USE OF [(1,5-DIPHENYL-1H-PYRAZOL-3-YL)OXY] ACETIC ACID DERIVATIVES AND THEIR SALTS AND COMPOSITIONS CONTAINING THEM, FOR REDUCING PHYTOTOXIC EFFECTS OF AGROCHEMICALS, IN PARTICULAR OF HERBICIDES, IN USEFUL PLANTS AND CROP PLANTS

Abstract

The present invention relates to the use of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy] acetic acid derivatives of the formula (I) and their salts (I)

##STR00001## and compositions containing them, for reducing phytotoxic effects of agrochemicals, in particular of herbicides, in useful plants and crop plants.

The invention also and in particular relates to certain [(1,5-diphenyl-1H-pyrazol-3-yl)oxy] acetic acid derivatives of the formula (I) and processes for preparing them.

Claims

1. A method of reducing phytotoxic effects of pesticides on plants, the method comprising use of compounds of general formula (I) or salts thereof ##STR00136## in which R.sup.1 and R.sup.2 are independently hydrogen, halogen, cyano, nitro, (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkenyl, (C.sub.1-C.sub.6)alkoxy and (C.sub.1-C.sub.6)alkylS(O).sub.p, where the latter seven radicals are unsubstituted or substituted by one or more radicals from the group of halogen, cyano, (C.sub.1-C.sub.6)alkoxy and (C.sub.1-C.sub.6)alkylS(O).sub.p, R.sup.3 is hydrogen and (C.sub.1-C.sub.6)alkyl, R.sup.4 is hydrogen, (C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkyl, (C.sub.1-C.sub.18)cyanoalkyl, (C.sub.2-C.sub.18)alkenyl, (C.sub.2-C.sub.18)alkynyl, (C.sub.3-C.sub.12)cycloalkyl, (C.sub.3-C.sub.12)cycloalkenyl, aryl, heteroaryl, (C.sub.1-C.sub.18)alkoxy-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkoxy-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)alkoxy-(C.sub.1-C.sub.18)haloalkyl, (C.sub.1-C.sub.18)alkylthio-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkylthio-(C.sub.1-C.sub.18)alkyl, (C.sub.2-C.sub.18)haloalkenyl, (C.sub.2-C.sub.18)haloalkynyl, heterocyclyl-(C.sub.1-C.sub.18)alkyl, aryl-(C.sub.1-C.sub.18)alkyl, (C.sub.3-C.sub.12)cycloalkyl-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)alkoxycarbonyl-(C.sub.1-C.sub.18)alkyl, and (C.sub.1-C.sub.18)alkoxycarbonyl-(C.sub.3-C.sub.12)cycloalkyl-(C.sub.1-C.sub.18)alkyl, or a radical of the formula —NR.sup.aR.sup.b or —N═CR.sup.cR.sup.d, where, in the former 2 radicals, each of the R.sup.a, R.sup.b, R.sup.c and R.sup.d radicals is independently hydrogen, (C.sub.1-C.sub.4)alkyl, (C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl, or R.sup.a and R.sup.b together with the nitrogen atom may form a 3- to 8-membered heterocycle which may contain one or two further ring heteroatoms from the group of N, O and S and which is unsubstituted or substituted by one or more radicals from the group of (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl, or R.sup.c and R.sup.d together with the carbon atom are a 3- to 8-membered carbocyclic or heterocyclic radical which may contain 1 to 3 ring heteroatoms from the group of N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted by one or more radicals from the group of (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl, n and m are independently a number from 0 to 5, and p is 0, 1 or 2.

2. The method of claim 1, wherein in compounds of the general formula (I) R.sup.1 and R.sup.2 are independently hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF.sub.3, CF.sub.2Cl, CH.sub.2F, CHF.sub.2, OCH.sub.3, OCF.sub.3, SCH.sub.3, SOCH.sub.3, SO.sub.2CH.sub.3 and SCF.sub.3, R.sup.3 is hydrogen and CH.sub.3, R.sup.4 is hydrogen, (C.sub.1-C.sub.10)alkyl, (C.sub.1-C.sub.10)haloalkyl, (C.sub.1-C.sub.10)cyanoalkyl, (C.sub.2-C.sub.10)alkenyl, (C.sub.2-C.sub.10)alkynyl, (C.sub.3-C.sub.9)cycloalkyl, (C.sub.3-C.sub.9)cycloalkenyl, aryl, heteroaryl, (C.sub.1-C.sub.10)alkoxy-(C.sub.1-C.sub.10)alkyl, (C.sub.1-C.sub.10)haloalkoxy-(C.sub.1-C.sub.10)alkyl, (C.sub.1-C.sub.10)alkoxy-(C.sub.1-C.sub.10)haloalkyl, (C.sub.1-C.sub.10)alkylthio-(C.sub.1-C.sub.10)alkyl, (C.sub.1-C.sub.10)haloalkylthio-(C.sub.1-C.sub.10)alkyl, (C.sub.2-C.sub.18)haloalkenyl, (C.sub.2-C.sub.18)haloalkynyl, heterocyclyl-(C.sub.1-C.sub.10)alkyl, aryl-(C.sub.1-C.sub.10)alkyl, (C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.10)alkyl, (C.sub.1-C.sub.10)alkoxycarbonyl-(C.sub.1-C.sub.10)alkyl and (C.sub.1-C.sub.10)alkoxycarbonyl-(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.10)alkyl, n and m are independently 0, 1, 2 or 3, and p is 0, 1 or 2.

3. The method of claim 1, wherein in compounds of the general formula (I) R.sup.1 and R.sup.2 are independently hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF.sub.3, CH.sub.2F, CHF.sub.2, OCH.sub.3, OCF.sub.3, SCH.sub.3, SOCH.sub.3, SO.sub.2CH.sub.3 and SCF.sub.3, R.sup.3 is hydrogen, R.sup.4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH.sub.2(4-Cl-Ph), CH.sub.2(4-F-Ph), CH.sub.2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacet-2-yl, ethylacet-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethyl-propanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloro-prop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, n and m are independently 0, 1, 2 or 3, where m and n must not both be 0.

4. The method of claim 1, wherein in compounds of the general formula (I), (R.sup.1).sub.n-phenyl is selected from the group consisting of Q-1.1 to Q-1.53 ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## and (R.sup.2).sub.m-phenyl is selected from the group consisting of Q-2.1 to Q-2.53 ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## R.sup.3 is hydrogen, and R.sup.4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH.sub.2(4-Cl-Ph), CH.sub.2(4-F-Ph), CH.sub.2(4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacet-2-yl, ethylacet-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

5. A plant-protecting composition, comprising: at least one compound of the general formula (I) or salts thereof as claimed in claim 1; and at least one agrochemical.

6. The composition as claimed in claim 5, comprising at least one herbicide.

7. A method of reducing phytotoxic effects of pesticides on plants, the method comprising use of one or more compounds of claim 1 or of the composition as claimed in claim 5.

8. A method of reducing phytotoxic effects of pesticides on plants, the method comprising: use of one or more compounds of the general formula (I) as claimed in claim 1; and use of pesticides deployed simultaneously or sequentially.

9. The method as claimed in claim 8, wherein the pesticides are one or more herbicides.

10. The method as claimed in claim 8, characterized in that compounds of the formula (I) or salts thereof as claimed in claim 1 are applied to the plants, parts of the plants, or seeds or seed material thereof.

11. A compound of general formula (I) or salt thereof ##STR00151## in which R.sup.1 and R.sup.2 are independently hydrogen, halogen, cyano, nitro, (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.3-C.sub.8)cycloalkyl, (C.sub.3-C.sub.8)cycloalkenyl, (C.sub.1-C.sub.6)alkoxy and (C.sub.1-C.sub.6)alkylS(O).sub.p, where the latter seven radicals are unsubstituted or substituted by one already more radicals from the group of halogen, cyano, (C.sub.1-C.sub.6)alkoxy and (C.sub.1-C.sub.6)alkylS(O).sub.p, R.sup.3 is hydrogen and (C.sub.1-C.sub.6)alkyl, R.sup.4 is hydrogen, (C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkyl, (C.sub.1-C.sub.18)cyanoalkyl, (C.sub.2-C.sub.18)alkenyl, (C.sub.2-C.sub.18)alkynyl, (C.sub.3-C.sub.12)cycloalkyl, (C.sub.3-C.sub.12)cycloalkenyl, aryl, heteroaryl, (C.sub.1-C.sub.18)alkoxy-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkoxy-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)alkoxy-(C.sub.1-C.sub.18)haloalkyl, (C.sub.1-C.sub.18)alkylthio-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkylthio-(C.sub.1-C.sub.18)alkyl, (C.sub.2-C.sub.18)haloalkenyl, (C.sub.2-C.sub.18)haloalkynyl, heterocyclyl-(C.sub.1-C.sub.18)alkyl, aryl-(C.sub.1-C.sub.18)alkyl, (C.sub.3-C.sub.12)cycloalkyl-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)alkoxycarbonyl-(C.sub.1-C.sub.18)alkyl, and (C.sub.1-C.sub.18)alkoxycarbonyl-(C.sub.3-C.sub.12)cycloalkyl-(C.sub.1-C.sub.18)alkyl, or a radical of the formula —NR.sup.aR.sup.b or —N═CR.sup.cR.sup.d, where, in the former 2 radicals, each of the R.sup.a, R.sup.b, R.sup.c and R.sup.d radicals is independently hydrogen, (C.sub.1-C.sub.4)alkyl, (C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl, or R.sup.a and R.sup.b together with the nitrogen atom may form a 3- to 8-membered heterocycle which may contain one or two further ring heteroatoms from the group of N, O and S and which is unsubstituted or substituted by one or more radicals from the group of (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl, or R.sup.c and R.sup.d together with the carbon atom are a 3- to 8-membered carbocyclic or heterocyclic radical which may contain 1 to 3 ring heteroatoms from the group of N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted by one or more radicals from the group of (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl, n and m are independently a number from 0 to 5, and p is 0, 1 or 2, excluding the following compounds: {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-73-0]) {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-75-2]) {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-76-3]) {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4]) {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-85-4]) {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-91-4]) [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS [73457-62-2]) sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS [73457-94-0]) {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1]) {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-89-0]) {[1,5-bis(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-05-3]) {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-79-6]) {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-00-8]) ethyl [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS [1246513-41-6]) {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-99-2]) ({1-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1076207-90-3]) ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-42-7]) {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-04-2]) {[1-phenyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-88-9]) {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-84-3]) ethyl {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-87-8]) ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-43-8]) ethyl {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-44-9]) ethyl {[1-(4-isopropylphenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-47-2]) ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1338378-37-2]) ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-46-1]) {[1-(4-tert-butylphenyl)-5-(3,4-dimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS 1076208-01-9) {[5-(2,4-dichlorophenyl)-1-(4-isopropylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-80-9]) ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-83-2]) ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-81-0]) ethyl {[1-(4-tert-butylphenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-93-6]) ethyl {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-03-1]) ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-98-1]) ethyl {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-48-3]) ethyl {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-50-7]) ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-86-5]) ethyl {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-97-0]) ethyl {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1310875-82-1]) ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-94-7]) ethyl {[1-phenyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-45-0]) ethyl {[1-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-02-0]) ethyl {[1-(4-fluorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-06-4]) {[5-(3,4-dimethoxyphenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-78-5]) ethyl {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-92-5]) ethyl {[1-(2,4-dichlorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-95-8]) ethyl {[5-(4-chlorophenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-96-9]).

12. The compound of claim 11, where R.sup.1 and R.sup.2 are independently hydrogen, halogen, cyano, nitro, (C.sub.1-C.sub.4)alkyl, (C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkenyl, (C.sub.1-C.sub.4)alkoxy and (C.sub.1-C.sub.4)alkylS(O).sub.p, where the latter seven radicals are unsubstituted or substituted by one already more radicals from the group of halogen, cyano, (C.sub.1-C.sub.4)alkoxy and (C.sub.1-C.sub.4)alkylS(O).sub.p, R.sup.3 is hydrogen and (C.sub.1-C.sub.4)alkyl, R.sup.4 is hydrogen, (C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkyl, (C.sub.1-C.sub.18)cyanoalkyl, (C.sub.2-C.sub.18)alkenyl, (C.sub.2-C.sub.18)alkynyl, (C.sub.3-C.sub.12)cycloalkyl, (C.sub.3-C.sub.12)cycloalkenyl, aryl, heteroaryl, (C.sub.1-C.sub.18)alkoxy-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkoxy-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)alkoxy-(C.sub.1-C.sub.18)haloalkyl, (C.sub.1-C.sub.18)alkylthio-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)haloalkylthio-(C.sub.1-C.sub.18)alkyl, (C.sub.2-C.sub.18)haloalkenyl, (C.sub.2-C.sub.18)haloalkynyl, heterocyclyl-(C.sub.1-C.sub.18)alkyl, aryl-(C.sub.1-C.sub.18)alkyl, (C.sub.3-C.sub.12)cycloalkyl-(C.sub.1-C.sub.18)alkyl, (C.sub.1-C.sub.18)alkoxycarbonyl-(C.sub.1-C.sub.18)alkyl, and (C.sub.1-C.sub.18)alkoxycarbonyl-(C.sub.3-C.sub.12)cycloalkyl-(C.sub.1-C.sub.18)alkyl, n and m are independently a number from 0 to 4, and p is 0, 1 or 2, excluding the following compounds: {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-73-0]) {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-75-2]) {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-76-3]) {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4]) {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-85-4]) {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-91-4]) [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS [73457-62-2]) sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS [73457-94-0]) {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1]) {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-89-0]) {[1,5-bis(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-05-3]) {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-79-6]) {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-00-8]) ethyl [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS [1246513-41-6]) {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-99-2]) ({1-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1076207-90-3]) ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-42-7]) {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-04-2]) {[1-phenyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-88-9]) {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-84-3]) ethyl {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-87-8]) ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-43-8]) ethyl {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-44-9]) ethyl {[1-(4-isopropylphenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-47-2]) ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1338378-37-2]) ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-46-1]) {[1-(4-tert-butylphenyl)-5-(3,4-dimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-01-9]) {[5-(2,4-dichlorophenyl)-1-(4-isopropylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-80-9]) ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-83-2]) ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-81-0]) ethyl {[1-(4-tert-butylphenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-93-6]) ethyl {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-03-1]) ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-98-1]) ethyl {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-48-3]) ethyl {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-50-7]) ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-86-5]) ethyl {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-97-0]) ethyl {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1310875-82-1]) ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-94-7]) ethyl {[1-phenyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-45-0]) ethyl {[1-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-02-0]) ethyl {[1-(4-fluorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-06-4]) {[5-(3,4-dimethoxyphenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-78-5]) ethyl {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-92-5]) ethyl {[1-(2,4-dichlorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-95-8]) ethyl {[5-(4-chlorophenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-96-9]).

13. The compound of claim 11, where R.sup.1 and R.sup.2 are independently hydrogen, halogen, cyano, methyl, ethyl, CF.sub.3, CF.sub.2Cl, CH.sub.2F, CHF.sub.2, OCH.sub.3, OCF.sub.3, SCH.sub.3, SOCH.sub.3, SO.sub.2CH.sub.3 and SCF.sub.3, R.sup.3 is hydrogen, R.sup.4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH.sub.2(4-Cl-Ph), CH.sub.2(4-F-Ph), CH.sub.2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethyl-propanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate-2-yl, methylacet-2-yl, ethylacet-2-yl, methyl-1-methyl-cyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-tri-fluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloro-prop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, n and m are independently 0, 1, 2 or 3, where m and n must not both be 0, excluding the following compounds: {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-73-0]) {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-75-2]) {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-76-3]) {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4]) {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-85-4]) {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-91-4]) [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS [73457-62-2]) sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS [73457-94-0]) {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1]) {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-89-0]) {[1,5-bis(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-05-3]) {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-79-6]) {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-00-8]) ethyl [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS [1246513-41-6]) {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-99-2]) ({1-phenyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1076207-90-3]) ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-42-7]) {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-04-2]) {[1-phenyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076207-88-9]) {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-84-3]) ethyl {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-87-8]) ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-43-8]) ethyl {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-44-9]) ethyl {[1-(4-isopropylphenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-47-2]) ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1338378-37-2]) ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-46-1]) {[1-(4-tert-butylphenyl)-5-(3,4-dimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-01-9]) {[5-(2,4-dichlorophenyl)-1-(4-isopropylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-80-9]) ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-83-2]) ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-81-0]) ethyl {[1-(4-tert-butylphenyl)-5-phenyl-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-93-6]) ethyl {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-03-1]) ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-98-1]) ethyl {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-48-3]) ethyl {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-50-7]) ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS [1310875-86-5]) ethyl {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-97-0]) ethyl {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1310875-82-1]) ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-94-7]) ethyl {[1-phenyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1246513-45-0]) ethyl {[1-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-02-0]) ethyl {[1-(4-fluorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076208-06-4]) {[5-(3,4-dimethoxyphenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-78-5]) ethyl {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-92-5]) ethyl {[1-(2,4-dichlorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-95-8]) ethyl {[5-(4-chlorophenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetate (CAS [1076207-96-9]).

14. The compounds of claim 11, where (R.sup.1).sub.n-phenyl is selected from the group consisting of Q-1.2 to Q-1.53 ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## and (R.sup.2).sub.m phenyl is selected from the group consisting of Q-2.2 to Q-2.53 ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## R.sup.3 is hydrogen, and R.sup.4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH.sub.2(4-Cl-Ph), CH.sub.2(4-F-Ph), CH.sub.2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacet-2-yl, ethylacet-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, excluding the following compounds: {[1,5-bis(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-05-3]) {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-79-6]) {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1076208-04-2]) {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-84-3])

15. The compound of claim 11, where (R.sup.1).sub.n-phenyl is selected from the group consisting of: Q-1.2, Q-1.3, Q-1.4, Q-1.5, Q-1.6, Q-1.7, Q-1.32, Q-1.33, Q-1.34, Q-1.3, Q-1.36, Q-1.37, Q-1.38, Q-1.39, Q-1.40, Q-1.41, Q-1.42, Q-1.43, Q-1.45, Q-1.46, Q-1.47, Q-1.48, Q-1.49, Q-1.50, Q-1.51, Q-1.52, Q-1.53 as defined in claim 14, (R.sup.2).sub.m-phenyl is selected from the group consisting of: Q-2.2, Q-2.3, Q-2.5, Q-2.6, Q-2.7, Q-2.33, Q-2.34, Q-2.35, Q-2.36, Q-2.37, Q-2.38, Q-2.39, Q-2.40, Q-2.41, Q-2.42, Q-2.43, Q-2.45, Q-2.46, Q-2.47, Q-2.48, Q-2.4, Q-2.50, Q-2.51, Q-2.52, Q-2.53 as defined in claim 14, R3 is hydrogen, and R4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacet-2-yl, ethylacet-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropane-carboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methyl-cyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethyl-cyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

16. The composition as claimed in claim 5, further comprising at least one formulation auxiliary.

17. The method of claim 7, further comprising use of at least one herbicide.

18. The method of claim 10, further comprising use of at least one herbicide.

Description

SYNTHESIS EXAMPLES

Synthesis Example No.: I.48-32

Synthesis Stage 1: 3-(4-Chloro-2-fluorophenyl)-N′-(2,4-dichlorophenyl)prop-2-yne hydrazide

[0412] ##STR00054##

[0413] 3-(4-Chloro-2-fluorophenyl)prop-2-ynoic acid (2.98 g, 15.00 mmol, 1.0 equiv) and DMF (0.10 ml, 1.35 mmol, 0.1 equiv) were dissolved in DCM (120 ml) and cooled down to 0° C. with an ice bath. Oxalyl chloride (2.28 g, 18.00 mmol, 1.2 equiv) was added in portions to the solution. Caution: evolution of gas! Subsequently, the ice bath was removed and the reaction mixture was stirred at room temperature for 1 h. The solvent was then removed under reduced pressure and the residue was dissolved in DCM (150 ml). (2,4-Dichlorophenyl)hydrazine (5.31 g, 30 mmol, 2.0 equiv) and triethylamine (3.04 g, 30.00 mmol, 2 equiv) were added to the solution, and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was extracted with water (150 ml). The aqueous phase was extracted twice with DCM (200 ml each time). The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. 3-(4-Chloro-2-fluorophenyl)-N′-(2,4-dichlorophenyl)prop-2-yne hydrazide was isolated in the form of a white solid (3.20 g, 59% of theory). .sup.1H NMR (400 MHz, DMSO-d.sup.6 δ, ppm)

Synthesis Stage 2: 5-(4-Chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1,2-dihydro-3H-pyrazol-3-one

[0414] ##STR00055##

[0415] 3-(4-Chloro-2-fluorophenyl)-N′-(2,4-dichlorophenyl)prop-2-yne hydrazide (2.86 g, 8.00 mmol, 1.0 equiv) was dissolved in n-butanol (60 ml), and then potassium carbonate (1.66 g, 12.00 mmol, 2.0 equiv) was added at room temperature. The solution turned pink after about 15-30 min, and a beige solid precipitated out. The reaction mixture was heated to boiling for 2 h and cooled down to room temperature, and the solvent was removed under reduced pressure. The residue was dissolved in DCM (150 ml) and water (100 ml). The organic phase was then washed with a saturated sodium chloride solution and dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate/heptane gradient). 5-(4-Chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1,2-dihydro-3H-pyrazol-3-one was isolated in the form of a beige solid (1.53 g, 71% of theory). .sup.1H NMR (400 MHz, DMSO-d.sup.6 δ, ppm)

Synthesis Stage 3: Ethyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetate (synthesis example I.47-32)

[0416] ##STR00056##

[0417] 1-(4-Chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol (1.7 g, 5.53 mmol, 1.0 equiv) and potassium carbonate (1.53 g, 11.05 mmol, 2 equiv) were suspended in acetonitrile (20 ml), and then ethyl bromoacetate (0.48 g, 6.63 mmol, 1.2 equiv) was added. Then the suspension was stirred at room temperature overnight, the solid was filtered off, and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate/heptane gradient). Ethyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetate was isolated in the form of a colourless oil (1.62 g, 76% of theory). .sup.1H NMR (400 MHz, CDCl.sub.3 δ, ppm)

Synthesis Stage 4: {[5-(4-Chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (Synthesis Example I.48-32)

[0418] ##STR00057##

[0419] Methyl {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (1.6 g, 4.21 mmol, 1.0 equiv) and lithium hydroxide (101 mg, 4.21 mmol, 1 equiv) was dissolved in a THF/water mixture (7:2, 20 ml) and then stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and adjusted to pH=2 with 2M hydrochloric acid, with precipitation of a pale yellow solid. The precipitate was filtered off with suction and dried at 55° C. in a vacuum drying cabinet. {[1-(4-Chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid was isolated in the form of a pale yellow solid (1.44 g, 92% of theory). .sup.1H NMR (400 MHz, DMSO-d.sup.6 δ, ppm)

[0420] In analogy to the preparation examples cited above and recited at the appropriate point, and taking account of the general details relating to the preparation of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives, the compounds listed below are obtained:

##STR00058##

[0421] Table I.1: Preferred compounds of the formula (I.1) are the compounds I.1-1 to I.1-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.1-1 to I.1-53 of Table I.1 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

TABLE-US-00001 TABLE 1 No Q 1 Q-2.1 2 Q-2.2 3 Q-2.3 4 Q-2.4 5 Q-2.5 6 Q-2.6 7 Q-2.7 8 Q-2.8 9 Q-2.9 10 Q-2.10 11 Q-2.11 12 Q-2.12 13 Q-2.13 14 Q-2.14 15 Q-2.15 16 Q-2.16 17 Q-2.17 18 Q-2.18 19 Q-2.19 20 Q-2.20 21 Q-2.21 22 Q-2.22 23 Q-2.23 24 Q-2.24 25 Q-2.25 26 Q-2.26 27 Q-2.27 28 Q-2.28 29 Q-2.29 30 Q-2.30 31 Q-2.31 32 Q-2.32 33 Q-2.33 34 Q-2.34 35 Q-2.35 36 Q-2.36 37 Q-2.37 38 Q-2.38 39 Q-2.39 40 Q-2.40 41 Q-2.41 42 Q-2.42 43 Q-2.43 44 Q-2.44 45 Q-2.45 46 Q-2.46 47 Q-2.47 48 Q-2.48 49 Q-2.49 50 Q-2.50 51 Q-2.51 52 Q-2.52 53 Q-2.53

##STR00059##

[0422] Table I.2: Preferred compounds of the formula (I.2) are the compounds I.2-1 to I.2-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.2-1 to I.2-53 of Table I.2 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00060##

[0423] Table I.3: Preferred compounds of the formula (I.3) are the compounds I.3-1 to I.3-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.3-1 to I.3-53 of Table I.3 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00061##

[0424] Table I.4: Preferred compounds of the formula (I.4) are the compounds I.4-1 to I.4-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.4-1 to I.4-53 of Table I.4 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00062##

[0425] Table I.5: Preferred compounds of the formula (I.5) are the compounds I.5-1 to I.5-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.5-1 to I.5-53 of Table I.5 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00063##

[0426] Table I.6: Preferred compounds of the formula (I.6) are the compounds I.6-1 to I.6-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.6-1 to I.6-53 of Table I.6 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00064##

[0427] Table I.7: Preferred compounds of the formula (I.7) are the compounds I.7-1 to I.7-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.7-1 to I.7-53 of Table I.7 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00065##

[0428] Table I.8: Preferred compounds of the formula (I.8) are the compounds I.8-1 to I.8-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.8-1 to I.8-53 of Table I.8 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00066##

[0429] Table I.9: Preferred compounds of the formula (I.9) are the compounds I.9-1 to I.9-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.9-1 to I.9-53 of Table I.9 are defined by the meaning of the respective entry nos. 1 to 53 for Q of Table 1.

##STR00067##

[0430] Table I.10: Preferred compounds of the formula (I.10) are the compounds I.10-1 to I.10-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.10-1 to I.10-53 of table I.10 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00068##

[0431] Table I.11: Preferred compounds of the formula (I.11) are the compounds I.11-1 to I.11-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.11-1 to I.11-53 of table I.11 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00069##

[0432] Table I.12: Preferred compounds of the formula (I.12) are the compounds I.12-1 to I.12-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.12-1 to I.12-53 of table I.12 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00070##

[0433] Table I.13: Preferred compounds of the formula (I.13) are the compounds I.13-1 to I.13-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.13-1 to I.13-53 of table I.13 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00071##

[0434] Table I.14: Preferred compounds of the formula (I.14) are the compounds I.14-1 to I.14-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.14-1 to I.14-53 of table I.14 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00072##

[0435] Table I.15: Preferred compounds of the formula (I.15) are the compounds I.15-1 to I.15-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.15-1 to I.15-53 of table I.15 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00073##

[0436] Table I.16: Preferred compounds of the formula (I.16) are the compounds I.16-1 to I.16-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.16-1 to I.16-53 of table I.16 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00074##

[0437] Table I.17: Preferred compounds of the formula (I.17) are the compounds I.17-1 to I.17-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.17-1 to I.17-53 of table I.17 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00075##

[0438] Table I.18: Preferred compounds of the formula (I.18) are the compounds I.18-1 to I.18-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.18-1 to I.18-53 of table I.18 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00076##

[0439] Table I.19: Preferred compounds of the formula (I.19) are the compounds I.19-1 to I.19-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.19-1 to I.19-53 of table I.19 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00077##

[0440] Table I.20: Preferred compounds of the formula (I.20) are the compounds I.20-1 to I.20-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.20-1 to I.20-53 of table I.20 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00078##

[0441] Table I.21: Preferred compounds of the formula (I.21) are the compounds I.21-1 to I.21-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.21-1 to I.21-53 of table I.21 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00079##

[0442] Table I.22: Preferred compounds of the formula (I.22) are the compounds I.22-1 to I.22-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.22-1 to I.22-53 of table I.22 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00080##

[0443] Table I.23: Preferred compounds of the formula (I.23) are the compounds I.23-1 to I.23-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.23-1 to I.23-53 of table I.23 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00081##

[0444] Table I.24: Preferred compounds of the formula (I.24) are the compounds I.24-1 to I.24-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.24-1 to I.24-53 of table I.24 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00082##

[0445] Table I.25: Preferred compounds of the formula (I.25) are the compounds I.25-1 to I.25-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.25-1 to I.25-53 of table I.25 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00083##

[0446] Table I.26: Preferred compounds of the formula (I.26) are the compounds I.26-1 to I.26-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.26-1 to I.26-53 of table I.26 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00084##

[0447] Table I.27: Preferred compounds of the formula (I.27) are the compounds I.27-1 to I.27-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.27-1 to I.27-53 of table I.27 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00085##

[0448] Table I.28: Preferred compounds of the formula (I.28) are the compounds I.28-1 to I.28-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.28-1 to I.28-53 of table I.28 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00086##

[0449] Table I.29: Preferred compounds of the formula (I.29) are the compounds I.29-1 to I.29-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.29-1 to I.29-53 of table I.29 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00087##

[0450] Table I.30: Preferred compounds of the formula (I.30) are the compounds I.30-1 to I.30-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.30-1 to I.30-53 of table I.30 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00088##

[0451] Table I.31: Preferred compounds of the formula (I.31) are the compounds I.31-1 to I.31-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.31-1 to I.31-53 of table I.31 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00089##

[0452] Table I.32: Preferred compounds of the formula (I.32) are the compounds I.32-1 to I.32-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.32-1 to I.32-53 of table I.32 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00090##

[0453] Table I.33: Preferred compounds of the formula (I.33) are the compounds I.33-1 to I.33-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.33-1 to I.33-53 of table I.33 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00091##

[0454] Table I.34: Preferred compounds of the formula (I.34) are the compounds I.34-1 to I.34-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.34-1 to I.34-53 of table I.34 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00092##

[0455] Table I.35: Preferred compounds of the formula (I.35) are the compounds I.35-1 to I.35-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.35-1 to I.35-53 of table I.35 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00093##

[0456] Table I.36: Preferred compounds of the formula (I.36) are the compounds I.36-1 to I.36-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.36-1 to I.36-53 of table I.36 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00094##

[0457] Table I.37: Preferred compounds of the formula (I.37) are the compounds I.37-1 to I.37-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.37-1 to I.37-53 of table I.37 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00095##

[0458] Table I.38: Preferred compounds of the formula (I.38) are the compounds I.38-1 to I.38-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.38-1 to I.38-53 of table I.38 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00096##

[0459] Table I.39: Preferred compounds of the formula (I.39) are the compounds I.39-1 to I.39-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.39-1 to I.39-53 of table I.39 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00097##

[0460] Table I.40: Preferred compounds of the formula (I.40) are the compounds I.40-1 to I.40-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.40-1 to I.40-53 of table I.40 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00098##

[0461] Table I.41: Preferred compounds of the formula (I.41) are the compounds I.41-1 to I.41-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.41-1 to I.41-53 of table I.41 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00099##

[0462] Table I.42: Preferred compounds of the formula (I.42) are the compounds I.42-1 to I.42-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.42-1 to I.42-53 of table I.42 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00100##

[0463] Table I.43: Preferred compounds of the formula (I.4) are the compounds I.43-1 to I.43-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.43-1 to I.43-53 of table I.43 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00101##

[0464] Table I.44: Preferred compounds of the formula (I.44) are the compounds I.44-1 to I.44-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.44-1 to I.44-53 of table I.44 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00102##

[0465] Table I.45: Preferred compounds of the formula (I.45) are the compounds I.45-1 to I.45-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.45-1 to I.45-53 of table I.45 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00103##

[0466] Table I.46: Preferred compounds of the formula (I.46) are the compounds I.46-1 to I.46-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.46-1 to I.46-53 of table I.46 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00104##

[0467] Table I.47: Preferred compounds of the formula (I.47) are the compounds I.47-1 to I.47-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.47-1 to I.47-53 of table I.47 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00105##

[0468] Table I.48: Preferred compounds of the formula (I.48) are the compounds I.48-1 to I.48-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.48-1 to I.48-53 of table I.48 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00106##

[0469] Table I.49: Preferred compounds of the formula (I.49) are the compounds I.49-1 to I.49-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.49-1 to I.49-53 of table I.49 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00107##

[0470] Table I.50: Preferred compounds of the formula (I.50) are the compounds I.50-1 to I.50-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.50-1 to I.50-53 of table I.50 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00108##

[0471] Table I.51: Preferred compounds of the formula (I.51) are the compounds I.51-1 to I.51-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.51-1 to I.51-53 of table I.2 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00109##

[0472] Table I.52: Preferred compounds of the formula (I.52) are the compounds I.52-1 to I.52-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.52-1 to I.52-53 of table I.52 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00110##

[0473] Table I.53: Preferred compounds of the formula (I.53) are the compounds I.53-1 to I.53-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.53-1 to I.53-53 of table I.53 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00111##

[0474] Table I.54: Preferred compounds of the formula (I.54) are the compounds I.54-1 to I.54-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.54-1 to I.54-53 of table I.54 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00112##

[0475] Table I.55: Preferred compounds of the formula (I.55) are the compounds I.55-1 to I.55-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.55-1 to I.55-53 of table I.55 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00113##

[0476] Table I.56: Preferred compounds of the formula (I.56) are the compounds I.56-1 to I.56-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.56-1 to I.56-53 of table I.56 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00114##

[0477] Table I.57: Preferred compounds of the formula (I.57) are the compounds I.57-1 to I.57-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.57-1 to I.57-53 of table I.57 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00115##

[0478] Table I.58: Preferred compounds of the formula (I.58) are the compounds I.58-1 to I.58-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.58-1 to I.58-53 of table I.58 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00116##

[0479] Table I.59: Preferred compounds of the formula (I.59) are the compounds I.59-1 to I.59-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.59-1 to I.59-53 of table I.59 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00117##

[0480] Table I.60: Preferred compounds of the formula (I.60) are the compounds I.60-1 to I.60-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.60-1 to I.60-53 of table I.60 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00118##

[0481] Table I.61: Preferred compounds of the formula (I.61) are the compounds I.61-1 to I.61-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.61-1 to I.61-53 of table I.61 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00119##

[0482] Table I.62: Preferred compounds of the formula (I.62) are the compounds I.62-1 to I.62-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.62-1 to I.62-53 of table I.62 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00120##

[0483] Table I.63: Preferred compounds of the formula (I.63) are the compounds I.63-1 to I.63-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.63-1 to I.63-53 of table I.63 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00121##

[0484] Table I.64: Preferred compounds of the formula (I.64) are the compounds I.64-1 to I.64-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.64-1 to I.64-53 of table I.64 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00122##

[0485] Table I.65: Preferred compounds of the formula (I.65) are the compounds I.65-1 to I.65-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.65-1 to I.65-53 of table I.65 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00123##

[0486] Table I.66: Preferred compounds of the formula (I.66) are the compounds I.66-1 to I.66-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.66-1 to I.66-53 of table I.66 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00124##

[0487] Table I.67: Preferred compounds of the formula (I.67) are the compounds I.67-1 to I.67-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.67-1 to I.67-53 of table I.67 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00125##

[0488] Table I.68: Preferred compounds of the formula (I.68) are the compounds I.68-1 to I.68-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.68-1 to I.68-53 of table I.68 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00126##

[0489] Table I.69: Preferred compounds of the formula (I.69) are the compounds I.69-1 to I.69-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.69-1 to I.69-53 of table I.69 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00127##

[0490] Table I.70: Preferred compounds of the formula (I.70) are the compounds I.70-1 to I.70-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.70-1 to I.70-53 of table I.70 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00128##

[0491] Table I.71: Preferred compounds of the formula (I.71) are the compounds I.71-1 to I.71-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.71-1 to I.71-53 of table I.71 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00129##

[0492] Table I.72: Preferred compounds of the formula (I.72) are the compounds I.72-1 to I.72-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.72-1 to I.72-53 of table I.72 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00130##

[0493] Table I.73: Preferred compounds of the formula (I.73) are the compounds I.73-1 to I.73-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.73-1 to I.73-53 of table I.73 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00131##

[0494] Table I.74: Preferred compounds of the formula (I.74) are the compounds I.74-1 to I.74-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.74-1 to I.74-53 of table I.74 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00132##

[0495] Table I.75: Preferred compounds of the formula (I.75) are the compounds I.75-1 to I.75-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.75-1 to I.75-53 of table I.75 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00133##

[0496] Table I.76: Preferred compounds of the formula (I.76) are the compounds I.76-1 to I.76-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.76-1 to I.76-53 of table I.76 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

##STR00134##

[0497] Table I.77: Preferred compounds of the formula (I.77) are the compounds I.77-1 to I.77-53 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.77-1 to I.77-53 of table I.77 are defined by the meaning of the respective entry nos. 1 to 53 for Q from table 1.

[0498] Spectroscopic data of selected table examples:

[0499] Selected detailed synthesis examples for the inventive compounds of the general formula (I) are adduced below. The .sup.1H NMR, .sup.13C-NMR and .sup.19F-NMR spectroscopy data reported for the chemical examples described in the sections which follow (400 MHz for .sup.1H NMR and 150 MHz for .sup.13C-NMR and 375 MHz for .sup.19F-NMR, solvent CDCl.sub.3, CD.sub.3OD or d.sub.6-DMSO, internal standard: tetramethylsilane δ=0.00 ppm) were obtained on a Bruker instrument, and the signals listed have the meanings given below: br=broad; s=singlet, d=doublet, t=triplet, dd=doublet of doublets, ddd=doublet of a doublet of doublets, m=multiplet, q=quartet, quint=quintet, sext=sextet, sept=septet, dq=doublet of quartets, dt=doublet of triplets. In the case of diastereomer mixtures, either the significant signals for each of the two diastereomers are reported or the characteristic signal of the main diastereomer is reported. The abbreviations used for chemical groups have, for example, the following meanings: Me=CH.sub.3, Et=CH.sub.2CH.sub.3, t-Hex=C(CH.sub.3).sub.2CH(CH.sub.3).sub.2, t-Bu=C(CH.sub.3).sub.3, n-Bu=unbranched butyl, n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl, c-Hex=cyclohexyl.

[0500] The spectroscopic data listed hereinafter for selected table examples were evaluated via conventional .sup.1H NMR interpretation or via NMR peak list methods.

[0501] Conventional .sup.1H NMR interpretation

Example No. I.77-49

[0502] .sup.1H-NMR (400 MHz, CDCl.sub.3 δ, ppm) 7.59 (m, 1H), 7.37 (t, 1H), 7.22 (m, 1H), 7.14 (dd, 1H), 6.97 (m, 1H), 6.77 (m, 1H), 4.92 (s, 2H), 4.20 (t, 2H), 1.67-1.63 (m, 2H), 1.32-1.26 (m, 4H), 0.87 (t, 3H).

Example No. I.71-49

[0503] .sup.1H-NMR (400 MHz, CDCl.sub.3 δ, ppm) 7.59 (m, 1H), 7.40 (t, 1H), 7.22 (dd, 1H), 7.14 (dd, 1H), 6.97 (dt, 1H), 6.77 (dt, 1H), 5.24 (q, 1H), 5.01 (s, 2H), 3.74 (s, 3H).

Example No. I.70-49

[0504] .sup.1H-NMR (400 MHz, CDCl.sub.3 δ, ppm) 7.60 (m, 1H), 7.40 (t, 1H), 7.21 (m, 1H), 7.14 (m, 1H), 6.96 (m, 1H), 6.77 (m, 1H), 5.05 (s, 2H), 4.75 (s, 2H), 3.77 (s, 3H).

Example No. I.72-49

[0505] .sup.1H-NMR (400 MHz, CDCl.sub.3 δ, ppm) 7.57 (m, 1H), 7.37 (t, 1H), 7.21 (m, 1H), 7.14 (dd, 1H), 6.96 (dt, 1H), 6.77 (dt, 1H), 4.93 (s, 2H), 3.99 (d, 2H), 1.95 (m, 1H), 0.90 (d, 6H).

[0506] NMR Peak List Method

[0507] The 1H NMR data of selected examples are noted in the form of 1H NMR peak lists. For each signal peak, first the 6 value in ppm and then the signal intensity in round brackets are listed. The 6 value-signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.

[0508] The peak list for one example therefore takes the form of: [0509] δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i); . . . ; δ.sub.n (intensity.sub.n)

[0510] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0511] For calibration of the chemical shift of 1H NMR spectra we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0512] The lists of the 1H NMR peaks are similar to the conventional 1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

[0513] In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds, which likewise form part of the subject matter of the invention, and/or peaks of impurities.

[0514] In the reporting of compound signals in the delta range of solvents and/or water, our lists of 1H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.

[0515] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

[0516] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”.

[0517] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 1H NMR interpretation.

[0518] Further details of 1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

TABLE-US-00002 I.2-2: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.4174 (0.9); 7.4130 (1.0); 7.3981 (1.6); 7.3937 (1.8); 7.3791 (1.1); 7.3747 (1.2); 7.3347 (0.5); 7.3303 (0.5); 7.3227 (0.6); 7.3181 (0.6); 7.3159 (0.9); 7.3140 (0.8); 7.3115 (0.8); 7.3096 (0.7); 7.3038 (1.1); 7.3020 (0.8); 7.2995 (1.1); 7.2975 (0.8); 7.2953 (0.9); 7.2907 (0.9); 7.2877 (0.9); 7.2836 (1.6); 7.2785 (1.2); 7.2755 (2.4); 7.2732 (4.2); 7.2708 (4.6); 7.2680 (2.4); 7.2651 (2.8); 7.2588 (38.5); 7.2553 (4.6); 7.2530 (3.6); 7.2470 (0.8); 7.2456 (0.8); 7.2412 (1.3); 7.2363 (0.5); 7.2322 (0.8); 7.2094 (0.6); 7.2027 (4.2); 7.1985 (4.1); 7.1940 (1.8); 7.1923 (1.3); 7.1884 (1.2); 7.1855 (2.6); 7.1832 (2.8); 7.1784 (2.2); 7.1629 (1.6); 7.1473 (0.7); 7.1455 (0.7); 7.1439 (0.7); 7.1424 (0.6); 7.0631 (1.1); 7.0599 (1.1); 7.0424 (1.0); 7.0385 (1.8); 7.0348 (1.1); 7.0174 (1.0); 7.0140 (0.9); 6.0859 (10.2); 4.8565 (16.0); 4.3009 (1.9); 4.2831 (6.0); 4.2652 (6.0); 4.2474 (2.0); 1.5460 (1.9); 1.3107 (7.5); 1.2929 (15.5); 1.2750 (7.5); −0.0002 (14.3) I.2-7: .sup.1H-NMR(400.4 MHZ, d.sub.6-DMSO): δ = 7.4511 (7.0); 7.4460 (2.4); 7.4333 (4.3); 7.4291 (8.0); 7.4215 (1.0); 7.4025 (6.6); 7.3941 (7.8); 7.3865 (7.4); 7.2680 (4.2); 7.2601 (3.9); 7.2547 (3.3); 7.2510 (3.3); 7.2441 (2.6); 7.1953 (8.1); 7.1900 (2.5); 7.1776 (3.7); 7.1733 (6.6); 7.1657 (0.7); 6.2573 (11.2); 4.8568 (14.7); 4.2062 (2.3); 4.1885 (7.0); 4.1707 (6.9); 4.1530 (2.2); 3.3805 (0.4); 3.3310 (68.4); 2.6800 (1.2); 2.6756 (1.3); 2.6063 (0.3); 2.5614 (1.1); 2.5566 (1.2); 2.5520 (0.9); 2.5150 (123.6); 2.5111 (208.3); 2.5068 (236.6); 2.5023 (156.2); 2.4243 (0.3); 2.3379 (1.2); 2.3338 (1.4); 1.9946 (0.4); 1.2276 (7.7); 1.2099 (16.0); 1.1922 (7.4) I.3-4: .sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): δ = 7.3686 (4.8); 7.3592 (6.2); 7.3524 (6.0); 7.3431 (0.8); 7.2381 (3.8); 7.2288 (5.3); 7.2202 (16.0); 7.2142 (4.0); 7.2033 (13.0); 6.1874 (6.2); 4.6995 (5.6); 3.6132 (0.7); 3.5967 (1.3); 3.5824 (0.6); 3.4477 (0.4); 3.3257 (5.7); 2.6664 (0.8); 2.5015 (118.1); 2.4973 (131.0); 2.4929 (86.0); 2.3285 (0.7); 2.3243 (0.8); 1.9035 (0.5); 1.7716 (0.6); 1.7640 (0.7); 1.7553 (1.4); 1.7470 (0.6); 1.7388 (0.4); 1.3508 (0.8); 1.2319 (0.6) I.12-7: .sup.1H-NMR(400.3 MHZ, d.sub.6-DMSO): δ = 7.5692 (0.4); 7.5498 (0.3); 7.4855 (0.4); 7.4505 (12.9); 7.4293 (15.0); 7.3187 (4.7); 7.2974 (11.3); 7.2834 (9.8); 7.2648 (10.2); 7.2428 (13.8); 7.2213 (5.4); 7.1970 (16.0); 7.1757 (13.4); 6.6593 (0.4); 6.5845 (0.5); 6.2017 (14.6); 4.6529 (13.8); 4.4634 (0.3); 3.8614 (0.3); 3.8318 (0.4); 3.8229 (0.4); 3.8095 (0.4); 3.7657 (0.4); 3.7058 (0.6); 3.6725 (0.5); 3.5517 (1.0); 3.5042 (1.6); 3.3397 (33.3); 3.1706 (2.5); 3.0883 (0.9); 3.0339 (0.9); 2.9978 (0.9); 2.9706 (0.9); 2.9483 (0.9); 2.8953 (0.7); 2.8320 (0.6); 2.7924 (0.7); 2.7685 (0.7); 2.6744 (4.7); 2.6078 (1.8); 2.5053 (644.0); 2.3327 (3.8); 2.1854 (0.7); 1.4657 (0.5); 1.4152 (0.3); 1.3576 (3.0); 1.3066 (0.7); 1.2720 (1.6); 1.2382 (10.7); 1.1721 (4.0); 1.1301 (0.6); 0.9410 (0.4); 0.9128 (0.3); 0.8573 (1.5); 0.8393 (1.0) I.10-20: .sup.1H-NMR(599.8 MHz, CDCl.sub.3): δ = 7.3856 (4.5); 7.3828 (4.9); 7.3727 (4.8); 7.3699 (5.1); 7.3278 (2.4); 7.3250 (2.3); 7.3142 (4.0); 7.3125 (3.7); 7.3014 (2.8); 7.2986 (2.6); 7.2608 (8.0); 7.1631 (0.9); 7.1583 (6.0); 7.1547 (2.6); 7.1493 (6.6); 7.1436 (7.1); 7.1382 (2.9); 7.1347 (6.7); 7.1298 (0.8); 7.0174 (2.9); 7.0155 (3.0); 7.0046 (5.2); 7.0028 (5.3); 6.9919 (2.6); 6.9901 (2.5); 6.9322 (0.9); 6.9274 (6.8); 6.9239 (2.2); 6.9128 (12.2); 6.9098 (2.6); 6.9017 (2.1); 6.8983 (5.9); 6.8934 (0.6); 6.8376 (5.1); 6.8362 (5.0); 6.8237 (4.8); 6.8224 (4.6); 6.0209 (19.0); 4.8803 (25.1); 3.7994 (50.0); 3.4471 (49.6); 3.4047 (0.4); 1.6676 (0.6); 0.0051 (0.7); −0.0001 (13.8); −0.0056 (0.5) I.41-1: .sup.1H-NMR(400.4 MHz, d.sub.6-DMSO): δ = 7.4932 (1.0); 7.4766 (1.2); 7.4719 (2.1); 7.4555 (2.1); 7.4507 (1.3); 7.4343 (1.1); 7.3777 (2.1); 7.3733 (1.0); 7.3597 (5.6); 7.3403 (5.4); 7.3218 (1.7); 7.3172 (1.8); 7.2996 (3.1); 7.2920 (1.4); 7.2866 (1.1); 7.2819 (3.0); 7.2761 (0.8); 7.2633 (1.0); 7.2116 (1.0); 7.2052 (1.0); 7.1902 (1.9); 7.1840 (1.8); 7.1667 (5.1); 7.1634 (6.8); 7.1450 (4.6); 6.2467 (9.3); 4.8705 (15.6); 4.2118 (2.3); 4.1941 (7.0); 4.1763 (7.2); 4.1586 (2.3); 3.3283 (17.0); 2.5292 (1.3); 2.5114 (37.4); 2.5070 (49.6); 2.5026 (35.8); 1.2298 (7.8); 1.2120 (16.0); 1.1943 (7.6) I.3-20: .sup.1H-NMR(400.4 MHZ, d.sub.6-DMSO): δ = 7.4175 (1.5); 7.4133 (1.4); 7.3967 (3.0); 7.3948 (2.8); 7.3781 (1.9); 7.3739 (1.7); 7.3412 (3.0); 7.3380 (2.5); 7.3222 (3.5); 7.2899 (7.1); 7.2818 (8.7); 7.2798 (7.9); 7.2741 (7.9); 7.1807 (4.7); 7.1733 (4.5); 7.1706 (4.1); 7.1668 (3.9); 7.1645 (3.8); 7.1625 (3.5); 7.1569 (2.9); 7.0565 (4.7); 7.0346 (6.4); 7.0149 (1.7); 6.1825 (3.8); 6.1776 (10.8); 4.7972 (16.0); 4.1903 (2.3); 4.1725 (6.9); 4.1548 (7.0); 4.1371 (2.3); 3.4045 (26.9); 3.3340 (16.4); 3.3292 (43.5); 2.5108 (46.2); 2.5064 (53.7); 1.2425 (0.8); 1.2328 (0.4); 1.2167 (7.7); 1.2036 (5.9); 1.1989 (15.4); 1.1812 (7.4); 1.1465 (0.4) I.1-3: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.3565 (0.6); 7.3521 (0.9); 7.3499 (0.6); 7.3445 (1.8); 7.3427 (2.9); 7.3397 (3.2); 7.3374 (1.6); 7.3340 (1.4); 7.3288 (1.1); 7.3246 (2.1); 7.3226 (2.0); 7.3154 (0.6); 7.3111 (0.9); 7.3016 (0.6); 7.2681 (0.5); 7.2673 (0.6); 7.2665 (0.7); 7.2657 (0.8); 7.2649 (0.9); 7.2641 (1.0); 7.2632 (1.2); 7.2591 (67.9); 7.2467 (2.6); 7.2425 (2.6); 7.2408 (1.0); 7.2380 (0.9); 7.2359 (0.8); 7.2328 (0.8); 7.2299 (1.2); 7.2276 (1.2); 7.2255 (1.0); 7.2225 (1.6); 7.2091 (0.7); 7.2043 (1.2); 7.1890 (1.2); 7.1842 (0.7); 7.1687 (0.7); 7.0301 (0.6); 7.0248 (1.1); 7.0190 (0.7); 7.0052 (0.6); 6.9997 (0.9); 6.9947 (0.8); 6.9428 (0.6); 6.9404 (1.7); 6.9392 (1.3); 6.9352 (1.3); 6.9332 (0.8); 6.9223 (0.6); 6.9192 (1.8); 6.9169 (1.2); 6.9146 (0.9); 6.9128 (1.0); 6.9105 (0.7); 6.0394 (6.9); 4.8921 (8.7); 3.8386 (0.8); 3.8241 (16.0); 1.5341 (11.0); 1.2551 (1.1); 0.8818 (0.6); 0.0080 (1.2); 0.0040 (0.6); −0.0002 (41.4); −0.0085 (1.1) I.20-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7853 (4.7); 7.7802 (4.5); 7.6015 (1.2); 7.5743 (7.9); 7.5687 (6.4); 7.5621 (5.0); 7.5402 (0.8); 7.5336 (0.9); 7.4366 (6.4); 7.4303 (2.4); 7.4140 (3.1); 7.4080 (8.2); 7.3998 (1.3); 7.2236 (8.2); 7.2171 (2.7); 7.2011 (2.7); 7.1950 (6.2); 6.3636 (11.4); 4.8126 (14.0); 4.1852 (2.2); 4.1615 (6.9); 4.1378 (7.0); 4.1142 (2.3); 3.6808 (0.3); 3.3207 (7.8); 2.5092 (6.9); 2.5034 (8.6); 2.4976 (6.0); 2.0761 (1.9); 1.2087 (7.8); 1.1850 (16.0); 1.1613 (7.4); 0.0001 (4.8) I.12-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7739 (5.7); 7.7671 (5.8); 7.6301 (0.5); 7.6111 (2.4); 7.5831 (8.3); 7.5653 (5.7); 7.5581 (5.1); 7.5369 (1.7); 7.5297 (1.7); 7.2742 (1.7); 7.2656 (1.1); 7.2535 (3.1); 7.2440 (6.8); 7.2243 (8.8); 7.1927 (7.4); 7.1705 (1.2); 7.1627 (2.2); 6.4392 (0.3); 6.2947 (13.2); 4.8116 (0.4); 4.7166 (16.0); 3.5057 (4.2); 2.5088 (13.6); 2.5030 (17.1); 2.4972 (11.8); 2.0748 (3.5); 0.0001 (6.2) I.21-38: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 13.0995 (0.4); 13.0844 (0.4); 13.0508 (0.4); 13.0230 (0.6); 12.9823 (0.6); 12.9214 (0.5); 12.8850 (0.4); 12.8614 (0.4); 7.7501 (0.4); 7.6490 (1.8); 7.6273 (3.7); 7.6119 (4.1); 7.5902 (1.8); 7.5374 (0.3); 7.4501 (12.6); 7.4338 (7.8); 7.4285 (15.4); 7.3974 (2.2); 7.3907 (2.0); 7.2626 (7.1); 7.2558 (16.0); 7.2393 (9.5); 7.2343 (14.0); 6.8776 (0.4); 6.3300 (14.4); 5.7691 (0.6); 4.7138 (13.7); 4.0630 (0.4); 4.0450 (0.6); 4.0271 (0.6); 3.6058 (0.8); 3.5575 (0.4); 3.5014 (0.6); 3.3421 (304.1); 3.2122 (0.5); 3.1407 (0.4); 3.1048 (0.4); 3.0848 (0.4); 3.0599 (0.4); 2.9946 (0.6); 2.9375 (0.5); 2.9099 (0.4); 2.9015 (0.4); 2.7371 (0.4); 2.6792 (5.3); 2.6165 (1.1); 2.5142 (609.2); 2.5102 (776.0); 2.4192 (1.6); 2.3374 (5.3); 2.3021 (0.4); 2.2510 (0.4); 2.1911 (0.8); 1.9975 (2.1); 1.9236 (0.4); 1.9165 (1.6); 1.7826 (0.5); 1.7749 (0.6); 1.7671 (0.8); 1.3885 (0.4); 1.3623 (4.4); 1.2433 (1.8); 1.2000 (0.9); 1.1821 (1.4); 1.1640 (0.9); 1.0918 (0.4); 0.8608 (0.5); 0.8477 (0.5); 0.8156 (0.4); −3.4820 (0.4) I.21-38: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 7.8283 (0.6); 7.8222 (4.0); 7.8174 (1.4); 7.8055 (1.5); 7.8007 (4.5); 7.7945 (0.6); 7.7214 (0.6); 7.7062 (0.7); 7.6994 (1.3); 7.6843 (1.2); 7.6775 (0.8); 7.6623 (0.8); 7.6576 (0.6); 7.6361 (0.8); 7.6247 (0.4); 7.6167 (0.4); 7.6030 (0.5); 7.5893 (0.8); 7.5824 (0.8); 7.5663 (1.0); 7.5628 (1.1); 7.5596 (1.0); 7.5563 (0.9); 7.5403 (0.8); 7.5335 (0.8); 7.5285 (1.0); 7.5238 (0.5); 7.5181 (0.4); 7.5118 (0.4); 7.5068 (0.8); 7.5019 (1.0); 7.4960 (4.9); 7.4913 (1.6); 7.4791 (1.6); 7.4745 (4.1); 7.4683 (0.6); 7.3117 (0.5); 7.3083 (0.6); 7.3046 (0.5); 7.3019 (0.5); 7.2878 (0.9); 7.2825 (0.9); 7.2690 (0.6); 7.2656 (0.6); 7.2619 (0.5); 6.4841 (6.0); 4.8346 (7.4); 4.0380 (0.4); 4.0202 (0.4); 3.8824 (1.9); 3.3502 (0.3); 2.8903 (0.3); 2.5124 (3.4); 2.5080 (7.2); 2.5035 (9.7); 2.4991 (7.0); 2.4947 (3.3); 1.9896 (1.8); 1.9114 (16.0); 1.2331 (0.3); 1.1922 (0.5); 1.1744 (1.0); 1.1566 (0.5); −0.0005 (3.5) I.48-38: .sup.1H-NMR(300.1 MHZ, d.sub.6-DMSO): δ = 7.5544 (1.4); 7.5325 (4.8); 7.4964 (4.8); 7.4759 (1.5); 7.4285 (1.5); 7.4197 (1.6); 7.3920 (2.6); 7.3627 (2.0); 7.3537 (2.2); 7.3319 (8.2); 7.3182 (7.0); 7.2900 (0.6); 7.2105 (1.4); 7.2063 (1.4); 7.1835 (2.4); 7.1541 (1.2); 6.3027 (9.1); 4.7527 (16.0); 4.7246 (0.7); 3.4986 (0.9); 3.3534 (5.9); 2.5109 (6.5); 2.5059 (7.5); 2.0761 (3.2); 1.2570 (0.5); 1.2339 (1.2); 0.0000 (1.9) I.21-1: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.6243 (0.4); 7.4371 (12.0); 7.4325 (4.4); 7.4204 (4.7); 7.4158 (14.9); 7.3959 (3.9); 7.3915 (1.9); 7.3779 (10.1); 7.3584 (8.2); 7.3308 (0.6); 7.3197 (4.3); 7.3065 (1.8); 7.3016 (5.5); 7.2831 (1.8); 7.2467 (2.1); 7.2406 (14.7); 7.2359 (4.9); 7.2239 (4.5); 7.2193 (12.0); 7.1934 (7.7); 7.1900 (11.2); 7.1718 (8.4); 6.1489 (16.0); 4.4382 (10.7); 4.3733 (0.3); 3.8025 (0.5); 3.7307 (1.6); 3.5480 (1.0); 3.3573 (8.8); 3.1694 (1.3); 2.6781 (1.5); 2.6736 (2.0); 2.6692 (1.5); 2.6043 (0.6); 2.5270 (6.9); 2.5220 (10.4); 2.5135 (111.2); 2.5091 (228.5); 2.5047 (308.1); 2.5002 (223.1); 2.4959 (107.5); 2.3360 (1.4); 2.3315 (1.9); 2.3270 (1.3); 1.3571 (0.6); 1.2962 (0.4); 1.2417 (1.8); 1.1827 (0.8); 1.1711 (1.0); 0.9994 (0.6); 0.8792 (0.5); 0.8626 (1.5); 0.8452 (0.6) I.3-1: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.4316 (0.8); 7.4239 (0.6); 7.4148 (0.7); 7.2516 (0.4); 6.2686 (0.5); 4.8205 (0.8); 3.3883 (4.8); 2.5667 (16.0) I.42-1: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 13.2081 (0.3); 13.1492 (0.3); 13.1159 (0.3); 13.0953 (0.4); 13.0407 (0.3); 7.4937 (3.5); 7.4771 (4.9); 7.4725 (5.4); 7.4562 (5.1); 7.4351 (2.2); 7.3764 (9.1); 7.3718 (7.6); 7.3585 (15.6); 7.3392 (11.5); 7.3237 (6.6); 7.3183 (6.2); 7.2991 (8.3); 7.2788 (6.2); 7.2629 (2.0); 7.2601 (2.1); 7.2090 (6.0); 7.2039 (6.3); 7.1886 (10.7); 7.1820 (11.0); 7.1738 (15.5); 7.1704 (16.0); 7.1524 (9.5); 6.2134 (14.2); 5.7654 (0.6); 4.7478 (15.7); 3.7142 (0.4); 3.6426 (0.4); 3.5941 (0.5); 3.3476 (7.5); 3.1774 (0.7); 3.0201 (0.5); 2.9868 (0.5); 2.9624 (0.4); 2.9491 (0.4); 2.8552 (0.4); 2.7769 (0.3); 2.7125 (0.6); 2.6817 (1.5); 2.6587 (0.4); 2.5163 (146.8); 2.5125 (180.7); 2.5082 (177.2); 2.5040 (110.4); 2.4722 (0.6); 2.3392 (1.1); 2.3350 (1.0); 1.3614 (1.7); 1.2437 (0.9); 1.1752 (0.3) I.44-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7061 (5.4); 7.6995 (5.3); 7.5716 (2.5); 7.5644 (2.5); 7.5368 (2.4); 7.5304 (2.4); 7.4892 (2.2); 7.4824 (1.9); 7.4615 (4.0); 7.4546 (3.8); 7.4396 (1.6); 7.4109 (4.2); 7.4039 (6.3); 7.3854 (3.8); 7.3760 (3.7); 7.3681 (4.0); 7.3612 (3.3); 7.3387 (1.4); 7.3319 (1.2); 6.3006 (11.5); 4.8513 (14.2); 4.2037 (2.2); 4.1800 (7.0); 4.1563 (7.1); 4.1326 (2.3); 3.3191 (12.9); 2.5087 (9.0); 2.5029 (11.3); 2.4972 (7.9); 2.0756 (1.6); 1.2180 (7.8); 1.1944 (16.0); 1.1707 (7.5); 0.0000 (6.1) I.11-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7753 (4.4); 7.7696 (3.6); 7.6340 (0.4); 7.5998 (1.7); 7.5718 (8.0); 7.5628 (5.0); 7.5560 (4.1); 7.5343 (0.8); 7.5276 (0.9); 7.2768 (1.9); 7.2682 (1.3); 7.2571 (3.1); 7.2466 (6.3); 7.2277 (7.2); 7.2229 (6.1); 7.1934 (5.8); 7.1636 (1.7); 6.3195 (11.1); 4.8132 (14.8); 4.1879 (2.5); 4.1642 (7.5); 4.1405 (7.5); 4.1169 (2.4); 3.3443 (24.4); 3.3400 (22.2); 2.5129 (4.2); 2.5072 (5.2); 2.5015 (3.7); 1.2299 (1.2); 1.2112 (8.0); 1.1876 (16.0); 1.1639 (7.5); 0.0003 (1.0) I.42-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 12.9048 (0.4); 7.7438 (4.8); 7.7408 (5.3); 7.7386 (5.6); 7.7356 (4.2); 7.5376 (0.7); 7.5091 (9.5); 7.5036 (13.5); 7.4771 (0.5); 7.3546 (1.5); 7.3462 (1.7); 7.3414 (1.5); 7.3194 (3.6); 7.3124 (4.3); 7.2903 (3.7); 7.2839 (2.5); 7.2625 (1.5); 7.1386 (1.4); 7.1329 (1.3); 7.1128 (2.2); 7.1044 (2.0); 7.0851 (1.1); 7.0760 (1.0); 6.2707 (8.4); 6.2679 (7.7); 4.7318 (16.0); 3.3731 (3.4); 2.5132 (16.2); 2.5074 (29.2); 2.5015 (36.6); 2.4957 (25.0); 2.0739 (0.5); 0.0108 (1.4); −0.0001 (24.9); −0.0111 (1.0) I.41-49: .sup.1H-NMR(300.3 MHZ, CDCl.sub.3): δ = 7.2801 (1.5); 7.2525 (2.9); 7.2254 (2.0); 7.1892 (16.0); 7.1150 (0.8); 7.0926 (2.5); 7.0884 (3.0); 7.0667 (2.7); 7.0600 (2.2); 7.0385 (1.0); 7.0076 (2.1); 7.0003 (1.8); 6.9754 (2.0); 6.9680 (1.8); 6.7925 (0.7); 6.7823 (0.9); 6.7638 (1.1); 6.7541 (2.3); 6.7440 (0.6); 6.7377 (0.6); 6.7270 (1.2); 6.7206 (1.7); 6.7116 (1.0); 6.6901 (1.1); 6.6821 (0.8); 6.0298 (5.2); 4.7671 (14.8); 4.2388 (1.8); 4.2151 (5.5); 4.1913 (5.6); 4.1676 (1.9); 1.4686 (1.8); 1.2468 (7.0); 1.2231 (13.0); 1.1993 (7.5); 1.1863 (3.7); 0.8111 (0.7); 0.7886 (0.4); 0.0000 (1.0) I.41-49: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.3482 (1.6); 7.3273 (2.6); 7.3070 (2.0); 7.2631 (8.4); 7.1776 (0.8); 7.1702 (1.5); 7.1671 (1.6); 7.1645 (1.7); 7.1617 (2.3); 7.1569 (1.6); 7.1488 (1.2); 7.1457 (1.3); 7.1404 (2.4); 7.1359 (1.0); 7.1201 (0.9); 7.0759 (2.1); 7.0704 (1.8); 7.0517 (2.1); 7.0462 (1.9); 6.8593 (0.6); 6.8568 (0.6); 6.8530 (0.7); 6.8506 (0.7); 6.8395 (0.8); 6.8374 (1.0); 6.8311 (1.4); 6.8177 (1.5); 6.8115 (1.3); 6.7953 (1.2); 6.7928 (1.2); 6.7894 (0.8); 6.7866 (0.9); 6.7709 (1.0); 6.7646 (0.8); 6.1051 (5.2); 6.1029 (5.1); 4.8409 (16.0); 4.3023 (1.9); 4.2845 (6.1); 4.2666 (6.1); 4.2488 (2.0); 1.5849 (6.2); 1.3133 (7.6); 1.2954 (15.6); 1.2776 (7.4); −0.0002 (11.0) I.7-3: .sup.1H-NMR(300.1 MHZ, CDCl.sub.6): δ = 7.3328 (0.6); 7.3129 (0.7); 7.3060 (1.1); 7.2864 (1.2); 7.2796 (1.0); 7.2599 (6.2); 7.2449 (0.7); 7.2389 (1.3); 7.2179 (1.2); 7.2119 (0.9); 7.1909 (0.7); 7.0795 (0.6); 7.0737 (0.7); 7.0513 (1.1); 7.0455 (1.2); 7.0430 (1.2); 7.0354 (0.9); 7.0266 (1.9); 7.0197 (2.6); 6.9944 (2.4); 6.9890 (1.9); 6.9790 (0.9); 6.9669 (1.2); 6.9521 (1.9); 6.9430 (2.4); 6.9363 (2.1); 6.9268 (1.5); 6.9231 (1.3); 6.9166 (1.5); 6.0551 (5.6); 4.8865 (9.7); 3.8219 (16.0); 1.5562 (3.2); −0.0001 (4.6) I.20-7: .sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): δ = 7.4731 (8.6); 7.4597 (9.6); 7.4515 (10.1); 7.2805 (7.5); 7.2604 (7.1); 7.2093 (7.3); 7.1888 (7.1); 7.1560 (0.4); 6.2997 (8.6); 4.8525 (15.1); 4.7603 (3.3); 4.2744 (3.4); 4.2010 (2.2); 4.1835 (6.6); 4.1649 (7.3); 4.1463 (3.3); 4.1279 (0.7); 3.3281 (36.2); 2.6753 (0.6); 2.5061 (77.4); 2.5024 (72.7); 2.3333 (0.5); 1.2655 (1.0); 1.2239 (8.5); 1.2064 (16.0); 1.1885 (8.1); 1.1737 (1.9); 1.0909 (0.5); 0.8670 (0.3); 0.8540 (0.4); 0.8010 (0.3) I.11-7: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 7.4536 (10.5); 7.4421 (9.0); 7.4335 (8.3); 7.3879 (0.5); 7.3034 (10.0); 7.2951 (10.6); 7.2619 (9.0); 7.2494 (8.7); 7.2407 (8.8); 7.2176 (5.8); 7.1896 (11.4); 7.1783 (8.6); 7.1702 (7.5); 6.2633 (7.1); 6.2542 (8.0); 4.8541 (13.7); 4.8452 (15.2); 4.1875 (8.3); 4.1779 (9.5); 4.1710 (8.7); 4.1605 (7.7); 3.3519 (23.7); 3.3344 (57.2); 3.3253 (63.6); 2.6733 (1.0); 2.5033 (127.2); 2.3306 (0.8); 1.2271 (10.3); 1.2097 (15.7); 1.2000 (16.0); 1.1842 (7.1) I.41-4: .sup.1H-NMR(400.3 MHZ, d.sub.6-DMSO): δ = 7.5015 (1.0); 7.4846 (1.9); 7.4802 (2.2); 7.4637 (2.5); 7.4593 (1.4); 7.4425 (1.1); 7.3651 (1.3); 7.3592 (1.2); 7.3395 (2.1); 7.3159 (1.3); 7.3099 (1.1); 7.2470 (1.3); 7.2401 (0.9); 7.2238 (8.4); 7.2169 (5.9); 7.2127 (7.8); 7.2035 (13.4); 7.1998 (10.8); 7.1797 (1.6); 6.2559 (9.3); 4.8682 (16.0); 4.2104 (2.4); 4.1926 (7.2); 4.1749 (7.2); 4.1571 (2.4); 3.3445 (34.2); 3.3402 (73.0); 2.6827 (0.7); 2.6786 (0.8); 2.5180 (59.4); 2.5138 (99.8); 2.5095 (111.8); 2.5053 (75.3); 2.4704 (0.5); 2.3408 (0.7); 2.3367 (0.7); 1.2288 (7.8); 1.2149 (7.1); 1.2111 (15.6); 1.1934 (7.4) I.20-20: .sup.1H-NMR(400.4 MHZ, d.sub.6-DMSO): δ = 7.4339 (1.3); 7.4300 (1.3); 7.4149 (2.3); 7.4130 (2.5); 7.4112 (2.6); 7.3945 (1.7); 7.3905 (1.8); 7.3785 (6.9); 7.3575 (9.3); 7.3439 (3.0); 7.3400 (2.6); 7.1886 (8.3); 7.1675 (6.3); 7.0701 (5.6); 7.0497 (7.9); 7.0309 (1.7); 6.2245 (11.2); 4.7966 (15.7); 4.1876 (2.3); 4.1700 (7.2); 4.1523 (7.1); 4.1344 (2.4); 3.4292 (27.4); 3.3251 (68.1); 2.6755 (1.1); 2.6067 (0.3); 2.5108 (150.6); 2.5065 (188.9); 2.5022 (130.9); 2.3337 (1.1); 1.2275 (0.3); 1.2138 (8.1); 1.1961 (16.0); 1.1783 (7.6) I.42-38: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 12.9647 (1.7); 12.9394 (1.8); 7.5000 (4.6); 7.4080 (3.1); 7.3791 (7.6); 7.3531 (9.0); 7.3251 (5.7); 7.3026 (3.3); 7.1982 (4.3); 7.1753 (6.2); 7.1534 (5.8); 7.1311 (5.9); 7.1113 (3.0); 6.2650 (11.5); 4.7221 (16.0); 4.0399 (3.6); 4.0225 (3.2); 3.6055 (2.1); 3.4093 (2.8); 3.3260 (815.9); 3.2707 (2.4); 3.2028 (1.7); 2.9073 (1.8); 2.8815 (1.6); 2.6732 (14.3); 2.5066 (2220.7); 2.3968 (2.3); 2.3325 (13.9); 1.9930 (8.6); 1.3602 (6.5); 1.2411 (4.2); 1.1966 (3.9); 1.1802 (5.6); 1.1616 (2.6) I.42-7: .sup.1H-NMR(400.4 MHZ, d.sub.6-DMSO): δ = 13.0414 (0.3); 7.5245 (1.5); 7.5079 (2.0); 7.5032 (3.6); 7.4870 (3.6); 7.4821 (2.4); 7.4657 (2.0); 7.4520 (1.2); 7.4444 (12.3); 7.4392 (4.1); 7.4275 (4.4); 7.4224 (14.7); 7.4148 (2.0); 7.3780 (1.9); 7.3718 (2.0); 7.3522 (2.8); 7.3478 (3.0); 7.3287 (1.9); 7.3224 (2.0); 7.2366 (1.7); 7.2318 (1.8); 7.2161 (3.4); 7.2104 (3.2); 7.1912 (15.8); 7.1743 (4.2); 7.1692 (12.4); 7.1616 (1.6); 6.8769 (0.4); 6.2491 (15.5); 4.7586 (16.0); 3.3284 (37.4); 3.2053 (0.4); 2.6805 (1.7); 2.6761 (2.4); 2.6715 (1.8); 2.6067 (0.5); 2.5683 (0.7); 2.5295 (7.2); 2.5160 (129.9); 2.5117 (269.6); 2.5072 (366.1); 2.5027 (266.9); 2.4985 (128.1); 2.4570 (0.9); 2.3385 (1.7); 2.3342 (2.3); 2.3296 (1.7); 2.1884 (0.6); 2.0801 (0.7); 1.9139 (0.5); 1.3609 (4.5); 1.2417 (0.9); 1.1749 (0.4) I.21-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7802 (6.4); 7.7734 (6.4); 7.6137 (2.6); 7.5855 (9.6); 7.5707 (6.5); 7.5637 (5.6); 7.5423 (1.6); 7.5353 (1.6); 7.4350 (8.2); 7.4065 (10.5); 7.2229 (10.6); 7.1943 (8.1); 6.3354 (14.1); 4.7048 (16.0); 3.4622 (0.3); 3.3193 (3.6); 2.5076 (28.5); 2.5019 (35.5); 2.4962 (25.2); 1.2361 (0.6); 0.0001 (22.6) I.21-32: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 13.2498 (0.3); 7.9050 (5.0); 7.9033 (5.8); 7.9004 (5.4); 7.8987 (5.2); 7.8235 (1.1); 7.8172 (8.6); 7.8123 (2.9); 7.8005 (3.1); 7.7956 (10.1); 7.7893 (1.4); 7.6566 (0.8); 7.6550 (1.0); 7.6354 (10.3); 7.6334 (13.6); 7.6281 (7.3); 7.6115 (0.7); 7.6068 (1.0); 7.4990 (1.3); 7.4929 (10.2); 7.4880 (3.1); 7.4760 (3.0); 7.4713 (8.9); 7.4651 (1.0); 6.4824 (13.5); 4.9453 (0.3); 4.8165 (16.0); 3.7025 (0.9); 3.5682 (0.4); 3.1697 (2.9); 2.8897 (0.4); 2.5419 (8.8); 2.5115 (5.6); 2.5071 (11.9); 2.5026 (16.3); 2.4981 (11.6); 2.4936 (5.3); 2.0760 (0.9); −0.0004 (6.7) I.42-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5871 (3.0); 7.5800 (3.0); 7.5528 (3.0); 7.5459 (3.0); 7.5043 (2.0); 7.4762 (4.5); 7.4488 (3.5); 7.4238 (1.4); 7.3954 (6.2); 7.3676 (5.2); 7.3615 (3.8); 7.3450 (2.1); 7.3333 (2.6); 7.3299 (2.5); 7.3024 (1.7); 7.2944 (1.5); 7.1747 (1.5); 7.1678 (1.4); 7.1466 (2.6); 7.1397 (2.4); 7.1180 (1.2); 7.1114 (1.1); 6.3003 (9.9); 4.7649 (16.0); 3.7895 (0.4); 3.7663 (0.5); 3.7419 (0.4); 3.5179 (1.0); 3.4695 (1.0); 2.5176 (3.1); 2.5123 (3.8); 2.0797 (1.6); 1.2346 (0.4) I.42-49: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 7.9704 (1.5); 7.9485 (3.2); 7.9314 (3.3); 7.9268 (2.2); 7.9095 (1.8); 7.8992 (1.7); 7.8782 (3.1); 7.8573 (1.7); 7.7231 (3.8); 7.7176 (4.0); 7.6976 (3.9); 7.6921 (3.9); 7.5966 (0.4); 7.5749 (0.5); 7.4607 (3.1); 7.4422 (2.9); 7.3712 (1.8); 7.3650 (1.9); 7.3477 (2.1); 7.3421 (3.4); 7.3361 (2.5); 7.3191 (1.8); 7.3135 (1.9); 7.1663 (1.8); 7.1606 (1.8); 7.1453 (3.3); 7.1394 (3.1); 7.1242 (1.7); 7.1180 (1.6); 6.0565 (3.2); 6.0508 (3.2); 4.3376 (5.0); 3.6949 (0.4); 3.5818 (0.5); 3.5728 (0.4); 3.5553 (0.5); 3.5046 (0.6); 3.3451 (2.8); 3.3389 (2.9); 3.1986 (0.5); 3.1673 (12.2); 2.9956 (0.8); 2.6752 (0.7); 2.6709 (0.6); 2.6660 (0.5); 2.5411 (2.0); 2.5107 (28.3); 2.5063 (57.5); 2.5018 (77.3); 2.4973 (55.3); 2.4929 (26.0); 2.3286 (0.4); 2.1744 (0.5); 1.9035 (0.5); 1.3953 (0.3); 1.2980 (1.1); 1.2580 (2.2); 1.2334 (16.0); 1.1567 (0.3); 1.1342 (0.3); 1.1188 (0.3); 1.1130 (0.4); 1.0286 (0.4); 0.8696 (0.8); 0.8530 (2.4); 0.8353 (1.1); 0.0076 (1.4); −0.0005 (34.4); −0.0088 (1.2) I.42-49: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.3598 (1.6); 7.3389 (2.7); 7.3187 (2.0); 7.2595 (14.6); 7.1799 (0.8); 7.1731 (1.5); 7.1700 (1.6); 7.1674 (1.7); 7.1644 (2.3); 7.1592 (1.6); 7.1517 (1.2); 7.1486 (1.3); 7.1458 (1.6); 7.1431 (2.7); 7.1382 (1.1); 7.1225 (1.0); 7.0802 (2.2); 7.0746 (2.0); 7.0560 (2.2); 7.0504 (2.0); 6.8618 (0.6); 6.8593 (0.6); 6.8555 (0.7); 6.8531 (0.8); 6.8421 (0.8); 6.8399 (1.1); 6.8336 (1.4); 6.8207 (1.6); 6.8144 (1.3); 6.8122 (0.9); 6.7989 (1.2); 6.7964 (1.3); 6.7932 (0.9); 6.7903 (1.0); 6.7745 (1.1); 6.7684 (0.8); 6.1062 (5.4); 6.1040 (5.5); 4.9131 (16.0); 1.4319 (1.9); −0.0002 (16.7) I.11-39: .sup.1H-NMR(400.0 MHz, d.sub.6-DMSO): δ = 3.3288 (16.0); 2.5110 (1.4); 2.5065 (3.1); 2.5019 (4.4); 2.4973 (3.2); 2.4927 (1.4) I.21-7: .sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): δ = 7.5848 (0.3); 7.5564 (0.3); 7.5343 (0.4); 7.5094 (0.3); 7.4707 (10.3); 7.4533 (15.1); 7.4494 (16.0); 7.4314 (12.8); 7.2688 (12.4); 7.2476 (10.1); 7.2038 (12.5); 7.1819 (10.4); 6.1774 (10.8); 4.4653 (7.6); 3.7880 (0.9); 3.3367 (16.8); 2.6775 (2.4); 2.6732 (3.0); 2.6687 (2.2); 2.6044 (1.0); 2.5689 (0.7); 2.5264 (12.8); 2.5087 (376.8); 2.5043 (488.4); 2.5000 (346.7); 2.4535 (1.7); 2.3356 (2.3); 2.3312 (2.9); 1.3571 (0.7); 1.2421 (2.7); 1.1830 (0.5); 1.1707 (0.7); 0.8793 (1.0); 0.8626 (2.7); 0.8451 (1.1) I.12-4: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 7.2861 (2.5); 7.2773 (3.4); 7.2696 (5.4); 7.2638 (5.5); 7.2555 (4.8); 7.2498 (5.1); 7.2399 (5.3); 7.2347 (7.9); 7.2260 (13.4); 7.2203 (16.0); 7.2096 (15.3); 7.2041 (14.6); 6.1531 (1.7); 6.1441 (5.3); 6.1388 (5.6); 4.5221 (7.2); 3.7131 (0.3); 3.4367 (1.4); 3.3664 (1.7); 3.1726 (1.0); 3.1670 (1.0); 3.1527 (0.6); 2.6761 (1.0); 2.6719 (1.0); 2.6066 (0.4); 2.5072 (130.4); 2.5027 (125.5); 2.3340 (0.8); 2.3297 (0.8); 2.1878 (0.5); 2.1831 (0.5); 1.9950 (0.4); 1.9894 (0.4); 1.3684 (1.0); 1.3598 (2.8); 1.3545 (3.0); 1.2379 (0.7); 1.1798 (0.5); 1.1740 (0.4) I.7-4: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ =7.2970 (0.5); 7.2823 (0.6); 7.2768 (1.0); 7.2597 (26.5); 7.2423 (0.7); 7.2013 (1.6); 7.1957 (0.6); 7.1893 (1.8); 7.1841 (1.0); 7.1786 (2.2); 7.1723 (0.7); 7.1666 (2.0); 7.0376 (0.6); 7.0229 (3.0); 7.0187 (1.1); 7.0169 (1.3); 7.0057 (0.8); 7.0024 (2.8); 7.0004 (2.2); 6.9970 (1.0); 6.9855 (0.7); 6.9798 (2.6); 6.9772 (1.2); 6.9759 (1.3); 6.9733 (1.0); 6.9605 (0.8); 6.9577 (0.9); 6.9566 (1.1); 6.9541 (0.9); 6.9268 (0.7); 6.9228 (0.7); 6.9207 (0.7); 6.9167 (0.5); 6.9029 (0.7); 6.8989 (0.7); 6.8968 (0.7); 6.8928 (0.5); 6.0481 (5.8); 5.2977 (1.5); 4.8765 (9.0); 3.8142 (16.0); 3.7980 (0.6); 1.5476 (0.6); −0.0002 (10.9) I.3-2: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.5182 (2.0); 7.4144 (0.8); 7.3995 (1.2); 7.3954 (1.4); 7.3804 (0.8); 7.3762 (1.1); 7.3413 (0.7); 7.3245 (0.9); 7.3165 (0.8); 7.3087 (2.0); 7.2894 (4.3); 7.2846 (2.7); 7.2686 (4.6); 7.2593 (367.9); 7.2089 (2.3); 7.2052 (2.5); 7.2003 (1.7); 7.1891 (1.6); 7.1847 (1.6); 7.1587 (0.6); 7.0823 (0.9); 7.0608 (1.4); 7.0395 (0.8); 6.9953 (2.0); 6.0925 (7.0); 4.9224 (12.2); 4.1150 (1.6); 4.0982 (1.4); 2.2968 (0.6); 2.0048 (0.5); 1.6411 (1.0); 1.2546 (16.0); 0.8800 (1.4); 0.1461 (0.6); 0.0493 (0.6); 0.0079 (5.0); −0.0002 (156.1); −0.0085 (4.3); −0.1494 (0.7) I.47-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.6040 (2.4); 7.5967 (2.5); 7.5696 (2.5); 7.5625 (2.6); 7.5459 (2.6); 7.5132 (2.4); 7.5097 (2.4); 7.4885 (1.6); 7.4603 (3.5); 7.4333 (3.0); 7.3971 (2.9); 7.3949 (2.9); 7.3899 (2.7); 7.3659 (1.9); 7.3609 (1.8); 7.3449 (6.2); 7.3395 (4.7); 7.3375 (4.7); 7.3308 (5.3); 7.3024 (0.4); 6.3490 (7.5); 4.8481 (13.9); 4.2018 (2.2); 4.1781 (6.9); 4.1544 (7.0); 4.1308 (2.3); 3.3328 (67.0); 2.5105 (5.5); 2.5047 (6.9); 2.4990 (4.8); 1.2344 (0.9); 1.2155 (7.8); 1.1919 (16.0); 1.1682 (7.4); 0.0000 (2.0) I.45-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7039 (6.8); 7.6974 (6.7); 7.5622 (3.3); 7.5552 (3.3); 7.5279 (3.3); 7.5210 (3.3); 7.4842 (3.0); 7.4775 (2.7); 7.4569 (6.6); 7.4497 (5.2); 7.4306 (5.5); 7.4035 (5.7); 7.3961 (8.7); 7.3682 (8.7); 7.3618 (4.3); 7.3386 (2.1); 7.3321 (1.9); 6.2598 (16.0); 4.7047 (13.9); 3.3669 (0.8); 3.3500 (0.7); 2.5088 (19.4); 2.5030 (24.1); 2.4973 (16.8); 1.2350 (0.8); 0.0002 (9.0) I.40-49: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.3447 (1.0); 7.3239 (1.6); 7.3036 (1.2); 7.2597 (14.5); 7.1684 (0.9); 7.1653 (0.9); 7.1627 (1.1); 7.1599 (1.3); 7.1556 (1.0); 7.1470 (0.7); 7.1439 (0.8); 7.1388 (1.3); 7.1345 (0.6); 7.1187 (0.6); 7.0758 (1.3); 7.0702 (1.1); 7.0516 (1.3); 7.0460 (1.1); 6.8352 (0.6); 6.8289 (0.8); 6.8157 (0.9); 6.8095 (0.8); 6.7936 (0.7); 6.7910 (0.7); 6.7848 (0.6); 6.7691 (0.6); 6.1019 (3.1); 6.0996 (3.1); 4.8607 (9.0); 3.8088 (16.0); 1.5385 (3.2); 1.2654 (0.5); 0.8819 (1.0); −0.0002 (14.6) I.40-49: .sup.1H-NMR(400.6 MHz, CDCl.sub.3): δ = 7.3457 (0.9); 7.3248 (1.5); 7.3046 (1.2); 7.2605 (16.0); 7.1693 (0.8); 7.1662 (0.9); 7.1637 (1.0); 7.1607 (1.3); 7.1558 (0.9); 7.1479 (0.7); 7.1449 (0.7); 7.1420 (1.0); 7.1395 (1.5); 7.1348 (0.6); 7.1191 (0.5); 7.0761 (1.2); 7.0706 (1.1); 7.0520 (1.2); 7.0464 (1.1); 6.8360 (0.6); 6.8298 (0.8); 6.8163 (0.8); 6.8102 (0.8); 6.7941 (0.7); 6.7916 (0.7); 6.7854 (0.5); 6.7697 (0.6); 6.1027 (3.1); 6.1004 (3.2); 4.8614 (8.9); 3.8097 (16.0); 1.5515 (1.2); 0.0695 (0.6); −0.0002 (12.4) I.10-1: .sup.1H-NMR(300.1 MHZ, CDCl.sub.3): δ = 7.3275 (0.4); 7.3210 (0.7); 7.3149 (0.4); 7.2988 (2.1); 7.2940 (1.2); 7.2911 (1.2); 7.2741 (3.0); 7.2595 (9.7); 7.2468 (0.7); 7.2379 (1.4); 7.2115 (4.0); 7.2051 (3.6); 7.1944 (2.3); 7.1889 (2.2); 7.1827 (4.0); 7.1725 (1.1); 7.1649 (2.1); 7.1556 (0.3); 7.0247 (0.4); 7.0154 (2.1); 7.0083 (0.7); 6.9865 (3.4); 6.9643 (0.6); 6.9574 (1.6); 6.0132 (4.9); 4.8925 (8.5); 3.8152 (16.0); 1.5624 (3.4); −0.0001 (6.8) I.20-38: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.6276 (1.0); 7.6124 (1.2); 7.6055 (2.1); 7.5905 (2.1); 7.5836 (1.3); 7.5685 (1.1); 7.4432 (6.6); 7.4386 (3.4); 7.4219 (8.2); 7.4151 (2.6); 7.3886 (1.1); 7.3818 (1.1); 7.2515 (9.2); 7.2302 (8.5); 7.2147 (1.0); 7.2121 (1.0); 7.2078 (0.9); 6.3520 (10.6); 4.8274 (16.0); 4.1895 (2.4); 4.1718 (7.4); 4.1540 (7.4); 4.1363 (2.5); 3.3208 (17.3); 2.5095 (25.2); 2.5053 (33.4); 2.5011 (25.0); 1.2080 (7.8); 1.1902 (15.7); 1.1725 (7.6) I.11-38: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 7.6295 (1.0); 7.6138 (1.5); 7.6074 (2.0); 7.5922 (2.2); 7.5855 (1.2); 7.5703 (1.1); 7.4381 (1.3); 7.4314 (1.2); 7.4151 (2.0); 7.4118 (2.2); 7.3894 (1.3); 7.3829 (1.1); 7.3113 (0.4); 7.2936 (2.8); 7.2796 (3.9); 7.2715 (5.2); 7.2578 (5.7); 7.2340 (7.0); 7.2118 (7.8); 7.1897 (2.3); 6.3151 (10.4); 4.8267 (15.0); 4.7871 (0.9); 4.7635 (0.4); 4.2795 (0.5); 4.1902 (2.4); 4.1724 (7.3); 4.1546 (7.4); 4.1370 (2.5); 3.7376 (0.4); 3.3739 (0.5); 3.3431 (60.2); 3.3395 (98.4); 2.6769 (1.3); 2.6074 (0.4); 2.5120 (180.8); 2.5078 (192.7); 2.3349 (1.2); 1.9949 (0.5); 1.2668 (0.4); 1.2367 (1.1); 1.2098 (8.2); 1.1919 (16.0); 1.1742 (7.6); 0.9169 (0.3) I.11-38: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 7.8460 (0.4); 7.8387 (2.9); 7.8333 (1.2); 7.8249 (3.3); 7.8165 (3.4); 7.8081 (1.3); 7.8027 (3.0); 7.7953 (0.4); 7.7155 (0.9); 7.7004 (1.0); 7.6935 (1.8); 7.6785 (1.8); 7.6716 (1.1); 7.6565 (1.0); 7.5912 (1.0); 7.5842 (1.0); 7.5683 (1.2); 7.5648 (1.3); 7.5616 (1.3); 7.5581 (1.2); 7.5422 (1.0); 7.5353 (1.0); 7.3140 (0.7); 7.3105 (0.9); 7.3070 (0.8); 7.3039 (0.7); 7.2847 (4.4); 7.2676 (2.0); 7.2624 (6.5); 7.2452 (1.0); 7.2401 (2.9); 6.4612 (9.7); 4.9391 (12.3); 4.1959 (2.1); 4.1781 (6.6); 4.1603 (6.7); 4.1426 (2.1); 3.3421 (49.5); 2.5130 (2.7); 2.5085 (5.8); 2.5040 (7.9); 2.4995 (5.7); 2.4951 (2.6); 1.9904 (0.3); 1.2321 (1.0); 1.2219 (7.7); 1.2041 (16.0); 1.1863 (7.4); −0.0004 (1.0) I.3-38: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.6302 (1.1); 7.6246 (1.0); 7.6085 (3.0); 7.6027 (2.2); 7.5931 (2.5); 7.5870 (3.0); 7.5710 (1.3); 7.3991 (2.2); 7.3930 (1.5); 7.3765 (3.5); 7.3732 (3.6); 7.3456 (10.3); 7.3422 (12.3); 7.3355 (16.0); 7.3296 (9.2); 7.2788 (0.4); 7.2263 (7.3); 7.2230 (7.7); 7.2202 (8.4); 7.2168 (8.1); 7.2137 (8.6); 7.2108 (9.0); 7.2052 (9.1); 7.1911 (2.1); 7.1883 (2.1); 7.1847 (1.9); 6.8765 (0.4); 6.2421 (10.1); 6.2360 (8.6); 4.6134 (12.4); 4.0617 (0.4); 4.0553 (0.4); 4.0438 (1.0); 4.0375 (0.9); 4.0260 (1.0); 4.0198 (0.9); 4.0083 (0.4); 4.0020 (0.4); 3.6175 (0.7); 3.6071 (1.0); 3.6009 (1.0); 3.5907 (0.8); 3.5373 (0.6); 3.5114 (0.8); 3.3898 (0.8); 3.3220 (0.8); 3.1940 (0.5); 3.1438 (0.4); 2.6721 (0.7); 2.5518 (1.2); 2.5079 (100.8); 2.5037 (98.5); 2.4586 (0.8); 2.3350 (0.6); 2.1840 (0.6); 1.9952 (4.0); 1.9889 (3.4); 1.9119 (1.6); 1.9058 (1.3); 1.7655 (0.7); 1.7590 (0.6); 1.3614 (3.5); 1.3555 (3.0); 1.2397 (2.9); 1.1982 (1.5); 1.1919 (1.3); 1.1805 (2.6); 1.1741 (2.3); 1.1627 (1.4); 1.1563 (1.1); 0.8589 (0.5); 0.8414 (0.4) I.41-7: .sup.1H-NMR(400.4 MHZ, d.sub.6-DMSO): δ = 7.5252 (0.9); 7.5090 (1.1); 7.5039 (1.9); 7.4877 (1.9); 7.4828 (1.4); 7.4664 (1.0); 7.4549 (0.8); 7.4473 (6.2); 7.4421 (2.8); 7.4305 (2.3); 7.4251 (7.6); 7.3792 (1.0); 7.3730 (1.1); 7.3533 (1.5); 7.3493 (1.5); 7.3299 (0.9); 7.3236 (1.0); 7.2390 (0.9); 7.2334 (1.0); 7.2179 (1.7); 7.2125 (1.7); 7.1859 (7.5); 7.1807 (3.1); 7.1690 (2.1); 7.1637 (6.4); 6.2815 (8.5); 4.8752 (13.3); 4.7623 (0.7); 4.2757 (0.8); 4.2109 (2.0); 4.1932 (6.5); 4.1755 (6.6); 4.1577 (2.1); 4.1479 (0.4); 3.3258 (56.9); 2.6813 (0.6); 2.6767 (0.9); 2.6722 (0.7); 2.5302 (3.1); 2.5255 (4.8); 2.5167 (46.6); 2.5123 (101.7); 2.5078 (143.4); 2.5033 (113.4); 2.4989 (60.4); 2.3394 (0.6); 2.3348 (0.9); 2.3301 (0.7); 1.2288 (7.6); 1.2111 (16.0); 1.1934 (7.4) I.21-20: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.4267 (2.0); 7.4228 (2.3); 7.4071 (4.1); 7.4030 (3.8); 7.3874 (2.8); 7.3834 (3.4); 7.3707 (15.2); 7.3543 (9.0); 7.3495 (16.0); 7.1841 (13.5); 7.1795 (4.3); 7.1673 (4.1); 7.1628 (11.0); 7.0636 (10.3); 7.0437 (9.1); 7.0278 (2.6); 6.8744 (0.3); 6.1694 (13.1); 4.6136 (8.3); 3.6038 (0.4); 3.5125 (0.7); 3.4250 (47.1); 3.3289 (28.4); 2.6787 (1.8); 2.6742 (2.5); 2.6698 (1.9); 2.6046 (0.5); 2.5274 (8.8); 2.5137 (155.7); 2.5097 (315.8); 2.5053 (425.3); 2.5009 (311.6); 2.4967 (152.3); 2.4559 (1.3); 2.3366 (2.0); 2.3322 (2.8); 2.3277 (2.0); 2.1869 (0.7); 1.9110 (0.6); 1.3589 (4.1); 1.2728 (0.4); 1.2395 (1.7); 1.1846 (1.2); 1.1730 (0.7) I.12-20: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 7.4228 (3.0); 7.4186 (2.8); 7.4029 (6.3); 7.3832 (4.2); 7.3786 (4.7); 7.3716 (6.3); 7.3673 (5.7); 7.3509 (6.8); 7.2828 (0.6); 7.2685 (0.6); 7.2478 (0.7); 7.2254 (5.6); 7.2101 (8.7); 7.2034 (10.3); 7.1950 (6.7); 7.1895 (8.8); 7.1590 (9.6); 7.1369 (13.5); 7.1197 (3.8); 7.1147 (4.9); 7.0932 (0.6); 7.0600 (12.9); 7.0408 (12.3); 7.0241 (3.6); 6.8800 (0.8); 6.6523 (0.4); 6.2526 (0.5); 6.1326 (16.0); 4.6234 (13.6); 4.1778 (0.3); 4.1592 (0.3); 4.0632 (0.4); 4.0457 (0.9); 4.0280 (0.9); 4.0097 (0.4); 3.9728 (0.3); 3.9580 (0.4); 3.9348 (0.3); 3.8074 (0.6); 3.7612 (0.4); 3.7179 (0.5); 3.6992 (0.5); 3.6098 (1.0); 3.5935 (0.8); 3.5156 (1.5); 3.4639 (3.7); 3.4315 (54.5); 3.3349 (85.7); 3.1434 (0.9); 3.1177 (0.8); 2.9862 (0.8); 2.9630 (0.8); 2.8971 (0.6); 2.8676 (0.5); 2.8255 (0.6); 2.7538 (0.5); 2.7299 (0.5); 2.6829 (4.0); 2.6785 (4.4); 2.6108 (1.3); 2.5139 (562.5); 2.5097 (623.7); 2.3408 (3.4); 2.3365 (3.8); 2.1911 (1.4); 1.9967 (2.8); 1.9208 (1.1); 1.9153 (2.4); 1.3632 (8.9); 1.2691 (1.2); 1.2456 (4.9); 1.1999 (1.3); 1.1885 (1.8); 1.1824 (1.8); 1.1704 (0.5); 1.1648 (0.9); 1.1529 (0.4); 0.9425 (0.4); 0.8620 (0.8) I.47-7: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5506 (2.6); 7.5443 (2.7); 7.5167 (2.7); 7.5114 (2.6); 7.4761 (1.7); 7.4543 (7.7); 7.4483 (5.6); 7.4249 (11.4); 7.4125 (5.4); 7.4063 (4.3); 7.3847 (1.7); 7.3784 (1.6); 7.3483 (0.4); 7.2097 (1.3); 7.2000 (8.0); 7.1931 (2.6); 7.1771 (2.6); 7.1706 (6.4); 7.1604 (0.8); 6.3014 (8.8); 4.8732 (13.8); 4.2152 (2.3); 4.1915 (7.0); 4.1678 (7.1); 4.1442 (2.5); 3.3229 (10.7); 2.5096 (6.3); 2.5039 (7.8); 2.4981 (5.4); 2.0765 (3.7); 1.2292 (8.1); 1.2056 (16.0); 1.1819 (7.6); 0.8995 (0.5); 0.8755 (0.7); 0.8530 (0.6); 0.0000 (4.1) I.7-1: .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.3298 (0.9); 7.3259 (1.1); 7.3213 (0.8); 7.3088 (3.1); 7.2898 (3.5); 7.2829 (1.9); 7.2723 (2.9); 7.2682 (3.4); 7.2586 (38.5); 7.2480 (2.7); 7.2220 (3.4); 7.2182 (3.9); 7.2008 (2.5); 7.0306 (0.7); 7.0243 (0.7); 7.0094 (1.3); 7.0030 (1.5); 6.9948 (2.1); 6.9758 (1.6); 6.9358 (1.0); 6.9314 (1.1); 6.9117 (1.0); 6.9075 (1.1); 6.0530 (5.6); 4.8932 (9.9); 3.8387 (0.9); 3.8157 (16.0); 1.5331 (6.2); −0.0002 (13.6) I.1-2: .sup.1H-NMR(300.1 MHz, CDCl.sub.3): δ = 7.3548 (0.6); 7.3497 (0.7); 7.3292 (1.3); 7.3241 (1.3); 7.3040 (0.8); 7.2988 (0.8); 7.2768 (0.4); 7.2720 (0.4); 7.2504 (0.9); 7.2461 (0.9); 7.2348 (1.0); 7.2244 (1.3); 7.2183 (1.6); 7.2085 (4.2); 7.2026 (4.5); 7.1891 (9.4); 7.1736 (1.0); 7.1685 (1.1); 7.1552 (0.8); 7.1354 (3.0); 7.1294 (3.1); 7.1206 (2.3); 7.1022 (1.7); 7.0975 (1.6); 7.0711 (0.6); 7.0031 (0.9); 6.9707 (1.4); 6.9424 (0.7); 6.0155 (5.2); 4.8098 (9.0); 3.7381 (16.0); 1.4855 (3.2); −0.0001 (8.5); −0.0701 (6.4) I.2-4: .sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): δ = 7.3784 (5.2); 7.3696 (6.7); 7.3624 (7.0); 7.2450 (4.0); 7.2364 (4.8); 7.2276 (11.4); 7.2114 (16.0); 6.2351 (8.9); 4.8450 (13.7); 4.7599 (0.8); 4.2742 (0.9); 4.2026 (2.0); 4.1848 (6.1); 4.1670 (6.2); 4.1493 (2.1); 3.3292 (21.9); 2.6735 (0.4); 2.5085 (45.7); 2.5044 (58.1); 2.3314 (0.4); 1.2240 (6.8); 1.2061 (13.7); 1.1885 (6.5) I.11-4: .sup.1H-NMR(400.4 MHz, d.sub.6-DMSO): δ = 7.3011 (2.6); 7.2796 (6.2); 7.2655 (6.5); 7.2492 (8.4); 7.2420 (10.1); 7.2322 (12.4); 7.2262 (13.6); 7.2219 (15.6); 7.2100 (3.6); 6.2430 (9.3); 4.8428 (16.0); 4.7615 (0.6); 4.2769 (0.6); 4.2013 (2.5); 4.1837 (7.0); 4.1659 (7.0); 4.1482 (2.4); 3.3327 (62.0); 2.6751 (1.4); 2.5091 (201.1); 2.5062 (209.5); 2.3326 (1.3); 1.2237 (7.7); 1.2060 (14.4); 1.1883 (6.9) I.10-2: .sup.1H-NMR(599.8 MHz, CDCl.sub.3): δ = 7.4117 (2.0); 7.4090 (2.2); 7.3988 (3.9); 7.3962 (4.1); 7.3862 (2.2); 7.3834 (2.3); 7.3405 (1.1); 7.3376 (1.1); 7.3324 (1.2); 7.3278 (2.1); 7.3268 (2.1); 7.3251 (2.1); 7.3188 (2.1); 7.3170 (2.1); 7.3158 (2.0); 7.3144 (1.9); 7.3112 (1.5); 7.3060 (1.5); 7.3032 (1.4); 7.2610 (18.1); 7.1941 (2.9); 7.1818 (5.4); 7.1772 (6.2); 7.1736 (3.0); 7.1684 (8.2); 7.1625 (7.0); 7.1572 (2.8); 7.1536 (6.5); 7.1488 (0.8); 7.0612 (2.4); 7.0594 (2.5); 7.0450 (4.2); 7.0307 (2.2); 7.0288 (2.2); 6.9735 (0.9); 6.9687 (6.6); 6.9652 (2.2); 6.9541 (11.5); 6.9431 (2.0); 6.9397 (5.7); 6.9348 (0.6); 6.0535 (18.2); 5.2981 (1.0); 4.9000 (0.4); 4.8731 (31.0); 3.8180 (1.1); 3.8068 (50.0); 3.7033 (3.6); 1.5727 (21.3); 1.2553 (0.5); 0.0052 (1.0); −0.0001 (20.0); −0.0056 (0.7) I.50-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5611 (2.6); 7.5539 (2.8); 7.5443 (2.8); 7.5357 (3.0); 7.5265 (2.8); 7.5196 (3.2); 7.5150 (3.1); 7.5062 (2.7); 7.4690 (1.9); 7.4483 (2.2); 7.4401 (2.8); 7.4307 (1.9); 7.4196 (2.6); 7.4023 (3.5); 7.3765 (3.5); 7.3595 (3.9); 7.3527 (3.4); 7.3303 (1.4); 7.3237 (1.3); 7.3045 (1.7); 7.2960 (1.5); 7.2764 (2.6); 7.2678 (2.4); 7.2481 (1.3); 7.2394 (1.1); 6.2751 (11.2); 4.8494 (14.6); 4.8067 (0.3); 4.2046 (2.3); 4.1809 (7.1); 4.1572 (7.2); 4.1336 (2.4); 3.3245 (35.6); 2.5095 (8.3); 2.5038 (10.4); 2.4982 (7.4); 1.2330 (2.1); 1.2193 (8.1); 1.1956 (16.0); 1.1720 (7.6); 0.0001 (3.2) I.48-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 12.9502 (1.0); 7.6011 (2.9); 7.5939 (2.9); 7.5668 (3.0); 7.5595 (3.2); 7.5479 (3.2); 7.5157 (2.9); 7.5115 (3.0); 7.5017 (2.2); 7.4736 (4.5); 7.4462 (3.6); 7.3967 (3.4); 7.3917 (3.1); 7.3680 (2.3); 7.3631 (2.4); 7.3435 (7.5); 7.3368 (5.5); 7.3291 (5.9); 7.3004 (0.5); 6.3253 (9.0); 4.7541 (16.0); 3.3398 (3.7); 2.5136 (9.9); 2.5080 (17.7); 2.5022 (21.9); 2.4964 (14.8); 2.0744 (0.8); 0.0000 (12.8) I.48-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7290 (6.6); 7.7245 (6.8); 7.5363 (1.4); 7.5298 (1.1); 7.5159 (4.8); 7.5081 (11.2); 7.5007 (14.1); 7.4826 (4.2); 7.4760 (4.1); 7.3062 (2.6); 7.2996 (2.3); 7.2781 (5.2); 7.2717 (5.0); 7.2400 (4.4); 7.2138 (5.1); 7.1864 (2.3); 6.1540 (9.0); 4.2267 (16.0); 3.3705 (7.9); 2.5097 (14.0); 2.5039 (17.3); 2.4982 (11.9); 0.0000 (8.6); −0.0109 (0.3) I.51-48: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5559 (3.2); 7.5485 (3.8); 7.5435 (3.6); 7.5348 (3.4); 7.5215 (3.6); 7.5142 (5.8); 7.5053 (3.2); 7.4680 (2.2); 7.4489 (3.4); 7.4392 (3.4); 7.4220 (5.6); 7.3958 (3.8); 7.3644 (3.8); 7.3573 (3.4); 7.3342 (1.8); 7.3285 (1.6); 7.3025 (1.9); 7.2939 (1.7); 7.2744 (3.0); 7.2657 (2.6); 7.2460 (1.4); 7.2373 (1.2); 6.2540 (13.1); 4.7589 (16.0); 3.5024 (2.3); 2.5106 (7.5); 2.5049 (9.1); 2.4993 (6.4); 2.0757 (1.9); 1.2350 (1.0); −0.0001 (4.1) I.48-48: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5907 (3.6); 7.5807 (3.7); 7.5760 (2.9); 7.5624 (4.4); 7.5521 (3.6); 7.5465 (3.0); 7.5259 (3.0); 7.5202 (3.0); 7.4925 (3.0); 7.4863 (2.9); 7.3513 (1.8); 7.3419 (1.7); 7.3241 (2.7); 7.3127 (3.8); 7.3061 (2.0); 7.2947 (2.0); 7.2846 (6.2); 7.2781 (5.2); 7.2662 (4.1); 7.2414 (3.8); 7.2137 (1.6); 6.2834 (7.9); 6.2802 (7.3); 4.7332 (16.0); 4.7092 (0.6); 3.5530 (0.3); 3.3393 (26.8); 3.2108 (0.3); 2.5096 (13.0); 2.5038 (16.2); 2.4980 (11.1); 2.0748 (0.3); 1.9894 (0.8); 1.2352 (1.4); 1.1750 (0.4); 0.0000 (4.1) I.20-1: .sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): δ = 7.4557 (0.7); 7.4494 (5.9); 7.4446 (2.2); 7.4329 (2.4); 7.4279 (7.6); 7.4216 (1.2); 7.4158 (1.3); 7.4128 (2.0); 7.4085 (1.0); 7.3952 (5.0); 7.3913 (2.8); 7.3796 (1.8); 7.3758 (4.0); 7.3696 (0.8); 7.3486 (1.2); 7.3454 (2.3); 7.3422 (1.5); 7.3328 (0.9); 7.3272 (2.7); 7.3208 (0.7); 7.3120 (0.6); 7.3089 (0.8); 7.2600 (1.0); 7.2537 (7.5); 7.2488 (2.4); 7.2372 (2.2); 7.2323 (6.1); 7.2259 (0.9); 7.1975 (3.7); 7.1939 (5.7); 7.1887 (1.4); 7.1761 (3.9); 7.1666 (0.5); 6.2760 (10.9); 4.8642 (0.6); 4.8475 (13.9); 4.7596 (0.7); 4.2733 (0.8); 4.2019 (2.2); 4.1841 (6.8); 4.1664 (6.8); 4.1486 (2.3); 3.8200 (0.4); 3.7564 (0.9); 3.3741 (0.3); 3.3254 (45.0); 2.6783 (0.4); 2.6738 (0.6); 2.6691 (0.4); 2.5583 (0.4); 2.5537 (0.7); 2.5494 (0.9); 2.5411 (0.8); 2.5272 (2.3); 2.5224 (3.2); 2.5137 (27.8); 2.5093 (56.9); 2.5048 (76.9); 2.5002 (55.0); 2.4958 (25.8); 2.3362 (0.4); 2.3315 (0.5); 2.3272 (0.4); 1.2361 (0.8); 1.2235 (7.8); 1.2058 (16.0); 1.1880 (7.5) I.3-7: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 13.0794 (0.8); 12.8319 (0.8); 7.5797 (0.8); 7.4389 (12.6); 7.4220 (5.2); 7.4169 (16.0); 7.3930 (10.9); 7.3838 (13.9); 7.3768 (15.1); 7.2609 (7.2); 7.2518 (7.9); 7.2432 (6.3); 7.2367 (4.9); 7.1926 (15.8); 7.1759 (4.5); 7.1707 (13.3); 6.2095 (13.3); 4.7130 (7.2); 3.5984 (2.3); 3.5695 (0.8); 3.4475 (0.8); 3.4212 (1.2); 3.3740 (2.8); 3.3218 (695.8); 3.2829 (3.2); 3.2530 (0.9); 3.1710 (0.8); 2.6721 (8.7); 2.6677 (12.3); 2.6631 (8.8); 2.6006 (2.0); 2.5558 (4.8); 2.5509 (3.8); 2.5209 (50.6); 2.5075 (650.4); 2.5032 (1360.8); 2.4987 (1862.8); 2.4943 (1397.4); 2.4902 (686.4); 2.4584 (7.4); 2.4542 (7.4); 2.4192 (1.9); 2.4110 (1.8); 2.3971 (1.5); 2.3301 (9.3); 2.3256 (12.0); 2.3212 (9.2); 2.1798 (1.0); 1.9051 (0.8); 1.7569 (2.2); 1.7407 (0.9); 1.3521 (3.8); 1.2301 (1.6); 0.8385 (0.8); −0.0684 (0.8) I.2-38: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 7.6121 (1.2); 7.5982 (3.0); 7.5768 (2.8); 7.5611 (1.3); 7.4194 (2.2); 7.3940 (3.6); 7.3478 (14.2); 7.3441 (14.8); 7.2214 (11.1); 6.3140 (4.3); 6.3105 (8.9); 6.3074 (7.7); 6.3049 (7.7); 4.8286 (16.0); 4.1874 (2.3); 4.1749 (6.6); 4.1571 (6.9); 4.1395 (2.6); 3.3382 (53.8); 3.3346 (101.0); 3.0099 (0.4); 2.9912 (0.4); 2.9761 (0.4); 2.6763 (2.6); 2.5905 (0.7); 2.5076 (350.3); 2.5036 (329.0); 2.3342 (2.3); 1.2361 (2.2); 1.2119 (7.0); 1.2064 (6.8); 1.1982 (7.8); 1.1943 (13.9); 1.1912 (12.6); 1.1887 (12.6); 1.1766 (7.6); 0.8541 (0.5) I.12-38: .sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): δ = 7.7896 (0.4); 7.7749 (0.5); 7.7686 (0.5); 7.7539 (0.4); 7.6370 (1.9); 7.6216 (2.2); 7.6147 (4.2); 7.5999 (4.0); 7.5932 (2.5); 7.5779 (2.2); 7.4240 (2.0); 7.4172 (2.3); 7.3953 (3.6); 7.3753 (2.2); 7.3685 (2.2); 7.2902 (4.4); 7.2754 (6.4); 7.2683 (10.0); 7.2546 (10.2); 7.2271 (12.5); 7.2049 (15.0); 7.1828 (5.2); 7.1527 (0.5); 7.1301 (0.6); 7.1083 (0.5); 6.8951 (0.4); 6.8731 (0.4); 6.5236 (0.6); 6.4827 (0.5); 6.2786 (16.0); 6.1734 (0.4); 4.9190 (0.3); 4.7079 (15.5); 3.7349 (0.8); 3.5021 (0.4); 3.3290 (58.8); 2.6736 (2.6); 2.6204 (0.5); 2.6010 (0.4); 2.5552 (3.9); 2.5443 (3.2); 2.5088 (281.8); 2.5045 (393.4); 2.5004 (308.7); 2.4545 (3.0); 2.4019 (0.3); 2.3316 (2.4); 2.0779 (14.5); 1.3578 (1.7); 1.2383 (2.4); 1.2019 (0.3); 1.1858 (0.5); 1.1674 (0.3); 0.9145 (0.6); 0.8563 (0.4) I.21-4: .sup.1H-NMR(400.2 MHZ, d.sub.6-DMSO): δ = 7.4581 (5.5); 7.4371 (6.7); 7.2728 (0.5); 7.2585 (7.3); 7.2494 (10.5); 7.2364 (7.5); 7.2320 (16.0); 6.2537 (8.3); 5.7601 (0.5); 4.7402 (10.4); 3.6021 (0.4); 3.3308 (12.4); 2.6725 (0.6); 2.5564 (0.9); 2.5073 (77.1); 2.5034 (97.9); 2.4995 (71.2); 2.4546 (0.7); 2.3301 (0.6); 1.7611 (0.5); 1.3565 (0.4); 1.2375 (0.6); 1.1822 (0.6); 1.1704 (0.4) I.3-20: .sup.1H-NMR(400.4 MHz, d.sub.6-DMSO): δ = 7.4487 (0.5); 7.4154 (2.9); 7.4114 (2.9); 7.3955 (5.4); 7.3759 (3.4); 7.3722 (3.4); 7.3532 (5.1); 7.3364 (5.9); 7.3328 (4.9); 7.2879 (12.4); 7.2795 (14.8); 7.2720 (14.7); 7.2626 (1.6); 7.1804 (8.2); 7.1721 (7.6); 7.1629 (6.0); 7.1564 (4.6); 7.0533 (12.9); 7.0337 (14.1); 7.0162 (2.8); 6.1413 (16.0); 4.6677 (11.3); 3.6600 (0.6); 3.5807 (0.4); 3.5675 (0.3); 3.5298 (0.4); 3.4026 (53.8); 3.3292 (45.2); 3.2185 (0.7); 2.6756 (2.8); 2.6717 (2.2); 2.5620 (1.4); 2.5109 (391.4); 2.5068 (486.3); 2.5025 (346.6); 2.4618 (1.8); 2.4015 (0.7); 2.3381 (2.5); 2.3336 (3.0); 2.1879 (0.4); 2.0799 (9.4); 1.9136 (0.8); 1.3607 (1.6); 1.2753 (0.4); 1.2427 (1.7); 1.1959 (0.4); 1.1752 (0.8); 1.1335 (0.4); 0.8923 (0.4) I.42-49: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 12.9548 (1.4); 12.9471 (1.4); 12.3152 (0.5); 11.5512 (0.6); 10.3512 (0.5); 7.5033 (1.1); 7.4800 (2.2); 7.4640 (2.2); 7.4427 (1.1); 7.3625 (1.5); 7.3330 (2.0); 7.3129 (1.0); 7.2231 (10.8); 7.2043 (16.0); 7.1793 (1.5); 6.7544 (0.5); 6.2298 (8.1); 4.7721 (11.7); 4.7494 (0.6); 4.7023 (0.5); 4.4979 (0.5); 4.4003 (0.6); 4.1969 (0.6); 4.1289 (0.5); 4.0449 (0.8); 3.9130 (0.5); 3.7151 (0.5); 3.6848 (0.6); 3.5919 (0.7); 3.5799 (0.6); 3.5529 (0.5); 3.5339 (0.6); 3.3320 (560.8); 3.3058 (3.2); 3.3032 (3.1); 3.2974 (2.8); 3.2611 (1.2); 3.1903 (0.9); 3.1710 (0.7); 3.1558 (0.7); 3.1061 (0.7); 3.0778 (0.7); 3.0317 (1.0); 3.0105 (1.0); 2.9845 (1.1); 2.9530 (1.1); 2.9259 (1.1); 2.8846 (0.9); 2.8750 (0.9); 2.8442 (0.9); 2.7948 (0.9); 2.7556 (0.8); 2.6778 (7.5); 2.5129 (989.6); 2.5089 (1064.2); 2.4797 (5.8); 2.4374 (1.7); 2.3360 (6.2); 1.9967 (1.1); 1.2846 (0.6); 1.2433 (1.4); 1.1995 (0.7); 1.1819 (0.7); 0.8652 (0.6); −2.0634 (0.5); −2.5399 (0.5) I.47-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7567 (4.6); 7.7507 (4.6); 7.5399 (1.6); 7.5335 (3.2); 7.5279 (2.7); 7.5116 (5.8); 7.5047 (6.9); 7.4988 (9.0); 7.4699 (1.3); 7.3277 (1.5); 7.3213 (1.3); 7.2998 (4.4); 7.2934 (4.3); 7.2815 (3.4); 7.2566 (3.3); 7.2289 (1.4); 6.3280 (6.8); 6.3250 (6.1); 4.8300 (13.8); 4.1902 (2.2); 4.1665 (7.0); 4.1428 (7.1); 4.1192 (2.3); 3.3328 (74.1); 2.5104 (7.5); 2.5047 (9.1); 2.4989 (6.2); 2.0764 (0.9); 1.2338 (2.3); 1.2121 (8.0); 1.1884 (16.0); 1.1647 (7.4); 0.8525 (0.3); 0.0000 (1.8) I.20-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.6095 (2.5); 7.6022 (2.7); 7.5800 (2.6); 7.5759 (3.0); 7.5684 (2.9); 7.5524 (4.2); 7.5247 (2.9); 7.4571 (6.6); 7.4507 (3.1); 7.4457 (3.3); 7.4423 (3.5); 7.4351 (5.2); 7.4287 (8.9); 7.4178 (2.3); 7.4142 (2.1); 7.4098 (1.8); 7.2653 (8.4); 7.2592 (2.8); 7.2369 (6.3); 6.3673 (11.1); 4.8332 (14.7); 4.1981 (2.3); 4.1745 (7.1); 4.1508 (7.2); 4.1271 (2.4); 3.3251 (5.5); 2.5105 (4.4); 2.5049 (5.5); 2.4993 (3.9); 2.0774 (2.0); 1.2134 (7.8); 1.1898 (16.0); 1.1661 (7.6); 0.0001 (2.8) I.20-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5297 (2.0); 7.5236 (2.1); 7.4955 (2.0); 7.4909 (2.0); 7.4484 (1.1); 7.4208 (2.7); 7.3970 (3.4); 7.3903 (4.3); 7.3843 (3.6); 7.3626 (1.0); 7.3564 (1.1); 7.2582 (0.4); 7.2463 (0.5); 7.2270 (9.2); 7.2032 (16.0); 6.2715 (7.4); 4.8635 (12.2); 4.2145 (1.9); 4.1908 (6.0); 4.1672 (6.1); 4.1435 (2.0); 3.3425 (79.2); 2.8925 (0.6); 2.7343 (0.6); 2.5110 (4.0); 2.5052 (5.0); 2.4995 (3.6); 2.0755 (4.6); 1.9897 (0.4); 1.2289 (7.1); 1.2052 (13.7); 1.1815 (6.5); 0.0000 (1.3) I.20-38: .sup.1H-NMR(300.1 MHZ, d.sub.6-DMSO): δ = 7.5319 (2.8); 7.5197 (1.5); 7.5102 (2.4); 7.4997 (2.7); 7.4953 (3.0); 7.4810 (1.4); 7.4609 (1.2); 7.4327 (1.1); 7.4235 (1.2); 7.4023 (1.5); 7.3967 (1.7); 7.3938 (1.7); 7.3882 (1.4); 7.3671 (1.3); 7.3580 (1.5); 7.3460 (0.7); 7.3325 (6.2); 7.3179 (4.7); 7.2891 (0.5); 7.2137 (1.0); 7.2092 (1.0); 7.2046 (1.0); 7.2003 (0.9); 7.1820 (1.6); 7.1569 (0.8); 7.1522 (0.8); 7.1476 (0.8); 6.3257 (7.3); 4.8441 (14.0); 4.8148 (0.5); 4.6566 (0.7); 4.2022 (2.3); 4.1785 (7.0); 4.1548 (7.1); 4.1444 (0.8); 4.1312 (2.4); 4.1204 (0.5); 3.4950 (0.5); 3.3331 (42.8); 2.5114 (4.5); 2.5056 (5.6); 2.4999 (4.0); 1.2334 (1.2); 1.2157 (8.0); 1.1920 (16.0); 1.1683 (7.5); 0.8742 (0.7); 0.8529 (0.5); 0.0000 (1.1) I.21-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5943 (4.3); 7.5906 (4.6); 7.5879 (4.6); 7.5621 (8.6); 7.5536 (4.1); 7.5349 (4.0); 7.4496 (9.1); 7.4432 (3.8); 7.4364 (4.3); 7.4328 (4.8); 7.4275 (7.2); 7.4211 (12.7); 7.4125 (2.5); 7.4081 (2.8); 7.4046 (2.8); 7.4005 (2.4); 7.2569 (11.8); 7.2505 (3.8); 7.2343 (3.7); 7.2283 (8.9); 6.3099 (15.7); 4.6487 (16.0); 3.8702 (0.3); 3.7430 (0.4); 3.6785 (0.4); 3.6032 (0.5); 3.5736 (0.5); 3.5123 (0.6); 3.4780 (0.5); 3.3855 (0.5); 3.2506 (0.4); 3.1996 (0.3); 2.5086 (16.3); 2.5028 (20.6); 2.4971 (14.4); 1.9863 (0.3); 1.2352 (2.2); 0.8533 (0.4); 0.0000 (7.9); −0.0109 (0.4) I.48-7: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 12.9577 (0.4); 7.5517 (3.0); 7.5456 (3.1); 7.5179 (3.1); 7.5126 (3.1); 7.4784 (1.9); 7.4555 (9.9); 7.4263 (14.2); 7.4125 (6.3); 7.4063 (5.0); 7.3847 (2.0); 7.3784 (1.8); 7.2074 (9.8); 7.2007 (3.3); 7.1781 (7.8); 7.1682 (1.1); 6.2797 (11.1); 4.7833 (16.0); 3.4269 (0.8); 3.3949 (0.7); 2.5095 (6.6); 2.5039 (8.2); 2.4983 (5.8); 2.0759 (1.9); 0.0001 (3.6) I.41-38: .sup.1H-NMR(400.3 MHZ, d.sub.6-DMSO): δ = 7.5279 (0.9); 7.5128 (1.0); 7.5058 (1.9); 7.4908 (1.9); 7.4837 (1.2); 7.4687 (0.9); 7.4250 (1.0); 7.4182 (1.1); 7.3991 (2.2); 7.3835 (1.4); 7.3783 (2.6); 7.3689 (1.5); 7.3618 (2.9); 7.3570 (2.0); 7.3407 (1.5); 7.3346 (1.7); 7.3310 (1.7); 7.3112 (1.0); 7.3049 (1.1); 7.2044 (0.9); 7.1979 (0.8); 7.1838 (1.6); 7.1648 (1.7); 7.1586 (1.7); 7.1443 (1.8); 7.1385 (1.8); 7.1238 (0.9); 7.1171 (0.9); 6.3031 (7.8); 4.8454 (15.0); 4.7654 (0.9); 4.2795 (1.1); 4.1983 (2.2); 4.1805 (7.0); 4.1627 (7.2); 4.1450 (2.4); 3.3841 (0.6); 3.3633 (1.4); 3.3595 (0.9); 3.3353 (222.0); 3.3166 (1.3); 2.6838 (1.1); 2.6795 (1.4); 2.6752 (1.1); 2.5546 (1.0); 2.5328 (5.7); 2.5192 (79.6); 2.5150 (160.0); 2.5106 (215.8); 2.5062 (163.0); 2.4503 (0.3); 2.3420 (1.0); 2.3376 (1.3); 2.3332 (1.0); 1.4064 (0.4); 1.2462 (1.7); 1.2313 (0.6); 1.2162 (8.0); 1.1985 (16.0); 1.1807 (7.4) I.41-38: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 7.9791 (0.9); 7.9622 (1.1); 7.9571 (1.9); 7.9403 (1.9); 7.9351 (1.1); 7.9182 (0.9); 7.7333 (0.9); 7.7183 (1.0); 7.7114 (1.8); 7.6963 (1.8); 7.6895 (1.1); 7.6744 (1.0); 7.6070 (1.0); 7.6001 (1.0); 7.5842 (1.2); 7.5807 (1.3); 7.5775 (1.3); 7.5740 (1.2); 7.5581 (1.0); 7.5512 (1.0); 7.4007 (0.9); 7.3943 (1.0); 7.3773 (1.1); 7.3714 (1.8); 7.3655 (1.1); 7.3485 (1.0); 7.3421 (1.0); 7.3265 (0.7); 7.3230 (0.8); 7.3195 (0.7); 7.3164 (0.7); 7.3026 (1.3); 7.3007 (1.2); 7.2971 (1.2); 7.2838 (0.7); 7.2803 (0.7); 7.2767 (0.6); 7.2737 (0.6); 7.1904 (0.8); 7.1886 (0.8); 7.1835 (0.8); 7.1682 (1.5); 7.1620 (1.5); 7.1480 (0.8); 7.1462 (0.8); 7.1411 (0.7); 6.3192 (4.2); 6.3106 (4.3); 4.9845 (12.1); 4.1919 (2.1); 4.1741 (6.7); 4.1563 (6.7); 4.1386 (2.2); 3.3401 (14.9); 2.5145 (1.8); 2.5101 (3.9); 2.5056 (5.3); 2.5011 (3.8); 2.4967 (1.7); 1.2145 (7.6); 1.1967 (16.0); 1.1789 (7.4) I.2-1: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 7.3909 (2.4); 7.3729 (12.9); 7.3689 (9.3); 7.3656 (9.7); 7.3564 (10.0); 7.3262 (3.0); 7.3233 (2.1); 7.3137 (1.4); 7.3083 (3.0); 7.3015 (0.9); 7.2928 (0.9); 7.2899 (1.0); 7.2458 (4.5); 7.2397 (4.6); 7.2342 (3.7); 7.2308 (4.4); 7.2250 (2.7); 7.2218 (3.0); 7.1877 (5.1); 7.1846 (6.4); 7.1668 (5.0); 6.2430 (1.5); 6.2338 (10.5); 4.8531 (15.5); 4.2081 (2.3); 4.1994 (1.2); 4.1904 (7.0); 4.1817 (1.5); 4.1726 (7.1); 4.1549 (2.4); 3.3931 (0.4); 3.3538 (31.9); 3.3446 (212.2); 2.6774 (0.6); 2.5128 (76.8); 2.5085 (91.7); 2.5041 (66.0); 2.3398 (0.5); 2.3354 (0.6); 1.9953 (1.0); 1.2387 (1.4); 1.2296 (7.8); 1.2210 (2.8); 1.2119 (16.0); 1.2034 (1.9); 1.1942 (7.6); 1.1804 (0.8); 1.1625 (0.4); 0.8664 (0.4); 0.8577 (0.4) I.20-4: .sup.1H-NMR(400.4 MHZ, d.sub.6-DMSO): δ = 7.4686 (3.3); 7.4622 (7.2); 7.4462 (5.0); 7.4409 (8.4); 7.2580 (12.7); 7.2532 (12.3); 7.2441 (12.4); 7.2367 (15.6); 6.2903 (4.0); 6.2834 (10.6); 5.7700 (0.4); 5.7641 (0.5); 4.8439 (16.0); 4.7608 (0.4); 4.2769 (0.4); 4.1993 (2.7); 4.1882 (3.1); 4.1816 (7.3); 4.1703 (3.4); 4.1638 (7.4); 4.1461 (2.6); 3.3386 (48.2); 3.3320 (91.7); 2.6744 (3.5); 2.6057 (1.3); 2.5095 (436.0); 2.5054 (445.5); 2.4046 (0.5); 2.3325 (3.4); 1.2213 (8.1); 1.2103 (6.8); 1.2036 (16.0); 1.1859 (7.6) I.11-20: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 7.4288 (1.2); 7.4248 (1.2); 7.4058 (2.3); 7.3895 (1.5); 7.3853 (1.7); 7.3580 (2.4); 7.3541 (2.3); 7.3392 (2.7); 7.3351 (2.4); 7.2290 (2.4); 7.2236 (1.2); 7.2150 (3.1); 7.2068 (4.8); 7.1992 (1.8); 7.1930 (4.4); 7.1718 (0.9); 7.1657 (4.6); 7.1435 (6.6); 7.1263 (1.1); 7.1215 (2.4); 7.0652 (5.1); 7.0450 (7.4); 7.0261 (1.7); 6.1845 (10.3); 4.7964 (15.6); 4.1912 (2.3); 4.1735 (7.0); 4.1557 (7.1); 4.1380 (2.4); 3.4671 (0.8); 3.4345 (27.0); 3.3302 (86.6); 2.6832 (1.2); 2.6790 (1.4); 2.5320 (7.1); 2.5144 (171.5); 2.5100 (223.0); 2.5057 (161.2); 2.4559 (0.6); 2.4515 (0.6); 2.3414 (1.1); 2.3368 (1.4); 2.3328 (1.0); 2.1257 (0.6); 1.2460 (0.8); 1.2180 (7.8); 1.2002 (16.0); 1.1825 (7.5); 1.1486 (1.4) I.41-20: .sup.1H-NMR(400.4 MHz, d.sub.6-DMSO): δ = 7.3716 (1.7); 7.3674 (1.7); 7.3528 (6.4); 7.3497 (7.1); 7.3308 (6.1); 7.3072 (1.6); 7.3015 (1.3); 7.2826 (2.9); 7.2580 (1.6); 7.2522 (1.1); 7.2028 (1.0); 7.1858 (2.2); 7.1817 (2.3); 7.1650 (2.8); 7.1440 (1.2); 7.0337 (3.3); 7.0182 (5.4); 6.9997 (6.2); 6.9788 (3.4); 6.1498 (7.6); 4.8114 (16.0); 4.1928 (2.4); 4.1750 (6.9); 4.1573 (6.9); 4.1396 (2.3); 3.4189 (25.8); 3.3371 (24.6); 3.3298 (58.2); 2.6744 (0.4); 2.5093 (52.8); 2.5054 (52.8); 2.3362 (0.4); 1.2407 (1.1); 1.2168 (7.5); 1.1990 (14.6); 1.1813 (7.1); 1.1447 (0.4) I.42-20: .sup.1H-NMR(400.3 MHz, d.sub.6-DMSO): δ = 13.1216 (0.4); 13.1136 (0.4); 13.0865 (0.5); 13.0620 (0.6); 13.0131 (0.9); 12.9756 (0.8); 12.8978 (0.6); 12.8286 (0.3); 7.3710 (13.6); 7.3520 (15.9); 7.3331 (5.0); 7.3288 (3.7); 7.3128 (3.7); 7.3063 (3.5); 7.2890 (5.1); 7.2635 (2.7); 7.2569 (2.0); 7.2039 (3.3); 7.1872 (4.5); 7.1827 (5.3); 7.1661 (5.0); 7.1449 (2.2); 7.0489 (7.0); 7.0410 (9.2); 7.0379 (8.9); 7.0273 (10.1); 7.0218 (12.2); 6.9998 (10.8); 6.9779 (5.5); 6.1218 (12.2); 4.6977 (16.0); 4.3477 (0.3); 4.1962 (0.3); 4.0435 (0.7); 4.0259 (0.5); 3.7520 (0.4); 3.7308 (0.3); 3.6370 (0.6); 3.6043 (0.7); 3.5057 (0.8); 3.4187 (50.6); 3.3395 (31.4); 3.2701 (1.3); 3.2346 (0.9); 3.2095 (0.6); 3.0988 (0.5); 3.0124 (0.7); 2.9490 (0.6); 2.8135 (0.4); 2.7387 (0.6); 2.6811 (2.6); 2.6769 (2.5); 2.6276 (1.0); 2.5164 (267.5); 2.5124 (335.6); 2.5079 (337.4); 2.5035 (213.4); 2.3392 (2.0); 2.3349 (2.0); 2.1926 (0.4); 2.0920 (1.0); 1.9953 (1.8); 1.3611 (2.0); 1.2426 (1.3); 1.1979 (1.0); 1.1862 (0.9); 1.1805 (1.4); 1.1628 (0.6) I.41-32: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.7447 (4.4); 7.7399 (4.6); 7.5349 (0.8); 7.5284 (0.6); 7.5064 (5.5); 7.4995 (7.5); 7.4962 (7.6); 7.4677 (1.0); 7.3516 (1.4); 7.3482 (1.5); 7.3442 (1.4); 7.3196 (3.5); 7.3130 (2.1); 7.2979 (2.4); 7.2910 (1.8); 7.2865 (1.5); 7.2776 (1.4); 7.2696 (1.4); 7.1434 (1.0); 7.1410 (1.1); 7.1348 (1.0); 7.1132 (1.8); 7.1063 (1.7); 7.0866 (0.8); 7.0842 (0.8); 7.0782 (0.8); 6.2974 (7.0); 6.2950 (6.5); 4.8314 (13.8); 4.1939 (2.2); 4.1702 (6.9); 4.1465 (7.0); 4.1229 (2.3); 3.3435 (53.4); 2.5140 (3.0); 2.5082 (3.9); 2.5024 (2.7); 2.0787 (2.2); 1.2339 (0.8); 1.2152 (7.8); 1.1915 (16.0); 1.1678 (7.5); 0.0000 (0.8) I.11-49: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5928 (3.8); 7.5584 (4.8); 7.5464 (5.3); 7.5186 (3.3); 7.4346 (4.4); 7.4077 (3.1); 7.3068 (3.2); 7.2788 (7.9); 7.2601 (7.4); 7.2436 (7.2); 7.2142 (8.2); 7.1855 (3.2); 6.3227 (9.4); 4.8274 (16.0); 4.1971 (2.8); 4.1737 (7.5); 4.1503 (7.7); 4.1270 (3.1); 3.3214 (9.7); 2.5037 (14.8); 1.9886 (0.3); 1.2134 (8.6); 1.1899 (15.4); 1.1665 (8.2); 0.0005 (3.4) I.47-48: .sup.1H-NMR(300.1 MHz, d.sub.6-DMSO): δ = 7.5963 (2.5); 7.5869 (2.7); 7.5790 (2.1); 7.5676 (2.9); 7.5588 (4.1); 7.5495 (2.5); 7.5276 (3.2); 7.5208 (2.6); 7.4930 (2.6); 7.4867 (2.6); 7.3500 (1.5); 7.3405 (1.4); 7.3227 (2.2); 7.3139 (3.2); 7.2933 (1.9); 7.2863 (4.8); 7.2801 (4.4); 7.2670 (3.4); 7.2421 (3.3); 7.2144 (1.4); 6.3074 (6.7); 6.3042 (6.2); 4.8267 (14.1); 4.1901 (2.2); 4.1664 (6.9); 4.1427 (7.0); 4.1191 (2.3); 3.3324 (88.1); 2.5099 (8.2); 2.5041 (10.3); 2.4984 (7.2); 2.0759 (0.8); 1.2342 (1.2); 1.2121 (7.8); 1.1884 (16.0); 1.1647 (7.5); 0.0000 (3.8) I.12-49: .sup.1H-NMR(300.1 MHZ, d.sub.6-DMSO): δ = 12.9233 (0.6); 7.5947 (3.0); 7.5873 (5.0); 7.5596 (6.8); 7.5540 (3.9); 7.5313 (3.2); 7.4396 (2.7); 7.4363 (2.9); 7.4323 (2.6); 7.4109 (1.8); 7.4077 (1.9); 7.4038 (1.8); 7.3080 (2.2); 7.3002 (1.2); 7.2892 (3.2); 7.2781 (6.1); 7.2679 (2.2); 7.2597 (5.5); 7.2507 (2.2); 7.2429 (5.9); 7.2352 (1.6); 7.2134 (7.5); 7.1908 (1.1); 7.1837 (2.4); 6.2995 (13.1); 4.7349 (16.0); 3.3551 (5.8); 2.5080 (15.0); 2.5023 (19.2); 2.4966 (13.5); 0.0000 (10.8); −0.0110 (0.5) I.48-4: .sup.1H-NMR(300.1 MHZ, d.sub.6-DMSO): δ =7.5300 (2.1); 7.5238 (2.1); 7.4961 (2.0); 7.4909 (2.0); 7.4524 (1.1); 7.4248 (2.7); 7.4006 (3.0); 7.3907 (4.1); 7.3845 (3.3); 7.3629 (1.2); 7.3567 (1.1); 7.2319 (14.8); 7.2095 (16.0); 6.2518 (7.4); 4.7770 (11.3); 3.7358 (0.4); 3.7112 (0.5); 3.5767 (0.8); 3.4301 (0.5); 3.4000 (0.4); 2.5133 (2.5); 2.5075 (3.1); 2.5017 (2.1); 0.0000 (0.9) I.47-38: .sup.1H-NMR(400.6 MHz, CDCl.sub.3): δ = 7.3947 (0.7); 7.3801 (0.7); 7.3732 (1.3); 7.3586 (1.3); 7.3517 (0.8); 7.3371 (0.8); 7.2630 (2.9); 7.1165 (0.7); 7.0943 (2.8); 7.0839 (1.1); 7.0807 (4.6); 7.0790 (5.8); 7.0777 (6.5); 7.0731 (1.8); 7.0620 (0.8); 7.0569 (0.8); 7.0544 (1.5); 7.0517 (1.8); 7.0483 (0.9); 6.9236 (0.6); 6.9199 (0.6); 6.9167 (0.6); 6.9130 (0.6); 6.9043 (0.6); 6.9009 (0.9); 6.8975 (1.1); 6.8941 (1.0); 6.8909 (0.6); 6.8821 (0.5); 6.8784 (0.5); 6.8752 (0.6); 6.8716 (0.6); 6.8206 (0.9); 6.8137 (0.8); 6.7995 (1.0); 6.7958 (1.0); 6.7927 (0.9); 6.7890 (0.9); 6.7747 (0.9); 6.7679 (0.8); 6.1148 (5.0); 6.1122 (5.0); 4.8399 (15.4); 4.2990 (1.8); 4.2811 (5.8); 4.2633 (5.9); 4.2455 (1.9); 1.5965 (1.5); 1.3090 (7.7); 1.2912 (16.0); 1.2733 (8.0); 1.2646 (1.6); 0.8979 (0.8); 0.8810 (3.1); 0.8633 (1.1); −0.0002 (4.0) I.46-38: .sup.1H-NMR(400.6 MHz, CDCl.sub.3): δ = 7.3736 (0.8); 7.3590 (0.8); 7.3521 (0.6); 7.3375 (0.5); 7.2620 (3.1); 7.0942 (1.8); 7.0854 (0.7); 7.0812 (4.2); 7.0793 (4.7); 7.0748 (1.2); 7.0562 (1.0); 7.0533 (1.2); 7.0501 (0.6); 6.9030 (0.6); 6.8996 (0.7); 6.8962 (0.7); 6.8234 (0.6); 6.8166 (0.5); 6.8023 (0.7); 6.7986 (0.7); 6.7956 (0.6); 6.7918 (0.6); 6.7776 (0.6); 6.7707 (0.5); 6.1149 (3.1); 6.1123 (3.0); 5.2988 (4.3); 4.8623 (9.1); 3.8074 (16.0); −0.0002 (4.4) I.48-38: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 7.9704 (1.5); 7.9485 (3.2); 7.9314 (3.3); 7.9268 (2.2); 7.9095 (1.8); 7.8992 (1.7); 7.8782 (3.1); 7.8573 (1.7); 7.7231 (3.8); 7.7176 (4.0); 7.6976 (3.9); 7.6921 (3.9); 7.5966 (0.4); 7.5749 (0.5); 7.4607 (3.1); 7.4422 (2.9); 7.3712 (1.8); 7.3650 (1.9); 7.3477 (2.1); 7.3421 (3.4); 7.3361 (2.5); 7.3191 (1.8); 7.3135 (1.9); 7.1663 (1.8); 7.1606 (1.8); 7.1453 (3.3); 7.1394 (3.1); 7.1242 (1.7); 7.1180 (1.6); 6.0565 (3.2); 6.0508 (3.2); 4.3376 (5.0); 3.6949 (0.4); 3.5818 (0.5); 3.5728 (0.4); 3.5553 (0.5); 3.5046 (0.6); 3.3451 (2.8); 3.3389 (2.9); 3.1986 (0.5); 3.1673 (12.2); 2.9956 (0.8); 2.6752 (0.7); 2.6709 (0.6); 2.6660 (0.5); 2.5411 (2.0); 2.5107 (28.3); 2.5063 (57.5); 2.5018 (77.3); 2.4973 (55.3); 2.4929 (26.0); 2.3286 (0.4); 2.1744 (0.5); 1.9035 (0.5); 1.3953 (0.3); 1.2980 (1.1); 1.2580 (2.2); 1.2334 (16.0); 1.1567 (0.3); 1.1342 (0.3); 1.1188 (0.3); 1.1130 (0.4); 1.0286 (0.4); 0.8696 (0.8); 0.8530 (2.4); 0.8353 (1.1); 0.0076 (1.4); −0.0005 (34.4); −0.0088 (1.2) I.21-38: .sup.1H-NMR(400.1 MHz, d.sub.6-DMSO): δ = 7.8283 (0.6); 7.8222 (4.0); 7.8174 (1.4); 7.8055 (1.5); 7.8007 (4.5); 7.7945 (0.6); 7.7214 (0.6); 7.7062 (0.7); 7.6994 (1.3); 7.6843 (1.2); 7.6775 (0.8); 7.6623 (0.8); 7.6576 (0.6); 7.6361 (0.8); 7.6247 (0.4); 7.6167 (0.4); 7.6030 (0.5); 7.5893 (0.8); 7.5824 (0.8); 7.5663 (1.0); 7.5628 (1.1); 7.5596 (1.0); 7.5563 (0.9); 7.5403 (0.8); 7.5335 (0.8); 7.5285 (1.0); 7.5238 (0.5); 7.5181 (0.4); 7.5118 (0.4); 7.5068 (0.8); 7.5019 (1.0); 7.4960 (4.9); 7.4913 (1.6); 7.4791 (1.6); 7.4745 (4.1); 7.4683 (0.6); 7.3117 (0.5); 7.3083 (0.6); 7.3046 (0.5); 7.3019 (0.5); 7.2878 (0.9); 7.2825 (0.9); 7.2690 (0.6); 7.2656 (0.6); 7.2619 (0.5); 6.4841 (6.0); 4.8346 (7.4); 4.0380 (0.4); 4.0202 (0.4); 3.8824 (1.9); 3.3502 (0.3); 2.8903 (0.3); 2.5124 (3.4); 2.5080 (7.2); 2.5035 (9.7); 2.4991 (7.0); 2.4947 (3.3); 1.9896 (1.8); 1.9114 (16.0); 1.2331 (0.3); 1.1922 (0.5); 1.1744 (1.0); 1.1566 (0.5); −0.0005 (3.5) I.64-38: .sup.1H-NMR(400.6 MHz, CDCl.sub.3): δ = 7.3736 (0.8); 7.3590 (0.8); 7.3521 (0.6); 7.3375 (0.5); 7.2620 (3.1); 7.0942 (1.8); 7.0854 (0.7); 7.0812 (4.2); 7.0793 (4.7); 7.0748 (1.2); 7.0562 (1.0); 7.0533 (1.2); 7.0501 (0.6); 6.9030 (0.6); 6.8996 (0.7); 6.8962 (0.7); 6.8234 (0.6); 6.8166 (0.5); 6.8023 (0.7); 6.7986 (0.7); 6.7956 (0.6); 6.7918 (0.6); 6.7776 (0.6); 6.7707 (0.5); 6.1149 (3.1); 6.1123 (3.0); 5.2988 (4.3); 4.8623 (9.1); 3.8074 (16.0); −0.0002 (4.4)

[0519] The invention also provides the method of protecting crop plants or useful plants from phytotoxic effects of agrochemicals, such as pesticides, or herbicides in particular, which cause damage to the crop plants or useful plants, characterized in that compounds of the general formula (I) or salts thereof are employed as safeners, preference being given to applying an effective amount of the compounds of the general formula (I) or salts thereof to the plants, parts of plants or seeds (or seed material) thereof.

[0520] The compounds of the general formula (I) (=safeners) as specified above are suitable for use together with active ingredients (pesticides) for selective control of harmful organisms in a number of crop cultures, for example in economically important crops such as cereal (wheat, barley, triticale, rye, rice, maize, millet/sorghum), sugar beet, sugar cane, oilseed rape, cotton, sunflower, peas, beans and soya.

[0521] The herbicide-safener combinations with safeners of the general formula (I) are also suitable for control of harmful plants on beds and areas of useful plants and ornamental plants, for example lawn areas with utility lawns or decorative lawns, specifically ryegrass, bluegrass or bermuda grass.

[0522] Also of interest in respect of the useful plants and crop plants in which the herbicide-safener combinations comprising the aforementioned compounds of the general formula (I) can be used are mutant crops that are wholly or partially tolerant or transgenic crops that are wholly or partially tolerant to some pesticides, for example maize crops resistant to glufosinate or glyphosate, or soya crops that are resistant to imidazolinones that have a plant-damaging effect.

[0523] However, the particular benefit of the safeners of the general formula (I) used in a novel manner is their effective action in crops that are not normally sufficiently tolerant to the pesticides to be employed. For common use with pesticides, the compounds of the general formula (I) can be deployed simultaneously or in any sequence with the active ingredients, and are then capable of reducing or entirely preventing damaging side effects of these active ingredients in the case of crop plants without impairing or significantly reducing the efficacy of these active ingredients with respect to unwanted harmful organisms.

[0524] It is also possible here to significantly reduce or entirely prevent damage resulting from the use of more than one pesticide, for example by more than one herbicide or by herbicides in combination with insecticides or fungicides.

[0525] This can quite considerably extend the field of use of conventional pesticides.

[0526] If the compositions of the invention contain pesticides, these compositions, at appropriate dilution, are applied either directly to the growing area, to the already germinated harmful plants and/or useful plants, or to the already emerged harmful plants and/or useful plants.

[0527] If the compositions of the invention do not contain any pesticide, these compositions may be used by what is called the tankmix method, meaning that the user mixes and dilutes the separately formulated products (=useful plant-protecting composition and pesticide) immediately prior to application to the area to be treated, or before the application of a pesticide, or after the application of a pesticide, or for seed pretreatment, i.e., for example, for dressing of the useful plant seed.

[0528] Preference is given to prompt application of the safener with the pesticide, especially when the safener is applied to the plants after the herbicide.

[0529] The advantageous effects of the compounds of the general formula (I) are observed when they are used together with the pesticides by the pre-emergence or post-emergence method, for example in the case of simultaneous application as a tankmix or as a co-formulation or in a separate application in parallel or successively (split application). It is also possible to repeat the application more than once. It can sometimes also be sensible to combine a pre-emergence application with a post-emergence application. One option is usually employment as post-emergence application to the useful plant or crop plant with simultaneous or later application of the pesticide. Another option is to employ the inventive compounds (I) in seed dressing, (dip) treatment of seedlings (e.g. rice) or treatment of other propagation material (e.g. potato tubers).

[0530] When the compounds of the general formula (I) are employed in combination with herbicides, it is often the case that not only the safener effect but also boosts in herbicidal action against harmful plants are observed. Moreover, the growth of the useful plants and crop plants is improved in many cases, and it is possible to increase the harvest yields.

[0531] The compositions of the invention may contain one or more pesticides. Examples of useful pesticides include herbicides, insecticides, fungicides, acaricides and nematicides which, when employed alone, would each result in phytotoxic damage to the crop plants or where damage would be likely.

[0532] Of particular interest are the corresponding active pesticidal ingredients from the group of the herbicides, insecticides, acaricides, nematicides and fungicides, especially herbicides.

[0533] The weight ratio of safeners (of the general formula (I)) to pesticide may be varied within wide limits and is generally in the range from 1:100 to 100:1, preferably 1:20 to 20:1, especially 1:10 to 10:1. The optimal weight ratio of safener to pesticide depends both on the respective safener used and the respective pesticide and on the type of useful plant or crop plant to be protected. According to the pesticide used and type of useful plant to be protected, the required application rate of safener may be varied within wide limits and is generally in the range from 0.001 to 10 kg, preferably 0.01 to 1 kg, especially 0.01 to 0.2 kg, of safener per hectare. The amounts and weight ratios needed for a successful treatment can be ascertained by simple preliminary tests.

[0534] In the case of seed dressing, for example, 0.005 to 20 g of safener (of the general formula (I)) per kilogram of seed, preferably 0.01 to 10 g of safener per kilogram of seed, especially 0.05 to 5 g of safener per kilogram of seed, are used.

[0535] When solutions of safeners (of the general formula (I)) are utilized in seed treatment and the seed or seedlings are wetted with the solutions, the suitable concentration is generally in the range from 1 to 10 000 ppm, preferably 100 to 1000 ppm, based on weight.

[0536] The amounts and weight ratios needed for a successful treatment can be ascertained by simple preliminary tests.

[0537] The safeners of the general formula (I) can be formulated in a customary manner, separately or together with the pesticides.

[0538] Also provided, therefore, are the useful plant- or crop plant-protecting compositions.

[0539] Preference is given to the joint use of safener and pesticide, especially that of safener and herbicide as a finished formulation or employment by the tankmix method.

[0540] Likewise preferred is the employment of the safener of the general formula (I) in seed treatment with later application of pesticides, preferably herbicides, after sowing by the pre- or post-emergence method.

[0541] The compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of tankmixes.

[0542] The combination formulations can be produced on the basis of the abovementioned formulations, taking account of the physical properties and stabilities of the active ingredients to be combined.

[0543] Combination partners usable for the compounds of the invention in mixed formulations or in a tankmix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as known, for example, from Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, and literature cited therein.

[0544] Known herbicides or plant growth regulators which can be combined with the compounds of the invention are, for example, the following, where said active ingredients are referred to either by their “common name” in accordance with the International Organization for Standardization (ISO) or by the chemical name or by the code number. They always encompass all the use forms, for example acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if they are not mentioned explicitly.

[0545] Examples of such herbicidal mixing partners are: [0546] acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

##STR00135##

[0547] Examples of plant growth regulators as possible mixing partners are: [0548] acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0549] In the case of employment as active ingredient formulations or co-formulations, these generally contain, as the case may be, the respectively customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors, and pH and viscosity modifiers.

[0550] The compounds of the general formula (I) and combinations thereof with one or more of the pesticides mentioned may be formulated in various ways depending on the defined physicochemical and biological parameters.

[0551] Suitable examples of types of formulation include: [0552] emulsifiable concentrates that are produced by dissolving the active ingredients in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers).

[0553] Suitable emulsifiers are, for example, calcium alkylarylsulfonates, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters; [0554] dusting products that are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, e.g. talc, natural clays, such as kaolin, bentonite and pyrophyllite, diatomaceous earth or flours; [0555] water- or oil-based suspension concentrates that can be produced, for example, by wet grinding by means of bead mills; [0556] water-soluble powders; [0557] water-soluble concentrates; [0558] granules, such as water-soluble granules, water-dispersible granules and granules for broadcasting and soil application; [0559] wettable powders which, as well as the active ingredient, also contain diluents or inert substances and surfactants; [0560] capsule suspensions and microcapsules; [0561] ultralow-volume formulations.

[0562] The abovementioned formulation types are known to the person skilled in the art and are described, for example, in: K. Martens, “Spray Drying Handbook”, 3rd ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y. 1973; Winacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition 1986; “Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, N.Y. 1973, pages 8-57.

[0563] The necessary formulation auxiliaries such as inert materials, surfactants, solvents and further additives are likewise known and are described, for example, in: [0564] McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; H. von Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; Schönfeldt, “Grenzflachenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J.; Winnacker-Küchler, “Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0565] Apart from the aforementioned formulation auxiliaries, the useful plant-protecting compositions may, as the case may be, contain customary wetters, stickers, dispersants, penetrants, emulsifiers, preservatives, antifreezes, fillers, carriers and dyes, defoamers, evaporation inhibitors, and pH or viscosity modifiers.

[0566] According to the type of formulation, the useful plant-protecting compositions contain generally 0.1% to 99% by weight, especially 0.2% to 95% by weight, of one or more safeners of the general formula (I) or a combination of safener and pesticide.

[0567] They additionally contain 1% to 99.9%, especially 4% to 99.5%, by weight of one or more solid or liquid additives and 0% to 25%, especially 0.1 to 25%, by weight of a surfactant. In emulsifiable concentrates, the active ingredient concentration, i.e. the concentration of safener and/or pesticide, is generally 1% to 90%, especially 5% to 80%, by weight.

[0568] Dusting products typically contain 1% to 30%, preferably 5% to 20%, by weight of active ingredient. In wettable powders, the active ingredient concentration is generally 10% to 90% by weight.

[0569] In the water-dispersible granules, the content of active ingredient is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0570] For application, the formulations in the commercial form are diluted if appropriate in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in dust form, granules and sprayable solutions are not normally diluted further with other inert substances prior to application.

[0571] The required application rate of the safeners of the general formula (I) varies with external conditions including temperature, humidity and the type of herbicide used.

[0572] In the examples which follow, which illustrate but do not limit the invention, statements of amount are based on weight unless defined otherwise.

EXAMPLES

1. Formulation Examples

[0573] 1.1 Dusting Product

[0574] A dusting product is obtained by mixing 10 parts by weight of a compound of the general formula (I) (safener) or of an active ingredient mixture composed of a pesticide (e.g. a herbicide) and a safener of the general formula (I) and 90 parts by weight of talc as inert substance, and comminuting in a bead mill.

[0575] 1.2 Water-Dispersible Powder

[0576] A readily water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of the general formula (I) or of an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.

[0577] 1.3 Water-Dispersible Concentrate

[0578] A water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the general formula (I) or of an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (@Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil, and grinding in a friction ball mill to a fineness below 5 microns.

[0579] 1.4 Emulsifiable Concentrate

[0580] An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the general formula (I) or of an active ingredient mixture composed of a pesticide (e.g. a herbicide) and a safener of the general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

[0581] 1.5 Water-Dispersible Granules Water-dispersible granules are obtained by mixing

TABLE-US-00003 75 parts by weight of a safener of the general formula (I) or a mixture of a pesticide and a safener of the general formula (I), 10 ″ of calcium lignosulfonate, 5 ″ of sodium laurylsulfate, 3 ″ of polyvinyl alcohol and 7 ″ of polyvinyl alcohol and 7 ″ of kaolin, [0582] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.

[0583] Water-dispersible granules are also obtained by homogenizing and comminuting, in a colloid mill,

TABLE-US-00004 25 parts by weight of a safener of the general formula (I) or a mixture of a pesticide and a safener of the general formula (I), 5 ″ of sodium 2,2-dinaphthylmethane-6,6′-disulfonate, 2 ″ of sodium oleoylmethyltaurinate, 17 ″ of calcium carbonate 50 ″ of water and 1 part by weight of polyvinyl alcohol, [0584] then grinding the mixture in a bead mill and atomizing and drying the suspension thus obtained in a spray tower by means of a one-phase nozzle.

2. Biological Examples

[0585] 2.1 Absolute Action of Selected Compounds of the Invention Using the Example of Reduction of Damage by Mesosulfuron-Methyl on Summer Wheat (TRZAS)

[0586] The seeds of the crop plants to be treated are laid out in sandy loam in wood fiber or plastic pots (diameter ˜4 cm), covered with soil and grown in a greenhouse under good conditions for germination and growth. The trial plants were treated at the early leaf stage (BBCH10-BBCH12). In the course of this, the inventive compounds of the general formula (D formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as an aqueous suspension with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% agrotin) in the specified dose.

[0587] This was followed by the application of the herbicide. For this purpose, mesosulfuron-methyl, formulated in the form of water-dispersible granules (WG), was sprayed onto the above-ground parts of the plants in the form of an aqueous dispersion with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% agrotin) in a dose of 20 g/ha. The dose of the herbicide was chosen here such that it causes visually apparent damage (min. 30%, max. 75%) compared to untreated crop plants at the evaluation time on a control group of crop plants without safener treatment that were included in the same trial.

[0588] After application, the plants were cultivated under good growth conditions in a greenhouse. The damage was visually assessed 14-21 days after application.

[0589] The damage effect was assessed visually on a scale of 0-100% by comparison with untreated control plants, and averaged over 2-3 repeats per treatment. Examples: [0590] 0%=no noticeable effect compared to the untreated plant [0591] 20%=the treated plant population has 20% damage compared to the untreated control population (e.g. growth height, leaf damage, etc.) [0592] 100%=treated plants completely damaged/killed.

[0593] The trials show that damage to the summer wheat crop plant (TRZAS; cv. Triso) caused by the herbicide mesosulfuron-methyl (=herbicide damage without compound of the formula (I) in the table below) is significantly reduced by treatment of inventive compounds selected by way of example (=herbicide damage with compound of the formula (I) in the table below):

TABLE-US-00005 Dose Herbicide Herbicide of the damage damage safener without with of the compound compound Absolute formula of the of the reduction Example (I) Crop formula (I) formula (I) in damage No. (g/ha) plant (%) (%) (difference) I.3-7 125 TRZAS 63 37 26 I.11-38 500 TRZAS 53 10 43 I.11-38 125 TRZAS 53 10 43 I.21-38 500 TRZAS 53 3 50 I.21-38 125 TRZAS 53 7 46 I.12-4 500 TRZAS 53 7 46 I.41-1 125 TRZAS 53 0 53 I.41-4 125 TRZAS 53 13 40 I.41-38 500 TRZAS 53 13 40 I.11-20 500 TRZAS 53 7 46 I.11-20 125 TRZAS 53 7 46 I.41-20 500 TRZAS 53 10 43 I.41-20 125 TRZAS 53 17 36 I.3-20 500 TRZAS 53 17 36 I.42-20 125 TRZAS 53 13 40 I.21-20 500 TRZAS 53 17 36 I.21-20 125 TRZAS 53 23 30 I.42-38 125 TRZAS 53 20 33

[0594] 2.2 Absolute Action of Selected Compounds of the Invention Using the Example of Reduction of Damage by Mesosulfuron-Methyl on Summer Barley (HORVS)

[0595] The seeds of the crop plants to be treated are laid out in sandy loam in wood fiber or plastic pots (diameter ˜4 cm), covered with soil and grown in a greenhouse under good conditions for germination and growth. The trial plants were treated at the early leaf stage (BBCH10-BBCH12). In the course of this, the inventive compounds of the general formula (I) formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as an aqueous suspension with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% agrotin) in the specified dose.

[0596] This was followed by the application of the herbicide. For this purpose, mesosulfuron-methyl, formulated in the form of water-dispersible granules (WG), was sprayed onto the above-ground parts of the plants in the form of an aqueous dispersion with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% agrotin) in a dose of 20 g/ha. The dose of the herbicide was chosen here such that it causes visually apparent damage (min. 30%, max. 75%) compared to untreated crop plants at the evaluation time on a control group of crop plants without safener treatment that were included in the same trial.

[0597] After application, the plants were cultivated under good growth conditions in a greenhouse. The damage was visually assessed 14-21 days after application.

[0598] The damage effect was assessed visually on a scale of 0-100% by comparison with untreated control plants, and averaged over 2-3 repeats per treatment. Examples: [0599] 0%=no noticeable effect compared to the untreated plant [0600] 20%=the treated plant population has 20% damage compared to the untreated control population (e.g. growth height, leaf damage, etc.) [0601] 100%=treated plants completely damaged/killed.

[0602] The trials show that damage to the summer barley crop plant (HORVS; cv. Montoya) caused by the herbicide mesosulfuron-methyl (=herbicide damage without compound of the formula (I) in the table below) is significantly reduced by treatment of inventive compounds selected by way of example (=herbicide damage with compound of the formula (I) in the table below):

TABLE-US-00006 Dose Herbicide Herbicide of the damage damage safener without with of the compound compound Absolute formula of the of the reduction Example (I) Crop formula (I) formula (I) in damage No. (g/ha) plant (%) (%) (difference) I.11-38 500 HORVS 60 27 33 I.11-38 125 HORVS 60 37 23 I.21-38 500 HORVS 60 27 33 I.21-38 125 HORVS 60 27 33 I.12-4 500 HORVS 60 33 27 I.41-4 125 HORVS 60 37 23 I.41-38 500 HORVS 60 27 33 I.42-38 125 HORVS 60 37 23

[0603] 2.3 Relative Action of Selected Compounds of the Invention Using the Example of Reduction of Damage by Mesosulfuron-Methyl on Summer Wheat (TRZAS)

[0604] The seeds of the crop plants to be treated are laid out in sandy loam in plastic pots (diameter μ4 cm), covered with soil and grown in a greenhouse under good conditions for germination and growth. The trial plants were treated at the early leaf stage (BBCH10-BBCH12). In the course of this, the inventive compounds of the general formula (I) formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as an aqueous suspension with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% Genapol-LRO or 0.2% Mero) in the specified dose.

[0605] This was followed by the application of the herbicide. For this purpose, mesosulfuron-methyl, formulated in the form of water-dispersible granules (WG), was sprayed onto the above-ground parts of the plants in the form of an aqueous dispersion with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% Genapol-LRO or 1 l/ha Biopower) in a dose of 40-60 g/ha. The dose of the herbicide was chosen here such that it causes visually apparent damage (min. 30%, max. 75%) compared to untreated crop plants at the evaluation time on a control group of crop plants without safener treatment that were included in the same trial.

[0606] After application, the plants were cultivated under good growth conditions in a greenhouse. 9-13 days after application, the efficacy of the test compounds was assessed visually. For this purpose, the appearance of the plants treated with the test compound and herbicide was compared to the corresponding herbicide controls (without safener; with clearly visible damage) and the untreated controls (without damage). The damage-reducing effect of the test compounds was expressed here in graded efficacy codes according to the following scheme: [0607] 0: no reduction in damage (appearance corresponding to the herbicide control) [0608] 1: slight reduction in damage [0609] 2: distinct reduction in damage [0610] 3: significant reduction in damage [0611] 4: complete reduction in damage (appearance corresponding to the untreated control)

[0612] The trials show clear efficacy of the inventive compounds selected by way of example with regard to the reduction in damage to the summer wheat crop plant (TRZAS; cv. Triso) caused by the herbicide mesosulfuron-methyl:

TABLE-US-00007 Dose of the Efficacy Example safener of the Crop of the safener No. formula (I) (g/ha) plant (efficacy code) I.47-49 500 TRZAS 3 I.50-49 500 TRZAS 3 I.50-49 100 TRZAS 2 I.20-49 500 TRZAS 3 I.20-49 100 TRZAS 3 I.11-32 500 TRZAS 2 I.11-32 100 TRZAS 2 I.47-7 500 TRZAS 2 I.47-7 100 TRZAS 2 I.47-48 500 TRZAS 4 I.47-48 100 TRZAS 3 I.42-49 500 TRZAS 4 I.42-49 100 TRZAS 3 I.48-38 500 TRZAS 2 I.48-38 100 TRZAS 2 I.41-49 500 TRZAS 4 I.41-49 100 TRZAS 3 I.40-49 500 TRZAS 3 I.40-49 100 TRZAS 3

[0613] 2.4 Relative Action of Selected Compounds of the Invention Using the Example of Reduction of Damage by Mesosulfuron-Methyl on Summer Barley (HORVS)

[0614] The seeds of the crop plants to be treated are laid out in sandy loam in plastic pots (diameter˜4 cm), covered with soil and grown in a greenhouse under good conditions for germination and growth. The trial plants were treated at the early leaf stage (BBCH10-BBCH12). In the course of this, the inventive compounds of the general formula (I) formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as an aqueous suspension with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% Genapol-LRO or 0.2% Mero) in the specified dose.

[0615] This was followed by the application of the herbicide. For this purpose, mesosulfuron-methyl, formulated in the form of water-dispersible granules (WG), was sprayed onto the above-ground parts of the plants in the form of an aqueous dispersion with a water application rate corresponding to 800 l/ha with addition of wetting agent (e.g. 0.2% Genapol-LRO or 1 l/ha Biopower) in a dose of 40-60 g/ha. The dose of the herbicide was chosen here such that it causes visually apparent damage (min. 30%, max. 75%) compared to untreated crop plants at the evaluation time on a control group of crop plants without safener treatment that were included in the same trial.

[0616] After application, the plants were cultivated under good growth conditions in a greenhouse. 9-13 days after application, the efficacy of the test compounds was assessed visually. For this purpose, the appearance of the plants treated with the test compound and herbicide was compared to the corresponding herbicide controls (without safener; with clearly visible damage) and the untreated controls (without damage). The damage-reducing effect of the test compounds was expressed here separately for 2 repeats in graded efficacy codes according to the following scheme: [0617] 0: no reduction in damage (appearance corresponding to the herbicide control) [0618] 1: slight reduction in damage [0619] 2: distinct reduction in damage [0620] 3: significant reduction in damage [0621] 4: complete reduction in damage (appearance corresponding to the untreated control)

[0622] The trials show clear efficacy of the inventive compounds selected by way of example with regard to the reduction in damage to the summer barley crop plant (HORVS; cv. Montoya) caused by the herbicide mesosulfuron-methyl:

TABLE-US-00008 Dose of the Efficacy of safener of the the safener Example formula (I) Crop (efficacy No. (g/ha) plant code) I.47-49 500 HORVS 3 I.47-49 100 HORVS 2 I.50-49 500 HORVS 3 I.50-49 100 HORVS 2-3 I.11-32 500 HORVS 2 I.47-48 500 HORVS 3 I.47-48 100 HORVS 2 I.42-49 500 HORVS 3 I.42-49 100 HORVS 2-3 I.41-49 500 HORVS 2 I.41-49 100 HORVS 2 I.40-49 500 HORVS 2-3 I.40-49 100 HORVS 2

USE OF [(1,5-DIPHENYL-1H-PYRAZOL-3-YL)OXY] ACETIC ACID DERIVATIVES AND THEIR SALTS AND COMPOSITIONS CONTAINING THEM, FOR REDUCING PHYTOTOXIC EFFECTS OF AGROCHEMICALS, IN PARTICULAR OF HERBICIDES, IN USEFUL PLANTS AND CROP PLANTS

Inventors

Cpc classification

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A01N43/54

HUMAN NECESSITIES

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A01P13/02

HUMAN NECESSITIES

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A01N25/32

HUMAN NECESSITIES

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C07D231/22

CHEMISTRY; METALLURGY

International classification

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A01N25/32

HUMAN NECESSITIES

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A01N43/54

HUMAN NECESSITIES

Classification Explorer

A01P13/02

HUMAN NECESSITIES

Classification Explorer

C07D231/22

CHEMISTRY; METALLURGY

Abstract

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