (Powdery Mildew on Cucurbits)

[0546]

TABLE-US-00014 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0547] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0548] The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0549] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants are incubated for 72 hours at 18 C. and at 100% relative humidity and then for 12 days at 20 C. and at 70-80% relative humidity.

[0550] The test is evaluated 15 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0551] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-38; I-47

[0552] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-09; I-17; I-33; I-43; I-46; I-57

[0553] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-05; I-07; I-16; I-18; I-19; I-29; I-31; I-32; I-34; I-41; I-42; I-44; I-45; I-48; I-49; I-50; I-51; I-52; I-53; I-54; I-59; I-60; I-61; I-62; I-63; I-64; I-65; I-66; I-67

Biological Example B5: In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)

[0554]

TABLE-US-00015 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

[0555] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

[0556] The young plants of bean are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.

[0557] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants are incubated for 24 hours at 20 C. and at 100% relative humidity and then for 10 days at 20 C. and at 70-80% relative humidity.

[0558] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0559] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-16; I-65; I-67

[0560] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-60; I-64

[0561] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-59

Biological Example B6: In Vivo Preventive Test on Alternaria solani (Tomatoes)

[0562]

TABLE-US-00016 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0563] 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 water to the desired concentration.

[0564] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 100%.

[0565] The test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed.

[0566] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 50 ppm of active ingredient: I-16

[0567] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 ppm of active ingredient: I-01; I-02; I-03; I-19; I-59; I-60; I-61; I-64

Biological Example B7: In Vivo Preventive Test on Phakopsora pachyrhizi (Soybeans)

[0568]

TABLE-US-00017 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0569] 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 water to the desired concentration.

[0570] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24 h without light in an incubation cabinet at approximately 24 C. and a relative atmospheric humidity of 95%.

[0571] The plants remain in the incubation cabinet at approximately 24 C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.

[0572] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0573] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 250 ppm of active ingredient: I-01; I-02; I-03; I-59

Biological Example B8: In Vivo Preventive Test on Sphaerotheca fuliginea (Cucumbers)

[0574]

TABLE-US-00018 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0575] 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 water to the desired concentration.

[0576] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at approximately 23 C. and a relative atmospheric humidity of approximately 70%.

[0577] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0578] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 ppm of active ingredient: I-01; I-02; I-64

Biological Example B9: In Vivo Preventive Test on Venturia inaequalis (Apples)

[0579]

TABLE-US-00019 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0580] 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 water to the desired concentration.

[0581] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 100%.

[0582] The plants are then placed in a greenhouse at approximately 21 C. and a relative atmospheric humidity of approximately 90%.

[0583] The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0584] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 250 ppm of active ingredient: I-01; I-02; I-03; I-05; I-16; I-19; I-59; I-60; I-61; I-64

Biological Examples C1 to C3: Comparative Examples

Biological Example C1: In Vivo Preventive Test on Alternaria solani (Tomatoes)

[0585]

TABLE-US-00020 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0586] 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 water to the desired concentration.

[0587] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 100%.

[0588] The test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed.

TABLE-US-00021 EFFICACY TABLE C1 in vivo preventive test on Alternaria solani (tomatoes) Rate of application of Effi- active compound cacy Active compound in ppm in % Known from WO 2010/101973: [00018] 50 40 According to the invention: Ex. I-01 [00019] 50 96

Biological Example C2: In Vivo Preventive Test on Phakopsora pachyrhizi (Soybeans)

[0589]

TABLE-US-00022 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0590] 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 water to the desired concentration.

[0591] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24 h without light in an incubation cabinet at approximately 24 C. and a relative atmospheric humidity of 95%. The plants remain in the incubation cabinet at approximately 24 C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.

[0592] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

TABLE-US-00023 EFFICACY TABLE C2 in vivo preventive test on Phakopsora pachyrhizi (soybeans) Rate of application of Effi- active compound cacy Active compound in ppm in % Known from WO 2010/101973: [00020] 250 53 According to the invention: Ex. I-01 [00021] 250 94

Biological Example C3: In Vivo Preventive Test on Sphaerotheca fuliginea (Cucumbers)

[0593]

TABLE-US-00024 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0594] 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 water to the desired concentration.

[0595] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at approximately 23 C. and a relative atmospheric humidity of approximately 70%.

[0596] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

TABLE-US-00025 EFFICACY TABLE C3 in vivo preventive test on Sphaerotheca fuliginea (cucumbers) Rate of application of Effi- active compound cacy Active compound in ppm in % Known from WO 2010/101973: [00022] 50 10 According to the invention: Ex. I-01 [00023] 50 98