# Patent

## Title
1-phenylpyrrolidine-2-one-3-carboxamides

## Abstract

The invention relates to 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I




where the variables R1, R2, R3, X, Y, A, n, Ra, Rb, Rc, Rd and Re are as defined in claim 1 and to their agriculturally useful salts.

Moreover, the invention relates to

    
    
        the use of compounds I and/or their salts as herbicides;
        crop protection compositions comprising at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I and/or at least one agriculturally useful salt of I as active substances; and also
        a method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I or an agriculturally useful salt of I to act on plants, their habitat or on seed.

## Background
CROSS REFERENCE TO RELATED APPLICATION
This application is a 35 USC § 371 National Phase Entry Application from PCT/EP2003/011557, filed Oct. 17, 2003, and designating the United States.
The present invention relates to 1-phenylpyrrolidin-2-one-3-carboxamides and their agriculturally useful salts, to compositions comprising such compounds and to the use of the 1-phenylpyrrolidin-2-one-3-carboxamides, of their salts or of compositions comprising them as herbicides.
WO 95/33719 describes 1-arylthiazolidinones, 1-aryloxazolidinones and 1-arylpyrrolidinones of the formula:




where A is an aromatic or heteroaromatic radical, n is 0 or 1, x is in particular S, O or CH2, Y is in particular S, O, CH2 or CH(CH3) or a group NR6, Z is in particular NH or O, R1 is preferably selected from unsubstituted or substituted alkyl, alkenyl, alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, benzyl or hetaryl, acyl, alkoxycarbonylalkyl and silyl, R2 and R3 are in particular hydrogen and R6 is inter alia hydrogen, formyl, unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl or unsubstituted or substituted aryl.

WO 95/33718 describes 1-phenylpyrrolidinethiones having herbicidal activity which, in the 3-position of the pyrrolidinethione ring, contain a group O—C(O)—NR1R2 where R1R2 are, for example, hydrogen, an unsubstituted or substituted hydrocarbon radical or hetaryl, or together with the nitrogen atom to which they are attached form a heterocycle.
Furthermore, U.S. Pat. No. 4,874,422 discloses herbicidally active 1-phenylpyrrolidin-2-one-3-carboxamides of the formula A




where X is hydrogen or halogen, Y and Z independently of one another are O or S, n is 0 or 1, R1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, phenyl, halophenyl, benzyl, halobenzyl, or alkyl which is substituted by alkoxy, alkylthio, phenyl, hydroxyl or cyano, R2 is hydrogen or alkyl, R3 is alkyl or alkenyl and R4 is selected from the group consisting of hydrogen, halogen, methyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyloxy, difluoromethoxy, trifluoromethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxyiminomethyl, methoxyimino-1-ethyl, benzyloxyiminomethyl and benzyloxyimino-1-ethyl.

The herbicidal activity of the 1-arylpyrrolidinones described in the prior art is not always satisfactory. Their selectivity for harmful plants is unsatisfactory, too. In particular, even at low application rates, such herbicides tend to interfere with the generation of chlorophyll even in crop plants, which is undesirable in principle and may lead to yield losses.
It is an object of the present invention to provide novel herbicidally active compounds which allow a better targeted control of unwanted plants than the known herbicides. Advantageously, the novel herbicides should be highly active against harmful plants. Moreover, high compatibility with crop plants is desirable. Moreover, the compounds should have no adverse effect on the chlorophyll synthesis in crop plants.
We have found that this object is achieved by 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I defined below and their agriculturally useful salts:




where the variables R1, R2, R3, X, Y, A, n, Ra, Rb, Rc, Rd and Re are as defined below:

    R1 is hydrogen, OH, Cl, Br, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C(O)R4 or OC(O)R4;
    R2 and R3 independently of one another are hydrogen, C1-C10-alkyl, C3-C10-cycloalkyl, C7-C10-polycycloalkyl, C3-C8-alkenyl, C3-C10-alkynyl, C5-C10-cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl or 3- to 7-membered heterocyclyl, where the 9 last-mentioned groups may be unsubstituted, partially or fully halogenated and/or contain 1, 2 or 3 radicals selected from the group consisting of OH, CN, NO2, COOH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylthio, C1-C4-haloalkyl-thio, unsubstituted or substituted phenyl, COOR5, NR6R7, C(O)NR8SO2R13, C(O)NR8R9 and 3- to 7-membered heterocyclyl, and each heterocyclyl may contain 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, a group NR10 and a group SO2, and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members; and/or may contain a ring-fused phenyl ring which is unsubstituted or substituted; or
    
        R2 and R3 with the group N-(A)n to which they are attached form a saturated 3- to 7-membered heterocycle which, in addition to the nitrogen atom, may contain 1, 2 or a further 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and a group NR10 and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members;
    
    
    Ra, Rb, Rc, Rd and Re independently of one another are hydrogen, OH, CN, NO2, halogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, C(O)R4, COOR5, NR6R7, C(O)NR8R9, S(O)2NR8R9, S(O)R11, S(O)2R11 or C1-C4-alkoxy-C1-C6-alkyl; or
    
        two adjacent radicals Ra to Re together with the atoms to which they are attached form a 5-, 6- or 7-membered saturated or unsaturated ring which may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and a group NR10 as ring-forming atom and/or may carry one, two, three or four radicals selected from the group consisting of halogen and C1-C4-alkyl;
    
    
    X, Y independently of one another are oxygen or sulfur;
    n is 0 or 1;
    A is O, S(O)k or NR12, where k is 0, 1 or 2;
    R4, R8, R9 independently of one another are hydrogen or C1-C4-alkyl;
    R5, R11 are C1-C4-alkyl;
    R6, R7 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C(O)R4, COOR5 or S(O)2R11;
    R10, R12 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; and
    R13 is phenyl which is unsubstituted or carries 1, 2, 3 or 4 substituents, where the substituents are selected from the group consisting of halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR5, NR6R7 and C(O)NR8R9.


Accordingly, the present invention relates to 1-phenyl-pyrrolidin-2-one-3-carboxamides of the formula I and their agriculturally useful salts.
Moreover, the present invention relates to

    
    
        the use of compounds I and/or their salts as herbicides;
        crop protection compositions comprising at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I and/or at least one agriculturally useful salt of I as active substances; and
        methods for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I or an agriculturally useful salt of I to act on plants, their habitat or on seed.
    
    


Depending on the substitution pattern, the compounds of the formula I may contain one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures. The invention also provides tautomers of compounds of the formula I.
If R1 represents hydrogen, the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I according to the invention can be present in the form of their agriculturally useful salts. In general, agriculturally useful salts are the salts of those bases or cations which have no adverse effect on the herbicidal action of the compounds I. Thus, suitable basic salts are in particular the salts of the alkali metals, preferably of sodium and potassium, of the alkaline earth metals, preferably of calcium, magnesium and barium, and of the transition metals, preferably of manganese, copper, zinc and iron, and also ammonium salts where the ammonium ion may, if desired, carry one to four C1-C4-alkyl substituents, C1-C4-hydroxyalkyl substituents, C1-C4-alkoxy-C1-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, trimethyl-2-hydroxyethylammonium, bis(2-hydroxyethyl)methylammonium, tris(2-hydroxyethyl)ammonium, bis(2-hydroxyethyl)-dimethylammonium, tris(2-hydroxyethyl)methylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
The organic moieties mentioned in the definition of the substituents R1 to R12 or as radicals on heterocyclic rings are—like the term halo—collective terms for individual listings of the individual group members. All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, aminoalkyl, aminocarbonylalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, alkynyl and alkenyl moieties, may be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. The term halo denotes in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:

    
    
        C1-C4-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
        C1-C6-alkyl: C1-C4-alkyl as mentioned above and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;
        C1-C10-alkyl: C1-C6-alkyl as mentioned above and also, for example, n-heptyl, 2-heptyl, 2-methylhexyl, n-octyl, 1-methylheptyl, 2-ethylhexyl, n-nonyl, 2-nonyl, n-decyl, 2-decyl, 2-propylheptyl and the like;
        C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl; in particular difluoromethyl, trifluoromethyl;
        C1-C6-haloalkyl: C1-C4-haloalkyl as mentioned above and also 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
        C1-C2-fluoroalkyl: C1-C2-alkyl which carries 1, 2, 3, 4 or 5 fluorine atoms, for example difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl and pentafluoroethyl;
        C1-C2-fluoroalkoxy: C1-C2-alkoxy which carries 1, 2, 3, 4 or 5 fluorine atoms, for example difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy and pentafluoroethoxy;
        C1-C4-alkoxy: for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
        C1-C6-alkoxy: C1-C4-alkoxy as mentioned above and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
        C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCH(Cl)2, OC(Cl)3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2—C2F5, OCF2—C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, preferably OCHF2 or OCHF3;
        C1-C4-alkoxy-C1-C6-alkyl: C1-C6-alkyl which is substituted by C1-C6-alkoxy—as mentioned above—, i.e., for example, CH2—OCH3, CH2—OC2H5, n-propoxymethyl, CH2—OCH(CH3) 2, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH2—OC(CH3)3, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl, 4-(1,1-dimethylethoxy)butyl, 2-(1-methylethoxy)pentyl, 2-(n-butoxy)pentyl, 2-(1-methylpropoxy)pentyl, 2-(2-methylpropoxy)pentyl, 2-(1,1-dimethylethoxy)pentyl, 3-(methoxy)pentyl, 3-(ethoxy)pentyl, 3-(n-propoxy)pentyl, 3-(1-methylethoxy)pentyl, 3-(n-butoxy)pentyl, 3-(1-methylpropoxy)pentyl, 3-(2-methylpropoxy)pentyl, 3-(1,1-dimethylethoxy)pentyl, 4-(methoxy)pentyl, 4-(ethoxy)pentyl, 4-(n-propoxy)pentyl, 4-(1-methylethoxy)pentyl, 4-(n-butoxy)pentyl, 4-(1-methylpropoxy)pentyl, 4-(2-methylpropoxy)pentyl, 4-(1,1-dimethylethoxy)pentyl, 4-(methoxy)pentyl, 5-(ethoxy)pentyl, 5-(n-propoxy)pentyl, 5-(1-methylethoxy)pentyl, 5-(n-butoxy)pentyl, 5-(1-methylpropoxy)pentyl, 5-(2-methylpropoxy)pentyl, 5-(1,1-dimethylethoxy)pentyl, 2-(1-methylethoxy)hexyl, 2-(n-butoxy)hexyl, 2-(1-methylpropoxy)hexyl, 2-(2-methylpropoxy)hexyl, 2-(1,1-dimethylethoxy)hexyl, 3-(methoxy)hexyl, 3-(ethoxy)hexyl, 3-(n-propoxy)hexyl, 3-(1-methylethoxy)hexyl, 3-(n-butoxy)hexyl, 3-(1-methylpropoxy)hexyl, 3-(2-methylpropoxy)hexyl 3-(1,1-dimethylethoxy)hexyl, 4-(methoxy)hexyl, 4-(ethoxy)hexyl, 4-(n-propoxy)hexyl, 4-(1-methylethoxy)hexyl, 4-(n-butoxy)hexyl, 4-(1-methylpropoxy)hexyl, 4-(2-methylpropoxy)hexyl, 4-(1,1-dimethylethoxy)hexyl, 4-(methoxy)hexyl, 5-(ethoxy)hexyl, 5-(n-propoxy)hexyl, 5-(1-methylethoxy)hexyl, 5-(n-butoxy)hexyl, 5-(1-methylpropoxy)hexyl, 5-(2-methylpropoxy)hexyl, 5-(1,1-dimethylethoxy)hexyl, 6-(ethoxy)hexyl, 6-(n-propoxy)hexyl, 6-(1-methylethoxy)hexyl, 6-(n-butoxy)hexyl, 6-(1-methylpropoxy)hexyl, 6-(2-methylpropoxy)hexyl, 6-(1,1-dimethylethoxy)hexyl;
        C1-C4-alkylthio: an alkylsulfanyl radical having 1 to 4 carbon atoms, for example SCH3, SC2H5, SCH2—C2H5, SCH(CH3)2, n-butylthio, SCH(CH3)—C2H5, SCH2—CH(CH3) 2 or SC(CH3) 3;
        C1-C6-alkylthio: C1-C4-alkylthio as mentioned above and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;
        C1-C4-haloalkylthio: a C1-C4-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;
        phenyl-C1-C4-alkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl or 1-(benzyl)prop-1-yl;
        C2-C6-alkenyl: a monounsaturated aliphatic hydrocarbon radical having 2 to 6 and in particular 2 to 4 carbon atoms, for example ethenyl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl;
        C3-C8-alkenyl: an aliphatic hydrocarbon radical which contains a C═C double bond and has 3 to 8, preferably 3 to 6 and in particular 3 or 4 carbon atoms as mentioned above, which is preferably not attached via a carbon atom of the double bond, for example one of the radicals mentioned under C2-C6-alkenyl and also 1-hepten-3-yl, 1-hepten-4-yl, 1-hepten-5-yl, 1-hepten-6-yl, 1-hepten-7-yl, 3-hepten-1-yl, 2-hepten-4-yl, 3-hepten-5-yl, 3-hepten-6-yl, 3-hepten-7-yl, 1-octen-3-yl, 1-octen-4-yl, 1-octen-5-yl, 1-octen-6-yl, 1-octen-7-yl, 1-octen-8-yl, 3-octen-1-yl, 2-octen-1-yl, 2-octen-4-yl, 3-octen-5-yl, 3-octen-6-yl, 3-octen-7-yl, 3-octen-8-yl and the like;
        C2-C6-haloalkenyl: C2-C6-alkenyl as mentioned above which is partially or fully substituted by fluorine, chlorine, and/or bromine, i.e., for example, 2-chlorovinyl, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl;
        C2-C6-alkynyl: an aliphatic hydrocarbon radical which contains a C—C triple bond and has 2 to 6 and in particular 2 to 4 carbon atoms: for example ethynyl, propargyl (2-propynyl), 1-propynyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;
        C3-C10-alkynyl: an aliphatic hydrocarbon radical which contains a triple bond and has 3 to 10, preferably 3 to 6 and in particular 3 or 4 carbon atoms as mentioned above, which is preferably not attached via a carbon atom of the triple bond, for example one of the radicals mentioned under C2-C6-alkynyl and also 1-heptyn-3-yl, 1-heptyn-4-yl, 1-heptyn-5-yl, 1-heptyn-6-yl, 1-heptyn-7-yl, 3-heptyn-1-yl, 2-heptyn-4-yl, 3-heptyn-5-yl, 3-heptyn-6-yl, 3-heptyn-7-yl, 1-octyn-3-yl, 1-octyn-4-yl, 1-octyn-5-yl, 1-octyn-6-yl, 1-octyn-7-yl, 1-octyn-8-yl, 3-octyn-1-yl, 2-octyn-1-yl, 2-octyn-4-yl, 3-octyn-5-yl, 3-octyn-6-yl, 3-octyn-7-yl, 3-octyn-8-yl and the like;
        C3-C10-cycloalkyl: a monocyclic hydrocarbon radical having 3 to 10 carbon atoms, in particular 3 to 8 carbon atoms and especially 3 to 6 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
        C7-C10-polycycloalkyl: a bicyclic, tricyclic or tetracyclic hydrocarbon radical having 7 to 10 carbon atoms, for example bicyclo[2.2.1]-hept-1-yl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.1]hept-7-yl, bicyclo[2.2.2]oct-1-yl, bicyclo[2.2.2]oct-2-yl or adamantan-1-yl;
        C3-C8-cycloalkyl-C1-C4-alkyl: C1-C4-alkyl which carries a C3-C8-cycloalkyl radical as defined above, for example cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl, 2-cyclopropylbut-1-yl, 3-cyclopropylbut-1-yl, 4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl, 2-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 4-cyclopropylbut-2-yl, 1-(cyclopropylmethyl)eth-1-yl, 1-(cyclopropylmethyl)-1-(methyl)eth-1-yl, 1-(cyclopropylmethyl)prop-1-yl, cyclobutylmethyl, 1-cyclobutylethyl, 2-cyclobutylethyl, 1-cyclobutylprop-1-yl, 2-cyclobutylprop-1-yl, 3-cyclobutylprop-1-yl, 1-cyclobutylbut-1-yl, 2-cyclobutylbut-1-yl, 3-cyclobutylbut-1-yl, 4-cyclobutylbut-1-yl, 1-cyclobutylbut-2-yl, 2-cyclobutylbut-2-yl, 3-cyclobutylbut-2-yl, 4-cyclobutylbut-2-yl, 1-(cyclobutylmethyl)eth-1-yl, 1-(cyclobutylmethyl)-1-(methyl)eth-1-yl, 1-(cyclobutylmethyl)prop-1-yl, cyclopentylmethyl, 1-cyclopentylethyl, 2-cyclopentylethyl, 1-cyclopentylprop-1-yl, 2-cyclopentylprop-1-yl, 3-cyclopentylprop-1-yl, 1-cyclopentylbut-1-yl, 2-cyclopentylbut-1-yl, 3-cyclopentylbut-1-yl, 4-cyclopentylbut-1-yl, 1-cyclopentylbut-2-yl, 2-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 4-cyclopentylbut-2-yl, 1-(cyclopentylmethyl)eth-1-yl, 1-(cyclopentylmethyl)-1-(methyl)eth-1-yl, 1-(cyclopentylmethyl)prop-1-yl, cyclohexylmethyl, 1-cyclohexylethyl, 2-cyclohexylethyl, 1-cyclohexylprop-1-yl, 2-cyclohexylprop-1-yl, 3-cyclohexylprop-1-yl, 1-cyclohexylbut-1-yl, 2-cyclohexylbut-1-yl, 3-cyclohexylbut-1-yl, 4-cyclohexylbut-1-yl, 1-cyclohexylbut-2-yl, 2-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 4-cyclohexylbut-2-yl, 1-(cyclohexylmethyl)eth-1-yl, 1-(cyclohexylmethyl)-1-(methyl)eth-1-yl, 1-(cyclohexylmethyl)prop-1-yl, cycloheptylmethyl, 1-cycloheptylethyl, 2-cycloheptylethyl, 1-cycloheptylprop-1-yl, 2-cycloheptylprop-1-yl, 3-cycloheptylprop-1-yl, 1-cycloheptylbut-1-yl, 2-cycloheptylbut-1-yl, 3-cycloheptylbut-1-yl, 4-cycloheptylbut-1-yl, 1-cycloheptylbut-2-yl, 2-cycloheptylbut-2-yl, 3-cycloheptylbut-2-yl, 4-cycloheptylbut-2-yl, 1-(cycloheptylmethyl)eth-1-yl, 1-(cycloheptylmethyl)-1-(methyl)eth-1-yl, 1-(cycloheptylmethyl)prop-1-yl, cyclooctylmethyl, 1-cyclooctylethyl, 2-cyclooctylethyl, 1-cyclooctylprop-1-yl, 2-cyclooctylprop-1-yl, 3-cyclooctylprop-1-yl, 1-cyclooctylbut-1-yl, 2-cyclooctylbut-1-yl, 3-cyclooctylbut-1-yl, 4-cyclooctylbut-1-yl, 1-cyclooctylbut-2-yl, 2-cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 4-cyclooctylbut-2-yl, 1-(cyclooctylmethyl)eth-1-yl, 1-(cyclooctylmethyl)-1-(methyl)eth-1-yl or 1-(cyclooctylmethyl)prop-1-yl, preferably cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.
    
    


C5-C10-cycloalkenyl: a mono- or bicyclic hydrocarbon radical having 5 to 10 carbon atoms, in particular 5 to 8 carbon atoms and especially 5 to 6 carbon atoms and which contains a C═C double bond, for example cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl, cyclohepten-1-yl, cyclohepten-3-yl, cyclohepten-4-yl, cycloocten-1-yl, cycloocten-3-yl, cycloocten-4-yl, cycloocten-5-yl, bicyclo[2.2.1]hept-2-en-1-yl, bicyclo[2.2.1]hept-2-en-2-yl, bicyclo[2.2.1]hept-2-en-5-yl, bicyclo[2.2.1]hept-2-en-7-yl, bicyclo[2.2.2]oct-2-en-1-yl, bicyclo[2.2.2]oct-2-en-2-yl, bicyclo[2.2.2]oct-2-en-5-yl, bicyclo[2.2.2]oct-2-en-7-yl;

    
    
        unsubstituted or substituted phenyl: a phenyl group which is unsubstituted or carries 1, 2, 3 or 4 substituents, where the substituents are selected from the group consisting of halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR5, NR6R7, C(O)NR8R9;
        3- to 7-membered heterocyclyl: a heterocyclic radical which has 3, 4, 5, 6 or 7 ring members, where 1, 2 or 3 of the ring members are heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, a group SO2 and a group NR10. Moreover, the heterocycle may optionally contain 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members. The heterocycle may furthermore contain a ring-fused unsubstituted or substituted phenyl ring. The heterocycle may be aromatic (heteroaryl) or partially or fully saturated.
        Examples of saturated heterocycles are: oxiran-1-yl, aziridin-1-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl, hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-4-yl, 1,3-dithiepan-5-yl, 1,3-dithiepan-6-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and hexahydro-1,4-diazepin-2-yl;
        Examples of unsaturated heterocycles are:
        dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl;
        Examples of aromatic heterocyclyl are the 5- and 6-membered aromatic, heterocyclic radicals, for example furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl, such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl, such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl, such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl, such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl, thiadiazolyl, such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl, such as 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl, such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particular pyridyl, pyrimidyl, furanyl and thienyl.
    
    


If the radicals R2 and R3 together with the nitrogen atom to which they are attached form a saturated heterocycle, n is preferably 0. In this case, the saturated heterocycle is selected, for example, from the group consisting of 1,3-oxazolidin-3-yl, 1,2-oxazolidin-2-yl, pyrrolidin-1-yl, pyrrolidin-2-on-1-yl, tetrahydropyrazol-1-yl, 2-methyltetrahydropyrazol-1-yl, piperidin-1-yl, piperidin-2-on-1-yl, morpholin-4-yl, hexahydropyrimidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, hexahydro-1,3,5-triazin-1-yl, 3,5-dimethyltriazin-1-yl, hexahydroazepin-1-yl, hexahydroazepin-2-on-1-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,4-diazepin-1-yl, in particular from the group consisting of pyrrolidin-1-yl, piperidin-1-yl and morpholin-4-yl.
If two adjacent radicals Ra to Re together with the atoms to which they are attached form a 5-, 6- or 7-membered saturated or unsaturated ring which may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and a group NR10 as ring-forming atom(s) and/or may carry one, two, three or four radicals selected from the group consisting of halogen and C1-C4-alkyl, two adjacent radicals Ra to Re, for example Rb and Rc or Rc and Rd, together are a 3-, 4- or 5-membered saturated or unsaturated carbon chain in which one or two non-adjacent carbon atoms of the chain may be replaced by heteroatoms selected from the group consisting of O, N, a group NR10 and S and in which the carbon atoms of the chain may carry one, two, three or four substituents selected from the group consisting of halogen and C1-C4-alkyl. For example, two adjacent radicals Ra to Re may be a chain of the formula —O—CH2—O—, —O—(CH2)2—O—, —O—(CH2)2—, —O—(CH2)3—, —(CH2)3—, —(CH2)4— or —(CH2)5—
With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables R1, R2, R3, X, Y, A, n, Ra, Rb, Rc, Rd and Re are preferably as defined below, independently of one another and in particular in combination:

    R1 is hydrogen, OH, Cl, Br, C1-C6-alkyl or OC(O)R4, particularly preferably hydrogen;
    R2 is C1-C10-alkyl, C3-C8-cycloalkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C8-cycloalkyl, C5-C8-cycloalkenyl or C3-C8-cycloalkyl-C1-C4-alkyl, where C1-C10-alkyl and C3-C8-cycloalkyl may be partially or fully halogenated and/or may carry one or two radicals selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7, C(O)NR8R9, phenyl which may be unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of halogen, nitro, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7, C(O)NR8R9. In particular, R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C5-C6-cycloalkenyl, C3-C6-cycloalkyl-C1-C4-alkyl or unsubstituted or substituted phenyl, where C1-C6-alkyl and C3-C6-cycloalkyl may be partially or fully halogenated and/or may carry one or two, in particular one, radical selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7, C(O)NR8R9. Particularly preferably, R2 is C1-C6-alkyl, C3-C8-cycloalkyl, unsubstituted or substituted phenyl, phenylalkyl or C3-C8-cycloalkyl-C1-C4-alkyl;
    R3 is hydrogen or C1-C6-alkyl;
    X is oxygen;
    Y is oxygen; and
    A if present, is oxygen, a group N—R12, where R12=hydrogen or alkyl, or a group SO2;
    n is 0;
    Ra, Rb, Rc, Rd, Re are hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, in particular halogen, CN, C1-C4-alkyl, C1-C2-fluoroalkyl and C1-C2-fluoroalkoxy and especially fluorine, chlorine, bromine, CN, C1-C4-alkyl, methoxy, CF3, CHF2, OCF3 and OCHF2.


With a view to the use as herbicides, preference is given to 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I according to the invention where not more than 3 of the radicals Ra, Rb, Rc, Rd and Re and in particular 3 or 4 of the abovementioned radicals are different from hydrogen. Particular preference is given to 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I where at least Rb and/or Rd are different from hydrogen. In this case, the other radicals Ra-Re, at least one of the radicals Ra and Re and especially both radicals Ra and Re are particularly preferably hydrogen. Particular preference is also given to compounds of the formula I in which Rb and Rc or Rd and Rc are different from hydrogen and the other radicals of the radicals Ra-Re are hydrogen. Another preferred embodiment of the invention relates to compounds in which the radicals Ra and Re or Ra and Rb or Ra and Rc are different from hydrogen and the other radicals of the radicals Ra-Re are hydrogen.
Preferred radicals Ra, Rb, Rc, Rd, Re are, in addition to hydrogen, the substituents halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, in particular halogen, CN, C1-C4-alkyl, C1-C2-fluoroalkyl and C1-C2-fluoroalkoxy and especially fluorine, chlorine, bromine, CN, C1-C4-alkyl, methoxy, CF3, CHF2, OCF3 and OCHF2.
A particularly preferred group of compounds of the formula I are those compounds in which Ra and Re are hydrogen. Here, the radical




denotes, for example, a group of the formulae Q1 to Q31:











Another preferred group of compounds of the formula I are those compounds in which Ra and, if appropriate, one of the radicals Rb, Rc or Re are different from hydrogen and the other radicals Ra-Re are hydrogen. Here, the radical




denotes, for example, a group of the formulae Q32 to Q39:





Particular preference is given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ia (≡I where Ra═Rb═H, X═O, Y═O, R1═H, R3═CH3 and n=0) where Rb, Rc, Rd and R2 have the meanings mentioned above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ia.1 to Ia.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.








TABLE 1








(Ia)








 











No.
Rb
Rc
Rd
R2














1.
Cl
H
H
H


2.
Br
H
H
H


3.
F
H
H
H


4.
CH3
H
H
H


5.
C2H5
H
H
H


6.
CH(CH3)2
H
H
H


7.
OCH3
H
H
H


8.
CN
H
H
H


9.
CF3
H
H
H


10.
OCF3
H
H
H


11.
OCHF2
H
H
H


12.
Cl
H
H
CH3


13.
Br
H
H
CH3


14.
F
H
H
CH3


15.
CH3
H
H
CH3


16.
C2H5
H
H
CH3


17.
CH(CH3)2
H
H
CH3


18.
OCH3
H
H
CH3


19.
CN
H
H
CH3


20.
CF3
H
H
CH3


21.
OCF3
H
H
CH3


22.
OCHF2
H
H
CH3


23.
Cl
H
H
C2H5


24.
Br
H
H
C2H5


25.
F
H
H
C2H5


26.
CH3
H
H
C2H5


27.
C2H5
H
H
C2H5


28.
CH(CH3)2
H
H
C2H5


29.
OCH3
H
H
C2H5


30.
CN
H
H
C2H5


31.
CF3
H
H
C2H5


32.
OCF3
H
H
C2H5


33.
OCHF2
H
H
C2H5


34.
Cl
H
H
n-C3H7


35.
Br
H
H
n-C3H7


36.
F
H
H
n-C3H7


37.
CH3
H
H
n-C3H7


38.
C2H5
H
H
n-C3H7


39.
CH(CH3)2
H
H
n-C3H7


40.
OCH3
H
H
n-C3H7


41.
CN
H
H
n-C3H7


42.
CF3
H
H
n-C3H7


43.
OCF3
H
H
n-C3H7


44.
OCHF2
H
H
n-C3H7


45.
Cl
H
H
CH(CH3)2


46.
Br
H
H
CH(CH3)2


47.
F
H
H
CH(CH3)2


48.
CH3
H
H
CH(CH3)2


49.
C2H5
H
H
CH(CH3)2


50.
CH(CH3)2
H
H
CH(CH3)2


51.
OCH3
H
H
CH(CH3)2


52.
CN
H
H
CH(CH3)2


53.
CF3
H
H
CH(CH3)2


54.
OCF3
H
H
CH(CH3)2


55.
OCHF2
H
H
CH(CH3)2


56.
Cl
H
H
n-C4H9


57.
Br
H
H
n-C4H9


58.
F
H
H
n-C4H9


59.
CH3
H
H
n-C4H9


60.
C2H5
H
H
n-C4H9


61.
CH(CH3)2
H
H
n-C4H9


62.
OCH3
H
H
n-C4H9


63.
CN
H
H
n-C4H9


64.
CF3
H
H
n-C4H9


65.
OCF3
H
H
n-C4H9


66.
OCHF2
H
H
n-C4H9


67.
Cl
H
H
C(CH3)3


68.
Br
H
H
C(CH3)3


69.
F
H
H
C(CH3)3


70.
CH3
H
H
C(CH3)3


71.
C2H5
H
H
C(CH3)3


72.
CH(CH3)2
H
H
C(CH3)3


73.
OCH3
H
H
C(CH3)3


74.
CN
H
H
C(CH3)3


75.
CF3
H
H
C(CH3)3


76.
OCF3
H
H
C(CH3)3


77.
OCHF2
H
H
C(CH3)3


78.
Cl
H
H
C6H5


79.
Br
H
H
C6H5


80.
F
H
H
C6H5


81.
CH3
H
H
C6H5


82.
C2H5
H
H
C6H5


83.
CH(CH3)2
H
H
C6H5


84.
OCH3
H
H
C6H5


85.
CN
H
H
C6H5


86.
CF3
H
H
C6H5


87.
OCF3
H
H
C6H5


88.
OCHF2
H
H
C6H5


89.
Cl
H
H
cyclopropyl


90.
Br
H
H
cyclopropyl


91.
F
H
H
cyclopropyl


92.
CH3
H
H
cyclopropyl


93.
C2H5
H
H
cyclopropyl


94.
CH(CH3)2
H
H
cyclopropyl


95.
OCH3
H
H
cyclopropyl


96.
CN
H
H
cyclopropyl


97.
CF3
H
H
cyclopropyl


98.
OCF3
H
H
cyclopropyl


99.
OCHF2
H
H
cyclopropyl


100.
Cl
H
H
CH2-cyclopropyl


101.
Br
H
H
CH2-cyclopropyl


102.
F
H
H
CH2-cyclopropyl


103.
CH3
H
H
CH2-cyclopropyl


104.
C2H5
H
H
CH2-cyclopropyl


105.
CH(CH3)2
H
H
CH2-cyclopropyl


106.
OCH3
H
H
CH2-cyclopropyl


107.
CN
H
H
CH2-cyclopropyl


108.
CF3
H
H
CH2-cyclopropyl


109.
OCF3
H
H
CH2-cyclopropyl


110.
OCHF2
H
H
CH2-cyclopropyl


111.
Cl
H
H
cyclobutyl


112.
Br
H
H
cyclobutyl


113.
F
H
H
cyclobutyl


114.
CH3
H
H
cyclobutyl


115.
C2H5
H
H
cyclobutyl


116.
CH(CH3)2
H
H
cyclobutyl


117.
OCH3
H
H
cyclobutyl


118.
CN
H
H
cyclobutyl


119.
CF3
H
H
cyclobutyl


120.
OCF3
H
H
cyclobutyl


121.
OCHF2
H
H
cyclobutyl


122.
Cl
H
H
cyclopentyl


123.
Br
H
H
cyclopentyl


124.
F
H
H
cyclopentyl


125.
CH3
H
H
cyclopentyl


126.
C2H5
H
H
cyclopentyl


127.
CH(CH3)2
H
H
cyclopentyl


128.
OCH3
H
H
cyclopentyl


129.
CN
H
H
cyclopentyl


130.
CF3
H
H
cyclopentyl


131.
OCF3
H
H
cyclopentyl


132.
OCHF2
H
H
cyclopentyl


133.
Cl
H
H
cyclohexyl


134.
Br
H
H
cyclohexyl


135.
F
H
H
cyclohexyl


136.
CH3
H
H
cyclohexyl


137.
C2H5
H
H
cyclohexyl


138.
CH(CH3)2
H
H
cyclohexyl


139.
OCH3
H
H
cyclohexyl


140.
CN
H
H
cyclohexyl


141.
CF3
H
H
cyclohexyl


142.
OCF3
H
H
cyclohexyl


143.
OCHF2
H
H
cyclohexyl


144.
H
Cl
H
H


145.
H
Br
H
H


146.
H
F
H
H


147.
H
CH3
H
H


148.
H
C2H5
H
H


149.
H
CH(CH3)2
H
H


150.
H
OCH3
H
H


151.
H
CN
H
H


152.
H
CF3
H
H


153.
H
OCF3
H
H


154.
H
OCHF2
H
H


155.
H
Cl
H
CH3


156.
H
Br
H
CH3


157.
H
F
H
CH3


158.
H
CH3
H
CH3


159.
H
C2H5
H
CH3


160.
H
CH(CH3)2
H
CH3


161.
H
OCH3
H
CH3


162.
H
CN
H
CH3


163.
H
CF3
H
CH3


164.
H
OCF3
H
CH3


165.
H
OCHF2
H
CH3


166.
H
Cl
H
C2H5


167.
H
Br
H
C2H5


168.
H
F
H
C2H5


169.
H
CH3
H
C2H5


170.
H
C2H5
H
C2H5


171.
H
CH(CH3)2
H
C2H5


172.
H
OCH3
H
C2H5


173.
H
CN
H
C2H5


174.
H
CF3
H
C2H5


175.
H
OCF3
H
C2H5


176.
H
OCHF2
H
C2H5


177.
H
Cl
H
n-C3H7


178.
H
Br
H
n-C3H7


179.
H
F
H
n-C3H7


180.
H
CH3
H
n-C3H7


181.
H
C2H5
H
n-C3H7


182.
H
CH(CH3)2
H
n-C3H7


183.
H
OCH3
H
n-C3H7


184.
H
CN
H
n-C3H7


185.
H
CF3
H
n-C3H7


186.
H
OCF3
H
n-C3H7


187.
H
OCHF2
H
n-C3H7


188.
H
Cl
H
CH(CH3)2


189.
H
Br
H
CH(CH3)2


190.
H
F
H
CH(CH3)2


191.
H
CH3
H
CH(CH3)2


192.
H
C2H5
H
CH(CH3)2


193.
H
CH(CH3)2
H
CH(CH3)2


194.
H
OCH3
H
CH(CH3)2


195.
H
CN
H
CH(CH3)2


196.
H
CF3
H
CH(CH3)2


197.
H
OCF3
H
CH(CH3)2


198.
H
OCHF2
H
CH(CH3)2


199.
H
Cl
H
n-C4H9


200.
H
Br
H
n-C4H9


201.
H
F
H
n-C4H9


202.
H
CH3
H
n-C4H9


203.
H
C2H5
H
n-C4H9


204.
H
CH(CH3)2
H
n-C4H9


205.
H
OCH3
H
n-C4H9


206.
H
CN
H
n-C4H9


207.
H
CF3
H
n-C4H9


208.
H
OCF3
H
n-C4H9


209.
H
OCHF2
H
n-C4H9


210.
H
Cl
H
C(CH3)3


211.
H
Br
H
C(CH3)3


212.
H
F
H
C(CH3)3


213.
H
CH3
H
C(CH3)3


214.
H
C2H5
H
C(CH3)3


215.
H
CH(CH3)2
H
C(CH3)3


216.
H
OCH3
H
C(CH3)3


217.
H
CN
H
C(CH3)3


218.
H
CF3
H
C(CH3)3


219.
H
OCF3
H
C(CH3)3


220.
H
OCHF2
H
C(CH3)3


221.
H
Cl
H
C6H5


222.
H
Br
H
C6H5


223.
H
F
H
C6H5


224.
H
CH3
H
C6H5


225.
H
C2H5
H
C6H5


226.
H
CH(CH3)2
H
C6H5


227.
H
OCH3
H
C6H5


228.
H
CN
H
C6H5


229.
H
CF3
H
C6H5


230.
H
OCF3
H
C6H5


231.
H
OCHF2
H
C6H5


232.
H
Cl
H
cyclopropyl


233.
H
Br
H
cyclopropyl


234.
H
F
H
cyclopropyl


235.
H
CH3
H
cyclopropyl


236.
H
C2H5
H
cyclopropyl


237.
H
CH(CH3)2
H
cyclopropyl


238.
H
OCH3
H
cyclopropyl


239.
H
CN
H
cyclopropyl


240.
H
CF3
H
cyclopropyl


241.
H
OCF3
H
cyclopropyl


242.
H
OCHF2
H
cyclopropyl


243.
H
Cl
H
CH2-cyclopropyl


244.
H
Br
H
CH2-cyclopropyl


245.
H
F
H
CH2-cyclopropyl


246.
H
CH3
H
CH2-cyclopropyl


247.
H
C2H5
H
CH2-cyclopropyl


248.
H
CH(CH3)2
H
CH2-cyclopropyl


249.
H
OCH3
H
CH2-cyclopropyl


250.
H
CN
H
CH2-cyclopropyl


251.
H
CF3
H
CH2-cyclopropyl


252.
H
OCF3
H
CH2-cyclopropyl


253.
H
OCHF2
H
CH2-cyclopropyl


254.
H
Cl
H
cyclobutyl


255.
H
Br
H
cyclobutyl


256.
H
F
H
cyclobutyl


257.
H
CH3
H
cyclobutyl


258.
H
C2H5
H
cyclobutyl


259.
H
CH(CH3)2
H
cyclobuty).


260.
H
OCH3
H
cyclobutyl


261.
H
CN
H
cyclobutyl


262.
H
CF3
H
cyclobutyl


263.
H
OCF3
H
cyclobutyl


264.
H
OCHF2
H
cyclobutyl


265.
H
Cl
H
cyclopentyl


266.
H
Br
H
cyclopentyl


267.
H
F
H
cyclopentyl


268.
H
CH3
H
cyclopentyl


269.
H
C2H5
H
cyclopentyl


270.
H
CH(CH3)2
H
cyclopentyl


271.
H
OCH3
H
cyclopentyl


272.
H
CN
H
cyclopentyl


273.
H
CF3
H
cyclopentyl


274.
H
OCF3
H
cyclopentyl


275.
H
OCHF2
H
cyclopentyl


276.
H
Cl
H
cyclohexyl


277.
H
Br
H
cyclohexyl


278.
H
F
H
cyclohexyl


279.
H
CH3
H
cyclohexyl


280.
H
C2H5
H
cyclohexyl


281.
H
CH(CH3)2
H
cyclohexyl


282.
H
OCH3
H
cyclohexyl


283.
H
CN
H
cyclohexyl


284.
H
CF3
H
cyclohexyl


285.
H
OCF3
H
cyclohexyl


286.
H
OCHF2
H
cyclohexyl


287.
CF3
Br
H
H


288.
CF3
OCH3
H
H


289.
CF3
Cl
H
H


290.
CF3
F
H
H


291.
CF3
CH3
H
H


292.
CF3
C2H5
H
H


293.
CF3
CF3
H
H


294.
CF3
OCF3
H
H


295.
CF3
OCHF2
H
H


296.
CF3
Br
H
CH3


297.
CF3
OCH3
H
CH3


298.
CF3
Cl
H
CH3


299.
CF3
F
H
CH3


300.
CF3
CH3
H
CH3


301.
CF3
C2H5
H
CH3


302.
CF3
CF3
H
CH3


303.
CF3
OCF3
H
CH3


304.
CF3
OCHF2
H
CH3


305.
CF3
Br
H
C2H5


306.
CF3
OCH3
H
C2H5


307.
CF3
Cl
H
C2H5


308.
CF3
F
H
C2H5


309.
CF3
CH3
H
C2H5


310.
CF3
C2H5
H
C2H5


311.
CF3
CF3
H
C2H5


312.
CF3
OCF3
H
C2H5


313.
CF3
OCHF2
H
C2H5


314.
CF3
Br
H
n-C3H7


315.
CF3
OCH3
H
n-C3H7


316.
CF3
Cl
H
n-C3H7


317.
CF3
F
H
n-C3H7


318.
CF3
CH3
H
n-C3H7


319.
CF3
C2H5
H
n-C3H7


320.
CF3
CF3
H
n-C3H7


321.
CF3
OCF3
H
n-C3H7


322.
CF3
OCHF2
H
n-C3H7


323.
CF3
Br
H
CH(CH3)2


324.
CF3
OCH3
H
CH(CH3)2


325.
CF3
Cl
H
CH(CH3)2


326.
CF3
F
H
CH(CH3)2


327.
CF3
CH3
H
CH(CH3)2


328.
CF3
C2H5
H
CH(CH3)2


329.
CF3
CF3
H
CH(CH3)2


330.
CF3
OCF3
H
CH(CH3)2


331.
CF3
OCHF2
H
CH(CH3)2


332.
CF3
Br
H
n-C4H9


333.
CF3
OCH3
H
n-C4H9


334.
CF3
Cl
H
n-C4H9


335.
CF3
F
H
n-C4H9


336.
CF3
CH3
H
n-C4H9


337.
CF3
C2H5
H
n-C4H9


338.
CF3
CF3
H
n-C4H9


339.
CF3
OCF3
H
n-C4H9


340.
CF3
OCHF2
H
n-C4H9


341.
CF3
Br
H
C(CH3)3


342.
CF3
OCH3
H
C(CH3)3


343.
CF3
Cl
H
C(CH3)3


344.
CF3
F
H
C(CH3)3


345.
CF3
CH3
H
C(CH3)3


346.
CF3
C2H5
H
C(CH3)3


347.
CF3
CF3
H
C(CH3)3


348.
CF3
OCF3
H
C(CH3)3


349.
CF3
OCHF2
H
C(CH3)3


350.
CF3
Br
H
C6H5


351.
CF3
OCH3
H
C6H5


352.
CF3
Cl
H
C6H5


353.
CF3
F
H
C6H5


354.
CF3
CH3
H
C6H5


355.
CF3
C2H5
H
C6H5


356.
CF3
CF3
H
C6H5


357.
CF3
OCF3
H
C6H5


358.
CF3
OCHF2
H
C6H5


359.
CF3
Br
H
cyclopropyl


360.
CF3
OCH3
H
cyclopropyl


361.
CF3
Cl
H
cyclopropyl


362.
CF3
F
H
cyclopropyl


363.
CF3
CH3
H
cyclopropyl


364.
CF3
C2H5
H
cyclopropyl


365.
CF3
CF3
H
cyclopropyl


366.
CF3
OCF3
H
cyclopropyl


367.
CF3
OCHF2
H
cyclopropyl


368.
CF3
Br
H
CH2-cyclopropyl


369.
CF3
OCH3
H
CH2-cyclopropyl


370.
CF3
Cl
H
CH2-cyclopropyl


371.
CF3
F
H
CH2-cyclopropyl


372.
CF3
CH3
H
CH2-cyclopropyl


373.
CF3
C2H5
H
CH2-cyclopropyl


374.
CF3
CF3
H
CH2-cyclopropyl


375.
CF3
OCF3
H
CH2-cyclopropyl


376.
CF3
OCHF2
H
CH2-cyclopropyl


377.
CF3
Br
H
cyclobutyl


378.
CF3
OCH3
H
cyclobutyl


379.
CF3
Cl
H
cyclobutyl


380.
CF3
F
H
cyclobutyl


381.
CF3
CH3
H
cyclobutyl


382.
CF3
C2H5
H
cyclobutyl


383.
CF3
CF3
H
cyclobutyl


384.
CF3
OCF3
H
cyclobutyl


385.
CF3
OCHF2
H
cyclobutyl


386.
CF3
Br
H
cyclopentyl


387.
CF3
OCH3
H
cyclopentyl


388.
CF3
Cl
H
cyclopentyl


389.
CF3
F
H
cyclopentyl


390.
CF3
CH3
H
cyclopentyl


391.
CF3
C2H5
H
cyclopentyl


392.
CF3
CF3
H
cyclopentyl


393.
CF3
OCF3
H
cyclopentyl


394.
CF3
OCHF2
H
cyclopentyl


395.
CF3
Br
H
cyclohexyl


396.
CF3
OCH3
H
cyclohexyl


397.
CF3
Cl
H
cyclohexyl


398.
CF3
F
H
cyclohexyl


399.
CF3
CH3
H
cyclohexyl


400.
CF3
C2H5
H
cyclohexyl


401.
CF3
CF3
H
cyclohexyl


402.
CF3
OCF3
H
cyclohexyl


403.
CF3
OCHF2
H
cyclohexyl


404.
CF3
H
Br
H


405.
CF3
H
OCH3
H


406.
CF3
H
Cl
H


407.
CF3
H
F
H


408.
CF3
H
CH3
H


409.
CF3
H
C2H5
H


410.
CF3
H
CF3
H


411.
CF3
H
OCF3
H


412.
CF3
H
OCHF2
H


413.
CF3
H
Br
CH3


414.
CF3
H
OCH3
CH3


415.
CF3
H
Cl
CH3


416.
CF3
H
F
CH3


417.
CF3
H
CH3
CH3


418.
CF3
H
C2H5
CH3


419.
CF3
H
CF3
CH3


420.
CF3
H
OCF3
CH3


421.
CF3
H
OCHF2
CH3


422.
CF3
H
Br
C2H5


423.
CF3
H
OCH3
C2H5


424.
CF3
H
Cl
C2H5


425.
CF3
H
F
C2H5


426.
CF3
H
CH3
C2H5


427.
CF3
H
C2H5
C2H5


428.
CF3
H
CF3
C2H5


429.
CF3
H
OCF3
C2H5


430.
CF3
H
OCHF2
C2H5


431.
CF3
H
Br
n-C3H7


432.
CF3
H
OCH3
n-C3H7


433.
CF3
H
Cl
n-C3H7


434.
CF3
H
F
n-C3H7


435.
CF3
H
CH3
n-C3H7


436.
CF3
H
C2H5
n-C3H7


437.
CF3
H
CF3
n-C3H7


438.
CF3
H
OCF3
n-C3H7


439.
CF3
H
OCHF2
n-C3H7


440.
CF3
H
Br
CH(CH3)2


441.
CF3
H
OCH3
CH(CH3)2


442.
CF3
H
Cl
CH(CH3)2


443.
CF3
H
F
CH(CH3)2


444.
CF3
H
CH3
CH(CH3)2


445.
CF3
H
C2H5
CH(CH3)2


446.
CF3
H
CF3
CH(CH3)2


447.
CF3
H
OCF3
CH(CH3)2


448.
CF3
H
OCHF2
CH(CH3)2


449.
CF3
H
Br
n-C4H9


450.
CF3
H
OCH3
n-C4H9


451.
CF3
H
Cl
n-C4H9


452.
CF3
H
F
n-C4H9


453.
CF3
H
CH3
n-C4H9


454.
CF3
H
C2H5
n-C4H9


455.
CF3
H
CF3
n-C4H9


456.
CF3
H
OCF3
n-C4H9


457.
CF3
H
OCHF2
n-C4H9


458.
CF3
H
Br
C(CH3)3


459.
CF3
H
OCH3
C(CH3)3


460.
CF3
H
Cl
C(CH3)3


461.
CF3
H
F
C(CH3)3


462.
CF3
H
CH3
C(CH3)3


463.
CF3
H
C2H5
C(CH3)3


464.
CF3
H
CF3
C(CH3)3


465.
CF3
H
OCF3
C(CH3)3


466.
CF3
H
OCHF2
C(CH3)3


467.
CF3
H
Br
C6H5


468.
CF3
H
OCH3
C6H5


469.
CF3
H
Cl
C6H5


470.
CF3
H
F
C6H5


471.
CF3
H
CH3
C6H5


472.
CF3
H
C2H5
C6H5


473.
CF3
H
CF3
C6H5


474.
CF3
H
OCF3
C6H5


475.
CF3
H
OCHF2
C6H5


476.
CF3
H
Br
cyclopropyl


477.
CF3
H
OCH3
cyclopropyl


478.
CF3
H
Cl
cyclopropyl


479.
CF3
H
F
cyclopropyl


480.
CF3
H
CH3
cyclopropyl


481.
CF3
H
C2H5
cyclopropyl


482.
CF3
H
CF3
cyclopropyl


483.
CF3
H
OCF3
cyclopropyl


484.
CF3
H
OCHF2
cyclopropyl


485.
CF3
H
Br
CH2-cyclopropyl


486.
CF3
H
OCH3
CH2-cyclopropyl


487.
CF3
H
Cl
CH2-cyclopropyl


488.
CF3
H
F
CH2-cyclopropyl


489.
CF3
H
CH3
CH2-cyclopropyl


490.
CF3
H
C2H5
CH2-cyclopropyl


491.
CF3
H
CF3
CH2-cyclopropyl


492.
CF3
H
OCF3
CH2-cyclopropyl


493.
CF3
H
OCHF2
CH2-cyclopropyl


494.
CF3
H
Br
cyclobutyl


495.
CF3
H
OCH3
cyclobutyl


496.
CF3
H
Cl
cyclobutyl


497.
CF3
H
F
cyclobutyl


498.
CF3
H
CH3
cyclobutyl


499.
CF3
H
C2H5
cyclobutyl


500.
CF3
H
CF3
cyclobutyl


501.
CF3
H
OCF3
cyclobutyl


502.
CF3
H
OCHF2
cyclobutyl


503.
CF3
H
Br
cyclopentyl


504.
CF3
H
OCH3
cyclopentyl


505.
CF3
H
Cl
cyclopentyl


506.
CF3
H
F
cyclopentyl


507.
CF3
H
CH3
cyclopentyl


508.
CF3
H
C2H5
cyclopentyl


509.
CF3
H
CF3
cyclopentyl


510.
CF3
H
OCF3
cyclopentyl


511.
CF3
H
OCHF2
cyclopentyl


512.
CF3
H
Br
cyclohexyl


513.
CF3
H
OCH3
cyclohexyl


514.
CF3
H
Cl
cyclohexyl


515.
CF3
H
F
cyclohexyl


516.
CF3
H
CH3
cyclohexyl


517.
CF3
H
C2H5
cyclohexyl


518.
CF3
H
CF3
cyclohexyl


519.
CF3
H
OCF3
cyclohexyl


520.
CF3
H
OCHF2
cyclohexyl


521.
OCF3
Br
H
H


522.
OCF3
OCH3
H
H


523.
OCF3
Cl
H
H


524.
OCF3
F
H
H


525.
OCF3
CH3
H
H


526.
OCF3
C2H5
H
H


527.
OCF3
CF3
H
H


528.
OCF3
OCF3
H
H


529.
OCF3
OCHF2
H
H


530.
OCF3
Br
H
CH3


531.
OCF3
OCH3
H
CH3


532.
OCF3
Cl
H
CH3


533.
OCF3
F
H
CH3


534.
OCF3
Cl3
H
CH3


535.
OCF3
C2H5
H
CH3


536.
OCF3
CF3
H
CH3


537.
OCF3
OCF3
H
CH3


538.
OCF3
OCHF2
H
CH3


539.
OCF3
Br
H
C2H5


540.
OCF3
OCH3
H
C2H5


541.
OCF3
Cl
H
C2H5


542.
OCF3
F
H
C2H5


543.
OCF3
CH3
H
C2H5


544.
OCF3
C2H5
H
C2H5


545.
OCF3
CF3
H
C2H5


546.
OCF3
OCF3
H
C2H5


547.
OCF3
OCHF2
H
C2H5


548.
OCF3
Br
H
n-C3H7


549.
OCF3
OCH3
H
n-C3H7


550.
OCF3
Cl
H
n-C3H7


551.
OCF3
F
H
n-C3H7


552.
OCF3
CH3
H
n-C3H7


553.
OCF3
C2H5
H
n-C3H7


554.
OCF3
CF3
H
n-C3H7


555.
OCF3
OCF3
H
n-C3H7


556.
OCF3
OCHF2
H
n-C3H7


557.
OCF3
Br
H
CH(CH3)2


558.
OCF3
OCH3
H
CH(CH3)2


559.
OCF3
Cl
H
CH(CH3)2


560.
OCF3
F
H
CH(CH3)2


561.
OCF3
CH3
H
CH(CH3)2


562.
OCF3
C2H5
H
CH(CH3)2


563.
OCF3
CF3
H
CH(CH3)2


564.
OCF3
OCF3
H
CH(CH3)2


565.
OCF3
OCHF2
H
CH(CH3)2


566.
OCF3
Br
H
n-C4H9


567.
OCF3
OCH3
H
n-C4H9


568.
OCF3
Cl
H
n-C4H9


569.
OCF3
F
H
n-C4H9


570.
OCF3
CH3
H
n-C4H9


571.
OCF3
C2H5
H
n-C4H9


572.
OCF3
CF3
H
n-C4H9


573.
OCF3
OCF3
H
n-C4H9


574.
OCF3
OCHF2
H
n-C4H9


575.
OCF3
Br
H
C(CH3)3


576.
OCF3
OCH3
H
C(CH3)3


577.
OCF3
Cl
H
C(CH3)3


578.
OCF3
F
H
C(CH3)3


579.
OCF3
CH3
H
C(CH3)3


580.
OCF3
C2H5
H
C(CH3)3


581.
OCF3
CF3
H
C(CH3)3


582.
OCF3
OCF3
H
C(CH3)3


583.
OCF3
OCHF2
H
C(CH3)3


584.
OCF3
Br
H
C6H5


585.
OCF3
OCH3
H
C6H5


586.
OCF3
Cl
H
C6H5


587.
OCF3
F
H
C6H5


588.
OCF3
CH3
H
C6H5


589.
OCF3
C2H5
H
C6H5


590.
OCF3
CF3
H
C6H5


591.
OCF3
OCF3
H
C6H5


592.
OCF3
OCHF2
H
C6H5


593.
OCF3
Br
H
cyclopropyl


594.
OCF3
OCH3
H
cyclopropyl


595.
OCF3
Cl
H
cyclopropyl


596.
OCF3
F
H
cyclopropyl


597.
OCF3
CH3
H
cyclopropyl


598.
OCF3
C2H5
H
cyclopropyl


599.
OCF3
CF3
H
cyclopropyl


600.
OCF3
OCF3
H
cyclopropyl


601.
OCF3
OCHF2
H
cyclopropyl


602.
OCF3
Br
H
CH2-cyclopropyl


603.
OCF3
OCH3
H
CH2-cyclopropyl


604.
OCF3
Cl
H
CH2-cyclopropyl


605.
OCF3
F
H
CH2-cyclopropyl


606.
OCF3
CH3
H
CH2-cyclopropyl


607.
OCF3
C2H5
H
CH2-cyclopropyl


608.
OCF3
OCF3
H
CH2-cyclopropyl


609.
OCF3
CF3
H
CH2-cyclopropyl


610.
OCF3
OCHF2
H
CH2-cyclopropyl


611.
OCF3
Br
H
cyclobutyl


612.
OCF3
OCH3
H
cyclobutyl


613.
OCF3
Cl
H
cyclobutyl


614.
OCF3
F
H
cyclobutyl


615.
OCF3
CH3
H
cyclobutyl


616.
OCF3
C2H5
H
cyclobutyl


617.
OCF3
QCF3
H
cyclobutyl


618.
OCF3
CF3
H
cyclobutyl


619.
OCF3
OCHF2
H
cyclobutyl


620.
OCF3
Br
H
cyclopentyl


621.
OCF3
OCH3
H
cyclopentyl


622.
OCF3
Cl
H
cyclopentyl


623.
OCF3
F
H
cyclopentyl


624.
OCF3
CH3
H
cyclopentyl


625.
OCF3
C2H5
H
cyclopentyl


626.
OCF3
OCF3
H
cyclopentyl


627.
OCF3
CF3
H
cyclopentyl


628.
OCF3
OCHF2
H
cyclopentyl


629.
OCF3
Br
H
cyclohexyl


630.
OCF3
OCH3
H
cyclohexyl


631.
OCF3
Cl
H
cyclohexyl


632.
OCF3
F
H
cyclohexyl


633.
OCF3
CH3
H
cyclohexyl


634.
OCF3
C2H5
H
cyclohexyl


635.
OCF3
OCF3
H
cyclohexyl


636.
OCF3
CF3
H
cyclohexyl


637.
OCF3
OCHF2
H
cyclohexyl


638.
OCF3
H
Br
H


639.
OCF3
H
OCH3
H


640.
OCF3
H
Cl
H


641.
OCF3
H
F
H


642.
OCF3
H
CH3
H


643.
OCF3
H
C2H5
H


644.
OCF3
H
CF3
H


645.
OCF3
H
OCF3
H


646.
OCF3
H
OCHF2
H


647.
OCF3
H
Br
CH3


648.
OCF3
H
OCH3
CH3


649.
OCF3
H
Cl
CH3


650.
OCF3
H
F
CH3


651.
OCF3
H
CH3
CH3


652.
OCF3
H
C2H5
CH3


653.
OCF3
H
CF3
CH3


654.
OCF3
H
OCF3
CH3


655.
OCF3
H
OCHF2
CH3


656.
OCF3
H
Br
C2H5


657.
OCF3
H
OCH3
C2H5


658.
OCF3
H
Cl
C2H5


659.
OCF3
H
F
C2H5


660.
OCF3
H
CH3
C2H5


661.
OCF3
H
C2H5
C2H5


662.
OCF3
H
CF3
C2H5


663.
OCF3
H
OCF3
C2H5


664.
OCF3
H
OCHF2
C2H5


665.
OCF3
H
Br
n-C3H7


666.
OCF3
H
OCH3
n-C3H7


667.
OCF3
H
Cl
n-C3H7


668.
OCF3
H
F
n-C3H7


669.
OCF3
H
CH3
n-C3H7


670.
OCF3
H
C2H5
n-C3H7


671.
OCF3
H
CF3
n-C3H7


672.
OCF3
H
OCF3
n-C3H7


673.
OCF3
H
OCHF2
n-C3H7


674.
OCF3
H
Br
CH(CH3)2


675.
OCF3
H
OCH3
CH(CH3)2


676.
OCF3
H
Cl
CH(CH3)2


677.
OCF3
H
F
CH(CH3)2


678.
OCF3
H
CH3
CH(CH3)2


679.
OCF3
H
C2H5
CH(CH3)2


680.
OCF3
H
CF3
CH(CH3)2


681.
OCF3
H
OCF3
CH(CH3)2


682.
OCF3
H
OCHF2
CH(CH3)2


683.
OCF3
H
Br
n-C4H9


684.
OCF3
H
OCH3
n-C4H9


685.
OCF3
H
Cl
n-C4H9


686.
OCF3
H
F
n-C4H9


687.
OCF3
H
CH3
n-C4H9


688.
OCF3
H
C2H5
n-C4H9


689.
OCF3
H
CF3
n-C4H9


690.
OCF3
H
OCF3
n-C4H9


691.
OCF3
H
OCHF2
n-C4H9


692.
OCF3
H
Br
C(CH3)3


693.
OCF3
H
OCH3
C(CH3)3


694.
OCF3
H
Cl
C(CH3)3


695.
OCF3
H
F
C(CH3)3


696.
OCF3
H
CH3
C(CH3)3


697.
OCF3
H
C2H5
C(CH3)3


698.
OCF3
H
CF3
C(CH3)3


699.
OCF3
H
OCF3
C(CH3)3


700.
OCF3
H
OCHF2
C(CH3)3


701.
OCF3
H
Br
C6H5


702.
OCF3
H
OCH3
C6H5


703.
OCF3
H
Cl
C6H5


704.
OCF3
H
F
C6H5


705.
OCF3
H
CH3
C6H5


706.
OCF3
H
C2H5
C6H5


707.
OCF3
H
CF3
C6H5


708.
OCF3
H
OCF3
C6H5


709.
OCF3
H
OCHF2
C6H5


710.
OCF3
H
Br
cyclopropyl


711.
OCF3
H
OCH3
cyclopropyl


712.
OCF3
H
Cl
cyclopropyl


713.
OCF3
H
F
cyclopropyl


714.
OCF3
H
CH3
cyclopropyl


715.
OCF3
H
C2H5
cyclopropyl


716.
OCF3
H
CF3
cyclopropyl


717.
OCF3
H
OCF3
cyclopropyl


718.
OCF3
H
OCHF2
cyclopropyl


719.
OCF3
H
Br
CH2-cyclopropyl


720.
OCF3
H
OCH3
CH2-cyclopropyl


721.
OCF3
H
Cl
CH2-cyclopropyl


722.
OCF3
H
F
CH2-cyclopropyl


723.
OCF3
H
CH3
CH2-cyclopropyl


724.
OCF3
H
C2H5
CH2-cyclopropyl


725.
OCF3
H
CF3
CH2-cyclopropyl


726.
OCF3
H
OCF3
CH2-cyclopropyl


727.
OCF3
H
OCHF2
CH2-cyclopropyl


728.
OCF3
H
Br
cyclobutyl


729.
OCF3
H
OCH3
cyclobutyl


730.
OCF3
H
Cl
cyclobutyl


731.
OCF3
H
F
cyclobutyl


732.
OCF3
H
CH3
cyclobutyl


733.
OCF3
H
C2H5
cyclobutyl


734.
OCF3
H
CF3
cyclobutyl


735.
OCF3
H
OCF3
cyclobutyl


736.
OCF3
H
OCHF2
cyclobutyl


737.
OCF3
H
Br
cyclopentyl


738.
OCF3
H
OCH3
cyclopentyl


739.
OCF3
H
Cl
cyclopentyl


740.
OCF3
H
F
cyclopentyl


741.
OCF3
H
CH3
cyclopentyl


742.
OCF3
H
C2H5
cyclopentyl


743.
OCF3
H
CF3
cyclopentyl


744.
OCF3
H
OCF3
cyclopentyl


745.
OCF3
H
OCHF2
cyclopentyl


746.
OCF3
H
Br
cyclohexyl


747.
OCF3
H
OCH3
cyclohexyl


748.
OCF3
H
Cl
cyclohexyl


749.
OCF3
H
F
cyclohexyl


750.
OCF3
H
CH3
cyclohexyl


751.
OCF3
H
C2H5
cyclohexyl


752.
OCF3
H
CF3
cyclohexyl


753.
OCF3
H
OCF3
cyclohexyl


754.
OCF3
H
OCHF2
cyclohexyl


755.
OCHF2
Br
H
H


756.
OCHF2
OCH3
H
H


757.
OCHF2
Cl
H
H


758.
OCHF2
F
H
H


759.
OCHF2
CH3
H
H


760.
OCHF2
C2H5
H
H


761.
OCHF2
OCF3
H
H


762.
OCHF2
CF3
H
H


763.
OCHF2
Br
H
CH3


764.
OCHF2
OCH3
H
CH3


765.
OCHF2
Cl
H
CH3


766.
OCHF2
F
H
CH3


767.
OCHF2
CH3
H
CH3


768.
OCHF2
C2H5
H
CH3


769.
OCHF2
OCF3
H
CH3


770.
OCHF2
CF3
H
CH3


771.
OCHF2
Br
H
C2H5


772.
OCHF2
OCH3
H
C2H5


773.
OCHF2
Cl
H
C2H5


774.
OCHF2
F
H
C2H5


775.
OCHF2
CH3
H
C2H5


776.
OCHF2
C2H5
H
C2H5


777.
OCHF2
OCF3
H
C2H5


778.
OCHF2
CF3
H
C2H5


779.
OCHF2
Br
H
n-C3H7


780.
OCHF2
OCH3
H
n-C3H7


781.
OCHF2
Cl
H
n-C3H7


782.
OCHF2
F
H
n-C3H7


783.
OCHF2
CH3
H
n-C3H7


784.
OCHF2
C2H5
H
n-C3H7


785.
OCHF2
OCF3
H
n-C3H7


786.
OCHF2
CF3
H
n-C3H7


787.
OCHF2
Br
H
CH(CH3)2


788.
OCHF2
OCH3
H
CH(CH3)2


789.
OCHF2
Cl
H
CH(CH3)2


790.
OCHF2
F
H
CH(CH3)2


791.
OCHF2
CH3
H
CH(CH3)2


792.
OCHF2
C2H5
H
CH(CH3)2


793.
OCHF2
OCF3
H
CH(CH3)2


794.
OCHF2
CF3
H
CH(CH3)2


795.
OCHF2
Br
H
n-C4H9


796.
OCHF2
OCH3
H
n-C4H9


797.
OCHF2
Cl
H
n-C4H9


798.
OCHF2
F
H
n-C4H9


799.
OCHF2
CH3
H
n-C4H9


800.
OCHF2
C2H5
H
n-C4H9


801.
OCHF2
OCF3
H
n-C4H9


802.
OCHF2
CF3
H
n-C4H9


803.
OCHF2
Br
H
C(CH3)3


804.
OCHF2
OCH3
H
C(CH3)3


805.
OCHF2
Cl
H
C(CH3)3


806.
OCHF2
F
H
C(CH3)3


807.
OCHF2
CH3
H
C(CH3)3


808.
OCHF2
C2H5
H
C(CH3)3


809.
OCHF2
OCF3
H
C(CH3)3


810.
OCHF2
CF3
H
C(CH3)3


811.
OCHF2
Br
H
C6H5


812.
OCHF2
OCH3
H
C6H5


813.
OCHF2
Cl
H
C6H5


814.
OCHF2
F
H
C6H5


815.
OCHF2
CH3
H
C6H5


816.
OCHF2
C2H5
H
C6H5


817.
OCHF2
OCF3
H
C6H5


818.
OCHF2
CF3
H
C6H5


819.
OCHF2
Br
H
cyclopropyl


820.
OCHF2
OCH3
H
cyclopropyl


821.
OCHF2
Cl
H
cyclopropyl


822.
OCHF2
F
H
cyclopropyl


823.
OCHF2
CH3
H
cyclopropyl


824.
OCHF2
C2H5
H
cyclopropyl


825.
OCHF2
OCF3
H
cyclopropyl


826.
OCHF2
CF3
H
cyclopropyl


827.
OCHF2
Br
H
CH2-cyclopropyl


828.
OCHF2
OCH3
H
CH2-cyclopropyl


829.
OCHF2
Cl
H
CH2-cyclopropyl


830.
OCHF2
F
H
CH2-cyclopropyl


831.
OCHF2
CH3
H
CH2-cyclopropyl


832.
OCHF2
C2H5
H
CH2-cyclopropyl


833.
OCHF2
OCF3
H
CH2-cyclopropyl


834.
OCHF2
CF3
H
CH2-cyclopropyl


835.
OCHF2
Br
H
cyclobutyl


836.
OCHF2
OCH3
H
cyclobutyl


837.
OCHF2
Cl
H
cyclobutyl


838.
OCHF2
F
H
cyclobutyl


839.
OCHF2
CH3
H
cyclobutyl


840.
OCHF2
C2H5
H
cyclobutyl


841.
OCHF2
OCF3
H
cyclobutyl


842.
OCHF2
CF3
H
cyclobutyl


843.
OCHF2
Br
H
cyclopentyl


844.
OCHF2
OCH3
H
cyclopentyl


845.
OCHF2
Cl
H
cyclopentyl


846.
OCHF2
F
H
cyclopentyl


847.
OCHF2
CH3
H
cyclopentyl


848.
OCHF2
C2H5
H
cyclopentyl


849.
OCHF2
OCF3
H
cyclopentyl


850.
OCHF2
CF3
H
cyclopentyl


851.
OCHF2
Br
H
cyclohexyl


852.
OCHF2
OCH3
H
cyclohexyl


853.
OCHF2
Cl
H
cyclohexyl


854.
OCHF2
F
H
cyclohexyl


855.
OCHF2
CH3
H
cyclohexyl


856.
OCHF2
C2H5
H
cyclohexyl


857.
OCHF2
OCF3
H
cyclohexyl


858.
OCHF2
CF3
H
cyclohexyl


859.
OCHF2
H
Br
H


860.
OCHF2
H
OCH3
H


861.
OCHF2
H
Cl
H


862.
OCHF2
H
F
H


863.
OCHF2
H
CH3
H


864.
OCHF2
H
C2H5
H


865.
OCHF2
H
OCF3
H


866.
OCHF2
H
CF3
H


867.
OCHF2
H
Br
CH3


868.
OCHF2
H
OCH3
CH3


869.
OCHF2
H
Cl
CH3


870.
OCHF2
H
F
CH3


871.
OCHF2
H
CH3
CH3


872.
OCHF2
H
C2H5
CH3


873.
OCHF2
H
OCF3
CH3


874.
OCHF2
H
CF3
CH3


875.
OCHF2
H
Br
C2H5


876.
OCHF2
H
OCH3
C2H5


877.
OCHF2
H
Cl
C2H5


878.
OCHF2
H
F
C2H5


879.
OCHF2
H
CH3
C2H5


880.
OCHF2
H
C2H5
C2H5


881.
OCHF2
H
OCF3
C2H5


882.
OCHF2
H
CF3
C2H5


883.
OCHF2
H
Br
n-C3H7


884.
OCHF2
H
OCH3
n-C3H7


885.
OCHF2
H
Cl
n-C3H7


886.
OCHF2
H
F
n-C3H7


887.
OCHF2
H
CH3
n-C3H7


888.
OCHF2
H
C2H5
n-C3H7


889.
OCHF2
H
OCF3
n-C3H7


890.
OCHF2
H
CF3
n-C3H7


891.
OCHF2
H
Br
CH(CH3)2


892.
OCHF2
H
OCH3
CH(CH3)2


893.
OCHF2
H
Cl
CH(CH3)2


894.
OCHF2
H
F
CH(CH3)2


895.
OCHF2
H
CH3
CH(CH3)2


896.
OCHF2
H
C2H5
CH(CH3)2


897.
OCHF2
H
OCF3
CH(CH3)2


898.
OCHF2
H
CF3
CH(CH3)2


899.
OCHF2
H
Br
n-C4H9


900.
OCHF2
H
OCH3
n-C4H9


901.
OCHF2
H
Cl
n-C4H9


902.
OCHF2
H
F
n-C4H9


903.
OCHF2
H
CH3
n-C4H9


904.
OCHF2
H
C2H5
n-C4H9


905.
OCHF2
H
OCF3
n-C4H9


906.
OCHF2
H
CF3
n-C4H9


907.
OCHF2
H
Br
C(CH3)3


908.
OCHF2
H
OCH3
C(CH3)3


909.
OCHF2
H
Cl
C(CH3)3


910.
OCHF2
H
F
C(CH3)3


911.
OCHF2
H
CH3
C(CH3)3


912.
OCHF2
H
C2H5
C(CH3)3


913.
OCHF2
H
OCF3
C(CH3)3


914.
OCHF2
H
CF3
C(CH3)3


915.
OCHF2
H
Br
C6H5


916.
OCHF2
H
OCH3
C6H5


917.
OCHF2
H
Cl
C6H5


918.
OCHF2
H
F
C6H5


919.
OCHF2
H
CH3
C6H5


920.
OCHF2
H
C2H5
C6H5


921.
OCHF2
H
OCF3
C6H5


922.
OCHF2
H
CF3
C6H5


923.
OCHF2
H
Br
cyclopropyl


924.
OCHF2
H
OCH3
cyclopropyl


925.
OCHF2
H
Cl
cyclopropyl


926.
OCHF2
H
F
cyclopropyl


927.
OCHF2
H
CH3
cyclopropyl


928.
OCHF2
H
C2H5
cyclopropyl


929.
OCHF2
H
OCF3
cyclopropyl


930.
OCHF2
H
CF3
cyclopropyl


931.
OCHF2
H
Br
CH2-cyclopropyl


932.
OCHF2
H
OCH3
CH2-cyclopropyl


933.
OCHF2
H
Cl
CH2-cyclopropyl


934.
OCHF2
H
F
CH2-cyclopropyl


935.
OCHF2
H
CH3
CH2-cyclopropyl


936.
OCHF2
H
C2H5
CH2-cyclopropyl


937.
OCHF2
H
OCF3
CH2-cyclopropyl


938.
OCHF2
H
CF3
CH2-cyclopropyl


939.
OCHF2
H
Br
cyclobutyl


940.
OCHF2
H
OCH3
cyclobutyl


941.
OCHF2
H
Cl
cyclobutyl


942.
OCHF2
H
F
cyclobutyl


943.
OCHF2
H
CH3
cyclobutyl


944.
OCHF2
H
C2H5
cyclobutyl


945.
OCHF2
H
OCF3
cyclobutyl


946.
OCHF2
H
CF3
cyclobutyl


947.
OCHF2
H
Br
cyclopentyl


948.
OCHF2
H
OCH3
cyclopentyl


949.
OCHF2
H
Cl
cyclopentyl


950.
OCHF2
H
F
cyclopentyl


951.
OCHF2
H
CH3
cyclopentyl


952.
OCHF2
H
C2H5
cyclopentyl


953.
OCHF2
H
OCF3
cyclopentyl


954.
OCHF2
H
CF3
cyclopentyl


955.
OCHF2
H
Br
cyclohexyl


956.
OCHF2
H
OCH3
cyclohexyl


957.
OCHF2
H
Cl
cyclohexyl


958.
OCHF2
H
F
cyclohexyl


959.
OCHF2
H
CH3
cyclohexyl


960.
OCHF2
H
C2H5
cyclohexyl


961.
OCHF2
H
OCF3
cyclohexyl


962.
OCHF2
H
CF3
cyclohexyl


963.
OCH3
Br
H
H


964.
OCH3
OCH3
H
H


965.
OCH3
Cl
H
H


966.
OCH3
F
H
H


967.
OCH3
CH3
H
H


968.
OCH3
C2H5
H
H


969.
OCH3
CF3
H
H


970.
OCH3
OCF3
H
H


971.
OCH3
OCHF2
H
H


972.
OCH3
Br
H
CH3


973.
OCH3
OCH3
H
CH3


974.
OCH3
Cl
H
CH3


975.
OCH3
F
H
CH3


976.
OCH3
CH3
H
CH3


977.
OCH3
C2H5
H
CH3


978.
OCH3
CF3
H
CH3


979.
OCH3
OCF3
H
CH3


980.
OCH3
OCHF2
H
CH3


981.
OCH3
Br
H
C2H5


982.
OCH3
OCH3
H
C2H5


983.
OCH3
Cl
H
C2H5


984.
OCH3
F
H
C2H5


985.
OCH3
CH3
H
C2H5


986.
OCH3
C2H5
H
C2H5


987.
OCH3
CF3
H
C2H5


988.
OCH3
OCF3
H
C2H5


989.
OCH3
OCHF2
H
C2H5


990.
OCH3
Br
H
n-C3H7


991.
OCH3
OCH3
H
n-C3H7


992.
OCH3
Cl
H
n-C3H7


993.
OCH3
F
H
n-C3H7


994.
OCH3
CH3
H
n-C3H7


995.
OCH3
C2H5
H
n-C3H7


996.
OCH3
CF3
H
n-C3H7


997.
OCH3
OCF3
H
n-C3H7


998.
OCH3
OCHF2
H
n-C3H7


999.
OCH3
Br
H
CH(CH3)2


1000.
OCH3
OCH3
H
CH(CH3)2


1001.
OCH3
Cl
H
CH(CH3)2


1002.
OCH3
F
H
CH(CH3)2


1003.
OCH3
CH3
H
CH(CH3)2


1004.
OCH3
C2H5
H
CH(CH3)2


1005.
OCH3
CF3
H
CH(CH3)2


1006.
OCH3
OCF3
H
CH(CH3)2


1007.
OCH3
OCHF2
H
CH(CH3)2


1008.
OCH3
Br
H
n-C4H9


1009.
OCH3
OCH3
H
n-C4H9


1010.
OCH3
Cl
H
n-C4H9


1011.
OCH3
F
H
n-C4H9


1012.
OCH3
CH3
H
n-C4H9


1013.
OCH3
C2H5
H
n-C4H9


1014.
OCH3
CF3
H
n-C4H9


1015.
OCH3
OCF3
H
n-C4H9


1016.
OCH3
OCHF2
H
n-C4H9


1017.
OCH3
Br
H
C(CH3)3


1018.
OCH3
OCH3
H
C(CH3)3


1019.
OCH3
Cl
H
C(CH3)3


1020.
OCH3
F
H
C(CH3)3


1021.
OCH3
CH3
H
C(CH3)3


1022.
OCH3
C2H5
H
C(CH3)3


1023.
OCH3
CF3
H
C(CH3)3


1024.
OCH3
OCF3
H
C(CH3)3


1025.
OCH3
OCHF2
H
C(CH3)3


1026.
OCH3
Br
H
C6H5


1027.
OCH3
OCH3
H
C6H5


1028.
OCH3
Cl
H
C6H5


1029.
OCH3
F
H
C6H5


1030.
OCH3
CH3
H
C6H5


1031.
OCH3
C2H5
H
C6H5


1032.
OCH3
CF3
H
C6H5


1033.
OCH3
OCF3
H
C6H5


1034.
OCH3
OCHF2
H
C6H5


1035.
OCH3
Br
H
cyclopropyl


1036.
OCH3
OCH3
H
cyclopropyl


1037.
OCH3
Cl
H
cyclopropyl


1038.
OCH3
F
H
cyclopropyl


1039.
OCH3
CH3
H
cyclopropyl


1040.
OCH3
C2H5
H
cyclopropyl


1041.
OCH3
CF3
H
cyclopropyl


1042.
OCH3
OCF3
H
cyclopropyl


1043.
OCH3
OCHF2
H
cyclopropyl


1044.
OCH3
Br
H
CH2-cyclopropyl


1045.
OCH3
OCH3
H
CH2-cyclopropyl


1046.
OCH3
Cl
H
CH2-cyclopropyl


1047.
OCH3
F
H
CH2-cyclopropyl


1048.
OCH3
CH3
H
CH2-cyclopropyl


1049.
OCH3
C2H5
H
CH2-cyclopropyl


1050.
OCH3
CF3
H
CH2-cyclopropyl


1051.
OCH3
OCF3
H
CH2-cyclopropyl


1052.
OCH3
OCHF2
H
CH2-cyclopropyl


1053.
OCH3
Br
H
cyclobutyl


1054.
OCH3
OCH3
H
cyclobutyl


1055.
OCH3
Cl
H
cyclobutyl


1056.
OCH3
F
H
cyclobutyl


1057.
OCH3
CH3
H
cyclobutyl


1058.
OCH3
C2H5
H
cyclobutyl


1059.
OCH3
CF3
H
cyclobutyl


1060.
OCH3
OCF3
H
cyclobutyl


1061.
OCH3
OCHF2
H
cyclobutyl


1062.
OCH3
Br
H
cyclopentyl


1063.
OCH3
OCH3
H
cyclopentyl


1064.
OCH3
Cl
H
cyclopentyl


1065.
OCH3
F
H
cyclopentyl


1066.
OCH3
CH3
H
cyclopentyl


1067.
OCH3
C2H5
H
cyclopentyl


1068.
OCH3
CF3
H
cyclopentyl


1069.
OCH3
OCF3
H
cyclopentyl


1070.
OCH3
OCHF2
H
cyclopentyl


1071.
OCH3
Br
H
cyclohexyl


1072.
OCH3
OCH3
H
cyclohexyl


1073.
OCH3
Cl
H
cyclohexyl


1074.
OCH3
F
H
cyclohexyl


1075.
OCH3
CH3
H
cyclohexyl


1076.
OCH3
C2H5
H
cyclohexyl


1077.
OCH3
CF3
H
cyclohexyl


1078.
OCH3
OCF3
H
cyclohexyl


1079.
OCH3
OCHF2
H
cyclohexyl


1080.
OCH3
H
Br
H


1081.
OCH3
H
OCH3
H


1082.
OCH3
H
Cl
H


1083.
OCH3
H
F
H


1084.
OCH3
H
CH3
H


1085.
OCH3
H
C2H5
H


1086.
OCH3
H
CF3
H


1087.
OCH3
H
OCF3
H


1088.
OCH3
H
OCHF2
H


1089.
OCH3
H
Br
CH3


1090.
OCH3
H
OCH3
CH3


1091.
OCH3
H
Cl
CH3


1092.
OCH3
H
F
CH3


1093.
OCH3
H
CH3
CH3


1094.
OCH3
H
C2H5
CH3


1095.
OCH3
H
CF3
CH3


1096.
OCH3
H
OCF3
CH3


1097.
OCH3
H
OCHF2
CH3


1098.
OCH3
H
Br
C2H5


1099.
OCH3
H
OCH3
C2H5


1100.
OCH3
H
Cl
C2H5


1101.
OCH3
H
F
C2H5


1102.
OCH3
H
CH3
C2H5


1103.
OCH3
H
C2H5
C2H5


1104.
OCH3
H
CF3
C2H5


1105.
OCH3
H
OCF3
C2H5


1106.
OCH3
H
OCHF2
C2H5


1107.
OCH3
H
Br
n-C3H7


1108.
OCH3
H
OCH3
n-C3H7


1109.
OCH3
H
Cl
n-C3H7


1110.
OCH3
H
F
n-C3H7


1111.
OCH3
H
CH3
n-C3H7


1112.
OCH3
H
C2H5
n-C3H7


1113.
OCH3
H
CF3
n-C3H7


1114.
OCH3
H
OCF3
n-C3H7


1115.
OCH3
H
OCHF2
n-C3H7


1116.
OCH3
H
Br
CH(CH3)2


1117.
OCH3
H
OCH3
CH(CH3)2


1118.
OCH3
H
Cl
CH(CH3)2


1119.
OCH3
H
F
CH(CH3)2


1120.
OCH3
H
CH3
CH(CH3)2


1121.
OCH3
H
C2H5
CH(CH3)2


1122.
OCH3
H
CF3
CH(CH3)2


1123.
OCH3
H
OCF3
CH(CH3)2


1124.
OCH3
H
OCHF2
CH(CH3)2


1125.
OCH3
H
Br
n-C4H9


1126.
OCH3
H
OCH3
n-C4H9


1127.
OCH3
H
Cl
n-C4H9


1128.
OCH3
H
F
n-C4H9


1129.
OCH3
H
CH3
n-C4H9


1130.
OCH3
H
C2H5
n-C4H9


1131.
OCH3
H
CF3
n-C4H9


1132.
OCH3
H
OCF3
n-C4H9


1133.
OCH3
H
OCHF2
n-C4H9


1134.
OCH3
H
Br
C(CH3)3


1135.
OCH3
H
OCH3
C(CH3)3


1136.
OCH3
H
Cl
C(CH3)3


1137.
OCH3
H
F
C(CH3)3


1138.
OCH3
H
CH3
C(CH3)3


1139.
OCH3
H
C2H5
C(CH3)3


1140.
OCH3
H
CF3
C(CH3)3


1141.
OCH3
H
OCF3
C(CH3)3


1142.
OCH3
H
OCHF2
C(CH3)3


1143.
OCH3
H
Br
C6H5


1144.
OCH3
H
OCH3
C6H5


1145.
OCH3
H
Cl
C6H5


1146.
OCH3
H
F
C6H5


1147.
OCH3
H
CH3
C6H5


1148.
OCH3
H
C2H5
C6H5


1149.
OCH3
H
CF3
C6H5


1150.
OCH3
H
OCF3
C6H5


1151.
OCH3
H
OCHF2
C6H5


1152.
OCH3
H
Br
cyclopropyl


1153.
OCH3
H
OCH3
cyclopropyl


1154.
OCH3
H
Cl
cyclopropyl


1155.
OCH3
H
F
cyclopropyl


1156.
OCH3
H
CH3
cyclopropyl


1157.
OCH3
H
C2H5
cyclopropyl


1158.
OCH3
H
CF3
cyclopropyl


1159.
OCH3
H
OCF3
cyclopropyl


1160.
OCH3
H
OCHF2
cyclopropyl


1161.
OCH3
H
Br
CH2-cyclopropyl


1162.
OCH3
H
OCH3
CH2-cyclopropyl


1163.
OCH3
H
Cl
CH2-cyclopropyl


1164.
OCH3
H
F
CH2-cyclopropyl


1165.
OCH3
H
CH3
CH2-cyclopropyl


1166.
OCH3
H
C2H5
CH2-cyclopropyl


1167.
OCH3
H
CF3
CH2-cyclopropyl


1168.
OCH3
H
OCF3
CH2-cyclopropyl


1169.
OCH3
H
OCHF2
CH2-cyclopropyl


1170.
OCH3
H
Br
cyclobutyl


1171.
OCH3
H
OCH3
cyclobutyl


1172.
OCH3
H
Cl
cyclobutyl


1173.
OCH3
H
F
cyclobutyl


1174.
OCH3
H
CH3
cyclobutyl


1175.
OCH3
H
C2H5
cyclobutyl


1176.
OCH3
H
CF3
cyclobutyl


1177.
OCH3
H
OCF3
cyclobutyl


1178.
OCH3
H
OCHF2
cyclobutyl


1179.
OCH3
H
Br
cyclopentyl


1180.
OCH3
H
OCH3
cyclopentyl


1181.
OCH3
H
Cl
cyclopentyl


1182.
OCH3
H
F
cyclopentyl


1183.
OCH3
H
CH3
cyclopentyl


1184.
OCH3
H
C2H5
cyclopentyl


1185.
OCH3
H
CF3
cyclopentyl


1186.
OCH3
H
OCF3
cyclopentyl


1187.
OCH3
H
OCHF2
cyclopentyl


1188.
OCH3
H
Br
cyclohexyl


1189.
OCH3
H
OCH3
cyclohexyl


1190.
OCH3
H
Cl
cyclohexyl


1191.
OCH3
H
F
cyclohexyl


1192.
OCH3
H
CH3
cyclohexyl


1193.
OCH3
H
C2H5
cyclohexyl


1194.
OCH3
H
CF3
cyclohexyl


1195.
OCH3
H
OCF3
cyclohexyl


1196.
OCH3
H
OCHF2
cyclohexyl


1197.
Cl
Cl
H
H


1198.
Cl
F
H
H


1199.
Cl
CH3
H
H


1200.
Cl
OCH3
H
H


1201.
Cl
Br
H
H


1202.
Cl
CF3
H
H


1203.
Cl
OCF3
H
H


1204.
Cl
Cl
H
CH3


1205.
Cl
F
H
CH3


1206.
Cl
CH3
H
CH3


1207.
Cl
OCH3
H
CH3


1208.
Cl
Br
H
CH3


1209.
Cl
CF3
H
CH3


1210.
Cl
OCF3
H
CH3


1211.
Cl
Cl
H
C2H5


1212.
Cl
F
H
C2H5


1213.
Cl
CH3
H
C2H5


1214.
Cl
OCH3
H
C2H5


1215.
Cl
Br
H
C2H5


1216.
Cl
CF3
H
C2H5


1217.
Cl
OCF3
H
C2H5


1218.
Cl
Cl
H
n-C3H7


1219.
Cl
F
H
n-C3H7


1220.
Cl
CH3
H
n-C3H7


1221.
Cl
OCH3
H
n-C3H7


1222.
Cl
Br
H
n-C3H7


1223.
Cl
CF3
H
n-C3H7


1224.
Cl
OCF3
H
n-C3H7


1225.
Cl
Cl
H
CH(CH3)2


1226.
Cl
F
H
CH(CH3)2


1227.
Cl
CH3
H
CH(CH3)2


1228.
Cl
OCH3
H
CH(CH3)2


1229.
Cl
Br
H
CH(CH3)2


1230.
Cl
CF3
H
CH(CH3)2


1231.
Cl
OCF3
H
CH(CH3)2


1232.
Cl
Cl
H
n-C4H9


1233.
Cl
F
H
n-C4H9


1234.
Cl
CH3
H
n-C4H9


1235.
Cl
OCH3
H
n-C4H9


1236.
Cl
Br
H
n-C4H9


1237.
Cl
CF3
H
n-C4H9


1238.
Cl
OCF3
H
n-C4H9


1239.
Cl
Cl
H
C(CH3)3


1240.
Cl
F
H
C(CH3)3


1241.
Cl
CH3
H
C(CH3)3


1242.
Cl
OCH3
H
C(CH3)3


1243.
Cl
Br
H
C(CH3)3


1244.
Cl
CF3
H
C(CH3)3


1245.
Cl
OCF3
H
C(CH3)3


1246.
Cl
Cl
H
C6H5


1247.
Cl
F
H
C6H5


1248.
Cl
CH3
H
C6H5


1249.
Cl
OCH3
H
C6H5


1250.
Cl
Br
H
C6H5


1251.
Cl
CF3
H
C6H5


1252.
Cl
OCF3
H
C6H5


1253.
Cl
Cl
H
cyclopropyl


1254.
Cl
F
H
cyclopropyl


1255.
Cl
CH3
H
cyclopropyl


1256.
Cl
OCH3
H
cyclopropyl


1257.
Cl
Br
H
cyclopropyl


1258.
Cl
CF3
H
cyclopropyl


1259.
Cl
OCF3
H
cyclopropyl


1260.
Cl
Cl
H
CH2-cyclopropyl


1261.
Cl
F
H
CH2-cyclopropyl


1262.
Cl
CH3
H
CH2-cyclopropyl


1263.
Cl
OCH3
H
CH2-cyclopropyl


1264.
Cl
Br
H
CH2-cyclopropyl


1265.
Cl
CF3
H
CH2-cyclopropyl


1266.
Cl
OCF3
H
CH2-cyclopropyl


1267.
Cl
Cl
H
cyclobutyl


1268.
Cl
F
H
cyclobutyl


1269.
Cl
CH3
H
cyclobutyl


1270.
Cl
OCH3
H
cyclobutyl


1271.
Cl
Br
H
cyclobutyl


1272.
Cl
CF3
H
cyclobutyl


1273.
Cl
OCF3
H
cyclobutyl


1274.
Cl
Cl
H
cyclopentyl


1275.
Cl
F
H
cyclopentyl


1276.
Cl
CH3
H
cyclopentyl


1277.
Cl
OCH3
H
cyclopentyl


1278.
Cl
Br
H
cyclopentyl


1279.
Cl
CF3
H
cyclopentyl


1280.
Cl
OCF3
H
cyclopentyl


1281.
Cl
Cl
H
cyclohexyl


1282.
Cl
F
H
cyclohexyl


1283.
Cl
CH3
H
cyclohexyl


1284.
Cl
OCH3
H
cyclohexyl


1285.
Cl
Br
H
cyclohexyl


1286.
Cl
CF3
H
cyclohexyl


1287.
Cl
OCF3
H
cyclohexyl


1288.
Cl
H
Cl
H


1289.
Cl
H
F
H


1290.
Cl
H
CH3
H


1291.
Cl
H
OCH3
H


1292.
Cl
H
Br
H


1293.
Cl
H
CF3
H


1294.
Cl
H
OCF3
H


1295.
Cl
H
Cl
CH3


1296.
Cl
H
F
CH3


1297.
Cl
H
CH3
CH3


1298.
Cl
H
OCH3
CH3


1299.
Cl
H
Br
CH3


1300.
Cl
H
CF3
CH3


1301.
Cl
H
OCF3
CH3


1302.
Cl
H
Cl
C2H5


1303.
Cl
H
F
C2H5


1304.
Cl
H
CH3
C2H5


1305.
Cl
H
OCH3
C2H5


1306.
Cl
H
Br
C2H5


1307.
Cl
H
CF3
C2H5


1308.
Cl
H
OCF3
C2H5


1309.
Cl
H
Cl
n-C3H7


1310.
Cl
H
F
n-C3H7


1311.
Cl
H
CH3
n-C3H7


1312.
Cl
H
OCH3
n-C3H7


1313.
Cl
H
Br
n-C3H7


1314.
Cl
H
CF3
n-C3H7


1315.
Cl
H
OCF3
n-C3H7


1316.
Cl
H
Cl
CH(CH3)2


1317.
Cl
H
F
CH(CH3)2


1318.
Cl
H
CH3
CH(CH3)2


1319.
Cl
H
OCH3
CH(CH3)2


1320.
Cl
H
Br
CH(CH3)2


1321.
Cl
H
CF3
CH(CH3)2


1322.
Cl
H
OCF3
CH(CH3)2


1323.
Cl
H
Cl
n-C4H9


1324.
Cl
H
F
n-C4H9


1325.
Cl
H
CH3
n-C4H9


1326.
Cl
H
OCH3
n-C4H9


1327.
Cl
H
Br
n-C4H9


1328.
Cl
H
CF3
n-C4H9


1329.
Cl
H
OCF3
n-C4H9


1330.
Cl
H
Cl
C(CH3)3


1331.
Cl
H
F
C(CH3)3


1332.
Cl
H
CH3
C(CH3)3


1333.
Cl
H
OCH3
C(CH3)3


1334.
Cl
H
Br
C(CH3)3


1335.
Cl
H
CF3
C(CH3)3


1336.
Cl
H
OCF3
C(CH3)3


1337.
Cl.
H
Cl
C6H5


1338.
Cl
H
F
C6H5


1339.
Cl
H
CH3
C6H5


1340.
Cl
H
OCH3
C6H5


1341.
Cl
H
Br
C6H5


1342.
Cl
H
CF3
C6H5


1343.
Cl
H
OCF3
C6H5


1344.
Cl
H
Cl
cyclopropyl


1345.
Cl
H
F
cyclopropyl


1346.
Cl
H
CH3
cyclopropyl


1347.
Cl
H
OCH3
cyclopropyl


1348.
Cl
H
Br
cyclopropyl


1349.
Cl
H
CF3
cyclopropyl


1350.
Cl
H
OCF3
cyclopropyl


1351.
Cl
H
Cl
CH2-cyclopropyl


1352.
Cl
H
F
CH2-cyclopropyl


1353.
Cl
H
CH3
CH2-cyclopropyl


1354.
Cl
H
OCH3
CH2-cyclopropyl


1355.
Cl
H
Br
CH2-cyclopropyl


1356.
Cl
H
CF3
CH2-cyclopropyl


1357.
Cl
H
OCF3
CH2-cyclopropyl


1358.
Cl
H
Cl
cyclobutyl


1359.
Cl
H
F
cyclobutyl


1360.
Cl
H
CH3
cyclobutyl


1361.
Cl
H
OCH3
cyclobutyl


1362.
Cl
H
Br
cyclobutyl


1363.
Cl
H
CF3
cyclobutyl


1364.
Cl
H
OCF3
cyclobutyl


1365.
Cl
H
Cl
cyclopentyl


1366.
Cl
H
F
cyclopentyl


1367.
Cl
H
CH3
cyclopentyl


1368.
Cl
H
OCH3
cyclopentyl


1369.
Cl
H
Br
cyclopentyl


1370.
Cl
H
CF3
cyclopentyl


1371.
Cl
H
OCF3
cyclopentyl


1372.
Cl
H
Cl
cyclohexyl


1373.
Cl
H
F
cyclohexyl


1374.
Cl
H
CH3
cyclohexyl


1375.
Cl
H
OCH3
cyclohexyl


1376.
Cl
H
Br
cyclohexyl


1377.
Cl
H
CF3
cyclohexyl


1378.
Cl
H
OCF3
cyclohexyl


1379.
Br
Cl
H
H


1380.
Br
F
H
H


1381.
Br
CH3
H
H


1382.
Br
OCH3
H
H


1383.
Br
Br
H
H


1384.
Br
CF3
H
H


1385.
Br
OCF3
H
H


1386.
Br
Cl
H
CH3


1387.
Br
F
H
CH3


1388.
Br
CH3
H
CH3


1389.
Br
OCH3
H
CH3


1390.
Br
Br
H
CH3


1391.
Br
CF3
H
CH3


1392.
Br
OCF3
H
CH3


1393.
Br
Cl
H
C2H5


1394.
Br
F
H
C2H5


1395.
Br
CH3
H
C2H5


1396.
Br
OCH3
H
C2H5


1397.
Br
Br
H
C2H5


1398.
Br
CF3
H
C2H5


1399.
Br
OCF3
H
C2H5


1400.
Br
Cl
H
n-C3H7


1401.
Br
F
H
n-C3H7


1402.
Br
CH3
H
n-C3H7


1403.
Br
OCH3
H
n-C3H7


1404.
Br
Br
H
n-C3H7


1405.
Br
CF3
H
n-C3H7


1406.
Br
OCF3
H
n-C3H7


1407.
Br
Cl
H
CH(CH3)2


1408.
Br
F
H
CH(CH3)2


1409.
Br
CH3
H
CH(CH3)2


1410.
Br
OCH3
H
CH(CH3)2


1411.
Br
Br
H
CH(CH3)2


1412.
Br
CF3
H
CH(CH3)2


1413.
Br
OCF3
H
CH(CH3)2


1414.
Br
Cl
H
n-C4H9


1415.
Br
F
H
n-C4H9


1416.
Br
CH3
H
n-C4H9


1417.
Br
OCH3
H
n-C4H9


1418.
Br
Br
H
n-C4H9


1419.
Br
CF3
H
n-C4H9


1420.
Br
OCF3
H
n-C4H9


1421.
Br
Cl
H
C(CH3)3


1422.
Br
F
H
C(CH3)3


1423.
Br
CH3
H
C(CH3)3


1424.
Br
OCH3
H
C(CH3)3


1425.
Br
Br
H
C(CH3)3


1426.
Br
CF3
H
C(CH3)3


1427.
Br
OCF3
H
C(CH3)3


1428.
Br
Cl
H
C6H5


1429.
Br
F
H
C6H5


1430.
Br
CH3
H
C6H5


1431.
Br
OCH3
H
C6H5


1432.
Br
Br
H
C6H5


1433.
Br
CF3
H
C6H5


1434.
Br
OCF3
H
C6H5


1435.
Br
Cl
H
cyclopropyl


1436.
Br
F
H
cyclopropyl


1437.
Br
CH3
H
cyclopropyl


1438.
Br
OCH3
H
cyclopropyl


1439.
Br
Br
H
cyclopropyl


1440.
Br
CF3
H
cyclopropyl


1441.
Br
OCF3
H
cyclopropyl


1442.
Br
Cl
H
CH2-cyclopropyl


1443.
Br
F
H
CH2-cyclopropyl


1444.
Br
CH3
H
CH2-cyclopropyl


1445.
Br
OCH3
H
CH2-cyclopropyl


1446.
Br
Br
H
CH2-cyclopropyl


1447.
Br
CF3
H
CH2-cyclopropyl


1448.
Br
OCF3
H
CH2-cyclopropyl


1449.
Br
Cl
H
cyclobutyl


1450.
Br
F
H
cyclobutyl


1451.
Br
CH3
H
cyclobutyl


1452.
Br
OCH3
H
cyclobutyl


1453.
Br
Br
H
cyclobutyl


1454.
Br
CF3
H
cyclobutyl


1455.
Br
OCF3
H
cyclobutyl


1456.
Br
Cl
H
cyclopentyl


1457.
Br
F
H
cyclopentyl


1458.
Br
CH3
H
cyclopentyl


1459.
Br
OCH3
H
cyclopentyl


1460.
Br
Br
H
cyclopentyl


1461.
Br
CF3
H
cyclopentyl


1462.
Br
OCF3
H
cyclopentyl


1463.
Br
Cl
H
cyclohexyl


1464.
Br
F
H
cyclohexyl


1465.
Br
CH3
H
cyclohexyl


1466.
Br
OCH3
H
cyclohexyl


1467.
Br
Br
H
cyclohexyl


1468.
Br
CF3
H
cyclohexyl


1469.
Br
00F3
H
cyclohexyl


1470.
Br
H
Cl
H


1471.
Br
H
F
H


1472.
Br
H
CH3
H


1473.
Br
H
OCH3
H


1474.
Br
H
Br
H


1475.
Br
H
CF3
H


1476.
Br
H
OCF3
H


1477.
Br
H
Cl
CH3


1478.
Br
H
F
CH3


1479.
Br
H
CH3
CH3


1480.
Br
H
OCH3
CH3


1481.
Br
H
Br
CH3


1482.
Br
H
CF3
CH3


1483.
Br
H
OCF3
CH3


1484.
Br
H
Cl
C2H5


1485.
Br
H
F
C2H5


1486.
Br
H
CH3
C2H5


1487.
Br
H
OCH3
C2H5


1488.
Br.
H
Br
C2H5


1489.
Br
H
CF3
C2H5


1490.
Br
H
OCF3
C2H5


1491.
Br
H
Cl
n-C3H7


1492.
Br
H
F
n-C3H7


1493.
Br
H
CH3
n-C3H7


1494.
Br
H
OCH3
n-C3H7


1495.
Br
H
Br
n-C3H7


1496.
Br
H
CF3
n-C3H7


1497.
Br
H
OCF3
n-C3H7


1498.
Br
H
Cl
CH(CH3)2


1499.
Br
H
F
CH(CH3)2


1500.
Br
H
CH3
CH(CH3)2


1501.
Br
H
OCH3
CH(CH3)2


1502.
Br
H
Br
CH(CH3)2


1503.
Br
H
CF3
CH(CH3)2


1504.
Br
H
OCF3
CH(CH3)2


1505.
Br
H
Cl
n-C4H9


1506.
Br
H
F
n-C4H9


1507.
Br
H
CH3
n-C4H9


1508.
Br
H
OCH3
n-C4H9


1509.
Br
H
Br
n-C4H9


1510.
Br
H
CF3
n-C4H9


1511.
Br
H
OCF3
n-C4H9


1512.
Br
H
Cl
C(CH3)3


1513.
Br
H
F
C(CH3)3


1514.
Br
H
CH3
C(CH3)3


1515.
Br
H
OCH3
C(CH3)3


1516.
Br
H
Br
C(CH3)3


1517.
Br
H
CF3
C(CH3)3


1518.
Br
H
OCF3
C(CH3)3


1519.
Br
H
Cl
C6H5


1520.
Br
H
F
C6H5


1521.
Br
H
CH3
C6H5


1522.
Br
H
OCH3
C6H5


1523.
Br
H
Br
C6H5


1524.
Br
H
CF3
C6H5


1525.
Br
H
OCF3
C6H5


1526.
Br
H
Cl
cyclopropyl


1527.
Br
H
F
cyclopropyl


1528.
Br
H
CH3
cyclopropyl


1529.
Br
H
OCH3
cyclopropyl


1530.
Br
H
Br
cyclopropyl


1531.
Br
H
CF3
cyclopropyl


1532.
Br
H
OCF3
cyclopropyl


1533.
Br
H
Cl
CH2-cyclopropyl


1534.
Br
H
F
CH2-cyclopropyl


1535.
Br
H
CH3
CH2-cyclopropyl


1536.
Br
H
OCH3
CH2-cyclopropyl


1537.
Br
H
Br
CH2-cyclopropyl


1538.
Br
H
CF3
CH2-cyclopropyl


1539.
Br
H
OCF3
CH2-cyclopropyl


1540.
Br
H
Cl
cyclobutyl


1541
Br
H
F
cyclobutyl


1542.
Br
H
CH3
cyclobutyl


1543.
Br
H
OCH3
cyclobutyl


1544.
Br
H
Br
cyclobutyl


1545.
Br
H
CF3
cyclobutyl


1546.
Br
H
OCF3
cyclobutyl


1547.
Br
H
Cl
cyclopentyl


1548.
Br
H
F
cyclopentyl


1549.
Br
H
CH3
cyclopentyl


1550.
Br
H
OCH3
cyclopentyl


1551.
Br
H
Br
cyclopentyl


1552.
Br
H
CF3
cyclopentyl


1553.
Br
H
OCF3
cyclopentyl


1554.
Br
H
Cl
cyclohexyl


1555.
Br
H
F
cyclohexyl


1556.
Br
H
CH3
cyclohexyl


1557.
Br
H
OCH3
cyclohexyl


1558.
Br
H
Br
cyclohexyl


1559.
Br
H
CF3
cyclohexyl


1560.
Br
H
OCF3
cyclohexyl


1561.
CH3
Cl
H
H


1562.
CH3
F
H
H


1563.
CH3
CH3
H
H


1564.
CH3
OCH3
H
H


1565.
CH3
Br
H
H


1566.
CH3
CF3
H
H


1567.
CH3
OCF3
H
H


1568.
CH3
Cl
H
CH3


1569.
CH3
F
H
CH3


1570.
CH3
CH3
H
CH3


1571.
CH3
Br
H
CH3


1572.
CH3
CF3
H
CH3


1573.
CH3
OCF3
H
CH3


1574.
CH3
Cl
H
C2H5


1575.
CH3
F
H
C2H5


1576.
CH3
CH3
H
C2H5


1577.
CH3
Br
H
C2H5


1578.
CH3
CF3
H
C2H5


1579.
CH3
OCF3
H
C2H5


1580.
CH3
Cl
H
n-C3H7


1581.
CH3
F
H
n-C3H7


1582.
CH3
CH3
H
n-C3H7


1583.
CH3
Br
H
n-C3H7


1584.
CH3
CF3
H
n-C3H7


1585.
CH3
OCF3
H
n-C3H7


1586.
CH3
Cl
H
CH(CH3)2


1587.
CH3
F
H
CH(CH3)2


1588.
CH3
CH3
H
CH(CH3)2


1589.
CH3
Br
H
CH(CH3)2


1590.
CH3
CF3
H
CH(CH3)2


1591.
CH3
OCF3
H
CH(CH3)2


1592.
CH3
Cl
H
n-C4H9


1593.
CH3
F
H
n-C4H9


1594.
CH3
CH3
H
n-C4H9


1595.
CH3
Br
H
n-C4H9


1596.
CH3
CF3
H
n-C4H9


1597.
CH3
OCF3
H
n-C4H9


1598.
CH3
Cl
H
C(CH3)3


1599.
CH3
F
H
C(CH3)3


1600.
CH3
CH3
H
C(CH3)3


1601.
CH3
Br
H
C(CH3)3


1602.
CH3
CF3
H
C(CH3)3


1603.
CH3
OCF3
H
C(CH3)3


1604.
CH3
Cl
H
C6H5


1605.
CH3
F
H
C6H5


1606.
CH3
CH3
H
C6H5


1607.
CH3
Br
H
C6H5


1608.
CH3
CF3
H
C6H5


1609.
CH3
OCF3
H
C6H5


1610.
CH3
Cl
H
cyclopropyl


1611.
CH3
F
H
cyclopropyl


1612.
CH3
CH3
H
cyclopropyl


1613.
CH3
Br
H
cyclopropyl


1614.
CH3
CF3
H
cyclopropyl


1615.
CH3
OCF3
H
cyclopropyl


1616.
CH3
Cl
H
CH2-cyclopropyl


1617.
CH3
F
H
CH2-cyclopropyl


1618.
CH3
CH3
H
CH2-cyclopropyl


1619.
CH3
Br
H
CH2-cyclopropyl


1620.
CH3
CF3
H
CH2-cyclopropyl


1621.
CH3
OCF3
H
CH2-cyclopropyl


1622.
CH3
Cl
H
cyclobutyl


1623.
CH3
F
H
cyclobutyl


1624.
CH3
CH3
H
cyclobutyl


1625.
CH3
Br
H
cyclobutyl


1626.
CH3
CF3
H
cyclobutyl


1627.
CH3
OCF3
H
cyclobutyl


1628.
CH3
Cl
H
cyclopentyl


1629.
CH3
F
H
cyclopentyl


1630.
CH3
CH3
H
cyclopentyl


1631.
CH3
Br
H
cyclopentyl


1632.
CH3
CF3
H
cyclopentyl


1633.
CH3
OCF3
H
cyclopentyl


1634.
CH3
Cl
H
cyclohexyl


1635.
CH3
F
H
cyclohexyl


1636.
CH3
CH3
H
cyclohexyl


1637.
CH3
Br
H
cyclohexyl


1638.
CH3
CF3
H
cyclohexyl


1639.
CH3
OCF3
H
cyclohexyl


1640.
CH3
H
Cl
H


1641.
CH3
H
F
H


1642.
CH3
H
CH3
H


1643.
CH3
H
Br
H


1644.
CH3
H
CF3
H


1645.
CH3
H
OCF3
H


1646.
CH3
H
Cl
CH3


1647.
CH3
H
F
CH3


1648.
CH3
H
CH3
CH3


1649.
CH3
H
Br
CH3


1650.
CH3
H
CF3
CH3


1651.
CH3
H
OCF3
CH3


1652.
CH3
H
Cl
C2H5


1653.
CH3
H
F
C2H5


1654.
CH3
H
CH3
C2H5


1655.
CH3
H
Br
C2H5


1656.
CH3
H
CF3
C2H5


1657.
CH3
H
OCF3
C2H5


1658.
CH3
H
Cl
n-C3H7


1659.
CH3
H
F
n-C3H7


1660.
CH3
H
CH3
n-C3H7


1661.
CH3
H
Br
n-C3H7


1662.
CH3
H
CF3
n-C3H7


1663.
CH3
H
OCF3
n-C3H7


1664.
CH3
H
Cl
CH(CH3)2


1665.
CH3
H
F
CH(CH3)2


1666.
CH3
H
CH3
CH(CH3)2


1667.
CH3
H
Br
CH(CH3)2


1668.
CH3
H
CF3
CH(CH3)2


1669.
CH3
H
OCF3
CH(CH3)2


1670.
CH3
H
Cl
n-C4H9


1671.
CH3
H
F
n-C4H9


1672.
CH3
H
CH3
n-C4H9


1673.
CH3
H
Br
n-C4H9


1674.
CH3
H
CF3
n-C4H9


1675.
CH3
H
OCF3
n-C4H9


1676.
CH3
H
Cl
C(CH3)3


1677.
CH3
H
F
C(CH3)3


1678.
CH3
H
CH3
C(CH3)3


1679.
CH3
H
Br
C(CH3)3


1680.
CH3
H
CF3
C(CH3)3


1681.
CH3
H
OCF3
C(CH3)3


1682.
CH3
H
Cl
C6H5


1683.
CH3
H
F
C6H5


1684.
CH3
H
CH3
C6H5


1685.
CH3
H
Br
C6H5


1686.
CH3
H
CF3
C6H5


1687.
CH3
H
OCF3
C6H5


1688.
CH3
H
Cl
cyclopropyl


1689.
CH3
H
F
cyclopropyl


1690.
CH3
H
CH3
cyclopropyl


1691.
CH3
H
Br
cyclopropyl


1692.
CH3
H
CF3
cyclopropyl


1693.
CH3
H
OCF3
cyclopropyl


1694.
CH3
H
Cl
CH2-cyclopropyl


1695.
CH3
H
F
CH2-cyclopropyl


1696.
CH3
H
CH3
CH2-cyclopropyl


1697.
CH3
H
Br
CH2-cyclopropyl


1698.
CH3
H
CF3
CH2-cyclopropyl


1699.
CH3
H
OCF3
CH2-cyclopropyl


1700.
CH3
H
Cl
cyclobutyl


1701.
CH3
H
F
cyclobutyl


1702.
CH3
H
CH3
cyclobutyl


1703.
CH3
H
Br
cyclobutyl


1704.
CH3
H
CF3
cyclobutyl


1705.
CH3
H
OCF3
cyclobutyl


1706.
CH3
H
Cl
cyclopentyl


1707.
CH3
H
F
cyclopentyl


1708.
CH3
H
CH3
cyclopentyl


1709.
CH3
H
Br
cyclopentyl


1710.
CH3
H
CF3
cyclopentyl


1711.
CH3
H
OCF3
cyclopentyl


1712.
CH3
H
Cl
cyclohexyl


1713.
CH3
H
F
cyclohexyl


1714.
CH3
H
CH3
cyclohexyl


1715.
CH3
H
Br
cyclohexyl


1716.
CH3
H
CF3
cyclohexyl


1717.
CH3
H
OCF3
cyclohexyl









Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ib (≡I where Ra═Re═H, X═O, Y═O, R1═H, R3═H and n=0) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ib.1 to Ib.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ic (≡I where Ra═Re═H, X═O, Y═O, R1═H, R3═C2H5 and n=0) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ic.1 to Ic.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Id (≡I where X═O, Y═O, R1═H, R3═CH(CH3)2 and n=0) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Id.1 to Id.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ie (≡I where X═O, Y═O, R1═H, R3═H, A═O and n=1) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ie.1 to Ie.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula If (≡I where X═O, Y═O, R1═H, R3═CH3, A═O and n=1) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds If.1 to If.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ig (≡I where X═O, Y═O, R1═H, R3 ═C2H5, A═O and n=1) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ig.1 to Ig.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ih (≡I where X═O, Y═O, R1H, R3═CH(CH3)2, A═O and n=1) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ih.1 to Ih.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ii (≡I where X═O, Y═O, R1═H, R3═H, n=1 and A═NR12 where R12═H) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ii.1 to Ii.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ij (≡I where X═O, Y═O, R1═H, R3═CH3, n=1 and A═NR12 where R12═H) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ij.1 to Ij.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ik (≡I where X═O, Y═O, R1═H, R3═C2H5, n=1 and A═NR12 where R12═H) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ik.1 to Ik.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula II (≡I where X═O, Y═O, R1═H, R3═CH(CH3)2, n=1 and A═NR12 where R12═H) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Il.1 to Il.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Im (≡I where X═O, Y═O, R1═H, R3═H, n=1 and A═NR12 where R12═CH3) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Im.1 to Im.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula In (≡I where X═O, Y═O, R1═H, R3═CH3, n=1 and A═NR12 where R12═CH3) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds In.1 to In.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Io (≡I where X═O, Y═O, R1═H, R3═C2H5, n=1 and A═NR12 where R12═CH3) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Io.1 to Io.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




Particular preference is also given to the 1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ip (≡I where X═O, Y═O, R1═H, R3═CH(CH3)2, n=1 and A═NR12 where R12═CH3) where Rb, Rc, Rd and R2 have the meanings given above, in particular the meanings mentioned as being preferred. Examples of such compounds are the compounds Ip.1 to Ip.1717 in which the variables Rb, Rc, Rd and R2 together have the meanings given in one row of Table 1.




The 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I according to the invention can be prepared, for example, by one of the processes A to G described below.
A) Amidation of a Carboxylic Acid II or a Carboxylic Acid Derivative of II
The preparation of the compound I according to the invention can be carried out, for example, according to Scheme 1 by reacting an activated form of a pyrrolidine-3-carboxylic acid of the formula II with an amine III.




In Scheme 1, the variables R1, X, Ra, Rb, Rc, Rd, Re, A, n, R2 and R3 are as defined above. Such reactions are known, for example from WO 01/83459, and can be applied in an analogous manner to the reaction illustrated in Scheme 1. The carboxylic acid II is preferably initially activated by carrying out the reaction in the presence of a coupling agent. Suitable coupling agents are, for example, N,N′-carbonyldiimidazole or carbodiimides, such as dicyclohexylcarbodiimide. These compounds are generally employed in an at least equimolar amount and up to a four-fold excess, based on the carboxylic acid II. If appropriate, it may be advantageous to carry out the reaction of the carboxylic acid II with the coupling agent in the presence of a catalytic amount of a tertiary aminopyridine, such as 4-dimethylaminopyridine (DMAP). In this case, the amount of aminopyridine added is preferably 5 to 10 mol %, based on the carboxylic acid II. The reaction is usually carried out in a solvent. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, carboxamides, such as dimethylformamide, N-methyllactams, such as N-methylpyrrolidone, nitriles, such as acetonitrile, aromatic hydrocarbons, such as toluene, or mixtures of these.
The molar ratio of amine III to carboxylic acid II is generally at least 0.9:1, preferably at least 1:1. If appropriate, it may be advantageous to employ the amine in a slight excess, for example in an excess of up to 30%, based on the carboxylic acid II.
In general, the reaction temperature is in the range from 0° C. to the boiling point of the solvent.
Alternatively, the carboxylic acid II can initially be activated by converting it into its acid halide, preferably its acid chloride. Means for this purpose are known, for example from U.S. Pat. No. 4,874,422. Suitable compounds are inorganic acid halides, preferably acid chlorides, such as thionyl chloride, phosphoryl chloride phosphorus pentachloride or phosphorus trichloride, and organic acid chlorides, such as oxalyl chloride. The acid halide of II formed can be isolated and then be reacted with the amine III. It is also possible to react the acid chloride of II formed directly, without isolation, with the amine III. If appropriate, the reactivity of the acid halide is enhanced by adding catalytic amounts of an N,N-dialkylcarboxamide, such as dimethylformamide. The halogenating agent is usually employed in an at least equimolar amount, based on the carboxylic acid II. The acid halides thionyl chloride, phosphorus trichloride or phosphoryl chloride can simultaneously act as solvent. Suitable solvents are furthermore-solvents which are inert under the reaction conditions, for example chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as benzene or toluene, aliphatic and cycloaliphatic hydrocarbons, such as hexane, petroleum ether, cyclohexane, and mixtures thereof. The reaction temperature is generally between room temperature and the boiling point of the solvent. After the reaction has ended, excess halogenating agent is generally removed. The resulting acid halide of II is then reacted with the amine III. In general, the amine III is dissolved in the solvent which was also used for preparing the carbonyl halide, unless the solvent is one of the acid halides mentioned above.
If appropriate, the reaction is carried out in the presence of an auxiliary base which is preferably employed in an equimolar amount or an up to four-fold excess, based on the carboxylic acid II. Suitable bases are, for example, amines such as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine, α-, β-, γ-lutidine or triethylamine.
It is, of course, also possible to use other methods for activating the carboxylic acid II. Such methods are described in the prior art, for example in J. Falbe, Houben Weyl, Methoden der Organischen Chemie [Methods of organic chemistry], Vol. E5, 4th Ed., 1985, p. 941 ff.
In a further process variant, the corresponding carboxylic acid ester of II (carboxylic acid ester VI), in particular the C1-C4-alkyl ester of II and especially the methyl or ethyl ester of II, is reacted with the amine III, if appropriate in the presence of a base. Regarding a suitable base, solvent and reaction temperatures, reference is made to what was said above. The preparation of the carboxylic acid ester VI is described below.
Compounds of the formula II where R1═H can be prepared, for example, similarly to a process described in Journal of Heterocyclic Chemistry, 3 (1966), 311. The synthesis is shown in Scheme 2.




In Scheme 2, the variables Ra, Rb, Rc, Rd, Re are as defined above and R is C1-C4-alkyl. The reaction of the aniline compound IV with butyrolactone is usually carried out in the presence of an inorganic acid, such as sulfuric acid, phosphoric acid or hydrochloric acid, or in the presence of an organic acid, such as acetic acid. The reaction can be carried out in the absence of a solvent or in the presence of a solvent. Suitable solvents are all solvents which are inert under the reaction conditions. However, the reaction is preferably carried out in the absence of a solvent. If the reaction is carried out in the absence of a solvent, the butyrolactone is employed in an excess, based on the aniline IV. The reaction temperatures are generally in the range of from 20° C. to the boiling point of the solvent.
In the next step, the resulting pyrrolidinone V is generally reacted without further purification, for example with a carbonate (RO)2CO or a synthetic equivalent, such as a chloroformic ester. To this end, the pyrrolidinone V is generally initially converted into the corresponding enolate by treatment with a suitable base. Suitable bases include in particular organolithium compounds, such as n-butyllithium, tert-butyllithium and phenyllithium, lithium amides, such as lithium diisopropylamide, and alkali metal hydrides, such as sodium hydride. The reaction is generally carried out in an organic solvent. Suitable solvents are inert solvents, such as aliphatic and cycloaliphatic hydrocarbons, such as hexane, petroleum ether, cyclohexane, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, and also mixtures of these. In general, the deprotonation of the compound V is carried out at low temperatures to about room temperature, preferably at about 0° C. To this end, the base is employed in an at least equimolar amount, preferably a 1.1- to 4-fold molar excess, based on the compound V.
The subsequent introduction of the alkoxycarbonyl group is carried out, for example, using a carbonic acid diester, such as dimethyl carbonate or diethyl carbonate. The carbonic acid diester and the enolate of the compound V are usually employed in equimolar amounts. It is, of course, possible for one of the two reactants to be employed in a slight excess. The temperature required for the reaction is generally in the range of from 0° C. to the boiling point of the solvent.
The carboxylic acid ester VI is then hydrolyzed by known methods (see, for example, Organikum, 17th Edition, VEB Deutscher Verlag der Wissenschaften, 1988, p. 415) to give the carboxylic acid II. The hydrolysis can be carried out either in acidic medium using strong mineral acids, such as concentrated hydrochloric acid or sulfuric acid, or organic acids, such as glacial acetic acid, or mixtures of these in the presence of water, or in alkaline medium using bases, such as alkali metal hydroxide, for example sodium hydroxide or potassium hydroxide, if appropriate in the presence of water.
Suitable solvents both for acidic and basic hydrolysis of esters are, for example, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, alcohols, water and mixtures of these solvents. The reaction temperature is usually between room temperature and the boiling point of the solvent.
The compounds II can furthermore be prepared by aminoethylation of malonic acid esters VII in which R1 is as defined above and R is C1-C4-alkyl with phenylaziridines VII and subsequent hydrolysis. The synthesis is shown in Scheme 3 and can be carried out similarly to known methods as described, for example, in Archiv der Pharmazie (Weinheim) 302(4) (1969), 253, Justus Liebigs Ann. Chem. 716 (1968), 121-126 or in Angew. Chem. 74, (1962), 694.




The reaction is generally carried out in the presence of LiH/LiI in a solvent. Suitable solvents include aromatic solvents, such as benzene, toluene or xylene. Frequently, the aziridine VII and the malonic acid ester are employed in approximately equimolar amounts. It may be advantageous to employ an excess of malonic acid ester VIII, preferably an excess of up to 30%, based on the aziridine VII. The resulting ester VIa is then converted according to known methods by hydrolysis in acidic or alkaline medium into the corresponding carboxylic acids II. With regard to ester hydrolysis, reference is made to what was said above.
Compounds of the formula II in which R1 is H can furthermore be prepared similarly to a process described in JP 2000143624-A. To this end, anilines IV are reacted with 1,1-cyclopropanedicarboxylic acid. The synthesis route is shown in Scheme 4. The reaction is usually carried out in water or in an aliphatic nitrile, such as acetonitrile, or in mixtures thereof with water, at temperatures between 40 and 100° C.




Compounds of the formula II in which R1 is H can furthermore be obtained similarly to processes described in J. Am. Chem. Soc. 97 (1975), 3239 or Organic Synthesis 60, (1981), 66. The reaction of the aniline IV with the dioxaspirooctanedione IX gives the carboxylic acid II. The synthesis route is shown in Scheme 5.




B) Linking a Pyrrolidinone X to an Aromatic Compound XI

Compounds of the formula I can furthermore be prepared by reacting suitably substituted pyrrolidinones X with aromatic compounds of the formula XI according to the synthesis shown in Scheme 6.




In Scheme 6, the variables Ra, Rb, Rc, Rd, Rd, Re, X, Y, A, n, R1, R2 and R3 are as defined above. Z is halogen, preferably fluorine, chlorine or bromine, or B(OH)2, B(OR′)2 or Sn(R′)3. In these radicals, R′ is aryl, such as phenyl, or C1-C10-alkyl.
The reaction is preferably carried out in a solvent, in particular a polar aprotic solvent, such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, dimethylacetamide, an ether, such as diethyl ether, tetrahydrofuran or dioxane, and mixtures of these solvents.
In general, the reaction is carried out at temperatures above room temperature, preferably in the range from 50 to 200° C. To this end, the compounds of the formulae X and XI are preferably employed in approximately equimolar amounts. It is, of course, also possible to use an excess of one of the components, the excess preferably being not more than 50 mol %, in particular not more than 20 mol %, based on the component which is present in a substoichiometric amount.
The compounds I according to the invention are furthermore obtained by coupling XI (for example Z=Cl, Br, I, B(OR)2, SnR3) with a pyrrolidinone X, preferably in the presence of catalytically active amounts of a palladium, copper or nickel compound, if appropriate in the presence of a base, in an organic solvent or a mixture of a solvent with water, at room temperature or elevated temperatures. Processes for coupling a phenylboronic acid are described, for example, in WO 02/42275.
Suitable palladium catalysts are, in addition to palladium carboxylates, such as palladium(II) acetate, also palladium/phosphine complexes, such as tetrakistriphenylphosphinepalladium, bistriphenylphosphinepalladium(II) chloride, bis(1,2-diphenylphosphinoethane)palladium(II) chloride, bis(1,3-diphenylphosphinopropane)palladium(II) chloride, bis(1,4-diphenylphosphinobutane)palladium(II) chloride and bis(diphenylphosphino)ferrocenylpalladium(II) chloride. However, it is also possible to react palladium halides such as palladium(II) chloride in situ with phosphine ligands, giving the catalytically active complexes. Suitable phosphine ligands are, for example, arylphosphines which are unsubstituted or substituted in the ortho-, meta- or para-position by halogen, alkyl and/or SO3H, such as triphenylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, bis(diphenylphosphino)ferrocene, hetarylphosphines, such as trifurylphosphine or tripyridylphosphine.
Suitable Ni catalysts are nickel(II) acetylacetonate alone or in combination with the abovementioned phosphine ligands, or Ni(II) acetylacetonate with imidazolium carbene ligands, and also complexes of nickel(II) salts with the above mentioned phosphine ligands, for example bis(triphenylphosphine)nickel(II) chloride, [1,3-bis(diphenylphosphino)propane]nickel(II) chloride, [1,4-bis(diphenylphosphino)butane]nickel(II) chloride and [bis(diphenylphosphino)ferrocene]nickel(II) chloride.
Suitable copper compounds are, in particular, copper(I) compounds, such as CuCl, CuBr and the like.
The catalyst is usually employed in substoichiometric amounts, preferably of 0.001-0.8 equivalents and particularly preferably of 0.01 to 0.5 equivalents, based on the pyrrolidinone XI used.
If appropriate, it may be advantageous to convert the compound X initially with a base into its salt. Suitable bases are, for example, alkali metal hydrides, such as sodium hydride, and sodium alkoxides, such as sodium methoxide and sodium ethoxide, lithium amides, such as lithium diisopropylamide, and also organolithium compounds, such as butyllithium and phenyllithium.
The molar ratio of compound XI to compound X is preferably in the range from 0.95:1 to 1:1.5.
Suitable bases are, if required, alkali metal and alkaline earth metal hydroxides, alkali metal (bi)carbonates and alkali metal phosphates, such as NaOH, NaHCO3, Na2CO3, KHCO3, K2CO3, Ba(OH)2, K3PO4, alkali metal, alkaline earth metal, thallium and transition metal alkoxides, such as sodium ethoxide and thallium ethoxide. Other suitable bases are alkali metal fluorides, such as potassium fluoride, cesium fluoride, ammonium fluorides and tetrabutylammonium fluoride. The base is usually employed in an approximately stoichiometric amount or in up to 10-fold excess, based on the compound II.
Suitable solvents are organic solvents, such as DMF, dimethylacetamide, toluene, tetrahydrofuran (THF), dioxane and dimethoxyethane. If the coupling is carried out with boronic acid, the abovementioned solvents can also be employed in a mixture with water, for example in a ratio of about 5:1 to 1:5, preferably in a ratio of about 2:1 to 1:2 and in particular of about 1:1.
The reaction temperature is usually above the melting point and can be up to the boiling point of the solvent. It is preferably in the range between 50 and 150° C.
The pyrrolidino compounds X can be prepared by customary processes, for example analogously to the procedure described in process A.
C) Alkylation of Compounds of the Formula I in which R1═H
Compounds of the formula I in which R1 is hydrogen can be prepared according to general methods by treatment with an alkylation agent R1-L in compounds of the formula I in which R1 is not hydrogen. The synthesis route is shown in Scheme 7.




In Scheme 7, the variables R1, Ra, Rb, Rc, Rd, Rd, Re, X, Y, A, n, R1, R2 and R3 are as defined above. L is a nucleophilically displaceable leaving group, such as halogen, for example chlorine, bromine, iodine, or imidazolyl, carboxylate, such as acetate, arylsulfonate or alkylsulfonate, for example mesylate or triflate. The reaction is usually carried out in the presence of a base. Suitable bases include alkali metal or alkaline earth metal hydroxides, metal hydrides, such as alkali metal hydrides, for example sodium hydride, tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, α-, β-, γ-lutidine, lithium diisopropylamide.
Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide.
In general, the reaction temperature is in the range from 0° C. to the boiling point of the reaction mixture.
D) Sulfurization of the Compounds of the Formula I in which X or Y is Oxygen.
Compounds of the formula I in which X or Y is oxygen can be prepared according to general methods by treatment with a sulfurizing agent in compounds of the formula I in which X or Y is sulfur. This synthesis route is illustrated in Scheme 8.




In Scheme 8, the variables Ra, Rb, Rc, Rd, Rd, Re, X, Y, A, n, R1, R2 and R3 are as defined above. Examples of suitable sulfurizing agents are phosphorus(V) sulfides, organotin sulfides, and also organophosphorus sulfides (see also J. March, Advanced Organic Synthesis, 2nd Edition, Wiley Interscience 1985, p. 794 and the literature cited therein). Particularly suitable sulfurizing agents are phosphorus(V) sulfide and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithia-diphosphetane-2,4-dithione (“Lawesson's reagent”). Sulfurization processes are described, for example, in WO 95/33718. The reaction can be carried out in a solvent or neat. Suitable solvents are all solvents which are inert under the reaction conditions, for example aromatic hydrocarbons, such as benzene, toluene, xylene, chlorobenzene, basic solvents, such as pyridine, ethers, such as diethyl ether, 1,2-dimethoxyethane or tetrahydrofuran, etc. The temperatures required for the reaction are generally above room temperature and in particular in the range of from 50° C. to the boiling point of the reaction mixture.
E) Condensation of an Anilide XII
A further route to the compounds I according to the invention is the reaction of an anilide XII with a suitable difunctional compound L-CH2—CH2-L′ with ring closure according to Scheme 9.




In Scheme 9, the variables Ra, Rb, Rc, Rd, Rd, Re, X, Y, A, n, R1, R2 and R3 are as defined above, L is as defined in C) and L′ has the meaning of L.
The cyclization is carried out in the presence of a base. Suitable bases are all bases mentioned under C). In general, the reaction is carried out in an inert solvent. Suitable solvents are in particular chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide. The starting material XII and the difunctional compound L-CH2—CH2-L′ are expediently employed in approximately equimolar amounts; however, to optimize the conversion, it may be advantageous to use an excess of one of the two components. The reaction is generally carried out at a temperature between room temperature and the boiling point of the reaction mixture.
The starting materials XII can be prepared in two steps similarly to the process described in Synlett 12 (1969), 1209. In the first step, an isocyanate XIII is reacted with meldrum acid (2,2-dimethyl-1,3-dioxane-4,6-dione). In the second step, the resulting product is then reacted with a suitable amine III. In Scheme 10, the variables Ra, Rb, Rc, Rd, Rd, Re, X, Y, A, n, R1, R2 and R3 are as defined above.




F) Condensations

F.1 Condensation of Anilines IV with tetrahydro-2-furanones XIV

The compounds I according to the invention can be prepared, for example, by condensing anilines IV with tetrahydro-2-furanones XIV according to the synthesis route shown in Scheme 11. Analogous reactions are known, for example from Tetrahedron Letters, 31 (21) (1990), 2991, and can be applied to the preparation of the compounds according to the invention.




In Scheme 11, the variables Ra, Rb, Rc, Rd, Rd, Re, X, Y, A, n, R1, R2 and R3 are as defined above. The reaction of the anilines IV is usually carried out in a carboxylic acid, such as acetic acid, at temperatures in the range from 0° C. to 100° C. In general, the starting materials are employed in equimolar amounts, or one of the two components is employed in excess.
F.2 Condensation of Anilines IV with Carboxylic Acid Derivatives XV and Subsequent Cyclization
The compounds I according to the invention can be prepared, for example, by condensing anilines IV with carboxylic acid derivatives XV according to the synthesis route shown in Scheme 12.




In Scheme 12, the variables Ra, Rb, Rc, Rd, Rd, Re, X, Y, A, n, R1, R2 and R3 are as defined above. L is as defined in C) and L′ has the meaning of L. The reaction of the aniline IV with the carboxylic acid derivative XV is usually carried out in the presence of a base. Suitable bases are, for example, amines, such as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine or triethylamine. The base is usually employed in up to six-fold excess, based on the carboxylic acid derivative XV. The reaction is generally carried out in a solvent. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, ethers, for example dialkyl ethers, such as diethyl ether, methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran or dioxane, carbonamides, such as dimethylformamide, N-methyllactams, such as N-methylpyrrolidone, nitrites, such as acetonitrile, aromatic hydrocarbons, such as toluene, aromatic amines, such as pyridine, or mixtures of these. In general, the reaction temperature is in a range of from 0° C. to the boiling point of the solvent.
G) Reaction of a Pyrrolidinone XVI with an iso(thio)cyanate XVII
Compounds of the formula I can be prepared by reacting pyrrolidinones XVI with an iso(thio)cyanate XVII in the presence of a base according to the synthesis route shown in Scheme 13. Such reactions are known, for example, from U.S. Pat. No. 5,185,349.




In Scheme 13, the variables Ra, Rb, Rc, Rd, Rd, Re, X, Y and R1 are as defined above. R3′ has the meanings mentioned for R3 which are different from hydrogen. To prepare compounds I where R3═H, preference is given to using the salt of an isocyanate or isothiocyanate, for example sodium iso(thio)cyanate or potassium iso(thio)cyanate.
Suitable bases include alkali metal hydrides, such as sodium hydride or potassium hydride, organolithium compounds, such as lithium diisopropylamide. In general, the reaction is carried out in a solvent. Suitable solvents include ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, 1,4-dioxane, anisole, glycol ethers, such as dimethyl glycol ether, hydrocarbons, such as hexane, petroleum ether or mixtures of these.
The compounds I and their agriculturally useful salts are suitable—both as isomer mixtures and in the form of the pure isomers—as herbicides. The herbicidal compositions comprising I permit very good control of plant growth on uncultivated areas. In crops such as wheat, rice, corn, soybean and cotton, they are effective against broad-leaved weeds and harmful grasses without significantly damaging the crops. This effect occurs in particular at low application rates.
Depending on the particular application method, the compounds I or the herbicidal compositions comprising them may be used in a further number of crops for eliminating unwanted plants. Suitable are, for example, the following crops:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. 
The compounds I may also be used in crops which are tolerant to the action of herbicides as a result of breeding, including the use of genetic engineering methods.
The compounds I or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, broadcasting agents or granules, by spraying, nebulizing, dusting, broadcasting or pouring, or for seed dressing or mixing with the seed. The application forms depend on the intended uses; they should in any case ensure very fine distribution of the active ingredients according to the invention.
The herbicidal compositions comprise a herbicidally effective amount of at least one active compound of the formula I and auxiliaries which are usually used in formulating crop protection agents.
Suitable inert auxiliaries are essentially:
mineral oil fractions having a medium to high boiling point, such as kerosine and diesel oil, and coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones, such as cyclohexanone, and strongly polar solvents, for example amines, such as N-methylpyrrolidone, and water.
Aqueous application forms can be prepared from emulsion concentrates, from suspensions, pastes, wettable powders or water-dispersible granules by adding water. For the preparation of emulsions, pastes or oil dispersions, the 1-phenylpyrrolidin-2-onecarboxamides I, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adherents, dispersants or emulsifiers. However, it is also possible to prepare concentrates which consist of active ingredient, wetting agent, adherent, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g. lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkylsulfonates and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ether; condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Powders, broadcasting agents and dusting agents can be prepared by mixing or milling the active ingredients together with a solid carrier.
Granules, for example coated, impregnated and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and vegetable products, such as grain flour, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carriers.
The concentrations of the active ingredients I in the ready-to-use formulations may be varied within wide ranges. In general, the formulations comprise from about 0.001 to 98, preferably from 0.01 to 95, % by weight of at least one active ingredient I. The active ingredients are used in a purity of from 90 to 100%, preferably from 95 to 100% (according to the NMR spectrum).
The compounds I according to the invention can be formulated, for example, as follows:

    I. 20 parts by weight of a compound I are dissolved in a mixture which consists of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of from 8 to 10 mol of ethylene oxide with 1 mol of N-monoethanololeamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which comprises 0.02% by weight of the active ingredient is obtained.
    II. 20 parts by weight of a compound I are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which comprises 0.02% by weight of the active ingredient is obtained.
    III. 20 parts by weight of a compound I are dissolved in a mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction boiling within the range from 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which comprises 0.02% by weight of the active ingredient is obtained.
    IV. 20 parts by weight of a compound I are thoroughly mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid obtained from a sulfite waste liquor and 60 parts by weight of silica gel powder, and the mixture is milled in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor which comprises 0.1% by weight of the active ingredient is obtained.
    V. 3 parts by weight of a compound I are mixed with 97 parts by weight of finely divided kaolin. A dusting agent which comprises 3% by weight of the active ingredient is obtained in this manner.
    VI. 20 parts by weight of a compound I are thoroughly mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
    VII. 1 part by weight of a compound I is dissolved in a mixture which consists of 70 parts by height of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
    VIII. 1 part by weight of a compound I is dissolved in a mixture which consists of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM31 (=nonionic emulsifier based on ethoxylated castor oil; BASF AG). A stable emulsion concentrate is obtained.


The active compounds I or the herbicidal compositions can be applied by the preemergence or postemergence method. The herbicidal compositions or active compounds can also be applied by sowing crop seed which has been pretreated with the herbicidal compositions or active compounds. If the active ingredients are less well tolerated by certain crops, it is possible to use application methods in which the herbicidal compositions are sprayed with the aid of the sprayers in such a way that the leaves of the sensitive crops are as far as possible not affected, while the active compounds reach the leaves of undesirable plants growing underneath or the uncovered soil surface (post-directed, lay-by).
The application rates of active compound I are from 0.001 to 3.0, preferably from 0.01 to 1.0, kg/ha of active ingredient (a.i.), depending on the aim of control, the season, the target plants and the state of growth.
In order to broaden the action spectrum and to achieve synergistic effects, the compounds I according to the invention may be mixed with many members of other groups of herbicidal or growth-regulating active ingredients and applied together with them.
Examples of suitable components of the mixture are 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and derivatives thereof, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanoic acids and derivatives thereof, benzoic acid and derivatives thereof, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetarylarylketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and derivatives thereof, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and derivatives thereof, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and derivatives thereof, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and derivatives thereof, 2-phenylpropionic acid and derivatives thereof, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and derivatives thereof, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolcarboxamides and uracils.
It may also be useful to apply the compounds I together, alone or in combination with other herbicides, also as a mixture with further crop-protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. The miscibility with mineral salt solutions which are used for eliminating nutrient and trace element deficiencies is also of interest. Nonphytotoxic oils and oil concentrates can also be added.
The examples below are intended to illustrate the invention without limiting it.


PREPARATION EXAMPLES
The products were characterized by HPLC/MS (high performance liquid chromatography/mass spectrometry), by 1H-NMR spectroscopy or by their melting point.
HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany).
Mobile phase: acetonitrile +0.1% trifluoroacetic acid (TFA)/water +0.1% TFA in a gradient from 5:95 to 95:5 over 5 minutes, at 40° C.
MS: quadrupole electrospray ionization, 80 V (positive mode)
Example 1
1-(3-trifluoromethyl)phenyl-3-(N-methyl)carboxamido-2-pyrrolidinone




1.1: 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone
54 g (0.34 mol) of 3-trifluoromethylaniline, 110 ml of butyrolactone and 5 ml of concentrated hydrochloric acid were heated at reflux for 13 hours. Excess butyrolactone was then removed under reduced pressure. The resulting crystalline residue was washed initially with an aqueous sodium bicarbonate solution and then with water and subsequently with pentane. Drying gave 65.5 g (85% of theory) of 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone.
1H-NMR (270 MHz, CDCl3) δ (ppm): 7.85 (m, 2H), 7.45 (t, 1H), 7.4 (d, 1H), 3.85 (t, 2H), 2.6 (t, 2H), 2.2 (qu, 2H).
1.2: 2-oxo-1-(3-trifluoromethyl)phenyl-3-pyrrolidinecarboxylic acid
Under nitrogen, 50 ml of absolute tetrahydrofuran were added to 13.6 g (0.06 mol) of 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone from 1.1, the mixture was cooled to 0° C. and 60 ml of 2M (0.12 mol) lithium diisoproylamide in a solvent mixture of heptane, tetrahydrofuran and ethylbenzene were added. The reaction mixture was stirred at 0° C. for 45 minutes. 5.4 g (0.06 mol) of dimethyl carbonate in 10 ml of absolute tetrahydrofuran were then added. After the addition had ended, the reaction mixture was allowed to warm to 20° C. and stirred for another 72 hours. The solvent was evaporated under reduced pressure and methyl tert-butyl ether and water were then added to the resulting residue, the phases were separated and the organic phase was extracted twice with water. The aqueous phase was acidified with hydrochloric acid (10% by weight) to pH=1. The mixture was extracted twice with in each case 100 ml of ethyl acetate and the combined organic phase was dried and concentrated under reduced pressure. This gave 5.61 g (34% of theory) of 2-oxo-1-(3-trifluoromethyl)phenyl-3-pyrrolidinecarboxylic acid of melting point 121° C.
1H-NMR (400 MHz, CDCl3) δ (ppm): 7.9 (s, 1H), 7.8 (d, 1H), 7.5 (t, 1H), 7.45 (d, 1H), 4.1-3.9 (m, 2H), 3.7 (t, 1H), 2.55 (m, 2H).
1.3: 1-(3-trifluoromethyl)phenyl-3-(N-methyl)carboxamido-2-pyrrolidinone
0.14 g (1.8 mmol) of a 40% strength aqueous methylamine solution was added to 0.5 g (1.8 mmol) of 2-oxo-1-(3-trifluoromethyl) phenyl-3-pyrrolidinecarboxylic acid from 1.2 in 50 ml of dichloromethane and 0.35 g (2 mmol) of 1,1′-carbonyldiimidazole. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was extracted with saturated aqueous ammonium chloride solution and the organic phase was then extracted with water. The organic phase was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure and the residue that remained was then titrated with methyl tert-butyl ether. The insoluble fraction was then separated off, and the residue was washed with methyl tert-butyl ether. This gave 0.166 g (32% of theory) of the title compound of melting point 128° C.
1H-NMR (400 MHz, CDCl3) δ (ppm): 7.9 (s, 1H), 7.75 (d, 1H), 7.5 (t, 1H), 7.4 (d, 1H), 7.3-7.2 (br, 1H), 4.0-3.8 (m, 2H), 3.5 (t, 1H), 2.9 (d, 3H), 2.75-2.6 (m, 1H), 2.55-2.45 (m, 1H).
Example 2
1-(3-trifluoromethoxy)phenyl-3-acetyloxy-3-(N-phenyl)carboxamido-2-pyrrolidinone




0.34 g (0.93 mmol) of 1-(3-trifluoromethoxy)phenyl-3-(N-phenyl)-carboxamido-2-pyrrolidinone, prepared analogously to Example 1 using the starting material 3-trifluoromethoxyaniline, was initially charged in 3 ml of dry dimethylformamide (DMF), and 0.04 g (0.093 mmol) of sodium hydride (60% in mineral oil) was added at 20° C. The mixture was then stirred at 20° C. for 30 min, 0.07 g (0.093 mmol) of acetyl chloride was then added and the mixture was stirred at 20° C. for another 18 h. Water was added and the mixture was extracted repeatedly with dichloromethane. The combined organic phases were washed with water, the solvent was removed and the residue was chromatographed. This gave 0.27 g of the title compound of melting point 140° C.
The compounds of Examples 3 to 191 were prepared in an analogous manner:







TABLE 2













 



















m.p. [° C.]








or RT


Example
(A)n
R*
R1
R2
R3
(HPLC/MS)
















1
—
3-CF3
H
methyl
H
128


2
—
3-OCF3
OC(O)CH3
phenyl
H
140


3
—
3-CF3
H
ethyl
H
122


4
—
3-CF3
H
n-propyl
H
112


5
—
3-CF3
H
n-butyl
H
111


6
—
3-CF3
H
tert-butyl
H
oil


7
—
3-CF3
H
cyclopentyl
H
oil


8
—
3-CF3
H
ethyl
ethyl
oil


9
—
3-CF3
H
methyl
n-butyl
oil


10
—
3-CF3
H
phenyl
H
oil


11
—
3-CF3
H
CH(CH3)2
H
136


12
—
3-CF3
H
cyclohexyl
H
141


13
—
3-CF3
H
CH2-cyclopropyl
H
108


14
—
3-CF3
H
cyclopropyl
H
oil


15
—
3-CF3
H
methyl
methyl
oil


16
—
3-CF3
H
cyclopropyl
methyl
oil


17
O
3-CF3
H
t-butyl
H
122


18
—
3-OCF3
H
methyl
H
103


19
—
3-OCF3
H
ethyl
H
111


20
—
3-OCF3
H
n-propyl
H
110


21
—
3-OCF3
H
tert-butyl
H
 89


22
—
3-OCF3
H
cyclopentyl
H
140


23
—
3-OCF3
H
methyl
n-butyl
oil


24
—
3-OCF3
H
phenyl
H
108


25
—
3-OCF3
H
CH(CH3)2
H
134


26
—
3-OCF3
H
cyclopropyl
H
134


27
—
3-OCF3
H
methyl
methyl
oil


28
—
3-OCF3
H
H
H
106


29
O
3-OCF3
H
H
H
124


30
—
3-OCF3
OC(O)CH3
cyclopentyl
H
oil


31
O
3-OCF3
H
methyl
H
 98


32
—
3-OCF3
CH3
tert-butyl
H
 40


33
O
3-OCF3
H
CH2-phenyl
H
108


34
O
3-OCF3
H
methyl
methyl
oil


35
O
3-OCF3
H
CH(CH3)2
H
123


36
O
3-OCF3
H
CH2CH═CH2
H
 75


37
O
3-OCF3
H
CH2C(Cl)═CH2
H
 68


38
O
3-OCF3
H
CH2CH2CH2

 29


39
O
3-OCF3
H
CH2CH═CHCH3
H
 87


40
O
3-OCF3
H
CH2CH═CHCl
H
 62


41
O
3-OCF3
H
CH2CH3
H
100


42
O
3-OCF3
H
CH2CH2OCH3
H
 85


43
O
3-OCF3
H
cylohexyl
H
152


44
O
3-OCF3
H
CH2-cylohexyl
H
135


45
—
3-CH(CH3)2
H
tert-butyl
H
 51


46
—
3-CH(CH3)2
CH3
tert-butyl
H
 78


47
O
3-CF3
H
tert-butyl
H
oil


48
O
3-OCF3
H
tert-butyl
H
112


49
—
2-Cl
H
tert-butyl
H
 76


50
—
3-Cl
H
tert-butyl
H
118


51
—
3-Cl; 5-Cl
H
tert-butyl
H
130


52
—
2-Cl; 4-Cl
H
tert-butyl
H
 93


53
—
2-F
H
tert-butyl
H
113


54
—
2-CF3
H
tert-butyl
H
 90


55
—
4-CF3
H
tert-butyl
H
155


56
—
2-CH3
H
tert-butyl
H
 93


57
—
3-CH3
H
tert-butyl
H
 88


58
—
4-CH3
H
tert-butyl
H
135


59
—
2-CH(CH3)2
H
tert-butyl
H
104


60
—
3-OCH3
H
tert-butyl
H
 43


61
—
4-OCH3
H
tert-butyl
H
132


62
—
2-OCH3
H
tert-butyl
H
oil


63
—
2-Cl; 6-Cl
H
tert-butyl
H
oil


64
—
2-Cl; 3-Cl
H
tert-butyl
H
oil


65
—
4-Cl
H
tert-butyl
H
155


 


66
—
3-OCH3
H




H
110-112


 


67
—
3-OCF3
H




H
3.78 min,m/z = 405[M + H]+


 


68
—
3-OCF3
H




H
4.09 min,m/z = 399[M + H]+


 


69
—
3-OCF3
H




H
3.62 min,m/z = 391[M + H]+


 


70
—
3-OCF3
H




H
3.89 min,m/z = 397[M + H]+


 


71
—
3-OCF3
H




H
4.30 min,m/z = 469[M + H]+


 


72
—
3-OCF3
H




H
4.03 min,m/z = 469[M + H]+


 


73
—
3-OCF3
H




H
3.95 min,m/z = 443[M + Na]+


 


74
—
3-OCF3
H




H
3.93 min,m/z = 443[M + Na]+


 


75
—
3-OCF3
H




H
3.61 min,m/z = 525[M + H]+


 


76
—
3-OCF3
H




H
3.75 min,m/z = 459[M + Na]+


 


77
—
3-OCF3
H




H
3.55 min,m/z = 489[M + Na]+


 


78
—
3-OCF3
H




H
3.84 min,m/z = 373[M + H]+


 


79
—
3-OCF3
H




H
4.11 min,m/z = 498[M + Na]+


 


80
—
3-OCF3
H




H
3.79 min,m/z = 443[M + H]+


 


81
—
3-OCF3
H




H
3.88 min,m/z = 373[M + H]+


 


82
—
3-OCF3
H




H
3.60 min,m/z = 387[M + H]+


 


83
—
3-OCF3
H




H
3.80 min,m/z = 429[M + Na]+


 


84
—
3-OCF3
H




H
3.37 min,m/z = 355[M + H]+


 


85
—
3-OCF3
H




H
3.17 min,m/z = 356[M + H]+


 


86
—
3-OCF3
H




H
4.20 min,m/z = 401[M + H]+


 


87
—
3-OCF3
H




H
3.33 min,m/z = 405[M + H]+


 


88
—
3-OCF3
H




H
3.52 min,m/z = 435[M + H]+


 


89
—
3-OCF3
H




H
3.91 min,m/z = 451[M + H]+


 


90
—
3-OCF3
H




H
4.20 min,m/z = 491[M + Na]+


 


91
—
3-OCF3
H




H
3.18 min,m/z = 389[M + H]+


 


92
—
3-OCF3
H




H
3.85 min,m/z = 460[M + Na]+


 


93
—
3-OCF3
H




H
4.03 min,m/z = 475[M + H]+


 


94
—
3-OCF3
H




H
3.82 min,m/z = 579[M + Na]+


 


95
—
3-OCF3
H




H
3.19 min,m/z = 401[M + H]+


 


96
—
3-OCF3
H




H
3.32 min,m/z = 481[M + H]+


 


97
—
3-OCF3
H




H
3.75 min,m/z = 383[M + H]+


 


98
—
3-OCF3
H




H
4.26 min,m/z = 401[M + H]+


 


99
—
3-OCF3
H




H
4.06 min,m/z = 411[M + H]+


 


100
—
3-OCF3
H




H
3.54 min,m/z = 415[M + H]+


 


101
—
3-OCF3
H




H
3.79 min,m/z = 429[M + H]+


 


102
—
3-OCF3
H




H
3.77 min,m/z = 429[M + H]+


 


103
—
3-OCF3
H




H
4.09 min,m/z = 435[M + H]+


 


104
—
3-OCF3
H




H
3.98 min,m/z = 439[M + H]+


 


105
—
3-OCF3
H




H
3.75 min,m/z = 383[M + H]+


 


106
—
3-OCF3
H




H
2.93 min,m/z = 421[M + H]+


 


107
—
3-OCF3
H




H
3.63 min,m/z = 504[M + H]+


 


108
—
3-OCHF2
H
phenyl
H
104


 


109
—
3-OCHF2
H




H
 80


 


110
—
3-OCHF2
H
tert-butyl
H
 64


 


111
—
3-OCHF2
H




H
oil


 


112
—
3-OCHF2
H




H
153


 


113
—
3-OCHF2
H




H
oil


 


114
—
3-OCHF2
H




H
oil


 


115
—
3-OCHF2
H




H
 48


 


116
—
3-OCHF2
H




H
oil


 


117
—
3-OCHF2
H




H
 82


 


118
—
3-OCHF2
H




H
oil


 


119
—
3-OCHF2
H
CH3
H
 74


120
—
3-OCHF2
H
ethyl
H
 70


121
—
3-OCHF2
H
isopropyl
H
126


122
—
3-OCHF2
H
cylopropyl
H
130


123
—
4-CH═C(Cl)2
H
tert-butyl
H
166-167


124
—
3-CF3;
H
tert-butyl
H
135-136




5-CF3


125
—
4-SCH3
H
tert-butyl
H
166-167


126
—
4-CH(CH3)2
H
tert-butyl
H
130-131


127
—
4-OCHF2
H
tert-butyl
H
152-153


128
—
3-Cl;
H
tert-butyl
H
160-163




4-Cl;




5-Cl


129
—
3-Br;
H
tert-butyl
H
140-141




5-Br


130
—
4-NO2;
H
tert-butyl
H
152-153




5-Cl


131
—
4-OCF2CF3
H
tert-butyl
H
66-67


 


132
—
3-OCF3
H




H
oil


 


133
—
3-OCF3
H




H
3.51 min,m/z = 357[M + H]+


 


134
—
3-OCF3
H




H
3.67 min,m/z = 359[M + H]+


 


135
—
3-OCF3
H




H
2.92 min,m/z = 361[M + H]+


 


136
—
3-OCF3
H




H
3.31 min,m/z = 370[M + H]+


 


137
—
3-OCF3
H




H
3.23 min,m/z = 370[M + H]+


 


138
—
3-CF3;
H
tert-butyl
H
3.65 min




4-Cl



m/z = 363








[M + H]+


139
—
3-OCH3;
H
tert-butyl
H
2.87 min




5-OCH3



m/z = 321








[M + H]+


140
—
3-SCH3
H
tert-butyl
H
3.14 min








m/z = 307








[M + H]+


141
—
3-tert-
H
tert-butyl
H
3.62 min




butyl



m/z = 317








[M + H]+


142
—
O—CH(CH3)2
H
tert-butyl
H
3.24 min








m/z = 319








[M + H]+


143
—
3-F;
H
tert-butyl
H
3.07 min




4-F



m/z = 297








[M + H]+


144
—
3-OCH3;
H
tert-butyl
H
2.64 min




4-OCH3;



m/z = 351




5-OCH3



[M + H]+


145
—
4-propyl
H
tert-butyl
H
3.53 min








m/z = 303








[M + H]+


146
—
4-O-tert-
H
tert-butyl
H
3.36 min




butyl



m/z = 333








[M + H]+


147
—
3-Cl;
H
tert-butyl
H
3.26 min




4-F



m/z = 313








[M + H]+


148
—
4-O-propyl
H
tert-butyl
H
3.67 min








m/z = 319








[M + H]+


149
—
4-Br
H
tert-butyl
H
3.19 min








m/z = 339








[M + H]+


150
—
4-SCH2CH3
H
tert-butyl
H
3.32 min








m/z = 321








[M + H]+


151
—
3-Br;
H
tert-butyl
H
3.49 min




4-OCH3;



m/z = 405




5-Cl



[M + H]+


152
—
3-Cl;
H
tert-butyl
H
3.58 min




4-O-propyl



m/z = 353








[M + H]+


153
—
3-F;
H
tert-butyl
H
2.97 min




4-NO2



m/z = 324








[M + H]+


154
—
3-Br;
H
tert-butyl
H
3.86 min




5-Br;



m/z = 452




4-Cl



[M + H]+


155
—
3-ethyl;
H
tert-butyl
H
3.47 min




5-CH3



m/z = 303








[M]+


156
—
3-CH2;
H
tert-butyl
H
3.22 min




5-CH3



m/z = 289








[M + H]+


157
—
3-Br
H
tert-butyl
H
3.21 min








m/z = 341








[M + H]+


158
—
3-ethyl
H
tert-butyl
H
3.23 min








m/z = 289








[M + H]+


159
—
3-iso-
H
tert-butyl
H
3.46 min




propyl;



m/z = 333




4-OCH3



[M + H]+


160
—
3,4-
H
tert-butyl
H
2.66 min




OCH2CH2O—



m/z = 319








[M + H]+


161
—
4-CN
H
tert-butyl
H
2.74 min








m/z = 286








[M + H]+


162
—
3-CN;
H
tert-butyl
H
2.74 min




4-OCH3



m/z = 316








[M + H]+


163
—
3-CN;
H
tert-butyl
H
2.79 min




4-F



m/z = 304








[M + H]+


164
—
3-F;
H
tert-butyl
H
3.22 min




4-CH3



m/z = 293








[M + H]+


165
—
3-CN;
H
tert-butyl
H
3.09 min




4-Cl



m/z = 320








[M + H]+


166
—
3-Cl;
H
tert-butyl
H
3.53 min




4-Cl



m/z = 329








[M]+


167
—
3-CH3;
H
tert-butyl
H
3.11 min




4-F



m/z = 293








[M + H]+


168
—
3-Cl;
H
tert-butyl
H
3.06 min




4-OCH3



m/z = 325








[M + H]+


169
—
4-heptyl
H
tert-butyl
H
4.50 min








m/z = 359








[M + H]+


170
—
4-tert-
H
tert-butyl
H
3.73 min




butyl



m/z = 317








[M + H]+


171
—
4-ethyl
H
tert-butyl
H
3.32 min








m/z = 289








[M + H]+


172
—
3-Cl;
H
tert-butyl
H
3.82 min




4-iso-



m/z = 337




propyl



[M + H]+


173
—
3-Cl;
H
tert-butyl
H
3.45 min




4-CH3



m/z = 309








[M]+


174
—
3-F
H
tert-butyl
H
3.96 min








m/z = 279








[M + H]+


175
—
3-CH3;
H
tert-butyl
H
94-96




5-propyl


176
—
3-ethyl;
H
tert-butyl
H
120-122




5-ethyl


177
—
3-O-ethyl
H
tert-butyl
H
86-88


178
—
3-OCH3;
H
tert-butyl
H
150-152




4-Br


179
—
3-OCH3;
H
tert-butyl
H
137-139




4-Cl


180
—
3-Cl;
H
tert-butyl
H
3.86 min




4-SCF3



m/z = 395








[M + H]+


181
—
4-F
H
tert-butyl
H
2.77 min








m/z = 278








[M + H]+


 


182
—
3-OCF3
H




H
4.16 minm/z = 423[M + H]+


 


183
—
3-OCF3
H




H
4.31 minm/z = 469[M + H]+


 


184
—
3-OCF3
H




H
3.87 minm/z = 443[M + H]+


 


185
—
3-OCF3
H




H
3.76 minm/z = 447[M + Na]+


 


186
—
3-OCF3
H




H
3.00 minm/z = 402[M + H]+


 


187
—
3-OCF3
H




H
3.75 minm/z = 453[M + Na]+


 


188
—
3-OCF3
H




H
3.94 minm/z = 463[M + Na]+


 


189
—
3-OCF3
H




H
4.42 minm/z = 553[M + Na]+


 


190
—
3-OCF3
H




H
3.85 minm/z = 473[M + Na]+


 


191
—
3-OCF3
H




H
4.49 minm/z = 611[M + Na]+





*The number in front of the substituent denotes the position of the substituent on the phenyl ring.


● Attachment site


RT = retention time, HPLC/MS


m.p. = melting point


phenyl = C6H5






Example 192
1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethylethyl))carboxamido-2-pyrrolidinethione and 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethylethyl))thiocarboxamido-2-pyrrolidinone




0.26 g (0.7 mmol) of 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-di-methylethyl))carboxamido-2-pyrrolidinone was initially charged in 3 ml of dry toluene, and 0.17 g (0.42 mmol) of 2,4-bis(4-methoxy-phenyl)-1,3-dithia-2,4-diphosphetane-2,4-dithione (Lawesson's reagent) was added at 20° C., and the mixture was heated at 70° C. for 7 h. The reaction mixture was then washed twice with water. The solvent was removed and the residue was chromatographed on silica gel using a mixture of cyclohexane/ethyl acetate as mobile phase. A first fraction gave 0.06 g (22%) of 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethyl-ethyl))thiocarboxamido-2-pyrrolidinone of melting point 65° C. and 0.08 g (29%) of 1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethyl-ethyl))carboxamido-2-pyrrolidinethione of melting point 116° C.
Use Examples
The herbicidal activity of the 1-phenylpyrrolidon-2-one-3-carboxamides of the formula I was demonstrated by the following greenhouse experiments:
The cultivation containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.
For the preemergence treatment, directly after sowing the active compounds, which had been suspended or emulsified in water, were applied by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this was adversely affected by the active compounds.
For the postemergence treatment, the test plants were first grown to a height of 3-15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to the treatment. The application rate for the pre- and postemergence treatment was 3.0 kg of a.i./ha.
Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth.
The plants used in the greenhouse experiments were of the following species:














Bayer code
Common name









ABUTH
Velvetleaf



AVEFA
wild Oat



LOLMU
italien Ryegrass



SETIT
Millet



SINAL
velvetleaf










At application rates of 3 kg/ha, the compound from Example 3, applied by the post-emergence method, shows very good herbicidal activity against AVEFA and SINAL.
At application rates of 3 kg/ha, the compound from Example 18, applied by the post-emergence method, shows very good herbicidal activity against ABUTH, SETIT and SINAL.
At application rates of 3 kg/ha, the compound from Example 18, applied by the pre-emergence method, shows very good herbicidal activity against ABUTH, SETIT and SINAL.
At application rates of 3 kg/ha, the compound from Example 19, applied by the pre-emergence method, shows very good herbicidal activity against ABUTH and SINAL.
At application rates of 3 kg/ha, the compound from Example 26, applied by the post-emergence method, shows very good herbicidal activity against AVEFA and SINAL.
At application rates of 3 kg/ha, the compound from Example 26, applied by the pre-emergence method, shows very good herbicidal activity against ABUTH, LOLMU and SINAL.

## Claims

1. A compound which is a 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I




where the variables R1, R2, R3, X, Y, A, n, Ra, Rb, Rc, Rd and Re are as defined below:
R1 is hydrogen, OH, Cl, Br, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C(O)R4 or OC(O)R4;
R2 is C1-C10-alkyl, C3-C8-cycloalkyl, C3-C8-alkenyl, C3-C8-alkynyl, C5-C8-cycloalkenyl or C3-C8-cycloalkyl-C1-C4 -alkyl, wherein C1-C10-alkyl and C3-C8-cycloalkyl may be partially or fully halogenated and/or may carry one or two radicals selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl group, COOR5, NR6R7 and C(O)NR8R9, and wherein said phenyl group may be unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of halogen, nitro, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7and C(O)NR8R9; is hydrogen, C1-C10-alkyl, C3-C10-cycloalkyl, C07-C10-polycycloalkyl, C3-C8-alkenyl, C3-C10-alkynyl, C5-C10-cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl or 3- to 7-membered heterocyclyl, where the 9 last-mentioned groups may be unsubstituted, partially or fully halogenated and/or substituted by 1, 2 or 3 radicals selected from the group consisting of OH, CN, NO2, COOH, C1-C6-alkyl, C1 -C6-haloalkyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7, C(O)NR8S02R13, C(O)NR8R9 and 3- to 7-membered heterocyclyl, wherein each heterocyclyl may contain 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, a group NR10 and a group SO2, and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members; and/or may contain a ring-fused phenyl ring which is unsubstituted or substituted; or
R2 and R3, together with the group N-(A)n to which they are attached, form a saturated 3-to 7-membered heterocycle which, in addition to the nitrogen atom, may contain 1, 2 or a further 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and a group NR10 and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members;
Ra, Rb, Rc, Rd and Re independently of one another are hydrogen, OH, CN, NO2, halogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, C(O)R4, COOR5, NR6R7, C(O)NR8R9, S(O)2NR8R9, S(O)R11, S(O)2R11 or C1-C4-alkoxy-C1-C6-alkyl; or two adjacent radicals Ra to Re, together with the atoms to which they are attached, form a 5-, 6- or 7-membered saturated or unsaturated ring which may contain one or two heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and a group NR10 as ring-forming atom and/or may carry one, two, three or four radicals selected from the group consisting of halogen and C1-C4-alkyl; X, Y independently of one another are oxygen or sulfur;
n is 0 or 1;
A is 0, S(O)k or NR12, where k is 0, 1 or 2;
R4, R8, R9 independently of one another are hydrogen or C1-C4-alkyl;
R5, R11 are C1-C4-alkyl;
R6, R7 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C(O)R4, COOR5 or S(O)2R11;
R10, R12 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl; and
R13 is phenyl which is unsubstituted or carries 1, 2, 3 or 4 substituents, where the substituents are selected from the group consisting of halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR5, NR6R7 and C(O)NR8R9; or an agriculturally useful salt thereof.

2. A compound as claimed in claim 1 wherein R3 is hydrogen, C1-C10-alkyl, C3-C10-cycloalkyl, C3-C8-alkenyl, C3-C8-alkynyl, C5-C10-cycloalkenyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl or 3-to 7-membered heterocyclyl, where the 8 last-mentioned groups may be unsubstituted, partially or fully halogenated and/or substituted by 1, 2 or 3 radicals selected from the group consisting of OH, CN, NO2, COOH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1 -C6-alkylthio, C1 -C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7, and C(O)NR8R9, wherein each heterocyclyl may contain 1, 2 or 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and a group NR10 and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members; or
R2 and R3, together with the group N-(A)n to which they are attached, form a saturated 3- to 7-membered heterocycle which, in addition to the nitrogen atom, may contain 1, 2 or a further 3 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur and a group NR10 and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring members.

3. A compound as claimed in claim 1 wherein R1 is hydrogen.

4. A compound as claimed in claim 1 wherein R3 is hydrogen or C1-C4-alkyl.

5. A compound as claimed in claim 1 wherein R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C5-C6-cycloalkenyl, substituted or unsubstituted phenyl, C3-C6-cycloalkyl-C1-C4-alkyl, where C1-C6-alkyl and C3-C6 cycloalkyl may be partially or fully halogenated and/or may contain at least one radical selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7 and C(O)NR8R9.

6. A compound as claimed in claim 1 wherein X and Y represent oxygen.

7. A compound as claimed in claim 1 wherein n=0.

8. A compound as claimed in claim 1 wherein the radicals Ra, Rb, Ro, Rd and Re are selected from the group consisting of hydrogen, halogen, CN, C1-C4-alkyl, OCH3, CF3, CHF2, OCF3 and OCHF2.

9. A compound as claimed in claim 1 wherein not more than 3 of the radicals Ra, Rb, Rc, Rd and Re are different from hydrogen.

10. A compound as claimed in claim 1 wherein 2 or 3 of the radicals Ra, Rb, Rc, Rd and Re are different from hydrogen.

11. A compound as claimed in claim 9 wherein the radicals Ra and Re represent hydrogen.

12. A composition, comprising a herbicidally effective amount of at least compound as claimed in claim 1, and at least one inert liquid and/or solid carrier, and, if desired, at least one surfactant.

13. A method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one compound as claimed in claim 1 to act on plants, their habitat or on a seed.

14. A method for controlling unwanted vegetation, comprising applying to plants, their habitat or to their seed a herbicidally effective amount of at least one compound of claim 1.

15. The method of claim 14, wherein said compound is applied at an application rate of from 0,001 to 3,0 kg/ha.

16. The method of claim 15, wherein the application rate of said compound is 0,01 to 1,0 kg/ha.

17. A compound of claim 1, wherein n is 1 and A, is oxygen, a group N-R12, where R12= hydrogen or alkyl, or a group SO2.

18. A compound of claim 1, wherein Ra, Rb, Rc, Rd, Re are independently hydrogen, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.

19. A compound of claim 1, wherein R1 is hydrogen, OH, Cl, Br, C1-C6-alkyl or OC(O)R4.

20. A compound of formula (Ia)




wherein
Rb, Rc, Rd independently of one another are hydrogen, OH, CN, NO2, halogen, C1-C10-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C4 -haloalkoxy, C1-C6-alkylthio, C1-C4 -haloalkylthio, C(O)R4, COOR5, NR6R7, C(O)NR8R9, S(O)2NR8R9, S(O)R11, S(O)2R11 or C1-C4-alkoxy- C1-C6-alkyl; and
R2 is C1-C10-alkyl, C3-C8-cycloalkyl, C3-C8-alkenyl, C3-C8-alkynyl, C5-C8-cycloalkenyl or C3-C8-cycloalkyl-C1-C4 -alkyl, wherein C1-C10-alkyl and C3-C8-cycloalkyl may be partially or fully halogenated and/or may carry one or two radicals selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl group, COOR5, NR6R7 and C(O)NR8R9, and wherein said phenyl group may be unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of halogen, nitro, OH, CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7 and C(O)NR8R9.

21. A compound as claimed in claim 1,
wherein R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C5-C6-cycloalkenyl, substituted or unsubstituted phenyl, C3-C6-cycloalkyl-C1-C4-alkyl, where C1-C6-alkyl and C3-C6 cycloalkyl may be partially or fully halogenated and/or may contain at least one radical selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7 and
C(O)NR8R9;
wherein R3 is hydrogen or C1-C4-alkyl; and
wherein X and Y represent oxygen.

22. A compound as claimed in claim 1,
wherein R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C5-C6-cycloalkenyl, substituted or unsubstituted phenyl, C3-C6-cycloalkyl-C1-C4-alkyl, where C1-C6-alkyl and C3-C6 cycloalkyl may be partially or fully halogenated and/or may contain at least one radical selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7 and
C(O)NR8R9;
wherein R3 is hydrogen or C1-C4-alkyl;
wherein X and Y represent oxygen; and
wherein n is 0.

23. A compound as claimed in claim 1,
wherein R1 is hydrogen;
wherein R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C5-C6-cycloalkenyl, substituted or unsubstituted phenyl, C3-C6-cycloalkyl-C1-C4-alkyl, where C1-C6-alkyl and C3-C6 cycloalkyl may be partially or fully halogenated and/or may contain at least one radical selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7 and
C(O)NR8R9;
wherein R3 is hydrogen or C1-C4-alkyl; and
wherein X and Y represent oxygen.

24. A compound as claimed in claim 1,
wherein R1 is hydrogen;
wherein R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C5-C6-cycloalkenyl, substituted or unsubstituted phenyl, C3-C6-cycloalkyl-C1-C4-alkyl, where C1-C6-alkyl and C3-C6 cycloalkyl may be partially or fully halogenated and/or may contain at least one radical selected from the group consisting of C1-C6-alkoxy, C1-C4-haloalkoxy, C1-C6-alkylthio, C1-C4-haloalkylthio, unsubstituted or substituted phenyl, COOR5, NR6R7 and
C(O)NR8R9;
wherein R3 is hydrogen or C1-C4-alkyl;
wherein X and Y represent oxygen; and
wherein n is 0.