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WO2000034247A2 - Procede de production de derives de pyrazolylbenzoyl et nouveaux derives de pyrazolylbenzoyl - Google Patents

Procede de production de derives de pyrazolylbenzoyl et nouveaux derives de pyrazolylbenzoyl Download PDF

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Publication number
WO2000034247A2
WO2000034247A2 PCT/EP1999/009343 EP9909343W WO0034247A2 WO 2000034247 A2 WO2000034247 A2 WO 2000034247A2 EP 9909343 W EP9909343 W EP 9909343W WO 0034247 A2 WO0034247 A2 WO 0034247A2
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hydrogen
compounds
substituent
row
corresponds
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PCT/EP1999/009343
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WO2000034247A3 (fr
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Ulf Neidlein
Norbert Götz
Ulf Misslitz
Ernst Baumann
Wolfgang Von Deyn
Steffen Kudis
Klaus Langemann
Guido Mayer
Matthias Witschel
Martina Otten
Karl-Otto Westphalen
Helmut Walter
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Basf Aktiengesellschaft
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Priority to AU20947/00A priority Critical patent/AU2094700A/en
Publication of WO2000034247A2 publication Critical patent/WO2000034247A2/fr
Publication of WO2000034247A3 publication Critical patent/WO2000034247A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5

Definitions

  • the present invention relates to a process for the preparation of pyrazolylbenzoyl derivatives, new pyrazolylbenzoyl derivatives, herbicidal compositions which comprise them and the use of the pyrazolylbenzoyl derivatives or compositions comprising weed control.
  • a 5-hydroxypyrazole is acylated with a benzoyl halide and the pyrazole ester formed is rearranged with a catalyst to give the pyrazolyl-benzoyl derivatives.
  • Another object of the present invention was to produce new pyrazolyl-benzoyl derivatives which are unsubstituted on the two nitrogen atoms.
  • R 1 is hydrogen, -CC alkyl or -CC haloalkyl
  • R 2 is hydrogen
  • Ci-C ⁇ -alkyl C 2 -C 6 -alkenyl, C -C 6 -alkynyl, benzyl, benzoyl, -C-C -alkylcarbonyl, hydroxycarbonyl -C ⁇ -C -alkyl,
  • A, B, D are independently hydrogen
  • C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, CC 6 alkynyl, C ⁇ -C 4 alkoxy, these groups being substituted by halogen, hydroxy, C ⁇ -C alkoxy or cyano may be substituted;
  • R 3 C ⁇ -C 4 -alkyl, C 4 haloalkyl or NR 5 R 6
  • R 4 C ⁇ -C 4 -alkyl, C 4 haloalkyl, C ⁇ * -C alkoxy, or NR 5 R 6
  • R 5 is hydrogen or -CC 4 alkyl
  • R 7 is branched C 3 -C 8 alkyl, C 3 -C 2 alkenyl, C -C 2 alkynyl which are optionally substituted by halogen or C 1 -C 4 alkoxy or benzyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl sulfonyl or C 1 -C 4 alkyl carbonyl is substituted, means treated with an inorganic or organic acid at a pH ⁇ 2 and reacted with elimination of an olefin or an alcohol .
  • the present invention relates to new pyrazole -4 -yl-benzoyl derivatives of the formula I according to claim 1
  • R 1 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 2 is hydrogen
  • C 1 -C 6 -alkyl C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, benzyl, benzoyl, C 1 -C 6 -alkylcarbonyl, hydroxycarbonyl -C ⁇ -C 4 -alkyl, C ⁇ -C 4 -alkoxycarbonyl-C ⁇ -C 4 - alkyl, C 1 -C 4 alkylsulfonyl or phenylsulfonyl, these groups being represented by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, halogen, hydroxy, amino,
  • Nitro or cyano may be substituted
  • A, B, D are independently hydrogen
  • Phenyl which can be substituted by C 1 -C 4 alkyl, C ⁇ -C haloalkyl, halogen, hydroxy, cyano or nitro; a 5- or 6-membered heterocyclic, saturated or unsaturated radical containing one to three heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, which may be replaced by halogen, cyano, nitro, a group -CO-R 4 , C 1 -C 4 -alkyl, -C-C 4 -haloalkyl, C 3 -Cg -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C ⁇ -C 4 -alkylthio, C ⁇ - C 4 -Halogenalkylthio, Di-C ⁇ -C 4 alkylamino, optionally by halogen, cyano,
  • the ratenf may also be in the tautomeric form as a hydroxyl group 4 -halogenoalkyl-substituted phenyl or an oxo group lls, substituted or fused with one, If appropriate, by halogen, cyano , Nitro, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl substituted phenyl ring, a fused carbocycle or a fused, optionally by halogen, cyano, nitro, C 1.
  • C ⁇ -C 4 -alkyl di-C ⁇ -C 4 - alkylamino, C ⁇ -C 4 -alkoxy, C 4 haloalkoxy, or C ⁇ -C 4 haloalkyl substituted hetero- second cyclus forms a bicyclic system, except for 5-isoxazolyl and 5-pyrazolyl;
  • R 3 C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl or NR 5 R 6 ⁇ -
  • R 4 C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, or NR 5 R 6 ⁇ -
  • R 5 is hydrogen or C 1 -C 4 alkyl
  • a pyrazolylbenzoyl derivative of the formula II is treated with an inorganic or organic acid at a pH ⁇ 2, where in the case that R 7 is branched C 3 -C 8 alkyl, C 3 -C alkenyl or C 4 -C 4 2- alkynyl means a corresponding C 3 -C 2 -olefin is split off, in the event that R 7 denotes optionally substituted benzoyl, the corresponding benzoyl alcohol is split off.
  • the reaction is preferably carried out in an organic solvent.
  • Suitable solvents are, for example, acetonitrile, DMF, dioxane, THF, toluene or chlorobenzene.
  • Preferred solvents are acetonitrile, THF or dioxane.
  • a particularly preferred solvent is acetonitrile.
  • Suitable acids are, for example, trifluoromethanesulfonic acid, trichloroacetic acid, sulfuric acid, nitric acid, hydrochloric acid and hydrobromic acid.
  • Preferred acids are trifluoromethanesulfonic acid and trichloroacetic acid. Trifluoromethanesulfonic acid is particularly preferred.
  • the reaction is carried out at a temperature of 20 to 150 ° C or up to the boiling point of the respective solvent.
  • a temperature of 50 to 100 ° C. or the boiling point of the solvent used is preferred if this is below 100 ° C.
  • the reaction can be carried out under normal pressure, positive pressure and negative pressure.
  • the pyrazolylbenzoyl derivative of the formula II is prepared by acylation of the pyrazoles of the formula III, in which the substituted R 1 and R 7 have the meaning given at the outset, with a benzoyl derivative of the formula IV, in which T is halogen and A, B, D and Z have the meaning given at the outset, and rearrangement of the pyrazole ester I formed in the presence of a catalyst to give the pyrazolylbenzoyl derivative I.
  • T halogen and A, B, D and Z have the meaning given above.
  • the reactants and the auxiliary base are expediently used in approximately equimolar amounts. A slight excess of the auxiliary base , for example 1.2 to 1.5 molar equivalents, based on III, may be advantageous.
  • Suitable auxiliary bases are e.g. tertiary alkyl amines, pyridine or alkali carbonates, while methylene chloride, diethyl ether, toluene or ethyl acetate can be used as the solvent.
  • the reaction mixture is advantageously cooled to 0 -10 ° C, then at a higher temperature, e.g. stirred at a temperature of 25-50 ° C until the reaction is complete.
  • the rearrangement of the 5-hydroxypyrazolesters to the compounds of the formula I is carried out in a solvent at temperatures from 50 ° C. to 90 ° C. or at the boiling point of the solvent and in the presence of an auxiliary base and with the aid of a cyano compound as a catalyst.
  • a solvent e.g. Acetonitrile, methylene chloride, 1, 2-dichloroethane, ethyl acetate or toluene can be used.
  • the preferred solvent is acetonitrile.
  • Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali carbonates, which are used in equimolar amounts or up to four times the excess.
  • auxiliary base is triethylamine in double amount.
  • Suitable catalysts are cyanide compounds such as potassium cyanide or acetone cyanohydrin, e.g. in an amount of 1 to 50, in particular 5-20 mole percent, based on the 5-hydroxy-pyrazol ester. Acetone cyanohydrin is preferably used e.g. in amounts of 10 mole percent.
  • the processing takes place in the usual way, e.g. the reaction mixture is acidified with dilute mineral acids such as 5% hydrochloric acid or sulfuric acid and extracted e.g. with methylene chloride or ethyl acetate.
  • the extract is extracted with cold 5-10% alkali carbonate solution, the end product passing into the aqueous phase.
  • the product of the formula Ic is precipitated by acidifying the aqueous solution, or extracted again with methylene chloride, dried and then freed from the solvent.
  • 5-hydroxypyrazoles of the formula III used as starting material are known and can be prepared by processes known per se (cf. EP-A 240 001 and J. Prakt. Chem. 315, 382 (1973)).
  • 1, 3-Dimethyl-5-hydroxypyrazole is a commercially available compound.
  • Benzoic acid derivatives of the formula IV are known, for example, from WO 96/26206.
  • Pyrazolylbenzoyl derivatives of the formula II are suitable for the process according to the invention, in which R 7 denotes branched C 3 -C 8 alkyl, C 3 -C alkenyl or C 4 -C 2 alkynyl in the ⁇ position, where these radicals can be substituted by halogen or C 1 -C 4 alkoxy, or benzyl by halogen, cyano, nitro, C 1 -C 4 haloalkyl, S0 -C ⁇ -C 4 alkyl or Ci -C 4 alkylcarbonyl can be substituted.
  • R 7 is preferably branched C -C 6 alkyl in the ⁇ position, which may be substituted by halogen or C 1 -C 4 alkoxy.
  • C 3 -C 6 -alkyl branched in the ⁇ -position means, for example, 1-methylethyl, 1, 1-dimethylethyl, 1-methylpropyl, 1-ethylpropyl, 1, 1-dimethylpropyl, 1-methyl-1-ethylpropyl, 1-methylbutyl, 1-ethylbutyl, 1, 1-dimethylbutyl and 1-methylpentyl.
  • ⁇ - position branched C 3 -C ⁇ alkyl means, for example in ⁇ -position branched C 3 -C 6 -alkyl as mentioned above, and 1.1 -Diethylpropyl, 1 - propylbutyl, 1-methyl - 1 -ethylbutyl, 1, 1-diethylbutyl, 1-methyl-1-propylbutyl, 1 -ethyl-1-propylbutyl, 1,1-di-propyl-butyl, 1-ethylpentyl, 1,1-di-methylpentyl, 1,1-diethylpen- tyl, 1-methylhexyl.
  • C 3 -C 2 alkenyl branched in the ⁇ position is to be understood as meaning at least one double bond containing C 3 -C 1 alkyl branched in the ⁇ position, as listed above.
  • C 4 -C ⁇ 2 alkynyl branched in the ⁇ position is to be understood as meaning at least one triple bond-containing c 4 " c i 2 " alkyl branched in the ⁇ position, as listed above under C 3 -C ⁇ 2 alkyl.
  • Optionally substituted benzyl means benzyl, 4-chlorobenzyl, 4-cyanobenzyl, 4 -nitrobenzyl, 4 -trifluoromethylbenzyl, 4 -methylsulfonylbenzyl or 4 -acylbenzyl.
  • Benzyl, 4-chlorobenzyl and 4 -nitrobenzyl are preferred. Benzyl is particularly preferred.
  • R 2 independently of one another hydrogen, benzoyl, 4-F-benzoyl,
  • Benzyl C 1 -C 4 alkyl, preferably hydrogen and
  • Ci -C 4 alkyl; A, B, D independently of one another are hydrogen, C 1 -C -alkyl,
  • D is hydrogen or methyl
  • Z is hydrogen, Ci-C 4 alkyl
  • Phenyl which can be substituted by C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, hydroxy, cyano or nitro; a 5- or 6-membered heterocyclic, completely unsaturated radical, preferably oxazolyl, 3-isoxazolyl, 4 -isoxazolyl, thiazolyl, isothiazolyl, 3-pyrazolyl,
  • a 5- or 6-membered heterocyclic, partially unsaturated radical preferably pyrrolinyl, oxazolinyl,
  • oxazolinyl particularly preferably oxazolinyl, isoxazolinyl, pyrazolinyl and imidazolinyl;
  • isoxazolinyl or a 5- or 6-membered heterocyclic, saturated radical.
  • the present invention further relates to pyrazole-4-yl-benzoyl derivatives of the formula I according to claim 1
  • R 1 is hydrogen, C 1 -C alkyl or C 1 -C 4 haloalkyl
  • R 2 is hydrogen; -C-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, benzyl,
  • A, B, D are independently hydrogen
  • R 3 is C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl or NR 5 R 6 ;
  • R 4 C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy, or NR 5 R 6 ;
  • R 5 is hydrogen or C ⁇ -C 4 alkyl
  • R 6 C ⁇ -C alkyl
  • R 1 is hydrogen
  • C ⁇ -C 4 alkyl such as methyl, ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, 1-dimethylethyl;
  • C ⁇ -C 4 haloalkyl a C ⁇ -C alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethyl, Dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2- Chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl,
  • C 2 -C 6 alkenyl such as 2-propenyl, 2-butenyl, 3-butenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 3- Methyl-2-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, l-methyl-3-butenyl,
  • C 2 -C 6 alkynyl such as propargyl, 2-butynyl, 3-butenyl,
  • C ⁇ -C 4 ⁇ alkylcarbonyl such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl and 1, 1-dimethylethylcarbonyl, especially methylcarbonyl;
  • C ⁇ -C 4 -alkoxycarbonyl-C ⁇ -C 4 -alkyl with C ⁇ -C 4 -alkoxy such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1, 1-dirnethylethoxy ,
  • C ⁇ -C 3 alkoxy such as methoxy, ethoxy, i-propoxy, particularly preferably methoxy
  • C X -C 4 alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1, 1-dimethylethylsulfonyl;
  • Phenylsulfonyl is preferably hydrogen and C ⁇ -C 4 alkylsulfonyl
  • C 1 -C 4 alkyl, Cx -C 4 alkoxy C ⁇ -C 4 alkylthio such as C ⁇ -C 4 ⁇ alkylthio such as methylthio, ethyl - thio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio and 1, 1-dimethylethylthio, especially methylthio ;
  • Halogen, hydroxy, arnino, nitro and cyano can be substituted
  • A, B, D are independently hydrogen
  • the group - (Y) n -S (0) m R 3 defined above stands for, for example
  • C ⁇ -C-alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl and 1, 1-dimethylethylsulfinyl, especially methylsulfinyl;
  • C ⁇ -C 4 ⁇ alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1, 1-dimethylethylsulfonyl, especially methylsulfonyl;
  • C ⁇ -C 4 -alkoxysulfonyl such as methoxysulfonyl, ethoxysulfonyl, n-propoxysulfonyl, 1-methylethoxysulfonyl, n-butoxysulfonyl, 1-methylpropoxysulfonyl, 2-methylpropoxysulfonyl and 1, l-dimethylethoxysulfonyl, especially methoxysulfonyl;
  • N-C ⁇ -C 4 ⁇ alkylsulfamoyl such as N-methylsulfamoyl, N-ethylsulfamoyl, Nn-propylsulfamoyl, Nl-methylethylsulfamoyl, Nn-butylsulfomoyl, N-1-methylpropylsulfamoyl, N-2-methylpropylsulfamoyl and especially N N-methyls
  • N-C ⁇ -C 4 ⁇ alkylsulfinamoyl such as N-methylsulfinamoyl, N-ethylsulfinamoyl, Nn-propylsulfinamoyl, N-1-methylethylsulfinamoyl, Nn-butylsulfinamoyl, N-1-methylpropylsulfinamoyl, N-2-n-propylsulfylamyl -Dimethylethylsulfinamoyl, especially N-methylsulfinamoyl;
  • Di-C ⁇ -C 4 alkylsulfamoyl such as dimethylsulfamoyl, diethylsulfamoyl, dipropylsulfamoyl, dibutylsulfamoyl, N-methyl-N-ethylsulfamoyl, N-methyl-N-propylsulfamoyl, N-methyl-N-1-methylethylsulfamoyl, N-methyl -Dimethylethylsulfamoyl, di-1-methylethylsulfamoyl, N-ethyl-N-1-methylethylsulfamoyl and N-ethyl-N-1, 1-dimethylethyl-sulfamoyl; especially dimethylsulfamoyl;
  • Di-C ⁇ -C 4 ⁇ alkylsulfinamoyl such as dimethylsulfinamoyl, diethylsulfinamoyl, dipropylsulfinamoyl, dibutylsulfinamoyl, N-methyl-N-ethylsulfinamoyl, N-methyl-N-propylsulfinamoyl, N-methyl-N-1-methyll-ethylsulfoyl -Nl, 1-dimethylethylsulfinamoyl, di-1-methylethylsulfinamoyl, N-ethyl-Nl-methylethylsulfinamoyl and N-ethyl-N-1, 1-dimethylethylsulfinamoyl; especially dimethylsulfinamoyl,
  • C ⁇ -C 4 alkylsulfinyloxy such as methylsulfinyloxy, ethylsulfinyloxy, n-propylsulfinyloxy, 1-methylethylsulfinyloxy, n-butylsulfonylyloxy, 1-methylpropylsulfinyloxy, 2-methylpropylsulfinyloxy and 1, 1-dimethylethylsulfinyloxy, especially methylsulfinyloxy;
  • C ⁇ -C-alkylsulfonyloxy such as methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, n-butylsulfonyloxy, 1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy and 1, 1-dimethylethylsulfonyloxy, in particular;
  • C ⁇ -C 4 alkylsulfinylamino such as methylsulfinylamino, ethylsulfinyl - a ino, n-propylsulfinylamino, 1-methylethylsulfinylamino, n-butylsulfinylamino, 1-methylpropylsulfinylamino, 2-methylpropylsul - finylamino and 1, 1-dimethylaminoethylsulfonamino;
  • C ⁇ -C 4 ⁇ alkylsulfonylamino such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, 1-methylethylsulfonylamino, n-butylsulfonylamino, 1-methylpropylsulfonylamino, 2-methylpropylsul- fonylamino and 1, 1-dimethylethylsulfonylamino, especially methylsulfonylamino;
  • N-C ⁇ -C 4 alkylsulfinyl-N-methyl-amino such as N-methylsulfinyl-N-methyl-amino, N-ethylsulfinyl-N-methyl-amino, Nn-propylsulfinyl-N-methyl-amino, N-1 -Methylethylsulfinyl-N-methyl-amino, Nn-butyl-sulfinyl-N-methyl-amino, N-1-methylpropylsulfinyl-N-methyl-amino, N-2-methylpropylsulfinyl-N-methyl-amino and Nl, 1-dimethylethyl - sulfinyl-N-methyl-amino, especially N-methylsulfinyl-N-methyl-amino;
  • N-C ⁇ -C-alkylsulfinyl-N-ethyl-amino such as N-methylsulfinyl-N-ethyl-amino, N-ethylsulfinyl-N-ethyl-amino, Nn-propylsulfinyl-N-ethyl-amino, N-1-methylethylsulfinyl N-ethyl-amino, Nn-butylsulfinyl-N-ethyl-amino, N-1-methylpropylsulfinyl-N-ethyl-amino, N-2-methylpropylsulfinyl-N-ethyl-amino and Nl, 1-dimethylethylsulfinyl-N- ethyl-amino, especially N-methylsulfinyl-N-ethyl-amino;
  • N-C ⁇ -C 4 alkylsulfonyl-N-methyl-amino such as N-methylsulfonyl-N-methyl-amino, N-ethylsulfonyl-N-methyl-amino, Nn-propylsulfonyl-N-methyl-amino, N-1 -Methylethylsulfonyl-N-methyl-amino, Nn-butyl-sulfonyl-N-methyl-amino, N-1-methylpropylsulfonyl-N-methyl-amino, N-2-methylpropylsulfonyl-N-methyl-amino and Nl, 1-dimethylethyl - sulfonyl-N-methylamino, especially N-methylsulfonyl-N-methylamino;
  • C ⁇ -C 4 -haloalkylthio such as chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2, 2-difluoroethyl, 2, 2-difluoroethyl -2, 2-difluoroethylthio, 2,2-dichloro-2 fluoroethylthio, 2, 2, 2-trichloroethylthio and pentafluoroethylthio, especially trifluoromethylthio.
  • the group - (Y) n -CO-R 4 defined above stands for, for example
  • C ⁇ -C 4 alkylcarbonyl such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl and 1, 1-dimethylethylcarbonyl, especially methylcarbonyl;
  • N-C ⁇ -C 4 alkylcarbamoyl such as N-methylcarbamoyl, N-ethylcarbamoyl, Nn-propylcarbamoyl, N-1-methylethylcarbamoyl, Nn-butylcarbamoyl, N-1-methylpropylcarbamoyl, N-2-methylpropylcarbamoyl and Nl, 1-dim , especially N-methylcarbamoyl;
  • Di-C ⁇ -C 4 alkylcarbamoyl such as dimethylcarbamoyl, diethylcarbamoyl, dipropylcarbamoyl, dibutylcarbamoyl, N-methyl-N-ethylcarbamoyl, N-methyl-N-propylcarbamoyl, N-methyl-N-1-methylethylcarbamoyl, N-methyl-N-1 , 1-dimethylethylcarbamoyl, di-1-methylethylcarbamoyl, N-ethyl-N-1-methylethylcarbamoyl and N-ethyl-N-1, 1-dimethylethylcarbamoyl; especially dimethylcarbamoyl;
  • C ⁇ -C4 ⁇ alkylcarbonyloxy such as methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy and 1, 1-dimethylethylcarbonyloxy, especially methylcarbonyloxy
  • C ⁇ -C 4 alkylcarbonylamino such as methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, 1-methylethylcarbonylamino, n-butylcarbonylamino, 1-methylpropylcarbonylamino, 2-methylpropylcarbonylamino and 1, 1-dimethylethylcarbonylamino, especially methylcarbonylamino
  • C ⁇ -C 4 alkylcarbonylamino such as methylcarbonylamino, ethyl
  • N-C ⁇ -C 4 -alkylcarbonyl-N-methyl-amino such as N-methylcarbonyl-N-methyl-amino, N-ethylcarbonyl-N-methyl-amino, Nn-propylcarbonyl-N-methyl-amino, N-1 -Methylethylcarbonyl-N-methyl-amino, Nn-butyl-carbonyl-N-methyl-amino, N-1-methylpropylcarbonyl-N-methyl-amino, N-2-methylpropylcarbonyl-N-methyl-amino and Nl, 1-dimethylethyl - Carbonyl-N-methyl-amino, especially N-methylcarbonyl-N-methyl-amino.
  • the radicals A, B and D are furthermore, independently of one another, hydrogen, C ⁇ -C 4 -alkyl, Cx -C 4 -alkoxy, C ⁇ -C 4 -alkyl-thio, C ⁇ -C-alkylsulfonyl, C ⁇ -C 4 -haloalkyl , Halogen, hydroxy, cyano or nitro.
  • radicals A, B and D preferably independently represent hydrogen, methyl, methoxy, methylthio, methylsulfonyl, trifloromethyl, chlorine, hydroxy, cyano or nitro.
  • the radicals A, B and D are also preferably independently of one another hydrogen, methyl, methoxy, methylthio, methylsulfonyl, chlorine or hydroxy.
  • Phenyl which can be substituted by C -C 4 alkyl as mentioned above, C ⁇ -C 4 haloalkyl as mentioned above, halogen, hydroxy, cyano or nitro;
  • heteroaromatics such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazol-3-yl, 1, 2, 4-oxadiazol-5-yl, 1,3, 4-oxadiazol-2-yl, 1,2, 3-oxadiazol-4-yl, 1, 2, 3-oxadiazol-5-yl, 1, 2, 5-oxadiazol-3-yl, 1, 2, 4-thiadiazol-3-yl, l, 2,4-thiadiazol-5-yl, 1, 3, 4-thiadiazol
  • heteroaromatics such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl , 1, 2, 4-triazin-5-yl and 1, 2, 4-triazin-3-yl, 1, 2, 4-triazin-6-yl, 1,2,4, 5-tetrazin-3-yl ; 5- to 6-membered, saturated or partially unsaturated heterocycles containing one to three nitrogen atoms and / or one or two oxygen or sulfur atoms such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrotienyl, tetrahydrothiopyran -2 -yl, tetrahydrothiopyran-3 -yl,
  • Tetrahydrothiopyran-4-yl 1, 3 -dithiolan-2 -yl, 1, 3 -dithiolan-4 -yl, l-3-dithian-2-yl, 1, 3 -dithian-4 -yl, 5, 6 - Dihydro-4H-1,3-thiazin-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5 -isothiazolidinyl, 3 -pyrazolidinyl, 4 -pyrazolidinyl, 5 -pyrazolidinyl, 2 -oxazolidinyl, 4 -oxazolidinyl, 5-o
  • the substituent Z is preferably a 5- or 6-membered heterocyclic, completely unsaturated radical.
  • Substituent Z further preferably represents oxazolyl, 3-isoxazolyl, 4-isoxazolyl, thiazolyl, isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, imidazolyl, pyridinyl, pyridazinyl, pyrimidinyl or pyrazinyl.
  • the substituent Z particularly preferably represents 2 -oxazolyl
  • the substituent Z is also preferably 5-oxazolyl, 3-isoxazolyl or 3-pyrazolyl.
  • the substituent Z is preferably also a 5- or 6-membered heterocyclic, partially unsaturated radical.
  • the substituent Z is preferably also pyrrolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, pyrazolinyl, imidazolinyl, dioxolanyl, pyridinyl, pyrimidinyl, pyridazinyl and pyrazidinyl.
  • Z particularly preferably represents oxazolinyl, isoxazolinyl, pyrazolinyl and imidazolinyl.
  • Z furthermore particularly preferably represents oxazolinyl or isoxazolinyl.
  • Z very particularly preferably represents isoxazolinyl.
  • Z is preferably also a 5- or 6-membered heterocyclic, completely saturated radical.
  • Z further preferably represents oxazolidinyl, isoxazolidinyl, thiazolidinyl, isothiazolidinyl, pyrazolidinyl, imidazolidinyl or piperidinyl.
  • Z is preferably oxazolidinyl or isoxazolidinyl.
  • the 5- or 6-membered heterocyclic, saturated or unsaturated radical is optionally substituted by halogen as mentioned above, in particular fluorine or chlorine, cyano, nitro,
  • a group -COR 4 for example alkylcarbonyl as mentioned above, alkoxycarbonyl as mentioned above, N-alkylcarbamoyl as mentioned above, dialkylcarbamoyl as mentioned above; C ⁇ -C 4 ⁇ alkyl as mentioned above,
  • C 3 -Cg-cycloalkyl such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, in particular cyclopropyl and cyclohexyl;
  • C ⁇ -C 4 haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2, 2-difluoroethoxy, 1, 1, 2 2-tetrafluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-l, 1, 2-trifluoroethoxy and pentafluoroethoxy, in particular C ⁇ -C 3 -haloalkoxy such as 2,2,2-trifluoroethyloxy and 2-chloro 2,2-difluoroethoxy;
  • Di-C ⁇ -C 4 ⁇ alkylamino such as dirnethylamino, diethylamino, dipropylamino, dibutylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-1-methylethylamino, N-methyl- N-1, 1-dimethylethylamino, di-1-methylethylamino, N-ethyl-N-1-methylethylamino and N-ethyl-N-1, 1-dimethylethylamino;
  • phenyl optionally substituted by halogen, cyano, nitro, C ⁇ -C 4 -alkyl as mentioned above or C ⁇ -C 4 -haloalkyl as mentioned above;
  • oxo group which may optionally also be present in the tautomeric form as a hydroxyl group, for example thiazolin-4, 5-dion-2-yl, 3-oxo-3H-l, 2, 4-dithiazolyl or 2-oxo-2H-l , 3, 4-dithiazolyl.
  • Benzo-fused 5- or 6-ring heteroaromatics are, for example, benzofuranyl, benzothienyl, indolyl, benzoxazolyl, benzisoxazolyl, benzthiazolyl, benzisothiazolyl, benzpyrazolyl, indazolyl, 1, 2, 3-benzothiadiazolyl, 2, 1, 3-benzothiadiazolyl, benzothiadiazolyl , Quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl or phthalazinyl. Examples of particularly preferred compounds of the general formula I are listed in Tables 1 to 600 below. Table A
  • Substituent Z corresponds to one row of Table A for each individual compound.
  • Substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • Substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Me and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B CI and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0 2 Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means OMe, B S0 Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0 2 Me, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0 2 Et, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 90 Connections 90.1 - 90.198
  • a S0Me, B CF 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0 2 Me, B CF 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0Me, B CI and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0, B S0Me and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0, B S0 2 Et and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means N0, B S0CH 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0CH 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0Et and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0 2 Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0 2 Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B S0Me, and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B CI and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means CI and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 109 Connections 109.1 - 109.198
  • AOMe, B means S0Me and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means OMe, B S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0 2 Me, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0 2 Me, B CF 3 and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0Me, B CF 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0 2 , B S0 2 Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0 2 , B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means N0, B S0 2 CH 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0 2 CH 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0Et and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0 2 Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 129 Connections 129.1 - 129.198
  • Table 139 Connections 139.1 - 139.198
  • Table 143 Connections 143.1 - 143.198 Compounds of the general formula I in which R 1 is hydrogen, R 2 Me, A N0, B S0Me and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Me and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B S0Me, and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 154 Compounds 154.1 - 154.198
  • a Me, B means S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B CI and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 159 Connections 159.1 - 159.198
  • a OMe, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means OMe, B S0Me and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means OMe, B S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Me, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Et, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 165 Compounds 165.1 - 165.198
  • a S0Me, B CF 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0 2 Me, B CF 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0 2 Me, B CI and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0, B S0Me and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0 2 , B S0 2 Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means N0, B S0 Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0CH 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0Et and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0 2 Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Me and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Et and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B S0Me, and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B CI and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0 2 Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0 Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means OMe, B S0 2 Me and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means OMe, B S0 2 Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Me, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Et, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Me, B CF 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0Me, B CF 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0Me, B CI and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0 2 , B S0 2 Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means N0, B S0 Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0 2 CH 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0 2 Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 221 Compounds 221.1 - 221.198 Compounds of the general formula I, in which R 1 is hydrogen, R 2 Ac, A N0, B S0 2 Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B S0 2 Me, and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B CI and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • AOMe, B means S0Me and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Me, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0 2 Et, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Me, B CF 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0 2 Me, B CF 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0Me, B CI and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0 2 , B S0 2 Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0, B S0 2 Et and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • Table 245 Connections 245.1 - 245.198
  • a N0 2 , B S0 2 CH 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0 2 CH 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0Et and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Me and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B S0Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B S0 2 Me, and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a Me, B means S0Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CI, B CI and D are hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0 2 Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a OMe, B S0 2 Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means OMe, B S0Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Me, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Et, B CI and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a S0Me, B CF 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0Me, B CF 3 and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means S0 2 Me, B CI and D Me and the substituent Z corresponds to one row of Table A for each individual compound
  • a N0 2 , B S0Me and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • a N0 2 , B S0 2 Et and D means hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means N0, B S0 Et and D Me and the substituent Z corresponds to one row of Table A for each individual compound.
  • a CF 3 , B S0 CH 3 and D is hydrogen and the substituent Z corresponds to one row of Table A for each individual compound.
  • A means CF 3 , B S0 2 Me, and D Me and the substituent Z corresponds to one row of Table A for each individual compound.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un procédé de production de dérivés de pyrazolylbenzoyl de la formule (I), où les substituants ont la signification donnée dans la description. L'invention est caractérisée en ce qu'un dérivé de pyrazolylbenzoyl de la formule (II), où les substituants R?1, R2, R7¿, A, B et D ont la signification susmentionnée réagit avec un acide inorganique ou organique pour un pH ∫2 et avec séparation d'une oléfine ou d'un alcool. L'invention concerne également de nouveaux dérivés de pyrazolylbenzoyl, des agents herbicides contenant ces dérivés de pyrazolylbenzoyl et un procédé permettant de lutter contre les plantes indésirables.
PCT/EP1999/009343 1998-12-04 1999-12-01 Procede de production de derives de pyrazolylbenzoyl et nouveaux derives de pyrazolylbenzoyl WO2000034247A2 (fr)

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Publication number Priority date Publication date Assignee Title
US7507860B2 (en) 2004-04-13 2009-03-24 Pfizer Inc. Androgen modulators
US7576128B2 (en) 2004-02-13 2009-08-18 Pfizer Inc. Androgen receptor modulators
US7674819B2 (en) 2005-05-05 2010-03-09 Warner-Lambert Company Llc Androgen modulators

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Publication number Priority date Publication date Assignee Title
WO1996026206A1 (fr) * 1995-02-24 1996-08-29 Basf Aktiengesellschaft Derives de pyrazol-4-yl-benzoyle et leur utilisation comme herbicides
WO1997041117A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Nouveaux derives du benzene substitues par des heterocycles, et herbicides
WO1997041116A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides
WO1997041118A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
WO1998021187A1 (fr) * 1996-11-13 1998-05-22 Nippon Soda Co., Ltd. Nouveaux derives de benzene a substitution heterocyclique, et herbicide

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JPS57212162A (en) * 1981-06-23 1982-12-27 Sankyo Co Ltd Pyrazole derivative and herbicide

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WO1996026206A1 (fr) * 1995-02-24 1996-08-29 Basf Aktiengesellschaft Derives de pyrazol-4-yl-benzoyle et leur utilisation comme herbicides
WO1997041117A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Nouveaux derives du benzene substitues par des heterocycles, et herbicides
WO1997041116A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides
WO1997041118A1 (fr) * 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Derives du benzene substitues par des heterocycles, et herbicides
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
WO1998021187A1 (fr) * 1996-11-13 1998-05-22 Nippon Soda Co., Ltd. Nouveaux derives de benzene a substitution heterocyclique, et herbicide

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7576128B2 (en) 2004-02-13 2009-08-18 Pfizer Inc. Androgen receptor modulators
US7507860B2 (en) 2004-04-13 2009-03-24 Pfizer Inc. Androgen modulators
US7674819B2 (en) 2005-05-05 2010-03-09 Warner-Lambert Company Llc Androgen modulators
US7799823B2 (en) 2005-05-05 2010-09-21 Warner-Lambert Company Llc Androgen modulators

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