# Patent

## Title
Tricyclic benzoylpyrazole derivatives used as a herbicide

## Abstract

Tricyclic benzoylpyrazole derivatives of the formula I




wherein X, Y, R1, R2, R6, R7, R3, R4, R5, l, R8 and R9 are as defined in the disclosure and their agriculturally useful salts; processes and intermediates for preparing the tricyclic benzoylpyrazole derivatives; compositions comprising them and the use of these derivatives or of the compositions comprising them for controlling undesirable plants are described.

## Background
This application is a 371 of PCT/EP00/02010 filed Mar. 8, 2000.
The present invention relates to novel tricyclic benzoylpyrazole derivatives of the formula I




where:

    
    
        X is oxygen, sulfur, S═O, S(═O)2, CR6R7, NR8 or a bond;
        Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle which contains one to three identical or different heteroatoms selected from the following group:
         oxygen, sulfur or nitrogen;
        R1,R2,R6,R7 are hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R3 is halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R4 is hydrogen, nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
        R5 is hydrogen, C1–C6-alkyl or halogen;
        R8 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkylcarbonyl, formyl, C1–C6-alkoxycarbonyl, C1–C6-haloalkoxycarbonyl, C1–C6-alkylsulfonyl or C1–C6-haloalkylsulfonyl;
        l is 0, 1 or 2;
        R9 is a radical IIa or IIb
    
    










    
    
        where
        R10 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14, NR15R16 or N-bonded heterocyclyl, where the heterocyclyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals:
         nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
        R11 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C3–C6-cycloalkyl, hydroxyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R12 is hydrogen, halogen, C1–C6-alkyl, C1–C6-haloalkyl, hydroxyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio or C1–C6-haloalkylthio;
        R13 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, C1–C20-alkylcarbonyl, C2–C20-alkenylcarbonyl, C2–C6-alkynylcarbonyl, C3–C6-cycloalkylcarbonyl, C1–C6-alkoxycarbonyl, C3–C6-alkenyloxycarbonyl, C3–C6-alkynyloxycarbonyl, C1–C6-alkylthiocarbonyl, C1–C6-alkylaminocarbonyl, C3–C6-alkenylaminocarbonyl, C3–C6-alkynylaminocarbonyl, N,N-di(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C1–C6-alkoxy)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkoxy)aminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkoxy)aminocarbonyl, di(C1–C6-alkyl)aminothiocarbonyl, C1–C6-alkylcarbonyl-C1–C6-alkyl, C1–C6-alkoxyimino-C1–C6-alkyl, N-(C1–C6-alkylamino)imino-C1–C6-alkyl or N,N-di(C1–C6-alkylamino)imino-C1–C6-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
         cyano, C1–C4-alkoxy, C1–C4-alkylthio, di(C1–C4-alkyl)amino, C1–C4-alkylcarbonyl, C1–C4-akoxycarbonyl, C1–C4-alkoxy-C1–C4-alkoxycarbonyl, di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
         is phenyl, heterocyclyl, phenyl-C1–C6-alkyl, heterocyclyl-C1–C6-alkyl, phenylcarbonyl-C1–C6-alkyl, heterocyclylcarbonyl-C1–C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenylaminocarbonyl, N-(C1–C6-alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl, N-(C1–C6-alkyl)-N-(heterocyclyl)aminocarbonyl, phenyl-C2–C6-alkenylcarbonyl or heterocyclyl-C2–C6-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
         nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy, C1–C4-haloalkoxy, heterocyclyl or N-bonded heterocyclyl, where the two lastmentioned substituents for their part may be partially or fully halogenated and/or may carry one to three of the following radicals:
         nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
        R14 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, C1–C6-alkoxy, di(C1–C6-alkyl)amino or di(C1–C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
         cyano, C1–C4-alkoxy, C1–C4-alkylthio, di(C1–C4-alkyl)amino, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, C1–C4-alkoxy-C1–C4-alkoxycarbonyl, di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
         is phenyl, heterocyclyl, phenyl-C1–C6-alkyl, heterocyclyl-C1–C6-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
         nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
        R15 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, C1–C6-alkoxy, C3–C6-alkenyloxy, C3–C6-alkynyloxy, di(C1–C6-alkyl)amino or C1–C6-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals of the following group:
         cyano, C1–C4-alkoxy, C1–C4-alkylthio, di(C1–C4-alkyl)amino, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, C1–C4-alkoxy-C1–C4-alkoxycarbonyl, di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
         is phenyl, heterocyclyl, phenyl-C1–C6-alkyl or heterocyclyl-C1–C6-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
         nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
        R16 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-alkynyl or C1–C6-alkylcarbonyl;

and their agriculturally useful salts.

    
    


Moreover, the invention relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them, and to the use of these derivatives or of the compositions comprising them for controlling harmful plants.
WO 97/19087 and EP-A 860 441 disclose tricyclic compounds which are characterized in that the respective benzoyl unit that they contain is fused via positions 3 and 4 with a bicycle. However, the herbicidal properties of the prior-art compounds and their compatibility with crop plants are not entirely satisfactory. It is an object of the present invention to provide novel, biologically, in particular herbicidally, active compounds having improved properties.
We have found that this object is achieved by the tricyclic benzoylpyrazole derivatives of the formula I and their herbicidal action.
Furthermore, we have found processes and intermediates for synthesizing the compounds of the formula I. Likewise, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they are present as enantiomers or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and their mixtures.
The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. Generally suitable are the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not negatively affect the herbicidal action of the compounds I.
Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C1–C4-alkyl, hydroxy-C1–C4-alkyl, C1–C4-alkoxy-C1–C4-alkyl, hydroxy-C1–C4-alkoxy-C1–C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1–C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1–C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1–C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
In the case of R10=hydroxyl or mercapto, IIa also represents the tautomeric forms IIa′ and IIa′′




Likewise, in the case of R10=hydroxyl or mercapto, IIb also represents the tautomeric forms IIb′ and IIb′′





The organic molecular moieties mentioned for the substituents R1–R17 or as radicals on phenyl and heterocyclyl radicals are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, hydroxyalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, N-alkylamino, N,N-dialkylamino, N-haloalkylamino, N,N-dihaloalkylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, hydroxyalkoxyalkyl, alkylcarbonylalkyl, alkoxyiminoalkyl, N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy and alkynyloxy moieties, may be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen denotes in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:

    
    
        C1–C4-alkyl and the alkyl moieties of hydroxy-C1–C4-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;
        C1–C6-alkyl, and the alkyl moieties of C1–C6-alkylcarbonyl-C1–C6-alkyl, C1–C6-alkoxyimino-C1–C6-alkyl, N-(C1–C6-alkylamino)imino-C1–C6-alkyl, N-(di-C1–C6-alkylamino)imino-C1–C6-alkyl, N-(C1–C6-alkoxy)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C1–C6-alkyl)-N-phenylaminocarbonyl, N-(C1–C6-alkyl)-N-heterocyclylaminocarbonyl, phenyl-C1–C6-alkyl, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino, heterocyclyl-C1–C6-alkyl, phenylcarbonyl-C1–C6-alkyl, heterocyclylcarbonyl-C1–C6-alkyl: C1–C4-alkyl as mentioned above, and also, for example, 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–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;
        C1–C6-haloalkyl, and the haloalkyl moieties of N-C1–C6-haloalkylamino and N,N-(di-C1–C6-haloalkyl)amino: C1–C4-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
        C1–C4-alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy;
        C1–C6-alkoxy, and the alkoxy moieties of C1–C6-alkoxyimino-C1–C6-alkyl, N-(C1–C6-alkoxy)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkoxy)aminocarbonyl and N-(C3–C6-alkynyl)-N-(C1–C6-alkoxy)aminocarbonyl: 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, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 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, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
        C1–C6-haloalkoxy: C1–C4-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
        C1–C4-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio;
        C1–C6-alkylthio, and the alkylthio moieties of C1–C6-alkylthiocarbonyl: 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–C6-haloalkylthio: a C1–C6-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, nonafluorobutylthio, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
        C1–C6-alkylsulfinyl (C1–C6-alkyl-S(═O)—): for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;
        C1–C6-haloalkylsulfinyl: a C1–C6-alkylsulfinyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl, 1-(chloromethyl)-2-chloroethylsulfinyl, 1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
        C1–C6-alkylsulfonyl (C1–C6-alkyl-S(═O)2—), and the alkylsulfonyl radicals of N-(C1–C6-alkylsulfonyl)amino and N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl;
        C1–C6-haloalkylsulfonyl, and the haloalkylsulfonyl radicals of N-(C1–C6-haloalkylsulfonyl)amino and N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino: a C1–C6-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;
        C1–C6-alkylamino, and the alkylamino radicals of N-(C1–C6-alkylamino)imino-C1–C6-alkyl: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;
        (C1–C6-alkylamino)sulfonyl: for example methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl, butylaminosulfonyl, 1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl, 1,1-dimethylethylaminosulfonyl, pentylaminosulfonyl, 1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl, 3-methylbutylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl, 1-ethylpropylaminosulfonyl, hexylaminosulfonyl, 1,1-dimethylpropylaminosulfonyl, 1,2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl, 2-methylpentylaminosulfonyl, 3-methylpentylaminosulfonyl, 4-methylpentylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl, 1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl, 2,2-dimethylbutylaminosulfonyl, 2,3-dimethylbutylaminosulfonyl, 3,3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl, 2-ethylbutylaminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl, 1,2,2-trimethylpropylaminosulfonyl, 1-ethyl-1-methylpropylaminosulfonyl or 1-ethyl-2-methylpropylaminosulfonyl;
        di(C1–C6-alkyl)aminosulfonyl: for example N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl, N,N-di(1-methylethyl)aminosulfonyl, N,N-dipropylaminosulfonyl, N,N-dibutylaminosulfonyl, N,N-di(1-methylpropyl)aminosulfonyl, N,N-di(2-methylpropyl)aminosulfonyl, N,N-di(1,1-dimethylethyl)aminosulfonyl, N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N-methyl-N-(1-methylethyl)aminosulfonyl, N-butyl-N-methylaminosulfonyl, N-methyl-N-(1-methylpropyl)aminosulfonyl, N-methyl-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-methylaminosulfonyl, N-ethyl-N-propylaminosulfonyl, N-ethyl-N-(1-methylethyl)aminosulfonyl, N-butyl-N-ethylaminosulfonyl, N-ethyl-N-(1-methylpropyl)aminosulfonyl, N-ethyl-N-(2-methylpropyl)aminosulfonyl, N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl, N-(1-methylethyl)-N-propylaminosulfonyl, N-butyl-N-propylaminosulfonyl, N-(1-methylpropyl)-N-propylaminosulfonyl, N-(2-methylpropyl)-N-propylaminosulfonyl, N-(1,1-dimethylethyl)-N-propylaminosulfonyl, N-butyl-N-(1-methylethyl)aminosulfonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl, N-butyl-N-(1-methylpropyl)aminosulfonyl, N-butyl-N-(2-methylpropyl)aminosulfonyl, N-butyl-N-(1,1-dimethylethyl)aminosulfonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl, N-methyl-N-pentylaminosulfonyl, N-methyl-N-(1-methylbutyl)aminosulfonyl, N-methyl-N-(2-methylbutyl)aminosulfonyl, N-methyl-N-(3-methylbutyl)aminosulfonyl, N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl, N-methyl-N-(1-ethylpropyl)aminosulfonyl, N-methyl-N-hexylaminosulfonyl, N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl, N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl, N-methyl-N-(1-methylpentyl)aminosulfonyl, N-methyl-N-(2-methylpentyl)aminosulfonyl, N-methyl-N-(3-methylpentyl)aminosulfonyl, N-methyl-N-(4-methylpentyl)aminosulfonyl, N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl, N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl, N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl, N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl, N-methyl-N-(1-ethylbutyl)aminosulfonyl, N-methyl-N-(2-ethylbutyl)aminosulfonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl, N-ethyl-N-pentylaminosulfonyl, N-ethyl-N-(1-methylbutyl)aminosulfonyl, N-ethyl-N-(2-methylbutyl)aminosulfonyl, N-ethyl-N-(3-methylbutyl)aminosulfonyl, N-ethyl-N-(2,2-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1-ethylpropyl)aminosulfonyl, N-ethyl-N-hexylaminosulfonyl, N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1,2-dimethylpropyl)aminosulfonyl, N-ethyl-N-(1-methylpentyl)aminosulfonyl, N-ethyl-N-(2-methylpentyl)aminosulfonyl, N-ethyl-N-(3-methylpentyl)aminosulfonyl, N-ethyl-N-(4-methylpentyl)aminosulfonyl, N-ethyl-N-(1,1-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl, N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl, N-ethyl-N-(1-ethylbutyl)aminosulfonyl, N-ethyl-N-(2-ethylbutyl)aminosulfonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminosulfonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl, N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl, N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl, N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or N,N-dihexylaminosulfonyl;
        di(C1–C4-alkyl)amino, and the dialkylamino radicals of di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl and N-(di-C1–C4-alkylamino)imino-C1–C6-alkyl: for example N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;
        di(C1–C6-alkyl)amino, and the dialkylamino radicals of di(C1–C6-alkyl)aminoimino-C1–C6-alkyl: di(C1–C4-alkyl)amino as mentioned above, and also N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino;
        C1–C4-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethylcarbonyl;
        C1–C6-alkylcarbonyl, and the alkylcarbonyl radicals of C1–C6-alkylcarbonyl-C1–C6-alkyl: C1–C4-alkylcarbonyl as mentioned above, and also, for example, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
        C1–C20-alkylcarbonyl: C1–C6-alkylcarbonyl as mentioned above, and also heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;
        C1–C4-alkoxycarbonyl, and the alkoxycarbonyl moieties of di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;
        (C1–C6-alkoxy)carbonyl: (C1–C4-alkoxy)carbonyl as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methyl-propoxycarbonyl or 1-ethyl-2-methyl-propoxycarbonyl;
        C1–C6-haloalkoxycarbonyl: a C1–C6-alkoxycarbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl, 1-(chloromethyl)-2-chloroethoxycarbonyl, 1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl, nonafluorobutoxycarbonyl, 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 5-iodopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-bromohexoxycarbonyl, 6-iodohexoxycarbonyl or dodecafluorohexoxycarbonyl;
        (C1–C4-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1,1-dimethylethylcarbonyloxy;
        (C1–C4-alkylamino)carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;
        (C1–C6-alkylamino)carbonyl: (C1–C4-alkylamino)carbonyl as mentioned above, and also, for example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl;
        di(C1–C4-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di(1-methylpropyl)aminocarbonyl, N,N-di(2-methylpropyl)aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;
        di(C1–C6-alkyl)aminocarbonyl: di(C1–C4-alkyl)aminocarbonyl as mentioned above, and also, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N-(1-methylbutyl)aminocarbonyl, N-Methyl-N-(2-methylbutyl)aminocarbonyl, N-methyl-N-(3-methylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethylpropyl)aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-methyl-N-(1-methylpentyl)aminocarbonyl, N-methyl-N-(2-methylpentyl)aminocarbonyl, N-methyl-N-(3-methylpentyl)aminocarbonyl, N-methyl-N-(4-methylpentyl)aminocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-methyl-N-(1-ethylbutyl)aminocarbonyl, N-methyl-N-(2-ethylbutyl)aminocarbonyl, N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-ethyl-N-pentylaminocarbonyl, N-ethyl-N-(1-methylbutyl)aminocarbonyl, N-ethyl-N-(2-methylbutyl)aminocarbonyl, N-ethyl-N-(3-methylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethylpropyl)aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl, N-ethyl-N-(1-methylpentyl)aminocarbonyl, N-ethyl-N-(2-methylpentyl)aminocarbonyl, N-ethyl-N-(3-methylpentyl)aminocarbonyl, N-ethyl-N-(4-methylpentyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl, N-ethyl-N-(1-ethylbutyl)aminocarbonyl, N-ethyl-N-(2-ethylbutyl)aminocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or N,N-dihexylaminocarbonyl;
        di(C1–C6-alkyl)aminothiocarbonyl: for example N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl, N,N-di(1-methylethyl)aminothiocarbonyl, N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl, N,N-di(1-methylpropyl)aminothiocarbonyl, N,N-di(2-methylpropyl)aminothiocarbonyl, N,N-di(1,1-dimethylethyl)aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N-(1-methylpropyl)aminothiocarbonyl, N-methyl-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl N-(1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(2-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N-(1-methylpropyl)-N-propylaminothiocarbonyl, N-(2-methylpropyl)-N-propylaminothiocarbonyl, N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl, N-butyl-N-(1-methylethyl)aminothiocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl, N-butyl-N-(1-methylpropyl)aminothiocarbonyl, N-butyl-N-(2-methylpropyl)aminothiocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl, N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N-(1-methylbutyl)aminothiocarbonyl, N-methyl-N-(2-methylbutyl)aminothiocarbonyl, N-methyl-N-(3-methylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethylpropyl)aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-methylpentyl)aminothiocarbonyl, N-methyl-N-(2-methylpentyl)aminothiocarbonyl, N-methyl-N-(3-methylpentyl)aminothiocarbonyl, N-methyl-N-(4-methylpentyl)aminothiocarbonyl, N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-methyl-N-(1-ethylbutyl)aminothiocarbonyl, N-methyl-N-(2-ethylbutyl)aminothiocarbonyl, N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N-ethyl-N-(1-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2-methylbutyl)aminothiocarbonyl, N-ethyl-N-(3-methylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-methylpentyl)aminothiocarbonyl, N-ethyl-N-(2-methylpentyl)aminothiocarbonyl, N-ethyl-N-(3-methylpentyl)aminothiocarbonyl, N-ethyl-N-(4-methylpentyl)aminothiocarbonyl, N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl, N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl, N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl, N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N,N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or N,N-dihexylaminothiocarbonyl;
        C1–C4-alkoxy-C1–C4-alkyl and the alkoxyalkyl moieties of hydroxy-C1–C4-alkoxy-C1–C4-alkyl: C1–C4-alkyl which is substituted by C1–C4-alkoxy as mentioned above, i.e., for example, methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl;
        C1–C4-alkoxy-C1–C4-alkoxy as alkoxyalkoxy moieties of C1–C4-alkoxy-C1–C4-alkoxycarbonyl: C1–C4-alkoxy which is substituted by C1–C4-alkoxy as mentioned above, i.e., for example, methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy)methoxy, butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy, 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;
        C3–C6-alkenyl, and the alkenyl moieties of C3–C6-alkenylcarbonyl, C3–C6-alkenyloxy, C3–C6-alkenyloxycarbonyl, C3–C6-alkenylaminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkoxy)aminocarbonyl: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl, 1-penten-4-yl, 2-penten-4-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-2-en-1-yl, 1-ethylprop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-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-2-en-1-yl, 1,2-dimethylbut-3-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-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-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 or 1-ethyl-2-methylprop-2-en-1-yl;
        C2–C6-alkenyl, and the alkenyl moieties of C2–C6-alkenylcarbonyl, phenyl-C2–C6-alkenylcarbonyl and heterocyclyl-C2–C6-alkenylcarbonyl: C3–C6-alkenyl as mentioned above, and also ethenyl;
        C2–C20-alkenyl as alkenyl moiety of C2–C20-alkenylcarbonyl: C2–C6-alkenyl as mentioned above, and also pentadecenyl or heptadecenyl;
        C3–C6-haloalkenyl: a C3–C6-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 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 or 2,3-dibromobut-2-enyl;
        C3–C6-alkynyl, and the alkynyl moieties of C3–C6-alkynylcarbonyl, C3–C6-alkynyloxy, C3–C6-alkynyloxycarbonyl, C3–C6-alkynylaminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkoxyamino)carbonyl: for example propargyl, 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;
        C2–C6-alkynyl, and the alkynyl moieties of C2–C6-alkynylcarbonyl: C3–C6-alkynyl as mentioned above, and also ethynyl;
        C3–C6-haloalkynyl: a C3–C6-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
        C3–C6-cycloalkyl, and the cycloalkyl moieties of C3–C6-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
        heterocyclyl, and the heterocyclyl moieties of heterocyclyloxy, heterocyclylcarbonyl, heterocyclyl-C1–C6-alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclyl-C2–C6-alkenylcarbonyl, heterocyclylcarbonyl-C1–C6-alkyl, N-(C1–C6-alkyl)-N-(heterocyclyl)aminocarbonyl, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which is attached via carbon and contains one to four identical or different heteroatoms selected from the following group: oxygen, sulfur and nitrogen, i.e., for example, 5-membered rings having, for example, one heteroatom, having two heteroatoms, having three heteroatoms or having four heteroatoms or, for example, 6-membered rings having, for example, one heteroatom, having two heteroatoms, having three heteroatoms or having four heteroatoms, i.e. 5-membered rings having one heteroatom, such as:
        tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl, 2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl, 2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl, 4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or pyrrol-3-yl;
        5-membered rings having two heteroatoms such as:
        tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl, tetrahydrothiazol-5-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-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl, 2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl, 2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, Δ3-1,2-dithiol-3-yl, Δ3-1,2-dithiol-4-yl, Δ3-1,2-dithiol-5-yl, 4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl, 4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl, 2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl, 2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl or thiazol-5-yl;
        5-membered rings having three heteroatoms such as:
        1,2,3-Δ2-oxadiazolin-4-yl, 1,2,3-Δ2-oxadiazolin-5-yl, 1,2,4-Δ4-oxadiazolin-3-yl, 1,2,4-Δ4-oxadiazolin-5-yl, 1,2,4-Δ2-oxadiazolin-3-yl, 1,2,4-Δ2-oxadiazolin-5-yl, 1,2,4-Δ3-oxadiazolin-3-yl, 1,2,4-Δ3-oxadiazolin-5-yl, 1,3,4-Δ2-oxadiazolin-2-yl, 1,3,4-Δ2-oxadiazolin-5-yl, 1,3,4-Δ3-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl, 1,2,3-Δ2-thiadiazolin-4-yl, 1,2,3-Δ2-thiadiazolin-5-yl, 1,2,4-Δ4-thiadiazolin-3-yl, 1,2,4-Δ4-thiadiazolin-5-yl, 1,2,4-Δ3-thiadiazolin-3-yl, 1,2,4-Δ3-thiadiazolin-5-yl, 1,2,4-Δ2-thiadiazolin-3-yl, 1,2,4-Δ2-thiadiazolin-5-yl, 1,3,4-Δ2-thiadiazolin-2-yl, 1,3,4-Δ2-thiadiazolin-5-yl, 1,3,4-Δ3-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl, 1,3,2-dioxathiolan-4-yl, 1,2,3-Δ2-triazolin-4-yl, 1,2,3-Δ2-triazolin-5-yl, 1,2,4-Δ2-triazolin-3-yl, 1,2,4-Δ2-triazolin-5-yl, 1,2,4-Δ3-triazolin-3-yl, 1,2,4-Δ3-triazolin-5-yl, 1,2,4-Δ1-triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl, 2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;
        5-membered rings having four heteroatoms such as:
        tetrazol-5-yl;
        6-membered rings having one heteroatom such as:
        tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl, 1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl, 2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl, 2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl, 2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl, 1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl, 1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl, 1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl, 2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl, 2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl, 1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl, 1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl, 3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl, 2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl, 2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl, 2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl;
        6-membered rings having two heteroatoms such as:
        1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-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, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl, tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl, tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl, tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl, 2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl, 2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl, 2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl, 4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl, 4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl, 4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl, 4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl, 2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl, 2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl, 2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl, 2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl, 2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl, 2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl, 2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl, 2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl, 2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl, 3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl, 1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl, 1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl, 4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl, 4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl, 4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl, 3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl, 3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl, 1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl, 1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl, 1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl, 2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl, 2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl, 2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl, 2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl, 2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl, 4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl, 4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl, 4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl, 6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl, 6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl, 2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl, 2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl, 2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl, 4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl, 4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl, 2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl, 2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl, 2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl, 4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl, 1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl, 1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or 3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;
        6-membered rings having three heteroatoms such as:
        1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl;
        6-membered rings having four heteroatoms such as:
        1,2,4,5-tetrazin-3-yl;
        where, if appropriate, the sulfur of the abovementioned heterocycles may be oxidized to S═O or S(═O)2 
        and where a bicyclic ring system may be formed with a fused-on phenyl ring or with a C3–C6-carbocycle or with a further 5- to 6-membered heterocycle.
        N-bonded heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered heterocyclic ring which is attached via nitrogen and contains at least one nitrogen and, if appropriate, one to three identical or different heteroatoms selected from the following group: oxygen, sulfur and nitrogen, i.e., for example,
        N-bonded 5-membered rings such as:
        tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl, 2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl, 2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl, 2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,4-Δ4-oxadiazolin-2-yl, 1,2,4-Δ2-oxadiazolin-4-yl, 1,2,4-Δ3-oxadiazolin-2-yl, 1,3,4-Δ2-oxadiazolin-4-yl, 1,2,4-Δ5-thiadiazolin-2-yl, 1,2,4-Δ3-thiadiazolin-2-yl, 1,2,4-Δ2-thiadiazolin-4-yl, 1,3,4-Δ2-thiadiazolin-4-yl, 1,2,3-Δ2-triazolin-1-yl, 1,2,4-Δ2-triazolin-1-yl, 1,2,4-Δ2-triazolin-4-yl, 1,2,4-Δ3-triazolin-1-yl, 1,2,4-Δ1-triazolin-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, tetrazol-1-yl;
        and also N-bonded 6-membered rings such as:
        piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl, 1,2-dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl, tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl, tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl, 2H-3,6-dihydro-1,2-oxazin-2-yl, 2H-3,6-dihydro-1,2-thiazin-2-yl, 2H-3,4-dihydro-1,2-oxazin-2-yl, 2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl, 1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl, 1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl, 1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl;
        and also N-bonded cyclic imides such as:
        phthalimide, tetrahydrophthalimide, succinimide, maleimide, glutarimide, 5-oxotriazolin-1-yl, 5-oxo-1,3,4-oxadiazolin-4-yl or 2,4-dioxo-(1H, 3H)-pyrimidin-3-yl;
        where a bicyclic ring system may be formed with a fused-on phenyl ring or with a C3–C6-carbocycle or a further 5- to 6-membered heterocycle.
    
    


All phenyl rings, heterocyclyl or N-heterocyclyl radicals and all phenyl components in phenoxy, phenyl-C1–C6-alkyl, phenylcarbonyl-C1–C6-alkyl, phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl and N-(C1–C6-alkyl)-N-phenylaminocarbonyl or heterocyclyl components in heterocyclyloxy, heterocyclyl-C1–C6-alkyl, heterocyclylcarbonyl-C1–C6-alkyl, heterocyclylcarbonyl, heterocyclyloxythiocarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl and N-(C1–C6-alkyl)-N-heterocyclylaminocarbonyl are, unless stated otherwise, preferably unsubstituted, or they carry one to three halogen atoms and/or one nitro group, one cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.
Furthermore, the expression “Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated heterocycle which contains one to three identical or different heteroatoms selected from the following group: oxygen, sulfur and nitrogen” denotes, for example, 5-membered rings having one heteroatom such as:
tetrahydrofurandiyl, tetrahydrothienediyl, tetrahydropyrrolediyl, dihydrofurandiyl, dihydrothienediyl, dihydropyrrolediyl, furandiyl, thienediyl or pyrrolediyl;
or 5-membered rings having two heteroatoms such as:
tetrahydropyrazolediyl, tetrahydroisoxazolediyl, 1,2-oxathiolanediyl, tetrahydroisothiazolediyl, 1,2-dithiolanediyl, tetrahydroimidazolediyl, tetrahydrooxazolediyl, tetrahydrothiazolediyl, 1,3-dioxolanediyl, 1,3-oxathiolanediyl, dihydropyrazolediyl, dihydroisoxazolediyl, dihydroisothiazolediyl, 1,2-dithiolediyl, dihydroimidazolediyl, dihydrooxazolediyl, dihydrothiazolediyl, dioxolediyl, oxathiolediyl, pyrazolediyl, isoxazolediyl, isothiazolediyl, imidazolediyl, oxazolediyl or thiazolediyl;

or 5-membered rings having three heteroatoms such as:

1,2,3-oxadiazolinediyl, 1,2,3-thiadiazolinediyl, 1,2,3-triazolinediyl, 1,2,3-oxadiazolediyl, 1,2,3-thiadiazolediyl or 1,2,3-triazolediyl;

or 6-membered rings having one heteroatom such as:

tetrahydropyrandiyl, piperidinediyl, tetrahydrothiopyrandiyl, dihydropyrandiyl, dihydrothiopyrandiyl, tetrahydropyridinediyl, pyrandiyl, thiopyrandiyl, dihydropyrinediyl or pyridinediyl;

or 6-membered rings having two heteroatoms such as:

1,3-dioxanediyl, 1,4-dioxanediyl, 1,3-dithianediyl, 1,4-dithianediyl, 1,3-oxathianediyl, 1,4-oxathianediyl, 1,2-dithianediyl, hexahydropyrimidinediyl, hexahydropyrazinediyl, hexahydropyridazinediyl, tetrahydro-1,3-oxazinediyl, tetrahydro-1,3-thiazinediyl, tetrahydro-1,4-oxazinediyl, tetrahydro-1,2-oxazinediyl, dihydro-1,2-oxazinediyl, dihydro-1,2-thiazinediyl, tetrahydropyridazinediyl, dihydro-1,3-oxazinediyl, dihydro-1,3-oxazinediyl, dihydro-1,3-thiazinediyl, tetrahydropyrimidinediyl, tetrahydropyrazinediyl, dihydro-1,4-thiazinediyl, dihydro-1,4-oxazinediyl, dihydro-1,4-dioxinediyl, dihydro-1,4-dithiinediyl, 1,2-oxazinediyl, 1,2-thiazinediyl, 1,3-oxazinediyl, 1,3-thiazinediyl, 1,4-oxazinediyl, 1,4-thiazinediyl, dihydropyridazinediyl, dihydropyrazinediyl, dihydropyrimidinediyl, pyridazinediyl, pyrimidinediyl or pyrazinediyl;

or 6-membered rings having 3 heteroatoms such as:

1,2,4-triazinediyl;

where, if appropriate, the sulfur of the abovementioned heterocycles may be oxidized to S═O or S(═O)2;

and where the moiety is fused to the skeleton via two adjacent carbon atoms.

The compounds of the formula I according to the invention where R9=IIa are referred to as compounds of the formula Ia, and compounds of the formula I where R9=IIb are referred to as Ib.
Preference is given to the compounds of the formula I, where

    R11 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, hydroxyl, C1–C6-alkoxy or C1–C6-haloalkoxy;


Preference is likewise given to the compounds of the formula Ia.
With respect to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case alone or in combination:

    X is oxygen, sulfur, S═O, S(═O)2, CR6R7, NR8 or a bond;
    Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle which contains one or two identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen;
    R1,R2 are hydrogen or C1–C6-alkyl;
    R3 is halogen, C1–C6-alkyl or C1–C6-alkoxy;
    R4 is nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
     in particular nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfonyl or C1–C6-haloalkylsulfonyl;
    R5 is hydrogen;
    R6,R7 are hydrogen or C1–C6-alkyl;
    R8 is C1–C6-alkyl, C1–C6-alkylcarbonyl or C1–C6-alkylsulfonyl;
    l is 0, 1 or 2;
    R9 is a radical IIa






where

    R10 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14 or N-bonded heterocyclyl, where the heterocyclyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals:
     nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
    R11 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl or C3–C6-cycloalkyl;
    R12 is hydrogen, C1–C6-alkyl or C1–C6-haloalkyl;
    R13 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C1–C6-alkylcarbonyl, C2–C6-alkenylcarbonyl, C3–C6-cycloalkylcarbonyl, C1–C6-alkoxycarbonyl, C3–C6-alkenyloxycarbonyl, C3–C6-alkynyloxycarbonyl, C1–C6-alkylthiocarbonyl, C1–C6-alkylaminocarbonyl, C3–C6-alkenylaminocarbonyl, C3–C6-alkynylaminocarbonyl, N,N-di(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C1–C6-alkoxy)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkoxy)aminocarbonyl N-(C3–C6-alkynyl)-N-(C1–C6-alkoxy)aminocarbonyl, di(C1–C6-alkyl)aminothiocarbonyl, C1–C6-alkylcarbonyl-C1–C6-alkyl, C1–C6-alkoxyimino-C1–C6-alkyl, N-(C1–C6-alkylamino)imino-C1–C6-alkyl or N,N-di(C1–C6-alkylamino)imino-C1–C6-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
     cyano, C1–C4-alkoxy, C1–C4-alkylthio, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, hydroxycarbonyl, di(C1–C4-alkyl)aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
     is phenyl, heterocyclyl, phenyl-C1–C6-alkyl, heterocyclyl-C1–C6-alkyl, phenylcarbonyl-C1–C6-alkyl, heterocyclylcarbonyl-C1–C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenyl-C2–C6-alkenylcarbonyl or heterocyclyl-C2–C6-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 14 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
     nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy, C1–C4-haloalkoxy, heterocyclyl or N-bonded heterocyclyl, where the two lastmentioned substituents for their part may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
    R14 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-cycloalkyl, C1–C6-alkoxy or di(C1–C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
     cyano, C1–C4-alkoxy, C1–C4-alkylthio, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, hydroxycarbonyl, di(C1–C4-alkyl)aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
     is phenyl, heterocyclyl, phenyl-C1–C6-alkyl, heterocyclyl-C1–C6-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
     nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy.


Particular preference is given to compounds of the formula I where the variables have the following meanings, either alone or in combination:

    X is oxygen, sulfur, S═O, S(═O)2, CR6R7 or a bond;
    Y together with the two carbons to which it is attached forms the following heterocycles:
     (in the embodiments of the heterocycles below, the upper undulating line represents in each case the link to the hydrocarbon which carries the radicals R1 and R2, and the lower undulating line represents the link to the meta-carbon of the benzoyl moiety).












where the sulfur of the abovementioned heterocycles may be oxidized to S═O or S(═O)2;

in particular, Y together with the two carbons to which it is attached forms the following heterocycles:








    R1,R2 are hydrogen;
    R3 is C1–C6-alkyl, such as methyl, ethyl or n-propyl;
     in particular methyl;
    R4 is nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-alkylsulfonyl;
     in particular nitro, halogen, such as fluorine, chlorine or bromine, C1–C6-haloalkyl such as trifluoromethyl, C1–C6-alkylthio, such as methylthio or ethylthio, or C1–C6-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl;
     particularly preferably nitro, chlorine, trifluoromethyl, methylthio or methylsulfonyl;
    R5 is hydrogen;
    R6,R7 are hydrogen or C1–C6-alkyl, such as methyl or ethyl;
     in particular hydrogen or methyl;
    l is 0, 1 or 2;
     in particular 0 or 1;
    R9 is a radical IIa






where

    R10 is hydroxyl;
    R11 is C1–C6-alkyl, such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 2-methylpropyl or 1,1-dimethylethyl or cyclopropyl;
     in particular methyl or ethyl;
     likewise particularly preferred cyclopropyl;
    R12 is hydrogen or C1–C6-alkyl, such as methyl, ethyl, n-propyl or 1-methylethyl;
     in particular hydrogen or methyl.


Very particular preference is given to the compounds Ia where

    X is oxygen, sulfur, S(═O)2, CH2 or a bond;
    Y together with the two carbons to which it is attached forms the following heterocycles:






    R1,R2 are hydrogen;
    R3 is C1–C4-alkyl;
    R4 is nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-alkylsulfonyl;
    R5 is hydrogen or C1–C6-alkyl;
    l is 0, 1 or 2;
    R9 is a radical IIa;
    R10 is hydroxyl;
    R11 is hydrogen, C1–C6-alkyl or cyclopropyl;
     in particular C1–C6-alkyl;
    R12 is hydrogen, C1–C6-alkyl or C1–C6-haloalkyl.


Very particular preference is also given to the compounds Ia where X is oxygen, sulfur or a bond.
Very particular preference is also given to the compounds Ia where

    Y together with the two carbons to which it is attached forms a heterocycle selected from the following group: dihydropyrazolediyl, dihydroisoxazolediyl, pyrazolediyl, isoxazolediyl or pyrimidinediyl.


Most preferably, Y together with the two carbons to which it is attached forms the following heterocycles:




Very particular preference is also given to the compounds of the formula I where

    R1, R2 are hydrogen;
    R3 is C1–C6-alkyl;
    R4 is nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-akylsulfonyl;
     in particular halogen, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-alkylsulfonyl;
    R5 is hydrogen;
    l is 0 oder 1.


Very particular preference is also given to the compounds of the formula I where

    R10 is hydroxyl or phenylcarbonyloxy which may be unsubstituted or partially or fully halogenated and/or may carry one to three of the following radicals:
     nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
     in particular hydroxyl;
    R11 is C1–C6-alkyl or C3–C6-cycloalkyl;
     in particular C1–C6-alkyl or
     also in particular cyclopropyl;
    R12 is hydrogen or C1–C6-alkyl;
     in particular hydrogen.


Very particular preference is also given to the compounds of the formula Ia1 (≡Ia where R1, R2, R5 and R12=H, l=0, meaning of the heterocycle according to structural formula), most particularly to compounds Ia1.n where the variables X, R4, R10 and R11 are as defined in Table 1.
The radical definitions of R1 to R12, X, Y and l given above and the meaning of the fused heterocycle are of particular importance for the compounds according to the invention, not only in combination with one another, but also taken on their own. (For reasons of clarity, in the formulae Ia1, Ia2 . . . , the meaning of the fused heterocycle is in each case as given in the corresponding structural formula.)















TABLE 1





n
X
R4
R10
R11



















1
bond
F
OH
CH3


2
bond
Cl
OH
CH3


3
bond
Br
OH
CH3


4
bond
NO2
OH
CH3


5
bond
SCH3
OH
CH3


6
bond
SO2CH3
OH
CH3


7
bond
SO2CH2CH3
OH
CH3


8
bond
CH3
OH
CH3


9
bond
CF3
OH
CH3


10
bond
OCHF2
OH
CH3


11
CH2
F
OH
CH3


12
CH2
Cl
OH
CH3


13
CH2
Br
OH
CH3


14
CH2
NO2
OH
CH3


15
CH2
SCH3
OH
CH3


16
CH2
SO2CH3
OH
CH3


17
CH2
SO2CH2CH3
OH
CH3


18
CH2
CH3
OH
CH3


19
CH2
CF3
OH
CH3


20
CH2
OCHF2
OH
CH3


21
O
F
OH
CH3


22
O
Cl
OH
CH3


23
O
Br
OH
CH3


24
O
NO2
OH
CH3


25
O
SCH3
OH
CH3


26
O
SO2CH3
OH
CH3


27
O
SO2CH2CH3
OH
CH3


28
O
CH3
OH
CH3


29
O
CF3
OH
CH3


30
O
OCHF2
OH
CH3


31
S
F
OH
CH3


32
S
Cl
OH
CH3


33
S
Br
OH
CH3


34
S
NO2
OH
CH3


35
S
SCH3
OH
CH3


36
S
SO2CH3
OH
CH3


37
S
SO2CH2CH3
OH
CH3


38
S
CH3
OH
CH3


39
S
CF3
OH
CH3


40
S
OCHF2
OH
CH3


41
SO2
F
OH
CH3


42
SO2
Cl
OH
CH3


43
SO2
Br
OH
CH3


44
SO2
NO2
OH
CH3


45
SO2
SCH3
OH
CH3


46
SO2
SO2CH3
OH
CH3


47
SO2
SO2CH2CH3
OH
CH3


48
SO2
CH3
OH
CH3


49
SO2
CF3
OH
CH3


50
SO2
OCHF2
OH
CH3


51
bond
F
OH
CH2CH3


52
bond
Cl
OH
CH2CH3


53
bond
Br
OH
CH2CH3


54
bond
NO2
OH
CH2CH3


55
bond
SCH3
OH
CH2CH3


56
bond
SO2CH3
OH
CH2CH3


57
bond
SO2CH2CH3
OH
CH2CH3


58
bond
CH3
OH
CH2CH3


59
bond
CF3
OH
CH2CH3


60
bond
OCHF2
OH
CH2CH3


61
CH2
F
OH
CH2CH3


62
CH2
Cl
OH
CH2CH3


63
CH2
Br
OH
CH2CH3


64
CH2
NO2
OH
CH2CH3


65
CH2
SCH3
OH
CH2CH3


66
CH2
SO2CH3
OH
CH2CH3


67
CH2
SO2CH2CH3
OH
CH2CH3


68
CH2
CH3
OH
CH2CH3


69
CH2
CF3
OH
CH2CH3


70
CH2
OCHF2
OH
CH2CH3


71
O
F
OH
CH2CH3


72
O
Cl
OH
CH2CH3


73
O
Br
OH
CH2CH3


74
O
NO2
OH
CH2CH3


75
O
SCH3
OH
CH2CH3


76
O
SO2CH3
OH
CH2CH3


77
O
SO2CH2CH3
OH
CH2CH3


78
O
CH3
OH
CH2CH3


79
O
CF3
OH
CH2CH3


80
O
OCHF2
OH
CH2CH3


81
S
F
OH
CH2CH3


82
S
Cl
OH
CH2CH3


83
S
Br
OH
CH2CH3


84
S
NO2
OH
CH2CH3


85
S
SCH3
OH
CH2CH3


86
S
SO2CH3
OH
CH2CH3


87
S
SO2CH2CH3
OH
CH2CH3


88
S
CH3
OH
CH2CH3


89
S
CF3
OH
CH2CH3


90
S
OCHF2
OH
CH2CH3


91
SO2
F
OH
CH2CH3


92
SO2
Cl
OH
CH2CH3


93
SO2
Br
OH
CH2CH3


94
SO2
NO2
OH
CH2CH3


95
SO2
SCH3
OH
CH2CH3


96
SO2
SO2CH3
OH
CH2CH3


97
SO2
SO2CH2CH3
OH
CH2CH3


98
SO2
CH3
OH
CH2CH3


99
SO2
CF3
OH
CH2CH3


100
SO2
OCHF2
OH
CH2CH3


101
bond
F
OCOC6H5
CH3


102
bond
Cl
OCOC6H5
CH3


103
bond
Br
OCOC6H5
CH3


104
bond
NO2
OCOC6H5
CH3


105
bond
SCH3
OCOC6H5
CH3


106
bond
SO2CH3
OCOC6H5
CH3


107
bond
SO2CH2CH3
OCOC6H5
CH3


108
bond
CH3
OCOC6H5
CH3


109
bond
CF3
OCOC6H5
CH3


110
bond
OCHF2
OCOC6H5
CH3


111
CH2
F
OCOC6H5
CH3


112
CH2
Cl
OCOC6H5
CH3


113
CH2
Br
OCOC6H5
CH3


114
CH2
NO2
OCOC6H5
CH3


115
CH2
SCH3
OCOC6H5
CH3


116
CH2
SO2CH3
OCOC6H5
CH3


117
CH2
SO2CH2CH3
OCOC6H5
CH3


118
CH2
CH3
OCOC6H5
CH3


119
CH2
CF3
OCOC6H5
CH3


120
CH2
OCHF2
OCOC6H5
CH3


121
O
F
OCOC6H5
CH3


122
O
Cl
OCOC6H5
CH3


123
O
Br
OCOC6H5
CH3


124
O
NO2
OCOC6H5
CH3


125
O
SCH3
OCOC6H5
CH3


126
O
SO2CH3
OCOC6H5
CH3


127
O
SO2CH2CH3
OCOC6H5
CH3


128
O
CH3
OCOC6H5
CH3


129
O
CF3
OCOC6H5
CH3


130
O
OCHF2
OCOC6H5
CH3


131
S
F
OCOC6H5
CH3


132
S
Cl
OCOC6H5
CH3


133
S
Br
OCOC6H5
CH3


134
S
NO2
OCOC6H5
CH3


135
S
SCH3
OCOC6H5
CH3


136
S
SO2CH3
OCOC6H5
CH3


137
S
SO2CH2CH3
OCOC6H5
CH3


138
S
CH3
OCOC6H5
CH3


139
S
CF3
OCOC6H5
CH3


140
S
OCHF2
OCOC6H5
CH3


141
SO2
F
OCOC6H5
CH3


142
SO2
Cl
OCOC6H5
CH3


143
SO2
Br
OCOC6H5
CH3


144
SO2
NO2
OCOC6H5
CH3


145
SO2
SCH3
OCOC6H5
CH3


146
SO2
SO2CH3
OCOC6H5
CH3


147
SO2
SO2CH2CH3
OCOC6H5
CH3


148
SO2
CH3
OCOC6H5
CH3


149
SO2
CF3
OCOC6H5
CH3


150
SO2
OCHF2
OCOC6H5
CH3


151
bond
F
OCOC6H5
CH2CH3


152
bond
Cl
OCOC6H5
CH2CH3


153
bond
Br
OCOC6H5
CH2CH3


154
bond
NO2
OCOC6H5
CH2CH3


155
bond
SCH3
OCOC6H5
CH2CH3


156
bond
SO2CH3
OCOC6H5
CH2CH3


157
bond
SO2CH2CH3
OCOC6H5
CH2CH3


158
bond
CH3
OCOC6H5
CH2CH3


159
bond
CF3
OCOC6H5
CH2CH3


160
bond
OCHF2
OCOC6H5
CH2CH3


161
CH2
F
OCOC6H5
CH2CH3


162
CH2
Cl
OCOC6H5
CH2CH3


163
CH2
Br
OCOC6H5
CH2CH3


164
CH2
NO2
OCOC6H5
CH2CH3


165
CH2
SCH3
OCOC6H5
CH2CH3


166
CH2
SO2CH3
OCOC6H5
CH2CH3


167
CH2
SO2CH2CH3
OCOC6H5
CH2CH3


168
CH2
CH3
OCOC6H5
CH2CH3


169
CH2
CF3
OCOC6H5
CH2CH3


170
CH2
OCHF2
OCOC6H5
CH2CH3


171
O
F
OCOC6H5
CH2CH3


172
O
Cl
OCOC6H5
CH2CH3


173
O
Br
OCOC6H5
CH2CH3


174
O
NO2
OCOC6H5
CH2CH3


175
O
SCH3
OCOC6H5
CH2CH3


176
O
SO2CH3
OCOC6H5
CH2CH3


177
O
SO2CH2CH3
OCOC6H5
CH2CH3


178
O
CH3
OCOC6H5
CH2CH3


179
O
CF3
OCOC6H5
CH2CH3


180
O
OCHF2
OCOC6H5
CH2CH3


181
S
F
OCOC6H5
CH2CH3


182
S
Cl
OCOC6H5
CH2CH3


183
S
Br
OCOC6H5
CH2CH3


184
S
NO2
OCOC6H5
CH2CH3


185
S
SCH3
OCOC6H5
CH2CH3


186
S
SO2CH3
OCOC6H5
CH2CH3


187
S
SO2CH2CH3
OCOC6H5
CH2CH3


188
S
CH3
OCOC6H5
CH2CH3


189
S
CF3
OCOC6H5
CH2CH3


190
S
OCHF2
OCOC6H5
CH2CH3


191
SO2
F
OCOC6H5
CH2CH3


192
SO2
Cl
OCOC6H5
CH2CH3


193
SO2
Br
OCOC6H5
CH2CH3


194
SO2
NO2
OCOC6H5
CH2CH3


195
SO2
SCH3
OCOC6H5
CH2CH3


196
SO2
SO2CH3
OCOC6H5
CH2CH3


197
SO2
SO2CH2CH3
OCOC6H5
CH2CH3


198
SO2
CH3
OCOC6H5
CH2CH3


199
SO2
CF3
OCOC6H5
CH2CH3


200
SO2
OCHF2
OCOC6H5
CH2CH3


201
bond
F
OCOC(CH3)3
CH3


202
bond
Cl
OCOC(CH3)3
CH3


203
bond
Br
OCOC(CH3)3
CH3


204
bond
NO2
OCOC(CH3)3
CH3


205
bond
SCH3
OCOC(CH3)3
CH3


206
bond
SO2CH3
OCOC(CH3)3
CH3


207
bond
SO2CH2CH3
OCOC(CH3)3
CH3


208
bond
CH3
OCOC(CH3)3
CH3


209
bond
CF3
OCOC(CH3)3
CH3


210
bond
OCHF2
OCOC(CH3)3
CH3


211
CH2
F
OCOC(CH3)3
CH3


212
CH2
Cl
OCOC(CH3)3
CH3


213
CH2
Br
OCOC(CH3)3
CH3


214
CH2
NO2
OCOC(CH3)3
CH3


215
CH2
SCH3
OCOC(CH3)3
CH3


216
CH2
SO2CH3
OCOC(CH3)3
CH3


217
CH2
SO2CH2CH3
OCOC(CH3)3
CH3


218
CH2
CH3
OCOC(CH3)3
CH3


219
CH2
CF3
OCOC(CH3)3
CH3


220
CH2
OCHF2
OCOC(CH3)3
CH3


221
O
F
OCOC(CH3)3
CH3


222
O
Cl
OCOC(CH3)3
CH3


223
O
Br
OCOC(CH3)3
CH3


224
O
NO2
OCOC(CH3)3
CH3


225
O
SCH3
OCOC(CH3)3
CH3


226
O
SO2CH3
OCOC(CH3)3
CH3


227
O
SO2CH2CH3
OCOC(CH3)3
CH3


228
O
CH3
OCOC(CH3)3
CH3


229
O
CF3
OCOC(CH3)3
CH3


230
O
OCHF2
OCOC(CH3)3
CH3


231
S
F
OCOC(CH3)3
CH3


232
S
Cl
OCOC(CH3)3
CH3


233
S
Br
OCOC(CH3)3
CH3


234
S
NO2
OCOC(CH3)3
CH3


235
S
SCH3
OCOC(CH3)3
CH3


236
S
SO2CH3
OCOC(CH3)3
CH3


237
S
SO2CH2CH3
OCOC(CH3)3
CH3


238
S
CH3
OCOC(CH3)3
CH3


239
S
CF3
OCOC(CH3)3
CH3


240
S
OCHF2
OCOC(CH3)3
CH3


241
SO2
F
OCOC(CH3)3
CH3


242
SO2
Cl
OCOC(CH3)3
CH3


243
SO2
Br
OCOC(CH3)3
CH3


244
SO2
NO2
OCOC(CH3)3
CH3


245
SO2
SCH3
OCOC(CH3)3
CH3


246
SO2
SO2CH3
OCOC(CH3)3
CH3


247
SO2
SO2CH2CH3
OCOC(CH3)3
CH3


248
SO2
CH3
OCOC(CH3)3
CH3


249
SO2
CF3
OCOC(CH3)3
CH3


250
SO2
OCHF2
OCOC(CH3)3
CH3


251
bond
F
OCOC(CH3)3
CH2CH3


252
bond
Cl
OCOC(CH3)3
CH2CH3


253
bond
Br
OCOC(CH3)3
CH2CH3


254
bond
NO2
OCOC(CH3)3
CH2CH3


255
bond
SCH3
OCOC(CH3)3
CH2CH3


256
bond
SO2CH3
OCOC(CH3)3
CH2CH3


257
bond
SO2CH2CH3
OCOC(CH3)3
CH2CH3


258
bond
CH3
OCOC(CH3)3
CH2CH3


259
bond
CF3
OCOC(CH3)3
CH2CH3


260
bond
OCHF2
OCOC(CH3)3
CH2CH3


261
CH2
F
OCOC(CH3)3
CH2CH3


262
CH2
Cl
OCOC(CH3)3
CH2CH3


263
CH2
Br
OCOC(CH3)3
CH2CH3


264
CH2
NO2
OCOC(CH3)3
CH2CH3


265
CH2
SCH3
OCOC(CH3)3
CH2CH3


266
CH2
SO2CH3
OCOC(CH3)3
CH2CH3


267
CH2
SO2CH2CH3
OCOC(CH3)3
CH2CH3


268
CH2
CH3
OCOC(CH3)3
CH2CH3


269
CH2
CF3
OCOC(CH3)3
CH2CH3


270
CH2
OCHF2
OCOC(CH3)3
CH2CH3


271
O
F
OCOC(CH3)3
CH2CH3


272
O
Cl
OCOC(CH3)3
CH2CH3


273
O
Br
OCOC(CH3)3
CH2CH3


274
O
NO2
OCOC(CH3)3
CH2CH3


275
O
SCH3
OCOC(CH3)3
CH2CH3


276
O
SO2CH3
OCOC(CH3)3
CH2CH3


277
O
SO2CH2CH3
OCOC(CH3)3
CH2CH3


278
O
CH3
OCOC(CH3)3
CH2CH3


279
O
CF3
OCOC(CH3)3
CH2CH3


280
O
OCHF2
OCOC(CH3)3
CH2CH3


281
S
F
OCOC(CH3)3
CH2CH3


282
S
Cl
OCOC(CH3)3
CH2CH3


283
S
Br
OCOC(CH3)3
CH2CH3


284
S
NO2
OCOC(CH3)3
CH2CH3


285
S
SCH3
OCOC(CH3)3
CH2CH3


286
S
SO2CH3
OCOC(CH3)3
CH2CH3


287
S
SO2CH2CH3
OCOC(CH3)3
CH2CH3


288
S
CH3
OCOC(CH3)3
CH2CH3


289
S
CF3
OCOC(CH3)3
CH2CH3


290
S
OCHF2
OCOC(CH3)3
CH2CH3


291
SO2
F
OCOC(CH3)3
CH2CH3


292
SO2
Cl
OCOC(CH3)3
CH2CH3


293
SO2
Br
OCOC(CH3)3
CH2CH3


294
SO2
NO2
OCOC(CH3)3
CH2CH3


295
SO2
SCH3
OCOC(CH3)3
CH2CH3


296
SO2
SO2CH3
OCOC(CH3)3
CH2CH3


297
SO2
SO2CH2CH3
OCOC(CH3)3
CH2CH3


298
SO2
CH3
OCOC(CH3)3
CH2CH3


299
SO2
CF3
OCOC(CH3)3
CH2CH3


300
SO2
OCHF2
OCOC(CH3)3
CH2CH3


301
bond
F
OCOSCH3
CH3


302
bond
Cl
OCOSCH3
CH3


303
bond
Br
OCOSCH3
CH3


304
bond
NO2
OCOSCH3
CH3


305
bond
SCH3
OCOSCH3
CH3


306
bond
SO2CH3
OCOSCH3
CH3


307
bond
SO2CH2CH3
OCOSCH3
CH3


308
bond
CH3
OCOSCH3
CH3


309
bond
CF3
OCOSCH3
CH3


310
bond
OCHF2
OCOSCH3
CH3


311
CH2
F
OCOSCH3
CH3


312
CH2
Cl
OCOSCH3
CH3


313
CH2
Br
OCOSCH3
CH3


314
CH2
NO2
OCOSCH3
CH3


315
CH2
SCH3
OCOSCH3
CH3


316
CH2
SO2CH3
OCOSCH3
CH3


317
CH2
SO2CH2CH3
OCOSCH3
CH3


318
CH2
CH3
OCOSCH3
CH3


319
CH2
CF3
OCOSCH3
CH3


320
CH2
OCHF2
OCOSCH3
CH3


321
O
F
OCOSCH3
CH3


322
O
Cl
OCOSCH3
CH3


323
O
Br
OCOSCH3
CH3


324
O
NO2
OCOSCH3
CH3


325
O
SCH3
OCOSCH3
CH3


326
O
SO2CH3
OCOSCH3
CH3


327
O
SO2CH2CH3
OCOSCH3
CH3


328
O
CH3
OCOSCH3
CH3


329
O
CF3
OCOSCH3
CH3


330
O
OCHF2
OCOSCH3
CH3


331
S
F
OCOSCH3
CH3


332
S
Cl
OCOSCH3
CH3


333
S
Br
OCOSCH3
CH3


334
S
NO2
OCOSCH3
CH3


335
S
SCH3
OCOSCH3
CH3


336
S
SO2CH3
OCOSCH3
CH3


337
S
SO2CH2CH3
OCOSCH3
CH3


338
S
CH3
OCOSCH3
CH3


339
S
CF3
OCOSCH3
CH3


340
S
OCHF2
OCOSCH3
CH3


341
SO2
F
OCOSCH3
CH3


342
SO2
Cl
OCOSCH3
CH3


343
SO2
Br
OCOSCH3
CH3


344
SO2
NO2
OCOSCH3
CH3


345
SO2
SCH3
OCOSCH3
CH3


346
SO2
SO2CH3
OCOSCH3
CH3


347
SO2
SO2CH2CH3
OCOSCH3
CH3


348
SO2
CH3
OCOSCH3
CH3


349
SO2
CF3
OCOSCH3
CH3


350
SO2
OCHF2
OCOSCH3
CH3


351
bond
F
OCOSCH3
CH2CH3


352
bond
Cl
OCOSCH3
CH2CH3


353
bond
Br
OCOSCH3
CH2CH3


354
bond
NO2
OCOSCH3
CH2CH3


355
bond
SCH3
OCOSCH3
CH2CH3


356
bond
SO2CH3
OCOSCH3
CH2CH3


357
bond
SO2CH2CH3
OCOSCH3
CH2CH3


358
bond
CH3
OCOSCH3
CH2CH3


359
bond
CF3
OCOSCH3
CH2CH3


360
bond
OCHF2
OCOSCH3
CH2CH3


361
CH2
F
OCOSCH3
CH2CH3


362
CH2
Cl
OCOSCH3
CH2CH3


363
CH2
Br
OCOSCH3
CH2CH3


364
CH2
NO2
OCOSCH3
CH2CH3


365
CH2
SCH3
OCOSCH3
CH2CH3


366
CH2
SO2CH3
OCOSCH3
CH2CH3


367
CH2
SO2CH2CH3
OCOSCH3
CH2CH3


368
CH2
CH3
OCOSCH3
CH2CH3


369
CH2
CF3
OCOSCH3
CH2CH3


370
CH2
OCHF2
OCOSCH3
CH2CH3


371
O
F
OCOSCH3
CH2CH3


372
O
Cl
OCOSCH3
CH2CH3


373
O
Br
OCOSCH3
CH2CH3


374
O
NO2
OCOSCH3
CH2CH3


375
O
SCH3
OCOSCH3
CH2CH3


376
O
SO2CH3
OCOSCH3
CH2CH3


377
O
SO2CH2CH3
OCOSCH3
CH2CH3


378
O
CH3
OCOSCH3
CH2CH3


379
O
CF3
OCOSCH3
CH2CH3


380
O
OCHF2
OCOSCH3
CH2CH3


381
S
F
OCOSCH3
CH2CH3


382
S
Cl
OCOSCH3
CH2CH3


383
S
Br
OCOSCH3
CH2CH3


384
S
NO2
OCOSCH3
CH2CH3


385
S
SCH3
OCOSCH3
CH2CH3


386
S
SO2CH3
OCOSCH3
CH2CH3


387
S
SO2CH2CH3
OCOSCH3
CH2CH3


388
S
CH3
OCOSCH3
CH2CH3


389
S
CF3
OCOSCH3
CH2CH3


390
S
OCHF2
OCOSCH3
CH2CH3


391
SO2
F
OCOSCH3
CH2CH3


392
SO2
Cl
OCOSCH3
CH2CH3


393
SO2
Br
OCOSCH3
CH2CH3


394
SO2
NO2
OCOSCH3
CH2CH3


395
SO2
SCH3
OCOSCH3
CH2CH3


396
SO2
SO2CH3
OCOSCH3
CH2CH3


397
SO2
SO2CH2CH3
OCOSCH3
CH2CH3


398
SO2
CH3
OCOSCH3
CH2CH3


399
SO2
CF3
OCOSCH3
CH2CH3


400
SO2
OCHF2
OCOSCH3
CH2CH3


401
bond
F
OCH3
CH3


402
bond
Cl
OCH3
CH3


403
bond
Br
OCH3
CH3


404
bond
NO2
OCH3
CH3


405
bond
SCH3
OCH3
CH3


406
bond
SO2CH3
OCH3
CH3


407
bond
SO2CH2CH3
OCH3
CH3


408
bond
CH3
OCH3
CH3


409
bond
CF3
OCH3
CH3


410
bond
OCHF2
OCH3
CH3


411
CH2
F
OCH3
CH3


412
CH2
Cl
OCH3
CH3


413
CH2
Br
OCH3
CH3


414
CH2
NO2
OCH3
CH3


415
CH2
SCH3
OCH3
CH3


416
CH2
SO2CH3
OCH3
CH3


417
CH2
SO2CH2CH3
OCH3
CH3


418
CH2
CH3
OCH3
CH3


419
CH2
CF3
OCH3
CH3


420
CH2
OCHF2
OCH3
CH3


421
O
F
OCH3
CH3


422
O
Cl
OCH3
CH3


423
O
Br
OCH3
CH3


424
O
NO2
OCH3
CH3


425
O
SCH3
OCH3
CH3


426
O
SO2CH3
OCH3
CH3


427
O
SO2CH2CH3
OCH3
CH3


428
O
CH3
OCH3
CH3


429
O
CF3
OCH3
CH3


430
O
OCHF2
OCH3
CH3


431
S
F
OCH3
CH3


432
S
Cl
OCH3
CH3


433
S
Br
OCH3
CH3


434
S
NO2
OCH3
CH3


435
S
SCH3
OCH3
CH3


436
S
SO2CH3
OCH3
CH3


437
S
SO2CH2CH3
OCH3
CH3


438
S
CH3
OCH3
CH3


439
S
CF3
OCH3
CH3


440
S
OCHF2
OCH3
CH3


441
SO2
F
OCH3
CH3


442
SO2
Cl
OCH3
CH3


443
SO2
Br
OCH3
CH3


444
SO2
NO2
OCH3
CH3


445
SO2
SCH3
OCH3
CH3


446
SO2
SO2CH3
OCH3
CH3


447
SO2
SO2CH2CH3
OCH3
CH3


448
SO2
CH3
OCH3
CH3


449
SO2
CF3
OCH3
CH3


450
SO2
OCHF2
OCH3
CH3


451
bond
F
OCH3
CH2CH3


452
bond
Cl
OCH3
CH2CH3


453
bond
Br
OCH3
CH2CH3


454
bond
NO2
OCH3
CH2CH3


455
bond
SCH3
OCH3
CH2CH3


456
bond
SO2CH3
OCH3
CH2CH3


457
bond
SO2CH2CH3
OCH3
CH2CH3


458
bond
CH3
OCH3
CH2CH3


459
bond
CF3
OCH3
CH2CH3


460
bond
OCHF2
OCH3
CH2CH3


461
CH2
F
OCH3
CH2CH3


462
CH2
Cl
OCH3
CH2CH3


463
CH2
Br
OCH3
CH2CH3


464
CH2
NO2
OCH3
CH2CH3


465
CH2
SCH3
OCH3
CH2CH3


466
CH2
SO2CH3
OCH3
CH2CH3


467
CH2
SO2CH2CH3
OCH3
CH2CH3


468
CH2
CH3
OCH3
CH2CH3


469
CH2
CF3
OCH3
CH2CH3


470
CH2
OCHF2
OCH3
CH2CH3


471
O
F
OCH3
CH2CH3


472
O
Cl
OCH3
CH2CH3


473
O
Br
OCH3
CH2CH3


474
O
NO2
OCH3
CH2CH3


475
O
SCH3
OCH3
CH2CH3


476
O
SO2CH3
OCH3
CH2CH3


477
O
SO2CH2CH3
OCH3
CH2CH3


478
O
CH3
OCH3
CH2CH3


479
O
CF3
OCH3
CH2CH3


480
O
OCHF2
OCH3
CH2CH3


481
S
F
OCH3
CH2CH3


482
S
Cl
OCH3
CH2CH3


483
S
Br
OCH3
CH2CH3


484
S
NO2
OCH3
CH2CH3


485
S
SCH3
OCH3
CH2CH3


486
S
SO2CH3
OCH3
CH2CH3


487
S
SO2CH2CH3
OCH3
CH2CH3


488
S
CH3
OCH3
CH2CH3


489
S
CF3
OCH3
CH2CH3


490
S
OCHF2
OCH3
CH2CH3


491
SO2
F
OCH3
CH2CH3


492
SO2
Cl
OCH3
CH2CH3


493
SO2
Br
OCH3
CH2CH3


494
SO2
NO2
OCH3
CH2CH3


495
SO2
SCH3
OCH3
CH2CH3


496
SO2
SO2CH3
OCH3
CH2CH3


497
SO2
SO2CH2CH3
OCH3
CH2CH3


498
SO2
CH3
OCH3
CH2CH3


499
SO2
CF3
OCH3
CH2CH3


500
SO2
OCHF2
OCH3
CH2CH3


501
bond
F
OCH(CH3)2
CH3


502
bond
Cl
OCH(CH3)2
CH3


503
bond
Br
OCH(CH3)2
CH3


504
bond
NO2
OCH(CH3)2
CH3


505
bond
SCH3
OCH(CH3)2
CH3


506
bond
SO2CH3
OCH(CH3)2
CH3


507
bond
SO2CH2CH3
OCH(CH3)2
CH3


508
bond
CH3
OCH(CH3)2
CH3


509
bond
CF3
OCH(CH3)2
CH3


510
bond
OCHF2
OCH(CH3)2
CH3


511
CH2
F
OCH(CH3)2
CH3


512
CH2
Cl
OCH(CH3)2
CH3


513
CH2
Br
OCH(CH3)2
CH3


514
CH2
NO2
OCH(CH3)2
CH3


515
CH2
SCH3
OCH(CH3)2
CH3


516
CH2
SO2CH3
OCH(CH3)2
CH3


517
CH2
SO2CH2CH3
OCH(CH3)2
CH3


518
CH2
CH3
OCH(CH3)2
CH3


519
CH2
CF3
OCH(CH3)2
CH3


520
CH2
OCHF2
OCH(CH3)2
CH3


521
O
F
OCH(CH3)2
CH3


522
O
Cl
OCH(CH3)2
CH3


523
O
Br
OCH(CH3)2
CH3


524
O
NO2
OCH(CH3)2
CH3


525
O
SCH3
OCH(CH3)2
CH3


526
O
SO2CH3
OCH(CH3)2
CH3


527
O
SO2CH2CH3
OCH(CH3)2
CH3


528
O
CH3
OCH(CH3)2
CH3


529
O
CF3
OCH(CH3)2
CH3


530
O
OCHF2
OCH(CH3)2
CH3


531
S
F
OCH(CH3)2
CH3


532
S
Cl
OCH(CH3)2
CH3


533
S
Br
OCH(CH3)2
CH3


534
S
NO2
OCH(CH3)2
CH3


535
S
SCH3
OCH(CH3)2
CH3


536
S
SO2CH3
OCH(CH3)2
CH3


537
S
SO2CH2CH3
OCH(CH3)2
CH3


538
S
CH3
OCH(CH3)2
CH3


539
S
CF3
OCH(CH3)2
CH3


540
S
OCHF2
OCH(CH3)2
CH3


541
SO2
F
OCH(CH3)2
CH3


542
SO2
Cl
OCH(CH3)2
CH3


543
SO2
Br
OCH(CH3)2
CH3


544
SO2
NO2
OCH(CH3)2
CH3


545
SO2
SCH3
OCH(CH3)2
CH3


546
SO2
SO2CH3
OCH(CH3)2
CH3


547
SO2
SO2CH2CH3
OCH(CH3)2
CH3


548
SO2
CH3
OCH(CH3)2
CH3


549
SO2
CF3
OCH(CH3)2
CH3


550
SO2
OCHF2
OCH(CH3)2
CH3


551
bond
F
OCH(CH3)2
CH2CH3


552
bond
Cl
OCH(CH3)2
CH2CH3


553
bond
Br
OCH(CH3)2
CH2CH3


554
bond
NO2
OCH(CH3)2
CH2CH3


555
bond
SCH3
OCH(CH3)2
CH2CH3


556
bond
SO2CH3
OCH(CH3)2
CH2CH3


557
bond
SO2CH2CH3
OCH(CH3)2
CH2CH3


558
bond
CH3
OCH(CH3)2
CH2CH3


559
bond
CF3
OCH(CH3)2
CH2CH3


560
bond
OCHF2
OCH(CH3)2
CH2CH3


561
CH2
F
OCH(CH3)2
CH2CH3


562
CH2
Cl
OCH(CH3)2
CH2CH3


563
CH2
Br
OCH(CH3)2
CH2CH3


564
CH2
NO2
OCH(CH3)2
CH2CH3


565
CH2
SCH3
OCH(CH3)2
CH2CH3


566
CH2
SO2CH3
OCH(CH3)2
CH2CH3


567
CH2
SO2CH2CH3
OCH(CH3)2
CH2CH3


568
CH2
CH3
OCH(CH3)2
CH2CH3


569
CH2
CF3
OCH(CH3)2
CH2CH3


570
CH2
OCHF2
OCH(CH3)2
CH2CH3


571
O
F
OCH(CH3)2
CH2CH3


572
O
Cl
OCH(CH3)2
CH2CH3


573
O
Br
OCH(CH3)2
CH2CH3


574
O
NO2
OCH(CH3)2
CH2CH3


575
O
SCH3
OCH(CH3)2
CH2CH3


576
O
SO2CH3
OCH(CH3)2
CH2CH3


577
O
SO2CH2CH3
OCH(CH3)2
CH2CH3


578
O
CH3
OCH(CH3)2
CH2CH3


579
O
CF3
OCH(CH3)2
CH2CH3


580
O
OCHF2
OCH(CH3)2
CH2CH3


581
S
F
OCH(CH3)2
CH2CH3


582
S
Cl
OCH(CH3)2
CH2CH3


583
S
Br
OCH(CH3)2
CH2CH3


584
S
NO2
OCH(CH3)2
CH2CH3


585
S
SCH3
OCH(CH3)2
CH2CH3


586
S
SO2CH3
OCH(CH3)2
CH2CH3


587
S
SO2CH2CH3
OCH(CH3)2
CH2CH3


588
S
CH3
OCH(CH3)2
CH2CH3


589
S
CF3
OCH(CH3)2
CH2CH3


590
S
OCHF2
OCH(CH3)2
CH2CH3


591
SO2
F
OCH(CH3)2
CH2CH3


592
SO2
Cl
OCH(CH3)2
CH2CH3


593
SO2
Br
OCH(CH3)2
CH2CH3


594
SO2
NO2
OCH(CH3)2
CH2CH3


595
SO2
SCH3
OCH(CH3)2
CH2CH3


596
SO2
SO2CH3
OCH(CH3)2
CH2CH3


597
SO2
SO2CH2CH3
OCH(CH3)2
CH2CH3


598
SO2
CH3
OCH(CH3)2
CH2CH3


599
SO2
CF3
OCH(CH3)2
CH2CH3


600
SO2
OCHF2
OCH(CH3)2
CH2CH3


601
bond
F
OCH2C6H5
CH3


602
bond
Cl
OCH2C6H5
CH3


603
bond
Br
OCH2C6H5
CH3


604
bond
NO2
OCH2C6H5
CH3


605
bond
SCH3
OCH2C6H5
CH3


606
bond
SO2CH3
OCH2C6H5
CH3


607
bond
SO2CH2CH3
OCH2C6H5
CH3


608
bond
CH3
OCH2C6H5
CH3


609
bond
CF3
OCH2C6H5
CH3


610
bond
OCHF2
OCH2C6H5
CH3


611
CH2
F
OCH2C6H5
CH3


612
CH2
Cl
OCH2C6H5
CH3


613
CH2
Br
OCH2C6H5
CH3


614
CH2
NO2
OCH2C6H5
CH3


615
CH2
SCH3
OCH2C6H5
CH3


616
CH2
SO2CH3
OCH2C6H5
CH3


617
CH2
SO2CH2CH3
OCH2C6H5
CH3


618
CH2
CH3
OCH2C6H5
CH3


619
CH2
CF3
OCH2C6H5
CH3


620
CH2
OCHF2
OCH2C6H5
CH3


621
O
F
OCH2C6H5
CH3


622
O
Cl
OCH2C6H5
CH3


623
O
Br
OCH2C6H5
CH3


624
O
NO2
OCH2C6H5
CH3


625
O
SCH3
OCH2C6H5
CH3


626
O
SO2CH3
OCH2C6H5
CH3


627
O
SO2CH2CH3
OCH2C6H5
CH3


628
O
CH3
OCH2C6H5
CH3


629
O
CF3
OCH2C6H5
CH3


630
O
OCHF2
OCH2C6H5
CH3


631
S
F
OCH2C6H5
CH3


632
S
Cl
OCH2C6H5
CH3


633
S
Br
OCH2C6H5
CH3


634
S
NO2
OCH2C6H5
CH3


635
S
SCH3
OCH2C6H5
CH3


636
S
SO2CH3
OCH2C6H5
CH3


637
S
SO2CH2CH3
OCH2C6H5
CH3


638
S
CH3
OCH2C6H5
CH3


639
S
CF3
OCH2C6H5
CH3


640
S
OCHF2
OCH2C6H5
CH3


641
SO2
F
OCH2C6H5
CH3


642
SO2
Cl
OCH2C6H5
CH3


643
SO2
Br
OCH2C6H5
CH3


644
SO2
NO2
OCH2C6H5
CH3


645
SO2
SCH3
OCH2C6H5
CH3


646
SO2
SO2CH3
OCH2C6H5
CH3


647
SO2
SO2CH2CH3
OCH2C6H5
CH3


648
SO2
CH3
OCH2C6H5
CH3


649
SO2
CF3
OCH2C6H5
CH3


650
SO2
OCHF2
OCH2C6H5
CH3


651
bond
F
OCH2C6H5
CH2CH3


652
bond
Cl
OCH2C6H5
CH2CH3


653
bond
Br
OCH2C6H5
CH2CH3


654
bond
NO2
OCH2C6H5
CH2CH3


655
bond
SCH3
OCH2C6H5
CH2CH3


656
bond
SO2CH3
OCH2C6H5
CH2CH3


657
bond
SO2CH2CH3
OCH2C6H5
CH2CH3


658
bond
CH3
OCH2C6H5
CH2CH3


659
bond
CF3
OCH2C6H5
CH2CH3


660
bond
OCHF2
OCH2C6H5
CH2CH3


661
CH2
F
OCH2C6H5
CH2CH3


662
CH2
Cl
OCH2C6H5
CH2CH3


663
CH2
Br
OCH2C6H5
CH2CH3


664
CH2
NO2
OCH2C6H5
CH2CH3


665
CH2
SCH3
OCH2C6H5
CH2CH3


666
CH2
SO2CH3
OCH2C6H5
CH2CH3


667
CH2
SO2CH2CH3
OCH2C6H5
CH2CH3


668
CH2
CH3
OCH2C6H5
CH2CH3


669
CH2
CF3
OCH2C6H5
CH2CH3


670
CH2
OCHF2
OCH2C6H5
CH2CH3


671
O
F
OCH2C6H5
CH2CH3


672
O
Cl
OCH2C6H5
CH2CH3


673
O
Br
OCH2C6H5
CH2CH3


674
O
NO2
OCH2C6H5
CH2CH3


675
O
SCH3
OCH2C6H5
CH2CH3


676
O
SO2CH3
OCH2C6H5
CH2CH3


677
O
SO2CH2CH3
OCH2C6H5
CH2CH3


678
O
CH3
OCH2C6H5
CH2CH3


679
O
CF3
OCH2C6H5
CH2CH3


680
O
OCHF2
OCH2C6H5
CH2CH3


681
S
F
OCH2C6H5
CH2CH3


682
S
Cl
OCH2C6H5
CH2CH3


683
S
Br
OCH2C6H5
CH2CH3


684
S
NO2
OCH2C6H5
CH2CH3


685
S
SCH3
OCH2C6H5
CH2CH3


686
S
SO2CH3
OCH2C6H5
CH2CH3


687
S
SO2CH2CH3
OCH2C6H5
CH2CH3


688
S
CH3
OCH2C6H5
CH2CH3


689
S
CF3
OCH2C6H5
CH2CH3


690
S
OCHF2
OCH2C6H5
CH2CH3


691
SO2
F
OCH2C6H5
CH2CH3


692
SO2
Cl
OCH2C6H5
CH2CH3


693
SO2
Br
OCH2C6H5
CH2CH3


694
SO2
NO2
OCH2C6H5
CH2CH3


695
SO2
SCH3
OCH2C6H5
CH2CH3


696
SO2
SO2CH3
OCH2C6H5
CH2CH3


697
SO2
SO2CH2CH3
OCH2C6H5
CH2CH3


698
SO2
CH3
OCH2C6H5
CH2CH3


699
SO2
CF3
OCH2C6H5
CH2CH3


700
SO2
OCHF2
OCH2C6H5
CH2CH3


701
bond
F
OSO2(4-CH3—C6H4)
CH3


702
bond
Cl
OSO2(4-CH3—C6H4)
CH3


703
bond
Br
OSO2(4-CH3—C6H4)
CH3


704
bond
NO2
OSO2(4-CH3—C6H4)
CH3


705
bond
SCH3
OSO2(4-CH3—C6H4)
CH3


706
bond
SO2CH3
OSO2(4-CH3—C6H4)
CH3


707
bond
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH3


708
bond
CH3
OSO2(4-CH3—C6H4)
CH3


709
bond
CF3
OSO2(4-CH3—C6H4)
CH3


710
bond
OCHF2
OSO2(4-CH3—C6H4)
CH3


711
CH2
F
OSO2(4-CH3—C6H4)
CH3


712
CH2
Cl
OSO2(4-CH3—C6H4)
CH3


713
CH2
Br
OSO2(4-CH3—C6H4)
CH3


714
CH2
NO2
OSO2(4-CH3—C6H4)
CH3


715
CH2
SCH3
OSO2(4-CH3—C6H4)
CH3


716
CH2
SO2CH3
OSO2(4-CH3—C6H4)
CH3


717
CH2
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH3


718
CH2
CH3
OSO2(4-CH3—C6H4)
CH3


719
CH2
CF3
OSO2(4-CH3—C6H4)
CH3


720
CH2
OCHF2
OSO2(4-CH3—C6H4)
CH3


721
O
F
OSO2(4-CH3—C6H4)
CH3


722
O
Cl
OSO2(4-CH3—C6H4)
CH3


723
O
Br
OSO2(4-CH3—C6H4)
CH3


724
O
NO2
OSO2(4-CH3—C6H4)
CH3


725
O
SCH3
OSO2(4-CH3—C6H4)
CH3


726
O
SO2CH3
OSO2(4-CH3—C6H4)
CH3


727
O
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH3


728
O
CH3
OSO2(4-CH3—C6H4)
CH3


729
O
CF3
OSO2(4-CH3—C6H4)
CH3


730
O
OCHF2
OSO2(4-CH3—C6H4)
CH3


731
S
F
OSO2(4-CH3—C6H4)
CH3


732
S
Cl
OSO2(4-CH3—C6H4)
CH3


733
S
Br
OSO2(4-CH3—C6H4)
CH3


734
S
NO2
OSO2(4-CH3—C6H4)
CH3


735
S
SCH3
OSO2(4-CH3—C6H4)
CH3


736
S
SO2CH3
OSO2(4-CH3—C6H4)
CH3


737
S
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH3


738
S
CH3
OSO2(4-CH3—C6H4)
CH3


739
S
CF3
OSO2(4-CH3—C6H4)
CH3


740
S
OCHF2
OSO2(4-CH3—C6H4)
CH3


741
SO2
F
OSO2(4-CH3—C6H4)
CH3


742
SO2
Cl
OSO2(4-CH3—C6H4)
CH3


743
SO2
Br
OSO2(4-CH3—C6H4)
CH3


744
SO2
NO2
OSO2(4-CH3—C6H4)
CH3


745
SO2
SCH3
OSO2(4-CH3—C6H4)
CH3


746
SO2
SO2CH3
OSO2(4-CH3—C6H4)
CH3


747
SO2
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH3


748
SO2
CH3
OSO2(4-CH3—C6H4)
CH3


749
SO2
CF3
OSO2(4-CH3—C6H4)
CH3


750
SO2
OCHF2
OSO2(4-CH3—C6H4)
CH3


751
bond
F
OSO2(4-CH3—C6H4)
CH2CH3


752
bond
Cl
OSO2(4-CH3—C6H4)
CH2CH3


753
bond
Br
OSO2(4-CH3—C6H4)
CH2CH3


754
bond
NO2
OSO2(4-CH3—C6H4)
CH2CH3


755
bond
SCH3
OSO2(4-CH3—C6H4)
CH2CH3


756
bond
SO2CH3
OSO2(4-CH3—C6H4)
CH2CH3


757
bond
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH2CH3


758
bond
CH3
OSO2(4-CH3—C6H4)
CH2CH3


759
bond
CF3
OSO2(4-CH3—C6H4)
CH2CH3


760
bond
OCHF2
OSO2(4-CH3—C6H4)
CH2CH3


761
CH2
F
OSO2(4-CH3—C6H4)
CH2CH3


762
CH2
Cl
OSO2(4-CH3—C6H4)
CH2CH3


763
CH2
Br
OSO2(4-CH3—C6H4)
CH2CH3


764
CH2
NO2
OSO2(4-CH3—C6H4)
CH2CH3


765
CH2
SCH3
OSO2(4-CH3—C6H4)
CH2CH3


766
CH2
SO2CH3
OSO2(4-CH3—C6H4)
CH2CH3


767
CH2
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH2CH3


768
CH2
CH3
OSO2(4-CH3—C6H4)
CH2CH3


769
CH2
CF3
OSO2(4-CH3—C6H4)
CH2CH3


770
CH2
OCHF2
OSO2(4-CH3—C6H4)
CH2CH3


771
O
F
OSO2(4-CH3—C6H4)
CH2CH3


772
O
Cl
OSO2(4-CH3—C6H4)
CH2CH3


773
O
Br
OSO2(4-CH3—C6H4)
CH2CH3


774
O
NO2
OSO2(4-CH3—C6H4)
CH2CH3


775
O
SCH3
OSO2(4-CH3—C6H4)
CH2CH3


776
O
SO2CH3
OSO2(4-CH3—C6H4)
CH2CH3


777
O
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH2CH3


778
O
CH3
OSO2(4-CH3—C6H4)
CH2CH3


779
O
CF3
OSO2(4-CH3—C6H4)
CH2CH3


780
O
OCHF2
OSO2(4-CH3—C6H4)
CH2CH3


781
S
F
OSO2(4-CH3—C6H4)
CH2CH3


782
S
Cl
OSO2(4-CH3—C6H4)
CH2CH3


783
S
Br
OSO2(4-CH3—C6H4)
CH2CH3


784
S
NO2
OSO2(4-CH3—C6H4)
CH2CH3


785
S
SCH3
OSO2(4-CH3—C6H4)
CH2CH3


786
S
SO2CH3
OSO2(4-CH3—C6H4)
CH2CH3


787
S
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH2CH3


788
S
CH3
OSO2(4-CH3—C6H4)
CH2CH3


789
S
CF3
OSO2(4-CH3—C6H4)
CH2CH3


790
S
OCHF2
OSO2(4-CH3—C6H4)
CH2CH3


791
SO2
F
OSO2(4-CH3—C6H4)
CH2CH3


792
SO2
Cl
OSO2(4-CH3—C6H4)
CH2CH3


793
SO2
Br
OSO2(4-CH3—C6H4)
CH2CH3


794
SO2
NO2
OSO2(4-CH3—C6H4)
CH2CH3


795
SO2
SCH3
OSO2(4-CH3—C6H4)
CH2CH3


796
SO2
SO2CH3
OSO2(4-CH3—C6H4)
CH2CH3


797
SO2
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH2CH3


798
SO2
CH3
OSO2(4-CH3—C6H4)
CH2CH3


799
SO2
CF3
OSO2(4-CH3—C6H4)
CH2CH3


800
SO2
OCHF2
OSO2(4-CH3—C6H4)
CH2CH3


801
bond
F
SCH3
CH3


802
bond
Cl
SCH3
CH3


803
bond
Br
SCH3
CH3


804
bond
NO2
SCH3
CH3


805
bond
SCH3
SCH3
CH3


806
bond
SO2CH3
SCH3
CH3


807
bond
SO2CH2CH3
SCH3
CH3


808
bond
CH3
SCH3
CH3


809
bond
CF3
SCH3
CH3


810
bond
OCHF2
SCH3
CH3


811
CH2
F
SCH3
CH3


812
CH2
Cl
SCH3
CH3


813
CH2
Br
SCH3
CH3


814
CH2
NO2
SCH3
CH3


815
CH2
SCH3
SCH3
CH3


816
CH2
SO2CH3
SCH3
CH3


817
CH2
SO2CH2CH3
SCH3
CH3


818
CH2
CH3
SCH3
CH3


819
CH2
CF3
SCH3
CH3


820
CH2
OCHF2
SCH3
CH3


821
O
F
SCH3
CH3


822
O
Cl
SCH3
CH3


823
O
Br
SCH3
CH3


824
O
NO2
SCH3
CH3


825
O
SCH3
SCH3
CH3


826
O
SO2CH3
SCH3
CH3


827
O
SO2CH2CH3
SCH3
CH3


828
O
CH3
SCH3
CH3


829
O
CF3
SCH3
CH3


830
O
OCHF2
SCH3
CH3


831
S
F
SCH3
CH3


832
S
Cl
SCH3
CH3


833
S
Br
SCH3
CH3


834
S
NO2
SCH3
CH3


835
S
SCH3
SCH3
CH3


836
S
SO2CH3
SCH3
CH3


837
S
SO2CH2CH3
SCH3
CH3


838
S
CH3
SCH3
CH3


839
S
CF3
SCH3
CH3


840
S
OCHF2
SCH3
CH3


841
SO2
F
SCH3
CH3


842
SO2
Cl
SCH3
CH3


843
SO2
Br
SCH3
CH3


844
SO2
NO2
SCH3
CH3


845
SO2
SCH3
SCH3
CH3


846
SO2
SO2CH3
SCH3
CH3


847
SO2
SO2CH2CH3
SCH3
CH3


848
SO2
CH3
SCH3
CH3


849
SO2
CF3
SCH3
CH3


850
SO2
OCHF2
SCH3
CH3


851
bond
F
SCH3
CH2CH3


852
bond
Cl
SCH3
CH2CH3


853
bond
Br
SCH3
CH2CH3


854
bond
NO2
SCH3
CH2CH3


855
bond
SCH3
SCH3
CH2CH3


856
bond
SO2CH3
SCH3
CH2CH3


857
bond
SO2CH2CH3
SCH3
CH2CH3


858
bond
CH3
SCH3
CH2CH3


859
bond
CF3
SCH3
CH2CH3


860
bond
OCHF2
SCH3
CH2CH3


861
CH2
F
SCH3
CH2CH3


862
CH2
Cl
SCH3
CH2CH3


863
CH2
Br
SCH3
CH2CH3


864
CH2
NO2
SCH3
CH2CH3


865
CH2
SCH3
SCH3
CH2CH3


866
CH2
SO2CH3
SCH3
CH2CH3


867
CH2
SO2CH2CH3
SCH3
CH2CH3


868
CH2
CH3
SCH3
CH2CH3


869
CH2
CF3
SCH3
CH2CH3


870
CH2
OCHF2
SCH3
CH2CH3


871
O
F
SCH3
CH2CH3


872
O
Cl
SCH3
CH2CH3


873
O
Br
SCH3
CH2CH3


874
O
NO2
SCH3
CH2CH3


875
O
SCH3
SCH3
CH2CH3


876
O
SO2CH3
SCH3
CH2CH3


877
O
SO2CH2CH3
SCH3
CH2CH3


878
O
CH3
SCH3
CH2CH3


879
O
CF3
SCH3
CH2CH3


880
O
OCHF2
SCH3
CH2CH3


881
S
F
SCH3
CH2CH3


882
S
Cl
SCH3
CH2CH3


883
S
Br
SCH3
CH2CH3


884
S
NO2
SCH3
CH2CH3


885
S
SCH3
SCH3
CH2CH3


886
S
SO2CH3
SCH3
CH2CH3


887
S
SO2CH2CH3
SCH3
CH2CH3


888
S
CH3
SCH3
CH2CH3


889
S
CF3
SCH3
CH2CH3


890
S
OCHF2
SCH3
CH2CH3


891
SO2
F
SCH3
CH2CH3


892
SO2
Cl
SCH3
CH2CH3


893
SO2
Br
SCH3
CH2CH3


894
SO2
NO2
SCH3
CH2CH3


895
SO2
SCH3
SCH3
CH2CH3


896
SO2
SO2CH3
SCH3
CH2CH3


897
SO2
SO2CH2CH3
SCH3
CH2CH3


898
SO2
CH3
SCH3
CH2CH3


899
SO2
CF3
SCH3
CH2CH3


900
SO2
OCHF2
SCH3
CH2CH3


901
bond
F
Cl
CH3


902
bond
Cl
Cl
CH3


903
bond
Br
Cl
CH3


904
bond
NO2
Cl
CH3


905
bond
SCH3
Cl
CH3


906
bond
SO2CH3
Cl
CH3


907
bond
SO2CH2CH3
Cl
CH3


908
bond
CH3
Cl
CH3


909
bond
CF3
Cl
CH3


910
bond
OCHF2
Cl
CH3


911
CH2
F
Cl
CH3


912
CH2
Cl
Cl
CH3


913
CH2
Br
Cl
CH3


914
CH2
NO2
Cl
CH3


915
CH2
SCH3
Cl
CH3


916
CH2
SO2CH3
Cl
CH3


917
CH2
SO2CH2CH3
Cl
CH3


918
CH2
CH3
Cl
CH3


919
CH2
CF3
Cl
CH3


920
CH2
OCHF2
Cl
CH3


921
O
F
Cl
CH3


922
O
Cl
Cl
CH3


923
O
Br
Cl
CH3


924
O
NO2
Cl
CH3


925
O
SCH3
Cl
CH3


926
O
SO2CH3
Cl
CH3


927
O
SO2CH2CH3
Cl
CH3


928
O
CH3
Cl
CH3


929
O
CF3
Cl
CH3


930
O
OCHF2
Cl
CH3


931
S
F
Cl
CH3


932
S
Cl
Cl
CH3


933
S
Br
Cl
CH3


934
S
NO2
Cl
CH3


935
S
SCH3
Cl
CH3


936
S
SO2CH3
Cl
CH3


937
S
SO2CH2CH3
Cl
CH3


938
S
CH3
Cl
CH3


939
S
CF3
Cl
CH3


940
S
OCHF2
Cl
CH3


941
SO2
F
Cl
CH3


942
SO2
Cl
Cl
CH3


943
SO2
Br
Cl
CH3


944
SO2
NO2
Cl
CH3


945
SO2
SCH3
Cl
CH3


946
SO2
SO2CH3
Cl
CH3


947
SO2
SO2CH2CH3
Cl
CH3


948
SO2
CH3
Cl
CH3


949
SO2
CF3
Cl
CH3


950
SO2
OCHF2
Cl
CH3


951
bond
F
Cl
CH2CH3


952
bond
Cl
Cl
CH2CH3


953
bond
Br
Cl
CH2CH3


954
bond
NO2
Cl
CH2CH3


955
bond
SCH3
Cl
CH2CH3


956
bond
SO2CH3
Cl
CH2CH3


957
bond
SO2CH2CH3
Cl
CH2CH3


958
bond
CH3
Cl
CH2CH3


959
bond
CF3
Cl
CH2CH3


960
bond
OCHF2
Cl
CH2CH3


961
CH2
F
Cl
CH2CH3


962
CH2
Cl
Cl
CH2CH3


963
CH2
Br
Cl
CH2CH3


964
CH2
NO2
Cl
CH2CH3


965
CH2
SCH3
Cl
CH2CH3


966
CH2
SO2CH3
Cl
CH2CH3


967
CH2
SO2CH2CH3
Cl
CH2CH3


968
CH2
CH3
Cl
CH2CH3


969
CH2
CF3
Cl
CH2CH3


970
CH2
OCHF2
Cl
CH2CH3


971
O
F
Cl
CH2CH3


972
O
Cl
Cl
CH2CH3


973
O
Br
Cl
CH2CH3


974
O
NO2
Cl
CH2CH3


975
O
SCH3
Cl
CH2CH3


976
O
SO2CH3
Cl
CH2CH3


977
O
SO2CH2CH3
Cl
CH2CH3


978
O
CH3
Cl
CH2CH3


979
O
CF3
Cl
CH2CH3


980
O
OCHF2
Cl
CH2CH3


981
S
F
Cl
CH2CH3


982
S
Cl
Cl
CH2CH3


983
S
Br
Cl
CH2CH3


984
S
NO2
Cl
CH2CH3


985
S
SCH3
Cl
CH2CH3


986
S
SO2CH3
Cl
CH2CH3


987
S
SO2CH2CH3
Cl
CH2CH3


988
S
CH3
Cl
CH2CH3


989
S
CF3
Cl
CH2CH3


990
S
OCHF2
Cl
CH2CH3


991
SO2
F
Cl
CH2CH3


992
SO2
Cl
Cl
CH2CH3


993
SO2
Br
Cl
CH2CH3


994
SO2
NO2
Cl
CH2CH3


995
SO2
SCH3
Cl
CH2CH3


996
SO2
SO2CH3
Cl
CH2CH3


997
SO2
SO2CH2CH3
Cl
CH2CH3


998
SO2
CH3
Cl
CH2CH3


999
SO2
CF3
Cl
CH2CH3


1000
SO2
OCHF2
Cl
CH2CH3


1001
bond
F
OH
CH(CH3)2


1002
bond
Cl
OH
CH(CH3)2


1003
bond
Br
OH
CH(CH3)2


1004
bond
NO2
OH
CH(CH3)2


1005
bond
SCH3
OH
CH(CH3)2


1006
bond
SO2CH3
OH
CH(CH3)2


1007
bond
SO2CH2CH3
OH
CH(CH3)2


1008
bond
CH3
OH
CH(CH3)2


1009
bond
CF3
OH
CH(CH3)2


1010
bond
OCHF2
OH
CH(CH3)2


1011
CH2
F
OH
CH(CH3)2


1012
CH2
Cl
OH
CH(CH3)2


2025
CH2
Br
OH
CH(CH3)2


2026
CH2
NO2
OH
CH(CH3)2


2027
CH2
SCH3
OH
CH(CH3)2


2028
CH2
SO2CH3
OH
CH(CH3)2


2029
CH2
SO2CH2CH3
OH
CH(CH3)2


2030
CH2
CH3
OH
CH(CH3)2


2031
CH2
CF3
OH
CH(CH3)2


2032
CH2
OCHF2
OH
CH(CH3)2


2033
O
F
OH
CH(CH3)2


2034
O
Cl
OH
CH(CH3)2


2035
O
Br
OH
CH(CH3)2


2036
O
NO2
OH
CH(CH3)2


2037
O
SCH3
OH
CH(CH3)2


2038
O
SO2CH3
OH
CH(CH3)2


2039
O
SO2CH2CH3
OH
CH(CH3)2


2040
O
CH3
OH
CH(CH3)2


2041
O
CF3
OH
CH(CH3)2


2042
O
OCHF2
OH
CH(CH3)2


2043
S
F
OH
CH(CH3)2


2044
S
Cl
OH
CH(CH3)2


2045
S
Br
OH
CH(CH3)2


2046
S
NO2
OH
CH(CH3)2


2047
S
SCH3
OH
CH(CH3)2


2048
S
SO2CH3
OH
CH(CH3)2


2049
S
SO2CH2CH3
OH
CH(CH3)2


2050
S
CH3
OH
CH(CH3)2


2051
S
CF3
OH
CH(CH3)2


2052
S
OCHF2
OH
CH(CH3)2


2053
SO2
F
OH
CH(CH3)2


2054
SO2
Cl
OH
CH(CH3)2


2055
SO2
Br
OH
CH(CH3)2


2056
SO2
NO2
OH
CH(CH3)2


2057
SO2
SCH3
OH
CH(CH3)2


2058
SO2
SO2CH3
OH
CH(CH3)2


2059
SO2
SO2CH2CH3
OH
CH(CH3)2


2060
SO2
CH3
OH
CH(CH3)2


2061
SO2
CF3
OH
CH(CH3)2


2062
SO2
OCHF2
OH
CH(CH3)2


2063
bond
F
OH
C(CH3)3


2064
bond
Cl
OH
C(CH3)3


2065
bond
Br
OH
C(CH3)3


2066
bond
NO2
OH
C(CH3)3


2067
bond
SCH3
OH
C(CH3)3


2068
bond
SO2CH3
OH
C(CH3)3


2069
bond
SO2CH2CH3
OH
C(CH3)3


2070
bond
CH3
OH
C(CH3)3


2071
bond
CF3
OH
C(CH3)3


2072
bond
OCHF2
OH
C(CH3)3


2073
CH2
F
OH
C(CH3)3


2074
CH2
Cl
OH
C(CH3)3


2075
CH2
Br
OH
C(CH3)3


2076
CH2
NO2
OH
C(CH3)3


2077
CH2
SCH3
OH
C(CH3)3


2078
CH2
SO2CH3
OH
C(CH3)3


2079
CH2
SO2CH2CH3
OH
C(CH3)3


2080
CH2
CH3
OH
C(CH3)3


2081
CH2
CF3
OH
C(CH3)3


2082
CH2
OCHF2
OH
C(CH3)3


2083
O
F
OH
C(CH3)3


2084
O
Cl
OH
C(CH3)3


2085
O
Br
OH
C(CH3)3


2086
O
NO2
OH
C(CH3)3


2087
O
SCH3
OH
C(CH3)3


2088
O
SO2CH3
OH
C(CH3)3


2089
O
SO2CH2CH3
OH
C(CH3)3


2090
O
CH3
OH
C(CH3)3


2091
O
CF3
OH
C(CH3)3


2092
O
OCHF2
OH
C(CH3)3


2093
S
F
OH
C(CH3)3


2094
S
Cl
OH
C(CH3)3


2095
S
Br
OH
C(CH3)3


2096
S
NO2
OH
C(CH3)3


2097
S
SCH3
OH
C(CH3)3


2098
S
SO2CH3
OH
C(CH3)3


2099
S
SO2CH2CH3
OH
C(CH3)3


2100
S
CH3
OH
C(CH3)3


2101
S
CF3
OH
C(CH3)3


2102
S
OCHF2
OH
C(CH3)3


2103
SO2
F
OH
C(CH3)3


2104
SO2
Cl
OH
C(CH3)3


2105
SO2
Br
OH
C(CH3)3


2106
SO2
NO2
OH
C(CH3)3


2107
SO2
SCH3
OH
C(CH3)3


2108
SO2
SO2CH3
OH
C(CH3)3


2109
SO2
SO2CH2CH3
OH
C(CH3)3


2110
SO2
CH3
OH
C(CH3)3


2111
SO2
CF3
OH
C(CH3)3


2112
SO2
OCHF2
OH
C(CH3)3


2113
bond
F
OCOC6H5
CH(CH3)2


2114
bond
Cl
OCOC6H5
CH(CH3)2


2115
bond
Br
OCOC6H5
CH(CH3)2


2116
bond
NO2
OCOC6H5
CH(CH3)2


2117
bond
SCH3
OCOC6H5
CH(CH3)2


2118
bond
SO2CH3
OCOC6H5
CH(CH3)2


2119
bond
SO2CH2CH3
OCOC6H5
CH(CH3)2


2120
bond
CH3
OCOC6H5
CH(CH3)2


2121
bond
CF3
OCOC6H5
CH(CH3)2


2122
bond
OCHF2
OCOC6H5
CH(CH3)2


2123
CH2
F
OCOC6H5
CH(CH3)2


2124
CH2
Cl
OCOC6H5
CH(CH3)2


2125
CH2
Br
OCOC6H5
CH(CH3)2


2126
CH2
NO2
OCOC6H5
CH(CH3)2


2127
CH2
SCH3
OCOC6H5
CH(CH3)2


2128
CH2
SO2CH3
OCOC6H5
CH(CH3)2


2129
CH2
SO2CH2CH3
OCOC6H5
CH(CH3)2


2130
CH2
CH3
OCOC6H5
CH(CH3)2


2131
CH2
CF3
OCOC6H5
CH(CH3)2


2132
CH2
OCHF2
OCOC6H5
CH(CH3)2


2133
O
F
OCOC6H5
CH(CH3)2


2134
O
Cl
OCOC6H5
CH(CH3)2


2135
O
Br
OCOC6H5
CH(CH3)2


2136
O
NO2
OCOC6H5
CH(CH3)2


2137
O
SCH3
OCOC6H5
CH(CH3)2


2138
O
SO2CH3
OCOC6H5
CH(CH3)2


2139
O
SO2CH2CH3
OCOC6H5
CH(CH3)2


2140
O
CH3
OCOC6H5
CH(CH3)2


2141
O
CF3
OCOC6H5
CH(CH3)2


2142
O
OCHF2
OCOC6H5
CH(CH3)2


2143
S
F
OCOC6H5
CH(CH3)2


2144
S
Cl
OCOC6H5
CH(CH3)2


2145
S
Br
OCOC6H5
CH(CH3)2


2146
S
NO2
OCOC6H5
CH(CH3)2


2147
S
SCH3
OCOC6H5
CH(CH3)2


2148
S
SO2CH3
OCOC6H5
CH(CH3)2


2149
S
SO2CH2CH3
OCOC6H5
CH(CH3)2


2150
S
CH3
OCOC6H5
CH(CH3)2


2151
S
CF3
OCOC6H5
CH(CH3)2


2152
S
OCHF2
OCOC6H5
CH(CH3)2


2153
SO2
F
OCOC6H5
CH(CH3)2


2154
SO2
Cl
OCOC6H5
CH(CH3)2


2155
SO2
Br
OCOC6H5
CH(CH3)2


2156
SO2
NO2
OCOC6H5
CH(CH3)2


2157
SO2
SCH3
OCOC6H5
CH(CH3)2


2158
SO2
SO2CH3
OCOC6H5
CH(CH3)2


2159
SO2
SO2CH2CH3
OCOC6H5
CH(CH3)2


2160
SO2
CH3
OCOC6H5
CH(CH3)2


2161
SO2
CF3
OCOC6H5
CH(CH3)2


2162
SO2
OCHF2
OCOC6H5
CH(CH3)2


2163
bond
F
OCOC6H5
C(CH3)3


2164
bond
Cl
OCOC6H5
C(CH3)3


2165
bond
Br
OCOC6H5
C(CH3)3


2166
bond
NO2
OCOC6H5
C(CH3)3


2167
bond
SCH3
OCOC6H5
C(CH3)3


2168
bond
SO2CH3
OCOC6H5
C(CH3)3


2169
bond
SO2CH2CH3
OCOC6H5
C(CH3)3


2170
bond
CH3
OCOC6H5
C(CH3)3


2171
bond
CF3
OCOC6H5
C(CH3)3


2172
bond
OCHF2
OCOC6H5
C(CH3)3


2173
CH2
F
OCOC6H5
C(CH3)3


2174
CH2
Cl
OCOC6H5
C(CH3)3


2175
CH2
Br
OCOC6H5
C(CH3)3


2176
CH2
NO2
OCOC6H5
C(CH3)3


2177
CH2
SCH3
OCOC6H5
C(CH3)3


2178
CH2
SO2CH3
OCOC6H5
C(CH3)3


2179
CH2
SO2CH2CH3
OCOC6H5
C(CH3)3


2180
CH2
CH3
OCOC6H5
C(CH3)3


2181
CH2
CF3
OCOC6H5
C(CH3)3


2182
CH2
OCHF2
OCOC6H5
C(CH3)3


2183
O
F
OCOC6H5
C(CH3)3


2184
O
Cl
OCOC6H5
C(CH3)3


2185
O
Br
OCOC6H5
C(CH3)3


2186
O
NO2
OCOC6H5
C(CH3)3


2187
O
SCH3
OCOC6H5
C(CH3)3


2188
O
SO2CH3
OCOC6H5
C(CH3)3


2189
O
SO2CH2CH3
OCOC6H5
C(CH3)3


2190
O
CH3
OCOC6H5
C(CH3)3


2191
O
CF3
OCOC6H5
C(CH3)3


2192
O
OCHF2
OCOC6H5
C(CH3)3


2193
S
F
OCOC6H5
C(CH3)3


2194
S
Cl
OCOC6H5
C(CH3)3


2195
S
Br
OCOC6H5
C(CH3)3


2196
S
NO2
OCOC6H5
C(CH3)3


2197
S
SCH3
OCOC6H5
C(CH3)3


2198
S
SO2CH3
OCOC6H5
C(CH3)3


2199
S
SO2CH2CH3
OCOC6H5
C(CH3)3


2200
S
CH3
OCOC6H5
C(CH3)3


2201
S
CF3
OCOC6H5
C(CH3)3


2202
S
OCHF2
OCOC6H5
C(CH3)3


2203
SO2
F
OCOC6H5
C(CH3)3


2204
SO2
Cl
OCOC6H5
C(CH3)3


2205
SO2
Br
OCOC6H5
C(CH3)3


2206
SO2
NO2
OCOC6H5
C(CH3)3


2207
SO2
SCH3
OCOC6H5
C(CH3)3


2208
SO2
SO2CH3
OCOC6H5
C(CH3)3


2209
SO2
SO2CH2CH3
OCOC6H5
C(CH3)3


2210
SO2
CH3
OCOC6H5
C(CH3)3


2211
SO2
CF3
OCOC6H5
C(CH3)3


2212
SO2
OCHF2
OCOC6H5
C(CH3)3


2213
bond
F
OCOC(CH3)3
CH(CH3)2


2214
bond
Cl
OCOC(CH3)3
CH(CH3)2


2215
bond
Br
OCOC(CH3)3
CH(CH3)2


2216
bond
NO2
OCOC(CH3)3
CH(CH3)2


2217
bond
SCH3
OCOC(CH3)3
CH(CH3)2


2218
bond
SO2CH3
OCOC(CH3)3
CH(CH3)2


2219
bond
SO2CH2CH3
OCOC(CH3)3
CH(CH3)2


2220
bond
CH3
OCOC(CH3)3
CH(CH3)2


2221
bond
CF3
OCOC(CH3)3
CH(CH3)2


2222
bond
OCHF2
OCOC(CH3)3
CH(CH3)2


2223
CH2
F
OCOC(CH3)3
CH(CH3)2


2224
CH2
Cl
OCOC(CH3)3
CH(CH3)2


2225
CH2
Br
OCOC(CH3)3
CH(CH3)2


2226
CH2
NO2
OCOC(CH3)3
CH(CH3)2


2227
CH2
SCH3
OCOC(CH3)3
CH(CH3)2


2228
CH2
SO2CH3
OCOC(CH3)3
CH(CH3)2


2229
CH2
SO2CH2CH3
OCOC(CH3)3
CH(CH3)2


2230
CH2
CH3
OCOC(CH3)3
CH(CH3)2


2231
CH2
CF3
OCOC(CH3)3
CH(CH3)2


2232
CH2
OCHF2
OCOC(CH3)3
CH(CH3)2


2233
O
F
OCOC(CH3)3
CH(CH3)2


2234
O
Cl
OCOC(CH3)3
CH(CH3)2


2235
O
Br
OCOC(CH3)3
CH(CH3)2


2236
O
NO2
OCOC(CH3)3
CH(CH3)2


2237
O
SCH3
OCOC(CH3)3
CH(CH3)2


2238
O
SO2CH3
OCOC(CH3)3
CH(CH3)2


2239
O
SO2CH2CH3
OCOC(CH3)3
CH(CH3)2


2240
O
CH3
OCOC(CH3)3
CH(CH3)2


2241
O
CF3
OCOC(CH3)3
CH(CH3)2


2242
O
OCHF2
OCOC(CH3)3
CH(CH3)2


2243
S
F
OCOC(CH3)3
CH(CH3)2


2244
S
Cl
OCOC(CH3)3
CH(CH3)2


2245
S
Br
OCOC(CH3)3
CH(CH3)2


2246
S
NO2
OCOC(CH3)3
CH(CH3)2


2247
S
SCH3
OCOC(CH3)3
CH(CH3)2


2248
S
SO2CH3
OCOC(CH3)3
CH(CH3)2


2249
S
SO2CH2CH3
OCOC(CH3)3
CH(CH3)2


2250
S
CH3
OCOC(CH3)3
CH(CH3)2


2251
S
CF3
OCOC(CH3)3
CH(CH3)2


2252
S
OCHF2
OCOC(CH3)3
CH(CH3)2


2253
SO2
F
OCOC(CH3)3
CH(CH3)2


2254
SO2
Cl
OCOC(CH3)3
CH(CH3)2


2255
SO2
Br
OCOC(CH3)3
CH(CH3)2


2256
SO2
NO2
OCOC(CH3)3
CH(CH3)2


2257
SO2
SCH3
OCOC(CH3)3
CH(CH3)2


2258
SO2
SO2CH3
OCOC(CH3)3
CH(CH3)2


2259
SO2
SO2CH2CH3
OCOC(CH3)3
CH(CH3)2


2260
SO2
CH3
OCOC(CH3)3
CH(CH3)2


2261
SO2
CF3
OCOC(CH3)3
CH(CH3)2


2262
SO2
OCHF2
OCOC(CH3)3
CH(CH3)2


2263
bond
F
OCOC(CH3)3
C(CH3)3


2264
bond
Cl
OCOC(CH3)3
C(CH3)3


2265
bond
Br
OCOC(CH3)3
C(CH3)3


2266
bond
NO2
OCOC(CH3)3
C(CH3)3


2267
bond
SCH3
OCOC(CH3)3
C(CH3)3


2268
bond
SO2CH3
OCOC(CH3)3
C(CH3)3


2269
bond
SO2CH2CH3
OCOC(CH3)3
C(CH3)3


2270
bond
CH3
OCOC(CH3)3
C(CH3)3


2271
bond
CF3
OCOC(CH3)3
C(CH3)3


2272
bond
OCHF2
OCOC(CH3)3
C(CH3)3


2273
CH2
F
OCOC(CH3)3
C(CH3)3


2274
CH2
Cl
OCOC(CH3)3
C(CH3)3


2275
CH2
Br
OCOC(CH3)3
C(CH3)3


2276
CH2
NO2
OCOC(CH3)3
C(CH3)3


2277
CH2
SCH3
OCOC(CH3)3
C(CH3)3


2278
CH2
SO2CH3
OCOC(CH3)3
C(CH3)3


2279
CH2
SO2CH2CH3
OCOC(CH3)3
C(CH3)3


2280
CH2
CH3
OCOC(CH3)3
C(CH3)3


2281
CH2
CF3
OCOC(CH3)3
C(CH3)3


2282
CH2
OCHF2
OCOC(CH3)3
C(CH3)3


2283
O
F
OCOC(CH3)3
C(CH3)3


2284
O
Cl
OCOC(CH3)3
C(CH3)3


2285
O
Br
OCOC(CH3)3
C(CH3)3


2286
O
NO2
OCOC(CH3)3
C(CH3)3


2287
O
SCH3
OCOC(CH3)3
C(CH3)3


2288
O
SO2CH3
OCOC(CH3)3
C(CH3)3


2289
O
SO2CH2CH3
OCOC(CH3)3
C(CH3)3


2290
O
CH3
OCOC(CH3)3
C(CH3)3


2291
O
CF3
OCOC(CH3)3
C(CH3)3


2292
O
OCHF2
OCOC(CH3)3
C(CH3)3


2293
S
F
OCOC(CH3)3
C(CH3)3


2294
S
Cl
OCOC(CH3)3
C(CH3)3


2295
S
Br
OCOC(CH3)3
C(CH3)3


2296
S
NO2
OCOC(CH3)3
C(CH3)3


2297
S
SCH3
OCOC(CH3)3
C(CH3)3


2298
S
SO2CH3
OCOC(CH3)3
C(CH3)3


2299
S
SO2CH2CH3
OCOC(CH3)3
C(CH3)3


2300
S
CH3
OCOC(CH3)3
C(CH3)3


2301
S
CF3
OCOC(CH3)3
C(CH3)3


2302
S
OCHF2
OCOC(CH3)3
C(CH3)3


2303
SO2
F
OCOC(CH3)3
C(CH3)3


2304
SO2
Cl
OCOC(CH3)3
C(CH3)3


2305
SO2
Br
OCOC(CH3)3
C(CH3)3


2306
SO2
NO2
OCOC(CH3)3
C(CH3)3


2307
SO2
SCH3
OCOC(CH3)3
C(CH3)3


2308
SO2
SO2CH3
OCOC(CH3)3
C(CH3)3


2309
SO2
SO2CH2CH3
OCOC(CH3)3
C(CH3)3


2310
SO2
CH3
OCOC(CH3)3
C(CH3)3


2311
SO2
CF3
OCOC(CH3)3
C(CH3)3


2312
SO2
OCHF2
OCOC(CH3)3
C(CH3)3


2313
bond
F
OCOSCH3
CH(CH3)2


2314
bond
Cl
OCOSCH3
CH(CH3)2


2315
bond
Br
OCOSCH3
CH(CH3)2


2316
bond
NO2
OCOSCH3
CH(CH3)2


2317
bond
SCH3
OCOSCH3
CH(CH3)2


2318
bond
SO2CH3
OCOSCH3
CH(CH3)2


2319
bond
SO2CH2CH3
OCOSCH3
CH(CH3)2


2320
bond
CH3
OCOSCH3
CH(CH3)2


2321
bond
CF3
OCOSCH3
CH(CH3)2


2322
bond
OCHF2
OCOSCH3
CH(CH3)2


2323
CH2
F
OCOSCH3
CH(CH3)2


2324
CH2
Cl
OCOSCH3
CH(CH3)2


2325
CH2
Br
OCOSCH3
CH(CH3)2


2326
CH2
NO2
OCOSCH3
CH(CH3)2


2327
CH2
SCH3
OCOSCH3
CH(CH3)2


2328
CH2
SO2CH3
OCOSCH3
CH(CH3)2


2329
CH2
SO2CH2CH3
OCOSCH3
CH(CH3)2


2330
CH2
CH3
OCOSCH3
CH(CH3)2


2331
CH2
CF3
OCOSCH3
CH(CH3)2


2332
CH2
OCHF2
OCOSCH3
CH(CH3)2


2333
O
F
OCOSCH3
CH(CH3)2


2334
O
Cl
OCOSCH3
CH(CH3)2


2335
O
Br
OCOSCH3
CH(CH3)2


2336
O
NO2
OCOSCH3
CH(CH3)2


2337
O
SCH3
OCOSCH3
CH(CH3)2


2338
O
SO2CH3
OCOSCH3
CH(CH3)2


2339
O
SO2CH2CH3
OCOSCH3
CH(CH3)2


2340
O
CH3
OCOSCH3
CH(CH3)2


2341
O
CF3
OCOSCH3
CH(CH3)2


2342
O
OCHF2
OCOSCH3
CH(CH3)2


2343
S
F
OCOSCH3
CH(CH3)2


2344
S
Cl
OCOSCH3
CH(CH3)2


2345
S
Br
OCOSCH3
CH(CH3)2


2346
S
NO2
OCOSCH3
CH(CH3)2


2347
S
SCH3
OCOSCH3
CH(CH3)2


2348
S
SO2CH3
OCOSCH3
CH(CH3)2


2349
S
SO2CH2CH3
OCOSCH3
CH(CH3)2


2350
S
CH3
OCOSCH3
CH(CH3)2


2351
S
CF3
OCOSCH3
CH(CH3)2


2352
S
OCHF2
OCOSCH3
CH(CH3)2


2353
SO2
F
OCOSCH3
CH(CH3)2


2354
SO2
Cl
OCOSCH3
CH(CH3)2


2355
SO2
Br
OCOSCH3
CH(CH3)2


2356
SO2
NO2
OCOSCH3
CH(CH3)2


2357
SO2
SCH3
OCOSCH3
CH(CH3)2


2358
SO2
SO2CH3
OCOSCH3
CH(CH3)2


2359
SO2
SO2CH2CH3
OCOSCH3
CH(CH3)2


2360
SO2
CH3
OCOSCH3
CH(CH3)2


2361
SO2
CF3
OCOSCH3
CH(CH3)2


2362
SO2
OCHF2
OCOSCH3
CH(CH3)2


2363
bond
F
OCOSCH3
C(CH3)3


2364
bond
Cl
OCOSCH3
C(CH3)3


2365
bond
Br
OCOSCH3
C(CH3)3


2366
bond
NO2
OCOSCH3
C(CH3)3


2367
bond
SCH3
OCOSCH3
C(CH3)3


2368
bond
SO2CH3
OCOSCH3
C(CH3)3


2369
bond
SO2CH2CH3
OCOSCH3
C(CH3)3


2370
bond
CH3
OCOSCH3
C(CH3)3


2371
bond
CF3
OCOSCH3
C(CH3)3


2372
bond
OCHF2
OCOSCH3
C(CH3)3


2373
CH2
F
OCOSCH3
C(CH3)3


2374
CH2
Cl
OCOSCH3
C(CH3)3


2375
CH2
Br
OCOSCH3
C(CH3)3


2376
CH2
NO2
OCOSCH3
C(CH3)3


2377
CH2
SCH3
OCOSCH3
C(CH3)3


2378
CH2
SO2CH3
OCOSCH3
C(CH3)3


2379
CH2
SO2CH2CH3
OCOSCH3
C(CH3)3


2380
CH2
CH3
OCOSCH3
C(CH3)3


2381
CH2
CF3
OCOSCH3
C(CH3)3


2382
CH2
OCHF2
OCOSCH3
C(CH3)3


2383
O
F
OCOSCH3
C(CH3)3


2384
O
Cl
OCOSCH3
C(CH3)3


2385
O
Br
OCOSCH3
C(CH3)3


2386
O
NO2
OCOSCH3
C(CH3)3


2387
O
SCH3
OCOSCH3
C(CH3)3


2388
O
SO2CH3
OCOSCH3
C(CH3)3


2389
O
SO2CH2CH3
OCOSCH3
C(CH3)3


2390
O
CH3
OCOSCH3
C(CH3)3


2391
O
CF3
OCOSCH3
C(CH3)3


2392
O
OCHF2
OCOSCH3
C(CH3)3


2393
S
F
OCOSCH3
C(CH3)3


2394
S
Cl
OCOSCH3
C(CH3)3


2395
S
Br
OCOSCH3
C(CH3)3


2396
S
NO2
OCOSCH3
C(CH3)3


2397
S
SCH3
OCOSCH3
C(CH3)3


2398
S
SO2CH3
OCOSCH3
C(CH3)3


2399
S
SO2CH2CH3
OCOSCH3
C(CH3)3


2400
S
CH3
OCOSCH3
C(CH3)3


2401
S
CF3
OCOSCH3
C(CH3)3


2402
S
OCHF2
OCOSCH3
C(CH3)3


2403
SO2
F
OCOSCH3
C(CH3)3


2404
SO2
Cl
OCOSCH3
C(CH3)3


2405
SO2
Br
OCOSCH3
C(CH3)3


2406
SO2
NO2
OCOSCH3
C(CH3)3


2407
SO2
SCH3
OCOSCH3
C(CH3)3


2408
SO2
SO2CH3
OCOSCH3
C(CH3)3


2409
SO2
SO2CH2CH3
OCOSCH3
C(CH3)3


2410
SO2
CH3
OCOSCH3
C(CH3)3


2411
SO2
CF3
OCOSCH3
C(CH3)3


2412
SO2
OCHF2
OCOSCH3
C(CH3)3


2413
bond
F
OCH3
CH(CH3)2


2414
bond
Cl
OCH3
CH(CH3)2


2415
bond
Br
OCH3
CH(CH3)2


2416
bond
NO2
OCH3
CH(CH3)2


2417
bond
SCH3
OCH3
CH(CH3)2


2418
bond
SO2CH3
OCH3
CH(CH3)2


2419
bond
SO2CH2CH3
OCH3
CH(CH3)2


2420
bond
CH3
OCH3
CH(CH3)2


2421
bond
CF3
OCH3
CH(CH3)2


2422
bond
OCHF2
OCH3
CH(CH3)2


2423
CH2
F
OCH3
CH(CH3)2


2424
CH2
Cl
OCH3
CH(CH3)2


2425
CH2
Br
OCH3
CH(CH3)2


2426
CH2
NO2
OCH3
CH(CH3)2


2427
CH2
SCH3
OCH3
CH(CH3)2


2428
CH2
SO2CH3
OCH3
CH(CH3)2


2429
CH2
SO2CH2CH3
OCH3
CH(CH3)2


2430
CH2
CH3
OCH3
CH(CH3)2


2431
CH2
CF3
OCH3
CH(CH3)2


2432
CH2
OCHF2
OCH3
CH(CH3)2


2433
O
F
OCH3
CH(CH3)2


2434
O
Cl
OCH3
CH(CH3)2


2435
O
Br
OCH3
CH(CH3)2


2436
O
NO2
OCH3
CH(CH3)2


2437
O
SCH3
OCH3
CH(CH3)2


2438
O
SO2CH3
OCH3
CH(CH3)2


2439
O
SO2CH2CH3
OCH3
CH(CH3)2


2440
O
CH3
OCH3
CH(CH3)2


2441
O
CF3
OCH3
CH(CH3)2


2442
O
OCHF2
OCH3
CH(CH3)2


2443
S
F
OCH3
CH(CH3)2


2444
S
Cl
OCH3
CH(CH3)2


2445
S
Br
OCH3
CH(CH3)2


2446
S
NO2
OCH3
CH(CH3)2


2447
S
SCH3
OCH3
CH(CH3)2


2448
S
SO2CH3
OCH3
CH(CH3)2


2449
S
SO2CH2CH3
OCH3
CH(CH3)2


2450
S
CH3
OCH3
CH(CH3)2


2451
S
CF3
OCH3
CH(CH3)2


2452
S
OCHF2
OCH3
CH(CH3)2


2453
SO2
F
OCH3
CH(CH3)2


2454
SO2
Cl
OCH3
CH(CH3)2


2455
SO2
Br
OCH3
CH(CH3)2


2456
SO2
NO2
OCH3
CH(CH3)2


2457
SO2
SCH3
OCH3
CH(CH3)2


2458
SO2
SO2CH3
OCH3
CH(CH3)2


2459
SO2
SO2CH2CH3
OCH3
CH(CH3)2


2460
SO2
CH3
OCH3
CH(CH3)2


2461
SO2
CF3
OCH3
CH(CH3)2


2462
SO2
OCHF2
OCH3
CH(CH3)2


2463
bond
F
OCH3
C(CH3)3


2464
bond
Cl
OCH3
C(CH3)3


2465
bond
Br
OCH3
C(CH3)3


2466
bond
NO2
OCH3
C(CH3)3


2467
bond
SCH3
OCH3
C(CH3)3


2468
bond
SO2CH3
OCH3
C(CH3)3


2469
bond
SO2CH2CH3
OCH3
C(CH3)3


2470
bond
CH3
OCH3
C(CH3)3


2471
bond
CF3
OCH3
C(CH3)3


2472
bond
OCHF2
OCH3
C(CH3)3


2473
CH2
F
OCH3
C(CH3)3


2474
CH2
Cl
OCH3
C(CH3)3


2475
CH2
Br
OCH3
C(CH3)3


2476
CH2
NO2
OCH3
C(CH3)3


2477
CH2
SCH3
OCH3
C(CH3)3


2478
CH2
SO2CH3
OCH3
C(CH3)3


2479
CH2
SO2CH2CH3
OCH3
C(CH3)3


2480
CH2
CH3
OCH3
C(CH3)3


2481
CH2
CF3
OCH3
C(CH3)3


2482
CH2
OCHF2
OCH3
C(CH3)3


2483
O
F
OCH3
C(CH3)3


2484
O
Cl
OCH3
C(CH3)3


2485
O
Br
OCH3
C(CH3)3


2486
O
NO2
OCH3
C(CH3)3


2487
O
SCH3
OCH3
C(CH3)3


2488
O
SO2CH3
OCH3
C(CH3)3


2489
O
SO2CH2CH3
OCH3
C(CH3)3


2490
O
CH3
OCH3
C(CH3)3


2491
O
CF3
OCH3
C(CH3)3


2492
O
OCHF2
OCH3
C(CH3)3


2493
S
F
OCH3
C(CH3)3


2494
S
Cl
OCH3
C(CH3)3


2495
S
Br
OCH3
C(CH3)3


2496
S
NO2
OCH3
C(CH3)3


2497
S
SCH3
OCH3
C(CH3)3


2498
S
SO2CH3
OCH3
C(CH3)3


2499
S
SO2CH2CH3
OCH3
C(CH3)3


2500
S
CH3
OCH3
C(CH3)3


2501
S
CF3
OCH3
C(CH3)3


2502
S
OCHF2
OCH3
C(CH3)3


2503
SO2
F
OCH3
C(CH3)3


2504
SO2
Cl
OCH3
C(CH3)3


2505
SO2
Br
OCH3
C(CH3)3


2506
SO2
NO2
OCH3
C(CH3)3


2507
SO2
SCH3
OCH3
C(CH3)3


2508
SO2
SO2CH3
OCH3
C(CH3)3


2509
SO2
SO2CH2CH3
OCH3
C(CH3)3


2510
SO2
CH3
OCH3
C(CH3)3


2511
SO2
CF3
OCH3
C(CH3)3


2512
SO2
OCHF2
OCH3
C(CH3)3


2513
bond
F
OCH(CH3)2
CH(CH3)2


2514
bond
Cl
OCH(CH3)2
CH(CH3)2


2515
bond
Br
OCH(CH3)2
CH(CH3)2


2516
bond
NO2
OCH(CH3)2
CH(CH3)2


2517
bond
SCH3
OCH(CH3)2
CH(CH3)2


2518
bond
SO2CH3
OCH(CH3)2
CH(CH3)2


2519
bond
SO2CH2CH3
OCH(CH3)2
CH(CH3)2


2520
bond
CH3
OCH(CH3)2
CH(CH3)2


2521
bond
CF3
OCH(CH3)2
CH(CH3)2


2522
bond
OCHF2
OCH(CH3)2
CH(CH3)2


2523
CH2
F
OCH(CH3)2
CH(CH3)2


2524
CH2
Cl
OCH(CH3)2
CH(CH3)2


2525
CH2
Br
OCH(CH3)2
CH(CH3)2


2526
CH2
NO2
OCH(CH3)2
CH(CH3)2


2527
CH2
SCH3
OCH(CH3)2
CH(CH3)2


2528
CH2
SO2CH3
OCH(CH3)2
CH(CH3)2


2529
CH2
SO2CH2CH3
OCH(CH3)2
CH(CH3)2


2530
CH2
CH3
OCH(CH3)2
CH(CH3)2


2531
CH2
CF3
OCH(CH3)2
CH(CH3)2


2532
CH2
OCHF2
OCH(CH3)2
CH(CH3)2


2533
O
F
OCH(CH3)2
CH(CH3)2


2534
O
Cl
OCH(CH3)2
CH(CH3)2


2535
O
Br
OCH(CH3)2
CH(CH3)2


2536
O
NO2
OCH(CH3)2
CH(CH3)2


2537
O
SCH3
OCH(CH3)2
CH(CH3)2


2538
O
SO2CH3
OCH(CH3)2
CH(CH3)2


2539
O
SO2CH2CH3
OCH(CH3)2
CH(CH3)2


2540
O
CH3
OCH(CH3)2
CH(CH3)2


2541
O
CF3
OCH(CH3)2
CH(CH3)2


2542
O
OCHF2
OCH(CH3)2
CH(CH3)2


2543
S
F
OCH(CH3)2
CH(CH3)2


2544
S
Cl
OCH(CH3)2
CH(CH3)2


2545
S
Br
OCH(CH3)2
CH(CH3)2


2546
S
NO2
OCH(CH3)2
CH(CH3)2


2547
S
SCH3
OCH(CH3)2
CH(CH3)2


2548
S
SO2CH3
OCH(CH3)2
CH(CH3)2


2549
S
SO2CH2CH3
OCH(CH3)2
CH(CH3)2


2550
S
CH3
OCH(CH3)2
CH(CH3)2


2551
S
CF3
OCH(CH3)2
CH(CH3)2


2552
S
OCHF2
OCH(CH3)2
CH(CH3)2


2553
SO2
F
OCH(CH3)2
CH(CH3)2


2554
SO2
Cl
OCH(CH3)2
CH(CH3)2


2555
SO2
Br
OCH(CH3)2
CH(CH3)2


2556
SO2
NO2
OCH(CH3)2
CH(CH3)2


2557
SO2
SCH3
OCH(CH3)2
CH(CH3)2


2558
SO2
SO2CH3
OCH(CH3)2
CH(CH3)2


2559
SO2
SO2CH2CH3
OCH(CH3)2
CH(CH3)2


2560
SO2
CH3
OCH(CH3)2
CH(CH3)2


2561
SO2
CF3
OCH(CH3)2
CH(CH3)2


2562
SO2
OCHF2
OCH(CH3)2
CH(CH3)2


2563
bond
F
OCH(CH3)2
C(CH3)3


2564
bond
Cl
OCH(CH3)2
C(CH3)3


2565
bond
Br
OCH(CH3)2
C(CH3)3


2566
bond
NO2
OCH(CH3)2
C(CH3)3


2567
bond
SCH3
OCH(CH3)2
C(CH3)3


2568
bond
SO2CH3
OCH(CH3)2
C(CH3)3


2569
bond
SO2CH2CH3
OCH(CH3)2
C(CH3)3


2570
bond
CH3
OCH(CH3)2
C(CH3)3


2571
bond
CF3
OCH(CH3)2
C(CH3)3


2572
bond
OCHF2
OCH(CH3)2
C(CH3)3


2573
CH2
F
OCH(CH3)2
C(CH3)3


2574
CH2
Cl
OCH(CH3)2
C(CH3)3


2575
CH2
Br
OCH(CH3)2
C(CH3)3


2576
CH2
NO2
OCH(CH3)2
C(CH3)3


2577
CH2
SCH3
OCH(CH3)2
C(CH3)3


2578
CH2
SO2CH3
OCH(CH3)2
C(CH3)3


2579
CH2
SO2CH2CH3
OCH(CH3)2
C(CH3)3


2580
CH2
CH3
OCH(CH3)2
C(CH3)3


2581
CH2
CF3
OCH(CH3)2
C(CH3)3


2582
CH2
OCHF2
OCH(CH3)2
C(CH3)3


2583
O
F
OCH(CH3)2
C(CH3)3


2584
O
Cl
OCH(CH3)2
C(CH3)3


2585
O
Br
OCH(CH3)2
C(CH3)3


2586
O
NO2
OCH(CH3)2
C(CH3)3


2587
O
SCH3
OCH(CH3)2
C(CH3)3


2588
O
SO2CH3
OCH(CH3)2
C(CH3)3


2589
O
SO2CH2CH3
OCH(CH3)2
C(CH3)3


2590
O
CH3
OCH(CH3)2
C(CH3)3


2591
O
CF3
OCH(CH3)2
C(CH3)3


2592
O
OCHF2
OCH(CH3)2
C(CH3)3


2593
S
F
OCH(CH3)2
C(CH3)3


2594
S
Cl
OCH(CH3)2
C(CH3)3


2595
S
Br
OCH(CH3)2
C(CH3)3


2596
S
NO2
OCH(CH3)2
C(CH3)3


2597
S
SCH3
OCH(CH3)2
C(CH3)3


2598
S
SO2CH3
OCH(CH3)2
C(CH3)3


2599
S
SO2CH2CH3
OCH(CH3)2
C(CH3)3


2600
S
CH3
OCH(CH3)2
C(CH3)3


2601
S
CF3
OCH(CH3)2
C(CH3)3


2602
S
OCHF2
OCH(CH3)2
C(CH3)3


2603
SO2
F
OCH(CH3)2
C(CH3)3


2604
SO2
Cl
OCH(CH3)2
C(CH3)3


2605
SO2
Br
OCH(CH3)2
C(CH3)3


2606
SO2
NO2
OCH(CH3)2
C(CH3)3


2607
SO2
SCH3
OCH(CH3)2
C(CH3)3


2608
SO2
SO2CH3
OCH(CH3)2
C(CH3)3


2609
SO2
SO2CH2CH3
OCH(CH3)2
C(CH3)3


2610
SO2
CH3
OCH(CH3)2
C(CH3)3


2611
SO2
CF3
OCH(CH3)2
C(CH3)3


2612
SO2
OCHF2
OCH(CH3)2
C(CH3)3


2613
bond
F
OCH2C6H5
CH(CH3)2


2614
bond
Cl
OCH2C6H5
CH(CH3)2


2615
bond
Br
OCH2C6H5
CH(CH3)2


2616
bond
NO2
OCH2C6H5
CH(CH3)2


2617
bond
SCH3
OCH2C6H5
CH(CH3)2


2618
bond
SO2CH3
OCH2C6H5
CH(CH3)2


2619
bond
SO2CH2CH3
OCH2C6H5
CH(CH3)2


2620
bond
CH3
OCH2C6H5
CH(CH3)2


2621
bond
CF3
OCH2C6H5
CH(CH3)2


2622
bond
OCHF2
OCH2C6H5
CH(CH3)2


2623
CH2
F
OCH2C6H5
CH(CH3)2


2624
CH2
Cl
OCH2C6H5
CH(CH3)2


2625
CH2
Br
OCH2C6H5
CH(CH3)2


2626
CH2
NO2
OCH2C6H5
CH(CH3)2


2627
CH2
SCH3
OCH2C6H5
CH(CH3)2


2628
CH2
SO2CH3
OCH2C6H5
CH(CH3)2


2629
CH2
SO2CH2CH3
OCH2C6H5
CH(CH3)2


2630
CH2
CH3
OCH2C6H5
CH(CH3)2


2631
CH2
CF3
OCH2C6H5
CH(CH3)2


2632
CH2
OCHF2
OCH2C6H5
CH(CH3)2


2633
O
F
OCH2C6H5
CH(CH3)2


2634
O
Cl
OCH2C6H5
CH(CH3)2


2635
O
Br
OCH2C6H5
CH(CH3)2


2636
O
NO2
OCH2C6H5
CH(CH3)2


2637
O
SCH3
OCH2C6H5
CH(CH3)2


2638
O
SO2CH3
OCH2C6H5
CH(CH3)2


2639
O
SO2CH2CH3
OCH2C6H5
CH(CH3)2


2640
O
CH3
OCH2C6H5
CH(CH3)2


2641
O
CF3
OCH2C6H5
CH(CH3)2


2642
O
OCHF2
OCH2C6H5
CH(CH3)2


2643
S
F
OCH2C6H5
CH(CH3)2


2644
S
Cl
OCH2C6H5
CH(CH3)2


2645
S
Br
OCH2C6H5
CH(CH3)2


2646
S
NO2
OCH2C6H5
CH(CH3)2


2647
S
SCH3
OCH2C6H5
CH(CH3)2


2648
S
SO2CH3
OCH2C6H5
CH(CH3)2


2649
S
SO2CH2CH3
OCH2C6H5
CH(CH3)2


2650
S
CH3
OCH2C6H5
CH(CH3)2


2651
S
CF3
OCH2C6H5
CH(CH3)2


2652
S
OCHF2
OCH2C6H5
CH(CH3)2


2653
SO2
F
OCH2C6H5
CH(CH3)2


2654
SO2
Cl
OCH2C6H5
CH(CH3)2


2655
SO2
Br
OCH2C6H5
CH(CH3)2


2656
SO2
NO2
OCH2C6H5
CH(CH3)2


2657
SO2
SCH3
OCH2C6H5
CH(CH3)2


2658
SO2
SO2CH3
OCH2C6H5
CH(CH3)2


2659
SO2
SO2CH2CH3
OCH2C6H5
CH(CH3)2


2660
SO2
CH3
OCH2C6H5
CH(CH3)2


2661
SO2
CF3
OCH2C6H5
CH(CH3)2


2662
SO2
OCHF2
OCH2C6H5
CH(CH3)2


2663
bond
F
OCH2C6H5
C(CH3)3


2664
bond
Cl
OCH2C6H5
C(CH3)3


2665
bond
Br
OCH2C6H5
C(CH3)3


2666
bond
NO2
OCH2C6H5
C(CH3)3


2667
bond
SCH3
OCH2C6H5
C(CH3)3


2668
bond
SO2CH3
OCH2C6H5
C(CH3)3


2669
bond
SO2CH2CH3
OCH2C6H5
C(CH3)3


2670
bond
CH3
OCH2C6H5
C(CH3)3


2671
bond
CF3
OCH2C6H5
C(CH3)3


2672
bond
OCHF2
OCH2C6H5
C(CH3)3


2673
CH2
F
OCH2C6H5
C(CH3)3


2674
CH2
Cl
OCH2C6H5
C(CH3)3


2675
CH2
Br
OCH2C6H5
C(CH3)3


2676
CH2
NO2
OCH2C6H5
C(CH3)3


2677
CH2
SCH3
OCH2C6H5
C(CH3)3


2678
CH2
SO2CH3
OCH2C6H5
C(CH3)3


2679
CH2
SO2CH2CH3
OCH2C6H5
C(CH3)3


2680
CH2
CH3
OCH2C6H5
C(CH3)3


2681
CH2
CF3
OCH2C6H5
C(CH3)3


2682
CH2
OCHF2
OCH2C6H5
C(CH3)3


2683
O
F
OCH2C6H5
C(CH3)3


2684
O
Cl
OCH2C6H5
C(CH3)3


2685
O
Br
OCH2C6H5
C(CH3)3


2686
O
NO2
OCH2C6H5
C(CH3)3


2687
O
SCH3
OCH2C6H5
C(CH3)3


2688
O
SO2CH3
OCH2C6H5
C(CH3)3


2689
O
SO2CH2CH3
OCH2C6H5
C(CH3)3


2690
O
CH3
OCH2C6H5
C(CH3)3


2691
O
CF3
OCH2C6H5
C(CH3)3


2692
O
OCHF2
OCH2C6H5
C(CH3)3


2693
S
F
OCH2C6H5
C(CH3)3


2694
S
Cl
OCH2C6H5
C(CH3)3


2695
S
Br
OCH2C6H5
C(CH3)3


2696
S
NO2
OCH2C6H5
C(CH3)3


2697
S
SCH3
OCH2C6H5
C(CH3)3


2698
S
SO2CH3
OCH2C6H5
C(CH3)3


2699
S
SO2CH2CH3
OCH2C6H5
C(CH3)3


2700
S
CH3
OCH2C6H5
C(CH3)3


2701
S
CF3
OCH2C6H5
C(CH3)3


2702
S
OCHF2
OCH2C6H5
C(CH3)3


2703
SO2
F
OCH2C6H5
C(CH3)3


2704
SO2
Cl
OCH2C6H5
C(CH3)3


2705
SO2
Br
OCH2C6H5
C(CH3)3


2706
SO2
NO2
OCH2C6H5
C(CH3)3


2707
SO2
SCH3
OCH2C6H5
C(CH3)3


2708
SO2
SO2CH3
OCH2C6H5
C(CH3)3


2709
SO2
SO2CH2CH3
OCH2C6H5
C(CH3)3


2710
SO2
CH3
OCH2C6H5
C(CH3)3


2711
SO2
CF3
OCH2C6H5
C(CH3)3


2712
SO2
OCHF2
OCH2C6H5
C(CH3)3


2713
bond
F
OSO2(4-CH3—C6H4)
CH(CH3)2


2714
bond
Cl
OSO2(4-CH3—C6H4)
CH(CH3)2


2715
bond
Br
OSO2(4-CH3—C6H4)
CH(CH3)2


2716
bond
NO2
OSO2(4-CH3—C6H4)
CH(CH3)2


2717
bond
SCH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2718
bond
SO2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2719
bond
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2720
bond
CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2721
bond
CF3
OSO2(4-CH3—C6H4)
CH(CH3)2


2722
bond
OCHF2
OSO2(4-CH3—C6H4)
CH(CH3)2


2723
CH2
F
OSO2(4-CH3—C6H4)
CH(CH3)2


2724
CH2
Cl
OSO2(4-CH3—C6H4)
CH(CH3)2


2725
CH2
Br
OSO2(4-CH3—C6H4)
CH(CH3)2


2726
CH2
NO2
OSO2(4-CH3—C6H4)
CH(CH3)2


2727
CH2
SCH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2728
CH2
SO2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2729
CH2
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2730
CH2
CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2731
CH2
CF3
OSO2(4-CH3—C6H4)
CH(CH3)2


2732
CH2
OCHF2
OSO2(4-CH3—C6H4)
CH(CH3)2


2733
O
F
OSO2(4-CH3—C6H4)
CH(CH3)2


2734
O
Cl
OSO2(4-CH3—C6H4)
CH(CH3)2


2735
O
Br
OSO2(4-CH3—C6H4)
CH(CH3)2


2736
O
NO2
OSO2(4-CH3—C6H4)
CH(CH3)2


2737
O
SCH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2738
O
SO2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2739
O
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2740
O
CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2741
O
CF3
OSO2(4-CH3—C6H4)
CH(CH3)2


2742
O
OCHF2
OSO2(4-CH3—C6H4)
CH(CH3)2


2743
S
F
OSO2(4-CH3—C6H4)
CH(CH3)2


2744
S
Cl
OSO2(4-CH3—C6H4)
CH(CH3)2


2745
S
Br
OSO2(4-CH3—C6H4)
CH(CH3)2


2746
S
NO2
OSO2(4-CH3—C6H4)
CH(CH3)2


2747
S
SCH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2748
S
SO2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2749
S
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2750
S
CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2751
S
CF3
OSO2(4-CH3—C6H4)
CH(CH3)2


2752
S
OCHF2
OSO2(4-CH3—C6H4)
CH(CH3)2


2753
SO2
F
OSO2(4-CH3—C6H4)
CH(CH3)2


2754
SO2
Cl
OSO2(4-CH3—C6H4)
CH(CH3)2


2755
SO2
Br
OSO2(4-CH3—C6H4)
CH(CH3)2


2756
SO2
NO2
OSO2(4-CH3—C6H4)
CH(CH3)2


2757
SO2
SCH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2758
SO2
SO2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2759
SO2
SO2CH2CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2760
SO2
CH3
OSO2(4-CH3—C6H4)
CH(CH3)2


2761
SO2
CF3
OSO2(4-CH3—C6H4)
CH(CH3)2


2762
SO2
OCHF2
OSO2(4-CH3—C6H4)
CH(CH3)2


2763
bond
F
OSO2(4-CH3—C6H4)
C(CH3)3


2764
bond
Cl
OSO2(4-CH3—C6H4)
C(CH3)3


2765
bond
Br
OSO2(4-CH3—C6H4)
C(CH3)3


2766
bond
NO2
OSO2(4-CH3—C6H4)
C(CH3)3


2767
bond
SCH3
OSO2(4-CH3—C6H4)
C(CH3)3


2768
bond
SO2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2769
bond
SO2CH2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2770
bond
CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2771
bond
CF3
OSO2(4-CH3—C6H4)
C(CH3)3


2772
bond
OCHF2
OSO2(4-CH3—C6H4)
C(CH3)3


2773
CH2
F
OSO2(4-CH3—C6H4)
C(CH3)3


2774
CH2
Cl
OSO2(4-CH3—C6H4)
C(CH3)3


2775
CH2
Br
OSO2(4-CH3—C6H4)
C(CH3)3


2776
CH2
NO2
OSO2(4-CH3—C6H4)
C(CH3)3


2777
CH2
SCH3
OSO2(4-CH3—C6H4)
C(CH3)3


2778
CH2
SO2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2779
CH2
SO2CH2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2780
CH2
CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2781
CH2
CF3
OSO2(4-CH3—C6H4)
C(CH3)3


2782
CH2
OCHF2
OSO2(4-CH3—C6H4)
C(CH3)3


2783
O
F
OSO2(4-CH3—C6H4)
C(CH3)3


2784
O
Cl
OSO2(4-CH3—C6H4)
C(CH3)3


2785
O
Br
OSO2(4-CH3—C6H4)
C(CH3)3


2786
O
NO2
OSO2(4-CH3—C6H4)
C(CH3)3


2787
O
SCH3
OSO2(4-CH3—C6H4)
C(CH3)3


2788
O
SO2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2789
O
SO2CH2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2790
O
CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2791
O
CF3
OSO2(4-CH3—C6H4)
C(CH3)3


2792
O
OCHF2
OSO2(4-CH3—C6H4)
C(CH3)3


2793
S
F
OSO2(4-CH3—C6H4)
C(CH3)3


2794
S
Cl
OSO2(4-CH3—C6H4)
C(CH3)3


2795
S
Br
OSO2(4-CH3—C6H4)
C(CH3)3


2796
S
NO2
OSO2(4-CH3—C6H4)
C(CH3)3


2797
S
SCH3
OSO2(4-CH3—C6H4)
C(CH3)3


2798
S
SO2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2799
S
SO2CH2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2800
S
CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2801
S
CF3
OSO2(4-CH3—C6H4)
C(CH3)3


2802
S
OCHF2
OSO2(4-CH3—C6H4)
C(CH3)3


2803
SO2
F
OSO2(4-CH3—C6H4)
C(CH3)3


2804
SO2
Cl
OSO2(4-CH3—C6H4)
C(CH3)3


2805
SO2
Br
OSO2(4-CH3—C6H4)
C(CH3)3


2806
SO2
NO2
OSO2(4-CH3—C6H4)
C(CH3)3


2807
SO2
SCH3
OSO2(4-CH3—C6H4)
C(CH3)3


2808
SO2
SO2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2809
SO2
SO2CH2CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2810
SO2
CH3
OSO2(4-CH3—C6H4)
C(CH3)3


2811
SO2
CF3
OSO2(4-CH3—C6H4)
C(CH3)3


2812
SO2
OCHF2
OSO2(4-CH3—C6H4)
C(CH3)3


2813
bond
F
SCH3
CH(CH3)2


2814
bond
Cl
SCH3
CH(CH3)2


2815
bond
Br
SCH3
CH(CH3)2


2816
bond
NO2
SCH3
CH(CH3)2


2817
bond
SCH3
SCH3
CH(CH3)2


2818
bond
SO2CH3
SCH3
CH(CH3)2


2819
bond
SO2CH2CH3
SCH3
CH(CH3)2


2820
bond
CH3
SCH3
CH(CH3)2


2821
bond
CF3
SCH3
CH(CH3)2


2822
bond
OCHF2
SCH3
CH(CH3)2


2823
CH2
F
SCH3
CH(CH3)2


2824
CH2
Cl
SCH3
CH(CH3)2


2825
CH2
Br
SCH3
CH(CH3)2


2826
CH2
NO2
SCH3
CH(CH3)2


2827
CH2
SCH3
SCH3
CH(CH3)2


2828
CH2
SO2CH3
SCH3
CH(CH3)2


2829
CH2
SO2CH2CH3
SCH3
CH(CH3)2


2830
CH2
CH3
SCH3
CH(CH3)2


2831
CH2
CF3
SCH3
CH(CH3)2


2832
CH2
OCHF2
SCH3
CH(CH3)2


2833
O
F
SCH3
CH(CH3)2


2834
O
Cl
SCH3
CH(CH3)2


2835
O
Br
SCH3
CH(CH3)2


2836
O
NO2
SCH3
CH(CH3)2


2837
O
SCH3
SCH3
CH(CH3)2


2838
O
SO2CH3
SCH3
CH(CH3)2


2839
O
SO2CH2CH3
SCH3
CH(CH3)2


2840
O
CH3
SCH3
CH(CH3)2


2841
O
CF3
SCH3
CH(CH3)2


2842
O
OCHF2
SCH3
CH(CH3)2


2843
S
F
SCH3
CH(CH3)2


2844
S
Cl
SCH3
CH(CH3)2


2845
S
Br
SCH3
CH(CH3)2


2846
S
NO2
SCH3
CH(CH3)2


2847
S
SCH3
SCH3
CH(CH3)2


2848
S
SO2CH3
SCH3
CH(CH3)2


2849
S
SO2CH2CH3
SCH3
CH(CH3)2


2850
S
CH3
SCH3
CH(CH3)2


2851
S
CF3
SCH3
CH(CH3)2


2852
S
OCHF2
SCH3
CH(CH3)2


2853
SO2
F
SCH3
CH(CH3)2


2854
SO2
Cl
SCH3
CH(CH3)2


2855
SO2
Br
SCH3
CH(CH3)2


2856
SO2
NO2
SCH3
CH(CH3)2


2857
SO2
SCH3
SCH3
CH(CH3)2


2858
SO2
SO2CH3
SCH3
CH(CH3)2


2859
SO2
SO2CH2CH3
SCH3
CH(CH3)2


2860
SO2
CH3
SCH3
CH(CH3)2


2861
SO2
CF3
SCH3
CH(CH3)2


2862
SO2
OCHF2
SCH3
CH(CH3)2


2863
bond
F
SCH3
C(CH3)3


2864
bond
Cl
SCH3
C(CH3)3


2865
bond
Br
SCH3
C(CH3)3


2866
bond
NO2
SCH3
C(CH3)3


2867
bond
SCH3
SCH3
C(CH3)3


2868
bond
SO2CH3
SCH3
C(CH3)3


2869
bond
SO2CH2CH3
SCH3
C(CH3)3


2870
bond
CH3
SCH3
C(CH3)3


2871
bond
CF3
SCH3
C(CH3)3


2872
bond
OCHF2
SCH3
C(CH3)3


2873
CH2
F
SCH3
C(CH3)3


2874
CH2
Cl
SCH3
C(CH3)3


2875
CH2
Br
SCH3
C(CH3)3


2876
CH2
NO2
SCH3
C(CH3)3


2877
CH2
SCH3
SCH3
C(CH3)3


2878
CH2
SO2CH3
SCH3
C(CH3)3


2879
CH2
SO2CH2CH3
SCH3
C(CH3)3


2880
CH2
CH3
SCH3
C(CH3)3


2881
CH2
CF3
SCH3
C(CH3)3


2882
CH2
OCHF2
SCH3
C(CH3)3


2883
O
F
SCH3
C(CH3)3


2884
O
Cl
SCH3
C(CH3)3


2885
O
Br
SCH3
C(CH3)3


2886
O
NO2
SCH3
C(CH3)3


2887
O
SCH3
SCH3
C(CH3)3


2888
O
SO2CH3
SCH3
C(CH3)3


2889
O
SO2CH2CH3
SCH3
C(CH3)3


2890
O
CH3
SCH3
C(CH3)3


2891
O
CF3
SCH3
C(CH3)3


2892
O
OCHF2
SCH3
C(CH3)3


2893
S
F
SCH3
C(CH3)3


2894
S
Cl
SCH3
C(CH3)3


2895
S
Br
SCH3
C(CH3)3


2896
S
NO2
SCH3
C(CH3)3


2897
S
SCH3
SCH3
C(CH3)3


2898
S
SO2CH3
SCH3
C(CH3)3


2899
S
SO2CH2CH3
SCH3
C(CH3)3


2900
S
CH3
SCH3
C(CH3)3


2901
S
CF3
SCH3
C(CH3)3


2902
S
OCHF2
SCH3
C(CH3)3


2903
SO2
F
SCH3
C(CH3)3


2904
SO2
Cl
SCH3
C(CH3)3


2905
SO2
Br
SCH3
C(CH3)3


2906
SO2
NO2
SCH3
C(CH3)3


2907
SO2
SCH3
SCH3
C(CH3)3


2908
SO2
SO2CH3
SCH3
C(CH3)3


2909
SO2
SO2CH2CH3
SCH3
C(CH3)3


2910
SO2
CH3
SCH3
C(CH3)3


2911
SO2
CF3
SCH3
C(CH3)3


2912
SO2
OCHF2
SCH3
C(CH3)3


2913
bond
F
Cl
CH(CH3)2


2914
bond
Cl
Cl
CH(CH3)2


2915
bond
Br
Cl
CH(CH3)2


2916
bond
NO2
Cl
CH(CH3)2


2917
bond
SCH3
Cl
CH(CH3)2


2918
bond
SO2CH3
Cl
CH(CH3)2


2919
bond
SO2CH2CH3
Cl
CH(CH3)2


2920
bond
CH3
Cl
CH(CH3)2


2921
bond
CF3
Cl
CH(CH3)2


2922
bond
OCHF2
Cl
CH(CH3)2


2923
CH2
F
Cl
CH(CH3)2


2924
CH2
Cl
Cl
CH(CH3)2


2925
CH2
Br
Cl
CH(CH3)2


2926
CH2
NO2
Cl
CH(CH3)2


2927
CH2
SCH3
Cl
CH(CH3)2


2928
CH2
SO2CH3
Cl
CH(CH3)2


2929
CH2
SO2CH2CH3
Cl
CH(CH3)2


2930
CH2
CH3
Cl
CH(CH3)2


2931
CH2
CF3
Cl
CH(CH3)2


2932
CH2
OCHF2
Cl
CH(CH3)2


2933
O
F
Cl
CH(CH3)2


2934
O
Cl
Cl
CH(CH3)2


2935
O
Br
Cl
CH(CH3)2


2936
O
NO2
Cl
CH(CH3)2


2937
O
SCH3
Cl
CH(CH3)2


2938
O
SO2CH3
Cl
CH(CH3)2


2939
O
SO2CH2CH3
Cl
CH(CH3)2


2940
O
CH3
Cl
CH(CH3)2


2941
O
CF3
Cl
CH(CH3)2


2942
O
OCHF2
Cl
CH(CH3)2


2943
S
F
Cl
CH(CH3)2


2944
S
Cl
Cl
CH(CH3)2


2945
S
Br
Cl
CH(CH3)2


2946
S
NO2
Cl
CH(CH3)2


2947
S
SCH3
Cl
CH(CH3)2


2948
S
SO2CH3
Cl
CH(CH3)2


2949
S
SO2CH2CH3
Cl
CH(CH3)2


2950
S
CH3
Cl
CH(CH3)2


2951
S
CF3
Cl
CH(CH3)2


2952
S
OCHF2
Cl
CH(CH3)2


2953
SO2
F
Cl
CH(CH3)2


2954
SO2
Cl
Cl
CH(CH3)2


2955
SO2
Br
Cl
CH(CH3)2


2956
SO2
NO2
Cl
CH(CH3)2


2957
SO2
SCH3
Cl
CH(CH3)2


2958
SO2
SO2CH3
Cl
CH(CH3)2


2959
SO2
SO2CH2CH3
Cl
CH(CH3)2


2960
SO2
CH3
Cl
CH(CH3)2


2961
SO2
CF3
Cl
CH(CH3)2


2962
SO2
OCHF2
Cl
CH(CH3)2


2963
bond
F
Cl
C(CH3)3


2964
bond
Cl
Cl
C(CH3)3


2965
bond
Br
Cl
C(CH3)3


2966
bond
NO2
Cl
C(CH3)3


2967
bond
SCH3
Cl
C(CH3)3


2968
bond
SO2CH3
Cl
C(CH3)3


2969
bond
SO2CH2CH3
Cl
C(CH3)3


2970
bond
CH3
Cl
C(CH3)3


2971
bond
CF3
Cl
C(CH3)3


2972
bond
OCHF2
Cl
C(CH3)3


2973
CH2
F
Cl
C(CH3)3


2974
CH2
Cl
Cl
C(CH3)3


2975
CH2
Br
Cl
C(CH3)3


2976
CH2
NO2
Cl
C(CH3)3


2977
CH2
SCH3
Cl
C(CH3)3


2978
CH2
SO2CH3
Cl
C(CH3)3


2979
CH2
SO2CH2CH3
Cl
C(CH3)3


2980
CH2
CH3
Cl
C(CH3)3


2981
CH2
CF3
Cl
C(CH3)3


2982
CH2
OCHF2
Cl
C(CH3)3


2983
O
F
Cl
C(CH3)3


2984
O
Cl
Cl
C(CH3)3


2985
O
Br
Cl
C(CH3)3


2986
O
NO2
Cl
C(CH3)3


2987
O
SCH3
Cl
C(CH3)3


2988
O
SO2CH3
Cl
C(CH3)3


2989
O
SO2CH2CH3
Cl
C(CH3)3


2990
O
CH3
Cl
C(CH3)3


2991
O
CF3
Cl
C(CH3)3


2992
O
OCHF2
Cl
C(CH3)3


2993
S
F
Cl
C(CH3)3


2994
S
Cl
Cl
C(CH3)3


2995
S
Br
Cl
C(CH3)3


2996
S
NO2
Cl
C(CH3)3


2997
S
SCH3
Cl
C(CH3)3


2998
S
SO2CH3
Cl
C(CH3)3


2999
S
SO2CH2CH3
Cl
C(CH3)3


3000
S
CH3
Cl
C(CH3)3


3001
S
CF3
Cl
C(CH3)3


3002
S
OCHF2
Cl
C(CH3)3


3003
SO2
F
Cl
C(CH3)3


3004
SO2
Cl
Cl
C(CH3)3


3005
SO2
Br
Cl
C(CH3)3


3006
SO2
NO2
Cl
C(CH3)3


3007
SO2
SCH3
Cl
C(CH3)3


3008
SO2
SO2CH3
Cl
C(CH3)3


3009
SO2
SO2CH2CH3
Cl
C(CH3)3


3010
SO2
CH3
Cl
C(CH3)3


3011
SO2
CF3
Cl
C(CH3)3


3012
SO2
OCHF2
Cl
C(CH3)3









Very particular preference is also given to the compounds of the formula Ia2 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=1), in particular to the compounds Ia2.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia3 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=1), in particular to the compounds Ia3.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia4 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=2), in particular to the compounds Ia4.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia5 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=1), in particular to the compounds Ia5.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia6 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=2), in particular to the compounds Ia6.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia7 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia7.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia8 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=1), in particular to the compounds Ia8.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia9 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia9.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia10 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia10.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia11 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia11.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia12 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia12.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia13 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia13.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia14 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=1), in particular to the compounds Ia14.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia15 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=1), in particular to the compounds Ia15.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia16 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia16.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia17 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia17.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia18 (≡Ia where R1, R2, R5 and R12=H, R13=CH3, l=1), in particular to the compounds Ia18.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia19 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia19.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia20 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia20.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia21 (≡Ia where R1, R2, R5 and R12=H, l=0), in particular to the compounds Ia21.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




Very particular preference is also given to the compounds of the formula Ia22 (≡Ia where R1, R2, R5 and R12=H, R3=CH3, l=1), in particular to the compounds Ia22.n, where the variables X, R4, R10 and R11 are as defined in Table 1.




The tricyclic benzoylpyrazole derivatives of the formula I can be obtained by various routes, for example by one of the following processes:

    A. Preparation of compounds of the formula I where R10=halogen by reacting a tricyclic benzoylpyrazole derivative of the formula Iα (≡I where R10=hydroxyl) with a halogenating agent:






    
    
        Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N,N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide, etc.
        The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
        Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures of these. However, it is also possible to carry out the reaction in the absence of solvent.
        The reaction temperature is generally in the range from 0° C. to the boiling point of the reaction mixture.
        Work-up can be carried out in a manner known per se to afford the product.
    
    
    B. Preparation of compounds of the formula I where R10=OR13, by reacting a tricyclic benzoylpyrazole derivative of the formula Iα (≡I where R10=hydroxyl) with an alkylating agent III.






    
    
        L1 is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate, etc.
        The compounds of the formula III can be employed directly, such as, for example, in the case of the carbonyl halides, or be generated in situ, for example activated carboxylic acids (using carboxylic acid and dicyclohexylcarbodiimide etc.).
        The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
        If appropriate, it may also be advantageous to carry out the reaction in the presence of a base. Here, the reactants and the base are advantageously employed in equimolar amounts. In certain cases, an excess of base, for example from 1.5 to 3 molar equivalents, may be advantageous.
        Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, for example sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine or pyridine.
        Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.
        The reaction temperature is generally in the range from 0° C. to the boiling point of the reaction mixture.
        Work-up can be carried out in a manner known per se to afford the product.
    
    
    C. Preparation of compounds of the formula I where R10=OR13, SR13, NR15R16 or N-bonded heterocyclyl by reacting compounds of the formula Iβ (≡I where R10=halogen) with a compound of the formula IVα, IVβ, IVγ or IVδ, if appropriate in the presence of a base or with prior formation of salt.

















Iβ +
HOR13
IVα




or



HSR13
IVβ →
I (where R10 = OR13, SR13,



or

NR15R16 or N-bonded heterocyclyl)



HNR15R16
IVγ



or



H(N-bonded
IVδ



heterocyclyl)









    
    
        The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
        If appropriate, it may also be advantageous to carry out the reaction in the presence of a base. Here, the reactants and the base are advantageously employed in equimolar amounts. An excess of base, for example from 1.5 to 3 molar equivalents, based on Iβ (where R10=halogen), may be advantageous in certain cases.
        Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, for example sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, or alkali metal hydrides, for example sodium hydride. Preference is given to using sodium hydride or potassium tert-butoxide.
        Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures of these.
        The reaction temperature is generally in the range from 0° C. to the boiling point of the reaction mixture.
        Work-up can be carried out in a manner known per se to afford the product.
    
    
    D. Preparation of compounds of the formula I where R10 SO2R14 by reacting compounds of the formula I where R10=SR10 (Iγ) with an oxidizing agent.






    
    
        Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst, such as tungstate.
        The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.
        Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example, toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyltert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile or dimethylformamide, or esters, such as ethyl acetate, or mixtures of these.
        The reaction temperature is generally in the range from 0° C. to the boiling point of the reaction mixture.
        Work-up can be carried out in a manner known per se to afford the product.
    
    
    E. Preparation of compounds of the formula I where R9=IIa (where R10≠hydroxyl or mercapto) by reacting a metalated pyrazole derivative of the formula V with a tricyclic benzoic acid derivative of the formula VIα:






    
    
        Here, M is a metal, in particular an alkali metal, such as lithium or sodium, an alkaline earth metal, such as, for example, magnesium, or a transition metal, such as palladium, nickel, etc. and L2 is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, alkylsulfonate, such as mesylate, haloalkylsulfonate, such as triflate, or cyanide.
        The reaction is generally carried out at temperatures of from −100° C. to the reflux temperature of the reaction mixture. Suitable solvents are inert aprotic solvents, such as ethers, for example diethyl ether, tetrahydrofuran. The compounds of the formula VIα are generally employed in excess, but it may also be advantageous to employ them in equimolar amounts or in substoichiometric amounts. Work-up is carried out to afford the product.
        The metalated pyrazole derivatives of the formula V can be formed in a manner known per se by reacting pyrazoles which are halogenated in the 4-position with metals, such as lithium, sodium, magnesium, etc., or with organometallic compounds, such as, for example, butyllithium. However, it is also possible to metalate pyrazoles which are linked in the 4 position to hydrogen directly, for example with the abovementioned metals or organometallic compounds. The reactions are generally carried out in an inert aprotic solvent, preferably in ether, such as diethyl ether, tetrahydrofuran, etc. The reaction temperature is in the range from −100° C. to the boiling point of the reaction mixture. The compounds of the formula V are generally directly reacted further or generated in situ.
    
    
    F. Preparation of compounds of the formula Iα (═I where R10=hydroxyl) by reacting an activated tricyclic benzoic acid of the formula VIβ or a tricyclic benzoic acid VIγ, preferably activated in situ, with a pyrazole of the formula VII to give the acylation product, followed by rearrangement.






L3 is a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.
The activated tricyclic benzoic acid VIβ can be employed directly, such as in the case of the tricyclic benzoyl halides, or be generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.
If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. Here, the reactants and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on VI, may be advantageous in certain cases.
Suitable auxiliary bases are tertiary alkylamines, pyridine, or alkali metal carbonates. 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 or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.
If tricyclic benzoyl halides are employed as activated carboxylic acid components, it may be advantageous to cool the reaction mixture to 0–10° C. when adding this reaction partner. The mixture is subsequently stirred at 20–100° C., preferably at 25–50° C., until the reaction has gone to completion. Work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are suitable for this purpose are, in particular, methylene chloride, diethyl ether and ethyl acetate. The organic phase is dried and the solvent removed, and the crude ester can then be employed for the rearrangement without further purification.
The rearrangement of the esters VIII to give the compounds of the formula Iα is advantageously carried out at from 20 to 100° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.
Solvents which may be used are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.
Suitable bases are tertiary amines, such as triethylamine, aromatic amines, such as pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in equimolar amounts or in an up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in double the equimolar ratio, based on the ester.
Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the ester.
Work-up may be carried out in a manner known per se. The reaction mixture is, for example, acidified using dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5–10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, the extract being dried and concentrated.
However, it is also possible to generate the ester VIII in situ by reacting a pyrazole of the formula VII, or an alkali metal salt thereof, with a tricyclic benzene derivative of the formula IX in the presence of carbon monoxide, a catalyst and a base.




L4 is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfonate such as mesylate or triflate; preference is given to bromine or triflate.
If appropriate, the ester VIII reacts directly to give the tricyclic benzoylpyrazole derivative of the formula Iα.
Suitable catalysts are palladium ligand complexes in which the palladium is present in oxidation state 0, metallic palladium, if appropriate applied to a support, and preferably palladium(II) salts. The reaction with palladium(II) salts and metallic palladium is preferably carried out in the presence of complex ligands.
A suitable palladium(0) ligand complex is, for example, tetrakis(triphenylphosphane)palladium.
Metallic palladium is preferably applied to an inert carrier, such as, for example, activated carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands, such as, for example, triphenylphosphane.
Suitable palladium(II) salts are, for example, palladium acetate and palladium chloride. Preference is given to carrying out the reaction in the presence of complex ligands such as, for example, triphenylphosphane.
Suitable complex ligands for the palladium ligand complexes, or complex ligands in whose presence the reaction with metallic palladium or palladium(II) salts is preferably carried out are tertiary phosphanes whose structure is represented by the following formulae:




where n is a number from 1 to 4 and the radicals Ra to Rg are C1–C6-alkyl, aryl-C1–C2-alkyl or preferably aryl. Aryl is, for example, naphthyl and unsubstituted or substituted phenyl such as, for example, 2-tolyl and in particular unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per se starting from commercially available palladium salts, such as palladium chloride or palladium acetate, and the corresponding phosphanes, such as, for example, triphenylphosphane or 1,2-bis(diphenylphosphano)ethane. A large number of complexed palladium salts is also commercially available. Preferred palladium salts are [(R)-(+)-2,2′-bis(diphenylphosphano)-1,1′-binaphthyl]palladium (II) chloride, bis(triphenylphosphane)palladium(II)acetate and in particular bis(triphenylphosphane)palladium(II) chloride.
The palladium catalyst is generally employed in a concentration of from 0.05 to 5 mol %, and preferably of 1–3 mol %.
Suitable bases are tertiary amines, such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene and in particular triethylamine. Also suitable are alkali metal carbonates, such as sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable.
In general, from 2 to 4 molar equivalents, in particular 2 molar equivalents, of the alkali metal carbonate, and from 1 to 4 molar equivalents, in particular 2 molar equivalents, of the tertiary amine are employed, based on the tricyclic benzene derivative of the formula IX.
Suitable solvents are nitrites, such as benzonitrile and acetonitrile, amides, such as dimethylformamide, dimethylacetamide, tetra-C1–C4-alkylureas or N-methylpyrrolidone, and preferably ethers, such as tetrahydrofuran, methyl tert-butyl ether. Particular preference is given to using, as solvents, ethers such as 1,4-dioxane and dimethoxyethane.
The tricyclic benzoyl halides of the formula VIβ where L3=Cl, Br can be prepared in a manner known per se by reacting the tricyclic benzoic acids of the formula VIγ (≡VIb) with halogenating agents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl bromide.
In a known manner, the tricyclic benzoic acids of the formula VIγ (≡VIb) can be prepared by acidic or basic hydrolysis from the corresponding esters VIc.
Tricyclic benzoic acid derivatives of the formula VI




where:

    
    
        x is oxygen, sulfur, S═O, S(═O)2, CR6R7, NR8 or a bond;
        Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle which contains one to three identical or different heteroatoms selected from the following group:
         oxygen, sulfur or nitrogen;
        R1,R2,R6,R7 are hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R3 is halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R4 is nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)-aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
        R5 is hydrogen, C1–C6-alkyl or halogen;
        R8 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkylcarbonyl, formyl, C1–C6-alkoxycarbonyl, C1–C6-haloalkoxycarbonyl, C1–C6-alkylsulfonyl or C1–C6-haloalkylsulfonyl;
        l is 0, 1 or 2;
        R17 is hydroxyl or a radical which can be removed by hydrolysis;

are novel.

    
    


Examples of radicals which can be removed by hydrolysis are alkoxy, phenoxy, alkylthio and phenylthio radicals which can be unsubstituted or substituted, halides, heteroaryl radicals which are attached via nitrogen, amino and imino radicals which may be unsubstituted or substituted, etc.
Preference is given to tricyclic benzoyl halides VIa (VI where R17=halogen)




where the variables X, Y, R1 to R5 and l are as defined under formula VI and

Hal is halogen, in particular chloride or bromide.
Preference is also given to tricyclic benzoic acids of the formula VIb (VI where R17=hydroxyl; ≡VIγ),




where the variables X, Y, R1 to R5 and l are as defined under formula VI.

Preference is also given to tricyclic benzoic esters of the formula VIc (VI where R17=T=C1–C6-alkoxy),




where the variables X, Y, R1 to R5 and l are as defined under formula VI and

T is C1–C6-alkoxy.
With respect to the variables X, Y, R1 to R5 and l, the particularly preferred embodiments of the tricyclic benzoic acid derivatives of the formulae VI, VIa, VIb and VIc correspond to those of the tricyclic benzoylpyrazole derivatives of the formula I.
Particular preference is given to the compounds VI, VIa, VIb and VIc where Y together with the two carbons to which it is attached forms the following heterocycles:




Here, extraordinary preference is given to the compounds VI, VIa, VIb and VIc where

    
    
        R4 is nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-alkylsulfonyl; in particular C1–C6-alkylsulfonyl.
    
    


The tricyclic benzoic esters VIc can be obtained in different ways.
For example, benzoic esters of the formula X, which are prepared in a manner known per se (cf., for example, Chem. Pharm. Bull. 1985, 33 (8), 3336; Helv. Chim. Acta 1987, 70, 1326; J. Chem. Soc. Perkin Trans. 1972, 2019; J. Chem. Soc. Perkin Trans. 1991, 2763; Tetrahydron Asymmetry 1998, 9, 1137), can be cyclized to cyclic ketones of the formula XI (cf., for example, Chem. Ber. 1923, 56, 1819; J. Chem. Soc. Perkin 11991, 2763; J. Med. Chem. 1988, 31, 230; Tetrahedron 1987, 43, 4549; Synlett 1991, 6, 443; Chem. Pharm. Bull. 1985, 33 (8), 3336). Analogously to known processes (cf., for example, J. Heterocyclic Chem. 1976, 13, 545; J. Heterocyclic Chem. 1972, 9, 1341; J. Org. Chem. 1978, 43, 3015; J. Chem. Soc. Perkin Trans. 11978, 86; J. Org. Chem. 1986, 51, 2021), these can be converted into the tricyclic benzoic esters of the formula VIc.




Furthermore, it may be suitable to cyclize the cyclic ketone of the formula XI in a manner known per se (XII), for example using an anhydride or acid anhydride, if appropriate in the presence of catalytic amounts of a Lewis acid, such as boron trifluoride (cf., for example, Can. J. Chem. 1979, 57, 3292; J. Am. Chem. Soc. 1953, 75, 626), followed by reaction with a hydrazine (cf. A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry, Vol. 5, p. 121, 277–280 (1984), Pergamon Press; J. Org. Chem. 1961, 26, 451; Org. Synth. 1949, 29, 54), where the resulting pyrazole radical can be modified further by customary processes.
Furthermore, the diketone XII can be reacted with hydroxylamine or equivalents thereof (cf. A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry, Vol. 6, p. 61–64, 118 (1984), Pergamon Press; Chem. Ber. 1967, 100, 3326). This gives the corresponding isoxazole derivatives which can be modified further by customary processes.
It is also possible to react the diketone XII with amidines (cf., for example, A. R. Katritzky et al., Comprehensive Heterocyclic Chemistry, Vol. 3, p. 112–114 (1924), Pergamon Press; J. Chem. Soc. C 1967, 1922; Org. Synth. 1963, IV, 182). If required, the resulting pyrimidine derivatives can be modified further by customary processes.




In the reactions mentioned above, it is also possible to employ, instead of the diketone XII, equivalents thereof, such as enol ethers or enamines, which can be prepared analogously to known processes.
It may also be possible to react the cyclic ketone of the formula XI analogously to known processes with an aldehyde or ketone to give (XIII) (cf., for example, Tetrahedron Lett. 1978, 2111; Tetrahedron Lett. 1981, 5251; Chem. Ber. 1960, 2294; J. Chem. Soc. Perkin Trans. 1, 1991, 1467; Tetrahedron Lett. 1992, 8091). The resulting unsaturated cyclic ketone of the formula XIII can be reacted with a hydrazine in a manner known per se (cf., for example, A. R. Katritzky et al. Comprehensive Heterocyclic Chemistry, Vol. 2, 6 (1984), Pergamon Press; J. Heterocyclic Chem. 1969, 533; J. Heterocyclic Chem. 1968, 853), where the resulting pyrazoline can be modified further by customary processes.
It is furthermore possible to react the unsaturated cyclic ketone of the formula XIII with hydroxylamine or equivalents thereof (Z. Chem. 1980, 20, 19). This gives the corresponding isoxazoline derivatives, which can be modified further by customary processes.




Furthermore, it is possible to convert aldehydes of the formula XIV, which can be prepared in a manner known per se, analogously to processes known from the literature by reaction with a hydrazine or hydroxylamine (or equivalents of these) into the corresponding hydrazones or oximes (cf., for example, Synth. Commun. 1990, 20, 1373; J. Org. Chem. 1980, 45, 3756). These in turn can be converted in a manner known per se into the corresponding 1,3-dipoles, which then react in a [3+2]-cycloaddition to give the compounds VIc (cf., for example, Synth. Commun. 1990, 20, 1373; EP-A 386 892; J. Org. Chem. 1980, 45, 3756; Tetrahedron Lett. 1981, 22, 1333.)
The resulting pyrazoles or pyrazolines and isoxazoles or isoxazolines can be modified further by customary processes.




It is also possible to react the cyclic ketone of the formula XI with a dithiol or a “mixed alcohol” analogously to processes known from the literature (cf., for example, T. W. Greene et al., Protective Groups in Organic Synthesis, John Wiley & Sons, 133–140), and to subject it subsequently to a rearrangement in the presence of bromine or a suitable Lewis acid, such as, for example, tellurium tetrachloride (cf. Tetrahedron 1991, 47, 4187; Synthesis 1991, 223; J. Chem. Soc. Chem. Commun. 1985, 1645).




The resulting heterocycles can, if desired, be modified further by processes known per se.
The abovementioned substituents R3a are hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, hydroxyl, C1–C6-alkoxy or C1–C6-haloalkoxy; furthermore, the abovementioned radicals R3b are hydrogen, C1–C6-alkyl or C1–C6-haloalkyl.
The tricyclic benzoic esters of the formula VIc or the tricyclic benzoic acids of the formula VIb can be obtained by reacting a tricyclic benzene derivative of the formula IX with a C1–C6-alcohol or water in the presence of carbon monoxide, a catalyst and a base. In general, the conditions mentioned under process F apply.




L4 is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfate, such as mesylate or triflate; preference is given to bromine or triflate.
Furthermore, the tricyclic benzoic acids of the formula VIb can be obtained by converting a tricyclic benzene derivative of the formula IX where L4 is halogen, such as chlorine or bromine, in particular bromine, by reaction with, for example, n-butyllithium or magnesium into the metalated derivative, followed by quenching with carbon dioxide (cf., for example, J. Org. Chem. 1990, 55, 773; Angew. Chem. Int. Ed. 1969, 8, 68).




It is also possible to obtain the tricyclic benzoic acids VIb by hydrolyzing the corresponding nitriles, analogously to processes known from the literature. The nitriles for their part can be obtained by halogen/nitrile exchange or by Sandmeyer reaction from the corresponding anilines XV.




The compounds of the formula IX,
where:


    
    
        X is oxygen, sulfur, S═O, S(═O)2, CR6R7, NR8 or a bond;
        Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle which contains one to three identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen;
        R1,R2,R6,R7 are hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R3 is halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R4 is nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
        R5 is hydrogen, C1–C6-alkyl or halogen;
        R8 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkylcarbonyl, formyl, C1–C6-alkoxycarbonyl, C1–C6-haloalkoxycarbonyl, C1–C6-alkylsulfonyl or C1–C6-haloalkylsulfonyl;
        l is 0, 1 or 2;
        L4 is halogen, C1–C6-alkylsulfonyloxy, C1–C6-haloalkylsulfonyloxy or phenylsulfonyloxy, where the phenyl ring of the lastmentioned radical may be unsubstituted or partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;

are novel.

    
    


Preference is given to compounds of the formula IX where L4 is halogen, in particular bromine.
The particularly preferred embodiments of the compounds of the formula IX with respect to the variables X, Y, R1 to R5 and l correspond to those of the tricyclic benzoylpyrazole derivatives of the formula I.
Particular preference is given to the compounds of the formula IX where

    
    
        Y together with the two carbons to which it is attached forms the following heterocycles:
    
    






Here, extraordinary preference is given to the compounds IX where

    
    
        R4 is nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-alkylsulfonyl; in particular C1–C6-alkylsulfonyl.
    
    


The compounds of the formula IX can be obtained in different ways, the fused system, for example, can be constructed analogously to the processes described for the compounds of the formula VIc.
However, it is also possible to construct the fused system from a suitable parent compound (analogously to the processes described for compounds of the formula VIc) and to introduce L4=halogen subsequently by customary halogenating reactions.
The anilines of the formula XV and the nitrites of the formula XVI




where:

    
    
        X is oxygen, sulfur, S═O, S(═O)2, CR6R7, NR8 or a bond;
        Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle which contains one to three identical or different heteroatoms selected from the following group:
         oxygen, sulfur or nitrogen;
        R1,R2,R6,R7 are hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R3 is halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
        R4 is nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
        R5 is hydrogen, C1–C6-alkyl or halogen;
        R8 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkylcarbonyl, formyl, C1–C6-alkoxycarbonyl, C1–C6-haloalkoxycarbonyl, C1–C6-alkylsulfonyl or C1–C6-haloalkylsulfonyl;
        l is 0, 1 or 2;

are also novel.

    
    


The particularly preferred embodiments of the compounds of the formulae XV and XVI with respect to the variables X, Y, R1 to R5 and l correspond to those of the tricyclic benzoylpyrazole derivatives of the formula I.
Particular preference is given to the compounds of the formula XV or XVI where

    
    
        Y together with the two carbons to which it is attached forms the following heterocycles:
    
    






Here, extraordinary preference is given to the compounds XV or XVI where

    
    
        R4 is nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-alkylsulfonyl; in particular C1–C6-alkylsulfonyl.
    
    


The compounds of the formula XV can be obtained in different ways; for example, the fused system can be constructed analogously to the processes described for the compounds of the formula VIc.
However, it is also possible to construct the fused system from a suitable parent compound (analogously to the processes described for the compounds of the formula VIc) and to introduce a nitro group subsequently by nitration para to R4, analogously to processes known from the literature, and to convert this group in a manner known per se by reduction into the amino group.
If appropriate, it may be advantageous in the synthesis variants described above to introduce protective groups for certain functionalities if the functionalities are not compatible with the reaction conditions required.
The selection of the protective groups depends both on the reaction conditions and on the structure of the molecule. The protective groups, their introduction and their removal are generally known from the literature (cf., for example, T. W. Greene et al., “Protective Groups in Organic Synthesis”, 2nd edition, Wiley, New York, 1991), and they can be employed analogously to processes known from the literature.
Furthermore, it may be necessary to carry out a combination of the synthesis variants described above.
It is also possible to introduce further substituents or to modify the substituents present by electrophilic, nucleophilic, free-radical or organometallic reactions and by oxidation or reduction reactions.


PREPARATION EXAMPLES
1. (5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methyl-sulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.2)
2-Allyl-6-chlorobenzaldehyde
Under an atmosphere of protective gas, a solution of 10.89 g (0.107 mol) of trimethylethylenediamine in 50 ml of anhydrous tetrahydrofuran was cooled to −10° C. and admixed dropwise with 66.6 ml of a 1.6 molar solution of n-butyllithium in hexane (0.107 mol). After 10 minutes, 15 g (0.107 mol) of 6-chlorobenzaldehyde in 70 ml of tetrahydrofuran were added dropwise, and the mixture was admixed with a further 0.214 mol of n-butyllithium in hexane (146.8 ml) and stirred at 0° C. for 2.5 hours. The mixture was cooled to −200° C., 12.42 g (0.139 mol) of copper(I) cyanide were added, the mixture was stirred at −10° C. for 30 minutes, and 28.42 g of allyl bromide in 100 ml of tetrahydrofuran were then added dropwise. The mixture was stirred at 0° C. for another 2.5 hours, and 230 ml of saturated ammonium chloride solution were then added dropwise. The resulting solid was separated off and the aqueous phase was extracted with diethyl ether. The combined organic phases were then washed with saturated ammonium chloride solution and dried, and the solvent was removed under reduced pressure. This gave 17.0 g of 2-allyl-6-chlorobenzaldehyde (89%) in the form of a dark oil.
1H NMR (CDCl3, δ in ppm): 3.73 (d, 2H); 5.05 (dd, 2H); 5.96 (m, 1H); 7.05–7.48 (m, 3H); 10.58 (s, 1H).
2-Allyl-6-chlorobenzaldehyde oxime
5.58 g of sodium bicarbonate were added to a solution of 4.62 g of hydroxylamine hydrochloride in 50 ml of water, and the mixture was cooled to 0° C. A solution of 9.7 g (44.32 mmol) of 2-allyl-6-chlorobenzaldehyde in 50 ml of methanol was then added dropwise, and the mixture was stirred at room temperature overnight. The methanol was subsequently removed under reduced pressure and the residue was stirred into 300 ml of water. The aqueous phase was extracted with diethyl ether and the combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 8.7 g (quantitative) of 2-allyl-6-chlorobenzaldehyde oxime in the form of a viscous oil.
1H NMR (CDCl3, δ in ppm): 3.58 (d, 2H); 5.02 (2d, 2H); 5.95 (m, 1H); 7.08–7.36 (m, 3H); 8.49 (s, 1H).
8-Chloro-3a,4-dihydro-3H-indeno[1,2-c]isoxazole
At room temperature, 37.0 ml of a sodium hypochlorite solution (12.5% of active chlorine) were added dropwise to a solution of 8.4 g (42.9 mmol) of 2-allyl-6-chlorobenzaldehyde oxime in 100 ml of methylene chloride, and a spatula tip of sodium acetate was added. The mixture was stirred at room temperature for 2 hours, the organic phase was separated off, the aqueous phase was extracted with methylene chloride and the combined organic phases were washed with saturated ammonium chloride solution. The organic phase was dried and the solvent was removed. This gave 7.0 g (94%) of 8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in the form of a viscous oil.
1H NMR (CDCl3, δ in ppm): 2.81 (dd, 1H); 3.24 (dd, 1H); 3.78–4.03 (s, 2H); 4.78 (t, 1H); 7.23–7.41 (m, 3H).
8-Methylthio-3a,4-dihydro-3H-indeno[1,2c]isoxazole
At room temperature, 3.6 g (52.0 mmol) of sodium thiomethoxide were added to a solution of 5.0 g (25.8 mmol) of 8-chloro-3a,4-dihydro-3H-indeno-[1,2-c]isoxazole in 60 ml of N-methylpyrrolidone, and the mixture was stirred overnight. The mixture was subsequently stirred into 800 ml of water, the aqueous phase was extracted with diethyl ether, the combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 4.6 g (87%) of 8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole in the form of a dark brown solid.
1H NMR (CDCl3, δ in ppm): 2.54 (s, 3H); 2.78 (dd, 1H); 3.21 (dd, 1H); 3.72–3.93 (s, 2H); 4.64 (t, 1H); 7.09–7.38 (m, 3H).
5-Bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole
120 ml of sulfuric acid (98 percent strength) were cooled to 0° C., and 11.2 g (54.8 mmol) of 8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole were added a little at a time. 9.2 g (57.5 mmol) of bromine were then added dropwise, and stirring was continued at 0° C. for another 2 hours. The resulting solution was poured into 2 l of a mixture of water and ice, this mixture was stirred for 1.5 hours and the precipitated solid was filtered off with suction and then washed and dried. This gave 11.4 g (73%) of 5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole of a brown solid having a m.p. of 127–135° C.
1H NMR (CDCl3, δ in ppm): 2.53 (s, 3H); 2.71 (dd, 1H); 3.24 (dd, 1H); 3.81–4.02 (s, 2H); 4.71 (t, 1H); 7.01 (d, 1H); 7.47 (d, 1H).
5-Bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole
A solution of 11.2 g (39.4 mmol) of 5-bromo-8-methylthio-3a,4-dihydro-3H-indeno[1,2-c]isoxazole and 1.55 g of sodium tungstate in 250 ml of toluene and 50 ml of glacial acetic acid was heated to 70° C. and mixed dropwise with 10.73 g (39 percent strength, 86.8 mmol) of hydrogen peroxide. Stirring was continued at 70° C. for another 3 hours, and a solid precipitated out. The mixture was allowed to cool to room temperature and stirred into 1 l of water, and the white solid was filtered off with suction. The organic phase of the filtrate was separated off and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. This gave a viscous brown oil which was stirred with hexane/ethyl acetate (4:1). The resulting precipitate was filtered off with suction and combined with the solid obtained above. This gave 7.3 g (59%) of 5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole.
1H-NMR (d6-DMSO, δ in ppm): 2.93 (dd, 1H); 3.23 (dd, 1H); 3.41 (s, 3H); 3.94 (dd, 1H); 4.16 (m, 1H); 4.81 (t, 1H); 7.82 (d, 1H); 8.03 (d, 1H).
(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.1)
0.62 g (6.33 mmol) of 5-hydroxy-1-methylpyrazole, 1.75 g (12.66 mmol) of dry potassium carbonate, 1.28 g (12.67 mmol) of triethylamine and 0.22 g (0.30 mmol) of bis-(triphenylphosphane)palladium dichloride were added to a suspension of 2.0 g (6.33 mmol) of 5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole in 100 ml of dioxane. In a miniautoclave, a carbon monoxide pressure of 20 bar was applied, the mixture was stirred for 5 minutes and the autoclave was vented. This procedure was repeated 3 times. The autoclave was subsequently heated to 1300° C., a carbon monoxide pressure of 20 bar was applied once more and the mixture was stirred for 24 hours. After cooling and venting, the solvent was removed, and the residue was taken up in water, adjusted to pH 11 and washed with methylene chloride. The mixture was subsequently acidified to pH 4 using 10 percent strength hydrochloric acid and extracted with methylene chloride. The combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 0.58 g (25%) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazole)-methanone in the form of a dark oil.
1H NMR (CDCl3, δ in ppm): 3.03 (dd, 1H); 3.42 (s, 3H); 3.40 (m, 1H); 3.51 (s, 3H); 4.05 (m, 2H); 4.85 (t, 1H); 7.57 (s, 1H); 7.92 (d, 1H); 8.22 (d, 1H).
(5-Phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methyl-sulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone (compound 2.2)
Under an atmosphere of protective gas, 0.18 g of triethylamine and 0.26 g (1.82 mmol) of benzoyl chloride in 10 ml of tetrahydrofuran were added at 0° C. to a suspension of 0.55 g (1.52 mmol) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazol-5-yl)methanone in 10 ml of tetrahydrofuran. The mixture was stirred overnight at room temperature, the solvent was removed, the residue was taken up in ethyl acetate, washed with water and dried, and the solvent was removed. The crude product was purified by silica gel chromatography (mobile phase: ethyl acetate: hexane=1:1). This gave 0.22 g (31%) of (5-phenylcarbonyloxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone in the form of a yellow solid having a m.p. of 86–93° C.
1H NMR (CDCl3, δ in ppm): 3.22 (s, 3H); 3.34 (m, 2H); 3.81 (s, 3H); 3.98 (m, 2H); 4.81 (t, 1H); 7.20–8.21 (m, 8H).
2. 4-(2-Methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl) carbonyl-5-hydroxy-1-methyl-1H-pyrazole (compound 3.1)
Methyl 2-chlorosulfonyl-4-chlorobenzoate
At from 0 to 5° C., a solution of 60.9 g (0.88 mol) of sodium nitrite in 100 ml of water was added dropwise to a solution of 139 g (0.75 mol) of methyl 2-amino-4-chlorobenzoate in 400 ml of concentrated hydrochloric acid and the mixture was stirred at 0° C. for another hour.
In a second apparatus, 3 g of copper(II) chloride, 3 g of benzyltriethylammonium chloride, 10 ml of water and 400 ml of 1,2-dichloroethane were combined and 64 g (1 mol) of sulfur dioxide were introduced.
The diazonium salt described above was subsequently added at from 10 to 150° C., and the mixture was slowly heated to 50° C. A further 54 g (0.84 mol) of sulfur dioxide were then introduced, and stirring was continued at 500° C. for another 30 minutes. After cooling, 7.4 g (0.1 mol) of chlorine gas were then introduced at room temperature, stirring was continued for 15 minutes and the phases which had formed were then separated. The organic phase was dried and the solvent was removed. This gave 207 g of methyl 2-chlorosulfonyl-4-chlorobenzoate.
1H NMR (CDCl3, δ in ppm): 4.00 (s, 3H); 7.75 (m, 2H); 8.18 (m, 1H)
Methyl 2-mercapto-4-chlorobenzoate
Over a period of 1.5 hours, 243.5 g (3.7 mol) of zinc powder were added a little at a time to a suspension of 205 g (0.75 mol) of methyl 2-chlorosulfonyl-4-chlorobenzoate in 1 l of concentrated hydrochloric acid and 375 g of ice. The mixture was stirred for another 3 hours and slowly heated to 70° C. After 2 hours at this temperature, the mixture was cooled. The reaction mixture was allowed to stand at room temperature for 12 hours and then extracted with ethyl acetate, the combined organic phases were dried and the solvent was removed. This gave 125.4 g (83%) of methyl 2-mercapto-4-chlorobenzoate.
1H NMR (CDCl3, δ in ppm): 3.95 (s, 3H); 4.88 (s, 1H); 7.10 (m, 1H); 7.30 (m, 1H); 7.96 (d, 1H).
Methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate
179.5 g (1.3 mol) of potassium carbonate and, a little at a time, 94.5 g (0.62 mol) of 3-bromopropionic acid were added to a solution of 125.4 g (0.62 mol) of methyl 2-mercapto-4-chlorobenzoate in 1.5 l of acetone, and the reaction mixture was stirred at room temperature for 12 hours. The solvent was distilled off, the residue was taken up in water and the mixture was extracted with diethyl ether. The aqueous phase was then made acidic using concentrated hydrochloric acid, and the resulting precipitate was filtered off with suction and dried. This gave 150 g (88%) of methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate.
M.p.: 133 to 1360° C.
Methyl 5-chloro-4-oxothiochromane-8-carboxylate
At 70° C., 50 g (0.18 mol) of methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate were added to 500 g of polyphosphoric acid, and the mixture was stirred for a further 30 minutes. The reaction mixture was then stirred into water and the resulting precipitate was filtered off with suction and dried. This gave 41.1 g (88%) of methyl 5-chloro-4-oxothiochromane-8-carboxylate.
1H NMR (CDCl3, δ in ppm): 3.08 (m, 4H); 3.96 (s, 3H); 7.14 (d, 1H); 7.95 (d, 1H).
Methyl 5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate
30 g (0.078 mol) of methyl 5-chloro-4-oxothiochromane-8-carboxylate in 300 ml of N,N-dimethylformamide dimethyl acetal were refluxed for 6 hours. Volatile components were then distilled off, the residue was taken up in methylene chloride and the organic phase was washed with water. Drying and removal of the solvent gave 35.3 g (97%) of methyl 5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate.
1H NMR (CDCl3, δ in ppm): 3.18 (s, 6H); 3.80 (s, 2H); 3.95 (s, 3H); 7.24 (d, 1H); 7.64 (s, 1H); 7.82 (d, 1H).
2-Methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole
1.3 g (29.2 mmol) of methylhydrazine were added dropwise to a solution of 7.0 g (22.5 mmol) of methyl 5-chloro-3-(N,N-dimethylaminomethylidene)-4-oxothiochromane-8-carboxylate in 700 ml of ethanol, and the mixture was refluxed for 2 hours. The solvent was removed and the residue was chromatographed over silica gel using ethyl acetate/cyclohexane (2:3) as mobile phase. This gave 4.0 g (60%) of 2-methyl-6-methoxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole.
1H NMR (CDCl3, δ in ppm): 3.76 (s, 2H); 3.95 (s, 3H); 4.00 (s, 3H); 7.24 (s, 1H); 7.36 (d, 1H); 7.70 (d, 1H).
2-Methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]pyrazole
4.0 g (13.6 mmol) of 2-methyl-6-methoxycarbonyl-9-chloro-[l]-thiochromano[4,3-c]pyrazole in 100 ml of methanol/water (1:1) were refluxed with 0.8 g (20 mmol) of sodium hydroxide for 1 hour. The organic solvent was removed under reduced pressure and the residue was extracted with ethyl acetate. The aqueous phase was acidified using concentrated hydrochloric acid and the resulting precipitate was filtered off with suction and dried. This gave 3.5 g (92%) of 2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole
1H NMR (CDCl3, δ in ppm): 3.80 (s, 2H); 3.96 (s, 3H); 7.40 (d, 1H); 7.65 (m, 2H).
4-(2-Methyl-9-chloro-[l]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydroxy-1-methyl-1H-pyrazole (compound 3.1)
A mixture of 0.60 g (2.1 mmol) of 2-methyl-6-hydroxycarbonyl-9-chloro-[1]-thiochromano[4,3-c]-pyrazole and 0.21 g (2.1 mmol) of N,N-dicyclohexylcarbodiimide in 20 ml of acetonitrile was stirred at room temperature overnight. The mixture was admixed with in each case 500 ml of ethyl acetate and 2% strength sodium carbonate solution, the resulting precipitate was filtered off, the organic phase was dried and the solvent was removed. The residue was then refluxed with 0.59 g (4.3 mmol) of potassium carbonate in 5 ml of 1,4-dioxane for 3 hours. After cooling, the mixture was extracted with diethyl ether and the aqueous phase was acidified to pH 3. The resulting precipitate was filtered off with suction and dried. This gave 0.14 g of 4-(2-methyl-9-chloro-[1]-thiochromano[4,3-c]pyrazol-6-yl)-carbonyl-5-hydroxy-1-methyl-1H-pyrazole.
M.p.: 168–1710° C.
3. (5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone (compound 2.3)
Methyl 2-hydroxy-3-formyl-4-methoxybenzoate
At from 0 to 5° C., a solution of 209.0 g (1.1 mol) of titanium tetrachloride in 150 ml of methylene chloride was added dropwise to a solution of 50.1 g (0.275 mol) of methyl 2-hydroxy-4-methoxybenzoate and 88 g (0.725 mol) of dichloromethoxymethane in 400 ml of methylene chloride, and the mixture was stirred at room temperature overnight. The mixture was then stirred into ice-water and extracted with methylene chloride. The combined organic phases were washed with sodium bicarbonate solution, water and sodium chloride solution and dried, and the solvent was then removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:1 gave 24.5 g (42%) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in the form of a colorless solid of m.p.: 123–1240° C.
1H NMR (CDCl3, δ in ppm): 3.92 (s, 3H); 3.98 (s, 3H); 6.49 (d, 1H); 8.19 (d, 1H); 10.39 (s, 1H).
Methyl 2-allyloxy-3-formyl-4-methoxybenzoate
At room temperature, 23.2 g (0.192 mol) of allyl bromide were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and 20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 4 hours. The mixture was subsequently stirred into 1.5 l of 3% strength aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:2 gave 7.7 g (36%) of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.
1H NMR (CDCl3, δ in ppm): 3.86 (s, 3H); 3.93 (s, 3H); 4.58 (d, 2H); 5.32 (d, 1H); 5.39 (d, 1H); 6.15 (m, 1H); 6.79 (d, 1H); 8.04 (d, 1H); 10.41 (s, 1H).
6-Methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline
Step a)
At room temperature, 4.6 g (18.4 mmol) of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in 70 ml of methanol were added dropwise to a solution of 2.25 g (32.3 mmol) of hydroxylammonium chloride and 2.7 g of pyridine in 70 ml of water. The mixture was stirred at room temperature overnight, 150 ml of water were added, the mixture was extracted with methylene chloride, the combined organic phases were washed with 3% strength aqueous hydrochloric acid and dried, and the solvent was removed. The resulting oxime has a melting point of 126–1290° C.
Step b)
This oxime was reacted further without any further purification by dissolving it in 40 ml of methylene chloride, followed by dropwise addition of 15.0 ml (25.0 mmol) of sodium hypochlorite solution (12.5% of active chlorine). A spatula tip of sodium acetate was added and the mixture was stirred at room temperature for 12 hours. The organic phase was separated off, the aqueous phase was extracted with methylene chloride, the combined organic phases were washed with water and dried, and the solvent was removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:1 gave 2.2 g (49%) of 6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline in the form of a colorless solid of m.p: 199–203° C.
1H NMR (CDCl3, δ in ppm): 3.84 (s, 3H); 3.98 (s, 3H); 3.8–4.0 (m, 2H); 4.16 (dt, 1H); 4.63 (t, 1H); 4.84 (dd, 1H); 6.61 (d, 1H); 7.93 (d, 1H).
6-Methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline
At room temperature, a solution of 0.8 g (20.0 mmol) of sodium hydroxide in 7 ml of water was added dropwise to a solution of 2.1 g (8.0 mmol) of 6-methoxy-9-methoxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline in 40 ml of methanol, and the mixture was refluxed for 6 hours. After cooling, the solvent was removed and the residue was taken up in about 50 ml of water and washed with methylene chloride. The aqueous phase was subsequently acidified using 10% strength hydrochloric acid (pH=1–2), and the precipitate was filtered off with suction, washed with water and dried at 600° C. This gave 1.7 g (86%) of 6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline in the form of colorless crystals.
1H NMR (CDCl3, δ in ppm): 3.73 (dd, 1H); 3.89 (s, 3H); 3.84–3.95 (m, 1H); 4.11 (dd, 1H); 4.54 (dd, 1H); 4.79 (dd, 1H); 6.61 (d, 1H); 7.81 (d, 1H).
(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone (compound 2.3)
Step a)
At room temperature, 0.26 g (2.2 mmol) of thionyl chloride and a drop of dimethylformamide were added to a solution of 0.50 g (2.0 mmol) of 6-methoxy-9-hydroxycarbonyl-3a,4-dihydro-3H-chromeno[(4,3-c)]isoxazoline in 30 ml of carbon tetrachloride, and the mixture was stirred at 40–50° C. for 3 hours. The solvent was subsequently removed under reduced pressure. This gave, in quantitative yield, 6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c] isoxazoline (0.54 g) as a brownish oil.
Step b)
0.54 g (2 mmol) of 6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazoline was dissolved in 30 ml of acetonitrile and, at 0° C., added dropwise to a solution of 0.2 g (2.0 mmol) of 1-methyl-5-hydroxypyrazole and 0.6 g (6.0 mmol) of triethylamine in 20 ml of acetonitrile. The mixture was stirred at room temperature overnight, the solvent was removed, and the residue was taken up in methylene chloride and washed with water. The solution was dried and the solvent was distilled off. The residue was dissolved in 30 ml of dioxane and admixed with 0.42 g (3.0 mmol) of potassium carbonate, and the mixture was refluxed for 7 hours. After cooling, the solvent was distilled off under reduced pressure, the residue was taken up in water and the solution was adjusted to pH=1 using 10% strength hydrochloric acid. The solution was extracted with methylene chloride, the combined organic phases were dried and the solvent was subsequently removed. This gave 0.45 g (68%) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl)methanone of m.p. 236–238° C.
1H NMR (CDCl3, δ in ppm): 3.66 (s, 3H); 3.84–4.2 (m, 2H); 4.02 (s, 3H); 4.12 (dd, 1H); 4.63–4.77 (m, 2H); 6.68 (d, 1H); 7.24 (s, 1H); 7.61 (d, 1H).
4. [5-Hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanone (compound 2.4)
0.54 g (2 mmol) of 6-methoxy-9-chloroformyl-3a,4-dihydro-3H-chromeno[4,3-c]-isoxazoline was dissolved in 30 ml of acetonitrile and, at 0° C., added dropwise to a solution of 0.28 g (2.0 mmol) of 1-(1,1-dimethyleth-1-yl)-5-hydroxy-1H-pyrazole and 0.6 g (6.0 mmol) of triethylamine in 20 ml of acetonitrile. The mixture was stirred at room temperature overnight, the solvent was removed, and the residue was taken up in methylene chloride and washed with water. The solution was dried, and the solvent was distilled off. The residue was dissolved in 30 ml of dioxane and admixed with 0.42 g (3.0 mmol) of potassium carbonate, and the mixture was refluxed for 7 hours. After cooling, the solvent was distilled off under reduced pressure, the residue was taken up in water and the solution was adjusted to pH=1 using 10% strength hydrochloric acid. The solution was extracted with methylene chloride, the combined organic phases were dried, and the solvent was subsequently removed. This gave 0.3 g (40%) of [5-hydroxy-1-(1,1-dimethyleth-1-yl)-1H-pyrazol-4-yl]-[6-methoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazolin-9-yl]methanone having a melting point of 223° C.–2250° C.
1H NMR (CDCl3, δ in ppm): 1.64 (s, 9H); 3.8–4.2 (m, 6H); 4.6–4.8 (m, 2H); 6.68 (d, 1H); 7.44 (s, 1H); 7.62 (d, 1H).
In addition to the compounds above, other tricyclic benzoylpyrazole derivatives of the formula I which were prepared or are preparable in a similar manner are listed in Tables 2 to







TABLE 2













 


Ia where 1 = 0, R5 = H,


Y together with the two carbons


to which it is attached forms the


following isoxazoline:


 








 



















physical data








(m.p.[° C.];








1H NMR


No.
X
R4
R10
R11
R12
[ppm])





2.1
Bond
SO2CH3
OH
CH3
H
3.03(dd, 1H);








3.42(s, 3H);








3.51(s, 3H);








4.05(m, 2H);








4.85(t, 1H);








7.57(s, 1H);








7.92(d, 1H);








8.22(d, 1H)


2.2
Bond
SO2CH3
OCOC6H5
CH3
H
3.22(s, 3H);








3.34(m, 2H);








3.81(s, 3H);








3.98(m, 2H);








4.81(t, 1H);








7.20–8.21(m,








8H);


2.3
O
OCH3
OH
CH3
H
236–238


2.4
O
OCH3
OH
C(CH3)3
H
223–225


2.5
O
OCH3
OCO(3-
CH3
H
oil





F—C6H4)
















TABLE 3













 


Ia where R5 = H,


Y together with the two carbons to which


it is attached forms the following


methyl-substituted pyrazole:


 








 













No.
X
R4
R10
R11
R12
physical data (m.p.[° C.])





3.1
S
Cl
OH
CH3
H
168–171


3.2
S
Cl
OH
CH2CH3
H
115


3.3
S
SCH3
OH
CH3
H
245


3.4
S
SCH3
OH
CH2CH3
H
222
















TABLE 4













 


Ia where R5 = H,


Y together with the two carbons to which


it is attached forms the following


methyl-substituted pyrimidine:


 








 



















physical data


No.
X
R4
R10
R11
R12
(m.p.[° C.]; 1H NMR [ppm])





4.1
S
Cl
OH
CH3
H
180° C.


4.2
S
Cl
OH
CH2CH3
H
112° C.
















TABLE 5













 



















physical data


Nr.
X
R4
R10
R11
R12
(m.p.[° C.]; 1H NMR [ppm])





5.1
O
SCH3
OH
CH3
H
201









The compounds of the formula I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
Depending on the application method in question, the compounds of the formula I, or herbicidal compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:
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. 
In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.
The compounds of the formula I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading or watering. The use forms depend on the intended purpose; in any case, they should guarantee the finest possible distribution of the active compounds according to the invention.
The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries which are customarily used for formulating crop protection agents.
Suitable for use as inert auxiliaries are essentially the following:
mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal-tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the tricyclic benzoylpyrazole derivatives of the formula I, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or 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, lignin-sulfite waste liquors or methylcellulose.
Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active compounds together with a solid carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds 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 and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise approximately from 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
The following formulation examples illustrate the preparation of such formulations:

    I. 20 parts by weight of the compound No. 2.2 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of from 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
    II. 20 parts by weight of the compound No. 3.1 are dissolved in a mixture composed 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 to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
    III. 20 parts by weight of the compound No. 2.3 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
    IV. 20 parts by weight of the compound No. 2.4 are mixed thoroughly with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.
    V. 3 parts by weight of the compound No. 2.3 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active compound.
    VI. 20 parts by weight of the compound No. 2.4 are mixed intimately with 2 parts by weight of 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. This gives a stable oily dispersion.
    VII. 1 part by weight of the compound No. 2.2 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.
    VIII. 1 part by weight of the compound No. 3.1 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.


The compounds of the formula I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
The rates of application of the compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
To widen the spectrum of action and to achieve synergistic effects, the tricyclic benzylpyrazole derivatives of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy-/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
It may furthermore be advantageous to apply the compounds of the formula I, alone or in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.
Use Examples
The herbicidal activity of the tricyclic benzylpyrazole derivatives of the formula I was demonstrated by the following greenhouse experiments:
The culture containers used were plastic pots 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 pre-emergence treatment, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing 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 post-emergence treatment, the test plants were first grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. For this purpose, the test plants were 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 post-emergence treatment was 0.5 or 0.25 kg of a.s./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 trials were of the following species:














Scientific Name
Common Name









Chenopodium album
lambsquarters (goosefoot)



Echinochloa crusgalli
barnyardgrass



Setaria viridis
green foxtail



Solanum nigrum
black nightshade



Veronica ssp.
speadwell










At application rates of 0.5 or 0.25 kg/ha, the compound 2.2 shows very good activity against the abovementioned undesired broad-leaved weeds and weed grasses when applied by the post-emergence method.

## Claims

1. A tricyclic benzoylpyrazole compound of formula I



where:
X is a bond;
Y together with the two carbons to which it is attached forms a 1,2-isoxazole ring which is saturated, partially saturated or unsaturated;
R1, R2, R6, R7 are hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
R3 is halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
R4 is hydrogen, nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
R5 is hydrogen, C1–C6-alkyl or halogen;
R8 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkylcarbonyl, formyl, C1–C6-alkoxycarbonyl, C1–C6-haloalkoxycarbonyl, C1–C6-alkylsulfonyl or C1–C6-haloalkylsulfonyl;
l is 0, 1 or 2;
R9 is a radical IIa




 where
R10 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14, NR15R16 or N-bonded heterocyclyl, where the heterocyclyl radical may be partially or fully halogenated and/or may carry one to three of the following radicals:
 nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
R11 is hydrogen, C1–C6-alkyl, C1–C6-haloalkyl, C3–C6-cycloalkyl, hydroxyl, C1–C6-alkoxy or C1–C6-haloalkoxy;
R12 is hydrogen, halogen, C1–C6-alkyl, C1–C6-haloalkyl, hydroxyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio or C1–C6-haloalkylthio;
R13 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, C1–C20-alkylcarbonyl, C2–C20-alkenylcarbonyl, C2–C6-alkynylcarbonyl, C3–C6-Cycloalkylcarbonyl, C1–C6-alkoxycarbonyl, C3–C6-alkenyloxycarbonyl, C3–C6-alkynyloxycarbonyl, C1–C6-alkylthiocarbonyl, C1–C6-alkylaminocarbonyl, C3–C6-alkenylaminocarbonyl, C3–C6-alkynylaminocarbonyl, N,N-di(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkyl)aminocarbonyl, N-(C1–C6-alkoxy)-N-(C1–C6-alkyl)aminocarbonyl, N-(C3–C6-alkenyl)-N-(C1–C6-alkoxy)aminocarbonyl, N-(C3–C6-alkynyl)-N-(C1–C6-alkoxy)aminocarbonyl, di(C1–C6-alkyl)aminothiocarbonyl, C1–C6-alkylcarbonyl-C1–C6-alkyl, C1–C6-alkoxyimino-C1–C6-alkyl, N-(C1–C6-alkylamino)imino-C1–C6-alkyl or N,N-di(C1–C6-alkylamino)imino-C1–C6-alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
 cyano, C1–C4-alkoxy, C1–C4-alkylthio, di(C1–C4-alkyl)amino, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, C1–C4-alkoxy-C1–C4-alkoxycarbonyl, di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
 is phenyl, heterocyclyl, phenyl-C1–C6-alkyl, heterocyclyl-C1–C6-alkyl, phenylcarbonyl-C1–C6-alkyl, heterocyclylcarbonyl-C1–C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenylaminocarbonyl, N-(C1–C6-alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl, N-(C1–C6-alkyl)-N-(heterocyclyl)aminocarbonyl, phenyl-C2–C6-alkenylcarbonyl or heterocyclyl-C2–C6-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
 nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy, C1–C4-haloalkoxy, heterocyclyl or N-bonded heterocyclyl, where the two lastmentioned substituents for their part may be partially or fully halogenated and/or may carry one to three of the following radicals:
 nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
R14 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, C1–C6-alkoxy, di(C1–C6-alkyl)amino or di(C1–C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
 cyano, C1–C4-alkoxy, C1–C4-alkylthio, di(C1–C4-alkyl)amino, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, C1–C4-alkoxy-C1–C4-alkoxycarbonyl, di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
 is phenyl, heterocyclyl, phenyl-C1–C6-alkyl, heterocyclyl-C1–C6-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
 nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
R15 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, C1–C6-alkoxy, C3–C6-alkenyloxy, C3–C6-alkynyloxy, di(C1–C6-alkyl)amino or C1–C6-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals of the following group:
 cyano, C1–C4-alkoxy, C1–C4-alkylthio, di(C1–C4-alkyl)amino, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, C1–C4-alkoxy-C1–C4-alkoxycarbonyl, di(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
 is phenyl, heterocyclyl, phenyl-C1–C6-alkyl or heterocyclyl-C1–C6-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
 nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
R16 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-alkynyl or C1–C6-alkylcarbonyl;

or an agriculturally useful salt thereof.

2. The tricyclic benzoylpyrazole compound of formula I defined in claim 1 where
R1, R2 are hydrogen;
R3 is C1–C6-alkyl;
R4 is nitro, halogen, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-alkylthio or C1–C6-alkylsulfonyl;
R5 is hydrogen;
l is 0 or 1.

3. The tricyclic benzoylpyrazole compound of formula I defined in claim 1 where
R10 is hydroxyl;
R11 is C1–C6-alkyl or C3–C6-cycloalkyl;
R12 is hydrogen or C1–C6-alkyl.

4. A process for preparing the compound of formula I where R10=halogen as claimed in claim 1, which comprises reacting a tricyclic benzoylpyrazole compound of formula Iα (=I where R10=hydroxyl),




where the variables R1 to R3, R11 and R12, X, Y and l are as defined in claim 1, with a halogenating agent.

5. A process for preparing the compound of formula I where R10=OR13 as claimed in claim 1, which comprises reacting a tricyclic benzoylpyrazole compound of formula Iα (=I where R10=hydroxyl),




where the variables R1 to R5, R11 and R12, X, Y and l are as defined in claim 1, with a compound of formula III


L1—R13  III


where the variable R13 is as defined in claim 1 and L1 is a nucleophilically replaceable leaving group.

6. A process for preparing the compound of formula I where R10=OR13, SR13, NR15R16 or N-bonded heterocyclyl as claimed in claim 1, which comprises reacting a compound of formula Iβ (≡I where R10=halogen),




where the variables R1 to R5, R11 and R12, X, Y and l are as defined in claim 1, with a compound of formula IVα, IVβ, IVγ or IVδ
















HOR13
HSR13
NHR15R16
H(N-bonded heterocyclyl)









IVα
IVβ
IVγ
IVδ










where the variables R13 to R16 are as defined in claim 1, optionally in the presence of a base.

7. A process for preparing the compound of formula I where R10=SO2R14 as claimed in claim 1, which comprises reacting a compound of formula Iγ (≡I where R10=SR14),




where the variables R1 to R5, R11 and R12, X, Y and l are as defined in claim 1, with an oxidizing agent.

8. A process for preparing the compound of formula I as claimed in claim 1, which comprises reacting a metalated pyrazole compound of formula V where M is a metal and R10 to R12 are as defined in claim 1, except for R10=hydroxyl and mercapto, with a tricyclic benzoic acid compound of formula VIα where R1 to R5, X, Y and l are as defined in claim 1 and L2 is a nucleophilically replaceable leaving group

9. A process for preparing the compound of formula Iα (=I where R10=hydroxyl) as claimed in claim 1, which comprises acylating a pyrazole of formula VII in which the variables R11 and R12 are as defined in claim 1




with an activated tricyclic benzoic acid of formula VIβ or with a tricyclic benzoic acid of formula VIγ,




where the variables R1 to R5, X, Y and l are as defined in claim 1 and L3 is a nucleophilically replaceable leaving group, and rearranging the acylation product, optionally in the presence of a catalyst.

10. A process for preparing the compound of formula Iα (≡I where R10=hydroxyl) as claimed in claim 1, which comprises reacting a pyrazole of formula VII in which the variables R11 and R12 are as defined in claim 1, or an alkali metal salt thereof,




with a tricyclic benzene compound of formula IX where L4 is a leaving group and the variables X, Y, R1 to R5 and l are as defined in claim 1




in the presence of carbon monoxide, a catalyst and a base.

11. A composition, comprising a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof as claimed in claim 1 and auxiliaries which are customary for formulating crop protection agents.

12. A process for preparing the composition defined in claim 11, which comprises mixing a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof and auxiliaries which are customary for formulating crop protection agents.

13. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof as claimed in claim 1 to act on plants, their habitat or on seed.

14. A tricyclic benzoic acid compound of formula VI




in which the variables X, Y, R1 to R3 and R5 and l are as defined in claim 1 and
R4 is nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
R17 is hydroxyl or a radical which can be removed by hydrolysis.

15. A tricyclic benzene compound of formula IX




in which the variables X, Y, R1 to R3 and R5 and l are as defined in claim 1 and
R4 is nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
R5 is hydrogen or C1–C6-alkyl;
L4 is halogen, C1–C6-alkylsulfonyloxy, C1–C6-haloalkylsulfonyloxy or phenylsulfonyloxy, where the phenyl ring of the lastmentioned radical may be unsubstituted or partially or fully halogenated and/or may carry one to three of the following radicals:
 nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy.

16. An aniline compound of formula XV



in which the variables X, Y, R1 to R3 and R5 and l are in each case as defined in claim 1 and

R4 is nitro, halogen, cyano, C1–C6-haloalkyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino.

17. A nitrile compound of formula XVI




in which the variables X, Y, R1 to R3 and l are in each case as defined in claim 1 and
R4 is nitro, halogen, cyano, C1–C6-haloalkyl, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkinylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N-(C1–C6-alkyl)aminosulfonyl, N,N-di-(C1–C6-alkyl)aminosulfonyl, N-(C1–C6-alkylsulfonyl)amino, N-(C1–C6-haloalkylsulfonyl)amino, N-(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino or N-(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino;
R5 is hydrogen or C1–C6-alkyl.

18. The compound of formula I defined in claim 1, wherein R10 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14 or NR15R16.