TREA

TRICYCLIC BENZOYLPYRAZOLE DERIVATIVES

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Information

  • Patent Application
  • 20070197393
  • Publication Number
    20070197393
  • Date Filed
    August 01, 2006
    18 years ago
  • Date Published
    August 23, 2007
    17 years ago
Information
Abstract
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.
Description

The present invention relates to novel tricyclic benzoylpyrazole derivatives of the formula I
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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
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      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″
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Likewise, in the case of R10=hydroxyl or mercapto, IIb also represents the tautomeric forms IIb′ and IIb″
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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
    embedded image

    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).
      embedded imageembedded image

      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:
      embedded imageembedded image
  • 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
    embedded image

    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:
    embedded image
  • 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:
embedded image


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 1Ia1embedded imagenXR4R10R11  1bondFOHCH3  2bondClOHCH3  3bondBrOHCH3  4bondNO2OHCH3  5bondSCH3OHCH3  6bondSO2CH3OHCH3  7bondSO2CH2CH3OHCH3  8bondCH3OHCH3  9bondCF3OHCH3 10bondOCHF2OHCH3 11CH2FOHCH3 12CH2ClOHCH3 13CH2BrOHCH3 14CH2NO2OHCH3 15CH2SCH3OHCH3 16CH2SO2CH3OHCH3 17CH2SO2CH2CH3OHCH3 18CH2CH3OHCH3 19CH2CF3OHCH3 20CH2OCHF2OHCH3 21OFOHCH3 22OClOHCH3 23OBrOHCH3 24ONO2OHCH3 25OSCH3OHCH3 26OSO2CH3OHCH3 27OSO2CH2CH3OHCH3 28OCH3OHCH3 29OCF3OHCH3 30OOCHF2OHCH3 31SFOHCH3 32SClOHCH3 33SBrOHCH3 34SNO2OHCH3 35SSCH3OHCH3 36SSO2CH3OHCH3 37SSO2CH2CH3OHCH3 38SCH3OHCH3 39SCF3OHCH3 40SOCHF2OHCH3 41SO2FOHCH3 42SO2ClOHCH3 43SO2BrOHCH3 44SO2NO2OHCH3 45SO2SCH3OHCH3 46SO2SO2CH3OHCH3 47SO2SO2CH2CH3OHCH3 48SO2CH3OHCH3 49SO2CF3OHCH3 50SO2OCHF2OHCH3 51bondFOHCH2CH3 52bondClOHCH2CH3 53bondBrOHCH2CH3 54bondNO2OHCH2CH3 55bondSCH3OHCH2CH3 56bondSO2CH3OHCH2CH3 57bondSO2CH2CH3OHCH2CH3 58bondCH3OHCH2CH3 59bondCF3OHCH2CH3 60bondOCHF2OHCH2CH3 61CH2FOHCH2CH3 62CH2ClOHCH2CH3 63CH2BrOHCH2CH3 64CH2NO2OHCH2CH3 65CH2SCH3OHCH2CH3 66CH2SO2CH3OHCH2CH3 67CH2SO2CH2CH3OHCH2CH3 68CH2CH3OHCH2CH3 69CH2CF3OHCH2CH3 70CH2OCHF2OHCH2CH3 71OFOHCH2CH3 72OClOHCH2CH3 73OBrOHCH2CH3 74ONO2OHCH2CH3 75OSCH3OHCH2CH3 76OSO2CH3OHCH2CH3 77OSO2CH2CH3OHCH2CH3 78OCH3OHCH2CH3 79OCF3OHCH2CH3 80OOCHF2OHCH2CH3 81SFOHCH2CH3 82SClOHCH2CH3 83SBrOHCH2CH3 84SNO2OHCH2CH3 85SSCH3OHCH2CH3 86SSO2CH3OHCH2CH3 87SSO2CH2CH3OHCH2CH3 88SCH3OHCH2CH3 89SCF3OHCH2CH3 90SOCHF2OHCH2CH3 91SO2FOHCH2CH3 92SO2ClOHCH2CH3 93SO2BrOHCH2CH3 94SO2NO2OHCH2CH3 95SO2SCH3OHCH2CH3 96SO2SO2CH3OHCH2CH3 97SO2SO2CH2CH3OHCH2CH3 98SO2CH3OHCH2CH3 99SO2CF3OHCH2CH3 100SO2OCHF2OHCH2CH3 101bondFOCOC6H5CH3 102bondClOCOC6H5CH3 103bondBrOCOC6H5CH3 104bondNO2OCOC6H5CH3 105bondSCH3OCOC6H5CH3 106bondSO2CH3OCOC6H5CH3 107bondSO2CH2CH3OCOC6H5CH3 108bondCH3OCOC6H5CH3 109bondCF3OCOC6H5CH3 110bondOCHF2OCOC6H5CH3 111CH2FOCOC6H5CH3 112CH2ClOCOC6H5CH3 113CH2BrOCOC6H5CH3 114CH2NO2OCOC6H5CH3 115CH2SCH3OCOC6H5CH3 116CH2SO2CH3OCOC6H5CH3 117CH2SO2CH2CH3OCOC6H5CH3 118CH2CH3OCOC6H5CH3 119CH2CF3OCOC6H5CH3 120CH2OCHF2OCOC6H5CH3 121OFOCOC6H5CH3 122OClOCOC6H5CH3 123OBrOCOC6H5CH3 124ONO2OCOC6H5CH3 125OSCH3OCOC6H5CH3 126OSO2CH3OCOC6H5CH3 127OSO2CH2CH3OCOC6H5CH3 128OCH3OCOC6H5CH3 129OCF3OCOC6H5CH3 130OOCHF2OCOC6H5CH3 131SFOCOC6H5CH3 132SClOCOC6H5CH3 133SBrOCOC6H5CH3 134SNO2OCOC6H5CH3 135SSCH3OCOC6H5CH3 136SSO2CH3OCOC6H5CH3 137SSO2CH2CH3OCOC6H5CH3 138SCH3OCOC6H5CH3 139SCF3OCOC6H5CH3 140SOCHF2OCOC6H5CH3 141SO2FOCOC6H5CH3 142SO2ClOCOC6H5CH3 143SO2BrOCOC6H5CH3 144SO2NO2OCOC6H5CH3 145SO2SCH3OCOC6H5CH3 146SO2SO2CH3OCOC6H5CH3 147SO2SO2CH2CH3OCOC6H5CH3 148SO2CH3OCOC6H5CH3 149SO2CF3OCOC6H5CH3 150SO2OCHF2OCOC6H5CH3 151bondFOCOC6H5CH2CH3 152bondClOCOC6H5CH2CH3 153bondBrOCOC6H5CH2CH3 154bondNO2OCOC6H5CH2CH3 155bondSCH3OCOC6H5CH2CH3 156bondSO2CH3OCOC6H5CH2CH3 157bondSO2CH2CH3OCOC6H5CH2CH3 158bondCH3OCOC6H5CH2CH3 159bondCF3OCOC6H5CH2CH3 160bondOCHF2OCOC6H5CH2CH3 161CH2FOCOC6H5CH2CH3 162CH2ClOCOC6H5CH2CH3 163CH2BrOCOC6H5CH2CH3 164CH2NO2OCOC6H5CH2CH3 165CH2SCH3OCOC6H5CH2CH3 166CH2SO2CH3OCOC6H5CH2CH3 167CH2SO2CH2CH3OCOC6H5CH2CH3 168CH2CH3OCOC6H5CH2CH3 169CH2CF3OCOC6H5CH2CH3 170CH2OCHF2OCOC6H5CH2CH3 171OFOCOC6H5CH2CH3 172OClOCOC6H5CH2CH3 173OBrOCOC6H5CH2CH3 174ONO2OCOC6H5CH2CH3 175OSCH3OCOC6H5CH2CH3 176OSO2CH3OCOC6H5CH2CH3 177OSO2CH2CH3OCOC6H5CH2CH3 178OCH3OCOC6H5CH2CH3 179OCF3OCOC6H5CH2CH3 180OOCHF2OCOC6H5CH2CH3 181SFOCOC6H5CH2CH3 182SClOCOC6H5CH2CH3 183SBrOCOC6H5CH2CH3 184SNO2OCOC6H5CH2CH3 185SSCH3OCOC6H5CH2CH3 186SSO2CH3OCOC6H5CH2CH3 187SSO2CH2CH3OCOC6H5CH2CH3 188SCH3OCOC6H5CH2CH3 189SCF3OCOC6H5CH2CH3 190SOCHF2OCOC6H5CH2CH3 191SO2FOCOC6H5CH2CH3 192SO2ClOCOC6H5CH2CH3 193SO2BrOCOC6H5CH2CH3 194SO2NO2OCOC6H5CH2CH3 195SO2SCH3OCOC6H5CH2CH3 196SO2SO2CH3OCOC6H5CH2CH3 197SO2SO2CH2CH3OCOC6H5CH2CH3 198SO2CH3OCOC6H5CH2CH3 199SO2CF3OCOC6H5CH2CH3 200SO2OCHF2OCOC6H5CH2CH3 201bondFOCOC(CH3)3CH3 202bondClOCOC(CH3)3CH3 203bondBrOCOC(CH3)3CH3 204bondNO2OCOC(CH3)3CH3 205bondSCH3OCOC(CH3)3CH3 206bondSO2CH3OCOC(CH3)3CH3 207bondSO2CH2CH3OCOC(CH3)3CH3 208bondCH3OCOC(CH3)3CH3 209bondCF3OCOC(CH3)3CH3 210bondOCHF2OCOC(CH3)3CH3 211CH2FOCOC(CH3)3CH3 212CH2ClOCOC(CH3)3CH3 213CH2BrOCOC(CH3)3CH3 214CH2NO2OCOC(CH3)3CH3 215CH2SCH3OCOC(CH3)3CH3 216CH2SO2CH3OCOC(CH3)3CH3 217CH2SO2CH2CH3OCOC(CH3)3CH3 218CH2CH3OCOC(CH3)3CH3 219CH2CF3OCOC(CH3)3CH3 220CH2OCHF2OCOC(CH3)3CH3 221OFOCOC(CH3)3CH3 222OClOCOC(CH3)3CH3 223OBrOCOC(CH3)3CH3 224ONO2OCOC(CH3)3CH3 225OSCH3OCOC(CH3)3CH3 226OSO2CH3OCOC(CH3)3CH3 227OSO2CH2CH3OCOC(CH3)3CH3 228OCH3OCOC(CH3)3CH3 229OCF3OCOC(CH3)3CH3 230OOCHF2OCOC(CH3)3CH3 231SFOCOC(CH3)3CH3 232SClOCOC(CH3)3CH3 233SBrOCOC(CH3)3CH3 234SNO2OCOC(CH3)3CH3 235SSCH3OCOC(CH3)3CH3 236SSO2CH3OCOC(CH3)3CH3 237SSO2CH2CH3OCOC(CH3)3CH3 238SCH3OCOC(CH3)3CH3 239SCF3OCOC(CH3)3CH3 240SOCHF2OCOC(CH3)3CH3 241SO2FOCOC(CH3)3CH3 242SO2ClOCOC(CH3)3CH3 243SO2BrOCOC(CH3)3CH3 244SO2NO2OCOC(CH3)3CH3 245SO2SCH3OCOC(CH3)3CH3 246SO2SO2CH3OCOC(CH3)3CH3 247SO2SO2CH2CH3OCOC(CH3)3CH3 248SO2CH3OCOC(CH3)3CH3 249SO2CF3OCOC(CH3)3CH3 250SO2OCHF2OCOC(CH3)3CH3 251bondFOCOC(CH3)3CH2CH3 252bondClOCOC(CH3)3CH2CH3 253bondBrOCOC(CH3)3CH2CH3 254bondNO2OCOC(CH3)3CH2CH3 255bondSCH3OCOC(CH3)3CH2CH3 256bondSO2CH3OCOC(CH3)3CH2CH3 257bondSO2CH2CH3OCOC(CH3)3CH2CH3 258bondCH3OCOC(CH3)3CH2CH3 259bondCF3OCOC(CH3)3CH2CH3 260bondOCHF2OCOC(CH3)3CH2CH3 261CH2FOCOC(CH3)3CH2CH3 262CH2ClOCOC(CH3)3CH2CH3 263CH2BrOCOC(CH3)3CH2CH3 264CH2NO2OCOC(CH3)3CH2CH3 265CH2SCH3OCOC(CH3)3CH2CH3 266CH2SO2CH3OCOC(CH3)3CH2CH3 267CH2SO2CH2CH3OCOC(CH3)3CH2CH3 268CH2CH3OCOC(CH3)3CH2CH3 269CH2CF3OCOC(CH3)3CH2CH3 270CH2OCHF2OCOC(CH3)3CH2CH3 271OFOCOC(CH3)3CH2CH3 272OClOCOC(CH3)3CH2CH3 273OBrOCOC(CH3)3CH2CH3 274ONO2OCOC(CH3)3CH2CH3 275OSCH3OCOC(CH3)3CH2CH3 276OSO2CH3OCOC(CH3)3CH2CH3 277OSO2CH2CH3OCOC(CH3)3CH2CH3 278OCH3OCOC(CH3)3CH2CH3 279OCF3OCOC(CH3)3CH2CH3 280OOCHF2OCOC(CH3)3CH2CH3 281SFOCOC(CH3)3CH2CH3 282SClOCOC(CH3)3CH2CH3 283SBrOCOC(CH3)3CH2CH3 284SNO2OCOC(CH3)3CH2CH3 285SSCH3OCOC(CH3)3CH2CH3 286SSO2CH3OCOC(CH3)3CH2CH3 287SSO2CH2CH3OCOC(CH3)3CH2CH3 288SCH3OCOC(CH3)3CH2CH3 289SCF3OCOC(CH3)3CH2CH3 290SOCHF2OCOC(CH3)3CH2CH3 291SO2FOCOC(CH3)3CH2CH3 292SO2ClOCOC(CH3)3CH2CH3 293SO2BrOCOC(CH3)3CH2CH3 294SO2NO2OCOC(CH3)3CH2CH3 295SO2SCH3OCOC(CH3)3CH2CH3 296SO2SO2CH3OCOC(CH3)3CH2CH3 297SO2SO2CH2CH3OCOC(CH3)3CH2CH3 298SO2CH3OCOC(CH3)3CH2CH3 299SO2CF3OCOC(CH3)3CH2CH3 300SO2OCHF2OCOC(CH3)3CH2CH3 301bondFOCOSCH3CH3 302bondClOCOSCH3CH3 303bondBrOCOSCH3CH3 304bondNO2OCOSCH3CH3 305bondSCH3OCOSCH3CH3 306bondSO2CH3OCOSCH3CH3 307bondSO2CH2CH3OCOSCH3CH3 308bondCH3OCOSCH3CH3 309bondCF3OCOSCH3CH3 310bondOCHF2OCOSCH3CH3 311CH2FOCOSCH3CH3 312CH2ClOCOSCH3CH3 313CH2BrOCOSCH3CH3 314CH2NO2OCOSCH3CH3 315CH2SCH3OCOSCH3CH3 316CH2SO2CH3OCOSCH3CH3 317CH2SO2CH2CH3OCOSCH3CH3 318CH2CH3OCOSCH3CH3 319CH2CF3OCOSCH3CH3 320CH2OCHF2OCOSCH3CH3 321OFOCOSCH3CH3 322OClOCOSCH3CH3 323OBrOCOSCH3CH3 324ONO2OCOSCH3CH3 325OSCH3OCOSCH3CH3 326OSO2CH3OCOSCH3CH3 327OSO2CH2CH3OCOSCH3CH3 328OCH3OCOSCH3CH3 329OCF3OCOSCH3CH3 330OOCHF2OCOSCH3CH3 331SFOCOSCH3CH3 332SClOCOSCH3CH3 333SBrOCOSCH3CH3 334SNO2OCOSCH3CH3 335SSCH3OCOSCH3CH3 336SSO2CH3OCOSCH3CH3 337SSO2CH2CH3OCOSCH3CH3 338SCH3OCOSCH3CH3 339SCF3OCOSCH3CH3 340SOCHF2OCOSCH3CH3 341SO2FOCOSCH3CH3 342SO2ClOCOSCH3CH3 343SO2BrOCOSCH3CH3 344SO2NO2OCOSCH3CH3 345SO2SCH3OCOSCH3CH3 346SO2SO2CH3OCOSCH3CH3 347SO2SO2CH2CH3OCOSCH3CH3 348SO2CH3OCOSCH3CH3 349SO2CF3OCOSCH3CH3 350SO2OCHF2OCOSCH3CH3 351bondFOCOSCH3CH2CH3 352bondClOCOSCH3CH2CH3 353bondBrOCOSCH3CH2CH3 354bondNO2OCOSCH3CH2CH3 355bondSCH3OCOSCH3CH2CH3 356bondSO2CH3OCOSCH3CH2CH3 357bondSO2CH2CH3OCOSCH3CH2CH3 358bondCH3OCOSCH3CH2CH3 359bondCF3OCOSCH3CH2CH3 360bondOCHF2OCOSCH3CH2CH3 361CH2FOCOSCH3CH2CH3 362CH2ClOCOSCH3CH2CH3 363CH2BrOCOSCH3CH2CH3 364CH2NO2OCOSCH3CH2CH3 365CH2SCH3OCOSCH3CH2CH3 366CH2SO2CH3OCOSCH3CH2CH3 367CH2SO2CH2CH3OCOSCH3CH2CH3 368CH2CH3OCOSCH3CH2CH3 369CH2CF3OCOSCH3CH2CH3 370CH2OCHF2OCOSCH3CH2CH3 371OFOCOSCH3CH2CH3 372OClOCOSCH3CH2CH3 373OBrOCOSCH3CH2CH3 374ONO2OCOSCH3CH2CH3 375OSCH3OCOSCH3CH2CH3 376OSO2CH3OCOSCH3CH2CH3 377OSO2CH2CH3OCOSCH3CH2CH3 378OCH3OCOSCH3CH2CH3 379OCF3OCOSCH3CH2CH3 380OOCHF2OCOSCH3CH2CH3 381SFOCOSCH3CH2CH3 382SClOCOSCH3CH2CH3 383SBrOCOSCH3CH2CH3 384SNO2OCOSCH3CH2CH3 385SSCH3OCOSCH3CH2CH3 386SSO2CH3OCOSCH3CH2CH3 387SSO2CH2CH3OCOSCH3CH2CH3 388SCH3OCOSCH3CH2CH3 389SCF3OCOSCH3CH2CH3 390SOCHF2OCOSCH3CH2CH3 391SO2FOCOSCH3CH2CH3 392SO2ClOCOSCH3CH2CH3 393SO2BrOCOSCH3CH2CH3 394SO2NO2OCOSCH3CH2CH3 395SO2SCH3OCOSCH3CH2CH3 396SO2SO2CH3OCOSCH3CH2CH3 397SO2SO2CH2CH3OCOSCH3CH2CH3 398SO2CH3OCOSCH3CH2CH3 399SO2CF3OCOSCH3CH2CH3 400SO2OCHF2OCOSCH3CH2CH3 401bondFOCH3CH3 402bondClOCH3CH3 403bondBrOCH3CH3 404bondNO2OCH3CH3 405bondSCH3OCH3CH3 406bondSO2CH3OCH3CH3 407bondSO2CH2CH3OCH3CH3 408bondCH3OCH3CH3 409bondCF3OCH3CH3 410bondOCHF2OCH3CH3 411CH2FOCH3CH3 412CH2ClOCH3CH3 413CH2BrOCH3CH3 414CH2NO2OCH3CH3 415CH2SCH3OCH3CH3 416CH2SO2CH3OCH3CH3 417CH2SO2CH2CH3OCH3CH3 418CH2CH3OCH3CH3 419CH2CF3OCH3CH3 420CH2OCHF2OCH3CH3 421OFOCH3CH3 422OClOCH3CH3 423OBrOCH3CH3 424ONO2OCH3CH3 425OSCH3OCH3CH3 426OSO2CH3OCH3CH3 427OSO2CH2CH3OCH3CH3 428OCH3OCH3CH3 429OCF3OCH3CH3 430OOCHF2OCH3CH3 431SFOCH3CH3 432SClOCH3CH3 433SBrOCH3CH3 434SNO2OCH3CH3 435SSCH3OCH3CH3 436SSO2CH3OCH3CH3 437SSO2CH2CH3OCH3CH3 438SCH3OCH3CH3 439SCF3OCH3CH3 440SOCHF2OCH3CH3 441SO2FOCH3CH3 442SO2ClOCH3CH3 443SO2BrOCH3CH3 444SO2NO2OCH3CH3 445SO2SCH3OCH3CH3 446SO2SO2CH3OCH3CH3 447SO2SO2CH2CH3OCH3CH3 448SO2CH3OCH3CH3 449SO2CF3OCH3CH3 450SO2OCHF2OCH3CH3 451bondFOCH3CH2CH3 452bondClOCH3CH2CH3 453bondBrOCH3CH2CH3 454bondNO2OCH3CH2CH3 455bondSCH3OCH3CH2CH3 456bondSO2CH3OCH3CH2CH3 457bondSO2CH2CH3OCH3CH2CH3 458bondCH3OCH3CH2CH3 459bondCF3OCH3CH2CH3 460bondOCHF2OCH3CH2CH3 461CH2FOCH3CH2CH3 462CH2ClOCH3CH2CH3 463CH2BrOCH3CH2CH3 464CH2NO2OCH3CH2CH3 465CH2SCH3OCH3CH2CH3 466CH2SO2CH3OCH3CH2CH3 467CH2SO2CH2CH3OCH3CH2CH3 468CH2CH3OCH3CH2CH3 469CH2CF3OCH3CH2CH3 470CH2OCHF2OCH3CH2CH3 471OFOCH3CH2CH3 472OClOCH3CH2CH3 473OBrOCH3CH2CH3 474ONO2OCH3CH2CH3 475OSCH3OCH3CH2CH3 476OSO2CH3OCH3CH2CH3 477OSO2CH2CH3OCH3CH2CH3 478OCH3OCH3CH2CH3 479OCF3OCH3CH2CH3 480OOCHF2OCH3CH2CH3 481SFOCH3CH2CH3 482SClOCH3CH2CH3 483SBrOCH3CH2CH3 484SNO2OCH3CH2CH3 485SSCH3OCH3CH2CH3 486SSO2CH3OCH3CH2CH3 487SSO2CH2CH3OCH3CH2CH3 488SCH3OCH3CH2CH3 489SCF3OCH3CH2CH3 490SOCHF2OCH3CH2CH3 491SO2FOCH3CH2CH3 492SO2ClOCH3CH2CH3 493SO2BrOCH3CH2CH3 494SO2NO2OCH3CH2CH3 495SO2SCH3OCH3CH2CH3 496SO2SO2CH3OCH3CH2CH3 497SO2SO2CH2CH3OCH3CH2CH3 498SO2CH3OCH3CH2CH3 499SO2CF3OCH3CH2CH3 500SO2OCHF2OCH3CH2CH3 501bondFOCH(CH3)2CH3 502bondClOCH(CH3)2CH3 503bondBrOCH(CH3)2CH3 504bondNO2OCH(CH3)2CH3 505bondSCH3OCH(CH3)2CH3 506bondSO2CH3OCH(CH3)2CH3 507bondSO2CH2CH3OCH(CH3)2CH3 508bondCH3OCH(CH3)2CH3 509bondCF3OCH(CH3)2CH3 510bondOCHF2OCH(CH3)2CH3 511CH2FOCH(CH3)2CH3 512CH2ClOCH(CH3)2CH3 513CH2BrOCH(CH3)2CH3 514CH2NO2OCH(CH3)2CH3 515CH2SCH3OCH(CH3)2CH3 516CH2SO2CH3OCH(CH3)2CH3 517CH2SO2CH2CH3OCH(CH3)2CH3 518CH2CH3OCH(CH3)2CH3 519CH2CF3OCH(CH3)2CH3 520CH2OCHF2OCH(CH3)2CH3 521OFOCH(CH3)2CH3 522OClOCH(CH3)2CH3 523OBrOCH(CH3)2CH3 524ONO2OCH(CH3)2CH3 525OSCH3OCH(CH3)2CH3 526OSO2CH3OCH(CH3)2CH3 527OSO2CH2CH3OCH(CH3)2CH3 528OCH3OCH(CH3)2CH3 529OCF3OCH(CH3)2CH3 530OOCHF2OCH(CH3)2CH3 531SFOCH(CH3)2CH3 532SClOCH(CH3)2CH3 533SBrOCH(CH3)2CH3 534SNO2OCH(CH3)2CH3 535SSCH3OCH(CH3)2CH3 536SSO2CH3OCH(CH3)2CH3 537SSO2CH2CH3OCH(CH3)2CH3 538SCH3OCH(CH3)2CH3 539SCF3OCH(CH3)2CH3 540SOCHF2OCH(CH3)2CH3 541SO2FOCH(CH3)2CH3 542SO2ClOCH(CH3)2CH3 543SO2BrOCH(CH3)2CH3 544SO2NO2OCH(CH3)2CH3 545SO2SCH3OCH(CH3)2CH3 546SO2SO2CH3OCH(CH3)2CH3 547SO2SO2CH2CH3OCH(CH3)2CH3 548SO2CH3OCH(CH3)2CH3 549SO2CF3OCH(CH3)2CH3 550SO2OCHF2OCH(CH3)2CH3 551bondFOCH(CH3)2CH2CH3 552bondClOCH(CH3)2CH2CH3 553bondBrOCH(CH3)2CH2CH3 554bondNO2OCH(CH3)2CH2CH3 555bondSCH3OCH(CH3)2CH2CH3 556bondSO2CH3OCH(CH3)2CH2CH3 557bondSO2CH2CH3OCH(CH3)2CH2CH3 558bondCH3OCH(CH3)2CH2CH3 559bondCF3OCH(CH3)2CH2CH3 560bondOCHF2OCH(CH3)2CH2CH3 561CH2FOCH(CH3)2CH2CH3 562CH2ClOCH(CH3)2CH2CH3 563CH2BrOCH(CH3)2CH2CH3 564CH2NO2OCH(CH3)2CH2CH3 565CH2SCH3OCH(CH3)2CH2CH3 566CH2SO2CH3OCH(CH3)2CH2CH3 567CH2SO2CH2CH3OCH(CH3)2CH2CH3 568CH2CH3OCH(CH3)2CH2CH3 569CH2CF3OCH(CH3)2CH2CH3 570CH2OCHF2OCH(CH3)2CH2CH3 571OFOCH(CH3)2CH2CH3 572OClOCH(CH3)2CH2CH3 573OBrOCH(CH3)2CH2CH3 574ONO2OCH(CH3)2CH2CH3 575OSCH3OCH(CH3)2CH2CH3 576OSO2CH3OCH(CH3)2CH2CH3 577OSO2CH2CH3OCH(CH3)2CH2CH3 578OCH3OCH(CH3)2CH2CH3 579OCF3OCH(CH3)2CH2CH3 580OOCHF2OCH(CH3)2CH2CH3 581SFOCH(CH3)2CH2CH3 582SClOCH(CH3)2CH2CH3 583SBrOCH(CH3)2CH2CH3 584SNO2OCH(CH3)2CH2CH3 585SSCH3OCH(CH3)2CH2CH3 586SSO2CH3OCH(CH3)2CH2CH3 587SSO2CH2CH3OCH(CH3)2CH2CH3 588SCH3OCH(CH3)2CH2CH3 589SCF3OCH(CH3)2CH2CH3 590SOCHF2OCH(CH3)2CH2CH3 591SO2FOCH(CH3)2CH2CH3 592SO2ClOCH(CH3)2CH2CH3 593SO2BrOCH(CH3)2CH2CH3 594SO2NO2OCH(CH3)2CH2CH3 595SO2SCH3OCH(CH3)2CH2CH3 596SO2SO2CH3OCH(CH3)2CH2CH3 597SO2SO2CH2CH3OCH(CH3)2CH2CH3 598SO2CH3OCH(CH3)2CH2CH3 599SO2CF3OCH(CH3)2CH2CH3 600SO2OCHF2OCH(CH3)2CH2CH3 601bondFOCH2C6H5CH3 602bondClOCH2C6H5CH3 603bondBrOCH2C6H5CH3 604bondNO2OCH2C6H5CH3 605bondSCH3OCH2C6H5CH3 606bondSO2CH3OCH2C6H5CH3 607bondSO2CH2CH3OCH2C6H5CH3 608bondCH3OCH2C6H5CH3 609bondCF3OCH2C6H5CH3 610bondOCHF2OCH2C6H5CH3 611CH2FOCH2C6H5CH3 612CH2ClOCH2C6H5CH3 613CH2BrOCH2C6H5CH3 614CH2NO2OCH2C6H5CH3 615CH2SCH3OCH2C6H5CH3 616CH2SO2CH3OCH2C6H5CH3 617CH2SO2CH2CH3OCH2C6H5CH3 618CH2CH3OCH2C6H5CH3 619CH2CF3OCH2C6H5CH3 620CH2OCHF2OCH2C6H5CH3 621OFOCH2C6H5CH3 622OClOCH2C6H5CH3 623OBrOCH2C6H5CH3 624ONO2OCH2C6H5CH3 625OSCH3OCH2C6H5CH3 626OSO2CH3OCH2C6H5CH3 627OSO2CH2CH3OCH2C6H5CH3 628OCH3OCH2C6H5CH3 629OCF3OCH2C6H5CH3 630OOCHF2OCH2C6H5CH3 631SFOCH2C6H5CH3 632SClOCH2C6H5CH3 633SBrOCH2C6H5CH3 634SNO2OCH2C6H5CH3 635SSCH3OCH2C6H5CH3 636SSO2CH3OCH2C6H5CH3 637SSO2CH2CH3OCH2C6H5CH3 638SCH3OCH2C6H5CH3 639SCF3OCH2C6H5CH3 640SOCHF2OCH2C6H5CH3 641SO2FOCH2C6H5CH3 642SO2ClOCH2C6H5CH3 643SO2BrOCH2C6H5CH3 644SO2NO2OCH2C6H5CH3 645SO2SCH3OCH2C6H5CH3 646SO2SO2CH3OCH2C6H5CH3 647SO2SO2CH2CH3OCH2C6H5CH3 648SO2CH3OCH2C6H5CH3 649SO2CF3OCH2C6H5CH3 650SO2OCHF2OCH2C6H5CH3 651bondFOCH2C6H5CH2CH3 652bondClOCH2C6H5CH2CH3 653bondBrOCH2C6H5CH2CH3 654bondNO2OCH2C6H5CH2CH3 655bondSCH3OCH2C6H5CH2CH3 656bondSO2CH3OCH2C6H5CH2CH3 657bondSO2CH2CH3OCH2C6H5CH2CH3 658bondCH3OCH2C6H5CH2CH3 659bondCF3OCH2C6H5CH2CH3 660bondOCHF2OCH2C6H5CH2CH3 661CH2FOCH2C6H5CH2CH3 662CH2ClOCH2C6H5CH2CH3 663CH2BrOCH2C6H5CH2CH3 664CH2NO2OCH2C6H5CH2CH3 665CH2SCH3OCH2C6H5CH2CH3 666CH2SO2CH3OCH2C6H5CH2CH3 667CH2SO2CH2CH3OCH2C6H5CH2CH3 668CH2CH3OCH2C6H5CH2CH3 669CH2CF3OCH2C6H5CH2CH3 670CH2OCHF2OCH2C6H5CH2CH3 671OFOCH2C6H5CH2CH3 672OClOCH2C6H5CH2CH3 673OBrOCH2C6H5CH2CH3 674ONO2OCH2C6H5CH2CH3 675OSCH3OCH2C6H5CH2CH3 676OSO2CH3OCH2C6H5CH2CH3 677OSO2CH2CH3OCH2C6H5CH2CH3 678OCH3OCH2C6H5CH2CH3 679OCF3OCH2C6H5CH2CH3 680OOCHF2OCH2C6H5CH2CH3 681SFOCH2C6H5CH2CH3 682SClOCH2C6H5CH2CH3 683SBrOCH2C6H5CH2CH3 684SNO2OCH2C6H5CH2CH3 685SSCH3OCH2C6H5CH2CH3 686SSO2CH3OCH2C6H5CH2CH3 687SSO2CH2CH3OCH2C6H5CH2CH3 688SCH3OCH2C6H5CH2CH3 689SCF3OCH2C6H5CH2CH3 690SOCHF2OCH2C6H5CH2CH3 691SO2FOCH2C6H5CH2CH3 692SO2ClOCH2C6H5CH2CH3 693SO2BrOCH2C6H5CH2CH3 694SO2NO2OCH2C6H5CH2CH3 695SO2SCH3OCH2C6H5CH2CH3 696SO2SO2CH3OCH2C6H5CH2CH3 697SO2SO2CH2CH3OCH2C6H5CH2CH3 698SO2CH3OCH2C6H5CH2CH3 699SO2CF3OCH2C6H5CH2CH3 700SO2OCHF2OCH2C6H5CH2CH3 701bondFOSO2(4-CH3—C6H4)CH3 702bondClOSO2(4-CH3—C6H4)CH3 703bondBrOSO2(4-CH3—C6H4)CH3 704bondNO2OSO2(4-CH3—C6H4)CH3 705bondSCH3OSO2(4-CH3—C6H4)CH3 706bondSO2CH3OSO2(4-CH3—C6H4)CH3 707bondSO2CH2CH3OSO2(4-CH3—C6H4)CH3 708bondCH3OSO2(4-CH3—C6H4)CH3 709bondCF3OSO2(4-CH3—C6H4)CH3 710bondOCHF2OSO2(4-CH3—C6H4)CH3 711CH2FOSO2(4-CH3—C6H4)CH3 712CH2ClOSO2(4-CH3—C6H4)CH3 713CH2BrOSO2(4-CH3—C6H4)CH3 714CH2NO2OSO2(4-CH3—C6H4)CH3 715CH2SCH3OSO2(4-CH3—C6H4)CH3 716CH2SO2CH3OSO2(4-CH3—C6H4)CH3 717CH2SO2CH2CH3OSO2(4-CH3—C6H4)CH3 718CH2CH3OSO2(4-CH3—C6H4)CH3 719CH2CF3OSO2(4-CH3—C6H4)CH3 720CH2OCHF2OSO2(4-CH3—C6H4)CH3 721OFOSO2(4-CH3—C6H4)CH3 722OClOSO2(4-CH3—C6H4)CH3 723OBrOSO2(4-CH3—C6H4)CH3 724ONO2OSO2(4-CH3—C6H4)CH3 725OSCH3OSO2(4-CH3—C6H4)CH3 726OSO2CH3OSO2(4-CH3—C6H4)CH3 727OSO2CH2CH3OSO2(4-CH3—C6H4)CH3 728OCH3OSO2(4-CH3—C6H4)CH3 729OCF3OSO2(4-CH3—C6H4)CH3 730OOCHF2OSO2(4-CH3—C6H4)CH3 731SFOSO2(4-CH3—C6H4)CH3 732SClOSO2(4-CH3—C6H4)CH3 733SBrOSO2(4-CH3—C6H4)CH3 734SNO2OSO2(4-CH3—C6H4)CH3 735SSCH3OSO2(4-CH3—C6H4)CH3 736SSO2CH3OSO2(4-CH3—C6H4)CH3 737SSO2CH2CH3OSO2(4-CH3—C6H4)CH3 738SCH3OSO2(4-CH3—C6H4)CH3 739SCF3OSO2(4-CH3—C6H4)CH3 740SOCHF2OSO2(4-CH3—C6H4)CH3 741SO2FOSO2(4-CH3—C6H4)CH3 742SO2ClOSO2(4-CH3—C6H4)CH3 743SO2BrOSO2(4-CH3—C6H4)CH3 744SO2NO2OSO2(4-CH3—C6H4)CH3 745SO2SCH3OSO2(4-CH3—C6H4)CH3 746SO2SO2CH3OSO2(4-CH3—C6H4)CH3 747SO2SO2CH2CH3OSO2(4-CH3—C6H4)CH3 748SO2CH3OSO2(4-CH3—C6H4)CH3 749SO2CF3OSO2(4-CH3—C6H4)CH3 750SO2OCHF2OSO2(4-CH3—C6H4)CH3 751bondFOSO2(4-CH3—C6H4)CH2CH3 752bondClOSO2(4-CH3—C6H4)CH2CH3 753bondBrOSO2(4-CH3—C6H4)CH2CH3 754bondNO2OSO2(4-CH3—C6H4)CH2CH3 755bondSCH3OSO2(4-CH3—C6H4)CH2CH3 756bondSO2CH3OSO2(4-CH3—C6H4)CH2CH3 757bondSO2CH2CH3OSO2(4-CH3—C6H4)CH2CH3 758bondCH3OSO2(4-CH3—C6H4)CH2CH3 759bondCF3OSO2(4-CH3—C6H4)CH2CH3 760bondOCHF2OSO2(4-CH3—C6H4)CH2CH3 761CH2FOSO2(4-CH3—C6H4)CH2CH3 762CH2ClOSO2(4-CH3—C6H4)CH2CH3 763CH2BrOSO2(4-CH3—C6H4)CH2CH3 764CH2NO2OSO2(4-CH3—C6H4)CH2CH3 765CH2SCH3OSO2(4-CH3—C6H4)CH2CH3 766CH2SO2CH3OSO2(4-CH3—C6H4)CH2CH3 767CH2SO2CH2CH3OSO2(4-CH3—C6H4)CH2CH3 768CH2CH3OSO2(4-CH3—C6H4)CH2CH3 769CH2CF3OSO2(4-CH3—C6H4)CH2CH3 770CH2OCHF2OSO2(4-CH3—C6H4)CH2CH3 771OFOSO2(4-CH3—C6H4)CH2CH3 772OClOSO2(4-CH3—C6H4)CH2CH3 773OBrOSO2(4-CH3—C6H4)CH2CH3 774ONO2OSO2(4-CH3—C6H4)CH2CH3 775OSCH3OSO2(4-CH3—C6H4)CH2CH3 776OSO2CH3OSO2(4-CH3—C6H4)CH2CH3 777OSO2CH2CH3OSO2(4-CH3—C6H4)CH2CH3 778OCH3OSO2(4-CH3—C6H4)CH2CH3 779OCF3OSO2(4-CH3—C6H4)CH2CH3 780OOCHF2OSO2(4-CH3—C6H4)CH2CH3 781SFOSO2(4-CH3—C6H4)CH2CH3 782SClOSO2(4-CH3—C6H4)CH2CH3 783SBrOSO2(4-CH3—C6H4)CH2CH3 784SNO2OSO2(4-CH3—C6H4)CH2CH3 785SSCH3OSO2(4-CH3—C6H4)CH2CH3 786SSO2CH3OSO2(4-CH3—C6H4)CH2CH3 787SSO2CH2CH3OSO2(4-CH3—C6H4)CH2CH3 788SCH3OSO2(4-CH3—C6H4)CH2CH3 789SCF3OSO2(4-CH3—C6H4)CH2CH3 790SOCHF2OSO2(4-CH3—C6H4)CH2CH3 791SO2FOSO2(4-CH3—C6H4)CH2CH3 792SO2ClOSO2(4-CH3—C6H4)CH2CH3 793SO2BrOSO2(4-CH3—C6H4)CH2CH3 794SO2NO2OSO2(4-CH3—C6H4)CH2CH3 795SO2SCH3OSO2(4-CH3—C6H4)CH2CH3 796SO2SO2CH3OSO2(4-CH3—C6H4)CH2CH3 797SO2SO2CH2CH3OSO2(4-CH3—C6H4)CH2CH3 798SO2CH3OSO2(4-CH3—C6H4)CH2CH3 799SO2CF3OSO2(4-CH3—C6H4)CH2CH3 800SO2OCHF2OSO2(4-CH3—C6H4)CH2CH3 801bondFSCH3CH3 802bondClSCH3CH3 803bondBrSCH3CH3 804bondNO2SCH3CH3 805bondSCH3SCH3CH3 806bondSO2CH3SCH3CH3 807bondSO2CH2CH3SCH3CH3 808bondCH3SCH3CH3 809bondCF3SCH3CH3 810bondOCHF2SCH3CH3 811CH2FSCH3CH3 812CH2ClSCH3CH3 813CH2BrSCH3CH3 814CH2NO2SCH3CH3 815CH2SCH3SCH3CH3 816CH2SO2CH3SCH3CH3 817CH2SO2CH2CH3SCH3CH3 818CH2CH3SCH3CH3 819CH2CF3SCH3CH3 820CH2OCHF2SCH3CH3 821OFSCH3CH3 822OClSCH3CH3 823OBrSCH3CH3 824ONO2SCH3CH3 825OSCH3SCH3CH3 826OSO2CH3SCH3CH3 827OSO2CH2CH3SCH3CH3 828OCH3SCH3CH3 829OCF3SCH3CH3 830OOCHF2SCH3CH3 831SFSCH3CH3 832SClSCH3CH3 833SBrSCH3CH3 834SNO2SCH3CH3 835SSCH3SCH3CH3 836SSO2CH3SCH3CH3 837SSO2CH2CH3SCH3CH3 838SCH3SCH3CH3 839SCF3SCH3CH3 840SOCHF2SCH3CH3 841SO2FSCH3CH3 842SO2ClSCH3CH3 843SO2BrSCH3CH3 844SO2NO2SCH3CH3 845SO2SCH3SCH3CH3 846SO2SO2CH3SCH3CH3 847SO2SO2CH2CH3SCH3CH3 848SO2CH3SCH3CH3 849SO2CF3SCH3CH3 850SO2OCHF2SCH3CH3 851bondFSCH3CH2CH3 852bondClSCH3CH2CH3 853bondBrSCH3CH2CH3 854bondNO2SCH3CH2CH3 855bondSCH3SCH3CH2CH3 856bondSO2CH3SCH3CH2CH3 857bondSO2CH2CH3SCH3CH2CH3 858bondCH3SCH3CH2CH3 859bondCF3SCH3CH2CH3 860bondOCHF2SCH3CH2CH3 861CH2FSCH3CH2CH3 862CH2ClSCH3CH2CH3 863CH2BrSCH3CH2CH3 864CH2NO2SCH3CH2CH3 865CH2SCH3SCH3CH2CH3 866CH2SO2CH3SCH3CH2CH3 867CH2SO2CH2CH3SCH3CH2CH3 868CH2CH3SCH3CH2CH3 869CH2CF3SCH3CH2CH3 870CH2OCHF2SCH3CH2CH3 871OFSCH3CH2CH3 872OClSCH3CH2CH3 873OBrSCH3CH2CH3 874ONO2SCH3CH2CH3 875OSCH3SCH3CH2CH3 876OSO2CH3SCH3CH2CH3 877OSO2CH2CH3SCH3CH2CH3 878OCH3SCH3CH2CH3 879OCF3SCH3CH2CH3 880OOCHF2SCH3CH2CH3 881SFSCH3CH2CH3 882SClSCH3CH2CH3 883SBrSCH3CH2CH3 884SNO2SCH3CH2CH3 885SSCH3SCH3CH2CH3 886SSO2CH3SCH3CH2CH3 887SSO2CH2CH3SCH3CH2CH3 888SCH3SCH3CH2CH3 889SCF3SCH3CH2CH3 890SOCHF2SCH3CH2CH3 891SO2FSCH3CH2CH3 892SO2ClSCH3CH2CH3 893SO2BrSCH3CH2CH3 894SO2NO2SCH3CH2CH3 895SO2SCH3SCH3CH2CH3 896SO2SO2CH3SCH3CH2CH3 897SO2SO2CH2CH3SCH3CH2CH3 898SO2CH3SCH3CH2CH3 899SO2CF3SCH3CH2CH3 900SO2OCHF2SCH3CH2CH3 901bondFClCH3 902bondClClCH3 903bondBrClCH3 904bondNO2ClCH3 905bondSCH3ClCH3 906bondSO2CH3ClCH3 907bondSO2CH2CH3ClCH3 908bondCH3ClCH3 909bondCF3ClCH3 910bondOCHF2ClCH3 911CH2FClCH3 912CH2ClClCH3 913CH2BrClCH3 914CH2NO2ClCH3 915CH2SCH3ClCH3 916CH2SO2CH3ClCH3 917CH2SO2CH2CH3ClCH3 918CH2CH3ClCH3 919CH2CF3ClCH3 920CH2OCHF2ClCH3 921OFClCH3 922OClClCH3 923OBrClCH3 924ONO2ClCH3 925OSCH3ClCH3 926OSO2CH3ClCH3 927OSO2CH2CH3ClCH3 928OCH3ClCH3 929OCF3ClCH3 930OOCHF2ClCH3 931SFClCH3 932SClClCH3 933SBrClCH3 934SNO2ClCH3 935SSCH3ClCH3 936SSO2CH3ClCH3 937SSO2CH2CH3ClCH3 938SCH3ClCH3 939SCF3ClCH3 940SOCHF2ClCH3 941SO2FClCH3 942SO2ClClCH3 943SO2BrClCH3 944SO2NO2ClCH3 945SO2SCH3ClCH3 946SO2SO2CH3ClCH3 947SO2SO2CH2CH3ClCH3 948SO2CH3ClCH3 949SO2CF3ClCH3 950SO2OCHF2ClCH3 951bondFClCH2CH3 952bondClClCH2CH3 953bondBrClCH2CH3 954bondNO2ClCH2CH3 955bondSCH3ClCH2CH3 956bondSO2CH3ClCH2CH3 957bondSO2CH2CH3ClCH2CH3 958bondCH3ClCH2CH3 959bondCF3ClCH2CH3 960bondOCHF2ClCH2CH3 961CH2FClCH2CH3 962CH2ClClCH2CH3 963CH2BrClCH2CH3 964CH2NO2ClCH2CH3 965CH2SCH3ClCH2CH3 966CH2SO2CH3ClCH2CH3 967CH2SO2CH2CH3ClCH2CH3 968CH2CH3ClCH2CH3 969CH2CF3ClCH2CH3 970CH2OCHF2ClCH2CH3 971OFClCH2CH3 972OClClCH2CH3 973OBrClCH2CH3 974ONO2ClCH2CH3 975OSCH3ClCH2CH3 976OSO2CH3ClCH2CH3 977OSO2CH2CH3ClCH2CH3 978OCH3ClCH2CH3 979OCF3ClCH2CH3 980OOCHF2ClCH2CH3 981SFClCH2CH3 982SClClCH2CH3 983SBrClCH2CH3 984SNO2ClCH2CH3 985SSCH3ClCH2CH3 986SSO2CH3ClCH2CH3 987SSO2CH2CH3ClCH2CH3 988SCH3ClCH2CH3 989SCF3ClCH2CH3 990SOCHF2ClCH2CH3 991SO2FClCH2CH3 992SO2ClClCH2CH3 993SO2BrClCH2CH3 994SO2NO2ClCH2CH3 995SO2SCH3ClCH2CH3 996SO2SO2CH3ClCH2CH3 997SO2SO2CH2CH3ClCH2CH3 998SO2CH3ClCH2CH3 999SO2CF3ClCH2CH31000SO2OCHF2ClCH2CH31001bondFOHCH(CH3)21002bondClOHCH(CH3)21003bondBrOHCH(CH3)21004bondNO2OHCH(CH3)21005bondSCH3OHCH(CH3)21006bondSO2CH3OHCH(CH3)21007bondSO2CH2CH3OHCH(CH3)21008bondCH3OHCH(CH3)21009bondCF3OHCH(CH3)21010bondOCHF2OHCH(CH3)21011CH2FOHCH(CH3)21012CH2ClOHCH(CH3)21013CH2BrOHCH(CH3)21014CH2NO2OHCH(CH3)21015CH2SCH3OHCH(CH3)21016CH2SO2CH3OHCH(CH3)21017CH2SO2CH2CH3OHCH(CH3)21018CH2CH3OHCH(CH3)21019CH2CF3OHCH(CH3)21020CH2OCHF2OHCH(CH3)21021OFOHCH(CH3)21022OClOHCH(CH3)21023OBrOHCH(CH3)21024ONO2OHCH(CH3)21025OSCH3OHCH(CH3)21026OSO2CH3OHCH(CH3)21027OSO2CH2CH3OHCH(CH3)21028OCH3OHCH(CH3)21029OCF3OHCH(CH3)21030OOCHF2OHCH(CH3)21031SFOHCH(CH3)21032SClOHCH(CH3)21033SBrOHCH(CH3)21034SNO2OHCH(CH3)21035SSCH3OHCH(CH3)21036SSO2CH3OHCH(CH3)21037SSO2CH2CH3OHCH(CH3)21038SCH3OHCH(CH3)21039SCF3OHCH(CH3)21040SOCHF2OHCH(CH3)21041SO2FOHCH(CH3)21042SO2ClOHCH(CH3)21043SO2BrOHCH(CH3)21044SO2NO2OHCH(CH3)21045SO2SCH3OHCH(CH3)21046SO2SO2CH3OHCH(CH3)21047SO2SO2CH2CH3OHCH(CH3)21048SO2CH3OHCH(CH3)21049SO2CF3OHCH(CH3)21050SO2OCHF2OHCH(CH3)21051bondFOHC(CH3)31052bondClOHC(CH3)31053bondBrOHC(CH3)31054bondNO2OHC(CH3)31055bondSCH3OHC(CH3)31056bondSO2CH3OHC(CH3)31057bondSO2CH2CH3OHC(CH3)31058bondCH3OHC(CH3)31059bondCF3OHC(CH3)31060bondOCHF2OHC(CH3)31061CH2FOHC(CH3)31062CH2ClOHC(CH3)31063CH2BrOHC(CH3)31064CH2NO2OHC(CH3)31065CH2SCH3OHC(CH3)31066CH2SO2CH3OHC(CH3)31067CH2SO2CH2CH3OHC(CH3)31068CH2CH3OHC(CH3)31069CH2CF3OHC(CH3)31070CH2OCHF2OHC(CH3)31071OFOHC(CH3)31072OClOHC(CH3)31073OBrOHC(CH3)31074ONO2OHC(CH3)31075OSCH3OHC(CH3)31076OSO2CH3OHC(CH3)31077OSO2CH2CH3OHC(CH3)31078OCH3OHC(CH3)31079OCF3OHC(CH3)31080OOCHF2OHC(CH3)31081SFOHC(CH3)31082SClOHC(CH3)31083SBrOHC(CH3)31084SNO2OHC(CH3)31085SSCH3OHC(CH3)31086SSO2CH3OHC(CH3)31087SSO2CH2CH3OHC(CH3)31088SCH3OHC(CH3)31089SCF3OHC(CH3)31090SOCHF2OHC(CH3)31091SO2FOHC(CH3)31092SO2ClOHC(CH3)31093SO2BrOHC(CH3)31094SO2NO2OHC(CH3)31095SO2SCH3OHC(CH3)31096SO2SO2CH3OHC(CH3)31097SO2SO2CH2CH3OHC(CH3)31098SO2CH3OHC(CH3)31099SO2CF3OHC(CH3)31100SO2OCHF2OHC(CH3)31101bondFOCOC6H5CH(CH3)21102bondClOCOC6H5CH(CH3)21103bondBrOCOC6H5CH(CH3)21104bondNO2OCOC6H5CH(CH3)21105bondSCH3OCOC6H5CH(CH3)21106bondSO2CH3OCOC6H5CH(CH3)21107bondSO2CH2CH3OCOC6H5CH(CH3)21108bondCH3OCOC6H5CH(CH3)21109bondCF3OCOC6H5CH(CH3)21110bondOCHF2OCOC6H5CH(CH3)21111CH2FOCOC6H5CH(CH3)21112CH2ClOCOC6H5CH(CH3)21113CH2BrOCOC6H5CH(CH3)21114CH2NO2OCOC6H5CH(CH3)21115CH2SCH3OCOC6H5CH(CH3)21116CH2SO2CH3OCOC6H5CH(CH3)21117CH2SO2CH2CH3OCOC6H5CH(CH3)21118CH2CH3OCOC6H5CH(CH3)21119CH2CF3OCOC6H5CH(CH3)21120CH2OCHF2OCOC6H5CH(CH3)21121OFOCOC6H5CH(CH3)21122OClOCOC6H5CH(CH3)21123OBrOCOC6H5CH(CH3)21124ONO2OCOC6H5CH(CH3)21125OSCH3OCOC6H5CH(CH3)21126OSO2CH3OCOC6H5CH(CH3)21127OSO2CH2CH3OCOC6H5CH(CH3)21128OCH3OCOC6H5CH(CH3)21129OCF3OCOC6H5CH(CH3)21130OOCHF2OCOC6H5CH(CH3)21131SFOCOC6H5CH(CH3)21132SClOCOC6H5CH(CH3)21133SBrOCOC6H5CH(CH3)21134SNO2OCOC6H5CH(CH3)21135SSCH3OCOC6H5CH(CH3)21136SSO2CH3OCOC6H5CH(CH3)21137SSO2CH2CH3OCOC6H5CH(CH3)21138SCH3OCOC6H5CH(CH3)21139SCF3OCOC6H5CH(CH3)21140SOCHF2OCOC6H5CH(CH3)21141SO2FOCOC6H5CH(CH3)21142SO2ClOCOC6H5CH(CH3)21143SO2BrOCOC6H5CH(CH3)21144SO2NO2OCOC6H5CH(CH3)21145SO2SCH3OCOC6H5CH(CH3)21146SO2SO2CH3OCOC6H5CH(CH3)21147SO2SO2CH2CH3OCOC6H5CH(CH3)21148SO2CH3OCOC6H5CH(CH3)21149SO2CF3OCOC6H5CH(CH3)21150SO2OCHF2OCOC6H5CH(CH3)21151bondFOCOC6H5C(CH3)31152bondClOCOC6H5C(CH3)31153bondBrOCOC6H5C(CH3)31154bondNO2OCOC6H5C(CH3)31155bondSCH3OCOC6H5C(CH3)31156bondSO2CH3OCOC6H5C(CH3)31157bondSO2CH2CH3OCOC6H5C(CH3)31158bondCH3OCOC6H5C(CH3)31159bondCF3OCOC6H5C(CH3)31160bondOCHF2OCOC6H5C(CH3)31161CH2FOCOC6H5C(CH3)31162CH2ClOCOC6H5C(CH3)31163CH2BrOCOC6H5C(CH3)31164CH2NO2OCOC6H5C(CH3)31165CH2SCH3OCOC6H5C(CH3)31166CH2SO2CH3OCOC6H5C(CH3)31167CH2SO2CH2CH3OCOC6H5C(CH3)31168CH2CH3OCOC6H5C(CH3)31169CH2CF3OCOC6H5C(CH3)31170CH2OCHF2OCOC6H5C(CH3)31171OFOCOC6H5C(CH3)31172OClOCOC6H5C(CH3)31173OBrOCOC6H5C(CH3)31174ONO2OCOC6H5C(CH3)31175OSCH3OCOC6H5C(CH3)31176OSO2CH3OCOC6H5C(CH3)31177OSO2CH2CH3OCOC6H5C(CH3)31178OCH3OCOC6H5C(CH3)31179OCF3OCOC6H5C(CH3)31180OOCHF2OCOC6H5C(CH3)31181SFOCOC6H5C(CH3)31182SClOCOC6H5C(CH3)31183SBrOCOC6H5C(CH3)31184SNO2OCOC6H5C(CH3)31185SSCH3OCOC6H5C(CH3)31186SSO2CH3OCOC6H5C(CH3)31187SSO2CH2CH3OCOC6H5C(CH3)31188SCH3OCOC6H5C(CH3)31189SCF3OCOC6H5C(CH3)31190SOCHF2OCOC6H5C(CH3)31191SO2FOCOC6H5C(CH3)31192SO2ClOCOC6H5C(CH3)31193SO2BrOCOC6H5C(CH3)31194SO2NO2OCOC6H5C(CH3)31195SO2SCH3OCOC6H5C(CH3)31196SO2SO2CH3OCOC6H5C(CH3)31197SO2SO2CH2CH3OCOC6H5C(CH3)31198SO2CH3OCOC6H5C(CH3)31199SO2CF3OCOC6H5C(CH3)31200SO2OCHF2OCOC6H5C(CH3)31201bondFOCOC(CH3)3CH(CH3)21202bondClOCOC(CH3)3CH(CH3)21203bondBrOCOC(CH3)3CH(CH3)21204bondNO2OCOC(CH3)3CH(CH3)21205bondSCH3OCOC(CH3)3CH(CH3)21206bondSO2CH3OCOC(CH3)3CH(CH3)21207bondSO2CH2CH3OCOC(CH3)3CH(CH3)21208bondCH3OCOC(CH3)3CH(CH3)21209bondCF3OCOC(CH3)3CH(CH3)21210bondOCHF2OCOC(CH3)3CH(CH3)21211CH2FOCOC(CH3)3CH(CH3)21212CH2ClOCOC(CH3)3CH(CH3)21213CH2BrOCOC(CH3)3CH(CH3)21214CH2NO2OCOC(CH3)3CH(CH3)21215CH2SCH3OCOC(CH3)3CH(CH3)21216CH2SO2CH3OCOC(CH3)3CH(CH3)21217CH2SO2CH2CH3OCOC(CH3)3CH(CH3)21218CH2CH3OCOC(CH3)3CH(CH3)21219CH2CF3OCOC(CH3)3CH(CH3)21220CH2OCHF2OCOC(CH3)3CH(CH3)21221OFOCOC(CH3)3CH(CH3)21222OClOCOC(CH3)3CH(CH3)21223OBrOCOC(CH3)3CH(CH3)21224ONO2OCOC(CH3)3CH(CH3)21225OSCH3OCOC(CH3)3CH(CH3)21226OSO2CH3OCOC(CH3)3CH(CH3)21227OSO2CH2CH3OCOC(CH3)3CH(CH3)21228OCH3OCOC(CH3)3CH(CH3)21229OCF3OCOC(CH3)3CH(CH3)21230OOCHF2OCOC(CH3)3CH(CH3)21231SFOCOC(CH3)3CH(CH3)21232SClOCOC(CH3)3CH(CH3)21233SBrOCOC(CH3)3CH(CH3)21234SNO2OCOC(CH3)3CH(CH3)21235SSCH3OCOC(CH3)3CH(CH3)21236SSO2CH3OCOC(CH3)3CH(CH3)21237SSO2CH2CH3OCOC(CH3)3CH(CH3)21238SCH3OCOC(CH3)3CH(CH3)21239SCF3OCOC(CH3)3CH(CH3)21240SOCHF2OCOC(CH3)3CH(CH3)21241SO2FOCOC(CH3)3CH(CH3)21242SO2ClOCOC(CH3)3CH(CH3)21243SO2BrOCOC(CH3)3CH(CH3)21244SO2NO2OCOC(CH3)3CH(CH3)21245SO2SCH3OCOC(CH3)3CH(CH3)21246SO2SO2CH3OCOC(CH3)3CH(CH3)21247SO2SO2CH2CH3OCOC(CH3)3CH(CH3)21248SO2CH3OCOC(CH3)3CH(CH3)21249SO2CF3OCOC(CH3)3CH(CH3)21250SO2OCHF2OCOC(CH3)3CH(CH3)21251bondFOCOC(CH3)3C(CH3)31252bondClOCOC(CH3)3C(CH3)31253bondBrOCOC(CH3)3C(CH3)31254bondNO2OCOC(CH3)3C(CH3)31255bondSCH3OCOC(CH3)3C(CH3)31256bondSO2CH3OCOC(CH3)3C(CH3)31257bondSO2CH2CH3OCOC(CH3)3C(CH3)31258bondCH3OCOC(CH3)3C(CH3)31259bondCF3OCOC(CH3)3C(CH3)31260bondOCHF2OCOC(CH3)3C(CH3)31261CH2FOCOC(CH3)3C(CH3)31262CH2ClOCOC(CH3)3C(CH3)31263CH2BrOCOC(CH3)3C(CH3)31264CH2NO2OCOC(CH3)3C(CH3)31265CH2SCH3OCOC(CH3)3C(CH3)31266CH2SO2CH3OCOC(CH3)3C(CH3)31267CH2SO2CH2CH3OCOC(CH3)3C(CH3)31268CH2CH3OCOC(CH3)3C(CH3)31269CH2CF3OCOC(CH3)3C(CH3)31270CH2OCHF2OCOC(CH3)3C(CH3)31271OFOCOC(CH3)3C(CH3)31272OClOCOC(CH3)3C(CH3)31273OBrOCOC(CH3)3C(CH3)31274ONO2OCOC(CH3)3C(CH3)31275OSCH3OCOC(CH3)3C(CH3)31276OSO2CH3OCOC(CH3)3C(CH3)31277OSO2CH2CH3OCOC(CH3)3C(CH3)31278OCH3OCOC(CH3)3C(CH3)31279OCF3OCOC(CH3)3C(CH3)31280OOCHF2OCOC(CH3)3C(CH3)31281SFOCOC(CH3)3C(CH3)31282SClOCOC(CH3)3C(CH3)31283SBrOCOC(CH3)3C(CH3)31284SNO2OCOC(CH3)3C(CH3)31285SSCH3OCOC(CH3)3C(CH3)31286SSO2CH3OCOC(CH3)3C(CH3)31287SSO2CH2CH3OCOC(CH3)3C(CH3)31288SCH3OCOC(CH3)3C(CH3)31289SCF3OCOC(CH3)3C(CH3)31290SOCHF2OCOC(CH3)3C(CH3)31291SO2FOCOC(CH3)3C(CH3)31292SO2ClOCOC(CH3)3C(CH3)31293SO2BrOCOC(CH3)3C(CH3)31294SO2NO2OCOC(CH3)3C(CH3)31295SO2SCH3OCOC(CH3)3C(CH3)31296SO2SO2CH3OCOC(CH3)3C(CH3)31297SO2SO2CH2CH3OCOC(CH3)3C(CH3)31298SO2CH3OCOC(CH3)3C(CH3)31299SO2CF3OCOC(CH3)3C(CH3)31300SO2OCHF2OCOC(CH3)3C(CH3)31301bondFOCOSCH3CH(CH3)21302bondClOCOSCH3CH(CH3)21303bondBrOCOSCH3CH(CH3)21304bondNO2OCOSCH3CH(CH3)21305bondSCH3OCOSCH3CH(CH3)21306bondSO2CH3OCOSCH3CH(CH3)21307bondSO2CH2CH3OCOSCH3CH(CH3)21308bondCH3OCOSCH3CH(CH3)21309bondCF3OCOSCH3CH(CH3)21310bondOCHF2OCOSCH3CH(CH3)21311CH2FOCOSCH3CH(CH3)21312CH2ClOCOSCH3CH(CH3)21313CH2BrOCOSCH3CH(CH3)21314CH2NO2OCOSCH3CH(CH3)21315CH2SCH3OCOSCH3CH(CH3)21316CH2SO2CH3OCOSCH3CH(CH3)21317CH2SO2CH2CH3OCOSCH3CH(CH3)21318CH2CH3OCOSCH3CH(CH3)21319CH2CF3OCOSCH3CH(CH3)21320CH2OCHF2OCOSCH3CH(CH3)21321OFOCOSCH3CH(CH3)21322OClOCOSCH3CH(CH3)21323OBrOCOSCH3CH(CH3)21324ONO2OCOSCH3CH(CH3)21325OSCH3OCOSCH3CH(CH3)21326OSO2CH3OCOSCH3CH(CH3)21327OSO2CH2CH3OCOSCH3CH(CH3)21328OCH3OCOSCH3CH(CH3)21329OCF3OCOSCH3CH(CH3)21330OOCHF2OCOSCH3CH(CH3)21331SFOCOSCH3CH(CH3)21332SClOCOSCH3CH(CH3)21333SBrOCOSCH3CH(CH3)21334SNO2OCOSCH3CH(CH3)21335SSCH3OCOSCH3CH(CH3)21336SSO2CH3OCOSCH3CH(CH3)21337SSO2CH2CH3OCOSCH3CH(CH3)21338SCH3OCOSCH3CH(CH3)21339SCF3OCOSCH3CH(CH3)21340SOCHF2OCOSCH3CH(CH3)21341SO2FOCOSCH3CH(CH3)21342SO2ClOCOSCH3CH(CH3)21343SO2BrOCOSCH3CH(CH3)21344SO2NO2OCOSCH3CH(CH3)21345SO2SCH3OCOSCH3CH(CH3)21346SO2SO2CH3OCOSCH3CH(CH3)21347SO2SO2CH2CH3OCOSCH3CH(CH3)21348SO2CH3OCOSCH3CH(CH3)21349SO2CF3OCOSCH3CH(CH3)21350SO2OCHF2OCOSCH3CH(CH3)21351bondFOCOSCH3C(CH3)31352bondClOCOSCH3C(CH3)31353bondBrOCOSCH3C(CH3)31354bondNO2OCOSCH3C(CH3)31355bondSCH3OCOSCH3C(CH3)31356bondSO2CH3OCOSCH3C(CH3)31357bondSO2CH2CH3OCOSCH3C(CH3)31358bondCH3OCOSCH3C(CH3)31359bondCF3OCOSCH3C(CH3)31360bondOCHF2OCOSCH3C(CH3)31361CH2FOCOSCH3C(CH3)31362CH2ClOCOSCH3C(CH3)31363CH2BrOCOSCH3C(CH3)31364CH2NO2OCOSCH3C(CH3)31365CH2SCH3OCOSCH3C(CH3)31366CH2SO2CH3OCOSCH3C(CH3)31367CH2SO2CH2CH3OCOSCH3C(CH3)31368CH2CH3OCOSCH3C(CH3)31369CH2CF3OCOSCH3C(CH3)31370CH2OCHF2OCOSCH3C(CH3)31371OFOCOSCH3C(CH3)31372OClOCOSCH3C(CH3)31373OBrOCOSCH3C(CH3)31374ONO2OCOSCH3C(CH3)31375OSCH3OCOSCH3C(CH3)31376OSO2CH3OCOSCH3C(CH3)31377OSO2CH2CH3OCOSCH3C(CH3)31378OCH3OCOSCH3C(CH3)31379OCF3OCOSCH3C(CH3)31380OOCHF2OCOSCH3C(CH3)31381SFOCOSCH3C(CH3)31382SClOCOSCH3C(CH3)31383SBrOCOSCH3C(CH3)31384SNO2OCOSCH3C(CH3)31385SSCH3OCOSCH3C(CH3)31386SSO2CH3OCOSCH3C(CH3)31387SSO2CH2CH3OCOSCH3C(CH3)31388SCH3OCOSCH3C(CH3)31389SCF3OCOSCH3C(CH3)31390SOCHF2OCOSCH3C(CH3)31391SO2FOCOSCH3C(CH3)31392SO2ClOCOSCH3C(CH3)31393SO2BrOCOSCH3C(CH3)31394SO2NO2OCOSCH3C(CH3)31395SO2SCH3OCOSCH3C(CH3)31396SO2SO2CH3OCOSCH3C(CH3)31397SO2SO2CH2CH3OCOSCH3C(CH3)31398SO2CH3OCOSCH3C(CH3)31399SO2CF3OCOSCH3C(CH3)31400SO2OCHF2OCOSCH3C(CH3)31401bondFOCH3CH(CH3)21402bondClOCH3CH(CH3)21403bondBrOCH3CH(CH3)21404bondNO2OCH3CH(CH3)21405bondSCH3OCH3CH(CH3)21406bondSO2CH3OCH3CH(CH3)21407bondSO2CH2CH3OCH3CH(CH3)21408bondCH3OCH3CH(CH3)21409bondCF3OCH3CH(CH3)21410bondOCHF2OCH3CH(CH3)21411CH2FOCH3CH(CH3)21412CH2ClOCH3CH(CH3)21413CH2BrOCH3CH(CH3)21414CH2NO2OCH3CH(CH3)21415CH2SCH3OCH3CH(CH3)21416CH2SO2CH3OCH3CH(CH3)21417CH2SO2CH2CH3OCH3CH(CH3)21418CH2CH3OCH3CH(CH3)21419CH2CF3OCH3CH(CH3)21420CH2OCHF2OCH3CH(CH3)21421OFOCH3CH(CH3)21422OClOCH3CH(CH3)21423OBrOCH3CH(CH3)21424ONO2OCH3CH(CH3)21425OSCH3OCH3CH(CH3)21426OSO2CH3OCH3CH(CH3)21427OSO2CH2CH3OCH3CH(CH3)21428OCH3OCH3CH(CH3)21429OCF3OCH3CH(CH3)21430OOCHF2OCH3CH(CH3)21431SFOCH3CH(CH3)21432SClOCH3CH(CH3)21433SBrOCH3CH(CH3)21434SNO2OCH3CH(CH3)21435SSCH3OCH3CH(CH3)21436SSO2CH3OCH3CH(CH3)21437SSO2CH2CH3OCH3CH(CH3)21438SCH3OCH3CH(CH3)21439SCF3OCH3CH(CH3)21440SOCHF2OCH3CH(CH3)21441SO2FOCH3CH(CH3)21442SO2ClOCH3CH(CH3)21443SO2BrOCH3CH(CH3)21444SO2NO2OCH3CH(CH3)21445SO2SCH3OCH3CH(CH3)21446SO2SO2CH3OCH3CH(CH3)21447SO2SO2CH2CH3OCH3CH(CH3)21448SO2CH3OCH3CH(CH3)21449SO2CF3OCH3CH(CH3)21450SO2OCHF2OCH3CH(CH3)21451bondFOCH3C(CH3)31452bondClOCH3C(CH3)31453bondBrOCH3C(CH3)31454bondNO2OCH3C(CH3)31455bondSCH3OCH3C(CH3)31456bondSO2CH3OCH3C(CH3)31457bondSO2CH2CH3OCH3C(CH3)31458bondCH3OCH3C(CH3)31459bondCF3OCH3C(CH3)31460bondOCHF2OCH3C(CH3)31461CH2FOCH3C(CH3)31462CH2ClOCH3C(CH3)31463CH2BrOCH3C(CH3)31464CH2NO2OCH3C(CH3)31465CH2SCH3OCH3C(CH3)31466CH2SO2CH3OCH3C(CH3)31467CH2SO2CH2CH3OCH3C(CH3)31468CH2CH3OCH3C(CH3)31469CH2CF3OCH3C(CH3)31470CH2OCHF2OCH3C(CH3)31471OFOCH3C(CH3)31472OClOCH3C(CH3)31473OBrOCH3C(CH3)31474ONO2OCH3C(CH3)31475OSCH3OCH3C(CH3)31476OSO2CH3OCH3C(CH3)31477OSO2CH2CH3OCH3C(CH3)31478OCH3OCH3C(CH3)31479OCF3OCH3C(CH3)31480OOCHF2OCH3C(CH3)31481SFOCH3C(CH3)31482SClOCH3C(CH3)31483SBrOCH3C(CH3)31484SNO2OCH3C(CH3)31485SSCH3OCH3C(CH3)31486SSO2CH3OCH3C(CH3)31487SSO2CH2CH3OCH3C(CH3)31488SCH3OCH3C(CH3)31489SCF3OCH3C(CH3)31490SOCHF2OCH3C(CH3)31491SO2FOCH3C(CH3)31492SO2ClOCH3C(CH3)31493SO2BrOCH3C(CH3)31494SO2NO2OCH3C(CH3)31495SO2SCH3OCH3C(CH3)31496SO2SO2CH3OCH3C(CH3)31497SO2SO2CH2CH3OCH3C(CH3)31498SO2CH3OCH3C(CH3)31499SO2CF3OCH3C(CH3)31500SO2OCHF2OCH3C(CH3)31501bondFOCH(CH3)2CH(CH3)21502bondClOCH(CH3)2CH(CH3)21503bondBrOCH(CH3)2CH(CH3)21504bondNO2OCH(CH3)2CH(CH3)21505bondSCH3OCH(CH3)2CH(CH3)21506bondSO2CH3OCH(CH3)2CH(CH3)21507bondSO2CH2CH3OCH(CH3)2CH(CH3)21508bondCH3OCH(CH3)2CH(CH3)21509bondCF3OCH(CH3)2CH(CH3)21510bondOCHF2OCH(CH3)2CH(CH3)21511CH2FOCH(CH3)2CH(CH3)21512CH2ClOCH(CH3)2CH(CH3)21513CH2BrOCH(CH3)2CH(CH3)21514CH2NO2OCH(CH3)2CH(CH3)21515CH2SCH3OCH(CH3)2CH(CH3)21516CH2SO2CH3OCH(CH3)2CH(CH3)21517CH2SO2CH2CH3OCH(CH3)2CH(CH3)21518CH2CH3OCH(CH3)2CH(CH3)21519CH2CF3OCH(CH3)2CH(CH3)21520CH2OCHF2OCH(CH3)2CH(CH3)21521OFOCH(CH3)2CH(CH3)21522OClOCH(CH3)2CH(CH3)21523OBrOCH(CH3)2CH(CH3)21524ONO2OCH(CH3)2CH(CH3)21525OSCH3OCH(CH3)2CH(CH3)21526OSO2CH3OCH(CH3)2CH(CH3)21527OSO2CH2CH3OCH(CH3)2CH(CH3)21528OCH3OCH(CH3)2CH(CH3)21529OCF3OCH(CH3)2CH(CH3)21530OOCHF2OCH(CH3)2CH(CH3)21531SFOCH(CH3)2CH(CH3)21532SClOCH(CH3)2CH(CH3)21533SBrOCH(CH3)2CH(CH3)21534SNO2OCH(CH3)2CH(CH3)21535SSCH3OCH(CH3)2CH(CH3)21536SSO2CH3OCH(CH3)2CH(CH3)21537SSO2CH2CH3OCH(CH3)2CH(CH3)21538SCH3OCH(CH3)2CH(CH3)21539SCF3OCH(CH3)2CH(CH3)21540SOCHF2OCH(CH3)2CH(CH3)21541SO2FOCH(CH3)2CH(CH3)21542SO2ClOCH(CH3)2CH(CH3)21543SO2BrOCH(CH3)2CH(CH3)21544SO2NO2OCH(CH3)2CH(CH3)21545SO2SCH3OCH(CH3)2CH(CH3)21546SO2SO2CH3OCH(CH3)2CH(CH3)21547SO2SO2CH2CH3OCH(CH3)2CH(CH3)21548SO2CH3OCH(CH3)2CH(CH3)21549SO2CF3OCH(CH3)2CH(CH3)21550SO2OCHF2OCH(CH3)2CH(CH3)21551bondFOCH(CH3)2C(CH3)31552bondClOCH(CH3)2C(CH3)31553bondBrOCH(CH3)2C(CH3)31554bondNO2OCH(CH3)2C(CH3)31555bondSCH3OCH(CH3)2C(CH3)31556bondSO2CH3OCH(CH3)2C(CH3)31557bondSO2CH2CH3OCH(CH3)2C(CH3)31558bondCH3OCH(CH3)2C(CH3)31559bondCF3OCH(CH3)2C(CH3)31560bondOCHF2OCH(CH3)2C(CH3)31561CH2FOCH(CH3)2C(CH3)31562CH2ClOCH(CH3)2C(CH3)31563CH2BrOCH(CH3)2C(CH3)31564CH2NO2OCH(CH3)2C(CH3)31565CH2SCH3OCH(CH3)2C(CH3)31566CH2SO2CH3OCH(CH3)2C(CH3)31567CH2SO2CH2CH3OCH(CH3)2C(CH3)31568CH2CH3OCH(CH3)2C(CH3)31569CH2CF3OCH(CH3)2C(CH3)31570CH2OCHF2OCH(CH3)2C(CH3)31571OFOCH(CH3)2C(CH3)31572OClOCH(CH3)2C(CH3)31573OBrOCH(CH3)2C(CH3)31574ONO2OCH(CH3)2C(CH3)31575OSCH3OCH(CH3)2C(CH3)31576OSO2CH3OCH(CH3)2C(CH3)31577OSO2CH2CH3OCH(CH3)2C(CH3)31578OCH3OCH(CH3)2C(CH3)31579OCF3OCH(CH3)2C(CH3)31580OOCHF2OCH(CH3)2C(CH3)31581SFOCH(CH3)2C(CH3)31582SClOCH(CH3)2C(CH3)31583SBrOCH(CH3)2C(CH3)31584SNO2OCH(CH3)2C(CH3)31585SSCH3OCH(CH3)2C(CH3)31586SSO2CH3OCH(CH3)2C(CH3)31587SSO2CH2CH3OCH(CH3)2C(CH3)31588SCH3OCH(CH3)2C(CH3)31589SCF3OCH(CH3)2C(CH3)31590SOCHF2OCH(CH3)2C(CH3)31591SO2FOCH(CH3)2C(CH3)31592SO2ClOCH(CH3)2C(CH3)31593SO2BrOCH(CH3)2C(CH3)31594SO2NO2OCH(CH3)2C(CH3)31595SO2SCH3OCH(CH3)2C(CH3)31596SO2SO2CH3OCH(CH3)2C(CH3)31597SO2SO2CH2CH3OCH(CH3)2C(CH3)31598SO2CH3OCH(CH3)2C(CH3)31599SO2CF3OCH(CH3)2C(CH3)31600SO2OCHF2OCH(CH3)2C(CH3)31601bondFOCH2C6H5CH(CH3)21602bondClOCH2C6H5CH(CH3)21603bondBrOCH2C6H5CH(CH3)21604bondNO2OCH2C6H5CH(CH3)21605bondSCH3OCH2C6H5CH(CH3)21606bondSO2CH3OCH2C6H5CH(CH3)21607bondSO2CH2CH3OCH2C6H5CH(CH3)21608bondCH3OCH2C6H5CH(CH3)21609bondCF3OCH2C6H5CH(CH3)21610bondOCHF2OCH2C6H5CH(CH3)21611CH2FOCH2C6H5CH(CH3)21612CH2ClOCH2C6H5CH(CH3)21613CH2BrOCH2C6H5CH(CH3)21614CH2NO2OCH2C6H5CH(CH3)21615CH2SCH3OCH2C6H5CH(CH3)21616CH2SO2CH3OCH2C6H5CH(CH3)21617CH2SO2CH2CH3OCH2C6H5CH(CH3)21618CH2CH3OCH2C6H5CH(CH3)21619CH2CF3OCH2C6H5CH(CH3)21620CH2OCHF2OCH2C6H5CH(CH3)21621OFOCH2C6H5CH(CH3)21622OClOCH2C6H5CH(CH3)21623OBrOCH2C6H5CH(CH3)21624ONO2OCH2C6H5CH(CH3)21625OSCH3OCH2C6H5CH(CH3)21626OSO2CH3OCH2C6H5CH(CH3)21627OSO2CH2CH3OCH2C6H5CH(CH3)21628OCH3OCH2C6H5CH(CH3)21629OCF3OCH2C6H5CH(CH3)21630OOCHF2OCH2C6H5CH(CH3)21631SFOCH2C6H5CH(CH3)21632SClOCH2C6H5CH(CH3)21633SBrOCH2C6H5CH(CH3)21634SNO2OCH2C6H5CH(CH3)21635SSCH3OCH2C6H5CH(CH3)21636SSO2CH3OCH2C6H5CH(CH3)21637SSO2CH2CH3OCH2C6H5CH(CH3)21638SCH3OCH2C6H5CH(CH3)21639SCF3OCH2C6H5CH(CH3)21640SOCHF2OCH2C6H5CH(CH3)21641SO2FOCH2C6H5CH(CH3)21642SO2ClOCH2C6H5CH(CH3)21643SO2BrOCH2C6H5CH(CH3)21644SO2NO2OCH2C6H5CH(CH3)21645SO2SCH3OCH2C6H5CH(CH3)21646SO2SO2CH3OCH2C6H5CH(CH3)21647SO2SO2CH2CH3OCH2C6H5CH(CH3)21648SO2CH3OCH2C6H5CH(CH3)21649SO2CF3OCH2C6H5CH(CH3)21650SO2OCHF2OCH2C6H5CH(CH3)21651bondFOCH2C6H5C(CH3)31652bondClOCH2C6H5C(CH3)31653bondBrOCH2C6H5C(CH3)31654bondNO2OCH2C6H5C(CH3)31655bondSCH3OCH2C6H5C(CH3)31656bondSO2CH3OCH2C6H5C(CH3)31657bondSO2CH2CH3OCH2C6H5C(CH3)31658bondCH3OCH2C6H5C(CH3)31659bondCF3OCH2C6H5C(CH3)31660bondOCHF2OCH2C6H5C(CH3)31661CH2FOCH2C6H5C(CH3)31662CH2ClOCH2C6H5C(CH3)31663CH2BrOCH2C6H5C(CH3)31664CH2NO2OCH2C6H5C(CH3)31665CH2SCH3OCH2C6H5C(CH3)31666CH2SO2CH3OCH2C6H5C(CH3)31667CH2SO2CH2CH3OCH2C6H5C(CH3)31668CH2CH3OCH2C6H5C(CH3)31669CH2CF3OCH2C6H5C(CH3)31670CH2OCHF2OCH2C6H5C(CH3)31671OFOCH2C6H5C(CH3)31672OClOCH2C6H5C(CH3)31673OBrOCH2C6H5C(CH3)31674ONO2OCH2C6H5C(CH3)31675OSCH3OCH2C6H5C(CH3)31676OSO2CH3OCH2C6H5C(CH3)31677OSO2CH2CH3OCH2C6H5C(CH3)31678OCH3OCH2C6H5C(CH3)31679OCF3OCH2C6H5C(CH3)31680OOCHF2OCH2C6H5C(CH3)31681SFOCH2C6H5C(CH3)31682SClOCH2C6H5C(CH3)31683SBrOCH2C6H5C(CH3)31684SNO2OCH2C6H5C(CH3)31685SSCH3OCH2C6H5C(CH3)31686SSO2CH3OCH2C6H5C(CH3)31687SSO2CH2CH3OCH2C6H5C(CH3)31688SCH3OCH2C6H5C(CH3)31689SCF3OCH2C6H5C(CH3)31690SOCHF2OCH2C6H5C(CH3)31691SO2FOCH2C6H5C(CH3)31692SO2ClOCH2C6H5C(CH3)31693SO2BrOCH2C6H5C(CH3)31694SO2NO2OCH2C6H5C(CH3)31695SO2SCH3OCH2C6H5C(CH3)31696SO2SO2CH3OCH2C6H5C(CH3)31697SO2SO2CH2CH3OCH2C6H5C(CH3)31698SO2CH3OCH2C6H5C(CH3)31699SO2CF3OCH2C6H5C(CH3)31700SO2OCHF2OCH2C6H5C(CH3)31701bondFOSO2(4-CH3—C6H4)CH(CH3)21702bondClOSO2(4-CH3—C6H4)CH(CH3)21703bondBrOSO2(4-CH3—C6H4)CH(CH3)21704bondNO2OSO2(4-CH3—C6H4)CH(CH3)21705bondSCH3OSO2(4-CH3—C6H4)CH(CH3)21706bondSO2CH3OSO2(4-CH3—C6H4)CH(CH3)21707bondSO2CH2CH3OSO2(4-CH3—C6H4)CH(CH3)21708bondCH3OSO2(4-CH3—C6H4)CH(CH3)21709bondCF3OSO2(4-CH3—C6H4)CH(CH3)21710bondOCHF2OSO2(4-CH3—C6H4)CH(CH3)21711CH2FOSO2(4-CH3—C6H4)CH(CH3)21712CH2ClOSO2(4-CH3—C6H4)CH(CH3)21713CH2BrOSO2(4-CH3—C6H4)CH(CH3)21714CH2NO2OSO2(4-CH3—C6H4)CH(CH3)21715CH2SCH3OSO2(4-CH3—C6H4)CH(CH3)21716CH2SO2CH3OSO2(4-CH3—C6H4)CH(CH3)21717CH2SO2CH2CH3OSO2(4-CH3—C6H4)CH(CH3)21718CH2CH3OSO2(4-CH3—C6H4)CH(CH3)21719CH2CF3OSO2(4-CH3—C6H4)CH(CH3)21720CH2OCHF2OSO2(4-CH3—C6H4)CH(CH3)21721OFOSO2(4-CH3—C6H4)CH(CH3)21722OClOSO2(4-CH3—C6H4)CH(CH3)21723OBrOSO2(4-CH3—C6H4)CH(CH3)21724ONO2OSO2(4-CH3—C6H4)CH(CH3)21725OSCH3OSO2(4-CH3—C6H4)CH(CH3)21726OSO2CH3OSO2(4-CH3—C6H4)CH(CH3)21727OSO2CH2CH3OSO2(4-CH3—C6H4)CH(CH3)21728OCH3OSO2(4-CH3—C6H4)CH(CH3)21729OCF3OSO2(4-CH3—C6H4)CH(CH3)21730OOCHF2OSO2(4-CH3—C6H4)CH(CH3)21731SFOSO2(4-CH3—C6H4)CH(CH3)21732SClOSO2(4-CH3—C6H4)CH(CH3)21733SBrOSO2(4-CH3—C6H4)CH(CH3)21734SNO2OSO2(4-CH3—C6H4)CH(CH3)21735SSCH3OSO2(4-CH3—C6H4)CH(CH3)21736SSO2CH3OSO2(4-CH3—C6H4)CH(CH3)21737SSO2CH2CH3OSO2(4-CH3—C6H4)CH(CH3)21738SCH3OSO2(4-CH3—C6H4)CH(CH3)21739SCF3OSO2(4-CH3—C6H4)CH(CH3)21740SOCHF2OSO2(4-CH3—C6H4)CH(CH3)21741SO2FOSO2(4-CH3—C6H4)CH(CH3)21742SO2ClOSO2(4-CH3—C6H4)CH(CH3)21743SO2BrOSO2(4-CH3—C6H4)CH(CH3)21744SO2NO2OSO2(4-CH3—C6H4)CH(CH3)21745SO2SCH3OSO2(4-CH3—C6H4)CH(CH3)21746SO2SO2CH3OSO2(4-CH3—C6H4)CH(CH3)21747SO2SO2CH2CH3OSO2(4-CH3—C6H4)CH(CH3)21748SO2CH3OSO2(4-CH3—C6H4)CH(CH3)21749SO2CF3OSO2(4-CH3—C6H4)CH(CH3)21750SO2OCHF2OSO2(4-CH3—C6H4)CH(CH3)21751bondFOSO2(4-CH3—C6H4)C(CH3)31752bondClOSO2(4-CH3—C6H4)C(CH3)31753bondBrOSO2(4-CH3—C6H4)C(CH3)31754bondNO2OSO2(4-CH3—C6H4)C(CH3)31755bondSCH3OSO2(4-CH3—C6H4)C(CH3)31756bondSO2CH3OSO2(4-CH3—C6H4)C(CH3)31757bondSO2CH2CH3OSO2(4-CH3—C6H4)C(CH3)31758bondCH3OSO2(4-CH3—C6H4)C(CH3)31759bondCF3OSO2(4-CH3—C6H4)C(CH3)31760bondOCHF2OSO2(4-CH3—C6H4)C(CH3)31761CH2FOSO2(4-CH3—C6H4)C(CH3)31762CH2ClOSO2(4-CH3—C6H4)C(CH3)31763CH2BrOSO2(4-CH3—C6H4)C(CH3)31764CH2NO2OSO2(4-CH3—C6H4)C(CH3)31765CH2SCH3OSO2(4-CH3—C6H4)C(CH3)31766CH2SO2CH3OSO2(4-CH3—C6H4)C(CH3)31767CH2SO2CH2CH3OSO2(4-CH3—C6H4)C(CH3)31768CH2CH3OSO2(4-CH3—C6H4)C(CH3)31769CH2CF3OSO2(4-CH3—C6H4)C(CH3)31770CH2OCHF2OSO2(4-CH3—C6H4)C(CH3)31771OFOSO2(4-CH3—C6H4)C(CH3)31772OClOSO2(4-CH3—C6H4)C(CH3)31773OBrOSO2(4-CH3—C6H4)C(CH3)31774ONO2OSO2(4-CH3—C6H4)C(CH3)31775OSCH3OSO2(4-CH3—C6H4)C(CH3)31776OSO2CH3OSO2(4-CH3—C6H4)C(CH3)31777OSO2CH2CH3OSO2(4-CH3—C6H4)C(CH3)31778OCH3OSO2(4-CH3—C6H4)C(CH3)31779OCF3OSO2(4-CH3—C6H4)C(CH3)31780OOCHF2OSO2(4-CH3—C6H4)C(CH3)31781SFOSO2(4-CH3—C6H4)C(CH3)31782SClOSO2(4-CH3—C6H4)C(CH3)31783SBrOSO2(4-CH3—C6H4)C(CH3)31784SNO2OSO2(4-CH3—C6H4)C(CH3)31785SSCH3OSO2(4-CH3—C6H4)C(CH3)31786SSO2CH3OSO2(4-CH3—C6H4)C(CH3)31787SSO2CH2CH3OSO2(4-CH3—C6H4)C(CH3)31788SCH3OSO2(4-CH3—C6H4)C(CH3)31789SCF3OSO2(4-CH3—C6H4)C(CH3)31790SOCHF2OSO2(4-CH3—C6H4)C(CH3)31791SO2FOSO2(4-CH3—C6H4)C(CH3)31792SO2ClOSO2(4-CH3—C6H4)C(CH3)31793SO2BrOSO2(4-CH3—C6H4)C(CH3)31794SO2NO2OSO2(4-CH3—C6H4)C(CH3)31795SO2SCH3OSO2(4-CH3—C6H4)C(CH3)31796SO2SO2CH3OSO2(4-CH3—C6H4)C(CH3)31797SO2SO2CH2CH3OSO2(4-CH3—C6H4)C(CH3)31798SO2CH3OSO2(4-CH3—C6H4)C(CH3)31799SO2CF3OSO2(4-CH3—C6H4)C(CH3)31800SO2OCHF2OSO2(4-CH3—C6H4)C(CH3)31801bondFSCH3CH(CH3)21802bondClSCH3CH(CH3)21803bondBrSCH3CH(CH3)21804bondNO2SCH3CH(CH3)21805bondSCH3SCH3CH(CH3)21806bondSO2CH3SCH3CH(CH3)21807bondSO2CH2CH3SCH3CH(CH3)21808bondCH3SCH3CH(CH3)21809bondCF3SCH3CH(CH3)21810bondOCHF2SCH3CH(CH3)21811CH2FSCH3CH(CH3)21812CH2ClSCH3CH(CH3)21813CH2BrSCH3CH(CH3)21814CH2NO2SCH3CH(CH3)21815CH2SCH3SCH3CH(CH3)21816CH2SO2CH3SCH3CH(CH3)21817CH2SO2CH2CH3SCH3CH(CH3)21818CH2CH3SCH3CH(CH3)21819CH2CF3SCH3CH(CH3)21820CH2OCHF2SCH3CH(CH3)21821OFSCH3CH(CH3)21822OClSCH3CH(CH3)21823OBrSCH3CH(CH3)21824ONO2SCH3CH(CH3)21825OSCH3SCH3CH(CH3)21826OSO2CH3SCH3CH(CH3)21827OSO2CH2CH3SCH3CH(CH3)21828OCH3SCH3CH(CH3)21829OCF3SCH3CH(CH3)21830OOCHF2SCH3CH(CH3)21831SFSCH3CH(CH3)21832SClSCH3CH(CH3)21833SBrSCH3CH(CH3)21834SNO2SCH3CH(CH3)21835SSCH3SCH3CH(CH3)21836SSO2CH3SCH3CH(CH3)21837SSO2CH2CH3SCH3CH(CH3)21838SCH3SCH3CH(CH3)21839SCF3SCH3CH(CH3)21840SOCHF2SCH3CH(CH3)21841SO2FSCH3CH(CH3)21842SO2ClSCH3CH(CH3)21843SO2BrSCH3CH(CH3)21844SO2NO2SCH3CH(CH3)21845SO2SCH3SCH3CH(CH3)21846SO2SO2CH3SCH3CH(CH3)21847SO2SO2CH2CH3SCH3CH(CH3)21848SO2CH3SCH3CH(CH3)21849SO2CF3SCH3CH(CH3)21850SO2OCHF2SCH3CH(CH3)21851bondFSCH3C(CH3)31852bondClSCH3C(CH3)31853bondBrSCH3C(CH3)31854bondNO2SCH3C(CH3)31855bondSCH3SCH3C(CH3)31856bondSO2CH3SCH3C(CH3)31857bondSO2CH2CH3SCH3C(CH3)31858bondCH3SCH3C(CH3)31859bondCF3SCH3C(CH3)31860bondOCHF2SCH3C(CH3)31861CH2FSCH3C(CH3)31862CH2ClSCH3C(CH3)31863CH2BrSCH3C(CH3)31864CH2NO2SCH3C(CH3)31865CH2SCH3SCH3C(CH3)31866CH2SO2CH3SCH3C(CH3)31867CH2SO2CH2CH3SCH3C(CH3)31868CH2CH3SCH3C(CH3)31869CH2CF3SCH3C(CH3)31870CH2OCHF2SCH3C(CH3)31871OFSCH3C(CH3)31872OClSCH3C(CH3)31873OBrSCH3C(CH3)31874ONO2SCH3C(CH3)31875OSCH3SCH3C(CH3)31876OSO2CH3SCH3C(CH3)31877OSO2CH2CH3SCH3C(CH3)31878OCH3SCH3C(CH3)31879OCF3SCH3C(CH3)31880OOCHF2SCH3C(CH3)31881SFSCH3C(CH3)31882SClSCH3C(CH3)31883SBrSCH3C(CH3)31884SNO2SCH3C(CH3)31885SSCH3SCH3C(CH3)31886SSO2CH3SCH3C(CH3)31887SSO2CH2CH3SCH3C(CH3)31888SCH3SCH3C(CH3)31889SCF3SCH3C(CH3)31890SOCHF2SCH3C(CH3)31891SO2FSCH3C(CH3)31892SO2ClSCH3C(CH3)31893SO2BrSCH3C(CH3)31894SO2NO2SCH3C(CH3)31895SO2SCH3SCH3C(CH3)31896SO2SO2CH3SCH3C(CH3)31897SO2SO2CH2CH3SCH3C(CH3)31898SO2CH3SCH3C(CH3)31899SO2CF3SCH3C(CH3)31900SO2OCHF2SCH3C(CH3)31901bondFClCH(CH3)21902bondClClCH(CH3)21903bondBrClCH(CH3)21904bondNO2ClCH(CH3)21905bondSCH3ClCH(CH3)21906bondSO2CH3ClCH(CH3)21907bondSO2CH2CH3ClCH(CH3)21908bondCH3ClCH(CH3)21909bondCF3ClCH(CH3)21910bondOCHF2ClCH(CH3)21911CH2FClCH(CH3)21912CH2ClClCH(CH3)21913CH2BrClCH(CH3)21914CH2NO2ClCH(CH3)21915CH2SCH3ClCH(CH3)21916CH2SO2CH3ClCH(CH3)21917CH2SO2CH2CH3ClCH(CH3)21918CH2CH3ClCH(CH3)21919CH2CF3ClCH(CH3)21920CH2OCHF2ClCH(CH3)21921OFClCH(CH3)21922OClClCH(CH3)21923OBrClCH(CH3)21924ONO2ClCH(CH3)21925OSCH3ClCH(CH3)21926OSO2CH3ClCH(CH3)21927OSO2CH2CH3ClCH(CH3)21928OCH3ClCH(CH3)21929OCF3ClCH(CH3)21930OOCHF2ClCH(CH3)21931SFClCH(CH3)21932SClClCH(CH3)21933SBrClCH(CH3)21934SNO2ClCH(CH3)21935SSCH3ClCH(CH3)21936SSO2CH3ClCH(CH3)21937SSO2CH2CH3ClCH(CH3)21938SCH3ClCH(CH3)21939SCF3ClCH(CH3)21940SOCHF2ClCH(CH3)21941SO2FClCH(CH3)21942SO2ClClCH(CH3)21943SO2BrClCH(CH3)21944SO2NO2ClCH(CH3)21945SO2SCH3ClCH(CH3)21946SO2SO2CH3ClCH(CH3)21947SO2SO2CH2CH3ClCH(CH3)21948SO2CH3ClCH(CH3)21949SO2CF3ClCH(CH3)21950SO2OCHF2ClCH(CH3)21951bondFClC(CH3)31952bondClClC(CH3)31953bondBrClC(CH3)31954bondNO2ClC(CH3)31955bondSCH3ClC(CH3)31956bondSO2CH3ClC(CH3)31957bondSO2CH2CH3ClC(CH3)31958bondCH3ClC(CH3)31959bondCF3ClC(CH3)31960bondOCHF2ClC(CH3)31961CH2FClC(CH3)31962CH2ClClC(CH3)31963CH2BrClC(CH3)31964CH2NO2ClC(CH3)31965CH2SCH3ClC(CH3)31966CH2SO2CH3ClC(CH3)31967CH2SO2CH2CH3ClC(CH3)31968CH2CH3ClC(CH3)31969CH2CF3ClC(CH3)31970CH2OCHF2ClC(CH3)31971OFClC(CH3)31972OClClC(CH3)31973OBrClC(CH3)31974ONO2ClC(CH3)31975OSCH3ClC(CH3)31976OSO2CH3ClC(CH3)31977OSO2CH2CH3ClC(CH3)31978OCH3ClC(CH3)31979OCF3ClC(CH3)31980OOCHF2ClC(CH3)31981SFClC(CH3)31982SClClC(CH3)31983SBrClC(CH3)31984SNO2ClC(CH3)31985SSCH3ClC(CH3)31986SSO2CH3ClC(CH3)31987SSO2CH2CH3ClC(CH3)31988SCH3ClC(CH3)31989SCF3ClC(CH3)31990SOCHF2ClC(CH3)31991SO2FClC(CH3)31992SO2ClClC(CH3)31993SO2BrClC(CH3)31994SO2NO2ClC(CH3)31995SO2SCH3ClC(CH3)31996SO2SO2CH3ClC(CH3)31997SO2SO2CH2CH3ClC(CH3)31998SO2CH3ClC(CH3)31999SO2CF3ClC(CH3)32000SO2OCHF2ClC(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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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:
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    • 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.
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    • 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.
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    • 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.
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    • 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:
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    • 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.
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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.
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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:
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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
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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)
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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),
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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),
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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:
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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.
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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.
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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.
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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.
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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).
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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.
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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).
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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.
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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:
      embedded image


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
embedded image

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:
      embedded image


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 2embedded imagephysical data (m.p. [° C.];No.XR4R10R11R121H NMR [ppm])2.1BondSO2CH3OHCH3H3.03 (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)2.2BondSO2CH3OCOC6H5CH3H3.22 (s, 3H); 3.34 (m, 2H); 3.81 (s, 3H); 3.98 (m, 2H); 4.81 (t, 1H); 7.20-8.21 (m, 8H);2.3OOCH3OHCH3H236-2382.4OOCH3OHC(CH3)3H223-2252.5OOCH3OCO (3-F—C6H4)CH3Hoil









TABLE 3















embedded image


















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















embedded image
























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















embedded image
























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 NameCommon NameChenopodium albumlambsquarters (goosefoot)Echinochloa crusgallibarnyardgrassSetaria viridisgreen foxtailSolanum nigrumblack nightshadeVeronica 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
  • 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),
  • 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),
  • 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),
  • 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),
  • 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
  • 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,
  • 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
  • 38. A tricyclic benzene compound of formula IX
  • 39. An aniline compound of formula XV
  • 40. A nitrile compound of formula XVI
  • 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.
Priority Claims (1)
Number Date Country Kind
19911219.3 Mar 1999 DE national
Divisions (1)
Number Date Country
Parent 09936356 Sep 2001 US
Child 11461491 Aug 2006 US