4-DIFLUOROMETHYL BENZOYL AMIDES WITH HERBICIDAL ACTION
20200055829 ยท 2020-02-20
Inventors
- Hartmut AHRENS (Langen, DE)
- Joerg TIEBES (Frankfurt, DE)
- Christian Waldraff (Bad Vilbel, DE)
- Hansjoerg Dietrich (Liederbach am Taunus, DE)
- Elmar Gatzweiler (Bad Nauheim, DE)
- Christopher Hugh Rosinger (Hofheim, DE)
- Anu Bheemaiah Machettira (Frankfurt am Main, DE)
Cpc classification
C07C317/14
CHEMISTRY; METALLURGY
C07D317/14
CHEMISTRY; METALLURGY
C07D271/04
CHEMISTRY; METALLURGY
A01N43/82
HUMAN NECESSITIES
C07C321/28
CHEMISTRY; METALLURGY
C07D271/06
CHEMISTRY; METALLURGY
International classification
C07D271/06
CHEMISTRY; METALLURGY
A01N43/82
HUMAN NECESSITIES
C07C317/14
CHEMISTRY; METALLURGY
C07C321/28
CHEMISTRY; METALLURGY
Abstract
Benzoylamides of the general formula (I) are described as herbicides.
##STR00001##
In this formula (I), X, R and R.sup.a represent radicals such as alkyl, cycloalkyl and halogen. Q represents a five-membered heterocycle.
Claims
1. A benzoylamide of formula (I) or a salt thereof ##STR00022## in which the symbols and indices are defined as follows: Q represents a radical Q1, Q2, Q3 or Q4, ##STR00023## X represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl or halogen, R represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, R.sup.a represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.1(O)C(C.sub.1-C.sub.6)-alkyl, R.sup.1O(O)C(C.sub.1-C.sub.6)-alkyl, (R.sup.1).sub.2N(O)C(C.sub.1-C.sub.6)-alkyl, NC(C.sub.1-C.sub.6)-alkyl, R.sup.1O(C.sub.1-C.sub.6)-alkyl, R.sup.1(O)CO(C.sub.1-C.sub.6)-alkyl, R.sup.2(O).sub.2SO(C.sub.1-C.sub.6)-alkyl, (R.sup.1).sub.2N(C.sub.1-C.sub.6)-alkyl, R.sup.1(O)C(R.sup.1)N(C.sub.1-C.sub.6)-alkyl, R.sup.2(O).sub.2S(R.sup.1)N(C.sub.1-C.sub.6)-alkyl, R.sup.2(O).sub.nS(C.sub.1-C.sub.6)-alkyl, R.sup.1O(O).sub.2S(C.sub.1-C.sub.6)-alkyl, (R.sup.1).sub.2N(O).sub.2S(C.sub.1-C.sub.6)-alkyl, R.sup.1(O)C, R.sup.1O(O)C, (R.sup.1).sub.2N(O)C, R.sup.1O, (R.sup.1).sub.2N, R.sup.2O(O)C(R.sup.1)N, (R.sup.1).sub.2N(O)C(R.sup.1)N, R.sup.2(O).sub.2S, or benzyl substituted in each case by s radicals from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen, R.sup.X represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, where the six radicals mentioned above are in each case substituted by s radicals from the group consisting of nitro, cyano, (R.sup.6).sub.3Si, (R.sup.5O).sub.2(O)P, R.sup.2(O).sub.nS, (R.sup.1).sub.2N, R.sup.1O, R.sup.1(O)C, R.sup.1O(O)C, R.sup.1(O)CO, R.sup.2O(O)CO, R.sup.1(O)C(R.sup.1)N, R.sup.2(O).sub.2S(R.sup.1)N, (C.sub.3-C.sub.6)-cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the four last-mentioned radicals are substituted by s radicals from the group consisting of (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and halogen, and where heterocyclyl carries n oxo groups, or R.sup.X represents (C.sub.3-C.sub.7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, where the four radicals mentioned above are in each case substituted by s radicals from the group consisting of halogen, nitro, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-S(O).sub.n, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl, R.sup.Y represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.7)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or represents heteroaryl, heterocyclyl or phenyl, each of which is substituted by s radicals from the group consisting of (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and halogen, and where heterocyclyl carries n oxo groups, R.sup.Z represents hydrogen, (C.sub.1-C.sub.6)-alkyl, R.sup.1O(C.sub.1-C.sub.6)-alkyl, RCH.sub.2, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, R.sup.1O, R.sup.1(H)N, methoxycarbonyl, ethoxycarbonyl, methylcarbonyl, dimethylamino, trifluoromethylcarbonyl, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl, or represents heteroaryl, heterocyclyl, benzyl or phenyl, each of which is substituted by s radicals from the group consisting of halogen, nitro, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-S(O).sub.n, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.4)-alkyl, where heterocyclyl carries n oxo groups, R.sup.1 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O(C.sub.1-C.sub.6)-alkyl, heteroaryl-O(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.3)(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.3)(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.3)(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n(C.sub.1-C.sub.6)-alkyl, where the fifteen last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.3O(O)C, (R.sup.3).sub.2N(O)C, R.sup.3O, (R.sup.3).sub.2N, R.sup.4(O).sub.nS, R.sup.3O(O).sub.2S, (R.sup.3).sub.2N(O).sub.2S and R.sup.3O(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl carries n oxo groups, R.sup.2 represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O(C.sub.1-C.sub.6)-alkyl, heteroaryl-O(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.3)(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.3)(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.3)(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n(C.sub.1-C.sub.6)-alkyl, where the fifteen last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.3O(O)C, (R.sup.3).sub.2N(O)C, R.sup.3O, (R.sup.3).sub.2N, R.sup.4(O).sub.nS, R.sup.3O(O).sub.2S, (R.sup.3).sub.2N(O).sub.2S and R.sup.3O(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl carries n oxo groups, R.sup.3 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.4 is (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6) cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.5 represents hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.6 represents (C.sub.1-C.sub.4)-alkyl, R represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C.sub.3-C.sub.6)-cycloalkyl, or represents heteroaryl or heterocyclyl, in each case substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, n represents 0, 1 or 2, s represents 0, 1, 2 or 3, with the proviso that the compounds 4-difluoromethyl-3-ethylsulfinyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and 4-difluoromethyl-3-ethylsulfonyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and sodium salts thereof are excluded.
2. The benzoylamide as claimed in claim 1, in which Q represents a radical Q1, Q2, Q3 or Q4, ##STR00024## X represents (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, R represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, R.sup.a represents hydrogen, R.sup.X represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, where the six radicals mentioned above are in each case substituted by s radicals from the group consisting of R.sup.2(O).sub.nS, (R.sup.1).sub.2N, R.sup.1O, R.sup.1(O)C, R.sup.1O(O)C, R.sup.1(O)CO, R.sup.2O(O)CO, R.sup.1(O)C(R.sup.1)N, R.sup.2(O).sub.2S(R.sup.1)N, (C.sub.3-C.sub.6)-cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the four last-mentioned radicals are substituted by s radicals from the group consisting of (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and halogen, and where heterocyclyl carries n oxo groups, or R.sup.X represents (C.sub.3-C.sub.7)-cycloalkyl, where this radical is substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl and halo-(C.sub.1-C.sub.6)-alkyl, R.sup.Y represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino, aminocarbonyl or methoxymethyl, R.sup.Z represents hydrogen, (C.sub.1-C.sub.6)-alkyl, R.sup.1O(C.sub.1-C.sub.6)-alkyl, RCH.sub.2, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.1O, R.sup.1(H)N, methoxycarbonyl, acetylamino or methylsulfonyl, R.sup.1 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O(C.sub.1-C.sub.6)-alkyl, heteroaryl-O(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O(C.sub.1-C.sub.6)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.3O(O)C, (R.sup.3).sub.2N(O)C, R.sup.3O, (R.sup.3).sub.2N, R.sup.4(O).sub.nS and R.sup.3O(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl carries n oxo groups, R.sup.2 represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O(C.sub.1-C.sub.6)-alkyl, heteroaryl-O(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O(C.sub.1-C.sub.6)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.3O(O)C, (R.sup.3).sub.2N(O)C, R.sup.3O, (R.sup.3).sub.2N, R.sup.4(O).sub.nS and R.sup.3O(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl carries n oxo groups, R.sup.3 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, R.sup.4 represents (C.sub.1-C.sub.6)-alkyl, R represents acetoxy, acetamido, methoxycarbonyl or (C.sub.3-C.sub.6)-cycloalkyl, n represents 0, 1 or 2, s represents 0, 1, 2 or 3.
3. The benzoylamide as claimed in claim 1, in which Q represents a radical Q1, Q2, Q3 or Q4, ##STR00025## X represents halogen, R represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, R.sup.a represents hydrogen, R.sup.X represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, where the six radicals mentioned above are in each case substituted by s radicals from the group consisting of R.sup.2(O).sub.nS, (R.sup.1).sub.2N, R.sup.1O, R.sup.1(O)C, R.sup.1O(O)C, R.sup.1(O)CO, R.sup.2O(O)CO, R.sup.1(O)C(R.sup.1)N, R.sup.2(O).sub.2S(R.sup.1)N, (C.sub.3-C.sub.6)-cycloalkyl, heteroaryl, heterocyclyl and phenyl, where the four last-mentioned radicals are substituted by s radicals from the group consisting of (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and halogen, and where heterocyclyl carries n oxo groups, or R.sup.X represents (C.sub.3-C.sub.7)-cycloalkyl, where this radical is substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl and halo-(C.sub.1-C.sub.6)-alkyl, R.sup.Y represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino, aminocarbonyl or methoxymethyl, R.sup.Z represents hydrogen, (C.sub.1-C.sub.6)-alkyl, R.sup.1O(C.sub.1-C.sub.6)-alkyl, RCH.sub.2, (C.sub.3-C.sub.7)-cycloalkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.1O, R.sup.1(H)N, methoxycarbonyl, acetylamino or methylsulfonyl, R.sup.1 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O(C.sub.1-C.sub.6)-alkyl, heteroaryl-O(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O(C.sub.1-C.sub.6)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.3O(O)C, (R.sup.3).sub.2N(O)C, R.sup.3O, (R.sup.3).sub.2N, R.sup.4(O).sub.nS and R.sup.3O(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl carries n oxo groups, R.sup.2 represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O(C.sub.1-C.sub.6)-alkyl, heteroaryl-O(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O(C.sub.1-C.sub.6)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.3O(O)C, (R.sup.3).sub.2N(O)C, R.sup.3O, (R.sup.3).sub.2N, R.sup.4(O).sub.nS and R.sup.3O(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl carries n oxo groups, R.sup.3 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, R.sup.4 represents (C.sub.1-C.sub.6)-alkyl, R represents acetoxy, acetamido, methoxycarbonyl or (C.sub.3-C.sub.6)-cycloalkyl, n represents 0, 1 or 2, s represents 0, 1, 2 or 3.
4. The benzoylamide as claimed in claim 1, in which Q represents a radical Q1, Q2, Q3 or Q4, ##STR00026## X represents methyl, ethyl or cyclopropyl, R represents methyl, ethyl, cyclopropylmethyl or methoxyethyl, R.sup.a represents hydrogen, R.sup.X represents methyl, ethyl or n-propyl, R.sup.Y represents methyl or chlorine, R.sup.Z represents methyl, n represents 0, 1 or 2.
5. The benzoylamide as claimed in claim 1, in which Q represents a radical Q1, Q2, Q3 or Q4, ##STR00027## X represents fluorine, chlorine, bromine or iodine, R represents methyl, ethyl, cyclopropylmethyl or methoxyethyl, R.sup.a represents hydrogen, R.sup.X represents methyl, ethyl or n-propyl, R.sup.Y represents methyl or chlorine, R.sup.Z represents methyl, n represents 0, 1 or 2.
6. A herbicidal composition comprising at least one compound as claimed in claim 1 mixed with one or more formulation auxiliaries.
7. The herbicidal composition as claimed in claim 6, comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.
8. A method for controlling one or more unwanted plants, comprising applying an effective amount of at least one compound of the formula (I) as claimed in claim 1 or of herbicidal compositions thereof to the plants or a site of unwanted vegetation.
9. A product comprising a compound as claimed in claim 1 or of herbicidal compositions thereof for controlling one or more unwanted plants.
10. The product as claimed in claim 9, wherein the compound is used for controlling unwanted plants in one or more crops of useful plants.
11. The product as claimed in claim 10, wherein the useful plants are transgenic useful plants.
12. A compound of the formula (II) ##STR00028## in which the symbols and indices are defined as follows: X represents (C.sub.3-C.sub.6)-cycloalkyl or halogen, R represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, n represents 0, 1 or 2.
13. The compound as claimed in claim 12, in which X represents cyclopropyl, fluorine, chlorine, bromine or iodine, R represents methyl, ethyl, cyclopropylmethyl or methoxyethyl, n represents 0, 1 or 2.
14. A compound of the formula (III), ##STR00029## in which the symbols and indices are defined as follows: X represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl or halogen, R represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, n represents 0, 1 or 2.
15. The compound as claimed in claim 14, in which X represents methyl, ethyl, cyclopropyl, fluorine, chlorine, bromine or iodine, R represents methyl, ethyl, cyclopropylmethyl or methoxyethyl, n represents 0, 1 or 2.
Description
CHEMICAL EXAMPLES
Synthesis of 4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)-N-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide (Example No. 4-1)
Step 1: Synthesis of ethyl 4-difluoromethyl-2-methoxy-3-methylthiobenzoate
[0086] 66.02 g (477.7 mmol) of potassium carbonate were added to 104.4 g (398.1 mmol) of ethyl 4-difluoromethyl-2-hydroxy-3-methylthiobenzoate in 310 ml of acetone. A mixture of 6.04 g (59.7 mmol) of triethylamine and 7.53 g (59.7 mmol) of dimethyl sulfate was then added. 57.74 g (457.8 mmol) of dimethyl sulfate were then added dropwise. The reaction mixture was then stirred at room temperature (RT) for 16 h. For work-up the reaction mixture was freed from the solvent and the residue was stirred with 1000 ml of 1M aqueous sodium hydroxide solution for 2 h. CH.sub.2Cl.sub.2 was added to the mixture and, after phase separation, the organic phase was dried. The filtrate was freed of the solvent. 104.7 g of the desired product were obtained as residue.
Step 2: Synthesis of 4-difluoromethyl-2-methoxy-3-methylthiobenzoic acid
[0087] 104.7 g (378.9 mmol) of ethyl 4-difluoromethyl-2-methoxy-3-methylthiobenzoate were stirred with a mixture of 420 ml of 1M aqueous sodium hydroxide solution and 715 ml of methanol at RT for 16 h. For workup, the methanol was removed. The residue was extracted with ethyl acetate and the aqueous phase was then acidified with hydrochloric acid. The mixture was then extracted twice with ethyl acetate. The combined organic phases were dried and the filtrate was freed of the solvent. 90.0 g of the desired product were obtained as residue.
Step 3: Synthesis of 2-[4-(difluoromethyl)-2-methoxy-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole
[0088] 1.24 ml (16.1 mmol) of N,N-dimethylformamide were added to 40.0 g (161.1 mmol) of 4-difluoromethyl-2-methoxy-3-methylthiobenzoate in 600 ml of dichloromethane. 23.2 ml (265.9 mmol) of oxalyl chloride were then added dropwise. The reaction mixture was stirred at RT for 16 h. To bring the reaction to completion, 2.81 ml (32.2 mmol) of oxalyl chloride were then added and the mixture was stirred at RT for a further 24 h. The content was then concentrated and the residue was re-dissolved in 300 ml of CH.sub.2Cl.sub.2. Subsequently, a solution of 15.08 g (169.2 mmol) of 2-amino-2-methyl-1-propanol in 10% strength aqueous sodium hydroxide solution was added dropwise with slight ice bath cooling. The mixture was stirred at RT for 24 h. For work-up, the mixture was diluted first with CH.sub.2Cl.sub.2 and then with a little water. After phase separation, the aqueous phase was extracted with CH.sub.2Cl.sub.2. The combined organic phases were extracted and the filtrate was concentrated. For the second reaction step, the residue was dissolved in 600 ml of CH.sub.2Cl.sub.2, and 32.9 ml (451.2 mmol) of thionyl chloride were added. The reaction mixture was then stirred at RT for 16 h. For work-up, 500 ml of 10% strength aqueous sodium hydroxide solution were added over 2 h with ice bath cooling, followed by the addition of a further 100 ml of 10% strength aqueous sodium hydroxide solution. After phase separation, the aqueous phase was extracted with CH.sub.2Cl.sub.2. The combined organic phases were dried and the filtrate was concentrated. 200 ml of 6M hydrochloric acid were added to the residue and the mixture was extracted three times with in each case 60 ml of CH.sub.2Cl.sub.2. The combined organic phases were extracted twice with in each case 25 ml of 6M hydrochloric acid and then twice with in each case 20 ml of 6M hydrochloric acid. The hydrochloric acid phases were cooled in an ice bath and made alkaline with solid NaOH added a little at a time. The mixture was then extracted twice with in each case 200 ml of CH.sub.2Cl.sub.2 and then once more with 100 ml of CH.sub.2Cl.sub.2. The organic phases were dried and the filtrate was freed of the solvent. 32.6 g of the desired product were obtained as residue.
Step 4: Synthesis of 2-[4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole
[0089] At RT, 84.6 ml of a 1M solution (84.6 mmol) of methylmagnesium bromide in THF were added dropwise to a solution of 17.0 g (56.4 mmol) of 2-[4-(difluoromethyl)-2-methoxy-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole in 280 ml of diethyl ether. After 2 h, a further 56 ml of the 1M solution (56 mmol) of methylmagnesium bromide in THF were added dropwise over 3 h. The mixture was stirred at RT for 72 h. For work-up, the content was carefully poured onto a mixture of ice and dilute hydrochloric acid. The mixture was neutralized with NaOH and extracted twice with diethyl ether. The organic phases were dried and the filtrate was freed of the solvent. 15.9 g of the desired product were obtained as residue.
Step 5: Synthesis of 4-difluoromethyl-2-methyl-3-methylthiobenzoic acid
[0090] 30.9 ml (497 mmol) of iodomethane were added to 15.47 g (54.2 mmol) of 2-[4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole in 250 ml of acetone and the mixture was then stirred at 40 C. for 2 h. A further 25 ml (402 mmol) of iodomethane were then added and the mixture was subsequently stirred at a temperature of 40 C. for 20 h. To bring the reaction to completion, another 10 ml (161 mmol) of iodomethane were then added and the mixture was subsequently stirred at a temperature of 40 C. for 15 h. For work-up, the reaction mixture was cooled to RT and concentrated. For the reaction of the second reaction step, 150 ml of methanol and 150 ml of 20% strength aqueous sodium hydroxide solution were added to the residue and the mixture was heated under reflux for 2 h. Finally, the reaction mixture was stirred at RT for 72 h. For work-up, the contents were concentrated and the residue was taken up in a little water. The mixture was washed with CH.sub.2Cl.sub.2 and the aqueous phase was acidified with concentrated hydrochloric acid. The mixture was then extracted with CH.sub.2Cl.sub.2. The organic phase was freed from the solvent. 11.8 g of the desired product were obtained as residue.
Step 6: Synthesis of 4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)-N-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide (No. 4-1)
[0091] At RT, 137.4 mg (1.4 mmol) of 1-methyl-1H-1,2,4-triazole-5-amine were added to 232.2 mg (1.0 mmol) of 4-difluoromethyl-2-methyl-3-methylthiobenzoic acid in 5 ml of pyridine. With cooling, 177.7 mg (1.4 mmol) of oxalyl chloride were added and the mixture was then stirred at RT for 16 h. For work-up, the mixture was concentrated and the residue was taken up in CH.sub.2Cl.sub.2. The mixture was extracted once with an aqueous NaHCO.sub.3 solution and then extracted once with water. The organic phase was dried and the filtrate was concentrated. The residue was purified by chromatography, and 62.6 mg of the desired product were isolated.
[0092] The examples listed in the tables below were prepared analogously to the methods mentioned above or can be obtained analogously to the methods mentioned above. These compounds are very particularly preferred.
[0093] The abbreviations used mean: [0094] Ph=phenyl Me=methyl Et=ethyl c-Pr=cyclopropyl
TABLE-US-00001 TABLE 1 Compounds of the general formula (I) according to the invention in which Q represents Q1 and R.sup.x represents a methyl group and R.sup.a represents hydrogen
TABLE-US-00002 TABLE 2 Compounds of the general formula (I) according to the invention in which Q represents Q1 and R.sup.x represents an ethyl group and R.sup.a represents hydrogen.
TABLE-US-00003 TABLE 3 Compounds of the general formula (I) according to the invention in which Q represents Q1 and R.sup.x represents an n-propyl group and R.sup.a represents hydrogen,
TABLE-US-00004 TABLE 4 Compounds of the general formula (I) according to the invention in which Q represents Q2 and R.sup.x represents a methyl group and R.sup.a represents hydrogen
TABLE-US-00005 TABLE 5 Compounds of the general formula (I) according to the invention in which Q represents Q3 and R.sup.y represents a methyl group and R.sup.a represents hydrogen
TABLE-US-00006 TABLE 6 Compounds of the general formula (I) according to the invention in which Q represents Q3 and R.sup.y represents chlorine and R.sup.a represents hydrogen
TABLE-US-00007 TABLE 7 Compounds of the general formula (I) according to the invention in which Q represents Q4 and R.sup.z represents a methyl group and R.sup.a represents hydrogen
TABLE-US-00008 TABLE 8 Inventive compounds of the general formula (I) in the form of the sodium salts, in which Q is Q1 and R.sup.x is a methyl group
TABLE-US-00009 TABLE 9 Compounds of the general formula (II) according to the invention
TABLE-US-00010 TABLE 10 Compounds of the general formula (III) according to the invention
[0095] NMR data for numerous compounds of the formula (I) according to the invention mentioned in the tables above are disclosed below using the NMR peak list method. Here, the .sup.1H NMR data of selected examples are stated in the form of .sup.1H NMR peak lists. For each signal peak, first the value in ppm and then the signal intensity in round brackets are listed. The valuesignal intensity number pairs for different signal peaks are listed with separation from one another by semicolons. The peak list for one example therefore takes the form of:
.sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n)
[0096] 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. The lists of the .sup.1H NMR peaks are similar to the conventional .sup.1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation. In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which are likewise provided by the invention, and/or peaks of impurities.
[0097] In the reporting of compound signals within the delta range of solvents and/or water, our lists of .sup.1H NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.
[0098] The peaks of stereoisomers of the compounds of the invention and/or peaks of impurities usually have a lower intensity on average than the peaks of the compounds of the invention (for example with a purity of >90%).
[0099] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to by-product fingerprints.
[0100] 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 compounds of the invention, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional .sup.1H NMR interpretation.
TABLE-US-00011 Example 1-1: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.79 (0.78); 7.77 (1.41); 7.723 (1.33); 7.703 (0.72); 7.518 (0.54); 7.506 (1.01); 7.368 (2.17); 7.26 (92.56); 7.229 (1.07); 6.996 (0.51); 4.127 (14.78); 2.797 (9.61); 2.308 (16); 2.252 (0.56); 1.553 (1.29); 0.008 (1.14); 0 (32.43); 0.008 (0.97) Example 1-2: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.755 (0.94); 7.995 (0.74); 7.923 (0.57); 7.902 (0.93); 7.842 (1.16); 7.821 (0.68); 4.007 (16); 3.311 (53.71); 3.002 (12.55); 2.674 (0.69); 2.669 (0.92); 2.665 (0.7); 2.59 (7.06); 2.523 (2.83); 2.518 (4.26); 2.51 (55.71); 2.505 (120.68); 2.5 (167.23); 2.496 (116.4); 2.491 (51.7); 2.45 (0.53); 2.332 (0.71); 2.327 (0.96); 2.323 (0.69); 0.008 (0.95); 0 (31.89); 0.008 (0.89) Example 1-3: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.829 (0.84); 8.047 (0.55); 7.937 (0.88); 7.919 (0.94); 7.783 (1.21); 7.646 (0.6); 4.021 (16); 3.446 (10.93); 3.309 (31.28); 2.75 (7.59); 2.669 (0.55); 2.523 (1.58); 2.518 (2.4); 2.509 (30.08); 2.505 (65.21); 2.5 (91.14); 2.496 (63.77); 2.491 (28.46); 2.327 (0.53); 0.008 (0.54); 0 (17.36) Example 1-4: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.778 (0.71); 7.761 (1.15); 7.715 (1.06); 7.523 (1.62); 7.519 (1.13); 7.385 (3.47); 7.27 (0.65); 7.27 (0.73); 7.269 (0.81); 7.268 (0.84); 7.267 (1.06); 7.266 (1.35); 7.26 (155.87); 7.247 (2); 6.996 (0.85); 4.128 (1.1); 4.117 (16); 2.784 (2.73); 2.773 (8.76); 2.766 (7.1); 2.747 (5.05); 2.728 (1.75); 2.042 (1.82); 1.57 (2.2); 1.284 (0.63); 1.275 (1.24); 1.265 (1.7); 1.257 (2.02); 1.239 (1.19); 1.234 (7.07); 1.216 (14.14); 1.197 (6.63); 0.899 (0.91); 0.882 (3.32); 0.864 (1.23); 0.008 (1.65); 0.006 (0.61); 0.006 (0.65); 0.005 (0.77); 0 (55.26); 0.006 (0.8); 0.007 (0.64); 0.008 (1.72) Example 1-5: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.757 (1); 7.932 (0.55); 7.912 (0.92); 7.856 (1.09); 7.836 (0.68); 5.753 (0.57); 4.008 (16); 3.31 (44.61); 3.227 (0.59); 3.208 (0.58); 3.126 (0.66); 3.107 (0.69); 2.568 (5.11); 2.523 (1.11); 2.518 (1.62); 2.509 (21.94); 2.505 (46.65); 2.5 (64.18); 2.496 (44.74); 2.491 (20.18); 1.3 (2.55); 1.282 (5.31); 1.263 (2.39); 0 (4.67) Example 1-6: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.826 (0.98); 8.065 (0.55); 7.964 (0.9); 7.944 (0.68); 7.914 (0.63); 7.778 (1.36); 7.641 (0.65); 4.022 (16); 3.542 (0.71); 3.524 (2.42); 3.506 (2.48); 3.488 (0.75); 3.309 (87.5); 2.742 (8.48); 2.669 (0.56); 2.523 (1.92); 2.509 (34.37); 2.505 (72.77); 2.5 (99.75); 2.496 (69.83); 2.491 (31.46); 2.327 (0.57); 1.267 (2.62); 1.248 (5.94); 1.23 (2.62); 0 (3.28) Example 1-13: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.763 (0.8); 7.743 (1.83); 7.713 (2.2); 7.693 (0.97); 7.524 (0.88); 7.386 (1.93); 7.267 (13.77); 7.248 (0.97); 4.104 (15.81); 3.235 (0.68); 3.216 (2.31); 3.198 (2.35); 3.179 (0.72); 2.331 (16); 1.27 (2.84); 1.252 (6.76); 1.233 (2.81); 0 (5.47) Example 1-14: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.796 (1.2); 8.121 (0.6); 7.962 (0.5); 7.942 (0.9); 7.892 (1.2); 7.871 (0.7); 4.010 (16.0); 3.310 (34.6); 3.044 (11.9); 3.032 (0.5); 2.523 (1.2); 2.518 (1.8); 2.509 (22.8); 2.505 (49.0); 2.500 (68.3); 2.496 (47.6); 2.491 (21.1); 1.242 (1.8); 1.223 (4.3); 1.205 (1.7); 0.008 (0.7); 0.000 (23.5); 0.009 (0.7) Example 1-15: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.890 (0.7); 7.958 (0.8); 7.938 (0.7); 7.777 (1.2); 7.641 (0.6); 4.026 (16.0); 3.440 (10.7); 3.310 (22.0); 3.226 (1.1); 3.208 (1.1); 2.518 (0.8); 2.510 (12.2); 2.505 (27.2); 2.500 (38.4); 2.496 (26.7); 2.491 (11.7); 1.281 (1.5); 1.263 (4.0); 1.244 (1.6); 0.000 (17.4) Example 1-16: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.792 (0.77); 7.772 (1.59); 7.735 (2.01); 7.715 (0.98); 7.537 (0.8); 7.399 (1.81); 7.261 (16.53); 5.298 (1.09); 4.119 (16); 3.253 (0.59); 3.234 (2.01); 3.216 (2.06); 3.197 (0.64); 2.797 (1.14); 2.778 (3.65); 2.76 (3.69); 2.741 (1.19); 1.258 (4.01); 1.239 (8.35); 1.228 (2.65); 1.221 (4.02); 1.21 (6.13); 1.191 (2.52); 0 (6.53) Example 1-17: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.805 (1.75); 7.967 (0.92); 7.947 (1.25); 7.895 (1.45); 7.875 (0.9); 4.01 (16); 3.31 (32.77); 3.286 (0.72); 3.268 (0.74); 3.253 (0.9); 3.235 (0.82); 3.112 (0.68); 3.093 (0.81); 3.078 (0.61); 3.06 (0.59); 2.889 (0.52); 2.669 (0.51); 2.523 (0.75); 2.518 (1.23); 2.509 (21.71); 2.505 (54.6); 2.5 (86.23); 2.496 (78.63); 2.491 (50.39); 2.45 (0.77); 2.327 (0.57); 1.333 (2.67); 1.314 (5.76); 1.295 (2.73); 1.236 (2.18); 1.218 (5.11); 1.199 (2.25); 0.008 (0.55); 0 (20.1) Example 1-18: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.893 (0.71); 7.984 (0.74); 7.963 (0.58); 7.907 (0.53); 7.771 (1.23); 7.634 (0.63); 4.026 (16); 3.512 (0.62); 3.494 (2.16); 3.475 (2.18); 3.457 (0.67); 3.31 (42.94); 3.208 (1); 3.19 (0.97); 2.523 (0.75); 2.518 (1.2); 2.51 (21.1); 2.505 (47.16); 2.5 (66.67); 2.496 (46.4); 2.491 (20.66); 2.45 (0.51); 1.276 (2.41); 1.267 (1.83); 1.257 (5.73); 1.249 (4.46); 1.239 (2.59); 1.231 (1.78); 0.008 (0.64); 0 (25.34); 0.009 (0.75) Example 1-25: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.6077 (1.3); 7.6627 (2.3); 7.6435 (0.5); 7.5981 (0.9); 7.4606 (2.0); 7.3232 (0.9); 4.0382 (16.0); 3.3110 (39.5); 2.5224 (1.2); 2.5048 (39.0); 2.5004 (50.9); 2.4959 (37.0); 2.4915 (18.2); 2.4274 (8.2); 1.1329 (0.5); 1.1211 (1.7); 1.1177 (1.7); 1.0998 (1.7); 1.0850 (0.6); 0.6649 (0.6); 0.6508 (2.0); 0.6390 (2.0); 0.6247 (0.5); 0.0002 (8.8) Example 1-26: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.4191 (0.9); 8.2814 (2.0); 8.1437 (1.0); 7.9077 (1.1); 7.8874 (1.8); 7.8205 (2.0); 7.8004 (1.3); 4.0383 (1.3); 4.0204 (1.6); 4.0088 (14.3); 3.3113 (10.0); 3.0436 (16.0); 2.5229 (1.6); 2.5182 (2.2); 2.5095 (22.6); 2.5050 (46.2); 2.5005 (62.8); 2.4959 (44.0); 2.4914 (20.3); 2.0763 (0.7); 1.9878 (5.4); 1.2587 (0.6); 1.2366 (2.5); 1.1923 (1.5); 1.1745 (3.0); 1.1567 (1.7); 1.1286 (0.8); 1.1188 (0.7); 1.0038 (0.6); 0.9920 (0.7); 0.8539 (0.5); 0.7331 (0.6); 0.7162 (1.5); 0.7078 (1.3); 0.7015 (1.4); 0.6834 (0.6); 0.0002 (12.8) Example 1-27: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.7346 (0.8); 7.9246 (0.7); 7.8507 (0.5); 7.7145 (1.3); 7.5784 (0.6); 4.0346 (16.0); 3.5507 (11.0); 3.3125 (58.4); 2.5229 (1.1); 2.5095 (18.7); 2.5050 (39.5); 2.5004 (54.9); 2.4958 (38.2); 2.4913 (17.4); 1.9877 (1.1); 1.9079 (0.9); 1.1745 (0.6); 1.0897 (1.0); 1.0679 (1.0); 0.7579 (1.0); 0.7454 (0.9); 0.0002 (2.7) Example 1-28: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.6295 (0.9); 7.6749 (2.0); 7.6085 (0.8); 7.4711 (1.7); 7.3336 (0.8); 4.0397 (16.0); 3.3095 (63.0); 2.9118 (1.4); 2.8935 (1.4); 2.8749 (0.5); 2.5229 (0.8); 2.5181 (1.2); 2.5094 (19.5); 2.5049 (42.9); 2.5003 (60.3); 2.4957 (43.1); 2.4912 (20.1); 1.1708 (1.7); 1.1525 (3.4); 1.1340 (1.7); 1.1148 (1.4); 1.1109 (1.5); 1.0992 (0.8); 1.0934 (1.4); 1.0896 (1.4); 0.6400 (1.7); 0.6288 (1.6); 0.0002 (13.9) Example 1-29: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.6711 (0.7); 8.4143 (0.8); 8.2767 (1.6); 8.1391 (0.9); 7.9189 (1.1); 7.8985 (1.7); 7.8399 (1.4); 7.8198 (0.9); 4.0561 (0.5); 4.0382 (2.1); 4.0306 (16.0); 4.0206 (1.8); 4.0028 (0.5); 3.3099 (19.0); 3.1895 (1.3); 3.1721 (1.8); 3.1543 (1.5); 3.1366 (0.5); 2.5226 (1.5); 2.5092 (20.9); 2.5049 (40.9); 2.5004 (54.3); 2.4960 (39.0); 2.4917 (19.0); 1.9878 (5.8); 1.3407 (2.8); 1.3222 (5.9); 1.3036 (2.7); 1.1923 (1.8); 1.1746 (3.4); 1.1655 (1.0); 1.1568 (2.0); 1.0269 (0.6); 1.0145 (0.8); 0.7196 (1.9); 0.7058 (2.0); 0.6916 (0.5); 0.0002 (10.8) Example 1-30: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.7409 (1.0); 7.9943 (0.8); 7.9747 (1.5); 7.9399 (2.1); 7.9199 (1.0); 7.8511 (0.9); 7.7150 (2.0); 7.5793 (1.0); 4.0265 (16.0); 3.6682 (1.0); 3.6498 (3.1); 3.6313 (3.2); 3.6128 (1.0); 3.3090 (28.7); 2.6694 (0.5); 2.6176 (0.7); 2.5046 (55.9); 2.5003 (70.6); 2.4960 (51.8); 1.9877 (1.9); 1.3642 (3.3); 1.3458 (7.0); 1.3273 (3.2); 1.1923 (0.5); 1.1745 (1.0); 1.1567 (0.5); 1.0801 (2.0); 1.0586 (1.9); 0.7547 (2.3); 0.7425 (2.2); 0.0002 (13.0) Example 1-37: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.7857 (1.1); 7.9334 (0.6); 7.9140 (0.8); 7.8969 (0.6); 7.6578 (1.1); 7.6371 (1.0); 7.5220 (0.6); 7.3856 (1.4); 7.2492 (0.6); 3.9824 (16.0); 3.3115 (48.1); 2.5230 (0.8); 2.5184 (1.1); 2.5097 (17.9); 2.5051 (39.4); 2.5005 (55.5); 2.4959 (39.4); 2.4914 (17.8); 2.4735 (7.9); 0.0002 (14.1) Example 1-38: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.1061 (0.8); 8.0870 (1.3); 8.0692 (1.0); 7.8970 (1.0); 7.7721 (1.8); 7.7607 (2.1); 7.7520 (1.7); 7.6243 (1.1); 3.9297 (16.0); 3.3095 (12.4); 3.0901 (13.2); 2.6694 (0.5); 2.5228 (1.8); 2.5181 (2.5); 2.5094 (28.2); 2.5049 (58.4); 2.5004 (80.0); 2.4958 (56.2); 2.4913 (26.2); 0.0079 (0.8); 0.0002 (22.5); 0.0085 (0.8) Example 1-39: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.2804 (0.9); 8.2607 (1.3); 8.2433 (1.0); 7.9003 (1.7); 7.8796 (1.6); 7.8690 (1.0); 7.7327 (2.1); 7.5967 (1.0); 3.9669 (16.0); 3.5139 (10.5); 3.3104 (80.6); 3.1748 (1.6); 3.1619 (1.6); 2.6740 (0.7); 2.6694 (0.9); 2.6648 (0.7); 2.5228 (3.8); 2.5181 (5.2); 2.5094 (52.7); 2.5049 (109.3); 2.5003 (150.0); 2.4957 (102.8); 2.4911 (46.4); 2.3317 (0.7); 2.3271 (0.9); 2.3224 (0.6); 1.9876 (0.6); 1.9077 (5.9); 1.2361 (0.8); 0.0081 (0.6); 0.0002 (20.8); 0.0085 (0.6) Example 1-40: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 7.9143 (2.3); 7.6397 (2.7); 7.6175 (2.2); 7.3770 (2.8); 3.9227 (16.0); 3.3088 (54.4); 2.9380 (4.1); 2.9203 (3.9); 2.9018 (1.9); 2.6694 (1.7); 2.5002 (303.4); 2.4959 (221.2); 2.3263 (1.7); 1.1770 (4.2); 1.1590 (8.6); 1.1410 (4.3); 0.0002 (77.2) Example 1-41: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.8887 (1.1); 8.0993 (1.5); 7.9430 (1.0); 7.8078 (2.7); 7.7950 (1.7); 7.6704 (1.4); 4.0555 (1.1); 4.0381 (3.4); 4.0203 (3.6); 4.0027 (1.1); 3.9461 (9.2); 3.4292 (1.2); 3.4110 (1.4); 3.3611 (2.9); 3.3468 (3.1); 3.3426 (5.5); 3.3096 (2040.4); 3.2729 (2.1); 3.2595 (9.3); 2.6785 (3.9); 2.6740 (8.5); 2.6693 (11.7); 2.6647 (8.4); 2.6600 (3.9); 2.6195 (1.2); 2.5612 (4.2); 2.5471 (2.8); 2.5228 (44.4); 2.5181 (62.7); 2.5094 (668.3); 2.5048 (1388.2); 2.5002 (1912.9); 2.4957 (1320.7); 2.4911 (600.8); 2.4649 (3.8); 2.4600 (5.1); 2.4553 (6.7); 2.4501 (7.0); 2.4056 (1.2); 2.3361 (4.1); 2.3316 (8.3); 2.3270 (11.7); 2.3224 (8.5); 2.0720 (2.4); 1.9876 (16.0); 1.9077 (13.6); 1.2530 (3.9); 1.2345 (8.9); 1.2165 (3.8); 1.1923 (4.6); 1.1745 (9.3); 1.1567 (4.6); 0.1458 (1.8); 0.0080 (17.5); 0.0002 (568.1); 0.0085 (16.8); 0.0505 (1.1); 0.1497 (1.7) Example 1-42: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.2076 (1.1); 7.8342 (2.7); 7.8051 (2.4); 7.7863 (1.8); 7.6979 (5.2); 7.5615 (2.4); 4.0559 (1.0); 4.0382 (2.8); 4.0203 (2.8); 4.0026 (0.9); 3.7961 (8.4); 3.5613 (2.0); 3.5428 (5.2); 3.5243 (5.3); 3.5076 (2.1); 3.4229 (0.7); 3.3778 (1.0); 3.3614 (1.5); 3.3443 (2.7); 3.3099 (734.5); 3.2789 (1.7); 3.2583 (1.0); 2.6740 (4.1); 2.6693 (5.6); 2.6646 (4.1); 2.6601 (2.1); 2.6302 (0.7); 2.5693 (1.2); 2.5227 (24.1); 2.5181 (34.2); 2.5094 (325.9); 2.5048 (662.1); 2.5003 (900.8); 2.4957 (622.0); 2.4912 (282.5); 2.4410 (1.2); 2.3316 (3.7); 2.3270 (5.3); 2.3224 (3.7); 2.1781 (0.7); 2.0719 (0.8); 1.9876 (12.3); 1.9073 (7.0); 1.2362 (13.8); 1.2240 (16.0); 1.2056 (7.5); 1.1923 (4.2); 1.1745 (7.6); 1.1567 (3.7); 1.1133 (0.7); 0.8539 (1.6); 0.8365 (0.6); 0.1459 (0.7); 0.0080 (6.8); 0.0002 (209.6); 0.0085 (6.7); 0.1497 (0.6) Example 1-49: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 7.904 (0.66); 7.885 (0.88); 7.795 (1.36); 7.775 (0.93); 7.611 (0.58); 7.474 (1.35); 7.338 (0.69); 4.014 (16); 3.309 (38.07); 2.669 (0.64); 2.523 (1.94); 2.518 (2.95); 2.51 (36.77); 2.505 (78.98); 2.5 (109.62); 2.496 (76.69); 2.491 (34.21); 2.426 (8.5); 2.327 (0.66); 0 (15.6) Example 1-50: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.958 (0.9); 8.2 (0.6); 8.063 (1.32); 8.045 (0.8); 8.01 (1.29); 7.926 (0.68); 4.01 (16); 3.305 (22.19); 3.097 (8.07); 2.669 (0.94); 2.522 (2.77); 2.518 (4.06); 2.509 (59.83); 2.505 (130.08); 2.5 (181.46); 2.495 (127.32); 2.491 (58.04); 2.327 (1.11); 0.008 (3.08); 0 (89.77); 0.008 (2.67) Example 1-51: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.036 (0.97); 8.194 (0.61); 8.074 (1.13); 8.053 (0.84); 7.94 (0.6); 7.803 (1.34); 7.666 (0.7); 4.028 (16); 3.571 (8.8); 3.301 (23.52); 2.674 (0.75); 2.669 (1.08); 2.664 (0.74); 2.55 (0.55); 2.522 (3.09); 2.518 (4.34); 2.509 (58.23); 2.504 (126.06); 2.5 (175.99); 2.495 (123.31); 2.49 (55.64); 2.456 (0.51); 2.331 (0.76); 2.326 (1.05); 2.322 (0.76); 0.008 (0.69); 0 (26.33); 0.008 (0.84) Example 1-52: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.775 (3.97); 7.772 (3.32); 7.47 (0.93); 7.332 (2.04); 7.26 (29.31); 7.195 (0.99); 4.144 (16); 2.963 (0.81); 2.944 (2.5); 2.926 (2.59); 2.907 (0.99); 1.257 (3.42); 1.239 (6.98); 1.22 (3.25); 1.216 (0.8); 0 (12.32) Example 1-53: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.966 (0.87); 8.098 (0.94); 8.028 (0.88); 4.038 (0.72); 4.02 (0.93); 4.012 (16); 3.314 (11.93); 3.29 (1.28); 3.271 (1.27); 2.523 (1.31); 2.518 (1.82); 2.51 (25.42); 2.505 (55.43); 2.5 (77.74); 2.496 (54.39); 2.491 (24.2); 2.455 (0.57); 2.45 (0.7); 2.446 (0.51); 1.988 (3.4); 1.332 (1.47); 1.314 (3.02); 1.295 (1.43); 1.192 (0.96); 1.174 (1.9); 1.157 (0.94); 0.008 (1.45); 0 (49.32); 0.008 (1.5) Example 1-54: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.042 (0.98); 8.104 (0.76); 8.083 (0.6); 7.941 (0.58); 7.805 (1.33); 7.668 (0.67); 4.031 (16); 3.695 (1.14); 3.676 (1.17); 3.313 (4.96); 2.518 (0.64); 2.51 (8.92); 2.505 (19.32); 2.5 (26.8); 2.496 (18.67); 2.491 (8.35); 1.269 (1.53); 1.251 (3.17); 1.232 (1.53); 0 (8.17) Example 1-61: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.891 (0.6); 7.845 (0.74); 7.834 (1.19); 7.623 (0.51); 7.486 (1.18); 7.349 (0.58); 4.04 (16); 3.309 (17.41); 2.523 (0.93); 2.518 (1.43); 2.509 (20.81); 2.505 (45.5); 2.5 (63.89); 2.496 (44.28); 2.491 (19.4); 2.45 (0.57); 2.422 (4.44); 0.008 (1.2); 0 (45.19); 0.003 (1.91); 0.004 (0.69); 0.005 (0.51); 0.008 (1.3) Example 1-62: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.95 (0.97); 8.119 (0.85); 8.042 (0.88); 8.009 (0.55); 7.982 (0.73); 4.032 (16); 3.313 (14.24); 3.091 (5.78); 2.523 (0.75); 2.518 (1.05); 2.51 (14.9); 2.505 (32.81); 2.5 (45.95); 2.496 (32.3); 2.491 (14.95); 2.451 (1.03); 0.008 (0.52); 0 (17.37); 0.008 (0.58) Example 1-63: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.024 (1.45); 8.156 (0.57); 8.136 (1.19); 8.109 (1.47); 8.088 (0.65); 7.945 (0.64); 7.809 (1.41); 7.672 (0.71); 4.052 (16); 4.033 (0.52); 3.578 (7.24); 3.315 (24.01); 2.523 (1.12); 2.518 (1.71); 2.509 (22.57); 2.505 (48.42); 2.5 (66.89); 2.496 (46.84); 2.491 (21.1); 2.45 (0.5); 1.908 (0.63); 0 (14.66) Example 1-64: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.895 (0.69); 7.847 (1.98); 7.623 (0.63); 7.487 (1.38); 7.35 (0.67); 4.039 (16); 3.31 (24.78); 2.947 (1.27); 2.929 (1.29); 2.523 (1.32); 2.518 (1.97); 2.51 (25.95); 2.505 (55.92); 2.5 (77.48); 2.496 (53.77); 2.491 (23.63); 2.45 (0.51); 1.18 (1.52); 1.162 (3.05); 1.143 (1.55); 0.008 (1.65); 0.005 (0.58); 0 (57.33); 0.006 (0.78); 0.007 (0.67); 0.008 (1.71) Example 1-65: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.952 (1.03); 8.144 (0.84); 8.072 (0.51); 8.051 (0.95); 8.008 (0.74); 5.754 (6.01); 4.03 (16); 3.312 (32.93); 3.29 (0.97); 3.273 (1.14); 3.255 (1.07); 3.238 (0.51); 2.523 (0.84); 2.518 (1.19); 2.51 (23.97); 2.505 (54.05); 2.5 (76.85); 2.496 (55.23); 2.491 (26.33); 2.448 (1.56); 2.327 (0.52); 1.358 (1.55); 1.34 (3.27); 1.321 (1.6); 0.008 (0.63); 0 (29.26); 0.008 (1.13) Example 1-66: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.024 (2); 8.178 (0.76); 8.158 (1.87); 8.135 (2.05); 8.115 (0.84); 7.945 (0.94); 7.809 (2.09); 7.673 (1.03); 4.052 (16); 4.032 (0.78); 3.736 (0.8); 3.718 (2.2); 3.699 (2.26); 3.681 (0.89); 3.408 (8.24); 2.523 (1.56); 2.518 (2.34); 2.51 (28.84); 2.505 (61.43); 2.501 (84.52); 2.496 (58.95); 2.492 (26.44); 2.451 (0.53); 2.327 (0.52); 1.908 (2.96); 1.285 (2.36); 1.266 (4.74); 1.248 (2.44); 0 (13.92) Example 1-73: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.838 (1.13); 7.83 (0.9); 7.81 (1.38); 7.747 (0.84); 7.728 (0.56); 7.616 (0.75); 7.479 (1.67); 7.342 (0.82); 4.072 (16); 3.308 (32.82); 2.669 (0.51); 2.523 (1.56); 2.518 (2.23); 2.509 (28.29); 2.505 (60.63); 2.5 (84.02); 2.496 (59.23); 2.491 (26.7); 2.389 (7.95); 0.008 (1.28); 0 (41.59); 0.008 (1.17) Example 1-74: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.8934 (2.0); 8.3097 (0.8); 8.1727 (1.5); 8.0599 (1.1); 8.0377 (1.5); 7.8836 (0.9); 7.8618 (0.7); 4.0630 (16.0); 3.3137 (92.6); 3.0611 (10.2); 2.6739 (0.8); 2.6693 (1.1); 2.6649 (0.8); 2.5093 (67.9); 2.5048 (133.1); 2.5003 (178.2); 2.4958 (128.5); 2.4914 (61.6); 2.4668 (0.9); 2.3316 (0.8); 2.3271 (1.0); 2.3226 (0.8); 1.9078 (1.0); 0.0079 (0.7); 0.0002 (15.6) Example 1-75: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.9573 (0.6); 8.0873 (0.6); 8.0668 (0.8); 8.0024 (0.8); 7.7909 (0.6); 4.6702 (16.0); 4.0858 (3.6); 3.7444 (0.6); 3.7272 (0.6); 3.5478 (3.4); 2.5073 (63.7); 1.1028 (1.1); 1.0860 (0.6); 0.0002 (7.0) Example 1-76: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.845 (1.1); 7.845 (1.01); 7.824 (1.49); 7.752 (0.93); 7.732 (0.73); 7.621 (0.84); 7.484 (1.79); 7.347 (0.91); 4.072 (16); 3.309 (22.23); 2.934 (0.71); 2.916 (1.87); 2.898 (1.91); 2.879 (0.72); 2.523 (1.04); 2.51 (23.62); 2.505 (50.6); 2.5 (69.98); 2.496 (49.39); 2.492 (22.64); 1.201 (2.17); 1.182 (4.37); 1.164 (2.23); 0.008 (0.79); 0 (25.78); 0 (26.27); 0.008 (0.89) Example 1-77: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): = 11.907 (1.26); 8.316 (0.51); 8.179 (1.11); 8.066 (1); 8.045 (1.52); 7.889 (0.71); 7.87 (0.59); 4.062 (16); 3.322 (71.9); 3.271 (0.71); 3.253 (0.65); 3.22 (0.94); 3.201 (1); 3.186 (0.58); 2.524 (1.42); 2.519 (1.95); 2.51 (18.46); 2.506 (38.47); 2.501 (53.07); 2.497 (37.86); 2.492 (17.47); 1.908 (0.81); 1.392 (2.57); 1.374 (5.24); 1.355 (2.46); 0 (2.75) Example 1-78: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): = 11.9547 (3.0); 8.1145 (1.7); 8.0944 (2.4); 8.0249 (2.0); 8.0044 (1.4); 7.9278 (1.3); 7.7916 (2.8); 7.6554 (1.4); 4.0838 (16.0); 4.0628 (1.2); 3.7147 (1.3); 3.6968 (3.4); 3.6786 (3.4); 3.6603 (1.3); 3.3498 (1.4); 3.3246 (83.1); 2.5054 (50.1); 2.5012 (64.4); 2.4972 (49.3); 1.3078 (3.6); 1.2898 (7.0); 1.2718 (3.6); 0.0002 (1.0) Example 2-1: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.782 (0.64); 7.762 (1.18); 7.717 (1.18); 7.697 (0.67); 7.518 (0.55); 7.504 (0.93); 7.366 (2.07); 7.26 (99.7); 7.228 (1.08); 6.996 (0.53); 4.505 (1.09); 4.487 (3.51); 4.469 (3.55); 4.451 (1.15); 2.795 (8.78); 2.306 (16); 1.655 (4); 1.637 (8.77); 1.619 (3.98); 0.008 (1.1); 0 (41.08); 0.008 (1.35) Example 2-2: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.653 (1.38); 7.996 (0.99); 7.913 (0.74); 7.893 (1.22); 7.858 (0.61); 7.843 (1.5); 7.823 (0.84); 4.381 (1.22); 4.362 (3.94); 4.344 (4.01); 4.326 (1.24); 3.308 (63.88); 3.004 (16); 2.674 (0.83); 2.669 (1.17); 2.665 (0.79); 2.588 (9.37); 2.523 (4.05); 2.518 (5.99); 2.509 (67.99); 2.505 (144.81); 2.5 (198.98); 2.496 (137.97); 2.491 (61.37); 2.332 (0.8); 2.327 (1.2); 2.322 (0.85); 1.495 (4.44); 1.476 (10.14); 1.458 (4.38); 0.008 (1.03); 0 (33.01); 0.008 (1) Example 2-3: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.725 (2.33); 8.062 (0.79); 8.04 (0.99); 7.94 (1.78); 7.92 (2.29); 7.784 (2.61); 7.648 (1.23); 4.396 (1.93); 4.378 (6.18); 4.36 (6.2); 4.342 (1.93); 3.953 (0.62); 3.448 (22.11); 3.307 (82.43); 2.749 (16); 2.678 (0.56); 2.674 (1.21); 2.669 (1.7); 2.665 (1.21); 2.66 (0.6); 2.554 (0.74); 2.55 (1.08); 2.545 (1.09); 2.54 (1.19); 2.523 (5.51); 2.518 (7.94); 2.509 (97.61); 2.505 (210.76); 2.5 (294.34); 2.496 (205.42); 2.491 (91.2); 2.449 (0.56); 2.444 (0.58); 2.336 (0.6); 2.332 (1.32); 2.327 (1.73); 2.322 (1.25); 2.318 (0.64); 1.499 (6.55); 1.488 (0.97); 1.481 (15.03); 1.463 (6.47); 0.008 (1.61); 0 (55.05); 0.008 (1.58) Example 2-4: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.734 (1.82); 7.713 (1.8); 7.523 (1.88); 7.518 (1.48); 7.385 (4.08); 7.259 (231.31); 7.247 (2.6); 6.995 (1.28); 5.298 (2.5); 4.501 (1.83); 4.483 (5.75); 4.464 (5.86); 4.446 (2); 2.781 (3.06); 2.771 (12.83); 2.763 (7.54); 2.744 (6.31); 2.726 (2.13); 2.042 (1.22); 1.657 (6.23); 1.639 (13.17); 1.62 (6.2); 1.549 (2.26); 1.331 (0.56); 1.284 (0.96); 1.275 (0.87); 1.258 (2.45); 1.234 (7.93); 1.215 (16); 1.197 (7.45); 0.882 (1.4); 0.864 (0.65); 0.008 (3.22); 0 (94.1); 0.008 (2.86) Example 2-5: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.658 (2.62); 8.018 (0.79); 7.923 (1.2); 7.902 (2.04); 7.857 (2.63); 7.837 (1.41); 5.753 (0.64); 4.381 (2.1); 4.363 (6.57); 4.345 (6.61); 4.326 (2.09); 3.36 (1.48); 3.31 (147.53); 3.242 (1.06); 3.227 (1.35); 3.208 (1.25); 3.127 (1.46); 3.108 (1.59); 3.094 (1.02); 3.075 (0.93); 2.674 (1.24); 2.669 (1.68); 2.665 (1.25); 2.566 (12.77); 2.55 (3.76); 2.523 (9.33); 2.518 (11.63); 2.509 (91.56); 2.505 (188.98); 2.5 (258.72); 2.496 (182.09); 2.491 (83.39); 2.439 (0.56); 2.336 (0.58); 2.332 (1.13); 2.327 (1.54); 2.322 (1.05); 1.494 (7.27); 1.476 (16); 1.458 (7.09); 1.301 (5.62); 1.283 (11.89); 1.264 (5.31); 0 (11.34) Example 2-6: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.971 (1); 7.952 (3.22); 7.922 (1.79); 7.902 (0.79); 7.814 (2.84); 7.676 (1.43); 7.518 (1.29); 7.259 (209.94); 6.995 (1.08); 4.515 (1.03); 4.496 (2.82); 4.478 (2.89); 4.46 (1.07); 3.345 (1.6); 3.326 (4.87); 3.307 (5); 3.288 (1.56); 2.869 (16); 1.66 (4.56); 1.642 (9.29); 1.624 (4.63); 1.565 (0.98); 1.446 (5.4); 1.428 (11.03); 1.409 (5.05); 1.33 (1); 1.284 (1.24); 1.255 (1.35); 0.008 (2.95); 0 (83.48); 0.008 (3.21) Example 2-13: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.776 (0.71); 7.756 (1.67); 7.728 (2.13); 7.708 (0.9); 7.522 (0.87); 7.384 (1.93); 7.26 (26.96); 7.246 (0.99); 4.513 (1.12); 4.494 (3.67); 4.476 (3.7); 4.458 (1.16); 3.234 (0.66); 3.215 (2.22); 3.196 (2.25); 3.178 (0.69); 2.331 (16); 2.279 (1.29); 1.653 (3.97); 1.634 (8.64); 1.616 (3.91); 1.259 (2.77); 1.24 (6.6); 1.222 (2.76); 0 (11.06) Example 2-14: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.692 (1.42); 8.122 (0.85); 7.95 (0.61); 7.93 (1.17); 7.892 (1.62); 7.872 (0.8); 4.382 (1.13); 4.364 (3.67); 4.345 (3.75); 4.327 (1.17); 3.36 (0.71); 3.31 (123.1); 3.045 (16); 3.028 (0.59); 2.884 (0.58); 2.867 (0.51); 2.674 (0.59); 2.669 (0.84); 2.665 (0.59); 2.555 (0.52); 2.551 (0.65); 2.523 (2.39); 2.518 (3.56); 2.51 (49.94); 2.505 (108.7); 2.5 (152.09); 2.496 (105.57); 2.491 (46.48); 2.45 (0.52); 2.332 (0.71); 2.327 (0.99); 2.323 (0.68); 1.496 (4.41); 1.478 (10.45); 1.46 (4.34); 1.243 (2.28); 1.224 (5.68); 1.206 (2.3); 0.008 (1.4); 0 (53); 0.008 (1.59) Example 2-15: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.786 (2.88); 8.099 (0.76); 8.079 (0.95); 7.961 (1.95); 7.941 (1.51); 7.914 (1.19); 7.778 (2.66); 7.641 (1.33); 4.398 (1.87); 4.38 (6.21); 4.362 (6.32); 4.344 (1.99); 3.442 (23.78); 3.31 (71.85); 3.26 (0.53); 3.243 (0.81); 3.224 (2.56); 3.206 (2.61); 3.188 (0.82); 2.674 (0.55); 2.669 (0.78); 2.665 (0.57); 2.523 (2.17); 2.518 (3.27); 2.509 (46.2); 2.505 (100.26); 2.5 (140.15); 2.496 (97.51); 2.491 (43.24); 2.455 (0.96); 2.45 (1.19); 2.446 (0.82); 2.332 (0.66); 2.327 (0.9); 2.322 (0.66); 1.508 (6.92); 1.49 (16); 1.471 (6.85); 1.283 (3.68); 1.265 (9.36); 1.246 (3.68); 0.008 (1.44); 0 (52.54); 0.009 (1.58) Example 2-16: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.697 (13.47); 7.536 (1.83); 7.519 (0.89); 7.398 (4.27); 7.26 (151.86); 7.21 (1.21); 6.996 (0.85); 5.299 (2.93); 4.495 (1.8); 4.476 (5.74); 4.458 (5.82); 4.44 (1.87); 3.234 (1.21); 3.215 (4.19); 3.196 (4.29); 3.178 (1.36); 2.791 (2.11); 2.773 (6.77); 2.754 (6.92); 2.736 (2.25); 1.649 (6.3); 1.63 (13.48); 1.612 (6.48); 1.562 (1.18); 1.258 (7.71); 1.239 (16); 1.23 (4.76); 1.221 (7.78); 1.211 (10.55); 1.192 (4.55); 0.008 (1.64); 0 (62.7); 0.008 (2.04); 0.05 (0.51) Example 2-17: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.702 (3.4); 8.105 (0.58); 7.957 (1.15); 7.938 (1.79); 7.898 (2.55); 7.878 (1.29); 4.384 (1.92); 4.366 (6.16); 4.348 (6.2); 4.329 (1.96); 3.408 (4.77); 3.287 (1.05); 3.269 (1.21); 3.254 (1.57); 3.236 (1.45); 3.115 (1.21); 3.096 (1.34); 3.081 (1.01); 3.063 (0.95); 3.003 (0.58); 2.91 (0.6); 2.892 (0.74); 2.873 (0.59); 2.67 (0.57); 2.523 (2.07); 2.518 (2.96); 2.51 (34.26); 2.505 (73.09); 2.5 (100.87); 2.496 (71.3); 2.491 (32.71); 2.455 (0.85); 2.45 (0.95); 2.446 (0.67); 2.327 (0.65); 1.498 (6.96); 1.48 (16); 1.462 (6.95); 1.334 (5.11); 1.316 (11.02); 1.297 (4.99); 1.238 (4.02); 1.22 (9.38); 1.201 (3.94); 1.097 (0.51); 0.008 (1.4); 0 (46.28); 0.008 (1.61) Example 2-25: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.4970 (5.3); 7.6651 (5.7); 7.5989 (1.8); 7.4617 (4.1); 7.3241 (2.0); 4.4055 (2.5); 4.3875 (7.8); 4.3694 (7.9); 4.3512 (2.6); 3.3109 (92.1); 2.6700 (0.7); 2.5048 (90.3); 2.5004 (124.7); 2.4960 (95.3); 2.4277 (17.1); 2.3269 (0.8); 2.2239 (1.1); 1.5140 (7.4); 1.4960 (16.0); 1.4778 (7.4); 1.1276 (1.2); 1.1124 (3.9); 1.0906 (3.8); 0.6604 (4.2); 0.6483 (4.2); 0.0002 (20.4) Example 2-26: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.5506 (0.6); 8.4204 (0.9); 8.2828 (2.0); 8.1452 (1.0); 7.9244 (1.2); 7.9043 (1.8); 7.8322 (1.3); 7.8122 (0.9); 4.3953 (1.4); 4.3771 (4.5); 4.3590 (4.6); 4.3408 (1.5); 3.3111 (15.5); 3.0501 (16.0); 2.5228 (1.4); 2.5180 (2.0); 2.5094 (19.3); 2.5049 (39.1); 2.5004 (52.9); 2.4959 (37.0); 2.4914 (17.0); 2.0912 (0.6); 1.5076 (5.0); 1.4895 (10.9); 1.4714 (4.8); 1.1359 (0.9); 1.1262 (0.7); 1.0041 (0.7); 0.9916 (0.8); 0.7379 (0.6); 0.7226 (1.7); 0.7149 (1.4); 0.7073 (1.6); 0.6910 (0.6); 0.0002 (9.7) Example 2-27: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.6185 (0.9); 7.9585 (0.6); 7.9220 (1.3); 7.9027 (0.7); 7.8503 (0.8); 7.7148 (1.8); 7.5785 (0.9); 4.3976 (1.2); 4.3794 (4.0); 4.3612 (4.0); 4.3430 (1.3); 3.5516 (16.0); 3.3127 (55.9); 2.6691 (0.6); 2.5230 (1.4); 2.5182 (2.1); 2.5095 (24.1); 2.5050 (50.8); 2.5004 (70.5); 2.4959 (49.0); 2.4913 (22.3); 1.9877 (0.8); 1.5026 (4.5); 1.4845 (10.3); 1.4663 (4.4); 1.0834 (1.6); 1.0612 (1.5); 0.7677 (1.4); 0.7550 (1.4); 0.0002 (3.4) Example 2-28: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.5133 (0.9); 7.6696 (7.3); 7.6086 (1.6); 7.4711 (3.7); 7.3337 (1.8); 4.4020 (2.1); 4.3838 (6.9); 4.3657 (7.0); 4.3475 (2.2); 4.1051 (0.8); 4.0870 (0.8); 3.3107 (89.4); 2.9283 (1.4); 2.9099 (4.2); 2.8915 (4.3); 2.8731 (1.5); 2.6696 (0.7); 2.6651 (0.5); 2.5502 (0.6); 2.5231 (1.9); 2.5184 (2.7); 2.5097 (38.7); 2.5051 (85.2); 2.5005 (119.6); 2.4959 (85.2); 2.4913 (39.3); 2.3319 (0.5); 2.3273 (0.7); 2.3227 (0.5); 2.1684 (0.6); 1.9878 (1.2); 1.5132 (7.1); 1.4950 (16.0); 1.4769 (7.1); 1.3132 (1.0); 1.2951 (2.0); 1.2770 (0.9); 1.2364 (1.2); 1.1745 (1.2); 1.1681 (5.3); 1.1497 (11.0); 1.1313 (5.2); 1.1173 (1.1); 1.1054 (2.8); 1.1016 (2.9); 1.0963 (1.6); 1.0900 (1.5); 1.0843 (2.8); 1.0803 (2.9); 1.0689 (1.0); 0.6665 (1.0); 0.6517 (3.6); 0.6406 (3.3); 0.6373 (2.9); 0.6256 (0.9); 0.0002 (8.6) Example 2-29: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.5628 (0.8); 8.4128 (1.7); 8.2753 (3.1); 8.1370 (1.8); 7.9186 (2.3); 7.8975 (3.2); 7.8340 (2.4); 7.8130 (1.5); 4.3916 (2.3); 4.3734 (6.9); 4.3552 (6.6); 4.3371 (2.1); 4.1055 (0.8); 4.0382 (1.1); 4.0207 (1.0); 3.3124 (98.0); 3.2069 (1.2); 3.1884 (2.6); 3.1736 (3.0); 3.1554 (2.7); 2.6694 (1.0); 2.5095 (67.8); 2.5051 (133.9); 2.5006 (178.2); 2.4961 (126.0); 2.4917 (59.2); 2.3274 (1.1); 2.0454 (1.2); 1.9879 (4.6); 1.9077 (1.2); 1.5063 (7.3); 1.4883 (16.0); 1.4701 (7.4); 1.3408 (5.8); 1.3223 (12.3); 1.3038 (6.0); 1.2363 (2.7); 1.1924 (1.4); 1.1746 (3.0); 1.1569 (2.7); 0.9953 (1.7); 0.7284 (3.6); 0.7134 (3.5); 0.0002 (8.2) Example 2-30: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.6232 (1.1); 7.9885 (0.7); 7.9676 (1.4); 7.9403 (2.8); 7.9201 (1.2); 7.8509 (1.3); 7.7150 (3.1); 7.5792 (1.5); 4.3930 (1.9); 4.3749 (6.1); 4.3567 (6.2); 4.3386 (1.9); 4.0382 (1.0); 4.0205 (1.0); 3.6699 (1.4); 3.6515 (4.9); 3.6330 (5.0); 3.6145 (1.5); 3.3090 (61.8); 2.6739 (0.6); 2.6693 (0.8); 2.6647 (0.6); 2.6166 (0.7); 2.5228 (3.1); 2.5181 (4.2); 2.5094 (43.8); 2.5048 (90.9); 2.5003 (124.8); 2.4957 (86.5); 2.4911 (39.4); 2.3316 (0.5); 2.3270 (0.7); 2.3224 (0.5); 1.9877 (4.5); 1.4994 (7.1); 1.4813 (16.0); 1.4631 (6.9); 1.3647 (5.2); 1.3463 (11.9); 1.3277 (5.1); 1.2477 (0.9); 1.1923 (1.3); 1.1745 (2.5); 1.1568 (1.2); 1.0902 (0.7); 1.0789 (2.4); 1.0755 (2.4); 1.0572 (2.3); 1.0538 (2.4); 1.0432 (0.8); 0.8584 (1.6); 0.8408 (0.5); 0.7623 (2.6); 0.7504 (2.6); 0.0080 (1.1); 0.0002 (34.1); 0.0085 (1.0) Example 2-37: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.6992 (0.6); 7.9256 (1.4); 7.9063 (2.0); 7.8890 (1.6); 7.6505 (2.7); 7.6303 (2.4); 7.5208 (1.3); 7.3840 (3.2); 7.2476 (1.4); 4.3607 (2.0); 4.3424 (6.3); 4.3242 (6.3); 4.3061 (2.1); 3.3121 (54.1); 2.6698 (0.6); 2.5231 (2.1); 2.5184 (3.1); 2.5098 (40.3); 2.5052 (87.1); 2.5006 (121.2); 2.4961 (85.1); 2.4915 (38.2); 2.4692 (18.3); 2.3273 (0.6); 1.4797 (7.2); 1.4615 (16.0); 1.4434 (7.1); 0.0081 (0.7); 0.0002 (24.4) Example 2-38: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.1029 (1.1); 8.0835 (1.7); 8.0657 (1.1); 7.8972 (1.3); 7.7619 (3.8); 7.7439 (1.9); 7.6243 (1.4); 4.3200 (1.4); 4.3019 (4.2); 4.2837 (4.3); 4.2656 (1.5); 4.0383 (1.5); 4.0205 (1.5); 3.3104 (14.2); 3.0864 (16.0); 2.6696 (0.6); 2.5353 (0.6); 2.5229 (2.5); 2.5183 (3.4); 2.5096 (38.0); 2.5050 (79.6); 2.5004 (109.8); 2.4959 (77.0); 2.4913 (35.5); 2.3273 (0.6); 1.9877 (7.0); 1.9077 (4.3); 1.4529 (4.7); 1.4348 (10.1); 1.4166 (4.7); 1.2363 (1.3); 1.1923 (1.9); 1.1745 (3.9); 1.1567 (1.9); 0.0080 (0.9); 0.0002 (30.6); 0.0085 (1.0) Example 2-39: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.2399 (2.3); 8.2215 (3.8); 8.2023 (2.3); 7.8493 (2.4); 7.8165 (4.9); 7.7959 (4.4); 7.7127 (4.9); 7.5765 (2.4); 4.2684 (3.2); 4.2503 (9.0); 4.2322 (9.1); 4.2142 (3.5); 3.4864 (25.8); 3.3109 (31.8); 3.1687 (2.0); 2.6693 (1.3); 2.5044 (158.8); 2.5004 (191.6); 2.4964 (145.5); 2.3270 (2.5); 1.9075 (2.4); 1.4240 (8.0); 1.4060 (16.0); 1.3879 (8.9); 1.2988 (1.5); 1.2589 (1.9); 1.2365 (5.0); 0.8541 (0.8); 0.0002 (32.4) Example 2-40: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.7204 (1.7); 7.9359 (2.4); 7.9183 (3.8); 7.9009 (2.4); 7.6571 (4.5); 7.6372 (3.7); 7.5194 (2.3); 7.3838 (4.3); 7.2484 (2.0); 4.3409 (2.6); 4.3242 (7.4); 4.3051 (7.4); 4.2869 (2.8); 3.3090 (49.0); 2.9597 (2.2); 2.9413 (6.4); 2.9230 (6.8); 2.9038 (2.8); 2.6687 (1.9); 2.5002 (293.9); 2.3271 (1.8); 1.4679 (7.5); 1.4498 (16.0); 1.4313 (8.1); 1.2334 (1.6); 1.1775 (7.4); 1.1591 (14.7); 1.1410 (8.1); 0.0002 (78.4) Example 2-41: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.1068 (2.0); 8.0885 (3.3); 8.0698 (2.0); 7.9403 (2.4); 7.8377 (0.6); 7.8038 (5.2); 7.7669 (4.1); 7.7464 (3.5); 7.7057 (0.6); 7.6674 (2.6); 4.2904 (2.6); 4.2722 (7.4); 4.2540 (7.7); 4.2360 (2.8); 4.0383 (1.4); 4.0206 (1.4); 3.5519 (0.6); 3.5341 (0.6); 3.3104 (49.0); 3.2792 (3.9); 3.2512 (2.9); 3.2323 (2.8); 3.2173 (1.8); 3.1990 (1.3); 3.1815 (0.6); 2.6740 (1.2); 2.6695 (1.5); 2.5092 (104.5); 2.5050 (194.7); 2.5005 (250.3); 2.4961 (176.6); 2.4918 (84.2); 2.3314 (1.1); 2.3272 (1.4); 2.3227 (1.1); 1.9877 (6.1); 1.4341 (7.8); 1.4160 (16.0); 1.3978 (8.2); 1.2987 (0.9); 1.2586 (2.0); 1.2455 (8.4); 1.2362 (6.9); 1.2272 (15.5); 1.2087 (7.9); 1.1924 (2.6); 1.1746 (3.6); 1.1568 (1.8); 0.8540 (0.8); 0.0078 (2.7); 0.0002 (52.5); 0.0084 (2.4) Example 2-42: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.2767 (1.8); 8.2576 (2.9); 8.2395 (1.9); 7.8731 (3.6); 7.8514 (4.7); 7.7140 (4.1); 7.5779 (2.0); 4.3036 (2.2); 4.2854 (6.8); 4.2673 (7.0); 4.2491 (2.6); 4.0383 (1.1); 4.0205 (1.1); 3.5835 (1.8); 3.5649 (5.2); 3.5465 (5.4); 3.5283 (2.1); 3.3105 (19.4); 2.6741 (0.8); 2.6695 (1.2); 2.6649 (0.9); 2.5391 (0.6); 2.5230 (4.3); 2.5183 (6.0); 2.5096 (65.2); 2.5051 (136.3); 2.5005 (187.8); 2.4959 (130.6); 2.4913 (60.0); 2.4746 (0.6); 2.4695 (0.6); 2.4647 (0.6); 2.3319 (0.8); 2.3273 (1.1); 2.3226 (0.8); 1.9877 (5.3); 1.9077 (5.4); 1.4445 (6.8); 1.4264 (14.1); 1.4083 (7.1); 1.3757 (0.8); 1.3568 (0.6); 1.2986 (0.8); 1.2523 (7.0); 1.2342 (16.0); 1.2155 (7.0); 1.1923 (1.9); 1.1791 (0.6); 1.1745 (3.3); 1.1567 (1.6); 0.8539 (0.8); 0.0079 (2.0); 0.0063 (0.9); 0.0054 (0.9); 0.0002 (60.8); 0.0068 (0.8); 0.0085 (1.9) Example 2-49: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.764 (6.0); 7.519 (0.6); 7.449 (1.5); 7.312 (3.2); 7.288 (0.6); 7.281 (0.7); 7.274 (1.0); 7.270 (1.1); 7.261 (99.8); 7.253 (0.8); 7.238 (1.0); 7.184 (0.8); 7.175 (1.8); 6.997 (0.5); 4.533 (1.4); 4.515 (4.3); 4.497 (4.4); 4.479 (1.5); 2.434 (16.0); 2.356 (2.5); 1.658 (5.4); 1.639 (11.0); 1.621 (5.6); 1.599 (1.1); 0.008 (1.1); 0.000 (31.9); 0.008 (0.9) Example 2-50: .sup.1H-NMR (400.0 MHz, CDCl3): = 8.132 (0.89); 8 (1.75); 7.992 (1.3); 7.983 (1.51); 7.902 (1.89); 7.882 (1.32); 7.858 (1.04); 7.519 (1.68); 7.312 (0.71); 7.31 (0.84); 7.26 (298.81); 7.25 (2.51); 7.246 (1.94); 7.245 (1.75); 7.238 (1.35); 7.235 (1.24); 7.23 (1.29); 7.226 (1.19); 7.212 (1.82); 7.21 (2.71); 6.996 (1.68); 4.516 (0.77); 4.498 (2.34); 4.479 (2.42); 4.462 (0.94); 3.491 (3.07); 3.113 (16); 1.65 (4.71); 1.632 (9.95); 1.613 (5.13); 1.581 (1.19); 1.284 (0.54); 1.264 (0.51); 0.008 (3.84); 0.006 (1.8); 0 (131.12); 0.006 (2.66); 0.007 (2.35); 0.008 (4.88); 0.012 (1.21); 0.014 (1.02); 0.015 (1);0.016 (0.93); 0.016 (0.92); 0.023 (0.72); 0.031 (0.65); 0.034 (0.59); 0.049 (0.89); 0.05 (1.13) Example 2-51: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.958 (4.87); 8.222 (1.31); 8.204 (1.63); 8.08 (2.62); 8.06 (2.11); 7.941 (1.46); 7.805 (3.15); 7.668 (1.59); 4.415 (2.72); 4.397 (8.24); 4.378 (8.39); 4.36 (2.91); 3.578 (16); 3.322 (26.13); 2.6 (0.51); 2.51 (30.41); 2.505 (58.09); 2.501 (76.3); 2.496 (56.56); 2.492 (29.5); 2.376 (0.86); 2.328 (0.51); 1.908 (0.61); 1.503 (7.09); 1.485 (14.54); 1.467 (7.11); 0 (5.05) Example 2-52: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.815 (4.01); 7.914 (0.97); 7.894 (1.25); 7.818 (2.55); 7.798 (1.69); 7.613 (1.3); 7.477 (2.89); 7.341 (1.5); 4.406 (2.74); 4.388 (8.88); 4.369 (9); 4.351 (2.81); 3.312 (50.97); 2.968 (1.01); 2.949 (2.73); 2.931 (2.85); 2.913 (1.15); 2.674 (0.97); 2.67 (1.36); 2.665 (1.01); 2.523 (3.6); 2.518 (5.5); 2.51 (74.19); 2.505 (159.44); 2.5 (220.37); 2.496 (153.51); 2.491 (68.91); 2.455 (1.13); 2.45 (1.5); 2.446 (1.22); 2.332 (1); 2.327 (1.36); 2.323 (0.97); 1.501 (7.28); 1.483 (16); 1.464 (7.26); 1.172 (3.24); 1.153 (6.44); 1.135 (3.27); 1.124 (0.96); 0.008 (1.66); 0 (55.84);0.008 (1.75) Example 2-53: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.8750 (1.0); 8.2361 (1.6); 8.0993 (3.4); 8.0449 (1.3); 8.0259 (3.8); 8.0088 (3.9); 7.9895 (1.2); 7.9615 (1.8); 4.3757 (1.5); 4.3582 (4.2); 4.3400 (4.2); 4.3230 (1.5); 4.0382 (1.0); 4.0205 (1.2); 3.3098 (43.4); 3.2858 (6.5); 3.2671 (6.4); 3.2486 (2.4); 2.6696 (1.3); 2.5229 (4.3); 2.5183 (6.1); 2.5095 (73.4); 2.5050 (154.6); 2.5004 (215.2); 2.4958 (148.1); 2.4912 (66.6); 2.3272 (1.3); 1.9877 (4.9); 1.4810 (6.8); 1.4630 (14.4); 1.1118 (6.4); 1.3330 (7.3); 1.3143 (16.0); 1.2958 (7.0); 1.1924 (1.4); 1.1745 (2.6); 1.1567 (1.4); 0.0080 (2.8); 0.0002 (81.0); 0.0086 (2.2) Example 2-54: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.942 (2); 8.228 (1.01); 8.207 (1.26); 8.097 (2.84); 8.076 (2.1); 7.94 (1.56); 7.804 (3.52); 7.668 (1.78); 4.409 (2.5); 4.391 (8.06); 4.373 (8.18); 4.355 (2.57); 4.019 (0.52); 3.713 (1.22); 3.695 (3.77); 3.676 (3.8); 3.658 (1.26); 3.359 (0.55); 3.309 (140.03); 2.679 (0.52); 2.674 (1.09); 2.669 (1.55); 2.665 (1.11); 2.66 (0.51); 2.55 (0.99); 2.546 (0.9); 2.523 (4.38); 2.518 (6.36); 2.509 (88.23); 2.505 (190); 2.5 (264.68); 2.496 (187.05); 2.491 (85.07); 2.336 (0.55); 2.332 (1.15); 2.327 (1.58); 2.322 (1.12); 2.318 (0.52); 1.908 (1.85); 1.5 (7.27); 1.482 (16); 1.464 (7.18); 1.269 (4.93); 1.251 (10.54); 1.232 (4.85); 0.008 (0.63); 0 (21.63); 0.008 (0.63) Example 2-61: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.789 (0.78); 7.832 (4.59); 7.624 (1.36); 7.488 (3.17); 7.351 (1.57); 4.425 (2.21); 4.407 (7.28); 4.389 (7.44); 4.371 (2.36); 3.313 (44.01); 2.67 (0.6); 2.523 (1.36); 2.518 (1.97); 2.51 (31.73); 2.505 (70.06); 2.501 (98.7); 2.496 (68.26); 2.491 (29.74); 2.455 (0.71); 2.451 (0.9); 2.446 (0.73); 2.423 (13.86); 2.327 (0.66); 2.323 (0.54); 1.506 (7.04); 1.488 (16); 1.477 (0.88); 1.47 (7.03); 1.295 (0.67); 0.008 (1.25); 0 (53.01);0.009 (1.52) Example 2-62: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.848 (1.55); 8.258 (0.92); 8.12 (1.77); 8.058 (1.16); 8.038 (2.12); 7.993 (1.36); 7.983 (1.5); 7.974 (0.79); 4.411 (1.93); 4.393 (6.15); 4.375 (6.27); 4.357 (1.93); 3.311 (34.49); 3.092 (16); 2.674 (0.61); 2.67 (0.82); 2.665 (0.6); 2.523 (2.33); 2.518 (3.43); 2.51 (46.02); 2.505 (100.05); 2.5 (138.84); 2.496 (96.41); 2.491 (42.71); 2.455 (0.73); 2.45 (0.99); 2.446 (0.72); 2.332 (0.63); 2.327 (0.89); 2.323 (0.63); 1.498 (6.39); 1.488 (0.97); 1.48 (14.61); 1.462 (6.34); 0.008 (1.18); 0 (40.28); 0.009 (1.17) Example 2-63: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.914 (5.85); 8.15 (1.2); 8.13 (2.85); 8.108 (3.49); 8.087 (1.51); 7.945 (1.55); 7.81 (3.19); 7.673 (1.6); 4.434 (3.14); 4.416 (10.37); 4.398 (10.6); 4.379 (3.5); 3.581 (16); 3.313 (71.82); 3.263 (0.56); 3.094 (0.55); 2.674 (1.08); 2.669 (1.51); 2.665 (1.14); 2.544 (0.83); 2.533 (0.85); 2.523 (4.25); 2.518 (6.48); 2.509 (87.05); 2.505 (187.69); 2.5 (260.68); 2.496 (183.67); 2.491 (83.21); 2.455 (1.32); 2.45 (1.82); 2.446 (1.48); 2.332 (1.2); 2.327 (1.64); 2.322 (1.21); 2.072 (0.73); 1.908 (1.31); 1.509 (7.03); 1.491 (14.66); 1.473 (6.98); 0.008 (1.03); 0 (32.97); 0.009 (1.01) Example 2-64: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.796 (3.41); 7.845 (5.27); 7.625 (1.35); 7.488 (3.09); 7.352 (1.52); 4.425 (2.64); 4.407 (8.62); 4.388 (8.82); 4.37 (2.87); 3.313 (85.07); 3.281 (0.78); 3.262 (1.54); 2.967 (1); 2.949 (2.87); 2.931 (2.97); 2.913 (1.17); 2.674 (0.67); 2.67 (0.96); 2.665 (0.65); 2.523 (2.38); 2.518 (3.4); 2.51 (52.5); 2.505 (116.35); 2.501 (163.67); 2.496 (116.08); 2.491 (54.4); 2.451 (3.76); 2.332 (0.79); 2.327 (1.09); 2.323 (0.81); 1.506 (7.17); 1.488 (16); 1.47 (7.33); 1.182 (3.23); 1.164 (6.44); 1.145 (3.41); 0.008 (1.54); 0 (58.7); 0.008 (2.17); 0.05 (0.55) Example 2-65: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.851 (3.1); 8.281 (0.9); 8.144 (2.02); 8.07 (1.29); 8.05 (2.28); 8.007 (2.18); 7.987 (0.74); 5.753 (3.48); 4.412 (2.63); 4.394 (8.03); 4.376 (8.01); 4.358 (2.49); 3.308 (51.28); 3.292 (1.78); 3.274 (2.42); 3.256 (2.06); 3.238 (0.73); 2.674 (0.84); 2.669 (1.13); 2.665 (0.81); 2.523 (3.61); 2.518 (5.24); 2.509 (62.91); 2.505 (134.1); 2.5 (185.44); 2.496 (128.96); 2.491 (57.39); 2.332 (0.81); 2.327 (1.13); 2.322 (0.77); 1.498 (7.2); 1.48 (16); 1.462 (7.08); 1.36 (3.86); 1.342 (7.87); 1.323 (3.7); 0.008 (1.31); 0 (44.58); 0.009 (1.27) Example 2-66: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.907 (6.58); 8.148 (3.05); 8.132 (4.16); 8.111 (1.56); 7.946 (2.21); 7.809 (4.95); 7.673 (2.56); 5.753 (3.58); 4.431 (4.08); 4.413 (12.83); 4.395 (13.14); 4.377 (4.33); 3.736 (1.64); 3.718 (4.27); 3.7 (4.27); 3.682 (1.67); 3.308 (154.84); 2.674 (2.34); 2.669 (3.29); 2.664 (2.34); 2.605 (0.68); 2.6 (0.69); 2.596 (0.52); 2.523 (11.08); 2.518 (16.52); 2.509 (186.01); 2.505 (391.83); 2.5 (538.2); 2.496 (378.66); 2.491 (170.21); 2.405 (0.58); 2.401 (0.55); 2.336 (1.18); 2.332 (2.34); 2.327 (3.22); 2.322 (2.24); 2.072 (0.74); 1.507 (7.73); 1.489 (16); 1.471 (7.64); 1.285 (4.92); 1.268 (9.62); 1.249 (5.24); 0.008 (3.72); 0 (118.16); 0.008 (3.62) Example 2-73: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.7312 (2.7); 7.8291 (1.6); 7.8091 (2.3); 7.7295 (1.2); 7.7094 (0.9); 7.6171 (1.2); 7.4801 (2.7); 7.3432 (1.4); 4.4651 (1.8); 4.4469 (5.8); 4.4287 (5.8); 4.4106 (1.9); 4.1047 (1.2); 4.0866 (1.2); 3.3096 (124.1); 2.6740 (0.8); 2.6694 (1.2); 2.6648 (0.8); 2.5396 (1.0); 2.5229 (4.2); 2.5182 (5.7); 2.5095 (67.9); 2.5049 (143.6); 2.5003 (198.8); 2.4958 (137.4); 2.4912 (62.6); 2.4282 (0.5); 2.3895 (14.3); 2.3318 (0.9); 2.3271 (1.2); 2.3225 (0.9); 2.0724 (1.2); 1.5146 (7.0); 1.4965 (16.0); 1.4784 (7.0); 1.3127 (1.3); 1.2947 (2.7); 1.2765 (1.2); 0.0002 (1.4) Example 2-75: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.8398 (0.9); 8.0607 (1.6); 8.0404 (2.3); 7.9492 (1.5); 7.9288 (1.3); 7.7868 (2.0); 7.6505 (1.0); 4.4498 (1.0); 4.4316 (3.1); 4.4135 (3.2); 4.3954 (1.1); 3.5447 (16.0); 3.3082 (73.5); 2.6738 (0.7); 2.6693 (1.0); 2.6645 (0.7); 2.5225 (4.7); 2.5178 (6.5); 2.5091 (57.0); 2.5047 (114.6); 2.5001 (153.9); 2.4956 (107.8); 2.4911 (49.8); 2.3315 (0.6); 2.3269 (0.9); 1.9076 (0.6); 1.5032 (4.2); 1.4851 (9.3); 1.4670 (4.2); 0.0079 (1.0); 0.0002 (22.9); 0.0085 (0.8) Example 2-76: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.734 (3.5); 7.845 (1.51); 7.825 (2.18); 7.736 (1.27); 7.719 (1); 7.622 (1.21); 7.485 (2.66); 7.348 (1.31); 4.465 (1.85); 4.447 (5.86); 4.429 (5.95); 4.411 (1.97); 3.31 (15.7); 2.935 (1.05); 2.917 (3.01); 2.898 (3.1); 2.88 (1.08); 2.523 (1.13); 2.518 (1.54); 2.51 (27.58); 2.505 (60.79); 2.5 (85.15); 2.496 (59.71); 2.491 (26.86); 1.516 (7.27); 1.497 (16); 1.479 (7.16); 1.202 (3.41); 1.184 (6.77); 1.165 (3.3); 0.008 (1.06); 0 (37.76); 0.009 (1) Example 2-77: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): = 11.804 (3.11); 8.317 (0.87); 8.18 (1.85); 8.065 (1.77); 8.044 (2.97); 7.875 (1.2); 7.856 (1); 5.756 (2.22); 4.45 (2.21); 4.432 (6.58); 4.414 (6.53); 4.396 (2.09); 3.371 (0.61); 3.348 (0.8); 3.344 (0.92); 3.321 (147.23); 3.3 (1.36); 3.295 (0.98); 3.274 (1.21); 3.256 (1.09); 3.238 (0.85); 3.22 (1.62); 3.202 (1.7); 3.187 (0.99); 3.168 (0.77); 2.674 (0.56); 2.67 (0.77); 2.665 (0.53); 2.524 (3.93); 2.519 (5.79); 2.51 (47.64); 2.506 (96.69); 2.501 (130.94); 2.496 (91.41); 2.492 (40.65); 2.48 (1.21); 2.476 (0.93); 2.333 (0.56); 2.328 (0.78); 2.324 (0.53); 1.908 (1.8); 1.508 (7.33); 1.49 (16); 1.472 (7.12); 1.394 (4.4); 1.375 (8.88); 1.357 (4.11); 0.008 (0.79); 0 (21.3); 0.009 (0.63) Example 2-78: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): = 11.8469 (6.1); 8.1145 (2.7); 8.0943 (3.8); 8.0140 (3.3); 7.9939 (2.3); 7.9290 (2.0); 7.7926 (4.4); 7.6569 (2.2); 4.4720 (2.6); 4.4539 (7.6); 4.4358 (7.6); 4.4177 (2.6); 3.7188 (1.9); 3.7008 (5.1); 3.6822 (5.2); 3.6641 (1.9); 3.3760 (1.3); 3.3530 (2.2); 3.3273 (264.9); 3.2765 (0.5); 2.6701 (0.7); 2.5237 (3.8); 2.5105 (42.7); 2.5060 (87.1); 2.5014 (118.0); 2.4969 (83.3); 2.4924 (37.8); 2.3332 (0.5); 2.3286 (0.7); 1.5170 (7.8); 1.4989 (16.0); 1.4808 (7.7); 1.3113 (5.4); 1.2930 (10.6); 1.2746 (5.3); 0.0002 (2.2) Example 3-1: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.765 (0.6); 7.745 (1.24); 7.713 (1.31); 7.693 (0.61); 7.518 (0.61); 7.504 (1.1); 7.365 (2.37); 7.26 (110.75); 7.227 (1.16); 6.996 (0.61); 4.432 (1.91); 4.414 (2.54); 4.395 (1.99); 2.79 (8.62); 2.305 (16); 2.065 (1.18); 2.047 (2.14); 2.028 (2.13); 2.01 (1.26); 1.018 (4.29); 0.999 (8.94); 0.98 (4.15); 0.008 (1.31); 0 (45.01); 0.008 (1.28) Example 3-2: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.635 (1.2); 7.994 (0.94); 7.9 (0.62); 7.88 (1.28); 7.857 (0.62); 7.847 (1.64); 7.827 (0.76); 4.323 (2.06); 4.305 (3.02); 4.287 (2.13); 3.31 (32.73); 3.006 (16); 2.669 (0.58); 2.587 (9.22); 2.523 (1.72); 2.518 (2.56); 2.51 (32.26); 2.505 (70.05); 2.5 (97.77); 2.496 (68.17); 2.491 (30.37); 2.327 (0.54); 1.918 (1.19); 1.9 (2.12); 1.882 (2.12); 1.864 (1.21); 0.908 (4.27); 0.89 (9.45); 0.871 (4.02); 0.008 (0.59); 0 (20.02); 0.009 (0.56) Example 3-3: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.709 (2.02); 8.042 (0.88); 8.022 (1.14); 7.94 (1.98); 7.92 (2.35); 7.783 (2.55); 7.646 (1.19); 4.332 (3.05); 4.314 (4.5); 4.296 (3.16); 3.449 (22.02); 3.31 (102.47); 3.175 (0.65); 3.162 (0.66); 2.747 (16); 2.674 (1.3); 2.669 (1.84); 2.665 (1.3); 2.551 (0.5); 2.54 (0.62); 2.535 (0.75); 2.523 (5.28); 2.518 (8); 2.51 (105.64); 2.505 (228.67); 2.5 (317.05); 2.496 (221.05); 2.491 (98.27); 2.463 (0.66); 2.45 (0.99); 2.332 (1.29); 2.327 (1.81); 2.322 (1.34); 1.919 (1.69); 1.901 (3.04); 1.882 (3.12); 1.864 (1.77); 0.913 (6.63); 0.895 (14.54); 0.876 (6.17); 0.008 (1.76); 0 (61.61); 0.009 (1.8) Example 4-1: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.677 (6.48); 7.521 (1.05); 7.382 (2.45); 7.261 (15.43); 7.244 (1.19); 7.1 (1.13); 3.881 (13.55); 2.72 (12.81); 2.272 (16); 0 (6.76) Example 4-2: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.857 (0.66); 7.837 (1.38); 7.803 (1.37); 7.783 (0.66); 7.644 (2.96); 7.268 (0.7); 7.26 (67.37); 4.063 (1.58); 3.915 (0.9); 3.908 (14.64); 3.905 (3.49); 3.055 (1.21); 2.967 (0.66); 2.958 (16); 2.62 (6.52); 0.008 (0.82); 0 (30.16); 0.008 (0.93) Example 4-3: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.945 (0.87); 7.854 (3.09); 7.807 (1.93); 7.668 (0.94); 7.603 (0.77); 7.519 (0.67); 7.26 (125.38); 6.996 (0.66); 3.971 (0.5); 3.898 (0.6); 3.874 (8.69); 3.195 (16); 2.844 (11.22); 0.008 (1.27); 0 (48.95); 0.008 (1.37) Example 4-4: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.678 (5.46); 7.536 (1.25); 7.397 (2.9); 7.288 (1.73); 7.26 (81.53); 3.889 (16); 2.754 (1.62); 2.735 (5.25); 2.726 (15.87); 2.716 (4.96); 2.698 (1.55); 1.589 (0.52); 1.223 (5.31); 1.204 (10.84); 1.186 (4.93); 0.008 (1.22); 0 (28.79); 0.008 (0.79) Example 4-5: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.86 (4.53); 7.842 (1.29); 7.796 (1.85); 7.776 (1.05); 7.262 (24.93); 5.299 (0.8); 3.965 (16); 3.281 (0.56); 3.262 (0.52); 3.016 (0.93); 2.997 (0.98); 2.983 (0.79); 2.964 (0.77); 2.608 (3.34); 1.425 (3.08); 1.406 (6.35); 1.388 (2.93); 1.285 (0.77); 1.255 (0.72); 0 (9.06) Example 4-6: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.957 (1.24); 7.899 (0.89); 7.879 (2.38); 7.862 (1.52); 7.841 (0.91); 7.818 (2.72); 7.68 (1.54); 7.665 (1.82); 7.518 (2.1); 7.355 (0.51); 7.259 (384.1); 6.995 (1.99); 5.298 (3.43); 3.966 (1.1); 3.869 (12.06); 3.296 (1.61); 3.277 (5.09); 3.258 (5.26); 3.24 (1.71); 2.85 (16); 1.539 (2.37); 1.461 (1.05); 1.43 (5.1); 1.412 (10.1); 1.393 (4.94); 1.37 (1.31); 1.332 (7.88); 1.284 (10.97); 1.256 (4.17); 0.88 (0.71); 0.008 (5.04); 0 (144.57); 0.008 (5.71) Example 4-25: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.0342 (1.2); 7.8979 (1.1); 7.6361 (2.6); 7.5898 (0.6); 7.4521 (1.3); 7.3146 (0.6); 3.8047 (16.0); 3.4855 (0.5); 3.3085 (38.0); 2.5227 (1.8); 2.5180 (2.6); 2.5093 (28.2); 2.5047 (58.3); 2.5001 (80.0); 2.4956 (54.8); 2.4910 (24.8); 2.4229 (4.6); 2.4014 (0.8); 2.3269 (0.5); 1.2364 (0.9); 1.1167 (1.4); 1.0965 (1.4); 0.6673 (1.5); 0.6553 (1.4); 0.0080 (1.2); 0.0064 (0.5); 0.0002 (34.3); 0.0085 (1.0) Example 4-28: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.0592 (1.8); 7.9013 (1.8); 7.6478 (3.8); 7.6011 (0.8); 7.4647 (1.5); 7.3261 (0.7); 3.8054 (16.0); 3.3130 (161.1); 2.9099 (1.7); 2.8917 (1.7); 2.6696 (0.9); 2.5230 (2.8); 2.5095 (54.6); 2.5050 (116.8); 2.5005 (162.6); 2.4959 (115.8); 2.4914 (53.3); 2.3274 (0.8); 2.1905 (0.8); 1.9878 (1.6); 1.2375 (0.6); 1.1688 (2.1); 1.1506 (3.6); 1.1319 (2.2); 1.1113 (2.3); 1.0889 (2.2); 0.6566 (2.3); 0.0002 (27.6) Example 4-29: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.1164 (3.0); 8.4288 (0.6); 8.2920 (1.2); 8.1534 (0.7); 7.9208 (2.8); 7.9027 (1.4); 7.8295 (1.3); 7.8110 (0.8); 3.8214 (16.0); 3.3277 (114.0); 3.2046 (1.0); 3.1861 (1.4); 3.1662 (1.1); 2.6853 (0.6); 2.5254 (40.1); 2.5208 (83.0); 2.5163 (114.3); 2.5117 (79.0); 2.5072 (35.9); 2.3431 (0.7); 2.0703 (0.7); 2.0037 (1.6); 1.3551 (2.0); 1.3370 (3.8); 1.3182 (2.1); 1.2747 (0.6); 1.2522 (0.8); 1.2080 (0.8); 1.1903 (1.4); 1.1726 (1.3); 1.0397 (0.8); 0.7382 (1.4) Example 4-30: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 7.9772 (0.5); 7.9574 (1.2); 7.9376 (1.9); 7.7136 (0.8); 4.5780 (1.8); 3.8021 (16.0); 3.6474 (1.3); 3.6289 (1.4); 3.6107 (0.5); 3.3705 (11.5); 3.1686 (4.0); 2.5234 (1.9); 2.5100 (26.7); 2.5056 (54.0); 2.5011 (72.8); 2.4966 (51.3); 2.4921 (23.8); 1.3612 (1.3); 1.3428 (2.8); 1.3247 (1.5); 1.2356 (0.6); 1.0850 (1.2); 1.0644 (1.1); 0.7614 (1.2); 0.7487 (1.2); 0.0002 (13.2) Example 4-37: .sup.1H-NMR (400.0 MHz, CDCl3): = 8.1451 (0.6); 8.1257 (1.1); 8.1066 (0.7); 7.7963 (3.7); 7.6484 (1.3); 7.6277 (1.2); 7.3332 (1.0); 7.2602 (77.4); 7.1961 (2.1); 7.0590 (1.0); 3.8658 (16.0); 2.4727 (10.8); 1.5622 (0.7); 0.0080 (0.9); 0.0002 (27.2); 0.0085 (0.7) Example 4-38: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.0690 (1.1); 7.9259 (1.1); 7.8977 (0.9); 7.7766 (1.7); 7.7613 (2.4); 7.6255 (1.0); 3.7408 (16.0); 3.3106 (71.9); 3.1751 (1.7); 3.1619 (1.7); 3.0900 (8.1); 3.0503 (0.6); 2.6693 (0.8); 2.5092 (52.8); 2.5049 (102.7); 2.5004 (136.0); 2.4959 (96.5); 2.4916 (46.0); 2.3268 (0.8); 1.2372 (0.8); 0.0002 (12.6) Example 4-39: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.2608 (0.7); 7.9077 (1.3); 7.8869 (1.1); 7.8573 (0.7); 7.7217 (1.7); 7.5859 (0.8); 3.7525 (16.0); 3.7397 (0.8); 3.5804 (1.2); 3.5620 (1.2); 3.3099 (117.1); 2.6740 (0.8); 2.6694 (1.0); 2.6649 (0.7); 2.5228 (4.2); 2.5181 (5.9); 2.5094 (59.8); 2.5049 (123.2); 2.5003 (168.7); 2.4958 (116.6); 2.4912 (53.3); 2.3317 (0.7); 2.3271 (1.0); 2.3225 (0.7); 1.2552 (2.2); 1.2367 (5.2); 1.2184 (2.2); 0.0080 (1.0); 0.0002 (30.6); 0.0085 (1.0) Example 4-40: .sup.1H-NMR (400.0 MHz, CDCl3): = 8.1662 (0.5); 8.1466 (0.8); 8.1276 (0.6); 7.8130 (3.5); 7.6678 (1.1); 7.6472 (1.0); 7.3586 (0.7); 7.2602 (83.1); 7.2215 (1.5); 7.0843 (0.8); 3.9896 (1.5); 3.8706 (16.0); 3.8331 (1.8); 3.6488 (1.5); 2.9588 (0.8); 2.9403 (2.4); 2.9219 (2.5); 2.9034 (0.8); 1.2712 (2.2); 1.2532 (4.4); 1.2348 (2.1); 0.0079 (0.9); 0.0002 (29.5); 0.0085 (0.8) Example 4-41: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.0781 (0.8); 7.9416 (1.1); 7.9227 (0.6); 7.8055 (3.0); 7.7846 (1.1); 7.6695 (1.0); 4.0382 (0.7); 4.0204 (0.7); 3.7485 (1.7); 3.7376 (16.0); 3.6589 (1.0); 3.3441 (0.8); 3.3097 (128.8); 3.2694 (0.8); 3.2490 (0.6); 2.6740 (0.8); 2.6694 (1.0); 2.6648 (0.8); 2.5229 (4.3); 2.5181 (6.0); 2.5094 (59.3); 2.5049 (121.8); 2.5003 (166.1); 2.4958 (114.4); 2.4912 (52.1); 2.3317 (0.7); 2.3271 (1.0); 2.3225 (0.7); 1.9876 (3.0); 1.2482 (2.1); 1.2297 (4.1); 1.2114 (2.3); 1.1923 (1.2); 1.1745 (1.8); 1.1567 (0.9); 0.0080 (0.9); 0.0002 (29.1); 0.0085 (0.9) Example 4-42: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.2633 (0.9); 7.8929 (1.3); 7.8750 (1.0); 7.8552 (0.8); 7.7189 (2.1); 7.5823 (0.9); 7.4594 (0.5); 3.7397 (8.9); 3.6685 (1.8); 3.6387 (0.9); 3.5752 (1.8); 3.5641 (1.6); 3.5559 (1.8); 3.5101 (0.6); 3.4853 (0.8); 3.3590 (2.0); 3.3475 (1.6); 3.3093 (409.3); 2.6740 (2.2); 2.6694 (3.0); 2.6647 (2.2); 2.5497 (2.2); 2.5228 (13.1); 2.5181 (18.6); 2.5094 (180.5); 2.5049 (368.1); 2.5003 (502.5); 2.4957 (348.7); 2.4912 (159.5); 2.4706 (1.3); 2.4655 (1.4); 2.3317 (2.1); 2.3270 (2.9); 2.3224 (2.1); 1.3196 (1.5); 1.2982 (0.8); 1.2538 (3.7); 1.2357 (16.0); 1.2178 (4.1); 1.2013 (1.0); 0.8538 (1.4); 0.8364 (0.6); 0.0080 (3.4); 0.0002 (158.0); 0.0085 (7.0); 0.1501 (0.6) Example 4-49: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.333 (0.88); 7.918 (0.83); 7.859 (0.7); 7.84 (0.92); 7.776 (1.1); 7.755 (0.72); 7.605 (0.64); 7.468 (1.32); 7.332 (0.65); 3.791 (16); 3.474 (2.91); 2.674 (0.65); 2.669 (0.91); 2.665 (0.62); 2.523 (2.01); 2.518 (3.06); 2.51 (48.55); 2.505 (107.49); 2.5 (151.19); 2.496 (105.96); 2.491 (47.61); 2.455 (1.15); 2.45 (1.42); 2.446 (1.18); 2.425 (5.59); 2.332 (0.73); 2.327 (1.04); 2.322 (0.75); 0.008 (1.02); 0 (43.65); 0.008 (1.4) Example 4-50: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.063 (0.72); 7.985 (0.92); 7.926 (0.75); 3.78 (16); 3.092 (3.3); 2.523 (1.85); 2.518 (2.82); 2.51 (30.57); 2.505 (63.43); 2.5 (86.36); 2.496 (61.52); 2.491 (28.65); 2.327 (0.55) Example 4-51: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.176 (1.48); 8.076 (1.77); 8.055 (1.58); 7.96 (2.24); 7.823 (1.95); 3.825 (16); 3.595 (10.57); 3.402 (63.21); 2.694 (1.86); 2.548 (4.42); 2.543 (6.94); 2.534 (108.49); 2.53 (231.87); 2.525 (318.71); 2.521 (225.86); 2.516 (103.46); 2.352 (1.86) Example 4-52: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.3456 (1.1); 7.9188 (1.0); 7.8657 (0.7); 7.8474 (1.0); 7.7935 (1.2); 7.7743 (0.8); 7.6052 (0.6); 7.4685 (1.2); 7.3325 (0.6); 3.7908 (16.0); 3.4179 (1.9); 3.1684 (5.6); 2.9482 (1.6); 2.9298 (1.6); 2.6695 (0.6); 2.5230 (1.3); 2.5183 (2.0); 2.5096 (33.3); 2.5050 (73.7); 2.5004 (103.6); 2.4958 (72.8); 2.4912 (33.0); 2.4549 (0.7); 2.4505 (0.9); 2.4459 (0.6); 2.3272 (0.7); 1.1703 (1.7); 1.1522 (3.2); 1.1342 (1.9); 0.0080 (0.7); 0.0002 (27.9); 0.0085 (0.9) Example 4-53: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.2356 (0.6); 8.0988 (1.2); 8.0019 (1.7); 7.9620 (0.9); 7.9317 (0.9); 5.7549 (2.5); 5.7532 (2.6); 3.7799 (16.0); 3.5748 (3.5); 3.2873 (1.5); 3.2691 (1.5); 2.5052 (49.2); 2.5013 (61.2); 2.4979 (46.0); 1.3319 (1.7); 1.3137 (3.2); 1.2961 (1.8); 0.0014 (8.0); 0.0002 (8.3) Example 4-54: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.1904 (0.7); 8.1708 (0.9); 8.0763 (1.0); 8.0562 (0.7); 7.9493 (1.4); 7.7989 (1.0); 4.7745 (1.3); 3.7990 (16.0); 3.7420 (0.7); 3.7242 (0.8); 3.6949 (1.3); 3.6772 (1.3); 3.6598 (0.6); 3.6191 (0.6); 3.3703 (14.0); 2.6701 (0.6); 2.5233 (3.0); 2.5100 (40.0); 2.5055 (79.0); 2.5010 (105.4); 2.4965 (74.2); 2.4920 (35.0); 2.3277 (0.6); 1.2679 (1.5); 1.2498 (2.8); 1.2322 (1.6); 1.1195 (0.8); 1.1018 (1.6); 1.0840 (0.8); 0.0080 (1.4); 0.0002 (36.1); 0.0085 (1.3) Example 4-61: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.317 (1.92); 7.912 (1.73); 7.8 (4.35); 7.617 (0.87); 7.48 (1.79); 7.344 (0.9); 3.815 (16); 3.311 (53.37); 3.261 (0.82); 2.674 (0.73); 2.669 (0.99); 2.665 (0.76); 2.552 (0.59); 2.523 (2.3); 2.518 (3.39); 2.51 (52.75); 2.505 (116.08); 2.5 (162.65); 2.496 (114.42); 2.491 (53.15); 2.451 (3.86); 2.421 (9.65); 2.332 (0.83); 2.327 (1.16); 2.322 (0.84); 0.008 (1.51); 0 (61.65); 0.008 (2.21) Example 4-63: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.473 (3.87); 8.107 (7.38); 7.969 (1.31); 7.946 (3.93); 7.832 (2.21); 7.696 (1.12); 3.855 (16); 3.603 (14.46); 3.338 (145.94); 2.697 (1.06); 2.528 (176.33); 2.355 (1.03); 2.015 (1.04); 1.202 (0.57) Example 4-64: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.328 (2.17); 7.912 (2.21); 7.816 (2.84); 7.619 (0.75); 7.483 (1.49); 7.346 (0.7); 3.815 (16); 3.315 (46.07); 3.263 (0.82); 2.968 (0.84); 2.949 (2.25); 2.931 (2.34); 2.913 (1.01); 2.674 (0.67); 2.67 (0.94); 2.665 (0.68); 2.523 (2.27); 2.518 (3.58); 2.51 (54.71); 2.505 (116.11); 2.5 (158.97); 2.496 (112.64); 2.491 (52.4); 2.447 (3.71); 2.332 (0.8); 2.327 (1.05); 2.323 (0.77); 1.182 (2.46); 1.164 (4.91); 1.146 (2.73); 0.008 (1.35); 0 (52.7); 0.008 (2.08) Example 4-65: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.174 (1.02); 8.052 (1.27); 7.986 (1.22); 7.955 (1.36); 3.828 (12.61); 3.548 (16); 3.297 (1.3); 2.698 (0.93); 2.533 (111.33); 2.528 (151.51); 2.524 (117.84); 2.354 (0.88); 1.388 (1.61); 1.368 (2.99) Example 4-66: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.098 (2.51); 7.949 (1.23); 7.805 (0.67); 5.754 (2.65); 4.135 (16); 3.824 (6.27); 3.716 (1.04); 3.698 (1.05); 2.507 (35.28); 2.503 (46.53); 2.499 (35.74); 1.282 (1.14); 1.263 (2.14); 1.245 (1.19); 0 (5.49) Example 4-73: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.258 (2.68); 7.908 (2.46); 7.808 (1.75); 7.789 (2.35); 7.684 (2.11); 7.665 (1.62); 7.61 (1.19); 7.473 (2.51); 7.336 (1.22); 3.852 (16); 3.309 (29.72); 2.669 (0.58); 2.523 (1.41); 2.518 (2.12); 2.509 (31.57); 2.505 (68.77); 2.5 (96.02); 2.496 (68.07); 2.491 (30.91); 2.387 (14.1); 2.332 (0.52); 2.327 (0.68); 2.322 (0.51); 0.008 (1.48); 0 (50.83); 0.009 (1.48) Example 4-74: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.201 (1.16); 8.066 (1.67); 7.951 (1.79); 7.849 (1.28); 7.828 (1.05); 3.865 (16); 3.086 (7.03); 2.698 (0.95); 2.529 (162.8); 2.354 (0.98) Example 4-75: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.0572 (2.0); 8.0369 (2.9); 7.9281 (4.6); 7.9137 (2.1); 7.7875 (2.1); 7.6509 (1.0); 3.8625 (16.0); 3.8380 (4.4); 3.7837 (15.1); 3.5457 (15.0); 3.0584 (0.7); 2.6744 (1.3); 2.6697 (1.8); 2.6653 (1.3); 2.5516 (1.8); 2.5449 (4.6); 2.5309 (9.4); 2.5097 (122.3); 2.5052 (234.2); 2.5007 (305.7); 2.4961 (214.7); 2.4916 (98.4); 2.4519 (1.3); 2.3321 (1.3); 2.3275 (1.8); 2.3229 (1.3); 0.0079 (1.3); 0.0002 (26.9); 0.0084 (0.9) Example 4-76: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.263 (2.98); 7.908 (3.37); 7.823 (1.96); 7.802 (2.43); 7.689 (2.25); 7.67 (1.89); 7.615 (1.23); 7.478 (2.49); 7.34 (1.24); 3.851 (16); 3.308 (51.97); 2.933 (1.48); 2.915 (3.76); 2.897 (3.97); 2.878 (1.5); 2.669 (0.84); 2.509 (53.27); 2.505 (113.96); 2.5 (157.5); 2.496 (110.8); 2.491 (50.03); 2.327 (0.81); 1.2 (4.11); 1.182 (8.11); 1.164 (4.14); 0.008 (1.49); 0 (46.07); 0.008 (1.32) Example 4-77: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 11.325 (4.98); 8.316 (0.92); 8.18 (1.86); 8.044 (2.62); 8.025 (2.17); 7.914 (3.12); 7.83 (2.03); 7.812 (1.72); 3.841 (16); 3.314 (108.52); 3.274 (2.19); 3.259 (1.75); 3.235 (1.04); 3.214 (1.46); 3.198 (1.43); 3.18 (1.13); 3.164 (0.82); 2.674 (1.48); 2.67 (1.94); 2.665 (1.38); 2.523 (7.61); 2.509 (130.64); 2.505 (254.8); 2.5 (331.08); 2.496 (233.82); 2.492 (114.74); 2.332 (1.64); 2.327 (2.06); 2.072 (0.76); 1.393 (3.77); 1.375 (7.41); 1.356 (3.97); 0.008 (2.62); 0.001 (36.17); 0 (52.19); 0.008 (2.17) Example 4-78: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.086 (1.73); 8.066 (2.41); 7.954 (2.16); 7.928 (3.89); 7.788 (1.83); 7.652 (0.87); 3.861 (13.04); 3.774 (16); 3.698 (3.82); 3.679 (3.57); 3.661 (1.52); 2.67 (1.78); 2.523 (4.5); 2.518 (6.77); 2.51 (98.48); 2.505 (213.47); 2.501 (296.57); 2.496 (207.91); 2.492 (92.34); 2.328 (1.65); 2.072 (1.37); 1.306 (3.22); 1.288 (6.95); 1.27 (3.01); 0.008 (1.64); 0 (58.19); 0.008 (1.91) Example 5-1: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.783 (0.59); 7.685 (0.8); 7.665 (1.75); 7.633 (1.65); 7.613 (0.77); 7.503 (0.93); 7.365 (2.03); 7.26 (83.93); 7.227 (0.97); 7.21 (0.55); 4.145 (1.68); 2.76 (10.22); 2.522 (1.57); 2.513 (12.53); 2.495 (1.81); 2.468 (1.37); 2.297 (16); 2.262 (1.93); 1.55 (1.06); 1.269 (0.93); 1.038 (0.9); 0.008 (0.97); 0 (35.94); 0.008 (1.14) Example 5-2: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.842 (0.83); 7.822 (1.2); 7.741 (1.21); 7.721 (0.83); 7.519 (0.81); 7.26 (149.61); 7.21 (1.2); 6.996 (0.81); 2.95 (16); 2.56 (6.37); 2.502 (15.6); 1.548 (1.99); 0.008 (1.71); 0 (63.1); 0.008 (1.72) Example 6-4: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.7 (1.58); 7.68 (2.83); 7.667 (1.09); 7.623 (2.63); 7.603 (1.55); 7.524 (1.52); 7.386 (3.25); 7.266 (0.59); 7.266 (0.68); 7.265 (0.87); 7.264 (1.12); 7.26 (67.17); 7.248 (1.69); 2.777 (2.16); 2.759 (6.92); 2.751 (16); 2.74 (6.59); 2.722 (2.12); 1.581 (1.4); 1.243 (7.3); 1.225 (15.01); 1.206 (6.88); 0.008 (0.78); 0 (26.31); 0.008 (0.67) Example 6-5: .sup.1H-NMR (400.0 MHz, CDCl3): = 9.616 (0.89); 7.825 (3.54); 7.805 (5.32); 7.738 (7.15); 7.718 (4.84); 7.519 (2.95); 7.295 (0.71); 7.287 (0.59); 7.283 (0.66); 7.281 (0.62); 7.28 (0.82); 7.279 (0.94); 7.278 (0.98); 7.277 (1.06); 7.276 (1.11); 7.276 (1.23); 7.275 (1.28); 7.274 (1.54); 7.273 (1.58); 7.272 (1.75); 7.272 (2.04); 7.271 (2.41); 7.27 (2.79); 7.269 (3.23); 7.269 (3.51); 7.268 (3.91); 7.267 (4.83); 7.266 (6.04); 7.265 (7.71); 7.264 (9.93); 7.26 (522.59); 7.256 (6); 7.255 (4.35); 7.254 (3.49); 7.253 (2.95); 7.252 (2.34); 7.252 (1.78); 7.251 (1.71); 7.25 (1.38); 7.249 (1.32); 7.248 (1.32); 7.248 (1.23); 7.247 (1.01); 7.246 (0.92); 7.245 (1); 7.244 (0.79); 7.244 (0.78); 7.243 (0.69); 7.242 (0.73); 7.241 (0.67); 7.24 (0.59); 7.24 (0.71); 7.239 (0.64); 7.236 (0.59); 7.232 (0.52); 7.228 (0.62); 7.21 (0.65); 6.996 (2.77); 5.298 (0.53); 3.265 (0.62); 3.247 (1.93); 3.229 (2.25); 3.214 (2.55); 3.195 (2.39); 3.177 (0.8); 2.982 (1.09); 2.963 (4.08); 2.948 (1.27); 2.944 (4.25); 2.93 (3.43); 2.925 (1.54); 2.91 (3.31); 2.892 (1.06); 2.506 (16); 1.576 (67.91); 1.49 (1.05); 1.421 (13.84); 1.402 (28.46); 1.383 (12.97); 1.37 (1); 1.33 (0.75); 1.285 (1.54); 1.256 (1.71); 0.146 (0.57); 0.008 (6.02); 0 (206.24); 0.008 (5.61); 0.149 (0.6) Example 6-6: .sup.1H-NMR (400.0 MHz, CDCl3): = 8.161 (0.52); 7.924 (1.71); 7.904 (2.51); 7.821 (1.51); 7.81 (1.18); 7.801 (1.07); 7.673 (1.84); 7.535 (0.94); 7.26 (73.64); 3.286 (1.79); 3.267 (5.88); 3.248 (5.99); 3.23 (1.85); 2.806 (16); 1.547 (3.33); 1.426 (5.36); 1.407 (11.09); 1.389 (5.05); 0.008 (1.08); 0 (28.46); 0.008 (0.85) Example 7-1: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.688 (0.76); 7.668 (1.42); 7.624 (1.56); 7.604 (0.83); 7.496 (1.04); 7.357 (2.44); 7.266 (0.56); 7.266 (0.68); 7.265 (0.85); 7.26 (52.32); 7.219 (1.26); 4.126 (0.93); 2.748 (10.89); 2.582 (0.99); 2.531 (16); 2.46 (0.81); 2.283 (15.03); 0.008 (0.75); 0 (22.28); 0.008 (0.61) Example 7-2: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 7.979 (1.0); 7.842 (0.5); 7.790 (5.8); 5.753 (1.6); 3.309 (25.9); 2.989 (16.0); 2.537 (9.3); 2.523 (1.4); 2.518 (1.8); 2.509 (19.5); 2.505 (41.8); 2.500 (58.2); 2.496 (41.3); 2.491 (19.5); 2.485 (13.1); 0.000 (13.3) Example 7-3: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.938 (1.26); 7.842 (1.97); 7.822 (0.54); 7.8 (2.82); 7.661 (1.44); 7.52 (1.23); 7.311 (0.5); 7.261 (208.56); 6.996 (1.21); 3.206 (16); 2.831 (14.52); 2.534 (13.34); 1.545 (2.44); 0.008 (2.67); 0 (92.86); 0.008 (2.76) Example 7-4: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.689 (1.07); 7.668 (2.22); 7.632 (1.94); 7.612 (0.94); 7.517 (0.93); 7.379 (2.09); 7.261 (28.01); 7.24 (1.03); 5.299 (1.21); 2.764 (1.27); 2.745 (4.06); 2.734 (11.3); 2.726 (4.32); 2.708 (1.29); 2.526 (16); 1.229 (4.49); 1.21 (9.27); 1.192 (4.23); 0 (10.2) Example 7-11: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.66 (1); 7.64 (2.9); 7.62 (2.1); 7.599 (0.76); 7.513 (1.11); 7.374 (2.53); 7.261 (31.84); 7.236 (1.28); 5.299 (2.55); 3.217 (0.86); 3.199 (2.88); 3.18 (2.94); 3.162 (0.9); 2.532 (16); 2.313 (15.92); 1.25 (1.49); 1.232 (2.93); 1.213 (1.43); 0 (13.53) Example 7-12: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.191 (0.74); 8.105 (0.88); 7.854 (0.51); 7.833 (2.41); 7.823 (1.92); 3.311 (26.21); 3.175 (0.51); 3.162 (0.51); 3.03 (16); 2.846 (0.55); 2.523 (0.76); 2.518 (1.24); 2.51 (16.09); 2.505 (34.38); 2.5 (47.68); 2.496 (33.94); 2.491 (18.19); 1.209 (2.47); 1.191 (5.96); 1.172 (2.44); 0 (12.07) Example 7-13: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.284 (1.91); 7.972 (2.8); 7.952 (5.13); 7.914 (6.07); 7.895 (4.46); 7.76 (5.53); 7.624 (2.74); 3.425 (40.65); 3.375 (0.71); 3.31 (156.79); 3.26 (1.2); 3.19 (4.01); 3.174 (4.57); 3.162 (2.89); 3.019 (0.57); 2.67 (1.54); 2.509 (103.43); 2.505 (199.64); 2.5 (263.74); 2.496 (199.47); 2.45 (2.82); 2.327 (1.79); 1.232 (7.42); 1.214 (16); 1.196 (7.18); 1.097 (0.77); 1.022 (0.74); 1.006 (0.65); 0 (45.05) Example 7-14: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.098 (1.07); 7.667 (3.86); 7.663 (4.92); 7.638 (1.19); 7.5 (3.23); 7.363 (1.46); 5.754 (3.08); 3.31 (89.88); 3.26 (0.78); 3.087 (0.6); 3.07 (1.7); 3.051 (1.72); 3.033 (0.63); 2.795 (1.75); 2.776 (5.81); 2.758 (5.86); 2.739 (1.86); 2.674 (0.64); 2.669 (0.87); 2.665 (0.63); 2.523 (1.96); 2.518 (2.92); 2.51 (47.85); 2.505 (105.77); 2.5 (149.11); 2.496 (104.09); 2.491 (46.99); 2.486 (16.77); 2.467 (0.77); 2.455 (1.29); 2.451 (1.37); 2.446 (0.86); 2.332 (0.69); 2.327 (0.94); 2.322 (0.68); 2.072 (0.57); 1.174 (7.09); 1.166 (3.91); 1.155 (16); 1.147 (9.93); 1.137 (7.11); 1.128 (3.84); 0.008 (2.34); 0.006 (0.52); 0.006 (0.55); 0.005 (0.65); 0.004 (0.88); 0.003 (1.49); 0.002 (2.69); 0.002 (4.22); 0 (83.52); 0.003 (4.54); 0.003 (2.92); 0.004 (1.79); 0.005 (1.32); 0.006 (1.09); 0.007 (0.97); 0.008 (0.99); 0.008 (2.5); 0.011 (0.55); 0.05 (0.54) Example 7-15: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.2 (1.5); 8.087 (0.69); 7.857 (1.06); 7.836 (4.77); 7.826 (4.02); 7.806 (0.88); 3.31 (124.99); 3.29 (0.62); 3.271 (1.38); 3.26 (1.29); 3.253 (1.64); 3.238 (2.02); 3.22 (1.95); 3.201 (0.56); 3.118 (0.5); 3.099 (1.68); 3.08 (1.8); 3.066 (1.33); 3.047 (1.22); 2.964 (0.58); 2.87 (0.72); 2.853 (0.89); 2.836 (0.66); 2.674 (0.8); 2.669 (1.14); 2.665 (0.82); 2.523 (2.79); 2.518 (4.14); 2.51 (63.33); 2.505 (140.43); 2.5 (198.05); 2.496 (137.85); 2.491 (63.3); 2.486 (24.91); 2.46 (0.94); 2.455 (1.39); 2.45 (1.88); 2.446 (1.55); 2.441 (0.97); 2.332 (0.98); 2.327 (1.27); 2.322 (0.96); 1.323 (7.23); 1.305 (16); 1.286 (6.94); 1.203 (5.31); 1.185 (13.1); 1.166 (5.3); 0.008 (1.44); 0 (59.62); 0.009 (1.78) Example 7-16: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.285 (1.74); 7.987 (1.13); 7.967 (2.5); 7.939 (3.39); 7.918 (1.49); 7.891 (1.53); 7.754 (3.59); 7.618 (1.8); 3.495 (1.78); 3.476 (6.1); 3.458 (6.27); 3.44 (1.93); 3.31 (113.65); 3.26 (0.7); 3.166 (1.64); 3.148 (1.68); 2.674 (0.9); 2.669 (1.26); 2.665 (0.92); 2.523 (3.54); 2.518 (5.03); 2.51 (67.76); 2.505 (148.13); 2.5 (208.18); 2.496 (146.16); 2.491 (71.36); 2.47 (0.55); 2.455 (1.22); 2.45 (1.56); 2.446 (1.18); 2.332 (0.94); 2.327 (1.33); 2.322 (0.95); 1.265 (6.82); 1.247 (16); 1.228 (7.02); 1.22 (4.53); 1.202 (10.39); 1.184 (4.33); 0.008 (2.23); 0 (85.2); 0.004 (1.13); 0.005 (0.79); 0.006 (0.68); 0.007 (0.63); 0.008 (2.41) Example 7-47: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.3070 (2.4); 11.4223 (0.7); 7.7989 (6.2); 7.7790 (14.0); 7.7563 (16.0); 7.7361 (5.9); 7.5962 (5.3); 7.4592 (11.9); 7.3226 (5.8); 4.0859 (0.7); 4.0077 (0.6); 3.8043 (0.6); 3.3105 (152.1); 3.1746 (3.3); 3.1626 (3.0); 2.6742 (2.9); 2.6696 (3.6); 2.6648 (2.8); 2.5868 (5.2); 2.5094 (218.0); 2.5050 (397.9); 2.5004 (513.0); 2.4960 (361.2); 2.4915 (177.5); 2.4520 (5.4); 2.4305 (19.4); 2.4139 (76.2); 2.3930 (3.2); 2.3629 (1.2); 2.3479 (1.8); 2.3321 (2.7); 2.3272 (3.4); 2.2618 (1.7); 2.1052 (5.1); 1.9153 (0.6); 1.2989 (0.5); 1.2353 (2.3); 0.0002 (43.6) Example 7-48: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.3984 (0.7); 8.2036 (0.9); 8.0666 (1.5); 7.9723 (2.9); 7.9652 (3.2); 7.9448 (0.5); 7.9295 (1.0); 3.3267 (60.2); 3.0981 (16.0); 2.5385 (2.0); 2.5338 (2.8); 2.5251 (27.8); 2.5205 (57.2); 2.5159 (78.4); 2.5114 (53.6); 2.5068 (25.0); 2.4994 (6.9) Example 7-49: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.4960 (1.2); 8.1011 (1.2); 8.0495 (2.0); 8.0291 (1.2); 7.9414 (1.0); 7.8049 (2.4); 7.6679 (1.2); 4.0541 (1.1); 4.0363 (1.0); 3.5704 (16.0); 3.3765 (0.6); 3.3257 (79.3); 3.3134 (1.8); 3.3089 (0.9); 3.3031 (0.5); 3.2759 (1.2); 3.0732 (0.6); 2.6895 (0.7); 2.6850 (1.0); 2.5892 (0.6); 2.5759 (0.8); 2.5711 (0.9); 2.5665 (0.8); 2.5501 (0.7); 2.5387 (3.2); 2.5340 (4.9); 2.5253 (52.3); 2.5208 (109.5); 2.5162 (152.1); 2.5116 (105.5); 2.5071 (49.3); 2.5002 (5.5); 2.4954 (2.7); 2.4715 (1.2); 2.4670 (1.8); 2.4623 (1.6); 2.4574 (1.1); 2.4540 (0.7); 2.4451 (0.6); 2.4404 (0.5); 2.4173 (0.7); 2.3430 (0.9); 2.2580 (0.6); 2.0036 (4.6); 1.2081 (1.4); 1.1904 (2.7); 1.1726 (1.4) Example 7-50: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 7.7852 (0.8); 7.7749 (1.0); 7.4596 (0.7); 3.3497 (16.0); 2.9360 (1.0); 2.9176 (1.0); 2.5123 (3.5); 2.5077 (7.3); 2.5031 (10.1); 2.4986 (7.0); 2.4940 (3.4); 2.4845 (1.4); 1.9175 (0.6); 1.1652 (1.2); 1.1468 (2.5); 1.1364 (0.6); 1.1284 (1.2) Example 7-51: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 7.9641 (0.7); 7.9515 (0.8); 3.3105 (16.0); 3.2738 (0.7); 3.2553 (0.7); 2.5229 (0.6); 2.5094 (10.1); 2.5049 (21.0); 2.5004 (28.8); 2.4958 (20.0); 2.4913 (9.1); 2.4774 (2.2); 1.3241 (0.8); 1.3055 (1.6); 1.2868 (0.8) Example 7-52: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.1218 (0.9); 7.9739 (9.1); 7.9528 (1.2); 7.9095 (1.7); 7.8961 (1.2); 7.8764 (1.1); 7.7728 (3.7); 7.6365 (1.8); 4.0383 (1.7); 4.0206 (1.7); 4.0028 (1.0); 3.6786 (3.5); 3.6600 (7.9); 3.6416 (7.8); 3.6227 (3.2); 3.3074 (136.1); 3.2562 (1.0); 2.6692 (6.8); 2.5089 (156.6); 2.5046 (276.6); 2.5001 (358.5); 2.4956 (270.3); 2.4461 (1.1); 2.4045 (17.7); 2.3269 (2.1); 2.1780 (0.7); 2.1232 (1.0); 1.9875 (5.0); 1.9077 (0.5); 1.2461 (8.2); 1.2276 (16.0); 1.2090 (7.3); 1.1923 (1.7); 1.1746 (2.9); 1.1567 (1.6); 0.8735 (0.8); 0.8545 (0.5); 0.0002 (25.6) Example 7-59: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.285 (11.15); 7.797 (7.79); 7.777 (16); 7.741 (11.02); 7.722 (6.04); 7.607 (7.23); 7.588 (1.37); 7.543 (1.25); 7.47 (15.69); 7.333 (7.54); 3.806 (2.57); 3.309 (308.67); 3.259 (2.39); 2.674 (3.82); 2.669 (5.18); 2.665 (3.73); 2.556 (1.87); 2.522 (21.21); 2.509 (336.55); 2.505 (677.17); 2.5 (910.54); 2.496 (647.97); 2.491 (314.67); 2.451 (8.82); 2.409 (92.72); 2.39 (5.64); 2.332 (4.77); 2.327 (6.16); 2.323 (4.7); 2.072 (8.25); 0.146 (1.44); 0.008 (16.38); 0 (391.24); 0.008 (14.27); 0.05 (2.19); 0.15 (1.69) Example 7-60: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 3.3107 (16.0); 3.0709 (3.6); 2.5228 (0.7); 2.5095 (13.7); 2.5050 (28.8); 2.5005 (39.6); 2.4959 (27.7); 2.4915 (12.6); 2.4611 (2.8) Example 7-62: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.297 (3.89); 7.813 (2.72); 7.793 (4.79); 7.745 (2.81); 7.725 (1.74); 7.608 (2.26); 7.471 (5.25); 7.335 (2.53); 3.312 (116.32); 3.279 (1.3); 3.262 (1.7); 3.243 (0.79); 2.954 (2.05); 2.935 (6.37); 2.917 (6.6); 2.898 (2.49); 2.674 (1.25); 2.67 (1.78); 2.665 (1.3); 2.551 (0.94); 2.523 (4.29); 2.518 (6.37); 2.51 (95.36); 2.505 (211.57); 2.5 (298.93); 2.496 (212.49); 2.491 (102.95); 2.451 (6.21); 2.332 (1.45); 2.327 (1.99); 2.323 (1.49); 2.073 (0.82); 1.174 (7.7); 1.156 (16); 1.137 (7.73); 0.008 (2.67); 0.006 (0.55); 0.006 (0.59); 0.005 (0.7); 0 (94.47); 0.005 (2.23); 0.006 (1.94); 0.007 (1.75); 0.008 (3.38); 0.051 (0.56) Example 7-71: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): = 7.808 (1.5); 7.789 (1.75); 7.615 (1.07); 7.595 (0.94); 7.583 (1.11); 7.446 (2.14); 7.309 (1.05); 4.152 (16); 3.187 (1.47); 3.183 (2.73); 3.179 (3.8); 3.175 (2.65); 3.171 (1.34); 2.58 (1.33); 2.551 (6.96); 2.547 (13.3); 2.542 (17.67); 2.538 (12.57); 2.533 (6.12); 2.502 (3.34); 2.393 (11.85); 2.375 (0.65); 2.047 (0.78); 0 (1.87) Example 7-72: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.3017 (0.6); 8.1636 (1.3); 8.0261 (0.7); 7.9259 (1.1); 7.9062 (1.2); 7.6232 (1.2); 7.6031 (1.1); 3.3090 (37.8); 3.0268 (16.0); 2.6739 (0.7); 2.6693 (1.0); 2.6646 (0.7); 2.5556 (0.5); 2.5507 (0.6); 2.5227 (3.6); 2.5180 (5.1); 2.5093 (54.6); 2.5048 (112.2); 2.5002 (152.6); 2.4956 (105.2); 2.4911 (47.9); 2.4561 (0.6); 2.4518 (0.6); 2.3878 (10.1); 2.3316 (0.7); 2.3270 (0.9); 2.3224 (0.6); 1.9075 (1.3); 0.0080 (1.2); 0.0002 (32.9); 0.0085 (1.0) Example 7-74: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 12.225 (3.02); 7.802 (3.59); 7.782 (4.31); 7.625 (2.36); 7.605 (4); 7.468 (4.83); 7.331 (2.29); 3.308 (31.48); 2.922 (2.06); 2.904 (6.48); 2.885 (6.79); 2.867 (2.46); 2.67 (0.72); 2.523 (2.24); 2.51 (44.57); 2.505 (95.06); 2.5 (132.34); 2.496 (96.1); 2.491 (47.54); 2.327 (0.76); 1.193 (7.72); 1.174 (16); 1.156 (7.79); 0.008 (1.47); 0 (50.69); 0.009 (1.57) Example 7-75: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 8.3100 (0.6); 8.1716 (1.3); 8.0333 (0.7); 7.8209 (1.7); 7.8009 (1.9); 7.4686 (2.2); 7.4487 (2.0); 4.0881 (0.7); 4.0747 (0.8); 3.3109 (62.3); 3.2707 (1.2); 3.2518 (0.8); 3.2372 (1.2); 3.2183 (1.1); 3.1743 (3.5); 3.1613 (3.8); 3.1444 (1.0); 3.1262 (1.1); 3.1106 (0.7); 3.0927 (0.6); 2.6693 (0.6); 2.5498 (0.7); 2.5450 (0.7); 2.5046 (66.7); 2.5001 (94.3); 2.4957 (73.7); 2.3270 (0.6); 2.2695 (16.0); 1.3734 (3.2); 1.3549 (6.7); 1.3363 (3.2); 0.0080 (0.9); 0.0002 (27.5); 0.0084 (1.6) Example 9-25: .sup.1H-NMR (400.0 MHz, CDCl3): = 7.963 (1.47); 7.942 (1.75); 7.712 (1.65); 7.692 (1.43); 7.518 (0.58); 7.449 (0.9); 7.312 (1.97); 7.271 (0.56); 7.271 (0.56); 7.268 (0.79); 7.259 (100.61); 7.174 (0.95); 6.995 (0.57); 2.423 (16); 0.008 (1.4); 0 (43.08); 0.008 (1.14)
B. Formulation Examples
[0101] a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill. [0102] b) A readily water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. [0103] c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to above 277 C), and grinding the mixture in a friction ball mill to a fineness of below 5 microns. [0104] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier. [0105] e) Water-dispersible granules are obtained by mixing [0106] 75 parts by weight of a compound of the formula (I) and/or salts thereof, [0107] 10 parts by weight of calcium lignosulfonate, [0108] 5 parts by weight of sodium lauryl sulfate, [0109] 3 parts by weight of polyvinyl alcohol and [0110] 7 parts by weight of kaolin, [0111] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid. [0112] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0113] 25 parts by weight of a compound of the formula (I) and/or salts thereof, [0114] 5 parts by weight of sodium 2,2-dinaphthylmethane-6,6-disulfonate [0115] 2 parts by weight of sodium oleoylmethyltaurate, [0116] 1 part by weight of polyvinyl alcohol, [0117] 17 parts by weight of calcium carbonate and [0118] 50 parts by weight of water, [0119] then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.
C. Biological Examples
[0120] The abbreviations used here mean:
TABLE-US-00012 ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE Amaranthus AVEFA Avena fatua retroflexus CYPES Cyperus serotinus MATIN Matricaria inodora PHBPU Pharbitis purpureum POLCO Polygonum convolvulus SETVI Setaria viridis STEME Stellaria media VERPE Veronica persica VIOTR Viola tricolor
1. Pre-Emergence Herbicidal Action Against Harmful Plants
[0121] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in sandy loam soil in wood-fiber pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, numerous compounds according to the invention showed, at an application rate of 320 g or less per hectare, an activity of at least 80% against a large number of important harmful plants.
[0122] In addition, some substances are also harmless to dicotyledonous crops such as soya, cotton, oilseed rape, sugar beet or potatoes. Some of the compounds according to the invention exhibit high selectivity and are therefore suitable for controlling unwanted vegetation in agricultural crops by the pre-emergence method. The data of Tables A and B below illustrate, in an exemplary manner, the pre-emergence herbicidal action of the compounds according to the invention, the herbicidal activity being stated in percent.
TABLE-US-00013 TABLE A Pre-emergence Example Dosage No. [g/ha] ALOMY AVEFA CYPES SETVI ABUTH 1-1 320 100 100 80 100 100 1-2 320 100 100 90 100 100 1-3 320 100 100 90 100 100 1-4 320 100 100 80 100 100 1-5 320 100 100 100 100 100 1-6 320 100 100 100 100 100 1-13 320 100 100 100 100 100 1-14 320 100 100 100 100 100 1-15 320 100 100 100 100 100 1-16 320 100 100 100 100 100 1-17 320 100 100 100 100 100 1-18 320 100 100 100 100 100 1-25 320 100 100 100 100 100 1-26 320 100 100 100 100 100 1-27 320 100 100 100 100 100 1-28 320 100 100 100 100 100 1-29 320 100 100 100 100 100 1-30 320 100 100 90 100 100 1-37 320 100 100 100 100 100 1-38 320 100 100 90 100 100 1-39 320 90 100 90 100 100 1-40 320 100 90 100 100 100 1-41 320 100 100 100 100 100 1-42 320 100 100 100 100 100 1-49 320 100 100 90 100 100 1-50 320 100 100 100 100 100 1-51 320 100 100 100 100 100 1-52 320 100 100 90 100 100 1-53 320 100 100 100 100 100 1-54 320 100 100 100 100 100 1-61 320 100 100 100 100 100 1-62 320 100 100 100 100 100 1-63 320 100 100 100 100 100 1-64 320 100 100 100 100 100 1-65 320 100 100 90 100 100 1-74 320 100 100 100 100 100 1-75 320 100 90 1-78 320 100 100 100 100 100 2-1 320 90 100 100 100 2-2 320 100 100 90 100 100 2-3 320 90 100 100 100 100 2-4 320 100 100 100 100 100 2-5 320 100 90 80 100 100 2-6 320 100 100 100 100 100 2-13 320 100 100 100 100 100 2-14 320 100 100 100 100 100 2-15 320 100 100 100 100 100 2-16 320 100 100 100 100 100 2-17 320 100 100 100 100 100 2-18 320 100 100 90 100 100 2-25 320 100 100 100 100 100 2-26 320 100 100 90 100 100 2-27 320 100 100 100 100 100 2-28 320 100 100 100 100 100 2-29 320 100 100 90 100 100 2-30 320 100 100 90 100 100 2-37 320 90 100 80 100 100 2-38 320 100 100 100 100 100 2-39 320 100 100 100 100 2-40 320 100 100 2-41 320 100 100 90 100 100 2-42 320 90 90 90 100 100 2-49 320 100 100 90 100 100 2-50 320 100 100 100 100 100 2-51 320 90 100 90 100 100 2-62 320 100 100 100 100 100 2-63 320 100 100 90 100 100 2-64 320 100 100 100 100 100 2-61 320 100 100 100 100 100 2-78 320 100 100 100 100 100 3-1 320 100 100 100 100 3-2 320 90 90 80 100 100 3-3 320 90 100 90 100 100 4-1 320 80 100 100 4-2 320 80 80 100 100 4-3 320 90 80 100 100 100 4-6 320 100 90 100 4-25 320 90 4-28 320 100 4-29 320 100 4-30 320 80 100 4-37 320 100 4-38 320 90 4-39 320 100 100 4-40 320 100 80 100 4-41 320 80 100 4-52 320 100 100 80 100 100 4-53 320 100 100 100 100 100 4-54 320 90 80 80 90 100 4-61 320 100 90 90 100 100 4-64 320 90 100 100 100 4-75 320 80 90 100 5-1 320 80 100 100 6-4 320 90 100 90 6-5 320 90 90 100 100 6-6 320 90 90 80 100 100 7-2 320 90 90 90 100 100 7-3 320 100 100 100 100 100 7-4 320 90 100 100 7-11 320 80 90 90 100 100 7-12 320 100 100 100 100 100 7-13 320 100 100 100 100 100 7-14 320 100 100 100 100 100 7-15 320 100 100 100 100 100 7-16 320 100 100 100 100 100 7-47 320 90 90 80 100 100 7-50 320 100 100 90 100 100 7-64 320 100 100 100 100 100 7-62 320 100 90 80 100 100 7-75 320 100 100 100 100 100
TABLE-US-00014 TABLE B Pre-emergence Example Dosage No. [g/ha] AMARE MATIN STEME VIOTR 1-1 320 100 100 100 100 1-2 320 100 100 90 100 1-3 320 100 100 100 100 1-4 320 100 100 100 100 1-5 320 100 100 90 100 1-6 320 100 100 100 100 1-13 320 100 100 100 100 1-14 320 100 100 100 100 1-15 320 100 100 100 100 1-16 320 100 100 100 100 1-17 320 100 100 100 100 1-18 320 100 100 100 100 1-25 320 100 100 100 100 1-26 320 100 100 100 100 1-27 320 100 100 100 100 1-28 320 100 100 100 100 1-29 320 100 100 100 100 1-30 320 100 100 100 100 1-37 320 100 100 100 100 1-38 320 100 100 100 100 1-39 320 100 100 100 100 1-40 320 100 100 100 100 1-41 320 100 100 100 100 1-42 320 100 100 100 100 1-49 320 100 100 90 100 1-50 320 100 100 90 100 1-51 320 100 100 100 100 1-52 320 100 100 100 100 1-53 320 100 100 100 100 1-54 320 100 100 100 100 1-61 320 100 100 100 100 1-62 320 100 100 100 100 1-63 320 100 100 100 100 1-64 320 100 100 100 100 1-65 320 100 100 100 100 1-74 320 100 100 100 100 1-75 320 90 90 100 90 1-78 320 100 100 100 2-2 320 100 100 100 2-1 320 100 100 100 2-3 320 100 100 90 100 2-4 320 100 100 90 100 2-5 320 100 100 90 100 2-6 320 100 100 100 100 2-13 320 100 100 100 100 2-14 320 100 100 100 100 2-15 320 100 100 100 100 2-16 320 100 100 100 100 2-17 320 100 100 100 100 2-18 320 100 100 100 100 2-25 320 100 100 100 100 2-26 320 100 100 100 100 2-27 320 100 100 100 100 2-28 320 100 100 100 100 2-29 320 100 100 100 100 2-30 320 100 100 100 100 2-37 320 100 100 100 100 2-38 320 100 100 100 100 2-39 320 100 100 100 100 2-40 320 100 100 100 100 2-41 320 100 100 100 100 2-42 320 100 100 90 100 2-49 320 100 100 90 100 2-50 320 100 100 100 100 2-51 320 100 100 90 100 2-62 320 100 100 100 100 2-63 320 100 100 100 100 2-64 320 100 100 100 100 2-61 320 100 100 100 100 2-78 320 100 100 100 100 3-1 320 100 100 100 100 3-2 320 100 100 90 100 3-3 320 100 100 100 4-1 320 100 90 90 100 4-2 320 100 100 100 90 4-3 320 100 100 100 100 4-4 320 100 100 100 100 4-5 320 100 90 100 4-6 320 100 100 90 100 4-25 320 90 90 90 100 4-28 320 90 90 90 100 4-29 320 90 90 90 100 4-30 320 90 100 90 90 4-37 320 100 100 100 90 4-39 320 100 90 100 100 4-40 320 100 100 100 100 4-41 320 100 80 90 4-52 320 100 100 100 100 4-53 320 100 100 100 100 4-54 320 100 100 100 100 4-61 320 100 100 90 100 4-64 320 100 100 100 100 4-75 320 100 100 100 90 5-1 320 100 100 90 100 6-4 320 100 90 90 100 6-5 320 100 90 90 100 6-6 320 90 100 90 100 7-1 320 100 80 80 100 7-2 320 100 90 80 100 7-3 320 100 100 100 100 7-4 320 100 80 90 100 7-11 320 100 80 100 7-12 320 100 100 100 100 7-13 320 100 100 100 100 7-14 320 100 90 100 100 7-15 320 100 100 100 100 7-16 320 100 100 100 100 7-47 320 100 100 90 100 7-50 320 90 90 100 100 7-62 320 100 90 100 100 7-64 320 100 100 100 7-75 320 100 100 100 100
2. Post-Emergence Herbicidal Action Against Harmful Plants
[0123] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha, with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants). Here, numerous compounds according to the invention showed, at an application rate of 80 g or less per hectare, an activity of at least 80% against a large number of important harmful plants. At the same time, inventive compounds leave Gramineae crops such as barley, wheat, rye, millet/sorghum, corn or rice virtually undamaged when applied post-emergence, even at high active compound dosages. In addition, some substances are also harmless to dicotyledonous crops such as soya, cotton, oilseed rape, sugar beet or potatoes. Some of the compounds according to the invention have high selectivity and are therefore suitable for controlling unwanted vegetation in agricultural crops by the post-emergence method. The data of Tables C and D below illustrate, in an exemplary manner, the pre-emergence herbicidal action of the compounds according to the invention, the herbicidal activity being stated in percent.
TABLE-US-00015 TABLE C Post-emergence Example No. Dosage [g/ha] ALOMY AVEFA ECHCG SETVI 1-1 80 90 100 100 100 1-2 80 90 100 90 90 1-3 80 90 100 90 90 1-4 80 90 100 100 100 1-5 80 100 100 100 100 1-6 80 100 100 100 100 1-13 80 90 100 90 90 1-14 80 90 90 100 100 1-15 80 90 100 90 80 1-16 80 90 90 90 90 1-17 80 90 90 90 90 1-18 80 90 100 90 100 1-25 80 100 100 100 100 1-26 80 90 100 100 100 1-27 80 100 100 100 100 1-28 80 90 100 100 100 1-29 80 100 90 100 100 1-30 80 100 100 100 100 1-37 80 80 100 100 100 1-38 80 90 90 100 100 1-39 80 90 80 90 100 1-40 80 90 80 100 100 1-41 80 90 100 90 90 1-42 80 80 90 1-49 80 90 100 80 90 1-50 80 100 100 100 100 1-51 80 100 100 100 100 1-52 80 100 100 90 90 1-53 80 100 100 90 100 1-54 80 90 100 90 100 1-61 80 90 100 90 90 1-62 80 100 100 100 100 1-63 80 90 100 90 100 1-64 80 90 100 90 90 1-65 80 100 100 100 100 1-74 80 90 90 90 100 1-78 80 90 80 100 100 2-1 80 90 100 90 90 2-2 80 90 90 90 100 2-3 80 80 90 90 100 2-4 80 90 100 90 90 2-5 80 90 100 100 100 2-6 80 80 100 90 90 2-13 80 80 90 90 100 2-14 80 90 100 100 2-15 80 80 100 90 100 2-16 80 90 90 90 90 2-17 80 90 100 90 90 2-18 80 80 100 90 90 2-25 80 100 100 100 100 2-26 80 90 100 100 100 2-27 80 90 100 100 100 2-28 80 90 100 100 100 2-29 80 100 90 100 100 2-30 80 90 90 100 100 2-37 80 80 90 100 100 2-38 80 90 90 100 100 2-39 80 80 90 100 2-40 80 80 100 100 2-41 80 80 90 100 100 2-42 80 100 100 2-49 80 100 100 100 100 2-50 80 100 90 100 2-51 80 90 90 90 2-61 80 90 90 90 90 2-62 80 90 100 100 100 2-63 80 100 100 100 100 2-64 80 100 100 100 100 2-78 80 80 90 90 90 3-1 80 90 100 100 100 3-2 80 90 90 90 100 3-3 80 90 90 90 90 4-1 80 80 90 100 4-2 80 80 100 80 4-3 80 90 100 100 4-5 80 90 90 4-4 80 100 90 4-6 80 100 100 4-37 80 80 90 4-38 80 80 4-40 80 90 90 4-41 80 80 4-52 80 90 100 100 100 4-53 80 90 100 90 100 4-54 80 90 100 100 100 4-61 80 100 100 100 100 4-64 80 100 100 100 100 6-4 80 100 100 6-5 80 100 90 6-6 80 80 80 90 90 7-1 80 90 100 100 7-2 80 90 90 100 7-3 80 100 100 90 100 7-4 80 90 90 100 100 7-11 80 90 90 90 7-12 80 90 90 100 90 7-13 80 90 100 100 100 7-14 80 90 100 90 90 7-15 80 90 100 90 100 7-16 80 90 90 90 100 7-47 80 80 100 100 100 7-50 80 90 90 100 100 7-62 80 90 100 100 100 7-64 80 90 100 100 100 7-75 80 80 100 100 90
TABLE-US-00016 TABLE D Post-emergence Example Dosage No. [g/ha] ABUTH AMARE PHBPU STEME VIOTR 1-1 80 100 100 90 100 100 1-2 80 80 80 90 100 100 1-3 80 80 100 100 100 1-4 80 100 100 100 100 100 1-5 80 90 100 100 100 100 1-6 80 90 100 100 100 100 1-13 80 100 100 100 100 100 1-14 80 100 90 90 100 90 1-15 80 90 100 90 100 100 1-16 80 100 100 100 100 1-17 80 100 100 90 100 100 1-18 80 100 100 90 100 100 1-25 80 100 100 100 100 100 1-26 80 100 100 90 100 100 1-27 80 100 100 90 100 100 1-28 80 100 100 100 100 100 1-29 80 100 100 100 100 100 1-30 80 100 90 90 100 100 1-37 80 90 100 90 100 100 1-38 80 100 90 90 100 100 1-39 80 90 100 100 100 100 1-40 80 100 100 100 90 90 1-41 80 100 100 90 100 100 1-42 80 90 100 100 100 100 1-49 80 90 80 90 100 100 1-50 80 100 100 100 100 100 1-51 80 100 100 100 100 100 1-52 80 100 100 100 100 100 1-53 80 100 100 100 100 100 1-54 80 100 100 100 100 100 1-61 80 100 90 100 100 100 1-62 80 100 100 100 100 100 1-63 80 100 100 100 100 100 1-64 80 100 100 100 100 100 1-65 80 100 100 100 100 100 1-74 80 100 100 100 100 100 1-75 80 90 80 100 1-78 80 80 100 100 100 90 2-1 80 90 100 100 100 100 2-2 80 90 80 90 100 100 2-3 80 80 80 100 100 100 2-4 80 100 100 100 2-5 80 100 100 90 100 100 2-6 80 100 90 100 100 100 2-13 80 100 100 100 100 100 2-14 80 100 100 90 100 100 2-15 80 100 100 80 100 100 2-16 80 100 100 100 100 100 2-17 80 100 100 100 100 100 2-18 80 100 100 100 100 100 2-25 80 100 100 100 100 100 2-26 80 90 100 90 100 100 2-27 80 100 100 90 100 100 2-28 80 100 100 100 100 100 2-29 80 100 100 90 100 100 2-30 80 100 100 90 100 100 2-37 80 100 100 100 100 90 2-38 80 90 100 90 100 100 2-39 80 100 90 90 100 100 2-40 80 100 100 90 100 100 2-41 80 100 90 90 100 100 2-42 80 100 90 90 100 100 2-49 80 100 100 100 100 100 2-50 80 100 100 100 100 100 2-51 80 100 100 90 100 100 2-61 80 100 90 100 100 100 2-62 80 100 100 100 100 100 2-63 80 100 100 100 100 100 2-64 80 100 100 100 100 100 2-78 80 80 100 90 100 90 3-1 80 100 100 90 100 100 3-2 80 80 90 100 100 3-3 80 90 80 90 90 100 4-1 80 100 100 100 100 100 4-2 80 90 100 90 90 100 4-3 80 100 100 100 90 100 4-5 80 80 90 90 90 100 4-4 80 80 100 80 90 100 4-6 80 100 100 80 100 100 4-25 80 90 80 100 90 4-28 80 80 90 100 80 4-29 80 80 80 90 90 90 4-30 80 80 90 90 80 4-37 80 80 100 80 80 4-38 80 90 90 90 90 100 4-39 80 90 90 90 100 90 4-40 80 80 100 90 80 4-41 80 100 90 90 90 90 4-52 80 90 100 100 90 90 4-53 80 100 100 90 90 100 4-54 80 90 90 100 100 100 4-61 80 100 100 100 100 100 4-64 80 100 100 100 100 100 4-75 80 100 80 90 80 5-1 80 100 80 90 100 100 6-4 80 90 80 90 100 6-5 80 80 90 100 6-6 80 80 80 100 100 100 7-1 80 100 100 90 90 100 7-2 80 100 100 90 100 100 7-3 80 100 90 90 100 100 7-4 80 100 90 100 7-11 80 90 90 90 90 100 7-12 80 100 100 90 100 100 7-13 80 100 100 100 100 100 7-14 80 100 100 90 100 100 7-15 80 100 100 90 100 100 7-16 80 100 100 90 100 100 7-47 80 90 90 90 100 100 7-50 80 100 90 90 100 7-62 80 100 100 90 100 100 7-64 80 100 100 100 90 90 7-75 80 90 100 80 80 100
3. Comparative Experiments
[0124] For comparison, the herbicidal activity of numerous compounds according to the invention was tested with the structurally closest compounds known from the documents WO 2011/035874, WO 2012/028579 and WO 2012/126932, by the pre- and post-emergence method. These data are listed in Tables E to M below, where in each comparison pair the first compound is the compound according to the invention and the second compound is the compound known from the prior art.
TABLE-US-00017 TABLE E Comparison with compounds known from WO 2011035874, applied by the post-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] ABUTH AMARE MATIN PHBPU STEME VIOTR VERPE 5-1 80 100 80 40 90 100 100 100 1-81 80 30 60 10 10 0 0 30
TABLE-US-00018 TABLE F Comparison with compounds known from WO2011035874, applied by the post-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] ABUTH MATIN PHBPU STEME VIOTR 5-1 80 100 100 1-51 80 80 40 5-1 80 40 90 100 100 1-77 80 0 40 80 60
TABLE-US-00019 TABLE G Comparison with compounds known from WO 2011035874, applied by the pre-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] ALOMY AVEFA CYPES ECHCG SETVI ABUTH 5-1 80 30 30 50 80 80 100 1-51 80 10 0 0 30 60 100 5-1 80 30 30 50 80 80 100 1-81 80 0 40 0 10 10 20 5-1 320 40 60 80 100 100 100 1-77 320 10 0 30 70 20 100
TABLE-US-00020 TABLE H Comparison with compounds known from WO 2011035874, applied by the pre-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] AMARE POLCO STEME VIOTR VERPE 5-1 80 100 80 80 100 100 1-51 80 100 0 90 60 100 5-1 80 100 80 80 100 100 1-81 80 60 10 50 90 70 5-1 320 100 100 90 100 100 1-77 320 100 30 80 60 90
TABLE-US-00021 TABLE I Comparison with compounds known from WO 2012/028579, applied by the post-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] ALOMY AVEFA CYPES SETVI STEME VIOTR 1-1 80 90 100 80 100 100 100 4-803 80 20 0 60 100 100 100 1-2 5 60 70 50 90 90 100 4-804 5 0 0 0 10 10 20 1-3 80 90 100 80 90 100 100 4-805 80 0 0 0 0 0 0 1-1 20 90 90 40 100 100 100 4-812 20 30 50 40 100 100 90 1-2 5 60 70 100 4-813 5 30 40 100 1-3 5 60 70 60 90 90 100 4-814 5 0 30 20 80 90 100 1-49 5 60 50 50 80 100 4-803 5 0 0 20 0 90 1-51 20 90 90 90 100 100 100 4-805 20 0 0 0 0 0 0 1-49 5 60 50 50 100 4-812 5 10 20 20 70 1-51 5 40 60 80 100 100 4-814 5 0 30 20 90 100 1-2 5 60 70 50 90 90 100 4-136 5 40 80 80 90 100 80 1-2 5 60 70 50 90 90 100 4-175 5 0 0 30 40 80 70 1-3 5 60 70 100 4-176 5 30 10 100 1-1 20 90 90 40 100 100 100 4-78 20 20 80 40 80 80 60 1-2 20 80 90 70 90 90 100 4-79 20 20 40 10 90 40 40 1-3 5 60 60 90 90 100 4-80 5 10 20 20 90 60 1-1 5 60 100 100 100 4-108 5 60 90 70 90 1-2 5 60 70 50 90 90 4-109 5 20 40 40 90 90 1-3 5 60 70 90 90 100 4-110 5 20 20 90 90 100 1-1 5 60 40 100 100 100 4-128 5 20 0 80 60 100 1-2 5 60 70 50 90 90 100 4-129 5 20 0 50 80 70 80 1-3 5 60 70 60 90 90 100 4-130 5 20 0 10 60 100 90 1-1 5 60 40 20 100 100 100 4-122 5 80 40 20 40 90 100 1-2 5 60 70 50 90 100 4-123 5 30 10 20 90 100 1-3 5 60 70 60 90 90 100 4-124 5 20 60 60 90 70 100 1-1 5 60 40 100 100 100 4-406 5 60 0 80 100 100 1-49 5 60 50 80 70 100 4-229 5 10 10 90 40 40 1-51 5 40 80 90 100 100 4-231 5 0 50 90 90 60 1-49 5 60 50 80 100 4-292 5 10 0 40 70 1-51 5 40 60 80 100 100 4-756 5 40 0 10 100 90 1-49 5 60 50 50 100 4-245 5 30 20 30 90 1-51 80 100 100 100 100 100 100 4-634 80 80 80 100 100 100 100 1-51 20 90 90 90 100 100 100 4-640 20 50 70 60 100 100 100 4-1 20 70 20 0 60 80 100 1-573 20 0 0 10 10 10 70 4-3 20 30 50 70 40 60 100 1-574 20 0 0 0 20 50 80 4-3 20 50 70 40 60 100 1-90 20 0 0 0 10 0 4-1 20 70 20 0 60 80 100 1-119 20 0 0 0 10 40 60 4-3 20 50 70 40 100 1-121 20 0 40 40 40 4-1 20 70 20 0 60 80 100 1-387 20 10 0 0 0 60 60 4-1 20 70 20 0 60 80 100 1-139 20 0 0 0 0 40 80
TABLE-US-00022 TABLE J Comparison with compounds known from WO 2012/028579, applied by the pre-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] ALOMY AVEFA CYPES ECHCG SETVI 1-1 20 90 30 80 70 4-803 20 0 0 0 0 1-2 320 100 100 90 100 100 4-804 320 0 10 10 0 0 1-2 80 90 70 80 100 90 4-804 80 0 0 10 0 0 1-3 320 100 100 90 100 100 4-805 320 0 0 0 0 0 1-3 80 90 100 90 100 100 4-805 80 0 0 0 0 0 1-1 20 90 30 70 4-812 20 50 0 40 1-3 80 90 100 90 100 4-814 80 40 20 20 20 1-3 20 50 80 30 70 4-814 20 20 10 10 10 1-49 20 40 50 50 50 90 4-803 20 0 0 0 0 0 1-50 320 100 100 100 100 100 4-804 320 0 10 10 0 0 1-50 80 100 90 100 100 100 4-804 80 0 0 10 0 0 1-51 320 100 100 100 100 100 4-805 320 0 0 0 0 0 1-51 80 100 90 90 100 100 4-805 80 0 0 0 0 0 1-50 20 90 100 4-813 20 0 10 1-51 80 100 90 90 100 4-814 80 40 20 20 20 1-51 20 80 90 100 4-814 20 20 10 10 1-1 20 90 30 4-135 20 60 0 1-3 20 80 90 4-137 20 0 20 1-1 20 90 30 80 70 4-174 20 0 10 0 0 1-2 20 70 20 60 40 4-175 20 20 0 0 0 1-3 20 50 80 90 70 4-176 20 20 20 20 40 1-1 80 90 90 70 100 100 4-78 80 10 30 10 0 70 1-2 80 90 70 80 100 90 4-79 80 20 20 0 0 20 1-3 20 50 80 30 90 70 4-80 20 0 10 0 0 0 1-1 20 90 30 4-108 20 50 0 1-2 20 60 4-109 20 0 1-3 20 80 70 4-110 20 10 20 1-1 20 90 30 80 70 4-128 20 10 0 0 10 1-2 80 90 70 4-129 80 30 50 1-3 20 50 80 30 90 70 4-130 20 20 0 0 70 20 1-1 20 30 80 4-122 20 0 50 1-2 20 70 20 60 4-123 20 20 0 0 1-3 20 50 80 30 4-124 20 10 0 10 1-1 20 90 80 70 4-406 20 0 10 0 1-49 20 40 50 50 50 90 4-229 20 0 0 0 10 50 1-50 80 100 100 4-230 80 60 40 1-50 20 90 70 90 100 4-230 20 40 0 0 60 1-51 20 80 90 100 4-231 20 20 50 70 1-49 20 40 50 90 4-292 20 20 0 20 1-50 80 100 90 100 100 100 4-293 80 20 0 40 0 10 1-51 20 80 90 100 100 4-756 20 40 0 0 40 1-49 80 80 70 4-245 80 60 30 1-49 20 50 4-245 20 0 1-50 20 90 70 90 100 4-246 20 70 50 60 70 1-51 20 80 90 4-247 20 60 70 1-49 80 90 80 70 100 4-632 80 30 0 20 70 1-50 20 90 70 100 4-633 20 0 20 10 1-51 20 80 90 100 100 4-634 20 60 60 80 30 1-49 20 50 50 4-638 20 0 0 1-50 20 90 100 4-639 20 30 70 1-51 20 90 4-640 20 0 4-1 320 40 80 50 100 100 1-573 320 0 0 0 60 0 4-3 320 90 80 100 100 100 1-574 320 0 0 50 30 0 4-1 80 30 30 70 80 1-146 80 0 0 30 0 4-3 80 60 30 100 100 90 1-148 80 0 0 0 0 0 4-1 80 30 30 70 80 1-186 80 0 0 0 0 4-3 80 60 30 100 100 90 1-188 80 10 0 0 0 0 4-3 320 90 80 100 100 1-90 320 0 10 30 20 4-1 320 40 80 50 100 100 1-119 320 0 40 0 20 40 4-3 80 60 30 100 100 90 1-121 80 0 0 20 0 0 4-1 80 30 30 70 80 1-387 80 0 0 0 0 4-3 80 60 30 100 100 90 1-389 80 30 0 0 0 0 4-1 320 40 80 100 100 1-139 320 0 30 20 0
TABLE-US-00023 TABLE K Comparison with compounds known from WO 2012/028579, applied by the pre-emergence method Dosage Herbicidal efficacy against Example No. [g/ha] ABUTH MATIN POLCO VIOTR 1-1 20 90 70 60 100 4-803 20 0 10 0 0 1-2 320 100 100 80 100 4-804 320 80 0 0 0 1-2 80 100 100 70 100 4-804 80 0 0 0 0 1-3 320 100 100 90 100 4-805 320 20 30 0 0 1-3 80 100 100 90 100 4-805 80 0 30 0 0 1-3 80 100 90 4-814 80 80 20 1-3 20 100 80 30 100 4-814 20 40 20 10 80 1-49 20 70 80 100 4-803 20 0 10 0 1-50 320 100 100 90 100 4-804 320 80 0 0 0 1-50 80 100 100 80 100 4-804 80 0 0 0 0 1-51 320 100 100 90 100 4-805 320 20 30 0 0 1-51 80 100 100 80 100 4-805 80 0 30 0 0 1-50 20 90 4-813 20 70 1-51 80 100 80 4-814 80 80 20 1-51 20 100 90 30 100 4-814 20 40 20 10 80 1-1 20 70 60 100 4-135 20 0 0 50 1-3 20 30 4-137 20 0 1-1 20 90 70 60 100 4-174 20 70 30 0 70 1-2 20 70 80 4-175 20 40 0 1-3 20 30 100 4-176 20 0 80 1-1 80 100 90 70 100 4-78 80 50 0 0 10 1-2 80 100 100 70 100 4-79 80 0 0 0 0 1-3 20 100 80 30 100 4-80 20 0 0 0 0 1-1 20 90 70 100 4-108 20 60 0 20 1-2 20 80 4-109 20 10 1-3 20 100 4-110 20 80 1-1 20 90 70 60 100 4-128 20 70 50 0 50 1-2 80 70 4-129 80 10 1-3 20 80 30 4-130 20 20 0 1-1 20 60 100 4-122 20 0 70 1-2 20 70 80 4-123 20 0 20 1-3 20 30 4-124 20 0 1-1 20 90 60 100 4-406 20 40 10 0 1-49 20 70 80 100 4-229 20 0 0 0 1-50 80 100 100 80 100 4-230 80 80 0 0 30 1-50 20 100 100 4-230 20 30 0 1-51 20 100 90 30 100 4-231 20 60 70 0 0 1-50 80 100 80 100 4-293 80 40 0 70 1-51 20 100 30 100 4-756 20 70 0 20 1-49 20 100 4-245 20 50 1-50 20 100 4-246 20 20 1-49 80 100 50 100 4-632 80 60 0 70 1-50 20 100 90 100 4-633 20 60 60 0 1-51 20 100 90 30 4-634 20 70 70 0 1-49 20 80 4-638 20 40 1-50 20 90 100 4-639 20 60 80 1-51 20 30 4-640 20 0 4-1 320 100 30 100 1-573 320 60 0 80 4-3 320 100 100 70 100 1-574 320 40 70 0 10 4-1 80 90 80 30 100 1-146 80 70 60 0 30 4-3 80 100 40 1-148 80 0 0 4-1 80 90 80 30 100 1-186 80 0 0 0 0 4-3 80 100 100 40 100 1-188 80 0 40 0 40 4-3 320 100 100 70 100 1-90 320 0 0 10 0 4-1 320 100 100 1-119 320 40 0 4-3 80 100 40 100 1-121 80 60 0 50 4-1 80 90 80 30 100 1-387 80 30 30 0 0 4-3 80 100 100 100 1-389 80 30 50 80 4-1 320 100 90 30 1-139 320 70 70 0
TABLE-US-00024 TABLE L Comparison with compounds known from WO2012126932, applied by the pre-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] ALOMY AVEFA CYPES LOLMU SETVI POLCO VIOTR 7-1 80 60 20 60 0 30 2-143 80 30 0 0 0 0 7-3 80 90 90 100 80 100 40 100 2-145 80 90 80 90 60 100 10 100 7-1 80 60 20 0 70 90 2-183 80 0 0 0 0 0 7-3 80 90 90 100 80 100 40 100 2-185 80 80 20 70 40 100 40 100 7-1 320 70 70 70 30 100 100 2-130 320 70 30 0 30 100 90 7-1 80 60 20 60 0 70 30 90 2-136 80 0 0 0 0 20 0 0 7-1 320 70 70 30 100 100 2-116 320 40 50 10 90 80 7-2 80 80 70 80 10 90 30 100 2-117 80 20 0 50 0 20 0 0 7-3 80 90 90 100 80 100 100 2-118 80 30 50 70 40 60 90 7-1 320 70 70 70 30 100 40 100 2-85 320 0 0 40 0 0 0 0 7-3 320 100 100 100 100 100 70 100 2-87 320 70 30 20 0 80 20 60
TABLE-US-00025 TABLE M Comparison with compounds known from WO2012126932, applied by the post-emergence method Example Dosage Herbicidal efficacy against No. [g/ha] ALOMY AVEFA SETVI MATIN VIOTR VERPE 7-1 20 70 40 100 100 90 2-143 20 50 20 100 60 80 7-2 20 70 100 70 100 100 2-144 20 70 90 90 60 100 7-1 20 70 40 100 100 2-183 20 20 10 70 70 7-1 20 70 40 100 40 100 90 2-130 20 40 20 80 10 30 80 7-1 20 70 40 100 40 100 90 2-136 20 30 0 90 20 30 60 7-1 20 70 40 100 40 100 90 2-116 20 70 40 70 40 60 50 7-2 20 70 100 70 100 100 2-117 20 60 70 30 90 70 7-3 80 100 100 100 100 100 100 2-118 80 70 100 90 70 100 90 7-3 20 60 90 90 90 100 100 2-118 20 60 90 90 50 90 80 7-1 20 70 40 100 40 100 90 2-85 20 0 0 40 20 0 50 7-3 80 100 100 100 100 100 100 2-87 80 60 70 80 0 70 80