N-phenyl-and n-pyridyi-pyrazole compounds and N-pyridyltetramethylene triazolidine diones which are herbicidally active are described, for example, in EP-A-0 370 332, DE-A-3 917 469, DE-A-19 518 054, DE-A-19 530 606, US-A-5 306 694 and US-A-4 406 689.

Also known as herbicides are N-pyridylimides, N- (2-pyridyl) pyridazinones and N- phenyluracils, as described, for example, in WO 92/00976, JP-A-58-213 776 and EP-A-0 438 209.

N- (phenyl) tetrahydroimidazoles having herbicidal activity are described, for example, in US- A-5 112 383.

There have now been found novel substituted N-pyridyl-nitrogen heterocycles which have herbicidal and growth-inhibitory properties.

The present invention thus relates to compounds of the formula I in which A =N-or Ri is hydrogen, fluorine, chlorine, bromine or methyl; R2 is C1-C4alkyl, C,-C4haloalkyl, halogen, R6O-, nitro, amino or cyano; R3 is halogen, nitro, amino, R4NH-, R4R5N-, azido or CIS (0) 2- ; R4 and R5 independently of one another are C,-Cealkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C8haloalkenyl,HCO-,C1-C4alkylcarbonyl,C3-C6cycloalkyl,C1- C8haloalkyl, C1-C4haloalkylcarbonyl, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, benzyl or benzyl which is mono-to trisubstituted on the phenyl ring by halogen, C1-C4alkyl or C1-C4haloalkyl; or R4 and R5 together with the N atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains O, N or S as further hetero atoms and which can be substited by halogen, C1-C3alkoxy,C1-C4alkoxycarbonyl,C1-C3haloalkyl, Ci-C3aIkylS (O) n,-, nitro or cyano; or R3 is R6O-; R6 is hydrogen, C,-C8alkyl, C3-C8alkenyl, C3-CBalkynyl, C3-C6cycloalkyl, C,-C8haloalkyl, hydroxy-C1-C4alkyl,C1-C4alkoxy-C1-C4alkyl,C3-cyano-C1-C8alky l,C3-C8haloalkenyl, C1-C4alkoxy-C1-C4alkoxy-C1-C4alkyl,C6alkenyloxy-C1-C4alkyl,C 3-C6alkynyloxy-C1-C4alkyl, C1-C8alkoxycarbonyl,C3-C1-C4alkylthio-C1-C4alkyl,C1-C8alkylc arbonyl, C8alkenyloxycarbonyl, benzyloxy-C,-or-C2alkyl, benzylcarbonyl, benzyloxycarbonyl, phenyl, phenyl-C2-C8alkyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, it being possible for these aromatic and heteroaromatic rings to be optionally mono-to trisubstituted bv halogen, C1-C4alkyl or C1-C4haloalkyl; or R6 is R7X, C (O)-C,-C8alkyl-or R7xlc (05 [cl-C. alkylenl- (C6Hs) X1 is oxygen, R8-N-or R7 is hydrogen, Ci-Cgatkyt, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, C,-Cehaloalkyl, C3- C3-C6-alkenyloxy-C1-C4alkyl,C1-C4alkylthio-C1-C4alkyl,C8halo alkenyl,C1-C4alkoxyC1-C4alkyl, phenyl, phenyl which is mono-to trisubstituted by halogen, C1-C4alkyl, or C,-C4haloalkyl, or benzyl or benzyl which is mono-to trisubstituted on the phenyl ring by halogen, C1-C4alkyl or C1-C4haloalkyl; Re is hydrogen, Ci-Cgatkyt, C3-C8alkenyl, C3-Cealkynyl, C3-C6cycloalkyl, C,-Cehaloalkyl or benzyl; or R3 is R9S (O)n1- ; n, is 0,1 or 2; R9 is C3-C8alkynyl,C3-C6cycloalkyl,C1-C8haloalkyl,carbocy-C1-C3-C8 alkenyl, benzyloxycarbonylC1-C4alkyl,C1-C4alkylthio-C(O)-C4-alkyl,C1- C4alkoxycarbonyl-C1-C4alkyl, C1-C4alkylaminocarbonyl-C1-C4alkyl,di-C1-C1-C4alkyl,C3-C5alk enyloxycarbonyl-C1-C4alkyl, C4alkylaminocarbonyl-C,-C4alkyl, C3-C5alkenylaminocarbonyl-C,-C4alkyl, C3-Cehaloalkenyl, C1-C4alkylthio-C1-C4alkyl,phenyl,C1-C4alkoxy-C1-C4alkyl,C3-C 6alkenyloxy-C1-C4alkyl, phenyl which is mono-to trisubstituted by halogen, C,-C4alkyl or C1-C4haloalkyl, or benzyl or benzyl which is mono-to trisubstituted on the phenyl ring by halogen, C1-C4alkyl or Cl- C4haloalkyl, and, if n, is 0, Rg is additionally hydrogen, C,-C8alkylcarbonyl, R10X2C(O)- or R10X2C(O)-C1- or -C2alkyl ; X2 is oxygen, sulfur or R11-N-; R10 is hydrogen, C3-C8alkynyl,C3-C6cycloalkyl,C1-C8haloalkyl,C3-C3-C8alkenyl, C8haloalkenyl,C1-C4alkylthio-C1-C4alkyl,C3-C6alkenyloxy-C1-C 4alkyl, phenyl, phenyl which is mono-to trisubstituted by halogen, C,-C4alkyl or C1-C4haloalkyl, or benzyl or benzyl which is mono-to trisubstituted on the phenyl ring by halogen, C,-C4alkyl or C1-C4haloalkyl; R"is hydrogen, C1-C8alkyl or C3-C8alkenyl; or R3 is R12R13NS(O)2-; hydrogen,C1-C8alkyl,C2-C8alkenyl,C3-C8alkynylorC1-C4alkoxy6c ycloalkyl;R12is Pis is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C8haloalkyl, C1-C4alkoxy-C1- C4alkyl, C1-C4alkylcarbonyl, C1-C4haloalkylcarbonyl, benzyl, benzyl, or benzyl or benzoyl which are mono-to trisubstituted on the phenyl ring by halogen, C1-C4alkyl or Cl- C4haloalkyl; W is a group (W3) or R14 is C1-C3alkyl, C1-C3haloalkyl or amino; C1-C3haloalkyl,C1-C3alkyl-S(O)n2-,C1-C3haloalkyl-S(O)n2-orcy ano;orR15is R, 5 and R14 together form a C3 or C4alkylene bridge which can be substituted by halogen, C1-C3haloalkyl or cyano; n2 is 0,1 or 2; R16 is hydrogen, C1-C3alkyl, halogen, C1-C3haloalkyl or cyano ; or R16 and R15 together form a C3 or C4alkylene bridge which can be substituted by halogen, C1-C3haloalkyl or cyano; R17 is hydrogen, C1-C3alkyl, halogen or cyano; R18 is C1-C3haloalkyl; or R, 8 and R17 together form a C3 or C4alkylene or C3 or C4alkenylene bridge, both of which can be substituted by halogen, Ci-C3alkyl or C1-C3haloalkyl; R19 is hydrogen, C1-C3alkyl or halogen; or R19 and R, 8 together form a C3 or C4alkylene or C3 or C4alkenylene bridge, both of which can be substituted by orC1-C3haloalkyl;C1-C3alkyl R20 and R2, independently of one another are hydrogen or C1-C4alkyl; or R2o and R2, together are a group of R25 and R26 independently of one another are C1-C4alkyl; or R25 and R26 together form a C4 or C5alkylene bridge; R22 is hydrogen or C1-C3alkyl; or R22 and R21 together form a C3-C5alkylene bridge which can be interrupted by oxygen and substituted by C1-C3haloalkyl,C2-C4alkenyl,C1-C3alkylcarbonyloxy,C1-C1-C4al kyl, C3alkoxycarbonyl, C,-C3alkylsulfonyloxy, hydroxyl or =O; R23 and R24 independently of one another are hydrogen or Ci-Caatky); or R23 and R24 together form a C2-C5alkylene bridge which can be interrupted by oxygen, sulfur,-C (O)-or-S (O) 2-; and X3, X4, X5, X6, X7, X8 and X9 independently of one another are oxygen or sulfur, and the agrochemically tolerated salts and stereoisomers of these compounds of the formula 1.

In the abovementioned definitions, halogen is to be understood as meaning iodine, preferably fluorine, chlorine and bromine.

The alkyl, alkenyl and alkynyl groups in the definitions of substituents can be straight-chain or branched, and this also applies to the alkyl, alkenyl and alkynyl moiety of the alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkenyloxyalkyl, alkylsulfonyloxy,alkylthioalkyl,alkoxyalkyl,alkoxyalkoxyalky l,alkynyloxyalkyl-,alkylS(O)n2-, alkylamino, dialkylamino, phenylalkyl and R7X1C(O)-C1-C8alkyl groups.

Alkyl groups, are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso- butyl, tert-butyl and the various isomeric pentyl, hexyl, heptyl and octyl radicals. Preferred are methyl, ethyl, n-propyl, iso-propyl and n-butyl.

Examples which may be mentioned of alkenyls are vinyl, allyl, methallyl, 1-methylvinyl, but- 2-en-1-yl, pentenyl, 2-hexenyl, 3-heptenyl and 4-octenyl, preferably alkenyl radicals having a chain length of 3 to 5 carbon atoms.

Examples of alkynyls which may be mentioned are propargyl, 1-methylpropargyl, 3-butinyl, but-2-yn-1-yl, 2-methylbutin-2-yl, but-3-yn-2-yl, 1-pentinyl, pent-4-yn-1-yl, 2-hexinyl, 3- heptin-1-yl and 4-octin-1-yl, preferably alkynyl radicals having a chain length of 3 or 4 carbon atoms.

Suitable as haloalkyl are alkyl groups which are mono-or polysubstituted, in particular mono-to trisubstituted, by halogen, halogen being specifically iodine and in particular fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl.

Suitable as haloalkenyl are alkenyl groups which are mono-or polysubstituted by halogen, halogen being specifically bromine, iodine and in particular fluorine and chlorine, for example 2-and 3-fluoropropenyl, 2-and 3-chloropropenyl, 2-and 3-bromopropenyl, 2,3,3- trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trifluorobut-2-en-1-yl and 4,4,4-trichlorobut-2- en-1-yl. Preferred amongst the alkenyl radicals which are mono-, di-or trisubstituted by halogen are those which have a chain length of 3 or 4 carbon atoms. The alkenyl groups can be substituted by halogen on saturated or unsaturated carbon atoms.

Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyt, tert-butylsulfonyl; preferably methylsulfonyl and ethylsulfonyl.

Haloalkylsulfonyl is, for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chloromethylsulfonyl, trichloromethylsulfonyl, 2-fluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and 2,2,2-trichloroethylsulfonyl.

Haloalkenylsulfonyi is, for example, 2-and 3-fluoropropenylsulfonyl, 2-and 3- chloropropenylsulfonyl, 2-and 3-bromopropenylsulfonyl, 2,3,3-trifluoropropenylsulfonyl, 2,3,3-trichloropropenylsulfonyl, 4,4,4-trifluoro-but-2-en-1-yl-sulfonyl and 4,4,4-trichlorobut-2- en-1-yl-sulfonyl.

Alkylcarbonyl is, in particular, acetyl and propionyl.

Haloalkylcarbonyl is, in particular, trifluoroacetyl, trichloroacetyl, 3,3,3-trifluoropropionyl and 3,3,3-trichloropropionyl.

Cyanoalkyl is, for example, cyanomethyl, cyanoethyl, cyanoeth-1-yl and cyanopropyl.

Hydroxyalkyl is, for example, 2-hydroxyethyl, 3-hydroxypropyl and 2,3-dihydroxypropyl.

Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, iso-propoxymethyl and iso-propoxyethyl.

Alkenyloxyalkyl is, for example, allyloxyalkyl, methallyloxyalkyl and but-2-en-1-yl-oxyalkyl.

Alkynyloxyalkyl is, for example, propargyloxyalkyl and 1-methylpropargyloxyalkyl.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso- propoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl and ethoxycarbonyl.

Alkenyloxycarbonyl is, for example, allyloxycarbonyl, methallyloxycarbonyl, but-2-en-1-yl- oxycarbonyl, pentenyloxycarbonyl and 2-hexenyloxycarbonyl.

The cycloalkyl radicals which are suitable are as substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkylthio is, for example, methylthio, ethylthio, propylthio and iso-propylthio.

Alkylthioalkyl is, for example, methylthioethyl, ethylthioethyl, methylthiopropyl and ethylthiopropyl.

L in the reagents of the formulae V, Vll, XXI, XXX, XXXllla and XXXIIIb in reaction schemes 1,2,4,6 and 7 is a leaving group such as, for example, halogen, for example chlorine, bromine or iodine, or sulfate, for example CH3S (O) 20- or L, in the reagent of the formula XXII (reaction scheme 4) is a leaving group such as, for example, HOS (0) 20-, R4 and R5 together with the N atom to which they are bonded form a saturated or unsaturated heterocyclic ring which can contain O, N or S as further heteroatoms, for example the following heterocycles: and , it being possible for these heterocycles additionally to be substituted by halogen, d-Csatky), C1-C3haloalkyl, C1-C3alkoxy, C1-C4alkoxycarboyl, C1-C3alkylS(O)n1-, nitro or cyano.

Corresponding meanings may also be assigned to the substituents in composite definitions such as, for example, alkenyloxycarbonylalkyl, alkenylaminocarbonylalkyl, alkylthio-C (O)- alkyl, haloalkylS (O) n2, R4NH-, R4R5N-, R10X2C(O)-, R6O-, R9S(O)n1-, R10X2C(O)-, R10X2C(O)- C, or-C2alkyl and R12R, 3NS (O) 2-.

In the definition of R6, the group R7 C (O)- [C-CBalkylen]- (C6H5) means that the R7X1C(O) -substituted C1-C8alkylene chain is additionally phenyl-substituted on one of the 8 carbon atoms, it being possible for the phenyl ring to be mono-to trisubstituted by halogen, Cl- C4alkyl or C,-C4haloalkyl and for the alkylene chain to be straight-chain or branched, for example methylene, ethylene, methylethylene, propylene, 1-methylpropylene and butyiene.

In the definitions cyanoalkyl, carboxyalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkenyloxycarbonyl and haloalkylcarbonyl, the carbonyl carbon atom is not included in the lower and upper limits of carbon atoms given in each case.

The invention also extends to the salts which the compounds of the formula I which have an acidic hydrogen, in particular the derivatives having carboxyl and sulfonamide groups (for example carboxyl-substituted alkyl and alkylene groups (R6), alkylS (O) 2NH-and haloalkylS (O) 2NH- substituted pyridyl groups (R3)), can form with bases. These salts are, for example, alkali metal salts such as, for example, sodium salts and potassium salts; alkaline earth metal salts such as, for example, calcium salts and magnesium salts; ammonium salts, i. e. unsubstituted ammonium salts and mono-or polysubstituted ammonium salts such as, for example, triethylammonium salts and methylammonium salts; or salts with other organic bases.

Amongst the alkali metal hydroxides and alkaline earth metal hydroxides, examples of salt formers which must be emphasized are the hydroxides of lithium, sodium, potassium, magnesium or calcium, but in particular those of sodium and potassium. Suitable salt formers are described, for example, in WO 97/41112.

Possible examples for amines which are suitable for ammonium salt formation are ammonia and also primary, secondary and tertiary C1-C18alkylamines, C1-C4hydroxyalkylamines and C2-C4alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso- propylamine, the four butylamine isomers, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methyl- hexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethyl- butylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, di-iso-propylamine, di-n-butylamine, di-n- amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n- propanolamine, iso-propanolamine, N, N-diethanolamine, N-ethylpropanolamine, N- butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl- 2-amine, di-butenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-n-butylamine, tri-iso-butylamine, tri- sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines such as, for example, pyridine, quinoline, iso-quinoline, morpholine, thiomorpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as, for example, anilines, methoxyanilines, ethoxyanilines, o, m, p-toluidines, phenylenediamines, benzidines, naphthylamines and o, m, p-chloroanilines; but in particular triethyl amine, iso- propylamine and di-iso-propylamine.

The salts of the compounds of the formula I which have basic groups, in particular basic pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and pyrazolyl rings or of the derivatives having amino groups such as, for example, alkylamino and dialkylamino groups in the definition of R2 or R3 are, for example, salts with inorganic and organic acids such as, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid, and also sulfuric acid, phosphoric acid, nitric acid and organic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid.

The presence of an asymmetric carbon atom in the compounds of the formula 1, for example in the substituent R2 or R3 = OR6, in which R6 is a branched alkyl, alkenyl, haloalkyl or alkoxyalkyl group, or R3 = S (O) n1Rg, in which, for example, n, = 1 and/or Rg is a branched alkyl, alkenyl, haloalkyl or alkoxyalkyl group, results in the fact that the compounds may occur not only in optically active single isomers, but also in the form of racemic mixtures.

The present invention is to be understood as meaning, by active ingredients of the formula I, not only the pure optical antipodes but also the racemates or diastereomers.

If an aliphatic C=C double bond is present, geometric isomerism may occur. The present invention also extends to these isomers.

Preferred compounds of the formula I are those in which R2 is methyl, halogen, hydroxyl, nitro, amino or cyano; R3 is nitro, amino, R4NH-, R4R5N-, azido or CIS (0) 2- ; Rg, if ni is 0, is additionally hydrogen, d-Csaikyicarbonyi or R, oX2C (O)- ; R, 3 is hydrogen, Ci-Cgatkyt, C3- C8alkenyl, C3-Cealkynyl, C,-Cehaloalkyl, C,-C4alkoxy-C,-C4alkyl, C,-C4alkylcarbonyl, C,- C4haloalkylcarbonyl, benzoyl or benzoyl which is mono-to trisubstituted on the phenyl ring by halogen, C1-C4alkyl or C,-C4haloalkyl; and R4, R5, R10 and X2 have the meanings given under formula 1.

Other preferred compounds of the formula I are those in which W is the group (W,), and R14, R, 5, R16, X3 and X4 have the meanings given under formula 1. Especially preferred amongst those are compounds in which R14 is methyl, R15 is trifluoromethyl, R16 is hydrogen, and X3 and X4 are oxygen.

Other preferred compounds of the formula I are those in which W is the group (W2), and R17, R18, R19 and X5 have the meanings given under formula 1. Especially preferred compounds are, in particular, those in which R17 and Rig <BR> <BR> independently of one another are hydrogen or Ci-Csatky); Ris is trifluoromethyl, and X5 is oxygen.

Other preferred compounds of the formula I are those in which W is the group (W3), R20, R2, and R22 have the meanings given under formula 1, and X6 and X7 are oxygen. Especially preferred amongst these compounds are, in particular, those in which R2, and R22 together form a C4alkylene bridge which can be substituted by halogen, hydroxyl or =O.

Other preferred compounds of the formula I are those in which W is the group (W4), R23 and R24 have the meanings given under formula 1, and X8 and Xg are oxygen. Especially preferred amongst these compounds are those in which R23 and R24 together form a C3 or C4alkylene bridge.

Other preferred compounds of the formula I are those in which R, is fluorine or chlorine, R2 is chlorine, bromine or cyano, R3 is R6O-, and R6 is C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C3- C6alkenyloxy-C1-C4alkyl, C3-C6alkenyl, C3-C6alkynyl or benzyl. Especially important amongst these compounds are, in particular, those in which R2 is chlorine or cyano.

Preferred compounds of the formula 1, are, furthermore, those in which R2 is methyl, halogen, hydroxyl, nitro, amino, cyano, C,-C4haloalkyl, C,-C4alkoxy or C1-C4haloalkoxy.

The process according to the invention for the preparation of compounds of the formula I is carried out in a manner similar to known processes and comprises, to prepare those compounds of the formulae la laa, lb and Ibb in which Ri, R2, R6 and W have the meanings given under formula 1, R2 preferably being halogen, oxidizing, for example, a compound of the formula III in a suitable solvent to first give the compound of the formula IV subsequently subjecting this compound to a rearrangement reaction in an inert solvent in the presence of an anhydride or of antimony pentachloride (so-called Katada reaction) and, after aqueous workup, obtaining the compounds of the formulae lb and Ibb the radicals RI, R2 und W in the compounds of the formulae lil, IV, lb and Ibb having the abovementioned meanings, and converting these compounds with a compound of the formula V R6-L (V) in which R6 has the meaning given under formula 1, with the exception of R6 being hydrogen, and L is a leaving group such as, for example, halogen, in particular chlorine, bromine or iodine, or a suifonate, in particular CH3S (O) 20- or , in the presence of an inert solvent and of a base to give the isomeric compounds of the formulae la, laa and 11 in which R,, R2, R6 and W have the abovementioned meanings, subsequently removing the compounds of the formula la and laa from the pyridone by-product of the formula 11 and, if appropriate, further functionalizing the compounds as defined for R3 under formula 1.

The process according to the invention for the preparation of compounds of the formula I is carried out by a method similar to known processes and comprises, to prepare those compounds of the formula lc in which Pi, R2, Rg, n, and W have the meanings given under formula 1, halogenating, for example, a compound of the formula lb in which Ri, R2 and W have the abovementioned meanings, with a halogenating agent such as, for example, phosphorus oxychloride, if appropriate in the presence of a base and of a suitable solvent and obtaining the compound of the formula vol the radicals R1, R2 and W in the compounds of the formulae lb and VI having the abovementioned meanings and Hal in the compound of the formula VI being fluorine, chlorine or bromine, converting these compounds with a sulfur reagent such as, for example, hydrogen sulfide or its alkaline earth metal salt in the presence of a base and of a suitable solvent to give the compound of the formula Id subsequently reacting this compound with a compound of the formula VII Rg-L (VIl) in which Rg has the meaning given under formula I with the exception of Rg being hydrogen, and L is a leaving group, if appropriate in the presence of a solvent and of a base, to give the compound of the formula Ic in which Ri, R2, Rg and W have the abovementioned meanings and n, is 0, and, if appropriate, oxidizing this compound to give the compound of the formula lc, in which n, is 1 or 2.

The compounds of the formula Ic in which ni is 2 and Rg is an unsubstituted or substituted C1-C4alkyl or phenyl can-like the compounds of the formula VI which are substituted in the 6-position by halogen-be used as intermediates for the preparation of compounds of the formula I by substituting the group R9S (O) 2- with 0-, N-or S-nucleophiles. The substitution of an alkylsulfonyl or phenylsulfonyl group on pyridine rings with nucleophiles is described, for example, in Bull. Chem. Soc. Jp. 60 (1987), 335 and 343, Het. 24 (1986), 3019 and J.

Het. Chem. 22 (1985), 1583.

The process according to the invention for the preparation of compounds of the formula I is carried out by a method similar to known processes and comprises, to prepare those compounds of the formula I in which A, Ri, R2 and W have the meanings given under formula I and R3 is R60-, R9S (O) nr, amino, R4NH-or R4R5N-, hatogenating, for example, a compound of the formula III or IV and obtaining the compound of the formula VI and subsequently either converting this compound a) with a compound of the formula IX, if appropriate in the presence of a base and of an inertsolvent, or IXa where R6 has the meaning given under formula 1, M in the compound of the formula IXa is an alkali metal atom or alkaline earth metal atom and t is 1 or 2 or b) with a compound of the formula X, if appropriate in the presence of a base and of an inert solvent, or Xa where Rg has the meanings given under formula 1, M in the compound of the formula Xa is an alkali metal atom or alkaline earth metal atom and t is 1 or 2, to give first the compound of the formula lc in which Ri, R2, Rg and W have the abovementioned meanings and ni is 0, and, if appropriate, oxidizing this compound to give the compound of the formula lc in which ni is 1 or 2, for example using hydrogen peroxide, or reacting the compound of the formula VI c) with a compound of the formula XI in which Rg has the abovementioned meaning and M1+ ils an alkali metal ion or d) with a compound of the formula XII, if appropriate in the presence of a base and of an inert solvent, or Xlla R4NH2 (XII) or R4NH M1 (Xlla) in which R4 has the meaning given under formula I and Mimis an alkali metal ion or e) with a compound of the formula XIII, if appropriate in the presence of a base and of an inert solvent, or Xllla R4R5NH (XIII) or R4R5N-M1 (Xlila) in which R4 and Rs have the meanings given under formula I and M1+ is an alkali metal ion, and, if appropriate, subsequently oxidizing the compounds of the formula I (A =N-) which have been obtained by the above variants a) to e) (A The process according to the invention for the preparation of compounds of the formula I is carried out by a method similar to known processes such as described, for example, in EP- A-0 438 209 or DE-OS-19 604 229 and comprises, to prepare those compounds of the formula le in which Ri, R2, R3, R14, R15, R16, X3 and X4 have the meanings given under formula I and R3 is additionally hydrogen, converting, for example a compound of the formula XIV in which R1, R2 and R3 have the abovementioned meanings and L2 is a leaving group such as, for example, halogen, e. g. fluorine, chlorine or bromine, or C,-Caalkyl-or phenylsulfonyl group or a C1-C4alkyl-or phenylsulfonyloxy group in the presence of an inert solvent and of ammonia, if appropriate in an autoclave, at temperatures of-10 to 180°C to give the compound of the formula XV converting this compound in the presence of a base and of a solvent a) with chloroformic ester of the formula XVI II3 X3 (XVI), C-C4alkyl-C-Cl in which X3 has the meaning given under formula I to give the compound of the formula XVII Ri x3 /3 (XVII, Or R2 (XVII), or N R3 b) with oxalyl chloride, phosgene or thiophosgene to give the compound of the formula XVIII subsequently subjecting the compound of the formula XVII or XVIII to a cyclization reaction with an enamine derivative of the formula XIX R15 X4 H2N/VOC1-C4alkYI (XIX) R16 in which R15 and R16 have the meanings given under formula I and X4 is oxygen in the presence of 0.1-1.5 equivalents of a base in an inert solvent, and obtaining the compound of the formula XX in which R1, R2, R3, R15, R, 6, X3 and X4 have the abovementioned meanings, further reacting this compound in the presence of an inert solvent and a base with a) a compound of the formula XXI R14-L (XXI), in which R14 is C1-C3alkyl or C1-C3haloalkyl and L is a leaving group or b) with a hydroxylamine derivative of the formula XXII NH2-L, (XXII) in which L, is a leaving group, and, if appropriate, treating the compounds of the formula le in which X4 is oxygen, which have been obtained by the above variants a) and b), with a thionizing reagent (X4 sulfur).

The process according to the invention for the preparation of compounds of the formula I is carried out by a method similar to known processes and comprises, to prepare those compounds of the formula If in which Pi, R2, R3, R17,?, Ris, Ri9 and X5 have the meanings given under formula I and R3 is additionally hydrogen, for example, either a) converting a compound of the formula XIV in which Ri, R2 and R3 have the abovementioned meanings and L2 is a leaving group such as, for example, halogen, e. g. fluorine, chlorine or bromine, or C1-C4alkyl-or phenylsulfonyl group or a C1-C4alkyl-or phenylsulfonyloxy group, with hydrazine, preferably in a protic solvent, to give the compound of the formula XXIII further reacting this compound with a compound of the formula XXIV or XXIVa in which R17 and R10 have the meanings given under formula I and Hal in the compound of the formula XXIVa is chlorine and bromine, or b) first diazotizing, advantageously with exclusion of water, a compound of the formula XV in which Ri, R2 and R3 have the abovementioned meanings, subsequently further reacting this compound with a compound of the formula XXVI in which R, 7 and R18 have the abovementioned meanings, and obtaining the compound of the formula XXV which is cyclized, if appropriate in the presence of a base such as, for example, 4- dimethylaminopyridine, and of a compound of the formula XXVII X5 P (phenyl) 3 (XXVII) Cl-c4alkyl-O-C-C-Ri. in which R19 has the abovementioned meaning and X5 is oxygen, and, if appropriate, treating this compound with a thionizing reagent (X5 sulfur).

The process according to the invention for the preparation of compounds of the formula I is carried out by a method similar to known methods such as described in, for example, EP-A- 0 272 594, EP-A-0 493 323, DE-A-3 643 748, WO 95/23509, US-A-5 665 681 and US-A-5 661 109 and comprises, to prepare those compounds of the formula 19 in which Ri, R2, R3, R20, R21, R22, X6 and X7 have the meanings given under formula I and R3 is additionally hydrogen, for example, either reacting a) in the presence of a solvent or of a base, a compound of the formula XVlla X /"'X, R24NH-C-OC-C4alkyl N R3 or b) if appropriate in a suitable solvent, a compound of the formula XVllla the radicals Ri, R2, R3 and X7 in the compounds of the formulae XVlla and Villa having the abovementioned meaning, with a compound of the formula XXVIII Rs IR21 ll6 (XXVIII) R22NH-CCOC1-C4alkyl R20 in which R20, R21, R22 and X6 have the abovementioned meanings and obtaining the compound of the formula XXIX /'Y X R2 NH-C-N-C-C-OC,-C4alkyl XXIX, R22 20 -N R22 h20 R3 subjecting this compound to cyciization in the presence of a suitable solvent and of a base, and, subsequently, if appropriate, c) if R22 is hydrogen, reacting this compound with a compound of the formula XXX R22-L (XXX) in which R22 is C1-C3alkyl and L is a leaving group and, d) if X6 and/or X7 are oxygen, treating this compound with a thionizing reagent (X6 and/or X7 sulfur).

The process according to the invention for the preparation of compounds of the formula I is carried out by a method similar to known methods such as described in, for example, EP-A- 0 210 137, DE-A-2 526 358, EP-A-0 075 267 and EP-A-0 370 955 and comprises, to prepare those compounds of the formula Ih in which Ri, R2, R3, R23, R24, X8 and Xg have the meanings given under formula I and R3 is additionally hydrogen, reacting, for example, a) in the presence of a solvent and of a base, a compound of the formula XVllb Ri R2 alkyl (XVllb) N R3 or b) if appropriate in a suitable solvent, a compound of the formula XVlllb in which the radicals Pi, R2, R3 and Xg in the compounds of formulae XVllb and XVlilb having the abovementioned meanings with a compound of the formula XXXI X8 R24 NH-N-C-OCl-c4alkyl R23 in which R23, R24 and X8 have the abovementioned meanings, and obtaining the compound of the formula XXXII R'X X, X, R2-NH-C-N-N-C-OCl-c4alkyl I I N R24 R23 DR3 subjecting this compound to cyclization in the presence of a suitable solvent and of a base, and subsequently if appropriate, c) if R23 and/or R24 are hydrogen, further reacting this compound with a compound of the formula XXXllla or XXXlllb R23-L (XXXllla) or R24-L (XXXlllb) in which R23 and R24 independently of one another are d-Csatkyt and L is a leaving group, or with a Michael acceptor, and, d) if X8 and/or Xg are oxygen, treating this compound with a thionizing reagent (X8 and/or X9 sulfur).

The process according to the invention for the preparation of compounds of the formula I is carried out by a method similar to known processes such as described, for example, in J.

Het. Chem. 15 (1978), 1221, and comprises reacting, for example, a compound of the formula XIV in which R,, R2 and R3 have the meanings given under formula 1, R3 is additionally hydrogen and L2 is a leaving group such as, for example, halogen, e. g. fluorine, chlorine or bromine, or a C,-C4alkyl-or penyl-sulfonyl group or a C,-C4alkyl-or phenyl-sulfonyloxy group with a compound of the formula Wol, W02, W03 or W04 in which the radicals R14 to R24 and X3 to Xg have the meanings given under formula 1, if appropriate in the presence of a suitable solvent and of a base, and subjecting the resulting compounds of the formula I (A =N-) to oxidation (A A further process according to the invention for the preparation of specifically substituted compounds of the formula I is carried out by a manner similar to known processes and comprises, to prepare those compounds of the formula I in which R, is hydrogen or fluorine, R2 is cyano, R3 is halogen, amino, R4NH-, R4R5N-, azido, R60-or R9S (O)n1- and R4, R5, R6, Rg, ni, A and W have the meanings given under formula 1, reacting, for example, a compound of the formula XIVa in which L2 is a leaving group such as, for example, chlorine, bromine or C1-C4alkylsulfonyl, R3 is chlorine or bromine and R, has the abovementioned meaning, with a compound of the formula W0"W02, W03 or W04 in which the radicals R14 to R24 and X3 to Xg have the meanings given under formula 1, or salts of these, if appropriate in a suitable organic solvent and in the presence of a base, such as, for example, carbonates, e. g. potassium carbonate, at elevated temperature or at the reflux temperature of the solvent used to give the compound of the formula li in which R3 is chlorine or bromine and R, and W have the abovementioned meanings, and subjecting this compound to a nucleophilic aromatic substitution reaction, either a) with a compound of the formula IX, if appropriate in the presence of a base and of an inert solvent, or IXa in which R6 has the meaning given under formula 1, M in the compound of the formula IXa is an alkali metal atom or alkaline earth metal atom and t is 1 or 2, or b) with a compound of the formula X, if appropriate in the presence of a base and of an inert solvent, or Xa in which Rg has the meaning given under formula 1, M in the compound of the formula Xa is an alkali metal atom or alkaline earth metal atom and t is 1 or 2, and first converting it into the compound of the formula li in which Ri, Rg and W have the abovementioned meanings and n, is 0 and, if appropriate, oxidizing this compound to give the compound of the formula li in which n, is 1 or 2, for example using hydrogen peroxide, or c) with a compound of the formula XI in which Rg has the abovementioned meanings and M, +is an alkali metal ion, or d) with a compound of the formula XII, if appropriate in the presence of a base and of an inert solvent, or Xlla R4NH2 (XII) or R4NH M1 (Xlla) in which R4 has the meaning given under formula I and M1+ ils an alkali metal ion or e) with a compound of the formula XIII, if appropriate in the presence of a base and of an inert solvent, or Xllla R4R5NH R4R5N-M1+(XIIIa)or in which R4 and R5 have the meanings given under formula I and M1+ ils an alkali metal ion, and, if appropriate, subsequently oxidizing the compounds of the formula li (A =N-) obtained by the above variants a) to e) (A The preparation of compounds of the formulae la, laa, lb and Ibb in which Ri, R2, R6 and W have the meanings given under formula 1, R2 preferably being halogen, is illustrated in reaction scheme lwhich follows.

Reaction scheme 1: Ri Ri R WOj : e. g. H202 NH2C (O) NH2 R W--1 carboxylic acids/anhydrides, solvent IN fiv 1) anhydride, solvent V 2) H20 W + HO<W base, soivent N N Katada reaction HO RUZ Ib Ibb (R2=CI) Ri Ri Ri N R2 ° R6 //i/ 'a'aa (P2=C')" OR6 R2 O R6 I I The pyridine N-oxides of the formula IV (reaction scheme 1) can be prepared by known methods (for example Org. Synth. 4 (1963), 828; ibid. 3 (1955), 619; US-A-3 047 579; and B. Iddon and H. Suschitzky in"Polychloroaromatic Compounds", Editor H. Suschitzky, Plenum Press, London 1974, page 197), expediently by reacting the pyridine derivatives of the formula III with oxidants such as, for example, organic peracids, for example m- chloroperbenzoic acid (MCPBA), peracetic acid and pertrifluoroacetic acid, or aqueous hydrogen peroxide solution or hydrogen peroxide/urea adduct together with carboxylic acids and/or carboxylic anhydrides, or inorganic peracids, for example pertungstic acid (Caro's acid). Suitable solvents are, for example, water, organic acids such as, for example, acetic acid and trifluoroacetic acid, halogenated hydrocarbons such as, for example, dichloromethane and 1,2-dichloroethane, esters, such as, for example, ethyl acetate, ethers such as, for example, tetrahydrofuran and dioxane, or mixtures of these. The reaction temperatures are in the range of-20°C to 100°C, depending on the solvent or solvent mixture used.

The 6-hydroxypyridine derivatives of the formula lb can be prepared by known methods (for example Quart. Rev. 10 (1956), 395; J. Am. Chem. Soc. 85 (1963), 958; and J. Org. Chem.

26 (1961), 428), expediently by means of subjecting the pyridine N-oxides of the formula IV to a rearrangement reaction in the presence of anhydrides, for example acetic anhydride, trifluoroacetic anhydride and methanesulfonic anhydride, in a suitable inert solvent such as, for example, halogenated hydrocarbons, e. g. dichloromethane and 1,2-dichloroethane, amides, e. g. N, N-dimethylformamide and 1-methyl-2-pyrrolidone (NMP), if appropriate in the presence of sodium acetate. The reaction temperatures are generally in the range of from -30°C to 80°C. The same reaction, in particular where R2 is chlorine, also gives the isomeric 6-chloro-5-hydroxypyridine derivatives of the formula Ibb by further rearranging the N-oxides of the formula IV.

The primary products 6-O-acyl-or 6-O-sulfonylpyridines can be hydrolyzed readily by means of aqueous work-up of the reaction mixture to give the desired 6-hydroxypyridines of the formula lb- Similarly to Tetrahedron 37 (1981), 187, antimony pentachloride (Katada reaction) is also suitable for the above rearrangement reaction as further variant. The same applies to the isomeric 5-O-acylated derivatives.

If appropriate, the isomers of the formula lb or Ibb can be separated by known methods.

However, they may also be reacted further as isomer mixture, the compounds of the formulae la, laa and 11 being obtained under identical reaction conditions.

The subsequent alkylation can be effected by known methods (for example Org. Prep.

Proced. Int. 9 (1977), 5; J. Org. Chem. 35 (1970), 2517; ibid. 32 (1967), 4040; and Tetrahedron Lett. 36 (1995), 8917, and Preparation Example H6), expediently with the aid of an alkylating reagent of the formula V. As a rule, alkylation leads to an isomer mixture composed of the compounds of the formulae la and, if appropriate, laa (O-alkylation) and II (N-alkylation).

A further variant of preparing the alkylation products is to react the hydroxypyridines of the formula lb or Ibb with an alcohol of the formula R6OH in which R6 has the meaning given under formula I in an inert solvent such as, for example, tetrahydrofuran, dioxane or dimethoxyethane in the presence of a phosphine such as, for example, triphenylphosphine and an azodicarboxylic acid derivative such as, for example, diethyl azodicarboxylate. Such Mitsunobu reactions are described, for example, in Tetrahedron Letters 1994,2819.

Suitable solvents are, for example, alcools, e. g. methanol, ethanol and isopropanol, amides, e. g. N, N-dimethylformamide (DMF) and 1-methyl-2-pyrrolidone (NMP), sulfoxides, e. g. dimethyl sulfoxide (DMSO) and sulfones, e. g. sulfolane, or mixtures of these with water, ethers, e. g. diethyl ether, tert-butyl methyl ether, dimethoxyethane (DME), dioxane and tetrahydrofuran (THF), esters, e. g. ethyi acetate, ketones, e. g. acetone and methyl ethyl ketone, and hydrocarbons, e. g. n-hexane, toluene and xylenes. Suitable bases are organic and inorganic bases such as, for example, alkali metal alkoxides, e. g. sodium methoxide, sodium ethoxide and potassium tert-butoxide, trialkylammonium hydroxides, trialkylammonium halides, e. g. triethylammonium iodide, alkali metal and alkaline earth metal hydrides, e. g. sodium hydride together with lithium bromide (2 equivalents), alkali metal carbonates, e. g. potassium carbonate, alkali metal hydroxides, e. g. sodium hydroxide and potassium hydroxide, and caesium fluoride.

The reaction temperatures for the alkylation are in the range of from-20°C to reflux temperature of the solvent used, preferably 0°C to 100°C.

The isomers of the formulae la, laya, lbb and 11 can be separated readily by silica gel chromatography or fractional crystallization.

If appropriate, the desired pyridine derivatives of the formulae las laa and bb, which have been separated from the by-product of the formula 11, can readily be functionalized further by known methods in accordance with the definition of R3 under formula 1.

The preparation of the compounds of the formula lc in which R"R2, Rg, n, and W have the meanings given under formula I is illustrated in reaction scheme 2 which follows.

In accordance with reaction scheme 2, the 6-halopyridines of the formula VI can be obtained from the corresponding 6-hydroxypyridines of the formula lb by means of halogenation, for example by means of phosphorus oxychloride or phenyl dichlorophosphate, if appropriate in the presence of a base in an inert solvent, by methods similar to"Pyridine and its Derivatives", Part 2, Editor E. Klingsberg, New York 1961, page 326 et seq.

The 6-halopyridines of the formula VI can be converted into the corresponding 6- mercaptopyridines of the formula Id by a method similar to known processes (for example as described in"Methoden der Organischen Chemie" [Methods in Organic Chemistry] (Houben-Weyl), Volume E/b, Heteroarene part 2, Georg Thieme Verlag Stuttgart, 1992, page 286 et seq.) using a suitable sulfur reagent such as, for example, hydrogen sulfide or its alkali metal salt, or thiourea in the presence of an inert solvent and of a base such as, for example, tertiary amines, alkali metal and alkaline earth metal hydroxides, or the corresponding alkali metal or alkaline earth metal oxides. The 6-mercaptopyridine derivative of the formula Id or its alkali metal salt is subsequently reacted with an alkylating reagent of the formula VII in which L is a leaving group, if appropriate in the presence of a base and of a suitable solvent, to give the 6-alkylmercapto derivative of the formula c.

If appropriate, the thioethers of the formula lc (n, =0) can be converted into the sulfoxides or sulfones lc (n, = 1 or 2) by known methods using an oxidant such as, for example, hydrogen peroxide, sodium periodate or m-chloroperbenzoic acid (m-CPBA) in an inert solvent such as, for example, dichloromethane. If appropriate, the reaction may also be stopped at the sulfoxide level.

Reaction scheme 2: Ri Ri halogenation, e. g. w sulfur reagent, e. g. R2 POC13 or POBr3, R2' W H2S, Na+HS or NH2C (S) NH2, solvent, base if appropriate solvent, Hase HO base vu b Ri R9-L, if appropriate base, Ri Ri \ VII-\ [O] e. g. solvent HS S (0)3 (0) bd ic (n1=0) Ic (ni=1, 2) The preparation of the compounds of the formula I in which A, Ri, Rs and W have the meanings given under formula I and R3 is R6O-, R9S (0) nu, amino, R4NH-or R4R5N-is illustrated in reaction scheme 3 which follows.

Reaction scheme 3: Ri Ri -halogenation R2t w or R25\/w > R2>\ w N+ N N han IV N N a) R60Hor pR6 (l Mt+, or Ri zut In ixia b) RgSH or iRgi ; M, or SN X Xa R3 c)CsSO) IR amino, R4NH-, R4R5N-) XI d) R4NH2, ; R4Ni Mr or NH, or exc. XII Xlla e) R4RsNH2or [R4R5N3 Mr b XIII Xllla optional base, solvent The 6-halopyridines of the formula VI can be obtained readily from the corresponding pyridine N-oxides of the formula IV or else from the pyridine derivatives of the formula III in accordance with reaction scheme 3 by known standard methods by means of halogenation, for example using phosphorus oxychloride or phosphorus oxybromide.

The reactive 6-halopyridines of the formula VI, in turn, can be reacted either a) with an alcohol of the formula IX, if appropriate in the presence of a base and of an inert solvent, or with the corresponding alkali metal alkoxide of the formula IXa, b) with a thiol of the formula X, if appropriate in the presence of a base and of an inert solvent, or with the corresponding alkali metal thiolate of the formula Xa, c) with an alkali metal sulfinate of the formula XI, or d) and e) with an excess of ammonia, with an amine of the formula XII or XIII, if appropriate in the presence of a base and of an inert solvent, or with the corresponding alkali metal salt of the formula Xlla or Xllla to give the desired compounds of the formula I in which R3 is either R6O-, R9S (O) n,-, amino, R4NH-or R4R5N-by methods similar to known nucleophilic substitution reactions.

The 6-mercaptopyridines of the formula I obtained in accordance with variant b) in which R3 is R9S (O) ni and n, is 0 can be converted, if appropriate, by known oxidation methods, for example using hydrogen peroxide, organic peracids, sodium perborate (NaBO3), (NH4) 2Ce (NO3) 6, sodium periodate (Na104) or manganese dioxide (MnO2) to give the compounds of the formula I in which R3 is R9S (O) ni- and ni is 1 or 2. Such oxidations are described, for example, in"Oxidations in Organic Chemistry", Editor M. Hudlicky, ACS Monograph 186, Washington DC, 1990.

The resulting sulfonyl derivatives of the formula I in which R3 is RgS (O) n1 and ni is 2 can be further derivatized in accordance with the definition of R3 by known methods, for example by nucleophilic aromatic substitution.

The above reactions in accordance with variants a), b), d) and e) are carried out with the non-deprotonated reagents of the formulae IX, X, XII and XIII, preferably in the presence of a base such as, for example, alkali metal hydroxides, alkaline earth metal hydroxides, alkaline earth metal oxides, alkali metal hydrides, e. g. sodium hydride, alkoxides, e. g. potassium tert-butoxide, quaternary ammonium hydroxides or tertiary amines, in a suitable inert solvent.

Compounds of the formula I in which R3 is nitro can be f) either obtained directly by means of nitration and separation of undesired position-isomeric nitro derivatives, g) obtained readily by means of oxidizing the amino group of the corresponding 6-aminopyridine derivative of the formula I (R3 amino), or) can be obtained by a method similar to what has been described, for example, in"Oxidations in Organic Chemistry", Editor M. Hudlicky, ACS Monograph 186, Washington DC, 1990, from the corresponding pyridine azides R3 Ñ=N=N_) orfrom the corresponding amines by oxidation, for example with an alkali metal peroxodisulfate or ammonium peroxodisulfate, for example in concentrated sulfuric acid as solvent at reaction temperatures of from-20° to +30°C.

Compounds of the formula I in which R3 is an amino group (NH2) can furthermore be obtained by rearranging corresponding acetamides (R3 =-OCH2CONH2) in the presence of a base, such as, for example, alkali metal carbonates, in an inert solvent such as, for example, dimethyl sulfoxide at temperatures of from 70° to 150°C.

Compounds of the formula I in which R2 or R3 is an amino group (NH2) can furthermore also be obtained by reducing the corresponding azides. For example, these azides can be prepared by a Mitsunobu reaction from the hydroxyintermediates, hydrazoic acid (HN3), a phosphine such as, for example, triphenylphosphine and an azo compound such as, for example, diethyl azodicarboxylate in an inert solvent. Such reactions are described, for example, in Synthesis 1992,367.

The other compounds which come under the scope of the formula I can be prepared readily by methods similar to known standard processes taking into consideration the chemical reactivities of the pyridyl moiety and of the pyridyl- (Heterocyclyl)-W moiety (groups W, to W4).

The preparation of the compounds of the formula le in which R"R2, R3, R, 4, R, 5, R, 6, X3 and X4 have the meanings given under formula I and R3 is additionally hydrogen is illustrated in reaction scheme 4 which follows.

Reaction scheme 4: R'R'a) CIC (X3) O-C,-C4alkyl or /=t NH3 (autoclave)-XVI R Nr-Hal Solven-10-180°C R2 nu base, solvent 3 R3 R X Ri X3 OC-C alk I R2-H, a Y C-C4alkyl R X4 Rs N H2N O. R3 XVII R6 R2 < N R1s XIX N N base, solvent R3 X3 H Ri XX c)c) R14-L or R2 NC=X3 xxi base, » N d) NH2-L1 solvent R3 xxi I XVIII XV ! ! f Ri /6R, X, R thionizing reagent) e. g./ Lawesson reagent R2 N R15 R2 N Ris solvent i(X, S)'e (X4 0) A multiplicity of known standard processes such as described, for example, in EP-A-0 438 209 and DE-OS-19 604 229 (R, 5 cyano) is suitable for the preparation of the compounds of the formula le according to the invention.

Reaction scheme 4 shows a selection of suitable preparation methods, the choice of reaction routes and reagents depending on the reactivities of the substituents at the intermediate levels.

For example, starting by reacting a compound of the formula XIV with ammonia in an inert solvent, if appropriate in an autoclave, at temperatures of-10 to 180°C, the aminopyridine of the formula XV can be obtained. The latter can be converted, in the presence of a base and of a solvent, either a) with chloroformic ester of the formula XVI (X3 oxygen or sulfur) to give a pyridylcarbamate of the formula XVII, or <BR> <BR> b) with oxalyl chloride, phosgene (X3 oxygen) or thiophosgene (X3 sulfur) to give an iso (thio) cyanate of the formula XVIII. Such reactions are described, for example, in Angew. 1971,407.

The carbamate and the iso (thio) cyanate of the formulae XVII and XVIII can be cyclized in the presence of the enamine derivative of the formula XIX in an inert solvent to give the uracil derivative of the formula XX, the reaction of the iso (thio) cyanate of the formula XVIII advantageously being carried out in the presence of 0.1-1.5 equivalents of a base such as, for example, sodium hydride, potassium tert-butoxide or alkaline earth metal oxide or alkaline earth metal hydroxide, for example barium hydroxide.

The desired compounds of the formula le can be obtained by standard processes by converting the uracils of the formula XX in the presence of an inert solvent and at least 1 equivalent of a base, for example alkali metal carbonate, e. g. potassium carbonate, c) with an alkylating agent of the formula XXI to give the N-alkyl derivative of the formula le (R, 4 alkyl), or d) by a method similar to WO 97/05116 with a hydroxylamine derivative of the formula XXII, in which L, is a leaving group, such as, for example, HOS (O) 20-, , for example 2,4-dinitrophenyl- hydroxylamine or hydroxylamine-O-sulfonic acid, to give the N-amino derivative of the formula! e (Ri4 amino). The thiono derivatives of the formula le (X3, X4 sulfur) can be obtained by means of thionation, for example with phosphorus pentasulfide or Lawesson reagent.

The preparation of the compounds of the formula If in which Ri, R2, R3, R, R18, R19 and X5 have the meanings given under formula I and R3 is additionally hydrogen is illustrated in reaction scheme 5 which follows.

Reaction scheme 5: Ri Ri NH2NH2, \ RZ Hal R2 \/)--NHNH2 solvent N N R3 R 3 3XXIII XIVO Re O R8 or B Br 4 R17 XXIV XXIVa X5 R, 9 R Ri Xs Rls C1-C4alkyl-O P (Ph) 3 Ri 0 XXVII R N R R2 NH R18 N N- XXV If 1) diazotization (preferably with exclusion of water) 2) ° R. 8 Japp-Klingemann 1 reaction COOH Pi7 XXVI Ri R2 ß NH2 N R3 XV The compounds of the formula I, can be prepared by known methods, for example in accordance. with reaction scheme 5 by reacting a 2-halopyridine derivative of the formula XIV with hydrazine, preferably in a protic solvent such as, for example, alcools, by a method similar to GB-A-2 230 261 to give the 2-hydrazino derivative of the formula XXIII.

The latter is reacted with a diketone of the formula XXIV by a method similar to DE-OS-19 754 348 or a dihaloketone of the formula XXIVa by a method similar to WO 97/07104 to give the hydrazone derivative of the formula XXV.

The subsequent cyclization which yields the desired compound of the formula If is carried out in the presence of the phosphorane derivative of the formula XXVII, if appropriate in the presence of a base, for example 4-dimethylaminopyridine. In the event that, in the compound of the formula If, X5 is 0, the product may subsequently be thionized by a<BR> method similar to what has been described under reaction scheme 4 (X5 S).

In accordance with reaction scheme 5, the hydrazone derivative of the formula XXV may also be obtained via diazotization, preferably with exclusion of water, and subsequent coupling with the keto acid of the formula XXVI (Japp-Klingemann reaction, similar to DE- OS-19 754 348), starting from the 2-aminopyridine derivative of the formula XV.

The preparation of the compounds of the formula 19 in which Ri, R2, R3, R20, R2"R22, X6 and X7 have the meanings given under formula I and R3 is additionally hydrogen is illustrated in reaction scheme 6 which follows.

Reaction scheme 6: R, l'i a) R O-C-C4alkyl X6 N RNH C,-C4alkyl 'C-C4alkyl "-'R R 3. R 0 Rs XVlla R2o Rz, XXVIII H 2i,/ ou base, solvent N N, , ruz2 R2 N=C=X XXIX base, solvent R3 XVllia 8 ( XV!) ta R, Xg R p Xg R alkylation, e. g. R22 Ri X6 R21 R2 \ N R2o XXX R i N Rzo R3 -N base, solvent Z \ N N nu X R R X''R 3 7 Ig (e. g. X70) Ig 'g thionation, e. g. Lawesson reagent Ri X6 R21 R2- N fun R3 X7 Rz I g (e. g. X, S) The compounds of the formula I9 can be prepared similarly to known methods such as described, for example, in EP-A-0 272 594, EP-A-0 493 323, DE-A-3 643 748, WO 95/23509, US-A-5 665 681 or US-A-5 661 109.

In accordance with reaction scheme 6, for example, either a) a carbamate derivative of the formula XVlla in the presence of a solvent and of a base or b) an iso (thio) cyanate of the formula XVllla, if appropriate in a suitable solvent, may be cyclized with an amino acid derivative of the formula XXVIII via the compound of the formula XXIX in the presence of a base and of a suitable solvent to give the compound of the formula tu. <BR> <BR> <BR> <P>In the event that, in the compound of the formula g, R22 is hydrogen and X6 and/or X7 are oxygen, the product can, if appropriate, be subsequently alkylated with an alkylating agent of the formula XXX on the free N atom of the hydantoin ring and the ring carbonyl group can be thionated (X6 and/or X7 sulfur).

In the starting compounds of the formulae XVlla and XVllla in reaction scheme 6, R3 may also be hydrogen. Functionalization in accordance with the definition of the substituent R3 in the compounds of the formula 19 may then be carried out by processes similar to those given in reaction schemes 1 to 3.

The preparation of the compounds of the formula Ih in which Ri, R2, R3, R23, R24, Xa and Xg have the meanings given under formula I and R3 is additionally hydrogen is illustrated in reaction scheme 7 which follows.

Reaction scheme 7: Ri X9 a) R N o-cl-c4alkyl R H R24NH R-C-C4alkyl XVlib R23 R, R23-C4alkyl or XXXI R-N \ ' Xa base, 10 R2 N N N R2 <\,) N=C=Xg b) xxxii N base, solvent Ra R3 XVIllb XVtHb Ra X8 R23 alkylation, e. gR23-LR R24-L, or Ri X8 R23 N XXXllla XXXlllb R2--N R2 N\ Michael acceptor base, X-N soivent R'', R24 3 X.'R 3 g p4 1 h (e. g. Xg 0) h h 3 9"24 thionation, e. g. Lawesson reagent Ri X, R R, X8 R23 N RZ N N joN ; NR3 X9 R24 Ih (e. g. Xg S) The compounds of the formula Ih can be prepared similarly to known processes such as described, for example, in EP-A-0 210 137, DE-OS-2 526 358, EP-A-0 075 267 or EP-A-0 370955.

In accordance with reaction scheme 7, for example, either a) a carbamate derivative of the formula XVllb in the presence of a solvent and of a base, or b) an iso (thio) cyanate of the formula XVlllb, if appropriate in a suitable solvent, may be cyclized with a carbazate of the formula XXXI via the compound of the formula XXXII in the presence of a base and of a suitable solvent to give the compound of the formula Ih.

In the event that, in the compound of the formula Ih, R23 and/or R24 are hydrogen and X8 and/or Xg are oxygen, the product can subsequently be alkylated with an alkylating reagent of the formula XX))) a or XXXlllb on the free N-atoms and the ring carbonyl group can be thionated with the thionating reagent (X8 and/or Xg sulfur).

To prepare compounds of the formula Ih in reaction scheme 7 in which R23 and R24 together form an alkylene bridge which is interrupted by, for example,-C (O)-or-S (O) 2-, for example the compound of the formula Ih, in which R23 and R24 are hydrogen can be reacted with a suitable Michael acceptor, such as, for example, CH2=CH-C (O) CH3, CH2=CH-S (O) 2CH3 or CH2=CH-S (O) 2-CH=CH2 and the resulting Michael adducts can be functionalized further.

The compounds of the formulae bX 1"19 and Ih in the preceding reaction schemes 4 to 7 in which X4, Xs, X7 and Xg are O and R3 is hydrogen can subsequently be functionalized, for example as shown in reaction schemes 1 to 3, to give the compounds of the formulae le, If,<BR> 19 and ih in which R3 has the meaning given under formula 1.

In accordance with reaction scheme 8 which follows, the compounds of the formula I may also be obtained expediently directly by substituting a 2-halopyridine of the formula XIV or XIVa (R2 = CN) with the desired heterocycles Wo, to W04 or salts thereof (for example alkali metal salts), if appropriate in the presence of a suitable solvent and of a base (variant a)).

Similar reactions are described, for example, in J. Het. Chem. 15, (1978), 1221.

In some cases it may be expedient to couple the heterocyclic group W, to W4, for example as shown in variant b) in reaction scheme 8 with reference to Wi, to the pyridyl moiety by means of direct alkylation with an imino-ether-modified heterocycle of the formula Pool.

Reaction scheme 8: Variant a): x 4 Ri HN R15 or Un X3R14 Wo, woi xi ris N- , N Ri Ri7 Ri -W _ R 2 L-2 + base. solvent R 2 w A X7 A A XIV (A =N-) HN NRZ or R3 I (A =N-) R20 8 H2 X3 Ho'"\ R N N' Xa Xe R23 Won Variant b) C-C4alkyl-X4 Rs R base, solvent \ R2 L2 + N \ Rs R2 \/)--W, R x3 R14 R3 R/X RR/ w XIV (A =N-) W'I (A =N-) L2 in the compound of the formula XIV in reaction scheme 8 is a leaving group such as, for example, halogen or a C1-C4alkyl or phenyl-sulfonyl group.

The heterocyles of formula Wo, in reaction scheme 8 above, wherein R14 is C1-C3alkyl (e. g. methyl), R, 5 is Ci-Cshatoatkyt (e. g. CF3), R, 6 is hydrogen and X3 and X4 are oxygen, are obtained either according to WO 98/08824 or by the reaction sequence as follows: An enamine derivative of formula XXXIV wherein R14 is d-Caatkyt, Ris is C1-C3haloalkyl and R27 is C1-C4alkyl, C1-or C2haloalkyl or optionally substituted benzyl, is converted in the presence of chlorocarbonyl isocyanate (CICONCO) in inert organic solvents to the compound of formula XXXV the ester function of which is then transferred to the corresponding carboxylic acid function as represented by compound of formula XXXVI which then is decarboxylated to yield the compound of formula W01 the radicals R14, R15, R27, X3, X4 and R16 in the compounds of formulae XXXV, XXXVI and Wo, having the abovementioned meaning.

This reaction sequence is novel and therefore instant invention also relates to this method of preparation.

Above reaction sequence is illustrated in reaction scheme 9 which follows.

Reaction scheme 9: R27 27 0 O Xa O O X4 ucoCICONCO, inert solvens SR15-30-+80°C HN, eR15 RsNv HN, X3 R14 \ 3"14 R14 cleavage by hydrolysis under acid conditions or by enzymatic methods or in presence of an oxidant or by hydrogenolysis (H2/cat) H 0 X X4 R16 X4 0 decarboxylation HN R15 HN-_ R s with or without inert solvens with or without a catalyst e. g Cu (0) 100-300°C XXXVI Wo,Rs=H) According to reaction scheme 9 above the enamine derivative of formula XXXIV, wherein R14 and R15 are as defined and R27 is C,-C4alkyl (e. g. t-butyl), C,-C2haloaikyl (e. g. 2,2,2- trichloroethyl) or optionally substituted benzyl (e. g. p-methoxybenzyl) is reacted with chlorocarbonyl isocyanate (CICONCO) in inert sovents such as dichloromethane at temperatures in the range of from-30°C to +8°C to obtain the pyrimidine derivative of formula XXXV.

The carboxylic ester function COOR27 of compound of formula XXXV is then cleaved for example by hydrolysis or hydrogenolysis to yield the corresponding carboxylic acid function of compound of formula XXXVI according to the following methods as described in 'Protective Groups in Organig Synthesis', Editor Th. Greene, New York, 1981; and Houben- Weyl, Band E5,'Carbonsauren und Carbonsaurederivate', Stuttgart, 1985: treatment with an acid (formic acid containing catalytic amounts of sulfuric acid as described in Houben-Weyl above, p. 227) if R27 in compound of formula XXXV is alkyl or benzyl; treatment with formic acid, trifluoroacetic acid or HBr if R27 in compound of formula XXXV is t-butyl or benzyl; treatment with tin (Zn) in acetic acid if R27 in compound of formula XXXV is 2,2,2- trichloroethyl; treatment with an oxidant such as ceric ammonium nitrate in water/acetonitril if R27 in compound of formula XXXV is 4-methoxybenzyl; cleavage by hydrogenolysis (H2/appropriate catalyst such as Pd-C in inert solvent) if R27 in compound of formula XXXV is benzyl or substituted benzyl; or by enzymatic cleavage (Ann. Rep. Med. Chem. 19,263 (1984); Angew. 24,617 (1985)).

Decarboxylation of the carboxylic acid derivative of formula XXXVI to the uracil compound of formula Wol, wherein R, 6 is hydrogen is achieved finally by heating net or in inert solvents such as decaline or quinoline with or whithout addition catalysts such as Cu (0) or Cu (I)- salts such as CuCI.

The compounds of the formulae XIV, XlVa and XV which are not already known can be prepared by known methods such as described in, for example, DE-A-3 917 469; WO 97/07114; WO 92/00976; JP-A-58-213 776; EP-A-0 012 117; EP- A-0 306 547; EP-A-0 030 215; EP-A-0 272 824; EP-A-0 500 209; US-A-4 996 323; US-A-5 017 705; WO 97/05112; J. Het. Chem. 11 (1974), 889; J. Het. Chem 21 (1984), 97; Tetrahedron 41 (1985), 4057; Heterocycles 22,117; Synth. 1988, 938; J. Med. Chem. 25 (1982), 96, Chem. Pharm. Bull. 35 (1987), 2280 and WO 98/11071.

The 2-aminopyridines of the formula XV can also be prepared from the corresponding pyridine derivatives which have carboxylic acid, carboxylic acid chloride, carboxylic acid azide, and carboxylic acid ester or carboxamide functions in the 2-position by Curtius, Hofmann or Lossen degradation reactions.

The reagents and starting compounds of the formulae V, Vll, IX, IXa, X, Xa, XI, XII, Xlla, XIII, Xllla, XVI, XVlla, XVllb, XVllla, XVlllb, XIX, XXI, XXII, XXIV, XXIVa, XXVI, XXVII, XXVIII, XXX, XXXI, XXXllla, XXXlllb and XXXIV which have been used in reaction schemes 1 to 9 are either known or can be prepared analogously to known processes.

The intermediates of the formulae III and IV in which Ri, R2 and W have the meanings given under formula 1, are novel. The invention thus also relates to these compounds.

The intermediates of the formula XVllb R'X /-9 (XVllb) R2 NH-COC1-C4alkyl (XVl lb) N R3 in which Ri, R2, R3 and Xg have the meanings given under formula I and R3 is additionally hydrogen are novel. The invention thus also relates to these compounds.

The reactions which give compounds of the formula I are advantageously carried out in aprotic, inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or proprionitrile, amides such as N, N-dimethylformamide, N, N- diethyiformamide or N-methylpyrrolidinone. The reaction temperatures are preferably between-20°C and +120°C. In some cases, the reactions are slightly exothermic and, as a rule, they may be carried out at room temperature. To reduce the reaction time, or else to start up the reaction, the reaction mixture may be warmed briefly to boiling point, if appropriate. The reaction times may also be reduced by adding a few drops of base as reaction catalyst. Suitable bases are, in particular, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 2]-octane, 0]-non-5- ene, 0]-undec-7-ene or 4-dimethylaminopyridine. However, inorganic bases such as hydrides, e. g. sodium hydride or calcium hydride, hydroxides such as sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate or potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate, may also be used as bases.

The compounds of the formula I can be isolated in the customary manner by concentrating and/or by evaporating the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, or by means of column chromatography and a suitable eluent.

Suitable uses according to the invention of the compounds of the formula I or compositions comprising them are all application methods which are customary in agriculture such as, for example, pre-emergence application, post-emergence application and seed treatment, and a variety of methods and techniques, such as, for example, the controlled release of active ingredient. To this end, the dissolved active ingredient is applied to mineral granule carriers or to polymerized granules (urea/formaldehyde) and dried. If appropriate, an addition coating can be applied (coated granules) which allows controlled release of the active ingredient over a specific period.

The compounds of the formula I can be employed as herbicides as pure active ingredients, i. e. as obtained in synthesis. Preferably, however, they are processed in the customary manner with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. The application methods, such as spraying, atomizing, dusting, wetting, scattering or pouring, and the nature of the compositions are chosen to suit the intended aims and prevailing circumstances.

The formulations, i. e. the compositions, preparations or combinations which comprise the active ingredient of the formula I or at least one active ingredient of the formula I and, as a rule, one or more solid or liquid formulation auxiliaries, are prepared in the known manner, for example by intimately mixing and/or grinding the active ingredients with the formulation auxiliaries such as, for example, solvents or solid carriers. Furthermore, surface-active compounds (surfactants) may additionally be used when preparing the formulations.

Examples of solvents and solid carriers are given, for example, in WO 97/34485 on page 6.

Suitable surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, non-ionic, cationic and/or anionic surfactants and surfactant mixtures which have good emulsifying, dispersing and wetting properties. Examples of suitable anionic, non-anionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8.

The surfactants conventionally used in the art of formulation described in, inter alia, "McCutcheon's Detergents and Emulsifiers Annual"MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H.,"Tensid-Taschenbuch" [Surfactants Guide], Carl Hanser Verlag, MunichNienna, 1981, and M. and J. Ash,"Encyclopedia of Surfactants", Vol 1-111, Chemical Publishing Co., New York, 1980-81 are furthermore also suitable for preparing the herbicidal compositions according to the invention.

As a rule, the herbicidal formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant. While concentrated compositions are more preferred as commercially available goods, the end user uses, as a rule, dilute compositions. The compositions may also comprise other additives such as stabilizers, e. g. epoxidized or unepoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e. g. silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients.

As a rule, the active ingredients of the formula I are applied to the plant or its environment at application rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the desired action can be determined by experiments. It depends on the type of action, the developmental stage of the crop plant and of the weed, and on the application (location, timing, method) and, due to these parameters, may vary within wide ranges.

The compounds of the formula I are distinguished by herbicidal and growth-inhibitory properties which allow them to be used in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, oilseed rape, maize and rice and for non-selective weed control. Crops are also to be understood as meaning those which have been made tolerant to herbicides, or classes of herbicides, by conventional breeding or genetic engineering methods. The weeds to be controlled may be monocotyledonous or dicotyledonous weeds such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. The examples which follow illustrate the invention in greater detail without imposing any limitation.

Preparation examples: Example H1: Preparation of 2-N-ethoxicarbonylamino-3-fluoro-5-chloropvridine 294 g of 2-amino-3-fluoro-5-chloropyridine are dissolved in 1 I of dry pyridine, the solution is cooled to 0°C, 220 g of ethyl chloroformate are added dropwise with stirring, and the mixture is stirred at 22°C until the reaction is complete. The reaction mixture is then poured into ice-water, brought to pH 4-5 using 2N hydrochloric acid and extracted with ethyl acetate. The combined extracts are washed with water, dried over sodium sulfate, evaporated and crystallized by adding n-hexane. The resulting precipitate is filtered off, washed with n-hexane and dried in vacuo. This gives the desired title compound of m. p.

132°C.

Example H2: Preparation of 1-(3-fluoro-5-chloropyridine-2-vl)-3-methvl-4-trifluoromethy l- pyrimidine-2,6-dione (compd. no. 600.001) A solution of 22.7 g of ethyl 4,4,4-trifluoro-3-amino-2-butenoate is added dropwise with<BR> <BR> stirring and cooling at 0-5°C under a nitrogen atmosphere to 5.1 g of a previously introduced sodium hydride dispersion (60%) in 60 ml of n-methylpyrrolidine, and stirring is continued at 22°C until the evolution of hydrogen has ceased. Then, 23.7 g of 2- ethoxycarbonylamino-3-fluoro-5-chloropyridine (Example H1) are added and the reaction <BR> <BR> mixture is heated for approx. 5 hours at 120°C. It is then cooled, 16.7 g of methyl iodide are added dropwise, and stirring is continued overnight at 22°C. After the reaction mixture has been taken up in ethyl acetate, it is washed with ice-water, dried over sodium sulfate, filtered and evaporated. The residue obtained is recrystallized from ethyl acetate/n-hexane.

This gives the desired title compound of m. p. 133-134°C.

Example H3: Preparation of 1-(3-fluoro-5-chloro-2-pvridvl-N-oxide)-3-methyl-4- trifluoromethyl-pyrimidine-2.6-dione (compd. no. 617.001) 24 g of 1- (3-fluoro-5-chloropyridine-2-yl)-3-methyl-4-trifluoromethylp yrimidine-2,6-dione<BR> (Example H2) in 150 ml of dichloromethane is cooled to-5°C and treated with 2 g of hydrogen peroxide/urea adduct. 2.7 ml of trifluoroacetic anhydride, dissolved in 2 ml of dichloromethane, are subsequently metered in and, when the exothermal reaction has subsided, the reaction mixture is stirred overnight. Then, again, 3 ml of trifluoroacetic anhydride and 5 g of hydrogen peroxide/urea adduct are added in two portions in the course of 3 hours and, when the exothermal reaction has subsided, the reaction mixture is heated at 25-35°C until the reaction is complete. It is subsequently cooled and, at-5°C, brought to pH 7.5, first with 2 N sodium hydroxide solution and then with saturated sodium hydrogen carbonate solution, the mixture is partitioned between dichloromethane and ice- water, and the organic phase which has been separated off is dried over sodium sulfate, filtered and concentrated by evaporation. The solid residue which remains is recrystallized from ethyl acetate/n-hexane. This gives the desired product of m. p. 142-143°C.

Example H4: Preparation of 1- 3-fluoro-5, 6-dichloro-2-pyridyl)-3-methyl-4-trifluoromethyl- pyrimidine-2,6-dione (compd. no. 1.396) A solution of 2.4 ml of phosphorus oxytrichloride in 20 ml of 1,2-dichloroethane, heated at 70°C, is treated with 6.8 g of 1- (3-fluoro-5-chloro-2-pyridyl-N-oxide)-3-methyl-4- trifluoromethyl-pyrimidine-2,6-dione (Example H3), a little at a time, and kept overnight at this temperature, a further 4.0 ml of phosphorus oxytrichloride are added, and the mixture is heated for a further 20 hours. It is subsequently cooled, poured into ice-water and extracted with dichloroethane, and the combined extracts are washed with ice-cooled 2N sodium hydroxide solution and water, dried over sodium sulfate and concentrated by evaporation.

The residue is purified by silica gel chromatography (eluent: hexane/ethyl acetate 9/1). This gives the desired title compound of m. p. 113-115°C.

Example H5: Preparation of 1 uoroyridine-6-yl)-3-methyl-4- trifluoromethylpyrimidine-2,6-dione and 1-(3-hvdroxy-2-chloro-5-f luoropyridine-6-vl !-3- methvl-4-trifluoromethylpyrimidine-2,6-dione ci F HO F Ouzo J'jL A rHJ'JL A rN compd. no. 1.002) and ciN"N"N"' HO NON N P o4CF3 ° CF3 0 '30 '3 A solution of 29.6 g of 1- (3-fluoro-5-chloro-2-pyridyi-N-oxide)-3-methyl-4-trifluorome thyl- pyrimidine-2,6-dione (Example H3) in 400 ml of dimethylformamide, cooled to-30°C, is treated dropwise with 182 g of trifluoroacetic anhydride, stirred overnight at-30°C and the next day at 22°C. Then, the mixture is freed from excess trifluoroacetic anhydride in vacuo, cooled to-5°C and carefully neutralized, first with dilute sodium hydroxide solution and then with sodium hydrogen carbonate solution. After addition of ice-water, the mixture is extracted with ethyl acetate, and the combined extracts are washed with water and dried over sodium sulfate. The mixture is then filtered, the filtrate is concentrated by evaporation and the residue obtained is purified over a silica gel column (eluent: n-hexane/ethyl acetate 8/2, increasing ethyl acetate gradient). This gives the desired title compound (compd. no.

1.002) of m. p. 200-202°C.

Besides that, a mixed fraction is obtained which, in addition to 1- (2-hydroxy-3-chloro-5- fluoro-pyridine-6-yl)-3-methyl-4-trifluoromethylpyrimidine-2 , 6-dione, furthermore also contains the isomer 1- (3-hydroxy-2-chloro-5-fluoropyridine-6-yl)-3-methyl-4- trifluoromethylpyrimidine-2,6-dione. The latter isomeric compound is obtained by a further rearrangement. The ratio of the two isomers 1- (2-hydroxy-3-chloro-5-fluoropyridine-6-yl)-3- methyl-4-trifluoromethylpyrimidine-2, 6-dione and 1- (3-hydroxy-2-chloro-5-fluoropyridine-6- yl)-3-methyl-4-trifluoromethypyrimidine-2, 6-dione varies, depending on the reaction conditions (approx. 3: 1). The isomer mixture of the mixed fraction can either be used directly in the next reaction step or separated by means of HPLC (Li-Chrospher Si60; eluent: ethyl acetate/hexane 15/85 to 30/70, increasing ethyl acetate gradient). This gives pure 1- (3-hydroxy-2-chloro-5- fluoropyridine-6-yl)-3-methyl-4-trifluoromethylpyrimidine-2, 6-dione of m. p. 189-192°C.

Example H6: Preparation of 1-(2-ProparqvloXv-3-chloro-5-fluoropyridine-6-yl)-3-methvl-4 - trifluoromethylpvrimidine-2. 6-dione. 1- (2-chloro-3-proparayloxv-5-fluoropyridine-6-yl)-3- methyl-4-trifluoromethylpvrimidine-2. 6-dione and 1- (1-propargyloxy-3-chloro-5-fluoro-2- pyridon-6l)-3-methvl-4-trifluoromethylpyrimidine-2. 6-dione (compd. no. 1.022) A suspension of 10.2 g of a mixture of 1-(2-hydroxy-3-chloro-5-fluoropyridine-6-yl)-3-methyl- 4-trifluoromethylpyrimidine-2,6-dione and 1- (2-chloro-3-hydroxy-5-fluoropyridine-6-yl)-3- methyl-4-trifluoromethylpyrimidine-2, 6-dione (Example H5), 7.5 g of potassium carbonate and 0.08 g of 18-crown-6 in 180 ml of acetonitrile is treated dropwise with 4.5 mi of propargyl bromide and subsequently heated overnight at 65 °C. The mixture is then concentrated by evaporation in vacuo, the residue obtained is treated with ethyl acetate/ice- water mixture and 1 N hydrochloric acid until the pH is 7, the aqueous phase is separated off and extracted with ethyl acetate, and the combined organic phases are washed with water, dried over sodium sulfate and filtered, and the filtrate is concentrated by evaporation.

The residue is purified by means of silica gel chromatography (eluent: n-hexane/ethyl acetate 8/2). This gives the desired isomers 1- (2-propargyloxy-3-chloro-5-fluoropyridine-6- yl)-3-methyl-4-trifluoromethylpyrimidine-2,6-dione, m. p. 121-122°C (compd. no. 1.022), 1- (2- <BR> <BR> chloro-3-propargyloxy-5-fluoropyridine-6-yl)-3-methyl-4-trif luoromethyl-pyrimidine-2, 6-dione, m. p. 69-71 °C and 1- (l-propargyioxy-3-chloro-5-fluoro-2-pyridon-6-yi)-3-methyl-4 - trifluoromethylpyrimidine-2,6-dione, m. p. 223-224°C.

Example H7: Preparation of tetrahydroimidazo [1. 5-a] pyridine-1.3-dione 34.6 g (0.193 mol) of methyl 2-piperidinecarboxylate hydrochloride are introduced into 260 ml of water in a reaction vessel and 17.4 g (0.216 mol) of potassium cyanate are added. 30 ml of glacial acetic acid are then added, and the homogenous solution formed is stirred for 4.5 hours at 22°C. The reaction solution is subsequently saturated with sodium chloride (NaCI) and extracted twice using in each case 200 ml of tert-butyl methyl ether. The organic fractions are combined, dried over sodium sulfate and concentrated. 11 g of a viscous oil, from which crystals separate out overnight, is obtained as residue. The crystals are separated off by decanting off the remaining oil and purified by triturating (digesting) with diethyl ether. This gives the desired product of m. p. 122-123°C in a yield of 5.75 g.

Example H8: Preparation of 2-(3-fluoro-6-chloro-5-cyano-2-pyridyl)tetrahydroimidazo[1, 5- alpvridine-1.3-dione (compd. no. 81.396) 0.77 g (0. 005 mol) of the hydantoin derivative of Example H7 is introduced into 50 mi of acetonitrile in a reaction vessel. This solution is treated in succession with 0.95 g (0.00688 mol) of finely pulverulent potassium carbonate and 0.96 g (0.00503 mol) of 2,6- dichloro-3-cyano-4-fluoropyridine and heated for 5 hours to reflux temperature, with stirring.

After this time, starting material can no longer be detected (TLC analysis). The reaction mixture is cooled and filtered, and the solvent is evaporated. The resulting dark brown viscous oil is chromatographed over a silica gel column (30 g) under pressure (eluent: hexane/ethyl acetate 2/1). The product-containing fractions which have an Rf value 0.26 are combined and freed from solvent. This gives the desired product as white crystals of m. p.

192-193°C. MS (FD): [M+, 40%] 308. Example H9: Preparation of 2-(3-luoro-5-cVano-6-methoxv-2-pyridyl ! tetrahydroimidazor15 alpyridine-1,3-dione (compd. no. 81.016) 0.85 g (0.00275 mol) of the compound of Example H8 is dissolved in 50 mi of dry acetonitrile and 0.56 ml (0.003 mol) of sodium methoxide (5.4 molar in methanol) is added.

This reaction mixture is heated to boiling point and kept at reflux temperature for 2.5 hours.

During this process, the reaction mixture slowly turns cloudy and a solid precipitate separates out. According to TLC analysis, less than 10% starting material is still present.

After the reaction mixture has been cooled, filtered and concentrated, 0.8 g of a viscous oil remains, and this is treated with 50 ml of water and extracted twice using in each case 50 mi of dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated, and the residue obtained is digested in diethyl ether. This gives the desired target compound as pale yellow crystals of m. p. 159-170°C.

Example H10: Preparation of 2- (5-chloro-3-fluoropyridin-2-yl)-7-hydroxvtetrahydroimidazo- [1. 5-a]-pyridine-1.3-dione (compd. no. 604.001) A reaction mixture composed of 100 ml of dioxane, 50 ml of N, N-dimethylformamide, 8 ml of propylene oxide, 6 mi of 0] undec-7-ene and 8.0 g of ethyl 4-hydroxypiperidine-2-carboxylate * hydrochloride is stirred overnight at 20°C. 4.4 g of potassium tert-butoxide and 50 ml of N, N-dimethylformamide are subsequently added, and the resulting suspension is heated for approx. 4 hours at 95°C. The reaction mixture is subsequently cooled, brought to pH 6.5 to 7.0 with cold aqueous 2N hydrochloric acid solution and extracted with ethyl acetate. The combined extracts are washed with sodium chloride solution and water and concentrated by evaporation, and the solid residue is purified by means of silica gel chromatography (eluent: hexane/ethyl acetate). This gives the title compound as a mixture of two diastereomers of m. p. 183-185°C and 184-186°C, which can be resolved. Example H11: Preparation of 2- (5-chloro-3-fluoropyridin-2-yl)-7-fluorotetrahydroimidazo-&l t;BR> <BR> [1, 5-al-pvridine-1,3-dione 2.6 g of 2- (5-chloro-3-fluoro-pyridin-2-yl)-7-hydroxitetrahydroimidazo- [1. 5-a]-pyridin-1,3- dione (isomer B, Example H10) in 80 ml dichloromethane is treated at-55°C to-65°C with 1.9 ml of diethylaminosulfur trifluoride (DAST) and stirred at the same temperature for 1 hour. The reaction mixture is then allowed to stir at 20°C over night. The resulting brownish solution is treated with ice and water and extracted with ethyl acetate. The combined extracts are washed with water, dried, filtered through a small silicagel column and evaporated to give the desired product with m. p. 154-157°C.

Example H12: Preparation of 1- (3-fluoro-5-cyano-6-chloro-2-pyridyl)-3-methyl-4- trifluoromethvl-pyrimidin-2,6-dione (compd. no. 3.396) A mixture of 0.776 g 1-methyl-6-trifluoromethyl-2, 4- (1 H, 3H » pyrimidin-dione, 0.760 g potassium carbonate and 0.768 g 2,6-dichloro-3-fluoro-5-cyanopyridine in 40 ml dimethylsulfoxide is stirred under nitrogen at 130°C until conversion is complete. Then the reaction mixture is cooled down and diluted with ice and water. The pH of the mixture is adjusted to neutral and the mixture is extracted several times with ethyl acetate. The organic layers are washed with water, dried, evaporated and the residue is purified by silicagel chromatography (hexane/ethyl acetate 7/3) to yield the title compound as a solid of m. p. 146-148°C.

Example H13: Preparation of 1-rriethyl-6-trifluoromethyl-2, 4 (1 H. 3H)-pyrimidin-dione Intermediate a): Preparation of 3-methylamino-4,4,4-trifluoromethyl-2-butenoic acid benzylester A mixture of 6.15 g 4,4,4-trifluoroaceto acetic acid benzylester and 4.6 g methylamine- hydrogene acetate in 250 ml cyclohexane is heated under nitrogen at reflux temperature for 2.5 hours. Water formed is absorbed in a column packed with molecular sieves A4. The vessel is then cooled down, and the mixture is filtered through silicagel and the filtrate evaporated to give the desired enamine as yellowish oil. 'H-NMR (CDCI3): 8.18 ppm (broad signal, 1H); 7.35 ppm (m, 5H); 5.15 ppm (m, 3H); 2.95 ppm (m, 3H).

Intermediate b): Preparation of 1-methyl-5-benzyloxycarbonyl-6-trifluoromethyl-2, 4- (1 H, 3H)- pyrimidin-dione A solution of 5.7 g 3-methylamino-4,4,4-trifluoromethyl-2-butenoic acid benzylester in 120 ml dichloromethane is treated at 20°C with a solution of 1.95 g chlorocarbonylisocyanate in 5ml of dichloromethane and stirred over night. Hydrogen chloride is splitted off during the reaction. The reaction is cooled down in an ice bath, neutralised with sodium hydrogencarbonate, washed with water and dried. After evaporation, the residue is filtered through a short column packed with silicagel (hexane/ethyl acetate 7/3). Evaporation of the eluate gives the desired product of m. p. 132-134°C.

Starting with 3-methylamino-4,4,4-trifuoromethyl-2-butenoic acid ethylester as the enamine leads to the corresponding 1-methyl-5-ethyoxycarbonyl-6-trifluoromethyl-2, 4- (1 H, 3H)- pyrimidin-dione with a m. p. of 131-133 °C. intermediate c): Preparation of 1-methyl-5-carboxy-6-trifluoromethyl-2,4- (1 H, 3H)-pyrimidin- dione A solution of 5.5 g 1-methyl-5-benzyloxycarbonyl-6-trifluormethyl-2, 4- (1 H, 3H)-pyrimidin- dione in 150 ml tetrahydrofurane is hydrogenated at 20°C over 0.560 g of Pd-C (5%). Then the reaction mixture is filtrated and the filtrate evaporated to dryness. The resulting desired carboxylic acid has a m. p. of 216°C (under decomposition).

Preparation of 1-methyl-6-trifluoromethyl-2, 4- (1 H, 3H)-pyrimidin-dione: 2.61 g 1-methyl-5- carboxy-6-trifluoromethyl-2, 4- (1 H, 3H)-pyrimidin-dione is heated under nitrogen at 220°C until decarboxylation has ceased. After cooling, the title compound with m. p. 140-142°C is obtained.

The preferred compounds given in Tables 1 to 194 below in which the substituents R, and R3 are defined as shown in Table A and in Tables 500 to 512 in which the substituents R, and R2 are defined as shown in Table B and in Tables 600 to 638 (intermediates with variable substituents R, and R2 as shown in Tables C and D) can also be prepared in a similar manner and by methods as they are shown in the general reaction schemes 1-9 and in the references indicated.

Table 1: A preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula I,.

Table 2: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 12.

Table 3: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 13.

Table 4: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 14.

Table 5: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 15- Table 6: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 16.

Table 7 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula I,, Table 8: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 18.

Table 9: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 19.

Table 10 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula ho.

Table 11: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula I".

Table 12 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1, 2.<BR> <BR> <P>Table 13 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 113 Table 14 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i14.

Table 15 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula! is.

Table 16 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 116- Table 17: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 117- Table 18: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula ha.

Table 19: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 119.

Table 20: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 120<BR> <BR> Table 21: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tri.

Table 22: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 122.

Table 23: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 123.

Table 24: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 124.

Table 25: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 125.

Table 26: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 126.

Table 27: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 127.

Table 28: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1289 Table 29: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 129.

Table 30: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 130.

Table 31: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 131- Table 32: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 132.

Table 33: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tus.

Table 34: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 134.

Table 35: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tau.

Table 36: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tau.<BR> <P>Table 37 : A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 137.

Table 38: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 138.

Table 39: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 139.

Table 40: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula lao.<BR> <BR> <P>Table 41: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula hui.

Table 42: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 142.

Table 43: A further preferred group of compounds of the formula I has the formula , where the meaning of the respective substituents Ri and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i43.

Table 44: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i44.

Table 45: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i45.

Table 46: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 146.

Table 47: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 147.<BR> <P>Table 48: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 148.

Table 49: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 149.

Table 50: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tso.

Table 51: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula iSr.

Table 52: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 152.

Table 53: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 153.

Table 54: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1s4.

Table 55: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula riss.

Table 56: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents Ri and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 155.

Table 57: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 157.

Table 58: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 158.

Table 59 : A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 159.

Table 60: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula teo.

Table 61 : A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 161.

Table 62: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i62@ Table 63: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 163.

Table 64: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula e4.

Table 65: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i65.

Table 66: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents Ri and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tee.

Table 67: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 167.

Table 68: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tea.

Table 69 : A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i69.

Table 70: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tao.

Table 71: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 171.

Table 72: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 172.

Table 73: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 173.

Table 74: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula a) 74.

Table 75: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 175.

Tabie 76: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tyg.

Table 77: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula ion.

Table 78: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 178- Table 79: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 179.

Table 80: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 180.

Table 81: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 18,.

Table 82: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents Ri and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 182.

Table 83: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tes.

Table 84: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 184.

Table 85: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 185.

Table 86: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tae.

Table 87: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 187.

Table 88: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tee.

Table 89: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula teg.

Table 90: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 190.

Table 91 : A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formulatri.

Table 92: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 192.

Table 93: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 193.

Table 94: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula ig4.<BR> <BR> <P>Table 95: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tus.<BR> <P>Table 96 : A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tge.

Table 97: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 197.

Table 98: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 198.

Table 99: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 199.

Table 100: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 11oo.

Table 101: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 11o,.

Table 102: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 11o2.

Table 103: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tios.

Table 104: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i104- Table 105: A further preferred group of compounds of the formula 1 has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula I, os.

Table 106: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 11o6.

Table 107: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1107- Table 108: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tics.

Table 109: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i109.

Table 110: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 111o.

Table 111: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula m.

Table 112: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tnz.

Table 113: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i113.

Table 114: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i114<BR> <BR> Table 115: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula i115.

Table 116: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1116.

Table 117: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tuv.

Table 118: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula ne.

Table 119: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1119.

Table 120: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1120.

Table 121: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1121.

Table 122: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1122.

Table 123: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1123.

Table 124: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1124- Table 125: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1125.

Table 126: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1126.

Table 127: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1127 Table 128: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1128.

Table 129: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1, 29.

Table 130: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents Ri and R3 are given in Table A, thus disclosing 412 specific compounds of the formula to.

Table 131: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula isi.

Table 132: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1132.

Table 133: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1133.

Table 134: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1134.

Table 135: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1135.

Table 136: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1, 36.

Table 137: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1, 37.

Table 138: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula hais.

Table 139: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1139.

Table 140: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 114o.

Table 141: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R1 and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1141.

Table 142: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1142.

Table 143: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1143.

Table 144: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1144.

Table 145: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents Ri and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1145.

Table 146: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1146.

Table 147: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1147.

Table 148: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1148- Table 149: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1149.

Table 150: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1150.

Table 151: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula! isi.

Table 152: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1152.

Table 153: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tirs.

Table 154: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1154.

Table 155: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1155.

Table 156: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1156.

Table 157: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1157.

Table 158: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1158.

Table 159: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula lirg.

Table 160: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tieo.

Table 161: A further preferred group of compounds of the formula I has the formula (116,), where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1, 61.

Table 162: A further preferred group of compounds of the formula I has the formula (1162), where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1162 Table 163: A further preferred group of compounds of the formula I has the formula (1163), where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1163.

Table 164: A further preferred group of compounds of the formula I has the formula (tu64), where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1164.

Tabie 165: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1165.

Table 166: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula1166.

Table 167: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1167.

Table 168: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formulatiers.

Table 169: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1169.

Table 170: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula I"o.

Table 171: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula I",.

Table 172: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula1172.

Table 173: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula hps.

Table 174: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula1174- Table 175: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1175.

Table 176: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1176.

Table 177: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula il-n.

Table 178: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1178- Table 179: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula tiyg.

Table 180: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1180.

Table 181: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1181- Table 182: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formulai182- Table 183: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formulaties.

Table 184: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula1184.

Table 185: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1185.

Table 186: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1186.

Table 187: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1187.

Table 188: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1188.

Table 189: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula1189.

Table 190: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 11go.

Table 191: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R1 and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 119,.

Table 192: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1192.

Table 193: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula 1193.

Table 194: A further preferred group of compounds of the formula I has the formula where the meaning of the respective substituents R, and R3 are given in Table A, thus disclosing 412 specific compounds of the formula It94.

Table A Comp. No. R3 .001 F NH2 .002 F OH .003 F SH SO2Cl.004F . 005 F NH (CH3) . 006 F N (CH2CH3) 2 .007 F NH (COCH3) .008 F NH (CH2CH=CH2) . 009 F N (CH3) (CH2C=CH) N(SO2CH3)2.010F NH(SO2CH2CH3).011F . 012 F N (CH2CH=CH2) (SO2CH2CH3) . 013 F N(CH2C#CH)(SO2CH (CH3) 2) N(CH2CF3)(CHO).014F .015 F NH (CH2C6H5) .016 F OCH3 .017 F OCH2CH3 . 018 F OCH (CH3) 2 . 019 F OCH (CH3) CH2CH2CH3 OCH2CH=CH2.020F . 021 F OCH (CH3) CH=CH2 OCH2C#CH.022F . 023 F OCH (CH3) C-CH OCH(cyclopentyl)2.024F .025 F OCH20CH2C6H5 .026 F OCH2 (C6H5) OCH2(2-F-C6H5).027F . 028 F OCH (CH3) (4-CH3-C6H5) .029 F OC6H5 O(4-pyrimidyl).030F . 031 F OCH2CH2CI .032 F OCH2CH=CHCI OCH2CH2OH.033F OCH2OCH3.034F Comp. No. Rires .035 F OCH2CH20CH2CH3 .036 F OCH2CH20CH2CH20CH2CH3 . 037 F OCH (CH3) CH20CH2CH=CH2 .038 F OCOCH3 .039 F OCOOCH3 .040 F OCOCH2C6H5 .041 F OCH2SCH3 .042 F OCH2CH2SCH2CH3 .043 F OCH2COOH . 044 F OCH (CH3) COOH . 045 F (R)-OCH (CH3) COOH . 046 F (S)-OCH (CH3) COOH .047 F OCH2COOCH2CH3 . 048 F OCH (CH3) COOCH3 . 049 F OCH (CH3) COOCH2CH=CH2 . 050 F OCH (CH3) COOCH2 (C6H5) . 051 F OCH (CH3) CH2COOH . 052 F OCH (CH3) CH2COOCH2CH3 .053 F OCH2COSCH3 . 054 F OCH (CH3) COSCH2CH3 . 055 F OCH (CH3) COSCH (CH3) 2 .056 F OCH2CONH2 . 057 F OCH2CON (CH2CH3) z . 058 F OCH (CH3) CON (CH3) 2 . 059 F OCH (CH3) CONH (CH2CH=CH2) . 060 F OCH (CH3) CON (CH3) (CH2C#CH) . 061 F OCH (CH3) CON (CH2C6H5) 2 . 062 F OCH (CH3) CON (CH3) (C6H5) .063 F OCH2COOCH2CH2SCH3 . 064 F OCH (CH (CH3) 2) COOH . 065 F OCH (CH3) COOCH2CH20CH2CH3 . 066 F OCH (C6H5) COOH . 067 F (R)-OCH (C6H5) COOH . 068 F (S)-OCH (C6H5) COOH . 069 F OCH (C6H5) COOCH3 Comp. No. R3 . 070 F OCH(C6H5) COOCH (CH3) C--CH . 071 F OCH (C6H5) COOCH2C6H5 . 072 F OCH (C6H5) COSCH (CH3) 2 . 073 F OCH (C6H5) CONH2 . 074 F OCH (C6H5) CONH (CH2C#CH) . 075 F OCH (C6H5) CON (CH2CH=CH2) 2 . 076 F OCH (C6H5) CON (CH3) CH2C6H5 . 077 F OCH (C6H5) CONH (CH2 (2-F-C6H5)) . 078 F OCH(C6H5) CONH (cyclopropyl) .079 F OCH2CH2COOH .080 F OCH2CH2COOCH2CH3 . 081 F OCH (CH3) CH2COOH .082 F SCH3 . 083 F SCH (CH3) 2 .084 F SCH2CH=CH2 SCH2C6H5.085F .086 F SCH2CH20CH3 .087 F SC6H5 SCH2COOH.088F . 089 F SCH2COOCH2C6H5 . 090 F SCH (CH3) COOH . 091 F SCH (CH3) COOCH2CH3 . 092 F SCH (CH3) COOCH2CH=CH2 . 093 F SCH (CH3) COSCH3 . 094 F SCH (CH3) CON (CH3) 2 . 095 F SCH (CH3) CONH (CH2CH=CH2) .096 F SOCH2CH3 .097 F S02CH3 .098 F S02NH2 . 099 F S02N (CH3) 2 SO2N(CH2CH3)2.100F . 101 F SO2N (CH3) (CH2 (4-CH3-C6H5)) SO2NHCH2CH2OCH3.102F .103 F SCOOCH3 . 104 F SCON (CH3) 2 Comp. No. R3 . 105 F SCONHCH2CH=CH2 . 106 F SCOOCH2CHCH2 . 107 F SCON (CH2CH3) COCF3 NH2.108Cl . 109 Cl OH SH.110Cl SO2Cl.111Cl . 112 Cl NH (CH3) N(CH2CH3)2.113Cl . 114 Cl NH (COCH3) . 115 Cl NH (CH2CH=CH2) . 116 Cl N (CH3) (CH2C=CH) . 117 Cl N (S02CH3) 2 . 118 Cl NH (S02CH2CH3) . 119 Cl N (CH2CH=CH2) (SO2CH2CH3) . 120 Cl N (CH2C-CH) (S02CH (CH3) 2) . 121 Cl N (CH2CF3) (CHO) . 122 Cl NH (CH2C6H5) .123 Cl OCH3 OCH2CH3.124Cl . 125 Cl OCH (CH3) 2 . 126 Cl OCH (CH3) CH2CH2CH3 OCH2CH=CH2.127Cl . 128 Cl OCH (CH3) CH=CH2 OCH2C#CH.129Cl OCH(CH3)C#CH.130Cl . 131 Cl OCH (cyclopentyl) . 132 Cl OCH2 (C6H5) . 133 Cl OCH2 (2-F-C6H5) . 134 Cl OCH (CH3) (4-CH3-C6H5) OC6H5.135Cl O(4-pyrimidyl).136Cl . 137 Cl OCH2CH2CI OCH2CH=CHCl.138Cl OCH2CH2OH.139Cl Comp. No. R, R 3 .140 Cl OCH2OCH3 .141 OCH2CH2OCH2CH3 .142 OCH2CH2OCH2CH2OCH2CH3 . 143 Cl OCH (CH3) CH20CH2CH=CH2 . 144 Cl OCOCH3 . 145 Cl OCOOCH3 OCOCH2C6H5.146Cl . 147 Cl OCH2SCH3 . 148 Cl OCH2CH2SCH2CH3 .149 Cl OCH2COOH . 150 Cl OCH (CH3) COOH . 151 Cl (R)-OCH (CH3) COOH . 125 Cl (S)-OCH (CH3) COOH OCH2COOCH2CH3.153Cl . 154 Cl OCH (CH3) COOCH3 . 155 Cl OCH (CH3) COOCH2CH=CH2 . 156 Ci OCH (CH3) COOCH2 (C6H5) . 157 Cl OCH (CH3) CH2COOH . 158 Cl OCH (CH3) CH2COOCH2CH3 OCH2COSCH3.159Cl . 160 Cl OCH (CH3) COSCH2CH3 . 161 Cl OCH (CH3) COSCH (CH3) 2 OCH2CONH2.162Cl . 163 Cl OCH2CON (CH2CH3) 2 . 164 Ci OCH (CH3) CON (CH3) 2 . 165 Cl OCH (CH3) CONH (CH2CH=CH2) . 166 Cl OCH (CH3) CON (CH3) (CH2C=CH) . 167 Cl OCH (CH3) CON (CH2C6H5) 2 . 168 Cl OCH (CH3) CON (CH3) (C6H5) OCH2COOCH2CH2SCH3.169Cl . 170 Cl OCH (CH (CH3) 2) COOH . 171 Cl OCH (CH3) COOCH2CH20CH2CH3 . 172 Cl OCH (C6H5) COOH . 173 Cl (R)-OCH (C6H5) COOH . 174 Cl (S)-OCH (C6H5) COOH Comp. No. R3 OCH(C6H5)COOCH3.175Cl OCH(C6H5)COOCH(CH3)C#CH.176Cl . 177 Cl OCH (C6H5) COOCH2C6H5 OCH(C6H5)COSCH(CH3)2.178Cl . 179 Cl OCH (C6H5) CONH2 . 180 Cl OCH(C6H5) CONH (CH2C_CH) OCH(C6H5)CON(CH2CH=CH2)2.181Cl OCH(C6H5)CON(CH3)CH2C6H5.182Cl . 183 Cl OCH (C6H5) CONH (CH2 (2-F-C6H5) . 184 Cl OCH(C6H5) CONH (cyclopropyl) OCH2CH2COOH.185Cl . 186 Cl OCH2CH2COOCH2CH3 . 187 Cl OCH (CH3) CH2COOH SCH3.188Cl . 189 Cl SCH (CH3) 2 SCH2CH=CH2.190Cl . 191 CI SCH2C6H5 . 192 Cl SCH2CH20CH3 SC6H5.193Cl SCH2COOH.194Cl . 195 Cl SCH2COOCH2C6H5 . 196 Cl SCH (CH3) COOH . 197 Cl SCH (CH3) COOCH2CH3 . 198 Cl SCH (CH3) COOCH2CH=CH2 . 199 Ci SCH (CH3) COSCH3 . 200 Cl SCH (CH3) CON (CH3) 2 . 201C ! SCH (CH3) CONH (CH2CH=CH2) SOCH2CH3.202Cl SO2CH3.203Cl SO2NH2.204Cl . 205 Cl SO2N (CH3) 2 SO2N(CH2CH3)2.206Cl . 207 Cl SO2N (CH3) (CH2 (4-CH3-C6H5)) .208 CI S02NHCH2CH2OCH3 SCOOCH3.209Cl Comp. No. R, R 3 . 210 Cl SCON (CH3) 2 SCONHCH2CH=CH2.211Cl . 212 Cl SCOOCH2CH=CH2 . 213 Cl SCON (CH2CH3) COCF3 .214 H NH2 .215 H OH .216 H SH .217 H S02CI .218 H NH (CH2C6H5) .219 H N (CH2CH=CH2) 2 N(SO2CH3)2.220H .221 H NH (S02CH2CH3 . 222 H NH (COCH3) .223 H OCH3 .224 H OCH2CH3 .225 H OCH2CH=CH2 OCH2C#CH.226H .227 H OCH2C6H5 .228 H OCH2CH2CI .229 H OCH2CH20H .230 H OCH20CH3 .231 H OCH2CH20CH2CH3 OCH2CH2OCH2CH2OCH3.232H .233 H OCOCH3 .234 H OCOOCH3 .235 H OCH2SCH3 .236 H OCH2CH2SCH3 .237 H OCH2COOH .238 H OCH2COOCH3 .239 H OCH2COOCH2C6H5 . 240 H OCH2CONH (CH3) . 241 H OCH (CH3) COOH . 242 H OCH (CH3) COOCH2CH3 . 243 H OCH (CH3) COOCH2CH=CH2 . 244 H OCH (CH3) COOCH2C6H5 Comp. No. R3 . 245 H OCH (CH3) CONH2 . 246 H OCH (CH3) CONH (CH2CH=CH2) . 247 H OCH (CH3) CON (CH3) 2 . 248 H OCH (CH3) COSCH (CH3) 2 OCH(C6H5)COOH.249H . 250 H OCH (C6H5) COOCH3 . 251 H OCH (C6H5) COOCH2CH=CH2 . 252 H OCH (C6H5) CONH2 . 253 H OCH(C6H5) CONH (CH2CH3) . 254 H OCH (C6H5) CON (CH3) 2 . 255 H OCH (C6H5) COSCH3 . 256 H OCH (C6H5) COSCH (CH3) 2 . 257 H OCH (CH3) CH2COOH . 258 H OCH (CH3) CH2COOCH2CH3 .259 H SCH3 . 260 H SCH (CH3) 2 SCH2C6H5.261H . 262 H SCH (CH3) COOH . 263 H SCH (CH3) COOCH2CH3 .264 H S02NH2 SO2NH(CH2CH=CH2).265H . 266 H S02N (CH3) 2 .267 H SCOCH3 .268 H SCOOCH2CH3 .269 CH3 NH2 .270 CH3 OH .271 CH3 SH .272 CH3 S02CI .273 CH3 NH (CH2C6H5) . 274 CH3 N (CH2CH=CH2) 2 . 275 CH3 N (S02CH3) 2 NH(SO2CH2CH3.276CH3 . 277 CH3 NH (COCH3) .278 CH3 OCH3 .279 CH3 OCH2CH3 Comp. No. R i R3 .280 CH3 OCH2CH=CH2 OCH2C#CH.281CH3 .282 CH3 OCH2C6H5 .283 CH3 OCH2CH2CI .284 CH3 OCH2CH20H OCH2OCH3.285CH3 OCH2CH2OCH2CH3.286CH3 .287 CH3 OCH2CH20CH2CH20CH3 .288 CH3 OCOCH3 .289 CH3 OCOOCH3 .290 CH3 OCH2SCH3 .291 CH3 OCH2CH2SCH3 .292 CH3 OCH2COOH .293 CH3 OCH2COOCH3 .294 CH3 OCH2COOCH2C6H5 . 295 CH3 OCH2CONH (CH3) . 296 CH3 OCH (CH3) COOH . 297 CH3 OCH (CH3) COOCH2CH3 . 298 CH3 OCH (CH3) COOCH2CH=CH2 . 299 CH3 OCH (CH3) COOCH2C6H5 . 300 CH3 OCH (CH3) CONH2 . 301 CH3 OCH (CH3) CONH (CH2CH=CH2) . 302 CH3 OCH (CH3) CON (CH3) 2 . 303 CH3 OCH (CH3) COSCH (CH3) 2 . 304 CH3 OCH (C6H5) COOH . 305 CH3 OCH (C6H5) COOCH3 . 306 CH3 OCH (C6H5) COOCH2CH=CH2 . 307 CH3 OCH (C6H5) CONH2 . 308 CH3 OCH(C6H5) CONH (CH2CH3) . 309 CH3 OCH(C6H5) CON (CH3) 2 OCH(C6H5)COSCH3.310CH3 . 311 CH3 OCH (C6H5) COSCH (CH3) 2 . 312 CH3 OCH (CH3) CH2COOH . 313 CH3 OCH (CH3) CH2COOCH2CH3 .314 CH3 SCH3 Comp. No. Rirez . 315 CH3 SCH (CH3) 2 . 316 CH3 SCH2C6H5 . 317 CH3 SCH (CH3) COOH . 318 CH3 SCH (CH3) COOCH2CH3 . 319 CH3 S02NH2 SO2NH(CH2CH=CH2).320CH3 . 321 CH3 S02N (CH3) 2 .322 CH3 SCOCH3 .323 CH3 SCOOCH2CH3 .324 H N-imidazolyl .325 F N-imidazolyl . 326 ci N-imidazolyl . 327 CH3 N-imidazolyl . 328 F N-1,2,4-triazol-1-yl . 329 F N-1,2,4-triazol-4-yl . 330 F N-1,2,3-triazol-1-yl . 331 Cl N-1,2, 4-triazol-1-yl . 332 CI N-1,2,4-triazol-4-yl . 333 CI N-1,2,3-triazol-1-yl N-pyrrolidinyl.334Cl .335 F N-pyrrolidinyl .336 F N-piperidinyl . 337 F N- (4-methyl-piperazinyl) . 338 CI N-pyrazolyl . 339 CH3 N-pyrazolyl . 340 F N-pyrazolyl . 341 H N-1, 2, 4-triazol-1-yl .342 H N-1,2,3-triazol-1-yl .343 H N-pyrrolidinyl .344 H N-piperidinyl .345 H N- (4-methyl-piperazinyl) . 346 H N-morpholinyl . 347 F N-morpholinyl . 348 CH3 N-imidazolyl . 349 F N (CH3) 2 Comp. No. R R 3 .350 F OCH2CH20CH2CH20CH3 .351 F OCH2COOCH2CH3 . 352 F OCH (CH3) COOCH2CH3 . 353 F OCH2CH (OH) CH20H . 354 F OCH2COOC (CH3) 3 .355 F OCH2CH2C6H5 N(CH2C#CH)(SO2CH2CH3).356F .357 F OCH2CH2CH2CH3 . 358 F OCH (C6H5) COOCH2CH3 .359 F OCH2CH2CH2COOCH2CH3 .360 F OCH2CH2CH3 .361 F OCH2CH=CHCI .362 F OCH2COOCH2C6H5 .363 F OCH2CN .364 H OCH2CN .365 F OCH2CF3 .366 F OCH2CONH2 OC3H7-n.367F .368 H OCH2CF3 .369 H OCH2CONH2 . 370 Cl OCH2CONH2 OCH2CN.371Cl . 372 F OCH (CH3) CN . 373 F OCH (CH3) CF3 .374 H OS02CH3 .375 H OS02CH3 OSO2CF3.376F .377 F OS02C4F9 .378 H OS02C4F9 .379 H S02C2H5 SO2CH3.380F SO2CH3.381Cl SO2CF3.382Cl SO2CH3.383F SO2C6H5.384F Comp. No. R R 3 .385 F S02C6H4-4CI .386 H SO2C6H5 SO2C6H5.387Cl .388 F OCH2CONH (CH3) . 389 F OCH2CON (CH3) 2 . 390 H OCH2CON (CH3) 2 Cl.391H .392 H Br .393 H .394 F F .395 H F Cl.396F .397 F Br .398 F Cl.399Cl F.400Cl Br.401Cl . 402 F OC (CH3) 2COOCH2CHCH2 . 403 F OC (CH3) 2COOCH2CCH . 404 F OCH (CH3) COOCH2CHCH2 . 405 Cl OC (CH3) 2COOCH2CHCH2 . 406 H OC (CH3) 2COOCH2CHCH2 . 407 H OCH (CF3) CH2COOC2H5 . 408 F OCH (CF3) CH2COOC2H5 . 409 F OCH (CH3) CH2COOCH3 . 410 F OCH (CH3) CH2COOCH3 . 411 H OCH (CH3) CH2COOCH3 .412 H OCH CH3 CH2COOC2H5 Table 500: A preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula soo.

Table 501: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Tabie B, thus disclosing 168 specific compounds of the formula 1501.

Table 502: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula 1502 Table 503: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula i503.

Table 504: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula iso4- Table 505: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula tsos.

Table 506: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents Ri and R2 are given in Table B, thus disclosing 168 specific compounds of the formula tsoe.

Table 507: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula i507.

Table 508: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula 1508.

Table 509: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula 1509.

Table 510: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula i510.

Table 511: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula tsu.

Table 512: A further preferred group of compounds of the formula I has the formula where the meanings of the respective substituents R, and R2 are given in Table B, thus disclosing 168 specific compounds of the formula 1512- Table B Comp. No. R R 2 .001 F NH2 .002 F OH .003 F OCH3 .004 F OCH2CH3 . 005 F OCH (CH3) 2 . 006 F OCH (CH3) CH2CH2CH3 . 007FOCH2CH=CH2 . 008 F OCH (CH3) CH=CH2 OCH2C#CH.010F . 011 F OCH (CH3) C=CH .012 F OCH2OCH2C6H5 .013 F OCH2 (C6H5) . 014 F OCH2 (2-F-C6H4) . 015 F OCH (CH3) (4-CH3-C6H4) .016 F OC6H5 . 017 F OCH2CH=CHCI .018 F OCH2CH20H .019 F OCH20CH3 OCH2CH2OCH2CH3.020F OCH2CH2OCH2CH2OCH2CH3.021F . 022 F OCH (CH3) CH20CH2CH=CH2 .023 F OCOCH3 .024 F OCOOCH3 OCOCH2C6H5.025F .026 F OCH2SCH3 .027 F OCH2CH2SCH2CH3 .028 F OCH2COOCH2CH3 . 029 F OCH (CH3) COOCH3 . 030 F OCH (CH3) 2COOCH2CH=CH2 O-tert-butyl.031F . 032 F OCH (CH3) CH2COOCH2CH3 .033 F OCH2COSCH3 . 034 F OCH2CONH2 . 035 F OCH2CON (CH2CH3) 2 Comp. No R2 OCH(CH3)CON(CH3)2.036F .037 F OCH (CH3) CONH (CH2CH=CH2) .038 F OCH (CH3) CON (CH3) (CH2C=CH) OCH(C6H5)CONH2.039F . 040 F OCH (C6H5) CONH (CH2C=-CH) . 041 F OCH (C6H5) CON (CH2CH=CH2) 2 . 042 F OCH2CH2COOCH2CH3 NH2.43Cl OH.44Cl . 45 Cl NH (CH3) .460OCH3 . 47 Cl OCH2CH3 . 48 Cl OCH (CH3) 2 . 49 Cl OCH (CH3) CH2CH2CH3 OCH2CH=CH2.50Cl . 51 Cl OCH (CH3) CH=CH2 . 52 CI OCH2C=CH . 53 Cl OCH (CH3) C--CH OCH(cyclopentyl).54Cl OCH2(C6H5).55Cl . 56 Cl OCH2 (2-F-C6H4) . 57 Cl OCH (CH3) (4-CH3-C6H4) OC6H5.58Cl OCH2CH2Cl.59Cl OCH2CH=CHCl.60Cl OCH2CH(Cl)CH2.61Cl . 62 Cl OCH20CH3 OCH2CH2OCH2CH3.63Cl OCH2CH2OCH2CH2OCH2CH3.64Cl . 65 Cl OCH (CH3) CH20CH2CH=CH2 OCOCH3.66Cl OCH2SCH3.67Cl OCH2CH2SCH2CH3.68Cl OCH2COOH.69Cl . 70 Cl OCH (CH3) COOH Comp. No. R2 . 71 Cl (R)-OCH (CH3) COOH . 72 Cl (S)-OCH (CH3) COOH OCH2COOH2CH3.73Cl . 74 Cl OCH (CH3) COOCH3 . 75 Cl OCH (CH3) COOCH2CH=CH2 OCH(CH3)COOCH2(C6H5).76Cl . 77 Cl OCH (CH3) CH2COOH . 78 Cl OCH (CH3) CH2COOCH2CH3 .79 Cl OCH2CONH2 . 80 Cl OCH2CON (CH2CH3) 2 . 81 Cl OCH (CH3) CON (CH3) 2 . 82 Cl OCH (CH3) CONH (CH2CH=CH2) . 83 Cl OCH (CH3) CON (CH3) (CH2C_CH) .84 F OCH (CH3)-cyclopropyl . 85 F OCH (CH3) CH2COOCH3 . 86 H OCH (CH3) CH2COOCH3 . 87 Cl OCH (C6H5) COOCH3 . 88 Cl OCH(C6H5) COOCH (CH3) C=CH OCH(C6H5)COOCH2C6H5.89Cl . 90 Cl OCH (C6H5) COSCH (CH3) 2 OCH(C6H5)CONH2.91Cl OCH(C6H5)CONH(CH2C#CH).92Cl . 93 Cl OCH (C6H5) CONH (cyclopropyl) . 94 Cl OCH2C (CI) CH2 OCH2CHCH-Cl.95Cl .96 H NH2 .97 H OH .98 H OCH3 .99 H OCH2CH3 OCH2CH=CH2.100H OCH2C#CH.101H . 102 H OCH2C6H5 . 103 H OCH2CH2CI . 104 H OCH2CH20H OCH2OCH3.105H Comp. No. R R 2 OCH2CH2OCH2CH3.106H .107 H OCH2CH20CH2CH20CH3 .108 H OCOCH3 . 109 H OCOOCH3 . 110 H OCH2SCH3 .111 H OCH2CH2SCH3 .112 H OCH2COOCH3 .113 H OCH2COOCH2C6H5 . 114 H OCH2CONH (CH3) . 115 H OCH (CH3) COOCH2CH3 . 116 H OCH (CH3) COOCH2CH=CH2 . 117 H OCH (CH3) COOCH2C6H5 . 118 H OCH (CH3) CONH2 . 119 H OCH (CH3) CONH (CH2CH=CH2) . 120 H OCH (CH3) CON (CH3) 2 . 121 H OCH (C6H5) COOCH3 . 122 H OCH (C6H5) COOCH2CH=CH2 . 123 H OCH (C6H5) CONH2 . 124 H OCH (C6H5) CONH (CH2CH3) . 125 H OCH (C6H5) CON (CH3) 2 . 126 F OCH (CF3) CH2COOC2H5 .127 CH3 OCH3 .128 CH3 OCH2CH3 . 129 CH3 OCH2CH=CH2 . 130 CH3 OCH2C=CH .131 CH3 OCH2C6H5 OCH2OCH3.132CH3 .133 CH3 OCH2CH20CH2CH3 .134 CH3 OCH2SCH3 .135 CH3 OCH2CF3 . 136 CH3 OCH (CH3) CONH2 .137 F OCH2CH20CH2CH20CH3 .138 F OCH2COOCH2CH3 . 139 F OCH (CH3) COOCH2CH3 .140 F N02 Comp. No. Rirez . 141 F OCH2COOC (CH3) 3 OCH2CH2C6H5.142F . 143 F OCH2CH2CH2CH3 OCH2-cyclopopyl.144F . 145 F OCH2CH2CH3 . 146 F OCH2CH=CHCI .147 F OCH2COOCH2C6H5 .147 F OCH2CN .148 H OCH2CN .149 F OCH2CF3 OC3H7-n.150F .151 H OCH2CF3 .152 H OCH2CONH2 OCH2CN.153Cl . 154 F OCH (CH3) CN . 155 F OCH (CH3) CF3 .156 H OS02CH3 .157 H OS02CH3 .158 F OS02CF3 OSO2C4F9.159F .160 H OS02C4F9 . 161 F OCH2CONH (CH3) . 162 F OCH2CON (CH3) 2 . 163 H OCH2CON (CH3) 2 . 164 F OCH (CH3) CF3 @.165F NO2.166Cl . 167 F OC (CH3) 2COOCH2CHCH2 OC(CH3)2COOCH2CCH.168F Table 600: A preferred group of compounds of the formula fit has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 111600.

Table 601: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 11160,.

Table 602: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 1116o2 Table 603: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula ttieos.

Table 604: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula111604.

Table 605: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 1116o5.

Table 606: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula theoe.

Table 607: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula II1,.

Table 608: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula lllwb.

Table 609: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 111609.

Table 610: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 11161ow Table 611: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula Xten.

Table 612: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 111612- Table 613: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 111613.

Table 614: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 111614e Table 615: A further preferred group of compounds of the formula I11 has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 11161s.

Table 616: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula Hteie.

Table 637: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 111637- Table 638: A further preferred group of compounds of the formula III has the formula where the meanings of the respective substituents R, and R2 are given in Table C, thus disclosing 25 specific compounds of the formula 111638.

Table C Comp. No. R R2 .001Cl .002 F CN .003 F OCH3 .004 F OCF3 .005 F CF3 .006 F Br NO2.007F .008 F CH3 OCH2C#CH.009F . 010 Cl CN OCH3.001Cl .012 Cl OCF3 CF3.013Cl Br.014Cl NO2.015Cl .016 Cl CH3 Cl.017Cl CF2H.018Cl Comp. No. R, R2 . 019 H F .020 H CI . 021 H Br .022 H CF3 .023 H OCF3 .024 H NO2 .025 H CN Table 617: A preferred group of compounds of the formula IV has the where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV617.

Table 618: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV6, 8.

Table 619: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV6, 9.

Table 620: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV62o.

Table 621: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV621 Table 622: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV622.

Table 623: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula In623.

Table 624: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV624.

Table 625: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV625.

Table 626: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV626.

Table 627: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV627.

Table 628: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV628.

Table 629 A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV629.

Table 630: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulatVgso.

Table 631: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV631.

Table 632: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Tabie D, thus disclosing 25 specific compounds of the formula IV632.

Table 633: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV633.

Table 634: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV634- Table 635: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formula IV635.

Table 636: A further preferred group of compounds of the formula IV has the formula where the meanings of the respective substituents R, and R2 are given in Table D, thus disclosing 25 specific compounds of the formulaIV636.

Table D Comp. No. R, R2 L Cl.001F .002 F CN .003 F OCH3 .004 F OCF3 .005 F CF3 .006 F Br NO2.007F .008 F CH3 OCH2C#CH.009F CN.010Cl OCH3.011Cl .012 Cl OCF3 . 013 ci CF3 . 014 Cl Br NO2.015Cl CH3.016Cl Cl.017Cl . 018 CI CF2H F.019H Cl.020H .021 H Br CF3.022H .023 H OCF3 .024 H N02 .025 H CN Table E: Physicochemical data for compounds in the abovementioned tables which have been prepared. The figure before the dot indicates the number of the table, for example 1.367 means compound No. 367 of Table A in Table 1, and 500.003 means Compound No.

003 of Table B in Table 500. Comp. No. Physicochemical data 1.001'H NMR (CDCI3; 8ppm): 7.62 (d, 1 H); 6.38 (s, 1 H); 5.83 (s, 2H); 3.47 (s, 3H). 1.002 m. p. 200-202°C (Example H5) 1.016 m. p. 120-122°C 1.0171.5139nD40 1.020 39 nô1.5240 1.022 m. p. 119-121 °C nD301.53451.025oil; 1.026 m. p. 146-147°C 1.047 m. p. 123-125°C 1.048 m. p. 128-130°C 1.123 m. p. 168-170°C 1.363m.p. 57-59°C 1.48811.365nD35 1.366 m. p. 115-117°C 1.367 au Oil; nD 1. 5037 1.396 m. p. 113-115°C 1.399 m. p. 183-184°C 1.402 m. p. 115-117°C 3.394 m. p. 145-147°C 3.396 m. p. 146-148°C 31.002 m. p. 161-163°C 31.017 m. p. 80-82°C 31.022 m. p. 88-90°C 31.365'H-NMR (CDCI3): 8. 10 ppm (s, 1H); 7.76 ppm (d, 1H); 7.34 ppm (s, 1 H); 4.76 ppm (m, 2H) 8.12 ppm (s, 1H); 7.83 ppm (d, 1H ; 7.35 ppm (s, Comp. No. Physicochemical data 1H) 81.396 m. p. 192-193°C 82.002'H-NMR (CDC13): 7.73 ppm (d, 1 H); 5.19 ppm (broad d, 1 H); 4.42 ppm (m, 1H); 4.17 ppm (m, 1H); 3.33 ppm (m, 1H); 2.62 ppm (m, 1 H); 1.68-2.23 ppm (2xm, 3H) (isomer B) 7.72 ppm (d, 1 H); 5.20 ppm (broad d, 1 H); 4.73 ppm (m, 2H); 4.40 ppm (m, 1H); 4.15 ppm (m, 1H); 3.33 ppm (m, 1H); 2.65 ppm (m, 1H); 2.15 ppm (m, 1H); 1.64-1.94 ppm (m, 2H) (isomer B) 155.396 m. p. 223-225°C 500.002 m. p. 189-192°C 500.003 m. p. 143-145°C 500.004 m. p. 149-151 °C 500.007 39 1. 5186 500.009 m. p. 69-71 °C 500.027 m. p. 139-141 °C 500.028 m. p. 80-81°C 1.5093500.019nD35 500.033 m. p. 193-195°C 500.144 m. p. 106-108°C 500.147 m. p. 134-136°C 500.149 m. p. 141-143°C 510.002'H-NMR (CDCI3): 8.14 ppm (s, 1H); 7.38 ppm (d, 1H); 7.22 ppm (s, 1H) 510.004 m. p. 92-94°C 510.010'H-NMR (CDCl3) : 8.10 ppm (s, 1H); 7.84 ppm (d, 1H); 7.33 ppm (s, 1 H); 4.90 ppm (s, 2H); 2.71 ppm (s, 1 H) 600.001 m. p. 133-134°C 600.021 m. p. 161-163°C 609.001 m. p. 114-116°C 613.001 m. p. 183-184°C 617.001 m. p. 142-143°C 626.001 m.. 143-145°C Comp. No. Physicochemical data 634.001 m. p. 180-183°C (isomer B) 635.001 m. p. 183-185°C;'H-NMR (CDCI3): 8.30 ppm (s, 1H); 7.25 ppm (d, 1H); 5.19 ppm (d, 1H); 4.41 ppm (m, 1H); 4.17 ppm (m, 1H); 3.32 ppm (m, 1H); 2.61 ppm (m, 1H); 2.14 ppm (m, 1H); 1.61-2.20 ppm (m, 2H) (isomer B) 637.001 m. p. 189-191 °C 638.001 m. p. 150-152°C Examples of specific formulations of active ingredients of the formula 1, such as mulsion concentrates, solutions, wettable powders, coated granules, extruder granules, dusts and suspension concentrates, are described in WO 97/34485 on pages 9 to 13.

Biological examples Example B1: Herbicidal action before plant emergence (pre-emergence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastic pots.

Immediately after sowing, the test substances are sprayed on as aqueous suspensions (prepared from a 25% strength wettable powder (Example F3, b) in accordance with WO 97/34485) or as emulsions (prepared from a 25% strength mulsion concentrate (Example F1, c) in accordance with WO 97/34485), corresponding to a dosage of 2 kg of a. i./ha (500 l of water/ha). The test plants are subsequently grown in the greenhouse under optimal conditions. After a test period of 3 weeks, the experiment is evaluated using a nine- level key (1 = complete damage, 9 = no effect). Score figures of 1 to 4 (in particular 1 to 3) signify a good to very good herbicidal action.

Test plants: Lolium, Setaria, Sinapis, SoJanum, Stellaria, Ipomea.

The compounds according to the invention exhibit good herbicidal activity.

Examples of the good herbicidal activity of the compounds of the formula I are given in Table B1.

Table B1: Pre-emergence action: Test plant: Lolium Setaria Sinapis Solanum Stellaria Ipomoea Dose [g a. i./ha] Active ingredient No.

1.002 7 1 1 1 5 1 2000 1.016 1 1 1 1 1 1 2000 1.017 1 1 1 1 1 1 2000 1.020 1 1 1 1 1 1 2000 1.022 1 1 1 1 1 1 2000 1.025 3 1 1 1 3 1 2000 1.026 1 1 1 1 3 1 2000 1.047 5 1 1 1 7 1 2000 1.048 1 1 1 1 1 1 2000 1.363 3 1 2 1 1 7 2000 1.365 1 1 1 1 1 1 2000 1.366 3 1 1 1 3 1 2000 1.367 1 1 1 1 1 1 2000 1.396 1 1 1 1 1 1 2000 1.402 1 1 1 1 1 4 2000 500.007 4 1 2000 500.009 2 1 3 1 1 3 2000 500.029 4 1 2000 500.033 2 1 2000 500.144 2 1 2000 500.147 1 1 2000 The same results are obtained when the compounds of the formula I are formulated as described in Examples F2 and F4 to F8 in accordance with WO 97/34485.

Example B2: Post-emeraence herbicidal action Monocotyledonous and dicotyledonous test plants are grown in the greenhouse in plastic pots containing standard soil and, in the 4-to 6-leaf stage, sprayed with an aqueous suspension of the test substances of the formula 1, prepared from a 25% strength wettable powder (Example F3, b) in accordance with WO 97/34485) or with an mulsion of the test substances of the formula 1, prepared from a 25% strength emuision concentrate (Example F1, c) in accordance with WO 97/34485), corresponding to a dosage of 2 kg/a. i./ha (500 1 of water/ha). The test plants are subsequently grown on in the greenhouse under optimal conditions. After a test period of approximately 18 days, the experiment is evaluated using a nine-level key (1 = complete damage, 9 = no effect). Score figures of 1 to 4 (in particular 1 to 3) signify a good to very good herbicidal action. tn this experiment, the compounds of the formula I exhibit a potent herbicidal activity.

Test plants: Lolium, Setaria, Sinapis, Solanum, Stellaria, ipomea.

In this experiment, again, the compounds of the formula I exhibit a potent herbicidal activity.

Examples of the good herbicidal activity of the compounds of the formula i are given in Table B2.

Table B2: Post-emeraence action: Test plant: Lolium Setaria Sinapis Solanum Stellaria Ipomoea Dose [g a. i./ha] Active ingredient No.

1.002 6 5 2 1 5 1 2000 1.016 1 1 1 1 1 1 2000 1.017 1 1 1 1 1 1 2000 1.020 1 1 1 1 1 1 2000 1.022 1 1 1 1 1 1 2000 1.025 1 3 1 1 1 1 2000 1.026 3 3 1 1 3 1 2000 1.047 3 1 1 1 4 1 2000 1.048 1 1 1 1 1 1 2000 1.363 1 1 1 1 1 1 2000 1.365 1 1 1 1 1 1 2000 1.366 1 1 1 1 1 1 2000 1.367 1 1 1 1 1 1 2000 1.396 3 3 1 1 3 1 2000 1.402 1 1 1 1 1 1 2000 500.004 2 1 3 2000 500.009 1 1 1 1 1 1 2000 500.029 1 1 1 2000 500. 033 1 1 1 2000 500.147 1 1 1 2000 500.149 1 1 1 2000 The same results are obtained when the compounds of the formula I are formulated as described in Examples F2 and F4 to F8 in accordance with WO 97/34485.

The active ingredients of the formula I of the invention may also be used for weed control as a mixture with known herbicides as co-herbicides, for example as ready-mixes or as a 'tank-mix'. Examples of co-herbicides which are suitable as components in mixtures with the active ingredients of the formula I are the following: Compound of the formula I + acetochlor; compound of the formula I + acifluorfen; compound of the formula I + aclonifen; compound of the formula I + alachlor; compound of the formula I + ametryn; compound of the formula I + aminotriazole; compound of the formula I + amidosulfuron; compound of the formula I + asulam; compound of the formula I + atrazine; compound of the formula I + BAY FOE 5043; compound of the formula I + benazolin; compound of the formula I + bensulfuron; compound of the formula I + bentazone; compound of the formula I + bifenox; compound of the formula I + bispyribac- sodium; compound of the formula I + bialaphos; compound of the formula I + bromacil; compound of the formula I + bromoxynil; compound of the formula I + bromophenoxim; compound of the formula I + butachlor; compound of the formula I + butylate; compound of the formula I + cafenstrole; compound of the formula I + carbetamide; compound of the formula I + chloridazone; compound of the formula I + chlorimuron-ethyl; compound of the formula I + chlorbromuron; compound of the formula I + chlorsulfuron; compound of the formula I + chlortoluron; compound of the formula I + cinosulfuron; compound of the formula I + clethodim; compound of the formula I + clodinafop; compound of the formula I + clomazone; compound of the formula I + clopyralid; compound of the formula I + cloransulam; compound of the formula I + cyanazine; compound of the formula I + cyhalofop; compound of the formula I + dalapon; compound of the formula I + 2,4-D; compound of the formula I + 2,4-DB; compound of the formula I + desmetryn; compound of the formula I + desmedipham; compound of the formula I + dicamba; compound of the formula I + diclofop; compound of the formula I + difenzoquat metilsulfate; compound of the formula I + diflufenican; compound of the formula I + dimefuron; compound of the formula I + dimepiperate; compound of the formula I + dimethachlor; compound of the formula I + dimethametryn; compound of the formula I + dimethenamid; compound of the formula I + S- dimethenamid; compound of the formula I + dinitramine; compound of the formula I + dinoterb; compound of the formula I + dipropetryn; compound of the formula I + diuron; compound of the formula I + diquat; compound of the formula I + DSMA; compound of the formula I + EPTC; compound of the formula I + esprocarb; compound of the formula I + ethalfluratin; compound of the formula I + ethametsulfuron; compound of the formula I + ethephon; compound of the formula I + ethofumesate; compound of the formula I + ethoxysulfuron; compound of the formula I + fenclorim; compound of the formula I + flamprop; compound of the formula I + fluazasulfuron; compound of the formula I + fluazifop; compound of the formula I + flumetralin; compound of the formula I + flumetsulam; compound of the formula I + fluometuron; compound of the formula I + flurchloridone; compound of the formula I + fluoxaprop; compound of the formula I + fluroxypyr; compound of the formula I + fluthiacet-methyl; compound of the formula I + fluxofenim; compound of the formula I + fomesafen; compound of the formula I + glufosinate; compound of the formula I + glyphosate; compound of the formula I + halosulfuron; compound of the formula I + haloxyfop; compound of the formula I + hexazinone; compound of the formula I + imazamethabenz; compound of the formula I + imazapyr; compound of the formula I + imazaquin; compound of the formula I + imazethapyr; compound of the formula I + imazosulfuron; compound of the formula I + ioxynil; compound of the formula I + isoproturon; compound of the formula I + isoxaben; compound of the formula I + isoxaflutole; compound of the formula I + Karbutylate; compound of the formula I + lactofen; compound of the formula I + lenacil; compound of the formula I + linuron; compound of the formula I + MCPP; compound of the formula I + metamitron; compound of the formula I + metazachlor; compound of the formula I + methabenzthiazuron; compound of the formula I + methazole; compound of the formula I + metobromuron; compound of the formula I + metolachlor; compound of the formula I + S- metolachlor; compound of the formula I + metosulam; compound of the formula I + metribuzin; compound of the formula I + metsulfuron-methyl; compound of the formula I + molinate; compound of the formula I + MCPA; compound of the formula I + MSMA; compound of the formula I + napropamide; compound of the formula I + NDA-402989; compound of the formula I + nefenacet; compound of the formula I + nicosulfuron; compound of the formula I + norflurazon; compound of the formula I + oryzalin; compound of the formula I + oxadiazon; compound of the formula I + oxasulfuron; compound of the formula I + oxyfluorfen; compound of the formula I + paraquat; compound of the formula I + pendimethalin; compound of the formula I + phenmedipham; compound of the formula I + fenoxaprop-P-ethyl (R); compound of the formula I + picloram; compound of the formula I + pretilachlor; compound of the formula I + primisulfuron; compound of the formula I + prometon; compound of the formula I + prometryn; compound of the formula I + propachlor; compound of the formula I + propanil; compound of the formula I + propazine; compound of the formula I + propaquizafop; compound of the formula I + propyzamide; compound of the formula I + prosulfuron; compound of the formula I + pyrazolynate; compound of the formula I + pyrazosulfuron-ethyl; compound of the formula I + pyrazoxyphen; compound of the formula I + pyridate; compound of the formula I + pyriminobac-methyl; compound of the formula I + pyrithiobac-sodium; compound of the formula I + quinclorac; compound of the formula I + quizalofop; compound of the formula I + rimsulfuron; compound of the formula I + Sequestren; compound of the formula I + sethoxydim; compound of the formula I + simetryn; compound of the formula I + simazine; compound of the formula I + sulcotrione; compound of the formula I + sulfosate; compound of the formula I + sulfosulfuron-methyl; compound of the formula I + tebutam; compound of the formula I + tebuthiuron; compound of the formula I + terbacil; compound of the formula I + terbumeton; compound of the formula I + terbuthylazine; compound of the formula I + terbutryn; compound of the formula I + thiazafluron; compound of the formula I + thiazopyr; compound of the formula I + thifensulfuron-methyl; compound of the formula I + thiobencarb; compound of the formula I + tralkoxydim; compound of the formula I + tri-allate; compound of the formula I + triasulfuron; compound of the formula I + trifluralin; compound of the formula I + tribenuron- methyl; compound of the formula I + triclopyr; compound of the formula I + triflusulfuron; compound of the formula I + trinexapac-ethyl, and esters and salts of these components with which the compound of the formula I can be mixed, for example those mentioned in The Pesticide Manual, Eleventh Edition, 1997, BCPC.