Indian Patents
Title of Invention

3-(4,5-DIHYDROISOXAZOLE-5-YL) BENZOYLPYRAZOLE
Abstract ABSTRACT IN/PCT/2002/01049/CHE 3—(4 , 5-dihydroisoxazol-5-yl) benzoylpyrasoles The present invention relates to 3_(4,5-dihydroi»oxazol-5-yl)benzoylpyrazoles of the formula I wherein the substituents are as described in the description and their agriculturally useful salts; processes and intermediates Cor preparing the 3-(4,5-dihydroiaoxazoL-5-yl)bensoylpyrazoles; compositions comprising then; and the use of these derivatives or the compositions comprising then for controlling undesirable plants are described.
Full Text

The present invention relates to
3~(4,5-dihydroisoxazol—5—yl)ben2oylpyrazoles of the formula I

where:
R1, R2 are hydrogen, nitro, halogen, cyano, Cj-Cg-alkyl, Cj.-C6-haloalkyl, Ci-Ce-alkoxy, Ci-Cg-haloalkoxy, Cj-Cg-alitylthio, Ci-Cs—haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg—haloalkylsulfinyl, Cj-Ce-alkylsulfonyl or Ci-Sg—haloalkylsulfonyl;
R3 is hydrogen, halogen or Ci-C6-a.lkyl;
R4 is hydrogen or Ci-C4—alkyl;
R5, R6 are hydrogen, halogen, cyano, nitro, Ci-C*-alkyl, C1-C4-alkoxy-Ci-C4—alkyl, di(Cj-C4—alkoxy)-C1-C4— alkyl, di(Ci-C4-alkyl)amino-Ci-C4-alkyl, di {C1-C4—alky 1) aminoijnino-Ci-C4—alkyl,
hydroxyimino-Ci-C4-alkyl, Ci-Cg—alkoxyimino-Ci~C4—alkyl, Ci-C4-alkbxycarbonyl-Ci-C4—alkyl, Cj-C4-alkylthio-Ci-C4-alkyl, Cj-C4-haloalkyl, Ci-C4-cyanoalkyl, C3-C8-cycIoalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-C2- nitro, cyano, C^^-alkyl, Ci-^-haloalkyl, Ci-C4-alkoxy or C1-C4—haloalkoxy;
or

R5 and R6 together form a C2-C6-alkanediyl chain which may be
mono- to tetrasubstituted by Ci-Cj-alkyl and/or may be interrupted by oxygen or an unsubstituted or Ci—C4-alkyl-substituted nitrogen;
R7 is halogen, cyano, hydroxy1, Ci-C6-alkyl,
Ci-C6-haloalkyl/ Cj-Cg-alkoxy, Ci-Cg-haloalkoxy,
Ci-c6—alkylthio, Cj-Cg-haloalkylthio,
Ci-C6-alkylsulfinyl, Cj-Cg—haloalkylsulfinyl,
Ci—C6-alkylsulfonylf Ci-Cg-haloalkylsulfonyl, amino,
Ci-Cg-alkylamino, di (Ci-Cs-alkyl) amino,
di(Ci-C4—alkoxy)methyl, hydroxyimino-C1-C4—alkyl,
Ci—C6—alkoxyimino-Ci—C4—alkyl or COR8;
R8 is hydrogen, Ci-Ct-alXyl, C1-C4—haloalkyl, hydroxyl, d—C4—alkoxy, C 1-C4—alkoxy—C2—C4—alkoxy, C1-C4—haloalkoxy, C3—Ce—alkenyloxy, C3-C6—alkynyloxy or NR9Ri°;
R9 is hydrogen or Ci-C^-alkyl;
R10 is Cj-C^-alkylj
Rii is a pyrazole, attached in the 4—position, of the
formula II

where
R12 is hydrogen, Ci-C4-alkyl, Ci-C4~haloalkyl, C3-c6-alkenyl, C3-C4-alkynyl, Cj^-C^-alkylcarbonyl, C1-C4-haloalkylcarbonyl, Ci-C4-alkylsulfonyl, C1-C4—haloalkylsulfonyl, thienylmethyl, phenyl, benzyl, phenylcarbonyl, phenyl su Ifonyl or phenylcarbonylmethyl, where the phenyl radical of the five last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, Cr^-alkyl, Ci-C4-^ialaalkyl, Ci-C4-alkoxy or Ci-c4—haloalkoxy;

R13 is Ci-Cg-alkyl, Cj-C6-haloalkyl or C3-C6-cycloalkyl;
R14 is hydrogen, Ci-Cs-alkyl or C3-C6—cycloalkyl;
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.
Pyrazol-4-ylbenzoyl derivatives have been disclosed in the literature, for example in WO 96/26206.
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, in particular herbicidally active, compounds which have improved properties.
We have found that this object is achieved by the
3— (4,5-dihydroisoxazol—5—yl)benzoylpyrazoles of the formula I and
by their herbicidal activity.
We have furthermore found herbicidal compositions which comprise the compounds I and which have very good herbicidal activity. 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 can exist as enantiomer or diastereomer mixtures. The present invention relates both to the pure enantiomers or diastereomers and to the mixtures thereof.
The compounds of the formula I may also exist in the form of their agriculturally useful salts, the type of salt generally being of no importance. In general, suitable salts are the salts of those cations or the acid addition salts of those acids whose cations, or anions, respectively, do not adversely affect the herbicidal activity 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, it being possible in this case, if desired, for one to four hydrogen atoms to be replaced by Cj-C(—alkyl or hydroxy-Ci-C^-alkyl and/or a phenyl or benzyl, preferably ammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri{Ci—C4—alkyljsulfonium, 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.
The organic moieties mentioned for the substituents R1—R1^ or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkenyloxy, alkynyloxy, alkylamino, dialkylamino, alkoxyalkyl, dialkoxymethyl, dialkoxyalkyl, alkylthioalkyl, dialkylaminoalkyl, dialkylaminoiminoalkyl, hydroxyiminoalkyl, alkoxyiminoalkyl, alkoxycarbonylalkyl and alkoxyalkoxy moieties may be straight-chain or branched. Unless otherwise specified, halogenated substituents preferably carry one to five identical or different halogen atoms. The meaning of halogen is in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are:
- Ci-C4-alkyl and the alkyl moieties of C1-C4—alkylcarbonyl,
di^Ci-Ci-alkoxyj-Ci-Ci-alkyl,
di (Ci—C^-alkyl) aminoimino-Ci—C4—alkyl,
Ci-C6-alkoxyiminc-Cr-C4-alkyl and hydroxyiminc—Ci-C4-alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl; '
— Ci-Cfi—alkyl: Ci-Cj-alkyl as mentioned above and also, for
example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,
2,2-dimethylpropyl, 1-ethylprppyl, hexyl, l,l- 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—ethy lbutyl, 1,1,2—trimethylpropyl, 1—ethyl— 1-aie thy Ipropyl and 1-ethyl—3-methylpropyl;
— C1-C4—haloalkyl and the haloalkyl moieties of
C1-C4—haloalkylcarbonyl: a Cj-C^—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, bromomethyl, iodomethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromomethyl, 1-iodoethyl, 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, l-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;
— Ci-Cg—haloalkyl: C1-C4—haloalkyl as mentioned above and also,
for example, 5—fluoropentyl, 5-chloropentyl, 5-bromopentyl,
5—iodopentyl, undecafluoropentyl, 6—fluorohexyl,
6-chlorohexyl, 6—bromohexy1, 6—iodohexyl and dodecafluorohexyl;
— Ci-Cj-cyanoalkyl: for example cyanomethyl, 1-cyanoeth-l-yl,
2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl,
3-cyanoprop-1-y1, 1-cyanoprop-2-y1, 2-cyanoprop-2-y1, 1-cyanobut-l-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l-yl, l-cyanobut-2-yl, 2-cyanobut-2~yl, l-cyanobut-3-yl, 2-cyanobut-3-yl, l-cyano-2-methylprop-3-yl, 2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl and 2-cyanomethylprop-2-y1;
C3-C4-alkenyl: for example prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethen-l-yl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-l-en-l-yl, 2-methylprop-l-en-l-yl, l-methylprop-2-en-Z-yl or 2-methylprop-2-en-l-yl;

C3-C4~alkynyl: for example prop-1-yn-l-yl, prop-2-yn-l-yl, but-1-yn-l-yl, but-l-yn-3-yl, but-l-yn-4-yl or but-2-yn-l-yl;
— Ci-C4~alJcoxy and the alkoxy moieties of di(Ci-C4—alkoxy)methyl and di(C],-C4—alkoxy)-Ci-C4-alkyl: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;
— Ci-Cg—alkoxy and the alkoxy moieties of Ci-Cs-alkoxyimino-Cr-C^-alkyl: Ci-C4—alkoxy as mentioned above and also, for example, pentoxy, 1-methylbutoxy,
2—methylbutoxy, 3-methoxylbutoxy, 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-l-methylpropoxy and l-ethyl-2-methylpropoxy;
~ Ci—C4—haloalkoxy: a Cj—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-bromomethoxy, 2—iodoethoxy, 2,2-difluoroethoxy, 2,2,2—trifluoroethoxy, 2-chloro—2—fluoroethoxy, 2-chlorc—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 and nonafluorobutoxy;
— Ci-Ce-haloalkoxy: C1-C4—haloalkoxy as mentioned above and
also, for example, 5—fluoropentoxy, 5—chloropentoxy,
5—broraopentoxy, 5—iodopentoxy, undecafluoropentoxy,
6—fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6—iodohexoxy
and dodecafluorohexoxy;

— Ci-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;
— Ci—C6—alkylthio: Ci-C 4—alkylthio as mentioned above and, 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-e thy 1-1 -methyl propyl thio and l-ethyl-2-methylpropylthio;
— C1-C4—haloalkylthio: a C1-C4—alkylthio radical as mentioned
above, which is partially or fully substituted by fluorine,
chlorine, bromine and/or iodine, i.e., for example
fluoromethylthio, difluoromethylthio, trifluoromethylthio,
chlorodifluoromethylthio, bromodifluoromethylthio,
2—fluor ethyl thio, 2-chloroethy lthio, 2—bromoethy lthio,
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^>entafluoropropylthio,
heptaf luoropropy lthio, l-(fluoromethyl)-2—f luoroethylthio,
1—(chloromethyl)-2-chloroethylthio,
l-{bromomethyl)-2-bromoethylthio, 4—fluorobutylthio,
4—chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio;
— Ci—C$-~haloalkylthioj Ci—C4—haloalkylthio as mentioned above
and also, for example, 5—fluoropentylthio,
5—chloropentylthio, 5-bromopentylthio, 5—iodopentylthio, undecafluoropentylthio, 6—fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio and dodecafluorohexylthio;
— Ci-C6-alkylsulfinyl (Ci-C6-alkyl-S(=0)--): for example
methylsulfinyl, ethylsulfinyl, propylsulfinyl,
1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl,
2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl,
pentylsulfinyl, 1-methylbutylsulfinvl. 2-ntethvlbutvlsulf invl,

3~methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,
1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,
1,2-dimethylpropylsulfinyl, hexylsulfinyl,
1-methylpentylsulfinyl, 2-methylpentylsulfinyI,
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—trimethylpropylsuIfinyl, 1,2,2—trimethylpropylsulfinyl,
1-ethyl— 1-niethylpropylsulfinyl and
1-ethyl—2-methylpropylsulf inyl;
— Ci-Ce—haloalkylsulfinyl: a Cr-Cg-alkylsulfinyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example fluorontethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluororaethylsulfinyl, 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, pentaf luoroethylsulf inyl, 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, l-(fluoromethyl)-2-fluoroethylsulfinyl, l-(chloromethyl}-2-chloroethylsulfinyl,
l-(bromomethyl)~2-bromoethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-*romobutylsulfinyl, nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl and dodecafluorohexylsulfinyl;

— Ci-C4-alkylsulfonyl (Cj-C^-alkyl-S^O^-): for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and l,l~dimethylethylsulfonyl;
— Ci-C6-alkylsulfonyl: Ci-C4-alkyl sulf onyl as mentioned above, and also for example pentylsulfonyl, 1—methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl,
1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,
2,2-*3imethylpropylsulfonyl, 1-ethylpropylsulfonyl,
hexylsulfonyl, 1-methylpentylsulfonyl,
2-methylpentylsulfonyl, 3-methylpentylsulfonyl,
4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,
1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,
2,2—dimethylbutylsulfony1, 2,3—dimethyIbutylsulfonyl,
3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,
2-ethylbutylsulfonyl, 1,1,2—triroethylpropylsulfonyl,
1,2,2—trimet hylpropy lsulf onyl, 1-ethyl—1 -methyl propylsulfonyl
and l-ethyl-2-methylpropylsulfonylj
— C1-C4—haloalkylsulfonyl: a C1-C4—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-chlorc—2,2-dif luoroethylsulf onyl,
2,2-dichloro-2-fluoroethylsulfonyl,
2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,
2-fluoropropylsulfonyl, 3—fluoropropylsulfonyl,
2-chloropropylsuZfonyl, 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,
l- chloroethylsulfonyl, l-{bromomethyl)—2-*romoethylsulfonyl,
4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl,
4—bromobutylsulfonyl and nonafluorobutylsulfonylj

— Ci-Cfi—haloalkylsulfonylt a C1-C4—haloalkylsulfonyl radical as
mentioned above, and also 5—fluoropentylsulfonyl,
5-chloropentylsulfonyl, 5-bromopentylsulfonyl,
5—iodopentylsulfonyl, 6—f luorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl and dodecafluorohexylsulfonyl;
— Ci~Ci~~alkoxycarbonyl: for example methoxycarbonyl,
ethoxycarbonyl, propoxycarbonyl, l-*nethylethoxycarbonyl,
butoxycarbony1, 1-methylpropoxycarbonyl,
2-me thy lpropoxycarbonyl and 1,1—dimethoxycarbonyl j
— Ci—Ca—haloalkoxycarbonyl: a Ci~C4—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-chlorc—2-f luoroethoxycarbonyl,
2—chloro—2,2—dif luoroethoxycarbonyl,
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-dif luoropropoxycarbonyl,
2,3-dichloropropoxycarbonyl, 3,3, 3-trif luoropropoxycarbonyl,
3,3,3—trichloropropoxycarbony1,
2,2,3,3,3—pentafluoropropoxycarbonyl,
heptafluoropropoxycarbonyl,
l-(fluoromethyl)-2-f luoroethoxycarbonyl,
l-(chloromethyl)-2-chloroethoxycarbonyl,
1- (bromomethyl )-2-bromoethoxycarbonyl,
4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl,
4-bromobutoxycarbonyl and 4-iodobutoxycarbonyl;
C3-Cfi-alkenyloxy: for example prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy, 1-methylprop-l-en-l-yloxy, 2-methylprop-l-en-l-yloxy, l-methylprop-2-en-l-yloxy, 2-methylprop-2-en-l-yloxy, penten-1-yloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-l-yloxy, 2-methylbut-l-en-l-yloxy, 3-methylbut-l-en-l-yloxy, 1-methylbut-2-en-l-yloxy, 2-methylbut-2-en-l-yloxy,

3-methylbut-2-en-l-yloxy, l-methylbut-3-en-l-yloxy, 2-methylbut-3-en-l-yloxy, 3-methylbut-3-en-l-yloxy, 1,l-dimethylprop-2-en-l-yloxy, \,2-dimethylprop-l-en-l-yloxy, l,2-dimethylprop~2-en-l-yloxy, l-ethylprop-l-en-2-yloxy, l-ethylprop-2-en-l-yloxy, hex-1-en-l-yloxy, hex-2-en-l-yloxy, hex-3-en-l-yloxy, hex-4-en-l-yloxy, hex-5-en-1-yloxy, 1-methylpent-l-en-l-yloxy, 2-methylpent-l-en-l-yloxy, 3-methylpent-l-en-l-yloxy, 4-methylpent-l-en-l-yloxy, l-methylpent-2-en-l-yloxy, 2-methylpent-2-en-l-yloxy, 3-methylpent-2-en-l-yloxy, 4-methylpent-2-en-l-yloxy, l-methylpent-3-en-l-yloxy, 2-methylpent-3-en-l-yloxy, 3-methylpent-3-en-l-yloxy, 4-methylpent-3-en-l~yloxy, l-methylpent-4-en-l-yloxy, 2-methylpent-4-en-l-yloxy, 3-methylpent-4-en-l-yloxy, 4-methylpent-4-en-l-yloxy, 1, l-dimethylbut-2-en-l -yloxy, 1, 1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-l-en-l-yloxy, l,2-dimethylbut-2-en-l-yloxy, 1,2-dimethylbut-3-en-l-yloxy, 1,3-dimethylbut-l-en-l-yloxy, l,3-dimethylbut-2-en-l-yloxy, l,3-dimet.hylbut-3-en-l-yloxy, 2,2-dimethylbut-3-en-l-yloxy, 2,3-dimethylbut-l-en-l-yloxy, 2,3-dimethylbut-2-en-l-yloxy, 2,3-dimethylbut-3-en-l-yloxy, 3,3-dimethylbut-l-en-l-yloxy, 3,3-dimethylbut-2-en-l-yloxy, 1-ethylbut-l-en-l-yloxy, l-ethylbut-2-en-l-yloxy, l-ethylbut-3-en-l-yloxy, 2-ethylbut-l-en-l-yloxy, 2-ethylbut-2-en-l-yloxy, 2-ethylbut-3-en-l-yloxy, 1,1,2-trimethylprop-2-en-l-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy, l-ethyl-2-methylprop-l-en-l-yloxy and l-ethyl-2-methylprop-2-en-l-yloxy;
C3-C6-alkynyloxy: for example prop-1-yn-l-yloxy, prop-2-yn-l-yloxy, but-1-yn-l-yloxy, but-l-yn-3-yloxy, but-l-yn-4-yloxy, but-2-yn-l-yloxy, pent-1-yn-l-yloxy, pent-l-yn-3-yloxy, pent-l-yn-4-yloxy, pent-l-yn-5-yloxy, pent-2-yn-l-yloxy, pent-2-yn-4-yloxy, pent-2-yn-5-yloxy, 3-methylbut-l-yn-3-yloxy, 3-methylbut-l-yn-4-yloxy, hex-l-yn-1-yloxy, hex-l-yn-3-yloxy, hex-l-yn-4-yloxy, hex-l-yn-5-yloxy, hex-l-yn-6-yloxy, hex-2-yn-l-yloxy, hex-2-yn-4-yloxy, hex-2-yn-5-yloxy, hex-2-yn-6-yloxy, hex-3-yn-l-yloxy, hex-3-yn-2-yloxy, 3-methylpent-l-yn-l-yloxy, 3 -me thylpent- l-yn-3 -yloxy, 3-methylpent-l-yn-4-yloxy, 3-methylpent-l-yn-5-yloxy, 4-methylpcnt-l-yn-l-yloxy, 4-methylpent-2-yn-4-yloxy and 4-methylpent-2-yn-5-yloxy;
d-Cg-alkylaminoi for example methylamino, ethylamino, propylamine, l-methylethylamino, butylamino, 1-methylpropyiamino, 2-methylpropylamino,

1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,
2-methylbutylamino, 3-methylbutylamino,
2,2~dimethylpropylamino, 1-ethylpropylamino, hexylamino,
1,1-dimethylpropylamino/ 1, 2-dimethylpropylami.no,
1-methylpentylamino, 2-methylpentylamino,
3-methylpentylamino, 4-methylpentylamina,
1,1-dimethylbutylamino, 1,2-dimethylbutylamino,
1,3-dimethylbutylamino, 2,2-dimethylbutylamino,
2,3-dimethylbutylamino, 3,3-dimethylbutylamino,
l~ethylbutylamino, 2-ethylbutylamino,
1,1,2-trimethy lpropylamino, 1,2,2-trimethylpropylamino,
1-ethyl-l-methylpropylamino or l-ethyl-2-methylpropylaminoj
di(Ci-C4-alkyl)amino and the dialJtylamino moieties of
di(Ci-C4-alkyl)aminoimino-Ci-C4-al)cyl: for example
N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino,
N, N-di (1-methylethy 1) amino, N, N-dibutylamino,
N,N-di(1-methylpropyl) amino, N,N-di(2-methylpropyl)amino,
N,H-di (1,1 -dimethylethyl) amino, N-ethy 1-K-methylamino,
N-methyl-N-propylamino, N-methyl-K-(l-methylethyl)amino,
N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,
H-methy1-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 J amino,
N-ethyl-N-(2-methylpropy1)amino,
N-ethyl-N-(1,1-dimethylethyl)amino,
N-(l-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-(l-methylethyl)amino,
N-(1-methylethy1)-N-(1-methylpropy1)amino,
N-(1 -methylethyl)-N-(2-methylpropyl) amino,
N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,
N-buty1-N-(1-methylpropy1) amino,
N-butyl-N-(2-methylpropyl) amino,
N-butyl-N-(1,1-dimethylethyl)amino,
N- (1 -methylpropyl) -N-{ 2-methylpropyl) amino,
N-(1,l-dimethylethyl)-N-(1-methylpropyl)amino and
N- (1,1-dimethylethyl) -N- (2-methylpropyl) amino j
- di(Ci-C6-alkyl)amino: di(Ci~C4-alkyl)amino as mentioned above, and also N,N-dipentylamino, N,N-dihexylamino, N-methyl—N—pentylamino, N-ethyl-4f-pentylami.no, N-methyl-N-hexylamino or N-ethy 1-N-hexylamino;

— di(Ci-C4-alkyl)amino-C1-C4-alkyl: Ci~C4-alkyl which is
substituted by di(Ci-C4-alkyl)aniino as mentioned above, i.e.,
for example N,N-dimethylaminoniethyl, N,N-diethylaminomethyl,
N,N-dipropylaminomethyl, N,N-di N,N—dibutylaminomethyl, N,N-di( 1—methylpropyl) aminomethyl,
H,N—di(2-methylpropyl)aminomethyl,
N,N-di(1,1—dimethylethy1)aminomethyl,
N—ethyl-N-methylaminomethyl, N-methyl—N—propylaminomethyl,
N-methyl—N— (1-methylethyl) aminomethyl ,
N—butyl-N-methylaminomethyl,
N-methyl—N—(1—methylpropyl) aminomethyl,
N-methyl-N—( 2-methylpropyl) aminomethyl,
N-{ 1, l-dimethylethyl)-«-methylaminomethyl,
N~ethy1-N-propylaminomethy1,
N~ethyl-N—(1-methylethyl)aminomethyl,
H—butyl—N—ethylaminomethyl,
H-ethyl-M~( 1-methylpropyl) aminomethyl,
N-ethy l-N-( 2-methy lpropyl) aminomethyl, N-ethyl—N—(1,1-di—
methylethy1)aminomethyl,
M-(1-methylethyl)-N-propylaminomethyl,
H—butyl-N—propylaminomethyl,
N—(1-methylpropyl)—N—propylaminomethyl,
N-(2-methylpropyl)^J-propylaminomethyl,
N-(l,l-dimethylethyl)^?-propylaminomethyl,
N-buty l-N-{1-methylethyl)aminomethyl,
N-{ 1-methylethyl )-N—(1-methylpropyl) aminomethyl,
N-( 1-methylethyl )-N-(2-methylpropyl) aminomethyl,
N-( 1,1-dimethylethyl )-H-( 1-methyl ethyl) aminomethyl,
N-buty 1-N- (1-methylpropyl) aminomethyl,
N-butyl-»-( 2-methylpropyl) aminomethyl, N-butyl-W—
(1,1-dimethylethy1)aminomethyl,
N-( 1-methylpropyl )-N-(2-methy lpropyl) aminomethyl,
N- (1,1-dimethy lethy 1 )-N- (1-methylpropyl) aminomethyl,
N~{1,1-dimethylethyl)-N-(2-methylpropyl) aminomethyl,
2-tH,K-dimethylamino)ethyl, 2-(N,N-diethylamino)ethyl,
2-(N,N-dipropylamino)ethyl,
2-[N,N-di(1-methylethyl) amino]ethyl,
2-[N,N-dibutylamino]ethyl,
2-[N,N-di(1-methylpropyl)amino]ethyl,
2-tN,N-di(2-methylpropyl)amino]ethyl, 2-[K,»-di(lt 1—
dimethylethyl) amino ]ethyl, 2-[N-ethy 1-N-methylamino ]ethyl,
2-[ N-methyl-N-propylamino]ethyl,
2- [ N-methyl-N- (1-methylethyl) amino ] ethyl,
2-[N-buty 1—N-methylamino]ethyl,
2-IN-methyl-N-( 1-methylpropyl )amino]ethyl,
2- [ N-methyl-N-( 2-methy lpropyl) amino ] ethyl,
2-[N-(l, 1-dimethy lethylj-H-methylaminolethYlf

2-iN-ethyl-N-propylaminoJethyl,
2-[ N-ethy l-N-( 1-methylethyl) amino ] ethyl,
2-[ N-buty 1-N-ethy lamino ] ethyl«
2- [ N-ethy l-N-( 1-methy lpropy 1) amino ] ethyl,
2-[N-ethyl-N-(2-methylpropyl) amino] ethyl,
2-[K-ethyl-K~( 1, l-dimethylethylamino]ethyl,
2~[N-( 1-methylethyl )-N-propylamino Jethyl,
2- [ N-buty 1—N-propy lamino ] ethyl,
2—[ N—(1-methylpropyl)—N-propylamino] ethyl,
2— [»-(2-methylpropyl )—N~propylamino ] ethyl,
2—[N—(1,1—dimethylethyl)-N-propy lamino] ethyl,
2~[N-butyl-N-( 1-methylethyl) amino ]ethyl,
2-[N-( l-methylethyl)-N-( 1-methylpropyl) amino J ethyl,
2-iN-(l-*nethylethyl)^M2-methylpropyl) amino] ethyl,
2-[N-( 1,1-dimethylethyl )-N-{ 1-methylethyl) amino ] ethyl,
2-j N-buty 1-N- (1-methylpropyl) amino ] ethyl,
2-[N-butyl-N- 2— [N-^>utyl-N-( 1,1-dimethylethyl) amino Jethyl,
2—[N—( 1-methylpropyl )—K—(2-methylpropyl)amino]ethyl, 2-[N~(l, 1-dimethylethyl)-N-( 1-methylpropyl )amino]ethyl, 2-[N—( 1,1-dimethylethyl J-N-( 2-methylpropyl) amino]ethyl, 3-(N,N-dimethylamino)propyl, 3-(N,N-diethylamino)propyl, 4—(N,N—dimethylamino)butyl and 4—(N,N—diethylaminoJbutyl;
Ci-C4-alkoxy-Ci-C4-alkyl: Ci-C4-alkyl which is substituted by
Ci-Cj-alkoxy as mentioned above, i.e., for example
methoxymethyl, ethoxymethyl, propoxymethyl,
(l-methylethoxy)methyl, butoxymethyl,
(1 -methylpropoxy)methyl, {2-methylpropoxy)methy 1,
(l,l-dimethylethoxy)methyl, 2-(methoxyJethyl,
2-(ethoxyJethyl, 2-(propoxy)ethyl, 2-(l-methylethoxy)ethyl,
2-(butoxy)ethyl, 2-(l-methylpropoxy)ethyl,
2-(2-methylpropoxyjethyl, 2-{l,l-dimethylethoxy)ethyl,
2-{methoxy)propyl, 2-(ethoxyJpropyl, 2-(propoxy)propyl,
2-(l-methylethoxy)propyl, 2-(butoxyJpropyl,
2-(1-methylpropoxyJpropyl, 2-(2-methylpropoxyJpropyl,
2-(1,1-dimethylethoxyjpropyl, 3-(methoxyJpropyl,
3-(ethoxy)propyl, 3-(propoxy J propyl,
3-(l-methylethoxy)propyl, 3-(butoxy)propyl,
3- (1 -methylpropoxy) propyl, 3- (2 -methylpropoxy J propyl,
3-(l,l-dimethylethoxy)propyl, 2-(methoxyJbutyl,
2-(ethoxy)butyl, 2-(propoxy)butyl, 2-(l-methylethoxy)butyl,
2-{butoxy)butyl, 2-(1-methylpropoxy)butyl,
2- (2-methylpropoxy) butyl, 2- (1,1-dime thy let hoxy) butyl, 3-(methoxy)butyl, 3-(ethoxyJbutyl, 3-(propoxy)butyl, 3-(l-methylethoxyJbutyl, 3-(butoxyJbutyl, 3-(l-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,

3-(l,l-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(propoxy)butyl, 4-(l-methylethoxy)butyl, 4-(butoxy)butyl, 4-{1-methylpropoxy)butyl, 4-{2-methylpropoxy)butyl and 4-(1,l-dimethylethoxy)butyl;
Ci-C4-alkylthio-Ci-C4-alkyl: Ci-C4-alkyl which is substituted
by Ci-C4-alkylthio as mentioned above, i.e., for example
methylthiomethyl, ethylthiomethyl, propylthiomethyl,
(l-methylethylthiojmethyl, butylthiomethyl,
(l-methylpropylthio)methyl, (2-methylpropylthio)methyl,
{1,l-dimethylethylthio)methyl, 2-methylthioethyl,
2-ethylthioethyl, 2-(propylthio)ethyl,
2-(1-methylethylthio)ethyl, 2-(butylthio)ethyl,
2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl,
2 - (1,1 -dimethy lethy lthio) ethyl, 2- (methy lthio) propyl,
3-(methylthio)propyl, 2-{ethylthio)propyl,
3-(ethylthio)propyl, 3-{propylthio)propyl,
3-(butylthio)propyl, 4-(methylthio)butyl, 4-(ethylthio)butyl,
4-(propylthio}butyl and 4-(butylthio)b\itylj
Ci-C4-alkoxycarbonyl-Ci-C4-alJcyl: Cj-C4-alkyl which is substituted by Ci-C4-alkoxycarbonyl as mentioned above, i.e., for example methoxycarbonylmethyl, e t hoxycarbony line thyl, propoxycarbonylmethy 1, (1 -methylethoxycarbonyl) methyl, butoxycarbonylmethyl, (1 -methylpropoxycarbonyl) methyl, (2-methylpropoxycarbonyl)methyl,
(l,l-dimethylethoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl,
2 - (1-methylethoxycarbonyl) ethyl, 2 - (butoxycarbony 1) ethyl,
2-{1-methylpropoxycarbonyl}ethyl,
2-{2-methylpropoxycarbonyl)ethyl,
2-(1,1-dimethylethoxycarbony1)ethyl,
2-(methoxycarbony 1)propyl, 2-(ethoxycarbonyl)propyl,
2-(propoxycarbony 1) propyl, 2-(1 -methylethoxycarbonyl) propyl,
2-(butoxycarbonyl)propyl, 2-(Z-methylpropoxycarbonyl)propyl,
2-(2-methylpropoxycarbonyl)propyl,
2-(1,1-dimethylethoxycarbonyl)propyl,
3- (methoxycarbony 1) propyl, 3- (ethoxycarbony 1)propyl,
3- (propoxycarbony 1) propyl, 3- (1-methylethoxycarbonyl)propyl,
3- (butoxycarbonyl) propyl, 3-(1 -methylpropoxycarbonyl) propyl,
3-(2-methylpropoxycarbonyl)propyl,
3 - (1,1-dimethylethoxycarbonyl)propyl,
2-(methoxycarbonyl)butyl, 2-(ethoxycarbonyl)butyl,
2-(propoxycarbony 1) butyl, 2- (1 -methylethoxycarbonyl) butyl,
2-{butoxycarbonyl)butyl, 2-(1-methylpropoxycarbonyl)butyl,
2-(2-methylpropoxycarbonyl)butyl,
2-(1,l-dimethylethoxycarbonyl)butyl.

3-(methoxycarbony1)butyl, 3-(ethoxycarbony1)butyl, 3-(propoxycarbonyl)butyl, 3-(l-methylethoxycarbonyl)butyl, 3-(butoxycarbonyl)butyl, 3-(1-methylpropoxycarbony1)butyl, 3-{2-methylpropoxycarbonyl)butyl,
3-(l,l-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)— butyl, 4-(ethoxycarbony1)butyl, 4-(propoxycarbony1)butyl, 4-{1-methylethoxycarbony1)butyl, 4-(butoxycarbonyl)butyl, 4-(l-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and 4-(1,1-dimethylethoxycarbonyl)butyl;
Ci-C4-alkoxy-C2-C4-alkoxy: C2-C4-alkoxy which is substituted
by Ci-C4-alkoxy as mentioned above, i.e., for example
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-methyIpropoxy) propoxy,
3-(l,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy,
2-(ethoxy)butoxy, 2-(propoxy)butoxy,
2-(1-methylethoxy)butoxy, 2-{butoxy)butoxy,
2-(1-methyIpropoxy)butoxy, 2-{2-methyIpropoxy)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-(methoxyJbutoxy, 4-(ethoxy)butoxy, 4-(propoxy)butoxy,
4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy,
4-(l-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and
4-(1,1-dimethylethoxy)butoxy;
— C2-C6—alkanediyl: for example ethane— 1,2-diyl, propane—1,3-diyl, butane-l^-diyl, pentane-1,5—diyl and hexane-1,6-diyl;
— C3-C6-cycloalkyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
— Ca-Cs-cycloalkyl: C3-C6-cycloalkyl as mentioned above, and also cycloheptyl and cyclooctyl.

All phenyl rings are preferably unsubstituted or have attached to them one to three halogen atoms and/or a nitro group, a cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.
With a view 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:
R1, R2 are nitro, halogen, cyano, Ci-C6-alkyl»
Ci—Ce—haloalkyl, Ci—Cg—alkoxy, Ci—C6—haloalkoxy, Ci-Cg—alkylthio, Ci-C6—haloalkylthio, Ci-C6—alkylsulfinyl, Ci-Cg—haloalkylsulfinyl, Ci—Cfi—alkylsulfonyl or Ci-Cg—haloalkylsulfonyl; particularly preferably nitro, halogen, such as, for example, chlorine and bromine, Ci-C6-alkyl, such as, for example, methyl and ethyl, Ci-C6-alkoxy, such as, for example, methoxy and ethoxy, Ci—Cg—haloalkyl, such as, for example, difluoromethyl and trifluoromethyl, Ci-Cg-aikylthio, such as, for example, methylthio and ethylthio, Ci-Cs-alKylsulfinyl, such as, for example, methylsulfinyl and ethylsulfinyl, Ci-Cg—alkylsulfonyl, such as, for example, methylsulfonyl, ethylsulfonyl and propylsulfonyl, or Ci—Ce—haloalkylsulfonyl, such as, for example, trifluoromethylsulfonyl and pentafluoroethylsulfonyl;
R3 is hydrogen;
R4 is hydrogen;
R5, R6 are hydrogen, halogen, cyano, nitro, C1—C4—alkyl, Cx-Cj—alkoxy-Ci-^U-alkyl, C1-C4-alkoxycarbonyl-Ci-C4—alkyl, Ci-C4—alkylthio~Ci-C4—alkyl, C1-C4—haloalkyl, Ci-C4-cyanoalkyl, Ca-Cs-^ydoalkyl, Cj-C4-alkoxy, C1-C4—alkoxy-C2-C4-alkoxy, C1-C4—haloalkoxy, C1-C4-alkylthio, Ci-C4-haloalkylthio,
di(CJ-C4—alkyl)amino, COR8, phenyl or benzyl, where the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, Ci-C4-alkyl, C1-C4—haloalkyl, Ci-C^-alkoxy or Ci—C4—haloalkoxy;

or
R5 and Rfi together form a C2—C6—alkanediyl chain which may be
mono- to tetrasubstituted by Cj—C4—alkyl and/or may be interrupted by oxygen or an unsubstituted or C1-C4—alkyl-substituted nitrogen;
R5 is particularly preferably hydrogen, halogen, cyano, nitro, Ci-C4-alJcyl, Ci-C4-alkoxy-<:i-c4-alkyl c1-c4-alkoxycarbonyl-ci-c4-alkyl ci-c4-alkylthio ci-cj-alkyl ci-c4-haloalkyl ci-ci-cyanoalkyl c3-cg d-c4-alkoxy c1-c4 alkoxy ci-c4-haloalkoxy ci-c4-haloalkylthio di cor8 phenyl or benzyl where the two last-mentioned substituents may be partially fully halogenated and carry one to three of following groups:> nitro, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4—alkoxy or C1-C4—haloalkoxy;
R6 is particularly preferably hydrogen or Ci-C4-alkyl; very particularly preferably, R5 is hydrogen, C1-C4—alkyl, Ci-C4-haloalkyl, c1-C4-alkoxycarbonyl or CONKER";
very particularly preferably, R6 is hydrogen or Ci-C4-alkyl;
most preferably, R5 is hydrogen or Ci-Ci-alkyl, in-particular hydrogen; most preferably, R6 is hydrogen;
R? is halogen, Cj-Ce-31^1' Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg—alkylthio, Ci-C^—alkylsulfinyl, Ci-Cg-alkylsulfonyl, amino, Ci-Cg-aikyiamino, di(Cr-C6~alkyl) amino, di{Ci-C4-alkoxy)methyl or CORB; particularly preferably Ci-C4~alkyl, such as, for example, methyl, ethyl, 1-methyletliyl or 1,1—dimethylethyl, hydroxycarbonyl or C1-C4—alkoxycarbonyl, such as, for example, methoxycarbonyl or ethoxycarbonyl;
R8 is Ci-C4-alkyl, hydroxyl, Ci^-alkoxy or KR9R10;
R9 is hydrogen or C1-C4—alkyl;
Rio is C1-C4—alkyl;
Ri2 is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylBulfonyl, Ci-C4-haloalkylsulfonyl, phenyl,

benzyl, phenylcarbonyl or phenylcarbonyl [sic] or
phenylsulfonyl, where the phenyl radical of the five
last-mentioned substituents may be partially or fully
halogenated and/or may carry one to three of the
following groups:
nitro, cyano, Cj-^-alkyl, C1-C4—haloalkyl, Ci-C4-alkoxy
or Ci-C4-haloalkoxy;
is particularly preferably hydrogen, Ci-C4-alkylf
C1-C4—alkylsulfonyl, Ci-C4-haloalkylsulfonyl, phenyl,
benzyl or phenylsulfonyl, where the phenyl radical of
the three last-mentioned substituents may be partially
or fully halogenated and/or may carry one to three of
the following groups:
nitro, cyano, Cj-C*—alkyl, C1-C4—haloalkyl, Ci-C4-alkoxy
or C1-C4—haloalkoxy;
is very particularly preferably hydrogen or
Cj-C4-alkylsulfonyl, Ci-C^-haloalkylsulfonyl or
phenylsulfonyl, where the phenyl radical may be
partially or fully halogenated and/or may carry one to
three of the following groups:
nitro, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy
or Ci-C4-haloalkoxy;
is likewise particularly preferably hydrogen, Ci-C4-alkyL, Ci-C4-alkylsulfonyl,
Ci-Cj-haloalkylsulfonyl, thienylmethyl, phenyl, benzyl, phenylsulfonyl or phenylcarbonylmethyl, where the phenyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4-alkyl, Ci-C4-haloalkyl, Ci-04-alkoxy or Ci-C4-haloalkoxy;
R13 is Ci-C6-alkyl or C3-C6-cycloalkyl;
particularly preferably methyl, ethyl, 1-methylethyl, 1,1—dimethylethyl or cyclopropyl;
R14 is hydrogen or Ci-Ce-alkylj
particularly preferably hydrogen or methyl.
The following embodiments of the
3— (4,5—dihydroisoxazol—5—yl)benzoylpyrazoles of the formula I are
to be emphasized:

1. In a preferred embodiment of the
3—(4,5-dihydroisoxazol—5—yl)benzoylpyrazoles of the formula I,
R1 is nitro, halogen, Ci-Cg—alkyl, Ci-Cg—haloalkyl, Ci-C6-alkoxy or Ci-Cg—haloalkoxy;
particularly preferably nitrogen, halogen, such as chlorine or bromine, Cj—C4—alkyl, such as methyl or ethyl, C1-C4—haloalkyl, such as difluoromethyl or trifluoromethyl, C1-C4—alkoxy, such as methoxy or ethoxy, or C1-C4—haloalkoxy such as difluoromethoxy or trifluoromethoxy;
particularly preferably halogen, such as chlorine or bromine, Ci-C^-alkyl, such as methyl or ethyl or Ci-C^-alkoxy, such as methoxy or ethoxy; most preferably halogen, such as chlorine or bromine, Ci-C4-alkyl, such as methyl or ethyl;
R2 is halogen, Cj-Cg—haloalkyl, Ci-Cg—alkylthio, Ci-Cfi-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-Ce—haloalkylsulfinyl, Ci-C$—alkylsulfonyl or -Cj-Ce-haloalkylsulfonyl;
particularly preferably halogen, such as fluorine or chlorine, C1-C4—haloalkyl, such as difluoromethyl or trifluoromethyl, or Ci-C4-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl;
very particularly preferably halogen, such as fluorine or chlorine, or Ci—C4—alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.
2. In a further preferred embodiment of the
3— {4,5-dihydroisoxazol—5-yl)benzoylpyrazoles of the formula
I*
R3 is hydrogen.
3. In a further preferred embodiment of the
3—{4,5-dihydroisoxazol—5—yl)benzoylpyrazoles of the formula
I#
R3 is halogen or Ci-Ct-alkyl;
particularly preferably chlorine or methyl.

4. In a further [lacuna] embodiment of the
3— (4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,
R4 is hydrogen;
R5 is hydrogen, halogen, cyano, nitro, C1-C4—alkyl,
Ci-C4-alkoxy-Ci-C4-alkyl, Ci-Ci-alkoxycarbonyl-Cj-Cn-alkyl, Ci-C^-alkylthio-Ci-Cr-alkyl, C1-C4-haloalkyl/ Ci-C^-cyanoalkyl, C3-CB-cycloalkyl, Cl-C4-alkoxy, Ci—C4—alkoxy-Cj-Ci-al^oxy, Ci-C4-haloalkoxy, Cx-C4-alkylthio, Cj-C4-haloalkylthio, di(Cj-C4—alkyl)amino, C1-C4—alkylcarbonyl, C1-C4—alkoxycarbonyl, CONR9R10, phenyl or ben2yl, where the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groupst nitro, cyano, Ci-Ca-alkyl, C1-C4—haloalkyl, Ci-C4-alkoxy or Ci-C4~haloalkoxy; is particularly preferably hydrogen, C1-C4—alkyl, C!-C4-haloalkyl, Ci-C4-alkoxycarbonyl or COHR'R10; very particularly preferably hydrogen or Cj-C4-alkyl, such as methyl or ethyl; most preferably hydrogen;
R6 is hydrogen or C1-C4—alkyl, such as methyl or ethyl; particularly preferably hydrogen.
5. In a further preferred embodiment of the
3—(4,5-dihydroisoxazol—5-yl)benzoylpyrazoles of the formula I,
R7 is halogen, Ci-Cg—alkyl, Ci—C6—haloalkyl,
Ci-C6-al^oxy/ Ci-Cs-alkylthio, Ci-Cg-alkylsulfinyl,
Ci-Cg-alkylsulfonyl, amino, Ci-Ce—alkylamino,
di(Ci-C6-alkyl)amino, di(Ci-Ce-alkoxy)methyl,
formyl, Ci-C4-alkylcarbonyl,
Ci—C4—haloalkylcarbonyl, hydroxycarbonyl/
C1-C4—alkoxycarbonyl, C1-C4—haloalkoxycarbonyl or
C0NR9R";
particularly preferably halogen, such as chlorine
or bromine, C1-C4—alkyl, such as methyl, ethyl,
l~methylethyl or 1,1-dimethylethyl, Ci-C4-alkoxy,
such as methoxy or ethoxy, C1-C4—alkylthio, such as
methylthio or ethylthio, Ci-Cj-alkylsulfinyl, such

as methylsulfinyl or ethylsulfinyl, Ci-Cfl-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, amino, Ci—C4—alkylaroino, such as methyl amino or ethylamino, di(Ci—C4—alkyljamino, such as dimethylamino or diethylamino, di(Ci-C4-alkoxy)methyl, such as dimethoxymethyl or diethoxymethyl, C1-C4-alkylcarbonyl, such as methylcarbonyl or ethylcarbonyl, hydroxycarbonyl, Ci—C4—alkoxycarbonyl, such as methoxycarbonyl or ethoxycarbonyl, or CONR9R10;
very particularly preferably C1-C4—alkyl, such as methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl, hydroxycarbonyl or Ci—C4—alkoxycarbonyl, such as methoxycarbonyl or ethoxycarbonyl; most preferably Ci-Cj-alkyl, such as methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl;
6. In a further preferred embodiment of the
3— (4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I,
R" is Cx-C Ci-C4-alkylcarbonyl, C1-C4—haloalkylcarbonyl, Ci-C4-alkylsulfonyl, C1-C4—haloalkylsulfonyl, phenyl, benzyl, phenylcarbonyl or phenylsulfonyl, where the phenyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, Ci-C4~alkyl, C1-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy; is particularly preferably Ci-C4-alkyl, C!-C4-alJcylsulfonyl, C1-C4-haloalkylsulfonyl, phenyl, benzyl or phenylsulfonyl, where the phenyl radical of the three last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or C1-C4-haloalkoxy; is very particularly preferably Ci-C4-alkylsulfonyl, C1-C4—haloalkyl sulfonyl or phenylsulfonyl, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, Ci—C4~a.lkyl, C1-C4—haloalkyl, Ci-C4-alkoxy or C1-C4—haloalkoxy;

is likewise particularly preferably benzyl, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, Ci—C4—alkyl, Ci-C4-haloalkyl, C1-C4—alkoxy or C1-C4—haloalkoxy.
7. In a further preferred embodiment of the
3-{4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula
I,
R12 is Ci-C4-alkyl, C3-C4-alkynyl, thienylmethyl, benzyl, phenylcarbonyl, phenylsulfonyl or phenylcarbonylmethyl, where the phenyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, Cj-C^-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy; is particularly preferably thienylmethyl, such as 3-thienylmethyl, benzyl, phenylcarbonyl, phenylsulfonyl or phenylcarbonylmethyl, where the phenyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, Cj-Ci-alkyl, Ci-C4-haloalkyl, C1-C4-alkoxy or Cj-04-haloalkoxy.
8. In a further preferred embodiment of the
3—(4,5-dihydroisoxazol—5—yl)ben2oylpyrazoles of the formula I, R12 is hydroxyl.
9. In a further preferred embodiment of the
3— (4,5-dihydroisoxazol—5-yl)benzoylpyrazoles of the formula I,
R" is CjH^-alkyl, such as methyl, ethyl, methylethyl or 1,1-dimethylethyl, or C3-Cg-cycloalkyl, such as cyclopropyl;
particularly preferably Ci-C4-alkyl, such as methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl; likewise preferably C3-C6-cycloalkyl, such as cyclopropyl;

R1* is hydrogen or C],—C4—alkyl, such as, for example, methyl or ethyl; particularly preferably hydrogen or methyl.
10. In a further preferred embodiment of the
3-(4,5~dihydroisoxazol-5-yl)ben2oylpyrazoles of the formula I,
R1 is halogen Ci-C4-alkyl or Cj-C4-alkoxy;
R2 is halogen or Ci-C4-alkylsulfonyl;
R3, R4 and R6 are hydrogen?
R5 is hydrogen or Ci-CValkyl; in particular hydrogen
R' is Ci-C4-alkyl, di(Ci-C4-alkoxy)methylf hydroxycarbonyl or Ci-C4-alkoxycarbonyl;
R12 is hydrogen, C3-C4-alkynyl, thienylmethyl, benzyl, phenylcarbonyl, phenylsulfonyl or phenylcarbonylmethyl, where the phenyl radical of the four last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups; nitro, cyano, Ci-C4-alkyl, Cj-C4-haloalkyl, Cj-C4-alJcoxy or Ci-C4-haloalkoxy;
Ri3 is Ci-Ci-alkyl, Ci-C4-haloalkyl or cyclopropyl; in particular Ci-C4-alkyl or cyclopropyl;
RH is hydrogen, Ci-C4-alkyl or cyclopropyl; in particular hydrogen or Ci-C4-alkyl.
Most particular preference is given to the
3-(4,S-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula Ial





Particular preference is likewise given to the compounds Ia3, in particular to the compounds Ia3.1 — Ia3.64 which differ from compounds Ial.l — lal.64 in that R13 is isopropyl.

Particular preference is likewise given to the compounds Ia4, in particular to the compounds Ia4.1 - Ia4.64 which differ from compounds Ial.l — lal.64 in that R13 is tert—butyl.

Particular preference is likewise given to the compounds Ia5, in particular to the compounds I&5.1 — Ia5.64 which differ from compounds Ial.l — lal.64 in that R14 is methyl.

Particular preference is likewise given to the compounds Ia6, in particular to the compounds Ia6.1 — Ia6.64 which differ from compounds Ial.l — lal.64 in that R13 is ethyl and R14 is methyl.


particular preference is likewise given to the compounds Ia7, in particular to the compounds Ia7.1 — Ia7.64 which differ from compounds lal.l — Ial.64 in that R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia8, in particular to the compounds Iafl.l — IaS.64 which differ from compounds lal.l — Ial.64 in that R13 is tert-butyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia9, in particular to the compounds ia9.1 — Ia9.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl.


Particular preference is likewise given to the compounds IalO, in particular to the compounds ialO.l — Ial0.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl and R13 is ethyl.

Particular preference is likewise given to the compounds Iall, in particular to the compounds lall.l — Iall.64 which differ from compounds ial.l — lal.64 in that R1 is methyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Xal2, in particular to the compounds lal2.1 — Ial2.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ial3, in particular to the compounds Ial3.1 — Ial3.64 which differ from compounds Ial.l — lal.64 in that R1 and R14 are methyl.


Particular preference is likewise given to the compounds Ial4, in particular to the compounds Ial4.1 — Ial4.64 which differ from compounds Ial.l — Ial.64 in that R1 and R14 are methyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ial5, in particular to the compounds Ial5.1 — Ial5.64 which differ from compounds Ial.l — ial.64 in that R1 and R14 are methyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ial6, in particular to the compounds Ial6.1 — Ial6.64 which differ from compounds ial.l — Ial.64 in that R1 and R14 are methyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ial7, in particular to the compounds Ial7.1 - Ial7.64 which differ from compounds Ial.l — Ial-64 in that R1 is trifluoromethyl.

Particular preference is likewise given to the compounds I&18, in particular to the compounds Ial8.1 - Ial8.64 which differ from compounds Ial.l - Ial.64 in that R1 is trif luoromethyl and Ri3 j.s ethyl.

Particular preference is likewise given to the compounds Ial9, in particular to the compounds Ial9.1 — Ial9.64 which differ from compounds Ial.l - ial.64 in that R1 is trif luoromethyl and R13 is isopropyl.

Particular preference is likewise given to the compounds 1420, in particular to the compounds Ia20.1 — la20.64 which differ from compounds Ial.l — Ial.64 in that R1 is trif luoromethyl and Ri3 is tert-butyl..


Particular preference is likewise given to the compounds Ia21, in particular to the compounds Ia21.1 — Ia21.64 which differ from compounds Ial.l - lal.64 in that R1 is trifluoromethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia22, in particular to the compounds Ia22.1 — Ia22.64 which differ from compounds Ial.l - lal.64 in that R1 is trifluoromethyl, R13 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia23, in particular to the compounds Ia23.1 — Ia23.64 which differ from compounds ial.l - lal.64 in that R1 is trifluoromethyl, R13 is isopropyl and R14 is methyl.


Particular preference is likewise given to the compounds ia24, in particular to the compounds Ia24.1 — Ia24.64 which differ from compounds lal-1 — lal.64 in that Rl is trifluoromethyl, R*3 is tert-butyl and B14 is methyl.

Particular preference is likewise given to the compounds Ia25, in particular to the compounds Ia25.1 — la25.64 which differ from compounds lal.l — lal.64 in that R1 is methoxy.

Particular preference is likewise given to the compounds Ia26, in particular to the compounds Ia26.1 - Xa26.64 which differ from compounds lal.l — lal.64 in that R1 is methoxy and R13 is ethyl.

Particular preference is likewise given to the compounds ia27, in particular to the compounds Ia27.1 — la27.64 which differ from compounds lal.l — lal.64 in that R1 is methoxy and R13 is isopropyl.


Particular preference is likewise given to the compounds Ia28, in particular to the compounds Ia28.1 - Ia28.64 which differ from compounds lal.l - ial.64 in that Ri is methoxy and R13 is tert-butyl.

Particular preference is likewise given to the compounds Xa29, in particular to the compounds la29.1 — Ia29.64 which differ from compounds lal.l — Ial.64 in that Rl is methoxy and R14 is methyl.

Particular preference is likewise given to the compounds Ia30, in particular to the compounds Ia30.1 - Ia30.64 which differ from compounds lal.l - ial.64 in that R1 is methoxy, R13 is ethyl and R" is methyl.


Particular preference is likewise given to the compounds Ia31, in particular to the compounds Ia31.1 - Ia31.64 which differ from compounds Ial.l - Ial.64 in that Ri is methoxy, R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia32, in particular to the compounds la32,l — Ia32.64 which differ from compounds Ial.l - Ial.64 in that R1 is methoxy, R13 is tert-butyl and R14 is methyl.

Particular preference is likewise given to the compounds la33, in particular to the compounds ia33.1 — Ia33.64 which differ from compounds Ial.l - Ial.64 in that R2 is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia34, in particular to the compounds Ia34.1 — Ia34.64 which differ from compounds Ial.l - Ial.64 in that R* is ethylsulfonyl and R" is ethyl.


Particular preference is likewise given to the compounds Ia35, in 'particular to the compounds Ia35.1 - Ia35.64 which differ from compounds Ial.l - Ial.64 in that R2 is ethylsulfonyl and R*3 is ethyl.

Particular preference is likewise given to the compounds Xa36, in particular to the compounds Ia36.1 — Ia36.64 which differ from compounds Ial.l — IaX.64 in that R2 is ethylsulfonyl and R13 is tert—butyl.

Particular preference is likewise given to the compounds Ia37, in particular to the compounds Ia37.1 — Ia37.64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia38, in particular to the compounds Ia38.1 - Ia38.64 which differ from compounds lal.l - Ial.64 in that R2 is ethylsulfonyl, R*3 iS ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia39, in particular to the compounds Ia39.1 — ia39.64 which differ from compounds lal.l — ial.64 in that R2 is ethylsulfonyl, R13 is isopropyl and R1* is methyl.
Particular preference is likewise given to the compounds Ia40, in particular to the compounds Ia40.1 — Ia40.64 which differ from compounds lal.l — Ial.64 in that R2 is ethylsulfonyl, R13 is tert-butyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia41, in particular to the compounds Ia41.1 — Ia41.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl and R2 is ethylsulfonyl.


Particular preference is likewise given to the compounds ia42, in particular to the compounds Ia42.1 — I&42.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl, R2 is ethylsulfonyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ia43, in particular to the compounds Ia43.1 — ia43.64 which differ from compounds Ial.l - lal.64 in that R1 is methyl, R* is ethylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia44, in particular to the compounds Ia44.1 — Ia44.64 which differ from compounds ial.l - lal.64 in that R1 is methyl, R* is ethylsulfonyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ia45, in particular to the compounds Ia45.1 - la45-64 which differ from compounds ial.l — lal.64 in that R1 and R14 are methyl and R2 is ethylsulfonyl.

Particular preference is likewise given to the compounds ia46, in particular to the compounds Ia46.1 — Ia46.64 which differ from compounds Ial.l — lal.64 in that R1 and R14 are methyl, R2 is ethylsulfonyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ia47, in particular to the compounds Ia47.1 — Ia47.64 which differ from compounds Ial.l - lal.64 in that R1 and R14 are methyl, R2 is ethylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia48, in particular to the compounds Ia48.1 — Ia48.64 which differ from compounds Ial.l — lal.64 in that R1 and R14 are methyl, R2 is ethylsulfonyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ia49, in particular to the compounds Ia49.1 - Ia49.64 which differ from compounds Ial.l — ial.64 in that R1 is trifluoromethyl and R2 is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia50, in particular to the compounds Ia50.1 — Ia50.64 which differ from compounds Ial.l — ial.64 in that R1 is trifluoromethyl, R2 is ethylsulfonyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ia51, in particular to the compounds Ia51.1 — Ia51.64 which differ from compounds Ial.l — Ial.64 in that R1 is trifluoromethyl, R2 is ethylsulfonyl and R13 is isopropyl.


Particular preference is likewise given to the compounds Ia52, in particular to the compounds Ia52.1 — Ia52.64 which differ from compounds lal.l — Ial.64 in that R1 is trifluoromethyl, R2 is ethylsulfonyl and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia53, in particular to the compounds Ia53.1 — Ia53.64 which differ from compounds lal.l — ial.64 in that R1 is trifluoromethyl, R2 is ethylsulfonyl and Ri* is methyl.

Particular preference is likewise given to the compounds Xa54, in particular to the compounds Xa54.1 — Ia54.64 which differ from compounds lal.l — ial.64 in that Ri is trifluoromethyl, R2 is ethylsulfonyl, R13 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia55, in particular to the compounds Ia55.1 — Ia55.64 which differ from compounds lal.l — Ial.64 in that R1 is trifluoromethyl, R2 is ethylsulfonyl, R13 is isopropyl and R1* is methyl.


particular preference is likewise given to the compounds Ia56, in particular to the compounds Ia56.1 - Ia56.64 which differ from compounds ial.l - Ial.64 in that R* is trifluorometnyl, R2 is ethylsulfonyl, R" is tert-butyl and a« is methyl.

Particular preference is likewise given to the compounds Ia57, in particular to the compounds la57.1 — Ia57.64 which differ from, compounds Ial.l — Ial.64 in that R* is methoxy and R2 is ethylsulfonyl.

particular preference is likewise given to the compounds Ia58, in particular to the compounds Ia58,l ~ la58.64 which differ from compounds Ial.l — Ial.64 in that R1 is methoxy, R2 is ethylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia59, in particular to the compounds Ia59.1 - Ia59.64 which differ from compounds lal.l - ial-64 in that R1 is methoxy, R2 is ethylsulfonyl and R*3 is isopropyl.

Particular preference is likewise given to the compounds Ia60, in particular to the compounds Ia60.1 — Ia60.64 which differ from compounds lal.l — ial.64 in that R1 is methoxy, R2 is ethylsulfonyl and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia61, in particular to the compounds la61.1 — Ia61.64 which differ from compounds lal.l — Ial.64 in that R1 is methoxy/ R2 is ethylsulfonyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia62, in particular to the compounds Ia62.1 - Ia62.64 which differ from compounds lal.l — Ial.64 in that R1 is methoxy, R2 is ethylsulfonyl, R13 is ethyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia63, in particular to the compounds ia63.1 - Ia63.64 which differ from compounds lal.l — Ial.64 in that R1 is methoxy, R2 is ethylsulfonyl, R" is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia64, in particular to the compounds Ia64.1 — Ia64.64 which differ from compounds lal.l — Ial.64 in that R1 is methoxy, R2 is ethylsulfonyl, R" is tert-butyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia65, in particular to the compounds ia65.1 — Ia65.64 which differ from compounds lal.l — Ial.64 in that R2 is chlorine.

Particular preference is likewise given to the compounds Ia66, in particular to the compounds ia66.1 — Ia66.64 which differ from compounds lal.l - Ial.64 in that R2 is chlorine and R13 is ethyl.


Particular preference is likewise given to the compounds Ia67, in particular to the compounds Ia67.1 - Ia67.64 which differ from compounds Ial.l - lal.64 in that R2 is chlorine and R13 is isopropyl.

Particular preference is likewise given to the compounds Xa68, in particular to the compounds Ia68.1 - Ia68.64 which differ from compounds Ial.l — lal.64 in that R2 is chlorine and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia69, in particular to the compounds Ia69.1 — Ia69.64 which differ from compounds Ial.l — lal.64 in that R2 is chlorine and R14 is methyl.

Particular preference is likewise given to the compounds Ia70, in particular to the compounds Ia70.1 — Ia70.64 which differ from compounds Ial.l — lal.64 in that R3 is chlorine, R13 is ethyl and Ri* is met&yl.


Particular preference is likewise given to the compounds Ia71, in particular to the compounds Ia71.1 — Ia71.64 which differ from compounds lal.l — ial.64 in that R2 is chlorine, R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia72, in particular to the compounds Ia72.1 — Ia72.64 which differ from compounds lal.l - Ial.64 in that R2 is chlorine, R13 is tert-butyl and R*4 is methyl.

Particular preference is likewise given to the compounds Ia73, in particular to the compounds Ia73.1 — Ia73.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl and R2 is chlorine.

Particular preference is likewise given to the compounds Ia74, in particular to the compounds Ia74.1 — Ia74.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl, R2 is chlorine and R13 is ethyl.


Particular preference is likewise given to the compounds 1875, in particular ±o the compounds Ia75.1 - Ia75.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl, R2 is chlorine and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia76, in particular to the compounds Ia76.1 — Ia76.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl, R2 is chlorine and Ri3 is tert-butyl.

Particular preference is likewise given to the compounds Ia77, in particular to the compounds Ia77.1 — la77.64 which differ from compounds Ial.l - lal.64 in that R1 and R14 are methyl and R2 is chlorine.


Particular preference is likewise given to the compounds Ia78, in particular to the compounds Ia78.1 — Ia78.64 which differ from compounds Ial.l - Ial.64 in that R1 and R14 are methyl, R2 is chlorine and Ri3 is ethyl.

Particular preference is likewise given to the compounds Ia79, in particular to the compounds Ia79.1 — Ia79.64 which differ from compounds Ial.l - Ial.64 in that R1 and R14 are methyl, R2 is chlorine and R*3 is isopropyl.

Particular preference is likewise given to the compounds Ia80, in particular to the compounds Ia80.1 — Ia80.64 which differ from compounds Ial.l — Ial.64 in that R1 and R14 are methyl, R2 is chlorine and R13 is tert—butyl.

Particular preference is likewise given to the compounds Xa81, in particular to the compounds Ia81.1 — Ia81.64 which differ from compounds Ial.l - ial.64 in that R1 is trifluoromethyl and R2 is chlorine.


Particular preference is likewise given to the compounds Ia82, in particular to the compounds Ia82.1 - Ia82.64 which differ from compounds Ial.l - lal.64 in that R1 is trifluoromethyl, R2 is chlorine and R13 is ethyl.

Particular preference is likewise given to the compounds 1883/ in particular to the compounds Ia83.1 — Ia83.64 which differ from compounds Ial.l — lal.64 in that R1 is trifluoromethyl, R2 is chlorine and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia84, in particular to the compounds Ia84.1 — Ia84.64 which differ from compounds Ial.l — lal.64 in that R1 is trifluoromethyl, R2 is chlorine and R13 is tert—butyl.

Particular preference is likewise given to the compounds Ia85, in particular to the compounds Ia85.1 — Ia85.64 which differ from compounds Ial.l — lal.64 in that R1 is trifluoromethyl, R2 is chlorine and R1* is methyl.


Particular preference is likewise given to the compounds Ia86, in particular to the compounds Ia86.l - Ia86.64 which differ from compounds Ial.l - lal.64 in that R1 is trifluoromethyl, R2 is chlorine, R13 is ethyl and R14 is methyl.

particular preference is likewise given to the compounds Ia87, in particular to the compounds Ia87.1 — Ia87.64 which differ from compounds ial.l — lal.64 in that R1 is trifluoromethyl, R2 is chlorine, R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Xa88, in particular to the compounds Ia88.1 - Ia88.64 which differ from compounds Ial.l — lal.64 in that RJ is trifluoromethyl, R2 is chlorine, R13 is tert-butyl and R14 is methyl.

particular preference is likewise given to the compounds Ia89, in particular to the compounds Ia89.1 — ia89.64 which differ from compounds Ial.l - lal.64 in that R1 is methoxy and R2 is chlorine.

Particular preference is likewise given to the compounds Ia90, in particular to the compounds Ia90.1 — Ia90.64 which differ from compounds Ial.l — lal.64 in that R1 is methoxy, R2 is chloR1ne and R13 is ethyl.

Particular preference is likewise given to the compounds Ia91, in particular to the compounds Ia91.1 — Ia91.64 which differ from compounds Ial.l — lal.64 in that R1 is methoxy, R2 is chloR1ne and R*3 is isopropyl.

Particular preference is likewise given to the compounds Ia92, in particular to the compounds Ia92.1 — ia92.64 which differ from compounds Ial.l — lal.64 in that Rl is methoxy, R2 is chloR1ne and R" is tert-butyl.





Particular preference is likewise given to the compounds Ia97, in particular to the compounds Ia97.1 - Ia97.64 which differ from compounds lal.l — lal.64 in that R2 is tR1fluoromethyl.

Particular preference is likewise given to the compounds Ia98, in particular to the compounds Ia98.1 — Ia98.64 which differ from compounds lal.l — lal.64 in that R2 is tR1fluoromethyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ia99, in particular to the compounds Ia99.1 — Ia99.64 which differ from compounds lal.l — lal.64 in that R2 is tR1fluoromethyl and R13 is ethyl.

Particular preference is likewise given to the compounds IalOO, in particular to the compounds IalOO.l — IalOO.64 which differ from compounds lal.l — lal.64 in that R2 is tR1fluoromethyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds lalOl, in particular to the compounds IalOl.l — Ial01.64 which differ from compounds Ial.l - lal.64 in that R2 is tR1fluoromethyl and R14 ig methyl.

Particular preference is likewise given to the compounds Ial02, in particular to the compounds Ial02.1 — Ial02.64 which differ from compounds Ial.l — lal.64 in that R2 is tR1fluoromethyl, R13 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ial03, in particular to the compounds Ial03.1 — Jal03.64 which differ from compounds Ial.l — lal.64 in that R2 is tR1fluoromethyl, R13 is isopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ial04, in particular to the compounds Ial04.I — Ial04.64 which differ from compounds Ial.l - Ial.64 in that R2 is tR1fluoromethyl, R13 is tert—butyl and R14 is methyl.

Particular preference is likewise given to the compounds Ial05, in particular to the compounds Ial05.1 — Ial05.64 which differ from compounds Ial.l — Ial.64 in that R1 is methyl and R2 is tR1fluoromethyl.

Particular preference is likewise given to the compounds Ial06, in particular to the compounds Ial06.1 — Ial06.64 which differ from compounds Ial.l - Ial.64 in that R1 is methyl, R2 is tR1fluoromethyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ial07, in particular to the compounds Ial07.1 — Ial07.64 which differ from compounds Ial.l — Ial.64 in that R1 is methyl, R2 is tR1fluoromethyl and R13 is isopropyl.


Particular preference is likewise given to the compounds I&108, in particular to the compounds Ial08.1 — Ial08.64 which differ from compounds Ial.l — Ial.64 in that R1 is methyl, R2 is tR1fluoromethyl and R13 is tert—butyl.

Particular preference is likewise given to the compounds I&109, in particular to the compounds Ial09.1 — Ial09.64 which differ from compounds Ial.l — Ial.64 in that R1 and R14 are methyl and R2 is tR1fluoromethyl.

Particular preference is likewise given to the compounds lailO, in particular to the compounds iallO.l — Iall0.64 which differ from compounds ial.l - Ial.64 in that R1 and R14 are methyl, R2 is tR1fluoromethyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ialll, in particular to the compounds Ialll.1 — Ialll.64 which differ from compounds Ial.l - ial.64 in that R1 and R14 are methyl, R2 is tR1fluoromethyl and R13 is isopropyl.
Particular preference is likewise given to the compounds Iall2, in particular to the compounds Iall2.1 — Iall2.64 which differ from compounds Ial.l - ial.64 in that R1 and R14 are methyl, R2 is tR1fluoromethyl and R1* is tert—butyl.

Particular preference is likewise given to the compounds Iall3, in particular to the compounds Iall3.1 - Iall3.64 which differ from compounds Ial.l - ial.64 in that R1 and R2 are tR1fluoromethyl.

Particular preference is likewise given to the compounds Iall4, in particular to the compounds lall4.1 — Iall4.64 which differ from compounds ial.l - ial.64 in that R1 and R2 are tR1fluoromethyl and R13 is ethyl.


Particular preference is likewise given to the compounds Iall5, in particular to the compounds Iall5.1 — Iall5.64 which differ from compounds Ial.l — Ial.64 in that R1 and R2 are tR1fluoromethyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Iall6, in particular to the compounds Iall6.1 — Iall6.64 which differ from compounds Ial.l — ial.64 in that R1 and R2 are tR1fluoromethyl and R13 is tert—butyl.

Particular preference is likewise given to the compounds Iall7, in particular to the compounds Iall7.1 — Iall7.64 which differ from compounds Ial.l — Ial.64 in that R1 and R2 are tR1fluoromethyl and R14 is methyl.


Particular preference is likewise given to the compounds IallS, in particular to the compounds Iall8.1 — Iall8.64 which differ from compounds Ial.l - Ial.64 in that R1 and R2 are tR1fluoromethyl, R13 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Iall9, in particular to the compounds Iall9.1 — Iall9.64 which differ from compounds Ial.l — ial.64 in that R1 and R2 are tR1fluoromethyl, R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ial20, in particular to the compounds Ial20.1 — Ial20.64 which differ from compounds Ial.l - ial.64 in that R1 and R2 are tR1fluoromethyl, R1-3 is tert-butyl and R14 is methyl.

Particular preference is likewise given to the compounds Ial21, in particular to the compounds Ial21.1 — Ial21.64 which differ from compounds Ial.l — Ial.64 in that R1 is methoxy and R2 is tR1fluoromethyl.


Particular preference is likewise given to the compounds Ial22, in particular to the compounds Ial22.1 — Ial22.64 which differ from compounds Ial.l — lal.64 in that R1 is methoxy, R2 is tR1fluoromethyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ial23, in particular to the compounds lal23.1 — Ial23.64 which differ from compounds Ial.l - lal.64 in that R1 is methoxy, R2 is tR1fluoromethyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ial24, in particular to the compounds Ial24.1 — Ial24.64 which differ from compounds Ial.l — lal.64 in that R1 is methoxy, R2 is tR1fluoromethyl and R13 is tert—butyl.


Particular preference is likewise given to the compounds Ial25, in particular to the compounds Ial25.1 — Ial25.64 which differ from compounds ial.l — ial-64 in that R1 is methoxy, R2 is tR1fluoromethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ial26, in particular to the compounds Ial26.1 — Ial26.64 which differ from compounds Ial.l — lal.64 in that R1 is methoxy, Ra is tR1fluoromethyl, R13 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ial27, in particular to the compounds lal27.1 — Ial27.64 which differ from compounds ial.l — lal.64 in that R1 is methoxy, R2 is tR1fluoromethyl, R13 is isopropyl and R1* is methyl.

Particular preference is likewise given to the compounds Ial28, in particular to the compounds ial28.1 — Ial28.64 which differ from compounds Ial.l — lal.64 in that R1 is methoxy, R2 is tR1fluoromethyl, R*3 is tert-butyl and R14 is methyl.


Particular preference is likewise given to the compounds Ial29, in particular to the compounds lal29.1 — Ial29.64 which differ from compounds Ial.l — Ial.64 in that R3 is chloR1ne.

Particular preference is likewise given to the compounds Ial30, in particular to the compounds lal30.1 — Ial30.64 which differ from compounds Ial.l — Ial.64 in that R3 is chloR1ne and R13 is ethyl.

Particular preference is likewise given to the compounds Ial31, in particular to the compounds Ial31.1 — Xal31.64 which differ from compounds Ial.l — Ial.64 in that R3 is chloR1ne and R13 is isopropyl.

Particular preference is likewise given to the compounds Ial32, in particular to the compounds Ial32.1 — Ial32.64 which differ from compounds Ial.l — Ial.64 in that R3 is chloR1ne and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ial33, in particular to the compounds Ial33.1 — Ial33.64 which differ from compounds lal.l - Ial.64 in that R3 is chloR1ne and R14 is methyl.

Particular preference is likewise given to the compounds Ial34, in particular to the compounds Ial34.1 — lal34.64 which differ from compounds lal.l — Ial.64 in that R3 is chloR1ne, R13 is ethyl and R14 is methyl.

particular preference is likewise given to the compounds Ial35, in particular to the compounds Ial35.1 — Ial35.64 which differ from compounds lal.l — lal.64 in that R3 is chloR1ne, R*3 is isopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ial36, in particular to the compounds Ial36.1 — Ial36.64 which differ from compounds Ial.l — Ial.64 in that R3 is chloR1ne, R13 is tert—butyl and K14 is methyl.

Particular preference is likewise given to the compounds Ial37, in particular to the compounds ial37.1 — Ial37.64 which differ from compounds Ial.l - Jal.64 in that R1 is methyl and R3 is chloR1ne.

Particular preference is likewise given to the compounds Ial38, in particular to the compounds Ial38.1 — Ial38.64 which differ from compounds Ial.l - ial.64 in that R1 is methyl, R3 is chloR1ne and R13 is ethyl.

Particular preference is likewise given to the compounds Ial39, in particular to the compounds Ial39.1 — Ial39.64 which differ from compounds Ial.l — ial.64 in that R1 is methyl, R3 is chloR1ne and R13 is isopropyl.


Particular preference is likewise given to the compounds Ial40, in particular to the compounds Ial40.1 — Ial40.64 which differ from compounds ial.l — Ial.64 in that R1 is methyl, R3 is chloR1ne and R13 is tert—butyl.

Particular preference is likewise given to the compounds Ial42, in particular to the compounds Ial42.1 — Ial42.64 which differ from compounds Ial.l — Ial.64 in that R1 and R14 are methyl, R3 is chloR1ne and R13 is ethyl.


Particular preference is likewise given to the compounds Ial43, in particular to the compounds Ial43.1 — Ial43.64 which differ from compounds Ial.l - Ial.64 in that R1 and R14 are methyl, R3 is chloR1ne and R13 is isopropyl.

Particular preference is likewise given to the compounds Ial44, in particular to the compounds Ial44.1 — Ial44.64 which differ from compounds Ial.l - Ial.64 in that R1 and R1* are methyl, R3 is chloR1ne and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ial45, in particular to the compounds Ial45.1 — Ial45.64 which differ from compounds Ial.l - Ial.64 in that R2 is ethylsulfonyl and R3 is chloR1ne.

Particular preference is likewise given to the compounds Ial46, in particular to the compounds lal46.1 — lal46»64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl/ R3 is chloR1ne and R13 is ethyl.


Particular preference is likewise given to the compounds Ial47, in particular to the compounds Ial47.1 — Ial47.64 which differ from compounds Ial.l - Ial.64 in that R2 is ethylsulfonyl, R3 iS chloR1ne and R13 is isopropyl.

Particular preference is likewise given to the compounds Ial49, in particular to the compounds Ial49.1 — Ial49.64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl, R3 is chloR1ne and R" is methyl.


Particular preference is likewise given to the compounds Ial50, in particular to the compounds Ial50.1 — Ial50.64 which differ from compounds Ial.l — lal.64 in that R2 is ethylsulfonyl, R3 is chloR1ne, R*3 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ial51, in particular to the compounds Ial51.1 — Ial51.64 which differ from compounds Ial.l — lal.64 in that R2 is ethylsulfonyl, R3 is chloR1ne, R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia253, in particular to the compounds Ial53.1 — Ial53.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl and R2 is ethylsulfonyl and R3 is chloR1ne.


Particular preference is likewise given to the compounds Ial54f in particular to the compounds ial54.1 — Ial54.64 which differ from compounds Ial.l — ial.64 in that R1 is methyl R2 is ethylsulfonyl, R3 is chloR1ne and R13 is ethyl.

Particular preference is likewise given to the compounds lal56, in particular to the compounds Ial56.1 — lal56.64 which differ from compounds Ial.l - Ial.64 in that R1 is methyl, R2 is ethylsulfonyl, R3 is chloR1ne and R13 is tert—butyl.


particular preference is likewise given to the compounds ial57, in particular to the compounds Ial57.1 — Ial57.64 vhich differ from compounds lal.l - lal.64 in that R* and R1* are methyl, R2 is ethylsulfonyl and R* is chloR1ne.

Particular preference is likewise given to the compounds Ial60, in particular to the compounds Ial60.1 — Ial60.64 which differ from compounds lal.l - ial.64 in that R1 and R14 are methyl, R2 is ethylsulfonyl, R3 is chloR1ne and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ial64, in particular to the compounds Ial64.1 — Ial64.64 which differ from compounds Ial.l — lal.64 in that Ra and R3 are chloR1ne and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ial65, in particular to the compounds Ial65.1 — Ial65.64 which differ from compounds ial.l - ial.64 in that R2 and R3 are chloR1ne and R14 is methyl.

Particular preference is likewise given to the compounds Ial66, in particular to the compounds Ial66.1 — Ial66.64 which differ from compounds Ial.l — ial.64 in that R2 and R3 are chloR1ne, R*3 is ethyl and R1A is methyl.

Particular preference is likewise given to the compounds la}67, in particular to the compounds Ial67.1 - Ial67.64 which differ from compounds Ial.l - ial.64 in that R2 and R3 are chloR1ne, R*3 is isopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ial68, in particular to the compounds Ial68.1 — Ial68.64 which differ from compounds Ial.l — lal.64 in that R2 and R3 are chloR1ne, R13 is tert—butyl and Rli is methyl.
Particular preference is likewise given to the compounds Ial69, in particular to the compounds Ial69.1 - Ial69.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl and R2 and R3 are chloR1ne.

Particular preference is likewise given to the compounds Ial70, in particular to the compounds lal7Q.l — Ial70.64 which differ from compounds ial.l - lal.64 in that R1 is methyl, Rz and R3 are chloR1ne and R13 is ethyl.

Particular preference is likewise given to the compounds Ial71, in particular to the compounds Ial71.1 — Ial71.64 which differ from compounds Ial.l - lal.64 in that R1 is methyl, R2 and R3 are chloR1ne and R13 is isopropyl.


Particular preference is likewise given to the compounds Ial72, in particular to the compounds Ial72.1 — Ial72.64 which differ from compounds Ial.l — ial.64 in that R1 is methyl, R2 and R3 are chloR1ne and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ial74, in particular to the compounds ial74.1 — Ial74.64 which differ from compounds Ial.l - Ial.64 in that R1 and R1J are methyl, R* and R3 are chloR1ne and R13 is ethyl.


Particular preference is likewise given to the compounds Ial75, in particular to the compounds Ial75.1 — Ial75.64 which differ from compounds ial.l — lal.64 in that R1 and R14 are methyl, R2 and R3 are chloR1ne and R13 is isopropyl.

Particular preference is likewise given to the compounds ial76, in particular to the compounds Ial76.1 — ial76.64 which differ from compounds Ial.l - lal.64 in that R* and R14 are methyl, Rz and R3 are chloR1ne and R13 is tert-butyl.

Particular preference is likewise given to the compounds ial77, in particular to the compounds Ial77.1 — Ial77.64 which differ from compounds ial.l - lal.64 in that R1 is chloR1ne and R3 is methyl-

Particular preference is likewise given to the compounds Ial78, in particular to the compounds Ial78.1 — Ial78.64 which differ from compounds ial.l — lal.64 in that R3 is methyl and R13 is ethyl.


particular preference is likewise given to the compounds Ial79, in particular to the compounds Ial79.1 — Ial78.64 [sic] which differ from compounds Ial.l — Ial.64 in that R3 is methyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ial81, in particular to the compounds Ial81.1 — Ial81.64 which differ from compounds ial.l - Ial.64 in that R3 is methyl and R14 is methyl.


Particular preference is likewise given to the compounds Ial82, in particular to the compounds Ial82.1 — Ial82.64 which differ from compounds Ial.l - Ial.64 in that R3 is methyl, R13 is ethyl and R*
particular preference is likewise given to the compounds Ial83, in particular to the compounds Ial83.1 - Ial83.64 which differ from compounds Ial.l — Ial.64 in that R3 is methyl, R13 is isopropyl and R1* is methyl.



Particular preference is likewise given to the compounds Ial86, in particular to the compounds Ial86.1 — Ial86.64 which differ from compounds ial.l — lal.64 in that R1 and R3 are methyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ial88, in particular to the compounds Ial88.1 — Ial88.64 which differ from compounds ial.l — lal.64 in that R1 and R3 are methyl and R13 is tert—butyl.


Particular preference is likewise given to the compounds lalB9, in particular to the compounds Ial89.1 — ial89.64 which differ from compounds lal.l - lal.64 in that Rl, R3 and R1* are methyl.



Particular preference is likewise given to the compounds Ial93, in particular to the compounds Ial93.1 — Ial93.64 which differ from compounds Ial.l - ial.64 in that R* is ethylsulfonyl and R3 is methyl.


Particular preference is likewise given to the compounds Ial96, in particular to the compounds Ial96.1 - Ial96.64 which differ from compounds lal.l - Ial-64 in that R2 is ethylsulfonyl, R3 is methyl and R13 is tart-butyl.



Particular preference is likewise given to the compounds Ia200, in particular to the compounds Ia200.1 — Ia200.64 which differ from compounds Ial.l - Ial.64 in that R* is ethylsulfonyl, R3 is methyl, R13 is tert-butyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia203, in particular to the compounds Ia203.1 — Ia2Q3.64 which differ from compounds Ial.l — Ial.64 in that R1 and R3 are methyl, R2 is ethylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia204, in particular to the compounds Ia204.1 - Ia204.64 which differ from compounds Ial.l - Ial.64 in that R1 and R3 are methyl, R2 is ethylsulfonyl and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia205, in particular to the compounds Ia205.1 — ia205.64 which differ from compounds Ial.l — Ial.64 in that R1, R3 and R1* are methyl and R2 is ethylsulfonyl.

Particular preference is likewise given to the compounds Ia206, in particular to the compounds Ia206.1 — Ia206.64 which differ from compounds Ial.l - Ial.64 in that R1, R3 and R14 are methyl, R2 is ethylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia207, in particular to the compounds Ia207.1 - Ia207.64 which differ from compounds lal.l - ial.64 in that R1, R3 and. R14 are methyl, R2 is ethylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia208, in particular to the compounds ia208.1 — Ia208.64 which differ from compounds lal.l — Ial.64 in that R1, R3 and R14 are methyl, R2 is ethylsulfonyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ia210f in particular to the compounds Ia210.1 — ia210.64 which differ from compounds Ial.l - Jal.64 in that R2 is chloR1ne, R3 is methyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ia211, in particular to the compounds Ia211.1 — Ia211.64 which differ from compounds Ial.l — Jal.64 in that R2 is chloR1ne, R3 is methyl and R13 is isopropyl.



Particular preference is likewise given to the compounds Ia214, in particular to the compounds Ia214.1 - Ia214-64 which differ from compounds Ial.l - Ial.64 in that R* is chloR1ne, R3 is methyl, R13 is ethyl and R" is methyl.

Particular preference is likewise given to the compounds Xa215, in particular to the compounds Ia215.1 - Ia215#64 which differ from compounds Ial.l - Ial.64 in that R2 is chloR1ne, R3 is methyl, R13 is isopropyl and R14 is methyl.


Particular preference is likewise given to the compounds la217, in particular to the compounds Ia217.1 - Ia217.64 which differ from compounds Ial.l — lal.64 in that R1 and R3 are methyl and Ra is chloR1ne.

Particular preference is likewise given to the compounds Ia218, in particular to the compounds Ia218.1 — Ia218.64 which differ from compounds Ial.l - lal.64 in that R1 and R3 are methyl, R2 is chloR1ne and R13 is ethyl.



Particular preference is likewise given to the compounds Ia221, in particular to the compounds Ia221.1 — Ia221.64 which differ from compounds Ial.l - Ial.64 in that R1, R3 and R14 are methyl and R2 is chloR1ne.

Particular preference is likewise given to the compounds Ia222, in particular to the compounds Ia222.1 — Ia222.64 which differ from compounds Ial.l — ial.64 in that Rl, R3 and R14 are methyl, R2 is chloR1ne and R13 is ethyl.


Particular preference is likewise given to the compounds Ia224, in particular to the compounds Ia224.1 — Ia224.64 which differ from compounds ial.l — Ial-64 in that R1, R3 and R14 are methyl, R2 is chloR1ne and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia225, in particular to the compounds Xa225.1 — Ia225.64 which differ from compounds Ial.l — Ial.64 in. that R12 is methylsulfonyl.


Particular preference is likewise given to the compounds Ia228, in particular to the compounds Ia228.1 — Ia228.64 which differ from compounds Ial. 1 — ial.64 in that R12 is methylsulfonyl and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia229, in particular to the compounds Ia229.1 — Ia229.64 which differ from compounds Ial. 1 — Ial.64 in that R12 is methylsulfonyl and RH is methyl-

Particular preference is likewise given to the compounds Ia230, in particular to the compounds Ia230.1 — ia230.64 which differ from compounds Ial.l — Ial.64 in that R12 is methylsulfonyl, R13 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia231, in particular to the compounds Ia231.1 — Ia231.64 which differ from compounds Ial.l - Ial.64 in that R12 is methylsulfonyl, R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia232, in particular to the compounds la232.1 - ia232.64 vhich differ from compounds Ial.l — Ial.64 in that R12 is methylsulfonyl, R13 is tert-butyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia233, in particular to the compounds Ia233.1 — Ia233.64 which differ from compounds Ial.l — Xal.64 in that R1 is methyl and R12 is methylsulfonyl.

Particular preference is likewise given to the compounds Ia234, in particular to the compounds Ia234.1 — Ia234.64 which differ from compounds Ial.l - Ial.64 in that R1 is methyl, R12 is methylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia235, in particular to the compounds Ia235.1 - Ia235.64 which differ from compounds Ial.l - Ial.64 in that R1 is methyl, R12 is methylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia238, in particular to the compounds Ia238.1 - Ia238.64 which differ from compounds ial.l - Ial.64 in that R1 and R14 are methyl, R1Z is methylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia239, in particular to the compounds Ia239.1 — Ia239.64 which differ from compounds Ial.l — ial.64 in that R1 and R14 are methyl, R*2 is methylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia240, in particular to the compounds Ia240.1 — Ia240.64 which differ from compounds Ial.l — Ial.64 in that R1 and R14 are methyl, Ri2 is methylsulfonyl and R13 is tert—butyl.

Particular preference is likewise given to the compounds la.241, in particular to the compounds Ia241.1 — Ia241.64 which differ from compounds Ial.l — ial.64 in that R2 is ethylsulfonyl and R12 is methylsulfonyl.


Particular preference is likewise given to the compounds Ia242, in particular to the compounds Ia242.I — Ia242.64 which differ from compounds ial.l — ial.64 in that R2 is ethylsulfonyl, R12 is methylsuIfonyl and R13 is ethyl.

Particular preference is likewise given to the compounds ia245, in particular to the compounds Ia245.1 — Ia245.64 which differ from compounds Ial.l - Ial.64 in that R2 is ethylsulfonyl, R12 is methylsulfonyl and R** is methyl.


Particular preference is likewise given to the compounds 13246, in particular to the compounds Ia246.1 — Ia246.64 which differ from compounds Ial.l - ial.64 in that R2 is ethylsulfonyl, R" is methylsulfonyl, R13 is ethyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia247, in particular to the compounds Ia247.1 — Ia247.64 which differ from compounds Ial.l - Ial.64 in that R2 is ethylsulfonyl, R12 is methylsulfonyl, R13 is isopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Xa248, in particular to the compounds Ia248.1 — Ia248.64 which differ from compounds Ial.l - Ial.64 in that R2 is ethylsulfonyl, R12 is methylsulfonyl, R13 is tert—butyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia249, in particular to the compounds Ia249.1 — Ia249.64 which differ from compounds Ial.l — Ial.64 in that R1 is methyl, R2 is ethylsulfonyl and R12 is methylsulfonyl.


Particular preference is likewise given to the compounds la252, in particular to the compounds Ia252.1 - Ia252.64 which differ from compounds lal.l - Ial.64 in that R1 is methyl, R2 is ethylsulfonyl, R" is methylsulfonyl and R1* is tert-butyl.


Particular preference is likewise given to the compounds Ia255, in particular to the compounds Ia255.1 — Ia255.64 which differ from compounds lal.l - lal.64 in that R1 and R14 are methyl, R2 is ethylsulfonyl, R12 is methylsulfonyl and R13 is isopropyl.


particular preference is likewise given to the compounds Ia2$8, in particular to the compounds Ia258.1 - Ia258.64 which differ from compounds Ial.l — lal.64 in that R2 is chlorine, R12 is
methylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia261, in particular to the compounds Ia261.1 — ia261.64 which differ from compounds Ial.1 — ial.64 in that R2 is chlorine, R13 is methylsulfonyl and R13 is methyl.


Particular preference is likewise given to the compounds Ia264, in particular to the compounds Ia264.1 — Ia264.64 which differ from compounds Ial.l — Ial.64 in that R2 is chlorine, R12 is methylsulfonyl, R13 is tert—butyl and R14 is methyl.
ne

Particular preference is likewise given to the compounds Ia267, in particular to the compounds Ia267.1 - Ia267.64 which differ from compounds lal.l — ial.64 in that R1 is methyl, R2 is chlorine, R12 is methylsulfonyl and R13 is isopropyl.


Particular preference is likewise given to the compounds Ia270, in particular to the compounds Ia270.1 - Ia270.64 which differ from compounds Ial.l - ial.64 in that R1 and R14 are methyl, K2 is chlorine, R12 is methylsulfonyl and R" is ethyl.


Particular preference is likewise given to the compounds Ia273, in particular to the compounds Ia273.1 — Ia273.64 which differ from compounds ial.l - lal.64 in that R12 is phenylsulfonyl.


Particular preference is likewise given to the compounds Ia276, in particular to the compounds Ia276.1 - Ia276.64 which differ from compounds ial.l - Ial.64 in that R12 is phenylsulfonyl and Ri3 is tert-butyl.


Particular preference is likewise given to the compounds Ia279, in particular to the compounds Ia279.1 — Ia279.64 which differ from compounds Ial.l — Ial.64 in that R12 is phenylsulfonyl, R" is isopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia282, in particular to the compounds Ia282.1 - Ia282.64 which differ from compounds Ial.l - ial.64 in that R1 is methyl, R12 is phenylsulfonyl and R1^ is ethyl.


Particular preference is likewise given to the compounds Ia285f in particular to the compounds Ia285.1 — Ia285.64 which differ from compounds ial.l — Ial.64 in that R* and R14 are methyl and R12 is phenylsulfonyl.


Particular preference is likewise given to the compounds Ia288, in particular to the compounds Ia288.1 — Ia288.64 which differ from compounds Ial.l — ial.64 in that R1 and R1* are methyl, R12 is phenylsulfonyl and R13 is tert—butyl.


Particular preference is likewise given to the compounds Ia291, in particular to the compounds Ia291.1 — Ia291.64 which differ from compounds lal.l — Ial.64 in that R2 is ethylsulfonyl, R12 is phenylsulfonyl and R13 is isopropyl.


Particular preference is likewise given to the compounds Xa294, in particular to the compounds Ia294.1 — Ia294.64 which differ from compounds Ial.l — lal.64 in that R2 is ethylsulfonyl, R12 is phenylsulfonyl, R13 J.S ethyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia297, in particular to the compounds Ia297.1 — Ia297.64 which differ from compounds lal.l — lal.64 in that R1 is methyl, R2 is ethylsulfonyl and R12 is phenylsulfonyl.


Particular preference is likewise given to the compounds Ia300, in particular to the compounds Ia300.1 — Ia300.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl, R2 is ethylsulfonyl, R12 is phenylsulfonyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ia303f in particular to the compounds Ia303.1 — Ia303.64 which differ from compounds lal.l - Ial.64 in that Rl and R1* are methyl, R2 is ethylsulfonyl, R** is phenylsulfonyl and R13 is isopropyl.


Particular preference is likewise given to the compounds Ia306, in particular to the compounds Ia306.1 - Ia306.64 which differ from compounds ial.l - lal.64 in that R2 is chlorine, R" is phenylsuIfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia309, in particular to the compounds Ia309.1 - Ia309.64 which differ from compounds lal.l — lal.64 in that R2 is chlorine, R12 is phenylsulfonyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia312, in particular to the compounds Ia312.1 - I&312.64 which differ from compounds ial.l - ial.64 in that R2 is chlorine, R12 is phenylsulfonyl, R13 is tert—butyl and R1* is methyl.


Particular preference is likewise given to the compounds Ia315, in particular to the compounds Ia315.1 — Ia315.64 which differ from compounds Ial.l - Ial.64 in that R1 is methyl, R2 is chlorine, R12 is phenylsuIfonyl and R13 is isopropyl.


Particular preference is likewise given to the compounds Ia3l8, in particular to the compounds Ia318.1 — Ia318.64 which differ from compounds Ial.i — lal.64 in that R1 and R14 are methyl, R2 is chlorine/ R12 is phenylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia321, in particular to the compounds Ia32l.l — Ia321.64 which differ from compounds Ial.l - ial.64 in that R12 is 4-methylphenylsulfonyl.


Particular preference is likewise given to the compounds Ia324, in particular to the compounds Ia324.1 — Ia324.64 which differ from compounds Ial.l — Ial.64 in that Rli is 4-methylphenylsulfonyl and R13 is tert-outyl.


Particular preference is likewise given to the compounds Ia327, in particular to the compounds Xa327.1 — Ia327.64 which differ from compounds lal.l — Ial.64 in that R12 is 4-methylphenylsulfonyl, R13 is isopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia330, in particular to the compounds la330.X - Ia330.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl, R12 is 4-*nethylphenylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia333, in particular to the compounds Ia333.1 — Ia333.64 which differ from compounds Ial.l - ial.64 in that R1 and R14 are methyl and R12 is 4-methylphenylsulfonyl.


Particular preference is likewise given to the compounds Ia336, in particular to the compounds Ia336.1 - Ia336..64 which differ from compounds ial.1 — Ial.64 in that R1 and R14 are methyl, Ri2 is 4-methylphenylsulfonyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds Ia339, in particular to the compounds Ia339.1 — Ia339.64 which differ from compounds ial.1 — lal.64 in that R2 is ethylsulfonyl, R12 is 4—methylphenylsulfonyl and R*3 is isopropyl.


Particular preference is likewise given to the compounds Ia342, in particular to the compounds Ia342.1 - Ia342.64 which differ froin compounds Ial.l - lal.64 in that R2 is ethylsulfonyl, R12 is 4-methylphenylsulfonyl and R1* is methyl.


Particular preference is likewise given to the compounds Ia345, in particular to the compounds Ia345.1 - Ia345.64 which differ from compounds lal.l - ial.64 in that R1 is methyl, R2 is ethylsulfonyl and R12 is 4-methylphenylsulfonyl.


Particular preference is likewise given to the compounds Ia348, in particular to the compounds Ia348.1 — Ia348.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl, R2 is ethylsulfonyl, R12 is 4-methylphenylsulfonyl and R13 is tert-butyl.


Particular preference is likewise given to the compounds ia351, in particular to the compounds Ia351.1 - Ia351.64 which differ from compounds Ial.l - ial.64 in that R1 and R" are methyl, R2 is ethylsulfonyl, R12 is 4-methylphenylsulfonyl and R13 is isopropyl.


Particular preference is likewise given to the compounds Ia354, in particular to the compounds Ia354.1 — Ia354.64 which differ from compounds lal.l — lal.64 in that R2 is chlorine, R12 is 4-methylphenylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia357, in particular to the compounds la357.1 — Ia357.64 which differ from compounds lal.l — Ial.64 in that R2 is chlorine, R12 is 4-methylphenylsulfonyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia360, in particular to the compounds Ia360.1 — Ia360.64 which differ from compounds Zal.l - Ial-64 in that R2 is chlorine, R12 is 4-raethylphenylsulfonyl, Ri3 is tert-butyl and Rl* is methyl.

Particular preference is likewise given to the compounds Ia361, in particular to the compounds la361.1 — ia361.64 which differ from compounds lal.l — ial.64 in that R1 is methyl, R2 is chlorine and R12 is 4-methylphenylsulfonyl.

Particular preference is likewise given to the compounds Ia362, in particular to the compounds Ia362.1 — Ia362.64 which differ from compounds lal.l - Ial.64 in that R1 is methyl, R2 is chlorine, R12 is 4—methylphenylsulfonyl and R13 is ethyl.


Particular preference is likewise given to the compounds Ia363, in particular to the compounds la363.1 — Ia363.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl, R2 is chlorine, R12 is 4-methylphenylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia364, in particular to the compounds Ia364.1 — Ia364.64 which differ from compounds lal.l — Ial.64 in that R1 is methyl, R2 is chlorine, R12 is 4-methylphenylsulfonyl and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia365, in particular to the compounds la365.1 — Ia365.64 which differ from compounds lal.l - Ial.64 in that R1 and R14 are methyl, R2 is chlorine and R12 is 4-methylphenylsulfonyl.


Particular preference is likewise given to the compounds Ia366, in particular to the compounds ia366.1 — ia366.64 which differ from compounds Ial.l — lal.64 in that R1 and R1* are methyl, R2 is chlorine, R12 is 4-methylphenylsulfonyl and R13 is ethyl.

Particular preference is likewise given to the compounds Ia367, in particular to the compounds Ia367.1 - Ia367.64 which differ from compounds Ial.l — lal.64 in that R1 and R14 are methyl, R2 is chlorine, R12 is 4-methylphenylsulfonyl and R13 is isopropyl.

Particular preference is likewise given to the compounds Ia368, in particular to the compounds la368.1 - la368.S4 which differ from compounds Ial.l — lal.64 in that R1 and R1* are methyl, R2 is chlorine, R12 is 4-methylphenylsulfonyl and R13 is tert-butyl.

Particular preference is likewise given to the compounds Ia369, in particular to the compounds Ia369.1-Ia369.64 which differ from compounds Ial.l - lal.64 in that R13 is cyclopropyl.


Particular preference is likewise given to the compounds Xa370, in particular to the compounds Ia370.1 to Ia370.64 which differ from compounds Ial.l — Ial.64 in that R13 is cyclopropyl and R1* is methyl.

Particular preference is likewise given to the compounds Ia371, in particular to the compounds Ia371.1 to Ia371.64 which differ from compounds Ial.l — Ial.64 in that R1 is methyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia372, in particular to the compounds Ia372.1 to Ia372.64 which differ from compounds Ial.l — Ial.64 in that R1 is methyl, R13 is cyclopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia373, in particular to the compounds ia373.1 to Ia373.64 which differ from compounds Ial.l — lal.64 in that R1 is trifluoromethyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds ia374, in particular to the compounds Xa374.1 to Ia374.64 which differ from compounds Ial.l — lal.64 in that R1 is trifluoromethyl, R13 is cyclopropyl and R" is methyl.

Particular preference is likewise given to the compounds Xa375, in particular to the compounds Xa375.1 to Ia375.64 which differ from compounds Ial.l - lal.64 in that R1 is methoxy and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia376, in particular to the compounds Xa376.1 to Ia376.64 which differ from compounds Ial.l - lal.64 in that R1 is methoxy, R13 is cyclopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia377, in particular to the compounds Ia377.1 to Xa377.64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia378, in particular to the compounds Xa378,l to Ia378.64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl, R13 is cyclopropyl and R14 is methyl.

Particular preference is likewise given to the compounds la379, in particular to the compounds Xa379.1 to Ia379.64 which differ from compounds Ial.l — Ial.64 in that R1 is methyl, R2 is ethylsulfonyl and R13 is cyclopropyl.


Particular preference is likewise given to the compounds Ia380, in particular to the compounds Ia380.1 to Ia380.64 which differ from compounds Ial.l - Ial.64 in that R1 is methyl, R2 is ethylsulfonyl, Ri3 is cyclopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia382, in particular to the compounds Ia382.1 to Ia382.64 which differ from compounds Ial.l - ial.64 in that RL is trifluoromethyl, R2 is ethylsulfonyl, R13 is cyclopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia383, in particular to the compounds la383.1 to Xa383.64 which differ from compounds Ial.l — la 1.64 in that R1 is methoxy, a2 is ethylsulfonyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia385, in particular to the compounds Ia385.1 to Ia385.64 which differ from compounds Ial.l — la 1.64 in that R2 is chlorine and R13 is cyclopropyl.


Particular preference is likewise given to the compounds Ia388, in particular to the compounds Ia388.1 to Ia388.64 which differ from compounds Ial.l - Ial.64 in that R1 is methyl, R2 is chlorine, R13 is cyclopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia389, in particular to the compounds Ia389.1 to ia389.64 which differ from compounds lal.l — lal.64 in that R1 is trifluoromethyl, R2 is chlorine and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia390, in particular to the compounds Ia390.1 to Ia390.64 which differ from compounds lal.l — lal.64 in that R1 is trifluoromethyl, R2 is chlorine, R13 is cyclopropyl and R" is methyl.


Particular preference is likewise given to the compounds 13391, in particular to the compounds Ia391.1 to Ia391.64 which differ from compounds Ial.l — Ial.64 in that R1 is methoxy, R2 is chlorine and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia392, in particular to the compounds Ia392.1 to Ia392.64 which differ from compounds Ial.l — Ial.64 in that R1 is methoxy, R2 is chlorine, R13 is cyclopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia394, in particular to the compounds Ia394.1 to Ia394.64 which differ from compounds lal.i — ial.64 in that Ri is trifluoromethyl, R" is cyclopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia395, in particular to the compounds la395.1 to Ia395.64 which differ from compounds lal.i — ial.64 in that R* methyl, R2 is trifluoromethyl and R13 is cyclopropyl.


Particular preference is likewise given to the compounds Ia397, in particular to the compounds la397.1 to ia397.64 which differ from compounds Ial.l — lal.64 in that R1 and Rz are trifluoromethyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia398, in particular to the compounds Ia398.1 to la398.64 which differ from compounds Ial.l — ial.64 in that R1 and R2 are trifluoromethyl, R13 is cyclopropyl and R1* is methyl.


Particular preference is likewise given to the compounds Ia400, in particular to the compounds Ia400.1 to Ia400.64 which differ from compounds Ial.l — ial.64 in that R1 is methoxy, R2 is trifluoromethyl, R13 is cyclopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Xa401, in particular to the compounds Ia401.1 to Ia401.64 which differ from compounds Ial.l — Ial.64 in that R3 is chlorine and R13 is cyclopropyl. i


Particular preference is likewise given to the compounds Ia403, in particular to the compounds la403.1 to Ia403.64 which differ from compounds ial.l — Ial.64 in that R2 is ethylsulfonyl, R3 is chlorine and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia404, in particular to the compounds Ia404.1 to Ia404.64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl, R3 is chlorine, R13 is cyclopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia406, in particular to the compounds Ia406.1 to Ia406.64 which differ from compounds ial.l — lal.64 in that R1, R3 and R14 are methyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia407, in particular to the compounds Ia407.1 to Ia407.64 which differ from compounds Ial.l — lal.64 in that. R1 and R3 are methyl, R2 is ethylsulfonyl and R13 is cyclopropyl.


Particular preference is likewise given to the compounds Ia409, .n particular to the compounds Ia409.1 to Ia409.64 which differ :rom compounds lal.l - lal.64 in that Rl and R3 are methyl, R2 is :hlorine and R13 is cyclopropyl.

articular preference is likewise given to the compounds Ia410, n particular to the compounds Ia410.1 to Ia410.64 which differ rom compounds lal.l - ial.64 in that R1, R3 and R» are methyl, 2 is chlorine and R13 is cyclopropyl.


Particular preference is likewise given to the compounds Ia412, in particular to the compounds Ia412.1 to Ia412.64 which differ from compounds lal.l - Ial.64 in that is R12 methylsulfonyl, R" is cyclopropyl and R14 is methyl.

Particular preference is likewise given to the compounds Ia413, in particular to the compounds Ia413.1 to Ia413.64 which differ from compounds lal.l - Ial.64 in that R1 is methyl, R12 is methylsulfonyl and R13 is cyclopropyl.


Particular preference is likewise given to the compounds Ia414, in particular to the compounds Ia414.1 to Ia414.64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl, R12 is methylsulfonyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Xa416, in particular to the compounds Ia416.1 to Ia4l6.64 which differ from compounds Ial.l — Ial.64 in that R2 is ethylsulfonyl, R12 is methylsulfonyl, R1* is cyclopropyl and R14 is methyl.


Particular preference is likewise given to the compounds Ia418, in particular to the compounds la418.1 to ia418.64 which differ from compounds Ial.l — lal.64 in that R1 and R14 are methyl, R2 is ethylsulfonyl, Ri2 is methylsulfonyl and R13 is cyclopropyl.

Particular preference is likewise given to the compounds Ia419, in particular to the compounds Ia419.1 to Xa419.64 which differ from compounds ial.l — lal.64 in that R2 is chlorine, R12 is methylsulfonyl and Ri3 is cyclopropyl.


particular preference is likewise given to the compounds 13421, in particular to the compounds Ia421.1 to Ia421.64 which differ from compounds Ial.l — lal.64 in that R1 is methyl/ R2 is chlorine, R12 is methylsuIfonyl and R13 is cyclopropyl.


particular preference is likewise given to the compounds Ia424, in particular to the compounds Xa424.1 to Ia424.64 which differ from compounds Ial.l — Ial.64 in that R12 is 4-methylph.enylsulfonyl, R13 is cyclopropyl and R1* is methyl.


Particular preference is likewise given to the compounds Ia427, in particular to the compounds Ia427.1 to Ia427.64 which differ from compounds Ial.l — ial.64 in that R2 is chlorine, R12 is 4-methylphenylsulfonyl and R13 is cyclopropyl.


Particular preference is likewise given to the compounds Ia430, in particular to the compounds ia430.1 to Ia430.64 which differ from compounds ial.l - Ial.64 in that R1 and R14 are methyl, R* is chlorine, R12 is 4-methylphenylsulfonyl and R13 is cyclopropyl.

The 3— Process As
Reaction of pyrazoles of the formula II (where Z = H) with an activated benzoic aC1d Ilia or a benzoic aC1d Hip, which is preferably activated in situ, to give the acylation product, followed by rearrangement.



L1 is a nucleophilically displaceable leaving group, such as halogen, for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, etc.
The activated benzoic aC1d can be employed directly, as in the case of the benzoyl halides, or be generated in situ, for example using dicyclohexylcarbodiimide,
triphenylphosphane/azodicarboxylic aC1d esters, 2—pyridine disulfide/triphenylphosphane, carbonyldiimidazole, etc.
If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. 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 II, may be advantageous in some cases.
Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2—dichloroethane, aromatic hydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures thereof.
if the activated carboxylic aC1d component used is a benzoyl halide, it may be advantageous to cool the reaction mixture to 0 — 10°C when adding this reactant. 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 particularly suitable for this purpose are methylene chloride, diethyl ether and ethyl acetate. The organic phase is dried and the solvent removed, and the crude ester can then be used for the rearrangement without further purification.
The rearrangement of the esters to the compounds of the formula I is advantageously carried out at 20 - 40°C in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, dimethoxyethane, ethyl acetate, toluene or mixtures thereof. Preferred solvents ate acetonitrile, dioxane and dimethoxyethane.
Suitable bases are tertiary amines, such as triethylamine, pyridine or alkali metal carbonates, such as sodium carbonate, potassium carbonate, which are preferably employed in equimolar amounts or in excess of up to four times, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in twice the equimolar ratio, based on the ester.
Suitable cyano compounds are inorganic cyanides, such as sodium cyanide, potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin, trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mole 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, mole percent, based on the ester.
work-up can be carried out in a manner known per se. The reaction mixture is, for example, aC1dified with dilute mineral aC1d, such as 5% strength hydrochloric aC1d or sulfuric aC1d, 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 aC1dified and the resulting preC1pitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated. (Examples of the preparation of esters of hydroxypyrazoles and the rearrangement of the esters are given, for example, in EP-A 282 944 and US 4 643 757).
However, it may also be advantageous to generate the crude ester in situ and to carry out the rearrangement without isolation or purification of the ester.
Process B:
Reaction of 3—{4,5-dihydroisoxazol-5—yljbenzoylpyrazoles of the formula I (where R*2 = H) with a compound of the formula V:


L2 is a nucleophilically replaceable leaving groups, such as halogen, for example bromine, chlorine, hetaryl, for example iraidazolyl, pyridyl, sulfonate.
The compounds of the formula V can be employed directly, such as, for example, in the case of the sulfonyl halides, sulfonic anhydrides, or be generated in situ, for example activated sulfonic aC1ds (using sulfonic aC1d and dicyclohexylcarbonyldiimide, carbonyIdiimidazole, etc.).
The starting materials are generally employed in equimolar amounts. However, it can also be advantageous to use an excess of one component or the other.
If appropriate, it may be advantageous to carry out the reaction in the presence of a base. The reactants and the auxiliary base are then advantageously employed in equimolar amounts. An excess of auxiliary base, for example 1.5 to 3 molar equivalents, based on II, may be advantageous in certain cases.
Suitable auxiliary bases are tertiary alkylamines, such as' triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate, potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine and pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2—dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures thereof.
In general, the reaction temperature is 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.
The pyrazoles of the formula II (where R12 = B) used as starting materials are known or can be prepared by processes known per se (for example EP-A 240 001 and J. Prakt. Chem. 31S (1973), 383).
3—(4,5—Dihydroisoxazol—5—yl)benzoic aC1d derivatives of the formula III

where:
R1, R2 are hydrogen, nitro, halogen, cyano, Cj—C6—alkyl, C1-Cfi—haloalkyl, C1-Cg—alkoxy, C\—Cg—haloalkoxy, C1-C6-alkylthio, C1-c6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-Cg-alkylsulfonyl or C1-Cfi—haloalkylsulfonyl;
R3 is hydrogen, halogen or C1-Ce-alkylj?
R4 is hydrogen or C1-c4-alkyl;
R5, Rfi are hydrogen, halogen, cyano, nitro, C1-C4—alkyl, C1-C^-elkoxy-C1-C^-alkyl, di(C1-C4-«lJcoxy)-Cj-C
C1-C4—alkylthio-C1-Cj-alkyl, C1-C4-haloalkyl,
C1-C4-cyanoalkyl, C3-CB-cycloalkyl, C1-C4—alkoxy,
C1-C4—alkoxy-C2-C4-alkoxy, C1-C4—haloalkoxy,
C1-C4-alkylthio, C1-C4-haloalkylthio,
di{C1-C4-alkyl)amino, COR8, phenyl or benzyl, where the
two last-mentioned substituents may be partially or fully
halogenated and/or may carry one to three of the
following groups:
nitro, cyano, Cj-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy
or C1—C4—haloalkoxy;
or
R5 and R6 together form a c2-Ce-alkanediyl chain which may be
mono- to tetrasubstituted by C1-C4—alkyl and/or may be interrupted by oxygen or an unsubstituted or Cj-C4—alkyl -substituted nitrogen;
R7 is halogen, cyano, hydroxyl, C1-C$—alkyl, C1-Cfi—haloalkyl, C1—C6—alkoxy, Cj-Cg-ihaloalkoxy, C1-Cg-alkylthio, C1-Cg—haloalkylthio, C1-Cg—alkylsulfinyl, C1—Ce—haloalkylsulfinyl, C1-Cg-alkylsulronyl, C1-Cg—haloalkylsulfonyl, amino, C1-Cg—alkylamino, di(C1-Ce-alkyl)amino, di{C1-C4-alkoxy)methyl, hydroxyimino-C1-C4—alkyl, C1-Cg-alkoxyiminc—C 1-C4—alkyl or
COR*;
R8 is hydrogen, C1-C4~alkyl, Cr-C-4-haloalkyl, hydroxyl,
C1—C4—alkoxy, Cx-C4-alkoxy-C2-C4—alkoxy, C1-C4-haloalkoxy, C3-C6—alkenyloxy, C3-C6—alkynyloxy or HR9R10;
RS is hydrogen or C1-C4-alkyl;
Rio is C1-C4-alkyl;
Ris 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 may be substituted, halides, hetaryl radicals which are attached via nitrogen, amino and imino radicals, which may be substituted, etc.

Preference is given to 3-(4,5-dihydroisoxazol-5-yl)benzoyl halides of the formula Ilia' where L*' - halogen (S III where R" = halogen)

where the variables R1 to R7 are as defined under III and L3 is C1—Cg—alkoxy.

The particularly preferred embodiments of the 3-(4,5-dihydroisoxazol-5-yi)benzoic aC1d derivatives of the formula III with respect to the variables R* to R? correspond to those of the 3— (4,5-dihydroisoxazol—5—yl)benzoylpyrazoles of the formula I.
The 3-(4,5-dihydroisoxazol-5-yl)benzoyl halides of the formula Ilia' (where L1' = C1, Br) can be prepared in a manner known per se by reacting the 3-(4,5-dihydroisoxazol-5-yl)benzoic aC1ds of the formula lll£ with halogenating agents, such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride, oxalyl bromide.
The 3—{4,5-dihydroisoxazol-5-yl)benzoic aC1ds of the formula Hip can be prepared in a known manner by aC1dic or basic hydrolysis from the corresponding esters of the formula Illy (L3 « C1-Cfi-alxoxy).

Likewise, the 3— (4,5-dihydroisoxazol—5-yl)benzoic aC1ds of the formula Hip can be obtained by reacting the corresponding halogen-substituted compounds of the formula VI (L4 = Hal), in particular the iodine or bromine compounds, in the presence of a palladium, nickel, cobalt or rhodium transition metal catalyst and a base with carbon monoxide and water under elevated pressure.


Furthermore, it is possible to convert, by Rosenmund-von Braun—reaction, compounds of the formula VI into the corresponding nitriles of the formula VII (cf., for example, Org. Synth. Vol. Ill (1955), 212), and to convert these by subsequent hydrolysis into the compounds of the formula IIIp,
The compounds of the formulae VI and VII

R1, R2 are hydrogen, nitro, halogen, cyano, C%—C$—alkyl, C1-C6-haloalkyl, C],-c6--alkoxy, C1-Cg-haloalkoxy, C1-c6-alkylthio, C1-c6-haloalkylthio, Cj-Cfi-alkylsulfinyl, C1-Ce-haloalkylsulfinyl, Cr-C6-aIkyl.sulfonyl or C1-Cfi-haloalkylsulfonyl;
R3 is hydrogen, halogen or C1—C«—alkyl;

R4

is hydrogen or C1—C4—alkyl;

R5, R* are hydrogen, halogen, cyano, nitro, C1-C4-alkyl, C1-C4—alkoxy-C1-C4-alkyl, di (C1-C4-alkoxy)-C1-C4— alkyl, di(C1-c4—alkyl )amino~C1-C4—alkyl, di (C1—C4—alkyl) aminoimino-C1—C4—alkyl,
hydroxyimino-C1-C4-alkyl, C1-C6-xilkoxyiminc—C1-C4-alkyl, Cj—C4—alkoxycarbonyl—C1—C4—alkyl, C1-C4—alkylthio-C1-C4—alkyl, C1-C4—haloalkyl, C1-C4-cyanoalkyl, C3-Cs~ di(C1-C4—alkyl)amino, COR8, phenyl or benzyl, where the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups:
nitro, cyano, C1-C4—alkyl, C1—C4—haloalkyl, Cj—C4—alkoxy or C1—C4—haloalkoxy;
R5 and R6 together form a C2-C6-alkanediyl chain which may be
mono- to tetrasubstituted by C1-C4—alkyl and/or may be interrupted by oxygen or an unsubstituted or Cj—C4—alky1-substituted nitrogen;
R7 is halogen, cyano, hydroxy!, C1-Cs-alkyl, C1-C«—haloalkyl, C1-Cfi—alkoxy, C1-c6—haloalkoxy, C1-Cfi—alkylthio, C1-Ce—haloalkylthio, C1-Ce-alkylsulfinyl, C1-Cg—haloalkylsulfinyl, C1-Ce-alkylsulfonyl, C1-Cg—haloalkylsulfonyl, amino, C1-Cg-alkylamino, di(C1-C6-alkyl)amino, di-(C1-C4-alkoxy)methyl, hydroxyimino-C1-C4-alkyl, Cj-C6-alkoxyiraino-C1.jC4-a.lkyl or COR8;
R8 is hydrogen, C1-C4—alkyl, C1-C4-haloalkyl, hydroxyl,
C1-C4-alkoxy, C1-C4-alkoxy-C;r-C4-alkoxy, C1-C4-haloalkoxy, C3~C6-alkenyloxy, C3-C6—alkynyloxy or NR'R10;
R» is hydrogen or cl-C4-alkyl;
Rio is C1-C4—alkyl;
L* is halogen;
are likewise novel.

The particular embodiments of the compounds of the formulae VI and VII with respect to the variables Rl to R7 correspond to those of the 3—{4,5—dihydroisoxazol—5—yl)benzoylpyrazoles of the formula I.
The esters of the formula Illy and the halogen compounds of the formula VI can be prepared by 1,3—dipolar cycloaddition of nitrile oxides to appropriate alkenes of the formula VIII and IX, respectively.

The nitrile oxides are prepared in situ in a manner known per se. Suitable starting materials are, for example, aldoximes (cf., for example, Houben—Weyl X5, p. 858ff.) or nitroalkanes (cf., for example, Houben-Weyl £5/2, p. 1594ff.). Tne synthesis the compounds of the formulae VIII and IX is known (cf., for example, WO 98/50337 or WO 98/50366), or is carried out analogously to processes known from the literature.
Preparation examples:
4-[ 2-Chloro~3— (3-methyl—4,5-dihydroisoxazol—5-jyl)—4-methyl-sulfonylbenzoyl]—5-hydroxy—1-methyl—lH-pyrazole (Compound 2.8)
At 0 — 5°C, a solution of 6.7 g (20 mmol) of
2-chloro~3— (3-methyl—4,5-dihydroisoxazol-5—yl )-4-*nethylsulf onyl-benzoyl chloride in 80 ml of dimethoxyethane was added dropwise to a solution of 2.0 g (20 mmol) of 5-ihydroxy—l-*nethylpyrazole and 3.3 g (24 mmol) of potassium carbonate in 30 ml of anhydrous dimethoxyethane. After 12 hours of stirring at room temperature/

a further 8.2 g (60 mmol) of potassium carbonate were added, and the batch was refluxed for six hours. After cooling, the reaction mixture was stirred into 1 1 of water and extracted with methylene chloride. The aqueous phase was then adjusted to pH 4 using 10% strength hydrochloric aC1d and extracted repeatedly with methylene chloride, with readjustment of the pH. The organic phase was dried and the solvent removed, giving 5.3 g (13 mmol, 67%) of the desired compound. M.p.: > 215°C
4—[2-Chloro-3— (3-methyl—4,5-dihydroisoxazol—5—yl)—4-^nethyl-sulfonylbenzoylj— 5—hydroxy—1-cyclopropyl—lH-pyrazole (Compound 2.36)
At 0 — 5°C, a solution of 1.0 g (3 mmol) of
2-chlorc—3—(3-methyl-4,5-dihydroisoxazol—5—yl)-4-methylsulfonyl-benzoyl chloride in 50 ml of dimethoxyethane was added dxopwise to a solution of 0.47 g (3 mmol) of
5—hydroxy— 1—eyelopropylpyrazole and 0.5 g (3.6 mmol) of potassium carbonate in 36 ml of anhydrous dimethoxyethane. After 12 hours of stirring at room temperature, a further 1.0 g (7.2 mmol) of potassium carbonate were added and the batch was refluxed for 6 hours. After cooling, the reaction mixture was stirred into 600 ml of water and extracted with methylene chloride. The aqueous phase was then adjusted to pH 4 using 10% strength hydrochloric aC1d and extracted with methylene chloride. Drying of the organic phase and removal of the solvent gave 0.8 g (1.8 mmol, 63%) of the desired compound. M.p.: > 220°C
In addition to the compounds mentioned above, further derivatives of the formula I which were prepared or are preparable in an analogous manner are listed in Table 2.









The syntheses of some starting materials are given below:
Methyl 2,4-dichlorc—3-( 3-tert~butyl-4,5-dihydroisoxazol-5-yl) -benzoate
At room temperature, 17 ml of a 12% strength aqueous sodium hypochlorite solution were added dropwise with vigorous stirring to a solution of 2,6 g (10 mmol) of methyl 2,4-dichloro-3-ethenylbenzoate and 1 g (10 mmol) of 2,2-dimethylpropionaldoxime in 100 ml of dichloromethane. Twice, in each case after 2 hours of stirring, a further 0.5 g (5 mmol) of the oxime and 9 ml of the hypochlorite solution were added. The reaction mixture was stirred at room temperature for a further 12 hours and then stirred into 350 ml of water. After extraction with dichloromethane, drying and removal of the solvent, the residue was chromatographed.
Yield: 1.5 g (45% of theory) of a yellow resin
Methyl 2-chloro-3-(3-«thoxycarbonyl—4,5-dihydroisoxazol—5—yl)—4— methyl-sulfonylbenzoate.
At room temperature, 6.4 ml (46 mmol) of triethylamine were slowly added dropwise to a solution of 8.5 g (31 mmol) of methyl 2-chloro-3-ethenyl-4-methylsulf onylbenzoate and 7.2 g (46 mmol) of ethyl 2-chloro-2~hydroxyiminoacetate in 200 ml of dichloromethane. 3 further portions of in each case 4.8 g (31 mmol) of ethyl 2-chloro-2-hydroxyiminoacetate and then 4.3 ml (31 mmol) of triethylamine were added, in each case after 2 hours of stirring. The reaction mixture was stirred at room temperature for another 12 hours and then stirred into 600 ml of water. After extraction with dichloromethane, drying and removal of the solvent, the residue was chromatographed.
Yield: 5.7 g (47% of theory) of a clear resin.
2-Chloro-3— (3-methyl-4,5-dihydroisoxazol—5-yl)—4-methylsulf onyl-benzoic aC1d
a) Methyl 2-chloro-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4^-methylsulfonylbenzoate.
A spatula tip of 4-dimethylaminopyridine was added to a solution of 40 g (145 mmol) of methyl 2-chlorc—3-ethenyl-4~methyleulfonylbenzoate and 50 g (220 mmol) of di-tert-butyl dicarbonate in 300 ml of

acetonitrile, and 50 g (640 mmol) of nitroethane were then slowly added dropwise. The mixture was stirred at room temperature for 12 hours, and a further 32.8 g (145 mmol) of di—tert-butyl dicarbonate and 22.9 g (290 mmol) of nitroethane were then added. After a further 12 hours, the solvent was distilled off and the residue was digested with ethyl acetate. The mixture was filtered off with suction, giving 32.1 g of the desired compound. A further 6.3 g were obtained from the mother liquor after removal of the solvent, followed by chromatography.
yields 39.4 g (B2% of theory) M.p.: 175°C
b) 2-Chloro-3— (3-methyl-4,5-dihydroisoxazol—5—yl)—4—methyl -sulfonylbenzoic aC1d
69.4 g (174 mmol) of 10% strength aqueous sodium hydroxide solution were added to a solution of 38.4 g (116 mmol) of methyl 2-chloro-3— (3-methyl—4, 5—dihydroisoxazol—5—yl )~4— methylsulfonylbenzoate in 400 ml of methanol and 400 ml of tetrahydrofuran. The mixture was stirred at room temperature for 12 hours, the solvent volume was reduced to half of the original volume and the mixture was poured into 1 1 of water. Using 10% strength hydrochloric aC1d the pB was adjusted to 1 and the resulting preC1pitate was filtered off with suction.
Yieldt 35.2 g (96% of theory) M.p.: > 220°C
2-Methyl—3— (3-methyl-4,5-dihydroisoxazol—5-yl)-4-methylsulfonyl-benzoic aC1d
a) 2-Hethyl-3—(3-methyl—4,5-dihydroisoxazol—5-yl)~4-Biethyl-su1fonylbromobenzene
A spatula tip of 4-dimethylaroinopyridine was added to a solution of 13.6 g (50 mmol) of 2-methyl—3-ethenyl-4— methylsulfonylbromobenzene and 16.7 g (74 mmol) of di-tert-butyl dicarbonate in 100 ml of acetonitrile, and 17.9 g (229 mmol) of nitroethane were then slowly added dropwise. The mixture was stirred at room temperature for 6 hours, and a further 11.1 g (50 mmol) of di—tert-butyl dicarbonate and 7.8 g (100 mmol) of nitroethane were then added, and the mixture was stirred at room temperature for 12 hours. The solvent was removed and the residue was

chromatographed.
Yield: 6.4 g (38% of theory)
b) 2-Methyl—3—(3-methyl-4,5-dihydroisoxazol—5—yl)—4-methyl-sulfonylbenzoic aC1d
6.4 g (19 mmol) of 2-methy 1-3-(3~methy 1-4,5-dihydro¬isoxazol—5-yl)—4-methylsulfonylbromobenzene were dissolved in 65 ml of toluene and 30 ml of water and admixed with 240 rog (1 mraol) of palladium acetate, 1.1 g (4 mmol) of tricyclohexylphosphane, 810 mg (19 mmol) of lithium chloride and 5.4 ml (38 mmol) of triethylamine. The resulting solution was then stirred in an autoclave at 140°C and under a carbon monoxide pressure of 20 bar for 36 hours. After cooling and venting, insoluble components were filtered off and the phases were separated. The organic phase was then extracted twice with water containing a little triethylamine. The combined aqueous phases were then adjusted to pH 1 using 10% hydrochloric aC1d, and the resulting preC1pitate was filtered off.
yield: 2.5 g (44% of theory) M.p.: 199-205°C
In addition to the compounds described above. Table 3 below lists further 3-(4,5-dihydroisoxazol-5-yl)benzoic aC1d derivatives of the formula III which are prepared or are preparable in a similar manner.





The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I and their agriculturally useful salts are suitable as herbiC1des, both in the form of isomer mixtures and in the form of the pure isomers. The herbiC1dal compositions comprising compounds of the formula I effect very good control of vegetation on non-crop areas, espeC1ally at high rates of application. In crops such as wheat, rice, maize, soybeans and cotton they act against broad-leaved weeds and grass weeds without damaging the crop plants substantially. This effect is observed espeC1ally at low rates of application.
Depending on the application method in question, the compounds of the formula I, or herbiC1dal 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 offiC1nalis. 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, C1trus limon. C1trus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca. GlyC1ne max, Gossypium hirsutum, (Gossypium arboreuro, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Bumulus lupulus, Zpomoea batatas, Juglans regia. Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec., Hicotiana 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, RiC1nus communis, Saccharum offiC1narum, Secale cereale, Solanum tuberosum. Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, ViC1a faba, Vitis vinifera and Zea mays.
Moreover, the compounds of the formula I can also be used in crops which tolerate the action of herbiC1des due to breeding including genetic engineering methods.
The compounds of the formula I, or the herbiC1dal compositions comprising them, can be employed, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or

dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.
The herbiC1dal compositions comprise a herbiC1dally active amount of at least one compound of the formula I or of an agriculturally useful salt of I and auxiliaries conventionally used for the formulation of crop protection products.
Suitable inert auxiliaries are essentially:
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, eg. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and 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 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and these concentrates are suitable for dilution with water.
Suitable surfactants (adjuvants) are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic aC1ds, for example ligno-, phenol-, naphthalene- and
dibutylnaphthalenesulfonic aC1d, and of fatty aC1ds, of alkyl-and alkylaryl sulfonates, of alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and of fatty alcohol glycol ether, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic aC1ds, with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctyl-, octyl-or nonylphenol, alkylphenyl, 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 spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calC1um sulfate, magnesium sulfate, magnesium oxide, ground synthetic material, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, 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 products 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 ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NKR spectrum).
The formulation examples below illustrate the preparation of such products t
I. 20 parts by weight of the compound No. 2.7 are dissolved in
a mixture composed of 80 parts by weight of alkylated
benzene, 10 parts by weight of the adduct of 8 to 10 mol of
ethylene oxide and 1 mol of oleic aC1d N-monoethanolamide,
5 parts by weight of calC1um dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 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 ingredient.
II. 20 parts by weight of the compound No. 2.7 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 and 1 mol of

isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 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 ingredient.
III. 20 parts by weight of the active ingredient NO. 2.7 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 and 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 ingredient.
IV. 20 parts by weight of the active ingredient No. 2.7 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic aC1d 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 20f000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active ingredient.
V. 3 parts by weight of the active ingredient No. 2.7 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active ingredient.
VI. 20 partB by weight of the active ingredient Ho. 2.7 are mixed intimately with 2 parts by weight of calC1um dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the 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 active ingredient No. 2.7 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 active ingredient No. 2.7 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 herbiC1dal compositions comprising them, can be applied pre- or post-emergence. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbiC1dal compositions are sprayed, with the aid of the spray apparatus, in such a way that they come into as little contact as possible, if any, with the leaves of the sensitive crop plants while reaching the leaves of undesirable plants which grow underneath, or the bare soil (post-directed, lay-by).
Depending on the intended aim of the control measures, the season, the target plants and the growth stage, the application rates 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.).
To widen the spectrum of action and to achieve synergistic effects, the 3-{4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I can be mixed and applied jointly with a large number of representatives of other groups of herbiC1dally or growth-regulatory active ingredients. Suitable components in mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric aC1d and its derivatives, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanic aC1ds and their derivatives, benzoic aC1d and its derivatives, benzothiadiazinones, 2—(hetaroyl/aroyl)—1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CFs-phenyl derivatives, carbamates, guinolinecarboxylic aC1d and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic aC1d and its derivatives, dihydrobenzofuranes, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic aC1ds and their derivatives, ureas, 3-phenyluraC1ls, imidazoles, imidazolinonea,
N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic aC1d and its derivatives, 2-phenylpropionic aC1d and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic aC1d and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolcarboxamides and uraC1ls.

Moreover, it may be advantageous to apply the compounds of the formula I, alone or in combination with other herbiC1des, in the form of a mixture with additional other crop protection agents, for example with pestiC1des or agents for controlling pftytopathogenic fungi or bacteria. Also of interest is the misC1bility with mineral salt solutions which are employed for treating nutritional and trace element defiC1enC1es. NOn-phytotoxic oils and oil concentrates can also be added.
use Examples
The herbiC1dal action of the
3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I was demonstrated by the following greenhouse experiments!
The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as substrate. The seeds of the test plants were sown separately for each speC1es.
For the pre-emergence treatment, the active ingredients, 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 caused uniform germination of the test plants unless this wa's adversely affected by the active ingredients.
For the post-emergence treatment, the test plants were grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. To this end, 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 treatment. The rate of application for the post-emergence treatment was 125 or 62.5 g/ha a.s. (active substance).
Depending on the speC1es, the plants were kept at from 10 to 25°C and 20 to 35°C, respectively. 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 of from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts, and 0 means no damage or normal course of growth.
The plants used in the greenhouse experiments belonged to the following speC1es:

At an application rate of 125 or 62.5 g/ha of a.s., the compound 2.7 showed very good activity against the abovementioned harmful plants and was compatible with spring wheat.
In contrast, at the same application rates, the comparative compound A (compound 20 from Table 1) known from WO 97/41118 caused damage in the crop plant spring wheat, and had a weaker herbiC1dal activity against the harmful plants mentioned.



We claim:
1. A 3-(4,5-dihydroisoxazol-S-yl)benzoylpyrazole of the formula I

wherei
R1, R2 are hydrogen, nitro, halogen, cyano, C1-C6-alkyl, C1-Cs-haloalkyl, C1-C«-alkoxy, Cx-C«-haloalkoxy, C1-C6-al)eylthiO/ C1-C6-haloalkylthio, C1-C6—alkylsulrinyl, C1-C«—haloalkylsulfinyl, Cx-c6-alkylsulfonyl or C1-C6—haloalkylsulfonyl;
R3 is hydrogen, halogen or C1-C6-alkyi;
R* ia hydrogen or C1-c4-alkyl?
R5, R6 are hydrogen, halogen, cyano, nitro, C1-C4—alJcyl, C1-Ca-alkoxy-C1-alkyl, di(C1-C4-alkoxy)-C1-C4— alkyl, di(Cl-C4-alkyl)amino-C1-V-alkyl, di(C1-C4-alkyl) aminoiminc-C1-C4-alkyl, hydroxy imino-C1-C4-alkyl, C1-C6-alkoxylmino--C1-C4-alkyZ, C1-C4-alkoxycart>onyl-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl, C3-Cs--cycloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C2-c«-alkoxy» C1-C4—haloalkoxy, C1-C4-alkylthio, C1-C1-haloalkylthio, di(C1-C4-alkyl)amino, COR*, phenyl or benzyl, where the two last-mentioned substituenta may be partially or fully halogen&ted and/or may carry one to three of the following groups1
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C'4-alkoxy or C1-C4-haloalkoxy;
or

R5 and R* together form a C2-c«-alkanediyl chain which may be mono- to tetrasubstituted by C1-C-alkyl and/or may be interrupted by oxygen or an unsubstituted or C1-C4—alky 1-substituted nitrogen;
R7 is halogen, cyano, hydroxyl, C1-C6-alkyl,
C1-C6-haloalkyl, C1-c«-alkoxy, C1-C6-haloalkoxy, C1-C6-alfcylthio, C1-C6-haloalkylthio, C1-C6—alkylsulfinyl, —haloalkylsulfinyl, C1-Cp-alkylsulfonyl, C1-C-haloalkylsulfonyl, amino, C1-C6-alkylamino, di(C1-C6-alkyl)amino, di (C1-C4-alkoxy) methyl, hydroxyimino-C1-C4-al)cy 1, C1-C6-alkoxyimino-Cl-C4-alkyl or COR8;
R8 is hydrogen, CfC1-alkyl, C1-C-ialoalkyl,
hydroxyl, C1-C-alkoxy, C1-C-alkoxy-CT-Cftr-alkoxy, C1-c4-haloalkoxy, C1-C6-alkenyloxy, C3-C6—alkynyloxy or NR9R™;
R* is hydrogen or C1-C4-alkyl;
RlO ia C1-C4-alkyl;
Ru is a pyrazole, attached in the 4—position, of the
formula II

where
R12 is hydrogen, C1-C4-alkyl, C1-C-haloalkyl, C3-C4-alkenyl, C3-C«-alkynyl, C1—c4—alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-c-alkylsulfony 1, C1-C1-haloalkylsulfonyl, thienylmethyl, phenyl, benzyl, phenylcarbonyl, phenylsulfonyl or phenylcarbonylmetbyl, where the phenyl radical of the five last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groupsi

nitro, cyano, C1—C4—alkyl, C1-Cf-haloalkyl, C1-C1-alkoxy or C1-C4-haloalkoxy;
R13 is C1-C6-alkyl, C1-Cs-haloalkyl or
C3-C6-cycloalkyl;
R1* i8 hydrogen, C1-Cg-alkyl or
C3-C6-CYcloalkyl;
and its agriculturally useful salts.
2. The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I aa claimed in claim 1 where R3 is hydrogen.
3. The 3-(4,5-dihydroisoxazol—5-yl)benzoylpyrazole of the formula I as claimed in claim 1 or 2 where
Ri, Ra are nitro, halogen, cyano, C1-c6-alkyl,
C1-Cs-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-c6-al]tylthio, C1-C1-haloalkylthio, C1-C6-alfcylsulfinyZ, C1-C6-haloalkylsulfinyl, C1-C6-al)cylsulfonyl or C1-Cs-haloalkylsulfonyl.
4. The 3—(4»5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula
I as claimed in any of claims 1 to 3 where
R12 is C1-C(-alkylsulfonyl, C1-C4-halosulfonyl or
phenylsulfonyl, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C1-C1-alkyl, C1-C4-haloalkyl, C1-C-alJcoxy or C1-C4-haloal)coxy.
5. The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula
X as claimed in any of claims 1 to 3 where
R12 is benzyl, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groupst
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C1-haloalkoxy.
6. The 3-(4,5-4lihydroisoxazol-5-yl)benzoylpyrazole of the
formula I as claimed in any of claims 1 to 3 where R13 is
hydrogen.

7. The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula I as claimed in any of claims 1 to 6 where
R5 is hydrogen, halogen, cyano, nitro, C1-C4—alkyl, C1-C(-alkoxy-C1-C4-alkyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl, C1-Cs-cycloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C2-C4-alkoxy/ C1—C4—haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, di(C1-C4-alkyl)amino, COR8, phenyl or benzyl, where the two last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups* nitro, cyano, C1—C4—alkyl, C1—C4—haloalkyl, C1-C4-alkoxy or C1-C4—haloalkoxy;
R6 is hydrogen or C1-04-alkyl.
6. The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the
formula I as claimed in any of claims 1 to 7 where Rs and R6 are hydrogen.
9. A proC6ss for preparing
3— (4,5-dihydroisoxa2ol-5-yl)benzoylpyrazoles of the formula I as claimed in claim 1, which comprises acylating the pyrazole of the formula II where R12 - H and where the variables R13 and R14 are as defined under claim 1


where the variables R1 to R' are as defined under claim 1 and L1 is a nucleophilically displaceable leaving group and rearranging the acylation product, if appropriate in the presence of a catalyst, to the compounds I (where R12 ■ 8), followed, if desired, by reaction with a compound of the formula V
where R2 is as defined under claim 1 except for hydrogen and L2 is a nucleophilically displaceable leaving group, to prepare 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazoles of the formula I where R1J * hydrogen.
10. A 3-(4,5-dihydroisoxazol—5-yl)benzoylpyrazole of the formula
III.
where R15 is hydroxyl or a radical that can be removed by hydrolysis and the variables R1 to R7 are as defined under claims 1 to 8.
11, The 3-(4,5-dihydroisoxazol-5-yl)benzoylpyrazole of the formula
III as claimed in claim 10 where
R15 is halogen, hydroxyl or Ci-Ce-alkoxy.


R1, R3 are nitro, halogen, cyano, C1-C6-alltyl,
C1-C6-haloalkyl, C1-C6-alkoxy, C1.-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C$-haloalkylsulfonyl;
and L* is halogen and the variables R3 to R7 are as defined under claims 1 to 8.
13. A compound of the formula VII

where the variables R1 to R7 are as defined under claims 1 to 8.

Documents:


« Previous Patent
Next Patent »
Patent Number 225101
Indian Patent Application Number IN/PCT/2002/1049/CHE
PG Journal Number 52/2008
Publication Date 26-Dec-2008
Grant Date 30-Oct-2008
Date of Filing 09-Jul-2002
Name of Patentee BASF AKTIENGESELLSCHAFT
Applicant Address D-67056, Ludwigshafen
Inventors:
# Inventor's Name Inventor's Address
1 BAUMANN, ERNST Falkenstrasse 6a, 67373 Dudenhofen
2 VON DEYN, WOLFGANG Wolfgang of an der bleiche 24, 67435 neustadt
3 KUDIS, STEFFEN Spelzenstrasse 10, 68167 Mannheim
4 LANGEMANN, KLAUS Goldbergstrasse 18, 67551 Worms
5 MAYER, GUIDO Gutleuthausstrasse 8, 67433 Neustadt
6 MIBLITZ, UIF Mandelring 74, 67433 Neustadt
7 NEIDLEIN, UIF Brahmsstrasse 3, 68165 Mannheim
8 WALTER, HELMUT Grünstadter Strasse 82, 67283 Obrigheim
9 WESTPHALEN, KARL-OTTO Zum Pfauenturm 17, 67346 Speyer
10 WITSCHEL, MATTHIAS Höhenweg 12b, 67098 Bad Dürkheim
PCT International Classification Number A01N43/80
PCT International Application Number PCT/EP2000/012950
PCT International Filing date 2000-12-19
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 100 10 551.3 2000-03-07 Germany
2 199 62 249.3 1999-12-22 Germany