Novel herbicides

Abstract

Compounds of formula I 1

Description

[0001] The present invention relates to novel herbicidally active benzoyl derivatives, to processes for their preparation, to compositions comprising said compounds, and to the use thereof for controlling weeds, in particular in crops of cultivated plants or for inhibiting plant growth.

[0002] Benzoyl derivatives with herbicidal activity are described for example in U.S. Pat. No. 5,094,685. Now, novel benzoyl derivatives with herbicidal and growth-inhibiting properties have been found.

[0003] The objects of the present invention are thus compounds of formula I 2

[0004] wherein

[0005] X is L1-Y1-R4, L2-Y2-L3-Y3-R5 or L4-Y4-L5-Y5-L6-Y6-R6;

[0006] L1,L2, L3, L4, L5-, L6, independently of one another, signify C1-C6-alkylene, which may be substituted by C1-C4-alkyl, halogen, C1-C4-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl; or C3-C6-alkenylene, which may be substituted by CG-C4-alkyl, halogen, C1-C4-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl; or C3-C6-alkynylene, which may be substituted by C1-C4-alkyl, halogen, C1-C4-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl;

[0007] Y1, Y3, Y6, independently of one another, signify oxygen, sulphur, SO, SO2, NR7, OC(O), NR8SO2 or OSO2;

[0008] Y2, Y4, Y5, independently of one another, signify oxygen, sulphur, SO, SO2, NR9, OC(O) or NR10SO2;

[0009] R7, R8, R9 and R10, independently of one another, signify hydrogen or C1-C6-alkyl;

[0010] R1 and R2, independently of one another, signify halogen, cyano, nitro, amino, C1-C6-alkyl,

[0011] C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-dialkylaminosulphonyl, C1-C6-alkylaminosulphonyl, C1-C4-alkylsulphonylamino, C1-C6-halogenalkoxy, OSO2-C1-C4-alkyl, C1-C6-halogenalkylthio, C1-C6-halogenalkylsulphinyl, C1-C6-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl;

[0012] R3 signifies hydrogen, C1-C4-alkyl or halogen;

[0013] R4, R5 and R6, independently of one another, signify hydrogen, C1-C6-alkyl, which may be substituted by the group A1; C3-C7-cycloalkyl, which may be substituted by the group A2; C3-C7-cycloalkyl, which may be interrupted by 1 to 2 oxygen atoms, sulphur or NR11; C2-C6-alkenyl, which may be substituted by the group A3; C3-C6-alkynyl, which may be substituted by the group A4; C3-C7-cycloalkyl-C1-C4-alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NR12; benzyl or phenyl which may in turn be substituted by halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, cyano, nitro, C1-C4-halogenalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-dialkylamino, C1-C4-alkylcarbonyl, C1-C4-dialkylaminosulphonyl or NR13-CO-R14;

[0014] R11, and R12, independently of one another, signify hydrogen or C1-C4-alkyl;

[0015] R13 and R14, independently of one another, signify hydrogen or C1-C4-Alkyl;

[0016] A1, A2, A3, A4, independently of one another, are hydroxy, formyl, COOH, C1-C6-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, OSO2-C1-C4-alkyl, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, nitro, halogen, cyano, C1-C4-alkoxyhalogen, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or phenyl, whereby the phenyl group may in turn be substituted by halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, cyano, nitro, C1-C4-halogenalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylcarbonyl, C1-C4-dialkylaminosulphonyl or NR15-CO-R16; R15 and R16, independently of one another, signify hydrogen or C1-C4-alkyl;

[0017] Q is the group Q1 3

[0018] wherein R39 signifies hydroxy, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-alkoxy-carbonyloxy, C1-C6-dialkylamino, COOH, C1-C6-alkenylthio, C1-C6-alkenylsulphinyl, C1-C6-alkenylsulphonyl, OSO2-C1-C6-alkyl, benzoyloxy or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano; V is C1-C4-alkylene, oxygen, sulphur, SO or SO2;

[0019] R17, R18, R19, R20, R21 and R22, independently of one another, signify hydrogen, C1-C6-alkyl, C1-C6-alkoxycarbonyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkylaminosulphonyl, C1-C4-halogenalkyl, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C6-alkoxy, cyano, nitro, halogen or phenyl,

[0020] q is 1 or 2;

[0021] or Q is the group Q24

[0022] wherein

[0023] R23 signifies hydroxy, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-alkoxy-carbonyloxy, C1-C6-dialkylamino, COOH, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxycarbonyl-C1-C4-alkylthio, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphinyl, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphonyl, C1-C6-alkenylthio, C1-C6-alkenylsulphinyl, C1-C6-alkenylsulphonyl, OSO2-C1-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano; R24 and R25, independently of one another, signify hydrogen, hydroxy, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkylaminosulphonyl, C1-C4-halogenalkyl, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C6-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, amino, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkyl-S(O)2O, C1-C4-halogenalkylthio, C1-C4-halogenalkylsulphinyl, C1-C4-halogenalkylsulphonyl, C1-C4-halogenalkyl-S(O)2O, C1-C4-alkyl-S(O)2NH, C1-C4-alkyl-S(O)2N(C1-C4-alkyl), halogen, nitro, COOH or cyano; or R24 and R25 together form a C2-C6-alkylene bridge,

[0024] R26 signifies hydrogen, C1-C4-alkyl, C1-C4-alkoxycarbonyl or phenyl, which may in turn be substituted by C1-C6-alkyl, C1-C6-halogenalkyl, C1-C6-alkoxy, C1-C6-halogenalkoxy, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, amino, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkyl-S(O)2O, C1-C4-halogen-alkylthio, C1-C4-halogenalkylsulphinyl, C1-C4-halogenalkylsulphonyl, C1-C4-halogenalkyl-S(O)2O, C1-C4-alkyl-S(O)2NH, C1-C4-alkyl-S(O)2N(C1-C4-alkyl), halogen, nitro, COOH or cyano;

[0025] or Q is the group Q35

[0026] wherein

[0027] R27 signifies hydroxy, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-alkoxy-carbonyloxy, C1-C6-dialkylamino, COOH, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxycarbonyl-C1-C4-alkylthio, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphinyl, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphonyl, C1-C1-alkenylthio, C1-C6-alkenylsulphinyl, C1-C6-alkenylsulphonyl, OSO2-C1-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano;

[0028] R28, R29 and R40, independently of one another, signify hydrogen, hydroxy, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkylaminosulphonyl, C1-C4-halogenalkyl, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C6-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, amino, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkyl-S(O)2O, C1-C4-halogenalkylthio, C1-C4-halogenalkylsulphinyl, C1-C4-halogenalkylsulphonyl, C1-C4-halogenalkyl-S(O)2O, C1-C4-alkyl-S(O)2NH, C1-C4-alkyl-S(O)2N(C1-C4-alkyl), halogen, nitro, COOH or cyano; or R28 and R29 together form a C2-C6-alkylene bridge,

[0029] R30 signifies C1-C6-alkyl, which may be substituted by a group A5; C2-C6-alkenyl, which may be substituted by a group A6; C2-C6-alkynyl, which may be substituted by a group A7; A5, A6 and A7, independently of one another, are hydroxy, formyl, COOH, C1-C6-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, OSO2-C1-C4-alkyl, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C6-alkylaminocarbonyl, C1-C6-dialkylaminocarbonyl, nitro, halogen, cyano, C1-C4-alkoxyhalogen, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or phenyl, whereby the phenyl is in turn substituted by halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, cyano, nitro, C1-C4-halogenalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkylcarbonyl, C1-C4-dialkylaminosulphonyl or NR31-CO-R32;

[0030] R31, R32, independently of one another, signify hydrogen or C1-C4-alkyl;

[0031] or Q is the group Q46

[0032] wherein

[0033] R33 signifies hydroxy, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-alkoxy-carbonyloxy, C1-C6-dialkylamino, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxycarbonyl-C1-C4-alkylthio, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphinyl, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphonyl, C1-C6-alkenylthio, C1-C6-alkenylsulphinyl, C1-C6-alkenylsulphonyl, OSO2-C1-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano;

[0034] W is oxygen, sulphur, SO, SO2, NR38 or C═O;

[0035] R38 signifies hydrogen or C1-C6-alkyl;

[0036] R34, R35, R36 and R37, independently of one another, signify hydrogen, hydroxy, C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkylaminosulphonyl, C1-C4-halogenalkyl, C1-C6-alkylamino, C1-C6-dialkylamino, C1-C6-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, amino, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkyl-S(O)2O, C1-C4-halogenalkylthio, C1-C4-halogenalkylsulphinyl, C1-C4-halogenalkylsulphonyl, C1-C4-halogenalkyl-S(O)2O, C1-C4-alkyl-S(O)2NH, C1-C4-alkyl-S(O)2N(C1-C4-alkyl), halogen, nitro, COOH or cyano; or R34 and R35 together form a C2-C6-alkylene bridge, as well as agronomically acceptable salts, isomers and enantiomers of these compounds.

[0037] The invention similarly relates to the salts that may be formed by the compounds of formula 1, especially those compounds of formula I in which R23, R27, R33 and R39 are hydroxy, with amines, alkali metal bases and alkaline earth metal bases, or quaternary ammonium bases.

[0038] Of the alkali metal hydroxides and alkaline earth metal hydroxides as salt-forming components, the hydroxides of lithium, sodium, potassium, magnesium or calcium are notable, especially those of sodium or potassium.

[0039] Examples of amines that are suitable for ammonium salt formation may be both ammonia and primary, secondary and tertiary C1-C18-alkylamines, C1-C4-hydroxyalkylamines and C2-C4-alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso-propylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, 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-butyl-ethanolamine, 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 pyridine, quinoline, iso-quinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines; but especially triethylamine, iso-propylamine and di-iso-propylamine.

[0040] The alkyl and alkylene groups present in the definitions of the substituents may be straight-chained or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec.-butyl, iso-butyl, tert.-butyl, pentyl and hexyl, as well as the branched isomers thereof. Alkoxy, alkenyl, alkenylene, alkynyl and alkynylene groups are derived from the said alkyl groups. The alkenyl, alkenylene, alkynyl and alkynylene groups may be mono- or multi-unsaturated.

[0041] Halogen normally signifies fluorine, chlorine, bromine or iodine. The same applies also to halogen in conjunction with other definitions such as halogenalkyl or halogenphenyl.

[0042] Halogenalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkyl is for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

[0043] Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is for example methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, iso-butoxy, sec.-butoxy and tert.-butoxy as well as the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl signifies for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec.-butoxycarbonyl or tert.-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Halogenalkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkoxy is e.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groups preferably have a chain length of 1 to 6 carbon atoms. Alkylthio is for example methylthio, ethylthio, propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec.-butylthio or tert.-butylthio, preferably methylthio and ethylthio. Alkylsulphinyl is for example methylsulphinyl, ethylsulphinyl, propylsulphinyl, iso-propylsulphinyl, n-butylsulphinyl, iso-butylsulphinyl, sec.-butylsulphinyl, tert.-butylsulphinyl; preferably methylsulphinyl and ethylsulphinyl.

[0044] C3-C7-cycloalkyl, which is interrupted by oxygen, is for example oxiranyl, oxetanyl, tetrahydrofuranyl, dioxolanyl, oxacyclohexyl, dioxacyclohexyl, oxacycloheptyl or dioxacycloheptyl.

[0045] C3-C7-cycloalkyl-C1-C3-alkyl, which may be interrupted by oxygen, is for example oxiranyl-methyl, oxetanyl-ethyl, tetrahydrofuranyl-n-propyl, dioxolanyl-C1-C3-alkyl, oxacyclohexyl-C1-C3-alkyl, dioxacyclohexyl-C1-C3-alkyl, oxacycloheptyl-C1-C3-alkyl or Dioxacycloheptyl-C1-C3-alkyl.

[0046] Alkylsulphonyl is for example methylsulphonyl, ethylsulphonyl, propylsulphonyl, iso-propylsulphonyl, n-butylsulphonyl, iso-butylsulphonyl, sec.-butylsulphonyl or tert.-butylsulphonyl; preferably methylsulphonyl or ethylsulphonyl Alkoxyalkoxy groups preferably have a chain length of 2 to 4 carbon atoms.

[0047] Examples of alkoxyalkoxy are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy.

[0048] Alkylamino is for example methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is for example dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino. Preference is given to alkylamino groups with a chain length of 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have 2 to 4 carbon atoms. Alkoxyalkyl signifies for example methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkyl groups preferably have 2 to 4 carbon atoms. Alkylthioalkyl signifies for example methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl. The cycloalkyl groups preferably have 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Phenyl, even as part of a substituent, such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl or phenoxyalkyl, may be present in substituted form.

[0049] Preference is given to compounds of formula I, in which R1 and R2, independently of one another, signify halogen, cyano, nitro, amino, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-dialkylaminosulphonyl, C1-C6-alkylaminosulphonyl, C1-C6-halogenalkoxy, OSO2-C1-C4-alkyl, C1-C6-halogenalkylthio, C1-C6-halogen-alkylsulphinyl, C1-C6-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl and

[0050] R33 signifies hydroxy, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-alkoxy-carbonyloxy, C1-C6-dialkylamino, COOH, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxycarbonyl-C1-C4-alkylthio, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphinyl, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphonyl, C1-C6-alkenylthio, C1-C6-alkenylsulphinyl, C1-C6-alkenylsulphonyl, OSO2-C1-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano.

[0051] Further preferred compounds of formula I are characterised in that Q is Q1 or Q2, whereby in the group Q2, R24, R25 and R26 are preferably hydrogen or C1-C6-alkyl. R23 and R39 denote hydroxy in particular. Also notable are those compounds of formula I, in which X is L1-Y1-R4. Of this group, the compounds in which L1 signifies methylene are preferred. In a further preferred group of compounds of formula I, R2 signifies C1-C6-alkylsulphonyl. Also of interest are compounds of formula I, in which R1 signifies methyl.

[0052] Particularly preferred individual compounds falling within the scope of formula I are: 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-bicyclo[3.2.1]oct-3-en-2-one and 5-hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-2,6,6-trimethyl-6.H.-[1,2]oxazin-3-one.

[0053] The compounds of formula I may be produced by known processes which are described, for example, in U.S. Pat. No. 5,565,410, U.S. Pat. No. 5,608,101 and EP-A-0 282 944, whereby e.g. a compound of formula II 7

[0054] wherein R1, R2, R3 and X have the significances given under formula I and Z signifies a leaving group, preferably halogen, especially chlorine or cyano, is reacted with a compound of formula III 8

[0055] (III), wherein the substituents are defined as in group Q1,

[0056] or with a compound of formula IV 9

[0057] wherein the substituents are defined as in group Q2, or with a compound of formula V 10

[0058] wherein the substituents are defined as in group Q3, or with a compound of formula VI 11

[0059] wherein the substituents are defined as in group Q4 and correspondingly R39, R23, R27 and R33 signify hydroxy, optionally in the presence of a base. The compounds of formulae II, III, IV or V are known from U.S. Pat. No. 5,565,410, U.S. Pat. No. 5,608,101 and EP-A-0 282 944 or may be produced analogously to the processes disclosed therein.

[0060] The reactions for obtaining the compounds of 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, nitrites such as acetonitrile or propionitrile, amides such as N,N-dimethyl formamide, diethyl formamide or N-methylpyrrolidinone. The reaction temperatures are preferably in the range from −200 to +120° C. The reactions are usually slightly exothermic and can as a rule be carried out at room temperature. The reaction mixture can be heated for a brief time to boiling point to shorten the reaction time or also to initiate the reaction. The reaction times can also be shortened by addition of a few drops of a base as reaction catalyst. Particularly suitable bases are tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene. Further suitable bases are also inorganic bases, typically hydrides such as sodium or calcium hydride, hydroxides such as sodium or potassium hydroxide, carbonates such as sodium and potassium carbonate, or hydrogen carbonates such as potassium and sodium hydrogen carbonate.

[0061] The compounds of formula I can be isolated in conventional manner by concentrating the reaction mixture and/or removing the solvent by evaporation and by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, typically ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

[0062] The compounds of formula I or compositions containing them may be used according to this invention by all standard methods of application used in agriculture, including preemergence application, postemergence application and seed dressing, as well as by different methods and techniques such as controlled release. For controlled release, a solution of the herbicide is applied to a mineral granular carrier or to a polymerised granulate (urea/formaldehyde) and then dried. A coating can then be additionally applied (coated granules) that allows the active ingredient to be released at a controlled rate over a specific period of time.

[0063] The compounds of formula I may be used as herbicides in unmodified form, i.e. as obtained in the synthesis. Preferably they are processed in conventional manner with the auxiliary agents customarily employed in formulation technology to emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. As with the type of agents, the methods of application such as spraying, atomising, dusting, wetting, scattering or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.

[0064] The formulations, i.e. the agents, preparations, or compositions containing the compound of formula I or at least one compound of formula I and usually one or more than one liquid or solid formulation assistant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the herbicide with said formulation auxiliaries, typically solvents or solid carriers. Surface-active compounds (surfactants) may additionally be used for preparing the formulations. Examples of solvents and solid carriers are described in WO 97/34485 on page 6.

[0065] Depending on the herbicide of formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.

[0066] Examples of suitable anionic, nonionic, and cationic surfactants are listed for example in WO 97/34485 on pages 7 and 8.

[0067] Also the surfactants customary in the art of formulation and described, inter alia, in “McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch” (Handbook of Surfactants), Carl Hanser Verlag, Munich/Vienna, 1981, and M. and J. Ash, “Encyclopedia of Surfactants”, Vol I-Ill, Chemical Publishing Co., New York, 1980-81, are suitable for manufacture of the herbicides according to the invention.

[0068] The herbicidal compositions will as a rule contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of herbicide, from 1 to 99.9% by weight, preferably from 5 to 99.8% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant. Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations. The compositions may also contain further ingredients, such as: stabilisers, e.g. where appropriate epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil, or soybean oil); anti-foaming agents, typically silicone oil; preservatives; viscosity regulators; binders; and tackifiers; as well as fertilisers or other chemical agents.

[0069] The compounds of formula I are usually applied with success to the plants or the locus thereof in concentrations of 0.001 to 4 kg/ha, preferably 0.005 to 2 kg/ha. The concentration required to achieve the desired action can be determined by experimentation. It will depend on the type of action, the development stage of the cultivated plant and of the weed, as well as on the application (locus, time, method), and as a resulty of these variables can vary over a wide range.

[0070] The compounds of formula I have excellent herbicidal and growth inhibiting properties, which make them suitable for application in crops of cultivated plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantations, rape, maize, and rice, and for the nonselective control of weeds. Crops will also be understood to mean those crops that have been made tolerant to herbicides or classes of herbicides by conventional breeding or genetic engineering methods. The weeds to be controlled may be monocot as well as dicot weeds, typically 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.

[0071] The invention is illustrated by the following non-limitative Examples.

PREPARATION EXAMPLES

Example P1

Preparation of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic Acid Chloride

[0072] 12

[0073] A solution of 1.5 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid in 15 ml of methylene chloride produced in accordance with EP-A-0 282 944 is mixed at a temperature of 20° C. with 2 drops of DMF. Then, whilst cooling lightly, a solution of 1.0 ml (11.6 mmols) of oxalyl chloride in 2 ml of methylene chloride is added dropwise. The reaction mixture is stirred until the evolution of gas has ended. Subsequently, the solvent is distilled off. The 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride is used without further purification directly for the next step of the process.

Example P2

Preparation of 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-bicyclo[3.2.1]oct-3-en-2-one

[0074] 13

[0075] 0.8 g (5.8 mmols) of bicyclo[3.2.1]octan-2,4-dione (the preparation thereof is described for example in U.S. Pat. No. 5,608,101 and in the references cited therein) are dissolved in 15 ml of methylene chloride at 20° C. The solution is mixed with 0.97 ml of triethylamine and cooled to a temperature of 0° C. Then, a solution of 1.6 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride in 10 ml of methylene chloride is added dropwise. The reaction mixture is stirred for half an hour at a temperature of 0° C. and is subsequently diluted with methylene chloride. After washing and drying, the organic phase is concentrated by evaporation. 2.23 g of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl-ester is obtained in amorphous form. This can be used for the next step without purification.

[0076] 2.23 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl-ester and 1.6 ml (11.6 mmols) of triethylamine are dissolved in 20 ml of acetonitrile. 0.2 ml of acetocyanohydrin are added at a temperature of 20° C. After stirring for 20 hours, the mixture is worked up and the crude product is purified by thick-layer chromatography. 1.0 g of 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-bicyclo[3.2.1]oct-3-en-2-one is obtained in amorphous form.

Example P3

Preparation of 5-hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-2,6,6-trimethyl-6.H.-[1,2]oxazin-3-one

[0077] 14

[0078] 0.79 g (5.04 mmols) of 2,6,6-trimethyl-2H-1,2-oxazin-3,5-dione (the preparation thereof is described for example in U.S. Pat. No. 5,565,410), 15 ml of methylene chloride and 0.97 ml of triethylamine are prepared, and at a temperature of 0° C., a solution of 1.3 g (4.7 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride in 10 ml methylene chloride is added dropwise. After stirring for 30 minutes, the solution is diluted with methylene chloride. The reaction solution is subsequently acidified with diluted hydrochloric acid, the organic phase separated, dried and concentrated. 2.0 g of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-2,6,6-trimethyl-5-oxo-5,6-dihydro-2.H.-[1,2]oxazin-3-yl-ester are obtained in amorphous form. The product may be further used directly without purification.

[0079] 2.0 g (5.04 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-2,6,6-trimethyl-5-oxo-5,6-dihydro-2.H.-[1,2]oxazin-3-yl-ester are dissolved in a mixture of 35 ml of acetonitrile and 10 ml of methylene chloride, then 1.4 ml (10.08 mmols) of triethylamine and 0.18 ml of acetocyanohydrin are added. After stirring for 20 hours at a temperature of 20° C. and then working up, recrystallisation is effected, and finally hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-2,6,6-trimethyl-6.H.-[1,2]oxazin-3-one is obtained with a melting point of 157° C.

[0080] The substances named in the following Tables 1 to 4 may also be prepared analogously to the methods described above. In Tables 1 to 4, X denotes the following groups:

[0081] X1=CH2OCH3, X2=CH2OC2H5, X3=CH2OH, X4=CH2CH2OCH3, X5=CH2CH2OC2H5, X6=CH2CH2OCH2CH2OCH3, X7=CH2CH2OCH2CH2OC2H5, X8=CH(CH3)OC2H5, X10=CH2OCH2CH═CH2, X11=CH2OCH2CH2CH3, X12=CH(C2H5)OC2H5, X13=C(CH3)2OH, X14=CH2CH2OCH(CH3)2, X15=CH2SO2CH3, X16=CH2N(CH3)C2H5, X17=CH2NHCH3, X18=CH2OCH(CH3)2, X19=C(CH3)2OCH3, X20=CH2CH2OH, X21=CH2OCH2CCH, X22=C(CH3)2OC2H5, X23=CH(C2H5)OCH3, X24=CH(CH3)OH, X25=CH(OH)C2H5, X26=CH2SCH3, X27=CH2N(CH3)2, X28=CH2CH2N(CH3)2, X29=CH2OCOCH3, X30=CH2OPh, X31=CH2CH2OPh, X32=CH2OCH2CH2OCH3, X33=CH2OCH2CH2OC2H5, 15

TABLE 1
Compounds of formula (Ia):
	(Ia)
Comp.							Phys.
No.	V	R17	R22	R1	X	R2	data
1,001	CH2	H	H	CH3	X1	SO2CH3	resin
1,002	CH2	H	H	CH3	X2	SO2CH3	—
1,003	CH2	H	H	CH3	X3	SO2CH3	—
1,004	CH2	H	H	CH3	X4	SO2CH3	—
1,005	CH2	H	H	CH3	X5	SO2CH3	—
1,006	CH2	H	H	CH3	X6	SO2CH3	—
1,007	CH2	H	H	CH3	X7	SO2CH3	—
1,008	CH2	H	H	CH3	X8	SO2CH3	—
1,009	CH2	H	H	CH3	X9	SO2CH3	—
1,010	CH2	H	H	CH3	X10	SO2CH3	—
1,011	CH2	H	H	CH3	X11	SO2CH3	—
1,012	CH2	H	H	CH3	X12	SO2CH3	—
1,013	CH2	H	H	CH3	X13	SO2CH3	—
1,014	CH2	H	H	CH3	X14	SO2CH3	—
1,015	CH2	H	H	CH3	X15	SO2CH3	—
1,016	CH2	H	H	CH3	X16	SO2CH3	—
1,017	CH2	H	H	CH3	X17	SO2CH3	—
1,018	CH2	H	H	CH3	X18	SO2CH3	—
1,019	CH2	H	H	CH3	X19	SO2CH3	—
1,020	CH2	H	H	CH3	X20	SO2CH3	—
1,021	CH2	H	H	CH3	X21	SO2CH3	—
1,022	CH2	H	H	CH3	X22	SO2CH3	—
1,023	CH2	H	H	CH3	X23	SO2CH3	—
1,024	CH2	H	H	CH3	X24	SO2CH3	—
1,025	CH2	H	H	CH3	X25	SO2CH3	—
1,026	CH2	H	H	CH3	X26	SO2CH3	—
1,027	CH2	H	H	CH3	X27	SO2CH3	—
1,028	CH2	H	H	CH3	X28	SO2CH3	—
1,029	CH2	H	H	CH3	X29	SO2CH3	—
1,030	CH2	H	H	CH3	X30	SO2CH3	—
1,031	CH2	H	H	CH3	X31	SO2CH3	—
1,032	CH2	H	H	CH3	X32	SO2CH3	—
1,033	CH2	H	H	CH3	X33	SO2CH3	—
1,034	CH2	H	H	CH3	X34	SO2CH3	—
1,035	CH2	H	H	CH3	X35	SO2CH3	—
1,036	CH2	H	H	CH3	X36	SO2CH3	—
1,037	CH2	H	H	CH3	X37	SO2CH3	—
1,038	CH2	H	H	CH3	X38	SO2CH3	—
1,039	CH2	H	H	CH3	X39	SO2CH3	—
1,040	CH2	H	H	CH3	X40	SO2CH3	—
1,041	CH2	H	H	CH3	X41	SO2CH3	—
1,042	CH2	H	H	CH3	X42	SO2CH3	—
1,043	CH2	H	H	CH3	X1	SCH2	—
1,044	CH2	H	H	CH3	X2	SCH2	—
1,045	CH2	H	H	CH3	X3	SCH2	—
1,046	CH2	H	H	CH3	X4	SCH2	—
1,047	CH2	H	H	CH3	X5	SCH2	—
1,048	CH2	H	H	CH3	X6	SCH2	—
1,049	CH2	H	H	CH3	X7	SCH2	—
1,050	CH2	H	H	CH3	X10	SCH2	—
1,051	CH2	H	H	CH3	X15	SCH2	—
1,052	CH2	H	H	CH3	X20	SCH2	—
1,053	CH2	H	H	CH3	X21	SCH2	—
1,054	CH2	H	H	CH3	X26	SCH2	—
1,055	CH2	H	H	CH3	X27	SCH2	—
1,056	CH2	H	H	CH3	X29	SCH2	—
1,057	CH2	H	H	CH3	X30	SCH3	—
1,058	CH3	CH3	CH3	CH3	X1	SO2CH3	—
1,059	CH3	CH3	CH3	CH3	X2	SO2CH3	—
1,060	CH3	CH3	CH3	CH3	X4	SO2CH3	—
1,061	CH3	CH3	CH3	CH3	X10	SO2CH3	—
1,062	CH3	CH3	CH3	CH3	X15	SO2CH3	—
1,063	CH3	CH3	CH3	CH3	X21	SO2CH3	—
1,064	CH3	CH3	CH3	CH3	X26	SO2CH3	—
1,065	O	CH3	CH3	CH3	X1	SO2CH3	—
1,066	O	CH3	CH3	CH3	X2	SO2CH3	—
1,067	O	CH3	CH3	CH3	X4	SO2CH3	—
1,068	O	CH3	CH3	CH3	X10	SO2CH3	—
1,069	O	CH3	CH3	CH3	X15	SO2CH3	—
1,070	O	CH3	CH3	CH3	X21	SO2CH3	—
1,071	O	CH3	CH3	CH3	X26	SO2CH3	—
1,072	CH2	H	H	Cl	X1	SO2CH3
1,073	CH2	H	H	Cl	X2	SO2CH3
1,074	CH2	H	H	Cl	X3	SO2CH3
1,075	CH2	H	H	Cl	X4	SO2CH3
1,076	CH2	H	H	Cl	X5	SO2CH3
1,077	CH2	H	H	Cl	X6	SO2CH3
1,078	CH2	H	H	Cl	X7	SO2CH3
1,079	CH2	H	H	Cl	X8	SO2CH3
1,080	CH2	H	H	Cl	X9	SO2CH3
1,081	CH2	H	H	Cl	X10	SO2CH3
1,082	CH2	H	H	Cl	X11	SO2CH3
1,083	CH2	H	H	Cl	X12	SO2CH3
1,084	CH2	H	H	Cl	X13	SO2CH3
1,085	CH2	H	H	Cl	X14	SO2CH3
1,086	CH2	H	H	Cl	X15	SO2CH3
1,087	CH2	H	H	Cl	X16	SO2CH3
1,088	CH2	H	H	Cl	X17	SO2CH3
1,089	CH2	H	H	Cl	X18	SO2CH3
1,090	CH2	H	H	Cl	X19	SO2CH3
1,091	CH2	H	H	Cl	X20	SO2CH3
1,092	CH2	H	H	Cl	X21	SO2CH3
1,093	CH2	H	H	Cl	X22	SO2CH3
1,094	CH2	H	H	Cl	X23	SO2CH3
1,095	CH2	H	H	Cl	X24	SO2CH3
1,096	CH2	H	H	Cl	X25	SO2CH3
1,097	CH2	H	H	Cl	X26	SO2CH3
1,098	CH2	H	H	Cl	X27	SO2CH3
1,099	CH2	H	H	Cl	X28	SO2CH3
1,100	CH2	H	H	Cl	X29	SO2CH3
1,101	CH2	H	H	Cl	X30	SO2CH3
1,102	CH2	H	H	Cl	X31	SO2CH3
1,103	CH2	H	H	Cl	X32	SO2CH3
1,104	CH2	H	H	Cl	X33	SO2CH3
1,105	CH2	H	H	Cl	X34	SO2CH3
1,106	CH2	H	H	Cl	X35	SO2CH3
1,107	CH2	H	H	Cl	X36	SO2CH3
1,108	CH2	H	H	Cl	X37	SO2CH3
1,109	CH2	H	H	Cl	X38	SO2CH3
1,110	CH2	H	H	Cl	X39	SO2CH3
1,111	CH2	H	H	Cl	X40	SO2CH3
1,112	CH2	H	H	Cl	X41	SO2CH3
1,113	CH2	H	H	Cl	X42	SO2CH3
1,114	CH2	H	H	CH3	X1	CF3
1,115	CH2	H	H	CH3	X2	CF3
1,116	CH2	H	H	CH3	X3	CF3
1,117	CH2	H	H	CH3	X4	CF3
1,118	CH2	H	H	CH3	X5	CF3
1,119	CH2	H	H	CH3	X6	CF3
1,120	CH2	H	H	CH3	X7	CF3
1,121	CH2	H	H	CH3	X10	CF3
1,122	CH2	H	H	CH3	X15	CF3
1,123	CH2	H	H	CH3	X21	CF3
1,124	CH2	H	H	CH3	X26	CF3
1,125	CH2	H	H	CH3	X27	CF3
1,126	CH2	H	H	CH3	X29	CF3
1,127	CH2	H	H	CH3	X30	CF3
1,128	CH2	H	H	CH3	X1	CF3
1,129	CH2	H	H	CH3	X2	Br
1,130	CH2	H	H	CH3	X3	Br
1,131	CH2	H	H	CH3	X4	Br
1,132	CH2	H	H	CH3	X5	Br
1,133	CH2	H	H	CH3	X6	Br
1,134	CH2	H	H	CH3	X7	Br
1,135	CH2	H	H	CH3	X10	Br
1,136	CH2	H	H	CH3	X15	Br
1,137	CH2	H	H	CH3	X20	Br
1,138	CH2	H	H	CH3	X21	Br
1,139	CH2	H	H	CH3	X26	Br
1,140	CH2	H	H	CH3	X27	Br
1,141	CH2	H	H	CH3	X29	Br
1,142	CH2	H	H	CH3	X30	Br
1,143	CH2	H	H	CH3	X1	Br
1,144	CH2	H	H	CH3	X2	CN
1,145	CH2	H	H	CH3	X3	CN
1,146	CH2	H	H	CH3	X4	CN
1,147	CH2	H	H	CH3	X6	CN
1,148	CH2	H	H	CH3	X6	CN
1,149	CH2	H	H	CH3	X10	CN
1,150	CH2	H	H	CH3	X15	CN
1,151	CH2	H	H	CH3	X21	CN
1,152	CH2	H	H	CH3	X26	CN
1,153	CH2	H	H	CH3	X30	CN
1,154	CH2	H	H	CF3	X1	SO2CH3
1,155	CH2	H	H	CF3	X2	SO2CH3
1,156	CH2	H	H	CF3	X3	SO2CH3
1,157	CH2	H	H	CF3	X4	SO2CH3
1,158	CH2	H	H	CF3	X6	SO2CH3
1,159	CH2	H	H	CF3	X10	SO2CH3
1,160	CH2	H	H	CF3	X15	SO2CH3
1,161	CH2	H	H	CF3	X21	SO2CH3
1,162	CH2	H	H	CF3	X26	SO2CH3
1,163	CH2	H	H	CF3	X30	SO2CH3
1,164	CH3	CH3	CH3	CF3	X1	SO2CH3
1,165	CH3	CH3	CH3	CF3	X2	SO2CH3
1,166	CH3	CH3	CH3	CF3	X4	SO2CH3
1,167	CH3	CH3	CH3	CF3	X10	SO2CH3
1,168	CH3	CH3	CH3	CF3	X15	SO2CH3
1,169	CH3	CH3	CH3	CF3	X21	SO2CH3
1,170	CH3	CH3	CH3	CF3	X26	SO2CH3
1,171	CH2	H	H	SO2CH3	X1	CF3
1,172	CH2	H	H	SO2CH3	X2	CF3
1,173	CH2	H	H	SO2CH3	X3	CF3
1,174	CH2	H	H	SO2CH3	X4	CF3
1,175	CH2	H	H	SO2CH3	X6	CF3
1,176	CH2	H	H	SO2CH3	X10	CF3
1,177	CH2	H	H	SO2CH3	X15	CF3
1,178	CH2	H	H	SO2CH3	X21	CF3
1,179	CH2	H	H	SO2CH3	X26	CF3
1,180	CH2	H	H	SO2CH3	X30	CF3
1,181	CH2	H	H	CH3	X1	Cl
1,182	CH2	H	H	CH3	X2	Cl
1,183	CH2	H	H	CH3	X3	Cl
1,184	CH2	H	H	CH3	X4	Cl
1,185	CH2	H	H	CH3	X6	Cl
1,186	CH2	H	H	CH3	X10	Cl
1,187	CH2	H	H	CH3	X15	Cl
1,188	CH2	H	H	CH3	X21	Cl
1,189	CH2	H	H	CH3	X26	Cl
1,190	CH2	H	H	CH3	X30	Cl
1,191	CH2	H	H	NO2	X1	SO2CH3
1,192	CH2	H	H	NO2	X2	SO2CH3
1,193	CH2	H	H	NO2	X4	SO2CH3
1,194	CH2	H	H	NO2	X10	SO2CH3
1,195	CH2	H	H	NO2	X15	SO2CH3
1,196	CH2	H	H	NO2	X21	SO2CH3
1,197	CH2	H	H	NO2	X26	SO2CH3

[0082]

TABLE 2
Compounds of formula (Ib):
	(Ib)
Comp.							m.p.
No.	R24	R25	R26	R1	X	R2	(° C.)
2,001	CH3	CH3	CH3	CH3	X1	SO2CH3	157° C.
2,002	CH3	CH3	CH3	CH3	X2	SO2CH3	—
2,003	CH3	CH3	CH3	CH3	X3	SO2CH3	—
2,004	CH3	CH3	CH3	CH3	X4	SO2CH3	—
2,005	CH3	CH3	CH3	CH3	X5	SO2CH3	—
2,006	CH3	CH3	CH3	CH3	X6	SO2CH3	—
2,007	CH3	CH3	CH3	CH3	X7	SO2CH3	—
2,008	CH3	CH3	CH3	CH3	X8	SO2CH3	—
2,009	CH3	CH3	CH3	CH3	X9	SO2CH3	—
2,010	CH3	CH3	CH3	CH3	X10	SO2CH3	—
2,011	CH3	CH3	CH3	CH3	X11	SO2CH3	—
2,012	CH3	CH3	CH3	CH3	X12	SO2CH3	—
2,013	CH3	CH3	CH3	CH3	X13	SO2CH3	—
2,014	CH3	CH3	CH3	CH3	X14	SO2CH3	—
2,015	CH3	CH3	CH3	CH3	X15	SO2CH3	—
2,016	CH3	CH3	CH3	CH3	X16	SO2CH3	—
2,017	CH3	CH3	CH3	CH3	X17	SO2CH3	—
2,018	CH3	CH3	CH3	CH3	X18	SO2CH3	—
2,019	CH3	CH3	CH3	CH3	X19	SO2CH3	—
2,020	CH3	CH3	CH3	CH3	X20	SO2CH3	—
2,021	CH3	CH3	CH3	CH3	X21	SO2CH3	—
2,022	CH3	CH3	CH3	CH3	X22	SO2CH3	—
2,023	CH3	CH3	CH3	CH3	X23	SO2CH3	—
2,024	CH3	CH3	CH3	CH3	X24	SO2CH3	—
2,025	CH3	CH3	CH3	CH3	X25	SO2CH3	—
2,026	CH3	CH3	CH3	CH3	X26	SO2CH3	—
2,027	CH3	CH3	CH3	CH3	X27	SO2CH3	—
2,028	CH3	CH3	CH3	CH3	X28	SO2CH3	—
2,029	CH3	CH3	CH3	CH3	X29	SO2CH3	—
2,030	CH3	CH3	CH3	CH3	X30	SO2CH3	—
2,031	CH3	CH3	CH3	CH3	X31	SO2CH3	—
2,032	CH3	CH3	CH3	CH3	X32	SO2CH3	—
2,033	CH3	CH3	CH3	CH3	X33	SO2CH3	—
2,034	CH3	CH3	CH3	CH3	X34	SO2CH3	—
2,035	CH3	CH3	CH3	CH3	X35	SO2CH3	—
2,036	CH3	CH3	CH3	CH3	X36	SO2CH3	—
2,037	CH3	CH3	CH3	CH3	X37	SO2CH3	—
2,038	CH3	CH3	CH3	CH3	X38	SO2CH3	—
2,039	CH3	CH3	CH3	CH3	X39	SO2CH3	—
2,040	CH3	CH3	CH3	CH3	X40	SO2CH3	—
2,041	CH3	CH3	CH3	CH3	X41	SO2CH3	—
2,042	CH3	CH3	CH3	CH3	X42	SO2CH3	—
2,043	CH3	CH3	CH3	Cl	X1	SO2CH3	—
2,044	CH3	CH3	CH3	Cl	X2	SO2CH3	—
2,045	CH3	CH3	CH3	Cl	X3	SO2CH3	—
2,046	CH3	CH3	CH3	Cl	X4	SO2CH3	—
2,047	CH3	CH3	CH3	Cl	X5	SO2CH3	—
2,048	CH3	CH3	CH3	Cl	X6	SO2CH3	—
2,049	CH3	CH3	CH3	Cl	X7	SO2CH3	—
2,050	CH3	CH3	CH3	Cl	X10	SO2CH3	—
2,051	CH3	CH3	CH3	Cl	X15	SO2CH3	—
2,052	CH3	CH3	CH3	Cl	X20	SO2CH3	—
2,053	CH3	CH3	CH3	Cl	X21	SO2CH3	—
2,054	CH3	CH3	CH3	Cl	X26	SO2CH3	—
2,055	CH3	CH3	CH3	Cl	X27	SO2CH3	—
2,056	CH3	CH3	CH3	Cl	X29	SO2CH3	—
2,057	CH3	CH3	CH3	Cl	X30	SO2CH3	—
2,058	CH3	CH3	CH3	CH3	X1	SCH3	—
2,059	CH3	CH3	CH3	CH3	X2	SCH3	—
2,060	CH3	CH3	CH3	CH3	X3	SCH3	—
2,061	CH3	CH3	CH3	CH3	X4	SCH3	—
2,062	CH3	CH3	CH3	CH3	X5	SCH3	—
2,063	CH3	CH3	CH3	CH3	X6	SCH3	—
2,064	CH3	CH3	CH3	CH3	X7	SCH3	—
2,065	CH3	CH3	CH3	CH3	X10	SCH3	—
2,066	CH3	CH3	CH3	CH3	X15	SCH3	—
2,067	CH3	CH3	CH3	CH3	X20	SCH3	—
2,068	CH3	CH3	CH3	CH3	X21	SCH3	—
2,069	CH3	CH3	CH3	CH3	X26	SCH3	—
2,070	CH3	CH3	CH3	CH3	X27	SCH3	—
2,071	CH3	CH3	CH3	CH3	X29	SCH3	—
2,072	CH3	CH3	CH3	CH3	X30	SCH3	—
2,073	H	H	C2H5	CH3	X1	SO2CH3	—
2,074	H	H	C2H5	CH3	X2	—
2,075	H	H	C2H5	CH3	X4	—
2,076	H	H	C2H5	CH3	X10	—
2,077	H	H	C2H5	CH3	X15	—
2,078	H	H	C2H5	CH3	X21	—
2,079	H	H	C2H5	CH3	X26	—
2,080	H	H	C3H7	CH3	X1	—
2,081	H	H	C3H7	CH3	X2	—
2,082	H	H	C3H7	CH3	X4	—
2,083	H	H	C3H7	CH3	X10	—
2,084	H	H	C3H7	CH3	X15	—
2,085	H	H	C3H7	CH3	X21	—
2,086	H	H	C3H7	CH3	X26	—
2,087	CH3	CH3	CH3	Cl	X1	—
2,088	CH3	CH3	CH3	Cl	X2	—
2,089	CH3	CH3	CH3	Cl	X4	—
2,090	CH3	CH3	CH3	Cl	X26	—
2,091	CH3	CH3	CH3	CH3	X1	—
2,092	CH3	CH3	CH3	CH3	X2	—
2,093	CH3	CH3	CH3	CH3	X3	—
2,094	CH3	CH3	CH3	CH3	X4	—
2,095	CH3	CH3	CH3	CH3	X6	—
2,096	CH3	CH3	CH3	CH3	X10	—
2,097	CH3	CH3	CH3	CH3	X15	—
2,098	CH3	CH3	CH3	CH3	X21	—
2,099	CH3	CH3	CH3	CH3	X26	—
2,100	CH3	CH3	CH3	CH3	X30	—
2,101	CH3	CH3	CH3	SO2CH3	X1	—
2,102	CH3	CH3	CH3	SO2CH3	X2	—
2,103	CH3	CH3	CH3	SO2CH3	X4	—
2,104	CH3	CH3	CH3	SO2CH3	X26	—
2,105	CH3	CH3	CH3	NO2	X1	—
2,106	CH3	CH3	CH3	NO2	X2	—
2,107	CH3	CH3	CH3	NO2	X4	—
2,108	CH3	CH3	CH3	NO2	X26	—
2,109	CH3	CH3	CH3	NO2	X1	—
2,110	CH3	CH3	CH3	NO2	X2	—
2,111	CH3	CH3	CH3	NO2	X4	—
2,112	CH3	CH3	CH3	NO2	X26	—
2,113	CH3	CH3	CH3	Br	X1	—
2,114	CH3	CH3	CH3	Br	X2	—
2,115	CH3	CH3	CH3	Br	X4	—
2,116	CH3	CH3	CH3	Br	X26	—

[0083]

TABLE 3
Compounds of formula (Ic):
	(Ic)
16
Comp.							Phys.
No.	R28	R29	R30	R1	X	R2	data
3,001	CH3	CH3	CH3	CH3	X1	SO2CH3	—
3,002	CH3	CH3	CH3	CH3	X2	SO2CH3	—
3,003	CH3	CH3	CH3	CH3	X3	SO2CH3	—
3,004	CH3	CH3	CH3	CH3	X4	SO2CH3	—
3,005	CH3	CH3	CH3	CH3	X5	SO2CH3	—
3,006	CH3	CH3	CH3	CH3	X6	SO2CH3	—
3,007	CH3	CH3	CH3	CH3	X7	SO2CH3	—
3,008	CH3	CH3	CH3	CH3	X8	SO2CH3	—
3,009	CH3	CH3	CH3	CH3	X9	SO2CH3	—
3,010	CH3	CH3	CH3	CH3	X10	SO2CH3	—
3,011	CH3	CH3	CH3	CH3	X11	SO2CH3	—
3,012	CH3	CH3	CH3	CH3	X12	SOhd 2CH3	—
3,013	CH3	CH3	CH3	CH3	X13	SOhd 2CH3	—
3,014	CH3	CH3	CH3	CH3	X14	SOhd 2CH3	—
3,015	CH3	CH3	CH3	CH3	X15	SOhd 2CH3	—
3,016	CH3	CH3	CH3	CH3	X16	SOhd 2CH3	—
3,017	CH3	CH3	CH3	CH3	X17	SOhd 2CH3	—
3,018	CH3	CH3	CH3	CH3	X18	SOhd 2CH3	—
3,019	CH3	CH3	CH3	CH3	X19	SOhd 2CH3	—
3,020	CH3	CH3	CH3	CH3	X20	SOhd 2CH3	—
3,021	CH3	CH3	CH3	CH3	X21	SOhd 2CH3	—
3,022	CH3	CH3	CH3	CH3	X22	SOhd 2CH3	—
3,023	CH3	CH3	CH3	CH3	X23	SOhd 2CH3	—
3,024	CH3	CH3	CH3	CH3	X24	SOhd 2CH3	—
3,025	CH3	CH3	CH3	CH3	X25	SOhd 2CH3	—
3,026	CH3	CH3	CH3	CH3	X26	SOhd 2CH3	—
3,027	CH3	CH3	CH3	CH3	X27	SOhd 2CH3	—
3,028	CH3	CH3	CH3	CH3	X28	SOhd 2CH3	—
3,029	CH3	CH3	CH3	CH3	X29	SOhd 2CH3	—
3,030	CH3	CH3	CH3	CH3	X30	SOhd 2CH3	—
3,031	CH3	CH3	CH3	CH3	X31	SOhd 2CH3	—
3,032	CH3	CH3	CH3	CH3	X32	SOhd 2CH3	—
3,033	CH3	CH3	CH3	CH3	X33	SOhd 2CH3	—
3,034	CH3	CH3	CH3	CH3	X34	SOhd 2CH3	—
3,035	CH3	CH3	CH3	CH3	X35	SOhd 2CH3	—
3,036	CH3	CH3	CH3	CH3	X36	SOhd 2CH3	—
3,037	CH3	CH3	CH3	CH3	X37	SOhd 2CH3	—
3,038	CH3	CH3	CH3	CH3	X38	SOhd 2CH3	—
3,039	CH3	CH3	CH3	CH3	X39	SOhd 2CH3	—
3,040	CH3	CH3	CH3	CH3	X40	SOhd 2CH3	—
3,041	CH3	CH3	CH3	CH3	X41	SOhd 2CH3	—
3,042	CH3	CH3	CH3	CH3	X42	SOhd 2CH3	—
3,043	CH3	CH3	CH3	CH3	X1	SCH3	—
3,044	CH3	CH3	CH3	CH3	X2	SCH3	—
3,045	CH3	CH3	CH3	CH3	X3	SCH3	—
3,046	CH3	CH3	CH3	CH3	X4	SCH3	—
3,047	CH3	CH3	CH3	CH3	X5	SCH3	—
3,048	CH3	CH3	CH3	CH3	X6	SCH3	—
3,049	CH3	CH3	CH3	CH3	X7	SCH3	—
3,050	CH3	CH3	CH3	CH3	X10	SCH3	—
3,051	CH3	CH3	CH3	CH3	X15	SCH3	—
3,052	CH3	CH3	CH3	CH3	X20	SCH3	—
3,053	CH3	CH3	CH3	CH3	X21	SCH3	—
3,054	CH3	CH3	CH3	CH3	X26	SCH3	—
3,055	CH3	CH3	CH3	CH3	X27	SCH3	—
3,056	CH3	CH3	CH3	CH3	X29	SCH3	—
3,057	CH3	CH3	CH3	CH3	X30	SCH3	—
3,058	CH3	CH3	CH3	Cl	X1	SO2CH3	—
3,059	CH3	CH3	CH3	Cl	X2	SO2CH3	—
3,060	CH3	CH3	CH3	Cl	X3	SO2CH3	—
3,061	CH3	CH3	CH3	Cl	X4	SO2CH3	—
3,062	CH3	CH3	CH3	Cl	X5	SO2CH3	—
3,063	CH3	CH3	CH3	Cl	X6	SO2CH3	—
3,064	CH3	CH3	CH3	Cl	X7	SO2CH3	—
3,065	CH3	CH3	CH3	Cl	X8	SO2CH3	—
3,066	CH3	CH3	CH3	Cl	X9	SO2CH3	—
3,067	CH3	CH3	CH3	Cl	X10	SO2CH3	—
3,068	CH3	CH3	CH3	Cl	X11	SO2CH3	—
3,069	CH3	CH3	CH3	Cl	X12	SO2CH3	—
3,070	CH3	CH3	CH3	Cl	X13	SO2CH3	—
3,071	CH3	CH3	CH3	Cl	X14	SO2CH3	—
3,072	CH3	CH3	CH3	Cl	X15	SO2CH3	—
3,073	CH3	CH3	CH3	Cl	X16	SO2CH3	—
3,074	CH3	CH3	CH3	Cl	X17	SO2CH3	—
3,075	CH3	CH3	CH3	Cl	X18	SO2CH3	—
3,076	CH3	CH3	CH3	Cl	X19	SO2CH3	—
3,077	CH3	CH3	CH3	Cl	X20	SO2CH3	—
3,078	CH3	CH3	CH3	Cl	X21	SO2CH3	—
3,079	CH3	CH3	CH3	Cl	X22	SO2CH3	—
3,080	CH3	CH3	CH3	Cl	X23	SO2CH3	—
3,081	CH3	CH3	CH3	Cl	X24	SO2CH3	—
3,082	CH3	CH3	CH3	Cl	X25	SO2CH3	—
3,083	CH3	CH3	CH3	Cl	X26	SO2CH3	—
3,084	CH3	CH3	CH3	Cl	X27	SO2CH3	—
3,085	CH3	CH3	CH3	Cl	X28	SO2CH3	—
3,086	CH3	CH3	CH3	Cl	X29	SO2CH3	—
3,087	CH3	CH3	CH3	Cl	X30	SO2CH3	—
3,088	CH3	CH3	CH3	Cl	X31	SO2CH3	—
3,089	CH3	CH3	CH3	Cl	X32	SO2CH3	—
3,090	CH3	CH3	CH3	Cl	X33	SO2CH3	—
3,091	CH3	CH3	CH3	Cl	X34	SO2CH3	—
3,092	CH3	CH3	CH3	Cl	X35	SO2CH3	—
3,093	CH3	CH3	CH3	Cl	X36	SO2CH3	—
3,094	CH3	CH3	CH3	Cl	X37	SO2CH3	—
3,095	CH3	CH3	CH3	Cl	X38	SO2CH3	—
3,096	CH3	CH3	CH3	Cl	X39	SO2CH3	—
3,097	CH3	CH3	CH3	Cl	X40	SO2CH3	—
3,098	CH3	CH3	CH3	Cl	X41	SO2CH3	—
3,099	CH3	CH3	CH3	Cl	X42	SO2CH3	—
3,100	CH3	CH3	CH3	CH3	X1	CF3	—
3,101	CH3	CH3	CH3	CH3	X2	CF3	—
3,102	CH3	CH3	CH3	CH3	X3	CF3	—
3,103	CH3	CH3	CH3	CH3	X4	CF3	—
3,104	CH3	CH3	CH3	CH3	X6	CF3	—
3,105	CH3	CH3	CH3	CH3	X10	CF3	—
3,106	CH3	CH3	CH3	CH3	X15	CF3	—
3,107	CH3	CH3	CH3	CH3	X21	CF3	—
3,108	CH3	CH3	CH3	CH3	X26	CF3	—
3,109	CH3	CH3	CH3	CH3	X30	CF3	—
3,110	CH3	CH3	CH3	NO2	X1	SO2CH3	—
3,111	CH3	CH3	CH3	NO2	X2	SO2CH3	—
3,112	CH3	CH3	CH3	NO2	X4	SO2CH3	—
3,113	CH3	CH3	CH3	NO2	X26	SO2CH3	—
3,114	CH3	CH3	CH3	NO2	X1	CF3	—
3,115	CH3	CH3	CH3	NO2	X2	CF3	—
3,116	CH3	CH3	CH3	NO2	X4	CF3	—
3,117	CH3	CH3	CH3	NO2	X26	CF3	—
3,118	CH3	C2H5	CH3	CH3	X1	SO2CH3	—
3,119	CH3	C2H5	CH3	CH3	X2	SO2CH3	—
3,120	CH3	C2H5	CH3	CH3	X3	SO2CH3	—
3,121	CH3	C2H5	CH3	CH3	X4	SO2CH3	—
3,122	CH3	C2H5	CH3	CH3	X6	SO2CH3	—
3,123	CH3	C2H5	CH3	CH3	X10	SO2CH3	—
3,124	CH3	C2H5	CH3	CH3	X15	SO2CH3	—
3,125	CH3	C2H5	CH3	CH3	X21	SO2CH3	—
3,126	CH3	C2H5	CH3	CH3	X26	SO2CH3	—
3,127	CH3	C2H5	CH3	CH3	X30	SO2CH3	—
3,128	C2H5	C2H5	CH3	CH3	X1	SO2CH3	—
3,129	C2H5	C2H5	CH3	CH3	X2	SO2CH3	—
3,130	C2H5	C2H5	CH3	CH3	X4	SO2CH3	—
3,131	C2H5	C2H5	CH3	CH3	X10	SO2CH3	—
3,132	C2H5	C2H5	CH3	CH3	X15	SO2CH3	—
3,133	C2H5	C2H5	CH3	CH3	X21	SO2CH3	—
3,134	C2H5	C2H5	CH3	CH3	X26	SO2CH3	—
3,135	CH3	CH3	CH3	Cl	X1	SCH3	—
3,136	CH3	CH3	CH3	Cl	X2	SCH3	—
3,137	CH3	CH3	CH3	Cl	X3	SCH3	—
3,138	CH3	CH3	CH3	Cl	X4	SCH3	—
3,139	CH3	CH3	CH3	Cl	X5	SCH3	—
3,140	CH3	CH3	CH3	Cl	X6	SCH3	—
3,141	CH3	CH3	CH3	Cl	X7	SCH3	—
3,142	CH3	CH3	CH3	Cl	X10	SCH3	—
3,143	CH3	CH3	CH3	Cl	X15	SCH3	—
3,144	CH3	CH3	CH3	Cl	X20	SCH3	—
3,145	CH3	CH3	CH3	Cl	X21	SCH3	—
3,146	CH3	CH3	CH3	Cl	X26	SCH3	—
3,147	CH3	CH3	CH3	Cl	X27	SCH3	—
3,148	CH3	CH3	CH3	Cl	X29	SCH3	—
3,149	CH3	CH3	CH3	Cl	X30	SCH3	—

[0084]

TABLE 4
Compounds of formula (Id):
	(Id)
17
Comp.							Phys.
No.	R36	R37	W	R1	X	R2	data
4,001	CH3	CH3	O	CH3	X2	SO2CH3	—
4,002	CH3	CH3	O	CH3	X2	SO2CH3	—
4,003	CH3	CH3	O	CH3	X3	SO2CH3	—
4,004	CH3	CH3	O	CH3	X4	SO2CH3	—
4,005	CH3	CH3	O	CH3	X5	SO2CH3	—
4,006	CH3	CH3	O	CH3	X6	SO2CH3	—
4,007	CH3	CH3	O	CH3	X7	SO2CH3	—
4,008	CH3	CH3	O	CH3	X8	SO2CH3	—
4,009	CH3	CH3	O	CH3	X9	SO2CH3	—
4,010	CH3	CH3	O	CH3	X10	SO2CH3	—
4,011	CH3	CH3	O	CH3	X11	SO2CH3	—
4,012	CH3	CH3	O	CH3	X12	SO2CH3	—
4,013	CH3	CH3	O	CH3	X13	SO2CH3	—
4,014	CH3	CH3	O	CH3	X14	SO2CH3	—
4,015	CH3	CH3	O	CH3	X15	SO2CH3	—
4,016	CH3	CH3	O	CH3	X16	SO2CH3	—
4,017	CH3	CH3	O	CH3	X17	SO2CH3	—
4,018	CH3	CH3	O	CH3	X18	SO2CH3	—
4,019	CH3	CH3	O	CH3	X19	SO2CH3	—
4,020	CH3	CH3	O	CH3	X20	SO2CH3	—
4,021	CH3	CH3	O	CH3	X21	SO2CH3	—
4,022	CH3	CH3	O	CH3	X22	SO2CH3	—
4,023	CH3	CH3	O	CH3	X23	SO2CH3	—
4,024	CH3	CH3	O	CH3	X24	SO2CH3	—
4,025	CH3	CH3	O	CH3	X25	SO2CH3	—
4,026	CH3	CH3	O	CH3	X26	SO2CH3	—
4,027	CH3	CH3	O	CH3	X27	SO2CH3	—
4,028	CH3	CH3	O	CH3	X28	SO2CH3	—
4,029	CH3	CH3	O	CH3	X29	SO2CH3	—
4,030	CH3	CH3	O	CH3	X30	SO2CH3	—
4,031	CH3	CH3	O	CH3	X31	SO2CH3	—
4,032	CH3	CH3	O	CH3	X32	SO2CH3	—
4,033	CH3	CH3	O	CH3	X33	SO2CH3	—
4,034	CH3	CH3	O	CH3	X34	SO2CH3	—
4,035	CH3	CH3	O	CH3	X35	SO2CH3	—
4,036	CH3	CH3	O	CH3	X36	SO2CH3	—
4,037	CH3	CH3	O	CH3	X37	SO2CH3	—
4,038	CH3	CH3	O	CH3	X38	SO2CH3	—
4,039	CH3	CH3	O	CH3	X39	SO2CH3	—
4,040	CH3	CH3	O	CH3	X40	SO2CH3	—
4,041	CH3	CH3	O	CH3	X41	SO2CH3	—
4,042	CH3	CH3	O	CH3	X42	SO2CH3	—
4,043	CH3	CH3	O	CH3	X1	SCH3	—
4,044	CH3	CH3	O	CH3	X2	SCH3	—
4,045	CH3	CH3	O	CH3	X3	SCH3	—
4,046	CH3	CH3	O	CH3	X4	SCH3	—
4,047	CH3	CH3	O	CH3	X5	SCH3	—
4,048	CH3	CH3	O	CH3	X6	SCH3	—
4,049	CH3	CH3	O	CH3	X7	SCH3	—
4,050	CH3	CH3	O	CH3	X10	SCH3	—
4,051	CH3	CH3	O	CH3	X15	SCH3	—
4,052	CH3	CH3	O	CH3	X20	SCH3	—
4,053	CH3	CH3	O	CH3	X21	SCH3	—
4,054	CH3	CH3	O	CH3	X26	SCH3	—
4,055	CH3	CH3	O	CH3	X27	SCH3	—
4,056	CH3	CH3	O	CH3	X29	SCH3	—
4,057	CH3	CH3	O	CH3	X30	SCH3	—
4,058	CH3	CH3	O	Cl	X1	SO2CH3	—
4,059	CH3	CH3	O	Cl	X2	SO2CH3	—
4,060	CH3	CH3	O	Cl	X3	SO2CH3	—
4,061	CH3	CH3	O	Cl	X4	SO2CH3	—
4,062	CH3	CH3	O	Cl	X5	SO2CH3	—
4,063	CH3	CH3	O	Cl	X6	SO2CH3	—
4,064	CH3	CH3	O	Cl	X7	SO2CH3	—
4,065	CH3	CH3	O	Cl	X8	SO2CH3	—
4,066	CH3	CH3	O	Cl	X9	SO2CH3	—
4,067	CH3	CH3	O	Cl	X10	SO2CH3	—
4,068	CH3	CH3	O	Cl	X11	SO2CH3	—
4,069	CH3	CH3	O	Cl	X12	SO2CH3	—
4,070	CH3	CH3	O	Cl	X13	SO2CH3	—
4,071	CH3	CH3	O	Cl	X14	SO2CH3	—
4,072	CH3	CH3	O	Cl	X15	SO2CH3	—
4,073	CH3	CH3	O	Cl	X16	SO2CH3	—
4,074	CH3	CH3	O	Cl	X17	SO2CH3	—
4,075	CH3	CH3	O	Cl	X18	SO2CH3	—
4,076	CH3	CH3	O	Cl	X19	SO2CH3	—
4,077	CH3	CH3	O	Cl	X20	SO2CH3	—
4,078	CH3	CH3	O	Cl	X21	SO2CH3	—
4,079	CH3	CH3	O	Cl	X22	SO2CH3	—
4,080	CH3	CH3	O	Cl	X23	SO2CH3	—
4,081	CH3	CH3	O	Cl	X24	SO2CH3	—
4,082	CH3	CH3	O	Cl	X25	SO2CH3	—
4,083	CH3	CH3	O	Cl	X26	SO2CH3	—
4,084	CH3	CH3	O	Cl	X27	SO2CH3	—
4,085	CH3	CH3	O	Cl	X28	SO2CH3	—
4,086	CH3	CH3	O	Cl	X29	SO2CH3	—
4,087	CH3	CH3	O	Cl	X30	SO2CH3	—
4,088	CH3	CH3	O	Cl	X31	SO2CH3	—
4,089	CH3	CH3	O	Cl	X32	SO2CH3	—
4,090	CH3	CH3	O	Cl	X33	SO2CH3	—
4,091	CH3	CH3	O	Cl	X34	SO2CH3	—
4,092	CH3	CH3	O	Cl	X35	SO2CH3	—
4,093	CH3	CH3	O	Cl	X36	SO2CH3	—
4,094	CH3	CH3	O	Cl	X37	SO2CH3	—
4,095	CH3	CH3	O	Cl	X38	SO2CH3	—
4,096	CH3	CH3	O	Cl	X39	SO2CH3	—
4,097	CH3	CH3	O	Cl	X40	SO2CH3	—
4,098	CH3	CH3	O	Cl	X41	SO2CH3	—
4,099	CH3	CH3	O	Cl	X42	SO2CH3	—
4,100	CH3	CH3	O	CH3	X1	CF3	—
4,101	CH3	CH3	O	CH3	X2	CF3	—
4,102	CH3	CH3	O	CH3	X3	CF3	—
4,103	CH3	CH3	O	CH3	X4	CF3	—
4,104	CH3	CH3	O	CH3	X6	CF3	—
4,105	CH3	CH3	O	CH3	X10	CF3	—
4,106	CH3	CH3	O	CH3	X15	CF3	—
4,107	CH3	CH3	O	CH3	X21	CF3	—
4,108	CH3	CH3	O	CH3	X26	CF3	—
4,109	CH3	CH3	O	CH3	X30	CF3	—
4,110	CH3	CH3	O	NO2	X1	SO2CH3	—
4,111	CH3	CH3	O	NO2	X2	SO2CH3	—
4,112	CH3	CH3	O	NO2	X4	SO2CH3	—
4,113	CH3	CH3	O	NO2	X26	SO2CH3	—
4,114	CH3	CH3	O	NO2	X1	CF3	—
4,115	CH3	CH3	O	NO2	X2	CF3	—
4,116	CH3	CH3	O	NO2	X4	CF3	—
4,117	CH3	CH3	O	NO2	X26	CF3	—
4,118	CH3	CH3	O	CH3	X1	SO2CH3	—
4,119	CH3	CH3	O	CH3	X2	SO2CH3	—
4,120	CH3	CH3	O	CH3	X3	SO2CH3	—
4,121	CH3	CH3	O	CH3	X4	SO2CH3	—
4,122	CH3	CH3	O	CH3	X6	SO2CH3	—
4,123	CH3	CH3	O	CH3	X10	SO2CH3	—
4,124	CH3	CH3	O	CH3	X15	SO2CH3	—
4,125	CH3	CH3	O	CH3	X21	SO2CH3	—
4,126	CH3	CH3	O	CH3	X26	SO2CH3	—
4,127	CH3	CH3	O	CH3	X30	SO2CH3	—
4,128	CH3	CH3	O	CH3	X1	SO2CH3	—
4,129	CH3	CH3	O	CH3	X2	SO2CH3	—
4,130	CH3	CH3	O	CH3	X4	SO2CH3	—
4,131	CH3	CH3	O	CH3	X10	SO2CH3	—
4,132	CH3	CH3	O	CH3	X15	SO2CH3	—
4,133	CH3	CH3	O	CH3	X21	SO2CH3	—
4,134	CH3	CH3	O	CH3	X26	SO2CH3	—
4,135	CH3	CH3	O	Cl	X1	SCH3	—
4,136	CH3	CH3	O	Cl	X2	SCH3	—
4,137	CH3	CH3	O	Cl	X3	SCH3	—
4,138	CH3	CH3	O	Cl	X4	SCH3	—
4,139	CH3	CH3	O	Cl	X5	SCH3	—
4,140	CH3	CH3	O	Cl	X6	SCH3	—
4,141	CH3	CH3	O	Cl	X7	SCH3	—
4,142	CH3	CH3	O	Cl	X10	SCH3	—
4,143	CH3	CH3	O	Cl	X15	SCH3	—
4,144	CH3	CH3	O	Cl	X20	SCH3	—
4,145	CH3	CH3	O	Cl	X21	SCH3	—
4,146	CH3	CH3	O	Cl	X26	SCH3	—
4,147	CH3	CH3	O	Cl	X27	SCH3	—
4,148	CH3	CH3	O	Cl	X29	SCH3	—
4,149	CH3	CH3	O	Cl	X30	SCH3	—
4,150	CH3	CH3	S	CH3	X1	SO2CH3	—
4,151	CH3	CH3	S	CH3	X2	SO2CH3	—
4,152	CH3	CH3	S	CH3	X4	SO2CH3	—
4,153	CH3	CH3	S	CH3	X26	SO2CH3	—
4,154	CH3	CH3	S	Cl	X1	SO2CH3	—
4,155	CH3	CH3	S	Cl	X2	SO2CH3	—
4,156	CH3	CH3	S	Cl	X4	SO2CH3	—
4,157	CH3	CH3	NCH3	CH3	X26	SO2CH3	—
4,158	CH3	CH3	NCH3	CH3	X1	SO2CH3	—
4,159	CH3	CH3	NCH3	CH3	X2	SO2CH3	—
4,160	CH3	CH3	NCH3	CH3	X4	SO2CH3	—
4,161	CH3	CH3	NCH3	CH3	X26	SO2CH3	—
4,162	H	H	O	CH3	X1	SO2CH3	—
4,163	H	H	O	CH3	X2	SO2CH3	—
4,164	H	H	O	CH3	X4	SO2CH3	—
4,165	H	H	O	CH3	X26	SO2CH3	—

BIOLOGICAL EXAMPLES

Example B1

Pre-Emergent Herbicidal Action

[0085] Monocot and dicot test plants are sown in standard soil in plastic pots. Immediately after sowing, the plants are sprayed at a concentration of 2 kg active substance/ha with an aqueous suspension of the test compound [prepared from a 25% wettable powder (Example F3, b) in accordance with WO 97/34485] or an emulsion of the test compound [prepared from a 25% emulsifiable concentrate (Example F1 c)] (500 l of water/ha). The test plants are then cultivated in the greenhouse under optimum conditions. The test is evaluated 3 weeks later oh a rating scale of 1-9 (1=total damage, 9=no action). Ratings of 1 to 4 (especially of 1 to 3) denote good to very good herbicidal action.

TABLE B1
Pre-emergent action:
Active	test plant
ingredient						dosage
No.	Setaria	Cyperus	Sinapsis	Solanig	Stellaria	[g AS/ha]
1,001	3	3	3	2	2	2000
2,001	3	3	2	2	2	2000

[0086] The same results are obtained by formulating the compounds of formula I in accordance with Examples F2 and F4 to F8 of WO 97/34485.

Example B2

Post-Emergent Herbicidal Action

[0087] In a greenhouse, monocot and dicot test plants are sown in standard soil in plastic pots and sprayed in the 4- to 6-leaf stage with an aqueous suspension of the test compounds of formula I prepared from a 25% wettable powder [Example F3, b) of WO 97/34485] or with an emulsion of the test compound of formula I prepared from a 25% emulsifiable concentrate [Example F1 c) of WO 97/34485] at a concentration of 2 kg active substance/ha (500 l of water/ha). The test plants are then further cultivated in the greenhouse under optimum conditions. The test is evaluated about 18 days later on a rating scale of 1-9 (1=total damage, 9=no action). Ratings of 1 to 4 (especially of 1 to 3) denote good to very good herbicidal action. In this test the compounds of formula I exhibit a pronounced herbicidal action.

TABLE B2
Post-emergent action
Active	test plant
ingredient						dosage
No.	Setaria	Cyperus	Sinapsis	Solanig	Stellaria	[g AS/ha]
1,001	2	3	2	2	2	2000
2,001	3	3	2	2	4	2000

[0088] The same results are obtained by formulating the compounds of formula I in accordance with Examples F2 and F4 to F8 of WO 97/34485.

Claims

1. Compounds of formula I

2. Compounds according to 1, whereby R1 and R2, independently of one another, signify halogen, cyano, nitro, amino, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-dialkylaminosulphonyl, C1-C6-alkylaminosulphonyl, C1-C6-halogenalkoxy, OSO2-C1-C4-alkyl, C1-C6-halogenalkylthio, C1-C6-halogen-alkylsulphinyl, C1-C6-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl and R33 signifies hydroxy, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyloxy, C1-C6-alkoxy-carbonyloxy, C1-C6-dialkylamino, COOH, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxycarbonyl-C1-C4-alkylthio, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphinyl, C1-C4-alkoxycarbonyl-C1-C4-alkylsulphonyl, C1-C6-alkenylthio, C1-C6-alkenylsulphinyl, C1-C6-alkenylsulphonyl, OSO2-C1-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano.

3. Compounds according to claim 1, whereby Q is Q1 or Q2.

4. Compounds according to claim 1, whereby X is L1-Y1-R4.

5. Compounds according to claim 4, whereby L1 signifies methylene.

6. Compounds according to claim 1, whereby R2 signifies C1-C6-alkylsulphonyl.

7. A herbicidal and plant growth inhibiting composition, which comprises a herbicidally effective amount of the compound of formula I on an inert carrier.

8. A method of controlling undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I or of a composition containing such a compound.

9. A method of inhibiting undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I or of a composition containing such a compound.

10. Use of a composition according to claim 7 for controlling undesirable plant growth.