SUBSTITUTED N-PHENYLURACILS AND SALTS THEREOF, AND USE THEREOF AS HERBICIDAL ACTIVE SUBSTANCES
20240025862 · 2024-01-25
Inventors
- Ines Heinemann (Hofheim, DE)
- Harald Jakobi (Frankfurt, DE)
- Hendrik Helmke (Liederbach, DE)
- Jens Frackenpohl (Frankfurt, DE)
- Christopher Hugh Rosinger (Hofheim, DE)
- Elmar Gatzweiler (Bad Nauheim, DE)
- Elisabeth ASMUS (Hoesbach, DE)
- Birgit BOLLENBACH-WAHL (Weiler/Bingen, DE)
Cpc classification
C07D409/12
CHEMISTRY; METALLURGY
C07D417/12
CHEMISTRY; METALLURGY
C07D405/12
CHEMISTRY; METALLURGY
C07D403/12
CHEMISTRY; METALLURGY
International classification
C07D405/12
CHEMISTRY; METALLURGY
C07D409/12
CHEMISTRY; METALLURGY
C07D403/12
CHEMISTRY; METALLURGY
C07D401/12
CHEMISTRY; METALLURGY
Abstract
Substituted N-phenyluracils and salts thereof and use thereof as herbicidal agents.
The present invention relates to substituted N-phenyluracils of the general formula (I) or salts thereof,
##STR00001##
where the radicals in the general formula (I) conform to the definitions given in the description, and to the use thereof as herbicides, especially for control of 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 N-phenyluracil of formula (I) and/or salt[[s thereof ##STR00113## in which R.sup.1 is hydrogen, halogen, cyano, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-haloalkoxy R.sup.2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C.sub.1-C.sub.8)-alkoxy, R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.8)-alkoxy, R.sup.4 is halogen, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkynyl, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen, halogen, cyano, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-haloalkoxy, G is unbranched or branched (C.sub.1-C.sub.8)-alkylene, Q is a radical of formula ##STR00114## R.sup.8 is hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-alkenyl, C(O)R.sup.13, C(O)OR.sup.13, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, R.sup.9 is hydrogen or (C.sub.1-C.sub.8)-alkyl, R.sup.10 is cyano, NO.sub.2, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, R.sup.11R.sup.12N(C.sub.1-C.sub.8)-alkyl, R.sup.13O(C.sub.1-C.sub.8)-alkyl, cyano-(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, arylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, OR.sup.13, NR.sup.11R.sup.12, SR.sup.14, S(O)R.sup.14, SO.sub.2R.sup.14, R.sup.14S(C.sub.1-C.sub.8)-alkyl, R.sup.14(O)S(C.sub.1-C.sub.8)-alkyl, R.sup.14O.sub.2S(C.sub.1-C.sub.8)-alkyl, tris[(C.sub.1-C.sub.8)-alkyl]silyl-(C.sub.1-C.sub.8)-alkyl, bis[(C.sub.1-C.sub.8)-alkyl](aryl)silyl(C.sub.1-C.sub.8)-alkyl, [(C.sub.1-C.sub.8)-alkyl]bis(aryl)silyl-(C.sub.1-C.sub.8)-alkyl, tris[(C.sub.1-C.sub.8)-alkyl]silyl, bishydroxyboryl-(C.sub.1-C.sub.8)-alkyl, bis[(C.sub.1-C.sub.8)-alkoxy]boryl-(C.sub.1-C.sub.8)-alkyl, tetramethyl-1,3,2-dioxaborolan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl-(C.sub.1-C.sub.8)-alkyl, nitro-(C.sub.1-C.sub.8)-alkyl, C(O)R.sup.14, bis(C.sub.1-C.sub.8)-alkoxymethyl, bis(C.sub.1-C.sub.8)-alkoxymethyl-(C.sub.1-C.sub.8)-alkyl, or R.sup.8 and R.sup.10 together with the carbon atom to which they are bonded form a fully saturated or partly saturated 3- to 10-membered monocyclic or bicyclic heterocyclyl optionally having further substitution, R.sup.11 and R.sup.12 are the same or different and are independently 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.3-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.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, COR.sup.13, SO.sub.2R.sup.14, heterocyclyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, bis[(C.sub.1-C.sub.8)-alkyl]aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylaminocarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkylaminocarbonyl-(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, or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are bonded form a fully saturated or partly saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution, R.sup.13 is 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.3-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)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, (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)-alkoxy-(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)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxy-(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, bis[(C.sub.1-C.sub.8)-alkyl]aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylaminocarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkylaminocarbonyl-(C.sub.1-C.sub.8)-alkyl, bis[(C.sub.1-C.sub.8)-alkyl]amino-(C.sub.2-C.sub.6)-alkyl, (C.sub.1-C.sub.8)-alkylamino-(C.sub.2-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.8)-alkylamino-(C.sub.2-C.sub.6)-alkyl, R.sup.14S(C.sub.1-C.sub.8)-alkyl, R.sup.14(O)S(C.sub.1-C.sub.8)-alkyl, R.sup.14O.sub.2S(C.sub.1-C.sub.8)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, tris[(C.sub.1-C.sub.8)-alkyl]silyl-(C.sub.1-C.sub.8)-alkyl, bis[(C.sub.1-C.sub.8)-alkyl](aryl)silyl(C.sub.1-C.sub.8)-alkyl, [(C.sub.1-C.sub.8)-alkyl]bis(aryl)silyl-(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, arylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, aryloxy-(C.sub.1-C.sub.8)-alkyl, heteroaryloxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, R.sup.14 is 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.3-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.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, bis[(C.sub.1-C.sub.8)-alkyl]amino, (C.sub.1-C.sub.8)-alkylamino, aryl-(C.sub.1-C.sub.8)-amino, aryl-(C.sub.1-C.sub.6)-alkylamino, aryl-[(C.sub.1-C.sub.8)-alkyl]amino; (C.sub.3-C.sub.8)-cycloalkylamino, (C.sub.3-C.sub.8)-cycloalkyl-[(C.sub.1-C.sub.8)-alkyl]amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, and X and Y are independently O (oxygen) or S (sulfur).
2. The compound of formula (I) as claimed in claim 1 and/or salt thereof, wherein R.sup.1 is hydrogen, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, R.sup.2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C.sub.1-C.sub.6)-alkoxy, R.sup.3 is hydrogen, halogen, (C.sub.1-C.sub.6)-alkoxy, R.sup.4 is halogen, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkynyl, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, G is unbranched or branched (C.sub.1-C.sub.6)-alkylene, Q is a radical of formula ##STR00115## R.sup.8 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-alkenyl, C(O)R.sup.13, C(O)OR.sup.13, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, R.sup.9 is hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.10 is cyano, NO.sub.2, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, R.sup.11R.sup.12N(C.sub.1-C.sub.6)-alkyl, R.sup.13O(C.sub.1-C.sub.6)-alkyl, cyano-(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, arylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, OR.sup.13, NR.sup.11R.sup.12, SR.sup.14, S(O)R.sup.14, SO.sub.2R.sup.14, R.sup.14S(C.sub.1-C.sub.6)-alkyl, R.sup.14(O)S(C.sub.1-C.sub.6)-alkyl, R.sup.14O.sub.2S(C.sub.1-C.sub.6)-alkyl, tris[(C.sub.1-C.sub.6)-alkyl]silyl-(C.sub.1-C.sub.6)-alkyl, bis[(C.sub.1-C.sub.6)-alkyl](aryl)silyl(C.sub.1-C.sub.6)-alkyl, [(C.sub.1-C.sub.6)-alkyl]bis(aryl)silyl-(C.sub.1-C.sub.6)-alkyl, tris[(C.sub.1-C.sub.6)-alkyl]silyl, bishydroxyboryl-(C.sub.1-C.sub.6)-alkyl, bis[(C.sub.1-C.sub.6)-alkoxy]boryl-(C.sub.1-C.sub.6)-alkyl, tetramethyl-1,3,2-dioxaborolan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl-(C.sub.1-C.sub.6)-alkyl, nitro-(C.sub.1-C.sub.6)-alkyl, C(O)R.sup.13, bis(C.sub.1-C.sub.6)-alkoxymethyl, bis(C.sub.1-C.sub.6)-alkoxymethyl-(C.sub.1-C.sub.6)-alkyl, R.sup.8 and R.sup.10 together with the carbon atom to which they are bonded form a fully saturated or partly saturated 3- to 10-membered monocyclic or bicyclic heterocyclyl optionally having further substitution, R.sup.11 and R.sup.12 are the same or different and are independently 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.3-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.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, COR.sup.13, SO.sub.2R.sup.14, heterocyclyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, bis[(C.sub.1-C.sub.6)-alkyl]aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkylaminocarbonyl-(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, or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are bonded form a fully saturated or partly saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution, R.sup.13 is 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.3-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)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, (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)-alkoxy-(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)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxy-(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, bis[(C.sub.1-C.sub.6)-alkyl]aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl, bis[(C.sub.1-C.sub.6)-alkyl]amino-(C.sub.2-C.sub.4)-alkyl, (C.sub.1-C.sub.6)-alkylamino-(C.sub.2-C.sub.4)-alkyl, aryl-(C.sub.1-C.sub.6)-alkylamino-(C.sub.2-C.sub.4)-alkyl, R.sup.14S(C.sub.1-C.sub.6)-alkyl, R.sup.14(O)S(C.sub.1-C.sub.6)-alkyl, R.sup.14O.sub.2S(C.sub.1-C.sub.6)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, tris[(C.sub.1-C.sub.6)-alkyl]silyl-(C.sub.1-C.sub.6)-alkyl, bis[(C.sub.1-C.sub.6)-alkyl](aryl)silyl(C.sub.1-C.sub.6)-alkyl, [(C.sub.1-C.sub.6)-alkyl]bis(aryl)silyl-(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, arylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, aryloxy-(C.sub.1-C.sub.6)-alkyl, heteroaryloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, R.sup.14 is 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.3-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.1)-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.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.1)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, bis[(C.sub.1-C.sub.6)-alkyl]amino, (C.sub.1-C.sub.6)-alkylamino, aryl-(C.sub.1-C.sub.6)-amino, aryl-(C.sub.1-C.sub.2)-alkylamino, aryl-[(C.sub.1-C.sub.6)-alkyl]amino; (C.sub.3-C.sub.6)-cycloalkylamino, (C.sub.3-C.sub.6)-cycloalkyl-[(C.sub.1-C.sub.6)-alkyl]amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, and X and Y are independently O (oxygen) or S (sulfur).
3. The compound of formula (I) as claimed in claim 1 and/or salt thereof, wherein R.sup.1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 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, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, R.sup.2 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-1-yloxy, but-1-yloxy, R.sup.3 is hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, R.sup.4 is fluorine, chlorine, bromine, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 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, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl)ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, 1,1,2-trimethylethyl-1-ene, 1,2,2-trimethylethyl-1-ene, 1,1,2,2-tetramethylethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene, n-hexylene, 1-methylpentyl-1-ene, 2-methylpentyl-1-ene, 3-methylpentyl-1-ene, 4-methylpentyl-1-ene, 1,1-dimethylbutyl-1-ene, 1,2-dimethylbutyl-1-ene, 1,3-dimethylbutyl-1-ene, 2,2-dimethylbutyl-1-ene, 2,3-dimethylbutyl-1-ene, 3,3-dimethylbutyl-1-ene, 1-ethylbutyl-1-ene, 2-ethylbutyl-1-ene, 1,1,2-trimethylpropyl-1-ene, 1,2,2-trimethylpropyl-1-ene, 1-ethyl-1-methylpropyl-1-ene, 1-ethyl-2-methylpropyl-1-ene, X and Y are independently O (oxygen) or S (sulfur) and Q is one of the moieties Q-1 to Q-406 specified below, where the arrow in the structural formulae in the table below represents a bond of the respective Q group to a carbonyl group in formula (I): ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156##
4. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, R.sup.2 is fluorine, R.sup.3 is hydrogen, fluorine, chlorine, bromine, methoxy, R.sup.4 is fluorine, chlorine, bromine, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, trifluoromethyl, ethynyl, propyn-1-yl, R.sup.5, R.sup.6, R.sup.7 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl)ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene, n-hexylene, X and Y are independently O (oxygen) or S (sulfur) and Q is one of the moieties Q-1 to Q-406.
5. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 is hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, R.sup.2 is fluorine, R.sup.3 is fluorine, R.sup.4 is chlorine, bromine, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, G is methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene, n-hexylene, X and Y are independently O (oxygen) or S (sulfur) and Q is one of the moieties Q-1 to Q-406.
6. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 is hydrogen, R.sup.2 is fluorine, R.sup.3 is fluorine, R.sup.4 is chlorine, bromine, cyano, NO.sub.2, R.sup.5 is hydrogen, fluorine, chlorine, bromine, R.sup.6 is hydrogen, fluorine, chlorine, bromine, cyano, R.sup.7 is hydrogen, G is methylene, (methyl)methylene, X is O (oxygen) or S (sulfur), Y is O (oxygen) and Q is one of the moieties Q-1 to Q-406.
7. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 is hydrogen, R.sup.2 is fluorine, R.sup.3 is fluorine, R.sup.4 is chlorine, bromine, cyano, NO.sub.2, R.sup.5 is hydrogen, fluorine, R.sup.6 is hydrogen, fluorine, bromine, cyano, R.sup.7 is hydrogen, G is methylene, (methyl)methylene, X is O (oxygen) or S (sulfur), Y is O (oxygen) and Q is one of the moieties Q-1 to Q-35, Q-41 to Q-45, Q-58, Q-71 to Q-80, Q-89, Q-94, Q-95, Q-115, Q-120 to Q-123, Q-152 to Q-155, Q-166 to Q-170, Q-176 to Q-190, Q-261 to Q-348, Q-352 to Q-372, Q-377, Q-391-Q-399.
8. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 is hydrogen, R.sup.2 is fluorine, R.sup.3 is fluorine, R.sup.4 is chlorine, bromine, cyano, NO.sub.2, R.sup.5 is hydrogen, fluorine, R.sup.6 is hydrogen, fluorine, bromine, cyano, R.sup.7 is hydrogen, G is methylene, (methyl)methylene, X is O (oxygen) or S (sulfur), Y is O (oxygen) and Q is one of the moieties Q-1, Q-2, Q-3, Q-4, Q-7, Q-8, Q-9, Q-17, Q-18, Q-23, Q-24, Q-26, Q-27, Q-41, Q-42, Q-43, Q-58, Q-71, Q-72, Q-89, Q-94, Q-115, Q-121, Q-176, Q-177, Q-179, Q-183, Q-272, Q-274, Q-275, Q-276, Q-277, Q-278, Q-281, Q-282, Q-283, Q-284, Q-286, Q-288, Q-291, Q-296, Q-301, Q-302, Q-303, Q-308, Q-309, Q-321, Q-327, Q-328, Q-329, Q-331, Q-335, Q-339, Q-356, Q-365, Q-366, Q-367, Q-371, Q-394.
9. A product comprising one or more compounds of formula (I) as defined in claim 1 and/or salts thereof, comprising a herbicide and/or plant growth regulator product, optionally adapted for one or more crops of one or more useful plants and/or ornamentals.
10. A herbicidal and/or plant growth-regulating composition, wherein the composition comprises one or more compounds of formula (I) as defined in claim 1 and/or salts thereof, and one or more further substances selected from groups (i) and/or (ii), comprising (i) one or more further agrochemically active substances, optionally 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.
11. A method of controlling one or more harmful plants and/or for regulating the growth of one or more plants, comprising applying an effective amount of one or more compounds of formula (I), as defined in claim 1 and/or salts thereof, or a composition thereof, to the plants, seeds of plants, soil in which or on which plants grow and/or an area under cultivation.
Description
SYNTHESIS EXAMPLES
Ex. I.1-1: 2-Methoxyethyl [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]acetate
[0179] ##STR00056##
[0180] To a solution of methylglycol (0.012 g, 0.155 mmol) in 4 ml of dichloromethane were added [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]acetic acid (0.060 g, 0.119 mmol) and then, in succession, 1-hydroxy-1H-benzotriazole hydrate (0.024 g, 0.155 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.030 g, 0.155 mmol) and 4-dimethylaminopyridine (10 mol %), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on silica gel with an n-heptane/ethyl acetate gradient. This gave 0.044 g (64% of theory) of 2-methoxyethyl [2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]acetate. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.44-7.41 (m, 1H), 7.34-7.30 (m, 2H), 7.08 (d, 1H), 7.01-6.97 (m, 1H), 6.78-6.76 (m, 1H), 6.27 (s, 1H), 4.70 (s, 2H), 4.29-4.26 (m, 2H), 3.58-3.56 (m, 2H), 3.50-3.49 (m, 3H), 3.35 (s, 3H).
Ex. I.2-1: 2-Methoxyethyl (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]propanoate
[0181] ##STR00057##
[0182] To a solution of methylglycol (0.011 g, 0.150 mmol) in 4 ml of dichloromethane were added (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]propanoic acid (0.060 g, 0.116 mmol) and then, in succession, 1-hydroxy-1H-benzotriazole hydrate (0.023 g, 0.150 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.029 g, 0.150 mmol) and 4-dimethylaminopyridine (10 mol %), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on silica gel with an n-heptane/ethyl acetate gradient. This gave 0.056 g (80% of theory) of 2-methoxyethyl (2RS)-2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}sulfanyl)phenoxy]propanoate. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.43-7.40 (m, 1H), 7.32-7.28 (m, 2H), 7.10-6.95 (m, 2H), 6.76-6.72 (m, 1H), 6.27-6.26 (m, 1H), 4.79-4.73 (m, 1H), 4.32-4.22 (m, 2H), 3.56-3.53 (m, 2H), 3.49 (m, 3H), 3.33 (s, 3H), 1.51-1.50 (m, 3H).
Ex. I.7-176: Cyanomethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0183] ##STR00058##
[0184] To a solution of glycolonitrile (0.027 g, 0.286 mmol) in 10 ml of dichloromethane were added (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.100 g, 0.205 mmol) and then, in succession, 1-hydroxy-1H-benzotriazole hydrate (0.041 g, 0.266 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.051 g, 0.266 mmol) and 4-dimethylaminopyridine (10 mol %), and the mixture was stirred at room temperature for 2 h. Water and dichloromethane were added to the reaction mixture, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with an n-heptane/ethyl acetate gradient, 0.095 g (79% of theory) of a colorless solid was obtained. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.39 (d, 1H), 7.18-7.12 (m, 1H), 7.11-7.03 (m, 2H), 6.94 (d, 1H), 6.68 (d, 1H), 6.29 (s, 1H), 4.76 (s, 2H), 4.74 (s, 2H), 3.50 (s, 3H).
Ex. I.7-71: Tetrahydrofuran-2-ylmethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0185] ##STR00059##
[0186] To a solution of tetrahydrofuran-2-ylmethanol (0.042 g, 0.412 mmol) in 15 ml of dichloromethane were added (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.160 g, 0.327 mmol) and then, in succession, 1-hydroxy-1H-benzotriazole hydrate (0.059 g, 0.383 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.073 g, 0.383 mmol) and 4-dimethylaminopyridine (10 mol %), and the mixture was stirred at room temperature for 2 h. Water and dichloromethane were added to the reaction mixture, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with an n-heptane/ethyl acetate gradient, 0.129 g (73% of theory) of a colorless solid was obtained. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.97 (m, 1H), 6.92 (d, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.70 (s, 2H), 4.21-4.18 (m, 1H), 4.13-4.05 (m, 2H), 3.83-3.73 (m, 2H), 3.50 (s, 3H), 2.04-1.83 (m, 3H), 1.59-1.52 (m, 1H).
Ex. I.7-276: Pyridin-2-ylmethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0187] ##STR00060##
[0188] To a solution of pyridin-2-ylmethanol (0.028 g, 0.258 mmol) in 10 ml of dichloromethane were added (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.100 g, 0.205 mmol) and then, in succession, 1-hydroxy-1H-benzotriazole hydrate (0.037 g, 0.239 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.046 g, 0.239 mmol) and 4-dimethylaminopyridine (10 mol %), and the mixture was stirred at room temperature for 2 h. Water and dichloromethane were added to the reaction mixture, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with an n-heptane/ethyl acetate gradient, 0.096 g (81% of theory) of a colorless solid was obtained. .sup.1H-NMR (CDCl.sub.3 , ppm) 8.57-8.55 (m, 1H), 7.66 (t, 1H), 7.32 (d, 1H), 7.26-7.21 (m, 2H), 7.14-7.08 (m, 2H), 7.02-6.94 (m, 2H), 6.75 (d, 1H), 6.24 (s, 1H), 5.28 (s, 2H), 4.77 (s, 2H), 3.48 (s, 3H).
Ex. I.7-183: 2-Nitroethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0189] ##STR00061##
[0190] To a solution of (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.150 g, 0.306 mmol) in 1.0 ml of toluene were successively added 2-nitroethanol (0.139 g, 1.531 mmol), concentrated acetic acid (0.092 g, 1.531 mmol), concentrated sulfuric acid (0.015 g, 0.153 mmol), and the mixture was stirred under reflux for 5 h. The reaction mixture was left to stand overnight and stirred under reflux for a further 5 h. Water and dichloromethane were added to the reaction mixture, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with an n-heptane/acetone gradient followed by a further purification by column chromatography on silica gel with an n-heptane/ethyl acetate gradient, 0.036 g (20% of theory) of 2-nitroethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate was obtained. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.37 (d, 1H), 7.16-7.12 (m, 1H), 7.09-7.07 (m, 1H), 7.04-7.00 (m, 1H), 6.90 (d, 1H), 6.67 (d, 1H), 6.28 (s, 1H), 4.67 (s, 2H), 4.66-4.64 (m, 2H), 4.59-4.56 (m, 2H), 3.50 (s, 3H).
Ex. I.7-177: 1-Cyanoethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0191] ##STR00062##
[0192] To a solution of (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (0.160 g, 0.327 mmol) in 4.0 ml of acetonitrile were successively added 4-dimethylaminopyridine (0.005 g, 0.039 mmol), potassium carbonate (0.056 g, 0.404 mmol), 2-bromopropanenitrile (0.052 g, 0.389 mmol), and the mixture was stirred at room temperature for 2 h and then under reflux for 1 h. Water and dichloromethane were added to the reaction mixture, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography with an n-heptane/ethyl acetate gradient and subsequent drying of the product obtained under reduced pressure at 40 C., 0.160 g (95% of theory) of 1-cyanoethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate was obtained. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.38 (d, 1H), 7.17-7.13 (m, 1H), 7.10-7.02 (m, 2H), 6.95-6.93 (m, 1H), 6.72-6.68 (m, 1H), 6.29 (d, 1H), 5.45-5.42 (m, 1H), 4.72 (s, 2H), 3.50 (s, 3H), 1.64-1.61 (m, 3H).
Ex. I.7-1: 2-Methoxyethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0193] ##STR00063##
[0194] Under a nitrogen atmosphere, indium(III) chloride (2.599 g, 11.749 mmol) was added to ethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (5.520 g, 10.681 mmol) in 46.32 ml of 2-methoxyethanol, and the mixture was stirred at 115 C. for 3 h. After cooling to room temperature, the reaction mixture was poured onto water, ethyl acetate was added, the aqueous phase was extracted repeatedly with ethyl acetate, the combined organic phases were washed with saturated aqueous sodium chloride solution, the organic phase was dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with an n-heptane/ethyl acetate gradient, 5.150 g (88% of theory) of a colorless solid was obtained. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.05 (m, 1H), 7.01-6.99 (m, 1H), 6.93-6.91 (m, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.70 (s, 2H), 4.29-4.27 (m, 2H), 3.56-3.54 (m, 2H), 3.50 (s, 3H), 3.33 (s, 3H).
Ex. I.7-94: 1-Methoxypropan-2-yl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0195] ##STR00064##
[0196] Under a nitrogen atmosphere, indium(III) chloride (0.116 g, 0.527 mmol) was added to 2-methoxyethyl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (0.160 g, 0.293 mmol) in 4.0 ml of 1-methoxypropan-2-ol, and the reaction mixture was heated at 125 C. in a microwave reactor for 1.5 h. After cooling to room temperature, the reaction mixture was poured onto water, dichloromethane was added, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography with an n-heptane/ethyl acetate gradient, 0.110 g (66% of theory) of 1-methoxypropan-2-yl (2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate was obtained. .sup.1H-NMR (CDCl.sub.3 , ppm) 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.96 (m, 1H), 6.93-6.90 (m, 1H), 6.79-6.76 (m, 1H), 6.28 (d, 1H), 5.16-5.12 (m, 1H), 4.65 (s, 2H), 3.50 (s, 3H), 3.44-3.36 (m, 2H), 3.33 (s, 3H), 1.23 (d, 3H).
Ex. I.6-1: 2-Methoxyethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate
[0197] ##STR00065##
[0198] To ethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate (100 mg, 0.19 mmol) in a microwave vessel under argon were added 2-methoxyethanol (505 mg, 6.63 mmol) and indium(III) chloride (51.2 mg, 0.23 mmol). The reaction mixture was stirred at a temperature of 115 C. under microwave conditions for 120 minutes. After cooling to room temperature, the reaction mixture was stirred with 50 ml of water, and 10 ml of dichloromethane was added. The organic phase was removed and concentrated. Column chromatography purification of the crude product obtained on silica gel with an n-heptane/ethyl acetate gradient afforded 2-methoxyethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate (78 mg, 73% of theory) in the form of a colorless oil.
[0199] .sup.1H-NMR (CDCl.sub.3 , ppm) 7.87 (d, 1H), 7.19 (m, 2H), 7.03 (t, 1H), 6.95 (d, 1H), 6.88 (d, 1H), 6.28 (s, 1H), 4.67 (s, 2H), 4.25 (t, 2H), 3.53 (t, 2H), 3.50 (s, 3H), 3.31 (s, 3H).
Ex. I.6-176: Cyanomethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate
[0200] ##STR00066##
[0201] An initial charge of (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetic acid (100 mg, 0.20 mmol) together with bromoacetonitrile (38 mg, 0.30 mmol) and triethylamine (30 mg, 0.30 mmol) in 1 ml of acetone under argon was stirred at room temperature for 2.5 hours. After TLC monitoring, further bromoacetonitrile (13 mg, 0.10 mmol) was added and the mixture was stirred at room temperature for a further hour. The reaction mixture was concentrated, and 10 ml of water and 10 ml of dichloromethane were added. The organic phase was removed and concentrated. Column chromatography purification of the crude product obtained on silica gel with an n-heptane/ethyl acetate gradient afforded cyanomethyl (2-{4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-nitrophenoxy}phenoxy)acetate (104 mg, 95% of theory) in the form of a colorless oil.
[0202] .sup.1H-NMR (CDCl.sub.3 , ppm) 7.89 (d, 1H), 7.24-7.20 (m, 2H), 7.09 (dt, 1H), 6.92 (dd, 1H), 6.82 (d, 1H), 6.30 (s, 1H), 4.75 (s, 2H), 4.71 (s, 2H), 3.51 (s, 3H).
Ex. I.8-176: Cyanomethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0203] ##STR00067##
[0204] An initial charge of (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetic acid (1.000 g, 1.86 mmol) together with bromoacetonitrile (337 mg, 2.81 mmol) and triethylamine (380 mg, 3.75 mmol) in 22 ml of dichloromethane under argon was stirred at room temperature for 5 hours. The mixture was left to stand overnight, 10 ml of water was added, and then the mixture was stirred. The organic phase was removed and concentrated. Column chromatography purification of the crude product obtained on silica gel with an n-heptane/ethyl acetate gradient afforded cyanomethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (598 mg, 55% of theory) in the form of a colorless oil.
[0205] .sup.1H-NMR (CDCl.sub.3 , ppm) 7.55 (d, 1H), 7.18-7.03 (m, 3H), 6.95 (dd, 1H), 6.64 (d, 1H), 6.29 (s, 1H), 4.76 (s, 2H), 4.75 (s, 2H), 3.50 (s, 3H).
Ex. I.9-176: Cyanomethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate
[0206] ##STR00068##
[0207] An initial charge of cyanomethyl (2-{2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (598 mg, 1.05 mmol) together with zinc cyanide (129 mg, 1.10 mmol) and tetrakis(triphenylphosphine)palladium (0) (121 mg, 0.10 mmol) in 15 ml of N,N-dimethylacetamide under argon was stirred at 180 degrees Celsius for 1 hour. After TLC monitoring, the reaction mixture was added to 10 ml of water and extracted with ethyl acetate. The combined organic phase was washed twice with saturated sodium chloride solution, then dried with sodium sulfate, filtered and then concentrated under reduced pressure. Column chromatography purification of the crude product obtained on silica gel with an n-heptane/ethyl acetate gradient afforded cyanomethyl (2-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}phenoxy)acetate (232 mg, 42% of theory) in the form of a colorless oil.
[0208] .sup.1H-NMR (CDCl.sub.3 , ppm) 7.53 (d, 1H), 7.23 (m, 2H), 7.09 (dt, 1H), 6.90 (d, 1H), 6.68 (d, 1H), 6.29 (s, 1H), 4.75 (s, 2H), 4.71 (s, 2H), 3.50 (s, 3H).
[0209] 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 substituted N-heterocyclyl- and N-heteroaryltetrahydropyrimidinones, the compounds cited below are obtained:
##STR00069##
[0210] Table I.1: Preferred compounds of the formula (I.1) are the compounds I.1-1 to I.1-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.1-1 to I.1-406 of table I.1 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
TABLE-US-00001 TABLE 1 No. Q 1 Q-1 2 Q-2 3 Q-3 4 Q-4 5 Q-5 6 Q-6 7 Q-7 8 Q-8 9 Q-9 10 Q-10 11 Q-11 12 Q-12 13 Q-13 14 Q-14 15 Q-15 16 Q-16 17 Q-17 18 Q-18 19 Q-19 20 Q-20 21 Q-21 22 Q-22 23 Q-23 24 Q-24 25 Q-25 26 Q-26 27 Q-27 28 Q-28 29 Q-29 30 Q-30 31 Q-31 32 Q-32 33 Q-33 34 Q-34 35 Q-35 36 Q-36 37 Q-37 38 Q-38 39 Q-39 40 Q-40 41 Q-41 42 Q-42 43 Q-43 44 Q-44 45 Q-45 46 Q-46 47 Q-47 48 Q-48 49 Q-49 50 Q-50 51 Q-51 52 Q-52 53 Q-53 54 Q-54 55 Q-55 56 Q-56 57 Q-57 58 Q-58 59 Q-59 60 Q-60 61 Q-61 62 Q-62 63 Q-63 64 Q-64 65 Q-65 66 Q-66 67 Q-67 68 Q-68 69 Q-69 70 Q-70 71 Q-71 72 Q-72 73 Q-73 74 Q-74 75 Q-75 76 Q-76 77 Q-77 78 Q-78 79 Q-79 80 Q-80 81 Q-81 82 Q-82 83 Q-83 84 Q-84 85 Q-85 86 Q-86 87 Q-87 88 Q-88 89 Q-89 90 Q-90 91 Q-91 92 Q-92 93 Q-93 94 Q-94 95 Q-95 96 Q-96 97 Q-97 98 Q-98 99 Q-99 100 Q-100 101 Q-101 102 Q-102 103 Q-103 104 Q-104 105 Q-105 106 Q-106 107 Q-107 108 Q-108 109 Q-109 110 Q-110 111 Q-111 112 Q-112 113 Q-113 114 Q-114 115 Q-115 116 Q-116 117 Q-117 118 Q-118 119 Q-119 120 Q-120 121 Q-121 122 Q-122 123 Q-123 124 Q-124 125 Q-125 126 Q-126 127 Q-127 128 Q-128 129 Q-129 130 Q-130 131 Q-131 132 Q-132 133 Q-133 134 Q-134 135 Q-135 136 Q-136 137 Q-137 138 Q-138 139 Q-139 140 Q-140 141 Q-141 142 Q-142 143 Q-143 144 Q-144 145 Q-145 146 Q-146 147 Q-147 148 Q-148 149 Q-149 150 Q-150 151 Q-151 152 Q-152 153 Q-153 154 Q-154 155 Q-155 156 Q-156 157 Q-157 158 Q-158 159 Q-159 160 Q-160 161 Q-161 162 Q-162 163 Q-163 164 Q-164 165 Q-165 166 Q-166 167 Q-167 168 Q-168 169 Q-169 170 Q-170 171 Q-171 172 Q-172 173 Q-173 174 Q-174 175 Q-175 176 Q-176 177 Q-177 178 Q-178 179 Q-179 180 Q-180 181 Q-181 182 Q-182 183 Q-183 184 Q-184 185 Q-185 186 Q-186 187 Q-187 188 Q-188 189 Q-189 190 Q-190 191 Q-191 192 Q-192 193 Q-193 194 Q-194 195 Q-195 196 Q-196 197 Q-197 198 Q-198 199 Q-199 200 Q-200 201 Q-201 202 Q-202 203 Q-203 204 Q-204 205 Q-205 206 Q-206 207 Q-207 208 Q-208 209 Q-209 210 Q-210 211 Q-211 212 Q-212 213 Q-213 214 Q-214 215 Q-215 216 Q-216 217 Q-217 218 Q-218 219 Q-219 220 Q-220 221 Q-221 222 Q-222 223 Q-223 224 Q-224 225 Q-225 226 Q-226 227 Q-227 228 Q-228 229 Q-229 230 Q-230 231 Q-231 232 Q-232 233 Q-233 234 Q-234 235 Q-235 236 Q-236 237 Q-237 238 Q-238 239 Q-239 240 Q-240 241 Q-241 242 Q-242 243 Q-243 244 Q-244 245 Q-245 246 Q-246 247 Q-247 248 Q-248 249 Q-249 250 Q-250 251 Q-251 252 Q-252 253 Q-253 254 Q-254 255 Q-255 256 Q-256 257 Q-257 258 Q-258 259 Q-259 260 Q-260 261 Q-261 262 Q-262 263 Q-263 264 Q-264 265 Q-265 266 Q-266 267 Q-267 268 Q-268 269 Q-269 270 Q-270 271 Q-271 272 Q-272 273 Q-273 274 Q-274 275 Q-275 276 Q-276 277 Q-277 278 Q-278 279 Q-279 280 Q-280 281 Q-281 282 Q-282 283 Q-283 284 Q-284 285 Q-285 286 Q-286 287 Q-287 288 Q-288 289 Q-289 290 Q-290 291 Q-291 292 Q-292 293 Q-293 294 Q-294 295 Q-295 296 Q-296 297 Q-297 298 Q-298 299 Q-299 300 Q-300 301 Q-301 302 Q-302 303 Q-303 304 Q-304 305 Q-305 306 Q-306 307 Q-307 308 Q-308 309 Q-309 310 Q-310 311 Q-311 312 Q-312 313 Q-313 314 Q-314 315 Q-315 316 Q-316 317 Q-317 318 Q-318 319 Q-319 320 Q-320 321 Q-321 322 Q-322 323 Q-323 324 Q-324 325 Q-325 326 Q-326 327 Q-327 328 Q-328 329 Q-329 330 Q-330 331 Q-331 332 Q-332 333 Q-333 334 Q-334 335 Q-335 336 Q-336 337 Q-337 338 Q-338 339 Q-339 340 Q-340 341 Q-341 342 Q-342 343 Q-343 344 Q-344 345 Q-345 346 Q-346 347 Q-347 348 Q-348 349 Q-349 350 Q-350 351 Q-351 352 Q-352 353 Q-353 354 Q-354 355 Q-355 356 Q-356 357 Q-357 358 Q-358 359 Q-359 360 Q-360 361 Q-361 362 Q-362 363 Q-363 364 Q-364 365 Q-365 366 Q-366 367 Q-367 368 Q-368 369 Q-369 370 Q-370 371 Q-371 372 Q-372 373 Q-373 374 Q-374 375 Q-375 376 Q-376 377 Q-377 378 Q-378 379 Q-379 380 Q-380 381 Q-381 382 Q-382 383 Q-383 384 Q-384 385 Q-385 386 Q-386 387 Q-387 388 Q-388 389 Q-389 390 Q-390 391 Q-391 392 Q-392 393 Q-393 394 Q-394 395 Q-395 396 Q-396 397 Q-397 398 Q-398 399 Q-399 400 Q-400 401 Q-401 402 Q-402 403 Q-403 404 Q-404 405 Q-405 406 Q-406
##STR00070##
[0211] Table I.2: Preferred compounds of the formula (I.2) are the compounds I.2-1 to I.2-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.2-1 to I.2-406 of table I.2 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00071##
[0212] Table I.3: Preferred compounds of the formula (I.3) are the compounds I.3-1 to I.3-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.3-1 to I.3-406 of table I.3 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00072##
[0213] Table I.4: Preferred compounds of the formula (I.4) are the compounds I.4-1 to I.4-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.4-1 to I.4-406 of table I.4 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00073##
[0214] Table I.5: Preferred compounds of the formula (I.5) are the compounds I.5-1 to I.5-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.5-1 to I.5-406 of table I.5 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00074##
[0215] Table I.6: Preferred compounds of the formula (I.6) are the compounds I.6-1 to I.6-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.6-1 to I.6-406 of table I.6 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00075##
[0216] Table I.7: Preferred compounds of the formula (I.7) are the compounds I.7-1 to I.7-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.7-1 to I.7-406 of table I.7 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00076##
[0217] Table I.8: Preferred compounds of the formula (I.8) are the compounds I.8-1 to I.8-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.8-1 to I.8-406 of table I.8 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00077##
[0218] Table I.9: Preferred compounds of the formula (I.9) are the compounds I.9-1 to I.9-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.9-1 to I.9-406 of table I.9 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00078##
[0219] Table I.10: Preferred compounds of the formula (I.10) are the compounds I.10-1 to I.10-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.10-1 to I.10-406 of table I.10 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00079##
[0220] Table I.11: Preferred compounds of the formula (I.11) are the compounds I.11-1 to I.11-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.11-1 to I.11-406 of table I.11 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00080##
[0221] Table I.12: Preferred compounds of the formula (I.12) are the compounds I.12-1 to I.12-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.12-1 to I.12-406 of table I.12 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00081##
[0222] Table I.13: Preferred compounds of the formula (I.13) are the compounds I.13-1 to I.13-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.13-1 to I.13-406 of table I.13 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00082##
[0223] Table I.14: Preferred compounds of the formula (I.14) are the compounds I.14-1 to I.14-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.14-1 to I.14-406 of table I.14 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00083##
[0224] Table I.15: Preferred compounds of the formula (I.15) are the compounds I.15-1 to I.15-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.15-1 to I.15-406 of table I.15 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00084##
[0225] Table I.16: Preferred compounds of the formula (I.16) are the compounds I.16-1 to I.16-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.16-1 to I.16-406 of table I.16 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00085##
[0226] Table I.17: Preferred compounds of the formula (I.17) are the compounds I.17-1 to I.17-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.17-1 to I.17-406 of table I.17 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00086##
[0227] Table I.18: Preferred compounds of the formula (I.18) are the compounds I.18-1 to I.18-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.18-1 to I.18-406 of table I.18 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00087##
[0228] Table I.19: Preferred compounds of the formula (I.19) are the compounds I.19-1 to I.19-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.19-1 to I.19-406 of table I.19 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00088##
[0229] Table I.20: Preferred compounds of the formula (I.20) are the compounds I.20-1 to I.20-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.20-1 to I.20-406 of table I.20 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00089##
[0230] Table I.21: Preferred compounds of the formula (I.21) are the compounds I.21-1 to I.21-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.21-1 to I.21-406 of table I.21 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00090##
[0231] Table I.22: Preferred compounds of the formula (I.22) are the compounds I.22-1 to I.22-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.22-1 to I.22-406 of table I.22 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00091##
[0232] Table I.23: Preferred compounds of the formula (I.23) are the compounds I.23-1 to I.23-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.23-1 to I.23-406 of table I.23 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00092##
[0233] Table I.24: Preferred compounds of the formula (I.24) are the compounds I.24-1 to I.24-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.24-1 to I.24-406 of table I.24 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00093##
[0234] Table I.25: Preferred compounds of the formula (I.25) are the compounds I.25-1 to I.25-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.25-1 to I.25-406 of table I.25 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00094##
[0235] Table I.26: Preferred compounds of the formula (I.26) are the compounds I.26-1 to I.26-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.26-1 to I.22-406 of table I.26 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00095##
[0236] Table I.27: Preferred compounds of the formula (I.27) are the compounds I.27-1 to I.27-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.27-1 to I.27-406 of table I.27 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00096##
[0237] Table I.28: Preferred compounds of the formula (I.28) are the compounds I.28-1 to I.28-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.28-1 to I.28-406 of table I.28 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00097##
[0238] Table I.29: Preferred compounds of the formula (I.29) are the compounds I.29-1 to I.29-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.29-1 to I.29-406 of table I.29 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00098##
[0239] Table I.30: Preferred compounds of the formula (I.30) are the compounds I.30-1 to I.30-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.30-1 to I.30-406 of table I.30 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00099##
[0240] Table I.31: Preferred compounds of the formula (I.31) are the compounds I.31-1 to I.31-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.31-1 to I.31-406 of table I.31 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00100##
[0241] Table I.32: Preferred compounds of the formula (I.32) are the compounds I.32-1 to I.32-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.32-1 to I.32-406 of table I.32 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
##STR00101##
[0242] Table I.33: Preferred compounds of the formula (I.33) are the compounds I.33-1 to I.33-406 in which Q has the meanings from table 1 indicated in the respective row. Thus, the compounds I.33-1 to I.33-406 of table I.33 are defined by the meaning of the respective entry nos. 1 to 406 for Q from table 1.
[0243] NMR data of selected examples: The .sup.1H NMR data of selected examples of compounds of the general formula (I) are stated in two different ways, namely (a) conventional NMR interpretation or (b) in the form of 1H NMR peak lists according to the method described below.
[0244] a) Conventional NMR Interpretation
[0245] Ex. I.7-23: .sup.1H-NMR (CDCl.sub.3 , ppm): 7.36 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.04 (m, 1H), 7.01-6.99 (m, 1H), 6.94-6.91 (m, 1H), 6.77 (d, 1H), 6.28 (s, 1H), 4.69 (s, 2H), 4.31-4.29 (m, 2H), 3.69-3.67 (m, 2H), 3.61-3.59 (m, 2H), 3.52-3.50 (m, 2H), 3.37 (s, 3H).
[0246] Ex. I.7-121: .sup.1H-NMR (CDCl.sub.3 , ppm): 7.37 (d, 1H), 7.14-7.10 (m, 1H), 7.07-7.05 (m, 1H), 7.02-6.98 (m, 1H), 6.91 (d, 1H), 6.74-6.71 (m, 1H), 6.28 (s, 1H), 5.36-5.33 (m, 1H), 4.65 (s, 2H), 3.88-3.77 (m, 4H), 3.50 (s, 3H), 2.17-2.10 (m, 1H), 1.99-1.95 (m, 1H).
[0247] Ex. I.7-286: .sup.1H-NMR (CDCl.sub.3 , ppm): 8.47 (d, 1H), 7.69 (d, 1H), 7.33 (d, 1H), 7.26-7.22 (m, 1H), 7.13-6.96 (m, 4H), 6.80 (d, 1H), 6.26 (s, 1H), 5.30 (s, 2H), 4.82 (s, 2H), 3.48 (s, 3H).
[0248] Ex. I.7-335: .sup.1H-NMR (CDCl.sub.3 , ppm): 8.65 (s, 1H), 7.75 (d, 1H), 7.67 (d, 1H), 7.32 (d, 1H), 7.12 (t, 1H), 7.07 (d, 1H), 7.03 (t, 1H), 6.93 (d, 1H), 6.68 (d, 1H), 6.28 (s, 1H), 5.24 (s, 2H), 4.71 (s, 2H), 3.50 (s, 3H).
[0249] Ex. I.8-335: .sup.1H-NMR (CDCl.sub.3 , ppm): 8.65 (s, 1H), 7.75 (d, 1H), 7.66 (d, 1H), 7.47 (d, 1H), 7.13 (t, 1H), 7.08 (d, 1H), 7.04 (t, 1H), 6.93 (d, 1H), 6.65 (d, 1H), 6.29 (s, 1H), 5.24 (s, 2H), 4.71 (s, 2H), 3.50 (s, 3H).
[0250] Ex. I.9-367: .sup.1H-NMR (CDCl.sub.3 , ppm): 7.46 (d, 1H), 7.22 (d, 1H), 7.15 (t, 1H), 7.07 (s, 1H), 7.03 (t, 1H), 6.85 (d, 1H), 6.80 (d, 1H), 6.25 (s, 1H), 5.19 (s, 2H), 4.68 (s, 2H), 3.48 (s, 3H), 2.69 (s, 3H).
[0251] Ex. I.23-365: .sup.1H-NMR (CDCl.sub.3 , ppm): 7.86 (s, 1H), 7.69 (s, 1H), 7.37 (d, 1H), 6.94-6.90 (m, 1H), 6.84 (d, 1H), 6.81-6.73 (m, 2H), 6.30 (s, 1H), 5.13 (s, 2H), 4.67 (s, 2H), 3.52 (s, 3H).
[0252] Ex. I.23-367: .sup.1H-NMR (CDCl.sub.3 , ppm): 7.36 (d, 1H), 7.11 (s, 1H), 6.95-6.90 (m, 1H), 6.86 (d, 1H), 6.79-6.74 (m, 2H), 6.29 (s, 1H), 5.23 (s, 2H), 4.68 (s, 2H), 3.51 (s, 3H), 2.71 (s, 3H).
[0253] Ex. I.20-176: .sup.1H-NMR (CDCl.sub.3 , ppm): 7.55 (d, 1H), 7.16-7.12 (m, 1H), 6.94-6.89 (m, 1H), 6.70-6.68 (m, 1H), 6.57 (d, 1H), 6.28 (s, 1H), 4.75 (s, 2H), 4.73 (s, 2H), 3.50 (s, 3H).
[0254] Ex. I.20-1: .sup.1H-NMR (CDCl.sub.3 , ppm): 7.52 (d, 1H), 7.11-7.08 (m, 1H), 6.88-6.85 (m, 1H), 6.69 (d, 1H), 6.68-6.66 (m, 1H), 6.26 (s, 1H), 4.69 (s, 2H), 4-28-4.25 (m, 2H), 3.55-3.52 (m, 2H), 3.49 (s, 3H), 3.32 (s, 3H).
[0255] b) NMR Peak List Method
[0256] The 1H NMR data of selected examples are noted in the form of 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.
[0257] The peak list for one example therefore has the form:
[0258] .sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n)
[0259] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.
[0260] For calibration of the chemical shift of 1H NMR spectra we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.
[0261] The lists of the 1H NMR peaks are similar to the conventional 1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.
[0262] 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.
[0263] In the reporting of compound signals in the delta range of solvents and/or water, our lists of 1H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.
[0264] 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 this case to identify reproduction of our preparation process with reference to by-product fingerprints.
[0265] 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.
[0266] Further details of 1H NMR peak lists can be found in Research Disclosure Database Number 564025.
[0267] I.1-72: .sup.1H-NMR (400.0 MHz, CDCl3):
[0268] =7.5190 (1.5); 7.4207 (1.6); 7.4169 (2.3); 7.4142 (1.8); 7.4015 (1.8); 7.3983 (2.4); 7.3949 (1.8); 7.3405 (1.7); 7.3335 (5.3); 7.3198 (2.2); 7.3108 (5.3); 7.3013 (2.1); 7.2969 (1.8); 7.2601 (268.7); 7.0646 (2.8); 7.0579 (2.9); 7.0460 (2.9); 7.0392 (2.8); 7.0209 (1.8); 7.0181 (1.9); 7.0019 (3.1); 6.9992 (3.2); 6.9962 (1.7); 6.9830 (1.6); 6.9803 (1.5); 6.7737 (2.9); 6.7531 (2.7); 6.2969 (4.7); 6.2768 (4.6); 4.6694 (16.0); 4.1622 (1.0); 4.1457 (1.1); 4.1403 (1.0); 4.1353 (1.5); 4.1309 (1.8); 4.1239 (1.0); 4.1190 (1.5); 4.1132 (3.0); 4.0968 (1.6); 4.0500 (1.6); 4.0295 (3.0); 4.0231 (1.0); 4.0090 (1.6); 4.0027 (2.0); 3.9822 (1.1); 3.8550 (0.9); 3.8413 (1.0); 3.8340 (2.0); 3.8205 (2.1); 3.8137 (1.5); 3.7998 (1.4); 3.7678 (1.2); 3.7645 (1.2); 3.7457 (3.7); 3.7276 (3.6); 3.7082 (1.9); 3.6871 (1.1); 3.5296 (1.3); 3.5167 (1.5); 3.5016 (12.4); 3.4987 (12.9); 3.4875 (1.3); 3.4742 (1.1); 2.5594 (0.8); 2.5426 (1.0); 2.5246 (0.8); 2.0450 (7.2); 2.0196 (0.8); 2.0064 (1.0); 1.9876 (1.1); 1.9743 (0.8); 1.5985 (0.6); 1.5798 (1.0); 1.5668 (1.4); 1.5411 (10.0); 1.5160 (0.7); 1.3037 (0.8); 1.2773 (3.0); 1.2595 (6.0); 1.2416 (2.2); 0.8991 (1.9); 0.8821 (6.5); 0.8643 (2.4); 0.1459 (0.6); 0.0080 (4.7); 0.0002 (160.7); 0.0086 (4.6); 0.1496 (0.6)
[0269] I.2-72: .sup.1H-NMR (400.0 MHz, CDCl3):
[0270] =7.3961 (0.6); 7.3926 (0.5); 7.3849 (0.8); 7.3802 (0.9); 7.3765 (0.7); 7.3735 (0.6); 7.3658 (0.8); 7.3369 (1.3); 7.3311 (1.4); 7.3143 (1.3); 7.3085 (1.4); 7.2970 (0.5); 7.2930 (0.6); 7.2781 (1.0); 7.2738 (1.2); 7.2600 (35.9); 7.2549 (0.9); 7.1025 (0.8); 7.0913 (0.8); 7.0839 (0.7); 7.0727 (0.8); 7.0105 (0.7); 6.9969 (0.8); 6.9918 (0.8); 6.9881 (1.0); 6.9854 (1.0); 6.9785 (0.8); 6.9691 (1.6); 6.9664 (1.6); 6.9502 (0.8); 6.9475 (0.7); 6.7229 (0.7); 6.7091 (0.8); 6.7013 (0.7); 6.6886 (0.7); 6.2969 (1.3); 6.2825 (2.2); 6.2685 (1.2); 4.7637 (1.0); 4.7467 (1.1); 4.7323 (0.9); 4.1304 (0.7); 4.1126 (0.6); 4.0548 (0.6); 4.0495 (0.7); 4.0380 (0.6); 4.0298 (0.7); 4.0061 (0.8); 3.9791 (0.5); 3.8202 (0.7); 3.8072 (0.6); 3.7992 (0.7); 3.7287 (0.8); 3.7235 (1.1); 3.7114 (1.1); 3.7057 (1.1); 3.7009 (1.0); 3.6921 (0.9); 3.6827 (0.7); 3.4952 (5.7); 3.4829 (0.8); 3.4694 (0.7); 3.4601 (0.9); 3.4468 (0.9); 2.0449 (1.7); 1.5412 (16.0); 1.5152 (4.7); 1.5109 (4.3); 1.4981 (4.5); 1.4940 (4.1); 1.2771 (1.0); 1.2647 (1.9); 1.2594 (2.0); 1.2415 (0.6); 0.8990 (1.0); 0.8820 (3.6); 0.8643 (1.4); 0.0079 (1.4); 0.0002 (46.0); 0.0085 (1.3)
[0271] I.2-71: .sup.1H-NMR (400.0 MHz, CDCl3):
[0272] =7.4207 (0.5); 7.4095 (0.6); 7.4051 (0.7); 7.4014 (0.6); 7.3904 (0.6); 7.3234 (1.1); 7.3183 (1.1); 7.3008 (1.6); 7.2959 (1.2); 7.2813 (0.8); 7.2600 (37.4); 7.1072 (0.6); 7.0972 (0.6); 7.0885 (0.6); 7.0785 (0.6); 7.0224 (0.6); 7.0186 (0.6); 7.0037 (0.6); 6.9999 (0.6); 6.9792 (0.6); 6.9614 (1.1); 6.9423 (0.5); 6.7456 (0.8); 6.7254 (0.5); 6.2736 (1.7); 6.2666 (1.0); 6.2610 (1.0); 4.7857 (0.6); 4.7695 (0.6); 4.7570 (0.5); 4.1854 (0.5); 4.1308 (0.7); 4.1135 (0.6); 4.0803 (0.6); 4.0682 (0.8); 4.0633 (0.9); 4.0440 (0.9); 3.7892 (0.7); 3.7726 (0.8); 3.7601 (0.5); 3.7557 (0.5); 3.4894 (3.1); 3.4864 (3.4); 2.0452 (1.3); 1.8965 (0.6); 1.8910 (0.6); 1.8837 (0.6); 1.8774 (0.7); 1.8716 (0.8); 1.8605 (0.5); 1.8545 (0.5); 1.5387 (16.0); 1.5148 (3.3); 1.4977 (3.2); 1.2773 (0.8); 1.2644 (1.7); 1.2597 (1.8); 1.2417 (0.5); 0.8990 (0.9); 0.8820 (3.1); 0.8643 (1.2); 0.0080 (1.5); 0.0002 (47.9); 0.0085 (1.2)
[0273] I.2-23: .sup.1H-NMR (400.0 MHz, CDCl3):
[0274] =7.4172 (1.0); 7.4130 (1.1); 7.4071 (1.0); 7.4029 (1.1); 7.3980 (1.1); 7.3938 (1.1); 7.3879 (1.0); 7.3837 (1.1); 7.3265 (1.9); 7.3209 (1.9); 7.3038 (2.4); 7.2985 (2.4); 7.2845 (1.3); 7.2826 (1.4); 7.2806 (1.3); 7.2602 (32.9); 7.0934 (1.8); 7.0748 (1.8); 7.0059 (1.7); 6.9873 (1.8); 6.9828 (1.1); 6.9803 (1.1); 6.9639 (1.9); 6.9614 (1.9); 6.9451 (0.9); 6.9425 (0.9); 6.7504 (1.0); 6.7377 (1.0); 6.7323 (1.0); 6.7194 (0.9); 6.2753 (5.0); 4.7680 (1.2); 4.7547 (1.2); 4.7509 (1.2); 4.7377 (1.2); 4.2900 (0.7); 4.2784 (2.4); 4.2658 (2.8); 4.2563 (1.9); 3.6811 (2.9); 3.6691 (3.7); 3.6571 (2.6); 3.6049 (0.8); 3.6009 (1.0); 3.5991 (1.1); 3.5946 (2.3); 3.5887 (2.5); 3.5847 (1.4); 3.5812 (2.8); 3.5745 (2.1); 3.5202 (2.5); 3.5125 (3.5); 3.5071 (2.4); 3.4907 (7.0); 3.4887 (6.7); 3.3717 (16.0); 3.3690 (16.0); 1.5447 (13.3); 1.5076 (8.9); 1.4906 (8.8); 1.2648 (0.8); 0.8820 (1.4); 0.8642 (0.6); 0.0080 (1.2); 0.0002 (42.0); 0.0085 (1.2)
[0275] I.2-2: .sup.1H-NMR (400.0 MHz, CDCl3):
[0276] =7.4253 (0.8); 7.4210 (0.8); 7.4179 (0.8); 7.4135 (0.8); 7.4061 (0.8); 7.4020 (0.9); 7.3985 (0.8); 7.3945 (0.8); 7.3237 (1.5); 7.3191 (1.5); 7.3010 (1.9); 7.2966 (2.0); 7.2778 (1.2); 7.2600 (44.7); 7.0984 (1.4); 7.0798 (1.4); 7.0118 (1.4); 6.9932 (1.4); 6.9804 (0.9); 6.9638 (1.5); 6.9612 (1.5); 6.9425 (0.7); 6.7493 (0.8); 6.7401 (0.8); 6.7311 (0.7); 6.7192 (0.8); 6.2735 (2.3); 6.2657 (2.3); 4.7719 (1.0); 4.7579 (1.0); 4.7548 (1.0); 4.7410 (1.0); 4.2748 (0.6); 4.2635 (1.8); 4.2570 (1.2); 4.2512 (2.4); 4.2415 (1.2); 3.6034 (2.4); 3.5914 (2.8); 3.5793 (2.1); 3.5096 (0.8); 3.5045 (0.9); 3.4921 (5.8); 3.4870 (7.0); 3.4746 (2.6); 3.4695 (2.6); 3.4571 (0.8); 3.4519 (0.9); 1.5378 (16.0); 1.5110 (7.3); 1.4939 (7.1); 1.2647 (1.3); 1.1993 (2.6); 1.1936 (2.7); 1.1818 (5.4); 1.1761 (5.4); 1.1643 (2.6); 1.1586 (2.6); 0.8989 (0.7); 0.8820 (2.2); 0.8643 (0.9); 0.0080 (1.8); 0.0002 (58.2); 0.0085 (1.6)
[0277] I.2-58: .sup.1H-NMR (400.0 MHz, CDCl3):
[0278] =7.5189 (0.8); 7.4260 (1.6); 7.4218 (1.9); 7.4163 (1.6); 7.4122 (1.8); 7.4068 (2.0); 7.4027 (2.0); 7.3971 (1.8); 7.3930 (1.9); 7.3435 (3.2); 7.3365 (3.3); 7.3206 (4.0); 7.3141 (4.2); 7.2996 (2.4); 7.2975 (2.3); 7.2954 (2.2); 7.2792 (1.6); 7.2749 (1.6); 7.2601 (152.7); 7.0526 (3.0); 7.0340 (3.1); 7.0079 (1.3); 7.0050 (2.4); 7.0020 (1.3); 6.9937 (3.1); 6.9890 (2.2); 6.9861 (3.8); 6.9832 (2.1); 6.9751 (3.1); 6.9700 (1.1); 6.9672 (1.9); 6.9643 (1.0); 6.7996 (1.6); 6.7750 (2.2); 6.7532 (1.6); 6.2920 (5.2); 6.2876 (4.9); 4.8190 (0.6); 4.8021 (1.9); 4.7850 (2.0); 4.7797 (2.0); 4.7626 (2.0); 4.7456 (0.6); 4.2560 (0.6); 4.2360 (1.3); 4.2266 (2.2); 4.2224 (2.5); 4.2182 (2.0); 4.2133 (4.7); 4.2089 (1.9); 4.2049 (2.6); 4.2027 (2.1); 4.1994 (1.8); 4.1932 (1.5); 4.1729 (0.6); 4.1486 (0.6); 4.1308 (1.8); 4.1131 (1.8); 4.0950 (0.6); 3.7542 (1.7); 3.7448 (3.2); 3.7352 (2.5); 3.5010 (13.1); 3.4981 (13.4); 2.0449 (8.6); 1.5454 (16.0); 1.5420 (15.1); 1.5284 (11.0); 1.5250 (10.3); 1.2843 (1.4); 1.2772 (3.6); 1.2594 (7.5); 1.2415 (2.8); 0.8990 (2.1); 0.8820 (7.3); 0.8643 (2.8); 0.0080 (4.6); 0.0002 (153.4); 0.0085 (4.3); 0.1496 (0.5)
[0279] I.1-26: .sup.1H-NMR (400.0 MHz, CDCl3):
[0280] =7.4316 (1.0); 7.4275 (1.1); 7.4125 (1.1); 7.4083 (1.1); 7.3405 (0.5); 7.3362 (0.5); 7.3253 (2.0); 7.3218 (0.8); 7.3199 (0.8); 7.3175 (0.8); 7.3158 (0.7); 7.3025 (2.1); 7.2969 (0.6); 7.2600 (24.5); 7.0896 (1.8); 7.0710 (1.8); 7.0140 (0.6); 7.0113 (0.7); 6.9952 (1.2); 6.9923 (1.2); 6.9762 (0.5); 6.9734 (0.6); 6.7728 (1.0); 6.7703 (1.0); 6.7521 (0.9); 6.7496 (0.9); 6.2872 (3.0); 4.6610 (5.8); 4.2291 (0.7); 4.2235 (0.8); 4.2127 (1.6); 4.2073 (1.6); 4.1965 (0.8); 4.1911 (0.8); 3.5000 (4.1); 3.4971 (4.2); 3.3932 (1.7); 3.3779 (3.6); 3.3626 (1.8); 3.2982 (16.0); 2.0069 (0.6); 1.8938 (1.5); 1.8781 (2.2); 1.8624 (1.5); 1.5395 (9.6); 0.0080 (0.9); 0.0002 (32.4); 0.0085 (0.9)
[0281] I.1-23: .sup.1H-NMR (400.0 MHz, CDCl3):
[0282] =7.4227 (1.0); 7.4186 (1.1); 7.4036 (1.1); 7.3994 (1.1); 7.3379 (0.6); 7.3336 (0.6); 7.3253 (2.0); 7.3191 (0.8); 7.3173 (0.8); 7.3150 (0.8); 7.3131 (0.7); 7.3027 (2.0); 7.2986 (0.8); 7.2943 (0.6); 7.2606 (7.8); 7.0826 (1.8); 7.0639 (1.8); 7.0115 (0.7); 7.0086 (0.7); 6.9925 (1.2); 6.9897 (1.2); 6.9736 (0.6); 6.9708 (0.6); 6.7872 (1.0); 6.7847 (1.0); 6.7665 (1.0); 6.7640 (0.9); 6.2781 (3.0); 4.6947 (5.7); 4.3023 (1.5); 4.2935 (1.1); 4.2904 (1.6); 4.2867 (1.0); 4.2782 (1.6); 3.7020 (1.8); 3.6933 (1.1); 3.6899 (1.8); 3.6870 (1.1); 3.6780 (1.6); 3.6251 (1.2); 3.6172 (1.4); 3.6144 (1.6); 3.6093 (1.4); 3.6026 (2.4); 3.5366 (2.5); 3.5300 (1.4); 3.5244 (1.6); 3.5222 (1.5); 3.5135 (1.2); 3.4979 (4.2); 3.4951 (4.3); 3.3763 (16.0); 1.2844 (0.5); 1.2550 (1.5); 0.0002 (10.2)
[0283] I.1-71: .sup.1H-NMR (400.0 MHz, CDCl3):
[0284] =7.4740 (16.0); 7.4228 (0.8); 7.4186 (0.9); 7.4036 (0.9); 7.3995 (1.0); 7.3473 (0.7); 7.3453 (0.7); 7.3431 (0.7); 7.3412 (0.6); 7.3351 (1.7); 7.3267 (0.6); 7.3224 (0.6); 7.3126 (1.6); 7.1128 (0.9); 7.1103 (0.9); 7.0943 (0.9); 7.0916 (0.9); 7.0228 (0.6); 7.0200 (0.6); 7.0039 (1.0); 7.0011 (1.0); 6.9849 (0.5); 6.8135 (0.9); 6.7928 (0.8); 6.2879 (1.5); 6.2823 (1.4); 4.7135 (3.6); 4.1625 (0.6); 4.0841 (1.0); 4.0806 (0.7); 4.0775 (0.6); 4.0678 (0.9); 4.0534 (0.5); 3.8216 (0.6); 3.8165 (0.5); 3.7678 (0.6); 3.4989 (3.5); 2.7526 (7.9); 2.5968 (2.3); 2.5921 (4.7); 2.5874 (6.5); 2.5827 (4.5); 2.5780 (2.0); 1.9141 (0.7); 1.9107 (0.8); 1.8944 (0.9); 1.8778 (0.6); 0.0080 (0.8); 0.0002 (21.7); 0.0085 (0.6)
[0285] I.7-276: .sup.1H-NMR (400.6 MHz, CDCl3):
[0286] =8.5693 (1.3); 8.5653 (1.7); 8.5623 (1.3); 8.5577 (1.2); 8.5547 (1.6); 8.5505 (1.4); 7.6829 (1.2); 7.6785 (1.2); 7.6636 (2.1); 7.6592 (2.3); 7.6444 (1.4); 7.6400 (1.4); 7.3311 (4.6); 7.3089 (4.6); 7.2654 (0.9); 7.2611 (74.1); 7.2554 (0.9); 7.2396 (3.5); 7.2382 (3.7); 7.2262 (1.6); 7.2249 (1.5); 7.2195 (3.8); 7.2074 (1.3); 7.1368 (1.1); 7.1323 (1.3); 7.1183 (1.6); 7.1166 (1.7); 7.1139 (2.0); 7.1122 (2.0); 7.0983 (1.8); 7.0938 (2.3); 7.0860 (2.1); 7.0816 (2.1); 7.0659 (3.9); 7.0616 (2.8); 7.0194 (2.1); 7.0157 (2.6); 7.0010 (2.0); 6.9995 (1.7); 6.9975 (2.5); 6.9957 (1.9); 6.9810 (1.1); 6.9774 (1.1); 6.9599 (2.9); 6.9563 (2.5); 6.9396 (2.3); 6.9361 (2.0); 6.7627 (4.3); 6.7463 (4.5); 6.2439 (7.6); 5.2819 (12.6); 4.7754 (16.0); 4.7671 (0.8); 3.4786 (10.2); 3.4756 (10.6); 2.0451 (2.3); 1.5909 (1.2); 1.2772 (1.0); 1.2641 (1.1); 1.2594 (2.1); 1.2415 (0.8); 0.8988 (0.6); 0.8819 (2.2); 0.8643 (0.8); 0.0080 (1.3); 0.0041 (0.6); 0.0002 (46.0); 0.0058 (0.7); 0.0085 (1.3)
[0287] I.7-176: .sup.1H-NMR (400.6 MHz, CDCl3):
[0288] =7.3991 (3.0); 7.3770 (3.1); 7.2607 (35.1); 7.1781 (0.8); 7.1734 (0.9); 7.1599 (1.2); 7.1579 (1.2); 7.1553 (1.4); 7.1533 (1.2); 7.1398 (1.2); 7.1351 (1.5); 7.1160 (1.0); 7.1114 (1.3); 7.0960 (2.7); 7.0914 (2.0); 7.0672 (1.7); 7.0636 (1.7); 7.0490 (1.4); 7.0471 (1.2); 7.0455 (1.4); 7.0435 (1.0); 7.0290 (0.7); 7.0253 (0.6); 6.9524 (1.8); 6.9488 (1.7); 6.9321 (1.6); 6.9286 (1.4); 6.6854 (2.9); 6.6691 (2.9); 6.2899 (5.0); 4.7595 (16.0); 4.7450 (12.5); 4.1305 (0.6); 4.1127 (0.6); 3.5050 (7.2); 3.5020 (7.2); 2.0450 (3.0); 1.5507 (6.0); 1.2772 (1.1); 1.2594 (2.1); 1.2415 (0.9); 0.8820 (1.2); 0.0080 (0.6); 0.0002 (22.3); 0.0084 (0.7)
[0289] I.7-2: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):
[0290] =7.8200 (3.9); 7.7969 (3.9); 7.2054 (0.8); 7.2006 (0.9); 7.1878 (1.1); 7.1843 (1.7); 7.1801 (1.6); 7.1672 (1.6); 7.1625 (1.7); 7.1165 (2.5); 7.1133 (2.8); 7.0959 (1.7); 7.0924 (1.6); 7.0844 (1.3); 7.0797 (1.6); 7.0645 (3.7); 7.0598 (3.0); 7.0458 (2.1); 7.0424 (1.9); 7.0282 (1.8); 7.0249 (2.0); 7.0084 (0.8); 7.0047 (0.7); 6.9635 (3.7); 6.9468 (3.8); 6.5141 (7.5); 5.7551 (4.4); 4.7852 (11.1); 4.1967 (3.0); 4.1884 (2.7); 4.1850 (3.4); 4.1811 (2.6); 4.1731 (3.3); 3.5366 (3.6); 3.5283 (2.5); 3.5247 (3.6); 3.5130 (3.2); 3.4239 (2.3); 3.4064 (7.4); 3.3889 (7.6); 3.3714 (2.8); 3.3558 (10.5); 3.3270 (108.8); 2.6753 (0.5); 2.6707 (0.7); 2.6661 (0.5); 2.5242 (1.8); 2.5195 (2.8); 2.5108 (43.0); 2.5063 (87.8); 2.5018 (115.2); 2.4971 (81.0); 2.4926 (37.6); 2.3332 (0.5); 2.3286 (0.7); 2.3240 (0.5); 1.9796 (1.0); 1.2353 (0.4); 1.0801 (7.8); 1.0627 (16.0); 1.0451 (7.5); 0.0002 (2.7)
[0291] I.9-1: .sup.1H-NMR (400.6 MHz, CDCl3):
[0292] =7.5023 (1.5); 7.4812 (1.5); 7.2605 (20.7); 7.2282 (0.7); 7.2241 (1.0); 7.2152 (0.6); 7.2084 (0.8); 7.2046 (1.3); 7.1959 (1.0); 7.1908 (0.6); 7.1758 (0.8); 7.1717 (0.6); 7.0552 (0.7); 7.0516 (0.8); 7.0358 (1.1); 7.0322 (1.0); 7.0165 (0.5); 6.8821 (0.9); 6.8786 (0.9); 6.8616 (0.8); 6.8583 (0.8); 6.8085 (1.4); 6.7940 (1.5); 6.2670 (2.6); 4.6660 (4.2); 4.2621 (0.9); 4.2596 (0.9); 4.2527 (1.0); 4.2510 (1.0); 4.2476 (1.0); 4.2454 (1.0); 4.2388 (1.0); 4.2362 (0.9); 3.5452 (1.8); 3.5335 (1.8); 3.5218 (1.7); 3.4892 (3.7); 3.4862 (3.8); 3.3156 (16.0); 1.5412 (8.4); 0.0080 (0.9); 0.0002 (33.1); 0.0085 (0.9)
[0293] I.7-41: .sup.1H-NMR (400.6 MHz, CDCl3):
[0294] =7.3781 (4.2); 7.3559 (4.2); 7.2602 (38.3); 7.1490 (1.0); 7.1444 (1.1); 7.1306 (1.5); 7.1287 (1.5); 7.1261 (1.8); 7.1242 (1.6); 7.1105 (1.6); 7.1060 (1.9); 7.0834 (1.5); 7.0788 (1.8); 7.0633 (3.6); 7.0588 (2.8); 7.0303 (2.1); 7.0267 (2.3); 7.0120 (1.9); 7.0101 (1.6); 7.0085 (1.9); 7.0067 (1.4); 6.9921 (0.9); 6.9884 (0.9); 6.9363 (2.6); 6.9328 (2.4); 6.9160 (2.2); 6.9125 (1.9); 6.7255 (4.1); 6.7091 (4.1); 6.2769 (7.1); 4.7037 (16.0); 4.6945 (0.6); 4.3814 (2.2); 4.3701 (2.9); 4.3582 (2.7); 4.1411 (4.9); 4.1360 (1.2); 4.1318 (2.8); 4.1292 (4.7); 4.1231 (1.1); 4.1176 (4.0); 4.1128 (0.6); 3.4984 (9.9); 3.4955 (9.9); 2.0448 (1.9); 1.5500 (1.3); 1.2770 (0.9); 1.2728 (0.7); 1.2646 (1.2); 1.2593 (1.9); 1.2551 (0.8); 1.2414 (0.6); 0.8990 (0.6); 0.8820 (2.2); 0.8644 (0.8); 0.0079 (0.7); 0.0002 (24.0); 0.0085 (0.7)
[0295] I.7-278: .sup.1H-NMR (400.6 MHz, CDCl3):
[0296] =8.5830 (2.1); 8.5700 (2.1); 7.5193 (0.6); 7.3136 (4.2); 7.2916 (4.2); 7.2674 (0.7); 7.2666 (0.7); 7.2607 (106.8); 7.1909 (3.2); 7.1762 (3.1); 7.1503 (1.0); 7.1455 (1.2); 7.1322 (1.5); 7.1301 (1.5); 7.1275 (1.9); 7.1254 (1.7); 7.1121 (1.6); 7.1073 (2.1); 7.0927 (1.4); 7.0881 (1.7); 7.0726 (3.8); 7.0680 (2.8); 7.0469 (2.2); 7.0432 (2.6); 7.0288 (1.8); 7.0268 (1.5); 7.0253 (1.9); 7.0232 (1.5); 7.0088 (0.9); 7.0051 (0.9); 6.9972 (0.6); 6.9502 (2.5); 6.9466 (2.4); 6.9299 (2.1); 6.9264 (2.0); 6.7028 (3.9); 6.6864 (4.0); 6.2559 (7.0); 5.1861 (7.2); 4.7523 (16.0); 3.4885 (9.6); 3.4855 (10.2); 2.1716 (3.8); 2.0452 (1.3); 1.2773 (0.7); 1.2639 (1.2); 1.2595 (1.5); 0.8989 (0.6); 0.8820 (2.2); 0.8642 (0.8); 0.0080 (1.9); 0.0002 (68.0); 0.0085 (2.1)
[0297] I.7-277: .sup.1H-NMR (400.2 MHz, d6-DMSO):
[0298] =8.5668 (4.0); 8.5624 (4.0); 8.5424 (2.9); 8.5384 (3.0); 8.5305 (3.1); 8.5264 (3.0); 8.3150 (0.5); 7.7915 (6.0); 7.7684 (6.0); 7.7509 (1.6); 7.7457 (2.4); 7.7410 (1.5); 7.7312 (1.8); 7.7259 (2.7); 7.7215 (1.7); 7.4052 (2.4); 7.4035 (2.4); 7.3931 (2.4); 7.3914 (2.4); 7.3856 (2.2); 7.3839 (2.2); 7.3736 (2.1); 7.3719 (2.1); 7.1993 (0.9); 7.1946 (1.0); 7.1821 (1.1); 7.1784 (2.8); 7.1738 (2.4); 7.1617 (2.8); 7.1572 (3.2); 7.1466 (3.9); 7.1423 (4.6); 7.1258 (1.9); 7.1218 (1.3); 7.0877 (1.6); 7.0831 (2.3); 7.0676 (5.1); 7.0634 (4.0); 7.0497 (3.0); 7.0455 (2.8); 7.0326 (2.4); 7.0287 (2.8); 7.0254 (1.2); 7.0130 (1.1); 7.0085 (1.1); 6.9453 (5.7); 6.9286 (5.8); 6.5024 (11.5); 5.7552 (12.8); 5.1930 (16.0); 4.8511 (14.8); 3.3411 (16.8); 3.3293 (276.4); 3.1752 (0.4); 3.1620 (0.4); 2.6799 (0.3); 2.6754 (0.7); 2.6709 (1.1); 2.6663 (0.8); 2.6616 (0.3); 2.5244 (2.7); 2.5197 (4.2); 2.5110 (65.0); 2.5065 (134.8); 2.5019 (178.0); 2.4973 (125.5); 2.4927 (58.4); 2.3378 (0.4); 2.3333 (0.8); 2.3288 (1.0); 2.3241 (0.8); 2.3197 (0.4); 0.0002 (3.9)
[0299] I.7-291: .sup.1H-NMR (400.6 MHz, CDCl3):
[0300] =9.1487 (1.2); 9.1423 (1.2); 7.5195 (0.6); 7.4664 (1.8); 7.4547 (2.2); 7.4508 (2.7); 7.4458 (2.6); 7.4297 (0.7); 7.3276 (4.3); 7.3057 (4.3); 7.2882 (0.5); 7.2610 (105.3); 7.2529 (0.9); 7.2512 (0.8); 7.1562 (1.0); 7.1516 (1.2); 7.1379 (1.5); 7.1360 (1.6); 7.1333 (1.9); 7.1315 (1.8); 7.1178 (1.7); 7.1132 (2.1); 7.0885 (1.6); 7.0840 (1.9); 7.0685 (3.7); 7.0640 (2.9); 7.0362 (2.1); 7.0326 (2.5); 7.0180 (1.9); 7.0163 (1.5); 7.0144 (2.0); 7.0127 (1.6); 6.9977 (1.3); 6.9944 (1.0); 6.9717 (2.7); 6.9682 (2.4); 6.9515 (2.2); 6.9480 (2.0); 6.6995 (4.1); 6.6832 (4.1); 6.2643 (7.3); 5.5141 (7.7); 5.5114 (8.0); 4.7744 (16.0); 4.7157 (0.5); 3.4946 (10.0); 3.4917 (10.4); 2.1777 (1.1); 2.1717 (5.7); 2.0452 (0.8); 1.2643 (0.9); 1.2596 (1.1); 0.8819 (1.8); 0.8643 (0.7); 0.0079 (1.9); 0.0002 (64.1); 0.0085 (2.0)
[0301] I.7-115: .sup.1H-NMR (400.6 MHz, CDCl3):
[0302] =7.3890 (4.1); 7.3669 (4.1); 7.2606 (39.0); 7.1594 (0.9); 7.1548 (1.1); 7.1411 (1.5); 7.1392 (1.5); 7.1365 (1.8); 7.1347 (1.5); 7.1210 (1.4); 7.1164 (1.7); 7.0956 (1.4); 7.0911 (1.7); 7.0755 (3.5); 7.0710 (2.6); 7.0433 (1.9); 7.0396 (2.1); 7.0250 (1.8); 7.0230 (1.6); 7.0214 (1.8); 7.0198 (1.3); 7.0050 (0.8); 7.0014 (0.8); 6.9456 (2.4); 6.9420 (2.3); 6.9253 (2.1); 6.9218 (1.9); 6.7145 (3.9); 6.6981 (3.9); 6.2819 (6.9); 5.4984 (1.1); 5.4958 (1.1); 5.4826 (2.2); 5.4694 (1.2); 5.4668 (1.2); 5.4537 (0.5); 4.8761 (2.5); 4.8577 (4.0); 4.8550 (3.1); 4.8389 (2.7); 4.6917 (16.0); 4.6268 (1.6); 4.6230 (1.8); 4.6201 (1.4); 4.6138 (1.6); 4.6074 (2.6); 4.6026 (1.4); 4.6012 (1.4); 4.5945 (1.4); 4.5921 (1.5); 4.5881 (1.2); 3.5011 (9.7); 3.4984 (9.6); 2.1711 (1.4); 1.5530 (5.1); 1.2650 (1.0); 0.8990 (0.5); 0.8821 (1.7); 0.8644 (0.7); 0.0080 (0.7); 0.0002 (23.5); 0.0085 (0.6)
[0303] I.7-356: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):
[0304] =7.7947 (2.6); 7.7716 (2.6); 7.5769 (4.4); 7.1853 (0.6); 7.1798 (0.6); 7.1686 (0.7); 7.1637 (1.2); 7.1595 (1.0); 7.1477 (1.0); 7.1423 (1.1); 7.0728 (1.9); 7.0652 (0.6); 7.0598 (1.0); 7.0550 (1.3); 7.0519 (1.3); 7.0455 (2.6); 7.0398 (2.5); 7.0348 (1.6); 7.0207 (1.2); 7.0176 (1.4); 7.0009 (0.4); 6.9976 (0.4); 6.9548 (2.5); 6.9381 (2.6); 6.5087 (5.0); 5.7533 (7.5); 4.9652 (8.4); 4.7377 (7.3); 3.7087 (16.0); 3.3478 (328.3); 2.6766 (0.4); 2.6720 (0.6); 2.6673 (0.4); 2.5254 (1.4); 2.5204 (2.1); 2.5119 (34.8); 2.5075 (72.7); 2.5030 (96.8); 2.4985 (69.9); 2.4940 (33.8); 2.3343 (0.4); 2.3298 (0.6); 2.3254 (0.4); 2.0741 (15.8); 0.0002 (0.5)
[0305] I.7-394: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):
[0306] =8.3127 (0.3); 7.8198 (5.4); 7.7967 (5.5); 7.2189 (1.2); 7.2140 (1.4); 7.1975 (2.8); 7.1936 (2.4); 7.1806 (2.2); 7.1759 (2.4); 7.1150 (4.4); 7.0970 (3.0); 7.0942 (2.8); 7.0861 (10.8); 7.0814 (2.2); 7.0662 (5.2); 7.0616 (4.6); 7.0496 (3.2); 7.0465 (3.1); 7.0319 (2.9); 7.0291 (3.2); 7.0123 (1.2); 7.0089 (1.1); 6.9526 (5.4); 6.9359 (5.4); 6.5432 (0.3); 6.5118 (10.7); 5.7534 (7.2); 5.0458 (0.4); 5.0366 (3.3); 5.0277 (6.9); 5.0189 (3.3); 4.8538 (0.6); 4.8170 (16.0); 4.1382 (0.8); 4.1292 (0.8); 4.1237 (0.5); 4.1088 (5.7); 4.1006 (9.7); 4.0924 (5.5); 4.0718 (0.7); 4.0629 (0.7); 3.8509 (1.0); 3.8460 (1.5); 3.8409 (1.4); 3.8346 (2.3); 3.8292 (4.7); 3.8220 (4.8); 3.8160 (5.7); 3.8112 (3.1); 3.8062 (3.6); 3.7995 (2.8); 3.7912 (5.3); 3.7858 (5.3); 3.7813 (5.0); 3.7768 (4.0); 3.7730 (4.0); 3.7654 (1.2); 3.7568 (1.1); 3.3922 (1.5); 3.3436 (666.4); 3.1755 (0.5); 3.1624 (0.4); 2.6762 (0.8); 2.6718 (1.1); 2.6675 (0.8); 2.5112 (74.2); 2.5072 (141.9); 2.5028 (182.1); 2.4983 (134.0); 2.3339 (0.8); 2.3296 (1.1); 2.3251 (0.8); 0.0002 (1.5)
[0307] I.7-72: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):
[0308] =8.3126 (0.4); 7.8184 (6.1); 7.7953 (6.1); 7.2183 (1.2); 7.2138 (1.3); 7.1971 (2.9); 7.1934 (2.6); 7.1800 (2.5); 7.1755 (2.8); 7.1381 (4.0); 7.1347 (4.6); 7.1175 (2.6); 7.1140 (2.4); 7.0947 (2.0); 7.0903 (2.5); 7.0747 (5.0); 7.0704 (4.3); 7.0490 (3.0); 7.0456 (2.9); 7.0311 (2.8); 7.0281 (3.2); 7.0115 (1.4); 7.0079 (1.3); 6.9472 (6.0); 6.9305 (6.0); 6.5072 (9.2); 5.7535 (8.8); 4.8306 (0.6); 4.7867 (16.0); 4.0760 (1.1); 4.0661 (1.0); 4.0594 (1.2); 4.0493 (2.8); 4.0393 (2.1); 4.0326 (2.0); 4.0227 (2.0); 3.9972 (2.1); 3.9882 (2.0); 3.9773 (2.1); 3.9688 (2.4); 3.9615 (1.2); 3.9504 (1.1); 3.9415 (1.1); 3.7074 (1.2); 3.6933 (1.4); 3.6870 (3.0); 3.6729 (3.1); 3.6668 (2.1); 3.6528 (2.0); 3.6435 (2.5); 3.6222 (3.4); 3.6105 (2.1); 3.6040 (3.1); 3.5914 (3.4); 3.5735 (3.0); 3.5534 (1.3); 3.3870 (3.3); 3.3809 (4.0); 3.3730 (5.3); 3.3462 (870.4); 3.1756 (0.6); 3.1625 (0.5); 2.6809 (0.4); 2.6766 (0.9); 2.6720 (1.2); 2.6675 (0.9); 2.6631 (0.4); 2.5253 (3.5); 2.5204 (5.6); 2.5120 (75.1); 2.5075 (152.8); 2.5030 (200.4); 2.4984 (142.5); 2.4940 (67.6); 2.4741 (1.6); 2.4556 (1.7); 2.4385 (1.2); 2.4207 (0.6); 2.3389 (0.4); 2.3343 (0.9); 2.3298 (1.2); 2.3252 (0.8); 1.9371 (0.7); 1.9230 (0.8); 1.9168 (1.2); 1.9045 (1.4); 1.8965 (0.9); 1.8921 (1.0); 1.8854 (1.5); 1.8717 (1.3); 1.8656 (0.9); 1.8514 (0.7); 1.5429 (0.8); 1.5264 (1.3); 1.5113 (1.7); 1.4921 (1.7); 1.4773 (1.1); 1.4606 (0.7); 0.0002 (0.8)
[0309] I.7-179: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):
[0310] =8.3122 (0.4); 7.8187 (5.4); 7.7956 (5.5); 7.2124 (0.9); 7.2078 (1.0); 7.1915 (2.7); 7.1871 (2.3); 7.1748 (2.7); 7.1704 (3.0); 7.1598 (4.0); 7.1556 (4.6); 7.1391 (1.8); 7.1351 (1.4); 7.0978 (1.7); 7.0932 (2.2); 7.0777 (4.8); 7.0735 (4.0); 7.0585 (2.8); 7.0544 (2.6); 7.0414 (2.3); 7.0376 (2.7); 7.0219 (1.1); 7.0174 (1.1); 6.9510 (5.4); 6.9343 (5.4); 6.5443 (0.3); 6.5140 (10.5); 5.7532 (7.3); 4.8551 (0.6); 4.8103 (16.0); 4.2862 (5.1); 4.2712 (10.2); 4.2561 (5.2); 3.4082 (0.5); 3.3924 (1.4); 3.3467 (706.0); 3.1758 (0.8); 3.1627 (0.7); 2.8933 (5.6); 2.8783 (10.4); 2.8633 (5.3); 2.6811 (0.4); 2.6766 (0.7); 2.6720 (1.0); 2.6675 (0.7); 2.6631 (0.3); 2.5254 (2.7); 2.5206 (4.1); 2.5120 (63.6); 2.5076 (129.7); 2.5030 (169.6); 2.4985 (120.3); 2.4940 (56.8); 2.3388 (0.4); 2.3344 (0.7); 2.3298 (1.0); 2.3252 (0.8); 2.3207 (0.4); 0.0001 (1.0)
[0311] I.6-41: .sup.1H-NMR (400.6 MHz, CDCl3):
[0312] =7.8876 (1.8); 7.8661 (1.8); 7.2606 (86.1); 7.2177 (0.7); 7.2138 (1.6); 7.1952 (2.0); 7.1933 (2.5); 7.1886 (0.7); 7.1736 (1.0); 7.1695 (0.6); 7.0718 (0.9); 7.0682 (0.9); 7.0524 (1.1); 7.0488 (1.2); 7.0330 (0.6); 7.0295 (0.5); 6.9065 (1.1); 6.9033 (0.9); 6.8861 (1.1); 6.8810 (2.0); 6.8658 (1.8); 6.2766 (3.4); 4.6734 (6.6); 4.3621 (1.0); 4.3509 (1.4); 4.3390 (1.3); 4.1362 (2.3); 4.1310 (0.6); 4.1271 (1.3); 4.1242 (2.2); 4.1183 (0.5); 4.1128 (1.9); 3.5007 (4.8); 3.4978 (4.8); 1.5426 (16.0); 0.0080 (1.3); 0.0002 (53.5); 0.0085 (1.5)
[0313] I.6-276: .sup.1H-NMR (400.6 MHz, CDCl3):
[0314] =8.5648 (1.9); 8.5605 (2.5); 8.5505 (2.5); 8.5466 (1.8); 7.8353 (5.1); 7.8138 (5.0); 7.7077 (1.2); 7.7032 (1.2); 7.6884 (2.6); 7.6841 (2.3); 7.6692 (1.4); 7.6647 (1.3); 7.5196 (0.6); 7.3962 (0.6); 7.2611 (104.1); 7.2522 (2.4); 7.2413 (4.9); 7.2326 (1.9); 7.2220 (4.6); 7.2149 (3.0); 7.2109 (3.5); 7.1949 (4.2); 7.1911 (4.9); 7.1752 (3.2); 7.1710 (2.2); 7.1550 (2.6); 7.1508 (1.9); 7.0549 (2.4); 7.0513 (2.5); 7.0355 (3.4); 7.0320 (3.1); 7.0161 (1.6); 7.0126 (1.5); 6.9975 (0.6); 6.9453 (5.0); 6.9304 (8.2); 6.9104 (3.0); 6.9071 (2.5); 6.2323 (9.6); 5.6502 (1.6); 5.2532 (15.0); 4.7542 (16.0); 4.1308 (0.5); 4.1130 (0.6); 3.4747 (13.9); 3.4719 (13.3); 2.0452 (2.5); 1.6105 (0.5); 1.2773 (0.8); 1.2595 (1.7); 1.2416 (0.8); 0.0080 (1.8); 0.0063 (0.6); 0.0002 (63.7); 0.0085 (2.1)
[0315] I.6-23: .sup.1H-NMR (400.6 MHz, CDCl3):
[0316] =7.8800 (1.6); 7.8584 (1.6); 7.2609 (47.9); 7.2040 (1.6); 7.1850 (2.9); 7.1661 (0.9); 7.1620 (0.5); 7.0526 (0.7); 7.0491 (0.8); 7.0342 (0.7); 7.0297 (1.1); 6.9504 (1.6); 6.9354 (1.6); 6.9034 (1.0); 6.8832 (1.0); 6.8799 (0.6); 6.2812 (3.2); 4.6639 (5.0); 4.2800 (1.4); 4.2682 (1.5); 4.2644 (1.1); 4.2560 (1.6); 3.6798 (1.8); 3.6677 (1.8); 3.6558 (1.7); 3.6048 (1.1); 3.5959 (1.6); 3.5941 (1.6); 3.5881 (1.5); 3.5817 (2.6); 3.5217 (2.6); 3.5153 (1.5); 3.5091 (1.7); 3.5074 (1.6); 3.4994 (5.4); 3.3672 (16.0); 1.5495 (11.9); 0.0079 (0.8); 0.0002 (28.0); 0.0085 (0.8)
[0317] I.6-2: .sup.1H-NMR (400.6 MHz, CDCl3):
[0318] =7.8796 (0.8); 7.8580 (0.8); 7.2606 (87.6); 7.2052 (0.6); 7.1860 (0.7); 7.1822 (0.7); 7.0326 (0.6); 6.9970 (0.5); 6.9606 (0.8); 6.9455 (0.8); 6.2777 (1.5); 4.6715 (2.4); 4.2627 (0.7); 4.2511 (0.7); 4.2387 (0.8); 3.5981 (1.0); 3.5889 (0.6); 3.5861 (0.9); 3.5833 (0.5); 3.5741 (0.9); 3.5032 (1.3); 3.4994 (2.1); 3.4965 (2.1); 3.4859 (1.8); 3.4685 (1.8); 3.4510 (0.6); 1.5434 (16.0); 1.2195 (0.6); 1.1910 (1.9); 1.1735 (3.8); 1.1560 (1.8); 0.0079 (1.4); 0.0002 (53.4); 0.0085 (1.5)
[0319] I.7-339: .sup.1H-NMR (400.6 MHz, CDCl3):
[0320] =7.5189 (0.5); 7.3854 (4.2); 7.3633 (4.2); 7.2605 (93.0); 7.1661 (1.0); 7.1616 (1.2); 7.1477 (1.6); 7.1458 (1.6); 7.1432 (1.9); 7.1414 (1.6); 7.1275 (1.6); 7.1230 (1.9); 7.1003 (1.7); 7.0959 (1.8); 7.0803 (3.5); 7.0759 (2.7); 7.0411 (2.0); 7.0374 (2.2); 7.0227 (1.9); 7.0210 (1.6); 7.0191 (1.9); 7.0174 (1.4); 7.0027 (1.0); 6.9990 (1.0); 6.9969 (0.6); 6.9378 (2.5); 6.9342 (2.3); 6.9174 (2.2); 6.9139 (1.9); 6.7112 (4.0); 6.6949 (4.1); 6.2808 (7.0); 4.6550 (16.0); 4.3722 (4.3); 4.3553 (9.2); 4.3385 (4.5); 4.2666 (3.8); 4.2519 (6.3); 4.2369 (4.0); 3.4996 (9.9); 3.4967 (9.7); 2.3435 (1.0); 2.3270 (2.5); 2.3118 (3.3); 2.2968 (2.6); 2.2801 (0.9); 1.5432 (8.3); 0.0080 (1.6); 0.0002 (55.1); 0.0085 (1.4)
[0321] I.8-23: .sup.1H-NMR (400.6 MHz, CDCl3):
[0322] =7.5334 (1.8); 7.5119 (1.8); 7.2607 (38.9); 7.1243 (0.6); 7.1224 (0.6); 7.1198 (0.7); 7.1180 (0.7); 7.1041 (0.6); 7.0996 (0.8); 7.0716 (0.7); 7.0672 (0.8); 7.0516 (1.4); 7.0472 (1.1); 7.0128 (0.8); 7.0091 (0.9); 6.9944 (0.7); 6.9908 (0.8); 6.9410 (1.1); 6.9374 (1.0); 6.9206 (0.9); 6.9171 (0.8); 6.7414 (1.7); 6.7252 (1.7); 6.2774 (2.8); 4.6901 (5.7); 4.3106 (1.4); 4.3017 (1.0); 4.2987 (1.4); 4.2950 (1.0); 4.2865 (1.5); 3.6936 (1.7); 3.6846 (1.0); 3.6815 (1.7); 3.6788 (1.0); 3.6695 (1.6); 3.6100 (1.1); 3.6023 (1.4); 3.5995 (1.5); 3.5944 (1.5); 3.5878 (2.5); 3.5231 (2.4); 3.5165 (1.4); 3.5108 (1.5); 3.5086 (1.5); 3.4970 (4.0); 3.4941 (4.0); 3.3683 (16.0); 2.0454 (1.2); 1.5508 (14.1); 1.2774 (0.5); 1.2596 (1.1); 0.8820 (1.1); 0.0079 (0.8); 0.0002 (26.8); 0.0085 (0.8)
[0323] I.8-41: .sup.1H-NMR (400.6 MHz, CDCl3):
[0324] =7.5409 (2.4); 7.5192 (2.5); 7.2657 (0.6); 7.2600 (48.9); 7.2552 (0.7); 7.1519 (0.5); 7.1474 (0.6); 7.1336 (0.8); 7.1317 (0.8); 7.1291 (1.0); 7.1271 (0.9); 7.1134 (0.8); 7.1089 (1.0); 7.0889 (0.9); 7.0844 (1.0); 7.0688 (1.9); 7.0644 (1.4); 7.0326 (1.0); 7.0290 (1.2); 7.0143 (1.0); 7.0126 (0.8); 7.0108 (1.0); 7.0091 (0.8); 6.9944 (0.5); 6.9396 (1.4); 6.9360 (1.3); 6.9193 (1.2); 6.9158 (1.0); 6.6887 (2.3); 6.6726 (2.4); 6.2729 (3.8); 4.7046 (8.4); 4.3800 (1.2); 4.3687 (1.5); 4.3567 (1.4); 4.1413 (2.6); 4.1362 (0.7); 4.1321 (1.6); 4.1294 (2.4); 4.1233 (0.6); 4.1178 (2.1); 3.4960 (5.2); 3.4931 (5.2); 2.7789 (0.9); 2.5515 (2.0); 2.0452 (1.4); 1.5454 (16.0); 1.2597 (1.0); 0.0080 (0.9); 0.0002 (33.8); 0.0085 (1.0)
[0325] I.8-176: .sup.1H-NMR (400.6 MHz, CDCl3):
[0326] =7.2600 (61.4); 6.2864 (0.7); 4.7584 (2.5); 4.7467 (1.8); 3.5033 (1.0); 3.5003 (1.0); 1.5335 (16.0); 0.0080 (2.5); 0.0055 (0.5); 0.0002 (90.9); 0.0067 (0.7); 0.0085 (2.5)
[0327] I.9-23: .sup.1H-NMR (400.6 MHz, CDCl3):
[0328] =7.7003 (0.5); 7.6971 (0.7); 7.6798 (0.9); 7.6762 (0.8); 7.6703 (0.5); 7.6670 (0.7); 7.6498 (0.8); 7.6462 (0.8); 7.5367 (0.5); 7.5098 (1.5); 7.4891 (2.0); 7.4825 (0.7); 7.4742 (0.5); 7.4709 (0.9); 7.4670 (0.7); 7.4637 (0.9); 7.3525 (0.5); 7.3479 (0.9); 7.3428 (1.1); 7.3354 (1.5); 7.3311 (1.3); 7.3255 (1.1); 7.3072 (0.7); 7.3004 (0.6); 7.2626 (47.5); 7.2262 (0.7); 7.2224 (1.1); 7.2193 (0.7); 7.2062 (0.7); 7.2031 (1.3); 7.1996 (1.3); 7.1948 (0.6); 7.1798 (0.8); 7.1757 (0.5); 7.0565 (0.7); 7.0530 (0.7); 7.0372 (1.0); 7.0337 (1.0); 6.8886 (0.9); 6.8852 (0.8); 6.8680 (0.8); 6.8653 (0.6); 6.8010 (1.5); 6.7864 (1.5); 6.2750 (2.8); 4.6624 (3.4); 4.2847 (1.2); 4.2729 (1.2); 4.2691 (0.9); 4.2608 (1.3); 3.6858 (1.6); 3.6767 (1.0); 3.6738 (1.6); 3.6619 (1.4); 3.6097 (1.0); 3.6010 (1.4); 3.5989 (1.4); 3.5929 (1.4); 3.5866 (2.4); 3.5267 (2.4); 3.5204 (1.4); 3.5143 (1.4); 3.5124 (1.3); 3.5047 (1.1); 3.4917 (3.8); 3.4890 (3.8); 3.3712 (16.0); 3.3216 (0.5); 3.1281 (0.5); 3.0165 (15.4); 2.9442 (9.5); 2.0870 (9.8); 1.5729 (1.1); 1.2539 (0.7); 0.0080 (2.0); 0.0002 (70.5); 0.0085 (2.0)
[0329] I.9-41: .sup.1H-NMR (400.6 MHz, CDCl3):
[0330] =7.5186 (0.6); 7.5127 (5.1); 7.4917 (5.1); 7.2601 (86.1); 7.2321 (2.2); 7.2282 (3.7); 7.2245 (2.2); 7.2203 (1.3); 7.2122 (2.3); 7.2090 (4.4); 7.2049 (4.4); 7.2001 (2.2); 7.1852 (2.6); 7.1810 (1.8); 7.0736 (2.3); 7.0700 (2.5); 7.0542 (3.6); 7.0507 (3.3); 7.0349 (1.6); 7.0313 (1.5); 6.8939 (3.0); 6.8905 (2.5); 6.8735 (2.8); 6.8705 (2.2); 6.7282 (5.0); 6.7137 (5.1); 6.2665 (9.3); 4.6709 (16.0); 4.3676 (2.6); 4.3564 (3.5); 4.3443 (3.4); 4.1395 (6.5); 4.1347 (1.6); 4.1304 (3.6); 4.1276 (5.9); 4.1214 (1.5); 4.1162 (5.1); 3.4914 (12.8); 3.4885 (13.1); 3.1263 (1.1); 2.4064 (0.8); 2.0453 (0.6); 1.5376 (9.0); 1.2510 (0.9); 0.0079 (3.7); 0.0002 (129.1); 0.0085 (3.7)
[0331] I.6-183: .sup.1H-NMR (400.2 MHz, d6-DMSO):
[0332] =13.0005 (0.4); 8.3149 (0.6); 8.2785 (0.7); 8.2726 (5.6); 8.2627 (0.4); 8.2561 (0.8); 8.2502 (5.6); 7.5164 (2.0); 7.4980 (2.1); 7.4798 (2.2); 7.4613 (2.2); 7.2627 (1.3); 7.2587 (1.7); 7.2403 (3.1); 7.2383 (3.0); 7.2260 (4.5); 7.2222 (4.5); 7.2060 (4.8); 7.2022 (3.2); 7.1736 (5.3); 7.1584 (5.8); 7.1235 (0.7); 7.1171 (3.3); 7.1139 (3.8); 7.0963 (2.8); 7.0934 (2.8); 7.0706 (0.5); 7.0651 (2.4); 7.0617 (2.1); 7.0552 (0.4); 7.0453 (3.1); 7.0267 (1.6); 7.0232 (1.4); 6.6432 (2.5); 6.6370 (2.5); 6.6065 (2.3); 6.6003 (2.3); 6.5659 (0.3); 6.5441 (11.8); 6.1897 (1.2); 6.1849 (1.3); 6.1719 (1.3); 6.1670 (1.2); 5.7551 (13.5); 4.8430 (0.3); 4.8339 (0.4); 4.8188 (0.5); 4.7440 (1.0); 4.7300 (0.8); 4.7203 (0.5); 4.7179 (0.8); 4.7149 (0.5); 4.7056 (0.8); 4.6474 (0.8); 4.6342 (16.0); 4.5637 (0.6); 4.5519 (0.4); 4.5403 (0.4); 3.9594 (0.7); 3.9471 (0.6); 3.9350 (0.6); 3.6223 (0.7); 3.3584 (17.5); 3.3280 (105.6); 3.2698 (0.6); 3.1748 (0.4); 2.6798 (0.4); 2.6754 (1.0); 2.6708 (1.3); 2.6663 (1.0); 2.6616 (0.4); 2.5243 (3.6); 2.5195 (5.9); 2.5109 (87.6); 2.5065 (177.7); 2.5019 (231.9); 2.4973 (163.4); 2.4927 (76.2); 2.3380 (0.5); 2.3332 (1.0); 2.3287 (1.4); 2.3241 (1.0); 2.3197 (0.5); 1.2982 (0.4); 1.2588 (0.7); 1.2353 (1.1); 0.0002 (6.1)
[0333] I.8-2: .sup.1H-NMR (400.6 MHz, CDCl3):
[0334] =7.5323 (4.1); 7.5108 (4.1); 7.2605 (34.2); 7.1395 (0.9); 7.1351 (1.1); 7.1211 (1.4); 7.1192 (1.4); 7.1167 (1.6); 7.1149 (1.5); 7.1009 (1.4); 7.0965 (1.8); 7.0748 (1.6); 7.0704 (1.8); 7.0547 (3.3); 7.0504 (2.5); 7.0119 (1.8); 7.0082 (2.1); 6.9935 (1.6); 6.9919 (1.4); 6.9899 (1.7); 6.9883 (1.5); 6.9735 (0.8); 6.9699 (0.9); 6.9377 (2.4); 6.9341 (2.2); 6.9173 (2.0); 6.9138 (1.8); 6.7480 (3.8); 6.7319 (3.9); 6.2812 (0.6); 6.2749 (6.4); 4.6967 (13.1); 4.6903 (1.3); 4.6831 (0.6); 4.2926 (3.2); 4.2838 (2.1); 4.2807 (3.2); 4.2771 (2.1); 4.2687 (3.6); 3.6128 (4.2); 3.6057 (1.5); 3.6038 (2.2); 3.6007 (4.0); 3.5980 (2.3); 3.5888 (3.9); 3.5097 (2.5); 3.4963 (9.8); 3.4925 (14.4); 3.4747 (7.7); 3.4572 (2.5); 2.0302 (1.8); 1.5499 (9.7); 1.1949 (7.9); 1.1826 (1.0); 1.1774 (16.0); 1.1651 (0.5); 1.1599 (7.6); 0.0080 (0.9); 0.0002 (33.9); 0.0085 (1.0)
[0335] I.8-1: .sup.1H-NMR (400.6 MHz, CDCl3):
[0336] =7.5322 (2.4); 7.5107 (2.3); 7.2608 (10.9); 7.1432 (0.9); 7.1389 (0.9); 7.1205 (1.6); 7.1046 (1.3); 7.1003 (1.3); 7.0796 (1.4); 7.0754 (1.4); 7.0596 (2.3); 7.0555 (1.9); 7.0139 (1.5); 7.0104 (1.5); 6.9922 (1.6); 6.9755 (0.8); 6.9721 (0.8); 6.9330 (2.0); 6.9297 (1.8); 6.9127 (1.6); 6.9094 (1.4); 6.7448 (2.2); 6.7287 (2.2); 6.2738 (4.0); 4.6977 (8.4); 4.2895 (2.5); 4.2783 (3.0); 4.2663 (2.5); 3.5625 (3.2); 3.5508 (3.8); 3.5392 (3.1); 3.4949 (8.2); 3.3398 (1.8); 3.3269 (16.0); 1.5588 (2.4); 0.0002 (7.9)
[0337] I.8-276: .sup.1H-NMR (400.6 MHz, CDCl3):
[0338] =8.5684 (1.4); 8.5643 (1.9); 8.5611 (1.3); 8.5569 (1.2); 8.5535 (1.7); 8.5495 (1.5); 7.6827 (1.2); 7.6783 (1.2); 7.6634 (2.2); 7.6590 (2.2); 7.6442 (1.4); 7.6397 (1.4); 7.4937 (4.9); 7.4722 (4.9); 7.2613 (16.8); 7.2366 (4.3); 7.2248 (1.5); 7.2220 (1.3); 7.2177 (4.5); 7.2060 (1.2); 7.1384 (1.1); 7.1340 (1.4); 7.1198 (1.7); 7.1182 (1.7); 7.1154 (2.1); 7.1138 (2.2); 7.0998 (1.8); 7.0954 (2.5); 7.0906 (2.1); 7.0862 (2.1); 7.0705 (3.9); 7.0662 (2.8); 7.0201 (2.2); 7.0164 (2.6); 7.0016 (1.9); 7.0002 (1.7); 6.9980 (2.1); 6.9964 (1.9); 6.9817 (1.1); 6.9780 (1.1); 6.9622 (3.0); 6.9585 (2.6); 6.9419 (2.4); 6.9383 (2.1); 6.7293 (4.6); 6.7132 (4.6); 6.2384 (7.7); 5.2809 (12.8); 4.7759 (16.0); 4.7626 (0.6); 4.6490 (0.5); 3.4749 (10.4); 3.4720 (10.8); 2.1681 (0.5); 1.2539 (1.2); 0.0080 (0.6); 0.0002 (21.0); 0.0085 (0.6)
[0339] I.9-2: .sup.1H-NMR (400.2 MHz, d6-DMSO):
[0340] =8.1472 (4.0); 8.1245 (4.0); 8.1171 (0.4); 7.3039 (2.2); 7.3001 (2.7); 7.2843 (3.3); 7.2806 (3.7); 7.2662 (2.3); 7.2468 (2.0); 7.2429 (1.6); 7.1690 (2.7); 7.1659 (3.0); 7.1483 (2.0); 7.1453 (1.9); 7.1014 (1.7); 7.0981 (1.6); 7.0822 (2.7); 7.0792 (2.4); 7.0630 (1.3); 7.0597 (1.1); 6.9792 (3.9); 6.9645 (4.0); 6.5342 (8.2); 5.7554 (5.2); 4.8341 (0.4); 4.7614 (12.2); 4.1781 (3.5); 4.1666 (4.1); 4.1546 (3.7); 3.5236 (4.0); 3.5117 (4.3); 3.5000 (3.5); 3.4197 (2.5); 3.4022 (7.8); 3.3847 (7.9); 3.3672 (2.8); 3.3470 (13.3); 3.3270 (149.5); 2.6752 (0.6); 2.6708 (0.8); 2.6663 (0.6); 2.5240 (2.5); 2.5105 (56.5); 2.5063 (111.7); 2.5018 (143.9); 2.4973 (103.4); 2.4931 (50.1); 2.3332 (0.6); 2.3287 (0.8); 2.3243 (0.6); 1.9841 (1.6); 1.2983 (0.4); 1.2588 (0.7); 1.2352 (0.9); 1.0788 (7.9); 1.0613 (16.0); 1.0438 (7.6); 0.0002 (2.9)
[0341] I.9-276: .sup.1H-NMR (400.6 MHz, CDCl3):
[0342] =8.5790 (2.2); 8.5745 (2.5); 8.5655 (2.6); 7.7554 (0.9); 7.7357 (1.6); 7.7166 (1.0); 7.5261 (0.6); 7.5190 (0.9); 7.4480 (5.9); 7.4269 (5.9); 7.2805 (3.2); 7.2606 (137.6); 7.2429 (0.9); 7.2307 (3.4); 7.2266 (4.0); 7.2107 (4.5); 7.2069 (5.6); 7.1900 (3.5); 7.1851 (2.8); 7.1701 (2.9); 7.1659 (2.3); 7.0584 (2.7); 7.0550 (3.1); 7.0391 (3.9); 7.0356 (4.0); 7.0199 (1.9); 7.0163 (1.8); 6.9969 (0.8); 6.9319 (3.3); 6.9287 (3.4); 6.9116 (2.9); 6.9084 (2.8); 6.7843 (5.6); 6.7698 (5.6); 6.2943 (0.8); 6.2237 (10.8); 5.3194 (0.5); 5.2799 (11.2); 4.7564 (12.3); 4.7545 (12.5); 4.7128 (0.6); 4.6431 (1.6); 3.5271 (0.5); 3.4955 (1.2); 3.4675 (15.7); 3.4648 (16.0); 3.3193 (2.2); 2.9660 (0.8); 2.8924 (0.6); 2.0499 (2.0); 2.0453 (1.9); 1.5717 (0.9); 1.3330 (2.4); 1.2843 (3.3); 1.2773 (1.7); 1.2545 (4.6); 1.2416 (1.5); 1.1745 (1.1); 1.1590 (1.0); 0.8803 (1.3); 0.8627 (0.7); 0.1456 (0.6); 0.0079 (5.5); 0.0002 (181.1); 0.0085 (6.8); 0.1497 (0.6)
[0343] I.8-183: .sup.1H-NMR (400.6 MHz, CDCl3):
[0344] =7.5498 (4.0); 7.5283 (4.0); 7.2606 (33.7); 7.1661 (1.0); 7.1616 (1.2); 7.1478 (1.4); 7.1459 (1.4); 7.1433 (1.7); 7.1414 (1.5); 7.1276 (1.5); 7.1231 (1.8); 7.0989 (1.5); 7.0944 (1.6); 7.0789 (3.4); 7.0744 (2.6); 7.0444 (2.1); 7.0407 (2.3); 7.0261 (1.7); 7.0244 (1.4); 7.0225 (1.8); 7.0208 (1.4); 7.0061 (0.9); 7.0025 (0.9); 6.9177 (2.3); 6.9141 (2.2); 6.8973 (2.0); 6.8937 (1.8); 6.6412 (3.7); 6.6251 (3.8); 6.2790 (6.2); 4.6717 (16.0); 4.6646 (1.2); 4.6594 (3.8); 4.6534 (1.9); 4.6482 (2.5); 4.6456 (2.5); 4.6399 (1.8); 4.5932 (1.8); 4.5874 (3.1); 4.5848 (2.5); 4.5798 (2.3); 4.5758 (2.5); 4.5736 (3.6); 4.5688 (0.9); 4.5643 (1.9); 4.5624 (1.8); 3.4990 (8.6); 3.4960 (8.8); 3.3192 (0.8); 2.0497 (0.7); 2.0451 (1.9); 1.2771 (0.7); 1.2593 (1.4); 1.2414 (0.6); 0.0080 (1.0); 0.0002 (32.5); 0.0085 (0.9)
[0345] I.8-291: .sup.1H-NMR (400.6 MHz, CDCl3):
[0346] =9.1478 (2.0); 9.1430 (2.1); 9.1363 (2.0); 9.1314 (2.0); 7.5537 (1.2); 7.5325 (1.4); 7.5185 (0.6); 7.4864 (4.8); 7.4725 (1.2); 7.4647 (5.5); 7.4514 (4.3); 7.4449 (3.6); 7.4400 (4.2); 7.4236 (1.4); 7.4187 (1.4); 7.2600 (81.1); 7.1571 (1.0); 7.1527 (1.3); 7.1495 (0.7); 7.1387 (1.5); 7.1369 (1.6); 7.1343 (1.8); 7.1325 (1.7); 7.1287 (0.6); 7.1240 (0.6); 7.1187 (1.6); 7.1141 (1.9); 7.1086 (1.0); 7.1042 (0.8); 7.0925 (1.7); 7.0880 (1.9); 7.0724 (4.0); 7.0681 (3.3); 7.0488 (0.6); 7.0364 (2.0); 7.0328 (3.0); 7.0181 (1.8); 7.0130 (2.1); 6.9981 (1.0); 6.9946 (1.0); 6.9731 (2.8); 6.9695 (2.4); 6.9529 (2.3); 6.9493 (2.0); 6.6697 (1.2); 6.6624 (4.5); 6.6537 (1.2); 6.6463 (4.5); 6.3007 (1.8); 6.2590 (7.4); 5.5090 (7.7); 5.5062 (7.8); 5.4536 (1.8); 4.7710 (16.0); 4.6626 (4.0); 3.5068 (2.6); 3.5040 (2.8); 3.4905 (10.1); 3.4878 (10.2); 2.7757 (1.4); 2.6225 (0.5); 2.5515 (1.3); 2.1772 (4.5); 1.2556 (0.6); 0.0080 (3.3); 0.0002 (116.1); 0.0085 (3.5)
[0347] I.9-291: .sup.1H-NMR (400.6 MHz, CDCl3):
[0348] =9.1797 (2.2); 9.1751 (2.4); 9.1678 (2.4); 9.1632 (2.4); 7.5628 (1.6); 7.5508 (1.4); 7.5416 (4.1); 7.5296 (4.3); 7.5162 (3.7); 7.5115 (4.1); 7.4949 (1.5); 7.4903 (1.3); 7.4614 (5.1); 7.4404 (5.0); 7.2606 (83.8); 7.2264 (5.4); 7.2070 (8.1); 7.2029 (2.1); 7.1879 (2.6); 7.1837 (1.7); 7.0738 (2.1); 7.0702 (2.4); 7.0536 (2.2); 7.0508 (3.4); 7.0351 (1.6); 7.0315 (1.5); 6.9969 (0.6); 6.9408 (2.8); 6.9381 (2.1); 6.9203 (2.6); 6.9169 (1.7); 6.6968 (4.8); 6.6823 (4.8); 6.2522 (9.0); 5.5236 (1.2); 5.4892 (7.8); 5.4812 (7.8); 5.4472 (0.9); 4.7661 (0.6); 4.7475 (16.0); 3.4875 (11.8); 3.4846 (12.2); 0.0079 (3.6); 0.0002 (126.7); 0.0085 (3.7)
[0349] I.8-291: .sup.1H-NMR (400.6 MHz, CDCl3):
[0350] =9.1478 (2.0); 9.1429 (2.0); 9.1362 (2.0); 9.1313 (2.0); 7.4894 (4.5); 7.4749 (1.3); 7.4679 (4.6); 7.4634 (1.1); 7.4537 (3.8); 7.4421 (4.2); 7.4355 (3.4); 7.4306 (3.7); 7.4143 (1.1); 7.4093 (0.8); 7.2613 (35.0); 7.1581 (1.0); 7.1536 (1.2); 7.1397 (1.5); 7.1380 (1.6); 7.1353 (1.8); 7.1335 (1.7); 7.1197 (1.6); 7.1151 (2.0); 7.0944 (1.7); 7.0900 (1.9); 7.0744 (3.7); 7.0700 (2.8); 7.0378 (2.0); 7.0341 (2.4); 7.0194 (1.8); 7.0178 (1.5); 7.0158 (2.0); 7.0142 (1.6); 6.9995 (0.9); 6.9958 (1.0); 6.9742 (2.8); 6.9706 (2.4); 6.9539 (2.2); 6.9504 (2.0); 6.6634 (4.4); 6.6473 (4.4); 6.2602 (7.2); 5.5118 (7.6); 5.5089 (7.7); 4.7741 (16.0); 4.1308 (1.1); 4.1129 (1.0); 3.4917 (9.9); 3.4888 (10.1); 3.3194 (0.8); 2.0499 (0.8); 2.0453 (5.0); 1.5781 (9.0); 1.2774 (1.4); 1.2595 (3.1); 1.2417 (1.4); 0.0079 (1.5); 0.0002 (52.1); 0.0085 (1.4)
[0351] I.9-291: .sup.1H-NMR (400.6 MHz, CDCl3):
[0352] =9.1592 (2.3); 9.1545 (2.4); 9.1474 (2.4); 9.1426 (2.4); 7.7008 (2.9); 7.6976 (4.1); 7.6939 (1.7); 7.6855 (1.2); 7.6803 (5.5); 7.6767 (4.6); 7.6709 (2.9); 7.6676 (4.2); 7.6640 (1.8); 7.6556 (1.2); 7.6504 (5.4); 7.6468 (4.5); 7.5736 (0.6); 7.5700 (1.2); 7.5662 (1.3); 7.5627 (0.6); 7.5575 (0.7); 7.5518 (2.6); 7.5476 (2.6); 7.5422 (0.9); 7.5366 (1.4); 7.5329 (3.1); 7.5291 (3.0); 7.5254 (1.3); 7.5197 (0.6); 7.5169 (1.7); 7.5050 (1.4); 7.4957 (4.5); 7.4888 (2.7); 7.4869 (3.9); 7.4838 (6.9); 7.4817 (3.4); 7.4797 (4.0); 7.4763 (2.0); 7.4717 (6.6); 7.4674 (8.3); 7.4641 (4.6); 7.4606 (9.8); 7.4570 (1.9); 7.4542 (1.3); 7.4505 (3.8); 7.4465 (2.6); 7.4430 (2.7); 7.4393 (5.8); 7.2613 (69.0); 7.2285 (2.0); 7.2244 (5.3); 7.2199 (1.0); 7.2086 (2.2); 7.2061 (4.7); 7.2043 (7.7); 7.1998 (2.1); 7.1848 (2.7); 7.1807 (1.8); 7.0713 (2.3); 7.0677 (2.5); 7.0518 (2.9); 7.0483 (3.4); 7.0326 (1.6); 7.0291 (1.6); 6.9379 (2.9); 6.9348 (2.2); 6.9174 (2.6); 6.6980 (4.7); 6.6835 (4.8); 6.2524 (9.1); 5.5183 (1.1); 5.4844 (7.9); 5.4756 (8.0); 5.4576 (0.9); 5.4419 (1.0); 4.7656 (0.8); 4.7469 (16.0); 3.4875 (12.1); 3.4845 (12.7); 2.1800 (2.3); 2.0453 (1.6); 1.5901 (3.0); 1.3332 (0.6); 1.2844 (0.9); 1.2773 (0.6); 1.2594 (1.4); 1.2562 (1.6); 1.2416 (0.5); 0.0080 (3.1); 0.0002 (104.0); 0.0058 (1.4); 0.0085 (3.1)
[0353] I.19-276: .sup.1H-NMR (400.0 MHz, CDCl3):
[0354] =8.5628 (1.0); 8.5581 (1.0); 8.5494 (1.0); 8.5450 (0.8); 7.6964 (0.7); 7.6920 (0.7); 7.6771 (1.5); 7.6726 (1.3); 7.6578 (0.8); 7.6534 (0.8); 7.3225 (2.6); 7.3004 (2.6); 7.2613 (7.0); 7.2450 (1.2); 7.2406 (1.3); 7.2364 (1.7); 7.2260 (1.0); 7.2167 (1.7); 7.1197 (0.7); 7.1047 (0.7); 7.0983 (1.4); 7.0835 (1.3); 7.0771 (0.8); 7.0623 (0.7); 6.8814 (0.8); 6.8781 (0.9); 6.8575 (1.3); 6.8368 (0.7); 6.8335 (0.6); 6.7192 (1.9); 6.7124 (1.0); 6.7088 (1.5); 6.7037 (2.0); 6.6912 (0.8); 6.6875 (1.2); 6.2209 (4.3); 5.2986 (16.0); 5.2901 (0.7); 5.2642 (7.1); 4.7605 (8.7); 3.4659 (6.0); 3.4632 (6.0); 2.0445 (0.9); 1.2589 (0.8); 0.0002 (10.0)
[0355] I.19-176: .sup.1H-NMR (400.0 MHz, CDCl3):
[0356] =7.3919 (3.5); 7.3699 (3.4); 7.2606 (8.0); 7.1737 (0.8); 7.1589 (0.9); 7.1524 (1.8); 7.1377 (1.8); 7.1312 (1.1); 7.1165 (1.0); 6.9356 (1.1); 6.9325 (1.2); 6.9116 (1.8); 6.8910 (0.9); 6.8879 (0.9); 6.7009 (1.2); 6.6975 (2.0); 6.6797 (1.1); 6.6763 (1.7); 6.6076 (2.4); 6.5916 (2.3); 6.2789 (6.0); 5.2989 (14.6); 4.7544 (2.0); 4.7484 (16.0); 4.7319 (13.5); 4.7225 (1.2); 4.1299 (0.5); 4.1120 (0.5); 3.5337 (0.7); 3.4998 (8.6); 3.4972 (8.7); 2.0442 (2.4); 1.5500 (2.3); 1.2767 (0.7); 1.2589 (1.4); 1.2410 (0.6); 0.0002 (11.4)
[0357] I.23-176: .sup.1H-NMR (400.0 MHz, CDCl3):
[0358] =7.4170 (3.4); 7.3949 (3.3); 7.2606 (12.4); 6.9813 (1.4); 6.9685 (1.5); 6.9589 (2.0); 6.9460 (1.9); 6.8642 (1.2); 6.8568 (1.4); 6.8452 (1.3); 6.8418 (1.0); 6.8377 (1.5); 6.8345 (1.2); 6.8227 (0.8); 6.8152 (1.1); 6.8079 (2.2); 6.7985 (3.6); 6.7861 (2.4); 6.7821 (3.4); 6.7790 (1.6); 6.3117 (5.7); 5.2995 (11.5); 4.7712 (16.0); 4.7655 (1.3); 4.7221 (13.9); 4.6879 (1.0); 3.5431 (0.7); 3.5234 (8.2); 3.5206 (8.2); 2.0448 (1.8); 1.5462 (4.8); 1.2771 (0.6); 1.2592 (1.2); 0.0079 (0.7); 0.0002 (17.8); 0.0084 (0.6)
[0359] I.23-1: .sup.1H-NMR (400.0 MHz, CDCl3):
[0360] =7.3903 (2.1); 7.3681 (2.0); 7.2611 (5.9); 6.9572 (0.9); 6.9443 (0.9); 6.9347 (1.2); 6.9219 (1.1); 6.8684 (2.0); 6.8520 (2.0); 6.8288 (0.6); 6.8214 (0.8); 6.8095 (0.7); 6.8065 (0.5); 6.8020 (0.8); 6.7990 (0.7); 6.7795 (0.7); 6.7702 (1.2); 6.7628 (0.9); 6.7483 (1.3); 6.7409 (0.9); 6.3017 (3.5); 5.2992 (6.3); 4.6717 (7.8); 4.6510 (0.5); 4.3027 (2.0); 4.2942 (1.2); 4.2911 (1.9); 4.2873 (1.1); 4.2793 (2.0); 3.5791 (2.3); 3.5707 (1.2); 3.5673 (2.2); 3.5644 (1.2); 3.5557 (2.1); 3.5177 (4.9); 3.5150 (5.0); 3.3523 (1.5); 3.3463 (16.0); 0.0002 (8.3)
[0361] I.19-1: .sup.1H-NMR (400.0 MHz, CDCl3):
[0362] =7.3607 (2.2); 7.3386 (2.2); 7.2610 (4.8); 7.1336 (0.5); 7.1186 (0.6); 7.1124 (1.1); 7.0975 (1.1); 7.0911 (0.7); 7.0763 (0.6); 6.8806 (0.8); 6.8774 (0.8); 6.8566 (1.2); 6.8359 (0.6); 6.8329 (0.6); 6.7243 (1.7); 6.7081 (1.6); 6.6752 (1.2); 6.6540 (1.1); 6.2630 (3.9); 5.2988 (12.2); 4.6853 (8.1); 4.2734 (1.3); 4.2654 (1.7); 4.2602 (1.5); 4.2521 (1.3); 3.5476 (2.5); 3.5360 (2.9); 3.5293 (1.0); 3.5244 (2.3); 3.4899 (5.8); 3.4876 (5.8); 3.3370 (1.3); 3.3171 (16.0); 1.5622 (1.3); 0.0002 (6.8)
[0363] I.19-23: .sup.1H-NMR (400.6 MHz, CDCl3):
[0364] =7.3611 (1.6); 7.3390 (1.6); 7.2614 (5.8); 7.1139 (0.9); 7.0990 (0.9); 7.0927 (0.5); 6.8797 (0.5); 6.8764 (0.5); 6.8583 (0.5); 6.8562 (0.7); 6.8531 (0.6); 6.7148 (1.0); 6.6986 (1.0); 6.6833 (0.8); 6.6620 (0.8); 6.2666 (2.6); 5.2990 (8.8); 4.6768 (5.3); 4.2950 (1.2); 4.2864 (0.9); 4.2832 (1.2); 4.2794 (0.8); 4.2711 (1.3); 3.6802 (1.6); 3.6733 (0.6); 3.6711 (0.9); 3.6682 (1.6); 3.6656 (1.0); 3.6635 (0.6); 3.6563 (1.4); 3.6022 (0.9); 3.6009 (0.9); 3.5933 (1.3); 3.5912 (1.3); 3.5903 (1.3); 3.5853 (1.4); 3.5789 (2.3); 3.5182 (2.3); 3.5117 (1.4); 3.5068 (1.3); 3.5057 (1.3); 3.5038 (1.3); 3.4945 (2.2); 3.4915 (3.5); 3.4885 (3.5); 3.3683 (1.9); 3.3660 (16.0); 1.5679 (1.8); 0.0002 (8.7)
[0365] I.23-23: .sup.1H-NMR (400.6 MHz, CDCl3):
[0366] =7.3919 (1.8); 7.3698 (1.8); 7.2627 (3.6); 6.9669 (0.8); 6.9540 (0.8); 6.9444 (1.0); 6.9315 (1.0); 6.8704 (1.8); 6.8540 (1.8); 6.8294 (0.6); 6.8219 (0.7); 6.8100 (0.6); 6.8025 (0.7); 6.7994 (0.7); 6.7800 (0.6); 6.7630 (1.1); 6.7556 (0.8); 6.7411 (1.1); 6.7337 (0.8); 6.3040 (3.1); 5.2991 (12.5); 4.6645 (6.7); 4.3206 (1.6); 4.3119 (1.0); 4.3087 (1.7); 4.3049 (1.0); 4.2966 (1.7); 3.7012 (1.9); 3.6928 (1.1); 3.6892 (1.9); 3.6860 (1.1); 3.6773 (1.7); 3.6199 (1.3); 3.6114 (1.5); 3.6091 (1.8); 3.6036 (1.5); 3.5970 (2.6); 3.5297 (2.7); 3.5227 (2.6); 3.5182 (5.9); 3.5156 (5.7); 3.5072 (1.4); 3.3700 (16.0); 1.5867 (0.9); 0.0002 (5.1)
[0367] I.23-276: .sup.1H-NMR (400.6 MHz, CDCl3):
[0368] =8.6265 (1.6); 8.6142 (1.6); 7.7696 (1.1); 7.7652 (1.1); 7.7503 (2.2); 7.7459 (2.1); 7.7310 (1.2); 7.7266 (1.2); 7.3548 (4.4); 7.3326 (6.4); 7.3122 (2.3); 7.3064 (1.4); 7.2997 (1.2); 7.2872 (1.1); 7.2612 (18.1); 6.9784 (1.8); 6.9657 (1.8); 6.9561 (2.2); 6.9433 (2.2); 6.8537 (4.2); 6.8374 (4.2); 6.8231 (1.3); 6.8156 (1.6); 6.8038 (1.4); 6.8009 (1.0); 6.7963 (1.7); 6.7934 (1.6); 6.7814 (1.0); 6.7783 (2.9); 6.7740 (1.6); 6.7710 (1.8); 6.7564 (2.7); 6.7491 (1.6); 6.2783 (7.5); 5.3150 (12.4); 5.2991 (11.1); 4.7495 (16.0); 4.6352 (0.8); 3.5034 (10.0); 3.5006 (10.3); 0.0080 (0.8); 0.0002 (27.4); 0.0085 (0.7)
[0369] I.8-278: .sup.1H-NMR (400.6 MHz, CDCl3):
[0370] =8.5803 (3.6); 8.5766 (2.5); 8.5689 (2.6); 8.5653 (3.5); 7.4781 (4.6); 7.4565 (4.5); 7.2610 (24.0); 7.2138 (0.5); 7.1798 (0.5); 7.1653 (4.6); 7.1613 (2.6); 7.1540 (3.1); 7.1515 (4.5); 7.1503 (4.4); 7.1332 (1.7); 7.1312 (1.6); 7.1286 (1.9); 7.1266 (1.6); 7.1132 (1.7); 7.1085 (2.2); 7.0970 (1.6); 7.0924 (1.8); 7.0770 (3.8); 7.0724 (2.7); 7.0466 (2.3); 7.0428 (2.5); 7.0284 (1.9); 7.0264 (1.6); 7.0248 (1.9); 7.0228 (1.5); 7.0084 (0.9); 7.0047 (0.9); 6.9519 (2.6); 6.9482 (2.4); 6.9316 (2.2); 6.9280 (1.9); 6.6679 (4.4); 6.6518 (4.5); 6.2706 (0.6); 6.2497 (7.2); 5.2988 (7.6); 5.1755 (6.6); 4.7510 (16.0); 4.7439 (0.9); 4.7352 (0.6); 4.7212 (1.2); 3.4992 (1.0); 3.4839 (10.0); 3.4810 (10.0); 2.1154 (1.1); 2.0932 (0.6); 2.0447 (0.6); 1.4365 (0.6); 1.4224 (0.6); 1.2590 (0.8); 1.2547 (0.7); 0.0080 (0.9); 0.0040 (0.8); 0.0002 (34.3); 0.0085 (1.0)
[0371] I.8-356: .sup.1H-NMR (400.6 MHz, CDCl3):
[0372] =7.4988 (2.8); 7.4772 (2.8); 7.2928 (3.7); 7.2610 (14.5); 7.1134 (0.7); 7.1086 (0.7); 7.0953 (1.0); 7.0932 (1.0); 7.0906 (1.2); 7.0885 (1.0); 7.0752 (1.0); 7.0704 (1.3); 7.0532 (0.9); 7.0486 (1.1); 7.0332 (2.4); 7.0285 (1.8); 7.0076 (1.4); 7.0039 (1.6); 6.9896 (1.1); 6.9859 (1.2); 6.9840 (0.9); 6.9695 (0.6); 6.9658 (0.5); 6.8875 (1.6); 6.8839 (1.5); 6.8672 (1.4); 6.8637 (1.2); 6.6953 (2.7); 6.6792 (2.6); 6.2774 (4.6); 5.2988 (11.1); 5.0117 (5.6); 4.6215 (9.5); 4.5971 (0.7); 3.7941 (16.0); 3.5135 (0.6); 3.4996 (6.3); 3.4968 (6.4); 2.2141 (1.6); 2.2078 (15.0); 2.1979 (0.6); 2.1207 (0.9); 1.2590 (0.5); 0.0079 (0.7); 0.0002 (21.4); 0.0085 (0.6)
[0373] I.7-17: .sup.1H-NMR (400.6 MHz, CDCl3):
[0374] =7.3747 (4.3); 7.3526 (4.3); 7.2601 (11.6); 7.1456 (0.9); 7.1411 (1.1); 7.1253 (1.7); 7.1226 (2.0); 7.1071 (1.5); 7.1026 (1.7); 7.0758 (1.6); 7.0714 (1.8); 7.0558 (3.6); 7.0514 (2.8); 7.0209 (1.9); 7.0174 (2.1); 6.9990 (2.1); 6.9826 (0.8); 6.9791 (0.8); 6.9375 (2.7); 6.9342 (2.6); 6.9171 (2.3); 6.9139 (2.1); 6.7555 (4.1); 6.7390 (4.2); 6.2779 (7.7); 5.9527 (0.6); 5.9426 (1.2); 5.9326 (0.6); 5.8147 (1.2); 5.8046 (2.5); 5.7945 (1.2); 5.6766 (0.6); 5.6666 (1.2); 5.6565 (0.6); 5.2985 (14.4); 4.6913 (16.0); 4.3081 (2.9); 4.2975 (3.3); 4.2932 (2.8); 4.2849 (3.3); 3.7434 (3.9); 3.7315 (4.8); 3.7200 (3.6); 3.6784 (2.4); 3.6683 (2.4); 3.6436 (4.9); 3.6335 (4.8); 3.6087 (2.5); 3.5986 (2.4); 3.4976 (11.2); 3.4954 (11.7); 1.5496 (3.4); 0.0002 (15.3)
[0375] I.7-3: .sup.1H-NMR (400.6 MHz, CDCl3):
[0376] =7.3685 (3.7); 7.3464 (3.7); 7.2606 (9.4); 7.1337 (1.0); 7.1292 (1.0); 7.1153 (1.4); 7.1134 (1.4); 7.1108 (1.6); 7.1089 (1.4); 7.0951 (1.4); 7.0906 (1.7); 7.0665 (1.5); 7.0620 (1.6); 7.0464 (3.2); 7.0420 (2.4); 7.0087 (1.8); 7.0050 (2.0); 6.9904 (1.6); 6.9887 (1.3); 6.9868 (1.7); 6.9850 (1.3); 6.9704 (0.8); 6.9667 (0.8); 6.9339 (2.3); 6.9303 (2.0); 6.9135 (1.9); 6.9100 (1.6); 6.7822 (3.6); 6.7657 (3.8); 6.2780 (6.2); 5.2977 (16.0); 4.6911 (12.6); 4.2946 (3.2); 4.2857 (2.1); 4.2827 (3.2); 4.2790 (2.0); 4.2705 (3.4); 3.6140 (3.9); 3.6051 (2.1); 3.6019 (3.7); 3.5989 (2.1); 3.5899 (3.6); 3.4980 (8.3); 3.4950 (8.4); 3.3969 (4.4); 3.3800 (9.0); 3.3632 (4.5); 1.5926 (1.7); 1.5756 (3.7); 1.5571 (3.7); 1.5401 (1.9); 1.5219 (0.5); 0.9161 (6.9); 0.8976 (14.1); 0.8790 (6.2); 0.0002 (12.9)
[0377] I.7-18: .sup.1H-NMR (400.6 MHz, CDCl3):
[0378] =7.3744 (4.3); 7.3522 (4.3); 7.2600 (12.8); 7.1457 (1.0); 7.1412 (1.2); 7.1273 (1.6); 7.1254 (1.5); 7.1228 (1.8); 7.1210 (1.6); 7.1072 (1.6); 7.1026 (1.9); 7.0783 (1.7); 7.0739 (1.8); 7.0583 (3.6); 7.0539 (2.8); 7.0223 (2.1); 7.0187 (2.3); 7.0040 (1.8); 7.0023 (1.5); 7.0004 (1.9); 6.9988 (1.4); 6.9841 (0.9); 6.9804 (0.9); 6.9358 (2.6); 6.9322 (2.3); 6.9155 (2.2); 6.9119 (1.9); 6.7488 (4.2); 6.7324 (4.2); 6.2759 (7.1); 5.2981 (16.0); 4.6933 (15.7); 4.3195 (2.3); 4.3175 (2.3); 4.3106 (2.7); 4.3079 (2.7); 4.3061 (2.6); 4.3027 (2.5); 4.2960 (2.5); 4.2944 (2.4); 3.8290 (2.6); 3.8074 (10.3); 3.7970 (4.4); 3.7857 (10.6); 3.7640 (2.8); 3.4971 (9.7); 3.4942 (9.8); 1.5506 (2.4); 0.0002 (17.5)
[0379] I.7-8: .sup.1H-NMR (400.6 MHz, CDCl3):
[0380] =7.3708 (3.8); 7.3487 (3.9); 7.2605 (10.2); 7.1443 (0.9); 7.1399 (1.0); 7.1258 (1.4); 7.1240 (1.4); 7.1215 (1.6); 7.1197 (1.4); 7.1057 (1.4); 7.1013 (1.6); 7.0767 (1.6); 7.0723 (1.7); 7.0566 (3.2); 7.0523 (2.4); 7.0136 (1.7); 7.0099 (1.9); 6.9950 (1.6); 6.9936 (1.4); 6.9915 (1.7); 6.9752 (0.8); 6.9716 (0.8); 6.9317 (2.3); 6.9281 (2.1); 6.9114 (2.0); 6.9078 (1.7); 6.7793 (3.7); 6.7628 (3.8); 6.2812 (6.5); 5.2983 (16.0); 4.6971 (13.5); 4.3229 (1.6); 4.3139 (2.6); 4.3106 (2.1); 4.3043 (2.1); 4.3003 (2.9); 4.2915 (1.7); 4.1155 (5.9); 4.1137 (5.7); 4.1096 (5.9); 4.1077 (5.4); 3.7076 (2.2); 3.7042 (2.3); 3.6958 (3.6); 3.6928 (3.3); 3.6845 (1.9); 3.6803 (1.8); 3.4996 (9.1); 3.4968 (8.9); 2.4400 (2.6); 2.4341 (5.2); 2.4281 (2.4); 1.5566 (1.9); 0.0002 (13.0)
[0381] I.7-7: .sup.1H-NMR (400.6 MHz, CDCl3):
[0382] =7.3688 (4.6); 7.3467 (4.7); 7.2603 (11.8); 7.1364 (1.0); 7.1319 (1.2); 7.1179 (1.7); 7.1161 (1.6); 7.1135 (2.0); 7.1117 (1.7); 7.0978 (1.6); 7.0934 (1.9); 7.0713 (1.8); 7.0669 (2.0); 7.0512 (3.8); 7.0469 (2.9); 7.0113 (2.1); 7.0076 (2.3); 6.9928 (2.0); 6.9910 (1.7); 6.9892 (2.0); 6.9729 (0.9); 6.9693 (1.0); 6.9323 (2.8); 6.9288 (2.5); 6.9120 (2.4); 6.9085 (2.0); 6.7791 (4.5); 6.7626 (4.5); 6.2764 (7.8); 5.8987 (0.6); 5.8845 (1.3); 5.8727 (0.8); 5.8704 (0.7); 5.8586 (1.5); 5.8557 (0.8); 5.8443 (0.8); 5.8414 (1.5); 5.8297 (0.9); 5.8273 (0.8); 5.8155 (1.6); 5.8014 (0.8); 5.2980 (13.2); 5.2813 (0.9); 5.2773 (2.4); 5.2732 (2.4); 5.2692 (0.9); 5.2383 (0.8); 5.2343 (2.0); 5.2302 (2.1); 5.2262 (0.8); 5.2046 (1.0); 5.2015 (2.2); 5.1980 (1.8); 5.1943 (0.8); 5.1787 (0.9); 5.1756 (2.0); 5.1721 (1.7); 5.1683 (0.7); 4.6942 (16.0); 4.3068 (3.6); 4.2978 (2.7); 4.2951 (3.6); 4.2911 (2.5); 4.2829 (3.9); 3.9768 (3.3); 3.9735 (5.4); 3.9699 (3.2); 3.9627 (3.3); 3.9594 (5.2); 3.9557 (3.0); 3.6219 (4.8); 3.6154 (1.6); 3.6124 (2.9); 3.6100 (4.8); 3.6046 (1.4); 3.5981 (4.3); 3.4959 (10.8); 3.4931 (10.5); 1.5595 (1.7); 0.0079 (0.5); 0.0002 (15.6)
[0383] I.7-27: .sup.1H-NMR (400.6 MHz, CDCl3):
[0384] =7.3706 (4.6); 7.3484 (4.6); 7.2605 (12.1); 7.1398 (1.0); 7.1354 (10.2); 7.1194 (2.0); 7.1169 (2.3); 7.1012 (1.6); 7.0968 (1.8); 7.0698 (1.7); 7.0655 (2.0); 7.0498 (3.7); 7.0455 (3.0); 7.0108 (2.0); 7.0073 (2.2); 6.9889 (2.4); 6.9724 (0.9); 6.9690 (0.9); 6.9219 (2.9); 6.9188 (2.8); 6.9016 (2.4); 6.8985 (2.2); 6.7717 (4.4); 6.7553 (4.4); 6.2836 (8.2); 5.2984 (8.8); 4.6524 (15.8); 4.2493 (3.8); 4.2332 (8.0); 4.2171 (3.9); 3.4999 (12.6); 3.4980 (12.8); 3.4571 (2.5); 3.4396 (7.7); 3.4329 (4.4); 3.4221 (8.3); 3.4174 (9.1); 3.4021 (4.8); 1.9129 (1.1); 1.8972 (4.1); 1.8814 (6.0); 1.8656 (3.9); 1.8497 (1.0); 1.5598 (2.0); 1.1867 (8.0); 1.1692 (16.0); 1.1517 (7.6); 0.0079 (0.6); 0.0002 (15.0)
[0385] I.7-24: .sup.1H-NMR (400.6 MHz, CDCl3):
[0386] =7.3699 (4.4); 7.3478 (4.4); 7.2608 (12.9); 7.1389 (1.0); 7.1345 (1.1); 7.1162 (2.2); 7.1004 (1.6); 7.0960 (1.8); 7.0650 (1.8); 7.0607 (1.9); 7.0450 (3.8); 7.0408 (2.9); 7.0095 (2.2); 7.0061 (2.2); 6.9899 (2.3); 6.9880 (2.3); 6.9713 (1.0); 6.9678 (0.9); 6.9374 (3.2); 6.9171 (2.6); 6.7773 (4.4); 6.7609 (4.4); 6.2802 (8.3); 5.2987 (5.8); 4.6874 (15.9); 4.3094 (4.0); 4.2975 (4.6); 4.2853 (4.2); 3.7000 (4.5); 3.6878 (4.9); 3.6760 (4.1); 3.6185 (1.9); 3.6161 (1.9); 3.6080 (4.8); 3.6010 (3.4); 3.5944 (5.6); 3.5668 (5.7); 3.5591 (3.6); 3.5521 (4.6); 3.5417 (4.1); 3.5242 (7.8); 3.5066 (9.0); 3.4987 (13.8); 3.4894 (3.3); 1.5659 (2.8); 1.2231 (8.0); 1.2056 (16.0); 1.1881 (7.8); 0.0079 (0.6); 0.0002 (17.3); 0.0085 (0.6)
[0387] I.7-4: .sup.1H-NMR (400.6 MHz, CDCl3):
[0388] =7.3681 (2.0); 7.3459 (2.0); 7.2605 (5.9); 7.1296 (0.5); 7.1157 (0.7); 7.1138 (0.7); 7.1113 (0.8); 7.1094 (0.7); 7.0956 (0.7); 7.0911 (0.8); 7.0659 (0.8); 7.0614 (0.8); 7.0458 (1.7); 7.0414 (1.2); 7.0080 (0.9); 7.0043 (1.0); 6.9896 (0.9); 6.9879 (0.7); 6.9860 (0.9); 6.9845 (0.7); 6.9348 (1.2); 6.9312 (1.1); 6.9145 (1.0); 6.9109 (0.9); 6.7864 (1.9); 6.7699 (2.0); 6.2794 (3.3); 5.2983 (5.2); 4.6894 (6.6); 4.2766 (1.6); 4.2645 (1.7); 4.2613 (1.1); 4.2520 (1.8); 3.6077 (2.1); 3.5978 (1.4); 3.5953 (2.1); 3.5908 (0.7); 3.5834 (2.6); 3.5686 (1.4); 3.5533 (1.0); 3.4989 (4.6); 3.4960 (4.5); 1.5618 (0.8); 1.1430 (16.0); 1.1366 (0.5); 1.1277 (16.0); 0.0002 (7.9)
[0389] I.8-277: .sup.1H-NMR (400.6 MHz, CDCl3):
[0390] =8.7665 (1.9); 8.7508 (1.0); 8.1424 (1.0); 8.1226 (1.0); 7.7385 (0.8); 7.7246 (0.9); 7.7187 (0.8); 7.7048 (0.7); 7.4650 (3.0); 7.4436 (3.0); 7.2609 (17.2); 7.1381 (0.6); 7.1334 (0.7); 7.1199 (1.1); 7.1180 (1.0); 7.1153 (1.3); 7.1133 (1.0); 7.1011 (1.5); 7.0960 (2.0); 7.0813 (2.6); 7.0768 (1.5); 7.0502 (1.5); 7.0463 (1.6); 7.0320 (1.2); 7.0286 (1.1); 7.0261 (0.8); 7.0120 (0.6); 7.0083 (0.5); 6.9286 (1.7); 6.9249 (1.5); 6.9084 (1.4); 6.9050 (1.2); 6.6521 (2.9); 6.6361 (2.9); 6.2720 (4.8); 5.2994 (16.0); 5.2917 (6.8); 4.7088 (6.0); 4.7062 (5.6); 3.4912 (6.6); 3.4884 (6.4); 0.0080 (0.9); 0.0002 (24.1); 0.0086 (0.6)
[0391] I.9-278: .sup.1H-NMR (400.6 MHz, CDCl3):
[0392] =8.8366 (3.0); 8.8332 (1.6); 8.8233 (1.7); 8.8201 (3.0); 7.6770 (2.5); 7.6606 (2.4); 7.4601 (2.6); 7.4392 (2.6); 7.2610 (19.6); 7.2564 (0.7); 7.2520 (1.3); 7.2498 (1.7); 7.2455 (1.5); 7.2340 (1.6); 7.2296 (2.3); 7.2257 (1.8); 7.2163 (1.5); 7.2121 (0.6); 7.1255 (1.1); 7.1219 (1.2); 7.1073 (1.0); 7.1048 (1.0); 7.1026 (1.7); 7.0868 (0.7); 7.0832 (0.6); 6.9864 (1.6); 6.9833 (1.4); 6.9656 (1.4); 6.9615 (1.1); 6.6828 (2.5); 6.6684 (2.6); 6.2711 (4.7); 5.3773 (5.6); 5.2997 (16.0); 4.7614 (6.6); 3.4992 (6.3); 3.4966 (6.2); 0.0080 (0.8); 0.0002 (26.4); 0.0085 (0.8)
[0393] I.9-277: .sup.1H-NMR (400.6 MHz, CDCl3):
[0394] =8.5953 (1.9); 8.5917 (1.9); 8.5832 (2.0); 8.5796 (1.9); 8.5544 (2.6); 8.5498 (2.6); 7.6475 (1.2); 7.6431 (1.9); 7.6386 (1.1); 7.6280 (1.3); 7.6235 (2.1); 7.6190 (1.1); 7.4407 (4.9); 7.4197 (4.9); 7.3156 (1.8); 7.3032 (1.8); 7.2961 (1.6); 7.2840 (1.7); 7.2613 (18.2); 7.2226 (2.3); 7.2186 (2.8); 7.2029 (2.8); 7.1990 (4.6); 7.1800 (2.7); 7.1757 (2.0); 7.1602 (1.9); 7.1560 (1.5); 7.0674 (1.9); 7.0639 (2.0); 7.0481 (2.8); 7.0446 (2.7); 7.0287 (1.2); 7.0253 (1.2); 6.8720 (2.8); 6.8686 (2.7); 6.8516 (2.6); 6.8482 (2.4); 6.7039 (4.7); 6.6893 (4.7); 6.2618 (8.7); 5.2991 (9.6); 5.1686 (10.9); 4.6586 (16.0); 3.4825 (11.8); 3.4800 (11.9); 2.1182 (1.1); 2.0447 (1.1); 1.4367 (0.6); 1.4224 (0.6); 1.2592 (1.0); 0.0084 (0.8); 0.0002 (26.3); 0.0078 (0.7)
[0395] I.9-356: .sup.1H-NMR (400.6 MHz, CDCl3):
[0396] =7.4347 (2.6); 7.4135 (2.6); 7.3124 (3.7); 7.2616 (12.6); 7.2126 (1.3); 7.2085 (1.6); 7.1929 (1.6); 7.1890 (2.6); 7.1853 (0.8); 7.1703 (1.4); 7.1659 (1.0); 7.1501 (1.2); 7.1459 (0.9); 7.0529 (1.1); 7.0493 (1.2); 7.0336 (1.6); 7.0300 (1.5); 7.0143 (0.7); 7.0107 (0.7); 6.8429 (1.5); 6.8394 (1.5); 6.8224 (1.4); 6.8190 (1.3); 6.7170 (2.5); 6.7024 (2.6); 6.2694 (4.7); 5.2989 (12.6); 4.9953 (4.6); 4.9917 (4.6); 4.5763 (8.4); 3.8108 (16.0); 3.4931 (6.1); 3.4903 (6.2); 2.2034 (15.3); 2.1191 (1.0); 2.0444 (1.6); 1.4352 (0.5); 1.4211 (0.5); 1.2769 (0.6); 1.2591 (1.3); 1.2413 (0.5); 0.0079 (0.5); 0.0002 (18.1); 0.0085 (0.5)
[0397] I.7-43: .sup.1H-NMR (400.6 MHz, CDCl3):
[0398] =7.3750 (4.5); 7.3529 (4.5); 7.2600 (20.5); 7.1494 (1.1); 7.1449 (1.3); 7.1311 (1.6); 7.1292 (1.6); 7.1266 (1.9); 7.1247 (1.8); 7.1109 (1.8); 7.1064 (2.1); 7.0831 (1.8); 7.0786 (2.0); 7.0630 (3.9); 7.0586 (3.0); 7.0263 (2.2); 7.0226 (2.5); 7.0079 (1.9); 7.0062 (1.6); 7.0043 (2.0); 7.0026 (1.6); 6.9879 (1.0); 6.9843 (1.0); 6.9244 (2.7); 6.9208 (2.5); 6.9041 (2.3); 6.9005 (2.0); 6.7336 (4.3); 6.7172 (4.5); 6.2775 (7.2); 5.2988 (6.5); 4.6625 (16.0); 4.2628 (3.5); 4.2474 (7.5); 4.2319 (3.7); 3.9891 (4.2); 3.9737 (8.8); 3.9584 (4.4); 3.4989 (9.7); 3.4959 (10.1); 2.0383 (0.6); 2.0232 (2.4); 2.0079 (3.5); 1.9926 (2.3); 1.9772 (0.6); 1.5456 (1.8); 0.0080 (0.8); 0.0002 (30.6); 0.0084 (1.0)
[0399] I.7-9: .sup.1H-NMR (400.6 MHz, CDCl3):
[0400] =7.3814 (3.3); 7.3593 (3.4); 7.2604 (12.6); 7.1560 (0.8); 7.1514 (0.9); 7.1377 (1.4); 7.1357 (1.4); 7.1331 (1.5); 7.1312 (1.2); 7.1175 (1.2); 7.1129 (1.4); 7.0780 (1.2); 7.0736 (1.4); 7.0581 (2.9); 7.0536 (2.2); 7.0279 (1.7); 7.0243 (1.8); 7.0096 (1.6); 7.0077 (1.4); 7.0061 (1.6); 6.9897 (0.7); 6.9861 (0.7); 6.9467 (2.2); 6.9433 (1.9); 6.9264 (1.8); 6.9230 (1.5); 6.7492 (3.3); 6.7328 (3.4); 6.2844 (5.8); 5.2990 (10.3); 4.6995 (12.5); 4.3412 (2.0); 4.3389 (1.8); 4.3326 (2.3); 4.3298 (2.4); 4.3277 (2.2); 4.3244 (2.0); 4.3182 (2.2); 4.2275 (16.0); 3.7797 (3.2); 3.7685 (4.4); 3.7572 (2.7); 3.5032 (8.8); 3.5006 (8.2); 1.5497 (2.2); 0.0080 (0.6); 0.0002 (19.0); 0.0085 (0.6)
[0401] I.7-42: .sup.1H-NMR (400.6 MHz, CDCl3):
[0402] =7.3781 (4.5); 7.3559 (4.5); 7.2599 (18.4); 7.1409 (1.0); 7.1362 (1.1); 7.1226 (1.6); 7.1206 (1.5); 7.1180 (1.8); 7.1161 (1.5); 7.1025 (1.5); 7.0979 (1.8); 7.0779 (1.6); 7.0733 (1.8); 7.0579 (3.8); 7.0533 (2.8); 7.0278 (2.1); 7.0241 (2.2); 7.0095 (1.8); 7.0059 (1.8); 6.9896 (0.8); 6.9859 (0.8); 6.9292 (2.7); 6.9256 (2.4); 6.9089 (2.2); 6.9053 (2.0); 6.7264 (4.3); 6.7099 (4.3); 6.2764 (7.4); 5.2988 (4.6); 4.6998 (16.0); 4.3979 (3.3); 4.3865 (4.0); 4.3827 (2.3); 4.3743 (4.3); 4.2099 (3.9); 4.1977 (3.9); 4.1863 (2.9); 3.4983 (10.2); 3.4955 (10.1); 1.5426 (3.2); 0.0079 (0.8); 0.0002 (26.8); 0.0085 (0.8)
[0403] I.7-303: .sup.1H-NMR (400.6 MHz, CDCl3):
[0404] =8.4246 (1.5); 8.4193 (1.5); 7.7194 (1.6); 7.7142 (1.6); 7.3442 (1.3); 7.3221 (1.4); 7.2607 (1.4); 7.1166 (0.5); 7.1141 (0.5); 7.1005 (0.5); 7.0961 (0.6); 7.0700 (0.7); 7.0535 (0.8); 7.0495 (0.9); 7.0078 (1.9); 6.9881 (1.6); 6.9852 (0.6); 6.7857 (1.3); 6.7693 (1.3); 6.2609 (2.2); 5.3547 (4.6); 5.2951 (16.0); 4.7924 (4.1); 3.4840 (3.0); 3.4812 (3.0); 2.1676 (1.2); 0.0002 (2.1)
[0405] I.7-309: .sup.1H-NMR (400.6 MHz, CDCl3):
[0406] =8.0746 (1.0); 8.0728 (1.0); 8.0552 (1.2); 7.8496 (1.2); 7.8301 (2.3); 7.8106 (1.2); 7.4580 (1.4); 7.4382 (1.1); 7.4363 (1.1); 7.3314 (2.1); 7.3093 (2.1); 7.2622 (5.9); 7.1336 (0.5); 7.1195 (0.7); 7.1180 (0.7); 7.1150 (0.9); 7.0997 (0.7); 7.0952 (1.0); 7.0832 (0.8); 7.0788 (0.9); 7.0632 (1.7); 7.0588 (1.2); 7.0246 (0.9); 7.0209 (1.1); 7.0062 (0.8); 7.0026 (0.9); 6.9807 (1.4); 6.9770 (1.1); 6.9604 (1.0); 6.9569 (0.8); 6.7582 (2.0); 6.7417 (2.0); 6.2447 (3.5); 5.3906 (4.8); 5.2988 (16.0); 4.7815 (6.7); 3.9993 (16.0); 3.4804 (4.7); 3.4777 (4.7); 2.0447 (0.9); 1.2587 (0.8); 0.0002 (8.7)
[0407] I.7-301: .sup.1H-NMR (400.6 MHz, CDCl3):
[0408] =8.3203 (1.8); 8.3144 (1.8); 7.3445 (2.3); 7.3223 (2.3); 7.2606 (4.8); 7.2451 (0.6); 7.2392 (0.6); 7.2250 (0.7); 7.2223 (0.7); 7.2192 (0.7); 7.2164 (0.6); 7.2023 (0.6); 7.1963 (0.6); 7.1211 (0.5); 7.1165 (0.6); 7.1026 (0.8); 7.1009 (0.8); 7.0982 (1.0); 7.0965 (0.9); 7.0826 (0.8); 7.0781 (1.0); 7.0612 (0.9); 7.0568 (1.0); 7.0411 (1.9); 7.0367 (1.4); 7.0033 (1.0); 6.9996 (1.2); 6.9849 (0.9); 6.9834 (0.8); 6.9813 (1.0); 6.9797 (0.9); 6.9449 (1.4); 6.9413 (1.2); 6.9246 (1.1); 6.9210 (1.0); 6.7653 (2.2); 6.7489 (2.2); 6.2790 (3.8); 5.3230 (3.2); 5.3181 (3.1); 5.2977 (16.0); 4.7390 (7.7); 3.4966 (5.2); 3.4938 (5.3); 0.0002 (7.0)
[0409] I.7-302: .sup.1H-NMR (400.6 MHz, CDCl3):
[0410] =8.3761 (1.4); 8.3714 (1.4); 7.4775 (1.1); 7.4726 (1.0); 7.4552 (1.0); 7.4503 (1.0); 7.3427 (2.0); 7.3205 (2.0); 7.2613 (1.8); 7.1048 (0.7); 7.1003 (0.8); 7.0851 (0.6); 7.0806 (0.8); 7.0642 (0.8); 7.0597 (0.8); 7.0442 (1.6); 7.0397 (1.2); 7.0056 (0.8); 7.0020 (0.9); 6.9870 (0.8); 6.9833 (0.9); 6.9509 (1.2); 6.9473 (1.0); 6.9306 (1.0); 6.9271 (0.8); 6.7651 (1.9); 6.7486 (1.9); 6.2744 (3.4); 5.3193 (3.7); 5.3142 (3.6); 5.2959 (16.0); 4.7451 (6.6); 3.4927 (4.6); 3.4902 (4.6); 0.0002 (2.7)
[0411] I.7-308: .sup.1H-NMR (400.6 MHz, CDCl3):
[0412] =9.1442 (0.9); 9.1423 (0.9); 9.1389 (0.9); 9.1371 (0.8); 8.2643 (0.8); 8.2590 (0.8); 8.2440 (0.8); 8.2386 (0.8); 7.3285 (1.3); 7.3061 (1.7); 7.2837 (0.9); 7.2819 (0.8); 7.2640 (1.9); 7.1332 (0.5); 7.1315 (0.5); 7.1287 (0.6); 7.1271 (0.5); 7.1087 (0.6); 7.0956 (0.5); 7.0912 (0.6); 7.0756 (1.1); 7.0712 (0.8); 7.0350 (0.6); 7.0313 (0.7); 7.0166 (0.6); 7.0149 (0.5); 7.0129 (0.6); 6.9801 (0.9); 6.9766 (0.7); 6.9598 (0.7); 6.9563 (0.6); 6.7401 (1.3); 6.7238 (1.3); 6.2429 (2.3); 5.3351 (3.7); 5.2973 (16.0); 4.7933 (4.6); 3.9580 (10.0); 3.4795 (3.2); 3.4767 (3.1); 0.0002 (2.6)
[0413] I.7-327: .sup.1H-NMR (400.6 MHz, CDCl3):
[0414] =8.1776 (1.0); 8.1721 (1.0); 7.7344 (0.7); 7.7282 (0.6); 7.3379 (2.0); 7.3158 (2.0); 7.2625 (2.6); 7.1177 (0.5); 7.1047 (0.7); 7.1024 (0.7); 7.0998 (0.8); 7.0976 (0.7); 7.0846 (0.7); 7.0797 (0.9); 7.0636 (0.6); 7.0587 (0.8); 7.0435 (1.9); 7.0387 (1.3); 7.0239 (1.1); 7.0203 (1.1); 7.0061 (0.8); 7.0027 (0.8); 7.0005 (0.5); 6.9203 (0.9); 6.9098 (1.3); 6.9061 (1.2); 6.8993 (0.8); 6.8899 (1.3); 6.8859 (0.9); 6.6944 (1.9); 6.6780 (1.9); 6.2764 (3.4); 5.2975 (16.0); 5.1583 (4.7); 4.6825 (7.4); 3.4984 (4.8); 3.4956 (4.6); 0.0002 (3.8)
[0415] I.7-321: .sup.1H-NMR (400.6 MHz, CDCl3):
[0416] =9.1882 (2.7); 8.7020 (6.3); 7.3460 (2.2); 7.3239 (2.2); 7.2628 (5.7); 7.1322 (0.5); 7.1273 (0.6); 7.1142 (0.8); 7.1120 (0.7); 7.1094 (1.0); 7.1072 (0.8); 7.0942 (0.8); 7.0893 (1.1); 7.0802 (0.7); 7.0755 (0.8); 7.0601 (2.0); 7.0554 (1.3); 7.0360 (1.2); 7.0323 (1.3); 7.0180 (0.9); 7.0159 (0.7); 7.0145 (0.9); 7.0122 (0.6); 6.9193 (1.3); 6.9156 (1.2); 6.8990 (1.1); 6.8955 (1.0); 6.6873 (2.1); 6.6709 (2.1); 6.2822 (3.6); 5.2987 (16.0); 5.1788 (5.8); 4.6983 (8.2); 3.4974 (4.8); 3.4945 (4.8); 0.0002 (8.0)
[0417] I.7-275: .sup.1H-NMR (400.6 MHz, CDCl3):
[0418] =7.3510 (4.6); 7.3288 (4.7); 7.3222 (4.4); 7.3166 (4.3); 7.2606 (16.2); 7.1109 (1.0); 7.1064 (1.2); 7.0924 (1.6); 7.0907 (1.6); 7.0881 (1.9); 7.0863 (1.7); 7.0724 (1.5); 7.0679 (2.0); 7.0601 (1.9); 7.0557 (2.0); 7.0400 (3.8); 7.0357 (2.7); 6.9959 (2.0); 6.9922 (2.2); 6.9774 (1.9); 6.9758 (1.8); 6.9739 (2.0); 6.9575 (1.0); 6.9539 (0.9); 6.9002 (2.7); 6.8966 (2.5); 6.8799 (2.3); 6.8764 (2.1); 6.7910 (4.4); 6.7745 (4.5); 6.2809 (7.8); 6.2216 (4.8); 6.2160 (4.7); 5.2984 (4.0); 5.1674 (14.8); 4.6860 (14.6); 4.0606 (4.3); 4.0429 (6.1); 4.0249 (4.4); 3.4972 (10.6); 3.4944 (10.6); 1.9123 (0.5); 1.8938 (2.3); 1.8756 (4.2); 1.8577 (4.2); 1.8395 (2.5); 1.8213 (0.6); 1.6035 (0.6); 0.9285 (7.7); 0.9101 (16.0); 0.8915 (7.1); 0.0079 (0.7); 0.0002 (23.8); 0.0085 (0.7)
[0419] I.7-282: .sup.1H-NMR (400.6 MHz, CDCl3):
[0420] =8.5353 (1.6); 8.5216 (1.6); 8.5142 (1.5); 8.5006 (1.5); 7.3386 (4.5); 7.3164 (4.5); 7.2607 (18.9); 7.1491 (1.0); 7.1447 (1.2); 7.1307 (1.5); 7.1290 (1.6); 7.1262 (2.0); 7.1245 (1.9); 7.1106 (1.7); 7.1062 (2.2); 7.0959 (1.9); 7.0916 (2.0); 7.0758 (3.8); 7.0715 (2.8); 7.0333 (2.1); 7.0295 (2.4); 7.0149 (1.9); 7.0134 (1.6); 7.0113 (2.0); 7.0096 (1.8); 6.9949 (1.1); 6.9911 (2.0); 6.9849 (2.0); 6.9837 (2.0); 6.9761 (1.6); 6.9704 (3.5); 6.9669 (3.6); 6.9617 (3.1); 6.9553 (2.3); 6.9503 (2.7); 6.9469 (2.2); 6.9416 (1.4); 6.9354 (0.8); 6.7443 (4.4); 6.7280 (4.4); 6.2554 (7.5); 5.2987 (6.5); 5.2765 (12.6); 4.7837 (16.0); 3.4857 (10.1); 3.4828 (10.5); 2.0446 (0.9); 1.2591 (0.9); 0.8819 (0.5); 0.0080 (0.7); 0.0002 (28.3); 0.0085 (0.8)
[0421] I.7-283: .sup.1H-NMR (400.6 MHz, CDCl3):
[0422] =8.4132 (3.2); 8.4060 (3.1); 7.3993 (1.0); 7.3921 (1.0); 7.3783 (1.9); 7.3711 (1.9); 7.3576 (1.5); 7.3504 (1.4); 7.3347 (4.4); 7.3125 (4.6); 7.2753 (2.0); 7.2607 (15.1); 7.2538 (1.4); 7.2429 (1.3); 7.1340 (1.0); 7.1295 (1.2); 7.1157 (1.6); 7.1139 (1.6); 7.1112 (1.9); 7.1094 (1.6); 7.0957 (1.6); 7.0911 (2.0); 7.0802 (1.7); 7.0757 (1.8); 7.0601 (3.8); 7.0557 (2.7); 7.0234 (2.1); 7.0197 (2.3); 7.0051 (1.9); 7.0034 (1.6); 7.0016 (1.9); 6.9998 (1.5); 6.9852 (0.9); 6.9815 (0.9); 6.9488 (2.8); 6.9452 (2.4); 6.9286 (2.3); 6.9250 (1.9); 6.7450 (4.3); 6.7286 (4.4); 6.2580 (7.4); 5.2987 (6.0); 5.2560 (9.9); 4.7531 (16.0); 3.4885 (10.3); 3.4856 (10.2); 0.0079 (0.7); 0.0002 (21.9); 0.0085 (0.6)
[0423] I.7-272: .sup.1H-NMR (400.6 MHz, CDCl3):
[0424] =7.3497 (2.5); 7.3275 (2.5); 7.2987 (2.4); 7.2932 (2.3); 7.2606 (7.4); 7.2592 (6.0); 7.1135 (0.5); 7.1091 (0.6); 7.0936 (1.1); 7.0911 (1.1); 7.0893 (1.2); 7.0750 (0.8); 7.0706 (1.0); 7.0620 (1.0); 7.0577 (1.0); 7.0419 (2.0); 7.0376 (1.4); 6.9984 (1.0); 6.9949 (1.2); 6.9788 (1.2); 6.9769 (1.2); 6.9751 (1.2); 6.9010 (1.6); 6.8976 (1.4); 6.8808 (1.3); 6.8774 (1.1); 6.7889 (2.3); 6.7724 (2.3); 6.2783 (4.5); 6.2196 (2.6); 6.2141 (2.5); 5.2985 (1.9); 5.2971 (1.5); 5.1564 (8.6); 4.6843 (8.6); 3.8733 (16.0); 3.4954 (6.6); 3.4939 (6.6); 1.5823 (1.7); 0.0002 (10.3); 0.0017 (8.6)
[0425] I.7-281: .sup.1H-NMR (400.6 MHz, CDCl3):
[0426] =8.4081 (1.4); 8.4047 (2.6); 8.4013 (1.5); 8.3966 (1.5); 8.3931 (2.6); 8.3898 (1.4); 7.4353 (1.2); 7.4320 (1.2); 7.4142 (1.8); 7.4113 (2.6); 7.3908 (1.7); 7.3875 (1.7); 7.3390 (5.1); 7.3243 (1.6); 7.3168 (5.4); 7.3134 (2.9); 7.3027 (2.3); 7.2924 (1.8); 7.2814 (1.0); 7.2607 (10.8); 7.1198 (1.0); 7.1155 (1.2); 7.1004 (1.9); 7.0961 (2.7); 7.0812 (1.6); 7.0768 (2.1); 7.0642 (2.0); 7.0601 (2.2); 7.0445 (3.6); 7.0401 (2.9); 6.9937 (1.8); 6.9901 (2.5); 6.9749 (2.0); 6.9709 (3.1); 6.9655 (3.6); 6.9624 (2.2); 6.9553 (1.0); 6.9517 (1.3); 6.9455 (2.6); 6.9420 (1.9); 6.7865 (4.9); 6.7700 (4.9); 6.2739 (8.6); 5.3626 (8.4); 5.3576 (8.4); 5.2979 (8.6); 4.7639 (16.0); 3.4916 (11.6); 3.4890 (11.9); 1.5990 (0.5); 1.2583 (0.6); 0.0002 (15.5)
[0427] I.7-274: .sup.1H-NMR (400.6 MHz, CDCl3):
[0428] =7.3503 (4.5); 7.3409 (4.2); 7.3354 (4.2); 7.3281 (4.4); 7.2609 (10.3); 7.1130 (1.0); 7.1085 (1.1); 7.0943 (1.6); 7.0927 (1.6); 7.0900 (2.0); 7.0745 (1.4); 7.0700 (1.9); 7.0612 (1.8); 7.0568 (1.9); 7.0411 (3.6); 7.0368 (2.6); 6.9967 (1.9); 6.9931 (2.0); 6.9781 (1.9); 6.9764 (1.9); 6.9746 (2.0); 6.9583 (0.8); 6.9547 (0.9); 6.9027 (2.6); 6.8993 (2.5); 6.8824 (2.2); 6.8790 (2.0); 6.7927 (4.2); 6.7762 (4.2); 6.2806 (7.7); 6.2278 (4.5); 6.2221 (4.4); 5.2978 (5.0); 5.1687 (14.9); 4.6864 (14.5); 4.6540 (1.2); 4.1711 (2.2); 4.1528 (6.7); 4.1345 (6.8); 4.1162 (2.3); 3.4965 (10.8); 3.4943 (10.9); 1.4903 (7.8); 1.4720 (16.0); 1.4538 (7.6); 1.3176 (0.6); 1.2998 (1.1); 1.2819 (0.6); 1.2587 (0.5); 0.0079 (0.6); 0.0002 (14.7)
[0429] I.28-1: .sup.1H-NMR (400.6 MHz, CDCl3):
[0430] =7.5410 (1.9); 7.5196 (2.0); 7.2611 (5.0); 7.2457 (1.0); 7.2398 (1.3); 7.2241 (1.0); 7.2182 (1.6); 7.2019 (2.7); 7.1961 (1.8); 6.8176 (2.1); 6.7959 (1.9); 6.7884 (1.9); 6.7724 (1.9); 6.2910 (3.1); 5.2991 (7.9); 4.6734 (6.5); 4.2890 (1.5); 4.2807 (1.0); 4.2775 (1.4); 4.2737 (1.0); 4.2657 (1.7); 3.5648 (2.0); 3.5589 (0.6); 3.5561 (1.1); 3.5531 (1.9); 3.5504 (1.1); 3.5475 (0.6); 3.5415 (1.9); 3.5111 (4.3); 3.5083 (4.3); 3.3374 (16.0); 1.5621 (1.6); 0.0002 (7.3)
[0431] I.28-23: .sup.1H-NMR (400.6 MHz, CDCl3):
[0432] =7.5421 (1.8); 7.5206 (1.8); 7.2622 (3.9); 7.2457 (1.0); 7.2398 (1.2); 7.2240 (1.0); 7.2181 (1.5); 7.1937 (2.5); 7.1878 (1.8); 6.8275 (2.0); 6.8058 (1.8); 6.7877 (1.8); 6.7717 (1.8); 6.2939 (3.0); 5.2990 (9.0); 4.6669 (5.8); 4.3077 (1.4); 4.2990 (1.1); 4.2959 (1.5); 4.2920 (1.0); 4.2837 (1.5); 3.6901 (1.7); 3.6813 (1.1); 3.6781 (1.7); 3.6750 (1.0); 3.6662 (1.5); 3.6097 (1.2); 3.6008 (1.5); 3.5989 (1.5); 3.5929 (1.4); 3.5865 (2.4); 3.5234 (2.5); 3.5165 (2.3); 3.5118 (5.6); 3.5090 (5.2); 3.5013 (1.2); 3.3704 (16.0); 1.5840 (0.5); 0.0002 (5.8)
[0433] I.28-335: .sup.1H-NMR (400.6 MHz, CDCl3):
[0434] =8.6662 (1.8); 8.6628 (1.8); 7.7710 (0.9); 7.7657 (0.9); 7.7511 (1.4); 7.7457 (1.4); 7.6918 (2.1); 7.6900 (2.2); 7.6719 (1.3); 7.6700 (1.3); 7.5005 (2.3); 7.4792 (2.3); 7.2615 (7.8); 7.2472 (1.3); 7.2413 (1.6); 7.2257 (1.2); 7.2198 (2.0); 7.2030 (3.2); 7.1973 (2.3); 6.8286 (2.6); 6.8070 (2.3); 6.7010 (2.2); 6.6852 (2.2); 6.2907 (4.1); 5.2998 (16.0); 5.2346 (6.8); 4.6836 (8.4); 3.5174 (6.6); 3.5150 (6.8); 2.0447 (0.8); 1.5586 (3.6); 1.2593 (0.6); 0.0002 (11.4)
[0435] I.28-277: .sup.1H-NMR (400.6 MHz, CDCl3):
[0436] =8.5959 (0.9); 8.5922 (1.0); 8.5842 (2.0); 8.5804 (1.9); 7.6400 (0.6); 7.6357 (0.8); 7.6302 (0.5); 7.6204 (0.6); 7.6160 (0.9); 7.6106 (0.5); 7.5027 (2.3); 7.4813 (2.3); 7.3050 (0.8); 7.2930 (0.8); 7.2855 (0.7); 7.2734 (0.7); 7.2624 (5.4); 7.2241 (1.2); 7.2182 (1.7); 7.2028 (1.0); 7.1968 (2.4); 7.1900 (3.3); 7.1845 (1.7); 6.7955 (2.3); 6.7741 (2.1); 6.7217 (2.2); 6.7058 (2.2); 6.2901 (3.8); 5.2986 (16.0); 5.1798 (6.2); 4.6679 (8.1); 3.5074 (5.5); 3.5046 (5.3); 2.0442 (0.8); 1.2587 (0.5); 0.0002 (7.9)
[0437] I.28-329: .sup.1H-NMR (400.6 MHz, CDCl3):
[0438] =8.4757 (0.9); 8.4715 (0.9); 8.4635 (0.9); 8.4593 (0.9); 7.5548 (0.8); 7.5510 (0.8); 7.5358 (0.8); 7.5318 (0.8); 7.4923 (2.2); 7.4708 (2.3); 7.2617 (9.2); 7.2268 (1.3); 7.2209 (1.7); 7.2054 (1.1); 7.1995 (2.4); 7.1902 (3.3); 7.1845 (1.9); 7.1380 (0.7); 7.1257 (0.8); 7.1191 (0.7); 7.1065 (0.7); 6.7987 (2.3); 6.7772 (2.1); 6.7238 (2.2); 6.7078 (2.2); 6.2784 (3.6); 5.2989 (16.0); 5.1863 (5.5); 4.6794 (7.6); 3.5048 (4.7); 3.5019 (4.8); 2.5385 (0.6); 2.5314 (9.6); 0.0002 (13.7)
[0439] I.28-321: .sup.1H-NMR (400.6 MHz, CDCl3):
[0440] =9.2019 (5.7); 8.7214 (10.2); 7.5180 (4.4); 7.4966 (4.4); 7.2616 (18.5); 7.2408 (2.1); 7.2349 (3.0); 7.2195 (1.6); 7.2136 (4.2); 7.2073 (6.3); 7.2017 (3.3); 6.8113 (4.5); 6.7900 (4.0); 6.6988 (4.3); 6.6830 (4.3); 6.2974 (7.7); 5.2997 (13.6); 5.1755 (13.1); 4.6772 (0.8); 4.6664 (16.0); 3.5116 (10.7); 3.5092 (11.1); 2.1263 (1.0); 2.0448 (1.2); 1.5804 (2.0); 1.2592 (0.9); 0.0080 (0.9); 0.0002 (26.7); 0.0085 (0.8)
[0441] I.28-356: .sup.1H-NMR (400.6 MHz, CDCl3):
[0442] =7.5095 (2.6); 7.4880 (2.6); 7.2845 (3.5); 7.2620 (7.3); 7.2138 (1.3); 7.2079 (1.7); 7.1922 (1.3); 7.1863 (2.1); 7.1684 (3.5); 7.1626 (2.4); 6.7658 (2.7); 6.7441 (2.6); 6.7372 (2.4); 6.7212 (2.4); 6.2954 (4.3); 5.2987 (16.0); 5.0093 (6.2); 4.5969 (8.7); 3.8818 (0.6); 3.8037 (0.8); 3.7959 (14.4); 3.5158 (5.7); 3.5133 (6.1); 2.4816 (0.6); 2.2231 (0.6); 2.2132 (14.0); 2.0443 (0.6); 1.2590 (0.6); 0.8817 (0.5); 0.0002 (10.5)
[0443] I.28-176: .sup.1H-NMR (400.6 MHz, CDCl3):
[0444] =7.5695 (3.3); 7.5481 (3.3); 7.2844 (1.8); 7.2785 (2.4); 7.2604 (13.8); 7.2571 (3.3); 7.2440 (4.5); 7.2383 (2.9); 6.8418 (3.6); 6.8202 (3.3); 6.6984 (3.2); 6.6826 (3.3); 6.3033 (5.7); 5.2995 (9.4); 4.7599 (16.0); 4.7197 (12.8); 3.8618 (1.0); 3.5179 (8.3); 3.5153 (8.3); 2.0448 (0.7); 1.6761 (1.4); 1.5460 (1.7); 1.2592 (0.7); 0.0079 (0.5); 0.0002 (19.1); 0.0085 (0.5)
[0445] I.33-1: .sup.1H-NMR (400.6 MHz, CDCl3):
[0446] =7.5437 (1.4); 7.5373 (4.6); 7.5320 (0.6); 7.5164 (3.2); 7.5113 (1.0); 7.2616 (8.2); 6.9190 (1.6); 6.8982 (1.5); 6.8153 (1.7); 6.8011 (1.7); 6.2799 (3.3); 5.3000 (6.8); 4.7354 (5.7); 4.2711 (1.6); 4.2633 (1.0); 4.2596 (1.6); 4.2557 (1.0); 4.2480 (1.8); 3.5549 (1.9); 3.5469 (1.2); 3.5433 (2.0); 3.5402 (1.2); 3.5318 (1.9); 3.5053 (4.3); 3.5027 (4.6); 3.3558 (0.5); 3.3509 (0.9); 3.3327 (16.0); 3.3145 (0.6); 2.0447 (0.6); 1.5581 (2.1); 0.0002 (12.0)
[0447] I.7-367: .sup.1H-NMR (400.6 MHz, CDCl3):
[0448] =7.3490 (2.0); 7.3269 (2.0); 7.2604 (12.8); 7.1098 (0.5); 7.0959 (0.7); 7.0941 (0.7); 7.0915 (0.9); 7.0897 (0.8); 7.0759 (0.8); 7.0711 (1.4); 7.0679 (2.5); 7.0663 (3.9); 7.0496 (1.7); 7.0453 (1.1); 7.0068 (0.9); 7.0031 (1.0); 6.9885 (0.9); 6.9867 (0.8); 6.9850 (0.9); 6.9831 (0.7); 6.9106 (1.2); 6.9069 (1.1); 6.8902 (1.0); 6.8868 (0.9); 6.7768 (1.9); 6.7604 (2.0); 6.2667 (3.4); 5.2992 (0.6); 5.2201 (5.7); 4.7124 (6.9); 3.4909 (4.7); 3.4882 (4.6); 2.6900 (16.0); 1.5681 (0.6); 0.0079 (0.6); 0.0002 (18.1)
[0449] I.7-366: .sup.1H-NMR (400.6 MHz, CDCl3):
[0450] =8.7702 (4.4); 8.7652 (4.3); 7.3467 (4.4); 7.3246 (4.4); 7.2823 (3.7); 7.2805 (2.7); 7.2773 (3.6); 7.2606 (16.3); 7.1197 (0.9); 7.1152 (1.1); 7.1011 (1.7); 7.0967 (2.1); 7.0813 (1.5); 7.0768 (2.1); 7.0733 (1.9); 7.0688 (1.9); 7.0532 (3.7); 7.0489 (2.6); 7.0112 (2.0); 7.0075 (2.1); 6.9927 (2.0); 6.9892 (2.0); 6.9729 (0.9); 6.9692 (0.9); 6.9157 (2.7); 6.9122 (2.5); 6.8954 (2.3); 6.8920 (2.0); 6.7514 (4.2); 6.7349 (4.3); 6.2679 (7.7); 5.7139 (0.6); 5.3390 (13.4); 5.2989 (0.8); 4.7238 (16.0); 3.4906 (11.2); 3.4882 (11.0); 1.5757 (1.7); 0.0078 (0.8); 0.0002 (23.0); 0.0085 (0.7)
[0451] I.7-371: .sup.1H-NMR (400.6 MHz, CDCl3):
[0452] =7.8613 (5.2); 7.3599 (3.0); 7.3377 (3.0); 7.2612 (11.0); 7.1251 (4.0); 7.1099 (1.1); 7.1076 (1.0); 7.1050 (1.3); 7.1028 (1.1); 7.0897 (1.1); 7.0848 (1.4); 7.0655 (0.9); 7.0608 (1.2); 7.0455 (2.7); 7.0408 (1.9); 7.0240 (1.6); 7.0204 (1.8); 7.0061 (1.3); 7.0025 (1.3); 7.0003 (0.8); 6.9861 (0.6); 6.9824 (0.6); 6.9163 (1.8); 6.9128 (1.6); 6.8961 (1.5); 6.8925 (1.3); 6.7124 (2.9); 6.6960 (2.9); 6.2843 (4.9); 5.2988 (16.0); 5.1864 (8.4); 4.6786 (11.3); 3.5021 (6.7); 3.4992 (6.8); 2.0444 (1.4); 1.2589 (0.9); 0.0002 (15.3)
[0453] I.7-365: .sup.1H-NMR (400.6 MHz, CDCl3):
[0454] =7.8420 (2.0); 7.6585 (2.3); 7.6564 (2.1); 7.3567 (2.1); 7.3345 (2.1); 7.2623 (3.1); 7.1153 (0.5); 7.1016 (0.7); 7.0997 (0.7); 7.0970 (0.9); 7.0951 (0.7); 7.0815 (0.7); 7.0769 (0.9); 7.0637 (0.8); 7.0591 (0.8); 7.0436 (1.8); 7.0391 (1.3); 7.0104 (1.0); 7.0067 (1.0); 6.9921 (0.8); 6.9901 (0.8); 6.9885 (0.8); 6.9868 (0.6); 6.9106 (1.2); 6.9070 (1.1); 6.8903 (1.0); 6.8868 (0.9); 6.7496 (2.0); 6.7331 (2.0); 6.2801 (3.4); 5.2977 (16.0); 5.1215 (5.2); 4.6918 (7.4); 3.4973 (4.6); 3.4945 (4.6); 2.0437 (0.8); 1.2584 (0.5); 0.0002 (4.5)
[0455] I.7-328: .sup.1H-NMR (400.6 MHz, CDCl3):
[0456] =8.4421 (2.8); 8.4353 (2.8); 8.3820 (2.8); 7.3698 (0.9); 7.3638 (1.2); 7.3587 (0.9); 7.3477 (1.0); 7.3416 (1.3); 7.3342 (4.6); 7.3120 (4.4); 7.2610 (14.5); 7.1350 (0.9); 7.1303 (1.1); 7.1168 (1.4); 7.1149 (1.4); 7.1122 (1.7); 7.1103 (1.5); 7.0968 (1.4); 7.0921 (1.9); 7.0819 (1.4); 7.0772 (1.7); 7.0618 (3.8); 7.0572 (2.6); 7.0354 (2.1); 7.0317 (2.2); 7.0172 (1.7); 7.0140 (1.7); 6.9973 (0.8); 6.9936 (0.7); 6.9242 (2.6); 6.9206 (2.4); 6.9040 (2.2); 6.9004 (1.9); 6.6968 (4.2); 6.6804 (4.2); 6.2770 (7.3); 5.2990 (10.6); 5.1953 (11.7); 4.7058 (16.0); 3.4963 (9.9); 3.4936 (10.0); 0.0079 (0.7); 0.0002 (21.0); 0.0085 (0.6)
[0457] I.7-296: .sup.1H-NMR (400.6 MHz, CDCl3):
[0458] =8.4873 (1.6); 8.4775 (1.6); 7.5620 (1.4); 7.5445 (1.6); 7.3720 (0.7); 7.3498 (0.7); 7.3185 (4.0); 7.2963 (4.0); 7.2607 (13.9); 7.2563 (1.7); 7.2438 (1.6); 7.2368 (1.4); 7.2246 (1.4); 7.1189 (1.0); 7.1145 (1.1); 7.0996 (1.8); 7.0969 (1.5); 7.0936 (1.4); 7.0804 (1.4); 7.0759 (1.8); 7.0656 (0.5); 7.0577 (1.5); 7.0529 (1.7); 7.0366 (3.3); 7.0326 (2.5); 7.0072 (0.8); 6.9955 (1.3); 6.9919 (2.6); 6.9832 (2.9); 6.9797 (2.9); 6.9770 (1.8); 6.9740 (2.5); 6.9630 (1.9); 6.9591 (2.0); 6.9530 (0.5); 6.7818 (3.8); 6.7653 (3.8); 6.7415 (0.6); 6.7250 (0.6); 6.2709 (1.2); 6.2583 (6.8); 5.3176 (12.0); 5.2983 (14.0); 4.8921 (0.6); 4.7658 (9.3); 4.6549 (1.6); 3.4828 (10.4); 3.4800 (9.9); 2.4083 (1.0); 2.3277 (16.0); 0.0080 (0.7); 0.0002 (20.0); 0.0085 (0.6)
[0459] I.7-284: .sup.1H-NMR (400.6 MHz, CDCl3):
[0460] =8.3421 (2.8); 8.3360 (2.9); 7.5983 (1.9); 7.5922 (1.8); 7.5779 (2.2); 7.5716 (2.1); 7.3366 (4.3); 7.3143 (5.1); 7.3118 (4.0); 7.2912 (3.1); 7.2609 (16.2); 7.1270 (0.9); 7.1221 (1.1); 7.1091 (1.6); 7.1067 (1.5); 7.1042 (1.9); 7.1019 (1.5); 7.0891 (1.5); 7.0841 (2.0); 7.0696 (1.2); 7.0648 (1.6); 7.0496 (3.9); 7.0448 (2.7); 7.0292 (2.3); 7.0255 (2.4); 7.0113 (1.9); 7.0077 (1.8); 7.0055 (1.1); 6.9912 (0.8); 6.9876 (0.7); 6.9120 (2.6); 6.9086 (2.4); 6.8918 (2.2); 6.8884 (1.9); 6.6922 (4.2); 6.6758 (4.2); 6.2749 (7.3); 5.2989 (7.3); 5.1512 (12.0); 4.6840 (16.0); 3.9833 (0.5); 3.4973 (10.6); 3.4945 (10.1); 1.4107 (1.6); 1.2937 (0.6); 1.2555 (1.4); 0.0080 (0.6); 0.0002 (23.6); 0.0085 (0.7)
[0461] I.19-365: .sup.1H-NMR (400.6 MHz, CDCl3):
[0462] =7.8368 (4.6); 7.6722 (0.6); 7.6701 (0.6); 7.6644 (4.9); 7.6622 (5.2); 7.3495 (4.4); 7.3274 (4.4); 7.2619 (11.4); 7.1100 (1.0); 7.0952 (1.1); 7.0888 (2.3); 7.0740 (2.4); 7.0676 (1.4); 7.0527 (1.3); 6.8777 (1.3); 6.8744 (1.6); 6.8534 (2.2); 6.8512 (2.1); 6.8331 (1.2); 6.8298 (1.2); 6.6845 (2.9); 6.6684 (3.0); 6.6540 (1.3); 6.6503 (2.3); 6.6469 (1.4); 6.6328 (1.2); 6.6291 (2.1); 6.6258 (1.2); 6.3230 (0.6); 6.2666 (7.4); 5.2988 (16.0); 5.1279 (0.9); 5.1054 (11.5); 4.6768 (15.9); 3.5313 (0.8); 3.5285 (0.8); 3.4898 (10.0); 3.4870 (10.5); 2.0443 (1.6); 1.5868 (6.9); 1.2767 (0.5); 1.2589 (1.2); 0.0002 (9.9)
[0463] I.19-89: .sup.1H-NMR (400.6 MHz, CDCl3):
[0464] =7.3737 (4.6); 7.3516 (4.6); 7.2611 (15.7); 7.1447 (1.4); 7.1299 (1.2); 7.1235 (2.5); 7.1088 (2.4); 7.1023 (1.5); 7.0876 (1.3); 6.8975 (1.4); 6.8942 (1.4); 6.8739 (2.1); 6.8710 (1.8); 6.8529 (1.4); 6.8496 (1.2); 6.6832 (1.5); 6.6796 (2.4); 6.6762 (1.4); 6.6594 (4.2); 6.6551 (1.4); 6.6444 (2.8); 6.3291 (0.6); 6.2758 (7.6); 5.2990 (13.7); 4.7661 (3.8); 4.7500 (4.4); 4.7468 (4.5); 4.7306 (4.1); 4.6583 (16.0); 4.3980 (2.5); 4.3892 (2.7); 4.3830 (4.4); 4.3739 (4.3); 4.3677 (7.4); 4.3586 (2.5); 4.3510 (5.1); 3.5369 (0.8); 3.5341 (0.8); 3.4972 (10.5); 3.4943 (10.5); 3.2693 (0.9); 3.2666 (0.9); 3.2647 (0.8); 3.2497 (1.4); 3.2349 (0.8); 3.2329 (0.9); 3.2303 (0.7); 2.0445 (1.5); 1.5667 (5.5); 1.5633 (6.1); 1.2768 (0.5); 1.2590 (1.1); 0.0002 (16.0)
[0465] I.8-329: .sup.1H-NMR (400.6 MHz, CDCl3):
[0466] =8.4643 (0.9); 8.4601 (0.9); 8.4521 (0.9); 8.4478 (0.8); 7.5504 (0.8); 7.5465 (0.7); 7.5312 (0.8); 7.5274 (0.8); 7.4805 (2.2); 7.4590 (2.2); 7.2613 (8.2); 7.1240 (1.1); 7.1190 (0.7); 7.1129 (0.8); 7.1056 (1.4); 7.1038 (1.0); 7.1009 (1.0); 7.0988 (0.9); 7.0938 (0.7); 7.0856 (0.8); 7.0808 (1.1); 7.0730 (0.8); 7.0684 (0.9); 7.0529 (1.9); 7.0484 (1.3); 7.0248 (1.1); 7.0210 (1.2); 7.0067 (0.9); 7.0046 (0.8); 7.0031 (0.9); 7.0011 (0.7); 6.9146 (1.2); 6.9110 (1.2); 6.8944 (1.1); 6.8908 (0.9); 6.6774 (2.1); 6.6613 (2.2); 6.2586 (3.5); 5.2982 (16.0); 5.1874 (5.4); 4.7082 (7.5); 3.4869 (4.7); 3.4840 (4.8); 2.5169 (9.6); 2.0442 (0.6); 1.2588 (0.9); 0.0002 (11.5)
[0467] I.7-329: .sup.1H-NMR (400.6 MHz, CDCl3):
[0468] =8.4641 (0.8); 8.4599 (0.9); 8.4519 (0.9); 8.4477 (0.8); 7.5509 (0.8); 7.5469 (0.8); 7.5317 (0.8); 7.5277 (0.8); 7.3168 (2.2); 7.2946 (2.2); 7.2615 (6.5); 7.1234 (0.8); 7.1201 (0.7); 7.1151 (0.7); 7.1113 (0.8); 7.1022 (1.1); 7.1000 (0.8); 7.0972 (1.0); 7.0950 (1.0); 7.0819 (0.8); 7.0771 (1.0); 7.0674 (0.7); 7.0626 (0.9); 7.0473 (2.0); 7.0426 (1.3); 7.0224 (1.1); 7.0187 (1.2); 7.0044 (0.8); 7.0009 (0.9); 6.9988 (0.7); 6.9098 (1.3); 6.9061 (1.2); 6.8895 (1.1); 6.8860 (1.0); 6.7134 (2.1); 6.6971 (2.0); 6.2628 (3.6); 5.2980 (16.0); 5.1883 (5.5); 4.7070 (7.6); 3.4895 (4.8); 3.4867 (5.0); 2.5155 (9.7); 2.0440 (0.6); 1.2586 (0.8); 0.0002 (9.3)
[0469] I.8-321: .sup.1H-NMR (400.6 MHz, CDCl3):
[0470] =9.1886 (2.6); 8.7036 (5.9); 7.5061 (2.0); 7.4846 (2.0); 7.2617 (5.9); 7.1179 (0.6); 7.1161 (0.7); 7.1134 (0.8); 7.1116 (0.8); 7.0980 (0.6); 7.0933 (0.9); 7.0867 (0.7); 7.0820 (0.8); 7.0666 (1.7); 7.0621 (1.2); 7.0386 (0.9); 7.0350 (1.0); 7.0205 (0.8); 7.0171 (0.8); 6.9239 (1.2); 6.9203 (1.1); 6.9036 (1.0); 6.9002 (0.9); 6.6470 (2.0); 6.6310 (2.0); 6.2777 (3.4); 5.2989 (16.0); 5.1759 (5.8); 4.6975 (7.4); 3.4945 (4.7); 3.4919 (4.9); 1.2580 (0.8); 0.0002 (8.2)
[0471] I.8-367: .sup.1H-NMR (400.6 MHz, CDCl3):
[0472] =7.5108 (2.0); 7.4892 (2.0); 7.2614 (4.9); 7.1113 (0.5); 7.0974 (0.7); 7.0956 (0.7); 7.0930 (0.8); 7.0912 (0.7); 7.0774 (0.7); 7.0732 (1.6); 7.0693 (1.1); 7.0649 (3.2); 7.0536 (1.6); 7.0494 (1.0); 7.0074 (0.9); 7.0037 (1.0); 6.9890 (0.8); 6.9873 (0.7); 6.9856 (0.8); 6.9837 (0.6); 6.9135 (1.2); 6.9099 (1.0); 6.8932 (1.0); 6.8898 (0.8); 6.7433 (1.9); 6.7271 (1.9); 6.2620 (3.2); 5.2979 (16.0); 5.2182 (5.1); 4.7129 (6.5); 3.4875 (4.3); 3.4847 (4.4); 2.6988 (0.6); 2.6884 (15.2); 2.0440 (0.6); 1.2586 (0.5); 0.0002 (6.9)
[0473] I.19-367: .sup.1H-NMR (400.6 MHz, CDCl3):
[0474] =7.3414 (2.0); 7.3193 (1.9); 7.2612 (7.5); 7.0981 (0.5); 7.0832 (0.7); 7.0769 (1.2); 7.0706 (3.4); 7.0620 (1.1); 7.0557 (0.6); 7.0409 (0.6); 6.8707 (0.6); 6.8675 (0.7); 6.8467 (0.9); 6.8443 (0.8); 6.8262 (0.5); 6.8230 (0.5); 6.7339 (1.2); 6.7178 (1.2); 6.6532 (0.6); 6.6496 (1.1); 6.6461 (0.6); 6.6321 (0.6); 6.6284 (0.9); 6.2500 (3.3); 5.2987 (0.9); 5.2258 (0.5); 5.1993 (5.2); 4.6972 (6.8); 3.4813 (4.4); 3.4784 (4.4); 2.6971 (1.4); 2.6830 (16.0); 1.5873 (1.5); 0.0002 (7.3)
[0475] I.19-71: .sup.1H-NMR (400.6 MHz, CDCl3):
[0476] =7.3585 (3.6); 7.3364 (3.6); 7.2617 (8.4); 7.1322 (0.9); 7.1173 (1.0); 7.1110 (1.9); 7.0961 (2.0); 7.0897 (1.1); 7.0749 (1.1); 6.8779 (1.2); 6.8746 (1.2); 6.8564 (1.3); 6.8543 (1.7); 6.8513 (1.4); 6.8333 (1.0); 6.8300 (0.9); 6.7228 (2.1); 6.7067 (2.1); 6.6825 (1.0); 6.6792 (1.7); 6.6760 (0.9); 6.6613 (1.0); 6.6580 (1.6); 6.2654 (3.3); 6.2611 (3.1); 5.2984 (16.0); 4.6905 (10.2); 4.1880 (1.0); 4.1815 (0.8); 4.1689 (1.2); 4.1624 (1.4); 4.1543 (1.0); 4.1047 (0.9); 4.0893 (1.9); 4.0742 (1.7); 4.0685 (1.0); 4.0620 (1.0); 4.0574 (2.6); 4.0501 (0.8); 4.0412 (0.9); 3.8169 (1.0); 3.8124 (0.7); 3.8004 (1.1); 3.7959 (1.7); 3.7838 (0.6); 3.7794 (1.7); 3.7713 (0.6); 3.7631 (0.7); 3.7595 (0.6); 3.7544 (1.2); 3.7427 (1.1); 3.7379 (0.9); 3.7337 (0.6); 3.7262 (0.6); 3.7220 (0.5); 3.5321 (0.6); 3.4884 (7.9); 2.0441 (0.5); 1.9711 (0.6); 1.9540 (0.8); 1.9372 (0.5); 1.9016 (0.6); 1.8931 (0.6); 1.8855 (1.3); 1.8767 (1.3); 1.8665 (1.8); 1.8580 (1.6); 1.8497 (1.4); 1.8412 (1.2); 1.5827 (2.6); 1.5802 (2.4); 1.5542 (0.6); 1.5398 (0.5); 1.5362 (0.6); 1.5259 (0.5); 1.5196 (0.5); 0.0002 (8.4)
[0477] I.19-72: .sup.1H-NMR (400.6 MHz, CDCl3):
[0478] =7.3676 (4.6); 7.3455 (4.6); 7.2614 (13.6); 7.1443 (1.1); 7.1295 (1.1); 7.1231 (2.3); 7.1083 (2.2); 7.1019 (1.4); 7.0871 (1.2); 6.8928 (1.4); 6.8896 (1.5); 6.8690 (2.2); 6.8664 (1.9); 6.8483 (1.3); 6.8450 (1.2); 6.6725 (3.8); 6.6576 (2.5); 6.6553 (2.5); 6.6507 (2.0); 6.2834 (3.9); 6.2645 (3.9); 5.2988 (15.7); 4.6476 (16.0); 4.1663 (0.8); 4.1499 (0.9); 4.1396 (1.8); 4.1234 (1.9); 4.1130 (1.4); 4.0968 (1.3); 4.0482 (1.4); 4.0280 (1.5); 4.0227 (1.7); 4.0021 (1.7); 3.9961 (0.9); 3.9757 (0.9); 3.8465 (0.8); 3.8330 (0.9); 3.8256 (1.8); 3.8120 (1.8); 3.8052 (1.3); 3.7916 (1.2); 3.7564 (1.1); 3.7535 (1.0); 3.7384 (2.2); 3.7313 (1.4); 3.7173 (2.6); 3.7002 (1.6); 3.6800 (0.7); 3.5342 (0.7); 3.5314 (0.8); 3.5194 (1.1); 3.5063 (1.6); 3.4931 (10.5); 3.4906 (10.5); 3.4785 (1.1); 3.4654 (1.0); 2.5513 (0.7); 2.5343 (0.9); 2.5168 (0.7); 2.0443 (0.9); 2.0149 (0.6); 2.0020 (0.9); 1.9923 (0.6); 1.9830 (0.9); 1.9699 (0.7); 1.5696 (4.7); 1.5604 (1.2); 1.5423 (1.0); 1.5282 (0.7); 1.2589 (0.7); 0.0002 (13.9)
[0479] I.19-41: .sup.1H-NMR (400.6 MHz, CDCl3):
[0480] =7.3695 (4.2); 7.3474 (4.2); 7.2606 (7.4); 7.1430 (1.3); 7.1281 (1.2); 7.1217 (2.4); 7.1069 (2.3); 7.1005 (1.4); 7.0858 (1.2); 6.8983 (1.5); 6.8950 (1.4); 6.8748 (2.4); 6.8719 (1.7); 6.8537 (1.4); 6.8504 (1.2); 6.6826 (1.7); 6.6791 (2.4); 6.6756 (1.3); 6.6614 (1.7); 6.6579 (2.3); 6.6542 (1.4); 6.6485 (3.0); 6.6324 (2.9); 6.3194 (0.6); 6.2610 (7.2); 5.2979 (11.5); 4.6900 (16.0); 4.3688 (2.5); 4.3590 (3.4); 4.3457 (2.8); 4.1293 (5.0); 4.1246 (1.8); 4.1198 (4.0); 4.1174 (5.0); 4.1105 (1.7); 4.1060 (3.8); 3.5314 (1.0); 3.4909 (11.8); 3.4882 (10.6); 1.5608 (3.2); 0.0002 (7.3)
[0481] I.19-356: .sup.1H-NMR (400.6 MHz, CDCl3):
[0482] =7.3264 (2.7); 7.3036 (4.2); 7.3018 (4.0); 7.2621 (7.2); 7.1054 (0.6); 7.0905 (0.8); 7.0842 (1.4); 7.0694 (1.4); 7.0630 (0.9); 7.0482 (0.8); 6.8779 (0.8); 6.8746 (0.9); 6.8542 (1.3); 6.8515 (1.1); 6.8333 (0.7); 6.8300 (0.7); 6.6562 (1.7); 6.6400 (1.7); 6.6260 (0.9); 6.6224 (1.5); 6.6190 (0.9); 6.6048 (0.8); 6.6012 (1.4); 6.5978 (0.8); 6.2647 (4.6); 5.2982 (10.8); 5.0219 (0.6); 5.0032 (4.8); 4.9999 (4.7); 4.6046 (1.0); 4.5971 (9.5); 3.7989 (16.0); 3.4934 (6.2); 3.4907 (6.3); 2.2045 (15.4); 2.1957 (1.3); 2.0441 (1.6); 1.6165 (0.7); 1.2766 (0.5); 1.2588 (1.3); 0.0002 (7.9)
[0483] I.19-278: .sup.1H-NMR (400.6 MHz, CDCl3):
[0484] =8.5908 (3.1); 8.5758 (3.2); 7.3045 (3.6); 7.2823 (3.6); 7.2622 (10.0); 7.1647 (3.9); 7.1607 (2.4); 7.1537 (2.6); 7.1497 (3.6); 7.1421 (1.0); 7.1272 (1.0); 7.1208 (1.9); 7.1061 (2.0); 7.0996 (1.2); 7.0849 (1.1); 6.9141 (1.1); 6.9108 (1.2); 6.8906 (1.7); 6.8877 (1.4); 6.8695 (1.0); 6.8662 (0.9); 6.6965 (1.2); 6.6930 (2.0); 6.6895 (1.1); 6.6754 (1.2); 6.6718 (1.8); 6.6684 (1.0); 6.6335 (2.3); 6.6175 (2.3); 6.2289 (6.2); 5.2983 (16.0); 5.1763 (0.8); 5.1640 (5.8); 4.7277 (13.4); 3.5208 (0.6); 3.5180 (0.6); 3.4734 (8.4); 3.4705 (8.5); 2.0440 (1.5); 1.2765 (0.5); 1.2586 (1.5); 1.2408 (0.5); 0.0002 (10.2)
[0485] I.19-321: .sup.1H-NMR (400.6 MHz, CDCl3):
[0486] =9.1915 (6.2); 8.6951 (14.7); 7.3396 (4.0); 7.3176 (4.1); 7.2621 (11.5); 7.1265 (0.9); 7.1194 (0.5); 7.1116 (1.0); 7.1052 (2.2); 7.0905 (2.2); 7.0843 (1.6); 7.0693 (1.2); 6.9045 (1.9); 6.8815 (2.9); 6.8600 (1.5); 6.6615 (2.8); 6.6403 (2.6); 6.5965 (3.3); 6.5805 (3.4); 6.3217 (0.6); 6.2683 (7.9); 5.2993 (11.2); 5.1770 (1.2); 5.1659 (14.4); 4.6747 (16.0); 3.5259 (1.2); 3.4877 (15.0); 2.1254 (0.8); 2.0443 (1.1); 1.5879 (8.5); 1.2767 (0.5); 1.2562 (1.8); 1.2412 (0.6); 0.0002 (12.3); 0.0021 (7.5); 0.0081 (0.8)
[0487] I.19-277: .sup.1H-NMR (400.6 MHz, CDCl3):
[0488] =8.5914 (1.6); 8.5878 (1.7); 8.5794 (1.7); 8.5757 (1.7); 8.5610 (2.2); 8.5562 (2.2); 7.6358 (1.0); 7.6303 (1.6); 7.6259 (1.1); 7.6162 (1.2); 7.6108 (1.8); 7.6063 (1.2); 7.3208 (4.4); 7.2988 (5.1); 7.2901 (1.6); 7.2826 (1.5); 7.2705 (1.3); 7.2688 (1.3); 7.2617 (14.3); 7.1162 (1.1); 7.1014 (1.1); 7.0950 (2.4); 7.0802 (2.4); 7.0738 (1.5); 7.0590 (1.3); 6.8933 (1.3); 6.8900 (1.4); 6.8692 (2.0); 6.8668 (1.8); 6.8487 (1.3); 6.8454 (1.2); 6.6563 (1.4); 6.6526 (2.4); 6.6492 (1.3); 6.6316 (4.9); 6.6157 (2.7); 6.3175 (0.6); 6.2567 (7.4); 5.2985 (15.0); 5.1873 (1.0); 5.1718 (10.9); 4.6738 (16.0); 3.5267 (0.8); 3.5238 (0.9); 3.4834 (9.8); 3.4805 (10.2); 2.0441 (1.3); 1.6578 (0.8); 1.2588 (1.3); 0.0002 (14.2)
[0489] I.28-276: .sup.1H-NMR (400.6 MHz, CDCl3):
[0490] =8.5994 (1.0); 8.5950 (1.3); 8.5905 (0.6); 8.5852 (1.3); 8.5811 (0.9); 7.7361 (0.8); 7.7316 (0.8); 7.7168 (1.6); 7.7124 (1.3); 7.6975 (0.9); 7.6931 (0.9); 7.5037 (3.1); 7.4822 (3.1); 7.2866 (1.1); 7.2765 (2.6); 7.2673 (1.2); 7.2605 (19.9); 7.2571 (2.8); 7.2314 (1.5); 7.2255 (2.4); 7.2072 (3.6); 7.2053 (8.6); 7.2016 (1.7); 6.8495 (0.6); 6.8456 (2.1); 6.8434 (1.6); 6.8255 (1.5); 6.8233 (1.8); 6.7760 (3.0); 6.7600 (3.0); 6.2617 (5.0); 5.2992 (16.0); 5.2877 (8.1); 4.7507 (10.0); 3.4939 (6.7); 3.4910 (6.6); 0.0079 (0.8); 0.0002 (26.9); 0.0085 (0.7)
[0491] I.28-331: .sup.1H-NMR (400.6 MHz, CDCl3):
[0492] =8.3728 (0.9); 8.3680 (0.9); 8.3608 (0.9); 8.3560 (0.8); 7.6663 (0.9); 7.6615 (0.9); 7.6474 (1.0); 7.6426 (0.9); 7.5070 (2.1); 7.4856 (2.1); 7.2607 (10.8); 7.2489 (1.3); 7.2432 (1.8); 7.2384 (1.1); 7.2271 (1.6); 7.2216 (1.9); 7.2110 (3.0); 7.2053 (1.7); 6.8330 (2.2); 6.8114 (2.0); 6.7375 (2.0); 6.7216 (2.0); 6.2751 (3.6); 5.2994 (16.0); 5.2623 (5.5); 4.7243 (7.1); 3.5053 (5.0); 3.5027 (5.1); 0.0079 (0.6); 0.0002 (15.5)
[0493] I.28-278: .sup.1H-NMR (400.6 MHz, CDCl3):
[0494] =8.6615 (1.8); 7.4808 (4.5); 7.4594 (4.5); 7.3411 (3.2); 7.3284 (3.0); 7.2607 (34.2); 7.2442 (2.0); 7.2383 (3.7); 7.2257 (6.1); 7.2200 (3.9); 6.8507 (4.9); 6.8292 (4.4); 6.7067 (4.3); 6.6908 (4.4); 6.2779 (8.1); 5.2996 (14.3); 5.2322 (11.2); 4.7403 (0.6); 4.7290 (16.0); 3.5080 (12.2); 1.2548 (0.9); 0.0079 (1.3); 0.0002 (47.4); 0.0084 (1.7)
[0495] I.33-176: .sup.1H-NMR (400.6 MHz, CDCl3):
[0496] =7.5787 (0.8); 7.5739 (3.4); 7.5673 (2.6); 7.5625 (2.7); 7.5562 (2.0); 7.5534 (2.2); 7.2610 (10.4); 6.9575 (1.8); 6.9350 (1.7); 6.7064 (1.8); 6.6923 (1.8); 6.3030 (3.4); 5.3000 (16.0); 4.8011 (0.5); 4.7816 (6.8); 4.7641 (9.1); 3.5165 (4.7); 3.5139 (4.9); 0.0080 (0.5); 0.0002 (15.0)
[0497] I.33-276: .sup.1H-NMR (400.6 MHz, CDCl3):
[0498] =8.5751 (1.7); 8.5713 (2.2); 8.5685 (1.7); 8.5633 (1.7); 8.5593 (2.1); 8.5567 (1.7); 7.7441 (1.4); 7.7397 (1.4); 7.7249 (3.1); 7.7205 (3.0); 7.7056 (1.9); 7.7012 (1.8); 7.5346 (5.7); 7.5296 (7.4); 7.5229 (0.8); 7.5199 (0.6); 7.5063 (3.8); 7.5012 (2.7); 7.4899 (5.3); 7.4849 (4.0); 7.4798 (3.3); 7.4691 (5.1); 7.2901 (2.0); 7.2777 (4.2); 7.2753 (4.3); 7.2616 (26.1); 6.9698 (5.2); 6.9484 (4.9); 6.8246 (4.9); 6.8103 (5.0); 6.7850 (0.5); 6.2396 (9.4); 6.2222 (0.9); 5.3041 (0.6); 5.2480 (11.8); 4.8297 (0.7); 4.8111 (15.6); 4.7169 (1.0); 3.5329 (0.5); 3.4815 (12.4); 3.4789 (12.8); 2.0068 (16.0); 0.0080 (1.0); 0.0002 (36.2); 0.0085 (1.1)
[0499] I.23-89: .sup.1H-NMR (400.6 MHz, CDCl3):
[0500] =7.4027 (3.1); 7.3807 (3.1); 7.2613 (12.8); 6.9584 (1.2); 6.9455 (1.4); 6.9359 (1.8); 6.9231 (1.8); 6.8450 (3.0); 6.8346 (1.2); 6.8286 (3.4); 6.8154 (1.2); 6.8122 (0.8); 6.8079 (1.4); 6.8048 (1.1); 6.7930 (0.8); 6.7855 (1.0); 6.7682 (1.8); 6.7609 (1.4); 6.7463 (1.9); 6.7390 (1.4); 6.3106 (5.2); 5.2995 (16.0); 4.7838 (3.5); 4.7679 (4.0); 4.7642 (3.9); 4.7483 (3.8); 4.6525 (11.8); 4.6313 (0.7); 4.4265 (1.7); 4.4211 (1.6); 4.4112 (2.9); 4.4059 (2.7); 4.3957 (1.8); 4.3892 (5.8); 4.3722 (5.4); 3.5230 (7.0); 3.5201 (7.0); 3.2919 (0.6); 3.2891 (0.6); 3.2872 (0.6); 3.2723 (1.0); 3.2575 (0.6); 3.2555 (0.6); 3.2528 (0.5); 1.5639 (2.5); 1.2592 (0.5); 0.0079 (0.5); 0.0002 (19.5); 0.0085 (0.5)
[0501] I.23-356: .sup.1H-NMR (400.6 MHz, CDCl3):
[0502] =7.3589 (2.6); 7.3368 (2.6); 7.3039 (3.5); 7.2620 (9.5); 6.9067 (1.0); 6.8939 (1.1); 6.8843 (1.5); 6.8714 (1.5); 6.8260 (2.5); 6.8096 (2.6); 6.7994 (0.9); 6.7920 (1.1); 6.7802 (0.9); 6.7770 (0.6); 6.7727 (1.1); 6.7697 (1.0); 6.7578 (0.6); 6.7503 (0.8); 6.7424 (1.5); 6.7351 (1.1); 6.7205 (1.6); 6.7131 (1.1); 6.3052 (4.3); 5.2990 (16.0); 5.0302 (0.7); 5.0223 (7.7); 4.5958 (9.9); 4.5769 (0.7); 3.8026 (0.5); 3.7952 (15.3); 3.5214 (5.8); 3.5185 (5.9); 2.2193 (14.8); 2.2150 (1.4); 0.0002 (14.0)
[0503] I.8-331: .sup.1H-NMR (400.6 MHz, CDCl3):
[0504] =8.3728 (0.6); 7.6768 (1.2); 7.6721 (1.1); 7.6578 (1.3); 7.6557 (1.0); 7.6531 (1.2); 7.4953 (3.2); 7.4738 (3.2); 7.2611 (13.8); 7.2525 (1.0); 7.2455 (0.9); 7.2335 (0.8); 7.1500 (0.7); 7.1454 (0.8); 7.1316 (1.1); 7.1297 (1.1); 7.1271 (1.4); 7.1253 (1.1); 7.1116 (1.1); 7.1071 (1.4); 7.0969 (1.2); 7.0924 (1.3); 7.0768 (2.6); 7.0723 (1.9); 7.0420 (1.4); 7.0383 (1.6); 7.0237 (1.3); 7.0217 (1.2); 7.0201 (1.3); 7.0183 (1.0); 7.0037 (0.6); 7.0000 (0.6); 6.9528 (1.8); 6.9492 (1.7); 6.9326 (1.5); 6.9290 (1.3); 6.6888 (3.1); 6.6727 (3.1); 6.2592 (5.2); 5.2993 (16.0); 5.2691 (7.9); 4.7544 (10.8); 3.4888 (7.2); 3.4860 (7.0); 0.0078 (0.6); 0.0002 (20.9); 0.0021 (1.1); 0.0029 (0.7); 0.0085 (0.6)
[0505] I.23-41: .sup.1H-NMR (400.6 MHz, CDCl3):
[0506] =7.3988 (4.1); 7.3767 (4.0); 7.2606 (12.5); 6.9624 (1.6); 6.9496 (1.7); 6.9399 (2.3); 6.9271 (2.3); 6.8355 (1.4); 6.8297 (4.2); 6.8163 (1.8); 6.8134 (4.8); 6.8089 (1.9); 6.8058 (1.5); 6.7939 (1.0); 6.7864 (1.3); 6.7780 (2.4); 6.7707 (1.7); 6.7561 (2.4); 6.7488 (1.7); 6.3014 (6.6); 5.2989 (13.5); 4.6813 (16.0); 4.6568 (1.0); 4.3906 (2.1); 4.3794 (2.8); 4.3677 (2.6); 4.1536 (4.8); 4.1483 (1.6); 4.1453 (2.2); 4.1418 (4.2); 4.1393 (2.4); 4.1362 (1.4); 4.1304 (4.0); 3.5423 (0.6); 3.5393 (0.6); 3.5184 (9.0); 3.5154 (9.2); 1.5519 (2.6); 0.0079 (0.5); 0.0002 (18.7); 0.0027 (0.8); 0.0085 (0.5)
[0507] I.23-71: .sup.1H-NMR (400.6 MHz, CDCl3):
[0508] =7.3889 (3.1); 7.3668 (3.2); 7.2618 (10.7); 6.9580 (1.2); 6.9451 (1.2); 6.9354 (1.7); 6.9226 (1.6); 6.8708 (2.3); 6.8544 (2.3); 6.8273 (1.1); 6.8198 (1.3); 6.8079 (1.2); 6.8048 (0.9); 6.8004 (1.3); 6.7973 (1.2); 6.7855 (0.7); 6.7780 (1.1); 6.7648 (1.9); 6.7574 (1.4); 6.7428 (1.9); 6.7354 (1.4); 6.3028 (3.1); 6.3008 (3.1); 5.2994 (16.0); 4.6765 (11.1); 4.6550 (0.6); 4.2193 (0.9); 4.2172 (1.0); 4.2002 (1.2); 4.1981 (1.2); 4.1836 (0.6); 4.1024 (0.7); 4.0981 (1.5); 4.0962 (1.8); 4.0907 (1.2); 4.0860 (1.7); 4.0841 (1.4); 4.0782 (1.0); 4.0716 (1.9); 3.8467 (0.6); 3.8425 (0.7); 3.8405 (0.7); 3.8364 (0.6); 3.8257 (1.1); 3.8195 (1.1); 3.8095 (0.6); 3.8032 (0.5); 3.7743 (0.9); 3.7692 (1.1); 3.7576 (0.6); 3.7525 (0.9); 3.7484 (0.5); 3.5175 (6.6); 3.5152 (6.8); 1.9663 (0.6); 1.9183 (0.6); 1.9145 (0.6); 1.9019 (1.4); 1.8982 (1.6); 1.8821 (1.8); 1.8789 (1.5); 1.8655 (1.1); 1.8620 (1.1); 1.5824 (0.6); 1.5731 (1.1); 1.5620 (0.6); 1.5510 (0.6); 0.0002 (15.1)
[0509] I.7-288: .sup.1H-NMR (400.6 MHz, CDCl3):
[0510] =8.5218 (0.7); 7.6636 (1.4); 7.6577 (1.4); 7.6428 (1.6); 7.6368 (1.5); 7.3329 (3.7); 7.3108 (3.7); 7.2608 (18.0); 7.2138 (0.8); 7.1931 (0.7); 7.1407 (0.8); 7.1361 (1.0); 7.1224 (1.3); 7.1204 (1.2); 7.1178 (1.5); 7.1159 (1.4); 7.1023 (1.4); 7.0977 (1.8); 7.0864 (1.4); 7.0820 (1.6); 7.0664 (3.2); 7.0619 (2.3); 7.0301 (1.8); 7.0264 (2.0); 7.0118 (1.5); 7.0100 (1.2); 7.0082 (1.6); 7.0063 (1.2); 6.9918 (0.8); 6.9881 (0.8); 6.9536 (2.1); 6.9500 (1.9); 6.9334 (1.8); 6.9298 (1.5); 6.7376 (3.5); 6.7212 (3.6); 6.2551 (5.9); 5.2992 (16.0); 5.2524 (7.7); 4.7596 (12.0); 3.4865 (7.8); 3.4836 (8.0); 0.0080 (0.8); 0.0002 (27.0); 0.0085 (0.7)
[0511] I.23-278: .sup.1H-NMR (400.6 MHz, CDCl3):
[0512] =8.5963 (4.5); 8.5923 (2.8); 8.5852 (2.8); 8.5812 (4.7); 7.3460 (3.7); 7.3239 (3.7); 7.2620 (12.4); 7.1945 (4.1); 7.1905 (2.5); 7.1834 (2.6); 7.1794 (4.1); 6.9662 (1.5); 6.9533 (1.6); 6.9438 (2.0); 6.9309 (2.1); 6.8334 (1.1); 6.8259 (1.5); 6.8142 (1.4); 6.8106 (4.2); 6.8068 (1.9); 6.8037 (1.7); 6.7942 (3.8); 6.7843 (1.4); 6.7815 (2.3); 6.7742 (1.6); 6.7596 (2.3); 6.7523 (1.6); 6.2867 (6.3); 5.2989 (16.0); 5.1832 (9.3); 4.7238 (14.3); 4.7002 (1.0); 3.5368 (0.6); 3.5340 (0.6); 3.5108 (8.5); 3.5079 (8.9); 2.0445 (0.8); 1.2589 (1.5); 1.2569 (1.3); 0.0002 (17.4); 0.0085 (0.6)
[0513] I.23-277: .sup.1H-NMR (400.6 MHz, CDCl3):
[0514] =8.5926 (3.1); 8.5887 (2.9); 8.5809 (1.7); 8.5767 (1.5); 7.6570 (0.8); 7.6525 (1.1); 7.6515 (1.1); 7.6470 (0.8); 7.6374 (0.9); 7.6330 (1.2); 7.6318 (1.3); 7.6274 (0.9); 7.3553 (3.2); 7.3331 (3.3); 7.3039 (1.1); 7.3020 (1.1); 7.2918 (1.1); 7.2898 (1.2); 7.2844 (1.1); 7.2823 (1.1); 7.2722 (1.0); 7.2702 (1.1); 7.2619 (13.4); 6.9332 (1.3); 6.9204 (1.4); 6.9109 (1.8); 6.8980 (1.9); 6.8142 (3.2); 6.8089 (1.3); 6.8014 (1.7); 6.7979 (3.4); 6.7897 (1.2); 6.7866 (0.8); 6.7823 (1.8); 6.7791 (1.3); 6.7673 (0.7); 6.7597 (3.0); 6.7522 (1.3); 6.7375 (2.0); 6.7303 (1.3); 6.3005 (5.5); 5.2990 (16.0); 5.1926 (8.8); 4.6698 (13.2); 4.6475 (0.9); 3.5357 (0.5); 3.5143 (7.4); 3.5113 (7.6); 2.0444 (0.5); 1.2589 (0.9); 1.2566 (0.8); 0.0079 (0.5); 0.0002 (19.1); 0.0085 (0.6)
[0515] I.7-331: .sup.1H-NMR (400.6 MHz, CDCl3):
[0516] =7.6719 (1.0); 7.6530 (1.1); 7.3331 (2.6); 7.3110 (2.6); 7.2612 (10.3); 7.1461 (0.6); 7.1414 (0.7); 7.1278 (0.9); 7.1259 (0.9); 7.1232 (1.1); 7.1213 (1.0); 7.1078 (0.9); 7.1031 (1.2); 7.0900 (1.0); 7.0855 (1.1); 7.0700 (2.3); 7.0655 (1.7); 7.0387 (1.2); 7.0351 (1.4); 7.0205 (1.0); 7.0186 (0.9); 7.0170 (1.1); 7.0151 (0.8); 7.0005 (0.5); 6.9970 (0.5); 6.9485 (1.4); 6.9449 (1.4); 6.9283 (1.2); 6.9247 (1.1); 6.7264 (2.5); 6.7100 (2.6); 6.2623 (4.3); 5.2991 (16.0); 5.2717 (5.1); 4.7541 (9.0); 3.4911 (5.8); 3.4883 (6.0); 0.0002 (14.4)
[0517] I.23-72: .sup.1H-NMR (400.6 MHz, CDCl3):
[0518] =7.3975 (3.6); 7.3755 (3.6); 7.2615 (13.1); 6.9469 (1.0); 6.9348 (1.0); 6.9245 (1.5); 6.9117 (1.5); 6.8496 (3.4); 6.8333 (3.6); 6.8281 (1.6); 6.8164 (1.4); 6.8132 (1.0); 6.8089 (1.6); 6.8057 (1.3); 6.7940 (0.9); 6.7865 (1.1); 6.7722 (1.4); 6.7711 (10.3); 6.7638 (1.0); 6.7504 (1.4); 6.7491 (10.4); 6.7430 (10.0); 6.7419 (1.0); 6.3151 (3.1); 6.3040 (3.1); 5.2994 (16.0); 4.6400 (13.7); 4.6172 (0.9); 4.1871 (0.6); 4.1714 (0.9); 4.1602 (1.0); 4.1565 (0.7); 4.1448 (1.4); 4.1296 (1.0); 4.0670 (1.1); 4.0546 (1.0); 4.0469 (1.2); 4.0401 (0.7); 4.0345 (1.1); 4.0277 (0.7); 4.0199 (0.7); 4.0075 (0.7); 3.8603 (0.7); 3.8467 (0.7); 3.8393 (1.4); 3.8256 (1.4); 3.8190 (1.1); 3.8053 (1.0); 3.7900 (0.9); 3.7687 (1.3); 3.7514 (1.9); 3.7332 (1.6); 3.7149 (1.3); 3.6938 (0.8); 3.5446 (1.4); 3.5324 (1.4); 3.5205 (9.2); 3.5176 (8.6); 3.4980 (0.8); 2.5736 (0.5); 2.5565 (0.7); 2.5392 (0.5); 2.0447 (0.6); 2.0311 (0.5); 2.0187 (0.7); 1.9990 (0.7); 1.9861 (0.6); 1.6001 (0.6); 1.5864 (0.9); 1.5668 (2.4); 1.5540 (0.6); 1.2591 (0.7); 0.0080 (0.5); 0.0002 (19.0)
[0519] I.23-321: .sup.1H-NMR (400.6 MHz, CDCl3):
[0520] =9.1982 (3.5); 8.7287 (8.0); 7.3716 (2.9); 7.3495 (2.9); 7.2627 (9.8); 6.9473 (1.1); 6.9345 (1.2); 6.9250 (1.6); 6.9121 (1.6); 6.8231 (0.9); 6.8156 (1.1); 6.8039 (1.0); 6.7973 (3.5); 6.7934 (1.2); 6.7813 (3.4); 6.7741 (2.6); 6.7668 (1.2); 6.7523 (1.7); 6.7449 (1.1); 6.3069 (4.8); 5.2998 (16.0); 5.2972 (0.5); 5.1888 (8.2); 4.6717 (11.2); 4.6483 (0.8); 3.5181 (6.4); 3.5153 (6.6); 1.2568 (0.8); 0.0002 (14.5); 0.0029 (0.6)
[0521] The present invention further provides for the use of one or more inventive compounds of the general 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.33) and/or salts thereof, in each case as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamentals.
[0522] The present invention further provides a method of controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount [0523] of one or more inventive compounds of the general 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.33) and/or salts thereof, in each case as defined above, or [0524] of a composition of the invention, as defined below,
[0525] 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.
[0526] The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount [0527] of one or more compounds of the general 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.33) and/or salts thereof, in each case as defined above, or [0528] of a composition of the invention, as defined below,
[0529] 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-growing land or non-crop-growing land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).
[0530] The present invention also further provides methods for controlling for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount [0531] of one or more compounds of the general 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.33) and/or salts thereof, in each case as defined above, or [0532] of a composition of the invention, as defined below,
[0533] 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).
[0534] In this context, the inventive compounds of the general formula (I) or the compositions of the invention can be deployed, for example, by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and/or post-emergence methods. 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.
[0535] In a method of the invention for controlling harmful plants or for regulating the growth of plants, preference is given to using one or more compounds of the general formula (I) and/or salts thereof for control of harmful plants or for regulation of growth in crops of useful plants or ornamental plants, where the useful plants or ornamental plants in a preferred configuration are transgenic plants.
[0536] The inventive compounds of the general formula (I) and/or salts thereof are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:
[0537] Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
[0538] Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
[0539] When the inventive compounds of the general formula (I) 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.
[0540] When the inventive compounds of the general formula (I) 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.
[0541] Although the inventive compounds of the general formula (I) display 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.
[0542] In addition, the inventive compounds of the general formula (I) (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.
[0543] By virtue of their herbicidal and plant growth regulatory properties, the inventive compounds of the general formula (I) 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.
[0544] It is preferred with a view to transgenic crops to use the inventive compounds of the general formula (I) and/or salts thereof 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.
[0545] It is preferable to employ the inventive compounds of the general formula (I) also 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.
[0546] By virtue of their herbicidal and plant growth regulatory properties, the inventive compounds of the general formula (I) 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.
[0547] Preference is given to the use of the inventive compounds of the general formula (I) or salts thereof in economically important transgenic crops of useful plants and ornamentals, 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.
[0548] It is preferable to employ the compounds of the general formula (I) 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.
[0549] 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.
[0550] 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 genetic 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 part sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.
[0551] 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.
[0552] 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.
[0553] 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. Sequences of this kind are known to the person 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.
[0554] 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.
[0555] Obtainable in this way are transgenic plants having properties altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.
[0556] It is preferable to employ the inventive compounds of the general formula (I) 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, glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
[0557] When the inventive compounds of the general formula (I) 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.
[0558] The invention therefore also relates to the use of the inventive compounds of the general formula (I) and/or salts thereof as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.
[0559] 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.
[0560] Preference is also given to the use in soybeans by the pre- or post-emergence method.
[0561] The use according to the invention for the control of harmful plants or for growth regulation of plants also includes the case in which a compound of the general formula (I) or its salt is not formed from a precursor substance (prodrug) until after application on the plant, in the plant or in the soil.
[0562] The invention also provides for the use of one or more compounds of the general formula (I) or salts thereof or of a composition of the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the general formula (I) 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.
[0563] The invention also provides a herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises [0564] (a) one or more compounds of the general 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.33) and/or salts thereof, in each case as defined above, [0565] and [0566] (b) one or more further substances selected from groups (i) and/or (ii): [0567] (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not conforming to the general formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, [0568] (ii) one or more formulation auxiliaries customary in crop protection.
[0569] The further agrochemically active substances of component (i) of a composition of 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.
[0570] A herbicidal or plant growth-regulating composition of 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 that are solid at 25 C. and 1013 mbar, preferably adsorptive 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.
[0571] The inventive compounds of the general formula (I) can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and/or salts thereof.
[0572] The inventive compounds of the general formula (I) and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are specified. 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.
[0573] These individual formulation types and the formulation auxiliaries, 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, Schnfeldt, Grenzflchenaktive thylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kchler, Chemische Technologie, Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
[0574] Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active ingredient, 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 active herbicidal ingredients 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.
[0575] Emulsifiable concentrates are produced by dissolving the active ingredient 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 alkylarylsulfonate salts, for example 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.
[0576] Dusting products are obtained by grinding the active ingredient with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
[0577] Suspension concentrates may be water- or oil-based. They can be produced, for example, by wet grinding by means of standard commercial bead mills and optionally the addition of surfactants, as have already been listed e.g. above for the other types of formulation.
[0578] Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants, as have already been listed e.g. above for the other formulation types.
[0579] Granules can be produced either by spraying the active ingredient onto granular inert material capable of adsorption or by applying active ingredient concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granulesif desired as a mixture with fertilizers.
[0580] 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.
[0581] For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, 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, pp. 8-57.
[0582] 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.
[0583] The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active ingredients of the general formula (I) and salts thereof.
[0584] In wettable powders, the active ingredient 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 ingredient 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 ingredient, preferably usually 5% to 20% by weight of active ingredient; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends partly on whether the active ingredient is in liquid or solid form and on which granulation auxiliaries, fillers, and so forth are used. In the water-dispersible granules, the content of active ingredient is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.
[0585] In addition, the active ingredient 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).
[0586] The inventive compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of a tankmix. The combination formulations can be produced on the basis of the abovementioned formulations, taking account of the physical properties and stabilities of the active ingredients to be combined.
[0587] Combination partners usable for the inventive compounds of the general formula (I) in mixed formulations or in a tankmix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, 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 the literature cited therein.
[0588] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the inventive compounds of the general formula (I) 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 inventive compounds of the general formula (I) that are of particular interest are those comprising the compounds (I) or combinations thereof 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.
[0589] 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 of the general formula (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.
[0590] For application, the herbicide formulations or herbicide-safener formulations in the commercial form are diluted if appropriate in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in dust form, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.
[0591] The application rate of the inventive compounds of the general formula (I) and/or salts thereof is affected to a certain extent by external conditions such as temperature, humidity, etc. The application rate may vary within wide limits. For application as a herbicide for controlling harmful plants, the total amount of inventive compounds of the general formula (I) and salts thereof 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 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies both to pre-emergence and to post-emergence application.
[0592] When the inventive compounds of the general formula (I) and/or salts thereof 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 preferably in the range from 20 to 250 g/ha. This applies both to pre-emergence and to post-emergence application.
[0593] 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.
[0594] As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. The application rate depends on the particular techniques and can be determined in preliminary tests.
[0595] Combination partners usable for the inventive compounds of the general formula (I) in compositions of the invention (e.g. mixed formulations or in a tankmix) are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as described, for example, from Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, and literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds of the invention are, for example, the following, where said active ingredients are referred to either by their common name in accordance with the International Organization for Standardization (ISO) or by the chemical name or by the code number. They always encompass all the use forms, for example acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if they are not mentioned explicitly.
[0596] Examples of such herbicidal mixing partners are: [0597] acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, 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 the following compounds:
##STR00102##
[0598] Examples of plant growth regulators as possible mixing partners are: [0599] acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
[0600] Useful combination partners for the inventive compounds of the general formula (I) also include, for example, the following safeners: [0601] S1) Compounds from the group of heterocyclic carboxylic acid derivatives: [0602] 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; [0603] 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 and EP-A-269806; [0604] 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; [0605] 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; [0606] 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. [0607] S2) Compounds from the group of the 8-quinolinoxy derivatives (S2): [0608] 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), [0609] methyl (5-chloro-8-quinolinoxy)acetate (S2-6), [0610] 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; [0611] 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. [0612] S3) Active ingredients of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), for example [0613] dichlormid (N,N-diallyl-2,2-dichloroacetamide) (S3-1), [0614] R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), [0615] R-28725 (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), [0616] benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), [0617] PPG-1292 (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5), [0618] DKA-24 (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S3-6), [0619] AD-67 or MON 4660 (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7), [0620] TI-35 (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8), [0621] diclonon (dicyclonon) or BAS145138 or LAB145138 (S3-9) [0622] ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, [0623] furilazole or MON 13900 ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and the (R) isomer thereof (S3-11). [0624] S4) Compounds from the class of the acylsulfonamides (S4): [0625] S4.sup.a) N-Acylsulfonamides of the formula (S4.sup.a) and salts thereof, as described in WO-A-97/45016,
##STR00103## [0626] in which [0627] 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; [0628] R.sub.A.sup.2 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0629] m.sub.A is 1 or 2; [0630] v.sub.A is 0, 1, 2 or 3; [0631] 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,
##STR00104## [0632] in which [0633] 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, [0634] 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 [0635] m.sub.B is 1 or 2, [0636] e.g. those in which [0637] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (cyprosulfamide, S4-1), [0638] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-2), [0639] R.sub.B.sup.1=ethyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-3), [0640] 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 [0641] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-5); [0642] S4.sup.c) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4.sup.c), as described in EP-A-365484,
##STR00105## [0643] in which [0644] 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, [0645] 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 [0646] m.sub.C is 1 or 2; [0647] for example [0648] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, [0649] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, [0650] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; [0651] 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,
##STR00106## [0652] in which [0653] R.sub.D.sup.4 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0654] m.sub.D is 1 or 2; [0655] R.sub.D.sup.5 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.5-C.sub.6)-cycloalkenyl. [0656] S5) Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example [0657] ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001. [0658] S6) Active ingredients from the class of the 1,2-dihydroquinoxalin-2-ones (S6), for example [0659] 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. [0660] 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. [0661] S8) Compounds of the formula (S8), as described in WO-A-98/27049,
##STR00107## [0662] in which the symbols and indices are defined as follows: [0663] 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, [0664] R.sub.D.sup.2 is hydrogen or (C.sub.1-C.sub.4)-alkyl, [0665] 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, [0666] n.sub.D is an integer from 0 to 2. [0667] S9) Active ingredients from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example [0668] 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-1999/000020. [0669] S10) Compounds of the formulae (S10.sup.a) or (S10.sup.b) [0670] as described in WO-A-2007/023719 and WO-A-2007/023764, [0671] in which
##STR00108## [0672] R.sub.E.sup.1 is halogen, (C.sub.1-C.sub.4)-alkyl, methoxy, nitro, cyano, CF.sub.3, OCF.sub.3, [0673] Y.sub.E, Z.sub.E are independently O or S, [0674] n.sub.E is an integer from 0 to 4, [0675] 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, [0676] R.sub.E.sup.3 is hydrogen or (C.sub.1-C.sub.6)-alkyl. [0677] S11) Active ingredients of the oxyimino compounds type (S11), which are known as seed-dressing agents, for example [0678] 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, [0679] 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 [0680] cyometrinil or CGA-43089 ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage. [0681] S12) Active ingredients 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. [0682] S13) One or more compounds from group (S13): [0683] naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for corn against thiocarbamate herbicide damage, [0684] fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, [0685] 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, CL 304415 (CAS Reg. No. 31541-57-8) [0686] (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, [0687] 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, [0688] MG 838 (CAS Reg. No. 133993-74-5) [0689] (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia [0690] disulfoton (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), [0691] dietholate (O,O-diethyl O-phenyl phosphorothioate) (S13-8), [0692] mephenate (4-chlorophenyl methylcarbamate) (S13-9). [0693] S14) Active ingredients which, in addition to herbicidal action against harmful plants, also have safener action on crop plants such as rice, for example [0694] 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, [0695] daimuron or SK 23 (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron, [0696] cumyluron=JC-940 (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known as a safener for rice against damage by some herbicides, [0697] methoxyphenone or NK 049 (3,3-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides, [0698] 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. [0699] S15) Compounds of the formula (S15) or tautomers thereof
##STR00109## [0700] as described in WO-A-2008/131861 and WO-A-2008/131860 [0701] in which [0702] R.sub.H.sup.1 is a (C.sub.1-C.sub.6)-haloalkyl radical and [0703] R.sub.H.sup.2 is hydrogen or halogen and [0704] R.sub.H.sup.3, R.sub.H.sup.4 are independently hydrogen, (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.16)-alkenyl or (C.sub.2-C.sub.16)-alkynyl, 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, [0705] 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, [0706] 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, [0707] or [0708] 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 [0709] R.sub.H.sup.4 is hydrogen or (C.sub.1-C.sub.4)-alkyl or [0710] 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. [0711] S16) Active ingredients which are used primarily as herbicides but also have safener action on crop plants, for example [0712] (2,4-dichlorophenoxy)acetic acid (2,4-D), [0713] (4-chlorophenoxy)acetic acid, [0714] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), [0715] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), [0716] (4-chloro-o-tolyloxy)acetic acid (MCPA), [0717] 4-(4-chloro-o-tolyloxy)butyric acid, [0718] 4-(4-chlorophenoxy)butyric acid, [0719] 3,6-dichloro-2-methoxybenzoic acid (dicamba), [0720] 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).
[0721] Preferred safeners in combination with the inventive compounds of the general formula (I) and/or salts thereof, especially with the compounds of the formulae (I.1) to (I.34) and/or salts thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, 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
A. Post-Emergence Herbicidal Action and Crop Plant Compatibility
[0722] 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.
[0723] Tables A1 to A14 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.33 on various harmful plants and at an application rate corresponding to 20 g/ha and less, which were obtained by the experimental method specified above. The appendices a, b and c give differentiation by different dosage with otherwise the same harmful plants tested.
TABLE-US-00002 TABLE A1a Post-emergence action at 1.25 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH I.1-72 1.25 100 I.1-1 1.25 100 I.2-23 1.25 100 I.2-2 1.25 80 I.2-58 1.25 100 I.1-26 1.25 100 I.1-23 1.25 100 I.1-71 1.25 100 I.7-23 1.25 100 I.7-276 1.25 100 I.7-2 1.25 100 I.9-1 1.25 100 I.7-41 1.25 100 I.7-278 1.25 100 I.7-277 1.25 90 I.7-291 1.25 100 I.7-71 1.25 100 I.7-115 1.25 80 I.7-356 1.25 90 I.7-394 1.25 100 I.7-72 1.25 100 I.7-179 1.25 100 I.7-177 1.25 100 I.7-94 1.25 100 I.6-1 1.25 100 I.6-176 1.25 100 I.6-41 1.25 100 I.6-276 1.25 100 I.6-23 1.25 100 I.6-2 1.25 100 I.7-339 1.25 90 I.8-23 1.25 100 I.8-41 1.25 80 I.8-176 1.25 100 I.9-23 1.25 80 I.9-41 1.25 100 I.8-2 1.25 100 I.8-1 1.25 100 I.8-276 1.25 100 I.7-183 1.25 100 I.9-2 1.25 100 I.9-176 1.25 100 I.9-276 1.25 100 I.8-291 1.25 100 I.9-291 1.25 100 I.19-276 1.25 100 I.19-176 1.25 100 I.23-176 1.25 80 I.23-1 1.25 100 I.19-1 1.25 100 I.23-276 1.25 90
TABLE-US-00003 TABLE A1b Post-emergence action at 5 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH I.1-72 5 100 I.1-1 5 100 I.2-72 5 100 I.2-71 5 100 I.2-1 5 100 I.2-23 5 100 I.2-2 5 100 I.2-58 5 100 I.1-26 5 100 I.1-23 5 100 I.1-71 5 100 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-2 5 100 I.9-1 5 100 I.7-41 5 100 I.7-278 5 100 I.7-277 5 100 I.7-291 5 100 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 100 I.7-94 5 100 I.6-1 5 100 I.6-176 5 100 I.6-41 5 100 I.6-276 5 100 I.6-23 5 100 I.6-2 5 100 I.7-339 5 100 I.8-23 5 100 I.8-41 5 100 I.8-176 5 100 I.9-23 5 100 I.9-41 5 100 I.6-183 5 100 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 100 I.19-276 5 100 I.19-176 5 100 I.23-176 5 100 I.23-1 5 100 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100 I.23-276 5 100
TABLE-US-00004 TABLE A1c Post-emergence action at 20 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 100 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 100 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00005 TABLE A2a Post-emergence action at 1.25 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY I.7-23 1.25 80 I.7-276 1.25 90 I.7-41 1.25 100 I.8-2 1.25 80 I.8-291 1.25 80 I.9-291 1.25 80
TABLE-US-00006 TABLE A2b Post-emergence action at 5 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY I.1-26 5 80 I.1-23 5 90 I.1-71 5 80 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-1 5 80 I.7-2 5 80 I.7-41 5 100 I.7-278 5 90 I.7-291 5 80 I.7-71 5 80 I.7-115 5 100 I.7-356 5 100 I.7-394 5 80 I.7-177 5 90 I.7-94 5 80 I.6-1 5 80 I.6-176 5 80 I.6-41 5 80 I.6-276 5 80 I.6-23 5 80 I.7-339 5 100 I.8-23 5 80 I.8-41 5 80 I.8-176 5 80 1.8-2 5 100 I.8-1 5 100 I.8-276 5 80 I.7-183 5 80 I.9-2 5 80 I.9-176 5 100 I.9-276 5 100 I.8-183 5 80 I.8-291 5 90 I.9-291 5 90 I.19-23 5 80
TABLE-US-00007 TABLE A2c Post-emergence action at 20 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY I.1-72 20 80 I.1-1 20 80 I.2-72 20 90 I.2-71 20 80 I.2-1 20 80 I.2-23 20 80 I.2-2 20 80 I.2-58 20 80 I.1-26 20 90 I.1-23 20 90 I.1-71 20 90 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 80 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 80 I.6-1 20 100 I.6-176 20 90 I.6-41 20 100 I.6-276 20 100 I.6-23 20 90 I.6-2 20 90 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 80 I.9-41 20 80 I.6-183 20 90 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 90 I.19-176 20 80 I.23-176 20 100 I.23-1 20 90 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00008 TABLE A3a Post-emergence action at 1.25 g/ha against AMARE in % Example Dosage number [g/ha] AMARE I.1-72 1.25 80 I.1-1 1.25 90 I.2-72 1.25 90 I.2-71 1.25 100 I.2-1 1.25 100 I.2-23 1.25 80 I.2-2 1.25 100 I.2-58 1.25 90 I.1-26 1.25 100 I.1-23 1.25 100 I.1-71 1.25 100 I.7-1 1.25 100 I.7-23 1.25 100 I.7-276 1.25 100 I.7-2 1.25 100 I.9-1 1.25 100 I.7-41 1.25 100 I.7-278 1.25 100 I.7-277 1.25 100 I.7-291 1.25 100 I.7-71 1.25 100 I.7-115 1.25 100 I.7-356 1.25 100 I.7-394 1.25 100 I.7-72 1.25 100 I.7-179 1.25 100 I.7-177 1.25 100 I.7-94 1.25 100 I.6-1 1.25 100 I.6-176 1.25 100 I.6-41 1.25 100 I.6-276 1.25 100 I.6-23 1.25 100 I.6-2 1.25 100 I.7-339 1.25 100 I.8-23 1.25 100 I.8-41 1.25 100 I.8-176 1.25 100 I.9-23 1.25 100 I.9-41 1.25 100 I.6-183 1.25 100 I.8-2 1.25 100 I.8-1 1.25 100 I.8-276 1.25 100 I.7-183 1.25 100 I.9-2 1.25 100 I.9-176 1.25 100 I.9-276 1.25 100 I.8-183 1.25 100 I.8-291 1.25 100 I.9-291 1.25 100 I.19-276 1.25 100 I.19-176 1.25 100 I.23-176 1.25 100 I.19-1 1.25 100 I.19-23 1.25 100 I.23-23 1.25 100 I.23-276 1.25 90
TABLE-US-00009 TABLE A3b Post-emergence action at 5 g/ha against AMARE in % Example Dosage number [g/ha] AMARE I.1-72 5 100 I.1-1 5 100 I.2-72 5 100 I.2-71 5 100 I.2-23 5 100 I.2-2 5 100 I.2-58 5 100 I.1-26 5 100 I.1-23 5 100 I.1-71 5 100 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-2 5 100 I.9-1 5 100 I.7-41 5 100 I.7-278 5 100 I.7-277 5 100 I.7-291 5 100 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 100 I.7-94 5 100 I.6-1 5 100 I.6-176 5 100 I.6-41 5 100 I.6-276 5 100 I.6-23 5 100 I.6-2 5 100 I.7-339 5 100 I.8-23 5 100 I.8-41 5 100 I.8-176 5 100 I.9-23 5 100 I.9-41 5 100 I.6-183 5 100 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 100 I.19-276 5 100 I.19-176 5 100 I.23-176 5 100 I.23-1 5 100 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100 I.23-276 5 100
TABLE-US-00010 TABLE A3c Post-emergence action at 20 g/ha against AMARE in % Example Dosage number [g/ha] AMARE I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 100 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 100 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00011 TABLE A4a Post-emergence action at 5 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA I.7-176 5 80 I.7-41 5 80 I.9-176 5 80 I.9-276 5 80 I.9-291 5 80
TABLE-US-00012 TABLE A4b Post-emergence action at 20 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA I.1-1 20 80 I.1-26 20 80 I.1-23 20 80 I.1-71 20 80 I.7-1 20 80 I.7-276 20 90 I.7-176 20 100 I.7-2 20 90 I.7-41 20 80 I.7-278 20 80 I.7-291 20 100 I.7-71 20 90 I.7-115 20 100 I.7-356 20 80 I.7-72 20 100 I.7-179 20 80 I.7-177 20 80 I.7-94 20 80 I.6-1 20 100 I.6-176 20 80 I.6-41 20 80 I.6-276 20 80 I.6-23 20 90 I.8-23 20 80 I.8-41 20 80 I.8-176 20 80 I.9-41 20 80 I.8-2 20 100 I.8-1 20 80 I.8-276 20 80 I.7-183 20 90 I.9-2 20 90 I.9-176 20 80 I.9-276 20 90 I.8-183 20 100 I.8-291 20 90 I.9-291 20 80
TABLE-US-00013 TABLE A5a Post-emergence action at 1.25 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG I.1-26 1.25 90 I.1-23 1.25 90 I.1-71 1.25 100 I.7-1 1.25 90 I.7-276 1.25 90 I.7-41 1.25 90 I.7-278 1.25 80 I.7-71 1.25 100 I.7-115 1.25 100 I.7-356 1.25 90 I.7-394 1.25 100 I.7-72 1.25 80 I.6-1 1.25 90 I.6-176 1.25 100 I.6-23 1.25 80 I.8-1 1.25 80 I.9-2 1.25 80 I.9-176 1.25 100 I.8-291 1.25 100 I.19-1 1.25 100 I.23-276 1.25 100
TABLE-US-00014 TABLE A5b Post-emergence action at 5 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG I.2-72 5 80 I.2-23 5 100 I.1-26 5 90 I.1-23 5 100 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-2 5 100 I.9-1 5 90 I.7-41 5 100 I.7-278 5 100 I.7-277 5 100 I.7-291 5 100 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 100 I.7-94 5 100 I.6-1 5 90 I.6-176 5 100 I.6-41 5 100 I.6-276 5 90 I.6-23 5 90 I.6-2 5 90 I.7-339 5 100 I.8-23 5 100 I.8-41 5 90 I.8-176 5 100 I.9-41 5 80 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 90 I.19-276 5 100 I.19-176 5 100 I.23-176 5 100 I.23-1 5 100 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100 I.23-276 5 100
TABLE-US-00015 TABLE A5c Post-emergence action at 20 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG I.1-72 20 100 I.1-1 20 80 I.2-72 20 80 I.2-71 20 80 I.2-1 20 100 I.2-23 20 100 I.2-2 20 90 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 90 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 80 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00016 TABLE A6a Post-emergence action at 5 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI I.1-26 5 80 I.7-276 5 80
TABLE-US-00017 TABLE A6b Post-emergence action at 20 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI I.1-23 20 80 I.1-26 20 90 I.6-1 20 80 I.6-176 20 90 I.6-2 20 90 I.6-23 20 90 I.6-276 20 90 I.7-1 20 80 I.7-176 20 80 I.7-177 20 80 I.7-179 20 100 I.7-183 20 80 I.7-2 20 80 I.7-276 20 100 I.7-278 20 80 I.7-41 20 80 I.7-71 20 80 I.7-72 20 80 I.8-1 20 80 I.8-2 20 90 I.8-276 20 100 I.8-291 20 80 I.9-291 20 90
TABLE-US-00018 TABLE A7a Post-emergence action at 1.25 g/ha against MATIN in % Example Dosage number [g/ha] MATIN I.1-26 1.25 80 I.1-23 1.25 80 I.1-71 1.25 80 I.7-1 1.25 100 I.7-23 1.25 90 I.7-276 1.25 100 I.7-2 1.25 80 I.7-41 1.25 90 I.7-71 1.25 80 I.7-115 1.25 100 I.7-356 1.25 80 I.7-179 1.25 80 I.7-177 1.25 80 I.7-94 1.25 80 I.6-23 1.25 80 I.8-41 1.25 90 I.9-41 1.25 100 I.8-2 1.25 100 I.8-1 1.25 100 I.8-276 1.25 80 I.7-183 1.25 80
TABLE-US-00019 TABLE A7b Post-emergence action at 5 g/ha against MATIN in % Example Dosage number [g/ha] MATIN I.1-72 5 90 I.1-1 5 100 I.2-71 5 80 I.2-1 5 80 I.2-23 5 80 I.2-2 5 80 I.2-58 5 80 I.1-26 5 80 I.1-23 5 100 I.1-71 5 90 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 90 I.7-2 5 80 I.9-1 5 80 I.7-41 5 90 I.7-278 5 80 I.7-277 5 80 I.7-291 5 100 1.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 80 I.7-72 5 100 I.7-179 5 100 I.7-177 5 80 I.7-94 5 80 I.6-1 5 100 I.6-176 5 80 I.6-41 5 80 I.6-276 5 100 I.6-23 5 100 I.6-2 5 90 I.7-339 5 100 I.8-23 5 100 I.8-41 5 90 I.8-176 5 100 I.9-23 5 80 I.9-41 5 100 I.6-183 5 80 I.8-2 5 100 I.8-1 5 100 I.8-276 5 80 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 80 I.9-291 5 80 I.19-276 5 100 I.19-176 5 100 I.23-1 5 80 I.19-1 5 90 I.19-23 5 100
TABLE-US-00020 TABLE A7c Post-emergence action at 20 g/ha against MATIN in % Example Dosage number [g/ha] MATIN I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 90 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 90 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 90 I.7-72 20 100 I.7-179 20 100 I.7-177 20 80 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 80 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 90
TABLE-US-00021 TABLE A8a Post-emergence action at 1.25 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU I.1-72 1.25 80 I.1-1 1.25 100 I.2-72 1.25 100 I.2-71 1.25 80 I.2-1 1.25 100 I.2-23 1.25 100 I.2-2 1.25 100 I.1-26 1.25 100 I.1-23 1.25 100 I.1-71 1.25 100 I.7-1 1.25 100 I.7-276 1.25 100 I.7-2 1.25 100 I.7-41 1.25 100 I.7-278 1.25 100 I.7-291 1.25 100 I.7-71 1.25 100 I.7-115 1.25 100 I.7-394 1.25 100 I.7-72 1.25 100 I.7-179 1.25 100 I.7-177 1.25 90 I.7-94 1.25 100 I.6-176 1.25 80 I.6-41 1.25 100 I.6-276 1.25 100 I.6-23 1.25 80 I.6-2 1.25 100 I.7-339 1.25 100 I.8-23 1.25 100 I.8-41 1.25 100 I.8-176 1.25 80 I.9-23 1.25 80 I.9-41 1.25 100 I.6-183 1.25 100 I.8-2 1.25 100 I.8-1 1.25 100 I.8-276 1.25 100 I.7-183 1.25 80 I.9-2 1.25 100 I.9-276 1.25 100 I.8-291 1.25 100 I.9-291 1.25 100 I.19-176 1.25 100 I.23-176 1.25 90 I.19-1 1.25 100 I.19-23 1.25 100 I.23-23 1.25 100 I.23-276 1.25 90
TABLE-US-00022 TABLE A8b Post-emergence action at 5 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU I.1-72 5 100 I.1-1 5 100 I.2-72 5 100 I.2-71 5 100 I.2-1 5 100 I.2-23 5 100 I.2-2 5 100 I.2-58 5 80 I.1-26 5 100 I.1-23 5 100 I.1-71 5 100 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-2 5 100 I.9-1 5 100 I.7-41 5 100 I.7-278 5 100 I.7-277 5 100 I.7-291 5 100 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 100 I.7-94 5 100 I.6-1 5 100 I.6-176 5 100 I.6-41 5 100 I.6-276 5 100 I.6-23 5 90 I.6-2 5 100 I.7-339 5 100 I.8-23 5 100 I.8-41 5 100 I.8-176 5 80 I.9-23 5 100 I.9-41 5 100 I.6-183 5 100 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 100 I.19-276 5 100 I.19-176 5 100 I.23-176 5 90 I.23-1 5 80 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100 I.23-276 5 100
TABLE-US-00023 TABLE A8c Post-emergence action at 20 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 100 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 100 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 80 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00024 TABLE 9a Post-emergence action at 1.25 g/ha against POLCO in % Example Dosage number [g/ha] POLCO I.1-72 1.25 80 I.2-58 1.25 100 I.1-26 1.25 100 I.1-23 1.25 100 I.1-71 1.25 100 I.7-72 1.25 80 I.6-23 1.25 90 I.8-41 1.25 80 I.8-1 1.25 90 I.9-291 1.25 80 I.19-176 1.25 100 I.23-1 1.25 90 I.19-23 1.25 100 I.23-23 1.25 100
TABLE-US-00025 TABLE A9b Post-emergence action at 5 g/ha against POLCO in % Example Dosage number [g/ha] POLCO I.1-72 5 100 I.1-1 5 100 I.2-72 5 80 I.2-71 5 100 I.2-1 5 80 I.2-23 5 100 I.2-2 5 100 I.2-58 5 100 I.1-26 5 100 I.1-23 5 100 I.1-71 5 100 I.7-1 5 80 I.7-23 5 100 I.7-176 5 100 I.7-41 5 100 I.7-278 5 80 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 80 I.6-1 5 100 I.6-23 5 100 I.6-2 5 100 I.7-339 5 100 I.8-23 5 100 I.8-41 5 90 I.8-176 5 80 I.9-23 5 100 I.9-41 5 90 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.9-2 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 90 I.19-276 5 100 I.19-176 5 100 I.23-176 5 100 I.23-1 5 100 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100
TABLE-US-00026 TABLE A9c Post-emergence action at 20 g/ha against POLCO in % Example Dosage number [g/ha] POLCO I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 100 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 100 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00027 TABLE A10a Post-emergence action at 1.25 g/ha against SETVI in % Example Dosage number [g/ha] SETVI I.1-72 1.25 100 I.1-1 1.25 100 I.2-72 1.25 90 I.2-71 1.25 90 I.2-1 1.25 100 I.2-2 1.25 100 I.2-58 1.25 100 I.1-26 1.25 100 I.1-23 1.25 100 I.1-71 1.25 100 I.7-1 1.25 100 I.7-23 1.25 100 I.7-276 1.25 100 I.7-2 1.25 100 I.9-1 1.25 80 I.7-41 1.25 100 I.7-278 1.25 100 I.7-277 1.25 100 I.7-291 1.25 100 I.7-71 1.25 100 I.7-115 1.25 100 I.7-356 1.25 100 I.7-394 1.25 100 I.7-72 1.25 100 I.7-179 1.25 100 I.7-177 1.25 100 I.7-94 1.25 100 I.6-1 1.25 100 I.6-176 1.25 100 I.6-41 1.25 100 I.6-276 1.25 100 I.6-23 1.25 100 I.6-2 1.25 100 I.7-339 1.25 100 I.8-23 1.25 100 I.8-41 1.25 100 I.8-176 1.25 100 I.9-23 1.25 100 I.9-41 1.25 100 I.8-2 1.25 100 I.8-1 1.25 100 I.8-276 1.25 100 I.7-183 1.25 100 I.9-2 1.25 100 I.9-176 1.25 100 I.9-276 1.25 100 I.8-183 1.25 100 I.8-291 1.25 100 I.9-291 1.25 100 I.19-276 1.25 100 I.19-176 1.25 90 I.23-176 1.25 100 I.23-1 1.25 100 I.19-1 1.25 100 I.19-23 1.25 100 I.23-23 1.25 100 I.23-276 1.25 100
TABLE-US-00028 TABLE A10b Post-emergence action at 5 g/ha against SETVI in % Example Dosage number [g/ha] SETVI I.1-72 5 100 I.1-1 5 100 I.2-72 5 100 I.2-71 5 100 I.2-1 5 100 I.2-23 5 100 I.2-2 5 100 I.2-58 5 100 I.1-26 5 100 I.1-23 5 100 I.1-71 5 100 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-2 5 100 I.9-1 5 100 I.7-41 5 100 I.7-278 5 100 I.7-277 5 100 I.7-291 5 100 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 100 I.7-94 5 100 I.6-1 5 100 I.6-176 5 100 I.6-41 5 100 I.6-276 5 100 I.6-23 5 100 I.6-2 5 100 I.7-339 5 100 I.8-23 5 100 I.8-41 5 100 I.8-176 5 100 I.9-23 5 100 I.9-41 5 100 I.6-183 5 100 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 100 I.19-276 5 100 I.19-176 5 100 I.23-176 5 100 I.23-1 5 100 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100 I.23-276 5 100
TABLE-US-00029 TABLE A10c Post-emergence action at 20 g/ha against SETVI in % Example Dosage number [g/ha] SETVI I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 100 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 100 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00030 TABLE A11a Post-emergence action at 1.25 g/ha against VERPE in % Example Dosage number [g/ha] VERPE I.1-72 1.25 100 I.1-1 1.25 80 I.2-72 1.25 100 I.2-71 1.25 100 I.2-1 1.25 90 I.2-23 1.25 80 I.2-2 1.25 100 I.1-26 1.25 100 I.1-23 1.25 100 I.1-71 1.25 100 I.7-1 1.25 100 I.7-23 1.25 90 I.7-276 1.25 100 I.7-2 1.25 80 I.9-1 1.25 100 I.7-41 1.25 80 I.7-278 1.25 100 I.7-277 1.25 100 I.7-71 1.25 100 I.7-115 1.25 100 I.7-356 1.25 100 I.7-394 1.25 100 I.7-72 1.25 90 I.7-179 1.25 100 I.7-177 1.25 90 I.7-94 1.25 100 I.6-176 1.25 80 I.6-23 1.25 100 I.6-2 1.25 100 I.7-339 1.25 80 I.8-23 1.25 80 I.8-176 1.25 100 I.9-23 1.25 80 I.8-2 1.25 100 I.8-1 1.25 100 I.8-276 1.25 100 I.9-2 1.25 100 I.9-176 1.25 100 I.9-276 1.25 80 I.8-291 1.25 100 I.9-291 1.25 100 I.19-276 1.25 100 I.19-176 1.25 100 I.23-176 1.25 100 I.23-1 1.25 80 I.19-1 1.25 100 I.19-23 1.25 100 I.23-276 1.25 80
TABLE-US-00031 TABLE A11b Post-emergence action at 5 g/ha against VERPE in % Example Dosage number [g/ha] VERPE I.1-72 5 100 I.1-1 5 100 I.2-72 5 100 I.2-71 5 100 I.2-1 5 100 I.2-23 5 100 I.2-2 5 100 I.2-58 5 80 I.1-26 5 100 I.1-23 5 100 I.1-71 5 100 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-2 5 100 I.9-1 5 100 I.7-41 5 100 I.7-278 5 100 I.7-277 5 100 I.7-291 5 100 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 100 I.7-94 5 100 I.6-1 5 100 I.6-176 5 90 I.6-41 5 100 I.6-276 5 100 I.6-23 5 100 I.6-2 5 100 I.7-339 5 100 I.8-23 5 100 I.8-41 5 100 I.8-176 5 100 I.9-23 5 100 I.9-41 5 100 I.6-183 5 100 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 100 I.19-276 5 100 I.19-176 5 100 I.23-176 5 100 I.23-1 5 100 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100 I.23-276 5 100
TABLE-US-00032 TABLE A11c Post-emergence action at 20 g/ha against VERPE in % Example Dosage number [g/ha] VERPE I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 100 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 100 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00033 TABLE A12a Post-emergence action at 1.25 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR I.1-72 1.25 100 I.1-1 1.25 100 I.2-72 1.25 100 I.2-71 1.25 100 I.2-1 1.25 100 I.2-2 1.25 100 I.2-58 1.25 100 I.1-26 1.25 100 I.1-23 1.25 100 I.1-71 1.25 100 I.7-1 1.25 100 I.7-23 1.25 100 I.7-276 1.25 100 I.7-2 1.25 100 I.9-1 1.25 100 I.7-41 1.25 100 I.7-278 1.25 90 I.7-277 1.25 80 I.7-291 1.25 100 I.7-71 1.25 100 I.7-115 1.25 100 I.7-356 1.25 100 I.7-394 1.25 100 I.7-72 1.25 100 I.7-179 1.25 100 I.7-177 1.25 100 I.7-94 1.25 80 I.6-1 1.25 100 I.6-176 1.25 100 I.6-41 1.25 100 I.6-276 1.25 100 I.6-23 1.25 100 I.6-2 1.25 100 I.7-339 1.25 100 I.8-23 1.25 100 I.8-41 1.25 100 I.8-176 1.25 90 I.9-23 1.25 100 I.9-41 1.25 90 I.6-183 1.25 90 I.8-2 1.25 100 I.8-1 1.25 100 I.8-276 1.25 100 I.7-183 1.25 100 I.9-2 1.25 100 I.9-176 1.25 100 I.9-276 1.25 100 I.8-183 1.25 100 I.8-291 1.25 100 I.9-291 1.25 100 I.19-276 1.25 100 I.19-176 1.25 80 I.23-176 1.25 90 I.23-1 1.25 80 I.19-1 1.25 100 I.23-23 1.25 100 I.23-276 1.25 80
TABLE-US-00034 TABLE A12b Post-emergence action at 5 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR I.1-72 5 100 I.1-1 5 100 I.2-72 5 100 I.2-71 5 100 I.2-1 5 100 I.2-23 5 100 I.2-2 5 100 I.2-58 5 100 I.1-26 5 100 I.1-23 5 100 I.1-71 5 100 I.7-1 5 100 I.7-23 5 100 I.7-276 5 100 I.7-176 5 100 I.7-2 5 100 I.9-1 5 100 I.7-41 5 100 I.7-278 5 100 I.7-277 5 100 I.7-291 5 100 I.7-71 5 100 I.7-115 5 100 I.7-356 5 100 I.7-394 5 100 I.7-72 5 100 I.7-179 5 100 I.7-177 5 100 I.7-94 5 100 I.6-1 5 100 I.6-176 5 100 I.6-41 5 100 I.6-276 5 100 I.6-23 5 100 I.6-2 5 100 I.7-339 5 100 I.8-23 5 100 I.8-41 5 100 I.8-176 5 100 I.9-23 5 100 I.9-41 5 100 I.6-183 5 100 I.8-2 5 100 I.8-1 5 100 I.8-276 5 100 I.7-183 5 100 I.9-2 5 100 I.9-176 5 100 I.9-276 5 100 I.8-183 5 100 I.8-291 5 100 I.9-291 5 100 I.19-276 5 100 I.19-176 5 100 I.23-176 5 100 I.23-1 5 100 I.19-1 5 100 I.19-23 5 100 I.23-23 5 100 I.23-276 5 100
TABLE-US-00035 TABLE A12c Post-emergence action at 20 g/ha against VIOTR in % Example Dosage number [g/ha] VIOTR I.1-72 20 100 I.1-1 20 100 I.2-72 20 100 I.2-71 20 100 I.2-1 20 100 I.2-23 20 100 I.2-2 20 100 I.2-58 20 100 I.1-26 20 100 I.1-23 20 100 I.1-71 20 100 I.7-1 20 100 I.7-276 20 100 I.7-176 20 100 I.7-2 20 100 I.9-1 20 100 I.7-41 20 100 I.7-278 20 100 I.7-277 20 100 I.7-291 20 100 I.7-71 20 100 I.7-115 20 100 I.7-356 20 100 I.7-394 20 100 I.7-72 20 100 I.7-179 20 100 I.7-177 20 100 I.7-94 20 100 I.6-1 20 100 I.6-176 20 100 I.6-41 20 100 I.6-276 20 100 I.6-23 20 100 I.6-2 20 100 I.7-339 20 100 I.8-23 20 100 I.8-41 20 100 I.8-176 20 100 I.9-23 20 100 I.9-41 20 100 I.6-183 20 100 I.8-2 20 100 I.8-1 20 100 I.8-276 20 100 I.7-183 20 100 I.9-2 20 100 I.9-176 20 100 I.9-276 20 100 I.8-183 20 100 I.8-291 20 100 I.9-291 20 100 I.19-276 20 100 I.19-176 20 100 I.23-176 20 100 I.23-1 20 100 I.19-1 20 100 I.19-23 20 100 I.23-23 20 100 I.23-276 20 100
TABLE-US-00036 TABLE A13a Post-emergence action at 5 g/ha against HORMU in % Example Dosage number [g/ha] HORMU I.1-23 5 80 I.1-26 5 80 I.1-71 5 80
TABLE-US-00037 TABLE A13b Post-emergence action at 20 g/ha against HORMU in % Example Dosage number [g/ha] HORMU I.1-1 20 100 I.1-23 20 100 I.1-26 20 90 I.1-71 20 90
TABLE-US-00038 TABLE A14a Post-emergence action at 1.25 g/ha against STEME in % Example Dosage number [g/ha] STEME I.1-1 1.25 80 I.1-23 1.25 80 I.1-26 1.25 100 I.1-71 1.25 90 I.2-1 1.25 80
TABLE-US-00039 TABLE A14b Post-emergence action at 5 g/ha against STEME in % Example Dosage number [g/ha] STEME I.1-1 5 100 I.1-23 5 100 I.1-26 5 100 I.1-71 5 100 I.1-72 5 100 I.2-1 5 100 I.2-2 5 100 I.2-23 5 100 I.2-58 5 100 I.2-71 5 100 I.2-72 5 100
TABLE-US-00040 TABLE A14c Post-emergence action at 20 g/ha against STEME in % Example Dosage number [g/ha] STEME I.1-1 20 100 I.1-23 20 100 I.1-26 20 100 I.1-71 20 100 I.1-72 20 100 I.2-1 20 100 I.2-2 20 100 I.2-23 20 100 I.2-58 20 100 I.2-71 20 100 I.2-72 20 100
[0724] Tables A15 to A19 below show the crop plant compatibilities of selected compounds of the general formula (I) according to tables I.1 to I.33 at an application rate corresponding to 5 g/ha or less, which were observed in trials by the experimental procedure mentioned above. The observed effects on selected crop plants are reported here in comparison to the untreated controls (values in %). The appendices a, b and c give differentiation by different dosage with otherwise the same crop plants tested.
TABLE-US-00041 TABLE A15a Post-emergence action at 1.25 g/ha against BRSNW in % Example Dosage number [g/ha] BRSNW I.1-23 1.25 20 I.1-26 1.25 20 I.1-71 1.25 20 I.2-2 1.25 10 I.2-23 1.25 20 I.2-58 1.25 20 I.2-71 1.25 10 I.2-72 1.25 10 I.7-1 1.25 20 I.7-23 1.25 20 I.7-115 1.25 20 I.7-276 1.25 20
TABLE-US-00042 TABLE A15b Post-emergence action at 5 g/ha against BRSNW in % Example Dosage number [g/ha] BRSNW I.2-23 5 20 I.7-176 5 20 I.7-276 5 20
TABLE-US-00043 TABLE A15c Post-emergence action at 20 g/ha against BRSNW in % Example Dosage number [g/ha] BRSNW I.7-176 20 20 I.7-276 20 20
TABLE-US-00044 TABLE A16a Post-emergence action at 1.25 g/ha against ZEAMX in % Example Dosage number [g/ha] ZEAMX I.1-1 1.25 20 I.1-23 1.25 10 I.1-26 1.25 10 I.1-71 1.25 20 I.1-72 1.25 10 I.19-276 1.25 20 I.2-1 1.25 10 I.23-1 1.25 20 I.23-176 1.25 20 I.23-23 1.25 20 I.2-58 1.25 10 I.6-1 1.25 20 I.6-176 1.25 10 I.6-183 1.25 20 I.6-2 1.25 20 I.6-23 1.25 10 I.6-276 1.25 10 I.6-41 1.25 20 I.7-115 1.25 20 I.7-179 1.25 0 I.7-1 1.25 20 I.7-2 1.25 0 I.7-277 1.25 0 I.7-278 1.25 0 I.7-291 1.25 10 I.7-339 1.25 20 I.7-356 1.25 20 I.7-394 1.25 10 I.7-72 1.25 20 I.7-94 1.25 10 I.8-1 1.25 20 I.8-2 1.25 20 I.8-276 1.25 20 I.8-41 1.25 20 I.9-1 1.25 10 I.9-176 1.25 0 I.9-276 1.25 0 I.9-41 1.25 10
TABLE-US-00045 TABLE A16b Post-emergence action at 5 g/ha against ZEAMX in % Example Dosage number [g/ha] ZEAMX I.1-72 5 20 I.2-1 5 10 I.1-26 5 20 I.6-23 5 20 I.6-183 5 20 I.9-276 5 0
TABLE-US-00046 TABLE A16c Post-emergence action at 20 g/ha against ZEAMX in % Example Dosage number [g/ha] ZEAMX I.2-1 20 20 I.9-276 20 20
TABLE-US-00047 TABLE A17a Post-emergence action at 1.25 g/ha against TRZAS in % Example Dosage number [g/ha] TRZAS I.1-1 1.25 20 I.1-23 1.25 20 I.1-71 1.25 10 I.1-72 1.25 20 I.19-1 1.25 20 I.19-176 1.25 20 I.19-23 1.25 10 I.19-276 1.25 20 I.2-1 1.25 20 I.2-2 1.25 20 I.2-23 1.25 20 I.23-1 1.25 20 I.23-176 1.25 10 I.23-23 1.25 20 I.23-276 1.25 20 I.2-71 1.25 20 I.2-72 1.25 20 I.6-1 1.25 10 I.6-176 1.25 20 I.6-183 1.25 0 I.6-2 1.25 20 I.6-23 1.25 10 I.6-276 1.25 10 I.6-41 1.25 10 I.7-1 1.25 20 I.7-115 1.25 0 I.7-177 1.25 0 I.7-179 1.25 0 I.7-183 1.25 20 I.7-2 1.25 20 I.7-23 1.25 10 I.7-276 1.25 20 I.7-277 1.25 0 I.7-291 1.25 0 I.7-339 1.25 0 I.7-356 1.25 10 I.7-394 1.25 0 I.7-41 1.25 0 I.7-71 1.25 0 I.7-72 1.25 10 I.7-94 1.25 20 I.8-1 1.25 20 I.8-176 1.25 0 I.8-183 1.25 0 I.8-23 1.25 10 I.8-276 1.25 20 I.8-291 1.25 10 I.8-41 1.25 0 I.9-1 1.25 0 I.9-176 1.25 0 I.9-2 1.25 20 I.9-23 1.25 0 I.9-276 1.25 0 I.9-291 1.25 20 I.9-41 1.25 0
TABLE-US-00048 TABLE A17b Post-emergence action at 5 g/ha against TRZAS in % Example Dosage number [g/ha] TRZAS I.2-72 5 20 I.2-71 5 20 I.2-1 5 20 I.2-2 5 20 I.1-71 5 20 I.7-276 5 20 I.7-2 5 20 I.9-1 5 10 I.7-41 5 20 I.7-277 5 20 I.7-291 5 0 I.7-179 5 0 I.6-1 5 20 I.6-176 5 20 I.6-41 5 20 I.6-276 5 10 I.6-23 5 20 I.6-2 5 20 I.7-339 5 20 I.8-23 5 20 I.8-41 5 20 I.8-176 5 20 I.9-23 5 20 I.9-41 5 10 I.6-183 5 20 I.8-276 5 20 I.9-176 5 20 I.8-183 5 20 I.8-291 5 20 I.9-291 5 20 I.23-276 5 20 I.2-72 5 20 I.2-71 5 20 I.2-1 5 20 I.2-2 5 20 I.1-71 5 20 I.7-276 5 20 I.7-2 5 20 I.9-1 5 10 I.7-41 5 20 I.7-277 5 20 I.7-291 5 0 I.7-179 5 0 I.6-1 5 20 I.6-176 5 20 I.6-41 5 20 I.6-276 5 10 I.6-23 5 20 I.6-2 5 20 I.7-339 5 20 I.8-23 5 20 I.8-41 5 20 I.8-176 5 20 I.9-23 5 20 I.9-41 5 10 I.6-183 5 20 I.8-276 5 20 I.9-176 5 20 I.8-183 5 20 I.8-291 5 20 I.9-291 5 20 I.23-276 5 20
TABLE-US-00049 TABLE A17c Post-emergence action at 20 g/ha against TRZAS in % Example Dosage number [g/ha] TRZAS I.9-1 20 10 I.6-176 20 20 I.6-41 20 20 I.6-23 20 20 I.9-23 20 20 I.9-41 20 20
TABLE-US-00050 TABLE A18a Post-emergence action at 1.25 g/ha against ORYSA in % Example Dosage number [g/ha] ORYSA I.1-72 1.25 10 I.1-1 1.25 10 I.2-72 1.25 0 I.2-71 1.25 20 I.2-1 1.25 10 I.2-23 1.25 10 I.2-2 1.25 10 I.2-58 1.25 10 I.1-26 1.25 10 I.1-23 1.25 20 I.7-23 1.25 10 I.7-276 1.25 0 I.7-2 1.25 0 I.9-1 1.25 0 I.7-41 1.25 0 I.7-278 1.25 0 I.7-277 1.25 0 I.7-291 1.25 20 I.7-71 1.25 20 I.7-115 1.25 0 I.7-356 1.25 0 I.7-394 1.25 0 I.7-72 1.25 0 I.7-179 1.25 0 I.7-177 1.25 0 I.7-94 1.25 0 I.6-1 1.25 0 I.6-176 1.25 0 I.6-41 1.25 10 I.6-276 1.25 0 I.6-23 1.25 0 I.6-2 1.25 0 I.7-339 1.25 0 I.8-23 1.25 0 I.8-41 1.25 0 I.8-176 1.25 0 I.9-23 1.25 0 I.9-41 1.25 0 I.6-183 1.25 0 I.8-2 1.25 0 I.8-1 1.25 0 I.8-276 1.25 20 I.7-183 1.25 0 I.9-2 1.25 0 I.9-176 1.25 0 I.9-276 1.25 0 I.8-183 1.25 0 I.8-291 1.25 0 I.9-291 1.25 0 I.19-276 1.25 0 I.19-176 1.25 0 I.23-176 1.25 0 I.23-1 1.25 0 I.19-23 1.25 10 I.23-276 1.25 0
TABLE-US-00051 TABLE A18b Post-emergence action at 5 g/ha against ORYSA in % Example Dosage number [g/ha] ORYSA I.1-72 5 20 I.1-1 5 10 I.2-72 5 20 I.2-71 5 20 I.2-1 5 10 I.2-23 5 10 I.2-2 5 10 I.2-58 5 10 I.7-23 5 20 I.9-1 5 20 I.7-41 5 20 I.7-277 5 0 I.7-356 5 20 I.7-394 5 20 I.7-94 5 20 I.6-1 5 10 I.6-176 5 20 I.6-41 5 10 I.6-276 5 10 I.6-23 5 10 I.6-2 5 0 I.7-339 5 10 I.8-23 5 0 I.8-41 5 20 I.8-176 5 20 I.9-23 5 0 I.9-41 5 0 I.6-183 5 0 I.8-2 5 0 I.8-1 5 20 I.9-176 5 20 I.9-276 5 0 I.8-183 5 0 I.8-291 5 20 I.9-291 5 0 I.19-276 5 0 I.23-176 5 20 I.23-276 5 10
TABLE-US-00052 TABLE A18c Post-emergence action at 20 g/ha against ORYSA in % Example Dosage number [g/ha] ORYSA I.2-2 20 20 I.2-58 20 20 I.7-277 20 20 I.6-1 20 20 I.6-41 20 20 I.6-276 20 20 I.6-23 20 20 I.6-2 20 20 I.8-23 20 20 I.9-23 20 20 I.6-183 20 0 I.9-276 20 0 I.8-183 20 0 I.9-291 20 20 I.23-276 20 10
TABLE-US-00053 TABLE A19a Post-emergence action at 1.25 g/ha against GLXMA in % Example Dosage number [g/ha] GLXMA I.1-72 1.25 10 I.1-1 1.25 0 I.2-72 1.25 0 I.2-71 1.25 10 I.2-1 1.25 0 I.2-23 1.25 0 I.2-2 1.25 0 I.2-58 1.25 10 I.7-1 1.25 10 I.7-356 1.25 0 I.7-394 1.25 20 I.7-177 1.25 0 I.6-1 1.25 20 I.6-176 1.25 20 I.6-276 1.25 20 I.6-23 1.25 20 I.6-2 1.25 20 I.9-276 1.25 0
TABLE-US-00054 TABLE A19b Post-emergence action at 5 g/ha against GLXMA in % Example Dosage number [g/ha] GLXMA I.1-72 5 20 I.1-1 5 20 I.2-72 5 10 I.2-1 5 10 I.2-23 5 10 I.2-2 5 0 I.2-58 5 10 I.7-1 5 10 I.7-356 5 0 I.6-176 5 20
TABLE-US-00055 TABLE A19c Post-emergence action at 20 g/ha against GLXMA in % Example Dosage number [g/ha] GLXMA I.2-1 20 20 I.2-23 20 20 I.2-2 20 10 I.7-1 20 10
[0725] As the results show, inventive compounds of the general formula (I) in the case of post-emergence treatment have good herbicidal efficacy against harmful plants, for example Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Echinochloa crus-galli (ECHCG), Hordeum murinum (HORMU), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Stellaria media (STEME), Veronica persica (VERPE) and Viola tricolor (VIOTR) at an application rate of 0.02 kg of active substance or less per hectare, and good crop plant compatibility in the case of organisms such as Oryza sativa (ORYSA), Zea mays (ZEAMX), Brassica napus (BRSNW), Glycine max (GLXMA) and Triticum aestivum (TRZAS) at an application rate of 0.02 kg or less per hectare.
B. Pre-Emergence Herbicidal Action and Crop Plant Compatibility
[0726] 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 to the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate equivalent to 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.
[0727] Tables B1 to B10 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.33 on various harmful plants and at an application rate corresponding to 80 g/ha and less, which were obtained by the experimental method specified above. The appendices a, b and c give differentiation by different dosage with otherwise the same harmful plants tested.
TABLE-US-00056 TABLE B1a Pre-emergence action at 20 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH I.7-1 20 100 I.7-23 20 100
TABLE-US-00057 TABLE B1b Pre-emergence action at 80 g/ha against ABUTH in % Example Dosage number [g/ha] ABUTH I.7-1 80 100 I.7-23 80 100
TABLE-US-00058 TABLE B2a Pre-emergence action at 20 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY I.7-1 20 80 I.7-23 20 90
TABLE-US-00059 TABLE B2b Pre-emergence action at 80 g/ha against ALOMY in % Example Dosage number [g/ha] ALOMY I.7-1 80 100 I.7-23 80 100
TABLE-US-00060 TABLE B3a Pre-emergence action at 20 g/ha against AMARE in % Example Dosage number [g/ha] AMARE I.7-1 20 100 I.7-23 20 100
TABLE-US-00061 TABLE B3b Pre-emergence action at 80 g/ha against AMARE in % Example Dosage number [g/ha] AMARE I.7-1 80 100 I.7-23 80 100
TABLE-US-00062 TABLE B4 Pre-emergence action at 80 g/ha against AVEFA in % Example Dosage number [g/ha] AVEFA I.7-1 80 100 I.7-23 80 90
TABLE-US-00063 TABLE B5a Pre-emergence action at 20 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA I.7-1 20 100 I.7-23 20 100
TABLE-US-00064 TABLE B5b Pre-emergence action at 80 g/ha against DIGSA in % Example Dosage number [g/ha] DIGSA I.7-1 80 100 I.7-23 80 100
TABLE-US-00065 TABLE B6a Pre-emergence action at 20 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG I.7-23 20 80
TABLE-US-00066 TABLE B6b Pre-emergence action at 80 g/ha against ECHCG in % Example Dosage number [g/ha] ECHCG I.7-1 80 90 I.7-23 80 90
TABLE-US-00067 TABLE B7a Pre-emergence action at 20 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI I.7-23 20 90
TABLE-US-00068 TABLE B7b Pre-emergence action at 80 g/ha against LOLRI in % Example Dosage number [g/ha] LOLRI I.7-1 80 100 I.7-23 80 100
TABLE-US-00069 TABLE B8a Pre-emergence action at 20 g/ha against MATIN in % Example Dosage number [g/ha] MATIN I.7-1 20 100 I.7-23 20 100
TABLE-US-00070 TABLE B8b Pre-emergence action at 80 g/ha against MATIN in % Example Dosage number [g/ha] MATIN I.7-1 80 100 I.7-23 80 100
TABLE-US-00071 TABLE B9a Pre-emergence action at 20 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU I.7-1 20 100 I.7-23 20 100
TABLE-US-00072 TABLE B9b Pre-emergence action at 80 g/ha against PHBPU in % Example Dosage number [g/ha] PHBPU I.7-1 80 100 I.7-23 80 100
TABLE-US-00073 TABLE B10a Pre-emergence action at 20 g/ha against VERPE in % Example Dosage number [g/ha] VERPE I.7-1 20 100 I.7-23 20 100
TABLE-US-00074 TABLE B10b Pre-emergence action at 80 g/ha against VERPE in % Example Dosage number [g/ha] VERPE I.7-1 80 100 I.7-23 80 100
[0728] Tables B11 and B12 below show the crop plant compatibilities of selected compounds of the general formula (I) according to tables I.1 to I.33 at an application rate corresponding to 80 g/ha or less, which were observed in trials by the experimental procedure mentioned above. The observed effects on selected crop plants are reported here in comparison to the untreated controls (values in %).
TABLE-US-00075 TABLE B11 Pre-emergence action at 20 g/ha against ZEAMX in % Example Dosage number [g/ha] ZEAMX I.7-1 20 0 I.7-23 20 20
TABLE-US-00076 TABLE B12 Pre-emergence action at 20 g/ha against GLXMA in % Example Dosage number [g/ha] GLXMA I.7-23 20 10
[0729] As the results show, inventive compounds of the general formula (I), in pre-emergence treatment, have good herbicidal efficacy against harmful plants, for example against harmful plants such as Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU) and Veronica persica (VERPE) at an application rate of 0.08 kg of active substance or less per hectare, and good crop plant compatibility in the case of organisms such as Zea mays (ZEAMX) Glycine max (GLXMA) at an application rate of 0.02 kg per hectare.
C. Comparative Herbicidal Action and Crop Plant Compatibility of Two Inventive Compounds (I.7-1 and I.7-115) with a Compound of Similar Structure Known from the Literature (WO2002/098227, a-17 and EP1106607, 3-14) in Post-Emergence Treatment.
[0730] Tables C1-C4 below show the effects of two inventive compounds (I.7-1 and I.7-115) together with a compound of similar structure known from the literature (a-17 in WO2002/098227, and 3-14 in EP1106607) in different crop plants at an application rate corresponding to 5 g/ha or less, which have been obtained by the aforementioned experimental procedure.
[0731] The two inventive compounds (I.7-1 and I.7-115) are distinguished here by variance in a significant structural feature from the compounds known from the literature with regard to the ester unit, with the same chain length of the ester functionality, via the incorporation of a heteroatom or via the incorporation of a heteroatom with simultaneous ring formation.
TABLE-US-00077 TABLE C1 Application ALOMY rate Compound (efficacy in %) [g/ha]
TABLE-US-00078 TABLE C2 ECHCG Application rate Compound (efficacy in %) [g/ha] I.7-1 (inventive) 90 1.25 I.7-115 (inventive) 100 1.25 a-17 (WO2002/098227), 3-14 60 1.25 (EP1106607)
TABLE-US-00079 TABLE C3 MATIN Application rate Compound (efficacy in %) [g/ha] I.7-1 (inventive) 100 1.25 I.7-115 (inventive) 100 1.25 a-17 (WO2002/098227), 3-14 30 1.25 (EP1106607)
TABLE-US-00080 TABLE C4 SETVI Application rate Compound (efficacy in %) [g/ha] I.7-1 (inventive) 100 1.25 I.7-115 (inventive) 100 1.25 a-17 (WO2002/098227), 3-14 80 1.25 (EP1106607)
[0732] As the results shown in tables C1 to C4 show, inventive compounds I.7-1 and I.7-115, by comparison with literature compound a-17 (WO2002/098227) or 3-14 (EP1106607) show a distinct improvement in herbicidal efficacy against harmful plants, such as Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Matricaria inodora (MATIN) and Setaria viridis (SETVI) at an application rate of 5 g or less per hectare.
[0733] Table C5 below shows the effects of two inventive compounds (I.7-1 and I.7-115) together with a compound of similar structure known from the literature (a-17 in WO2002/098227 and 3-14 in EP1106607) in the crop plant Oryza sativa (ORYSA) at an application rate corresponding to 1.25 g/ha, which have been obtained by the aforementioned experimental procedure.
TABLE-US-00081 TABLE C5 ORYSA Application rate Compound (efficacy in %) [g/ha] I.7-1 (inventive) 0 1.25 I.7-115 (inventive) 0 1.25 a-17 (WO2002/098227), 3-14 20 1.25 (EP1106607)
[0734] As the results shown in table C5 show, the inventive compounds I.7-1 and I.7-115, by comparison with the literature compound a-17 (WO2002/098227) or 3-14 (EP1106607), show a distinct improvement in compatibility with respect to the crop plant Oryza sativa (ORYSA) at an application rate of 1.25 g per hectare.