TRICYCLIC BENZOYLPYRAZOLE DERIVATIVES

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; R1, R2, R6, R7 are hydrogen, alkyl, haloalkyl, alkoxy or haloalkoxy; R3 is halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; R4 is hydrogen, nitro, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, unsubstituted or substituted aminosulfonyl or unsubstituted or substituted sulfonylamino; R5 is hydrogen, alkyl or halogen; l is 0, 1 or 2; R8 is hydrogen, alkyl, haloalkyl, alkylcarbonyl, formyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylsulfonyl or haloalkylsulfonyl; R9 is substituted pyrazol-4-ylcarbonyl or substituted 5-oxopyrazolin-4-ylmethylidene; 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.

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Description

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-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 substitutents 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 substitutents 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 above-mentioned 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 substitutents 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 substitutents 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 substitutents 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 substitutents 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-phenyl, 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 above-mentioned 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 substitutents.

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 substitutents 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 substitutents 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 substitutents 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 1a 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 1a 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-alkylsulfonyl;
    • 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 Ia1 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 1013 CH2 Br OH CH(CH3)2 1014 CH2 NO2 OH CH(CH3)2 1015 CH2 SCH3 OH CH(CH3)2 1016 CH2 SO2CH3 OH CH(CH3)2 1017 CH2 SO2CH2CH3 OH CH(CH3)2 1018 CH2 CH3 OH CH(CH3)2 1019 CH2 CF3 OH CH(CH3)2 1020 CH2 OCHF2 OH CH(CH3)2 1021 O F OH CH(CH3)2 1022 O Cl OH CH(CH3)2 1023 O Br OH CH(CH3)2 1024 O NO2 OH CH(CH3)2 1025 O SCH3 OH CH(CH3)2 1026 O SO2CH3 OH CH(CH3)2 1027 O SO2CH2CH3 OH CH(CH3)2 1028 O CH3 OH CH(CH3)2 1029 O CF3 OH CH(CH3)2 1030 O OCHF2 OH CH(CH3)2 1031 S F OH CH(CH3)2 1032 S Cl OH CH(CH3)2 1033 S Br OH CH(CH3)2 1034 S NO2 OH CH(CH3)2 1035 S SCH3 OH CH(CH3)2 1036 S SO2CH3 OH CH(CH3)2 1037 S SO2CH2CH3 OH CH(CH3)2 1038 S CH3 OH CH(CH3)2 1039 S CF3 OH CH(CH3)2 1040 S OCHF2 OH CH(CH3)2 1041 SO2 F OH CH(CH3)2 1042 SO2 Cl OH CH(CH3)2 1043 SO2 Br OH CH(CH3)2 1044 SO2 NO2 OH CH(CH3)2 1045 SO2 SCH3 OH CH(CH3)2 1046 SO2 SO2CH3 OH CH(CH3)2 1047 SO2 SO2CH2CH3 OH CH(CH3)2 1048 SO2 CH3 OH CH(CH3)2 1049 SO2 CF3 OH CH(CH3)2 1050 SO2 OCHF2 OH CH(CH3)2 1051 bond F OH C(CH3)3 1052 bond Cl OH C(CH3)3 1053 bond Br OH C(CH3)3 1054 bond NO2 OH C(CH3)3 1055 bond SCH3 OH C(CH3)3 1056 bond SO2CH3 OH C(CH3)3 1057 bond SO2CH2CH3 OH C(CH3)3 1058 bond CH3 OH C(CH3)3 1059 bond CF3 OH C(CH3)3 1060 bond OCHF2 OH C(CH3)3 1061 CH2 F OH C(CH3)3 1062 CH2 Cl OH C(CH3)3 1063 CH2 Br OH C(CH3)3 1064 CH2 NO2 OH C(CH3)3 1065 CH2 SCH3 OH C(CH3)3 1066 CH2 SO2CH3 OH C(CH3)3 1067 CH2 SO2CH2CH3 OH C(CH3)3 1068 CH2 CH3 OH C(CH3)3 1069 CH2 CF3 OH C(CH3)3 1070 CH2 OCHF2 OH C(CH3)3 1071 O F OH C(CH3)3 1072 O Cl OH C(CH3)3 1073 O Br OH C(CH3)3 1074 O NO2 OH C(CH3)3 1075 O SCH3 OH C(CH3)3 1076 O SO2CH3 OH C(CH3)3 1077 O SO2CH2CH3 OH C(CH3)3 1078 O CH3 OH C(CH3)3 1079 O CF3 OH C(CH3)3 1080 O OCHF2 OH C(CH3)3 1081 S F OH C(CH3)3 1082 S Cl OH C(CH3)3 1083 S Br OH C(CH3)3 1084 S NO2 OH C(CH3)3 1085 S SCH3 OH C(CH3)3 1086 S SO2CH3 OH C(CH3)3 1087 S SO2CH2CH3 OH C(CH3)3 1088 S CH3 OH C(CH3)3 1089 S CF3 OH C(CH3)3 1090 S OCHF2 OH C(CH3)3 1091 SO2 F OH C(CH3)3 1092 SO2 Cl OH C(CH3)3 1093 SO2 Br OH C(CH3)3 1094 SO2 NO2 OH C(CH3)3 1095 SO2 SCH3 OH C(CH3)3 1096 SO2 SO2CH3 OH C(CH3)3 1097 SO2 SO2CH2CH3 OH C(CH3)3 1098 SO2 CH3 OH C(CH3)3 1099 SO2 CF3 OH C(CH3)3 1100 SO2 OCHF2 OH C(CH3)3 1101 bond F OCOC6H5 CH(CH3)2 1102 bond Cl OCOC6H5 CH(CH3)2 1103 bond Br OCOC6H5 CH(CH3)2 1104 bond NO2 OCOC6H5 CH(CH3)2 1105 bond SCH3 OCOC6H5 CH(CH3)2 1106 bond SO2CH3 OCOC6H5 CH(CH3)2 1107 bond SO2CH2CH3 OCOC6H5 CH(CH3)2 1108 bond CH3 OCOC6H5 CH(CH3)2 1109 bond CF3 OCOC6H5 CH(CH3)2 1110 bond OCHF2 OCOC6H5 CH(CH3)2 1111 CH2 F OCOC6H5 CH(CH3)2 1112 CH2 Cl OCOC6H5 CH(CH3)2 1113 CH2 Br OCOC6H5 CH(CH3)2 1114 CH2 NO2 OCOC6H5 CH(CH3)2 1115 CH2 SCH3 OCOC6H5 CH(CH3)2 1116 CH2 SO2CH3 OCOC6H5 CH(CH3)2 1117 CH2 SO2CH2CH3 OCOC6H5 CH(CH3)2 1118 CH2 CH3 OCOC6H5 CH(CH3)2 1119 CH2 CF3 OCOC6H5 CH(CH3)2 1120 CH2 OCHF2 OCOC6H5 CH(CH3)2 1121 O F OCOC6H5 CH(CH3)2 1122 O Cl OCOC6H5 CH(CH3)2 1123 O Br OCOC6H5 CH(CH3)2 1124 O NO2 OCOC6H5 CH(CH3)2 1125 O SCH3 OCOC6H5 CH(CH3)2 1126 O SO2CH3 OCOC6H5 CH(CH3)2 1127 O SO2CH2CH3 OCOC6H5 CH(CH3)2 1128 O CH3 OCOC6H5 CH(CH3)2 1129 O CF3 OCOC6H5 CH(CH3)2 1130 O OCHF2 OCOC6H5 CH(CH3)2 1131 S F OCOC6H5 CH(CH3)2 1132 S Cl OCOC6H5 CH(CH3)2 1133 S Br OCOC6H5 CH(CH3)2 1134 S NO2 OCOC6H5 CH(CH3)2 1135 S SCH3 OCOC6H5 CH(CH3)2 1136 S SO2CH3 OCOC6H5 CH(CH3)2 1137 S SO2CH2CH3 OCOC6H5 CH(CH3)2 1138 S CH3 OCOC6H5 CH(CH3)2 1139 S CF3 OCOC6H5 CH(CH3)2 1140 S OCHF2 OCOC6H5 CH(CH3)2 1141 SO2 F OCOC6H5 CH(CH3)2 1142 SO2 Cl OCOC6H5 CH(CH3)2 1143 SO2 Br OCOC6H5 CH(CH3)2 1144 SO2 NO2 OCOC6H5 CH(CH3)2 1145 SO2 SCH3 OCOC6H5 CH(CH3)2 1146 SO2 SO2CH3 OCOC6H5 CH(CH3)2 1147 SO2 SO2CH2CH3 OCOC6H5 CH(CH3)2 1148 SO2 CH3 OCOC6H5 CH(CH3)2 1149 SO2 CF3 OCOC6H5 CH(CH3)2 1150 SO2 OCHF2 OCOC6H5 CH(CH3)2 1151 bond F OCOC6H5 C(CH3)3 1152 bond Cl OCOC6H5 C(CH3)3 1153 bond Br OCOC6H5 C(CH3)3 1154 bond NO2 OCOC6H5 C(CH3)3 1155 bond SCH3 OCOC6H5 C(CH3)3 1156 bond SO2CH3 OCOC6H5 C(CH3)3 1157 bond SO2CH2CH3 OCOC6H5 C(CH3)3 1158 bond CH3 OCOC6H5 C(CH3)3 1159 bond CF3 OCOC6H5 C(CH3)3 1160 bond OCHF2 OCOC6H5 C(CH3)3 1161 CH2 F OCOC6H5 C(CH3)3 1162 CH2 Cl OCOC6H5 C(CH3)3 1163 CH2 Br OCOC6H5 C(CH3)3 1164 CH2 NO2 OCOC6H5 C(CH3)3 1165 CH2 SCH3 OCOC6H5 C(CH3)3 1166 CH2 SO2CH3 OCOC6H5 C(CH3)3 1167 CH2 SO2CH2CH3 OCOC6H5 C(CH3)3 1168 CH2 CH3 OCOC6H5 C(CH3)3 1169 CH2 CF3 OCOC6H5 C(CH3)3 1170 CH2 OCHF2 OCOC6H5 C(CH3)3 1171 O F OCOC6H5 C(CH3)3 1172 O Cl OCOC6H5 C(CH3)3 1173 O Br OCOC6H5 C(CH3)3 1174 O NO2 OCOC6H5 C(CH3)3 1175 O SCH3 OCOC6H5 C(CH3)3 1176 O SO2CH3 OCOC6H5 C(CH3)3 1177 O SO2CH2CH3 OCOC6H5 C(CH3)3 1178 O CH3 OCOC6H5 C(CH3)3 1179 O CF3 OCOC6H5 C(CH3)3 1180 O OCHF2 OCOC6H5 C(CH3)3 1181 S F OCOC6H5 C(CH3)3 1182 S Cl OCOC6H5 C(CH3)3 1183 S Br OCOC6H5 C(CH3)3 1184 S NO2 OCOC6H5 C(CH3)3 1185 S SCH3 OCOC6H5 C(CH3)3 1186 S SO2CH3 OCOC6H5 C(CH3)3 1187 S SO2CH2CH3 OCOC6H5 C(CH3)3 1188 S CH3 OCOC6H5 C(CH3)3 1189 S CF3 OCOC6H5 C(CH3)3 1190 S OCHF2 OCOC6H5 C(CH3)3 1191 SO2 F OCOC6H5 C(CH3)3 1192 SO2 Cl OCOC6H5 C(CH3)3 1193 SO2 Br OCOC6H5 C(CH3)3 1194 SO2 NO2 OCOC6H5 C(CH3)3 1195 SO2 SCH3 OCOC6H5 C(CH3)3 1196 SO2 SO2CH3 OCOC6H5 C(CH3)3 1197 SO2 SO2CH2CH3 OCOC6H5 C(CH3)3 1198 SO2 CH3 OCOC6H5 C(CH3)3 1199 SO2 CF3 OCOC6H5 C(CH3)3 1200 SO2 OCHF2 OCOC6H5 C(CH3)3 1201 bond F OCOC(CH3)3 CH(CH3)2 1202 bond Cl OCOC(CH3)3 CH(CH3)2 1203 bond Br OCOC(CH3)3 CH(CH3)2 1204 bond NO2 OCOC(CH3)3 CH(CH3)2 1205 bond SCH3 OCOC(CH3)3 CH(CH3)2 1206 bond SO2CH3 OCOC(CH3)3 CH(CH3)2 1207 bond SO2CH2CH3 OCOC(CH3)3 CH(CH3)2 1208 bond CH3 OCOC(CH3)3 CH(CH3)2 1209 bond CF3 OCOC(CH3)3 CH(CH3)2 1210 bond OCHF2 OCOC(CH3)3 CH(CH3)2 1211 CH2 F OCOC(CH3)3 CH(CH3)2 1212 CH2 Cl OCOC(CH3)3 CH(CH3)2 1213 CH2 Br OCOC(CH3)3 CH(CH3)2 1214 CH2 NO2 OCOC(CH3)3 CH(CH3)2 1215 CH2 SCH3 OCOC(CH3)3 CH(CH3)2 1216 CH2 SO2CH3 OCOC(CH3)3 CH(CH3)2 1217 CH2 SO2CH2CH3 OCOC(CH3)3 CH(CH3)2 1218 CH2 CH3 OCOC(CH3)3 CH(CH3)2 1219 CH2 CF3 OCOC(CH3)3 CH(CH3)2 1220 CH2 OCHF2 OCOC(CH3)3 CH(CH3)2 1221 O F OCOC(CH3)3 CH(CH3)2 1222 O Cl OCOC(CH3)3 CH(CH3)2 1223 O Br OCOC(CH3)3 CH(CH3)2 1224 O NO2 OCOC(CH3)3 CH(CH3)2 1225 O SCH3 OCOC(CH3)3 CH(CH3)2 1226 O SO2CH3 OCOC(CH3)3 CH(CH3)2 1227 O SO2CH2CH3 OCOC(CH3)3 CH(CH3)2 1228 O CH3 OCOC(CH3)3 CH(CH3)2 1229 O CF3 OCOC(CH3)3 CH(CH3)2 1230 O OCHF2 OCOC(CH3)3 CH(CH3)2 1231 S F OCOC(CH3)3 CH(CH3)2 1232 S Cl OCOC(CH3)3 CH(CH3)2 1233 S Br OCOC(CH3)3 CH(CH3)2 1234 S NO2 OCOC(CH3)3 CH(CH3)2 1235 S SCH3 OCOC(CH3)3 CH(CH3)2 1236 S SO2CH3 OCOC(CH3)3 CH(CH3)2 1237 S SO2CH2CH3 OCOC(CH3)3 CH(CH3)2 1238 S CH3 OCOC(CH3)3 CH(CH3)2 1239 S CF3 OCOC(CH3)3 CH(CH3)2 1240 S OCHF2 OCOC(CH3)3 CH(CH3)2 1241 SO2 F OCOC(CH3)3 CH(CH3)2 1242 SO2 Cl OCOC(CH3)3 CH(CH3)2 1243 SO2 Br OCOC(CH3)3 CH(CH3)2 1244 SO2 NO2 OCOC(CH3)3 CH(CH3)2 1245 SO2 SCH3 OCOC(CH3)3 CH(CH3)2 1246 SO2 SO2CH3 OCOC(CH3)3 CH(CH3)2 1247 SO2 SO2CH2CH3 OCOC(CH3)3 CH(CH3)2 1248 SO2 CH3 OCOC(CH3)3 CH(CH3)2 1249 SO2 CF3 OCOC(CH3)3 CH(CH3)2 1250 SO2 OCHF2 OCOC(CH3)3 CH(CH3)2 1251 bond F OCOC(CH3)3 C(CH3)3 1252 bond Cl OCOC(CH3)3 C(CH3)3 1253 bond Br OCOC(CH3)3 C(CH3)3 1254 bond NO2 OCOC(CH3)3 C(CH3)3 1255 bond SCH3 OCOC(CH3)3 C(CH3)3 1256 bond SO2CH3 OCOC(CH3)3 C(CH3)3 1257 bond SO2CH2CH3 OCOC(CH3)3 C(CH3)3 1258 bond CH3 OCOC(CH3)3 C(CH3)3 1259 bond CF3 OCOC(CH3)3 C(CH3)3 1260 bond OCHF2 OCOC(CH3)3 C(CH3)3 1261 CH2 F OCOC(CH3)3 C(CH3)3 1262 CH2 Cl OCOC(CH3)3 C(CH3)3 1263 CH2 Br OCOC(CH3)3 C(CH3)3 1264 CH2 NO2 OCOC(CH3)3 C(CH3)3 1265 CH2 SCH3 OCOC(CH3)3 C(CH3)3 1266 CH2 SO2CH3 OCOC(CH3)3 C(CH3)3 1267 CH2 SO2CH2CH3 OCOC(CH3)3 C(CH3)3 1268 CH2 CH3 OCOC(CH3)3 C(CH3)3 1269 CH2 CF3 OCOC(CH3)3 C(CH3)3 1270 CH2 OCHF2 OCOC(CH3)3 C(CH3)3 1271 O F OCOC(CH3)3 C(CH3)3 1272 O Cl OCOC(CH3)3 C(CH3)3 1273 O Br OCOC(CH3)3 C(CH3)3 1274 O NO2 OCOC(CH3)3 C(CH3)3 1275 O SCH3 OCOC(CH3)3 C(CH3)3 1276 O SO2CH3 OCOC(CH3)3 C(CH3)3 1277 O SO2CH2CH3 OCOC(CH3)3 C(CH3)3 1278 O CH3 OCOC(CH3)3 C(CH3)3 1279 O CF3 OCOC(CH3)3 C(CH3)3 1280 O OCHF2 OCOC(CH3)3 C(CH3)3 1281 S F OCOC(CH3)3 C(CH3)3 1282 S Cl OCOC(CH3)3 C(CH3)3 1283 S Br OCOC(CH3)3 C(CH3)3 1284 S NO2 OCOC(CH3)3 C(CH3)3 1285 S SCH3 OCOC(CH3)3 C(CH3)3 1286 S SO2CH3 OCOC(CH3)3 C(CH3)3 1287 S SO2CH2CH3 OCOC(CH3)3 C(CH3)3 1288 S CH3 OCOC(CH3)3 C(CH3)3 1289 S CF3 OCOC(CH3)3 C(CH3)3 1290 S OCHF2 OCOC(CH3)3 C(CH3)3 1291 SO2 F OCOC(CH3)3 C(CH3)3 1292 SO2 Cl OCOC(CH3)3 C(CH3)3 1293 SO2 Br OCOC(CH3)3 C(CH3)3 1294 SO2 NO2 OCOC(CH3)3 C(CH3)3 1295 SO2 SCH3 OCOC(CH3)3 C(CH3)3 1296 SO2 SO2CH3 OCOC(CH3)3 C(CH3)3 1297 SO2 SO2CH2CH3 OCOC(CH3)3 C(CH3)3 1298 SO2 CH3 OCOC(CH3)3 C(CH3)3 1299 SO2 CF3 OCOC(CH3)3 C(CH3)3 1300 SO2 OCHF2 OCOC(CH3)3 C(CH3)3 1301 bond F OCOSCH3 CH(CH3)2 1302 bond Cl OCOSCH3 CH(CH3)2 1303 bond Br OCOSCH3 CH(CH3)2 1304 bond NO2 OCOSCH3 CH(CH3)2 1305 bond SCH3 OCOSCH3 CH(CH3)2 1306 bond SO2CH3 OCOSCH3 CH(CH3)2 1307 bond SO2CH2CH3 OCOSCH3 CH(CH3)2 1308 bond CH3 OCOSCH3 CH(CH3)2 1309 bond CF3 OCOSCH3 CH(CH3)2 1310 bond OCHF2 OCOSCH3 CH(CH3)2 1311 CH2 F OCOSCH3 CH(CH3)2 1312 CH2 Cl OCOSCH3 CH(CH3)2 1313 CH2 Br OCOSCH3 CH(CH3)2 1314 CH2 NO2 OCOSCH3 CH(CH3)2 1315 CH2 SCH3 OCOSCH3 CH(CH3)2 1316 CH2 SO2CH3 OCOSCH3 CH(CH3)2 1317 CH2 SO2CH2CH3 OCOSCH3 CH(CH3)2 1318 CH2 CH3 OCOSCH3 CH(CH3)2 1319 CH2 CF3 OCOSCH3 CH(CH3)2 1320 CH2 OCHF2 OCOSCH3 CH(CH3)2 1321 O F OCOSCH3 CH(CH3)2 1322 O Cl OCOSCH3 CH(CH3)2 1323 O Br OCOSCH3 CH(CH3)2 1324 O NO2 OCOSCH3 CH(CH3)2 1325 O SCH3 OCOSCH3 CH(CH3)2 1326 O SO2CH3 OCOSCH3 CH(CH3)2 1327 O SO2CH2CH3 OCOSCH3 CH(CH3)2 1328 O CH3 OCOSCH3 CH(CH3)2 1329 O CF3 OCOSCH3 CH(CH3)2 1330 O OCHF2 OCOSCH3 CH(CH3)2 1331 S F OCOSCH3 CH(CH3)2 1332 S Cl OCOSCH3 CH(CH3)2 1333 S Br OCOSCH3 CH(CH3)2 1334 S NO2 OCOSCH3 CH(CH3)2 1335 S SCH3 OCOSCH3 CH(CH3)2 1336 S SO2CH3 OCOSCH3 CH(CH3)2 1337 S SO2CH2CH3 OCOSCH3 CH(CH3)2 1338 S CH3 OCOSCH3 CH(CH3)2 1339 S CF3 OCOSCH3 CH(CH3)2 1340 S OCHF2 OCOSCH3 CH(CH3)2 1341 SO2 F OCOSCH3 CH(CH3)2 1342 SO2 Cl OCOSCH3 CH(CH3)2 1343 SO2 Br OCOSCH3 CH(CH3)2 1344 SO2 NO2 OCOSCH3 CH(CH3)2 1345 SO2 SCH3 OCOSCH3 CH(CH3)2 1346 SO2 SO2CH3 OCOSCH3 CH(CH3)2 1347 SO2 SO2CH2CH3 OCOSCH3 CH(CH3)2 1348 SO2 CH3 OCOSCH3 CH(CH3)2 1349 SO2 CF3 OCOSCH3 CH(CH3)2 1350 SO2 OCHF2 OCOSCH3 CH(CH3)2 1351 bond F OCOSCH3 C(CH3)3 1352 bond Cl OCOSCH3 C(CH3)3 1353 bond Br OCOSCH3 C(CH3)3 1354 bond NO2 OCOSCH3 C(CH3)3 1355 bond SCH3 OCOSCH3 C(CH3)3 1356 bond SO2CH3 OCOSCH3 C(CH3)3 1357 bond SO2CH2CH3 OCOSCH3 C(CH3)3 1358 bond CH3 OCOSCH3 C(CH3)3 1359 bond CF3 OCOSCH3 C(CH3)3 1360 bond OCHF2 OCOSCH3 C(CH3)3 1361 CH2 F OCOSCH3 C(CH3)3 1362 CH2 Cl OCOSCH3 C(CH3)3 1363 CH2 Br OCOSCH3 C(CH3)3 1364 CH2 NO2 OCOSCH3 C(CH3)3 1365 CH2 SCH3 OCOSCH3 C(CH3)3 1366 CH2 SO2CH3 OCOSCH3 C(CH3)3 1367 CH2 SO2CH2CH3 OCOSCH3 C(CH3)3 1368 CH2 CH3 OCOSCH3 C(CH3)3 1369 CH2 CF3 OCOSCH3 C(CH3)3 1370 CH2 OCHF2 OCOSCH3 C(CH3)3 1371 O F OCOSCH3 C(CH3)3 1372 O Cl OCOSCH3 C(CH3)3 1373 O Br OCOSCH3 C(CH3)3 1374 O NO2 OCOSCH3 C(CH3)3 1375 O SCH3 OCOSCH3 C(CH3)3 1376 O SO2CH3 OCOSCH3 C(CH3)3 1377 O SO2CH2CH3 OCOSCH3 C(CH3)3 1378 O CH3 OCOSCH3 C(CH3)3 1379 O CF3 OCOSCH3 C(CH3)3 1380 O OCHF2 OCOSCH3 C(CH3)3 1381 S F OCOSCH3 C(CH3)3 1382 S Cl OCOSCH3 C(CH3)3 1383 S Br OCOSCH3 C(CH3)3 1384 S NO2 OCOSCH3 C(CH3)3 1385 S SCH3 OCOSCH3 C(CH3)3 1386 S SO2CH3 OCOSCH3 C(CH3)3 1387 S SO2CH2CH3 OCOSCH3 C(CH3)3 1388 S CH3 OCOSCH3 C(CH3)3 1389 S CF3 OCOSCH3 C(CH3)3 1390 S OCHF2 OCOSCH3 C(CH3)3 1391 SO2 F OCOSCH3 C(CH3)3 1392 SO2 Cl OCOSCH3 C(CH3)3 1393 SO2 Br OCOSCH3 C(CH3)3 1394 SO2 NO2 OCOSCH3 C(CH3)3 1395 SO2 SCH3 OCOSCH3 C(CH3)3 1396 SO2 SO2CH3 OCOSCH3 C(CH3)3 1397 SO2 SO2CH2CH3 OCOSCH3 C(CH3)3 1398 SO2 CH3 OCOSCH3 C(CH3)3 1399 SO2 CF3 OCOSCH3 C(CH3)3 1400 SO2 OCHF2 OCOSCH3 C(CH3)3 1401 bond F OCH3 CH(CH3)2 1402 bond Cl OCH3 CH(CH3)2 1403 bond Br OCH3 CH(CH3)2 1404 bond NO2 OCH3 CH(CH3)2 1405 bond SCH3 OCH3 CH(CH3)2 1406 bond SO2CH3 OCH3 CH(CH3)2 1407 bond SO2CH2CH3 OCH3 CH(CH3)2 1408 bond CH3 OCH3 CH(CH3)2 1409 bond CF3 OCH3 CH(CH3)2 1410 bond OCHF2 OCH3 CH(CH3)2 1411 CH2 F OCH3 CH(CH3)2 1412 CH2 Cl OCH3 CH(CH3)2 1413 CH2 Br OCH3 CH(CH3)2 1414 CH2 NO2 OCH3 CH(CH3)2 1415 CH2 SCH3 OCH3 CH(CH3)2 1416 CH2 SO2CH3 OCH3 CH(CH3)2 1417 CH2 SO2CH2CH3 OCH3 CH(CH3)2 1418 CH2 CH3 OCH3 CH(CH3)2 1419 CH2 CF3 OCH3 CH(CH3)2 1420 CH2 OCHF2 OCH3 CH(CH3)2 1421 O F OCH3 CH(CH3)2 1422 O Cl OCH3 CH(CH3)2 1423 O Br OCH3 CH(CH3)2 1424 O NO2 OCH3 CH(CH3)2 1425 O SCH3 OCH3 CH(CH3)2 1426 O SO2CH3 OCH3 CH(CH3)2 1427 O SO2CH2CH3 OCH3 CH(CH3)2 1428 O CH3 OCH3 CH(CH3)2 1429 O CF3 OCH3 CH(CH3)2 1430 O OCHF2 OCH3 CH(CH3)2 1431 S F OCH3 CH(CH3)2 1432 S Cl OCH3 CH(CH3)2 1433 S Br OCH3 CH(CH3)2 1434 S NO2 OCH3 CH(CH3)2 1435 S SCH3 OCH3 CH(CH3)2 1436 S SO2CH3 OCH3 CH(CH3)2 1437 S SO2CH2CH3 OCH3 CH(CH3)2 1438 S CH3 OCH3 CH(CH3)2 1439 S CF3 OCH3 CH(CH3)2 1440 S OCHF2 OCH3 CH(CH3)2 1441 SO2 F OCH3 CH(CH3)2 1442 SO2 Cl OCH3 CH(CH3)2 1443 SO2 Br OCH3 CH(CH3)2 1444 SO2 NO2 OCH3 CH(CH3)2 1445 SO2 SCH3 OCH3 CH(CH3)2 1446 SO2 SO2CH3 OCH3 CH(CH3)2 1447 SO2 SO2CH2CH3 OCH3 CH(CH3)2 1448 SO2 CH3 OCH3 CH(CH3)2 1449 SO2 CF3 OCH3 CH(CH3)2 1450 SO2 OCHF2 OCH3 CH(CH3)2 1451 bond F OCH3 C(CH3)3 1452 bond Cl OCH3 C(CH3)3 1453 bond Br OCH3 C(CH3)3 1454 bond NO2 OCH3 C(CH3)3 1455 bond SCH3 OCH3 C(CH3)3 1456 bond SO2CH3 OCH3 C(CH3)3 1457 bond SO2CH2CH3 OCH3 C(CH3)3 1458 bond CH3 OCH3 C(CH3)3 1459 bond CF3 OCH3 C(CH3)3 1460 bond OCHF2 OCH3 C(CH3)3 1461 CH2 F OCH3 C(CH3)3 1462 CH2 Cl OCH3 C(CH3)3 1463 CH2 Br OCH3 C(CH3)3 1464 CH2 NO2 OCH3 C(CH3)3 1465 CH2 SCH3 OCH3 C(CH3)3 1466 CH2 SO2CH3 OCH3 C(CH3)3 1467 CH2 SO2CH2CH3 OCH3 C(CH3)3 1468 CH2 CH3 OCH3 C(CH3)3 1469 CH2 CF3 OCH3 C(CH3)3 1470 CH2 OCHF2 OCH3 C(CH3)3 1471 O F OCH3 C(CH3)3 1472 O Cl OCH3 C(CH3)3 1473 O Br OCH3 C(CH3)3 1474 O NO2 OCH3 C(CH3)3 1475 O SCH3 OCH3 C(CH3)3 1476 O SO2CH3 OCH3 C(CH3)3 1477 O SO2CH2CH3 OCH3 C(CH3)3 1478 O CH3 OCH3 C(CH3)3 1479 O CF3 OCH3 C(CH3)3 1480 O OCHF2 OCH3 C(CH3)3 1481 S F OCH3 C(CH3)3 1482 S Cl OCH3 C(CH3)3 1483 S Br OCH3 C(CH3)3 1484 S NO2 OCH3 C(CH3)3 1485 S SCH3 OCH3 C(CH3)3 1486 S SO2CH3 OCH3 C(CH3)3 1487 S SO2CH2CH3 OCH3 C(CH3)3 1488 S CH3 OCH3 C(CH3)3 1489 S CF3 OCH3 C(CH3)3 1490 S OCHF2 OCH3 C(CH3)3 1491 SO2 F OCH3 C(CH3)3 1492 SO2 Cl OCH3 C(CH3)3 1493 SO2 Br OCH3 C(CH3)3 1494 SO2 NO2 OCH3 C(CH3)3 1495 SO2 SCH3 OCH3 C(CH3)3 1496 SO2 SO2CH3 OCH3 C(CH3)3 1497 SO2 SO2CH2CH3 OCH3 C(CH3)3 1498 SO2 CH3 OCH3 C(CH3)3 1499 SO2 CF3 OCH3 C(CH3)3 1500 SO2 OCHF2 OCH3 C(CH3)3 1501 bond F OCH(CH3)2 CH(CH3)2 1502 bond Cl OCH(CH3)2 CH(CH3)2 1503 bond Br OCH(CH3)2 CH(CH3)2 1504 bond NO2 OCH(CH3)2 CH(CH3)2 1505 bond SCH3 OCH(CH3)2 CH(CH3)2 1506 bond SO2CH3 OCH(CH3)2 CH(CH3)2 1507 bond SO2CH2CH3 OCH(CH3)2 CH(CH3)2 1508 bond CH3 OCH(CH3)2 CH(CH3)2 1509 bond CF3 OCH(CH3)2 CH(CH3)2 1510 bond OCHF2 OCH(CH3)2 CH(CH3)2 1511 CH2 F OCH(CH3)2 CH(CH3)2 1512 CH2 Cl OCH(CH3)2 CH(CH3)2 1513 CH2 Br OCH(CH3)2 CH(CH3)2 1514 CH2 NO2 OCH(CH3)2 CH(CH3)2 1515 CH2 SCH3 OCH(CH3)2 CH(CH3)2 1516 CH2 SO2CH3 OCH(CH3)2 CH(CH3)2 1517 CH2 SO2CH2CH3 OCH(CH3)2 CH(CH3)2 1518 CH2 CH3 OCH(CH3)2 CH(CH3)2 1519 CH2 CF3 OCH(CH3)2 CH(CH3)2 1520 CH2 OCHF2 OCH(CH3)2 CH(CH3)2 1521 O F OCH(CH3)2 CH(CH3)2 1522 O Cl OCH(CH3)2 CH(CH3)2 1523 O Br OCH(CH3)2 CH(CH3)2 1524 O NO2 OCH(CH3)2 CH(CH3)2 1525 O SCH3 OCH(CH3)2 CH(CH3)2 1526 O SO2CH3 OCH(CH3)2 CH(CH3)2 1527 O SO2CH2CH3 OCH(CH3)2 CH(CH3)2 1528 O CH3 OCH(CH3)2 CH(CH3)2 1529 O CF3 OCH(CH3)2 CH(CH3)2 1530 O OCHF2 OCH(CH3)2 CH(CH3)2 1531 S F OCH(CH3)2 CH(CH3)2 1532 S Cl OCH(CH3)2 CH(CH3)2 1533 S Br OCH(CH3)2 CH(CH3)2 1534 S NO2 OCH(CH3)2 CH(CH3)2 1535 S SCH3 OCH(CH3)2 CH(CH3)2 1536 S SO2CH3 OCH(CH3)2 CH(CH3)2 1537 S SO2CH2CH3 OCH(CH3)2 CH(CH3)2 1538 S CH3 OCH(CH3)2 CH(CH3)2 1539 S CF3 OCH(CH3)2 CH(CH3)2 1540 S OCHF2 OCH(CH3)2 CH(CH3)2 1541 SO2 F OCH(CH3)2 CH(CH3)2 1542 SO2 Cl OCH(CH3)2 CH(CH3)2 1543 SO2 Br OCH(CH3)2 CH(CH3)2 1544 SO2 NO2 OCH(CH3)2 CH(CH3)2 1545 SO2 SCH3 OCH(CH3)2 CH(CH3)2 1546 SO2 SO2CH3 OCH(CH3)2 CH(CH3)2 1547 SO2 SO2CH2CH3 OCH(CH3)2 CH(CH3)2 1548 SO2 CH3 OCH(CH3)2 CH(CH3)2 1549 SO2 CF3 OCH(CH3)2 CH(CH3)2 1550 SO2 OCHF2 OCH(CH3)2 CH(CH3)2 1551 bond F OCH(CH3)2 C(CH3)3 1552 bond Cl OCH(CH3)2 C(CH3)3 1553 bond Br OCH(CH3)2 C(CH3)3 1554 bond NO2 OCH(CH3)2 C(CH3)3 1555 bond SCH3 OCH(CH3)2 C(CH3)3 1556 bond SO2CH3 OCH(CH3)2 C(CH3)3 1557 bond SO2CH2CH3 OCH(CH3)2 C(CH3)3 1558 bond CH3 OCH(CH3)2 C(CH3)3 1559 bond CF3 OCH(CH3)2 C(CH3)3 1560 bond OCHF2 OCH(CH3)2 C(CH3)3 1561 CH2 F OCH(CH3)2 C(CH3)3 1562 CH2 Cl OCH(CH3)2 C(CH3)3 1563 CH2 Br OCH(CH3)2 C(CH3)3 1564 CH2 NO2 OCH(CH3)2 C(CH3)3 1565 CH2 SCH3 OCH(CH3)2 C(CH3)3 1566 CH2 SO2CH3 OCH(CH3)2 C(CH3)3 1567 CH2 SO2CH2CH3 OCH(CH3)2 C(CH3)3 1568 CH2 CH3 OCH(CH3)2 C(CH3)3 1569 CH2 CF3 OCH(CH3)2 C(CH3)3 1570 CH2 OCHF2 OCH(CH3)2 C(CH3)3 1571 O F OCH(CH3)2 C(CH3)3 1572 O Cl OCH(CH3)2 C(CH3)3 1573 O Br OCH(CH3)2 C(CH3)3 1574 O NO2 OCH(CH3)2 C(CH3)3 1575 O SCH3 OCH(CH3)2 C(CH3)3 1576 O SO2CH3 OCH(CH3)2 C(CH3)3 1577 O SO2CH2CH3 OCH(CH3)2 C(CH3)3 1578 O CH3 OCH(CH3)2 C(CH3)3 1579 O CF3 OCH(CH3)2 C(CH3)3 1580 O OCHF2 OCH(CH3)2 C(CH3)3 1581 S F OCH(CH3)2 C(CH3)3 1582 S Cl OCH(CH3)2 C(CH3)3 1583 S Br OCH(CH3)2 C(CH3)3 1584 S NO2 OCH(CH3)2 C(CH3)3 1585 S SCH3 OCH(CH3)2 C(CH3)3 1586 S SO2CH3 OCH(CH3)2 C(CH3)3 1587 S SO2CH2CH3 OCH(CH3)2 C(CH3)3 1588 S CH3 OCH(CH3)2 C(CH3)3 1589 S CF3 OCH(CH3)2 C(CH3)3 1590 S OCHF2 OCH(CH3)2 C(CH3)3 1591 SO2 F OCH(CH3)2 C(CH3)3 1592 SO2 Cl OCH(CH3)2 C(CH3)3 1593 SO2 Br OCH(CH3)2 C(CH3)3 1594 SO2 NO2 OCH(CH3)2 C(CH3)3 1595 SO2 SCH3 OCH(CH3)2 C(CH3)3 1596 SO2 SO2CH3 OCH(CH3)2 C(CH3)3 1597 SO2 SO2CH2CH3 OCH(CH3)2 C(CH3)3 1598 SO2 CH3 OCH(CH3)2 C(CH3)3 1599 SO2 CF3 OCH(CH3)2 C(CH3)3 1600 SO2 OCHF2 OCH(CH3)2 C(CH3)3 1601 bond F OCH2C6H5 CH(CH3)2 1602 bond Cl OCH2C6H5 CH(CH3)2 1603 bond Br OCH2C6H5 CH(CH3)2 1604 bond NO2 OCH2C6H5 CH(CH3)2 1605 bond SCH3 OCH2C6H5 CH(CH3)2 1606 bond SO2CH3 OCH2C6H5 CH(CH3)2 1607 bond SO2CH2CH3 OCH2C6H5 CH(CH3)2 1608 bond CH3 OCH2C6H5 CH(CH3)2 1609 bond CF3 OCH2C6H5 CH(CH3)2 1610 bond OCHF2 OCH2C6H5 CH(CH3)2 1611 CH2 F OCH2C6H5 CH(CH3)2 1612 CH2 Cl OCH2C6H5 CH(CH3)2 1613 CH2 Br OCH2C6H5 CH(CH3)2 1614 CH2 NO2 OCH2C6H5 CH(CH3)2 1615 CH2 SCH3 OCH2C6H5 CH(CH3)2 1616 CH2 SO2CH3 OCH2C6H5 CH(CH3)2 1617 CH2 SO2CH2CH3 OCH2C6H5 CH(CH3)2 1618 CH2 CH3 OCH2C6H5 CH(CH3)2 1619 CH2 CF3 OCH2C6H5 CH(CH3)2 1620 CH2 OCHF2 OCH2C6H5 CH(CH3)2 1621 O F OCH2C6H5 CH(CH3)2 1622 O Cl OCH2C6H5 CH(CH3)2 1623 O Br OCH2C6H5 CH(CH3)2 1624 O NO2 OCH2C6H5 CH(CH3)2 1625 O SCH3 OCH2C6H5 CH(CH3)2 1626 O SO2CH3 OCH2C6H5 CH(CH3)2 1627 O SO2CH2CH3 OCH2C6H5 CH(CH3)2 1628 O CH3 OCH2C6H5 CH(CH3)2 1629 O CF3 OCH2C6H5 CH(CH3)2 1630 O OCHF2 OCH2C6H5 CH(CH3)2 1631 S F OCH2C6H5 CH(CH3)2 1632 S Cl OCH2C6H5 CH(CH3)2 1633 S Br OCH2C6H5 CH(CH3)2 1634 S NO2 OCH2C6H5 CH(CH3)2 1635 S SCH3 OCH2C6H5 CH(CH3)2 1636 S SO2CH3 OCH2C6H5 CH(CH3)2 1637 S SO2CH2CH3 OCH2C6H5 CH(CH3)2 1638 S CH3 OCH2C6H5 CH(CH3)2 1639 S CF3 OCH2C6H5 CH(CH3)2 1640 S OCHF2 OCH2C6H5 CH(CH3)2 1641 SO2 F OCH2C6H5 CH(CH3)2 1642 SO2 Cl OCH2C6H5 CH(CH3)2 1643 SO2 Br OCH2C6H5 CH(CH3)2 1644 SO2 NO2 OCH2C6H5 CH(CH3)2 1645 SO2 SCH3 OCH2C6H5 CH(CH3)2 1646 SO2 SO2CH3 OCH2C6H5 CH(CH3)2 1647 SO2 SO2CH2CH3 OCH2C6H5 CH(CH3)2 1648 SO2 CH3 OCH2C6H5 CH(CH3)2 1649 SO2 CF3 OCH2C6H5 CH(CH3)2 1650 SO2 OCHF2 OCH2C6H5 CH(CH3)2 1651 bond F OCH2C6H5 C(CH3)3 1652 bond Cl OCH2C6H5 C(CH3)3 1653 bond Br OCH2C6H5 C(CH3)3 1654 bond NO2 OCH2C6H5 C(CH3)3 1655 bond SCH3 OCH2C6H5 C(CH3)3 1656 bond SO2CH3 OCH2C6H5 C(CH3)3 1657 bond SO2CH2CH3 OCH2C6H5 C(CH3)3 1658 bond CH3 OCH2C6H5 C(CH3)3 1659 bond CF3 OCH2C6H5 C(CH3)3 1660 bond OCHF2 OCH2C6H5 C(CH3)3 1661 CH2 F OCH2C6H5 C(CH3)3 1662 CH2 Cl OCH2C6H5 C(CH3)3 1663 CH2 Br OCH2C6H5 C(CH3)3 1664 CH2 NO2 OCH2C6H5 C(CH3)3 1665 CH2 SCH3 OCH2C6H5 C(CH3)3 1666 CH2 SO2CH3 OCH2C6H5 C(CH3)3 1667 CH2 SO2CH2CH3 OCH2C6H5 C(CH3)3 1668 CH2 CH3 OCH2C6H5 C(CH3)3 1669 CH2 CF3 OCH2C6H5 C(CH3)3 1670 CH2 OCHF2 OCH2C6H5 C(CH3)3 1671 O F OCH2C6H5 C(CH3)3 1672 O Cl OCH2C6H5 C(CH3)3 1673 O Br OCH2C6H5 C(CH3)3 1674 O NO2 OCH2C6H5 C(CH3)3 1675 O SCH3 OCH2C6H5 C(CH3)3 1676 O SO2CH3 OCH2C6H5 C(CH3)3 1677 O SO2CH2CH3 OCH2C6H5 C(CH3)3 1678 O CH3 OCH2C6H5 C(CH3)3 1679 O CF3 OCH2C6H5 C(CH3)3 1680 O OCHF2 OCH2C6H5 C(CH3)3 1681 S F OCH2C6H5 C(CH3)3 1682 S Cl OCH2C6H5 C(CH3)3 1683 S Br OCH2C6H5 C(CH3)3 1684 S NO2 OCH2C6H5 C(CH3)3 1685 S SCH3 OCH2C6H5 C(CH3)3 1686 S SO2CH3 OCH2C6H5 C(CH3)3 1687 S SO2CH2CH3 OCH2C6H5 C(CH3)3 1688 S CH3 OCH2C6H5 C(CH3)3 1689 S CF3 OCH2C6H5 C(CH3)3 1690 S OCHF2 OCH2C6H5 C(CH3)3 1691 SO2 F OCH2C6H5 C(CH3)3 1692 SO2 Cl OCH2C6H5 C(CH3)3 1693 SO2 Br OCH2C6H5 C(CH3)3 1694 SO2 NO2 OCH2C6H5 C(CH3)3 1695 SO2 SCH3 OCH2C6H5 C(CH3)3 1696 SO2 SO2CH3 OCH2C6H5 C(CH3)3 1697 SO2 SO2CH2CH3 OCH2C6H5 C(CH3)3 1698 SO2 CH3 OCH2C6H5 C(CH3)3 1699 SO2 CF3 OCH2C6H5 C(CH3)3 1700 SO2 OCHF2 OCH2C6H5 C(CH3)3 1701 bond F OSO2(4-CH3—C6H4) CH(CH3)2 1702 bond Cl OSO2(4-CH3—C6H4) CH(CH3)2 1703 bond Br OSO2(4-CH3—C6H4) CH(CH3)2 1704 bond NO2 OSO2(4-CH3—C6H4) CH(CH3)2 1705 bond SCH3 OSO2(4-CH3—C6H4) CH(CH3)2 1706 bond SO2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1707 bond SO2CH2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1708 bond CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1709 bond CF3 OSO2(4-CH3—C6H4) CH(CH3)2 1710 bond OCHF2 OSO2(4-CH3—C6H4) CH(CH3)2 1711 CH2 F OSO2(4-CH3—C6H4) CH(CH3)2 1712 CH2 Cl OSO2(4-CH3—C6H4) CH(CH3)2 1713 CH2 Br OSO2(4-CH3—C6H4) CH(CH3)2 1714 CH2 NO2 OSO2(4-CH3—C6H4) CH(CH3)2 1715 CH2 SCH3 OSO2(4-CH3—C6H4) CH(CH3)2 1716 CH2 SO2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1717 CH2 SO2CH2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1718 CH2 CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1719 CH2 CF3 OSO2(4-CH3—C6H4) CH(CH3)2 1720 CH2 OCHF2 OSO2(4-CH3—C6H4) CH(CH3)2 1721 O F OSO2(4-CH3—C6H4) CH(CH3)2 1722 O Cl OSO2(4-CH3—C6H4) CH(CH3)2 1723 O Br OSO2(4-CH3—C6H4) CH(CH3)2 1724 O NO2 OSO2(4-CH3—C6H4) CH(CH3)2 1725 O SCH3 OSO2(4-CH3—C6H4) CH(CH3)2 1726 O SO2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1727 O SO2CH2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1728 O CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1729 O CF3 OSO2(4-CH3—C6H4) CH(CH3)2 1730 O OCHF2 OSO2(4-CH3—C6H4) CH(CH3)2 1731 S F OSO2(4-CH3—C6H4) CH(CH3)2 1732 S Cl OSO2(4-CH3—C6H4) CH(CH3)2 1733 S Br OSO2(4-CH3—C6H4) CH(CH3)2 1734 S NO2 OSO2(4-CH3—C6H4) CH(CH3)2 1735 S SCH3 OSO2(4-CH3—C6H4) CH(CH3)2 1736 S SO2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1737 S SO2CH2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1738 S CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1739 S CF3 OSO2(4-CH3—C6H4) CH(CH3)2 1740 S OCHF2 OSO2(4-CH3—C6H4) CH(CH3)2 1741 SO2 F OSO2(4-CH3—C6H4) CH(CH3)2 1742 SO2 Cl OSO2(4-CH3—C6H4) CH(CH3)2 1743 SO2 Br OSO2(4-CH3—C6H4) CH(CH3)2 1744 SO2 NO2 OSO2(4-CH3—C6H4) CH(CH3)2 1745 SO2 SCH3 OSO2(4-CH3—C6H4) CH(CH3)2 1746 SO2 SO2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1747 SO2 SO2CH2CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1748 SO2 CH3 OSO2(4-CH3—C6H4) CH(CH3)2 1749 SO2 CF3 OSO2(4-CH3—C6H4) CH(CH3)2 1750 SO2 OCHF2 OSO2(4-CH3—C6H4) CH(CH3)2 1751 bond F OSO2(4-CH3—C6H4) C(CH3)3 1752 bond Cl OSO2(4-CH3—C6H4) C(CH3)3 1753 bond Br OSO2(4-CH3—C6H4) C(CH3)3 1754 bond NO2 OSO2(4-CH3—C6H4) C(CH3)3 1755 bond SCH3 OSO2(4-CH3—C6H4) C(CH3)3 1756 bond SO2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1757 bond SO2CH2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1758 bond CH3 OSO2(4-CH3—C6H4) C(CH3)3 1759 bond CF3 OSO2(4-CH3—C6H4) C(CH3)3 1760 bond OCHF2 OSO2(4-CH3—C6H4) C(CH3)3 1761 CH2 F OSO2(4-CH3—C6H4) C(CH3)3 1762 CH2 Cl OSO2(4-CH3—C6H4) C(CH3)3 1763 CH2 Br OSO2(4-CH3—C6H4) C(CH3)3 1764 CH2 NO2 OSO2(4-CH3—C6H4) C(CH3)3 1765 CH2 SCH3 OSO2(4-CH3—C6H4) C(CH3)3 1766 CH2 SO2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1767 CH2 SO2CH2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1768 CH2 CH3 OSO2(4-CH3—C6H4) C(CH3)3 1769 CH2 CF3 OSO2(4-CH3—C6H4) C(CH3)3 1770 CH2 OCHF2 OSO2(4-CH3—C6H4) C(CH3)3 1771 O F OSO2(4-CH3—C6H4) C(CH3)3 1772 O Cl OSO2(4-CH3—C6H4) C(CH3)3 1773 O Br OSO2(4-CH3—C6H4) C(CH3)3 1774 O NO2 OSO2(4-CH3—C6H4) C(CH3)3 1775 O SCH3 OSO2(4-CH3—C6H4) C(CH3)3 1776 O SO2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1777 O SO2CH2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1778 O CH3 OSO2(4-CH3—C6H4) C(CH3)3 1779 O CF3 OSO2(4-CH3—C6H4) C(CH3)3 1780 O OCHF2 OSO2(4-CH3—C6H4) C(CH3)3 1781 S F OSO2(4-CH3—C6H4) C(CH3)3 1782 S Cl OSO2(4-CH3—C6H4) C(CH3)3 1783 S Br OSO2(4-CH3—C6H4) C(CH3)3 1784 S NO2 OSO2(4-CH3—C6H4) C(CH3)3 1785 S SCH3 OSO2(4-CH3—C6H4) C(CH3)3 1786 S SO2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1787 S SO2CH2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1788 S CH3 OSO2(4-CH3—C6H4) C(CH3)3 1789 S CF3 OSO2(4-CH3—C6H4) C(CH3)3 1790 S OCHF2 OSO2(4-CH3—C6H4) C(CH3)3 1791 SO2 F OSO2(4-CH3—C6H4) C(CH3)3 1792 SO2 Cl OSO2(4-CH3—C6H4) C(CH3)3 1793 SO2 Br OSO2(4-CH3—C6H4) C(CH3)3 1794 SO2 NO2 OSO2(4-CH3—C6H4) C(CH3)3 1795 SO2 SCH3 OSO2(4-CH3—C6H4) C(CH3)3 1796 SO2 SO2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1797 SO2 SO2CH2CH3 OSO2(4-CH3—C6H4) C(CH3)3 1798 SO2 CH3 OSO2(4-CH3—C6H4) C(CH3)3 1799 SO2 CF3 OSO2(4-CH3—C6H4) C(CH3)3 1800 SO2 OCHF2 OSO2(4-CH3—C6H4) C(CH3)3 1801 bond F SCH3 CH(CH3)2 1802 bond Cl SCH3 CH(CH3)2 1803 bond Br SCH3 CH(CH3)2 1804 bond NO2 SCH3 CH(CH3)2 1805 bond SCH3 SCH3 CH(CH3)2 1806 bond SO2CH3 SCH3 CH(CH3)2 1807 bond SO2CH2CH3 SCH3 CH(CH3)2 1808 bond CH3 SCH3 CH(CH3)2 1809 bond CF3 SCH3 CH(CH3)2 1810 bond OCHF2 SCH3 CH(CH3)2 1811 CH2 F SCH3 CH(CH3)2 1812 CH2 Cl SCH3 CH(CH3)2 1813 CH2 Br SCH3 CH(CH3)2 1814 CH2 NO2 SCH3 CH(CH3)2 1815 CH2 SCH3 SCH3 CH(CH3)2 1816 CH2 SO2CH3 SCH3 CH(CH3)2 1817 CH2 SO2CH2CH3 SCH3 CH(CH3)2 1818 CH2 CH3 SCH3 CH(CH3)2 1819 CH2 CF3 SCH3 CH(CH3)2 1820 CH2 OCHF2 SCH3 CH(CH3)2 1821 O F SCH3 CH(CH3)2 1822 O Cl SCH3 CH(CH3)2 1823 O Br SCH3 CH(CH3)2 1824 O NO2 SCH3 CH(CH3)2 1825 O SCH3 SCH3 CH(CH3)2 1826 O SO2CH3 SCH3 CH(CH3)2 1827 O SO2CH2CH3 SCH3 CH(CH3)2 1828 O CH3 SCH3 CH(CH3)2 1829 O CF3 SCH3 CH(CH3)2 1830 O OCHF2 SCH3 CH(CH3)2 1831 S F SCH3 CH(CH3)2 1832 S Cl SCH3 CH(CH3)2 1833 S Br SCH3 CH(CH3)2 1834 S NO2 SCH3 CH(CH3)2 1835 S SCH3 SCH3 CH(CH3)2 1836 S SO2CH3 SCH3 CH(CH3)2 1837 S SO2CH2CH3 SCH3 CH(CH3)2 1838 S CH3 SCH3 CH(CH3)2 1839 S CF3 SCH3 CH(CH3)2 1840 S OCHF2 SCH3 CH(CH3)2 1841 SO2 F SCH3 CH(CH3)2 1842 SO2 Cl SCH3 CH(CH3)2 1843 SO2 Br SCH3 CH(CH3)2 1844 SO2 NO2 SCH3 CH(CH3)2 1845 SO2 SCH3 SCH3 CH(CH3)2 1846 SO2 SO2CH3 SCH3 CH(CH3)2 1847 SO2 SO2CH2CH3 SCH3 CH(CH3)2 1848 SO2 CH3 SCH3 CH(CH3)2 1849 SO2 CF3 SCH3 CH(CH3)2 1850 SO2 OCHF2 SCH3 CH(CH3)2 1851 bond F SCH3 C(CH3)3 1852 bond Cl SCH3 C(CH3)3 1853 bond Br SCH3 C(CH3)3 1854 bond NO2 SCH3 C(CH3)3 1855 bond SCH3 SCH3 C(CH3)3 1856 bond SO2CH3 SCH3 C(CH3)3 1857 bond SO2CH2CH3 SCH3 C(CH3)3 1858 bond CH3 SCH3 C(CH3)3 1859 bond CF3 SCH3 C(CH3)3 1860 bond OCHF2 SCH3 C(CH3)3 1861 CH2 F SCH3 C(CH3)3 1862 CH2 Cl SCH3 C(CH3)3 1863 CH2 Br SCH3 C(CH3)3 1864 CH2 NO2 SCH3 C(CH3)3 1865 CH2 SCH3 SCH3 C(CH3)3 1866 CH2 SO2CH3 SCH3 C(CH3)3 1867 CH2 SO2CH2CH3 SCH3 C(CH3)3 1868 CH2 CH3 SCH3 C(CH3)3 1869 CH2 CF3 SCH3 C(CH3)3 1870 CH2 OCHF2 SCH3 C(CH3)3 1871 O F SCH3 C(CH3)3 1872 O Cl SCH3 C(CH3)3 1873 O Br SCH3 C(CH3)3 1874 O NO2 SCH3 C(CH3)3 1875 O SCH3 SCH3 C(CH3)3 1876 O SO2CH3 SCH3 C(CH3)3 1877 O SO2CH2CH3 SCH3 C(CH3)3 1878 O CH3 SCH3 C(CH3)3 1879 O CF3 SCH3 C(CH3)3 1880 O OCHF2 SCH3 C(CH3)3 1881 S F SCH3 C(CH3)3 1882 S Cl SCH3 C(CH3)3 1883 S Br SCH3 C(CH3)3 1884 S NO2 SCH3 C(CH3)3 1885 S SCH3 SCH3 C(CH3)3 1886 S SO2CH3 SCH3 C(CH3)3 1887 S SO2CH2CH3 SCH3 C(CH3)3 1888 S CH3 SCH3 C(CH3)3 1889 S CF3 SCH3 C(CH3)3 1890 S OCHF2 SCH3 C(CH3)3 1891 SO2 F SCH3 C(CH3)3 1892 SO2 Cl SCH3 C(CH3)3 1893 SO2 Br SCH3 C(CH3)3 1894 SO2 NO2 SCH3 C(CH3)3 1895 SO2 SCH3 SCH3 C(CH3)3 1896 SO2 SO2CH3 SCH3 C(CH3)3 1897 SO2 SO2CH2CH3 SCH3 C(CH3)3 1898 SO2 CH3 SCH3 C(CH3)3 1899 SO2 CF3 SCH3 C(CH3)3 1900 SO2 OCHF2 SCH3 C(CH3)3 1901 bond F Cl CH(CH3)2 1902 bond Cl Cl CH(CH3)2 1903 bond Br Cl CH(CH3)2 1904 bond NO2 Cl CH(CH3)2 1905 bond SCH3 Cl CH(CH3)2 1906 bond SO2CH3 Cl CH(CH3)2 1907 bond SO2CH2CH3 Cl CH(CH3)2 1908 bond CH3 Cl CH(CH3)2 1909 bond CF3 Cl CH(CH3)2 1910 bond OCHF2 Cl CH(CH3)2 1911 CH2 F Cl CH(CH3)2 1912 CH2 Cl Cl CH(CH3)2 1913 CH2 Br Cl CH(CH3)2 1914 CH2 NO2 Cl CH(CH3)2 1915 CH2 SCH3 Cl CH(CH3)2 1916 CH2 SO2CH3 Cl CH(CH3)2 1917 CH2 SO2CH2CH3 Cl CH(CH3)2 1918 CH2 CH3 Cl CH(CH3)2 1919 CH2 CF3 Cl CH(CH3)2 1920 CH2 OCHF2 Cl CH(CH3)2 1921 O F Cl CH(CH3)2 1922 O Cl Cl CH(CH3)2 1923 O Br Cl CH(CH3)2 1924 O NO2 Cl CH(CH3)2 1925 O SCH3 Cl CH(CH3)2 1926 O SO2CH3 Cl CH(CH3)2 1927 O SO2CH2CH3 Cl CH(CH3)2 1928 O CH3 Cl CH(CH3)2 1929 O CF3 Cl CH(CH3)2 1930 O OCHF2 Cl CH(CH3)2 1931 S F Cl CH(CH3)2 1932 S Cl Cl CH(CH3)2 1933 S Br Cl CH(CH3)2 1934 S NO2 Cl CH(CH3)2 1935 S SCH3 Cl CH(CH3)2 1936 S SO2CH3 Cl CH(CH3)2 1937 S SO2CH2CH3 Cl CH(CH3)2 1938 S CH3 Cl CH(CH3)2 1939 S CF3 Cl CH(CH3)2 1940 S OCHF2 Cl CH(CH3)2 1941 SO2 F Cl CH(CH3)2 1942 SO2 Cl Cl CH(CH3)2 1943 SO2 Br Cl CH(CH3)2 1944 SO2 NO2 Cl CH(CH3)2 1945 SO2 SCH3 Cl CH(CH3)2 1946 SO2 SO2CH3 Cl CH(CH3)2 1947 SO2 SO2CH2CH3 Cl CH(CH3)2 1948 SO2 CH3 Cl CH(CH3)2 1949 SO2 CF3 Cl CH(CH3)2 1950 SO2 OCHF2 Cl CH(CH3)2 1951 bond F Cl C(CH3)3 1952 bond Cl Cl C(CH3)3 1953 bond Br Cl C(CH3)3 1954 bond NO2 Cl C(CH3)3 1955 bond SCH3 Cl C(CH3)3 1956 bond SO2CH3 Cl C(CH3)3 1957 bond SO2CH2CH3 Cl C(CH3)3 1958 bond CH3 Cl C(CH3)3 1959 bond CF3 Cl C(CH3)3 1960 bond OCHF2 Cl C(CH3)3 1961 CH2 F Cl C(CH3)3 1962 CH2 Cl Cl C(CH3)3 1963 CH2 Br Cl C(CH3)3 1964 CH2 NO2 Cl C(CH3)3 1965 CH2 SCH3 Cl C(CH3)3 1966 CH2 SO2CH3 Cl C(CH3)3 1967 CH2 SO2CH2CH3 Cl C(CH3)3 1968 CH2 CH3 Cl C(CH3)3 1969 CH2 CF3 Cl C(CH3)3 1970 CH2 OCHF2 Cl C(CH3)3 1971 O F Cl C(CH3)3 1972 O Cl Cl C(CH3)3 1973 O Br Cl C(CH3)3 1974 O NO2 Cl C(CH3)3 1975 O SCH3 Cl C(CH3)3 1976 O SO2CH3 Cl C(CH3)3 1977 O SO2CH2CH3 Cl C(CH3)3 1978 O CH3 Cl C(CH3)3 1979 O CF3 Cl C(CH3)3 1980 O OCHF2 Cl C(CH3)3 1981 S F Cl C(CH3)3 1982 S Cl Cl C(CH3)3 1983 S Br Cl C(CH3)3 1984 S NO2 Cl C(CH3)3 1985 S SCH3 Cl C(CH3)3 1986 S SO2CH3 Cl C(CH3)3 1987 S SO2CH2CH3 Cl C(CH3)3 1988 S CH3 Cl C(CH3)3 1989 S CF3 Cl C(CH3)3 1990 S OCHF2 Cl C(CH3)3 1991 SO2 F Cl C(CH3)3 1992 SO2 Cl Cl C(CH3)3 1993 SO2 Br Cl C(CH3)3 1994 SO2 NO2 Cl C(CH3)3 1995 SO2 SCH3 Cl C(CH3)3 1996 SO2 SO2CH3 Cl C(CH3)3 1997 SO2 SO2CH2CH3 Cl C(CH3)3 1998 SO2 CH3 Cl C(CH3)3 1999 SO2 CF3 Cl C(CH3)3 2000 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.
    • 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. I 1978, 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 reactA123ions 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 substitutents 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 nitrites, 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 nitriles 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 substitutents or to modify the substitutents 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 −20° 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 130° 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-methylsulfonyl-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 15° 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 50° 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 136° 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 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-[1]-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-[1]-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.: 168-171° 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.: 123-124° 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 126-129° 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 60° 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.-225° 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 5:

TABLE 2 physical data (m.p. [° C.]; No. X R4 R10 R11 R12 1H NMR [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-F—C6H4) CH3 H oil

TABLE 3 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 physical data (m.p. [° C.]; No. X R4 R10 R11 R12 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 (m.p. [° C.]; Nr. X R4 R10 R11 R12 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, 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, phenylactic 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.-20. (canceled)

21. A tricyclic benzoylpyrazole compound of formula I

where:
X is oxygen, sulfur, S═O, S(═O)2, CR6R7, or NR8;
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 and 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-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 substitutents 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 substitutents 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 substitutents 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 substitutents 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.

22. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where R9 is IIa.

23. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where X is oxygen, sulfur or CR6R7.

24. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where

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

25. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 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 oder 1.

26. The tricyclic benzoylpyrazole compound of formula I defined in claim 21 where

R10 is hydroxyl;
R11 is C1-C6-alkyl or C3-C6-cycloalkyl;
R12 is hydrogen or C1-C6-alkyl.

27. A process for preparing the compound of formula I where R10=halogen as claimed in claim 21, 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 21, with a halogenating agent.

28. A process for preparing the compound of formula I where R10=OR13 as claimed in claim 21, 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 21, with a compound of formula III L1R13  III where the variable R13 is as defined in claim 21 and L1 is a nucleophilically replaceable leaving group.

29. A process for preparing the compound of formula I where R10=OR13, SR13, NR15R16 or N-bonded heterocyclyl as claimed in claim 21, 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 21, with a compound of formula IVα, IVβ, IVγ or IVδ HOR13HSR13NHR15R16H(N-bonded heterocyclyl) Ivo. IVp ivy IV8 where the variables R13 to R16 are as defined in claim 21, optionally in the presence of a base.

30. A process for preparing the compound of formula I where R10=SO2R14 as claimed in claim 21, 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 21, with an oxidizing agent.

31. A process for preparing the compound of formula I where R9=IIa as claimed in claim 21, which comprises reacting a metalated pyrazole compound of formula V where M is a metal and R10 to R12 are as defined in claim 21, 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 21 and L2 is a nucleophilically replaceable leaving group.

32. A process for preparing the compound of formula Iα (=I where R10=hydroxyl) as claimed in claim 21, which comprises acylating a pyrazole of formula VII in which the variables R11 and R12 are as defined in claim 21 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 21 and L3 is a nucleophilically replaceable leaving group, and rearranging the acylation product, optionally in the presence of a catalyst.

33. A process for preparing the compound of formula Iα (≡I where R10=hydroxyl) as claimed in claim 21, which comprises reacting a pyrazole of formula VII in which the variables R11 and R12 are as defined in claim 21, 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 21 in the presence of carbon monoxide, a catalyst and a base.

34. 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 21 and auxiliaries which are customary for formulating crop protection agents.

35. A process for preparing the composition defined in claim 34, 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.

36. 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 21 to act on plants, their habitat or on seed.

37. 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 21 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.

38. 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 21 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.

39. An aniline compound of formula XV in which the variables X, Y, R1 to R3 and R5 and 1 are in each case as defined in claim 21 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.

40. 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 21 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.

41. The compound of formula I defined in claim 21, wherein

X is O or S;
Y together with the two carbons to which it is attached forms an isoxazole ring which is saturated, partially saturated or unsaturated; and
R9 is a radical IIa.

42. The compound of formula I defined in claim 41, wherein R10 is hydroxyl, mercapto, halogen, OR13, SR13, SO2R14 or NR15R16.

Patent History
Publication number: 20070197393
Type: Application
Filed: Aug 1, 2006
Publication Date: Aug 23, 2007
Inventors: Matthias Witschel (Ludwigshafen), Steffen Kudis (Mannheim), Klaus Langemann (Worms), Ernst Baumann (Dudenhofen), Wolfgang von Deyn (Neustadt), Guido Mayer (Neustadt), Ulf Misslitz (Neustadt), Ulf Neidlein (Mannheim), Martina Otten (Ludwigshafen), Karl-Otto Westphalen (Speyer), Helmut Walter (Obrigheim)
Application Number: 11/461,491
Classifications
Current U.S. Class: 504/288.000; 504/235.000; 504/238.000; 504/292.000; 514/248.000; 514/454.000; 548/356.100; 548/373.100; 548/376.100; 549/228.000; 549/23.000
International Classification: A01N 43/02 (20060101); A01N 43/08 (20060101); A01N 43/16 (20060101); A01N 43/18 (20060101); A01N 43/58 (20060101);