SUBSTITUTED N-PHENYL-N-AMINOUARCILS AND SALTS THEREOF AND USE THEREOF AS HERBICIDAL AGENTS

Abstract

The present invention relates to substituted N-phenyl-N-aminouracils of the general formula (I) or salts thereof

##STR00001##

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

Claims

1. A substituted N-phenyl-N-aminouracil of formula (I) or salt thereof, ##STR00103## in which R.sup.1 represents hydrogen, (C.sub.1-C.sub.8)-haloalkyl, R.sup.2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C.sub.1-C.sub.8)-alkoxy, R.sup.3 represents hydrogen, halogen, (C.sub.1-C.sub.8)-alkoxy, R.sup.4 represents halogen, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.2-C.sub.8)-alkynyl, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, halogen, cyano, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.1-C.sub.8)-alkoxy, (C.sub.1-C.sub.8)-haloalkoxy, G represents straight-chain or branched (C.sub.1-C.sub.8)-alkylene, Q represents hydroxy or a radical of formula below ##STR00104## R.sup.8 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.2-C.sub.8)-alkenyl, C(O)R.sup.13, C(O)OR.sup.13, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, R.sup.9 represents hydrogen or (C.sub.1-C.sub.8)-alkyl, R.sup.10 represents hydrogen, halogen, cyano, NO.sub.2, (C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-halocycloalkyl, (C.sub.3-C.sub.8)-halocycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, R.sup.11R.sup.12N—(C.sub.1-C.sub.8)-alkyl, R.sup.13O—(C.sub.1-C.sub.8)-alkyl, cyano-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, arylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, OR.sup.13, NR.sup.11R.sup.12, SR.sup.14, S(O)R.sup.14, SO.sub.2R.sup.14, R.sup.14S—(C.sub.1-C.sub.8)-alkyl, R.sup.14(O)S—(C.sub.1-C.sub.8)-alkyl, R.sup.14O.sub.2S—(C.sub.1-C.sub.8)-alkyl, tris-[(C.sub.1-C.sub.8)-alkyl]silyl-(C.sub.1-C.sub.8)-alkyl, bis-[(C.sub.1-C.sub.8)-alkyl](aryl)silyl(C.sub.1-C.sub.8)-alkyl, [(C.sub.1-C.sub.8)-alkyl]-bis-(aryl)silyl-(C.sub.1-C.sub.8)-alkyl, tris-[(C.sub.1-C.sub.8)-alkyl]silyl, bis-hydroxyboryl-(C.sub.1-C.sub.8)-alkyl, bis-[(C.sub.1-C.sub.8)-alkoxy]boryl-(C.sub.1-C.sub.8)-alkyl, tetramethyl-1,3,2-dioxaborolan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl-(C.sub.1-C.sub.8)-alkyl, nitro-(C.sub.1-C.sub.8)-alkyl, C(O)OR.sup.13, C(O)R.sup.13, C(O)NR.sup.11R.sup.12, R.sup.13O(O)C—(C.sub.1-C.sub.8)-alkyl, R.sup.11R.sup.12N(O)C—(C.sub.1-C.sub.8)-alkyl, bis-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, or R.sup.8 and R.sup.10 together with the carbon atom to which they are attached form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution, R.sup.11 and R.sup.12 are identical or different and independently of one another represent hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.3-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylthio-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkylthio-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, COR.sup.13, SO.sub.2R.sup.14, heterocyclyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, bis-[(C.sub.1-C.sub.8)-alkyl]aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkyl-aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkyl-aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxycarbonyl, heteroaryl-(C.sub.1-C.sub.8)-alkoxycarbonyl, (C.sub.2-C.sub.8)-alkenyloxycarbonyl, (C.sub.2-C.sub.8)-alkynyloxycarbonyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution, R.sup.13 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.3-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-haloalkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, bis-[(C.sub.1-C.sub.8)-alkyl]aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkyl-aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkyl-aminocarbonyl-(C.sub.1-C.sub.8)-alkyl, bis-[(C.sub.1-C.sub.8)-alkyl]amino-(C.sub.2-C.sub.6)-alkyl, (C.sub.1-C.sub.8)-alkyl-amino-(C.sub.2-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.8)-alkyl-amino-(C.sub.2-C.sub.6)-alkyl, R.sup.14S—(C.sub.1-C.sub.8)-alkyl, R.sup.14(O)S—(C.sub.1-C.sub.8)-alkyl, R.sup.14O.sub.2S—(C.sub.1-C.sub.8)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, tris-[(C.sub.1-C.sub.8)-alkyl]silyl-(C.sub.1-C.sub.8)-alkyl, bis-[(C.sub.1-C.sub.8)-alkyl](aryl)silyl(C.sub.1-C.sub.8)-alkyl, [(C.sub.1-C.sub.8)-alkyl]-bis-(aryl)silyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, arylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.8)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.10-alkyl, aryloxy-(C.sub.1-C.sub.8)-alkyl, heteroaryloxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxycarbonyl, R.sup.14 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.2-C.sub.8)-alkynyl, (C.sub.1-C.sub.8)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.8)-haloalkenyl, (C.sub.3-C.sub.8)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.8)-alkoxy-(C.sub.1-C.sub.8)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.8)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.8)-alkyl, heterocyclyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.8)-alkyl, bis-[(C.sub.1-C.sub.8)-alkyl]amino, (C.sub.1-C.sub.8)-alkyl-amino, aryl-(C.sub.1-C.sub.8)-amino, aryl-(C.sub.1-C.sub.6)-alkyl-amino, aryl-[(C.sub.1-C.sub.8)-alkyl]amino, (C.sub.3-C.sub.8)-cycloalkyl-amino, (C.sub.3-C.sub.8)-cycloalkyl-[(C.sub.1-C.sub.8)-alkyl]amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, R.sup.15 and R.sup.16 independently of one another represent hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, C(O)R.sup.13, C(O)OR.sup.13, C(O)NR.sup.11R.sup.12, SO.sub.2R.sup.14, or R.sup.15 and R.sup.16 together with the nitrogen atom to which they are attached form an imino group which is optionally substituted further by hydrogen, (C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, aryl, heteroaryl, heterocyclyl, (C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl, aryl-(C.sub.1-C.sub.8)-alkoxycarbonyl-(C.sub.1-C.sub.8)-alkyl and X and Y independently of one another represent O (oxygen) or S (sulfur).

2. The compound of formula (I) as claimed in claim 1 and/or salt thereof, wherein R.sup.1 represents hydrogen, R.sup.2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C.sub.1-C.sub.6)-alkoxy, R.sup.3 represents hydrogen, halogen, (C.sub.1-C.sub.6)-alkoxy, R.sup.4 represents halogen, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.6)-alkynyl, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, G represents straight-chain or branched (C.sub.1-C.sub.6)-alkylene, Q represents hydroxy or a radical of formula below ##STR00105## R.sup.8 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-alkenyl, C(O)R.sup.13, C(O)OR.sup.13, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, R.sup.9 represents hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.10 represents hydrogen, halogen, cyano, NO.sub.2, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, aryl, aryl-(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, R.sup.11R.sup.12N—(C.sub.1-C.sub.6)-alkyl, R.sup.13O—(C.sub.1-C.sub.6)-alkyl, cyano-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, arylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, OR.sup.13, NR.sup.11R.sup.12, SR.sup.14, S(O)R.sup.14, SO.sub.2R.sup.14, R.sup.14S—(C.sub.1-C.sub.6)-alkyl, R.sup.14(O)S—(C.sub.1-C.sub.6)-alkyl, R.sup.14O.sub.2S—(C.sub.1-C.sub.6)-alkyl, tris-[(C.sub.1-C.sub.6)-alkyl]silyl-(C.sub.1-C.sub.6)-alkyl, bis-[(C.sub.1-C.sub.6)-alkyl](aryl)silyl(C.sub.1-C.sub.6)-alkyl, [(C.sub.1-C.sub.6)-alkyl]-bis-(aryl)silyl-(C.sub.1-C.sub.6)-alkyl, tris-[(C.sub.1-C.sub.6)-alkyl]silyl, bis-hydroxyboryl-(C.sub.1-C.sub.6)-alkyl, bis-[(C.sub.1-C.sub.6)-alkoxy]boryl-(C.sub.1-C.sub.6)-alkyl, tetramethyl-1,3,2-dioxaborolan-2-yl, tetramethyl-1,3,2-dioxaborolan-2-yl-(C.sub.1-C.sub.6)-alkyl, nitro-(C.sub.1-C.sub.6)-alkyl, C(O)OR.sup.13, C(O)R.sup.13, C(O)NR.sup.11R.sup.12, R.sup.13O(O)C—(C.sub.1-C.sub.6)-alkyl, R.sup.11R.sup.12N(O)C—(C.sub.1-C.sub.6)-alkyl, bis-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, or R.sup.8 and R.sup.10 together with the carbon atom to which they are attached form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution, R.sup.11 and R.sup.12 are identical or different and independently of one another represent hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.3-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, COR.sup.13, SO.sub.2R.sup.14, heterocyclyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, bis-[(C.sub.1-C.sub.6)-alkyl]aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkyl-aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl, heteroaryl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.2-C.sub.6)-alkenyloxycarbonyl, (C.sub.2-C.sub.6)-alkynyloxycarbonyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, or R.sup.11 and R.sup.12 together with the nitrogen atom to which they are attached form a fully saturated or partially saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution, R.sup.13 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.3-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, bis-[(C.sub.1-C.sub.6)-alkyl]aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkyl-aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, bis-[(C.sub.1-C.sub.6)-alkyl]amino-(C.sub.2-C.sub.4)-alkyl, (C.sub.1-C.sub.6)-alkyl-amino-(C.sub.2-C.sub.4)-alkyl, aryl-(C.sub.1-C.sub.6)-alkyl-amino-(C.sub.2-C.sub.4)-alkyl, R.sup.14S—(C.sub.1-C.sub.6)-alkyl, R.sup.14(O)S—(C.sub.1-C.sub.6)-alkyl, R.sup.14O.sub.2S—(C.sub.1-C.sub.6)-alkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, tris-[(C.sub.1-C.sub.6)-alkyl]silyl-(C.sub.1-C.sub.6)-alkyl, bis-[(C.sub.1-C.sub.6)-alkyl](aryl)silyl(C.sub.1-C.sub.6)-alkyl, [(C.sub.1-C.sub.6)-alkyl]-bis-(aryl)silyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, arylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heteroarylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, heterocyclylcarbonyloxy-(C.sub.1-C.sub.6)-alkyl, aryloxy-(C.sub.1-C.sub.6)-alkyl, heteroaryloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, R.sup.14 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.10)-haloalkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.3-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.10)-cycloalkyl, (C.sub.3-C.sub.10)-halocycloalkyl, (C.sub.4-C.sub.10)-cycloalkenyl, (C.sub.4-C.sub.10)-halocycloalkenyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-haloalkyl, aryl, aryl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.4-C.sub.10)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, bis-[(C.sub.1-C.sub.6)-alkyl]amino, (C.sub.1-C.sub.6)-alkyl-amino, aryl-(C.sub.1-C.sub.6)-amino, aryl-(C.sub.1-C.sub.2)-alkyl-amino, aryl-[(C.sub.1-C.sub.6)-alkyl]amino, (C.sub.3-C.sub.6)-cycloalkyl-amino, (C.sub.3-C.sub.6)-cycloalkyl-[(C.sub.1-C.sub.6)-alkyl]amino; N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, R.sup.15 and R.sup.16 independently of one another represent hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, C(O)R.sup.13, C(O)OR.sup.13, C(O)NR.sup.11R.sup.12, SO.sub.2R.sup.14, or R.sup.15 and R.sup.16 together with the nitrogen atom to which they are attached form an imino group which is optionally substituted further by hydrogen, (C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, aryl, heteroaryl, heterocyclyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl and X and Y independently of one another represent O (oxygen) or S (sulfur).

3. The compound of formula (I) as claimed in claim 1 and/or salt thereof, wherein R.sup.1 represents hydrogen, R.sup.2 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, prop-1-yloxy, but-1-yloxy, R.sup.3 represents hydrogen, fluorine, chlorine, bromine, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, R.sup.4 represents fluorine, chlorine, bromine, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, trifluoromethyl, difluoromethyl, pentafluoroethyl, ethynyl, propyn-1-yl, 1-butyn-1-yl, pentyn-1-yl, hexyn-1-yl, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, prop-1-yloxy, prop-2-yloxy, but-1-yloxy, but-2-yloxy, 2-methylprop-1-yloxy, 1,1-dimethyleth-1-yloxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, G represents methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-yl)methylene, (dimethyl)methylene, (diethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, 1,1-dimethylethyl-1-ene, 2,2-dimethylethyl-1-ene, 1-ethylethyl-1-ene, 2-ethylethyl-1-ene, 1-(prop-1-yl)ethyl-1-ene, 2-(prop-1-yl)ethyl-1-ene, 1-(prop-2-yl)ethyl-1-ene, 2-(prop-2-yl)ethyl-1-ene, 1,1,2-trimethylethyl-1-ene, 1,2,2-trimethylethyl-1-ene, 1,1,2,2-tetramethylethyl-1-ene, n-pentylene, 1-methylbutyl-1-ene, 2-methylbutyl-1-ene, 3-methylbutyl-1-ene, 4-methylbutyl-1-ene, 1,1-dimethylpropyl-1-ene, 2,2-dimethylpropyl-1-ene, 3,3-dimethylpropyl-1-ene, 1,2-dimethylpropyl-1-ene, 1,3-dimethylpropyl-1-ene, 1-ethylpropyl-1-ene, n-hexylene, 1-methylpentyl-1-ene, 2-methylpentyl-1-ene, 3-methylpentyl-1-ene, 4-methylpentyl-1-ene, 1,1-dimethylbutyl-1-ene, 1,2-dimethylbutyl-1-ene, 1,3-dimethylbutyl-1-ene, 2,2-dimethylbutyl-1-ene, 2,3-dimethylbutyl-1-ene, 3,3-dimethylbutyl-1-ene, 1-ethylbutyl-1-ene, 2-ethylbutyl-1-ene, 1,1,2-trimethylpropyl-1-ene, 1,2,2-trimethylpropyl-1-ene, 1-ethyl-1-methylpropyl-1-ene, 1-ethyl-2-methylpropyl-1-ene, R.sup.15 and R.sup.16 independently of one another represent hydrogen, methyl, ethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butyloxycarbonyl, X and Y independently of one another represent O (oxygen) or S (sulfur) and Q represents one of the moieties Q-1 to Q-486 specifically mentioned below: ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184##

4. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 represents hydrogen, R.sup.2 represents fluorine, R.sup.3 represents fluorine, R.sup.4 represents chlorine, bromine, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, G represents methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene, n-hexylene, R.sup.15 and R.sup.16 represent hydrogen, X and Y independently of one another represent O (oxygen) or S (sulfur) and Q represents one of the moieties Q-1 to Q-486.

5. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 represents hydrogen, R.sup.2 represents fluorine, R.sup.3 represents fluorine, R.sup.4 represents chlorine, bromine, cyano, NO.sub.2, C(O)NH.sub.2, C(S)NH.sub.2, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, G represents methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (1-methyl)ethyl-1-ene, (2-methyl)ethyl-1-ene, n-butylene, 1-methylpropyl-1-ene, 2-methylpropyl-1-ene, 3-methylpropyl-1-ene, n-pentylene, n-hexylene, R.sup.15 and R.sup.16 represent hydrogen, X and Y independently of one another represent O (oxygen) or S (sulfur) and Q represents one of the moieties Q-1 to Q-481.

6. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 represents hydrogen, R.sup.2 represents fluorine, R.sup.3 represents fluorine, R.sup.4 represents chlorine, bromine, cyano, NO.sub.2, R.sup.5, R.sup.6 and R.sup.7 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, G represents methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, R.sup.15 and R.sup.16 represent hydrogen, X and Y independently of one another represent O (oxygen) or S (sulfur) and Q represents one of the moieties Q-1 to Q-486.

7. The compound of formula (I) as claimed in claim 3 and/or salt thereof, wherein R.sup.1 represents hydrogen, R.sup.2 represents fluorine, R.sup.3 represents fluorine, R.sup.4 represents chlorine, NO.sub.2, R.sup.5 represents hydrogen, R.sup.6 represents hydrogen, fluorine, R.sup.7 represents hydrogen, G represents methylene, (methyl)methylene, ethylene, n-propylene, R.sup.15 and R.sup.16 represent hydrogen, X represents O (oxygen) or S (sulfur), Y represents O (oxygen) and Q represents one of the moieties Q-1, Q-2, Q-23, Q-115, Q-176, Q-286, Q-441, Q-442, Q-447, Q-448, Q-457, Q-471, Q-481.

8. A product comprising one or more compounds of formula (I) as defined in claim 1 and/or salts thereof, as herbicide and/or plant growth regulator, optionally in crops of useful plants and/or ornamentals.

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

10. A method for controlling one or more harmful plants or for regulating the growth of one or more plants, comprising applying an effective amount of one or more compounds of formula (I), as defined in claim 1 and/or salts thereof, or a composition thereof, to the plants, seed of plants, soil in which or on which plants grow or an area under cultivation.

Description

SYNTHESIS EXAMPLES

No. I.1-2: 2-Ethoxyethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate

[0200] ##STR00046##

[0201] Successively, 2-fluoro-4-chloroaniline (145 g, 996 mmol) and triethylamine (202 g, 2000 mmol) were added carefully to a solution of triphosgene (119 g, 401 mmol) in abs. dichloromethane (1000 ml) such that the temperature of the resulting reaction mixture remained below 20° C. After the addition had ended, the reaction mixture was stirred at room temperature overnight and then washed with water (3×500 ml) and 1N hydrochloric acid (500 ml), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting 2-fluoro-4-chlorophenyl isocyanate was used in the next stage without further purification. Sodium hydride (5.60 g, 140 mmol, 60% dispersion in mineral oil) was suspended in abs. N,N-dimethylformamide, and ethyl (2E)-3-amino-4,4,4-trifluorobut-2-enoate (14.2 g, 77.5 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and then cooled to a temperature of −30° C., and 2-fluoro-4-chlorophenyl isocyanate (12.0 g, 70.0 mmol) was added. After the addition had ended, the resulting reaction mixture was stirred at room temperature for a further 4 h and then added to ice-water. After addition of ethyl acetate and acidification with 1N hydrochloric acid, the aqueous phase was extracted thoroughly with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave 3-(4-chloro-2-fluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (15.2 g, 50.2 mmol, 65%), which was used in the next stage without further purification. It was also possible to prepare 3-(4-chloro-2-fluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione on a larger scale, either by repeating the synthesis route described above or via the following, slightly modified synthesis route. Ethyl 4,4,4-trifluoro-3-oxobutanoate (200 g, 1087 mmol) was dissolved in ethanol (1.3 l), ammonium acetate (334.7 g, 4347 mmol) was added and the mixture was then stirred under reflux conditions for 16 h. After addition of ethyl acetate and water, the aqueous phase was extracted thoroughly with ethyl acetate. The combined organic phases were washed with water and sat. NaCl solution, dried over sodium sulfate and filtered, and the crude product was then purified carefully by distillation (500 mm/Hg at about 40 to 45° C.). Ethyl (2Z)-3-amino-4,4,4-trifluorobut-2-enoate (180 g, 983 mmol), which was obtained as a slightly yellowish liquid, was then used for the next reaction step without further purification and added to a suspension, cooled to 0° C., of sodium hydride (98.3 g, 2458 mmol) in abs. N,N-dimethylformamide (1.5 l). The resulting reaction mixture was stirred at 0° C. for 1 h and at room temperature for 1 h. After once more cooling to 0° C., dimethylcarbamoyl chloride (210.4 g, 1967 mmol) was added. The reaction mixture was stirred at room temperature for another 2 h. After addition of ethyl acetate and water, the aqueous phase was extracted thoroughly with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification of the crude product obtained by column chromatography gave ethyl (2Z)-3-[(dimethylcarbamoyl)amino]-4,4,4-trifluorobut-2-enoate (120 g, 38% of theory) in the form of a slightly brownish oil. 2-Chloro-4-fluoroaniline (50 g, 344.8 mmol) and ethyl (2Z)-3-[(dimethylcarbamoyl)amino]-4,4,4-trifluorobut-2-enoate (87.6 g, 344.8 mmol) were dissolved in acetic acid (500 ml) and stirred under reflux conditions for 48 h. After the reaction had ended, the reaction mixture was cooled to room temperature and added to ice-water. The aqueous mixture was filtered and the resulting filtered solid was dissolved in ethyl acetate and washed with sat. NaCl solution. The organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography gave 3-(4-chloro-2-fluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (40.0 g, 38% of theory) as a colorless solid. 3-(4-Chloro-2-fluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (40 g, 130 mmol) was then added a little at a time to chlorosulfonic acid (60 ml) in a round-bottom flask which had been dried by heating. The resulting reaction mixture was then stirred at a temperature of 130° C. under an atmosphere of nitrogen for 5 h and, after cooling to room temperature, added to ice-water and extracted repeatedly with ethyl acetate (3×300 ml). The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave 2-chloro-5-[2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluorobenzenesulfonyl chloride (30.0 g, 57% of theory), which was used in the next stage without further purification. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 9.49 (br. s, 1H), 8.15 (d, 1H), 7.57 (d, 1H), 6.29 (s, 1H). 2-Chloro-5-[2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluorobenzenesulfonyl chloride (30.0 g, 74 mmol) was initially charged in a round-bottom flask, and hydrochloric acid (105 ml), acetic acid (225 ml) and tin dichloride dihydrate (79 g, 251 mmol) were added in succession. The resulting reaction mixture was stirred at a temperature of 80° C. for 5 h and, after cooling to room temperature, added to ice-water and extracted thoroughly with dichloromethane (3×400 ml). The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. Final purification by column chromatography gave 3-(4-chloro-2-fluoro-5-sulfanylphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (25.0 g, 98% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.85 (br. s, 1H), 7.35 (d, 1H), 7.29 (d, 1H), 6.26 (s, 1H), 3.88 (s, 1H). 3-(4-Chloro-2-fluoro-5-sulfanylphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (25.00 g, 73.5 mmol) was dissolved in abs. dichloromethane (500 ml), and trityl chloride (34.15 g, 73.5 mmol) and pyridine (5.81 g, 73.53 mmol) were added. The resulting reaction mixture was stirred at room temperature for 3 h and then water was added and the mixture was extracted thoroughly. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. Final purification by column chromatography gave 3-[4-chloro-2-fluoro-5-(tritylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (25 g, 43% of theory) in the form of a colorless solid. .sup.1H NMR (CDCl.sub.3 δ, ppm) 9.40 (br. s, 1H), 7.39-7.23 (m, 15H), 7.20 (m, 1H), 6.74 (d, 1H), 6.13 (s, 1H). 3-[4-Chloro-2-fluoro-5-(tritylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (25 g, 1 equiv.) was dissolved in abs. tetrahydrofuran (625 ml), and sodium carbonate (3 equiv.) was added. O-Mesitylenesulfonylhydroxylamine (3 equiv.) was then added carefully, a little at a time. The resulting reaction mixture was subsequently stirred under nitrogen for 12 h. After complete conversion, water and ethyl acetate were added and the mixture was repeatedly thoroughly extracted. The combined organic phases were dried over sodium sulfate, filtered and carefully concentrated under reduced pressure. Final purification by column chromatography gave 1-amino-3-[4-chloro-2-fluoro-5-(tritylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (21.1 g, 82% of theory) in the form of a colorless solid. .sup.1H-NMR (d.sub.6-DMSO δ, ppm) 7.61 (d, 1H), 7.33-7.23 (m, 15H), 6.88 (d, 1H), 6.34 (s, 1H), 5.54 (br. s, 2H, NH.sub.2). Under argon, 1-amino-3-[4-chloro-2-fluoro-5-(tritylsulfanyl)phenyl]-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (5.0 g, 8.53 mmol) was dissolved in dichloromethane (50 ml), and the mixture was cooled to 0° C. Trifluoroacetic acid (2.30 ml, 29.86 mmol) and triisopropylsilane (9.16 ml, 44.79 mmol) were then added. The resulting reaction mixture was stirred at room temperature for about 3 h. After complete conversion, water and dichloromethane were added and the mixture was extracted thoroughly. The combined organic phases were dried over sodium sulfate, filtered and carefully concentrated under reduced pressure. Final purification by column chromatography gave 1-amino-3-(4-chloro-2-fluoro-5-sulfanylphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (2.98 g, 98% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 7.36 (d, 1H), 7.29 (d, 1H), 6.28 (s, 1H), 4.59 (s, 2H), 3.88 (s, 1H). Under argon, 1-amino-3-(4-chloro-2-fluoro-5-sulfanylphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (600 mg, 1.69 mmol) was dissolved in dioxane (18 ml) in a microwave vessel and, after degassing of the solvent, tris(dibenzylideneacetone)dipalladium (39 mg, 0.04 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (49 mg, 0.08 mmol), N,N-diisopropylethylamine (0.59 ml, 3.37 mmol) and 3-bromo-2-hydroxypyridine (333 mg, 1.86 mmol) were added. The resulting reaction mixture was stirred under microwave conditions at a temperature of 160° C. for 2 h. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. Purification of the resulting crude product by column chromatography gave 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (720 mg, 86% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 12.64 (br. s, 1H), 7.45 (d, 1H), 7.40 (d, 1H), 7.35 (d, 1H), 7.24 (d, 1H), 6.30 (m, 1H), 6.23 (s, 1H), 4.58 (s, 2H). In a microwave vessel and under argon, n-hexane (19 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (300 mg, 0.69 mmol). Silver(I)carbonate (223 mg, 0.80 mmol) and 2-ethoxyethyl iodoacetate (431 mg, 1.34 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 40 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. Purification of the resulting crude product by column chromatography gave 2-ethoxyethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate (119 mg, 31% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.12 (d, 1H), 7.77 (m, 1H), 7.32 (d, 1H), 7.24 (d, 1H), 6.95 (m, 1H), 6.19 (s, 1H), 4.99-4.87 (q, 2H), 4.62 (s, 2H), 4.36-4.29 (m, 1H), 4.17-4.11 (m, 1H), 3.64-3.61 (m, 2H), 3.53 (q, 2H), 1.20 (t, 3H).

No. I.1-23: 2-(2-Methoxyethoxy)ethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate

[0202] ##STR00047##

[0203] In a microwave vessel and under argon, n-hexane (15 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (200 mg, 0.45 mmol). Silver(I) carbonate (147 mg, 0.54 mmol) and 2-(2-methoxyethoxy)ethyl iodoacetate (257 mg, 0.89 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 48 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave 2-(2-methoxyethoxy)ethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate (68 mg, 23% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.12 (d, 1H), 7.78 (m, 1H), 7.34 (d, 1H), 7.26 (d, 1H), 6.95 (m, 1H), 6.19 (s, 1H), 4.98-4.87 (q, 2H), 4.66 (s, 2H), 4.35-4.30 (m, 1H), 4.16-4.11 (m, 1H), 3.71-3.66 (m, 2H), 3.62-3.59 (m, 2H), 3.54-3.51 (m, 2H), 3.36 (s, 3H).

No. I.1-441: Methyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate

[0204] ##STR00048##

[0205] In a microwave vessel and under argon, n-hexane (6 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (150 mg, 0.33 mmol). Silver(I) carbonate (111 mg, 0.40 mmol) and methyl 2-iodoacetate (0.08 ml, 0.67 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 30 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave methyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate (34 mg, 19% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.12 (d, 1H), 7.73 (m, 1H), 7.35 (d, 1H), 7.25 (d, 1H), 6.95 (m, 1H), 6.20 (s, 1H), 4.97-4.84 (q, 2H), 4.52 (s, 2H), 3.70 (s, 3H).

No. I.1-442: Ethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate

[0206] ##STR00049##

[0207] In a microwave vessel and under argon, n-hexane (17 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (300 mg, 0.67 mmol). Silver(I) carbonate (223 mg, 0.80 mmol) and ethyl 2-iodoacetate (0.16 ml, 1.34 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 30 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave ethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate (81 mg, 32% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.11 (d, 1H), 7.72 (m, 1H), 7.35 (d, 1H), 7.28 (d, 1H), 6.94 (m, 1H), 6.19 (s, 1H), 4.95-4.83 (q, 2H), 4.52 (s, 2H), 4.16-4.10 (m, 2H), 1.26 (t, 3H).

No. I.1-447: n-Butyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate

[0208] ##STR00050##

[0209] In a microwave vessel and under argon, n-hexane (17 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (200 mg, 0.45 mmol). Silver(I) carbonate (149 mg, 0.54 mmol) and n-pentyl 2-iodoacetate (270 mg, 0.89 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 40 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave n-butyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate (16 mg, 6% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.11 (d, 1H), 7.72 (m, 1H), 7.33 (d, 1H), 7.28 (d, 1H), 6.94 (m, 1H), 6.19 (s, 1H), 4.95-4.83 (q, 2H), 4.58 (s, 2H), 4.14-4.05 (m, 2H), 1.65-1.55 (m, 4H), 1.41-1.30 (m, 2H), 0.92 (t, 3H).

No. I.1-448: n-Pentyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate

[0210] ##STR00051##

[0211] In a microwave vessel and under argon, n-hexane (17 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (180 mg, 0.40 mmol). Silver(I) carbonate (134 mg, 0.48 mmol) and n-pentyl 2-iodoacetate (257 mg, 0.80 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 40 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave n-pentyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate (23 mg, 10% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.11 (d, 1H), 7.47-7.43 (m, 2H), 7.13 (d, 1H), 6.98 (m, 1H), 6.25 (s, 1H), 4.68 (s, 2H), 4.58 (s, 2H), 4.16 (t, 2H), 1.68-1.63 (m, 2H), 1.39-1.30 (m, 4H), 0.91 (t, 3H).

No. I.1-457: Benzyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate

[0212] ##STR00052##

[0213] In a microwave vessel and under argon, n-hexane (17 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (180 mg, 0.40 mmol). Silver(I) carbonate (134 mg, 0.48 mmol) and benzyl 2-iodoacetate (226 mg, 0.80 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 40 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave benzyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}acetate (21 mg, 9% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.07 (d, 1H), 7.72 (m, 1H), 7.38-7.22 (m, 7H), 6.94 (m, 1H), 6.16 (s, 1H), 5.13 (s, 2H), 5.01-4.90 (q, 2H), 4.45 (s, 2H).

No. I.2-442: Ethyl 2-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}propanoate

[0214] ##STR00053##

[0215] In a microwave vessel and under argon, n-hexane (6 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (160 mg, 0.36 mmol). Silver(I) carbonate (118 mg, 0.43 mmol) and ethyl 2-iodopropionate (166 mg, 0.71 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 2 h. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave ethyl 2-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}propanoate (96 mg, 47% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.09 (m, 1H), 7.72 (m, 1H), 7.33 (d, 1H), 7.19 (d, 1H), 6.91 (m, 1H), 6.19 (s, 1H), 5.22 (m, 1H), 4.52 (s, 2H), 4.18-4.09 (m, 2H), 1.49 (d, 3H), 1.23 (t, 3H).

No. I.5-442: Ethyl 3-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}propanoate

[0216] ##STR00054##

[0217] In a microwave vessel and under argon, n-hexane (7 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (150 mg, 0.33 mmol). Silver(I) carbonate (111 mg, 0.40 mmol) and ethyl 3-iodopropionate (161 mg, 0.67 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 30 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave ethyl 3-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}propanoate (65 mg, 34% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.10 (d, 1H), 7.55 (m, 1H), 7.38 (d, 1H), 7.12 (d, 1H), 6.88 (m, 1H), 6.23 (s, 1H), 4.65-4.57 (m, 4H), 4.15 (q, 2H), 2.70 (t, 2H), 1.25 (t, 3H).

No. I.5-457: Benzyl 3-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}propanoate

[0218] ##STR00055##

[0219] In a microwave vessel and under argon, n-hexane (5 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (140 mg, 0.31 mmol). Silver(I) carbonate (103 mg, 0.37 mmol) and benzyl 3-iodopropionate (201 mg, 0.62 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 30 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave benyl 3-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}propanoate (70 mg, 35% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.09 (m, 1H), 7.57 (m, 1H), 7.37-7.30 (m, 6H), 7.09 (d, 1H), 6.88 (m, 1H), 6.21 (s, 1H), 5.22 (s, 2H), 4.68-4.62 (m, 2H), 4.50 (s, 2H), 2.77 (t, 2H).

No. I.6-441: Methyl 4-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}butanoate

[0220] ##STR00056##

[0221] In a microwave vessel and under argon, n-hexane (7 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (150 mg, 0.33 mmol). Silver(I) carbonate (111 mg, 0.40 mmol) and ethyl 3-iodopropionate (161 mg, 0.67 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 30 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave methyl 4-{[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)pyridin-2-yl]oxy}butanoate (104 mg, 54% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.11 (d, 1H), 7.60 (m, 1H), 7.38 (d, 1H), 7.10 (d, 1H), 6.87 (m, 1H), 6.22 (s, 1H), 4.62 (s, 2H), 4.37-4.31 (m, 2H), 3.66 (s, 3H), 2.41-2.36 (m, 2H), 2.08-2.00 (m, 2H).

No. I.14-442: Ethyl [(3-{5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluoro-2-nitrophenoxy}pyridin-2-yl)oxy]acetate

[0222] ##STR00057##

[0223] Successively, 2,5-difluoroaniline (1 equiv.) and triethylamine (2 equiv.) were added carefully to a solution of triphosgene (0.4 equiv.) in abs. dichloromethane such that the temperature of the resulting reaction mixture remained below 20° C. After the addition had ended, the reaction mixture was stirred at room temperature overnight and then washed with water and 1N hydrochloric acid, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting 2,5-difluorophenyl isocyanate was used in the next stage without further purification. Sodium hydride (2 equiv., 60% dispersion in mineral oil) was suspended in abs. N,N-dimethylformamide, and ethyl (2E)-3-amino-4,4,4-trifluorobut-2-enoate (1.1 equiv.) was added. The reaction mixture was stirred at room temperature for 1 h and then cooled to a temperature of −30° C., and 2,5-difluorophenyl isocyanate (1 equiv) was added. After the addition had ended, the resulting reaction mixture was stirred at room temperature for a further 4 h and then added to ice-water. After addition of ethyl acetate and acidification with 1N hydrochloric acid, the aqueous phase was extracted thoroughly with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave 3-(2,5-difluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, which was used in the next stage without further purification. Sulfuric acid was added to 3-(2,5-difluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (1 equiv.), and the resulting reaction mixture was cooled to 0° C. Potassium nitrate (1.1 equiv.) was then added carefully, a little at a time. The resulting reaction mixture was stirred at a temperature of 100° C. for 10 h and, after cooling to room temperature, added to ice-water. Ethyl acetate was then added, and the aqueous phase was repeatedly extracted thoroughly with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and carefully concentrated under reduced pressure, which gave 3-(2,5-difluoro-4-nitrophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione in the form of a colorless solid. 3-(2,5-Difluoro-4-nitrophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (1 equiv.) was dissolved in abs. N,N-dimethylformamide, and a solution of sodium hydride (1.2 equiv., 60% strength dispersion in mineral oil) in N,N-dimethylformamide was added. 2,4-Dinitrophenylhydroxylamine (1.5 equiv.) was then added carefully, a little at a time. The resulting reaction mixture was subsequently stirred under nitrogen for 12 h. After complete conversion, water and ethyl acetate were added and the mixture was repeatedly thoroughly extracted. The combined organic phases were dried over sodium sulfate, filtered and carefully concentrated under reduced pressure. Final purification by column chromatography gave 1-amino-3-(2,5-difluoro-4-nitrophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione in the form of a colorless solid. Under argon, N,N-dimethylformamide (5 ml) was added to 1-amino-3-(2,5-difluoro-4-nitrophenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (150 mg, 0.43 mmol) in a round-bottom flask which had been dried by heating. Ethyl [(3-hydroxypyridin-2-yl)oxy]acetate (84 mg, 0.43 mmol) and potassium carbonate (65 mg, 0.47 mmol) were then added. The reaction mixture was stirred at a temperature of 65° C. for 3 h. After cooling to room temperature, water and dichloromethane were added to the reaction mixture and the mixture was extracted thoroughly. The combined organic phases were dried over sodium sulfate, filtered and carefully concentrated under reduced pressure. Final purification by column chromatography gave ethyl [(3-{5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-4-fluoro-2-nitrophenoxy}pyridin-2-yl)oxy]acetate (81 mg, 36% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.01 (m, 1H), 7.89 (d, 1H), 7.72 (m, 1H), 7.53 (m, 1H), 7.18 (d, 1H), 7.00 (m, 1H), 6.19 (s, 1H), 4.99 (d, 1H), 4.85 (d, 2H), 4.51 (s, 2H), 4.15-4.10 (m, 2H), 1.26 (t, 3H).

No. I.31-23: 2-(2-Methoxyethoxy)ethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)-5-fluoropyridin-2-yl]oxy}acetate

[0224] ##STR00058##

[0225] Under argon, 1-amino-3-(4-chloro-2-fluoro-5-sulfanylphenyl)-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (800 mg, 2.25 mmol) was dissolved in dioxane (18 ml) in a microwave vessel and, after degassing of the solvent, tris(dibenzylideneacetone)dipalladium (51 mg, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (65 mg, 0.11 mmol), N,N-diisopropylethylamine (0.78 ml, 4.49 mmol) and 3-bromo-5-fluoro-2-hydroxypyridine (475 mg, 2.47 mmol) were added. The resulting reaction mixture was stirred under microwave conditions at a temperature of 160° C. for 2 h. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. Purification of the resulting crude product by column chromatography gave 1-amino-3-{4-chloro-2-fluoro-5-[(5-fluoro-2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (660 mg, 63% of theory) in the form of a colorless solid. .sup.1H-NMR (d.sub.6-DMSO δ, ppm) 12.02 (br. s, 1H), 7.98 (d, 1H), 7.70 (d, 1H), 7.59 (m, 1H), 6.97 (m, 1H), 6.41 (s, 1H), 5.59 (s, 2H). In a microwave vessel and under argon, n-hexane (15 ml) was added to 1-amino-3-{4-chloro-2-fluoro-5-[(5-fluoro-2-hydroxypyridin-3-yl)sulfanyl]phenyl}-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione (220 mg, 0.47 mmol). Silver(I) carbonate (156 mg, 0.57 mmol) and 2-(2-methoxyethoxy)ethyl iodoacetate (272 mg, 0.94 mmol) were then added. The reaction mixture was stirred at a temperature of 140° C. under microwave conditions for 48 minutes. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the resulting crude product by column chromatography gave 2-(2-methoxyethoxy)ethyl {[3-({5-[3-amino-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-2-chloro-4-fluorophenyl}sulfanyl)-5-fluoropyridin-2-yl]oxy}acetate (33 mg, 10% of theory) in the form of a colorless solid. .sup.1H-NMR (CDCl.sub.3 δ, ppm) 7.91 (m, 1H), 7.43 (m, 1H), 7.38 (m, 2H), 6.22 (s, 1H), 4.95 (d, 1H), 4.91 (d, 1H), 4.65 (s, 2H), 4.35-4.30 (m, 1H), 4.20-4.17 (m, 1H), 3.72-3.66 (m, 2H), 3.62-3.59 (m, 2H), 3.58-3.53 (m, 5H), 3.37 (s, 3H).

[0226] In analogy to the preparation examples cited above and recited at the appropriate point, and taking account of the general details relating to the preparation of substituted N-heterocyclyl- and N-heteroaryltetrahydropyrimidinones, the compounds cited below are obtained. If in Table 1 a structural element is defined by a structural formula containing a broken line, this broken line means that at this position the group in question is attached to the remainder of the molecule. If in Table 1 a structural element is defined by a structural formula containing an arrow, the arrow represents a bond of the respective group Q to the carbonyl group in the general formula (I).

##STR00059##

[0227] Table I.1: Preferred compounds of the formula (I.1) are the compounds I.1-1 to I.1-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.1-1 to I.1-486 of Table I.1 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

TABLE-US-00001 TABLE 1 No. Q 1 Q-1 2 Q-2 3 Q-3 4 Q-4 5 Q-5 6 Q-6 7 Q-7 8 Q-8 9 Q-9 10 Q-10 11 Q-11 12 Q-12 13 Q-13 14 Q-14 15 Q-15 16 Q-16 17 Q-17 18 Q-18 19 Q-19 20 Q-20 21 Q-21 22 Q-22 23 Q-23 24 Q-24 25 Q-25 26 Q-26 27 Q-27 28 Q-28 29 Q-29 30 Q-30 31 Q-31 32 Q-32 33 Q-33 34 Q-34 35 Q-35 36 Q-36 37 Q-37 38 Q-38 39 Q-39 40 Q-40 41 Q-41 42 Q-42 43 Q-43 44 Q-44 45 Q-45 46 Q-46 47 Q-47 48 Q-48 49 Q-49 50 Q-50 51 Q-51 52 Q-52 53 Q-53 54 Q-54 55 Q-55 56 Q-56 57 Q-57 58 Q-58 59 Q-59 60 Q-60 61 Q-61 62 Q-62 63 Q-63 64 Q-64 65 Q-65 66 Q-66 67 Q-67 68 Q-68 69 Q-69 70 Q-70 71 Q-71 72 Q-72 73 Q-73 74 Q-74 75 Q-75 76 Q-76 77 Q-77 78 Q-78 79 Q-79 80 Q-80 81 Q-81 82 Q-82 83 Q-83 84 Q-84 85 Q-85 86 Q-86 87 Q-87 88 Q-88 89 Q-89 90 Q-90 91 Q-91 92 Q-92 93 Q-93 94 Q-94 95 Q-95 96 Q-96 97 Q-97 98 Q-98 99 Q-99 100 Q-100 101 Q-101 102 Q-102 103 Q-103 104 Q-104 105 Q-105 106 Q-106 107 Q-107 108 Q-108 109 Q-109 110 Q-110 111 Q-111 112 Q-112 113 Q-113 114 Q-114 115 Q-115 116 Q-116 117 Q-117 118 Q-118 119 Q-119 120 Q-120 121 Q-121 122 Q-122 123 Q-123 124 Q-124 125 Q-125 126 Q-126 127 Q-127 128 Q-128 129 Q-129 130 Q-130 131 Q-131 132 Q-132 133 Q-133 134 Q-134 135 Q-135 136 Q-136 137 Q-137 138 Q-138 139 Q-139 140 Q-140 141 Q-141 142 Q-142 143 Q-143 144 Q-144 145 Q-145 146 Q-146 147 Q-147 148 Q-148 149 Q-149 150 Q-150 151 Q-151 152 Q-152 153 Q-153 154 Q-154 155 Q-155 156 Q-156 157 Q-157 158 Q-158 159 Q-159 160 Q-160 161 Q-161 162 Q-162 163 Q-163 164 Q-164 165 Q-165 166 Q-166 167 Q-167 168 Q-168 169 Q-169 170 Q-170 171 Q-171 172 Q-172 173 Q-173 174 Q-174 175 Q-175 176 Q-176 177 Q-177 178 Q-178 179 Q-179 180 Q-180 181 Q-181 182 Q-182 183 Q-183 184 Q-184 185 Q-185 186 Q-186 187 Q-187 188 Q-188 189 Q-189 190 Q-190 191 Q-191 192 Q-192 193 Q-193 194 Q-194 195 Q-195 196 Q-196 197 Q-197 198 Q-198 199 Q-199 200 Q-200 201 Q-201 202 Q-202 203 Q-203 204 Q-204 205 Q-205 206 Q-206 207 Q-207 208 Q-208 209 Q-209 210 Q-210 211 Q-211 212 Q-212 213 Q-213 214 Q-214 215 Q-215 216 Q-216 217 Q-217 218 Q-218 219 Q-219 220 Q-220 221 Q-221 222 Q-222 223 Q-223 224 Q-224 225 Q-225 226 Q-226 227 Q-227 228 Q-228 229 Q-229 230 Q-230 231 Q-231 232 Q-232 233 Q-233 234 Q-234 235 Q-235 236 Q-236 237 Q-237 238 Q-238 239 Q-239 240 Q-240 241 Q-241 242 Q-242 243 Q-243 244 Q-244 245 Q-245 246 Q-246 247 Q-247 248 Q-248 249 Q-249 250 Q-250 251 Q-251 252 Q-252 253 Q-253 254 Q-254 255 Q-255 256 Q-256 257 Q-257 258 Q-258 259 Q-259 260 Q-260 261 Q-261 262 Q-262 263 Q-263 264 Q-264 265 Q-265 266 Q-266 267 Q-267 268 Q-268 269 Q-269 270 Q-270 271 Q-271 272 Q-272 273 Q-273 274 Q-274 275 Q-275 276 Q-276 277 Q-277 278 Q-278 279 Q-279 280 Q-280 281 Q-281 282 Q-282 283 Q-283 284 Q-284 285 Q-285 286 Q-286 287 Q-287 288 Q-288 289 Q-289 290 Q-290 291 Q-291 292 Q-292 293 Q-293 294 Q-294 295 Q-295 296 Q-296 297 Q-297 298 Q-298 299 Q-299 300 Q-300 301 Q-301 302 Q-302 303 Q-303 304 Q-304 305 Q-305 306 Q-306 307 Q-307 308 Q-308 309 Q-309 310 Q-310 311 Q-311 312 Q-312 313 Q-313 314 Q-314 315 Q-315 316 Q-316 317 Q-317 318 Q-318 319 Q-319 320 Q-320 321 Q-321 322 Q-322 323 Q-323 324 Q-324 325 Q-325 326 Q-326 327 Q-327 328 Q-328 329 Q-329 330 Q-330 331 Q-331 332 Q-332 333 Q-333 334 Q-334 335 Q-335 336 Q-336 337 Q-337 338 Q-338 339 Q-339 340 Q-340 341 Q-341 342 Q-342 343 Q-343 344 Q-344 345 Q-345 346 Q-346 347 Q-347 348 Q-348 349 Q-349 350 Q-350 351 Q-351 352 Q-352 353 Q-353 354 Q-354 355 Q-355 356 Q-356 357 Q-357 358 Q-358 359 Q-359 360 Q-360 361 Q-361 362 Q-362 363 Q-363 364 Q-364 365 Q-365 366 Q-366 367 Q-367 368 Q-368 369 Q-369 370 Q-370 371 Q-371 372 Q-372 373 Q-373 374 Q-374 375 Q-375 376 Q-376 377 Q-377 378 Q-378 379 Q-379 380 Q-380 381 Q-381 382 Q-382 383 Q-383 384 Q-384 385 Q-385 386 Q-386 387 Q-387 388 Q-388 389 Q-389 390 Q-390 391 Q-391 392 Q-392 393 Q-393 394 Q-394 395 Q-395 396 Q-396 397 Q-397 398 Q-398 399 Q-399 400 Q-400 401 Q-401 402 Q-402 403 Q-403 404 Q-404 405 Q-405 406 Q-406 407 Q-407 408 Q-408 409 Q-409 410 Q-410 411 Q-411 412 Q-412 413 Q-413 414 Q-414 415 Q-415 416 Q-416 417 Q-417 418 Q-418 419 Q-419 420 Q-420 421 Q-421 422 Q-422 423 Q-423 424 Q-424 425 Q-425 426 Q-426 427 Q-427 428 Q-428 429 Q-429 430 Q-430 431 Q-431 432 Q-432 433 Q-433 434 Q-434 435 Q-435 436 Q-436 437 Q-437 438 Q-438 439 Q-439 440 Q-440 441 Q-441 442 Q-442 443 Q-443 444 Q-444 445 Q-445 446 Q-446 447 Q-447 448 Q-448 449 Q-449 450 Q-450 451 Q-451 452 Q-452 453 Q-453 454 Q-454 455 Q-455 456 Q-456 457 Q-457 458 Q-458 459 Q-459 460 Q-460 461 Q-461 462 Q-462 463 Q-463 464 Q-464 465 Q-465 466 Q-466 467 Q-467 468 Q-468 469 Q-469 470 Q-470 471 Q-471 472 Q-472 473 Q-473 474 Q-474 475 Q-475 476 Q-476 477 Q-477 478 Q-478 479 Q-479 480 Q-480 481 Q-481 482 Q-482 483 Q-483 484 Q-484 485 Q-485 486 Q-486

##STR00060##

[0228] Table I.2: Preferred compounds of the formula (I.2) are the compounds I.2-1 to I.2-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.2-1 to I.2-486 of Table 1.2 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00061##

[0229] Table I.3: Preferred compounds of the formula (I.3) are the compounds I.3-1 to I.3-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.3-1 to I.3-486 of Table 1.3 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00062##

[0230] Table I.4: Preferred compounds of the formula (I.4) are the compounds I.4-1 to I.4-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.4-1 to I.4-486 of Table 1.4 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00063##

[0231] Table I.5: Preferred compounds of the formula (I.5) are the compounds I.5-1 to I.5-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.5-1 to I.5-486 of Table 1.5 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00064##

[0232] Table I.6: Preferred compounds of the formula (I.6) are the compounds I.6-1 to I.6-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.6-1 to I.6-486 of Table 1.6 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00065##

[0233] Table I.7: Preferred compounds of the formula (I.7) are the compounds I.7-1 to I.7-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.7-1 to I.7-486 of Table 7.1 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00066##

[0234] Table I.8: Preferred compounds of the formula (I.8) are the compounds I.8-1 to I.8-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.8-1 to I.8-486 of Table 8.1 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00067##

[0235] Table I.9: Preferred compounds of the formula (I.9) are the compounds I.9-1 to I.9-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.9-1 to I.9-486 of Table 1.9 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00068##

[0236] Table I.10: Preferred compounds of the formula (I.10) are the compounds I.10-1 to I.10-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.10-1 to I.10-486 of Table I.1 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00069##

[0237] Table I.11: Preferred compounds of the formula (I.11) are the compounds I.11-1 to I.11-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.11-1 to I.11-486 of Table I.11 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00070##

[0238] Table I.12: Preferred compounds of the formula (I.12) are the compounds I.12-1 to I.12-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.12-1 to I.12-486 of Table I.12 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00071##

[0239] Table I.13: Preferred compounds of the formula (I.13) are the compounds I.13-1 to I.13-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.13-1 to I.13-486 of Table I.13 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00072##

[0240] Table I.14: Preferred compounds of the formula (I.14) are the compounds I.14-1 to I.14-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.14-1 to I.14-486 of Table I.14 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00073##

[0241] Table I.15: Preferred compounds of the formula (I.15) are the compounds I.15-1 to I.15-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.15-1 to I.15-486 of Table I.15 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00074##

[0242] Table I.16: Preferred compounds of the formula (I.16) are the compounds I.16-1 to I.16-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.16-1 to I.16-486 of Table I.16 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00075##

[0243] Table I.17: Preferred compounds of the formula (I.17) are the compounds I.17-1 to I.17-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.17-1 to I.17-486 of Table I.17 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00076##

[0244] Table I.18: Preferred compounds of the formula (I.18) are the compounds I.18-1 to I.18-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.18-1 to I.18-486 of Table I.18 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00077##

[0245] Table I.19: Preferred compounds of the formula (I.19) are the compounds I.19-1 to I.19-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.19-1 to I.19-486 of Table I.19 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00078##

[0246] Table I.20: Preferred compounds of the formula (I.20) are the compounds I.20-1 to I.20-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.20-1 to I.20-486 of Table I.20 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00079##

[0247] Table I.21: Preferred compounds of the formula (I.21) are the compounds I.21-1 to I.21-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.21-1 to I.21-486 of Table I.21 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00080##

[0248] Table I.22: Preferred compounds of the formula (I.22) are the compounds I.22-1 to I.22-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.22-1 to I.22-486 of Table I.22 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00081##

[0249] Table I.23: Preferred compounds of the formula (I.23) are the compounds I.23-1 to I.23-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.23-1 to I.23-486 of Table I.23 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00082##

[0250] Table I.24: Preferred compounds of the formula (I.24) are the compounds I.24-1 to I.24-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.24-1 to I.24-486 of Table I.24 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00083##

[0251] Table I.25: Preferred compounds of the formula (I.25) are the compounds I.25-1 to I.25-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.25-1 to I.25-486 of Table I.25 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00084##

[0252] Table I.26: Preferred compounds of the formula (I.26) are the compounds I.26-1 to I.26-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.26-1 to I.26-486 of Table I.26 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00085##

[0253] Table I.27: Preferred compounds of the formula (I.27) are the compounds I.27-1 to I.27-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.27-1 to I.27-486 of Table I.27 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00086##

[0254] Table I.28: Preferred compounds of the formula (I.28) are the compounds I.28-1 to I.28-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.28-1 to I.28-486 of Table I.28 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00087##

[0255] Table I.29: Preferred compounds of the formula (I.29) are the compounds I.29-1 to I.29-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.29-1 to I.29-486 of Table I.29 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00088##

[0256] Table I.30: Preferred compounds of the formula (I.30) are the compounds I.30-1 to I.30-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.30-1 to I.30-486 of Table I.30 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00089##

[0257] Table I.31: Preferred compounds of the formula (I.31) are the compounds I.31-1 to I.31-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.31-1 to I.31-486 of Table I.31 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00090##

[0258] Table I.32: Preferred compounds of the formula (I.32) are the compounds I.32-1 to I.32-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.32-1 to I.32-486 of

[0259] Table I.32 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00091##

[0260] Table I.33: Preferred compounds of the formula (I.33) are the compounds I.33-1 to I.33-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.33-1 to I.33-486 of Table I.33 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

##STR00092##

[0261] Table I.34: Preferred compounds of the formula (I.34) are the compounds I.34-1 to I.34-486 in which Q has the meanings of Table 1 indicated in the respective row. Thus, the compounds I.34-1 to I.34-486 of Table I.34 are defined by the meaning of the respective entries Nos. 1 to 486 for Q of Table 1.

[0262] NMR data of selected examples: The .sup.1H NMR data of selected examples of compounds of the general formula (I) are stated in two different ways, namely (a) conventional NMR evaluation and interpretation or (b) in the form of .sup.1H NMR peak lists according to the method described below.

a) Conventional NMR Interpretation

Example No. I.1-1

[0263] .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.12 (d, 1H), 7.77 (m, 1H), 7.34 (d, 1H), 7.26 (d, 1H), 6.96 (m, 1H), 6.19 (s, 1H), 4.98-4.88 (q, 2H), 4.61 (s, 2H), 4.32-4.27 (m, 1H), 4.17-4.11 (m, 1H), 3.58-3.56 (m, 2H), 3.36 (s, 3H).

Example No. I.1-115

[0264] .sup.1H-NMR (CDCl.sub.3, δ, ppm) 8.08 (m, 1H), 7.67 (m, 1H), 7.36 (d, 1H), 7.17 (d, 1H), 6.95 (m, 1H), 6.21 (s, 1H), 5.42 (quin, 1H), 5.00-4.87 (dd, 2H), 4.86-4.83 (m, 2H), 4.63-4.59 (m, 2H), 4.54 (s, 2H).

Example No. I.1-176

[0265] .sup.1H-NMR (CDCl.sub.3, δ, ppm) 8.10 (m, 1H), 7.75 (m, 1H), 7.36 (d, 1H), 7.14 (d, 1H), 6.99 (m, 1H), 6.22 (s, 1H), 4.96 (s, 2H), 4.72 (s, 1H), 4.58 (s, 2H).

Example No. I.1-286

[0266] .sup.1H-NMR (CDCl.sub.3, δ, ppm) 8.54 (m, 1H), 8.10 (m, 1H), 7.76 (m, 1H), 7.72-7.68 (m, 1H), 7.33 (d, 1H), 7.33-7.30 (m, 1H), 7.28-7.22 (m, 1H), 7.16 (d, 1H), 6.13 (s, 1H), 5.26 (d, 1H), 5.21 (d, 1H), 5.08 (d, 1H), 4.95 (d, 1H), 4.76 (s, 2H).

Example No. I.1-471

[0267] .sup.1H-NMR (CDCl.sub.3 δ, ppm) 8.11 (d, 1H), 7.73 (m, 1H), 7.35 (d, 1H), 7.26 (d, 1H), 6.97-6.93 (m, 1H), 6.19 (s, 1H), 5.93-5.85 (m, 1H), 5.33-5.23 (m, 2H), 4.99 (d, 1H), 4.92 (d, 1H), 4.59 (m, 2H), 4.51 (s, 2H).

b) NMR Peak List Method

[0268] The NMR data of selected examples may also be stated in the form of NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The pairs of δ value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons. The peak list for one example therefore takes the form of:

δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i); . . . ; δ.sub.n (intensity.)

[0269] 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. For calibration of the chemical shift of NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists. The lists of the NMR peaks are similar to the conventional NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation. In addition, like conventional 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. In the reporting of compound signals within the delta range of solvents and/or water, our lists of NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average. The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%). Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional NMR interpretation.

[0270] Further details of NMR peak lists can be found in the Research Disclosure Database Number 564025.

[0271] I.31-1: .sup.1H-NMR (599.6 MHz, CDCl.sub.3):

[0272] δ=7.9013 (8.2); 7.8966 (8.2); 7.4147 (4.0); 7.4099 (3.8); 7.4023 (4.2); 7.3976 (3.9); 7.3923 (6.3); 7.3861 (6.8); 7.3801 (6.4); 7.3711 (6.5); 7.2609 (13.8); 6.9275 (0.3); 6.2150 (13.9); 4.9445 (2.3); 4.9179 (11.7); 4.9070 (11.5); 4.8803 (2.2); 4.6156 (18.3); 4.3155 (1.5); 4.3070 (2.7); 4.2987 (1.8); 4.2956 (2.3); 4.2882 (2.5); 4.2860 (2.6); 4.2788 (2.0); 4.1948 (2.0); 4.1882 (3.0); 4.1804 (2.1); 4.1748 (1.5); 4.1677 (2.9); 4.1605 (1.4); 3.7651 (0.4); 3.7361 (0.6); 3.5981 (0.4); 3.5864 (7.1); 3.5793 (11.1); 3.5708 (5.8); 3.5581 (0.3); 3.4019 (1.1); 3.3989 (1.1); 3.3882 (0.5); 3.3651 (50.0); 2.0435 (1.3); 1.5688 (28.2); 1.2704 (0.6); 1.2651 (0.6); 1.2585 (1.1); 1.2466 (0.5); 0.8935 (0.6); 0.8820 (1.4); 0.8700 (0.7); 0.0052 (0.8); -0.0001 (18.3); -0.0056 (0.6)

[0273] I.31-442: .sup.1H-NMR (599.6 MHz, CDCl.sub.3):

[0274] δ=7.8899 (11.6); 7.8852 (11.5); 7.4322 (0.4); 7.4192 (8.8); 7.4069 (9.2); 7.4005 (9.2); 7.3856 (9.0); 7.3547 (5.7); 7.3499 (5.4); 7.3422 (5.8); 7.3375 (5.1); 7.2604 (27.9); 6.2204 (19.3); 4.9135 (6.2); 4.8870 (13.8); 4.8487 (13.8); 4.8222 (6.2); 4.5478 (25.9); 4.2296 (0.3); 4.1862 (0.5); 4.1742 (1.4); 4.1683 (2.5); 4.1624 (3.8); 4.1564 (7.1); 4.1506 (7.5); 4.1444 (7.4); 4.1388 (7.2); 4.1326 (3.4); 4.1270 (3.2); 4.1209 (1.1); 4.1153 (1.0); 4.1090 (0.3); 4.1034 (0.3); 3.6847 (0.4); 2.0438 (4.4); 1.5527 (50.0); 1.3017 (0.8); 1.2919 (1.3); 1.2838 (1.4); 1.2798 (2.0); 1.2713 (18.7); 1.2594 (36.4); 1.2475 (17.6); 0.8936 (1.5); 0.8821 (3.5); 0.8701 (1.7); 0.0052 (2.2); -0.0001 (36.7); -0.0056 (1.3)

[0275] I.1-481: .sup.1H-NMR (599.6 MHz, CDCl.sub.3):

[0276] δ=8.1359 (2.5); 8.1331 (2.6); 8.1277 (2.6); 8.1248 (2.5); 7.7639 (2.5); 7.7610 (2.6); 7.7515 (2.7); 7.7486 (2.6); 7.3577 (3.9); 7.3427 (3.9); 7.2602 (39.9); 7.0566 (3.6); 7.0444 (3.6); 6.9885 (2.5); 6.9802 (2.5); 6.9761 (2.5); 6.9678 (2.4); 6.2255 (8.5); 5.2992 (6.9); 4.9646 (2.4); 4.9378 (5.0); 4.8955 (4.9); 4.8686 (2.3); 4.6087 (7.2); 2.1723 (0.5); 2.0906 (0.3); 1.3128 (0.4); 1.3016 (0.8); 1.2900 (1.0); 1.2801 (1.0); 1.2653 (2.2); 0.8937 (2.1); 0.8822 (4.9); 0.8702 (2.4); 0.0052 (2.1); −0.0001 (50.0); −0.0054 (2.0)

[0277] The present invention furthermore provides the use of one or more compounds of the general formula (I) according to the invention and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1) to (I.34) and/or salts thereof, in each case as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamental plants.

[0278] The present invention further provides a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount [0279] of one or more compounds of the general formula (I) according to the invention and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1) to (I.34) and/or salts thereof, in each case as defined above, or [0280] of a composition according to the invention, as defined below,
is applied to the (harmful) plants, seeds of (harmful) plants, the soil in which or on which the (harmful) plants grow or the area under cultivation.

[0281] The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount [0282] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1) to (I.34) and/or salts thereof, in each case as defined above, or [0283] of a composition according to the invention, as defined below,
is applied to unwanted plants (for example harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).

[0284] The present invention also further provides methods for controlling for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount [0285] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1) to (I.34) and/or salts thereof, in each case as defined above, or [0286] of a composition according to the invention, as defined below,
is applied to the plant, the seed of the plant (i.e. plant seed, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the plants will grow).

[0287] In this context, the compounds according to the invention or the compositions according to the invention can be applied for example by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and/or post-emergence processes. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are as follows, though there is no intention to restrict the enumeration to particular species.

[0288] In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and/or salts thereof are preferably employed for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, where in a preferred embodiment the useful plants or ornamental plants are transgenic plants.

[0289] The compounds of the general formula (I) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants: Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0290] Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0291] When the compounds according to the invention are applied to the soil surface before germination of the harmful plants (weed grasses and/or broad-leaved weeds) (pre-emergence method), either the seedlings of the weed grasses or broad-leaved weeds are prevented completely from emerging or they grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.

[0292] If the active compounds are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

[0293] Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.

[0294] In addition, the compounds of the general formula (I) according to the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.

[0295] By virtue of their herbicidal and plant growth regulatory properties, the compounds of the general formula (I) according to the invention can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

[0296] It is preferred with a view to transgenic crops to use the compounds according to the invention and/or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

[0297] It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0298] By virtue of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further special properties may be tolerance or resistance to abiotic stressors, for example heat, cold, drought, salinity and ultraviolet radiation.

[0299] Preference is given to the use of the compounds of the general formula (I) according to the invention or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potatoes, tomatoes, peas and other vegetables.

[0300] It is preferable to employ the compounds of the general formula (I) as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0301] Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods.

[0302] A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known to the person skilled in the art. For such genetic manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove part sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.

[0303] For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

[0304] To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.

[0305] When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

[0306] The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.

[0307] Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

[0308] It is preferable to employ the compounds of the general formula (I) according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active compounds.

[0309] When the active compounds of the invention are employed in transgenic crops, not only do the effects towards harmful plants to be observed in other crops occur, but frequently also effects which are specific to the application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

[0310] The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.

[0311] Preference is given to the use in cereals, here preferably corn, wheat, barley, rye, oats, millet or rice, by the pre- or post-emergence method.

[0312] Preference is also given to the use in soybeans by the pre- or post-emergence method.

[0313] The use according to the invention for the control of harmful plants or for growth regulation of plants also includes the case in which a compound of the general formula (I) or its salt is not formed from a precursor substance (“prodrug”) until after application on the plant, in the plant or in the soil. The invention also provides the use of one or more compounds of the general formula (I) or salts thereof or of a composition according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the general formula (I) or salts thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.

[0314] The invention also provides a herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises

[0315] (a) one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1) to (I.34) and/or salts thereof, in each case as defined above, and

[0316] (b) one or more further substances selected from groups (i) and/or (ii): [0317] (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not conforming to the general formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, [0318] (ii) one or more formulation auxiliaries customary in crop protection.

[0319] Here, the further agrochemically active substances of component (i) of a composition according to the invention are preferably selected from the group of substances mentioned in “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0320] A herbicidal or plant growth-regulating composition according to the invention comprises preferably one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-formers, thickeners, inorganic salts, dusting agents, carriers solid at 25° C. and 1013 mbar, preferably adsorptive granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25° C. and 1013 mbar.

[0321] The compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and/or salts thereof.

[0322] The compounds of the general formula (I) and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are required. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0323] These individual formulation types and the formulation assistants, such as inert materials, surfactants, solvents and further additives, are known to the person skilled in the art and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

[0324] Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active compound, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the herbicidal active compounds are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

[0325] Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts, for example calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

[0326] Dusting products are obtained by grinding the active compound with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0327] Suspension concentrates may be water- or oil-based. They can be produced, for example, by wet grinding by means of standard commercial bead mills and optionally the addition of surfactants, as have already been listed e.g. above for the other types of formulation.

[0328] Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants, as have already been listed e.g. above for the other formulation types.

[0329] Granules can be prepared either by spraying the active compound onto granular inert material capable of adsorption or by applying active compound concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules—if desired as a mixture with fertilizers.

[0330] Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0331] For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw Hill, New York 1973, p. 8-57.

[0332] For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0333] The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of from 0.1 to 99% by weight, preferably 0.5 to 95% by weight, particularly preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active compounds of the general formula (I) and their salts.

[0334] In wettable powders, the active compound concentration is, for example, about 10% to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active compound concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight of active compound; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends partially on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used. In the water-dispersible granules, the content of active compound is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0335] In addition, the active compound formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described, inter alia, in “Chemistry and Technology of Agrochemical Formulations”, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

[0336] The compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of a tank mix. The combination formulations can be prepared on the basis of the abovementioned formulations, while taking account of the physical properties and stabilities of the active compounds to be combined.

[0337] Active compounds which can be employed in combination with the compounds of the general formula (I) according to the invention in mixture formulations or in a tank mix are, for example, known active compounds based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and literature cited therein.

[0338] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the compounds of the general formula (I) according to the invention have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of compounds of the general formula (I) according to the invention are of particular interest which comprise the compounds (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.

[0339] The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds of the general formula (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tank mix with the herbicides.

[0340] For application, the herbicide or herbicide/safener formulations present in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

[0341] The application rate of the compounds of the general formula (I) and/or their salts is affected to a certain extent by external conditions such as temperature, humidity, etc. Here, the application rate may vary within wide limits. For the application as a herbicide for controlling harmful plants, the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, with preference in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies both to the pre-emergence and the post-emergence application.

[0342] When compounds of the general formula (I) and/or their salts are used as plant growth regulator, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of from 0.001 to 2 kg/ha, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha, very particularly preferably in the range from 20 to 250 g/ha. This applies both to the pre-emergence and the post-emergence application.

[0343] The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tittering phase, at the beginning of the longitudinal growth.

[0344] As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. Here, the application rate depends on the particular techniques and can be determined in preliminary tests.

[0345] Active compounds which can be employed in combination with the compounds of the general formula (I) according to the invention in compositions according to the invention (for example in mixed formulations or in the tank mix) are, for example, known active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds of the invention are, for example, the following, where said active compounds are designated either with their “common name” in accordance with the International Organization for Standardization (ISO) or with the chemical name or with the code number. They always encompass all the use forms, for example acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if they are not mentioned explicitly.

[0346] Examples of such herbicidal mixing partners are:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium,-triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium,-sodium and -trimesium, H-9201, i.e. 0-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium,-potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

##STR00093##

[0347] Examples of plant growth regulators as possible mixing partners are:

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

[0348] Useful combination partners for the compounds of the general formula (I) according to the invention also include, for example, the following safeners: [0349] S1) Compounds from the group of heterocyclic carboxylic acid derivatives: [0350] S1.sup.a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1.sup.a), preferably compounds such as [0351] 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (“mefenpyr-diethyl”), and related compounds as described in WO-A-91/07874; [0352] S1.sup.b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1.sup.b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806;

[0353] S1.sup.c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1.sup.c), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554;

[0354] S1.sup.d) Compounds of the triazolecarboxylic acid type (S1.sup.d), preferably compounds such as fenchlorazole(-ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (51-7), and related compounds, as described in EP-A-174562 and EP-A-346620;

[0355] S1.sup.e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1.sup.e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (51-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (51-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (“isoxadifen-ethyl”) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (51-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (51-13) as described in patent application WO-A-95/07897.

[0356] S2) Compounds from the group of the 8-quinolinoxy derivatives (S2):

[0357] S2.sup.a) Compounds of the 8-quinolinoxyacetic acid type (S2.sup.a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (“cloquintocet-mexyl”) (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), [0358] methyl (5-chloro-8-quinolinoxy)acetate (S2-6), [0359] allyl (5-chloro-8-quinolinoxy)acetate (52-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (52-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (52-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (52-10), hydrates and salts thereof, for example the lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002/34048; [0360] S2.sup.b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2.sup.b), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198. [0361] S3) Active compounds of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), for example [0362] “dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (53-1), [0363] “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), [0364] “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (53-3), [0365] “benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (53-4), [0366] “PPG-1292” (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (53-5), [0367] “DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (53-6), [0368] “AD-67” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7), [0369] “TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8), [0370] “diclonon” (dicyclonon) or “BAS145138” or “LAB145138” (S3-9) [0371] ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, [0372] “furilazole” or “MON 13900” ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (53-10), and the (R) isomer thereof (S3-11). [0373] S4) Compounds from the class of the acylsulfonamides (S4): [0374] S4.sup.a) N-Acylsulfonamides of the formula (S4.sup.a) and salts thereof, as described in WO-A-97/45016,

##STR00094## [0375] in which [0376] R.sub.A.sup.1 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, where the 2 latter radicals are substituted by VA substituents from the group of halogen, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio and, in the case of cyclic radicals, also by (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl; [0377] R.sub.A.sup.2 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0378] m.sub.A represents 1 or 2; [0379] v.sub.A represents 0, 1, 2 or 3; [0380] S4.sup.b) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4.sup.b) and salts thereof, as described in WO-A-99/16744,

##STR00095## [0381] in which [0382] R.sub.B.sup.1, R.sub.B.sup.2 independently of one another represent hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0383] R.sub.B.sup.3 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or (C.sub.1-C.sub.4)-alkoxy and [0384] m.sub.B represents 1 or 2, [0385] e.g. those in which [0386] R.sub.B′=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (“cyprosulfamide”, S4-1), [0387] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-2), [0388] R.sub.B.sup.1=ethyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-3), [0389] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-4) and [0390] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-5); [0391] S4.sup.c) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4.sup.c), as described in EP-A-365484,

##STR00096## [0392] in which [0393] R.sub.C.sup.1, R.sub.C.sup.2 independently of one another represent hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0394] R.sub.C.sup.3 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3 and [0395] m.sub.C represents 1 or 2; [0396] for example [0397] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, [0398] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, [0399] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; [0400] S4.sup.d) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4.sup.d) and salts thereof, which are known, for example, from CN 101838227,

##STR00097## [0401] in which [0402] R.sub.D.sup.4 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0403] m.sub.D is 1 or 2; [0404] R.sub.D.sup.5 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.5-C.sub.6)-cycloalkenyl. [0405] S5) Active compounds from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example [0406] ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001. [0407] S6) Active compounds from the class of the 1,2-dihydroquinoxalin-2-ones (S6), for example [0408] 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630. [0409] S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856. [0410] S8) Compounds of the formula (S8), as described in WO-A-98/27049,

##STR00098##

in which the symbols and indices are defined as follows: [0411] R.sub.D.sup.1 represents halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, [0412] R.sub.D.sup.2 represents hydrogen or (C.sub.1-C.sub.4)-alkyl, [0413] R.sub.D.sup.3 represents hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, [0414] n.sub.D represents an integer from 0 to 2. [0415] S9) Active compounds from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example [0416] 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020. [0417] S10) Compounds of the formulae (S10.sup.a) or (S10.sup.b) [0418] as described in WO-A-2007/023719 and WO-A-2007/023764,

##STR00099## [0419] in which [0420] R.sub.E.sup.1 represents halogen, (C.sub.1-C.sub.4)-alkyl, methoxy, nitro, cyano, CF.sub.3, OCF.sub.3, [0421] Y.sub.E, Z.sub.E independently of one another represent O or S, [0422] n.sub.E represents an integer from 0 to 4, [0423] R.sub.E.sup.2 represents (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, aryl; benzyl, halobenzyl, [0424] R.sub.E.sup.3 represents hydrogen or (C.sub.1-C.sub.6)-alkyl. [0425] S11) Active compounds of the oxyimino compounds type (S11), which are known as seed-dressing agents, for example [0426] “oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, [0427] “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyfloxime) (S11-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and [0428] “cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage. [0429] S12) Active compounds from the class of the isothiochromanones (S12), for example methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. [0430] S13) One or more compounds from group (S13): [0431] “naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for corn against thiocarbamate herbicide damage, [0432] “fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, [0433] “flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage, [0434] “CL 304415” (CAS Reg. No. 31541-57-8) [0435] (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage by imidazolinones, [0436] “MG 191” (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn, [0437] “MG 838” (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia [0438] “disulfoton” (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), [0439] “dietholate” (0,0-diethyl 0-phenyl phosphorothioate) (513-8), [0440] “mephenate” (4-chlorophenyl methylcarbamate) (S13-9). [0441] S14) Active compounds which, in addition to herbicidal action against harmful plants, also have safener action on crop plants such as rice, for example [0442] “dimepiperate” or “MY-93” (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate, [0443] “daimuron” or “SK 23” (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron, [0444] “cumyluron”=“JC-940” (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known as a safener for rice against damage by some herbicides, [0445] “methoxyphenone” or “NK 049” (3,3′-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides, [0446] “CSB” (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice. [0447] S15) Compounds of the formula (S15) or tautomers thereof

##STR00100## [0448] as described in WO-A-2008/131861 and WO-A-2008/131860 [0449] in which [0450] R.sub.H.sup.1 is a (C.sub.1-C.sub.6)-haloalkyl radical and [0451] R.sub.H.sup.2 is hydrogen or halogen and [0452] R.sub.H.sup.3, R.sub.H.sup.4 independently of one another represent hydrogen, (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.16)-alkenyl or [0453] (C.sub.2-C.sub.16)-alkynyl, [0454] where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylamino, di[(C.sub.1-C.sub.4)-alkyl]amino, [(C.sub.1-C.sub.4)-alkoxy]carbonyl, [(C.sub.1-C.sub.4)-haloalkoxy]carbonyl, (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0455] or (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.4-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C.sub.4-C.sub.6)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, [0456] where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylamino, di[(C.sub.1-C.sub.4)-alkyl]amino, [(C.sub.1-C.sub.4)-alkoxy]carbonyl, [(C.sub.1-C.sub.4)-haloalkoxy]carbonyl, (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0457] or [0458] R.sub.H.sup.3 is (C.sub.1-C.sub.4)-alkoxy, (C.sub.2-C.sub.4)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy or (C.sub.2-C.sub.4)-haloalkoxy and [0459] R.sub.H.sup.4 is hydrogen or (C.sub.1-C.sub.4)-alkyl or [0460] R.sub.H.sup.3 and R.sub.H.sup.4 together with the directly attached nitrogen atom represent a four- to eight-membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio. [0461] S16) Active compounds which are used primarily as herbicides but also have safener action on crop plants, for example [0462] (2,4-dichlorophenoxy)acetic acid (2,4-D), [0463] (4-chlorophenoxy)acetic acid, [0464] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), [0465] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), [0466] (4-chloro-o-tolyloxy)acetic acid (MCPA), [0467] 4-(4-chloro-o-tolyloxy)butyric acid, [0468] 4-(4-chlorophenoxy)butyric acid, [0469] 3,6-dichloro-2-methoxybenzoic acid (dicamba), [0470] 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).

[0471] Preferred safeners in combination with the compounds of the general formula (I) according to the invention and/or salts thereof, in particular with the compounds of the formulae (I.1) to (I.34) and/or salts thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

Biological Examples

A. Post-Emergence Herbicidal Action and Crop Plant Compatibility

[0472] Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in plastic or wood-fiber pots, covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then sprayed onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 6001/ha (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0473] Tables A1 to A14 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.34 on various harmful plants and at an application rate corresponding to 20 g/ha and less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00002 TABLE A1 Compound Alopecurus myosuroides Application rate Example No. (efficacy in %) [g/ha] I.1-1 90 20 I.1-2 100 20 I.1-23 90 20 I.1-115 100 20 I.1-115 80 5 I.1-176 100 20 I.1-176 90 5 I.1-286 100 20 I.1-286 100 5 I.1-447 90 20 I.1-447 80 5 I.1-457 80 20 I.1-457 80 5 I.1-471 100 20 I.1-471 80 5 I.1-481 100 20 I.1-481 100 5 I.6-441 80 20 I.14-442 90 20 I.31-1 80 20 I.31-23 100 20 I.31-442 90 20 I.31-442 80 5

TABLE-US-00003 TABLE A2 Compound Digitaria sanguinalis Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 100 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 100 5 I.1-441 100 20 I.1-441 90 5 I.1-442 100 20 I.1-447 100 20 I.1-447 100 5 I.1-448 100 20 I.1-457 100 20 I.1-457 100 5 I.2-442 100 20 I.6-441 100 20 I.6-441 80 5 I.14-442 100 20

TABLE-US-00004 TABLE A3 Compound Echinochloa crus-galli Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 90 5 I.1-2 100 20 I.1-2 90 5 I.1-23 100 20 I.1-23 80 5 I.1-115 100 20 I.1-115 90 5 I.1-176 100 20 I.1-176 90 5 I.1-286 100 20 I.1-286 90 20 I.1-441 100 20 I.1-441 80 5 I.1-442 100 20 I.1-442 100 5 I.1-447 100 20 I.1-447 100 5 I.1-457 100 20 I.1-457 80 5 I.1-471 100 20 I.1-471 90 5 I.1-481 100 20 I.1-481 90 5 I.1-441 100 20 I.1-442 100 20 I.2-442 100 20 I.5-457 80 20 I.6-441 90 20 I.6-441 80 5 I.14-442 100 20 I.31-1 90 20 I.31-23 100 20 I.31-23 80 5 I.31-442 90 20 I.31-442 90 5

TABLE-US-00005 TABLE A4 Compound Lolium rigidum Application rate Example No. (efficacy in %) [g/ha] I.1-2 80 20 I.1-23 80 20 I.1-441 80 20 I.1-471 80 20 I.1-481 80 20

TABLE-US-00006 TABLE A5 Compound Setaria viridis Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 100 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 100 5 I.1-441 100 20 I.1-441 100 5 I.1-442 100 20 I.1-442 100 5 I.1-447 100 20 I.1-447 100 5 I.1-448 100 20 I.1-448 80 5 I.1-457 100 20 I.1-457 100 5 I.2-442 100 20 I.2-442 100 5 I.5-442 90 5 I.5-457 100 20 I.5-457 100 5 I.6-441 100 20 I.6-441 90 5 I.14-442 100 20 I.14-442 100 5

TABLE-US-00007 TABLE A6 Compound Abutilon theophrasti Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 100 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 100 5 I.1-115 100 20 I.1-115 90 5 I.1-176 100 20 I.1-176 100 5 I.1-286 100 20 I.1-286 100 5 I.1-441 100 20 I.1-441 100 5 I.1-442 100 20 I.1-442 100 5 I.1-447 100 20 I.1-447 100 5 I.1-448 80 20 I.1-448 80 5 I.1-457 100 20 I.1-457 100 5 I.1-471 100 20 I.1-471 100 5 I.1-481 100 20 I.1-481 100 5 I.2-442 100 20 I.2-442 100 5 I.5-442 100 5 I.5-457 80 20 I.6-441 100 20 I.6-441 100 5 I.31-1 100 20 I.31-1 100 5 I.14-442 100 20 I.14-442 100 5 I.31-23 100 20 I.31-23 100 5 I.31-442 100 20 I.31-442 100 5

TABLE-US-00008 TABLE A7 Compound Amaranthus retroflexus Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 100 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 100 5 I.1-115 100 20 I.1-115 100 5 I.1-176 100 20 I.1-176 100 5 I.1-286 100 20 I.1-286 100 5 I.1-441 100 20 I.1-441 100 5 I.1-442 100 20 I.1-442 100 5 I.1-447 100 20 I.1-447 100 5 I.1-448 100 20 I.1-448 100 5 I.1-457 100 20 I.1-457 100 5 I.1-471 100 20 I.1-471 100 5 I.1-481 100 20 I.1-481 100 5 I.2-442 100 20 I.2-442 100 5 I.5-442 100 5 I.5-457 100 20 I.5-457 100 5 I.6-441 100 20 I.6-441 100 5 I.14-442 100 20 I.14-442 100 5 I.31-1 100 20 I.31-1 100 5 I.31-23 100 20 I.31-23 100 5 I.31-442 100 20 I.31-442 100 5

TABLE-US-00009 TABLE A8 Compound Matricaria inodora Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 90 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 80 5 I.1-115 100 20 I.1-115 100 5 I.1-176 100 20 I.1-176 100 5 I.1-286 100 20 I.1-286 100 5 I.1-441 100 20 I.1-441 100 5 I.1-442 100 20 I.1-442 90 5 I.1-447 100 20 I.1-447 100 5 I.1-457 90 20 I.1-471 100 20 I.1-471 100 5 I.1-481 100 20 I.1-481 90 5 I.2-442 90 20 I.5-442 80 5 I.6-441 80 20 I.14-442 100 20 I.14-442 100 5 I.31-1 100 20 I.31-1 80 5 I.31-23 100 20 I.31-23 100 5 I.31-442 100 20

TABLE-US-00010 TABLE A9 Compound Pharbitis purpurea Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 100 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 80 5 I.1-115 100 20 I.1-115 100 5 I.1-176 100 20 I.1-176 100 5 I.1-286 100 5 I.1-441 100 20 I.1-441 100 5 I.1-442 100 5 I.1-448 100 20 I.5-442 100 5 I.1-447 100 20 I.1-447 100 5 I.1-457 100 20 I.1-457 100 5 I.1-471 100 20 I.1-471 100 5 I.1-481 100 20 I.1-481 80 5 I.5-457 90 20 I.5-457 90 5 I.6-441 90 20 I.6-441 80 5 I.14-442 100 20 I.14-442 90 5 I.31-1 100 20 I.31-1 100 5 I.31-23 100 20 I.31-23 100 5 I.31-442 100 20 I.31-442 80 5

TABLE-US-00011 TABLE A10 Compound Polygonum convolvulus Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 80 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 100 5 I.1-441 100 20 I.1-441 80 5 I.1-442 100 20 I.1-448 100 20 I.1-447 100 20 I.1-447 100 5 I.1-457 100 20 I.1-457 100 5 I.2-442 100 20 I.2-442 100 5 I.5-442 100 5 I.5-457 100 20 I.5-457 90 5 I.6-441 100 20 I.6-441 100 5 I.14-442 100 20

TABLE-US-00012 TABLE A11 Compound Stellaria media Application rate Example No. (efficacy in %) [g/ha] I.1-441 100 5 I.1-442 100 20 I.2-442 100 20 I.2-442 80 5 I.5-457 100 20 I.5-457 80 5 I.6-441 100 20 I.6-441 100 5

TABLE-US-00013 TABLE A12 Compound Viola tricolor Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 100 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 100 5 I.1-115 100 20 I.1-115 100 5 I.1-176 100 20 I.1-176 100 5 I.1-286 100 20 I.1-286 100 5 I.1-441 100 20 I.1-441 100 5 I.1-442 100 20 I.1-442 100 5 I.1-447 100 20 I.1-447 100 5 I.1-448 100 20 I.1-448 100 5 I.1-457 100 20 I.1-457 100 5 I.1-471 100 20 I.1-471 100 5 I.1-481 100 20 I.1-481 100 5 I.2-442 100 20 I.2-442 100 5 I.5-442 100 5 I.5-457 100 20 I.5-457 100 5 I.6-441 100 20 I.6-441 100 5 I.14-442 100 20 I.14-442 100 5 I.31-1 100 20 I.31-1 100 5 I.31-23 100 20 I.31-23 100 5 I.31-442 100 20 I.31-442 100 5

TABLE-US-00014 TABLE A13 Compound Veronica persica Application rate Example No. (efficacy in %) [g/ha] I.1-1 100 20 I.1-1 100 5 I.1-2 100 20 I.1-2 100 5 I.1-23 100 20 I.1-23 100 5 I.1-115 100 20 I.1-115 100 5 I.1-176 100 20 I.1-176 100 5 I.1-286 100 20 I.1-286 100 5 I.1-441 100 20 I.1-441 100 5 I.1-442 100 20 I.1-442 100 5 I.1-447 100 20 I.1-447 100 5 I.1-448 80 20 I.1-448 80 5 I.1-457 100 20 I.1-457 100 5 I.1-471 100 20 I.1-471 100 5 I.1-481 100 20 I.1-481 100 5 I.2-442 100 20 I.2-442 100 5 I.5-442 100 5 I.5-457 100 20 I.5-457 100 5 I.6-441 100 20 I.6-441 100 5 I.14-442 100 20 I.14-442 100 5 I.31-1 100 20 I.31-1 100 5 I.31-23 100 20 I.31-23 100 5 I.31-442 100 20 I.31-442 100 5

TABLE-US-00015 TABLE A14 Compound Hordeum murinum Application rate Example No. (efficacy in %) [g/ha] I.1-441 100 20 I.1-441 80 5

TABLE-US-00016 TABLE A15 Compound Avena fatua Application rate Example No. (efficacy in %) [g/ha] I.1-1 80 20 I.1-2 80 20 I.1-23 100 20 I.1-176 80 20 I.1-286 80 20 I.1-457 80 20 I.1-471 80 20 I.14-442 80 20 I.31-23 80 20

[0474] Tables A16 to A20 below show the crop plant compatibilities of selected compounds of the general formula (I) according to Tables I.1 to I.34 at an application rate corresponding to 5 g/ha and less, which were observed in trials by the experimental procedure mentioned above. Here, the observed effects on selected crop plants are stated in comparison to the untreated controls (values in %).

TABLE-US-00017 TABLE A16 Compound Oryza sativa Application rate Example No. (efficacy in %) [g/ha] I.1-1 10 1.25 I.1-2 10 5 I.1-2 0 1.25 I.1-23 20 1.25 I.1-286 0 1.25 I.1-447 10 5 I.1-447 0 1.25 I.1-448 0 5 I.1-457 0 1.25 I.1-481 20 5 I.1-481 10 1.25 I.2-442 0 5 I.31-1 10 5 I.31-1 0 1.25 I.31-23 20 5 I.1-441 20 5 I.1-441 10 1.25 I.1-442 20 5 I.1-442 10 1.25 I.1-471 0 1.25 I.2-442 0 5 I.5-442 20 5 I.5-457 10 5 I.5-457 0 1.25 I.6-441 20 5 I.14-442 20 5 I.14-442 10 1.25 I.31-442 10 5 I.31-442 0 1.25

TABLE-US-00018 TABLE A17 Compound Zea mays Application rate Example No. (efficacy in %) [g/ha] I.1-23 20 1.25 I.1-441 20 1.25 I.1-442 20 1.25 I.1-448 20 5 I.1-457 20 1.25 I.1-471 20 5 I.2-442 20 5 I.2-442 10 1.25 I.5-457 20 5 I.6-441 20 5 I.6-441 10 1.25 I.14-442 20 1.25

TABLE-US-00019 TABLE A18 Compound Brassica napus Application rate Example No. (efficacy in %) [g/ha] I.1-442 10 1.25 I.5-442 20 5 I.5-442 0 1.55 I.5-457 10 5 I.5-457 0 1.25 I.6-441 20 1.25

TABLE-US-00020 TABLE A19 Compound Glycine max Application rate Example No. (efficacy in %) [g/ha] I.1-441 20 5 I.1-442 20 5 I.1-442 10 1.25 I.2-442 10 1.25 I.5-457 10 5 I.5-457 0 1.25 I.14-442 20 1.25

TABLE-US-00021 TABLE A20 Compound Triticum aestivum Application rate Example No. (efficacy in %) [g/ha] I.1-1 0 1.25 I.1-2 0 1.25 I.1-23 20 1.25 I.1-115 20 1.25 I.1-176 20 1.25 I.1-286 20 1.25 I.1-441 20 1.25 I.1-448 10 5 I.1-448 0 1.25 I.1-457 20 1.25 I.2-442 20 5 I.31-1 10 5 I.31-23 20 5 I.31-23 10 5 I.1-447 10 1.25 I.1-471 20 5 I.1-471 10 1.25 I.1-481 20 1.25 I.2-442 20 5 I.5-442 20 5 I.5-442 10 1.25 I.5-457 20 5 I.6-441 20 5 I.14-442 20 1.25 I.31-442 20 5 I.31-442 10 1.25

[0475] As the results show, compounds of the general formula (I) according to the invention, in post-emergence treatment, have good herbicidal activity against harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Hordeum murinum, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor at an application rate of between 0.005 and 0.02 kg of active substance or less per hectare, and good crop plant compatibility with organisms such as Oryza sativa, Zea mays, Brassica napus, Glycine max and Triticum aestivum at an application rate of 0.005 kg and less per hectare.

B. Pre-Emergence Herbicidal Action and Crop Plant Compatibility

[0476] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in plastic or organic planting pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied to the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate equivalent to 6001/ha (converted). After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0477] Tables B1 to B11 below show the effects of selected compounds of the general formula (I) according to Tables I.1 to I.34 on various harmful plants and at an application rate corresponding to 80 g/ha and less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00022 TABLE B1 Compound Alopecurus myosuroides Application rate Example No. (efficacy in %) [g/ha] I.1-442 90 80 I.5-442 80 80

TABLE-US-00023 TABLE B2 Compound Digitaria sanguinalis Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.1-442 100 20 I.5-442 80 80

TABLE-US-00024 TABLE B3 Compound Echinochloa crus-galli Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.5-442 80 80

TABLE-US-00025 TABLE B4 Compound Setaria viridis Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.1-442 90 20 I.5-442 100 80

TABLE-US-00026 TABLE B5 Compound Abutilon theophrasti Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.5-442 100 80

TABLE-US-00027 TABLE B6 Compound Amaranthus retroflexus Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.1-442 100 20 I.5-442 100 80 I.5-442 100 20

TABLE-US-00028 TABLE B7 Compound Matricaria inodora Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.1-442 100 20 I.5-442 90 80

TABLE-US-00029 TABLE B8 Compound Pharbitis purpurea Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.5-442 100 80

TABLE-US-00030 TABLE B9 Compound Polygonum convolvulus Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.1-442 90 20 I.5-442 100 80 I.5-442 100 20

TABLE-US-00031 TABLE B10 Compound Viola tricolor Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.1-442 100 20 I.5-442 100 20 I.5-442 100 20

TABLE-US-00032 TABLE B11 Compound Veronica persica Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80 I.1-442 80 20 I.5-442 100 80 I.5-442 90 20

TABLE-US-00033 TABLE B12 Compound Lolium rigidum Application rate Example No. (efficacy in %) [g/ha] I.1-442 100 80

[0478] Tables B13 to B16 below show the crop plant compatibilities of selected compounds of the general formula (I) according to Tables I.1 to I.34 at an application rate corresponding to 80 g/ha or less, which were observed in trials by the experimental procedure mentioned above. Here, the observed effects on selected crop plants are stated in comparison to the untreated controls (values in %).

TABLE-US-00034 TABLE B13 Compound Zea mays Application rate Example No. (efficacy in %) [g/ha] I.1-442 0 20 I.5-442 20 80 I.5-442 0 20

TABLE-US-00035 TABLE B14 Compound Brassica napus Application rate Example No. (efficacy in %) [g/ha] I.1-442 0 20 I.5-442 0 20

TABLE-US-00036 TABLE B15 Compound Glycine max Application rate Example No. (efficacy in %) [g/ha] I.5-442 0 80

TABLE-US-00037 TABLE B16 Compound Triticum aestivum Application rate Example No. (efficacy in %) [g/ha] I.1-442 10 20 I.5-442 20 20

[0479] As the results show, compounds of the general formula (I) according to the invention, in pre-emergence treatment, have good herbicidal activity against harmful plants, for example against harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at an application rate of 0.08 kg of active substance or less per hectare, and good crop plant compatibility with organisms such as Zea mays, Brassica napus, Glycine max and Triticum aestivum at an application rate of 0.08 kg or less per hectare.

C. Comparative Herbicidal Action and Crop Plant Compatibility of a Compound According to the Invention (I.14-442) with a Structurally Related Compound Known from the Literature (WO2019/101551, No. 16) by the Post-Emergence Method

[0480] Seeds of mono- or dicotyledonous weed plants were sown in pots (diameter 7 cm) with sandy loam soil, germinated under optimium growth conditions and cultivated for 21 days.

[0481] The compounds, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were sprayed onto the green parts of the plants as aqueous suspension or emulsion with addition of 1.5 l/ha Mero and 2 kg/ha AMS at a water application rate of 300 l/ha (converted).

[0482] After the test plants had been kept in the greenhouse under optimum growth conditions for 21 days, the activity of the preparations was rated visually in comparison to untreated control plants.

[0483] For example, 100% action=the plants have died and

[0484] 0% action=like control plants.

[0485] Tables C.sub.1-C.sub.3 below show the effects of a compound according to the invention (I.14-442) and a structurally related compound from WO2019/101551 (No. 16) on various harmful plants and at an application rate corresponding to 18 g/ha and less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00038 TABLE C1 Polygonum Application convolvulus rate Compound (efficacy in %) [g/ha] I.14-442 (according to the invention) 100 18 [00101] No. 16 (from WO2019/101551) 75 18 [00102] I.14-442 (according to the invention) 99 6 No. 16 (from WO2019/101551) 65 6

TABLE-US-00039 TABLE C2 Application Solanum nigrum rate Compound (efficacy in %) [g/ha] I.14-442 (according to the invention) 100 18 No. 16 (from WO2019/101551) 80 18 I.14-442 (according to the invention) 100 6 No. 16 (from WO2019/101551) 80 6

TABLE-US-00040 TABLE C3 Xanthium Application strumarium rate Compound (efficacy in %) [g/ha] I.14-442 (according to the invention) 100 18 No. 16 (from WO2019/101551) 85 18 I.14-442 (according to the invention) 96 6 No. 16 (from WO2019/101551) 50 6

[0486] As shown by the results displayed in Tables C1 to C3, compound 114-442 according to the invention, in comparison to the compound known from the literature (WO2019/101551, No. 16), has a considerably improved herbicidal action against harmful plants such as Polygonum convolvulus, Solanum nigrum and Xanthium strumarium at an application rate of 18 g or less per hectare.

[0487] Tables C4 and C5 below show the effects of a compound according to the invention (114-442) and a compound from WO2019/101551 (No. 16) on various crop plants and at an application rate corresponding to 6 g/ha and less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00041 TABLE C4 Application Compound Zea mays rate Example No. (efficacy in %) [g/ha] I.14-442 (according to the invention) 20 6 No. 16 (from WO2019/101551) 50 6 I.14-442 (according to the invention) 20 2 No. 16 (from WO2019/101551) 40 2

TABLE-US-00042 TABLE C5 Application Compound Glycine max rate Example No. (efficacy in %) [g/ha] I.14-442 (according to the invention) 20 6 No. 16 (from WO2019/101551) 50 6 I.14-442 (according to the invention) 10 2 No. 16 (from WO2019/101551) 40 2

[0488] As shown by the results displayed in Tables C4 and C5, compound 114-442 according to the invention, in comparison to the compound known from the literature (WO2019/101551, No. 16), has a considerably improved crop plant compatibility with organisms such as Zea mays and Glycine max at an application rate of 6 g and less per hectare.