SUBSTITUTED HETEROARYL PYRROLONES AND SALTS THEREOF AND USE THEREOF AS HERBICIDAL ACTIVE SUBSTANCES
20200079765 ยท 2020-03-12
Inventors
- Jens Frackenpohl (Frankfurt, DE)
- Jana FRANKE (Mainz, DE)
- Hendrik Helmke (Liederbach, DE)
- Anna Maria REINGRUBER (Heppenheim, DE)
- Hansjoerg Dietrich (Liederbach am Taunus, DE)
- Anu Bheemaiah Machettira (Frankfurt am Main, DE)
- Elmar Gatzweiler (Bad Nauheim, DE)
- Christopher Hugh Rosinger (Hofheim, GB)
- Dirk Schmutzler (Hattersheim, DE)
- Peter LUEMMEN (Idstein, DE)
Cpc classification
C07D413/04
CHEMISTRY; METALLURGY
C07D419/04
CHEMISTRY; METALLURGY
A01N43/90
HUMAN NECESSITIES
A01N43/82
HUMAN NECESSITIES
A01N43/52
HUMAN NECESSITIES
A01N43/80
HUMAN NECESSITIES
C07D403/04
CHEMISTRY; METALLURGY
A01N43/713
HUMAN NECESSITIES
C07D401/04
CHEMISTRY; METALLURGY
International classification
C07D417/04
CHEMISTRY; METALLURGY
C07D403/04
CHEMISTRY; METALLURGY
C07D413/04
CHEMISTRY; METALLURGY
A01N43/80
HUMAN NECESSITIES
A01N43/82
HUMAN NECESSITIES
A01N43/713
HUMAN NECESSITIES
A01N43/90
HUMAN NECESSITIES
C07D401/04
CHEMISTRY; METALLURGY
A01N43/52
HUMAN NECESSITIES
Abstract
The present invention relates to substituted heteroarylpyrrolones of the general formula (I) or salts 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 broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants.
Claims
1. A substituted heteroarylpyrrolone of formula (I) and/or a salt thereof in which ##STR00866## Q represents the moieties Q-1 to Q-29 ##STR00867## ##STR00868## ##STR00869## A.sup.1, A2, A.sup.3, A.sup.4 are identical or different and independently of one another represent N (nitrogen) or the moiety CR.sup.8, but there are never more than two adjacent nitrogen atoms, and where R.sup.8 in the moiety CR.sup.8 in each case has identical or different meanings according to the definition below, X and Y independently of one another represent CH or the moiety CR.sup.1, where X represents CH if Y represents the moiety CR.sup.1 and X represents the moiety CR.sup.1 if Y represents CH, R.sup.1 represents halogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.1-C.sub.8)-hydroxyalkyl, (C.sub.1-C.sub.8)-alkoxyalkyl, (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, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, tris-[(C.sub.1-C.sub.8)-alkyl]silyl-(C.sub.2-C.sub.8)-alkynyl, NR.sup.10R.sup.11, R.sup.3 represents hydroxy, hydrothio, halogen, NR.sup.10R.sup.11, (C.sub.1-C.sub.8)-alkoxy, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.8)-alkoxy, aryl-(C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy, arylcarbonyloxy, (C.sub.1-C.sub.8)-alkylcarbonyloxy, aryl-(C.sub.1-C.sub.8)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C.sub.3-C.sub.10)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (C.sub.1-C.sub.8)-haloalkylcarbonyloxy, (C.sub.2-C.sub.8)-alkenylcarbonyloxy, OC(O)OR.sup.12, OC(O)SR.sup.12, OC(S)OR.sup.12, OC(S)SR.sup.12, OSO.sub.2R.sup.13, OSO.sub.2OR.sup.12, OCHO, R.sup.4 and R.sup.7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, aryl-(C.sub.2-C.sub.8)-alkenyl, heteroaryl-(C.sub.2-C.sub.8)-alkenyl, heterocyclyl-(C.sub.2-C.sub.8)-alkenyl, aryl-(C.sub.2-C.sub.8)-alkynyl, heteroaryl-(C.sub.2-C.sub.8)-alkynyl, heterocyclyl-(C.sub.2-C.sub.8)-alkynyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.2-C.sub.8)-alkynyl, arylcarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl-(C.sub.1-C.sub.8)-alkyl, heteroarylcarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.10)-cycloalkylcarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, arylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, heteroaryl-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, CHO, C(O)R.sup.12, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, OR.sup.12, SR.sup.13, SOR.sup.13, SO.sub.2R.sup.13, NR.sup.10R.sup.11, R.sup.10R.sup.11N(C.sub.1-C.sub.8)-alkyl, cyano-(C.sub.1-C.sub.8)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.8)-alkyl, hydroxycarbonyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-alkylthio-(C.sub.1-C.sub.8)-alkylene, (C.sub.1-C.sub.8)-haloalkylthio-(C.sub.1-C.sub.8)-alkylthio, (C.sub.1-C.sub.8)-alkylthio-(C.sub.1-C.sub.8)-alkylthio, aminocarbonyl, aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylaminocarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyloxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkoxycarbonyl-C.sub.1-C.sub.8)-alkyl, cyano, hydroxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyloxy-(C.sub.1-C.sub.8)-alkyl, or where R.sup.4 and R.sup.7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19, R.sup.5 represents hydrogen, formyl, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, hydroxy-(C.sub.1-C.sub.8)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, aryl, heteroaryl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, NR.sup.10R.sup.11, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-cyanoalkyl, C(O)R.sup.12, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, SO.sub.2R.sup.13, (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyloxycarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, heteroaryl-(C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, aryloxycarbonyl-(C.sub.1-C.sub.8)-alkyl, arylcarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyl-(C.sub.1-C.sub.8)-alkyl, heteroarylcarbonyl-(C.sub.1-C.sub.8)-alkyl, heterocyclylcarbonyl-(C.sub.1-C.sub.8)-alkyl, or where R.sup.4 and R.sup.5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15, R.sup.6 represents hydrogen or (C.sub.1-C.sub.8)-alkyl, R.sup.8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR.sup.10R.sup.11, OR.sup.12, SR.sup.13, SOR.sup.13, SO.sub.2R.sup.13, thiocyanato, isothiocyanato, formyl, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, pentafluorothio, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-haloalkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(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(O)OR.sup.12, C(O)NR.sup.10R.sup.11, C(O)R.sup.12, CNOR.sup.12, CNOH, R.sup.10R.sup.11N(C.sub.1-C.sub.8)-alkyl, R.sup.12O(O)C(C.sub.1-C.sub.8)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkynyl, heteroaryl-(C.sub.1-C.sub.8)-alkynyl, heterocyclyl-(C.sub.1-C.sub.8)-alkynyl, tris-[(C.sub.1-C.sub.8)-alkyl]silyl-(C.sub.2-C.sub.8)-alkynyl, bis-[(C.sub.1-C.sub.8)-alkyl](aryl)silyl-(C.sub.2-C.sub.8)-alkynyl, bis-aryl[(C.sub.1-C.sub.8)-alkyl]silyl-(C.sub.2-C.sub.8)-alkynyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.2-C.sub.8)-alkynyl, aryl-(C.sub.2-C.sub.8)-alkenyl, heteroaryl-(C.sub.2-C.sub.8)-alkenyl, heterocyclyl-(C.sub.2-C.sub.8)-alkenyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.2-C.sub.8)-alkenyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylaminosulfonylamino, (C.sub.3-C.sub.8)-cycloalkylaminosulfonylamino, diazo, aryldiazo, tris-[(C.sub.1-C.sub.8)-alkyl]silyl, bis-[(C.sub.1-C.sub.8)-alkyl](aryl)silyl, bis-aryl[(C.sub.1-C.sub.8)-alkyl]silyl, or where A.sup.1 and A.sup.2, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.2 and A.sup.3, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.3 and A.sup.4, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, R.sup.10 and R.sup.11 are identical or different and independently of one another represent hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (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)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, COR.sup.12, SO.sub.2R.sup.13 (C.sub.1-C.sub.8)-alkyl-HNO.sub.2S, (C.sub.3-C.sub.10)-cycloalkyl-HNO.sub.2S, heterocyclyl, (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, aryl-(C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxycarbonyl, heteroaryl-(C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.2-C.sub.8)-alkenyloxycarbonyl, (C.sub.2-C.sub.8)-alkynyloxycarbonyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, R.sup.12 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyloxycarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, R.sup.13 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.2-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, NR.sup.10R.sup.11, and W represents oxygen or sulfur, where the cyclic structural elements of the radicals mentioned in R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.10, R.sup.11, R.sup.12 and R.sup.13, respectively, are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, hydroxy, cyano, NR.sup.10R.sup.11, (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)-alkylsulfoxy, (C.sub.1-C.sub.4)-alkylsulfone, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-haloalkylsulfoxy, (C.sub.1-C.sub.4)-haloalkylsulfone, (C.sub.1-C.sub.4)-alkoxycarbonyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl, (C.sub.1-C.sub.4)-alkylcarboxy, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.4)-alkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C.sub.1-C.sub.4)-alkyl, R.sup.10R.sup.11N-carbonyl, and where the structural elements cycloalkyl and heterocyclyl have n oxo groups, where n=0, 1 or 2.
2. The compound of formula (I) as claimed in claim 1 and/or the salt thereof, wherein Q represents the moieties Q-1 to Q-29 ##STR00870## ##STR00871## ##STR00872## A.sup.1, A2, A.sup.3, A.sup.4 are identical or different and independently of one another represent N (nitrogen) or the moiety CR.sup.8, but there are never more than two adjacent nitrogen atoms, and where R.sup.8 in the moiety CR.sup.8 in each case has identical or different meanings according to the definition below, X and Y independently of one another represent CH or the moiety CR.sup.1, where X represents CH if Y represents the moiety CR.sup.1 and X represents the moiety CR.sup.1 if Y represents CH, R.sup.1 represents halogen, (C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-haloalkyl, (C.sub.1-C.sub.7)-hydroxyalkyl, (C.sub.1-C.sub.7)-alkoxyalkyl, (C.sub.1-C.sub.7)-alkoxy, (C.sub.1-C.sub.7)-haloalkoxy, (C.sub.1-C.sub.7)-alkylthio, (C.sub.1-C.sub.7)-haloalkylthio, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.7)-halocycloalkyl, (C.sub.3-C.sub.7)-halocycloalkyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylcarbonyl, (C.sub.2-C.sub.7)-alkenyl, (C.sub.2-C.sub.7)-alkynyl, tris-[(C.sub.1-C.sub.7)-alkyl]silyl-(C.sub.2-C.sub.7)-alkynyl, NR.sup.10R.sup.11, R.sup.3 represents hydroxy, hydrothio, halogen, NR.sup.10R.sup.11, (C.sub.1-C.sub.7)-alkoxy, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.7)-alkoxy, aryl-(C.sub.1-C.sub.7)-alkoxy, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkoxy, arylcarbonyloxy, (C.sub.1-C.sub.7)-alkylcarbonyloxy, aryl-(C.sub.1-C.sub.7)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C.sub.3-C.sub.10)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (C.sub.1-C.sub.7)-haloalkylcarbonyloxy, (C.sub.2-C.sub.7)-alkenylcarbonyloxy, OC(O)OR.sup.12, OC(O)SR.sup.12, OC(S)OR.sup.12, OC(S)SR.sup.12, OSO.sub.2R.sup.13, OSO.sub.2OR.sup.12, OCHO, R.sup.4 and R.sup.7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-haloalkyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.7)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(C.sub.1-C.sub.7)-alkyl, heteroaryl-(C.sub.1-C.sub.7)-alkyl, heterocyclyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyl, (C.sub.2-C.sub.7)-alkynyl, (C.sub.2-C.sub.7)-haloalkenyl, (C.sub.2-C.sub.7)-haloalkynyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, aryl-(C.sub.2-C.sub.7)-alkenyl, heteroaryl-(C.sub.2-C.sub.7)-alkenyl, heterocyclyl-(C.sub.2-C.sub.7)-alkenyl, aryl-(C.sub.2-C.sub.7)-alkynyl, heteroaryl-(C.sub.2-C.sub.7)-alkynyl, heterocyclyl-(C.sub.2-C.sub.7)-alkynyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.2-C.sub.7)-alkynyl, arylcarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylcarbonyl-(C.sub.1-C.sub.7)-alkyl, heteroarylcarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.10)-cycloalkylcarbonyl-(C.sub.1-C.sub.7)-alkyl, aryl-(C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, arylcarbonyloxy-(C.sub.1-C.sub.7)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.7)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylcarbonyloxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.7)-cycloalkylcarbonyloxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-haloalkoxy-(C.sub.1-C.sub.7)-alkyl, aryl-(C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, heteroaryl-(C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, CHO, C(O)R.sup.12, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, OR.sup.12, SR.sup.13, SOR.sup.13, SO.sub.2R.sup.13, NR.sup.10R.sup.11, R.sup.10R.sup.11N(C.sub.1-C.sub.7)-alkyl, cyano-(C.sub.1-C.sub.7)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.7)-alkyl, hydroxycarbonyl, (C.sub.1-C.sub.7)-haloalkoxy-(C.sub.1-C.sub.7)-alkylthio, (C.sub.1-C.sub.7)-alkylthio-(C.sub.1-C.sub.7)-alkylene, (C.sub.1-C.sub.7)-haloalkylthio-(C.sub.1-C.sub.7)-alkylthio, (C.sub.1-C.sub.7)-alkylthio-(C.sub.1-C.sub.7)-alkylthio, aminocarbonyl, aminocarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylaminocarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.7)-cycloalkylaminocarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyloxycarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, cyano, hydroxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyloxy-(C.sub.1-C.sub.7)-alkyl, or where R.sup.4 and R.sup.7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19, R.sup.5 represents hydrogen, formyl, (C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-haloalkyl, hydroxy-(C.sub.1-C.sub.7)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, aryl, heteroaryl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.7)-alkyl, heterocyclyl, (C.sub.2-C.sub.7)-alkenyl, (C.sub.2-C.sub.7)-alkynyl, NR.sup.10R.sup.11, aryl-(C.sub.1-C.sub.7)-alkyl, heteroaryl-(C.sub.1-C.sub.7)-alkyl, heterocyclyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-cyanoalkyl, C(O)R.sup.12, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, SO.sub.2R.sup.13, (C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyloxycarbonyl-(C.sub.1-C.sub.7)-alkyl, aryl-(C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, heteroaryl-(C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, aryloxycarbonyl-(C.sub.1-C.sub.7)-alkyl, arylcarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylcarbonyl-(C.sub.1-C.sub.7)-alkyl, heteroarylcarbonyl-(C.sub.1-C.sub.7)-alkyl, heterocyclylcarbonyl-(C.sub.1-C.sub.7)-alkyl, or where R.sup.4 and R.sup.5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15, R.sup.6 represents hydrogen or (C.sub.1-C.sub.7)-alkyl, R.sup.8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR.sup.10R.sup.11, OR.sup.12, SR.sup.13, SOR.sup.13, SO.sub.2R.sup.13, thiocyanato, isothiocyanato, formyl, (C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyl, (C.sub.2-C.sub.7)-alkynyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.7)-haloalkenyl, (C.sub.2-C.sub.7)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, pentafluorothio, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-haloalkyl, (C.sub.1-C.sub.7)-haloalkoxy-(C.sub.1-C.sub.7)-haloalkyl, (C.sub.1-C.sub.7)-haloalkoxy-(C.sub.1-C.sub.7)-alkyl, aryl, aryl-(C.sub.1-C.sub.7)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.7)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylthio-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-haloalkylthio-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylcarbonyl-(C.sub.1-C.sub.7)-alkyl, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, C(O)R.sup.12, CNOR.sup.12, CNOH, R.sup.10R.sup.11N(C.sub.1-C.sub.7)-alkyl, R.sup.12O(O)C(C.sub.1-C.sub.7)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C.sub.1-C.sub.7)-alkyl, aryl-(C.sub.1-C.sub.7)-alkynyl, heteroaryl-(C.sub.1-C.sub.7)-alkynyl, heterocyclyl-(C.sub.1-C.sub.7)-alkynyl, tris-[(C.sub.1-C.sub.7)-alkyl]silyl-(C.sub.2-C.sub.7)-alkynyl, bis-[(C.sub.1-C.sub.7)-alkyl](aryl)silyl-(C.sub.2-C.sub.7)-alkynyl, bis-aryl[(C.sub.1-C.sub.7)-alkyl]silyl-(C.sub.2-C.sub.7)-alkynyl, (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.2-C.sub.7)-alkynyl, aryl-(C.sub.2-C.sub.7)-alkenyl, heteroaryl-(C.sub.2-C.sub.7)-alkenyl, heterocyclyl-(C.sub.2-C.sub.7)-alkenyl, (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.2-C.sub.7)-alkenyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylaminosulfonylamino, (C.sub.3-C.sub.7)-cycloalkylaminosulfonylamino, diazo, aryldiazo, tris-[(C.sub.1-C.sub.7)-alkyl]silyl, bis-[(C.sub.1-C.sub.7)-alkyl](aryl)silyl, bis-aryl[(C.sub.1-C.sub.7)-alkyl]silyl, or where A.sup.1 and A.sup.2, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.2 and A.sup.3, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.3 and A.sup.4, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, R.sup.10 and R.sup.11 are identical or different and independently of one another represent hydrogen, (C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyl, (C.sub.2-C.sub.7)-alkynyl, (C.sub.1-C.sub.7)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.7)-haloalkenyl, (C.sub.2-C.sub.7)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-haloalkoxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkylthio-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-haloalkylthio-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.7)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.7)-alkyl, COR.sup.12, SO.sub.2R.sup.13 (C.sub.1-C.sub.7)-alkyl-HNO.sub.2S, (C.sub.3-C.sub.10)-cycloalkyl-HNO.sub.2S, heterocyclyl, (C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxycarbonyl, aryl-(C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, aryl-(C.sub.1-C.sub.7)-alkoxycarbonyl, heteroaryl-(C.sub.1-C.sub.7)-alkoxycarbonyl, (C.sub.2-C.sub.7)-alkenyloxycarbonyl, (C.sub.2-C.sub.7)-alkynyloxycarbonyl, heterocyclyl-(C.sub.1-C.sub.7)-alkyl, R.sup.12 represents (C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyl, (C.sub.2-C.sub.7)-alkynyl, (C.sub.1-C.sub.7)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.7)-haloalkenyl, (C.sub.2-C.sub.7)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.7)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyloxycarbonyl-(C.sub.1-C.sub.7)-alkyl, aryl-(C.sub.1-C.sub.7)-alkoxycarbonyl-(C.sub.1-C.sub.7)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.7)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.7)-alkyl, R.sup.13 represents (C.sub.1-C.sub.7)-alkyl, (C.sub.2-C.sub.7)-alkenyl, (C.sub.2-C.sub.7)-alkynyl, (C.sub.1-C.sub.7)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.7)-haloalkenyl, (C.sub.2-C.sub.7)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-alkyl, (C.sub.1-C.sub.7)-alkoxy-(C.sub.1-C.sub.7)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.7)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.7)-alkyl, heterocyclyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.7)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.7)-alkyl, NR.sup.10R.sup.11, and W represents oxygen or sulfur.
3. The compound of formula (I) as claimed in claim 1 and/or the salt thereof, wherein Q represents the groups Q-1 to Q-29 ##STR00873## ##STR00874## ##STR00875## A.sup.1, A2, A.sup.3, A.sup.4 are identical or different and independently of one another represent N (nitrogen) or the moiety CR.sup.8, but there are never more than two adjacent nitrogen atoms, and where R.sup.8 in the moiety CR.sup.8 in each case has identical or different meanings according to the definition below, X and Y independently of one another represent CH or the moiety CR.sup.1, where X represents CH if Y represents the moiety CR.sup.1 and X represents the moiety CR.sup.1 if Y represents CH, R.sup.1 represents halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, (C.sub.1-C.sub.6)-alkoxyalkyl, (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, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, tris-[(C.sub.1-C.sub.6)-alkyl]silyl-(C.sub.2-C.sub.6)-alkynyl, NR.sup.10R.sup.11, R.sup.3 represents hydroxy, hydrothio, halogen, NR.sup.10R.sup.11, (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy, aryl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, arylcarbonyloxy, (C.sub.1-C.sub.6)-alkylcarbonyloxy, aryl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C.sub.3-C.sub.10)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.2-C.sub.6)-alkenylcarbonyloxy, OC(O)OR.sup.12, OC(O)SR.sup.12, OC(S)OR.sup.12, OC(S)SR.sup.12, OSO.sub.2R.sup.13, OSO.sub.2OR.sup.12, OCHO, R.sup.4 and R.sup.7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, aryl-(C.sub.2-C.sub.6)-alkenyl, heteroaryl-(C.sub.2-C.sub.6)-alkenyl, heterocyclyl-(C.sub.2-C.sub.6)-alkenyl, aryl-(C.sub.2-C.sub.6)-alkynyl, heteroaryl-(C.sub.2-C.sub.6)-alkynyl, heterocyclyl-(C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.2-C.sub.6)-alkynyl, arylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, heteroarylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.10)-cycloalkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, arylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, CHO, C(O)R.sup.12, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, OR.sup.12, SR.sup.13, SOR.sup.13, SO.sub.2R.sup.13, NR.sup.10R.sup.11, R.sup.10R.sup.11N(C.sub.1-C.sub.6)-alkyl, cyano-(C.sub.1-C.sub.6)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkyl, hydroxycarbonyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylene, (C.sub.1-C.sub.6)-haloalkylthio-(C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylthio, aminocarbonyl, aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyloxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, cyano, hydroxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyloxy-(C.sub.1-C.sub.6)-alkyl, or where R.sup.4 and R.sup.7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19, R.sup.5 represents hydrogen, formyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, hydroxy-(C.sub.1-C.sub.6)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, aryl, heteroaryl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, NR.sup.10R.sup.11, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-cyanoalkyl, C(O)R.sup.12, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, SO.sub.2R.sup.13, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyloxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aryloxycarbonyl-(C.sub.1-C.sub.6)-alkyl, arylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, heteroarylcarbonyl-(C.sub.1-C.sub.6)-alkyl, heterocyclylcarbonyl-(C.sub.1-C.sub.6)-alkyl, or where R.sup.4 and R.sup.5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15, R.sup.6 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, R.sup.8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR.sup.10R.sup.11, OR.sup.12, SR.sup.13, SOR.sup.13, SO.sub.2R.sup.13, thiocyanato, isothiocyanato, formyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, pentafluorothio, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, C(O)OR.sup.12, C(O)NR.sup.10R.sup.11, C(O)R.sup.12, CNOR.sup.12, CNOH, R.sup.10R.sup.11N(C.sub.1-C.sub.6)-alkyl, R.sup.12O(O)C(C.sub.1-C.sub.6)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkynyl, heteroaryl-(C.sub.1-C.sub.6)-alkynyl, heterocyclyl-(C.sub.1-C.sub.6)-alkynyl, tris-[(C.sub.1-C.sub.6)-alkyl]silyl-(C.sub.2-C.sub.6)-alkynyl, bis-[(C.sub.1-C.sub.6)-alkyl](aryl)silyl-(C.sub.2-C.sub.6)-alkynyl, bis-aryl[(C.sub.1-C.sub.6)-alkyl]silyl-(C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.2-C.sub.6)-alkynyl, aryl-(C.sub.2-C.sub.6)-alkenyl, heteroaryl-(C.sub.2-C.sub.6)-alkenyl, heterocyclyl-(C.sub.2-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.2-C.sub.6)-alkenyl, (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)-alkylaminosulfonylamino, (C.sub.3-C.sub.6)-cycloalkylaminosulfonylamino, diazo, aryldiazo, tris-[(C.sub.1-C.sub.6)-alkyl]silyl, bis-[(C.sub.1-C.sub.6)-alkyl](aryl)silyl, bis-aryl[(C.sub.1-C.sub.6)-alkyl]silyl, or where A.sup.1 and A.sup.2, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.2 and A.sup.3, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.3 and A.sup.4, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, R.sup.10 and R.sup.11 are identical or different and independently of one another represent hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (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)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, COR.sup.12, SO.sub.2R.sup.13 (C.sub.1-C.sub.6)-alkyl-HNO.sub.2S, (C.sub.3-C.sub.10)-cycloalkyl-HNO.sub.2S, heterocyclyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl, heteroaryl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.2-C.sub.6)-alkenyloxycarbonyl, (C.sub.2-C.sub.6)-alkynyloxycarbonyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, R.sup.12 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyloxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, R.sup.13 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.10)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, NR.sup.10R.sup.11 and W represents oxygen or sulfur.
4. The compound of formula (I) as claimed in claim 1 and/or the salt thereof, wherein Q represents the groups Q-1 to Q-29 ##STR00876## ##STR00877## ##STR00878## A.sup.1, A2, A.sup.3, A.sup.4 are identical or different and independently of one another represent N (nitrogen) or the moiety CR.sup.8, but there are never more than two adjacent nitrogen atoms, and where R.sup.8 in the moiety CR.sup.8 in each case has identical or different meanings according to the definition above, X and Y independently of one another represent CH or the moiety CR.sup.1, where X represents CH if Y represents the moiety CR.sup.1 and X represents the moiety CR.sup.1 if Y represents CH, R.sup.1 represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1-bi(cyclopropyl)-1-yl, 1,1-bi(cyclopropyl)-2-yl, 2-methyl-1,1-bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-1-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, trifluoromethoxy, difluoromethoxy, pentafluoroethoxy, 2,2,1,1-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5-bis(trifluoromethyl)-phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethylthiophenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, prop-2-en-1-yloxy, but-3-en-1-yloxy, pent-4-en-1-yloxy, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 2-(trimethylsilyl)ethyn-1-yl, 2-(triethyl silyl)ethyn-1-yl, 2-(triisopropylsilyl)ethyn-1-yl, amino, dimethylamino, diethylamino, methylamino, ethylamino, cyclopropylamino, n-propylamino, isopropylamino, R.sup.3 represents hydroxy, hydrothio, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propyloxy, 1-methylethoxy, n-butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2-methylpropyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, p-chlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, p-methoxyphenylmethoxy, p-nitrophenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, methoxy-n-butyloxy, ethoxymethoxy, ethoxyethoxy, ethoxy-n-propyloxy, ethoxy-n-butyloxy, n-propyloxymethoxy, isopropyloxymethoxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylcarbonyloxy, 1-ethyl-2-methylpropylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy, thiophen-2-ylcarbonyloxy, furan-2-ylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, isopropyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4-trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, cyclopropylsulfonyloxy cyclobutylsulfonyloxy, cyclopentylsulfonyloxy, cyclohexylsulfonyloxy, phenylsulfonyloxy, p-chlorophenylsulfonyloxy, m-chlorophenylsulfonyloxy, o-chlorophenylsulfonyloxy, p-fluorophenylsulfonyloxy, m-fluorophenylsulfonyloxy, o-fluorophenylsulfonyloxy, p-methoxyphenylsulfonyloxy, m-methoxyphenylsulfonyloxy, o-methoxyphenylsulfonyloxy, p-methylphenylsulfonyloxy, m-methylphenylsulfonyloxy, o-methylphenylsulfonyloxy, R.sup.4 and R.sup.7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, hydrothio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, 1-fluoroprop-1-yl, 1-trifluoromethylprop-1-yl, 2-trifluoromethylprop-2-yl, 1-fluoroprop-1-yl, 2-fluoroprop-2-yl, 2-chloroprop-2-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-1-yl, 2,3-dimethylcyclopropyl, 1-cyanocycloprop-1-yl, 2-cyanocycloprop-1-yl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1l-yl, spiro[3.3]hept-2-yl, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl, adamantan-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5-bis(trifluoromethyl)-phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethylthiophenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 2-ethoxycarbonylphenyl, 3-ethoxycarbonylphenyl, 4-ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloro-pyrazin-2-yl, 3-bromo-pyrazin-2-yl, 3-methoxy-pyrazin-2-yl, 3-ethoxy-pyrazin-2-yl, 3-trifluoromethylpyrazin-2-yl, 3-cyanopyrazin-2-yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl)methyl, (3-chloropyridin-4-yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5-yl)methyl, (2,6-dichloropyridin-4-yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloropyridin-2-yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5-chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5-fluorothiophen-3-yl, 3,5-dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5-methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chlorofuran-2-yl, 5-bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 1-(4-methylphenyl)ethyl, 1-(3-methylphenyl)ethyl, 1-(2-methylphenyl)ethyl, 1-(4-chlorophenyl)ethyl, 1-(3-chlorophenyl)ethyl, 1-(2-chlorophenyl)ethyl, benzyl, (4-fluorophenyl)methyl, (3-fluorophenyl)methyl, (2-fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl, (3-bromophenyl)methyl, (2-bromophenyl)methyl, (4-iodophenyl)methyl, (3-iodophenyl)methyl, (2-iodophenyl)methyl, (3-chloro-5-trifluoromethyl-pyridin-2-yl)methyl, (2-bromo-4-fluorophenyl)methyl, (2-bromo-4-chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3-bromo-4-chlorophenyl)methyl, (3-bromo-5-fluorophenyl)methyl, (3-bromo-5-chlorophenyl)methyl, (2-fluoro-4-bromophenyl)methyl, (2-chloro-4-bromophenyl)methyl, (3-fluoro-4-bromophenyl)methyl, (3-chloro-4-bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4-fluorophenyl)methyl, (2-fluoro-3-chlorophenyl)methyl, (2-fluoro-4-chlorophenyl)methyl, (2-fluoro-5-chlorophenyl)methyl, (3-fluoro-4-chlorophenyl)methyl, (3-fluoro-5-chlorophenyl)methyl, (2-fluoro-6-chlorophenyl)methyl, 2-phenyleth-1-yl, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridin-2-yl, (3,6-dichloropyridin-2-yl)methyl, (4-trifluoromethylphenyl)methyl, (3-trifluoromethylphenyl)methyl, (2-trifluoromethylphenyl)methyl, (4-trifluoromethoxyphenyl)methyl, (3-trifluoromethoxyphenyl)methyl, (2-trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (4-methylphenyl)methyl, (3-methylphenyl)methyl, (2-methylphenyl)methyl, (4-cyanophenyl)methyl, (3-cyanophenyl)methyl, (2-cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3,5-diethylphenyl)methyl, (3,4-dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, 1-phenyleth-1-yl, 1-(o-chlorophenyl)eth-1-yl, 1,3-thiazol-2-yl, 4-methyl-1,3-thiazol-2-yl, 1,3-thiazol-2-yl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 1-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4-difluorocyclohexyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, n-butyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropyloxyethyl, methoxy-n-propyl, methoxy-n-butyl, trifluoromethoxymethyl, difluoromethoxymethyl, 2,2-difluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, trifluoromethoxyethyl, difluoromethoxyethyl, 2,2-difluoroethoxyethyl, 2,2,2-trifluoroethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-chlorophenylcarbonyl, m-chlorophenylcarbonyl, o-chlorophenylcarbonyl, p-fluorophenylcarbonyl, m-fluorophenylcarbonyl, o-fluorophenylcarbonyl, p-methoxyphenylcarbonyl, m-methoxyphenylcarbonyl, o-methoxyphenylcarbonyl, p-trifluoromethylphenylcarbonyl, m-trifluoromethylphenylcarbonyl, o-trifluoromethylphenylcarbonyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, benzyloxy, p-chlorophenylmethoxy, phenyloxy, p-chlorophenyloxy, m-chlorophenyloxy, o-chlorophenyloxy, p-fluorophenyloxy, m-fluorophenyloxy, o-fluorophenyloxy, p-methoxyphenyloxy, m-methoxyphenyloxy, o-methoxyphenyloxy, p-trifluoromethylphenyloxy, m-trifluoromethylphenyloxy, o-trifluoromethylphenyloxy, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cyclopropylmethylaminocarbonyl, cyclobutylmethylaminocarbonyl, cyclopentylmethylaminocarbonyl, cyclohexylmethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, benzylmethylaminocarbonyl, methylamino, dimethylamino, ethylamino, diethylamino, n-propylamino, isopropylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, benzylamino, cyanomethyl, cyanoethyl, 3-cyanoprop-1-yl, 2-cyanoprop-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-2-yl, 2-cyano-1,1-dimethyleth-1-yl, 1-(cyanomethyl)-1-methylprop-1-yl, hydroxycarbonyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, CHO, methoxyethylthio, ethoxyethylthio, trifluoromethoxyethylthio, pentafluoroethoxyethylthio, methylthioethylthio, ethylthioethylthio, trifluoromethylthioethylthio, pentafluorothioethylthio, benzylthio, p-chlorophenylmethylthio, m-chlorophenylmethylthio, o-chlorophenylmethylthio, p-fluorophenylmethylthio, m-fluorophenylmethylthio, o-fluorophenylmethylthio, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, phenylthio, pyrid-2-ylthio, pyrid-3-ylthio, pyrid-4-ylthio, p-chlorophenylthio, m-chlorophenylthio, o-chlorophenylthio, p-fluorophenylthio, m-fluorophenylthio, o-fluorophenylthio, p-methoxyphenylthio, m-methoxyphenylthio, o-methoxyphenylthio, p-methylphenylthio, m-methylphenylthio, o-methylphenylthio, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, phenylsulfonyloxy, p-chlorophenylsulfonyl, m-chlorophenylsulfonyl, o-chlorophenylsulfonyl, p-fluorophenylsulfonyl, m-fluorophenylsulfonyl, o-fluorophenylsulfonyl, p-methoxyphenylsulfonyl, m-methoxyphenylsulfonyl, o-methoxyphenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, o-methylphenylsulfonyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n-propyloxyprop-2-yl, 2-n-butyloxyprop-2-yl, 2-benzyloxyprop-2-yl, 2-phenylethyloxyprop-2-yl, 2-trifluoromethyloxyprop-2-yl, 2-difluoromethyloxyprop-2-yl, 2,2,2-trifluoroethyloxyprop-2-yl, 2,2-difluoroethyloxyprop-2-yl, 2-(4-chlorophenylmethoxy)prop-2-yl, 2-(4-fluorophenylmethoxy)prop-2-yl, 2-(4-bromophenylmethoxy)prop-2-yl, 2-(4-trifluoromethylphenylmethoxy)prop-2-yl, 2-(4-methylphenylmethoxy)prop-2-yl, 2-(3-chlorophenylmethoxy)prop-2-yl, 2-(3-fluorophenylmethoxy)prop-2-yl, 2-(3-bromophenylmethoxy)prop-2-yl, 2-(3-trifluoromethylphenylmethoxy)prop-2-yl, 2-(3-methylphenylmethoxy)prop-2-yl, 2-(2-chlorophenylmethoxy)prop-2-yl, 2-(2-fluorophenylmethoxy)prop-2-yl, 2-(2-bromophenylmethoxy)prop-2-yl, 2-(2-trifluoromethylphenylmethoxy)prop-2-yl, 2-(2-methylphenylmethoxy)prop-2-yl, 2-(methoxymethyl)prop-2-yl, 2-(ethoxymethyl)prop-2-yl, 2-methoxycarbonylprop-2-yl, 2-ethoxycarbonylprop-2-yl, 2-hydroxycarbonylprop-2-yl, 2-aminocarbonylprop-2-yl, aminocarbonyl, aminocarbonylmethyl, aminocarbonylethyl, cyano, hydroxymethyl, hydroxyethyl, 2-hydroxyprop-2-yl, allyloxymethyl, 2-allyloxyethyl, 2-allyloxyprop-2-yl, or where R.sup.4 and R.sup.7 together with the carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-3, Q-4, Q-8, Q-9, Q-12 or Q-19, R.sup.5 represents hydrogen, formyl, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy-n-propyl, methoxy-n-butyl, ethoxy-n-propyl, ethoxy-n-butyl, hydroxyethyl, hydroxy-n-propyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl-n-propyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylethyl, isopropyloxycarbonylethyl, tert-butyloxycarbonylethyl, methoxycarbonyl-n-propyl, ethoxycarbonyl-n-propyl, benzyloxycarbonylmethyl, benzyloxycarbonylethyl, allyloxycarbonylmethyl, allyloxycarbonylethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-1-yl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyanomethyl, 2-cyanoeth-1-yl, 1-cyanoeth-1-yl, cyano-n-propyl, methoxycarbonyl, ethoxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, n-butyloxycarbonyl, allyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-chlorophenylcarbonyl, m-chlorophenylcarbonyl, o-chlorophenylcarbonyl, p-fluorophenylcarbonyl, m-fluorophenylcarbonyl, o-fluorophenylcarbonyl, p-methoxyphenylcarbonyl, m-methoxyphenylcarbonyl, o-methoxyphenylcarbonyl, p-trifluoromethylphenylcarbonyl, m-trifluoromethylphenylcarbonyl, o-trifluoromethylphenylcarbonyl, methylaminocarbonyl, ethylaminocarbonyl, isopropylaminocarbonyl, n-propylaminocarbonyl, phenylaminocarbonyl, p-Clphenylaminocarbonyl, m-Clphenylaminocarbonyl, o-Clphenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cyclopropylmethylaminocarbonyl, cyclobutylmethylaminocarbonyl, cyclopentylmethylaminocarbonyl, cyclohexylmethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, benzyl(methyl)aminocarbonyl, prop-2-en-1-yl, prop-2-yn-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 3,3-difluorocyclobut-1-yl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2,3-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,4,5-trimethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-trifluoromethoxyphenyl, 3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 3-difluoromethoxyphenyl, 4-difluoromethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 3-difluoromethylphenyl, 4-difluoromethylphenyl, 3,5-bis(trifluoromethyl)phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-trifluoromethylthiophenyl, 3-trifluoromethylthiophenyl, 4-trifluoromethylthiophenyl, methoxymethyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4-methoxycarbonylphenyl, 2-ethoxycarbonylphenyl, 3-ethoxycarbonylphenyl, 4-ethoxycarbonylphenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazin-2-ylmethyl, 3-chloro-pyrazin-2-yl, 3-bromo-pyrazin-2-yl, 3-methoxy-pyrazin-2-yl, 3-ethoxy-pyrazin-2-yl, 3-trifluoromethylpyrazin-2-yl, 3-cyanopyrazin-2-yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl)methyl, (3-chloropyridin-4-yl)methyl, (2-chloropyridin-3-yl)methyl, (2-chloropyridin-4-yl)methyl, (2-chloropyridin-5-yl)methyl, (2,6-dichloropyridin-4-yl)methyl, (3-chloropyridin-5-yl)methyl, (3,5-dichloropyridin-2-yl)methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5-chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophen-2-yl, 3-methylthiophen-2-yl, 5-fluorothiophen-3-yl, 3,5-dimethylthiophen-2-yl, 3-ethylthiophen-2-yl, 4,5-dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5-methylfuran-2-yl, 5-ethylfuran-2-yl, 5-methoxycarbonylfuran-2-yl, 5-chlorofuran-2-yl, 5-bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, benzyl, (4-fluorophenyl)methyl, (3-fluorophenyl)methyl, (2-fluorophenyl)methyl, (2,4-difluorophenyl)methyl, (3,5-difluorophenyl)methyl, (2,5-difluorophenyl)methyl, (2,6-difluorophenyl)methyl, (2,4,5-trifluorophenyl)methyl, (2,4,6-trifluorophenyl)methyl, (4-chlorophenyl)methyl, (3-chlorophenyl)methyl, (2-chlorophenyl)methyl, (2,4-dichlorophenyl)methyl, (3,5-dichlorophenyl)methyl, (2,5-dichlorophenyl)methyl, (2,6-dichlorophenyl)methyl, (2,4,5-trichlorophenyl)methyl, (2,4,6-trichlorophenyl)methyl, (4-bromophenyl)methyl, (3-bromophenyl)methyl, (2-bromophenyl)methyl, (4-iodophenyl)methyl, (3-iodophenyl)methyl, (2-iodophenyl)methyl, (3-chloro-5-trifluoromethyl-pyridin-2-yl)methyl, (2-bromo-4-fluorophenyl)methyl, (2-bromo-4-chlorophenyl)methyl, (3-bromo-4-fluorophenyl)methyl, (3-bromo-4-chlorophenyl)methyl, (3-bromo-5-fluorophenyl)methyl, (3-bromo-5-chlorophenyl)methyl, (2-fluoro-4-bromophenyl)methyl, (2-chloro-4-bromophenyl)methyl, (3-fluoro-4-bromophenyl)methyl, (3-chloro-4-bromophenyl)methyl, (2-chloro-4-fluorophenyl)methyl, (3-chloro-4-fluorophenyl)methyl, (2-fluoro-3-chlorophenyl)methyl, (2-fluoro-4-chlorophenyl)methyl, (2-fluoro-5-chlorophenyl)methyl, (3-fluoro-4-chlorophenyl)methyl, (3-fluoro-5-chlorophenyl)methyl, (2-fluoro-6-chlorophenyl)methyl, phenylethyl, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridin-2-yl, (3,6-dichloropyridin-2-yl)methyl, (4-trifluoromethylphenyl)methyl, (3-trifluoromethylphenyl)methyl, (2-trifluoromethylphenyl)methyl, (4-trifluoromethoxyphenyl)methyl, (3-trifluoromethoxyphenyl)methyl, (2-trifluoromethoxyphenyl)methyl, (4-methoxyphenyl)methyl, (3-methoxyphenyl)methyl, (2-methoxyphenyl)methyl, (4-methylphenyl)methyl, (3-methylphenyl)methyl, (2-methylphenyl)methyl, (4-cyanophenyl)methyl, (3-cyanophenyl)methyl, (2-cyanophenyl)methyl, (2,4-diethylphenyl)methyl, (3,5-diethylphenyl)methyl, (3,4-dimethylphenyl)methyl, (3,5-dimethoxyphenyl)methyl, 1-phenyleth-1-yl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, phenylsulfonyloxy, p-chlorophenylsulfonyl, m-chlorophenylsulfonyl, o-chlorophenylsulfonyl, p-fluorophenylsulfonyl, m-fluorophenylsulfonyl, o-fluorophenylsulfonyl, p-methoxyphenylsulfonyl, m-methoxyphenylsulfonyl, o-methoxyphenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, o-methylphenylsulfonyl, phenylcarbonylmethyl, p-chlorophenylcarbonylmethyl, m-chlorophenylcarbonylmethyl, o-chlorophenylcarbonylmethyl, p-fluorophenylcarbonylmethyl, m-fluorophenylcarbonylmethyl, o-fluorophenylcarbonylmethyl, methylcarbonylmethyl, ethylcarbonylmethyl, n-propylcarbonylmethyl, isopropylcarbonylmethyl, n-butylcarbonylmethyl, tert-butylcarbonylmethyl, or where R.sup.4 and R.sup.5 together with the nitrogen atom or carbon atom to which they are respectively attached form a partially saturated ring having a total of 3 to 7 members which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and optionally substituted further, if Q represents Q-13, Q-14 or Q-15, R.sup.6 represents hydrogen, methyl, ethyl, R.sup.8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, methylamino, ethylamino, isopropylamino, n-propylamino, dimethylamino, diethylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino, ethoxycarbonylmethylamino, ethoxycarbonylethylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butyloxycarbonylamino, phenylamino, N-piperidinyl, N-pyrrolidinyl, N-morpholinyl, methylaminocarbonylamino, ethylaminocarbonylamino, n-propylaminocarbonylamino, isopropylaminocarbonylamino, benzylaminocarbonylamino, phenylaminocarbonylamino, p-Clphenylaminocarbonylamino, m-Clphenylaminocarbonylamino, o-Clphenylaminocarbonylamino, cyclopropylaminocarbonylamino, cyclobutylaminocarbonylamino, cyclopentylaminocarbonylamino, cyclohexylaminocarbonylamino, dimethylaminocarbonylamino, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, tert-butyloxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy, cyclopropylaminocarbonyloxy, cyclobutylaminocarbonyloxy, cyclopentylaminocarbonyloxy, cyclohexylaminocarbonyloxy, dimethylaminocarbonyloxy, phenyloxy, p-Clphenyloxy, o-Clphenyloxy, m-Clphenyloxy, m-trifluoromethylphenyloxy, p-trifluoromethylphenyloxy, trifluoromethyloxy, difluoromethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, methylthio, ethylthio, n-propylthio, isopropylthio, phenylthio, p-Clphenylthio, m-Clphenylthio, o-Clphenylthio, pyridin-2-ylthio, pyridin-3-ylthio, benzylthio, trifluoromethylthio, pentafluoroethylthio, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, tert-butylsulfinyl, phenylsulfinyl, benzylsulfinyl, pyridin-2-ylsulfinyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, tert-butylsulfonyl, phenylsulfonyl, benzylsulfonyl, pyridin-2-ylsulfonyl, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, thiocyanato, isothiocyanato, formyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 3,3-difluorcyclobut-1-yl, 3-fluorocyclobut-1-yl, 1-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4-difluorocyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-1-yl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl, adamantan-2-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, n-propyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, allylaminocarbonyl, pentafluorothio, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, ethoxyethyl, methoxyethyl, n-propyloxyethyl, methoxy-n-propyl, ethoxy-n-propyl, 1-methoxyeth-1-yl, 1-methoxyprop-1-yl, 1-ethoxyeth-1-yl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, methylthiomethyl, methylthioethyl, methylthio-n-propyl, ethylthiomethyl, trifluoromethylthiomethyl, petntafluoroethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, methylcarbonyl, ethylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, o-Clphenylcarbonyl, m-Clphenylcarbonyl, p-Clphenylcarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, tert-butyloxycarbonylethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, isopropylaminocarbonylmethyl, benzylaminocarbonylmethyl, phenylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, allylaminocarbonylmethyl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, isopropylaminomethyl, n-propylaminomethyl, n-butylaminomethyl, methylaminoethyl, dimethylaminoethyl, diethylaminoethyl, N-pyrrolidinylmethyl, N-piperidinylmethyl, hydroxyimino, methoxyimino, ethoxyimino, n-propyloxyimino, n-butyloxyimino, isopropyloxyimino, tert-butyloxyimino, cyclopropylmethoxyimino, cyclobutylmethoxyimino, cyclopentylmethoxyimino, cyclohexylmethoxyimino, benzyloxyimino, phenyloxyimino, allyloxyimino, p-Clphenylmethyloxyimino, phenylethynyl, p-Clphenylethynyl, m-Clphenylethynyl, o-Clphenylethynyl, p-F-phenylethynyl, m-F-phenylethynyl, o-F-phenylethynyl, pyridin-2-ylethynyl, pyridin-3-ylethynyl, thiophen-2-ylethynyl, trimethylsilylethynyl, triethyl silylethynyl, tri(isopropyl)silylethynyl, cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, phenyl, benzyl, p-Clphenyl, m-Clphenyl, o-Clphenyl, p-F-phenyl, m-F-phenyl, o-F-phenyl, p-trifluoromethylphenyl, m-trifluoromethylphenyl, o-trifluoromethylphenyl, p-methylphenyl, m-methylphenyl, o-methylphenyl, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, p-Clphenylmethyl, m-Clphenylmethyl, o-Clphenylmethyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrimidin-2-yl, pyrazin-2-yl, methoxymethoxymethyl, ethoxyethoxymethyl, methoxyethoxymethyl, methylaminosulfonylamino, dimethylaminosulfonylamino, ethylaminosulfonylamino, diethylaminosulfonylamino, isopropylaminosulfonylamino, cyclopropylaminosulfonylamino, cyclobutylaminosulfonylamino, cyclopentylaminosulfonylamino, cyclohexylaminosulfonylamino, diazo, phenyldiazo, trimethylsilyl, tri(isopropyl)silyl, triethylsilyl, dimethyl(phenyl)silyl, diphenyl(methyl)silyl, or where A.sup.1 and A.sup.2, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.2 and A.sup.3, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further, or where A.sup.3 and A.sup.4, when each is a group CR.sup.8, together with the atoms to which they are attached form a partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally substituted further and W represents oxygen.
5. The compound of formula (I) as claimed in claim 1 and/or the salt thereof, wherein X and Y independently of one another represent CH or the moiety CR.sup.1, where X represents CH if Y represents the moiety CR.sup.1 and X represents the moiety CR.sup.1 if Y represents CH, R.sup.1 represents chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1-bi(cyclopropyl)-1-yl, 1,1-bi(cyclopropyl)-2-yl, 2-methyl-1,1-bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-1-yl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, prop-2-en-1-yloxy, but-3-en-1-yloxy, pent-4-en-1-yloxy, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1-pentynyl, 1-hexynyl, 2-(trimethylsilyl)ethyn-1-yl, 2-(triethyl silyl)ethyn-1-yl, 2-(triisopropylsilyl)ethyn-1-yl, amino, methylamino, ethylamino, dimethylamino, diethylamino, R.sup.3 represents hydroxy, methoxy, ethoxy, n-propyloxy, 1-methylethoxy, n-butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethoxy, n-pentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, p-chlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, p-methoxyphenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, ethoxymethoxy, ethoxyethoxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, isopropyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4-trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethyl sulfonyloxy, cyclopropylsulfonyloxy, R.sup.6 represents hydrogen, W represents oxygen and Q represents one of the moieties Q-1.1 to Q-29.5: ##STR00879## ##STR00880## ##STR00881## ##STR00882## ##STR00883## ##STR00884## ##STR00885## ##STR00886## ##STR00887## ##STR00888## ##STR00889## ##STR00890## ##STR00891## ##STR00892## ##STR00893## ##STR00894## ##STR00895## ##STR00896## ##STR00897## ##STR00898## ##STR00899## ##STR00900## ##STR00901## ##STR00902## ##STR00903## ##STR00904## ##STR00905## ##STR00906## ##STR00907## ##STR00908## ##STR00909## ##STR00910## ##STR00911## ##STR00912## ##STR00913## ##STR00914## ##STR00915## ##STR00916## ##STR00917## ##STR00918## ##STR00919## ##STR00920## ##STR00921## ##STR00922## ##STR00923## ##STR00924## ##STR00925## ##STR00926## ##STR00927## ##STR00928## ##STR00929## ##STR00930## ##STR00931## ##STR00932## ##STR00933## ##STR00934## ##STR00935## ##STR00936## ##STR00937## ##STR00938## ##STR00939## ##STR00940## ##STR00941## ##STR00942## ##STR00943## ##STR00944## ##STR00945## ##STR00946## ##STR00947## ##STR00948## ##STR00949## ##STR00950## ##STR00951## ##STR00952## ##STR00953## ##STR00954## ##STR00955## ##STR00956## ##STR00957## ##STR00958## ##STR00959## ##STR00960## ##STR00961## ##STR00962## ##STR00963## ##STR00964## ##STR00965## ##STR00966## ##STR00967## ##STR00968## ##STR00969## ##STR00970## ##STR00971## ##STR00972##
6. The compound of formula (I) as claimed in claim 5 and/or the salt thereof, wherein X and Y independently of one another represent CH or the moiety CR.sup.1, where X represents CH if Y represents the moiety CR.sup.1 and X represents the moiety CR.sup.1 if Y represents CH, R.sup.1 represents methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-1-yl, adamantan-2-yl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1,1-bi(cyclopropyl)-1-yl, 1,1-bi(cyclopropyl)-2-yl, 2-methyl-1,1-bi(cyclopropyl)-2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-1-yl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, p-Clphenyloxy, thiophen-2-yl, thiophen-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, prop-2-en-1-yloxy, but-3-en-1-yloxy, pent-4-en-1-yloxy, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1-pentynyl, 1-hexynyl, 2-(trimethylsilyl)ethyn-1-yl, 2-(triethyl silyl)ethyn-1-yl, 2-(triisopropylsilyl)ethyn-1-yl, R.sup.3 represents hydroxy, methoxy, ethoxy, n-propyloxy, 1-methylethoxy, n-butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethoxy, n-pentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, benzyloxy, p-chlorophenylmethoxy, m-chlorophenylmethoxy, o-chlorophenylmethoxy, p-methoxyphenylmethoxy, methoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, ethoxymethoxy, ethoxyethoxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, isopropyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, pyridin-2-ylcarbonyloxy, pyridin-3-ylcarbonyloxy, pyridin-4-ylcarbonyloxy, 4-trifluoromethylpyridin-3-ylcarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, cyclopropylsulfonyloxy, R.sup.6 represents hydrogen, W represents oxygen and Q represents one of the moieties Q-1.1 to Q-29.5.
7. A product comprising one or more compounds of formula (I) and/or salts thereof, as defined in claim 1, as herbicide and/or plant growth regulator.
8. A herbicidal and/or plant growth-regulating composition, comprising one or more compounds of the formula (I) and/or salts 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.
9. A method for controlling one or more harmful plants and/or for regulating the growth of plants, comprising applying an effective amount of one or more compounds of the formula (I) and/or salts thereof, as defined in claim 1, of a composition thereof to the plants, seeds of plants, soil in which or on which the plants grow and/or an area under cultivation.
Description
SYNTHESIS EXAMPLES
No. I.1-162: 5-Hydroxy-4-methyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one
[0186] ##STR00732##
[0187] Citraconic anhydride (2000 mg, 17.84 mmol, 1.0 equiv) and 3-amino-5-tert-butyl-1,2-isoxazole (2501 mg, 17.84 mmol, 1.0 equiv) were dissolved in acetic acid (50 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-1-(5-tert-butyl-1,2-isoxazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (3220 mg, 77% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.54 (m, 1H), 6.32 (s, 1H), 2.19 (s, 3H), 1.37 (s, 9H). 4-Methyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-pyrrole-2,5-dione (480 mg, 2.05 mmol, 1.0 equiv) was dissolved in methanol (5 ml) and cooled to a temperature 30 C., and sodium borohydride (155 mg, 4.09 mmol, 2.0 equiv) was added a little at a time. The resulting reaction mixture was stirred at 30 C. for 1 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final purification by column chromatography (gradient ethyl acetate/heptane) of the resulting crude product, it was possible to separate 5-hydroxy-4-methyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one from the isomeric 5-hydroxy-3-methyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one 1.2-162 and to isolate the compound in the form of a colorless solid (155 mg, 32% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.72 (s, 1H), 5.95 (m, 1H), 5.90 (br. d, 1H), 4.44 (br. d, 1H), 2.16 (s, 3H), 1.36 (s, 9H).
No. I.1-290: 5-Hydroxy-4-methyl-1-(3-tert-butyl-1,2-isoxazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one
[0188] ##STR00733##
[0189] Citraconic anhydride (2000 mg, 17.84 mmol, 1.0 equiv) and 5-amino-3-tert-butyl-1,2-isoxazole (2752 mg, 19.63 mmol, 1.1 equiv) were dissolved in acetic acid (50 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-1-(3-tert-butyl-1,2-isoxazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (3620 mg, 78% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.56 (m, 1H), 6.22 (s, 1H), 2.19 (s, 3H), 1.35 (s, 9H). 4-Methyl-1-(3-tert-butyl-1,2-isoxazol-5-yl)pyrrole-2,5-dione (3500 mg, 14.94 mmol, 1.0 equiv) was dissolved in methanol (90 ml) and cooled to a temperature 30 C., and sodium borohydride (790 mg, 20.92 mmol, 1.4 equiv) was added a little at a time. The resulting reaction mixture was stirred at 30 C. for 1 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final purification by column chromatography (gradient ethyl acetate/heptane) of the resulting crude product, it was possible to separate 5-hydroxy-4-methyl-1-(3-tert-butyl-1,2-isoxazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one from the isomeric 5-hydroxy-3-methyl-1-(3-tert-butyl-1,2-isoxazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one 1.2-290 and to isolate the compound in the form of a colorless solid (350 mg, 10% of theory). .sup.1H-NMR (400 MHz, d.sub.6-DMSO , ppm) 7.09 (br. d, 1H), 6.21 (s, 1H), 6.03 (m, 1H), 5.90 (br. d, 1H), 2.04 (s, 3H), 1.27 (s, 9H).
No. I.1-387: 5-Hydroxy-4-methyl-1-(1,5-diphenyl-1,2-pyrazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one
[0190] ##STR00734##
[0191] Citraconic anhydride (519 mg, 4.64 mmol, 1.1 equiv) and 3-amino-1,5-diphenyl-1,2-pyrazole (1000 mg, 4.21 mmol, 1.0 equiv) were dissolved in acetonitrile (20 ml), pyridine (0.14 ml, 1.69 mmol, 0.4 equiv) was added and the mixture was stirred under reflux conditions for 14 h. After cooling to room temperature, water and ethyl acetate were added and the mixture was extracted thoroughly. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-1-(1,5-diphenyl-1,2-pyrazol-3-yl)pyrrole-2,5-dione in the form of a colorless solid (100 mg, 7% of theory). 4-Methyl-1-(1,5-diphenyl-1,2-pyrazol-3-yl)pyrrole-2,5-dione (80 mg, 0.24 mmol, 1.0 equiv) was dissolved in a mixture of methanol and tetrahydrofuran (20 ml, 1:1 mixture) and cooled to a temperature 30 C., and sodium borohydride (18 mg, 0.48 mmol, 2.0 equiv) was added. The resulting reaction mixture was stirred at 30 C. for 2 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4-methyl-1-(1,5-diphenyl-1,2-pyrazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (11 mg, 13% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.36-7.24 (m, 10H), 7.06 (s, 1H), 5.98 (s, 1H), 5.95 (br. d, 1H), 4.81 (br. m, 1H), 2.16 (s, 3H).
No. I.1-451: 5-Hydroxy-4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one
[0192] ##STR00735##
[0193] 5-Ethylcarbonyloxy -4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one (130 mg, 0.37 mmol, 1.0 equiv) and lithium hydroxide (10 mg, 0.41 mmol, 1.1 equiv) were dissolved in a mixture of tetrahydrofuran and water (9 ml, 1:1 mixture) and stirred at room temperature for 4 h. After the reaction had ended, buffer solution was added carefully to adjust the pH to 4-5, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (50 mg, 46% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 8.76 (s, 1H), 8.41 (s, 1H), 6.07 (m, 1H), 5.96 (s, 1H), 4.93 (d, 1H), 2.18 (s, 3H).
No. I.1-558: 5-Hydroxy-4-methyl-1-(3-ethyl-1,2,4-thiadiazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one
[0194] ##STR00736##
[0195] Citraconic anhydride (400 mg, 3.57 mmol, 1.0 equiv), p-toluenesulfonic acid (92 mg, 0.54 mmol) and 5-amino-3-ethyl-1,2,4-thiadiazole (461 mg, 3.57 mmol, 1.0 equiv) were dissolved in toluene (12 ml) and stirred under microwave conditions at a temperature of 85 C. for 60 minutes. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-1-(3-ethyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (120 mg, 15% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.67 (m, 1H), 3.04 (q, 2H), 2.25 (s, 3H), 1.40 (t, 3H). 4-Methyl-1-(3-ethyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione (100 mg, 0.45 mmol, 1.0 equiv) was dissolved in a mixture of tetrahydrofuran and methanol (10 ml, 1:1) and cooled to a temperature of 30 C., and sodium borohydride (17 mg, 0.45 mmol, 1.0 equiv) was added. The resulting reaction mixture was stirred at 30 C. for 2 h and then slowly warmed to room temperature. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4-methyl-1-(3-ethyl-1,2,4-thiadiazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (30 mg, 30% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.08 (m, 1H), 6.03 (br. s, 1H), 4.77 (d, 1H), 2.92-2.86 (q, 2H), 2.23 (s, 3H), 1.37 (t, 3H).
No. I.1-560: 5-Hydroxy-4-methyl-1-(3-isopropyl-1,2,4-thiadiazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one
[0196] ##STR00737##
[0197] Citraconic anhydride (400 mg, 3.57 mmol, 1.0 equiv), p-toluenesulfonic acid (92 mg, 0.54 mmol) and 5-amino-3-isopropyl-1,2,4-thiadiazole (511 mg, 3.57 mmol, 1.0 equiv) were dissolved in toluene (12 ml) and stirred under microwave conditions at a temperature of 95 C. for 60 minutes. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 4-methyl-1-(3-isopropyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (90 mg, 11% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.66 (m, 1H), 3.35 (sept, 1H), 2.24 (s, 3H), 1.41 (d, 6H). 4-Methyl-1-(3-isopropyl-1,2,4-thiadiazol-5-yl)pyrrole-2,5-dione (75 mg, 0.32 mmol, 1.0 equiv) was dissolved in a mixture of tetrahydrofuran and methanol (8 ml, 1:1) and cooled to a temperature of 30 C., and sodium borohydride (12 mg, 0.45 mmol, 1.0 equiv) was added. The resulting reaction mixture was stirred at 30 C. for 2 h and then slowly warmed to room temperature. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-hydroxy-4-methyl-1-(3-isopropyl-1,2,4-thiadiazol-5-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (7 mg, 9% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.08 (m, 1H), 6.05 (d, 1H), 4.81 (d, 1H), 3.23-3.15 (sept, 1H), 2.23 (s, 3H), 1.37 (d, 6H).
No. I.5-451: 5-Ethylcarbonyloxy-4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one
[0198] ##STR00738##
[0199] 5-Hydroxy-4-methyl-2,5-dihydrofuran-2-one (300 mg, 2.63 mmol, 1.0 equiv) and 2-amino-5-chloro-4-trifluoromethylpyridine (568 mg, 2.89 mmol, 1.1 equiv) were dissolved in abs. toluene (12 ml) and stirred under reflux conditions for 16 h. After cooling to room temperature, the reaction mixture was filtered off with suction and, after thorough drying, 5-(5-chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one was isolated without any further purification in the form of a colorless solid (530 mg, 68% of theory).). .sup.1H-NMR (400 MHz, d.sub.6-DMSO , ppm) 8.43 (s, 1H), 8.36 (d, 1H), 7.06 (s, 1H), 6.78 (d, 1H), 6.15 (m, 1H), 2.07 (s, 3H). 5-(5-Chloro-4-trifluoromethylpyridin-2-yl)amino-4-methyl-2,5-dihydrofuran-2-one (250 mg, 0.85 mmol, 1.0 equiv) was dissolved in propionic anhydride (2.22 g, 20 equiv) and stirred at a temperature of 155 C. for 4 h. After cooling to room temperature, the reaction mixture was filtered off with suction, and final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethylcarbonyloxy-4-methyl-1-(5-chloro-4-trifluoromethylpyridin-2-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (35 mg, 12% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 8.67 (s, 1H), 8.39 (s, 1H), 7.42 (s, 1H), 6.02 (m, 1H), 2.39-2.32 (m, 2H), 2.08 (s, 3H), 1.17 (t, 3H).
No. I.11-162: 5-Ethoxycarbonyloxy-4-methyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one
[0200] ##STR00739##
[0201] 5-Hydroxy-4-methyl-2,5-dihydrofuran-2-one (1000 mg, 8.76 mmol, 1.0 equiv) and 3-amino-5-tert-butyl-1,2-isoxazole (1351 mg, 9.64 mmol, 1.1 equiv) were dissolved in abs. toluene (20 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, the reaction mixture was filtered off with suction and, after thorough drying, 5-(5-tert-butyl-1,2-isoxazol-3-yl)amino-4-methyl-2,5-dihydrofuran-2-one was isolated without any further purification in the form of a colorless solid (1470 mg, 71% of theory).). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.12 (m, 1H), 5.96 (d, 1H), 5.65 (s, 1H), 4.95 (br. d, 1H), 2.14 (s, 3H), 1.31 (s, 9H). 5-(5-tert-Butyl-1,2-isoxazol-3-yl)amino-4-methyl-2,5-dihydrofuran-2-one (150 mg, 0.64 mmol, 1.0 equiv) was dissolved in diethyl carbonate (1.54 ml, 20 equiv) and stirred at a temperature of 120 C. for 8 h. After cooling to room temperature, the reaction mixture was filtered off with suction, and final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethoxycarbonyloxy-4-methyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (63 mg, 32% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.95 (s, 1H), 6.68 (s, 1H), 6.02 (m, 1H), 4.37-4.32 (m, 2H), 2.12 (s, 3H), 1.39 (t, 3H), 1.34 (s, 9H).
No. I.22-162: 5-Hydroxy-3-tert-butyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one
[0202] ##STR00740##
[0203] 3-tert-Butylfuran-2,5-dione (1600 mg, 10.38 mmol, 1.0 equiv) and 3-amino-5-tert-butyl-1,2-isoxazole (1600 mg, 11.42 mmol, 1.1 equiv) were dissolved in acetic acid (40 ml) and stirred under reflux conditions for 8 h. After cooling to room temperature, water, sat. sodium bicarbonate solution and ethyl acetate were added and the reaction mixture was extracted. The aqueous phase was repeatedly re-extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 3-tert-butyl-1-(5-tert-butyl-1,2-isoxazol-5-yl)pyrrole-2,5-dione in the form of a colorless solid (1550 mg, 54% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.43 (2, 1H), 6.33 (s, 1H), 1.37 (s, 9H), 1.36 (s, 9H). 3-tert-Butyl-1-(5-tert-butyl-1,2-isoxazol-5-yl)pyrrole-2,5-dione (1400 mg, 5.07 mmol, 1.0 equiv) was dissolved in methanol (20 ml) and cooled to a temperature of 30 C., and sodium borohydride (2.0 equiv) was added a little at a time. The resulting reaction mixture was stirred at 30 C. for 1 h and then slowly warmed to room temperature and stirred at room temperature for another 1 h. After the reaction had ended, acetic acid was added carefully to adjust the pH to 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted vigorously with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. By final purification by column chromatography (gradient ethyl acetate/heptane) of the resulting crude product, it was possible to separate 5-hydroxy-3-tert-butyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one from the isomeric 5-hydroxy-4-tert-butyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one 1.21-162 and to isolate the compound in the form of a colorless solid (990 mg, 70% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.77 (s, 1H), 6.66 (s, 1H), 5.97 (br. d, 1H), 4.28 (br. d, 1H), 1.35 (s, 9H), 1.30 (s, 9H).
No. I.26-162: 5-Ethylcarbonyloxy-3-tert-butyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one
[0204] ##STR00741##
[0205] Under argon, 5-hydroxy-3-tert-butyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one (950 mg, 3.41 mmol, 1.0 equiv) was dissolved in abs. dichloromethane (75 ml), diisopropylethylamine (706 mg, 5.46 mmol, 1.6 equiv), propionyl chloride (474 mg, 5.12 mmol, 1.5 equiv) and 4-dimethylaminopyridine (42 mg, 0.34 mmol, 0.1 equiv) were added and the mixture was stirred at room temperature for 2 h. This was followed by the addition of water and dichloromethane and thorough extraction. The aqueous phase was repeatedly re-extracted vigorously with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification by column chromatography of the resulting crude product (gradient ethyl acetate/heptane) gave 5-ethylcarbonyloxy-3-tert-butyl-1-(5-tert-butyl-1,2-isoxazol-3-yl)-1,5-dihydro-2H-pyrrol-2-one in the form of a colorless solid (450 mg, 39% of theory). .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.90 (s, 1H), 6.75 (s, 1H), 6.71 (m, 1H), 2.52-2.34 (m, 2H), 1.34 (s, 9H), 1.29 (s, 9H), 1.17 (t, 3H).
[0206] 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 monosubstituted heteroarylpyrrolones, the compounds cited below are obtained. If in Table 1 a structural element is defined by a structural formula containing a broken line, this broken line means that at this position the group in question is attached to the remainder of the molecule.
##STR00742##
[0207] Table I.1: Preferred compounds of the formula (I.1) are the compounds I.1-1 to I.1-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.1-1 to I.1-708 of Table I.1 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
TABLE-US-00002 TABLE 1 No. Q 1 Q-1.1 2 Q-1.2 3 Q-1.3 4 Q-1.4 5 Q-1.5 6 Q-1.6 7 Q-1.7 8 Q-1.8 9 Q-1.9 10 Q-1.10 11 Q-1.11 12 Q-1.12 13 Q-1.13 14 Q-1.14 15 Q-1.15 16 Q-1.16 17 Q-1.17 18 Q-1.18 19 Q-1.19 20 Q-1.20 21 Q-2.1 22 Q-2.2 23 Q-2.3 24 Q-2.4 25 Q-2.5 26 Q-2.6 27 Q-2.7 28 Q-2.8 29 Q-2.9 30 Q-2.10 31 Q-2.11 32 Q-2.12 33 Q-2.13 34 Q-2.14 35 Q-2.15 36 Q-2.16 37 Q-2.17 38 Q-2.18 39 Q-2.19 40 Q-2.20 41 Q-3.1 42 Q-3.2 43 Q-3.3 44 Q-3.4 45 Q-3.5 46 Q-3.6 47 Q-3.7 48 Q-3.8 49 Q-3.9 50 Q-3.10 51 Q-3.11 52 Q-3.12 53 Q-3.13 54 Q-3.14 55 Q-3.15 56 Q-3.16 57 Q-3.17 58 Q-3.18 59 Q-3.19 60 Q-3.20 61 Q-3.21 62 Q-3.22 63 Q-3.23 64 Q-3.24 65 Q-3.25 66 Q-3.26 67 Q-3.27 68 Q-3.28 69 Q-3.29 70 Q-3.30 71 Q-4.1 72 Q-4.2 73 Q-4.3 74 Q-4.4 75 Q-4.5 76 Q-4.6 77 Q-4.7 78 Q-4.8 79 Q-4.9 80 Q-4.10 81 Q-4.11 82 Q-4.12 83 Q-4.13 84 Q-4.14 85 Q-4.15 86 Q-4.16 87 Q-4.17 88 Q-4.18 89 Q-4.19 90 Q-4.20 91 Q-5.1 92 Q-5.2 93 Q-5.3 94 Q-5.4 95 Q-5.5 96 Q-5.6 97 Q-5.7 98 Q-5.8 99 Q-5.9 100 Q-5.10 101 Q-5.11 102 Q-5.12 103 Q-5.13 104 Q-5.14 105 Q-5.15 106 Q-5.16 107 Q-5.17 108 Q-5.18 109 Q-5.19 110 Q-5.20 111 Q-6.1 112 Q-6.2 113 Q-6.3 114 Q-6.4 115 Q-6.5 116 Q-6.6 117 Q-6.7 118 Q-6.8 119 Q-6.9 120 Q-6.10 121 Q-6.11 122 Q-6.12 123 Q-6.13 124 Q-6.14 125 Q-6.15 126 Q-6.16 127 Q-6.17 128 Q-6.18 129 Q-6.19 130 Q-6.20 131 Q-6.21 132 Q-6.22 133 Q-6.23 134 Q-6.24 135 Q-6.25 136 Q-7.1 137 Q-7.2 138 Q-7.3 139 Q-7.4 140 Q-7.5 141 Q-7.6 142 Q-7.7 143 Q-7.8 144 Q-7.9 145 Q-7.10 146 Q-7.11 147 Q-7.12 148 Q-7.13 149 Q-7.14 150 Q-7.15 151 Q-7.16 152 Q-7.17 153 Q-7.18 154 Q-7.19 155 Q-7.20 156 Q-8.1 157 Q-8.2 158 Q-8.3 159 Q-8.4 160 Q-8.5 161 Q-8.6 162 Q-8.7 163 Q-8.8 164 Q-8.9 165 Q-8.10 166 Q-8.11 167 Q-8.12 168 Q-8.13 169 Q-8.14 170 Q-8.15 171 Q-8.16 172 Q-8.17 173 Q-8.18 174 Q-8.19 175 Q-8.20 176 Q-8.21 177 Q-8.22 178 Q-8.23 179 Q-8.24 180 Q-8.25 181 Q-8.26 182 Q-8.27 183 Q-8.28 184 Q-8.29 185 Q-8.30 186 Q-8.31 187 Q-8.32 188 Q-8.33 189 Q-8.34 190 Q-8.35 191 Q-8.36 192 Q-8.37 193 Q-8.38 194 Q-8.39 195 Q-8.40 196 Q-8.41 197 Q-8.42 198 Q-8.43 199 Q-8.44 200 Q-8.45 201 Q-8.46 202 Q-8.47 203 Q-8.48 204 Q-8.49 205 Q-8.50 206 Q-8.51 207 Q-8.52 208 Q-8.53 209 Q-8.54 210 Q-8.55 211 Q-8.56 212 Q-8.57 213 Q-8.58 214 Q-8.59 215 Q-8.60 216 Q-8.61 217 Q-8.62 218 Q-8.63 219 Q-8.64 220 Q-8.65 221 Q-8.66 222 Q-8.67 223 Q-8.68 224 Q-8.69 225 Q-8.70 226 Q-8.71 227 Q-8.72 228 Q-8.73 229 Q-8.74 230 Q-8.75 231 Q-9.1 232 Q-9.2 233 Q-9.3 234 Q-9.4 235 Q-9.5 236 Q-9.6 237 Q-9.7 238 Q-9.8 239 Q-9.9 240 Q-9.10 241 Q-9.11 242 Q-9.12 243 Q-9.13 244 Q-9.14 245 Q-9.15 246 Q-9.16 247 Q-9.17 248 Q-9.18 249 Q-9.19 250 Q-9.20 251 Q-10.1 252 Q-10.2 253 Q-10.3 254 Q-10.4 255 Q-10.5 256 Q-10.6 257 Q-10.7 258 Q-10.8 259 Q-10.9 260 Q-10.10 261 Q-10.11 262 Q-10.12 263 Q-10.13 264 Q-10.14 265 Q-10.15 266 Q-10.16 267 Q-10.17 268 Q-10.18 269 Q-10.19 270 Q-10.20 271 Q-11.1 272 Q-11.2 273 Q-11.3 274 Q-11.4 275 Q-11.5 276 Q-11.6 277 Q-11.7 278 Q-11.8 279 Q-11.9 280 Q-11.10 281 Q-11.11 282 Q-11.12 283 Q-11.13 284 Q-11.14 285 Q-11.15 286 Q-12.1 287 Q-12.2 288 Q-12.3 289 Q-12.4 290 Q-12.5 291 Q-12.6 292 Q-12.7 293 Q-12.8 294 Q-12.9 295 Q-12.10 296 Q-12.11 297 Q-12.12 298 Q-12.13 299 Q-12.14 300 Q-12.15 301 Q-12.16 302 Q-12.17 303 Q-12.18 304 Q-12.19 305 Q-12.20 306 Q-12.21 307 Q-12.22 308 Q-12.23 309 Q-12.24 310 Q-12.25 311 Q-13.1 312 Q-13.2 313 Q-13.3 314 Q-13.4 315 Q-13.5 316 Q-13.6 317 Q-13.7 318 Q-13.8 319 Q-13.9 320 Q-13.10 321 Q-13.11 322 Q-13.12 323 Q-13.13 324 Q-13.14 325 Q-13.15 326 Q-13.16 327 Q-13.17 328 Q-13.18 329 Q-13.19 330 Q-13.20 331 Q-13.21 332 Q-13.22 333 Q-13.23 334 Q-13.24 335 Q-13.25 336 Q-13.26 337 Q-13.27 338 Q-13.28 339 Q-13.29 340 Q-13.30 341 Q-13.31 342 Q-13.32 343 Q-13.33 344 Q-13.34 345 Q-13.35 346 Q-13.36 347 Q-13.37 348 Q-13.38 349 Q-13.39 350 Q-13.40 351 Q-13.41 352 Q-13.42 353 Q-13.43 354 Q-13.44 355 Q-13.45 356 Q-13.46 357 Q-13.47 358 Q-13.48 359 Q-13.49 360 Q-13.50 361 Q-13.51 362 Q-13.52 363 Q-13.53 364 Q-13.54 365 Q-13.55 366 Q-13.56 367 Q-13.57 368 Q-13.58 369 Q-13.59 370 Q-13.60 371 Q-13.61 372 Q-13.62 373 Q-13.63 374 Q-13.64 375 Q-13.65 376 Q-13.66 377 Q-13.67 378 Q-13.68 379 Q-13.69 380 Q-13.70 381 Q-13.71 382 Q-13.72 383 Q-13.73 384 Q-13.74 385 Q-13.75 386 Q-13.76 387 Q-13.77 388 Q-13.78 389 Q-13.79 390 Q-13.80 391 Q-14.1 392 Q-14.2 393 Q-14.3 394 Q-14.4 395 Q-14.5 396 Q-14.6 397 Q-14.7 398 Q-14.8 399 Q-14.9 400 Q-14.10 401 Q-14.11 402 Q-14.12 403 Q-14.13 404 Q-14.14 405 Q-14.15 406 Q-14.16 407 Q-14.17 408 Q-14.18 409 Q-14.19 410 Q-14.20 411 Q-15.1 412 Q-15.2 413 Q-15.3 414 Q-15.4 415 Q-15.5 416 Q-15.6 417 Q-15.7 418 Q-15.8 419 Q-15.9 420 Q-15.10 421 Q-15.11 422 Q-15.12 423 Q-15.13 424 Q-15.14 425 Q-15.15 426 Q-15.16 427 Q-15.17 428 Q-15.18 429 Q-15.19 430 Q-15.20 431 Q-15.21 432 Q-15.22 433 Q-15.23 434 Q-15.24 435 Q-15.25 436 Q-15.26 437 Q-15.27 438 Q-15.28 439 Q-15.29 440 Q-15.30 441 Q-16.1 442 Q-16.2 443 Q-16.3 444 Q-16.4 445 Q-16.5 446 Q-16.6 447 Q-16.7 448 Q-16.8 449 Q-16.9 450 Q-16.10 451 Q-16.11 452 Q-16.12 453 Q-16.13 454 Q-16.14 455 Q-16.15 456 Q-16.16 457 Q-16.17 458 Q-16.18 459 Q-16.19 460 Q-16.20 461 Q-16.21 462 Q-16.22 463 Q-16.23 464 Q-16.24 465 Q-16.25 466 Q-16.26 467 Q-16.27 468 Q-16.28 469 Q-16.29 470 Q-16.30 471 Q-16.31 472 Q-16.32 473 Q-16.33 474 Q-16.34 475 Q-16.35 476 Q-16.36 477 Q-16.37 478 Q-16.38 479 Q-16.39 480 Q-16.40 481 Q-16.41 482 Q-16.42 483 Q-16.43 484 Q-16.44 485 Q-16.45 486 Q-16.46 487 Q-16.47 488 Q-16.48 489 Q-16.49 490 Q-16.50 491 Q-16.51 492 Q-16.52 493 Q-16.35 494 Q-16.45 495 Q-16.55 496 Q-16.56 497 Q-16.57 498 Q-16.58 499 Q-16.59 500 Q-16.60 501 Q-16.61 502 Q-16.62 503 Q-16.63 504 Q-16.64 505 Q-16.65 506 Q-16.66 507 Q-16.67 508 Q-16.68 509 Q-16.69 510 Q-16.70 511 Q-16.71 512 Q-16.72 513 Q-16.73 514 Q-16.74 515 Q-16.75 516 Q-16.76 517 Q-16.77 518 Q-16.78 519 Q-16.79 520 Q-16.80 521 Q-17.1 522 Q-17.2 523 Q-17.3 524 Q-17.4 525 Q-17.5 526 Q-17.6 527 Q-17.7 528 Q-17.8 529 Q-17.9 530 Q-17.10 531 Q-18.1 532 Q-18.2 533 Q-18.3 534 Q-18.4 535 Q-18.5 536 Q-18.6 537 Q-18.7 538 Q-18.8 539 Q-18.9 540 Q-18.10 541 Q-19.1 542 Q-19.2 543 Q-19.3 544 Q-19.4 545 Q-19.5 546 Q-19.6 547 Q-19.7 548 Q-19.8 549 Q-19.9 550 Q-19.10 551 Q-19.11 552 Q-19.12 553 Q-19.13 554 Q-19.14 555 Q-19.15 556 Q-23.1 557 Q-23.2 558 Q-23.3 559 Q-23.4 560 Q-23.5 561 Q-23.6 562 Q-23.7 563 Q-23.8 564 Q-23.9 565 Q-23.10 566 Q-23.11 567 Q-23.12 568 Q-23.13 569 Q-23.14 570 Q-23.15 571 Q-23.16 572 Q-23.17 573 Q-23.18 574 Q-23.19 575 Q-23.20 576 Q-23.21 577 Q-23.22 578 Q-23.23 579 Q-23.24 580 Q-23.25 581 Q-23.26 582 Q-23.27 583 Q-23.28 584 Q-23.29 585 Q-23.30 586 Q-23.31 587 Q-23.32 588 Q-23.33 589 Q-23.34 590 Q-23.35 591 Q-23.36 592 Q-23.37 593 Q-23.38 594 Q-23.39 595 Q-23.40 596 Q-23.41 597 Q-23.42 598 Q-23.43 599 Q-23.44 600 Q-23.45 601 Q-23.46 602 Q-23.47 603 Q-23.48 604 Q-23.49 605 Q-23.50 606 Q-23.51 607 Q-23.52 608 Q-23.53 609 Q-23.54 610 Q-23.55 611 Q-23.56 612 Q-23.57 613 Q-23.58 634 Q-25.1 635 Q-25.2 636 Q-25.3 637 Q-25.4 638 Q-25.5 639 Q-25.6 640 Q-25.7 641 Q-25.8 642 Q-25.9 643 Q-25.10 644 Q-25.11 645 Q-25.12 646 Q-25.13 647 Q-25.14 648 Q-25.15 649 Q-25.16 650 Q-25.17 651 Q-25.18 652 Q-25.19 653 Q-25.20 654 Q-25.21 655 Q-25.22 656 Q-25.23 657 Q-25.24 658 Q-25.25 659 Q-25.26 660 Q-25.27 661 Q-25.28 662 Q-25.29 663 Q-25.30 664 Q-25.31 665 Q-25.32 666 Q-25.33 667 Q-25.34 668 Q-25.35 669 Q-25.36 670 Q-25.37 671 Q-25.38 672 Q-25.39 673 Q-25.40 674 Q-25.41 675 Q-25.42 676 Q-25.43 677 Q-25.44 678 Q-25.45 679 Q-26.1 680 Q-26.2 681 Q-26.3 682 Q-26.4 683 Q-26.5 684 Q-26.6 685 Q-26.7 686 Q-26.8 687 Q-26.9 688 Q-26.10 689 Q-26.11 690 Q-26.12 691 Q-26.13 692 Q-26.14 693 Q-26.15 694 Q-12.26 695 Q-12.27 696 Q-12.28 697 Q-12.29 698 Q-12.30 699 Q-27.1 700 Q-27.2 701 Q-27.3 702 Q-27.4 703 Q-27.5 704 Q-28.1 705 Q-28.2 706 Q-28.3 707 Q-28.4 708 Q-28.5
##STR00743##
[0208] Table I.2: Preferred compounds of the formula (I.2) are the compounds I.2-1 to I.2-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.2-1 to I.2-708 of Table I.2 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00744##
[0209] Table I.3: Preferred compounds of the formula (I.3) are the compounds I.3-1 to I.3-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.3-1 to I.3-708 of Table I.3 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00745##
[0210] Table I.4: Preferred compounds of the formula (I.4) are the compounds I.4-1 to I.4-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.4-1 to I.4-708 of Table I.4 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00746##
[0211] Table I.5: Preferred compounds of the formula (I.5) are the compounds I.5-1 to I.5-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.5-1 to I.5-708 of Table I.5 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00747##
[0212] Table I.6: Preferred compounds of the formula (I.6) are the compounds I.6-1 to I.6-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.6-1 to I.6-708 of Table I.6 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00748##
[0213] Table I.7: Preferred compounds of the formula (I.7) are the compounds I.7-1 to I.7-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.7-1 to I.7-708 of Table I.7 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00749##
[0214] Table I.8: Preferred compounds of the formula (I.8) are the compounds I.8-1 to I.8-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.8-1 to I.8-708 of Table I.8 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00750##
[0215] Table I.9: Preferred compounds of the formula (I.9) are the compounds I.9-1 to I.9-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.9-1 to I.9-708 of Table I.9 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00751##
[0216] Table I.10: Preferred compounds of the formula (I.10) are the compounds I.10-1 to I.10-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.10-1 to I.10-708 of Table I.10 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00752##
[0217] Table I.11: Preferred compounds of the formula (I.11) are the compounds I.11-1 to I.11-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.11-1 to I.11-708 of Table I.11 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00753##
[0218] Table I.12: Preferred compounds of the formula (I.12) are the compounds I.12-1 to I.12-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.12-1 to I.12-708 of Table I.12 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00754##
[0219] Table I.13: Preferred compounds of the formula (I.13) are the compounds I.13-1 to I.13-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.13-1 to I.13-708 of Table I.13 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00755##
[0220] Table I.14: Preferred compounds of the formula (I.14) are the compounds I.14-1 to I.14-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.14-1 to I.14-708 of Table I.14 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00756##
[0221] Table I.15: Preferred compounds of the formula (I.15) are the compounds I.15-1 to I.15-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.15-1 to I.15-708 of Table I.15 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00757##
[0222] Table I.16: Preferred compounds of the formula (I.16) are the compounds I.16-1 to I.16-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.16-1 to I.16-708 of Table I.16 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00758##
[0223] Table I.17: Preferred compounds of the formula (I.17) are the compounds I.17-1 to I.17-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.17-1 to I.17-708 of Table I.17 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00759##
[0224] Table I.18: Preferred compounds of the formula (I.18) are the compounds I.18-1 to I.18-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.18-1 to I.18-708 of Table I.18 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00760##
[0225] Table I.19: Preferred compounds of the formula (I.19) are the compounds I.19-1 to I.19-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.19-1 to I.19-708 of Table I.19 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00761##
[0226] Table I.20: Preferred compounds of the formula (I.20) are the compounds I.20-1 to I.20-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.20-1 to I.20-708 of Table I.20 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00762##
[0227] Table I.21: Preferred compounds of the formula (I.21) are the compounds I.21-1 to I.21-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.21-1 to I.21-708 of Table I.21 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00763##
[0228] Table I.22: Preferred compounds of the formula (I.22) are the compounds I.22-1 to I.22-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.22-1 to I.22-708 of Table I.22 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00764##
[0229] Table I.23: Preferred compounds of the formula (I.23) are the compounds I.23-1 to I.23-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.23-1 to I.23-708 of Table I.23 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00765##
[0230] Table I.24: Preferred compounds of the formula (I.24) are the compounds I.24-1 to I.24-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.24-1 to I.24-708 of Table I.24 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00766##
[0231] Table I.25: Preferred compounds of the formula (I.25) are the compounds I.25-1 to I.25-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.25-1 to I.25-708 of Table I.25 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00767##
[0232] Table I.26: Preferred compounds of the formula (I.26) are the compounds I.26-1 to I.26-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.26-1 to I.26-708 of Table I.26 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00768##
[0233] Table I.27: Preferred compounds of the formula (I.27) are the compounds I.27-1 to I.27-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.27-1 to I.27-708 of Table I.27 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00769##
[0234] Table I.28: Preferred compounds of the formula (I.28) are the compounds I.28-1 to I.28-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.28-1 to I.28-708 of Table I.28 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00770##
[0235] Table I.29: Preferred compounds of the formula (I.29) are the compounds I.29-1 to I.29-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.29-1 to I.29-708 of Table I.29 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00771##
[0236] Table I.30: Preferred compounds of the formula (I.30) are the compounds I.30-1 to I.30-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.30-1 to I.30-708 of Table I.30 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00772##
[0237] Table I.31: Preferred compounds of the formula (I.31) are the compounds I.31-1 to I.31-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.31-1 to I.31-708 of Table I.31 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00773##
[0238] Table I.32: Preferred compounds of the formula (I.32) are the compounds I.32-1 to I.32-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.32-1 to I.32-708 of Table I.32 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00774##
[0239] Table I.33: Preferred compounds of the formula (I.33) are the compounds I.33-1 to I.33-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.33-1 to I.33-708 of Table I.33 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00775##
[0240] Table I.34: Preferred compounds of the formula (I.34) are the compounds I.34-1 to I.34-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.34-1 to I.34-708 of Table I.34 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00776##
[0241] Table I.35: Preferred compounds of the formula (I.35) are the compounds I.35-1 to I.35-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.35-1 to I.35-708 of Table I.35 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00777##
[0242] Table I.36: Preferred compounds of the formula (I.36) are the compounds I.36-1 to I.36-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.36-1 to I.36-708 of Table I.36 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00778##
[0243] Table I.37: Preferred compounds of the formula (I.37) are the compounds I.37-1 to I.37-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.37-1 to I.37-708 of Table I.37 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00779##
[0244] Table I.38: Preferred compounds of the formula (I.38) are the compounds I.38-1 to I.38-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.38-1 to I.38-708 of Table I.38 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00780##
[0245] Table I.39: Preferred compounds of the formula (I.39) are the compounds I.39-1 to I.39-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.39-1 to I.39-708 of Table I.39 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00781##
[0246] Table I.40: Preferred compounds of the formula (I.40) are the compounds I.40-1 to I.40-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.40-1 to I.40-708 of Table I.40 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00782##
[0247] Table I.41: Preferred compounds of the formula (I.41) are the compounds I.41-1 to I.41-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.41-1 to I.41-708 of Table I.41 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00783##
[0248] Table I.42: Preferred compounds of the formula (I.42) are the compounds I.42-1 to I.42-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.42-1 to I.42-708 of Table I.42 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00784##
[0249] Table I.43: Preferred compounds of the formula (I.43) are the compounds I.43-1 to I.43-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.43-1 to I.43-708 of Table I.43 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00785##
[0250] Table I.44: Preferred compounds of the formula (I.44) are the compounds I.44-1 to I.44-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.44-1 to I.44-708 of Table I.44 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00786##
[0251] Table I.45: Preferred compounds of the formula (I.45) are the compounds I.45-1 to I.45-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.45-1 to I.45-708 of Table I.45 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00787##
[0252] Table I.46: Preferred compounds of the formula (I.46) are the compounds I.46-1 to I.46-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.46-1 to I.46-708 of Table I.46 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00788##
[0253] Table I.47: Preferred compounds of the formula (I.47) are the compounds I.47-1 to I.47-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.47-1 to I.47-708 of Table I.47 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00789##
[0254] Table I.48: Preferred compounds of the formula (I.48) are the compounds I.48-1 to I.48-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.48-1 to I.48-708 of Table I.48 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00790##
[0255] Table I.49: Preferred compounds of the formula (I.49) are the compounds I.49-1 to I.49-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.49-1 to I.49-708 of Table I.49 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00791##
[0256] Table I.50: Preferred compounds of the formula (I.50) are the compounds I.50-1 to I.50-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.50-1 to I.50-708 of Table I.50 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00792##
[0257] Table I.51: Preferred compounds of the formula (I.51) are the compounds I.51-1 to I.51-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.51-1 to I.51-708 of Table I.51 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00793##
[0258] Table I.52: Preferred compounds of the formula (I.52) are the compounds I.52-1 to I.52-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.52-1 to I.52-708 of Table I.52 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00794##
[0259] Table I.53: Preferred compounds of the formula (I.53) are the compounds I.53-1 to I.53-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.53-1 to I.53-708 of Table I.53 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00795##
[0260] Table I.54: Preferred compounds of the formula (I.54) are the compounds I.54-1 to I.54-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.54-1 to I.54-708 of Table I.54 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00796##
[0261] Table I.55: Preferred compounds of the formula (I.55) are the compounds I.55-1 to I.55-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.55-1 to I.55-708 of Table I.55 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00797##
[0262] Table I.56: Preferred compounds of the formula (I.56) are the compounds I.56-1 to I.56-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.56-1 to I.56-708 of Table I.56 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00798##
[0263] Table I.57: Preferred compounds of the formula (I.57) are the compounds I.57-1 to I.57-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.57-1 to I.57-708 of Table I.57 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00799##
[0264] Table I.58: Preferred compounds of the formula (I.58) are the compounds I.58-1 to I.58-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.58-1 to I.58-708 of Table I.58 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00800##
[0265] Table I.59: Preferred compounds of the formula (I.59) are the compounds I.59-1 to I.59-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.59-1 to I.59-708 of Table I.59 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00801##
[0266] Table I.60: Preferred compounds of the formula (I.60) are the compounds I.60-1 to I.60-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.60-1 to I.60-708 of Table I.60 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00802##
[0267] Table I.61: Preferred compounds of the formula (I.61) are the compounds I.61-1 to I.61-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.61-1 to I.61-708 of Table I.61 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00803##
[0268] Table I.62: Preferred compounds of the formula (I.62) are the compounds I.62-1 to I.62-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.62-1 to I.62-708 of Table I.62 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00804##
[0269] Table I.63: Preferred compounds of the formula (I.63) are the compounds I.63-1 to I.63-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.63-1 to I.63-708 of Table I.63 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00805##
[0270] Table I.64: Preferred compounds of the formula (I.64) are the compounds I.64-1 to I.64-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.64-1 to I.64-708 of Table I.64 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00806##
[0271] Table I.65: Preferred compounds of the formula (I.65) are the compounds I.65-1 to I.65-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.65-1 to I.65-708 of Table I.65 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00807##
[0272] Table I.66: Preferred compounds of the formula (I.66) are the compounds I.66-1 to I.66-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.66-1 to I.66-708 of Table I.66 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00808##
[0273] Table I.67: Preferred compounds of the formula (I.67) are the compounds I.67-1 to I.67-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.67-1 to I.67-708 of Table I.67 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00809##
[0274] Table I.68: Preferred compounds of the formula (I.68) are the compounds I.68-1 to I.68-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.68-1 to I.68-708 of Table I.68 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00810##
[0275] Table I.69: Preferred compounds of the formula (I.69) are the compounds I.69-1 to I.69-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.69-1 to I.69-708 of Table I.69 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00811##
[0276] Table I.70: Preferred compounds of the formula (I.70) are the compounds I.70-1 to I.70-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.70-1 to I.70-708 of Table I.70 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00812##
[0277] Table I.71: Preferred compounds of the formula (I.71) are the compounds I.71-1 to I.71-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.71-1 to I.71-708 of Table I.71 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00813##
[0278] Table I.72: Preferred compounds of the formula (I.72) are the compounds I.72-1 to I.72-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.72-1 to I.72-708 of Table I.72 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00814##
[0279] Table I.73: Preferred compounds of the formula (I.73) are the compounds I.73-1 to I.73-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.73-1 to I.73-708 of Table I.73 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00815##
[0280] Table I.74: Preferred compounds of the formula (I.74) are the compounds I.74-1 to I.74-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.74-1 to I.74-708 of Table I.74 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00816##
[0281] Table I.75: Preferred compounds of the formula (I.75) are the compounds I.75-1 to I.75-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.75-1 to I.75-708 of Table I.75 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00817##
[0282] Table I.76: Preferred compounds of the formula (I.76) are the compounds I.76-1 to I.76-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.76-1 to I.76-708 of Table I.76 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00818##
[0283] Table I.77: Preferred compounds of the formula (I.77) are the compounds I.77-1 to I.77-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.77-1 to I.77-708 of Table I.77 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00819##
[0284] Table I.78: Preferred compounds of the formula (I.78) are the compounds I.78-1 to I.78-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.78-1 to I.78-708 of Table I.78 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00820##
[0285] Table I.79: Preferred compounds of the formula (I.79) are the compounds I.79-1 to I.79-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.79-1 to I.79-708 of Table I.79 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00821##
[0286] Table I.80: Preferred compounds of the formula (I.80) are the compounds I.80-1 to I.80-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.80-1 to I.80-708 of Table I.80 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00822##
[0287] Table I.81: Preferred compounds of the formula (I.81) are the compounds I.81-1 to I.81-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.81-1 to I.81-708 of Table I.81 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00823##
[0288] Table I.82: Preferred compounds of the formula (I.82) are the compounds I.82-1 to I.82-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.82-1 to I.82-708 of Table I.82 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00824##
[0289] Table I.83: Preferred compounds of the formula (I.83) are the compounds I.83-1 to I.83-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.83-1 to I.83-708 of Table I.83 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00825##
[0290] Table I.84: Preferred compounds of the formula (I.84) are the compounds I.84-1 to I.84-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.84-1 to I.84-708 of Table I.84 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00826##
[0291] Table I.85: Preferred compounds of the formula (I.85) are the compounds I.85-1 to I.85-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.85-1 to I.85-708 of Table I.85 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00827##
[0292] Table I.86: Preferred compounds of the formula (I.86) are the compounds I.86-1 to I.86-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.86-1 to I.86-708 of Table I.86 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00828##
[0293] Table I.87: Preferred compounds of the formula (I.87) are the compounds I.87-1 to I.87-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.87-1 to I.87-708 of Table I.87 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00829##
[0294] Table I.88: Preferred compounds of the formula (I.88) are the compounds I.88-1 to I.88-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.88-1 to I.88-708 of Table I.88 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00830##
[0295] Table I.89: Preferred compounds of the formula (I.89) are the compounds I.89-1 to I.89-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.89-1 to I.89-708 of Table I.89 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00831##
[0296] Table I.90: Preferred compounds of the formula (I.90) are the compounds I.90-1 to I.90-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.90-1 to I.90-708 of Table I.90 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00832##
[0297] Table I.91: Preferred compounds of the formula (I.91) are the compounds I.91-1 to I.91-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.91-1 to I.91-708 of Table I.91 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00833##
[0298] Table I.92: Preferred compounds of the formula (I.92) are the compounds I.92-1 to I.92-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.92-1 to I.92-708 of Table I.92 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00834##
[0299] Table I.93: Preferred compounds of the formula (I.93) are the compounds I.93-1 to I.93-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.93-1 to I.93-708 of Table I.93 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00835##
[0300] Table I.94: Preferred compounds of the formula (I.94) are the compounds I.94-1 to I.94-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.94-1 to I.94-708 of Table I.94 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00836##
[0301] Table I.95: Preferred compounds of the formula (I.95) are the compounds I.95-1 to I.95-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.95-1 to I.95-708 of Table I.95 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00837##
[0302] Table I.96: Preferred compounds of the formula (I.96) are the compounds I.96-1 to I.96-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.96-1 to I.96-708 of Table I.96 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00838##
[0303] Table I.97: Preferred compounds of the formula (I.97) are the compounds I.97-1 to I.97-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.97-1 to I.97-708 of Table I.97 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00839##
[0304] Table I.98: Preferred compounds of the formula (I.98) are the compounds I.98-1 to I.98-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.98-1 to I.98-708 of Table I.98 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00840##
[0305] Table I.99: Preferred compounds of the formula (I.99) are the compounds I.99-1 to I.99-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.99-1 to I.99-708 of Table I.99 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00841##
[0306] Table I.100: Preferred compounds of the formula (I.100) are the compounds I.100-1 to I.100-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.100-1 to 1.100-708 of Table I.100 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00842##
[0307] Table I.101: Preferred compounds of the formula (I.101) are the compounds I.101-1 to I.101-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.101-1 to 1.101-708 of Table I.101 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00843##
[0308] Table I.102: Preferred compounds of the formula (I.102) are the compounds I.102-1 to I.102-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.102-1 to I.102-708 of Table I.102 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00844##
[0309] Table I.103: Preferred compounds of the formula (I.103) are the compounds I.103-1 to I.103-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.103-1 to I.103-708 of Table I.103 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1.
##STR00845##
[0310] Table I.104: Preferred compounds of the formula (I.104) are the compounds I.104-1 to I.104-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.104-1 to 1.104-708 of Table I.104 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00846##
[0311] Table I.105: Preferred compounds of the formula (I.105) are the compounds I.105-1 to I.105-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.105-1 to 1.105-708 of Table I.105 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00847##
[0312] Table I.106: Preferred compounds of the formula (I.106) are the compounds I.106-1 to I.106-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.106-1 to 1.106-708 of Table I.106 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00848##
[0313] Table I.107: Preferred compounds of the formula (I.107) are the compounds I.107-1 to I.107-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.107-1 to 1.107-708 of Table I.107 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00849##
[0314] Table I.108: Preferred compounds of the formula (I.108) are the compounds I.108-1 to I.108-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.108-1 to I.108-708 of Table I.108 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00850##
[0315] Table I.109: Preferred compounds of the formula (I.109) are the compounds I.109-1 to I.109-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.109-1 to I.109-708 of Table I.109 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00851##
[0316] Table I.110: Preferred compounds of the formula (I.110) are the compounds I.110-1 to I.110-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.110-1 to I.110-708 of Table I.110 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00852##
[0317] Table I.111: Preferred compounds of the formula (I.111) are the compounds I.111-1 to I.111-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.111-1 to I.111-708 of Table I.111 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00853##
[0318] Table I.112: Preferred compounds of the formula (I.112) are the compounds I.112-1 to I.112-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.112-1 to I.112-708 of Table I.112 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00854##
[0319] Table I.113: Preferred compounds of the formula (I.113) are the compounds I.113-1 to I.113-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.113-1 to I.113-708 of Table I.113 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00855##
[0320] Table I.114: Preferred compounds of the formula (I.114) are the compounds I.114-1 to I.114-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.114-1 to I.114-708 of Table I.114 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00856##
[0321] Table I.115: Preferred compounds of the formula (I.115) are the compounds I.115-1 to I.115-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.115-1 to I.115-708 of Table I.115 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
##STR00857##
[0322] Table I.116: Preferred compounds of the formula (I.116) are the compounds I.116-1 to I.116-708 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.116-1 to I.116-708 of Table I.116 are defined by the meaning of the respective entries Nos. 1 to 708 for Q of Table 1 above.
[0323] Spectroscopic data of selected table examples:
[0324] 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
Example No. I.1-287
[0325] .sup.1H-NMR (400 MHz, d.sub.6-DMSO , ppm) 7.14 (br. d, 1H), 6.11 (s, 1H), 6.03 (m, 1H), 5.90 (br. d, 1H), 2.21 (s, 3H), 2.04 (s, 3H).
Example No. I.1-288
[0326] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.31 (s, 1H), 6.18 (br. d, 1H), 6.03 (br. d, 1H), 5.95 (s, 1H), 2.69 (q, 2H), 2.16 (s, 3H), 1.30 (t, 3H).
Example No. I.1-289
[0327] .sup.1H-NMR (400 MHz, d.sub.6-DMSO , ppm) 7.13 (br. d, 1H), 6.21 (s, 1H), 6.04 (m, 1H), 5.91 (br. d, 1H), 3.00-2.92 (sept, 1H), 2.04 (s, 3H), 1.23 (d, 6H).
Example No. I.1-449
[0328] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 8.66 (s, 1H), 8.45 (d, 1H), 7.24 (m, 1H), 6.09 (d, 1H), 5.96 (s, 1H), 5.27 (br. d, 1H), 2.18 (s, 3H).
Example No. I.1-697
[0329] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.28 (s, 1H), 6.15 (br. d, 1H), 6.03 (br. d, 1H), 5.95 (s, 1H), 2.58-2.49 (m, 2H), 2.17 (s, 3H), 2.07-1.99 (m, 1H), 0.98 (d, 6H).
Example No. I.2-162
[0330] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.92 (m, 1H), 6.22 (m, 1H), 5.65 (s, 1H), 4.72 (br. d, 1H), 1.99 (s, 3H), 1.31 (s, 9H).
Example No. I.2-290
[0331] .sup.1H-NMR (400 MHz, d.sub.6-DMSO , ppm) 6.97 (m, 1H), 6.90 (d, 1H), 6.25 (s, 1H), 6.00 (m, 1H), 1.85 (s, 3H), 1.27 (s, 9H).
Example No. I.3-162
[0332] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.11 (s, 1H), 6.70 (s, 1H), 6.00 (m, 1H), 2.19 (s, 3H), 1.34 (s, 9H).
Example No. I.3-287
[0333] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.14 (s, 1H), 6.22 (s, 1H), 6.03 (m, 1H), 2.27 (s, 3H), 2.18 (s, 3H), 2.07 (s, 3H).
Example No. I.3-289
[0334] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.14 (s, 1H), 6.26 (s, 1H), 6.03 (m, 1H), 3.08-2.98 (sept, 1H), 2.19 (s, 3H), 2.07 (s, 3H), 1.30 (d, 6H).
Example No. I.3-290
[0335] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.14 (s, 1H), 6.40 (s, 1H), 6.03 (m, 1H), 2.20 (s, 3H), 2.07 (s, 3H), 1.33 (s, 9H).
Example No. I.5-162
[0336] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.13 (s, 1H), 6.70 (s, 1H), 6.00 (m, 1H), 2.55-2.40 (m, 2H), 2.06 (s, 3H), 1.34 (s, 9H), 1.20 (t, 3H).
Example No. I.5-287
[0337] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.16 (s, 1H), 6.22 (s, 1H), 6.02 (m, 1H), 2.53-2.38 (m, 2H), 2.27 (s, 3H), 2.07 (s, 3H), 1.19 (t, 3H).
Example No. I.5-290
[0338] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.15 (s, 1H), 6.29 (s, 1H), 6.03 (m, 1H), 2.57-2.39 (m, 2H), 2.06 (s, 3H), 1.33 (s, 9H), 1.20 (t, 3H).
Example No. I.5-449
[0339] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 8.72 (m, 1H), 7.57 (m, 1H), 7.53 (m, 1H), 7.32 (s, 1H), 5.72 (m, 1H), 2.28-2.22 (m, 1H), 2.11 (s, 3H), 2.10-2.00 (m, 1H).
Example No. I.6-290
[0340] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.01 (m, 1H), 6.92 (m, 1H), 6.34 (s, 1H), 2.52-2.35 (m, 2H), 2.00 (m, 3H), 1.34 (s, 9H), 1.18 (t, 3H).
Example No. I.11-287
[0341] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.96 (s, 1H), 6.22 (s, 1H), 6.03 (m, 1H), 4.38-4.30 (m, 2H), 2.28 (s, 3H), 2.12 (s, 3H), 1.36 (t, 3H).
Example No. I.11-290
[0342] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.96 (s, 1H), 6.29 (s, 1H), 6.03 (m, 1H), 4.34 (q, 2H), 2.12 (s, 3H), 1.37 (t, 3H), 1.33 (s, 9H).
Example No. I.21-162
[0343] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.72 (s, 1H), 6.13 (br. d, 1H), 5.94 (s, 1H), 4.38 (br. d, 1H), 1.35 (s, 9H), 1.30 (s, 9H).
Example No. I.25-162
[0344] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.38 (s, 1H), 6.70 (s, 1H), 6.01 (s, 1H), 2.52-2.33 (m, 2H), 1.33 (s, 9H), 1.24 (s, 9H), 1.17 (t, 3H).
Example No. I.31-162
[0345] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 7.18 (s, 1H), 6.69 (s, 1H), 6.01 (s, 1H), 4.38-4.33 (m, 2H), 1.33 (s, 9H), 1.37-1.33 (t, 3H), 1.34 (s, 9H).
Example No. I.106-162
[0346] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.67 (s, 1H), 6.48 (s, 1H), 6.03 (br. d, 1H), 4.57 (br. d, 1H), 1.36 (s, 9H).
Example No. I.93-162
[0347] .sup.1H-NMR (400 MHz, CDCl.sub.3 , ppm) 6.69 (s, 1H), 5.95 (br. d, 1H), 5.18 (s, 1H), 4.40 (br. d, 1H), 3.93 (s, 3H), 1.35 (s, 9H).
b) NMR Peak List Method
[0348] The .sup.1H NMR data of selected examples are stated in the form of .sup.1H NMR peak lists. For each signal peak, first the value in ppm and then the signal intensity in round brackets are listed. The value signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.
[0349] Accordingly, the peak list of an example has the form: .sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n) The intensity of sharp signals correlates with the height of the signals (in cm) in a printed example of an NMR spectrum and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum. For calibration of the chemical shift of .sup.1H NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.
[0350] The lists of the .sup.1H NMR peaks are similar to the conventional .sup.1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.
[0351] In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds, which likewise form part of the subject-matter of the invention, and/or peaks of impurities. In the reporting of compound signals within the delta range of solvents and/or water, our lists of .sup.1H NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average. The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%). Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to by-product fingerprints. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 1H NMR interpretation. Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025. Text ignore boxes
[0352] Example No. I.5-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0353] =7.2614 (6.2); 7.1310 (0.9); 6.6953 (2.1); 2.4798 (0.5); 2.4609 (0.6); 2.4441 (0.6); 2.4254 (0.5); 2.0585 (1.8); 2.0572 (1.8); 2.0545 (1.9); 2.0532 (1.7); 1.3375 (16.0); 1.2168 (1.4); 1.1979 (2.9); 1.1791 (1.3); -0.0002 (2.4)
[0354] Example No. I.1-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0355] =7.2614 (4.7); 6.7184 (2.2); 2.1611 (1.7); 2.1597 (1.8); 2.1571 (1.9); 2.1557 (1.8); 1.3567 (16.0); -0.0002 (1.7)
[0356] Example No. I.2-449: .sup.1H-NMR (400.0 MHz, CDCl3):
[0357] =8.3621 (2.4); 8.3491 (2.4); 7.2614 (33.2); 7.0104 (2.0); 7.0085 (2.0); 6.9973 (2.1); 6.9954 (2.0); 6.9467 (0.8); 6.9427 (2.9); 6.9386 (4.6); 6.9345 (3.1); 6.9305 (0.8); 6.8535 (0.6); 6.8270 (1.4); 6.8226 (2.0); 6.8178 (3.3); 6.8157 (3.7); 6.8141 (4.2); 6.8052 (0.5); 6.8007 (1.4); 6.7963 (1.9); 6.7919 (1.3); 6.1807 (0.6); 5.2638 (0.7); 5.2380 (0.7); 2.0111 (8.8); 2.0068 (16.0); 2.0024 (8.7); 1.9773 (1.4); 1.9735 (2.3); 1.9696 (1.4); 1.5873 (1.2); 0.0002 (11.5)
[0358] Example No. I.1-449: .sup.1H-NMR (400.0 MHz, CDCl3):
[0359] =8.6599 (4.7); 8.4501 (3.3); 8.4370 (3.4); 7.2610 (27.0); 7.2432 (2.6); 7.2404 (2.6); 7.2306 (2.5); 7.2272 (2.4); 6.0893 (3.7); 6.0808 (3.7); 5.9614 (3.7); 5.9578 (3.6); 5.2747 (5.4); 5.2660 (5.2); 2.1808 (16.0); 2.1769 (15.9); 1.5614 (5.9); 0.0002 (9.4)
[0360] Example No. I.1-451: .sup.1H-NMR (400.0 MHz, CDCl3):
[0361] =8.7554 (8.0); 8.4067 (7.6); 7.2608 (34.4); 6.0731 (3.5); 6.0639 (3.6); 5.9651 (3.6); 5.9612 (3.7); 4.9272 (4.4); 4.9179 (4.3); 2.1805 (15.0); 2.1794 (15.5); 2.1766 (16.0); 2.1755 (15.1); 1.5581 (4.5); -0.0002 (12.2)
[0362] Example No. I.3-162: .sup.1H-NMR (400.6 MHz, CDCl3):
[0363] =7.2606 (19.6); 7.1139 (1.0); 6.7033 (1.8); 5.9989 (0.6); 5.9950 (0.6); 2.1862 (5.7); 2.0667 (2.3); 2.0631 (2.3); 1.5502 (5.0); 1.3414 (16.0); 1.2619 (1.0); 0.0077 (1.3); 0.0002 (33.5); 0.0083 (1.3)
[0364] Example No. I.11-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0365] =7.2624 (4.4); 6.9487 (0.7); 6.9475 (0.9); 6.9462 (0.7); 6.6835 (2.2); 5.2989 (0.6); 4.3568 (0.6); 4.3474 (0.6); 4.3389 (0.6); 4.3296 (0.6); 2.1190 (1.7); 2.1176 (1.9); 2.1149 (1.8); 2.1135 (1.7); 1.5628 (0.8); 1.3823 (1.4); 1.3645 (3.0); 1.3466 (1.6); 1.3425 (1.6); 1.3360 (16.0); 0.0002 (1.7)
[0366] Example No. I.5-451: .sup.1H-NMR (400.0 MHz, CDCl3):
[0367] =8.6680 (3.8); 8.6669 (4.7); 8.3887 (4.4); 7.4246 (3.5); 7.4234 (4.4); 7.4220 (3.4); 7.2612 (29.6); 6.0158 (1.0); 6.0128 (2.6); 6.0117 (2.6); 6.0087 (2.7); 6.0077 (2.6); 6.0047 (1.0); 2.3792 (1.1); 2.3739 (1.1); 2.3601 (3.4); 2.3551 (3.5); 2.3411 (3.6); 2.3363 (3.6); 2.3221 (1.3); 2.3176 (1.3); 2.0850 (9.0); 2.0835 (9.5); 2.0809 (9.8); 2.0794 (9.1); 1.5498 (9.4); 1.1738 (7.5); 1.1549 (16.0); 1.1360 (7.0); 0.0002 (11.2)
[0368] Example No. I.5-449: .sup.1H-NMR (400.0 MHz, CDCl3):
[0369] =8.7142 (2.7); 8.7016 (2.7); 7.5644 (2.1); 7.5518 (2.0); 7.5243 (3.8); 7.3226 (2.7); 7.2616 (51.9); 5.7196 (0.8); 5.7158 (2.8); 5.7120 (4.2); 5.7081 (2.9); 5.7044 (0.8); 5.2993 (2.6); 2.2798 (1.6); 2.2613 (1.5); 2.2565 (0.8); 2.2428 (0.6); 2.2379 (2.0); 2.2194 (2.1); 2.2009 (0.7); 2.1630 (1.0); 2.1609 (0.9); 2.1012 (10.4); 2.0994 (11.8); 2.0978 (12.0); 2.0960 (11.1); 2.0812 (0.7); 2.0629 (1.8); 2.0446 (1.9); 2.0395 (0.6); 2.0263 (0.7); 2.0210 (1.3); 2.0026 (1.3); 1.5528 (5.4); 1.5001 (0.7); 1.4823 (0.7); 1.1401 (7.9); 1.1217 (16.0); 1.1033 (7.3); 0.0079 (0.6); 0.0002 (18.2); 0.0083 (0.5)
[0370] Example No. I.3-67: .sup.1H-NMR (599.8 MHz, d.sub.6-DMSO):
[0371] =6.9076 (2.8); 6.2424 (1.6); 6.2404 (1.5); 5.7535 (0.8); 5.2114 (0.4); 5.2010 (0.9); 5.1977 (0.4); 5.1906 (1.2); 5.1802 (0.8); 5.1698 (0.3); 3.3239 (50.0); 2.5199 (0.4); 2.5167 (0.4); 2.5078 (6.0); 2.5051 (12.2); 2.5021 (16.6); 2.4991 (12.8); 2.4963 (6.6); 2.0838 (5.4); 2.0819 (5.6); 2.0463 (12.0); 1.3474 (10.5); 1.3401 (3.4); 1.3369 (10.7); 1.3216 (0.6); 1.3182 (0.6); 1.3114 (0.4); 0.0001 (0.4)
[0372] Example No. I.5-67: .sup.1H-NMR (400.0 MHz, CDCl3):
[0373] =7.2620 (29.0); 6.9919 (3.0); 6.0520 (1.5); 6.0506 (1.6); 6.0479 (1.6); 6.0466 (1.6); 5.2994 (0.6); 5.2837 (1.4); 5.2680 (1.8); 5.2523 (1.3); 2.3877 (1.2); 2.3688 (4.0); 2.3499 (4.4); 2.3310 (1.6); 2.0955 (5.7); 2.0944 (6.1); 2.0916 (6.3); 2.0904 (5.9); 2.0819 (0.8); 2.0802 (0.8); 2.0778 (0.7); 2.0762 (0.6); 1.5566 (3.9); 1.4146 (1.3); 1.4113 (1.4); 1.3987 (2.0); 1.3930 (16.0); 1.3773 (15.6); 1.2833 (0.5); 1.2646 (1.4); 1.2588 (0.6); 1.2457 (0.5); 1.2193 (0.5); 1.2005 (0.9); 1.1816 (0.5); 1.1397 (0.9); 1.1213 (0.5); 1.1151 (4.9); 1.0963 (9.9); 1.0901 (0.8); 1.0774 (4.5); 0.8818 (1.2); 0.0002 (10.6)
[0374] Example No. I.3-451: .sup.1H-NMR (400.0 MHz, CDCl3):
[0375] =8.6633 (2.5); 8.4067 (2.4); 7.4097 (2.3); 7.2605 (19.9); 6.0143 (1.4); 6.0103 (1.4); 6.0065 (0.5); 2.0953 (16.0); 2.0914 (5.3); 2.0902 (5.2); 2.0874 (5.1); 2.0862 (4.9); 2.0565 (1.2); 1.5433 (5.4); 0.0002 (7.4)
[0376] Example No. I.1-67: .sup.1H-NMR (400.0 MHz, CDCl3):
[0377] =7.2608 (37.0); 5.9826 (0.8); 5.9650 (2.1); 5.9612 (2.7); 5.2922 (1.1); 5.2765 (1.5); 5.2609 (1.1); 2.9916 (0.6); 2.9687 (0.6); 2.1645 (5.7); 2.1597 (5.9); 2.1177 (1.8); 2.1164 (1.9); 2.1139 (2.0); 2.1124 (1.9); 1.5731 (2.6); 1.3975 (16.0); 1.3818 (15.9); 1.2557 (1.3); 0.0002 (13.5)
[0378] Example No. I.21-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0379] =7.2608 (5.7); 6.7172 (2.1); 6.1289 (0.6); 6.1274 (0.6); 6.1191 (0.6); 6.1176 (0.6); 5.9369 (1.1); 4.3820 (0.6); 4.3732 (0.6); 4.3722 (0.6); 1.5912 (0.6); 1.3534 (16.0); 1.3074 (14.2); 1.2979 (0.6); 0.9660 (1.0); -0.0002 (2.1)
[0380] Example No. I.31-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0381] =7.2620 (5.2); 7.1842 (1.4); 6.6903 (2.2); 6.0060 (1.4); 4.3699 (0.6); 4.3557 (0.6); 4.3519 (0.7); 4.3380 (0.6); 1.5638 (0.6); 1.3716 (1.4); 1.3538 (5.0); 1.3359 (2.0); 1.3305 (16.0); 1.3077 (2.0); 1.2673 (14.7); -0.0002 (1.9)
[0382] Example No. I.12-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0383] =7.2615 (5.0); 6.8512 (1.0); 6.8461 (1.1); 6.7438 (1.1); 6.7387 (1.0); 6.7329 (2.2); 4.3094 (1.3); 4.2916 (1.4); 1.3641 (1.4); 1.3463 (3.2); 1.3381 (16.0); 1.3285 (1.6); 1.2898 (11.4); 0.0002 (2.0)
[0384] Example No. I.1-290: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
[0385] =6.2080 (2.2); 6.0345 (0.8); 6.0316 (0.7); 3.3116 (1.2); 2.5051 (3.3); 2.5007 (4.3); 2.4964 (3.1); 2.0450 (2.8); 2.0421 (2.7); 1.2703 (16.0); 0.0002 (1.3)
[0386] Example No. I.1-289: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
[0387] =7.1279 (1.3); 7.1065 (1.3); 6.2130 (0.9); 6.1678 (11.2); 6.0352 (3.1); 6.0337 (3.2); 6.0312 (3.2); 6.0297 (3.1); 5.9091 (1.4); 5.8884 (1.3); 5.7527 (1.2); 3.3102 (20.7); 2.9910 (0.7); 2.9737 (1.8); 2.9564 (2.5); 2.9390 (1.9); 2.9217 (0.8); 2.5230 (0.8); 2.5183 (1.2); 2.5096 (12.9); 2.5051 (27.0); 2.5004 (37.2); 2.4959 (25.5); 2.4913 (11.5); 2.0447 (10.7); 2.0436 (11.1); 2.0408 (11.3); 2.0397 (10.6); 1.8529 (0.7); 1.8491 (1.1); 1.8453 (0.7); 1.2282 (15.9); 1.2259 (16.0); 1.2108 (15.4); 1.2086 (15.5); 0.0002 (13.6)
[0388] Example No. I.1-287: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):
[0389] =7.1423 (2.8); 7.1194 (2.9); 6.1115 (5.5); 6.1110 (5.4); 6.0302 (1.6); 6.0289 (1.6); 6.0262 (1.6); 6.0249 (1.6); 5.9081 (1.3); 5.9068 (1.9); 5.9055 (1.3); 5.8854 (1.3); 5.8840 (1.8); 5.8826 (1.2); 3.3118 (6.5); 2.5098 (3.8); 2.5052 (8.0); 2.5006 (11.1); 2.4961 (7.5); 2.4915 (3.4); 2.2135 (1.6); 2.2095 (0.5); 2.2088 (0.5); 2.2019 (16.0); 2.0441 (6.2); 2.0428 (6.7); 2.0401 (6.5); 2.0388 (6.4); 1.8491 (0.7); 0.0002 (4.1)
[0390] Example No. I.5-290: .sup.1H-NMR (400.0 MHz, CDCl3):
[0391] =7.2627 (4.3); 7.1531 (0.7); 7.1517 (0.9); 6.2931 (2.1); 2.4893 (0.5); 2.4703 (0.5); 2.4576 (0.5); 2.4388 (0.5); 2.0648 (1.8); 2.0634 (1.9); 2.0607 (1.9); 2.0594 (1.8); 1.5643 (0.7); 1.3265 (16.0); 1.2164 (1.4); 1.1976 (2.9); 1.1787 (1.3); 0.0002 (1.6)
[0392] Example No. I.3-290: .sup.1H-NMR (400.0 MHz, CDCl3):
[0393] =7.2627 (4.1); 7.1359 (0.9); 6.2987 (2.0); 6.0302 (0.5); 2.1954 (5.9); 2.0716 (2.0); 2.0687 (2.0); 2.0676 (1.9); 1.5635 (0.6); 1.3299 (16.0); 0.0002 (1.6)
[0394] Example No. I.11-290: .sup.1H-NMR (400.0 MHz, CDCl3):
[0395] =7.2622 (4.4); 6.9617 (1.0); 6.2896 (2.0); 6.0348 (0.5); 6.0337 (0.5); 6.0308 (0.5); 4.3401 (1.2); 4.3222 (1.2); 2.1224 (2.0); 2.1212 (2.0); 2.1184 (2.1); 2.1174 (1.9); 1.5590 (0.7); 1.3786 (1.4); 1.3608 (2.9); 1.3429 (1.5); 1.3274 (16.0); 0.0002 (1.7)
[0396] Example No. I.6-290: .sup.1H-NMR (400.0 MHz, CDCl3):
[0397] =7.2627 (4.1); 7.0050 (0.5); 6.8195 (0.7); 6.3402 (2.0); 2.4410 (0.5); 2.4220 (0.5); 2.4007 (0.5); 2.3819 (0.5); 2.0018 (1.6); 1.9981 (2.5); 1.9944 (1.6); 1.5654 (1.0); 1.3356 (16.0); 1.3259 (1.5); 1.1858 (1.4); 1.1670 (2.8); 1.1481 (1.3); 0.0002 (1.5)
[0398] Example No. I.5-287: .sup.1H-NMR (400.0 MHz, CDCl3):
[0399] =7.2631 (12.6); 7.1555 (3.1); 6.2185 (4.6); 6.0315 (0.8); 6.0289 (1.6); 6.0276 (1.7); 6.0248 (1.7); 6.0234 (1.7); 2.4831 (0.6); 2.4664 (1.0); 2.4641 (2.0); 2.4478 (2.2); 2.4451 (2.2); 2.4290 (2.1); 2.4263 (1.0); 2.4103 (0.7); 2.2716 (16.0); 2.0715 (6.2); 2.0702 (7.0); 2.0675 (6.7); 2.0661 (6.6); 1.5755 (1.0); 1.2179 (4.7); 1.1990 (9.4); 1.1801 (4.4); 0.0002 (4.6)
[0400] Example No. I.3-287: .sup.1H-NMR (400.0 MHz, CDCl3):
[0401] =7.2629 (9.8); 7.1394 (1.8); 7.1381 (2.3); 6.2217 (3.5); 6.0337 (0.5); 6.0311 (1.2); 6.0298 (1.2); 6.0270 (1.2); 6.0257 (1.2); 6.0231 (0.5); 2.2749 (12.7); 2.1833 (16.0); 2.0782 (4.9); 2.0768 (5.2); 2.0742 (5.1); 2.0728 (4.8); 1.5702 (1.5); 0.0002 (3.8)
[0402] Example No. I.11-287: .sup.1H-NMR (400.0 MHz, CDCl3):
[0403] =7.2635 (10.1); 6.9646 (3.0); 6.2166 (4.5); 6.0359 (1.6); 6.0348 (1.7); 6.0319 (1.6); 6.0307 (1.6); 6.0281 (0.7); 5.2993 (3.5); 4.3664 (0.6); 4.3570 (0.5); 4.3486 (2.2); 4.3310 (2.9); 4.3139 (2.1); 4.3054 (0.5); 4.2961 (0.6); 2.2751 (16.0); 2.1265 (6.8); 2.1238 (6.5); 2.1225 (6.5); 1.5751 (1.2); 1.3796 (4.7); 1.3618 (9.5); 1.3439 (4.6); 0.0002 (4.0)
[0404] Example No. I.3-289: .sup.1H-NMR (400.0 MHz, CDCl3):
[0405] =7.2624 (13.1); 7.1398 (1.9); 7.1385 (2.4); 6.2609 (4.2); 6.0323 (1.3); 6.0309 (1.3); 6.0282 (1.3); 6.0269 (1.2); 5.2993 (8.8); 3.0289 (0.8); 3.0115 (1.1); 2.9941 (0.8); 2.1911 (16.0); 2.0757 (5.0); 2.0743 (5.2); 2.0716 (5.3); 2.0703 (4.7); 1.5631 (1.9); 1.3019 (7.5); 1.2982 (7.3); 1.2846 (7.5); 1.2808 (7.1); -0.0002 (5.1)
[0406] Example No. I.81-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0407] =7.7713 (0.7); 7.7632 (0.8); 7.7544 (0.8); 7.7475 (0.8); 7.4810 (1.5); 7.4729 (1.6); 7.4650 (1.4); 7.2594 (3.6); 6.7860 (1.9); 6.5529 (0.8); 6.5434 (0.8); 6.5092 (1.6); 4.6193 (0.7); 4.6098 (0.8); 1.6168 (0.5); 1.3785 (16.0); 0.0002 (1.3)
[0408] Example No. I.1-697: .sup.1H-NMR (400.0 MHz, CDCl3):
[0409] =7.2611 (36.6); 6.7636 (0.5); 6.2847 (1.4); 6.2513 (9.1); 6.1473 (1.1); 6.1361 (1.1); 6.0288 (2.4); 6.0131 (2.0); 5.9556 (2.6); 5.9541 (2.6); 5.9517 (2.7); 5.9502 (2.5); 2.5370 (1.2); 2.5275 (5.3); 2.5195 (1.7); 2.5099 (6.6); 2.1687 (10.3); 2.1676 (10.9); 2.1648 (11.0); 2.1638 (10.4); 2.0567 (0.8); 2.0397 (1.4); 2.0229 (1.8); 2.0060 (1.5); 1.9885 (1.0); 1.9857 (1.5); 1.9818 (2.0); 1.9780 (1.3); 1.5741 (2.6); 1.0384 (0.5); 1.0210 (0.7); 0.9932 (15.6); 0.9896 (16.0); 0.9766 (15.5); 0.9730 (15.6); 0.9552 (1.0); 0.0079 (0.5); 0.0002 (13.8); 0.0085 (0.6)
[0410] Example No. I.83-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0411] =7.8291 (1.4); 7.8284 (1.4); 7.6532 (0.6); 7.6336 (0.7); 7.4755 (1.2); 7.4711 (1.1); 7.4575 (0.6); 7.2610 (4.2); 6.7773 (2.3); 6.5347 (1.3); 5.2984 (1.8); 2.0895 (6.2); 1.5559 (0.5); 1.3601 (16.0); 0.0002 (2.6)
[0412] Example No. I.85-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0413] =7.8493 (1.4); 7.8483 (1.4); 7.6515 (0.5); 7.6322 (0.6); 7.4714 (1.2); 7.4667 (0.9); 7.4585 (0.6); 7.4538 (0.6); 7.2611 (4.2); 6.7681 (2.4); 6.5331 (1.3); 6.5326 (1.2); 5.2983 (1.3); 1.3559 (16.0); 1.1174 (1.4); 1.0986 (3.0); 1.0797 (1.3); 0.0002 (2.5)
[0414] Example No. I.89-162: .sup.1H-NMR (400.0 MHz, CDCl3):
[0415] =7.6879 (0.5); 7.6690 (0.6); 7.6552 (1.4); 7.6542 (1.4); 7.4852 (1.3); 7.4800 (0.9); 7.4722 (0.6); 7.4678 (0.6); 7.2605 (4.7); 6.7616 (2.5); 6.5268 (1.3); 5.2977 (1.7); 1.5524 (0.5); 1.3556 (16.0); 1.3217 (1.5); 1.3039 (3.1); 1.2860 (1.5); 0.0002 (3.0)
[0416] Example No. I.1-560: .sup.1H-NMR (400.0 MHz, CDCl3):
[0417] =7.2604 (52.2); 6.0801 (2.2); 6.0782 (2.1); 6.0761 (2.2); 6.0460 (2.4); 6.0386 (1.9); 6.0372 (2.4); 4.8070 (2.9); 4.7982 (2.9); 3.2203 (0.8); 3.2030 (2.0); 3.1857 (2.8); 3.1684 (2.1); 3.1511 (0.8); 2.2292 (10.4); 2.2278 (10.5); 2.2251 (10.7); 2.2237 (10.0); 1.6069 (3.4); 1.3726 (1.4); 1.3682 (16.0); 1.3659 (15.9); 1.3553 (1.5); 1.3509 (15.8); 1.3486 (15.9); 0.0079 (0.6); 0.0002 (18.9); 0.0085 (0.5) Example No. I.1-558: .sup.1H-NMR (400.0 MHz, CDCl3):
[0418] =7.5185 (0.9); 7.2596 (155.7); 6.9956 (0.9); 6.0829 (1.9); 6.0810 (2.1); 6.0788 (2.0); 6.0769 (2.0); 6.0280 (1.7); 4.7701 (0.9); 4.7632 (0.9); 2.9179 (2.1); 2.8989 (6.8); 2.8800 (7.4); 2.8611 (2.5); 2.2286 (9.2); 2.2272 (9.5); 2.2246 (9.6); 2.2231 (9.2); 1.5634 (4.1); 1.3811 (7.7); 1.3680 (0.8); 1.3623 (16.0); 1.3433 (7.5); 0.0080 (1.7); 0.0002 (58.0); 0.0085 (1.6)
[0419] Example No. I.1-387: .sup.1H-NMR (400.0 MHz, CDCl3):
[0420] =7.5179 (5.1); 7.3569 (2.1); 7.3398 (5.8); 7.3337 (3.4); 7.3253 (5.5); 7.3215 (10.2); 7.3188 (12.4); 7.3131 (12.8); 7.3067 (8.6); 7.3005 (9.4); 7.2979 (9.3); 7.2883 (5.3); 7.2761 (12.2); 7.2729 (16.3); 7.2684 (15.4); 7.2591 (917.5); 7.2305 (1.0); 7.1132 (1.0); 7.0744 (1.2); 7.0617 (17.6); 6.9950 (5.0); 6.0069 (1.1); 5.9833 (3.8); 5.9752 (4.2); 5.9532 (4.0); 4.8069 (5.2); 4.7987 (5.3); 3.8644 (5.7); 3.7503 (5.2); 2.2089 (2.9); 2.2049 (2.8); 2.1587 (15.8); 2.1554 (16.0); 2.1046 (2.7); 2.1006 (2.7); 2.0045 (1.8); 1.5331 (165.8); 0.1465 (1.2); 0.0080 (10.7); 0.0002 (320.4); 0.0085 (8.5); 0.1496 (1.2)
[0421] Example No. I.1-86: .sup.1H-NMR (400.0 MHz, CDCl3):
[0422] =7.9481 (0.8); 7.9382 (4.8); 7.9344 (6.9); 7.9292 (2.2); 7.9213 (3.4); 7.9173 (6.9); 7.9141 (5.6); 7.9083 (1.0); 7.9020 (0.6); 7.5183 (0.9); 7.4495 (2.0); 7.4455 (2.8); 7.4411 (1.4); 7.4280 (7.5); 7.4244 (3.2); 7.4235 (3.3); 7.4131 (3.6); 7.4098 (6.1); 7.4080 (4.4); 7.4037 (1.5); 7.3958 (2.8); 7.3920 (4.7); 7.3884 (2.7); 7.3806 (2.3); 7.3761 (19.7); 7.3665 (1.3); 7.3560 (1.4); 7.3527 (0.8); 7.3091 (0.6); 7.3048 (0.7); 7.2594 (159.5); 7.2358 (1.0); 7.2238 (1.0); 7.1592 (0.5); 6.9954 (0.9); 6.8154 (0.5); 5.9503 (3.6); 5.9469 (3.5); 5.6627 (2.1); 4.1274 (1.2); 4.1095 (1.2); 2.2944 (0.6); 2.2015 (15.2); 2.2002 (15.8); 2.1974 (16.0); 2.1962 (15.2); 2.0409 (5.4); 1.9709 (1.0); 1.9671 (1.6); 1.9632 (1.0); 1.5628 (1.2); 1.4318 (2.6); 1.2833 (0.8); 1.2744 (1.7); 1.2655 (0.8); 1.2566 (3.5); 1.2387 (1.6); 0.0080 (2.7); 0.0065 (1.0); 0.0056 (1.2); -0.0002 (88.6); 0.0066 (2.2); 0.0084 (3.5)
[0423] Example No. I.1-72: .sup.1H-NMR (400.0 MHz, CDCl3):
[0424] =7.5185 (2.1); 7.2596 (345.8); 7.2097 (1.0); 6.9956 (2.0); 6.8994 (4.8); 6.8906 (1.8); 6.8297 (0.6); 6.8153 (0.5); 6.0701 (2.0); 5.6581 (2.4); 3.6993 (0.7); 2.6908 (0.8); 2.4867 (16.0); 2.4746 (3.3); 2.4691 (5.6); 2.4365 (2.1); 2.4225 (0.8); 2.2418 (7.9); 2.2381 (8.3); 2.2046 (0.9); 2.0797 (0.5); 2.0165 (1.8); 2.0128 (2.6); 2.0089 (1.7); 1.8039 (0.6); 1.4521 (0.8); 1.4115 (0.6); 1.3579 (0.5); 1.3394 (0.6); 1.3029 (0.7); 1.2826 (0.8); 1.2640 (1.8); 1.2554 (2.3); 1.2458 (1.4); 0.3307 (0.7); 0.2376 (0.6); 0.1571 (0.8); 0.1456 (0.6); 0.0080 (4.7); 0.0002 (147.2); 0.0085 (7.6); 0.1494 (0.6)
[0425] Example No. I.1-91: .sup.1H-NMR (400.0 MHz, CDCl3):
[0426] =8.5337 (5.3); 8.0554 (3.4); 7.5188 (1.2); 7.2931 (0.5); 7.2878 (0.6); 7.2599 (219.6); 7.2333 (1.1); 7.2293 (1.0); 7.2111 (0.6); 6.9959 (1.2); 5.9897 (3.6); 5.9860 (3.7); 5.7489 (6.0); 2.9984 (0.5); 2.9772 (0.6); 2.1955 (15.6); 2.1923 (16.0); 2.0424 (1.0); 1.9920 (0.9); 1.9881 (1.4); 1.9844 (1.0); 1.3789 (0.7); 1.2755 (0.5); 1.2579 (1.4); 1.2508 (0.9); 1.2328 (0.7); 0.1566 (1.0); 0.0079 (2.7); 0.0002 (93.1); 0.0085 (4.3)
[0427] Example No. I.1-177: .sup.1H-NMR (400.0 MHz, CDCl3):
[0428] =7.2602 (13.1); 5.8756 (0.8); 2.1427 (1.8); 2.1398 (1.8); 2.1387 (1.8); 2.0940 (0.5); 2.0844 (5.4); 1.4027 (1.9); 1.3979 (16.0); 1.3769 (0.9); 1.3446 (0.8); 0.0002 (5.6)
[0429] Example No. I.2-177: .sup.1H-NMR (400.0 MHz, CDCl3):
[0430] =7.2597 (64.8); 6.7656 (1.2); 6.7612 (1.8); 6.7568 (1.2); 6.0209 (0.6); 2.0961 (16.0); 2.0052 (0.8); 1.9775 (4.0); 1.9736 (6.5); 1.9697 (4.0); 1.5493 (1.6); 1.4035 (45.6); 0.0080 (0.8); 0.0002 (23.6); -0.0085 (0.7)
[0431] Example No. I.1-300: .sup.1H-NMR (400.0 MHz, CDCl3):
[0432] =7.2602 (17.6); 5.9397 (0.5); 5.9356 (0.5); 2.1548 (1.9); 2.1537 (2.1); 2.1509 (2.1); 2.1497 (2.1); 2.0600 (0.7); 2.0503 (6.4); 1.5535 (0.6); 1.3601 (3.0); 1.3547 (1.5); 1.3493 (16.0); 1.3213 (0.7); 0.0002 (7.8)
[0433] Example No. I.2-300: .sup.1H-NMR (400.0 MHz, CDCl3):
[0434] =7.2601 (11.8); 5.9378 (0.7); 5.9338 (0.7); 2.1545 (2.8); 2.1518 (2.5); 2.1507 (2.5); 2.0594 (0.5); 2.0493 (6.0); 1.3546 (1.4); 1.3435 (16.0); 0.0002 (4.4)
[0435] Example No. I.2-709: .sup.1H-NMR (400.0 MHz, CDCl3):
[0436] =7.2603 (20.8); 5.9743 (0.8); 5.9728 (0.9); 5.9702 (1.4); 5.9688 (1.5); 5.9661 (1.6); 5.9649 (1.6); 5.9624 (0.8); 2.5721 (16.0); 2.1818 (4.6); 2.1802 (4.1); 2.1779 (4.1); 2.1762 (4.6); 0.0002 (12.4)
[0437] The present invention furthermore provides the use of one or more compounds of the formula (I) and/or salts 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.1) to (I.116) and/or salts thereof, in each case as defined above,
[0438] as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamental plants.
[0439] 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 [0440] of one or more compounds of the formula (I) and/or salts 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.1) to (I.116) and/or salts thereof, in each case as defined above, or [0441] of a composition according to the invention, as defined below,
[0442] 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.
[0443] The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount [0444] of one or more compounds of the formula (I) and/or salts 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.1) to (I.116) and/or salts thereof, in each case as defined above, or [0445] of a composition according to the invention, as defined below,
[0446] 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).
[0447] The present invention furthermore also provides methods for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount [0448] of one or more compounds of the formula (I) and/or salts 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.1) to (I.116) and/or salts thereof, in each case as defined above, or [0449] of a composition according to the invention, as defined below,
[0450] 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).
[0451] 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.
[0452] In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the formula (I) and/or salts 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.
[0453] The compounds of the formula (I) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:
Monocotyledonous Harmful Plants of the Genera:
[0454] 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.
Dicotyledonous Harmful Plants of the Genera:
[0455] 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.
[0456] 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.
[0457] 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.
[0458] 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.
[0459] 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.
[0460] 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.
[0461] It is preferred with a view to transgenic crops to use the compounds according to the invention and/or their salts 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.
[0462] 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.
[0463] 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.
[0464] Preference is given to the use of the compounds of the formula (I) according to the invention or salts thereof 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.
[0465] The compounds of the 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.
[0466] 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.
[0467] 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.
[0468] 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.
[0469] 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.
[0470] 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.
[0471] 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.
[0472] 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.
[0473] 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.
[0474] 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.
[0475] The invention therefore also relates to the use of the compounds of the formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.
[0476] 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.
[0477] Preference is also given to the use in soybeans by the pre- or post-emergence method.
[0478] 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 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. The invention also provides for the use of one or more compounds of the formula (I) or salts 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 formula (I) or salts 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.
[0479] The invention also provides a herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises
[0480] (a) one or more compounds of the formula (I) and/or salts 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.1) to (I.116) and/or salts thereof, in each case as defined above, and
[0481] (b) one or more further substances selected from groups (i) and/or (ii): [0482] (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 formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, [0483] (ii) one or more formulation auxiliaries customary in crop protection.
[0484] 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.
[0485] 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 adsorbant 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.
[0486] The compounds (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 formula (I) and/or salts thereof.
[0487] The compounds of the formula (I) and/or salts 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.
[0488] 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; Schonfeldt, Grenzflchenaktive thylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-KUichler, Chemische Technologie [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.
[0489] 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.
[0490] 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.
[0491] 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.
[0492] 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.
[0493] 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.
[0494] 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.
[0495] 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.
[0496] 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.
[0497] 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.
[0498] 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 formula (I) and their salts.
[0499] 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.
[0500] 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).
[0501] The compounds of the formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of 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.
[0502] Active compounds which can be employed in combination with the compounds of 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.
[0503] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds (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 (I) according to the invention are of particular interest which comprise the compounds (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.
[0504] The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener 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.
[0505] 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.
[0506] The application rate of the compounds of the formula (I) and/or their salts 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 formula (I) and their salts is 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 I.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.
[0507] When the compounds of the formula (I) and/or their salts are used as plant growth regulator, 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.
[0508] 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 tillering phase, at the beginning of the longitudinal growth.
[0509] 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.
[0510] Active compounds which can be employed in combination with the compounds of the 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.
[0511] Examples of such herbicidal mixing partners are:
[0512] acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-ylphenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. O-2,4-dimethyl-6-nitrophenyl O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfony)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and also the following compounds:
##STR00858##
[0513] Examples of plant growth regulators as possible mixing partners are:
[0514] acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenoxide mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
[0515] Suitable combination partners for the compounds of the formula (I) according to the invention also include, for example, the following safeners: [0516] S1) Compounds from the group of heterocyclic carboxylic acid derivatives: [0517] 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; [0518] 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 (S1-4) and related compounds as described in EP-A-333131 131 and EP-A-269806; [0519] 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; [0520] 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; [0521] 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. [0522] S2) Compounds from the group of the 8-quinolinoxy derivatives (S2): [0523] S2.sup.a) Compounds of the 8-quinolinoxyacetic acid type (S2.sup.a), 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; [0524] 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. [0525] S3) Active compounds of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), for example [0526] dichlormid (N,N-diallyl-2,2-dichloroacetamide) (S3-1), [0527] R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), [0528] R-28725 (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), [0529] benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), [0530] PPG-1292 (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5), [0531] DKA-24 (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S3-6), [0532] AD-67 or MON 4660 (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7), [0533] TI-35 (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8), [0534] Diclonon (Dicyclonon) or BAS145138 or LAB145138 (S3-9) [0535] ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, [0536] furilazole or MON 13900 ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and the (R) isomer thereof (S3-11). [0537] S4) Compounds from the class of the acylsulfonamides (S4): [0538] S4.sup.a)N-Acylsulfonamides of the formula (S4.sup.a) and salts thereof, as described in WO-A-97/45016,
##STR00859## [0539] in which [0540] 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; [0541] R.sub.A.sup.2 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0542] m.sub.A is 1 or 2; [0543] v.sub.A is 0, 1, 2 or 3; [0544] 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,
##STR00860## [0545] in which [0546] 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, [0547] 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 [0548] m.sub.B is 1 or 2, [0549] for example those in which [0550] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (cyprosulfamide, S4-1), [0551] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-2), [0552] R.sub.B.sup.1=ethyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-3), [0553] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-4) and [0554] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-5); [0555] S4.sup.c) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4.sup.c), as described in EP-A-365484,
##STR00861## [0556] in which [0557] 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, [0558] 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 [0559] m.sub.C is 1 or 2; [0560] for example [0561] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, [0562] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, [0563] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; [0564] 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,
##STR00862## [0565] in which [0566] R.sub.D4 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0567] m.sub.D is 1 or 2; [0568] R.sub.D5 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. [0569] 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. [0570] 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. [0571] 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. [0572] S8) Compounds of the formula (S8), as described in WO-A-98/27049,
##STR00863##
in which the symbols and indices are defined as follows: [0573] 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, [0574] R.sub.D.sup.2 is hydrogen or (C.sub.1-C.sub.4)-alkyl, [0575] 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, [0576] n.sub.D is an integer from 0 to 2. [0577] 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; [0578] S10) Compounds of the formula (S10.sup.a) or (S10.sup.b)
##STR00864## [0579] as described in WO-A-2007/023719 and WO-A-2007/023764
in which [0580] R.sub.E.sup.1 is halogen, (C.sub.1-C.sub.4)-alkyl, methoxy, nitro, cyano, CF.sub.3, OCF.sub.3 [0581] Y.sub.E, Z.sub.E are independently O or S, [0582] n.sub.E is an integer from 0 to 4, [0583] 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, [0584] R.sub.E.sup.3 is hydrogen or (C.sub.1-C.sub.6)-alkyl. [0585] S11) Active compounds of the oxyimino compound type (S11), which are known as seed-dressing agents, for example [0586] 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, [0587] 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 [0588] cyometrinil or CGA-43089 ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage. [0589] 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. [0590] S13) One or more compounds from group (S13): [0591] naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for corn against thiocarbamate herbicide damage, [0592] fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, [0593] 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, [0594] CL 304415 (CAS Reg. No. 31541-57-8) [0595] (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, [0596] 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, [0597] MG 838 (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia [0598] disulfoton (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), [0599] dietholate (O,O-diethyl O-phenyl phosphorothioate) (S13-8), [0600] mephenate (4-chlorophenyl methylcarbamate) (S13-9). [0601] S14) active compounds which, in addition to herbicidal action against weeds, also have safener action on crop plants such as rice, for example [0602] 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, [0603] daimuron or SK 23 (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as safener for rice against imazosulfuron herbicide damage, [0604] 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, [0605] methoxyphenone or NK 049 (3,3-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides, [0606] 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. [0607] S15) Compounds of the formula (S15) or tautomers thereof
##STR00865## [0608] as described in WO-A-2008/131861 and WO-A-2008/131860 [0609] in which [0610] R.sub.H.sup.1 is a (C.sub.1-C.sub.8)-haloalkyl radical and [0611] R.sub.H.sup.2 is hydrogen or halogen and [0612] 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, [0613] 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, [0614] 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, [0615] 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, [0616] or [0617] 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 [0618] R.sub.H.sup.4 is hydrogen or (C.sub.1-C.sub.4)-alkyl or [0619] 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. [0620] S16) Active compounds which are used primarily as herbicides but also have safener action on crop plants, for example [0621] (2,4-dichlorophenoxy)acetic acid (2,4-D), [0622] (4-chlorophenoxy)acetic acid, [0623] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), [0624] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), [0625] (4-chloro-o-tolyloxy)acetic acid (MCPA), [0626] 4-(4-chloro-o-tolyloxy)butyric acid, [0627] 4-(4-chlorophenoxy)butyric acid, [0628] 3,6-dichloro-2-methoxybenzoic acid (dicamba), [0629] 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).
[0630] Preferred safeners in combination with the compounds of the formula (I) according to the invention and/or salts thereof, in particular with the compounds of the formulae (I.1) to (I.116) and/or salts 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
Experimental Part 1
A. Post-Emergence Herbicidal Action and Crop Plant Compatibility
[0631] Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in plastic or wood-fiber pots, covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then sprayed onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 l/ha (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.
[0632] Tables A1 to A14 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
TABLE-US-00003 TABLE A1 Compound Application rate Example No. Alopecurus myosuroides [g/ha] I.1-162 100 1280 I.1-162 90 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 90 320 I.11-162 100 320
TABLE-US-00004 TABLE A2 Compound Application rate Example No. Echinochloa crus-galli [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 90 320 I.5-162 100 1280 I.11-162 90 320
TABLE-US-00005 TABLE A3 Compound Application rate Example No. Setaria viridis [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00006 TABLE A4 Compound Application rate Example No. Abutilon theophrasti [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00007 TABLE A5 Compound Application rate Example No. Amaranthus retroflexus [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 90 320 I.5-162 100 1280 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00008 TABLE A6 Compound Application rate Example No. Matricaria inodora [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.11-162 100 320 I.12-451 100 1280 I.12-451 90 320
TABLE-US-00009 TABLE A7 Compound Application rate Example No. Polygonum convolvulus [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00010 TABLE A8 Compound Application rate Example No. Stellaria media [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00011 TABLE A9 Compound Application rate Example No. Viola tricolor [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00012 TABLE A10 Compound Application rate Example No. Veronica persica [g/ha] I.1-162 100 1280 I.3-162 100 1280 I.5-162 100 1280 I.11-162 100 320 I.12-451 100 1280
TABLE-US-00013 TABLE A11 Compound Application rate Example No. Hordeum murinum [g/ha] I.1-162 100 1280 I.3-162 100 1280 I.5-162 100 1280
TABLE-US-00014 TABLE A12 Compound Application rate Example No. Lolium rigidum [g/ha] I.3-162 90 1280 I.5-162 90 1280
TABLE-US-00015 TABLE A13 Compound Application rate Example No. Avena fatua [g/ha] I.1-162 100 1280 I.1-162 90 320 I.3-162 90 1280 I.3-162 90 320 I.5-162 100 1280
TABLE-US-00016 TABLE A14 Compound Application rate Example No. Ipomoea purpurea [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 90 1280 I.5-162 90 1280 I.11-162 90 320 I.12-451 100 1280 I.12-451 100 320
[0633] As demonstrated by the results, the compounds according to the invention of the general formula (I) have, in post-emergence applications, good herbicidal activity on harmful plants such as Alopecurus myorsuroides, Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Polygonum convolvulus, Stellaria media, Viola tricolor, Veronica persica, Hordeum murinum, Lolium rigidum, Avena fatua and Ipomoea purpurea at an application rate of 1.28 kg of active substance or less per hectare. At the same time, some of the compounds according to the invention leave Gramineae crops such as barley, wheat, rye, millet/sorghum, corn, rice or sugar cane, virtually undamaged when applied post-emergence, even at high active compound dosages. In addition, some substances are also harmless to dicotyledonous crops such as soya, cotton, oilseed rape or sugar beet. Some of the compounds according to the invention have high selectivity and are therefore suitable for controlling unwanted vegetation in agricultural crops by the post-emergence method.
B. Pre-emergence herbicidal action and crop plant compatibility
[0634] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in plastic or organic planting pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 l/ha (converted). After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 0% activity=like control plants.
[0635] Tables B1 to B14 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
TABLE-US-00017 TABLE B1 Compound Application rate Example No. Alopecurus myosuroides [g/ha] I.1-162 100 1280 I.1-162 90 320 I.3-162 90 1280 I.3-162 90 320 I.5-162 90 1280 I.5-162 90 320 I.11-162 100 320 I.12-451 90 1280
TABLE-US-00018 TABLE B2 Compound Application rate Example No. Echinochloa crus-galli [g/ha] I.1-162 100 1280 I.3-162 100 1280 I.5-162 100 1280 I.11-162 100 320
TABLE-US-00019 TABLE B3 Compound Application rate Example No. Setaria viridis [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 90 320
TABLE-US-00020 TABLE B4 Compound Application rate Example No. Abutilon theophrasti [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280
TABLE-US-00021 TABLE B5 Compound Application rate Example No. Amaranthus retroflexus [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.3-290 90 1280 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00022 TABLE B6 Compound Application rate Example No. Matricaria inodora [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 90 1280
TABLE-US-00023 TABLE B7 Compound Application rate Example No. Polygonum convolvulus [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280
TABLE-US-00024 TABLE B8 Compound Application rate Example No. Stellaria media [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 90 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00025 TABLE B9 Compound Application rate Example No. Viola tricolor [g/ha] I.1-162 100 1280 I.1-162 100 320 I.3-162 100 1280 I.3-162 100 320 I.5-162 100 1280 I.5-162 100 320 I.11-162 100 320 I.12-451 100 1280 I.12-451 100 320
TABLE-US-00026 TABLE B10 Compound Application rate Example No. Veronica persica [g/ha] I.1-162 100 1280 I.3-162 100 1280 I.5-162 100 1280
TABLE-US-00027 TABLE B11 Compound Application rate Example No. Hordeum murinum [g/ha] I.1-162 100 1280 I.1-162 90 320 I.3-162 100 1280 I.3-162 90 320 I.5-162 100 1280
TABLE-US-00028 TABLE B12 Compound Application rate Example No. Lolium rigidum [g/ha] I.1-162 100 1280 I.3-162 90 1280 I.5-162 90 1280 I.11-162 90 1280
TABLE-US-00029 TABLE B13 Compound Application rate Example No. Avena fatua [g/ha] I.1-162 100 1280 I.1-162 90 320 I.3-162 90 1280 I.3-162 90 320 I.5-162 90 1280 I.5-162 90 320 I.11-162 90 320 I.12-451 90 1280
TABLE-US-00030 TABLE B14 Compound Application rate Example No. Ipomoea purpurea [g/ha] I.1-162 100 1280 I.3-162 90 1280 I.5-162 90 1280 I.11-162 90 320
[0636] As demonstrated by the results, the compounds according to the invention of the general formula (I) have, in pre-emergence applications, good herbicidal activity on harmful plants, for example harmful plants such as Alopecurus myosuroides, Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Polygonum convolvolus, Stellaria media, Viola tricolor, Veronica persica, Hordeum murinum, Lolium rigidum, Avena fatua, Ipomoea purpurea at an application rate of 1.28 kg of active substance or less per hectare. At the same time, some of the compounds according to the invention leave Gramineae crops such as barley, wheat, rye, millet/sorghum, corn, rice or sugar cane, virtually undamaged when applied pre-emergence, even at high active compound dosages. In addition, some substances are also harmless to dicotyledonous crops such as soya, cotton, oilseed rape or sugar beet.
[0637] Some of the compounds according to the invention exhibit high selectivity and are therefore suitable for controlling unwanted vegetation in agricultural crops by the pre-emergence method.
Experimental Part 2
[0638] C. Herbicidal Post-Emergence Action
[0639] Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot), covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were applied onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.
[0640] Tables C1 to C8 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
TABLE-US-00031 TABLE C1 Compound Application rate Example No. Echinochloa crus-galli [g/ha] I.1-177 100 1280 I.1-300 100 1280 I.1-451 100 1280 I.2-162 100 320 I.2-177 100 320 1.2-290 100 1280 1.6-290 100 1280
TABLE-US-00032 TABLE C2 Compound Application rate Example No. Lolium rigidum [g/ha] I.2-162 90 320 I.2-177 90 320 1.2-290 100 1280 1.6-290 90 1280
TABLE-US-00033 TABLE C3 Compound Application rate Example No. Poa Annua [g/ha] I.1-177 100 1280 I.1-300 100 320 I.1-451 100 320 I.2-162 100 320 I.2-177 100 320 I.2-290 100 320 1.3-290 100 1280 I.3-451 100 320 I.5-451 100 1280 1.6-290 100 320
TABLE-US-00034 TABLE C4 Compound Application rate Example No. Setaria viridis [g/ha] I.1-91 100 1280 I.1-177 100 1280 I.1-300 100 320 I.2-162 100 320 1.2-290 100 320 1.2-300 90 1280 I.5-451 90 1280 1.6-290 100 320
TABLE-US-00035 TABLE C5 Compound Application rate Example No. Abutilon theophrasti [g/ha] I.1-91 100 1280 I.1-177 100 1280 I.1-289 100 1280 I.1-290 100 320 I.1-300 100 320 I.1-451 100 320 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.2-300 100 1280 I.3-290 100 1280 I.3-451 100 320 I.5-290 100 1280 I.5-451 100 320 1.6-290 100 320
TABLE-US-00036 TABLE C6 Compound Application rate Example No. Amaranthus retroflexus [g/ha] I.1-72 100 320 I.1-91 100 320 I.1-177 100 1280 I.1-289 100 320 I.1-300 100 320 I.1-451 100 1280 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.2-300 100 320 I.3-451 100 1280 1.6-290 100 320
TABLE-US-00037 TABLE C7 Compound Application rate Example No. Matricaria inodora [g/ha] I.1-72 100 1280 I.1-91 100 1280 I.1-177 100 320 I.1-289 100 1280 I.1-290 100 1280 I.1-300 100 320 I.1-451 90 320 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 I.3-290 90 1280 I.3-451 90 320 I.5-290 100 1280 I.5-451 90 1280 1.6-290 100 320
TABLE-US-00038 TABLE C8 Compound Application rate Example No. Stellaria media [g/ha] I.1-91 100 1280 I.1-177 100 320 I.1-290 100 1280 I.1-300 100 320 I.1-451 100 320 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.2-300 100 1280 I.3-451 100 320 I.5-290 100 1280 I.5-451 100 1280 1.6-290 100 320
[0641] As the results show, compounds of the general formula (I) according to the invention, in post-emergence applications, have very good herbicidal activity against harmful plants. For example, compounds of the general formula (I), applied post-emergence, have very good herbicidal activity (80% to 100% herbicidal activity) against harmful plants such as Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Poa annua, Setaria viridis and Stellaria media at an application rate of 1280 g or 320 g of active substance or less per hectare.
[0642] D. Herbicidal Pre-Emergence Action
[0643] Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species of mono- or dicotyledonous weed plants per pot) and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 liters per hectare (converted). After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 0% activity=like control plants.
[0644] Tables D1 to D8 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.116 on various harmful plants and an application rate corresponding to 1280 g/ha or 320 g/ha, which were obtained by the experimental procedure mentioned above.
TABLE-US-00039 TABLE D1 Compound Application rate Example No. Echinochloa crus-galli [g/ha] I.1-177 100 1280 I.1-300 100 320 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.6-290 90 320
TABLE-US-00040 TABLE D2 Compound Application rate Example No. Lolium rigidum [g/ha] I.1-177 90 320 I.1-300 90 1280 I.2-162 90 320 I.2-177 90 320 1.2-290 100 1280 I.3-451 90 1280 I.5-290 90 1280 I.5-451 90 1280 1.6-290 90 320
TABLE-US-00041 TABLE D3 Compound Application rate Example No. Poa Annua [g/ha] I.1-177 100 1280 I.1-289 100 1280 I.1-290 90 320 I.1-300 90 320 I.1-451 90 1280 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.2-300 90 1280 I.3-290 90 1280 I.3-451 90 320 I.5-290 90 320 I.5-451 100 320 1.6-290 100 320
TABLE-US-00042 TABLE D4 Compound Application rate Example No. Setaria viridis [g/ha] I.1-177 100 320 I.1-289 90 1280 I.1-290 90 1280 I.1-300 100 1280 I.1-451 100 1280 I.2-162 100 320 I.2-177 100 320 1.2-290 100 1280 1.2-300 90 320 I.3-290 90 1280 I.3-451 100 1280 I.5-290 90 1280 I.5-451 100 320 1.6-290 90 320
TABLE-US-00043 TABLE D5 Compound Application rate Example No. Abutilon theophrasti [g/ha] I.1-91 100 1280 I.1-177 100 320 I.1-289 100 1280 I.1-290 90 1280 I.1-300 100 320 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.2-300 90 320 I.3-290 100 1280 I.5-290 100 1280 1.6-290 100 320
TABLE-US-00044 TABLE D6 Compound Application rate Example No. Amaranthus retroflexus [g/ha] I.1-72 90 1280 I.1-91 100 320 I.1-177 90 1280 I.1-289 90 1280 I.1-290 100 1280 I.1-300 90 1280 I.1-451 90 1280 I.2-162 100 320 I.2-177 90 320 1.2-290 100 320 1.2-300 100 320 I.3-290 90 1280 1.6-290 100 320
TABLE-US-00045 TABLE D7 Compound Application rate Example No. Matricaria inodora [g/ha] I.1-91 90 1280 I.1-177 100 1280 I.1-289 100 1280 I.1-290 100 320 I.1-300 100 320 I.1-451 100 1280 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.2-300 90 1280 I.3-290 100 1280 I.5-290 100 320 I.5-451 90 1280 1.6-290 100 320
TABLE-US-00046 TABLE D8 Compound Application rate Example No. Stellaria media [g/ha] I.1-72 90 1280 I.1-177 100 1280 I.1-289 100 1280 I.1-290 100 320 I.1-300 100 320 I.1-451 100 320 I.2-162 100 320 I.2-177 100 320 1.2-290 100 320 1.2-300 90 320 I.3-290 100 1280 I.3-451 100 320 I.5-290 100 320 I.5-451 100 1280 1.6-290 100 320
[0645] As the results show, compounds of the general formula (I) according to the invention, in pre-emergence applications, have very good herbicidal activity against harmful plants. For example, compounds of the general formula (I), applied pre-emergence, have very good activity (80% to 100% herbicidal activity) against harmful plants such as Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Poa annua, Setaria viridis and Stellaria media at an application rate of 1280 g or 320 g of active substance or less per hectare.
Experimental Part 3
Measurement of the PS II Activity in Thylakoid Membranes
[0646] Cooled fresh spinach leaves were comminuted and homogenized in 50 mM phosphate buffer, pH 6.8. 10 mM KCl, 0.34 M sucrose (sucrose buffer) (blender, 1 g of plant material/ml). The homogenate was subsequently filtered through 4 layers of Miracloth and the chloroplasts were isolated by centrifugation, i.e. 10 min of centrifugation at 4400g (4 C.). The sediment was suspended in 25 ml of sucrose buffer and re-centrifuged for 10 min at 4400g (4 C.). The sediment was then suspended in 40 ml of 50 mM phosphate buffer, pH 6.8, 10 mM KCl, without sucrose. In this step, the chloroplasts were osmotically ruptured and the thylakoid membranes were then obtained by centrifugation (10 min, 4400g, 4 C.). The membrane sediment was finally suspended in about 20 ml of 50 mM phosphate buffer, pH 6.8, 10 mM KCl. Following protein determination and activity determination, the membrane suspension was divided into aliquots and frozen in liquid nitrogen. The aliquots were stored at 80 C. Under these conditions, the photosystem II preparation was storage stable for at least three months. The activity determination of photosystem II (PS II) was then carried out using the following test principle: The electron transfer from PS II to an artificial electron acceptor, 2,6-dichlorophenolindophenol (DCPIP), was measured with exposure to light. The concentration of the blue oxidized form of DCPIP was determined spectrophotometrically at wavelength =595 nm. The enzyme-catalyzed reduction of DCPIP resulted in a colorless leuco form and thus in a decrease of the absorption at 595 nm in the reaction batch, which decrease was measured as a function of time. The activity determination was carried out in microtiter plates (96 cavities) in a reaction volume of 200 l. Here, 155 l of dilute membrane suspension were initially charged in 50 mM of phosphate buffer, pH 6.8, 10 mM KCl. Depending on the activity of the PS II preparation, the dilution was adjusted such that the measurement of the decrease in absorption (=595 nm) was linear for at least 10 min. In each case 5 l solution of the test compounds of a concentration of 100 M in DMSO were added to the enzyme suspension; controls contained 5 l DMSO; the final concentration of DMSO in the reaction batch was thus 2.5% (v/v); this concentration had no adverse effect on the enzymatic activity. On each microtiter plate, a known PS II inhibitor, for example metribuzin, was used as standard, which allowed the quality of the PS II test to be assessed. The reaction was started by addition of 40 l DCPIP solution (600 M in distilled water); the final concentration of DCPIP was 120 M. Measurement of absorption was carried out over a period of 10 min at 22 C. and with exposure to light. Using metribuzin as comparative substance, the results for the efficacy of the compounds of the general formula (I) at 100 M are stated in the table below using the following classification: ++++ (inhibition90%), +++ (90%>inhibition70%), ++ (70%>inhibition50%), + (50%>inhibition30%).
[0647] Effects of selected compounds of the general formula (I) according to the following table E1:
TABLE-US-00047 TABLE E1 No. Substance Effect 1 metribuzin ++++ 2 I.1-72 ++++ 3 I.1-86 ++++ 4 I.1-162 ++++ 5 I.1-177 ++++ 6 I.1-290 ++++ 7 I.1-300 +++ 8 I.1-315 ++++ 9 I.1-449 ++++ 10 I.1-451 ++++ 11 I.1-697 ++++ 12 I.2-72 ++ 13 I.2-86 ++++ 14 I.2-162 ++++ 15 I.2-177 ++++ 16 I.2-290 ++++ 17 I.2-300 ++++ 18 I.3-451 +++ 19 I.5-162 +++ 20 I.25-162 ++++
[0648] Similar results were also achievable with further compounds of the general formula (I).