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SUBSTITUTED PYRIDAZINONES, SALTS OR N-OXIDES THEREOF AND THEIR USE AS HERBICIDALLY ACTIVE SUBSTANCES

20240239755 ยท 2024-07-18

    Inventors

    Cpc classification

    International classification

    Abstract

    The present invention relates to substituted pyridazinones of the general formula (I), salts or N-oxides thereof,

    ##STR00001## where the radicals in the general formula (I) correspond to the definitions given in the description, and to their use as herbicides, in particular for controlling weed grasses and/or broad-leaved weeds in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants.

    Claims

    1. Substituted pyridazinones of the general formula (I), salts or N-oxides thereof ##STR00034## in which W represents oxygen or sulfur, R.sup.1 represents hydrogen, halogen, formyl, cyano, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8) haloalkoxy, (C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-alkylsulfinyl, (C.sub.1-C.sub.8)-alkylsulfonyl, (C.sub.2-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.1-C.sub.8) alkylcarbonyloxy, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylthio-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkylthio-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.8)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, R.sup.2 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8) haloalkoxy, (C.sub.2-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylthio-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkylthio-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.8)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, R.sup.3 represents (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkenyl, aryl, heteroaryl, heterocyclyl, a bicyclic or a heterobicyclic residue, wherein each of the previously mentioned seven residues is unsubstituted or is independently substituted by one to five residues selected from the group R.sup.4, G represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.8)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, C(?O)R.sup.5, C(?S)R.sup.5, CO.sub.2R.sup.6, (C.sub.1-C.sub.8)-alkyl-OCO.sub.2R.sup.6, C(?O)SR.sup.6, S(O).sub.2R.sup.5, CONR.sup.7R.sup.8, S(O).sub.2NR.sup.7R.sup.8 or P(?O)R.sup.9R.sup.9, or represents phenyl-(C.sub.1-C.sub.8)-carbonyl-(C.sub.1-C.sub.8)-alkyl, unsubstituted or independently substituted by one to five residues selected from halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.4 represents halogen, cyano, nitro, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-haloalkoxy, (C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-haloalkylthio, (C.sub.1-C.sub.8)-alkylsulfinyl, (C.sub.1-C.sub.8)-haloalkylsulfinyl, (C.sub.1-C.sub.8)-alkylsulfonyl, (C.sub.1-C.sub.8)-haloalkylsulfonyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.1-C.sub.8)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-halocycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-halocycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.8)-haloalkyl-(C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.9)-trialkylsilyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to five residues selected from halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.5 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.8)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to five residues selected from halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.6 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.8)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to five residues selected from halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.7 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.1-C.sub.8)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to five residues selected from halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.8 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, R.sup.7/R.sup.8 represent, together with the nitrogen atom to which they are bonded, a fully or partially saturated 3- to 10-membered monocyclic or bicyclic ring system optionally interrupted by heteroatoms and optionally having further substitution, R.sup.9 represents (C.sub.1-C.sub.8)-alkyl or (C.sub.1-C.sub.8)-alkoxy.

    2. The compound of the general formula (I) as claimed in claim 1 and/or salts or N-oxides thereof, characterized in that W represents oxygen or sulfur, R.sup.1 represents hydrogen, halogen, formyl, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.2 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.3 represents (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned five residues is unsubstituted or is independently substituted by one to four residues selected from the group R.sup.4, G represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, C(?O)R.sup.5, C(?S)R.sup.5, CO.sub.2R.sup.6, (C.sub.1-C.sub.6)-alkyl-OCO.sub.2R.sup.6, S(O).sub.2R.sup.8, CONR.sup.7R.sup.8, S(O).sub.2NR.sup.7R.sup.8 or P(?O)R.sup.9R.sup.9, or represents phenyl-(C.sub.1-C.sub.6)-carbonyl-(C.sub.1-C.sub.6)-alkyl, unsubstituted or independently substituted by one to four residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.4 represents halogen, cyano, nitro, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to four residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.5 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to four residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.6 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to four residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.7 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, or represents benzyl, aryl, heteroaryl or heterocyclyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to four residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.8 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.7/R.sup.8 represent, together with the nitrogen atom to which they are bonded, a fully or partially saturated 3- to 9-membered monocyclic or bicyclic ring system optionally interrupted by heteroatoms and optionally having further substitution selected from the residues halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.9 represents (C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkoxy.

    3. The compound of the general formula (I) as claimed in claim 1 and/or salts or N-oxides thereof, characterized in that W represents oxygen or sulfur, R.sup.1 represents hydrogen, halogen, cyano, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, R.sup.2 represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.4)-alkyl, R.sup.3 represents aryl or heteroaryl, wherein each of the previously mentioned residues is unsubstituted or is independently substituted by one to three residues selected from the group R.sup.4, G represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, C(?O)R.sup.5, CO.sub.2R.sup.6, (C.sub.1-C.sub.4)-alkyl-OCO.sub.2R.sup.6, S(O).sub.2R.sup.6, CONR.sup.7R.sup.8 or P(?O)R.sup.9R.sup.9, or represents phenyl-(C.sub.1-C.sub.4)-carbonyl-(C.sub.1-C.sub.4)-alkyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.4 represents halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl or (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.4)-alkyl, or represents aryl or heteroaryl, wherein each of the previously mentioned two residues is unsubstituted or is independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.5 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, or represents phenyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.6 represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, or represents phenyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.7 represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, or represents phenyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.8 represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.7/R.sup.8 represent, together with the nitrogen atom to which they are bonded, a fully or partially saturated 3- to 8-membered monocyclic or bicyclic ring system optionally interrupted by heteroatoms, R.sup.9 represents (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkoxy.

    4. The compound of the general formula (I) as claimed in claim 1 and/or salts or N-oxides thereof, characterized in that W represents oxygen or sulfur, R.sup.1 represents hydrogen, halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.2 represents hydrogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.3 represents phenyl, thienyl, pyrazolyl or pyridyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to three residues selected from the group R.sup.4, G represents hydrogen, C(?O)R.sup.5, CO.sub.2R.sup.6, (C.sub.1-C.sub.4)-alkyl-OCO.sub.2R.sup.6, S(O).sub.2R.sup.6, CONR.sup.7R or P(?O)R.sup.9R.sup.9, or represents phenyl-(C.sub.1-C.sub.4)-carbonyl-(C.sub.1-C.sub.4)-alkyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.4 represents halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, or represents phenyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.5 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.6 represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, or represents phenyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.7 represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or (C.sub.2-C.sub.4)-alkynyl, R.sup.8 represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or (C.sub.2-C.sub.4)-alkynyl, R.sup.7/R.sup.8 represent, together with the nitrogen atom to which they are bonded, a fully or partially saturated 3- to 6-membered monocyclic ring system optionally interrupted by heteroatoms, R.sup.9 represents (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkoxy.

    5. The compound of the general formula (I) as claimed in claim 1 and/or salts or N-oxides thereof, characterized in that W represents oxygen, R.sup.1 represents (C.sub.1-C.sub.4)-alkyl, R.sup.2 represents (C.sub.1-C.sub.4)-alkyl, R.sup.3 represents phenyl, thienyl, pyrazolyl or pyridyl, wherein each of the previously mentioned four residues is unsubstituted or is independently substituted by one to three residues selected from the group R.sup.4, G represents hydrogen, C(?O)R.sup.5, CO.sub.2R.sup.6, (C.sub.1-C.sub.4)-alkyl-OCO.sub.2R.sup.6, S(O).sub.2R.sup.6, CONR.sup.7R.sup.8, P(?O)R.sup.9R.sup.9 or phenyl-(C.sub.1-C.sub.4)-carbonyl-(C.sub.1-C.sub.4)-alkyl, R.sup.4 represents halogen, cyano, nitro, phenyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.5 represents (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, R.sup.6 represents (C.sub.1-C.sub.4)-alkyl, or represents phenyl, unsubstituted or independently substituted by one to three residues selected from halogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, R.sup.7 represents (C.sub.1-C.sub.4)-alkyl, R.sup.8 represents (C.sub.1-C.sub.4)-alkyl, R.sup.7/R.sup.8 represent, together with the nitrogen atom to which they are bonded, a fully saturated 3- to 6-membered monocyclic ring system optionally interrupted by oxygen, R.sup.9 represents (C.sub.1-C.sub.4)-alkoxy.

    6. The compound of the general formula (I) as claimed in claim 1 and/or salts or N-oxides thereof, characterized in that W represents oxygen, R.sup.1 represents methyl, R.sup.2 represents methyl, R.sup.3 represents phenyl, 2-methylphenyl, 2-isopropylphenyl, 2-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-chloro-3-fluorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,3,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2-chloro-6-methylphenyl, 2-bromophenyl, 2-bromo-5-fluorophenyl, 2-bromo-3,5-difluorophenyl, 2-bromo-4,5-difluorophenyl, 2-bromo-5-chlorophenyl, 4-bromophenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-methoxyphenyl, 2-difluoromethoxyphenyl, 2-trifluoromethoxyphenyl, 2-cyanophenyl, 2-nitrophenyl, 2-cyclopropylphenyl, 2-cyclopropyl-3-fluorophenyl, 2-cyclopropyl-4-fluorophenyl, 2-cyclopropyl-5-fluorophenyl, 2-cyclopropyl-6-fluorophenyl, 2-cyclopropyl-3,5-difluorophenyl, 2-cyclopropyl-4,5-difluorophenyl, 3-chloro-2-cyclopropylphenyl, 4-chloro-2-cyclopropylphenyl, 5-chloro-2-cyclopropylphenyl, 2-cyclopropyl-3-methylphenyl, 2-cyclopropyl-4-methylphenyl, 2-cyclopropyl-5-methylphenyl, 2-phenylphenyl, 3-pyridyl, 6-chloro-5-fluoro-2-pyridyl, 6-chloro-5-trifluoromethyl-2-pyridyl, 2-chloro-3-pyridyl or 1-methylpyrazol-4-yl, G represents hydrogen, methylcarbonyl, n-pentylcarbonyl, iso-propylcarbonyl, tert-butylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, methoxycarbonyl, ethoxycarbonyl, dimethylcarbamoyl, piperidine-1-carbonyl, morpholine-4-carbonyl, para-tolylsulfonyl, diethoxyphosphoryl or phenacyl.

    7. The compound of the general formula (I) as claimed in claim 1 and/or salts or N-oxides thereof, characterized in that W represents oxygen, R.sup.1 represents methyl, R.sup.2 represents methyl, R.sup.3 represents phenyl, 2-methylphenyl, 2-isopropylphenyl, 2-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-chloro-3-fluorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 3,5-dichlorophenyl, 2,3,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2-chloro-6-methylphenyl, 2-bromophenyl, 2-bromo-5-fluorophenyl, 2-bromo-3,5-difluorophenyl, 2-bromo-4,5-difluorophenyl, 2-bromo-5-chlorophenyl, 4-bromophenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 2-methoxyphenyl, 2-difluoromethoxyphenyl, 2-trifluoromethoxyphenyl, 2-cyanophenyl, 2-cyclopropylphenyl, 2-cyclopropyl-3-fluorophenyl, 2-cyclopropyl-4-fluorophenyl, 2-cyclopropyl-6-fluorophenyl, 2-cyclopropyl-4,5-difluorophenyl, 4-chloro-2-cyclopropylphenyl, 5-chloro-2-cyclopropylphenyl, 2-cyclopropyl-4-methylphenyl or 2-cyclopropyl-5-methylphenyl, G represents hydrogen, methylcarbonyl, iso-propylcarbonyl or ethoxycarbonyl.

    8. The use of one or more compounds of the general formula (I) and/or salts or N-oxides thereof, as defined in claim 1, as herbicide and/or plant growth regulator.

    9. An herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises one or more compounds of the formula (I) and/or salts or N-oxides thereof as defined in claim 1, and one or more further substances selected from groups (i) and/or (ii), with (i) one or more further agrochemically active substances, selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and/or further growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.

    10. A method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the formula (I) and/or salts or N-oxides thereof, as defined in claim 1 is applied to the plants, seeds of plants, the soil in which or on which the plants grow or the area under cultivation.

    11. A method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of a composition as claimed in claim 9, is applied to the plants, seeds of plants, the soil in which or on which the plants grow or the area under cultivation.

    Description

    SYNTHESIS EXAMPLES

    No. IVa: ethyl 2-[2-(trifluoromethyl)phenoxy]acetate

    [0140] ##STR00010##

    [0141] To a stirred mixture of O-trifluoromethylphenol (10.0 g, 0.062 mol, 1.0 eq.) and K.sub.2CO.sub.3 (12.8 g, 0.093 mol, 1.5 eq.) in DMF (100 mL) at RT was added ethyl bromoacetate (12.4 g, 0.074 mol, 1.20 eq.) dropwise under an atmosphere of nitrogen. The resulting mixture was stirred at 80? C. for 3 h. The reaction mixture was diluted with sat. aq. NH.sub.4Cl (100 mL) and extracted with EtOAc (3?50 mL). The combined organic extracts were washed with brine (3?50 mL), dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc (20:1) to afford compound IVa (12.9 g, 84% yield) as a colorless oil.

    No. Va: 2-[2-(trifluoromethyl)phenoxy]acetic acid

    [0142] ##STR00011##

    [0143] To a stirred solution of compound IVa (12.0 g, 0.048 mol, 1.0 eq.) in THF (50 mL) at RT was added a solution of LiOH (2.32 g, 0.097 mol, 2.0 eq.) in H.sub.2O (50 mL) dropwise under an atmosphere of nitrogen. The resulting mixture was stirred at RT for 16 h. The reaction mixture was concentrated under reduced pressure and then acidified to pH 4 using conc. HCl. The precipitated solid was collected by filtration washing with water (5?50 mL) to afford compound Va (8.0 g, 75% yield) as a white solid. The product was used directly in the next step without further purification.

    No. VIa: ethyl 2-(methylhydrazono)propanoate

    [0144] ##STR00012##

    [0145] To a stirred mixture of ethyl pyruvate (4.79 mL, 43 mmol) and Et.sub.3N (6.00 mL, 43 mmol) in THF (215 mL) at 0? C. under an atmosphere of argon was added methylhydrazine (2.29 mL, 43 mmol). The resulting mixture was allowed to warm to RT and stirred for 6 h. The reaction mixture was concentrated under reduced pressure to afford compound VIa (5.63 g, 91% yield) as a yellow oil. .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 5.70 (br. s, 1H), 4.29 (q, 2H), 3.22 (s, 3H), 1.92 (s, 3H), 1.33 (t, 3H).

    No. VIIa: ethyl 2-[methyl-[2-[2-(trifluoromethyl)phenoxy]acetyl]hydrazono]propanoate

    [0146] ##STR00013##

    [0147] A stirred mixture of compound Va (2.00 g, 9.09 mmol, 1.0 eq.) in SOCl.sub.2 (80 mL) under an atmosphere of nitrogen was heated to 80? C. for 1 h. The resulting mixture was cooled to RT and concentrated under reduced pressure. The resulting residue was diluted with CH.sub.2Cl.sub.2 (50 mL) and Et.sub.3N (2.67 g, 26.4 mmol, 3.0 eq.) was added at 0? C. A mixture of compound VIa (1.27 g, 8.81 mmol, 1.0 eq.) in CH.sub.2Cl.sub.2 (50 mL) was then added dropwise under an atmosphere of nitrogen and the resulting mixture was warmed to RT and left to stir for 16 h. The reaction mixture was diluted with water and extracted with EtOAc (3?100 mL). The combined organic extracts were washed with water (3?100 mL), dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with water/MeCN (30%.fwdarw.60%) to afford compound VIIa (900 mg, 27% yield) as a pale yellow solid.

    No. 1-007: 5-hydroxy-2,6-dimethyl-4-[2-(trifluoromethyl)phenoxy]pyridazin-3-one

    [0148] ##STR00014##

    [0149] To a stirred mixture of compound VIIa (350 mg, 1.01 mmol, 1.0 eq.) in THF (20 mL) at RT was added Cs.sub.2CO.sub.3 (659 mg, 2.02 mmol, 2.0 eq.) portionwise. The resulting mixture was stirred at 80? C. for 16 h. The reaction mixture was cooled to RT and filtered washing with a mixture of CH.sub.2Cl.sub.2/MeOH (15:1) (6?50 mL). The filtrate was concentrated under reduced pressure and the resulting residue was purified by reverse phase chromatography eluting with water (0.1% formic acid)/MeCN (33%.fwdarw.55%) to afford compound I-007 (100 mg, 33% yield) as a white solid.

    No. I-009: [1,3-dimethyl-6-oxo-5-[2-(trifluoromethyl)phenoxy]pyridazin-4-yl] ethyl carbonate

    [0150] ##STR00015##

    [0151] To a stirred mixture of compound I-007 (40.0 mg, 0.133 mmol, 1.0 eq.) and Et.sub.3N (80.9 mg, 0.799 mmol, 6.0 eq.) in CH.sub.2Cl.sub.2 (3 mL) at RT was added and ethyl chloroformate (57.8 mg, 0.533 mmol, 4.0 eq.).

    [0152] The resulting mixture was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by reverse phase chromatography eluting with water/MeCN (10%.fwdarw.80%) to afford compound I-009 (43 mg, 86% yield) as an off-white solid.

    No. IVb: ethyl 2-(2,4-dichlorophenoxy)acetate

    [0153] ##STR00016##

    [0154] To a stirred mixture of 2,4-dichlorophenol (5.0 g, 30.6 mmol) and K.sub.2CO.sub.3 (6.36 g, 46 mmol) in DMF (62 mL) at RT under an atmosphere of argon was added ethyl bromoacetate (4.08 mL, 36.8 mmol). The resulting mixture was stirred at 80? C. for 4 h. The reaction mixture was cooled to RT, diluted with sat. aq. ammonium chloride (60 mL) and extracted with EtOAc (3?30 mL). The combined organic extracts were washed with brine, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to afford compound IVb (6.85 g, 90% yield) as a yellow solid. The product was used directly in the next step without further purification. .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.39 (s, 1H), 7.17 (dd, 1H), 6.78 (d, 1H), 4.68 (s, 2H), 4.27 (q, 2H), 1.30 (t, 3H).

    No. Vb: 2-(2,4-dichlorophenoxy)acetic acid

    [0155] ##STR00017##

    [0156] To a stirred mixture of compound IVb (6.85 g, 27.5 mmol) in a mixture of THF/water (138 mL, 7:3) at RT was added LiOH (1.98 g, 82.5 mmol). The resulting mixture was stirred at RT for 5 h. The reaction mixture was acidified with 2 M HCl and extracted with EtOAc (3?30 mL). The combined organic extracts were dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to afford compound Vb (5.99 g, 99% yield) as a white solid. The product was used directly in the next step without further purification. .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 13.2 (br. s, 1H), 7.58 (s, 1H), 7.35 (dd, 1H), 7.07 (d, 1H), 4.83 (s, 2H).

    No. VIIb: ethyl 2-[[2-(2,4-dichlorophenoxy)acetyl]-methyl-hydrazono]propanoate

    [0157] ##STR00018##

    [0158] To a stirred mixture of compound Vb (5.99 g, 27 mmol) in CH.sub.2Cl.sub.2 (54 mL) at 0? C. under an atmosphere of argon was added oxalyl chloride (2.48 mL, 28.4 mmol). The resulting mixture was allowed to warm to RT and was stirred for 1 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in CH.sub.2Cl.sub.2 (135 mL). To this solution at RT was added compound VIa (4.30 g, 29.8 mmol), Et.sub.3N (8.50 mL, 60.9 mmol) and propanephosphonic acid anhydride (16.13 mL, 27 mmol). The resulting mixture was stirred at RT for 6 h and then concentrated under reduced pressure. The resulting residue was diluted with pH 4.65 acetate buffer (50 mL) and extracted with EtOAc (3?25 mL). The combined organic extracts were dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to afford compound VIIb (8.42 g, 90% yield) as a yellow solid. The product was used directly in the next step without further purification. .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.56 (s, 1H), 7.32 (dd, 1H), 7.00 (d, 1H), 5.16 (s, 2H), 4.21 (q, 2H), 3.37 (s, 3H), 2.29 (s, 3H), 1.26 (t, 3H).

    No. I-019: 4-(2,4-dichlorophenoxy)-5-hydroxy-2,6-dimethyl-pyridazin-3-one

    [0159] ##STR00019##

    [0160] To a stirred mixture of compound VIIb (3.72 g, 10.7 mmol) in toluene (54 mL) at RT and added DBU (6.53 mL, 42.8 mmol). The resulting mixture was fitted with a Dean Stark apparatus and was refluxed for 5 h. The reaction mixture was cooled to RT and concentrated under reduced pressure. The resulting residue was diluted with HCl (50 mL, 1M) and was extracted with EtOAc (3?25 mL). The combined organic extracts were dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with heptane/EtOAc (0%.fwdarw.50%) to afford compound l -019 (0.50 g, 16% yield) as a white solid.

    No. I-043: [5-(2,4-dichlorophenoxy)-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate

    [0161] ##STR00020##

    [0162] To a stirred mixture of compound l -019 (0.1 g, 0.33 mmol), Et.sub.3N (0.1 mL, 0.66 mmol) and 4-dimethylaminopyridine (0.004 g, 0.033 mmol) in CH.sub.2Cl.sub.2 (10 mL) at 0? C. under an atmosphere of argon was added 2-methylpropionyl chloride. The resulting mixture was allowed to warm to RT and stirred for 2 h. The reaction mixture was directly purified by flash column chromatography on silica gel eluting with heptane/EtOAc (0%.fwdarw.50%) to afford compound l -043 (0.01 g, 8% yield) as a white solid.

    No. IVc: ethyl 2-[(2-chloro-3-pyridyl)oxy]acetate

    [0163] ##STR00021##

    [0164] To a stirred mixture of 2-chloropyridin-3-ol (2.0 g, 15.4 mmol) and K.sub.2CO.sub.3 (3.20 g, 23.1 mmol) in DMF (31 mL) at RT under an atmosphere of argon was added ethyl bromoacetate (2.05 mL, 18.5 mmol). The resulting mixture was stirred at 80? C. for 4 h. The reaction mixture was diluted with sat. aq. ammonium chloride (30 mL) and extracted with EtOAc (3?30 mL). The combined organic extracts were washed with brine, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to afford compound IVc (2.54 g, 76% yield) as a yellow solid. The product was used directly in the next step without further purification. .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 8.06 (d, 1H), 7.30-7.15 (m, 2H), 4.74 (s, 1H), 4.28 (q, 2H), 1.30 (t, 3H).

    No. Vc: 2-[(2-chloro-3-pyridyl)oxy]acetic acid

    [0165] ##STR00022##

    [0166] To a stirred mixture of compound IVc (2.54 g, 11.7 mmol) in a mixture of THF/water (59 mL, 7:3) at RT was added LiOH (0.85 g, 35.3 mmol). The resulting mixture was stirred at RT for 5 h. The reaction was then acidified with 2M HCl and extracted with EtOAc (3?30 mL). The combined organic extracts were dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to afford compound Vc (2.13 g, 99% yield) as a white solid. .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 13.2 (br. s, 1H), 8.00 (d, 1H), 7.50 (d, 1H), 7.38 (dd, 1H), 4.89 (s, 2H).

    No. VIIc: ethyl 2-[[2-[(2-chloro-3-pyridyl)oxy]acetyl]-methyl-hydrazono]propanoate

    [0167] ##STR00023##

    [0168] To a stirred mixture of compound Vc (2.13 g, 11.3 mmol) in CH.sub.2Cl.sub.2 (57 mL) at 0? C. under an atmosphere of argon was added oxalyl chloride (1.04 mL, 11.9 mmol). The resulting mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with CH.sub.2Cl.sub.2 (57 mL). Compound VIa (2.04 g, 14.1 mmol), Et.sub.3N (3.55 mL, 25.4 mmol) and propanephosphonic acid anhydride (13.46 mL, 22.6 mmol) were added and the resulting mixture was stirred at RT for 6 h. The reaction mixture was concentrated under reduced pressure, diluted with pH 4.65 acetate buffer (50 mL) and extracted with EtOAc (3?25 mL). The combined organic extracts were dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to afford compound VIIc (3.29 g, 93% yield) as a yellow oil. .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.32-7.28 (m, 3H), 4.97 (s, 2H), 4.10 (q, 2H), 3.38 (s, 3H), 2.33 (s, 3H), 1.20 (t, 3H).

    No. I-059: 4-[(2-chloro-3-pyridyl)oxy]-5-hydroxy-2,6-dimethyl-pyridazin-3-one

    [0169] ##STR00024##

    [0170] To a stirred mixture of compound VIIc (3.29 g, 10.4 mmol) in toluene (52 mL) at RT was added DBU (6.39 mL, 41.9 mmol). The resulting mixture was equipped with a Dean Stark apparatus and then stirred at reflux for 5 h. The reaction mixture was allowed to cool to RT and was then concentrated under reduced pressure. The resulting residue was diluted with 1M HCl (50 mL) and extracted with EtOAc (3?25 mL). The combined organic extracts were dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The resulting residue was passed through a plug of silica gel eluting with CH.sub.2Cl.sub.2/MeOH (9:1) and then purified by prep. HPLC to afford compound I-059 (0.08 g, 3% yield) as a yellow solid.

    No. XI: methyl 2-(2-cyclopropylphenoxy)acetate

    [0171] ##STR00025##

    [0172] To a stirred mixture of methyl 2-(2-iodophenoxy)acetate (3.02 g, 10.3 mmol), cyclopropylboronic acid (0.98 g, 11.4 mmol) and potassium phosphate (6.58 g, 31.0 mmol) in 1,4-dioxane at RT under an atmosphere of nitrogen was added Pd.sub.2(dba).sub.3 (161 mg, 0.155 mmol) and SPhos (132 mg, 0.321 mmol). The resulting mixture was heated to reflux for 8 h. The reaction mixture was diluted with water (20 mL) and CH.sub.2Cl.sub.2 (20 mL) and then filtered through a pad of celite. The phases were separated and the aqueous phase was extracted with CH.sub.2Cl.sub.2 (3?10 mL). The combined organic extracts were dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with heptane/EtOAc (4:1) to afford compound XI (805 mg, 46% yield) as a pale yellow oil.

    [0173] 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 pyridazinones, the compounds cited below are obtained.

    TABLE-US-00001 TABLE 1 Examples of preferred compounds of the general formula (I) [00026]embedded image (I) Ex. No. R.sup.1 R.sup.2 G R.sup.3 W I-001 Me Me H phenyl O I-002 Me Me H 4-chlorophenyl O I-003 Me Me H 2-chlorophenyl O I-004 Me Me H 3-chlorophenyl O I-005 Me Me H 3-trifluoromethylphenyl O I-006 Me Me H 4-trifluoromethylphenyl O I-007 Me Me H 2-trifluoromethylphenyl O I-008 Me Me H 2-trifluoromethoxyphenyl O I-009 Me Me ethoxycarbonyl 2-trifluoromethylphenyl O I-010 Me Me ethoxycarbonyl 2-chlorophenyl O I-011 Me Me H 2-bromophenyl O I-012 Me Me ethoxycarbonyl 2-cyclopropylphenyl O I-013 Me Me ethoxycarbonyl 2-trifluoromethoxyphenyl O I-014 Me Me H 2-cyclopropylphenyl O I-015 Me Me H 2,3-dichlorophenyl O I-016 Me Me H 2,5-dichlorophenyl O I-017 Me Me H 2-methylphenyl O I-018 Me Me H 2,6-dichlorophenyl O I-019 Me Me H 2,4-dichlorophenyl O I-020 Me Me H 3,4-dichlorophenyl O I-021 Me Me H 2-fluorophenyl O I-022 Me Me H 2-isopropylphenyl O I-023 Me Me H 2-chloro-6-methylphenyl O I-024 Me Me H 2-methoxyphenyl O I-025 Me Me H 2-chloro-3-fluorophenyl O I-026 Me Me H 2-bromo-5-fluorophenyl O I-027 Me Me H 3,5-dichlorophenyl O I-028 Me Me H 2-cyanophenyl O I-029 Me Me acetyl 2-trifluoromethoxyphenyl O I-030 Me Me acetyl 2-trifluoromethylphenyl O I-031 Me Me H 2-nitrophenyl O I-032 Me Me H 2-phenylphenyl O I-033 Me Me H 2-cyclopropyl-4-fluorophenyl O I-034 Me Me ethoxycarbonyl 2-cyclopropyl-4-fluorophenyl O I-035 Me Me H 4-chloro-2-cyclopropylphenyl O I-036 Me Me ethoxycarbonyl 4-chloro-2-cyclopropylphenyl O I-037 Me Me H 2-cyclopropyl-4-methylphenyl O I-038 Me Me ethoxycarbonyl 2-cyclopropyl-4-methylphenyl O I-039 Me Me H 2-cyclopropyl-5-methylphenyl O I-040 Me Me ethoxycarbonyl 2-cyclopropyl-5-methylphenyl O I-041 Me Me H 1-methyl-pyrazol-4-yl O I-042 Me Me morpholin-4- 2,4-dichlorophenyl O ylcarbonyl I-043 Me Me 2-methylpropanoyl 2,4-dichlorophenyl O I-044 Me Me ethoxycarbonyl 2,4-dichlorophenyl O I-045 Me Me ethoxycarbonyl 2-cyclopropyl-5-fluorophenyl O I-046 Me Me H 2-cyclopropyl-5-fluorophenyl O I-047 Me Me ethoxycarbonyl 3-chloro-2-cyclopropylphenyl O I-048 Me Me H 3-chloro-2-cyclopropylphenyl O I-049 Me Me 2,2- 2,4-dichlorophenyl O dimethylpropanoyl I-050 Me Me methoxycarbonyl 2,4-dichlorophenyl O I-051 Me Me piperidin-1- 2,4-dichlorophenyl O ylcarbonyl I-052 Me Me H 6-chloro-5-fluoropyridin-2-yl O I-053 Me Me phenacyl 2,4-dichlorophenyl O I-054 Me Me 2-methylpropanoyl 6-chloro-5-fluoropyridin-2-yl O I-055 Me Me H 6-chloro-5- O trifluoromethylpyridin-2-yl I-056 Me Me morpholin-4- 6-chloro-5-fluoro-2-pyridyl O ylcarbonyl I-057 Me Me morpholin-4- 6-chloro-5- O ylcarbonyl trifluoromethylpyridin-2-yl I-058 Me Me ethoxycarbonyl 2-cyclopropyl-3-fluorophenyl O I-059 Me Me H 2-chloro-3-pyridyl O I-060 Me Me p-tolylsulfonyl 2,4-dichlorophenyl O I-061 Me Me dimethylcarbamoyl 2,4-dichlorophenyl O I-062 Me Me diethoxyphosphoryl 2,4-dichlorophenyl O I-063 Me Me cyclopropylcarbonyl 2,4-dichlorophenyl O I-064 Me Me cyclobutylcarbonyl 2,4-dichlorophenyl O I-065 Me Me n-pentylcarbonyl 2,4-dichlorophenyl O I-066 Me Me ethoxycarbonyl 2-cyclopropyl-3-methylphenyl O I-067 Me Me morpholin-4- 1-methylpyrazol-4-yl O ylcarbonyl I-068 Me Me H 4-bromophenyl O I-069 Me Me ethoxycarbonyl 4-bromophenyl O I-070 Me Me ethoxycarbonyl 5-chloro-2-cyclopropylphenyl O I-071 Me Me H 5-chloro-2-cyclopropylphenyl O I-072 Me Me H 2-cyclopropyl-3-methylphenyl O I-073 Me Me H 2-cyclopropyl-3-fluorophenyl O I-074 Me Me ethoxycarbonyl 2-(difluoromethoxy)phenyl O I-075 Me Me 2-methylpropanoyl 4-bromophenyl O I-076 Me Me tert-butoxycarbonyl 4-bromophenyl O I-077 Me Me H 3,4,5-trichlorophenyl O I-078 Me Me morpholin-4- 4-bromophenyl O ylcarbonyl I-079 Me Me ethoxycarbonyl 2-bromophenyl O I-080 Me Me diethoxyphosphoryl 2-bromophenyl O I-081 Me Me acetyl 2-(difluoromethoxy)phenyl O I-082 Me Me H 2-(difluoromethoxy)phenyl O I-083 Me Me H pyridin-3-yl O I-084 Me Me H 2-cyclopropyl-6-fluorophenyl O I-085 Me Me ethoxycarbonyl 2-cyclopropyl-6-fluorophenyl O I-086 Me Me ethoxycarbonyl 2,5-dichlorophenyl O I-087 Me Me H 2-bromo-4,5-difluorophenyl O I-088 Me Me ethoxycarbonyl 2-bromo-5-fluorophenyl O I-089 Me Me 2-methylpropanoyl 2-bromo-5-fluorophenyl O I-090 Me Me H 2-bromo-3,5-difluorophenyl O I-091 Me Me H 2-bromo-5-chlorophenyl O I-092 Me Me 2-methylpropanoyl 2-bromo-5-chlorophenyl O I-093 Me Me ethoxycarbonyl 2-bromo-4,5-difluorophenyl O I-094 Me Me 2-methylpropanoyl 2-bromo-4,5-difluorophenyl O I-095 Me Me 2-methylpropanoyl 2,5-dichlorophenyl O I-096 Me Me H 2,3,5-trichlorophenyl O I-097 Me Me ethoxycarbonyl 2,3,5-trichlorophenyl O I-098 Me Me ethoxycarbonyl 2-bromo-3,5-difluorophenyl O I-099 Me Me 2-methylpropanoyl 2-bromo-3,5-difluorophenyl O I-100 Me Me 2-methylpropanoyl 2,3,5-trichlorophenyl O I-101 Me Me H 2-cyclopropyl-4,5- O difluorophenyl I-102 Me Me 2-methylpropanoyl 2-cyclopropyl-4,5- O difluorophenyl I-103 Me Me H 2-cyclopropyl-3,5- O difluorophenyl I-104 Me Me ethoxycarbonyl 2-cyclopropyl-3,5- O difluorophenyl I-105 Me Me 2-methylpropanoyl 2-cyclopropyl-3,5- O difluorophenyl I-106 Me Me ethoxycarbonyl 2-cyclopropyl-4,5- O difluorophenyl

    Spectroscopic Data of Selected Table Examples:

    [0174] The spectroscopic data listed hereinafter for selected table examples were evaluated via conventional .sup.1H-NMR interpretation or via NMR peak list methods.

    a) Conventional .SUP.1.H-NMR Interpretation

    [0175] No. I-016: .sup.1H-NMR (300 MHz, DMSO-d.sub.6): ?.sub.H 7.48 (d, J=8.5 Hz, 1H), 7.08-7.04 (m, 1H), 6.79-6.78 (m, 1H), 3.50 (s, 3H), 2.14 (s, 3H).

    [0176] No. I-017: .sup.1H-NMR (300 MHz, DMSO-d.sub.6): ?.sub.H 11.24 (br. s, 1H), 7.23-7.20 (m, 1H), 7.05-6.91 (m, 2H), 6.55-6.52 (m, 1H), 3.53 (s, 3H), 2.33 (s, 3H), 2.24 (s, 3H).

    [0177] No. I-037: .sup.1H-NMR (300 MHz, DMSO-d.sub.6): ?.sub.H 11.22 (br. s, 1H), 6.79-6.76 (m, 1H), 6.71 (s, 1H), 6.43-6.41 (m, 1H), 3.51 (s, 3H), 2.92-2.19 (m, 7H), 0.92-0.86 (m, 2H), 0.75-0.72 (m, 2H).

    [0178] No. I-038: .sup.1H-NMR (300 MHz, CDCl.sub.3): ?.sub.H 6.86-6.82 (m, 1H), 6.70-6.66 (m, 2H), 4.21 (q, J=7.0 Hz, 2H), 3.74 (s, 3H), 2.28 (s, 3H), 2.25 (s, 3H), 2.16-2.08 (m, 1H), 1.29 (t, J=7.0 Hz, 3H), 0.92-0.88 (m, 2H), 0.74-0.60 (m, 2H).

    [0179] No. I-039: .sup.1H-NMR (300 MHz, DMSO-d.sub.6): ?.sub.H 6.84-6.71 (m, 2H), 6.35 (s, 1H), 3.51 (s, 3H), 2.31-2.01 (m, 7H), 0.90-0.83 (m, 2H), 0.71-0.66 (m, 2H).

    [0180] No. I-040: .sup.1H-NMR (300 MHz, DMSO-d.sub.6): ?.sub.H 6.83-6.80 (m, 2H), 6.54 (s, 1H), 4.20 (q, J=7.0 Hz, 2H), 3.65 (s, 3H), 2.23 (s, 3H), 2.17 (s, 3H), 2.04-1.95 (m, 1H), 1.20 (t, J=7.0 Hz, 3H), 0.88-0.81 (m, 2H), 0.70-0.60 (m, 2H).

    [0181] No. I-041: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.27 (s, 1H), 7.15 (s, 1H), 4.50 (s, 3H), 3.82 (s, 3H), 2.26 (s, 3H).

    [0182] No. I-042: .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.42 (s, 1H), 7.14 (dd, 1H), 6.91 (d, 1H), 3.74 (s, 3H), 3.66 (m, 4H), 3.56 (m, 2H), 3.46 (m, 2H), 2.28 (s, 3H).

    [0183] No. I-043: .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.40 (s, 1H), 7.13 (dd, 1H), 6.84 (d, 1H), 3.74 (s, 3H), 2.79 (sept., 1H), 2.25 (s, 3H), 1.26 (d, 6H).

    [0184] No. I-044: .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.42 (s, 1H), 7.14 (dd, 1H), 6.89 (d, 1H), 4.29 (q, 2H), 3.73 (s, 3H), 2.31 (s, 3H), 1.34 (t, 3H).

    [0185] No. I-049: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.70 (s, 1H), 7.32 (dd, 1H), 6.97 (d, 1H), 3.65 (s, 3H), 2.21 (s, 3H), 1.20 (s, 9H).

    [0186] No. I-050: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.71 (s, 1H), 7.33 (dd, 1H), 7.05 (d, 1H), 3.85 (s, 3H), 3.64 (s, 3H), 2.26 (s, 3H).

    [0187] No. I-063: .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.41 (s, 1H), 7.12 (d, 1H), 6.86 (d, 1H), 3.73 (s, 3H), 2.25 (s, 3H), 1.79 (m, 1H), 1.13-1.12 (m, 2H), 1.06-1.04 (m, 2H).

    [0188] No. I-064: .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.40 (s, 1H), 7.13 (d, 1H), 6.86 (d, 1H), 3.74 (s, 3H), 3.36 (m, 1H), 2.35-2.29 (m, 4H), 2.25 (s, 3H), 2.04 (m, 1H), 1.95 (m, 1H).

    [0189] No. I-065: .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.40 (s, 1H), 7.12 (d, 1H), 6.86 (d, 1H), 3.73 (s, 3H), 2.53 (t, 2H), 2.25 (s, 3H), 1.69 (t, 2H), 1.32-1.30 (m, 4H), 0.86 (t, 3H).

    [0190] No. I-080: .sup.1H-NMR (400 MHz, CDCl.sub.3): ?.sub.H 7.58 (dd, 1H), 7.21 (dt, 1H), 6.98 (dt, 1H), 6.91 (dd, 1H), 4.26-4.19 (m, 4H), 3.69 (s, 3H), 2.44 (s, 3H), 1.33-1.29 (m, 6H).

    [0191] No. I-098: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.33-7.26 (m, 1H), 7.00-6.94 (m, 1H), 4.28 (q, J=7.0 Hz, 2H), 3.67 (s, 3H), 2.28 (s, 3H), 1.24 (t, J=7.0 Hz, 3H).

    [0192] No. I-099: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.30-7.23 (m, 1H), 6.95-6.90 (m, 1H), 3.67 (s, 3H), 2.89-2.81 (m, 1H), 2.23 (s, 3H), 1.14 (d, J=7.0 Hz, 6H).

    [0193] No. I-100: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.63-7.62 (m, 1H), 7.23-7.22 (m, 1H), 3.66 (s, 3H), 2.92-2.82 (m, 1H), 2.30 (s, 3H), 1.14 (d, J=7.0 Hz, 6H).

    [0194] No. I-101: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 11.36 (s, 1H), 7.03-6.97 (m, 1H), 6.78-6.73 (m, 1H), 3.53 (s, 3H), 2.28-2.17 (m, 4H), 0.94-0.91 (m, 2H), 0.78-0.76 (m, 2H).

    [0195] No. I-102: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.06-7.01 (m, 1H), 6.98-6.93 (m, 1H), 3.67 (s, 3H), 2.83-2.76 (m, 1H), 2.21 (s, 3H), 2.03-1.99 (m, 1H), 1.14-1.10 (m, 6H), 0.95-0.89 (m, 2H), 0.75-0.70 (m, 2H).

    [0196] No. I-103: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 11.42 (br s, 1H), 6.87-6.81 (m, 1H), 6.43-6.39 (m, 1H), 3.54 (m, 3H), 2.23 (m, 3H), 1.84-1.77 (m, 1H), 1.01-0.95 (m, 2H), 0.90-0.80 (m, 2H).

    [0197] No. I-104: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 6.99-6.91 (m, 1H), 6.67-6.62 (m, 1H), 4.27 (q, J=7.0 Hz, 2H), 3.65 (m, 3H), 2.26 (m, 3H), 1.76-1.67 (m, 1H), 1.23 (t, J=7.0 Hz, 3H), 0.91-0.74 (m, 4H).

    [0198] No. I-105: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 6.97-6.91 (m, 1H), 6.62-6.58 (m, 1H), 3.66 (s, 3H), 2.88-2.77 (m, 1H), 2.21 (s, 3H), 1.75-1.70 (m, 1H), 1.14 (d, J=7.0 Hz, 6H), 0.90-0.81 (m, 4H).

    [0199] No. I-106: .sup.1H-NMR (400 MHz, DMSO-d.sub.6): ?.sub.H 7.10-7.01 (m, 2H), 4.25 (q, J=7.0 Hz, 2H), 3.65 (m, 3H), 2.25 (m, 3H), 2.05-1.97 (m, 1H), 1.22 (t, J=7.0 Hz, 3H), 0.93-0.98 (m, 2H), 0.75-0.71 (m, 2H).

    b) NMR Peak List Method

    [0200] .sup.1H-NMR data of selected examples are written in form of .sup.1H-NMR-peak lists. To each signal peak are listed the ?-value in ppm and the signal intensity in round brackets. Between the ?-value?signal intensity pairs are semicolons as delimiters.

    [0201] The peak list of an example has therefore the form: [0202] ?.sub.1 (intensity.sub.1); ?.sub.2 (intensity.sub.2); . . . ; ?.sub.i (intensity.sub.i); . . . ; ?.sub.n (intensity.) Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

    [0203] For calibrating chemical shift for .sup.1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore, in NMR peak lists tetramethylsilane peak can occur but not necessarily.

    [0204] The .sup.1H-NMR peak lists are similar to classical .sup.1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

    [0205] Additionally, they can show like classical .sup.1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.

    [0206] To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown in our .sup.1H-NMR peak lists and have usually on average a high intensity.

    [0207] The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).

    [0208] Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore, their peaks can help to recognize the reproduction of our preparation process via side-products-fingerprints.

    [0209] An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical .sup.1H-NMR interpretation.

    [0210] Further details of NMR-data description with peak lists you find in the publication Citation of NMR Peaklist Data within Patent Applications of the Research Disclosure Database Number 564025.

    TABLE-US-00002 I-001: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.3047 (4.2); 7.3158 (1.8); 7.3088 (0.9); 7.2909 (3.1); 7.2877 (3.0); 7.2626 (2.5); 7.0496 (1.1); 7.0252 (1.9); 7.0006 (0.9); 6.9687 (0.4); 6.9413 (0.4); 6.8919 (3.5); 6.8662 (3.0); 4.6613 (0.4); 4.4459 (0.6); 3.5379 (16.0); 3.3626 (10.1); 2.6606 (0.5); 2.6450 (0.5); 2.5071 (11.3); 2.5013 (14.4); 2.4956 (10.1); 2.2277 (15.7); 2.0748 (0.9); ?0.0004 (1.8) I-002: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.3973 (1.1); 7.3641 (0.7); 7.3561 (0.8); 7.3443 (4.7); 7.3367 (1.7); 7.3217 (1.8); 7.3142 (5.1); 7.3026 (0.6); 6.9931 (0.6); 6.9632 (0.6); 6.9465 (0.7); 6.9348 (5.2); 6.9273 (1.6); 6.9123 (1.7); 6.9048 (4.4); 6.8928 (0.4); 4.4608 (0.9); 3.5365 (16.0); 3.3550 (5.0); 2.6538 (0.8); 2.6384 (0.8); 2.5073 (13.8); 2.5015 (17.4); 2.4957 (11.8); 2.2247 (15.7); 2.0754 (0.6); 1.2364 (0.4); 1.2129 (0.4); 1.1743 (0.5); ?0.0004 (3.9) I-003: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.4328 (2.2); 7.5040 (1.5); 7.4987 (1.6); 7.4777 (1.8); 7.4723 (1.8); 7.2171 (0.7); 7.2116 (0.7); 7.1921 (1.3); 7.1866 (1.2); 7.1651 (1.2); 7.1596 (1.1); 7.0733 (1.1); 7.0683 (1.2); 7.0478 (1.5); 7.0426 (1.7); 7.0221 (0.8); 7.0172 (1.0); 6.7900 (1.7); 6.7852 (1.7); 6.7628 (1.6); 6.7580 (1.4); 5.7547 (1.1); 4.5737 (0.9); 3.5282 (16.0); 3.3417 (36.7); 2.6724 (0.8); 2.6570 (0.8); 2.5128 (12.8); 2.5069 (25.0); 2.5009 (33.0); 2.4950 (22.3); 2.4893 (10.2); 2.2391 (15.8); ?0.0001 (2.9) I-004: .sup.1H-NMR (300.1 MHz, MeOD): ? = 7.2224 (1.1); 7.1953 (2.4); 7.1684 (1.5); 6.9546 (1.0); 6.9517 (1.2); 6.9482 (1.3); 6.9453 (1.2); 6.9282 (0.9); 6.9252 (1.0); 6.9217 (1.2); 6.9189 (1.0); 6.8904 (1.5); 6.8832 (2.5); 6.8764 (1.6); 6.8549 (1.4); 6.8521 (1.3); 6.8468 (1.0); 6.8441 (0.8); 6.8273 (1.1); 6.8245 (1.1); 6.8193 (0.9); 6.8165 (0.8); 5.4861 (4.2); 4.8558 (56.8); 3.6299 (16.0); 3.3156 (11.9); 3.3102 (21.3); 3.3048 (28.5); 3.2994 (19.6); 3.2939 (9.9); 2.2396 (15.6); 2.0296 (1.5); 1.9311 (0.4); 1.2968 (0.6); 0.0106 (0.5); ?0.0003 (8.7) I-005: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 7.5376 (0.7); 7.5176 (1.7); 7.4974 (1.1); 7.4051 (1.4); 7.3855 (1.1); 7.2378 (1.9); 7.2253 (0.6); 7.1700 (1.1); 7.1644 (1.0); 7.1495 (1.0); 7.1436 (0.9); 4.8106 (1.3); 3.6210 (0.9); 3.5448 (16.0); 3.3404 (2.2); 3.0184 (0.5); 3.0092 (0.5); 2.5421 (3.0); 2.5115 (11.6); 2.5072 (24.1); 2.5027 (32.4); 2.4982 (23.1); 2.4939 (10.7); 2.2269 (13.5); 1.7941 (0.7); 1.7627 (0.5); 0.0000 (5.7) I-006: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.5084 (2.2); 7.6754 (3.2); 7.6459 (3.2); 7.1009 (3.2); 7.0727 (2.9); 3.7082 (0.4); 3.6470 (0.4); 3.6213 (0.4); 3.5507 (15.6); 3.4828 (1.1); 3.3281 (342.1); 3.0390 (0.7); 3.0049 (0.4); 2.9870 (0.5); 2.7275 (3.3); 2.7216 (2.4); 2.5072 (405.2); 2.5015 (499.2); 2.4957 (346.2); 2.2770 (4.2); 2.2712 (4.7); 2.2395 (16.0); 2.0754 (0.9); 2.0021 (0.4); 1.9088 (0.4); 1.2356 (0.4); 1.1468 (2.1); ?0.0005 (20.8) I-007: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 11.3937 (1.0); 7.6998 (1.2); 7.6831 (1.3); 7.6803 (1.2); 7.5280 (0.6); 7.5095 (1.2); 7.4911 (0.7); 7.2174 (0.8); 7.1984 (1.4); 7.1795 (0.7); 6.8938 (1.6); 6.8729 (1.5); 5.0951 (0.3); 3.5235 (16.0); 3.3274 (3.7); 3.0022 (0.6); 2.5105 (10.7); 2.5060 (22.0); 2.5015 (29.5); 2.4970 (21.0); 2.4925 (9.8); 2.2431 (15.4); 2.0754 (0.9); 0.0000 (5.3) I-008: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.4137 (1.2); 7.4086 (1.0); 7.3915 (1.0); 7.3867 (1.4); 7.3819 (1.0); 7.2570 (0.7); 7.2517 (0.7); 7.2318 (1.3); 7.2268 (1.3); 7.2049 (1.2); 7.1995 (1.1); 7.1274 (1.0); 7.1224 (1.1); 7.1012 (1.3); 7.0967 (1.4); 7.0756 (0.7); 7.0707 (0.6); 6.8728 (1.7); 6.8680 (1.7); 6.8454 (1.5); 6.8406 (1.4); 3.5163 (16.0); 3.4578 (0.4); 3.3394 (78.7); 2.7281 (0.8); 2.7223 (0.6); 2.5139 (51.1); 2.5080 (98.1); 2.5021 (128.9); 2.4961 (90.1); 2.4905 (42.6); 2.2780 (0.6); 2.2721 (0.8); 2.2662 (0.5); 2.2155 (14.0); 0.0108 (1.4); ?0.0002 (37.3); ?0.0112 (1.4) I-009: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.7429 (1.3); 7.7172 (1.4); 7.5917 (0.6); 7.5669 (1.3); 7.5404 (0.8); 7.3091 (1.0); 7.2838 (1.6); 7.2582 (0.7); 7.0407 (1.8); 7.0128 (1.6); 5.7587 (0.7); 4.2545 (1.3); 4.2309 (4.2); 4.2073 (4.3); 4.1837 (1.3); 3.6586 (15.8); 3.3236 (15.4); 3.3003 (0.7); 2.5069 (38.4); 2.5011 (49.0); 2.4953 (34.2); 2.2692 (16.0); 1.2350 (0.6); 1.2015 (4.5); 1.1779 (9.4); 1.1542 (4.4); ?0.0005 (6.2) I-010: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.5401 (1.6); 7.5346 (1.6); 7.5138 (1.9); 7.5084 (1.8); 7.2756 (0.7); 7.2700 (0.7); 7.2492 (1.4); 7.2451 (1.4); 7.2237 (1.3); 7.2182 (1.1); 7.1676 (1.2); 7.1625 (1.3); 7.1415 (1.5); 7.1367 (1.6); 7.1165 (0.7); 7.1114 (0.6); 6.9903 (2.0); 6.9855 (1.9); 6.9632 (1.6); 6.9584 (1.5); 4.2726 (1.4); 4.2491 (4.3); 4.2254 (4.3); 4.2018 (1.4); 3.6472 (15.9); 3.3179 (8.3); 3.1749 (0.4); 3.1614 (0.4); 2.5065 (14.8); 2.5006 (19.0); 2.4949 (13.4); 2.2510 (16.0); 2.0737 (0.8); 1.2301 (4.5); 1.2065 (9.4); 1.1828 (4.3); ?0.0005 (1.4) I-011: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.4483 (0.7); 7.6510 (1.8); 7.6460 (1.8); 7.6247 (2.0); 7.6197 (1.9); 7.2552 (0.8); 7.2501 (0.9); 7.2279 (1.5); 7.2033 (1.2); 7.1982 (1.0); 7.0068 (1.2); 7.0022 (1.2); 6.9811 (1.8); 6.9769 (1.6); 6.9558 (1.0); 6.9512 (1.0); 6.7604 (2.0); 6.7560 (1.9); 6.7330 (1.8); 6.7286 (1.6); 5.7608 (1.6); 5.0440 (0.7); 4.7807 (0.4); 4.5725 (0.8); 3.5250 (16.0); 3.3363 (38.0); 3.0031 (1.3); 2.6759 (0.7); 2.6603 (0.7); 2.5074 (32.3); 2.5017 (41.0); 2.4960 (29.4); 2.2716 (0.4); 2.2650 (0.4); 2.2363 (15.8); ?0.0004 (2.7) I-012: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.2607 (10.0); 7.0735 (0.4); 7.0569 (1.2); 7.0500 (2.0); 7.0384 (2.6); 7.0260 (2.7); 7.0203 (1.8); 7.0024 (0.6); 6.9324 (1.6); 6.9246 (0.9); 6.9136 (1.1); 6.9012 (1.0); 6.8930 (0.5); 6.8647 (0.3); 6.7821 (1.5); 6.7737 (1.0); 6.7642 (0.8); 6.7573 (1.0); 6.7513 (1.4); 4.6673 (1.3); 4.2863 (0.7); 4.2619 (0.7); 4.2481 (1.3); 4.2244 (3.9); 4.2006 (4.0); 4.1769 (1.3); 3.7470 (16.0); 3.2559 (0.4); 2.3063 (1.9); 2.2849 (15.8); 2.2002 (0.5); 2.1893 (0.6); 2.1716 (1.1); 2.1539 (0.6); 2.1436 (0.6); 1.6198 (0.4); 1.3522 (0.5); 1.3280 (1.2); 1.3139 (4.2); 1.3020 (1.5); 1.2901 (8.3); 1.2781 (0.8); 1.2663 (4.0); 0.9676 (0.4); 0.9625 (0.4); 0.9469 (0.8); 0.9319 (2.1); 0.9246 (2.1); 0.9109 (1.1); 0.9030 (1.9); 0.8962 (1.9); 0.8828 (0.9); 0.7459 (0.8); 0.7318 (2.1); 0.7266 (2.3); 0.7145 (2.0); 0.7086 (2.2); 0.6924 (1.0); 0.6683 (0.4); ?0.0002 (8.2) I-013: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.4819 (1.1); 7.4774 (0.9); 7.4597 (1.0); 7.4553 (1.4); 7.4507 (1.0); 7.3297 (0.6); 7.3241 (0.7); 7.3042 (1.4); 7.2988 (1.3); 7.2775 (1.4); 7.2717 (1.2); 7.2369 (1.2); 7.2314 (1.4); 7.2107 (1.4); 7.2054 (1.5); 7.1851 (0.7); 7.1797 (0.6); 7.0595 (1.9); 7.0542 (1.9); 7.0323 (1.6); 7.0271 (1.5); 4.2611 (1.3); 4.2374 (4.2); 4.2137 (4.3); 4.1902 (1.4); 3.6470 (15.8); 3.3536 (0.6); 3.3294 (75.3); 3.3076 (0.5); 2.7282 (0.4); 2.5137 (29.4); 2.5080 (53.7); 2.5020 (68.6); 2.4961 (47.3); 2.2631 (16.0); 2.0749 (0.4); 1.2202 (4.4); 1.1966 (9.3); 1.1730 (4.2); 0.0106 (1.0); ?0.0002 (19.9); ?0.0112 (0.6) I-014: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 6.8883 (0.7); 6.8793 (0.8); 6.8673 (0.9); 6.8587 (1.3); 6.8527 (1.0); 6.8399 (1.0); 6.8313 (1.1); 6.7478 (0.3); 6.7393 (0.8); 6.7218 (3.2); 6.7196 (3.2); 6.7153 (3.8); 6.6981 (1.4); 6.6946 (1.4); 6.6729 (0.4); 6.6694 (0.4); 6.4389 (2.0); 6.4127 (1.7); 6.4097 (1.7); 3.3757 (17.3); 3.3479 (46.3); 2.5127 (6.8); 2.5069 (13.4); 2.5011 (18.1); 2.4952 (13.6); 2.3463 (0.3); 2.3283 (0.7); 2.3176 (0.7); 2.3107 (0.6); 2.3000 (1.3); 2.2893 (0.6); 2.2822 (0.8); 2.2715 (0.8); 2.2538 (0.4); 2.0740 (0.5); 1.9713 (16.0); 0.9165 (0.7); 0.9024 (1.9); 0.8950 (2.3); 0.8883 (1.3); 0.8828 (1.3); 0.8739 (2.0); 0.8666 (2.2); 0.8544 (1.0); 0.7159 (0.9); 0.7035 (2.2); 0.6969 (2.6); 0.6858 (2.3); 0.6788 (2.2); 0.6645 (0.8) I-015: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.5653 (0.5); 7.3302 (1.5); 7.3259 (1.5); 7.3033 (2.5); 7.2988 (2.3); 7.2333 (2.1); 7.2059 (3.2); 7.1788 (1.4); 6.8091 (2.0); 6.8044 (1.9); 6.7814 (1.8); 6.7769 (1.6); 5.7610 (0.4); 4.8633 (0.8); 3.5284 (16.0); 3.3297 (34.1); 2.9962 (0.4); 2.5132 (15.8); 2.5074 (30.0); 2.5016 (38.9); 2.4957 (27.2); 2.2716 (0.3); 2.2327 (14.9); 2.0754 (0.8); 0.0107 (0.6); ?0.0002 (14.6); ?0.0113 (0.7) I-018: .sup.1H-NMR (400.2 MHz, MeOD): ? = 7.3129 (6.9); 7.3034 (0.4); 7.2927 (8.3); 7.0604 (2.2); 7.0403 (3.0); 7.0200 (1.7); 4.8996 (37.6); 3.5665 (16.0); 3.3440 (0.5); 3.3133 (3.4); 3.3093 (6.6); 3.3052 (9.4); 3.3011 (6.6); 3.2970 (3.4); 2.2401 (13.6); 1.2842 (0.6); 0.0001 (1.7) I-019: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.5952 (3.9); 7.5869 (3.9); 7.2284 (2.3); 7.2199 (2.2); 7.1988 (2.7); 7.1903 (2.5); 6.7653 (3.3); 6.7358 (3.0); 3.4855 (21.9); 3.4221 (0.4); 3.3628 (0.3); 3.2485 (0.3); 2.5071 (11.8); 2.5012 (15.3); 2.4954 (10.8); 2.1446 (16.0); 1.9885 (0.6); 1.1740 (0.4); ?0.0004 (2.8) I-020: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.4692 (4.2); 7.4396 (4.6); 7.0083 (3.2); 6.8388 (2.0); 6.8294 (1.7); 6.8091 (1.9); 3.4603 (24.6); 3.3410 (2.9); 3.2243 (0.9); 3.1885 (0.6); 3.1461 (0.4); 3.0190 (0.3); 2.7274 (0.4); 2.5385 (0.5); 2.5130 (19.3); 2.5072 (38.1); 2.5012 (50.5); 2.4954 (35.5); 2.0832 (16.0); 1.7902 (0.4); 1.1982 (0.3); ?0.0004 (6.2) I-021: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 8.1453 (0.8); 7.2761 (0.5); 7.2681 (0.4); 7.2605 (0.4); 7.2529 (0.4); 7.2437 (0.8); 7.2373 (0.6); 7.2310 (0.5); 7.2128 (0.6); 7.2053 (0.7); 7.0310 (0.4); 7.0129 (1.2); 7.0065 (1.3); 6.9943 (1.7); 6.9865 (1.3); 6.9807 (1.4); 6.9705 (0.7); 6.9634 (0.6); 6.7928 (0.6); 6.7835 (0.4); 6.7768 (0.4); 6.7631 (0.8); 6.7398 (0.4); 6.7311 (0.5); 4.7008 (0.4); 4.5485 (0.6); 3.7320 (0.8); 3.5007 (16.0); 3.2644 (0.7); 3.1743 (0.4); 3.1571 (0.3); 2.6616 (0.6); 2.6461 (0.6); 2.5142 (4.6); 2.5083 (6.1); 2.5025 (4.4); 2.1665 (11.7) I-022: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.2818 (1.2); 7.2752 (1.2); 7.2585 (1.4); 7.2511 (1.4); 7.0543 (0.4); 7.0471 (0.6); 7.0295 (1.4); 7.0226 (1.4); 7.0041 (2.0); 6.9965 (2.4); 6.9771 (1.3); 6.9523 (0.4); 6.5350 (1.8); 6.5296 (1.8); 6.5086 (1.5); 6.5041 (1.5); 3.5042 (16.0); 3.4908 (1.5); 3.4663 (1.6); 3.4432 (1.5); 3.4200 (1.4); 3.3433 (177.4); 2.5082 (33.5); 2.5023 (44.4); 2.4965 (31.9); 2.2133 (12.8); 1.7527 (0.5); 1.2646 (14.1); 1.2415 (14.0); ?0.0004 (0.7) I-023: .sup.1H-NMR (300.1 MHz, MeOD): ? = 7.0242 (1.1); 7.0204 (1.2); 6.9979 (1.3); 6.9940 (1.4); 6.9578 (1.0); 6.9550 (1.0); 6.9327 (1.5); 6.9300 (1.3); 6.8164 (1.7); 6.7906 (2.4); 6.7649 (1.0); 4.7922 (9.4); 3.4905 (0.4); 3.4643 (16.0); 3.2394 (1.3); 3.2115 (0.6); 3.2061 (1.1); 3.2006 (1.6); 3.1952 (1.1); 3.1897 (0.5); 2.2171 (0.4); 2.1763 (11.5); 2.0889 (15.6); 1.9253 (0.4) I-024: .sup.1H-NMR (300.1 MHz, MeOD): ? = 7.0459 (0.4); 7.0270 (3.0); 7.0226 (2.2); 7.0194 (2.3); 7.0068 (1.4); 7.0014 (1.3); 6.9744 (0.4); 6.8503 (0.5); 6.8416 (0.4); 6.8299 (0.4); 6.8235 (1.2); 6.8157 (1.0); 6.8024 (0.9); 6.7947 (0.9); 6.7750 (1.8); 6.7499 (0.8); 6.7451 (0.6); 4.8714 (24.4); 3.8539 (16.0); 3.6294 (15.4); 3.3151 (2.5); 3.3096 (4.8); 3.3042 (6.6); 3.2988 (4.6); 3.2933 (2.3); 2.3034 (15.1); 0.0963 (0.4); ?0.0003 (1.4) I-025: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.5826 (0.6); 7.2624 (0.7); 7.2576 (0.8); 7.2412 (0.8); 7.2357 (1.6); 7.2304 (1.1); 7.2141 (1.1); 7.2092 (1.0); 7.0956 (0.9); 7.0899 (0.9); 7.0678 (1.7); 7.0621 (1.6); 7.0403 (0.8); 7.0346 (0.8); 6.8801 (1.0); 6.8752 (1.0); 6.8524 (1.5); 6.8495 (1.5); 6.8264 (0.8); 6.8216 (0.7); 3.5366 (16.0); 3.3314 (3.9); 2.5069 (5.2); 2.5012 (6.7); 2.4954 (4.8); 2.2337 (15.8); ?0.0004 (0.4) I-026: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 11.4864 (0.9); 7.6915 (1.4); 7.6764 (1.5); 7.6695 (1.5); 7.6544 (1.4); 6.9064 (0.8); 6.8993 (0.9); 6.8856 (1.1); 6.8783 (1.2); 6.8641 (0.8); 6.8571 (0.8); 6.7824 (1.5); 6.7754 (1.3); 6.7570 (1.5); 6.7500 (1.3); 3.5360 (16.0); 3.3316 (46.1); 2.5107 (13.9); 2.5063 (29.0); 2.5017 (39.5); 2.4972 (28.2); 2.4928 (13.1); 2.2334 (15.4); 0.0080 (0.4); ?0.0001 (12.0); ?0.0084 (0.4) I-027: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 15.5894 (0.4); 11.4850 (1.2); 11.3343 (0.3); 7.2827 (2.0); 7.2768 (3.9); 7.2709 (2.3); 7.0348 (7.6); 7.0288 (7.4); 6.0479 (0.4); 3.5525 (16.0); 3.4955 (0.3); 3.4667 (0.4); 3.4317 (0.4); 3.4010 (0.5); 3.3311 (267.0); 3.2398 (0.9); 3.2170 (0.6); 3.0757 (0.5); 2.7272 (1.2); 2.7209 (0.9); 2.5133 (69.2); 2.5076 (133.2); 2.5017 (173.5); 2.4958 (121.9); 2.2713 (1.1); 2.2259 (15.7); 1.1465 (0.8); 1.1057 (1.3); ?0.0003 (13.8); ?0.0112 (0.6) I-028: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.7740 (1.5); 7.7689 (1.6); 7.7484 (1.7); 7.7433 (1.6); 7.5393 (0.8); 7.5337 (0.8); 7.5142 (1.2); 7.5102 (1.6); 7.5056 (1.2); 7.4861 (1.1); 7.4805 (1.1); 7.1514 (1.1); 7.1283 (1.9); 7.1034 (1.0); 6.8374 (2.1); 6.8096 (2.0); 4.8826 (0.4); 3.6220 (0.3); 3.6124 (0.3); 3.5032 (16.0); 3.4569 (0.7); 3.3793 (0.7); 3.3697 (0.7); 3.2674 (0.6); 3.0486 (0.5); 2.5136 (14.4); 2.5079 (27.1); 2.5021 (35.2); 2.4962 (25.0); 2.1488 (13.1); 1.9890 (0.5); ?0.0002 (4.7) I-029: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.4746 (1.1); 7.4474 (1.2); 7.3175 (0.7); 7.2972 (1.4); 7.2915 (1.4); 7.2704 (1.4); 7.2647 (1.2); 7.2259 (1.2); 7.2201 (1.3); 7.1993 (1.4); 7.1940 (1.5); 7.1738 (0.6); 7.1687 (0.7); 7.0336 (1.9); 7.0284 (2.0); 7.0063 (1.8); 7.0010 (1.3); 5.5906 (0.3); 3.6403 (16.0); 3.3250 (163.9); 3.3014 (23.8); 3.0761 (0.4); 2.9785 (0.4); 2.7278 (1.0); 2.5131 (61.8); 2.5073 (120.8); 2.5014 (159.3); 2.4955 (112.7); 2.4396 (0.7); 2.4230 (1.1); 2.2751 (1.4); 2.2468 (15.8); 2.2253 (15.9); 1.9089 (0.4); 1.2334 (0.4); 1.1436 (0.7); ?0.0002 (13.5) I-030: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.7322 (1.1); 7.7093 (1.2); 7.5809 (0.5); 7.5564 (1.1); 7.5314 (0.7); 7.2958 (0.8); 7.2703 (1.4); 7.2450 (0.7); 7.0106 (1.5); 6.9824 (1.4); 3.6549 (15.7); 3.4163 (0.4); 3.3958 (0.4); 3.3277 (141.7); 3.2077 (0.4); 2.7336 (0.5); 2.7277 (0.6); 2.7220 (0.4); 2.5134 (29.6); 2.5075 (56.6); 2.5016 (74.3); 2.4956 (51.7); 2.4898 (25.0); 2.2774 (0.5); 2.2715 (0.7); 2.2652 (0.7); 2.2442 (16.0); 2.2321 (15.8); 2.0751 (0.8); 0.0108 (1.8); ?0.0001 (40.7); ?0.0112 (1.6) I-031: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 8.0433 (1.6); 8.0378 (1.6); 8.0162 (1.8); 8.0110 (1.6); 7.6307 (0.8); 7.6255 (0.9); 7.6026 (1.5); 7.5784 (1.1); 7.5730 (0.9); 7.2998 (1.1); 7.2723 (1.7); 7.2477 (0.9); 7.1049 (1.9); 7.0769 (1.6); 3.6616 (16.0); 3.5325 (1.3); 3.4904 (0.4); 3.4516 (0.3); 3.3238 (10.0); 3.2040 (0.4); 2.7275 (1.4); 2.7211 (1.1); 2.6806 (0.4); 2.5131 (83.2); 2.5074 (152.9); 2.5015 (198.5); 2.4956 (142.6); 2.2713 (1.2); 2.2651 (1.0); 2.2185 (0.9); 2.1201 (14.8); 2.0743 (0.3); 0.0107 (1.9); ?0.0002 (56.6); ?0.0112 (3.7); ?0.0998 (0.4); ?0.1980 (0.3) I-032: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.3015 (0.7); 7.8159 (3.7); 7.7923 (4.2); 7.4390 (2.0); 7.4155 (4.6); 7.4005 (2.7); 7.3901 (3.5); 7.3820 (2.8); 7.3762 (2.4); 7.3463 (2.0); 7.3222 (2.2); 7.2973 (0.8); 7.2552 (0.9); 7.2495 (0.9); 7.2302 (1.8); 7.2248 (1.7); 7.2037 (1.5); 7.1980 (1.3); 7.1581 (1.6); 7.1338 (2.2); 7.1091 (0.9); 6.7529 (2.3); 6.7263 (2.1); 3.5404 (16.0); 3.3356 (9.8); 2.5064 (15.0); 2.5011 (18.1); 2.2167 (15.5); 2.0752 (0.4); ?0.0002 (4.5) I-033: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 6.8087 (0.8); 6.7984 (0.9); 6.7800 (1.3); 6.7700 (1.7); 6.7521 (1.0); 6.7416 (1.3); 6.7307 (1.8); 6.7208 (1.3); 6.6973 (1.8); 6.6875 (1.3); 6.5603 (1.8); 6.5440 (1.9); 6.5307 (1.4); 6.5145 (1.4); 3.4996 (17.9); 3.4622 (1.2); 3.1673 (0.8); 2.7271 (0.4); 2.5069 (52.2); 2.5014 (65.5); 2.4959 (48.7); 2.3199 (0.6); 2.3092 (0.7); 2.2933 (1.2); 2.2764 (1.1); 2.2489 (0.4); 2.1920 (16.0); 2.1131 (0.8); 1.9889 (1.0); 1.1741 (0.5); 0.9671 (0.8); 0.9519 (2.2); 0.9447 (2.6); 0.9318 (1.6); 0.9238 (2.3); 0.9165 (2.4); 0.9038 (1.1); 0.7902 (1.1); 0.7773 (2.7); 0.7719 (3.0); 0.7600 (2.8); 0.7541 (2.6); 0.7383 (0.8); ?0.0003 (12.9) I-034: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.2619 (7.0); 6.7603 (0.4); 6.7476 (2.8); 6.7388 (1.5); 6.7311 (2.0); 6.7234 (1.4); 6.7146 (1.3); 6.6026 (1.0); 6.5950 (0.9); 6.5711 (1.2); 6.5625 (1.0); 4.2831 (0.4); 4.2749 (1.3); 4.2511 (3.9); 4.2273 (4.0); 4.2035 (1.4); 3.7410 (16.0); 3.7319 (1.8); 2.3068 (1.3); 2.2845 (15.8); 2.1978 (0.4); 2.1869 (0.5); 2.1697 (0.8); 2.1546 (0.5); 2.1428 (0.5); 1.5697 (3.3); 1.3695 (0.3); 1.3456 (0.8); 1.3352 (4.1); 1.3114 (8.4); 1.2876 (4.0); 0.9872 (0.7); 0.9716 (1.9); 0.9651 (1.9); 0.9504 (1.1); 0.9433 (1.9); 0.9367 (1.7); 0.9224 (0.8); 0.7324 (0.9); 0.7174 (2.2); 0.7119 (2.1); 0.7005 (1.9); 0.6946 (2.2); 0.6784 (0.6); ?0.0002 (5.7) I-035: .sup.1H-NMR (300.1 MHz, MeOD): ? = 6.9020 (1.2); 6.8934 (1.4); 6.8731 (1.3); 6.8646 (1.6); 6.7983 (2.6); 6.7899 (2.2); 6.4800 (2.8); 6.4512 (2.5); 4.7881 (8.1); 4.0095 (0.4); 3.9857 (0.4); 3.5371 (15.8); 3.2178 (1.9); 3.2124 (3.5); 3.2070 (4.8); 3.2016 (3.4); 3.1962 (1.7); 2.2689 (0.5); 2.2583 (0.6); 2.2513 (0.4); 2.2405 (1.2); 2.2231 (16.0); 2.1949 (0.4); 1.9317 (0.4); 1.9107 (1.6); 1.2734 (0.5); 1.1880 (2.9); 1.1615 (0.7); 1.1377 (1.0); 1.1139 (0.5); 0.9118 (0.7); 0.8969 (1.8); 0.8898 (2.0); 0.8758 (1.1); 0.8683 (1.9); 0.8614 (1.8); 0.8475 (0.9); 0.8199 (0.4); 0.7997 (0.8); 0.7763 (0.6); 0.6947 (0.9); 0.6806 (2.0); 0.6755 (2.1); 0.6633 (1.9); 0.6575 (2.0); 0.6412 (0.6); ?0.0002 (0.9) I-036: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.2649 (1.5); 7.0173 (1.4); 7.0090 (1.4); 6.9886 (1.5); 6.9803 (1.8); 6.8697 (2.7); 6.8616 (2.5); 6.7206 (3.0); 6.6919 (2.5); 4.6410 (0.6); 4.2772 (1.4); 4.2533 (4.1); 4.2295 (4.1); 4.2058 (1.4); 3.7440 (16.0); 2.2921 (15.7); 2.1773 (0.6); 2.1667 (0.6); 2.1606 (0.5); 2.1491 (1.2); 2.1381 (0.5); 2.1317 (0.7); 2.1210 (0.6); 2.0058 (0.5); 1.3365 (4.2); 1.3128 (8.4); 1.2982 (1.0); 1.2890 (4.1); 1.2748 (0.4); 0.9816 (0.8); 0.9660 (2.1); 0.9595 (2.4); 0.9448 (1.2); 0.9377 (2.1); 0.9313 (2.1); 0.9168 (0.9); 0.7487 (0,9); 0.7292 (2.5); 0.7166 (2.2); 0.7114 (2.5); 0.6948 (0.7); ?0.0004 (1.2) I-045: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.2613 (20.6); 6.9226 (0.9); 6.9015 (1.0); 6.8941 (1.2); 6.8729 (1.2); 6.7670 (0.7); 6.7589 (0.7); 6.7394 (1.1); 6.7309 (1.2); 6.7115 (0.5); 6.7030 (0.5); 6.5329 (1.4); 6.5244 (1.3); 6.5015 (1.4); 6.4932 (1.3); 4.2976 (1.3); 4.2739 (4.0); 4.2501 (4.0); 4.2264 (1.3); 3.7548 (15.9); 2.3037 (16.0); 2.1166 (0.4); 2.1057 (0.5); 2.0879 (0.9); 2.0705 (0.5); 2.0602 (0.5); 1.5605 (2.0); 1.3403 (4.1); 1.3165 (8.4); 1.2928 (4.1); 1.2535 (0.4); 0.9211 (0.6); 0.9062 (1.7); 0.8993 (1.9); 0.8855 (1.0); 0.8776 (1.8); 0.8711 (1.7); 0.8571 (0.8); 0.7009 (0.8); 0.6864 (1.9); 0.6819 (2.0); 0.6689 (1.8); 0.6631 (2.0); 0.6472 (0.6); 0.0105 (0.6); ?0.0003 (17.5); ?0.0113 (0.8) I-046: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.3454 (1.0); 6.9787 (1.1); 6.9558 (1.4); 6.9505 (1.7); 6.9281 (1.4); 6.7873 (0.9); 6.7790 (0.9); 6.7596 (1.5); 6.7512 (1.5); 6.7313 (0.7); 6.7235 (0.6); 6.4717 (1.6); 6.4633 (1.6); 6.4370 (1.7); 6.4285 (1.5); 3.5341 (16.0); 3.3244 (8.1); 2.7273 (0.6); 2.5065 (80.2); 2.5013 (98.4); 2.4405 (0.5); 2.2714 (0.7); 2.2334 (15.9); 2.2057 (0.8); 2.1867 (1.3); 2.1706 (0.8); 2.1594 (0.7); 2.1398 (0.3); 0.9246 (0.7); 0.9097 (2.2); 0.9026 (2.4); 0.8903 (1.4); 0.8810 (2.1); 0.8743 (2.2); 0.8617 (1.0); 0.7444 (1.1); 0.7315 (2.6); 0.7258 (2.9); 0.7138 (2.5); 0.7091 (2.4); 0.6929 (0.8); ?0.0003 (10.6) I-047: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 8.1339 (0.5); 7.2049 (1.3); 7.2020 (1.5); 7.1848 (2.3); 7.1819 (2.2); 7.1303 (1.4); 7.1100 (2.3); 7.0906 (1.0); 6.7292 (1.7); 6.7264 (1.8); 6.7087 (1.6); 6.7060 (1.6); 4.2643 (1.3); 4.2466 (4.3); 4.2288 (4.4); 4.2111 (1.4); 3.6327 (16.0); 3.3252 (25.6); 2.6706 (0.4); 2.5106 (19.6); 2.5061 (42.0); 2.5016 (57.9); 2.4970 (41.3); 2.4925 (19.0); 2.2462 (15.7); 2.0753 (1.5); 1.7964 (0.5); 1.7892 (0.5); 1.7826 (0.4); 1.7751 (1.0); 1.7673 (0.3); 1.7612 (0.6); 1.7535 (0.6); 1.2278 (4.7); 1.2101 (9.9); 1.1924 (4.4); 0.9692 (0.6); 0.9581 (1.6); 0.9523 (1.9); 0.9421 (1.1); 0.9363 (1.7); 0.9305 (1.8); 0.9208 (1.0); 0.8313 (1.0); 0.8211 (1.9); 0.8166 (2.2); 0.8074 (1.8); 0.8021 (1.7); 0.7904 (0.6); ?0.0001 (6.5) I-048: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 11.3094 (1.4); 7.1150 (0.9); 7.1115 (1.1); 7.0950 (2.6); 7.0915 (2.4); 7.0765 (1.9); 7.0565 (2.4); 7.0366 (0.9); 6.5595 (1.7); 6.5560 (1.8); 6.5395 (1.7); 6.5361 (1.7); 3.5152 (16.0); 3.3282 (14.1); 2.5240 (0.4); 2.5105 (11.5); 2.5061 (24.9); 2.5016 (34.7); 2.4971 (25.5); 2.4926 (12.7); 2.2287 (14.9); 2.0755 (0.4); 1.8458 (0.5); 1.8385 (0.6); 1.8318 (0.4); 1.8247 (1.1); 1.8171 (0.4); 1.8109 (0.6); 1.8032 (0.6); 1.7895 (0.3); 1.0841 (0.6); 1.0724 (1.7); 1.0671 (1.9); 1.0585 (2.2); 1.0534 (1.9); 1.0437 (0.9); 0.9518 (0.7); 0.9422 (1.9); 0.9368 (1.6); 0.9306 (1.0); 0.9209 (1.8); 0.9154 (1.8); 0.9041 (0.5); ?0.0001 (5.7) I-051: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): ? = 7.9521 (0.6); 7.7120 (2.0); 7.7057 (2.1); 7.3323 (1.2); 7.3259 (1.1); 7.3102 (1.3); 7.3038 (1.3); 7.0092 (2.3); 6.9871 (2.0); 5.7564 (4.6); 3.6400 (9.8); 3.3895 (0.8); 3.3178 (16.0); 2.8900 (5.4); 2.7302 (4.4); 2.5188 (0.7); 2.5100 (14.8); 2.5055 (33.5); 2.5009 (47.8); 2.4963 (34.4); 2.4918 (15.9); 2.2098 (9.7); 1.5399 (0.7); 1.5278 (0.6); 1.4124 (1.3); 0.0080 (1.0); ?0.0002 (37.2); ?0.0086 (1.2) I-052: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): ? = 8.1267 (3.8); 8.1187 (3.6); 8.1077 (4.0); 8.0997 (3.4); 8.0774 (3.3); 8.0695 (3.2); 8.0587 (3.4); 8.0508 (3.0); 7.6827 (3.9); 7.6744 (6.6); 7.6714 (4.7); 7.6660 (3.8); 7.6631 (5.2); 7.6542 (2.7); 5.7556 (16.0); 5.0033 (2.3); 4.9648 (2.8); 4.6971 (3.1); 4.6585 (2.5); 3.9882 (0.6); 3.9642 (0.9); 3.9546 (1.1); 3.9465 (1.0); 3.9372 (0.8); 3.9156 (0.8); 3.9066 (1.0); 3.8963 (1.0); 3.8875 (1.0); 3.8629 (0.5); 3.4262 (1.9); 3.4128 (2.3); 3.3985 (2.0); 3.3113 (2.2); 3.2955 (4.5); 3.2795 (2.2); 2.6704 (0.6); 2.5242 (1.6); 2.5195 (2.6); 2.5108 (37.3); 2.5062 (82.3); 2.5016 (115.1); 2.4970 (81.7); 2.4924 (36.6); 2.4746 (0.9); 2.4705 (0.8); 2.4664 (0.6); 2.4394 (1.9); 2.4251 (3.6); 2.4097 (2.0); 2.3332 (0.5); 2.3287 (0.7); 2.3240 (0.5); 2.0394 (0.6); 2.0297 (0.6); 2.0220 (0.8); 2.0136 (0.8); 2.0054 (0.8); 1.9971 (0.7); 1.9549 (0.8); 1.9460 (0.8); 1.9371 (0.8); 1.9195 (0.6); 1.7864 (0.8); 1.7534 (1.9); 1.3999 (0.9); 1.3838 (1.2); 1.3683 (1.2); 1.3535 (1.2); 1.3364 (0.9); 1.3200 (0.5); 1.1760 (0.9); 0.0080 (1.6); ?0.0002 (68.5); ?0.0085 (2.4) I-053: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): ? = 7.7164 (1.0); 7.7135 (1.3); 7.6957 (1.4); 7.6925 (1.3); 7.6326 (0.8); 7.6140 (0.5); 7.4704 (1.1); 7.4515 (1.4); 7.4501 (1.4); 7.4316 (0.8); 7.3970 (1.6); 7.3906 (1.7); 7.2170 (1.0); 7.2106 (0.9); 7.1948 (1.1); 7.1885 (1.0); 6.7841 (1.8); 6.7619 (1.6); 5.8472 (3.6); 3.5674 (0.6); 3.5587 (7.7); 3.3200 (16.0); 2.5189 (0.7); 2.5102 (10.9); 2.5056 (24.0); 2.5010 (33.7); 2.4964 (23.8); 2.4918 (10.6); 2.3381 (7.5); 2.0854 (0.8); 0.0080 (0.5); ?0.0002 (21.6); ?0.0085 (0.7) I-054: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.6032 (1.4); 7.5955 (1.4); 7.5857 (1.4); 7.5779 (1.4); 7.2636 (3.9); 7.0763 (1.4); 7.0681 (1.8); 7.0591 (1.4); 5.3003 (0.6); 3.8257 (16.0); 2.7627 (1.0); 2.7453 (1.4); 2.7278 (1.1); 2.2845 (15.8); 1.2023 (7.8); 1.1849 (7.7); 1.1642 (7.8); 1.1467 (7.6); ?0.0002 (5.4) I-055: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): ? = 8.3437 (2.2); 8.3222 (2.2); 8.2377 (4.7); 8.2161 (4.9); 8.1834 (0.8); 8.1619 (0.8); 8.0720 (0.9); 7.3125 (1.6); 7.2924 (1.6); 7.1070 (3.4); 7.1055 (3.4); 7.0855 (3.3); 7.0840 (3.2); 7.0703 (0.5); 7.0482 (0.5); 5.2582 (2.9); 4.7897 (14.4); 3.5643 (16.0); 3.0798 (0.8); 2.9925 (4.4); 2.8911 (2.0); 2.7324 (1.7); 2.7309 (1.6); 2.6710 (0.7); 2.6345 (13.6); 2.6230 (13.5); 2.5247 (2.0); 2.5200 (3.1); 2.5113 (39.1); 2.5067 (86.5); 2.5021 (120.5); 2.4975 (84.6); 2.4929 (37.5); 2.4742 (0.7); 2.4698 (0.6); 2.3338 (0.6); 2.3292 (0.7); 2.3246 (0.5); 2.2491 (15.5); 0.0080 (2.1); ?0.0002 (79.8); ?0.0059 (1.3); ?0.0085 (2.6) I-056: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 8.1662 (10.9); 8.1594 (11.1); 8.1590 (10.9); 7.6243 (8.9); 7.6174 (8.3); 7.6069 (8.9); 7.6000 (8.1); 7.2654 (9.6); 5.2997 (3.6); 3.7795 (9.6); 3.7693 (14.4); 3.7653 (11.9); 3.7564 (16.0); 3.7342 (4.6); 3.7267 (4.6); 3.6006 (4.0); 3.5895 (4.8); 1.6495 (1.1); ?0.0002 (13.3) I-057: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 8.0311 (1.8); 8.0099 (1.9); 7.2611 (14.0); 7.0787 (1.5); 7.0576 (1.4); 5.2999 (3.6); 3.7629 (16.0); 3.7002 (1.4); 3.6893 (1.2); 3.6763 (0.6); 3.6327 (1.0); 3.5545 (1.2); 3.5384 (1.2); 3.5253 (1.1); 3.2237 (0.8); 3.2062 (0.8); 2.3178 (15.6); 1.5573 (1.0); 1.1427 (0.7); 1.1250 (1.4); 1.1073 (0.6); 0.0080 (0.6); ?0.0002 (19.0) I-058: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.2616 (7.0); 7.0361 (0.6); 7.0157 (0.8); 7.0088 (1.3); 6.9883 (1.4); 6.9814 (1.0); 6.9611 (0.8); 6.7993 (1.0); 6.7661 (1.3); 6.7373 (0.9); 6.5357 (1.8); 6.5083 (1.7); 4.7964 (0.5); 4.2939 (1.4); 4.2701 (4.0); 4.2464 (4.0); 4.2226 (1.4); 3.7415 (16.0); 3.6920 (0.8); 3.2482 (0.3); 2.3510 (0.8); 2.3383 (0.4); 2.2992 (15.6); 2.2198 (0.9); 2.0460 (0.4); 1.9192 (0.4); 1.9008 (0.7); 1.8903 (0.7); 1.8806 (0.6); 1.8722 (1.3); 1.8608 (0.6); 1.8533 (0.7); 1.8428 (0.7); 1.8246 (0.4); 1.6209 (0.3); 1.3410 (4.3); 1.3173 (8.4); 1.2935 (4.1); 1.2598 (0.4); 1.0546 (0.3); 1.0303 (0.7); 1.0073 (2.2); 0.9950 (2.5); 0.9891 (2.1); 0.9764 (1.2); 0.9634 (0.7); 0.9473 (0.6); 0.9367 (0.6); 0.9181 (1.2); 0.9075 (2.1); 0.8923 (1.5); 0.8785 (2.0); 0.8564 (0.6); ?0.0001 (5.9) I-059: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): ? = 8.0517 (0.8); 8.0395 (0.8); 7.9983 (2.9); 7.9946 (2.9); 7.9867 (3.1); 7.9830 (2.8); 7.7877 (2.6); 7.7752 (2.7); 7.5119 (2.3); 7.5082 (2.2); 7.4913 (3.1); 7.4876 (2.7); 7.3878 (3.4); 7.3762 (3.4); 7.3672 (2.6); 7.3557 (2.5); 7.3090 (0.7); 7.2990 (0.6); 7.0045 (2.1); 6.9919 (2.0); 5.7564 (1.0); 5.0473 (0.7); 5.0015 (1.2); 4.8911 (16.0); 4.7187 (1.6); 4.6677 (9.1); 4.1039 (0.8); 4.0863 (0.7); 3.7230 (3.4); 3.5454 (1.6); 3.5287 (3.5); 3.5122 (1.7); 3.4314 (1.5); 3.4070 (1.2); 3.3167 (1.1); 3.3030 (14.8); 3.2548 (1.5); 3.2359 (1.0); 3.1588 (2.7); 3.0918 (1.0); 3.0800 (0.5); 3.0638 (0.6); 3.0142 (7.1); 3.0056 (0.9); 2.9897 (0.6); 2.9753 (0.5); 2.9572 (3.8); 2.7368 (0.5); 2.6989 (2.0); 2.6824 (4.3); 2.6752 (1.4); 2.6709 (1.9); 2.6660 (3.1); 2.6093 (63.9); 2.5245 (4.8); 2.5192 (9.8); 2.5111 (96.4); 2.5065 (211.8); 2.5020 (295.1); 2.4974 (209.1); 2.4928 (94.0); 2.4727 (0.7); 2.4635 (0.7); 2.4451 (1.5); 2.4315 (13.7); 2.4162 (2.1); 2.3851 (1.0); 2.3455 (1.5); 2.3301 (3.2); 2.3246 (1.4); 2.3079 (1.0); 2.1275 (1.7); 2.1245 (1.8); 2.0657 (3.2); 1.9206 (0.6); 1.8996 (1.2); 1.8868 (1.3); 1.7905 (2.2); 1.7820 (5.2); 1.7647 (6.3); 1.7550 (4.0); 1.6419 (1.5); 1.5499 (2.6); 1.5342 (2.6); 1.2163 (0.8); 1.2039 (0.7); 1.1987 (1.8); 1.1808 (1.0); 1.1115 (1.4); 1.0936 (2.0); 1.0755 (0.8); 1.0044 (0.8); 0.0080 (3.6); 0.0056 (1.0); ?0.0002 (138.6); ?0.0059 (2.5); ?0.0085 (4.8); ?0.1490 (0.5) I-060: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.7981 (2.9); 7.7938 (0.9); 7.7816 (1.0); 7.7773 (3.1); 7.3309 (2.6); 7.3247 (2.7); 7.2601 (17.1); 7.2425 (2.3); 7.2224 (2.1); 7.0882 (1.6); 7.0820 (1.4); 7.0663 (1.7); 7.0601 (1.6); 6.6319 (2.9); 6.6100 (2.6); 5.2996 (1.6); 4.9705 (0.6); 3.7024 (16.0); 2.4528 (15.7); 2.3901 (9.2); 1.5424 (11.4); 0.0079 (0.9); ?0.0002 (25.6); ?0.0085 (0.6) I-061: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.4165 (0.8); 7.4101 (1.0); 7.4052 (2.6); 7.3989 (2.7); 7.2620 (6.8); 7.1404 (1.5); 7.1342 (1.4); 7.1185 (1.9); 7.1123 (1.7); 6.9565 (3.0); 6.9346 (2.4); 6.8416 (0.7); 6.8197 (0.6); 4.5128 (1.8); 3.7336 (16.0); 3.0024 (9.7); 2.9511 (1.7); 2.9386 (1.8); 2.9254 (9.6); 2.2747 (15.4); 1.5703 (2.5); ?0.0002 (10.2) I-062: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.4230 (3.0); 7.4168 (5.7); 7.4103 (3.0); 7.2616 (14.5); 7.2391 (1.4); 7.2330 (1.4); 7.2172 (1.6); 7.2110 (1.5); 7.1517 (1.6); 7.1454 (1.5); 7.1298 (1.8); 7.1236 (1.7); 6.9154 (3.2); 6.8935 (2.7); 6.8414 (2.8); 6.8194 (2.5); 5.2998 (1.8); 4.6658 (0.5); 4.5124 (7.6); 4.2646 (1.2); 4.2467 (4.2); 4.2286 (5.1); 4.2093 (4.0); 4.1915 (1.3); 3.6930 (15.5); 3.2515 (0.6); 2.9514 (6.5); 2.9390 (6.4); 2.4282 (16.0); 1.5809 (1.4); 1.3493 (4.9); 1.3464 (4.8); 1.3316 (9.9); 1.3287 (9.6); 1.3139 (4.8); 1.3110 (4.7); 0.0082 (0.7); ?0.0002 (19.3) I-066: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.2612 (26.5); 7.0209 (0.7); 6.9954 (1.8); 6.9694 (1.5); 6.9328 (1.7); 6.9100 (1.0); 6.6151 (1.4); 6.5901 (1.2); 5.1059 (0.4); 4.2391 (1.2); 4.2154 (4.0); 4.1916 (4.1); 4.1678 (1.3); 3.7330 (16.0); 3.2454 (0.6); 2.4359 (11.0); 2.4168 (0.8); 2.2736 (16.0); 2.0108 (0.8); 1.6590 (0.5); 1.6498 (0.5); 1.6308 (0.9); 1.6118 (0.5); 1.6022 (0.5); 1.5619 (3.7); 1.3143 (4.2); 1.2905 (8.6); 1.2667 (4.2); 1.2527 (0.8); 0.9336 (0.6); 0.9186 (1.4); 0.9117 (1.8); 0.8982 (1.0); 0.8896 (1.5); 0.8827 (1.6); 0.8699 (0.8); 0.7744 (0.9); 0.7609 (1.8); 0.7551 (2.2); 0.7418 (1.8); 0.7201 (0.5); 0.0690 (1.5); 0.0106 (0.8); ?0.0002 (21.5); ?0.0111 (0.8) I-067: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.2627 (22.3); 7.2445 (4.9); 5.9932 (1.5); 5.9890 (1.5); 5.4761 (1.5); 5.4720 (1.5); 4.3224 (0.7); 4.3046 (2.1); 4.2911 (1.0); 4.2869 (2.2); 4.2801 (0.5); 4.2734 (2.3); 4.2692 (1.1); 4.2613 (1.0); 4.2592 (1.0); 4.2556 (2.4); 4.2519 (0.6); 4.2433 (2.3); 4.2414 (2.2); 4.2378 (1.0); 4.2254 (2.4); 4.2238 (2.1); 4.2074 (1.0); 3.8893 (0.6); 3.7513 (1.4); 3.7411 (2.6); 3.7323 (3.3); 3.7280 (3.7); 3.7204 (3.6); 3.7069 (4.1); 3.7007 (1.6); 3.6946 (3.4); 3.6820 (2.8); 3.6719 (1.6); 3.6592 (3.2); 3.6504 (1.6); 3.6459 (2.2); 3.6353 (1.2); 3.5529 (1.2); 3.5460 (2.9); 3.5416 (1.8); 3.5372 (2.0); 3.5334 (2.6); 3.5219 (1.9); 3.2349 (4.1); 2.4466 (16.0); 2.0106 (0.5); 2.0063 (0.5); 1.9825 (1.0); 1.9222 (5.6); 1.9094 (0.8); 1.7599 (11.3); 1.5388 (0.5); 1.5088 (0.8); 1.3562 (2.4); 1.3387 (5.6); 1.3330 (1.2); 1.3269 (0.9); 1.3215 (6.3); 1.3149 (1.3); 1.3109 (4.5); 1.3038 (3.0); 1.2930 (8.2); 1.2844 (1.6); 1.2753 (4.2); 1.2650 (1.3); 1.2545 (1.9); 1.2332 (0.6); 1.2156 (0.6); 0.0080 (0.9); ?0.0002 (34.1); ?0.0085 (1.1) I-068: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.7316 (0.6); 7.7286 (0.6); 7.4381 (1.0); 7.4295 (6.5); 7.4240 (2.2); 7.4184 (1.0); 7.4102 (5.5); 7.4069 (7.1); 7.3946 (2.9); 7.3874 (6.6); 7.3857 (5.9); 7.3797 (3.4); 7.3736 (3.0); 7.3689 (2.6); 7.3631 (5.9); 7.3551 (2.1); 7.3485 (1.6); 7.3211 (1.0); 7.2988 (1.0); 7.2619 (35.9); 6.8865 (1.2); 6.8693 (0.5); 6.8639 (1.1); 6.8418 (1.7); 6.8386 (2.6); 6.8306 (2.9); 6.8218 (8.9); 6.8163 (4.8); 6.8088 (8.6); 6.8045 (4.3); 6.7993 (7.6); 6.7917 (2.8); 6.7862 (6.0); 6.7777 (0.8); 6.7310 (1.5); 6.7087 (1.0); 6.5174 (0.6); 5.0762 (2.9); 5.0331 (1.0); 5.0273 (1.1); 5.0069 (0.7); 4.6590 (0.6); 4.6411 (4.2); 4.6262 (11.5); 4.6125 (0.6); 4.5900 (1.1); 4.4666 (10.6); 4.4542 (2.3); 4.4388 (1.0); 4.4209 (1.1); 4.3339 (0.6); 4.3161 (0.8); 4.3006 (0.6); 3.8856 (4.6); 3.6868 (15.7); 3.5306 (4.9); 3.4634 (2.7); 3.4221 (0.5); 3.4040 (1.1); 3.3935 (0.7); 3.3815 (1.8); 3.3633 (1.5); 3.3409 (0.7); 3.3165 (0.6); 3.2976 (0.5); 3.2825 (0.6); 3.2667 (0.6); 3.2436 (2.8); 3.2342 (2.1); 3.2228 (1.5); 3.0737 (0.9); 2.9733 (0.7); 2.9202 (9.2); 2.9077 (9.2); 2.5669 (0.5); 2.5398 (4.2); 2.4762 (2.6); 2.4519 (1.1); 2.3911 (0.6); 2.3528 (16.0); 2.3399 (1.8); 2.2477 (2.4); 2.2446 (2.3); 2.1001 (14.7); 2.0550 (1.4); 2.0454 (1.5); 2.0420 (1.2); 1.7497 (0.5); 1.7347 (0.6); 1.6904 (0.6); 1.6570 (0.9); 1.6424 (0.8); 1.4318 (2.8); 1.4136 (2.3); 1.3958 (1.2); 1.3917 (0.8); 1.3817 (1.2); 1.3738 (1.4); 1.3638 (2.4); 1.3559 (0.8); 1.3460 (1.2); 1.3314 (0.9); 1.3141 (0.6); 1.2962 (1.1); 1.2767 (0.7); 1.2724 (0.5); 1.2587 (1.1); 1.2411 (0.5); 1.2281 (1.2); 1.2217 (0.6); 1.2104 (2.2); 1.1927 (1.1); 1.1508 (1.1); 1.1330 (2.2); 1.1153 (1.1); 0.0080 (1.4); ?0.0002 (51.4); ?0.0085 (1.6) I-069: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.4136 (4.0); 7.4081 (1.1); 7.3967 (1.1); 7.3911 (4.3); 7.2652 (0.5); 7.2604 (85.1); 7.2562 (1.8); 6.9041 (4.2); 6.8985 (1.2); 6.8872 (1.1); 6.8816 (3.9); 4.2892 (1.2); 4.2713 (4.0); 4.2535 (4.0); 4.2357 (1.3); 3.7405 (16.0); 2.3054 (15.6); 1.5432 (5.3); 1.3335 (4.2); 1.3157 (8.8); 1.2979 (4.1); 1.2553 (0.9); 0.0080 (3.0); 0.0056 (0.5); 0.0047 (0.8); ?0.0002 (109.9); ?0.0058 (1.5); ?0.0067 (1.2); ?0.0084 (3.2); ?0.0106 (0.7) I-070: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.0904 (1.4); 7.0843 (1.4); 7.0630 (2.3); 7.0566 (2.3); 6.9916 (3.6); 6.9639 (2.1); 6.8695 (3.8); 6.8632 (3.4); 4.2746 (1.4); 4.2511 (4.3); 4.2275 (4.4); 4.2038 (1.6); 3.6576 (16.0); 3.3356 (19.2); 2.7285 (0.4); 2.5027 (57.8); 2.2504 (15.9); 2.0663 (0.4); 2.0505 (0.7); 2.0388 (0.8); 2.0320 (0.8); 2.0218 (1.4); 2.0040 (0.9); 1.9940 (0.8); 1.9761 (0.4); 1.5069 (0.4); 1.4975 (0.3); 1.2334 (5.0); 1.2098 (9.4); 1.1862 (4.8); 0.9458 (0.9); 0.9308 (2.5); 0.9239 (2.8); 0.9106 (2.1); 0.9028 (2.6); 0.8959 (2.6); 0.8831 (1.3); 0.8330 (0.4); 0.7249 (1.2); 0.7063 (3.2); 0.6946 (3.0); 0.6892 (3.0); 0.6726 (1.0); ?0.0003 (7.1) I-071: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.0028 (1.1); 6.9966 (1.0); 6.9752 (2.9); 6.9691 (2.8); 6.9483 (4.0); 6.9207 (1.4); 6.6045 (3.8); 6.5984 (3.2); 4.0408 (0.4); 4.0171 (0.4); 3.5371 (15.7); 3.3517 (1.0); 3.3011 (0.8); 2.5076 (14.5); 2.5024 (17.2); 2.2660 (0.7); 2.2315 (16.0); 2.2034 (1.5); 2.1926 (1.3); 2.1750 (0.8); 1.9896 (1.9); 1.2347 (0.4); 1.1982 (0.5); 1.1744 (0.9); 1.1507 (0.5); 0.9601 (0.7); 0.9452 (2.2); 0.9382 (2.5); 0.9250 (1.6); 0.9170 (2.4); 0.9102 (2.4); 0.8974 (1.2); 0.8761 (0.4); 0.8489 (0.4); 0.7688 (1.1); 0.7554 (2.7); 0.7501 (3.0); 0.7383 (2.9); 0.7329 (2.8); 0.7167 (1.1); ?0.0005 (0.9) I-072: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.6064 (0.5); 7.2606 (98.0); 7.0184 (0.8); 6.9932 (2.2); 6.9672 (1.7); 6.9181 (2.5); 6.8935 (1.4); 6.5291 (1.8); 6.5035 (1.6); 6.0164 (5.1); 4.1332 (0.3); 4.1099 (0.3); 3.6841 (12.4); 2.4516 (16.0); 2.3548 (12.4); 2.0456 (1.6); 1.7183 (0.6); 1.6952 (1.1); 1.6717 (0.6); 1.6489 (0.3); 1.5494 (28.4); 1.2833 (0.5); 1.2595 (1.0); 1.2359 (0.4); 1.0066 (0.6); 0.9845 (2.5); 0.9712 (1.4); 0.9618 (2.0); 0.9563 (2.1); 0.9436 (1.0); 0.9232 (0.3); 0.8764 (1.1); 0.8633 (2.5); 0.8577 (2.7); 0.8446 (2.4); 0.8227 (0.6); 0.1952 (0.3); 0.0691 (1.5); 0.0106 (3.4); ?0.0001 (87.0); ?0.0111 (3.6); ?0.1986 (0.4) I-073: .sup.1H-NMR (300.1 MHz, CDCl3): ? = 7.2615 (15.5); 7.0278 (0.4); 7.0005 (1.1); 6.9799 (1.1); 6.9734 (0.8); 6.9525 (0.6); 6.7719 (1.0); 6.7390 (1.2); 6.7099 (0.8); 6.4513 (1.6); 6.4239 (1.5); 6.3453 (0.7); 5.3015 (0.3); 3.6686 (14.9); 2.3537 (16.0); 2.0070 (0.5); 1.9526 (0.5); 1.9423 (0.6); 1.9339 (0.4); 1.9241 (1.1); 1.9135 (0.4); 1.9054 (0.6); 1.8953 (0.6); 1.6015 (1.1); 1.0895 (0.5); 1.0675 (2.1); 1.0548 (2.3); 1.0496 (2.0); 1.0358 (0.8); 0.9560 (0.7); 0.9425 (1.7); 0.9150 (1.7); 0.8941 (0.4); 0.0105 (0.5); ?0.0002 (12.1); ?0.0111 (0.5) I-074: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.4179 (1.6); 7.3056 (1.0); 7.2869 (1.3); 7.2734 (1.5); 7.2610 (0.4); 7.2043 (0.6); 7.1892 (3.2); 7.1713 (5.7); 7.1568 (3.1); 7.1460 (0.5); 7.1416 (0.5); 7.0403 (0.4); 7.0283 (2.0); 7.0172 (1.3); 7.0142 (1.3); 7.0054 (1.0); 6.9959 (1.4); 6.9250 (1.7); 4.2772 (1.5); 4.2535 (4.4); 4.2299 (4.4); 4.2063 (1.5); 3.6365 (16.0); 3.3457 (6.4); 2.5084 (8.8); 2.5027 (10.6); 2.4970 (7.3); 2.2525 (15.9); 1.9899 (1.2); 1.2381 (4.8); 1.2145 (9.7); 1.1909 (4.4); 1.1744 (0.8); 1.1507 (0.4); ?0.0001 (0.6) I-075: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.4008 (3.1); 7.3952 (1.0); 7.3837 (1.0); 7.3782 (3.5); 7.3594 (0.6); 7.2600 (55.5); 6.8662 (3.3); 6.8605 (0.9); 6.8492 (0.9); 6.8437 (3.2); 5.0820 (1.1); 3.7427 (13.0); 3.3215 (1.8); 2.7545 (0.8); 2.7371 (1.2); 2.7196 (0.9); 2.2432 (12.8); 1.5365 (16.0); 1.2332 (15.6); 1.2158 (14.8); 0.0079 (2.6); ?0.0002 (81.1); ?0.0085 (2.3) I-076: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.4312 (1.9); 7.4256 (0.5); 7.4141 (0.6); 7.4085 (2.0); 7.2601 (28.6); 6.8135 (1.9); 6.8078 (0.5); 6.7964 (0.5); 6.7908 (1.7); 4.4652 (3.0); 2.9226 (2.8); 2.9101 (2.7); 1.5385 (16.0); 0.0080 (1.4); ?0.0002 (41.6); ?0.0084 (1.0) I-077: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.2611 (33.4); 7.0528 (2.6); 6.9929 (16.0); 6.9653 (2.8); 6.9183 (2.9); 4.6901 (1.0); 4.6403 (2.4); 4.5921 (2.0); 4.4964 (5.3); 4.4816 (1.4); 4.2957 (0.7); 4.2778 (0.7); 3.7474 (0.9); 3.4401 (0.6); 3.3878 (0.6); 3.3654 (0.7); 3.0815 (1.7); 3.0179 (1.4); 2.9469 (6.1); 2.9346 (6.2); 2.3837 (0.6); 1.7117 (0.9); 1.4012 (0.7); 1.3286 (0.8); 1.3107 (1.6); 1.2930 (1.0); 1.2761 (2.3); 1.2588 (4.7); 1.2415 (2.2); 0.0080 (1.2); ?0.0002 (47.3); ?0.0083 (2.5); ?0.0277 (0.6) I-078: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.4309 (0.8); 7.4134 (0.6); 7.4081 (0.9); 7.2596 (34.3); 6.8131 (0.8); 6.7905 (0.6); 4.4650 (1.2); 3.7461 (1.6); 2.9226 (1.1); 2.9102 (1.1); 2.2749 (1.6); 1.5357 (16.0); 0.0079 (1.5); ?0.0002 (49.9); ?0.0086 (1.6) I-079: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 7.5914 (0.9); 7.5874 (1.0); 7.5715 (1.0); 7.5675 (1.0); 7.2609 (23.0); 7.2299 (0.5); 7.2153 (0.7); 7.2135 (0.7); 7.2113 (0.7); 7.2095 (0.7); 7.1950 (0.7); 7.1910 (0.7); 7.0232 (0.6); 7.0196 (0.7); 7.0046 (0.7); 7.0034 (0.7); 7.0010 (0.8); 6.9998 (0.8); 6.9848 (0.5); 6.9812 (0.6); 6.9158 (1.1); 6.9123 (1.0); 6.8955 (1.0); 6.8919 (0.9); 4.3029 (1.0); 4.2851 (3.1); 4.2673 (3.2); 4.2495 (1.0); 3.7400 (12.4); 2.3058 (12.1); 1.5529 (16.0); 1.3462 (3.2); 1.3284 (6.8); 1.3105 (3.2); 0.0080 (1.0); 0.0023 (1.3); ?0.0002 (33.7); ?0.0058 (0.6); ?0.0067 (0.5); ?0.0084 (1.1) I-081: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.4168 (1.4); 7.2999 (0.8); 7.2916 (0.6); 7.2837 (0.9); 7.2682 (1.4); 7.2015 (0.4); 7.1854 (1.8); 7.1811 (2.0); 7.1769 (1.9); 7.1696 (4.8); 7.1573 (1.8); 7.1528 (2.2); 7.1496 (2.0); 7.1332 (0.6); 7.0025 (1.8); 6.9932 (1.1); 6.9863 (1.2); 6.9782 (1.0); 6.9701 (1.4); 6.9236 (1.6); 3.6302 (15.7); 3.5655 (0.3); 3.5457 (0.4); 3.5266 (0.4); 3.5059 (0.4); 3.3338 (290.0); 3.1488 (0.4); 2.7336 (0.6); 2.7280 (0.6); 2.7218 (0.5); 2.5077 (62.4); 2.5020 (75.5); 2.4962 (51.1); 2.4266 (0.6); 2.2715 (1.0); 2.2534 (16.0); 2.2125 (15.1); 2.0751 (1.3); 0.0000 (15.6); ?0.0111 (0.4) I-082: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.8351 (0.6); 7.5845 (1.1); 7.3923 (0.5); 7.3325 (0.8); 7.2391 (2.0); 7.2350 (2.0); 7.2131 (2.6); 7.2089 (2.6); 7.1979 (1.4); 7.1721 (1.5); 7.1587 (1.2); 7.1532 (1.2); 7.1413 (1.5); 7.1333 (2.6); 7.1280 (2.1); 7.1070 (2.1); 7.1013 (1.7); 7.0877 (0.7); 7.0601 (2.1); 7.0558 (2.0); 7.0348 (2.2); 7.0303 (2.0); 7.0090 (1.0); 7.0044 (1.1); 6.9776 (0.6); 6.8907 (0.5); 6.8445 (0.4); 6.8277 (2.9); 6.8228 (2.6); 6.8008 (2.4); 6.7959 (2.0); 4.7661 (2.5); 3.6210 (1.1); 3.5625 (0.6); 3.4959 (22.1); 3.4703 (1.9); 3.3591 (2.7); 3.1475 (0.4); 3.0203 (0.4); 3.0076 (0.4); 2.7338 (1.0); 2.7278 (1.3); 2.7217 (1.0); 2.5132 (83.6); 2.5077 (147.6); 2.5019 (184.4); 2.4961 (129.6); 2.2776 (1.3); 2.2717 (1.6); 2.2658 (1.2); 2.1707 (16.0); 2.1174 (0.9); 2.0760 (0.4); 1.9894 (0.4); 1.7940 (0.6); 1.1555 (0.3); 0.0103 (2.0); ?0.0003 (46.8); ?0.0112 (2.7) I-083: .sup.1H-NMR (400.6 MHz, CDCl3): ? = 8.0885 (1.7); 8.0768 (1.8); 7.7130 (2.3); 7.7066 (2.2); 7.2638 (15.4); 7.2321 (0.9); 7.2199 (0.9); 7.2110 (1.2); 7.1988 (1.2); 7.0840 (1.3); 7.0795 (1.2); 7.0628 (1.0); 7.0584 (0.9); 5.3003 (3.0); 5.1598 (0.6); 3.7092 (16.0); 3.2470 (0.9); 3.2067 (0.7); 2.3713 (14.6); 2.0890 (15.2); 2.0625 (0.6); 2.0495 (0.6); 1.9134 (0.8); 1.2557 (1.6); 0.0698 (0.8); ?0.0002 (16.9) I-084: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 11.2324 (1.1); 7.0302 (0.4); 7.0234 (0.4); 6.9957 (1.6); 6.9870 (1.8); 6.9760 (4.0); 6.9519 (2.4); 6.9436 (1.4); 6.7409 (1.4); 6.7280 (0.9); 6.7206 (1.3); 6.7119 (0.8); 4.4003 (0.4); 4.0407 (0.5); 4.0166 (0.4); 3.9917 (0.3); 3.9297 (0.3); 3.8865 (0.4); 3.8791 (0.4); 3.8716 (0.4); 3.8470 (0.4); 3.8333 (0.4); 3.7912 (0.4); 3.7104 (0.5); 3.6771 (0.5); 3.6310 (0.6); 3.6074 (0.6); 3.5525 (0.8); 3.4776 (19.0); 3.4477 (1.5); 3.3306 (794.9); 2.7336 (3.0); 2.7277 (3.8); 2.7216 (2.8); 2.6934 (0.6); 2.6773 (0.6); 2.6248 (0.7); 2.5134 (253.8); 2.5076 (463.2); 2.5017 (593.0); 2.4957 (417.0); 2.4902 (205.8); 2.2833 (2.6); 2.2776 (3.9); 2.2715 (4.6); 2.2654 (3.7); 2.2383 (1.0); 2.2107 (16.0); 2.1792 (1.3); 2.1689 (1.2); 2.1508 (1.6); 2.1331 (1.0); 2.1224 (0.9); 2.1046 (0.5); 2.0746 (2.5); 1.9888 (0.8); 1.2353 (1.0); 1.1742 (0.5); 0.8908 (0.5); 0.8756 (1.8); 0.8684 (2.3); 0.8556 (1.4); 0.8473 (2.1); 0.8401 (2.3); 0.8276 (1.1); 0.7108 (0.8); 0.6979 (2.3); 0.6916 (2.7); 0.6806 (2.5); 0.6740 (2.4); 0.6584 (0.8); 0.0106 (1.8); ?0.0003 (81.7); ?0.0113 (5.3); ?0.0627 (0.8); ?0.1991 (0.5) I-085: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.1314 (0.4); 7.1042 (1.1); 7.0803 (2.7); 7.0725 (1.6); 7.0600 (1.3); 7.0525 (0.7); 7.0443 (1.4); 7.0382 (1.3); 7.0168 (0.6); 7.0109 (0.4); 6.7799 (1.5); 6.7581 (1.3); 4.2063 (1.4); 4.1826 (4.3); 4.1590 (4.4); 4.1354 (1.5); 3.6317 (16.0); 3.3597 (18.4); 2.5073 (24.7); 2.5014 (31.8); 2.4956 (23.1); 2.4022 (0.3); 2.1879 (16.0); 2.0743 (2.2); 1.9778 (0.6); 1.9672 (0.7); 1.9497 (1.2); 1.9326 (0.7); 1.9217 (0.6); 1.2269 (4.7); 1.2032 (9.5); 1.1796 (4.6); 0.9143 (0.8); 0.8996 (2.1); 0.8921 (2.3); 0.8786 (1.3); 0.8712 (2.1); 0.8640 (2.1); 0.8509 (0.9); 0.7078 (1.0); 0.6945 (2.5); 0.6882 (2.5); 0.6774 (2.4); 0.6709 (2.4); 0.6552 (0.7); ?0.0001 (6.1) I-086: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.5887 (3.0); 7.5604 (3.5); 7.2506 (1.8); 7.2428 (2.2); 7.2223 (1.3); 7.2145 (2.3); 7.1976 (4.0); 7.1900 (2.6); 5.7585 (1.7); 4.2962 (1.3); 4.2725 (4.3); 4.2489 (4.2); 4.2252 (1.4); 4.0408 (0.5); 4.0168 (0.5); 3.6557 (15.9); 3.4398 (0.4); 3.3469 (47.9); 3.2590 (0.5); 3.2317 (0.4); 2.7315 (0.5); 2.5828 (0.4); 2.5132 (28.5); 2.5075 (53.6); 2.5017 (68.8); 2.4958 (47.9); 2.2621 (16.0); 2.0751 (3.4); 1.9890 (1.9); 1.2447 (4.5); 1.2211 (9.5); 1.1977 (4.8); 1.1744 (1.2); 1.1508 (0.8); ?0.0001 (8.3); ?0.0110 (0.4) I-087: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 11.5141 (0.4); 7.9297 (1.2); 7.9087 (1.4); 7.9048 (1.3); 7.8838 (1.1); 7.1294 (0.6); 7.1112 (0.7); 7.0996 (0.7); 7.0817 (0.6); 3.5262 (16.0); 3.3473 (233.5); 2.6719 (0.5); 2.6673 (0.4); 2.5117 (28.9); 2.5074 (59.3); 2.5030 (79.7); 2.4985 (57.7); 2.4943 (27.5); 2.3345 (0.4); 2.3299 (0.5); 2.3256 (0.4); 2.2234 (14.2); 1.2346 (0.5); 1.1055 (0.5); 0.0079 (0.8); ?0.0001 (19.1); ?0.0084 (0.7) I-088: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.7381 (1.2); 7.7182 (1.1); 7.7093 (1.4); 7.6885 (1.1); 7.0258 (0.9); 7.0168 (2.2); 7.0046 (0.5); 6.9858 (4.4); 6.9765 (1.0); 6.9583 (1.1); 6.9490 (0.7); 6.7757 (0.4); 5.2607 (0.4); 5.0875 (0.4); 4.9034 (0.5); 4.7591 (0.4); 4.2964 (1.3); 4.2727 (4.2); 4.2491 (4.3); 4.2255 (1.4); 3.6580 (16.0); 3.3389 (142.3); 3.1482 (0.8); 3.0308 (1.2); 3.0024 (0.8); 2.5085 (23.2); 2.5027 (29.5); 2.4971 (21.0); 2.2620 (16.0); 1.9905 (0.4); 1.9733 (0.4); 1.2459 (4.6); 1.2223 (9.5); 1.1987 (4.3); ?0.0001 (9.2) I-089: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.7273 (0.9); 7.7070 (1.0); 7.6964 (1.2); 7.6858 (0.4); 7.6762 (0.9); 6.9933 (0.4); 6.9838 (1.2); 6.9753 (1.4); 6.9673 (1.6); 6.9609 (1.4); 6.9564 (1.3); 6.9517 (0.6); 6.9422 (1.3); 6.9331 (2.2); 3.6641 (13.8); 3.3303 (14.9); 2.8603 (0.4); 2.8372 (1.1); 2.8139 (1.5); 2.7908 (1.1); 2.7675 (0.4); 2.5145 (3.6); 2.5086 (6.8); 2.5027 (8.9); 2.4968 (6.2); 2.2131 (13.7); 1.2351 (0.6); 1.1419 (16.0); 1.1187 (15.5); 1.0419 (0.5); 1.0192 (0.4); ?0.0001 (4.0) I-090: .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): ? = 7.1594 (0.7); 7.1526 (0.7); 7.1369 (1.4); 7.1301 (1.3); 7.1144 (0.7); 7.1077 (0.7); 6.6892 (1.0); 6.6640 (1.0); 4.8864 (0.7); 3.5267 (16.0); 3.3207 (4.4); 2.5054 (11.4); 2.5010 (15.1); 2.4965 (11.3); 2.4924 (5.8); 2.2048 (13.8); ?0.0002 (4.2) I-091: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 7.7092 (0.3); 7.6756 (3.6); 7.6624 (0.3); 7.6543 (3.7); 7.0807 (1.9); 7.0748 (2.0); 7.0594 (1.8); 7.0536 (1.9); 6.8849 (3.5); 6.8790 (3.2); 4.2395 (0.4); 4.2231 (0.8); 4.2067 (0.4); 3.5402 (16.0); 3.3701 (1.8); 3.3305 (158.4); 3.3061 (2.0); 2.5107 (8.0); 2.5062 (15.6); 2.5016 (20.7); 2.4970 (14.5); 2.4925 (6.5); 2.2386 (15.8); 1.9877 (0.4); 1.2356 (0.8); 0.9308 (0.7); 0.9124 (1.4); 0.8939 (0.6); ?0.0002 (1.4) I-092: .sup.1H-NMR (300.1 MHz, d.sub.6-DMSO): ? = 7.7042 (2.7); 7.6759 (3.0); 7.1557 (1.6); 7.1479 (1.9); 7.1274 (1.3); 7.1197 (2.0); 7.0935 (3.5); 7.0859 (2.5); 3.6653 (13.7); 3.3283 (12.2); 2.8659 (0.4); 2.8426 (1.1); 2.8194 (1.5); 2.7962 (1.1); 2.7731 (0.4); 2.5145 (2.6); 2.5088 (4.8); 2.5029 (6.0); 2.4969 (4.2); 2.2154 (13.6); 1.2344 (0.6); 1.1459 (16.0); 1.1227 (15.4); 1.0943 (0.3); 1.0693 (0.3); 1.0425 (0.7); 1.0198 (0.6); ?0.0001 (2.7) I-093: .sup.1H-NMR (300.0 MHz, d.sub.6-DMSO): ? = 7.9810 (1.3); 7.9529 (1.5); 7.9476 (1.5); 7.9197 (1.2); 7.3657 (1.3); 7.3417 (1.3); 7.3272 (1.3); 7.3031 (1.2); 4.3039 (1.4); 4.2802 (4.3); 4.2566 (4.3); 4.2330 (1.3); 3.6496 (16.0); 3.3961 (0.3); 3.3694 (0.8); 3.3163 (204.7); 2.5129 (10.1); 2.5070 (18.7); 2.5011 (24.2); 2.4953 (16.7); 2.2574 (15.8); 2.0716 (1.2); 1.2567 (4.6); 1.2331 (10.1); 1.2095 (4.4); ?0.0002 (5.8) I-094: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 7.9742 (1.0); 7.9531 (1.1); 7.9492 (1.2); 7.9285 (1.0); 7.3186 (1.0); 7.3006 (1.0); 7.2895 (1.1); 7.2716 (1.0); 3.6541 (14.0); 3.3810 (0.5); 3.3439 (277.7); 2.8683 (0.4); 2.8507 (1.1); 2.8333 (1.5); 2.8159 (1.2); 2.7987 (0.5); 2.6719 (0.4); 2.5117 (19.9); 2.5073 (42.2); 2.5029 (58.1); 2.4984 (43.0); 2.4940 (21.5); 2.3298 (0.3); 2.2129 (13.8); 1.7535 (0.7); 1.1557 (16.0); 1.1383 (15.8); 1.0646 (0.4); 1.0471 (0.4); 0.0080 (0.8); ?0.0001 (20.2); ?0.0084 (0.9) I-095: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 7.5739 (2.8); 7.5524 (3.0); 7.2232 (1.6); 7.2173 (1.8); 7.2017 (1.4); 7.1959 (1.6); 7.1411 (3.2); 7.1354 (2.6); 5.3215 (0.4); 4.2216 (0.5); 3.6619 (14.1); 3.3292 (92.2); 3.2893 (1.0); 2.8587 (0.4); 2.8412 (1.1); 2.8238 (1.5); 2.8063 (1.1); 2.7890 (0.4); 2.5105 (18.1); 2.5062 (35.5); 2.5017 (46.9); 2.4973 (33.4); 2.4929 (15.5); 2.2377 (0.4); 2.2153 (14.0); 1.2338 (0.8); 1.1394 (16.0); 1.1220 (15.6); 1.0999 (1.1); 1.0830 (1.0); 1.0344 (0.9); 1.0174 (0.9); 0.9304 (0.4); 0.9119 (0.8); 0.8934 (0.4); 0.0080 (1.1); ?0.0002 (26.5); ?0.0084 (1.1) I-096: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 11.5859 (0.6); 7.5335 (3.5); 7.5278 (3.4); 7.4356 (0.4); 7.4299 (0.4); 7.2522 (0.3); 7.2466 (0.4); 7.0249 (2.7); 7.0193 (2.5); 4.9398 (1.0); 3.9021 (0.3); 3.6544 (0.6); 3.5422 (16.0); 3.3317 (140.5); 2.6714 (0.3); 2.5107 (22.5); 2.5063 (44.9); 2.5018 (60.2); 2.4973 (42.9); 2.4930 (20.0); 2.3286 (0.4); 2.2337 (14.7); 2.1044 (0.5); 1.9891 (0.3); 0.0080 (1.7); ?0.0002 (39.8); ?0.0084 (1.6) I-097: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): ? = 7.6540 (3.4); 7.6484 (3.5); 7.2822 (3.5); 7.2765 (3.5); 4.2976 (1.4); 4.2799 (4.3); 4.2622 (4.3); 4.2446 (1.4); 3.6544 (16.0); 3.3437 (457.2); 2.6721 (0.5); 2.5071 (55.8); 2.5030 (69.7); 2.4990 (50.8); 2.3299 (0.4); 2.2701 (15.7); 2.0768 (0.9); 1.2451 (4.6); 1.2273 (9.3); 1.2097 (4.3); 0.0000 (10.5)

    [0211] The present invention furthermore provides the use of one or more compounds of the general formula (I), salts or N-oxides thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-106), salts or N-oxides thereof, in each case as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamental plants.

    [0212] The present invention furthermore provides a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount [0213] of one or more compounds of the general formula (I), salts or N-oxides thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-106), salts or N-oxides thereof, in each case as defined above, or [0214] of a composition according to the invention, as defined below, is applied to the (harmful) plants, seeds of (harmful) plants, the soil in which or on which the (harmful) plants grow or the area under cultivation.

    [0215] The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount [0216] of one or more compounds of the general formula (I), salts or N-oxides thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-106), salts or N-oxides thereof, in each case as defined above, or [0217] of a composition according to the invention, as defined below, [0218] is applied to unwanted plants (for example harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e., plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).

    [0219] The present invention furthermore also provides methods for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount [0220] of one or more compounds of the general formula (I), salts or N-oxides thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-001) to (I-106), salts or N-oxides thereof, in each case as defined above, or [0221] of a composition according to the invention, as defined below, [0222] is applied to the plant, the seed of the plant (i.e., plant seed, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e., the area on which the plants will grow).

    [0223] In this context, the compounds according to the invention or the compositions according to the invention can be applied for example by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and/or post-emergence processes. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are as follows, though there is no intention to restrict the enumeration to particular species.

    [0224] In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I), salts or N-oxides thereof are preferably employed for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, where in a preferred embodiment the useful plants or ornamental plants are transgenic plants.

    [0225] The compounds of the general formula (I) according to the invention and/or their salts and N-oxides are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants: [0226] Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. [0227] Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

    [0228] When the compounds according to the invention are applied to the soil surface before germination of the harmful plants (weed grasses and/or broad-leaved weeds) (pre-emergence method), either the seedlings of the weed grasses or broad-leaved weeds are prevented completely from emerging or they grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.

    [0229] If the active compounds are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

    [0230] Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, triticale, triticum, Zea, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.

    [0231] In addition, the compounds of the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.

    [0232] By virtue of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

    [0233] It is preferred with a view to transgenic crops to use the compounds according to the invention and/or their salts and N-oxides in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

    [0234] It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

    [0235] By virtue of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further special properties may be tolerance or resistance to abiotic stressors, for example heat, cold, drought, salinity and ultraviolet radiation.

    [0236] Preference is given to the use of the compounds of the general formula (I) according to the invention and/or their salts and N-oxides in economically important transgenic crops of useful plants and ornamental plants, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potatoes, tomatoes, peas and other vegetables.

    [0237] The compounds of the general formula (I) can preferably be used as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

    [0238] Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods.

    [0239] A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known to the person skilled in the art. For such recombinant manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove parts of sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.

    [0240] For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

    [0241] To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but are not completely identical to them.

    [0242] When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

    [0243] The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e., not only monocotyledonous but also dicotyledonous plants.

    [0244] Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

    [0245] It is preferred to employ the compounds (I) according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active compounds.

    [0246] When the active compounds of the invention are employed in transgenic crops, not only do the effects toward harmful plants observed in other crops occur, but frequently also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

    [0247] The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and/or their salts and N-oxides as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.

    [0248] Preference is given to the use in cereals, here preferably corn, wheat, barley, rye, oats, millet or rice, by the pre- or post-emergence method.

    [0249] Preference is also given to the use in soybeans by the pre- or post-emergence method.

    [0250] The use according to the invention for the control of harmful plants or for growth regulation of plants also includes the case in which the active compound of the general formula (I) or its salt is not formed from a precursor substance (prodrug) until after application on the plant, in the plant or in the soil.

    [0251] The invention also provides for the use of one or more compounds of the general formula (I), salts or N-oxides thereof or of a composition according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the general formula (I), salts or N-oxides thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.

    [0252] The invention also provides an herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises [0253] (a) one or more compounds of the general formula (I), salts or N-oxides thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1-001) to (1-106), salts or N-oxides thereof, in each case as defined above, and [0254] (b) one or more further substances selected from groups (i) and/or (ii): [0255] (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not corresponding to the general formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, [0256] (ii) one or more formulation auxiliaries customary in crop protection.

    [0257] Here, the further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances mentioned in The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

    [0258] A herbicidal or plant growth-regulating composition according to the invention comprises preferably one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-formers, thickeners, inorganic salts, dusting agents, carriers solid at 25? C. and 1013 mbar, preferably adsorbent granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25? C. and 1013 mbar.

    [0259] The compounds of general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I), salts or N-oxides thereof.

    [0260] The compounds of the general formula (I), salts or N-oxides thereof can be formulated in various ways according to which biological and/or physicochemical parameters are required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

    [0261] These individual formulation types and the formulation assistants, such as inert materials, surfactants, solvents and further additives, are known to the person skilled in the art and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Darland Books, Caldwell N.J.; H. v. Olphen, Introduction to Clay Colloid Chemistry, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, Solvents Guide, 2nd ed., Interscience, N.Y. 1963; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964; Sch?nfeldt, Grenzfl?chenaktive Athylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-K?chler, Chemische Technologie [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

    [0262] Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2-dinaphthylmethane-6,6-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

    [0263] Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

    [0264] Dusting products are obtained by grinding the active compound with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

    [0265] Suspension concentrates may be water- or oil-based. They may be prepared, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as have, for example, already been listed above for the other formulation types.

    [0266] Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

    [0267] Granules can be produced either by spraying the active compound onto adsorptive granular inert material or by applying active compound concentrates to the surface of carriers, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granulesif desired as a mixture with fertilizers.

    [0268] Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

    [0269] For the production of pan, fluidized-bed, extruder and spray granules, see e.g., processes in Spray Drying Handbook 3rd Ed. 1979, G. Goodwin Ltd., London, J. E. Browning, Agglomeration, Chemical and Engineering 1967, pages 147 ff; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw Hill, New York 1973, p. 8-57.

    [0270] For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, Weed Control Handbook, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

    [0271] The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, particularly preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active compounds of the general formula (I), salts or N-oxides thereof.

    [0272] In wettable powders, the active compound concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight of active compound; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

    [0273] In addition, the active compound formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described inter alia in Chemistry and Technology of Agrochemical Formulations, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

    [0274] The compounds of the general formula (I), salts or N-oxides 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 a tank mix. The combination formulations can be prepared on the basis of the abovementioned formulations, while taking account of the physical properties and stabilities of the active compounds to be combined.

    [0275] Active compounds which can be employed in combination with the compounds of general formula (I) according to the invention in mixture formulations or in a tank mix are, for example, known active compounds based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and literature cited therein.

    [0276] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds of general formula (I) according to the invention have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of compounds of general formula (I) according to the invention are of particular interest which comprise the compounds of general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.

    [0277] The weight ratios of herbicide (mixture) to safeners depend generally on the herbicide application rate and the efficacy of the safeners in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tank mix with the herbicides.

    [0278] For application, the herbicide or herbicide/safener formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

    [0279] The application rate of the compounds of the general formula (I), salts or N-oxides thereof is affected to a certain extent by external conditions such as temperature, humidity, etc. Here, the application rate may vary within wide limits. For the application as a herbicide for controlling harmful plants, the total amount of compounds of the general formula (I), salts or N-oxides thereof are preferably in the range from 0.001 to 10.0 kg/ha, with preference in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, in particular preferably in the range from 0.05 to 1 kg/ha. This applies both to the pre-emergence and the post-emergence application.

    [0280] When the compounds of the general formula (I), salts or N-oxides thereof are used as plant growth regulators, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of from 0.001 to 2 kg/ha, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha, very particularly in the range from 20 to 250 g/ha. This applies both to the pre-emergence and the post-emergence application.

    [0281] The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tilling phase, at the beginning of the longitudinal growth.

    [0282] As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. Here, the application rate depends on the particular techniques and can be determined in preliminary tests.

    [0283] Active compounds which can be employed in combination with the compounds of the general formula (I) according to the invention in compositions according to the invention (for example in mixed formulations or in the tank mix) are, for example, known active compounds which are based on the 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, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active compounds, where the compounds are designated either with the common name in accordance with the International Organization for Standardization (ISO) or with the chemical name or with the code number. They always encompass all of the application forms such as, for example, acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if not explicitly mentioned.

    [0284] Examples of such herbicidal mixing partners are: [0285] Acetochlor, acifluorfen, acifluorfen-methyl, 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, aminopyralid-dimethylammonium, aminopyralid-tripromine, amitrole, ammoniumsulfamate, anilofos, asulam, asulam-potassium, asulam sodium, atrazine, azafenidin, azimsulfuron, beflubutamid, (S)-(?)-beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, benazolin-dimethylammonium, benazolin-potassium, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, bentazone-sdium, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromacil-lithium, bromacil-sodium, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, cambendichlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chlroamben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(?)-cinmethylin, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, clopyralid-tripomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D (including theammonium, butotyl, -butyl, choline, diethylammonium, -dimethylammonium, -diolamine, -doboxyl, -dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecylammonium, triethylammonium, triisopropanolammonium, tripromine and trolamine salt thereof), 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl-pyrazolate (DTP), dicamba and its salts, e. g. dicamba-biproamine, dicamba-N,N-Bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolaminemmonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolaminedicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine, 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-butotyl, dichlroprop-dimethylammonium, dichhlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-postassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-etexyl, dichlorprop-P-potassium, dichlorprop-sodium, diclofop, diclofop-methyl, diclofop-P, diclofop-P-methyl, diclosulam, difenzoquat, difenzoquat-metilsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, dinoterb-acetate, diphenamid, diquat, diquat-dibromid, diquat-dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium, Epyrifenacil (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5231, i.e. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethansulfonamid, F-7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluormethyl)pyrimidin-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupropanate-sdium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron sodium salt, fosamine, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosiante-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium, sesquisodium and -trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, haloxifop-sodium, hexazinone, HNPC-A8169, i.e. prop-2-yn-1-yl (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoate, HW-02, i.e. 1-(Dimethoxyphosphoryl)-ethyl-(2,4-dichlorphenoxy)acetat, hydantocidin, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazaquin.methyl, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, ioxynil-lithium, -octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-1-methyl-3-(trifluormethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazol, ketospiradox, ketospiradox-potassium, lactofen, lancotrione, lenacil, linuron, MCPA, MCPA-butotyl, -butyl, -dimethylammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, isoctyl, -isopropyl, -isopropylammonium, -methyl, olamine, -potassium, -sodium and -trolamine, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-butotyl, mecoprop-demethylammonium, mecoprop-diolamine, mecoprop-etexyl, mecoprop-ethadyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, and mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mefluidide-diolamine, mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron sodium salt, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-methyl, MT-5950, i.e. N-[3-chlor-4-(1-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-1-methyl-5-benzyloxypyrazol, NC-656, i.e. 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat-dichloride, paraquat-dimethylsulfate, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, phenmedipham-ethyl, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-triethylammonium, picloram-tripromine, picloram-trolamine, 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, quinclorac-dimethylammonium, quinclorac-methyl, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201, i.e. 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, i.e. 1-Ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. 1-[7-Fluor-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (trichloro acetic acid) and its salts, e.g. TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1 (2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, ethyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate; cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, prop-2-yn-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluormethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluormethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazolin-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazolin-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate).

    [0286] Examples of plant growth regulators as possible mixing partners are: [0287] Abscisic acid, acibenzolar, acibenzolar-S-methyl, 1-aminocyclopro-1-yl carboxylic acid and derivatives thereof, 5-Aminolavulinsaure, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, catechin, chitooligosaccharides (CO; COs differ from LCOs in that they lack the pendant fatty acid chain that is characteristic of LCOs. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc residues but have side chain decorations that make them different from chitin molecules [(C.sub.8C.sub.13NO.sub.5).sub.n, CAS No. 1398-61-4] and chitosan molecules [(C.sub.5H.sub.11NO.sub.4).sub.n, CAS No. 9012-76-4]), chitinous compounds, chlormequat chloride, cloprop, cyclanilide, 3-(Cycloprop-1-enyl)propionic acid, daminozide, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, Jasmonic acid or derivatives thereof (e.g. Jasmonic acid methyl ester), lipo-chitooligosaccharides (LCO, sometimes referred to as symbiotic nodulation (Nod) signals (or Nod factors) or as Myc factors, consist of an oligosaccharide backbone of 3-1,4-linked N-acetyl-D-glucosamine (GlcNAc) residues with an N-linked fatty acyl chain condensed at the non-reducing end. As understood in the art, LCOs differ in the number of GlcNAc residues in the backbone, in the length and degree of saturation of the fatty acyl chain and in the substitutions of reducing and non-reducing sugar residues), linoleic acid or derivatives thereof, linolenic acid or derivatives thereof, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methyl abscisic acid, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmon, salicylic acid, salicylic acid methyl ester, strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine.

    [0288] Suitable combination partners for the compounds of the general formula (I) according to the invention also include, for example, the following safeners: [0289] S1) Compounds from the group of heterocyclic carboxylic acid derivatives: [0290] S1.sup.a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1.sup.a), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (mefenpyr-diethyl), and related compounds as described in WO-A-91/07874; [0291] S1.sup.b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1.sup.b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (51-4) and related compounds as described in EP-A-333131 131 and EP-A-269806; [0292] S1.sup.c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1.sup.c), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554; [0293] S1.sup.d) Compounds of the triazolecarboxylic acid type (S1.sup.d), preferably compounds such as fenchlorazole (ethyl ester), i.e., ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (S1-7), and related compounds, as described in EP-A-174562 and EP-A-346620; [0294] S1.sup.e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1.sup.e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (isoxadifen-ethyl) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), as described in patent application WO-A-95/07897. [0295] S2) Compounds from the group of the 8-quinolinoxy derivatives (S2): [0296] S2.sup.a) Compounds of the 8-quinolinoxyacetic acid type (S2a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (cloquintocet-mexyl) (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), methyl 5-chloro-8-quinolinoxyacetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and salts thereof, for example the lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002/34048; [0297] S2.sup.b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2.sup.b), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198. [0298] S3) Active compounds of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), for example [0299] dichlormid (N,N-diallyl-2,2-dichloroacetamide) (S3-1), [0300] R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), [0301] R-28725 (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), [0302] benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), [0303] PPG-1292 (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5), [0304] DKA-24 (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S3-6), [0305] AD-67 or MON 4660 (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or [0306] Monsanto (S3-7), [0307] TI-35 (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8), [0308] Diclonon (Dicyclonon) or BAS145138 or LAB145138 (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, [0309] furilazole or MON 13900 ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and the (R) isomer thereof (S3-11). [0310] S4) Compounds from the class of the acylsulfonamides (S4): [0311] S4.sup.a) N-Acylsulfonamides of the formula (S4a) and salts thereof, as described in WO-A-97/45016,

    ##STR00027## [0312] in which [0313] R.sub.A.sup.1 is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, where the 2 latter radicals are substituted by v.sub.A substituents from the group of halogen, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio and, in the case of cyclic radicals, also by (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl; [0314] R.sub.A.sup.2 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0315] m.sub.A is 1 or 2; [0316] v.sub.A is 0, 1, 2 or 3; [0317] S4.sup.b) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4.sup.b) and salts thereof, as described in WO-A-99/16744,

    ##STR00028## [0318] in which [0319] R.sub.B.sup.1, R.sub.B.sup.2 are independently hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0320] R.sub.B.sup.3 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or (C.sub.1-C.sub.4)-alkoxy and [0321] m.sub.B is 1 or 2, [0322] for example those in which [0323] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (cyprosulfamide, S4-1), [0324] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-C.sub.1-2-OMe (S4-2), [0325] R.sub.B.sup.1=ethyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-3), [0326] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-C.sub.1-2-OMe (S4-4) and [0327] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-5); [0328] S4.sup.c ) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4.sup.c), as described in EP-A-365484,

    ##STR00029## [0329] in which [0330] R.sub.C.sup.1, R.sub.C.sup.2 are independently hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0331] R.sub.C.sup.3 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3 and [0332] m.sub.C is 1 or 2; [0333] for example [0334] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, [0335] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, [0336] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; [0337] S4.sup.d) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4.sup.d) and salts thereof, which are known, for example, from CN 101838227,

    ##STR00030## [0338] in which [0339] R.sub.D.sup.4 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0340] m.sub.D is 1 or 2; [0341] R.sub.D.sup.5 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl or (C.sub.5-C.sub.6)-cycloalkenyl. [0342] S5) Active compounds from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001. [0343] S6) Active compounds from the class of the 1,2-dihydroquinoxalin-2-ones (S6), for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630. [0344] S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856. [0345] S8) Compounds of the formula (S8), as described in WO-A-98/27049,

    ##STR00031## [0346] in which the symbols and indices are defined as follows: [0347] R.sub.D.sup.1 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, [0348] R.sub.D.sup.2 is hydrogen or (C.sub.1-C.sub.4)-alkyl, [0349] R.sub.D.sup.3 is hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, [0350] n.sub.D is an integer from 0 to 2. [0351] S9) active compounds from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-199/000020; [0352] S10) Compounds of the formula (S10.sup.a) or (S10.sup.b) [0353] as described in WO-A-2007/023719 and WO-A-2007/023764

    ##STR00032## [0354] in which [0355] R.sub.E.sup.1 is halogen, (C.sub.1-C.sub.4)-alkyl, methoxy, nitro, cyano, CF.sub.3, OCF.sub.3 [0356] Y.sub.E, Z.sub.E are independently O or S, [0357] n.sub.E is an integer from 0 to 4, [0358] R.sub.E.sup.2 is (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, aryl; benzyl, halobenzyl, [0359] R.sub.E.sup.3 is hydrogen or (C.sub.1-C.sub.6)-alkyl. [0360] S11) Active compounds of the oxyimino compound type (S11), which are known as seed-dressing agents, for example [0361] oxabetrinil ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, [0362] fluxofenim (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and [0363] cyometrinil or CGA-43089 ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage. [0364] S12) active compounds from the class of the isothiochromanones (S12), for example methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. [0365] S13) One or more compounds from group (S13): [0366] naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (513-1), which is known as a seed-dressing safener for corn against thiocarbamate herbicide damage, [0367] fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, [0368] flurazole (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage, [0369] CL 304415 (CAS Reg. No. 31541-57-8) [0370] (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage by imidazolinones, [0371] MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn, [0372] MG 838 (CAS Reg. No. 133993-74-5) [0373] (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia [0374] disulfoton (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), [0375] dietholate (0,0-diethyl 0-phenyl phosphorothioate) (S13-8), [0376] mephenate (4-chlorophenyl methylcarbamate) (S13-9). [0377] S14) active compounds which, in addition to herbicidal action against weeds, also have safener action on crop plants such as rice, for example [0378] dimepiperate or MY-93 (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate, [0379] daimuron or SK 23 (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as safener for rice against imazosulfuron herbicide damage, [0380] cumyluron=JC-940 (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known as safener for rice against damage by some herbicides, [0381] methoxyphenone or NK 049 (3,3-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides, [0382] CSB (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice. [0383] S15) Compounds of the formula (S15) or tautomers thereof

    ##STR00033## [0384] as described in WO-A-2008/131861 and WO-A-2008/131860 [0385] in which [0386] R.sub.H.sup.1 is a (C.sub.1-C.sub.6)-haloalkyl radical and [0387] R.sub.H.sup.2 is hydrogen or halogen and [0388] R.sub.H.sup.3, R.sub.H.sup.4 are each independently hydrogen, (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.16)-alkenyl or (C.sub.2-C.sub.16)-alkynyl, [0389] where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylamino, di[(C.sub.1-C.sub.4)-alkyl]amino, [(C.sub.1-C.sub.4)-alkoxy]carbonyl, [(C.sub.1-C.sub.4)-haloalkoxy]carbonyl, (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0390] or (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.4-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C.sub.4-C.sub.6)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, [0391] where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylamino, di[(C.sub.1-C.sub.4)alkyl]amino, [(C.sub.1-C.sub.4)alkoxy]carbonyl, [(C.sub.1-C.sub.4)haloalkoxy]carbonyl, (C.sub.3-C.sub.6)cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0392] or [0393] R.sub.H.sup.3 is (C.sub.1-C.sub.4)-alkoxy, (C.sub.2-C.sub.4)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy or (C.sub.2-C.sub.4)-haloalkoxy and [0394] R.sub.H.sup.4 is hydrogen or (C.sub.1-C.sub.4)-alkyl or [0395] R.sub.H.sup.3 and R.sub.H.sup.4 together with the directly bonded nitrogen atom are a four- to eight-membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to 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 halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio. [0396] S16) Active compounds which are used primarily as herbicides but also have safener action on crop plants, for example [0397] (2,4-dichlorophenoxy)acetic acid (2,4-D), [0398] (4-chlorophenoxy)acetic acid, [0399] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), [0400] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), [0401] (4-chloro-o-tolyloxy)acetic acid (MCPA), [0402] 4-(4-chloro-o-tolyloxy)butyric acid, [0403] 4-(4-chlorophenoxy)butyric acid, [0404] 3,6-dichloro-2-methoxybenzoic acid (dicamba), [0405] 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).

    [0406] Preferred safeners in combination with the compounds of the general formula (I) according to the invention and/or their salts and N-oxides, in particular with the compounds of the formulae (I-001) to (I-106), salts or N-oxides thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

    Biological Examples

    [0407] The following abbreviations are used in the examples and tables below:

    Tested Harmful Plants:

    [0408] ABUTH: Abutilon theophrasti [0409] ALOMY: Alopecurus myosuroides [0410] AMARE: Amaranthus retroflexus [0411] DIGSA: Digitaria sanguinalis [0412] ECHCG: Echinochloa crus-galli [0413] KCHSC: Kochia scoparia [0414] LOLRI: Lolium rigidum [0415] MATIN: Matricaria inodora [0416] POAAN: Poa annua [0417] SETVJ: Setaria viridis [0418] STEME: Stellaria media [0419] VERPE: Veronica persica

    A. Herbicidal Pre-Emergence Action

    [0420] Seeds of mono- and dicotyledonous weed plants were sown in plastic pots (double sowings with one species of mono- and one species of dicotyledonous weed plants per pot), in sandy loam, and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsifiable concentrates (EC), were applied to the surface of the covering soil as an aqueous suspension or as an emulsion, with the addition of 0.5% of an additive, at an application rate of 600 litres of water per hectare (converted). Following treatment, the pots were placed in a greenhouse and kept under optimum growth conditions for the test plants. The visual grading of the damage to the test plants was carried out after ca. 3 weeks in comparison to untreated controls (herbicidal effect in percent (%): 100% effect=plants have died, 0% effect=as control plants).

    [0421] Tables A1 to A11 below, show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g/ha obtained by the experimental procedure mentioned above.

    TABLE-US-00003 TABLE A1 Example Number Dosage [g/ha] ABUTH I-012 1280 100 I-014 1280 90 I-027 1280 100 I-029 1280 90 I-045 1280 90 I-046 1280 90 I-070 1280 100 I-071 1280 90 I-091 1280 90 I-092 1280 90 I-097 1280 100

    TABLE-US-00004 TABLE A2 Example Number Dosage [g/ha] ALOMY I-008 1280 100

    TABLE-US-00005 TABLE A3 Example Number Dosage [g/ha] DIGSA I-077 1280 100

    TABLE-US-00006 TABLE A4 Example Number Dosage [g/ha] KCHSC I-002 1280 90 I-004 1280 90 I-011 1280 100 I-012 1280 100 I-013 1280 90 I-022 1280 90 I-026 1280 90 I-027 1280 90 I-029 1280 90 I-030 1280 90 I-035 1280 100 I-049 1280 90 I-058 1280 90 I-077 1280 90 I-093 1280 90 I-101 1280 100 I-102 1280 90

    TABLE-US-00007 TABLE A5 Example Number Dosage [g/ha] LOLRI I-003 1280 100 I-007 1280 90 I-010 1280 100 I-011 1280 90 I-012 1280 100 I-013 1280 100 I-014 1280 100 I-016 1280 100 I-019 1280 90 I-022 1280 100 I-024 1280 90 I-026 1280 100 I-027 1280 100 I-029 1280 100 I-030 1280 100 I-033 1280 100 I-034 1280 100 I-036 1280 90 I-045 1280 100 I-046 1280 100 I-058 1280 90 I-070 1280 100 I-071 1280 100 I-073 1280 90 I-074 1280 90 I-081 1280 90 I-082 1280 90 I-084 1280 90 I-085 1280 100 I-086 1280 100 I-087 1280 90 I-088 1280 100 I-089 1280 90 I-090 1280 90 I-091 1280 100 I-092 1280 100 I-095 1280 100 I-096 1280 90 I-097 1280 100 I-100 1280 90 I-101 1280 100 I-102 1280 90

    TABLE-US-00008 TABLE A6 Example Number Dosage [g/ha] MATIN I-010 1280 100 I-011 1280 90 I-012 1280 90 I-013 1280 100 I-014 1280 100 I-016 1280 100 I-022 1280 90 I-023 1280 90 I-025 1280 100 I-026 1280 100 I-027 1280 100 I-028 1280 100 I-029 1280 100 I-030 1280 100 I-034 1280 100 I-036 1280 100 I-045 1280 90 I-046 1280 90 I-066 1280 90 I-070 1280 100 I-071 1280 100 I-073 1280 90 I-077 1280 100 I-081 1280 90 I-082 1280 90 I-086 1280 100 I-088 1280 100 I-089 1280 100 I-090 1280 90 I-091 1280 100 I-092 1280 100 I-093 1280 90 I-094 1280 100 I-095 1280 90 I-096 1280 100 I-098 1280 100 I-099 1280 90 I-101 1280 100 I-102 1280 100

    TABLE-US-00009 TABLE A7 Example Number Dosage [g/ha] POAAN I-003 1280 90 I-007 1280 100 I-008 1280 100 I-010 1280 90 I-012 1280 90 I-014 1280 90 I-021 1280 90 I-022 1280 90 I-026 1280 90 I-028 1280 100 I-077 1280 100

    TABLE-US-00010 TABLE A8 Example Number Dosage [g/ha] SETVI I-009 1280 100 I-012 1280 100 I-014 1280 90 I-045 1280 90 I-068 1280 90 I-071 1280 90 I-092 1280 90 I-101 1280 90

    TABLE-US-00011 TABLE A9 Example Number Dosage [g/ha] STEME I-003 1280 100 I-007 1280 100 I-010 1280 90 I-011 1280 100 I-012 1280 100 I-013 1280 100 I-014 1280 100 I-016 1280 100 I-019 1280 100 I-022 1280 100 I-023 1280 90 I-024 1280 90 I-025 1280 100 I-026 1280 100 I-027 1280 100 I-028 1280 100 I-029 1280 100 I-030 1280 100 I-033 1280 90 I-036 1280 100 I-045 1280 100 I-046 1280 100 I-049 1280 100 I-058 1280 90 I-070 1280 90 I-071 1280 90 I-073 1280 90 I-074 1280 90 I-081 1280 90 I-082 1280 90 I-085 1280 90 I-086 1280 100 I-088 1280 90 I-089 1280 90 I-090 1280 100 I-091 1280 100 I-092 1280 100 I-095 1280 100 I-096 1280 100 I-097 1280 100 I-098 1280 100 I-099 1280 90 I-100 1280 100 I-101 1280 100 I-102 1280 100

    TABLE-US-00012 TABLE A10 Example Number Dosage [g/ha] VERPE I-030 1280 90 I-086 1280 90

    TABLE-US-00013 TABLE A11 Example Number Dosage [g/ha] AMARE I-001 1280 90 I-003 1280 90 I-004 1280 90 I-005 1280 100 I-010 1280 90 I-011 1280 100 I-012 1280 100 I-013 1280 90 I-014 1280 100 I-016 1280 90 I-022 1280 90 I-023 1280 90 I-026 1280 100 I-029 1280 100 I-030 1280 100 I-033 1280 90 I-034 1280 90 I-035 1280 90 I-039 1280 90 I-045 1280 100 I-046 1280 90 I-066 1280 100 I-068 1280 90 I-077 1280 100 I-086 1280 90 I-088 1280 100 I-090 1280 90 I-091 1280 100 I-092 1280 100 I-093 1280 90 I-094 1280 100 I-095 1280 100 I-096 1280 90 I-097 1280 100 I-098 1280 100 I-101 1280 100 I-102 1280 100

    [0422] As the results show, various compounds of the general formula (I) according to the invention have very good herbicidal pre-emergence efficacy against a broad spectrum of harmful mono- and dicotyledonous plants such as Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Digitaria sanguinalis (DIGSA), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME) and Veronica persica (VERPE) at an application rate of 1280 g of active ingredient per hectare.

    B. Herbicidal Post-Emergence Action

    [0423] Seeds of mono- and dicotyledonous weed plants were sown in plastic pots (double sowings with one species of mono- and one species of dicotyledonous weed plants per pot), in sandy loam, covered with soil and grown under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were sprayed in the single-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsifiable concentrates (EC), were sprayed onto the green plant parts as an aqueous suspension or as an emulsion, with the addition of 0.5% of an additive, at an application rate of 600 litres of water per hectare (converted). The test plants were placed in the greenhouse for ca. 3 weeks under optimum growth conditions, and then the effect of the preparations was assessed visually in comparison with untreated controls (herbicidal effect in percent (%): 100% effect=plants have died, 0% effect=as control plants).

    [0424] Tables B1 to B11 below, show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants using an application rate corresponding to 1280 g/ha obtained by the experimental procedure mentioned above.

    TABLE-US-00014 TABLE B1 Example Number Dosage [g/ha] ABUTH I-003 1280 90 I-004 1280 90 I-010 1280 100 I-012 1280 100 I-013 1280 100 I-016 1280 100 I-017 1280 90 I-019 1280 90 I-022 1280 100 I-026 1280 100 I-027 1280 90 I-029 1280 100 I-030 1280 100 I-033 1280 90 I-034 1280 90 I-035 1280 90 I-036 1280 90 I-038 1280 90 I-045 1280 100 I-046 1280 100 I-049 1280 90 I-058 1280 100 I-066 1280 90 I-070 1280 100 I-071 1280 100 I-073 1280 100 I-074 1280 100 I-081 1280 100 I-082 1280 100 I-084 1280 90 I-085 1280 100 I-086 1280 90 I-087 1280 100 I-089 1280 90 I-093 1280 90 I-094 1280 90 I-098 1280 90 I-099 1280 100 I-100 1280 90 I-101 1280 100 I-102 1280 100

    TABLE-US-00015 TABLE B2 Example Number Dosage [g/ha] DIGSA I-034 1280 90 I-052 1280 90 I-068 1280 90

    TABLE-US-00016 TABLE B3 Example Number Dosage [g/ha] ECHCG I-010 1280 90 I-016 1280 90 I-022 1280 90 I-029 1280 90 I-030 1280 90 I-034 1280 90 I-064 1280 100 I-077 1280 90

    TABLE-US-00017 TABLE B4 Example Number Dosage [g/ha] KCHSC I-003 1280 100 I-007 1280 100 I-010 1280 100 I-011 1280 90 I-012 1280 100 I-013 1280 100 I-014 1280 100 I-016 1280 100 I-017 1280 100 I-019 1280 90 I-026 1280 90 I-027 1280 90 I-029 1280 90 I-030 1280 90 I-033 1280 90 I-034 1280 90 I-035 1280 90 I-036 1280 90 I-045 1280 90 I-046 1280 90 I-049 1280 90 I-058 1280 100 I-064 1280 100 I-068 1280 90 I-073 1280 90 I-074 1280 90 I-081 1280 100 I-084 1280 90 I-085 1280 100 I-087 1280 100 I-094 1280 90 I-098 1280 90 I-099 1280 90 I-101 1280 90 I-102 1280 100

    TABLE-US-00018 TABLE B5 Example Number Dosage [g/ha] LOLRI I-003 1280 90 I-007 1280 90 I-010 1280 100 I-012 1280 100 I-013 1280 100 I-014 1280 90 I-016 1280 90 I-022 1280 90 I-029 1280 90 I-030 1280 90 I-034 1280 90 I-036 1280 90 I-045 1280 100 I-046 1280 100 I-058 1280 100 I-070 1280 100 I-074 1280 90 I-081 1280 90 I-085 1280 100 I-086 1280 100 I-088 1280 90 I-091 1280 90 I-092 1280 90 I-095 1280 90 I-101 1280 90 I-102 1280 90

    TABLE-US-00019 TABLE B6 Example Number Dosage [g/ha] MATIN I-003 1280 100 I-007 1280 90 I-010 1280 100 I-012 1280 100 I-013 1280 100 I-014 1280 90 I-016 1280 90 I-019 1280 90 I-022 1280 90 I-026 1280 100 I-029 1280 90 I-030 1280 90 I-033 1280 90 I-034 1280 90 I-035 1280 90 I-036 1280 90 I-045 1280 100 I-046 1280 100 I-049 1280 90 I-058 1280 100 I-064 1280 100 I-066 1280 90 I-070 1280 90 I-073 1280 90 I-074 1280 90 I-081 1280 100 I-082 1280 90 I-085 1280 100 I-086 1280 90 I-087 1280 100 I-088 1280 90 I-089 1280 90 I-090 1280 90 I-092 1280 90 I-093 1280 90 I-094 1280 90 I-095 1280 90 I-098 1280 90 I-099 1280 90 I-101 1280 90 I-102 1280 100

    TABLE-US-00020 TABLE B7 Example Number Dosage [g/ha] POAAN I-010 1280 100

    TABLE-US-00021 TABLE B8 Example Number Dosage [g/ha] SETVI I-030 1280 90 I-034 1280 90 I-036 1280 90 I-045 1280 90 I-064 1280 90 I-088 1280 90 I-092 1280 90 I-093 1280 90

    TABLE-US-00022 TABLE B9 Example Number Dosage [g/ha] STEME I-003 1280 100 I-004 1280 100 I-005 1280 90 I-007 1280 100 I-010 1280 100 I-012 1280 100 I-013 1280 100 I-014 1280 100 I-016 1280 100 I-019 1280 90 I-022 1280 100 I-023 1280 90 I-024 1280 90 I-026 1280 90 I-027 1280 90 I-029 1280 100 I-030 1280 100 I-033 1280 90 I-034 1280 90 I-035 1280 90 I-036 1280 90 I-037 1280 90 I-039 1280 90 I-045 1280 100 I-046 1280 100 I-058 1280 90 I-064 1280 100 I-066 1280 100 I-070 1280 100 I-071 1280 100 I-073 1280 100 I-074 1280 100 I-077 1280 100 I-081 1280 90 I-082 1280 100 I-084 1280 90 I-085 1280 100 I-086 1280 100 I-088 1280 90 I-090 1280 90 I-091 1280 90 I-092 1280 100 I-093 1280 90 I-095 1280 90 I-096 1280 100 I-097 1280 90 I-098 1280 90 I-099 1280 90 I-100 1280 100 I-101 1280 100 I-102 1280 100

    TABLE-US-00023 TABLE B10 Example Number Dosage [g/ha] VERPE I-003 1280 100 I-007 1280 90 I-010 1280 90 I-012 1280 90 I-013 1280 100 I-014 1280 90 I-016 1280 90 I-017 1280 90 I-019 1280 90 I-024 1280 90 I-026 1280 90 I-027 1280 90 I-029 1280 90 I-030 1280 90 I-033 1280 90 I-034 1280 90 I-035 1280 90 I-036 1280 90 I-045 1280 100 I-046 1280 100 I-049 1280 90 I-058 1280 90 I-064 1280 90 I-068 1280 90 I-070 1280 90 I-071 1280 90 I-074 1280 90 I-081 1280 100 I-082 1280 90 I-084 1280 90 I-085 1280 100 I-087 1280 90 I-093 1280 90 I-094 1280 90 I-098 1280 90 I-099 1280 90 I-101 1280 100 I-102 1280 90

    TABLE-US-00024 TABLE B11 Example Number Dosage [g/ha] AMARE I-003 1280 100 I-005 1280 100 I-007 1280 90 I-010 1280 100 I-011 1280 90 I-012 1280 90 I-013 1280 90 I-014 1280 90 I-016 1280 100 I-017 1280 90 I-019 1280 90 I-022 1280 90 I-023 1280 90 I-024 1280 90 I-026 1280 100 I-027 1280 100 I-028 1280 90 I-029 1280 90 I-030 1280 90 I-033 1280 100 I-034 1280 100 I-035 1280 90 I-036 1280 100 I-038 1280 90 I-039 1280 90 I-040 1280 90 I-045 1280 100 I-046 1280 100 I-049 1280 100 I-058 1280 90 I-064 1280 100 I-070 1280 100 I-071 1280 100 I-073 1280 90 I-074 1280 100 I-081 1280 100 I-082 1280 90 I-084 1280 90 I-085 1280 100 I-086 1280 100 I-087 1280 100 I-088 1280 100 I-089 1280 100 I-090 1280 90 I-092 1280 90 I-093 1280 100 I-094 1280 100 I-095 1280 90 I-096 1280 90 I-097 1280 90 I-098 1280 100 I-099 1280 90 I-100 1280 90 I-101 1280 100 I-102 1280 100

    [0425] As the results show, various compounds of the general formula (I) according to the invention have very good herbicidal post-emergence efficacy against a broad spectrum of harmful mono- and dicotyledonous plants such as Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME) and Veronica persica (VERPE) at an application rate of 1280 g of active ingredient per hectare.

    C. Herbicidal Pre-Emergence Action

    [0426] Seeds of mono- and dicotyledonous weed plants were sown in plastic pots (double sowings with one species of mono- and one species of dicotyledonous weed plants per pot), in sandy loam, and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsifiable concentrates (EC), were applied to the surface of the covering soil as an aqueous suspension or as an emulsion, with the addition of 0.5% of an additive, at an application rate of 600 litres of water per hectare (converted). Following treatment, the pots were placed in a greenhouse and kept under optimum growth conditions for the test plants. The visual grading of the damage to the test plants was carried out after ca. 3 weeks in comparison to untreated controls (herbicidal effect in percent (%): 100% effect=plants have died, 0% effect=as control plants).

    [0427] Tables C1 to C6 below, show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants using an application rate corresponding to 320 g/ha obtained by the experimental procedure mentioned above.

    TABLE-US-00025 TABLE C1 Example Number Dosage [g/ha] KCHSC I-002 320 90 I-102 320 90

    TABLE-US-00026 TABLE C2 Example Number Dosage [g/ha] LOLRI I-016 320 90 I-022 320 100 I-026 320 90 I-029 320 90 I-030 320 90 I-033 320 100 I-045 320 90 I-046 320 90 I-086 320 90 I-088 320 90 I-091 320 100 I-092 320 100 I-095 320 90 I-096 320 90 I-101 320 90

    TABLE-US-00027 TABLE C3 Example Number Dosage [g/ha] MATIN I-026 320 90 I-027 320 100 I-028 320 100 I-030 320 100 I-091 320 90

    TABLE-US-00028 TABLE C4 Example Number Dosage [g/ha] POAAN I-008 320 100 I-012 320 90

    TABLE-US-00029 TABLE C5 Example Number Dosage [g/ha] STEME I-011 320 90 I-012 320 90 I-014 320 100 I-022 320 100 I-025 320 100 I-026 320 100 I-027 320 100 I-028 320 100 I-030 320 100 I-045 320 90 I-046 320 100 I-070 320 90 I-073 320 90 I-090 320 90 I-091 320 100 I-092 320 90 I-095 320 90 I-096 320 100 I-097 320 90 I-099 320 90 I-100 320 100 I-102 320 90

    TABLE-US-00030 TABLE C6 Example Number Dosage [g/ha] AMARE I-003 320 90 I-012 320 100 I-014 320 90 I-030 320 90 I-033 320 90 I-091 320 90 I-092 320 90 I-095 320 90

    [0428] As the results show, various compounds of the general formula (I) according to the invention have very good herbicidal pre-emergence efficacy against a broad spectrum of harmful mono- and dicotyledonous plants such as Amaranthus retroflexus (AMARE), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Poa annua (POAAN) and Stellaria media (STEME) at an application rate of 320 g of active ingredient per hectare.

    D. Herbicidal Post-Emergence Action

    [0429] Seeds of mono- and dicotyledonous weed plants were sown in plastic pots (double sowings with one species of mono- and one species of dicotyledonous weed plants per pot), in sandy loam, covered with soil and grown under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were sprayed in the single-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsifiable concentrates (EC), were sprayed onto the green plant parts as an aqueous suspension or as an emulsion, with the addition of 0.5% of an additive, at an application rate of 600 litres of water per hectare (converted). The test plants were placed in the greenhouse for ca. 3 weeks under optimum growth conditions, and then the effect of the preparations was assessed visually in comparison with untreated controls (herbicidal effect in percent (%): 100% effect=plants have died, 0% effect=as control plants).

    [0430] Tables D1 to D8 below, show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants using an application rate corresponding to 320 g/ha obtained by the experimental procedure mentioned above.

    TABLE-US-00031 TABLE D1 Example Number Dosage [g/ha] ABUTH I-010 320 90 I-012 320 100 I-016 320 100 I-017 320 90 I-019 320 90 I-022 320 90 I-026 320 90 I-027 320 90 I-029 320 90 I-030 320 90 I-033 320 90 I-034 320 90 I-035 320 90 I-036 320 90 I-045 320 100 I-046 320 100 I-058 320 90 I-070 320 100 I-071 320 100 I-073 320 100 I-081 320 90 I-082 320 90 I-085 320 90 I-101 320 90

    TABLE-US-00032 TABLE D2 Example Number Dosage [g/ha] ECHCG I-016 320 90 I-064 320 100

    TABLE-US-00033 TABLE D3 Example Number Dosage [g/ha] KCHSC I-003 320 90 I-010 320 100 I-012 320 100 I-013 320 100 I-014 320 100 I-016 320 90 I-019 320 90 I-036 320 90 I-045 320 90 I-049 320 90 I-058 320 90 I-064 320 100 I-074 320 90 I-087 320 90 I-098 320 90

    TABLE-US-00034 TABLE D4 Example Number Dosage [g/ha] LOLRI I-012 320 100 I-016 320 90 I-030 320 90 I-045 320 100 I-058 320 90 I-081 320 90 I-085 320 90 I-086 320 90 I-095 320 90

    TABLE-US-00035 TABLE D5 Example Number Dosage [g/ha] MATIN I-010 320 100 I-013 320 90 I-014 320 90 I-016 320 90 I-026 320 90 I-045 320 90 I-046 320 90 I-064 320 90 I-081 320 90 I-087 320 90 I-093 320 90 I-094 320 90

    TABLE-US-00036 TABLE D6 Example Number Dosage [g/ha] STEME I-003 320 90 I-004 320 90 I-010 320 100 I-012 320 100 I-013 320 100 I-014 320 100 I-016 320 100 I-022 320 90 I-027 320 90 I-029 320 90 I-030 320 90 I-034 320 90 I-045 320 90 I-046 320 90 I-058 320 90 I-064 320 90 I-070 320 90 I-071 320 90 I-077 320 90 I-081 320 90 I-082 320 90 I-085 320 100 I-086 320 90 I-091 320 90 I-092 320 90 I-095 320 90 I-096 320 90 I-097 320 90 I-098 320 90 I-099 320 90 I-100 320 90 I-101 320 90 I-102 320 90

    TABLE-US-00037 TABLE D7 Example Number Dosage [g/ha] VERPE I-003 320 100 I-010 320 90 I-013 320 90 I-017 320 90 I-026 320 90 I-045 320 100 I-046 320 90 I-085 320 90 I-087 320 90 I-101 320 90 I-102 320 90

    TABLE-US-00038 TABLE D8 Example Number Dosage [g/ha] AMARE I-003 320 90 I-005 320 90 I-007 320 90 I-010 320 100 I-013 320 90 I-014 320 90 I-016 320 100 I-017 320 90 I-019 320 90 I-022 320 90 I-026 320 90 I-027 320 90 I-029 320 90 I-030 320 90 I-033 320 90 I-034 320 90 I-035 320 90 I-036 320 90 I-045 320 90 I-046 320 90 I-058 320 90 I-064 320 100 I-070 320 90 I-071 320 90 I-081 320 90 I-084 320 90 I-085 320 90 I-086 320 90 I-087 320 90 I-088 320 90 I-101 320 90 I-102 320 90

    [0431] As the results show, various compounds of the general formula (I) according to the invention have very good herbicidal post-emergence efficacy against a broad spectrum of harmful mono- and dicotyledonous plants such as Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Stellaria media (STEME) and Veronica persica (VERPE) at an application rate of 320 g of active ingredient per hectare.