WO2007101859A1 - Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant - Google Patents

Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant Download PDF

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WO2007101859A1
WO2007101859A1 PCT/EP2007/052104 EP2007052104W WO2007101859A1 WO 2007101859 A1 WO2007101859 A1 WO 2007101859A1 EP 2007052104 W EP2007052104 W EP 2007052104W WO 2007101859 A1 WO2007101859 A1 WO 2007101859A1
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compounds
hydrogen
alkyl
formula
chlorine
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PCT/EP2007/052104
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German (de)
English (en)
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Jochen Dietz
Thomas Grote
Wassilios Grammenos
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to substituted pyrazolopyrimidines of the formula I.
  • R 1 is hydrogen, Ci-Ci 2 -alkyl, C 2 -haloalkyl, C 2 -C 2 -alkenyl, C 2 -C 2 halo-alkenyl, C 2 -C 2 alkynyl, C 2 -C 2 - haloalkynyl, C3-C8 cycloalkyl, C3-C cycloalkyl 8-halo, C3-C6-cycloalkenyl, C3-C6 halocycloalkenyl, C 8 -alkoxy, C 8 - haloalkoxy, C 2 -C 8 alkenyloxy , C 2 -C 8 -alkynyloxy, C 3 -C 8 -cycloalkoxy, NH 2 ,
  • R 3, R 4, R 5, R 6, R 7, R 8 independently of one another hydrogen, C -C -alkyl 8 -alkyl, Ci-C 8 - haloalkyl, C 2 -C 8 -alkenyl -alkyl, C 2 -C 8 Haloalkenyl, C 2 -C 8 -alkynyl, C 2 -C 8 -halo-genalkinyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 -
  • R 5 can also form, with R 3 or R 7 together with the atoms to which these radicals are bonded, a five, six, seven, eight, nine or ten-membered saturated or partially unsaturated ring which, in addition to carbon atoms, may contain two or three heteroatoms from the group O, N and S as a ring member and / or may carry one or more substituents R a ;
  • R 3 with R 4, R 5 with R 6, R 7 with R 8 may each represent together also to form carbonyl oxygen and the formation of the spiro groups, a C 2 -C 6 alkylene or alkenylene, alkynylene form, by a , two or three heteroatoms from the group O, N and S may be interrupted;
  • R 1 and R 3 may together with the nitrogen atom and the carbon atom to which they are attached form a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle which, in addition to carbon atoms, may contain two or three further heteroatoms from the group O, N and S as a ring member;
  • R 1 and R 3 to R 8 may each independently carry one, two, three or four identical or different groups R a :
  • R a is halogen, cyano, nitro, amino, guanidino, hydroxy, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 8 -alkynyl, C 2 -C 8 -haloalkenyl, C 2 -C 6 -Al kinyl, C 2 -C 6 haloalkynyl, C3-C6-cycloalkyl, C3-C8 cycloalkenyl, Ci-C ⁇ -alkoxy, Ci-C ⁇ -haloalkoxy, C2-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3 -C 6 -alkynyloxy, C 3 -C 6 -haloalkynyloxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -CCCl 10 -alkenyloxy, formyl
  • R b is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, Alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, the alkyl groups in these radicals containing from 1 to 6 carbon atoms and the alkenyl or alkynyl groups mentioned in these radicals
  • Radicals contain 2 to 8 carbon atoms; Cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, wherein the cyclic systems contain 3 to 10 ring members; Aryl, aryloxy, arylthio, aryl-Ci-C ⁇ -alkoxy, aryl C 1 -C 6 -alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members, the hetaryl radicals contain 5 or 6 ring members, where the cyclic systems may be partially or completely halogenated and / or substituted by alkyl or haloalkyl groups ;
  • Z is hydrogen, carboxyl, formyl, C 5 -C 8 alkyl, d-C ⁇ -haloalkyl, C 2 -C 8 -alkenyl -alkyl, C2-C8 haloalkenyl, C 2 -Cs-Al kinyl, C2-C8-haloalkynyl, C3-C6-cycloalkyl,
  • R A , R B independently of one another are hydrogen or one of the groups mentioned for R ⁇ ;
  • R A and R B together with the nitrogen atom to which they are attached, or R A and R ⁇ together with the carbon atoms and heteroatoms via which they are attached can also have a five- or six-membered saturated, partially unsaturated or form an aromatic ring which, in addition to carbon atoms, has one, two or three further heteroatoms from the group O,
  • N and S as a ring member and / or can carry one or more substituents R a ;
  • Z can also form with R 6 or R 8 a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group N and S as ring member and / or one or more substituents R a can carry, as defined above;
  • the group Z may be partially or completely halogenated and / or carry one, two or three groups R b ;
  • R 1 and R 2 may also together with the nitrogen atom to which they are attached form a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or heterocycle which, in addition to carbon atoms, has one, two or three carbon atoms further heteroatoms from the group O, N and S may contain as ring member and which contains at least one substituent selected from UO #, VS # and VY- (CR 5 R 6 ) q -CR 3 R 4 - #, and # is the point of attachment to the heterocycle and the heterocycle can also carry one, two or three groups R a ;
  • V is hydrogen or one of the groups mentioned at U;
  • p is zero, 1, 2, 3, 4 or 5;
  • q is zero or 1;
  • W 1, W 2 are each independently hydrogen, halogen, cyano, nitro, Ci-C 4 - alkyl kinyl 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C, Ci-C4-haloalkyl, hydroxy-Ci C4-alkyl, Ci-C4-alkoxy-Ci-C 4 alkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C3-C6 cycloalkyl, C3-C6-halocycloalkyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, -C 4 - alkylthio, C 1 -C 4 AI ky I su If iny I or Ci-C 4 alkylsulfonyl, formyl, thiocarbamoyl,
  • R 10 , R 11 , R 12 independently of one another are hydrogen, C 1 -C 8 -alkyl, C 3 -C 6 -cycloalkyl,
  • R 13 is hydrogen or C 1 -C 6 -alkyl
  • R 14 is C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 3 -C 6 -cycloalkyl, phenyl, phenylamino, where the phenyl groups may be substituted by one to five groups R b ;
  • X is halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
  • n is zero, 1, 2, 3, 4 or 5;
  • L is halogen, hydroxy, carboxy, cyanato (OCN), cyano, nitro, C 1 -C 8 -alkyl,
  • Ci-Cs-haloalkyl C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, Ci-Cs-alkoxy, Ci- Cs-haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -C 10 -alkynyloxy, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkenyloxy, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 ) -alkylamino, C 1 -C 4 -alkyl 4- alkylcarbonylamino, C (O) -R, C (S) -R, S (O) n -R, CrC 6 -
  • two radicals L bound to adjacent ring carbon atoms may also together 1, 3-propanediyl, 1, 4-butanediyl, methylenedioxy or 1, 2-ethylenedioxy, where the four last mentioned radicals may be mono- or polysubstituted by identical or different halogen, Alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; R is hydrogen, Ci -C 6 alkyl-Al, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, C 2 -C 4 -alkenyl oxy, C2-C4-alkynyloxy, amino, Ci-C4-alkylamino, di - (Ci-C4) alkylamino; wherein the groups R may be substituted by one, two or three identical or different groups R b as defined above;
  • n zero, 1 or 2;
  • the invention relates to processes and intermediates for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
  • 5-halogen-7-amino-pyrazolopyrimidines are generally known, which are substituted in the 6-position by a heterocycle. These compounds are known for controlling harmful fungi.
  • the compounds of the invention differ from those described in the cited document by the design of the group R 2 at the 7-amino group.
  • the object of the present invention is to provide compounds with improved activity and / or broadened spectrum of activity.
  • the compounds of the invention can be obtained in various ways.
  • they are prepared by reacting 7-Dihalogenpyrazolopyrimidinen of formula II with amines of the formula IM in which the variables are defined as for formula I.
  • This reaction is advantageously carried out at 0 0 C to 70 0 C, preferably 10 0 C to 35 0 C, preferably in the presence of an inert solvent such as ethers, eg. Eg oxane, diethyl ether or in particular tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane and aromatic hydrocarbons, such as, for example, toluene [cf. WO 05/000851].
  • ethers eg. Eg oxane, diethyl ether or in particular tetrahydrofuran
  • halogenated hydrocarbons such as dichloromethane
  • aromatic hydrocarbons such as, for example, toluene [cf. WO 05/000851].
  • a base such as tertiary amines, for example triethylamine or inorganic amines, such as potassium carbonate is preferred; Excess amine of the formula IM can also serve as a base.
  • the 5-chloropyrazolopyrimidines of the formula I are thus available. They represent a preferred subject of the invention.
  • Other 5,7-dihalo-pyrazolopyrimidines are accessible analogously to the cited literature.
  • Amines of the formulas IM are known in the literature, can be prepared by known methods or are commercially available.
  • Compounds of the formula I in which X is cyano, alkoxy or haloalkoxy can advantageously be obtained from the reaction of compounds I in which X is halogen, preferably chlorine, with compounds M-X '(formula IV).
  • compounds IV represent an inorganic cyanide, an alkoxylate or a haloalkoxylate.
  • the reaction is advantageously carried out in the presence of an inert solvent.
  • the cation M in formula IV has little significance; For practical reasons, ammonium, tetraalkylammonium or alkali or alkaline earth metal salts are usually preferred.
  • the reaction temperature is usually 0 to 120 ° C., preferably 10 to 40 ° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • Suitable solvents include ethers such as dioxane, diethyl ether and, preferably tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene.
  • compounds of the formula I in which X denotes C 1 -C 4 -alkyl may also be prepared from compounds I in which X is halogen, in particular chlorine, and malonates of the formula VI are prepared.
  • X is hydrogen or C 1 -C 3 -alkyl and R is C 1 -C 4 -alkyl They are converted into compounds of formula VII and decarboxylated to compounds I [see US 5,994,360]
  • the compounds of formula VII are novel.
  • the subsequent saponification of the ester VII is carried out under generally customary conditions, depending on the various structural elements, the alkaline or the acidic saponification of the compounds VII may be advantageous. Under the conditions of the ester saponification, the decarboxylation to I can already take place completely or partially.
  • the decarboxylation is usually carried out at temperatures of 20 0 C to 180 0 C, preferably 50 0 C to 120 0 C, in an inert solvent, optionally in the presence of an acid.
  • Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid.
  • Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • Compounds of the formula I in which X is C 1 -C 4 -alkyl can also be obtained by coupling 5-halopyrazolopyrimidines of the formula I with organometallic reagents of the formula VIII.
  • the reaction is carried out under transition metal catalysis, such as Ni or Pd catalysis.
  • M stands for a metal ion of valency Y, such as B, Zn or Sn and X "for CrC 4 -AlkVl.
  • This reaction can be carried out, for example, by the following methods: J. Chem. Soc. Perkin Trans 187 (1994), ibid. 1, 2345 (1996); WO 99/41255; Aust. J. Chem., 43, 733 (1990); J. Org. Chem., 43, 358 (1978); Chem. Soc. Chem. Commun., 866 (1979); Tetrahedron Lett, Vol. 34, 8267 (1993); ibid., Vol. 33, 413 (1992).
  • the compounds of the formula I can also be prepared from hydroxy- or mercaptopyrrazolopyrimidines of the formula Ia.
  • the 7-hydroxy, or mercaptoaminopyrazolopyrimidine of the formula Ia is reacted with an alkylating or acylating agent Z-LG, where LG is a nucleophilic cleavable group.
  • LG is a nucleophilic cleavable group.
  • carboxylic anhydrides such as.
  • acetic anhydride, or carboxylic acid chlorides carboxylic acids used in conjunction with coupling reagents such as dicyclohexylcarbodiimide or acids such as HCl.
  • the reaction conditions suitable for the etherification or esterification are generally known to the person skilled in the art [cf .: Organikum, VEB Deutscher Verlag dermaschineen, Berlin (1981)].
  • the compounds of formula Ia are z. T. from the documents cited above.
  • reaction mixtures are worked up in a conventional manner, for. B. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products fall z. T. in the form of colorless or pale brownish, viscous oils, which under reduced pressure and moderately elevated temperature of volatile fractions freed or cleaned. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • Articles of the invention are both the pure enantiomers or diastereomers and their mixtures or the inventive use of the pure enantiomers or diastereomers of the compound I or mixtures thereof.
  • Suitable compounds of the general formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • Suitable agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, the desired one to four Ci -C 4 -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium and sulfoxonium ions, preferably tris
  • Anions of acceptable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 alkanoic acids, preferably formate, acetate , Propionate and butyrate.
  • You can by reaction of I with an acid of the corresponding Anions preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid, are formed.
  • Suitable pharmaceutically acceptable salts are, in particular, physiologically tolerated salts of compound I, in particular the acid addition salts with physiologically tolerated acids.
  • suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, C 1 -C 4 -alkylsulfonic acids, such as methanesulfonic acid, aromatic sulfonic acids, such as benzenesulfonic acid and toluenesulfonic acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid.
  • suitable acids are described, for example, in Fort Whitney der Arzneistoffforschung, Volume 10, pages 224 et seq., Birkhäuser Verlag, Basel and Stuttgart, 1966, to which reference is hereby made in their entirety.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 carbon atoms, eg. C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3 Methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4, 6, 8 or 12 carbon atoms (as mentioned above), wherein in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl such as Chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroeth
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6 or 8 or 12 carbon atoms and one or two double bonds in any position, for.
  • C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2- Pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), wherein in these groups the hydrogen atoms partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine could be;
  • Alkynyl straight-chain or branched hydrocarbon groups having 2 to 4, 6 or 8 or 12 carbon atoms and one or two triple bonds in any position, for.
  • B. C 2 -C 6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1 Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-penty
  • Cycloalkyl mono- or bicyclic, saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, e.g.
  • C 1 -C 8 -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom 5-membered heteroaryl groups which contain, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur atom. or oxygen atom may contain as ring members, for. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl,
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-membered ring heteroaryl groups, which in addition to carbon atoms may contain one to three or one to four nitrogen atoms as ring members, for. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl;
  • Alkylene divalent linear chains of 1 to 6 CH 2 groups, e.g. CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 21 CH 2 CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylene divalent unbranched chains of 1 to 4 CH 2 groups, wherein a valence is bonded via an oxygen atom to the skeleton, z. OCH 2 , OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylenoxy divalent unbranched chains of 1 to 3 CH 2 groups, wherein both valences are bonded via an oxygen atom to the skeleton, z. OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • R 1 is hydrogen or C 1 -C 4 -alkyl, such as hydrogen or methyl or ethyl, in particular hydrogen.
  • a preferred embodiment relates to compounds I in which R 1 and R 2 together with the nitrogen atom to which they are attached form a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle, in addition to Carbon atoms one, two or three further heteroatoms from the group O, N and S may contain as a ring member and which contains at least one substituent selected from UO- #, VS- # and VY-CR 3 R 4 - #, wherein the Heterocycle may contain one or two groups R a .
  • a further embodiment relates to compounds I in which U is carboxyl, formyl, C 5 -C 8 -alkyl, C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 - C 8 -alkenyl, C 2 -C 8 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , C (NR A ) SR ⁇ , C (S) R ⁇ , C (NR ⁇ ) NR A R B , C (NR ⁇ ) R A , C ( NR ⁇ ) OR A , C (O) NR A R B , C (NR ⁇ ) R A , C (
  • U does not mean Ci-C 8 alkyl.
  • V is not Ci-C 8 alkyl.
  • V is hydrogen.
  • a further embodiment relates to compounds I in which the group NR 1 R 2 is one of ethylglycinol, leucinol, tert-leucinol, valinol, norvalinol, methioninol, phenylalaninol, lysinol, argininol, histidinol, asparaginol, glutaminol, serinol, isoleucinol, Cysteinol, hydroxymethylpiperidine, prolinol, cis-2-hydroxymethyl-4-methylpiperidine, trans-2-hydroxymethyl-4-methylpiperidine, cyclohexylglycinol, cyclopentylglycinol, butylglycinol, pentylglycinol, cis-2-aminocyclohexanol, trans-2- Aminocyclohexanol, cis-2-aminocyclopentanol, trans-2-amino
  • R 2 is ZY- (CR 7 R 8 ) P -CR 5 R 6 -CR 3 R 4 - # wherein p is zero or 1.
  • a further embodiment relates to compounds I in which R 3 is straight-chain or branched C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl or C 3 -C 6 -cycloalkyl, in particular C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, is preferred iso-propyl, iso-butyl, tert. Butyl, sec. Pen- tyl, cyclopropyl or cyclopentyl, in particular tert. Butyl.
  • Another embodiment relates to compounds I in which R 3 is not hydrogen or methyl.
  • the group R 3 has a branching on the ⁇ -carbon atom.
  • the group R 3 is substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or formyl, carboxyl, alkoxycarbonyl, alkoxythiocarbonyl or alkenyl, alkynyl groups or C 2 -C 5 -alkylene, both being Valences are bonded to the same carbon atom.
  • the group R 3 is substituted by C 3 -C 6 -cycloalkyl or C 3 -C 8 -cycloalkenyl.
  • the group R 3 is C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , carbamoyl, C (O) NHR ⁇ , C (O) NR ⁇ 2 , thiocarbamoyl, C (S) NHR ⁇ , C (S) NR ⁇ 2 C (NR ⁇ ) R ⁇ , C (NH) R ⁇ , C (O) SR ⁇ or C (S) SR ⁇ substituted.
  • R ⁇ Ci -C 8 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 kinyl -alkyl, C 3 -C 6 - cycloalkyl or C 3 -C 6 cycloalkenyl.
  • Z is C (O) R ⁇ or C (S) R ⁇
  • R ⁇ may also be phenyl, wherein R ⁇ may be partially or fully halogenated and / or may carry one, two or three groups R b .
  • R ⁇ is preferably C 1 -C 8 -alkyl or C 3 -C 6 -cycloalkyl, which groups may be partially or fully halogenated.
  • the group R 3 is represented by a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, substituted.
  • R a is halogen, cyano, nitro, hydroxy, carboxyl, Ci-C ⁇ alkyl, Ci-C ⁇ -halo- genalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C6-AI kinyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C8 cycloalkenyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, C 2 -C 6 - alkenyloxy, C3-C6-haloalkenyloxy, C3-C6 alkynyloxy, C3- C 6 -haloalkynyloxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR
  • R a may also have the following meanings: amino, formyl, carbamoyl, thiocarbamoyl, C (S) NHR ⁇ , C (S) NR ⁇ 2 , C (NH) R ⁇ or C (NR ⁇ ) ⁇ R, wherein R ⁇ is C 8 alkyl, C 3 -C 8 -alkenyl -alkyl, C 3 -C 8 kinyl -alkyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 cycloalkenyl stands.
  • a further embodiment relates to compounds I in which R 4 is hydrogen, straight-chain or branched C 1 -C 8 -alkyl or C 3 -C 6 -cycloalkyl, in particular hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, are preferred Hydrogen, iso-propyl, tert. Butyl. If R 4 is an alkyl group, R 4 preferably has the same meaning as R 3 .
  • R 3 and R 4 together form a C 3 -C 6 -alkylene, in particular a C 3 -C 4 -alkylene group, where the carbon chains may be substituted by heteroatom-bonded groups, such as halogen, alkoxy , Alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.
  • R 3 and R 4 form a C 2 -C 5 -alkylene, alkenylene or alkynylene chain which may be interrupted by one, two or three heteroatoms from the group consisting of O, N and S.
  • R 3 and R 4 together form a C 3 -C 6 -alkylene, in particular a C 3 -C 4 -alkylene group, where the carbon chains are replaced by one or two heteroatoms from the group O, N and S are interrupted and may be substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.
  • R 4 , R 5 , R 6 , R 7 and R 8 are each hydrogen or C 1 -C 4 -alkyl, preferably hydrogen, methyl or ethyl, in particular hydrogen.
  • the substitution of the groups R 4 , R 5 , R 6 , R 7 and R 8 can be carried out according to the group R 3 .
  • R 3 and R 5 together form a C 3 -C 6 -alkylene, C 3 -C 6 -oxyalkylene or C 1 -C 8 -oxyalkyleneoxy, in particular a C 3 -C 4 -alkylene group.
  • R 5 and R 6 and / or R 7 and R 8 each together form a C 3 -C 6 -alkylene, C 3 -C 6 -oxyalkylene or C 2 -C 5 -oxyalkyenoxy, in particular a C 3 C4-Alkyen distruv.
  • the index q has the value zero.
  • Another embodiment relates to compounds I in which the index q is 1.
  • Another embodiment relates to compounds I in which the index p is zero or 1, in particular zero.
  • R 5 and R 6 are preferably hydrogen, provided that the index p has the value zero.
  • R 7 is not hydrogen and R 8 is hydrogen, provided that the index p has the value zero.
  • the index p has the value zero or 1 and the index q the value 1.
  • Y is oxygen
  • Z represents a monovalent group.
  • Z in formula I is hydrogen, carboxyl, formyl, Cs-Cs-alkyl, Ci-Cs haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl , C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , C (NR A ) SR ⁇ , C (S) R ⁇ , C (NR ⁇ ) NR A R B , C (NR ⁇ ) R A , C (NR ⁇ ) OR A , C (O) NR A R B, C (S) NR A R B, d-C ⁇ -alkylsulfinyl, Ci
  • R A and R B are independently hydrogen, C2-alkenyl, C 2 alkynyl, Ci -C 8 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 -alkyl kinyl, C 3 - C 6 cycloalkyl or C 3 -C 6 - cycloalkenyl.
  • a further embodiment relates to compounds I in which Z is C 1 -C 4 -alkylcarbonyl, in particular acetyl, n-propan-1-one, 2-methylpropan-1-one or butan-1-one.
  • a further embodiment relates to compounds I in which Z is carboxyl or formyl.
  • Another embodiment relates to compounds I in which Z is hydrogen.
  • Another embodiment relates to compounds I in which Z is carboxyl.
  • Another embodiment relates to compounds I in which Z is formyl.
  • Another embodiment relates to compounds I in which Z is Cs-Cs-alkyl.
  • a further embodiment relates to compounds I in which Z is C 1 -C 8 -haloalkyl.
  • a further embodiment relates to compounds I in which Z is C 2 -C 8 -alkenyl.
  • a further embodiment relates to compounds I in which Z is C 2 -C 8 -haloalkenyl.
  • a further embodiment relates to compounds I in which Z is C 2 -C 8 -alkynyl.
  • a further embodiment relates to compounds I in which Z is C 2 -C 8 -haloalkynyl.
  • Another embodiment relates to compounds I in which Z is C 3 -C 6 -cycloalkyl.
  • Another embodiment relates to compounds I in which Z is C 3 -C 8 -cycloalkenyl.
  • a further embodiment relates to compounds I in which Z is C (O) R ⁇ .
  • a further embodiment relates to compounds I in which Z is C (O) OR ⁇ .
  • a further embodiment relates to compounds I in which Z is C (S) OR ⁇ .
  • Another embodiment relates to compounds I in which ZC (O) SR is ⁇ .
  • a further embodiment relates to compounds I in which ZC (S) SR is ⁇ .
  • a further embodiment relates to compounds I in which Z is C (NR A ) SR ⁇ .
  • a further embodiment relates to compounds I in which Z is C (S) R ⁇ .
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) NR A R B.
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) R A.
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) OR A means.
  • Another embodiment relates to compounds I in which Z is C (O) NR A R B.
  • Another embodiment relates to compounds I in which Z is C (S) NR A R B.
  • Another embodiment relates to compounds I in which Z is C 1 -C 5 -alkylsulfinyl.
  • a further embodiment relates to compounds I in which Z is C 1 -C 5 -alkylthio.
  • a further embodiment relates to compounds I in which Z is C 1 -C 5 -alkylsulfonyl.
  • a further embodiment relates to compounds I in which Z is C (O) -Ci-C 4 -alkylene-NR A C (NR ⁇ ) NR A R B.
  • a further embodiment relates to compounds I in which Z is C (S) -Ci-C 4 -alkylene-NR A C (NR ⁇ ) NR A R B.
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) -Ci-C 4 -alkylene-NR A C (NR ⁇ ) NR A R B.
  • Another embodiment relates to compounds I in which Z is phenyl.
  • Another embodiment relates to compounds I in which Z is naphthyl.
  • a further embodiment relates to compounds I in which Z represents a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic see a heterocycle containing one, two, three or four heteroatoms from the group O, N and S which is bonded directly or via a carbonyl, thiocarbonyl, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkylthiocarbonyl group, means.
  • the abovementioned groups Z can be substituted by one or more groups R b .
  • a preferred embodiment relates to compounds I in which Z is hydrogen, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 8 -alkylaminocarbonyl, C6-alkylthiocarbonyl, Ci-C ⁇ -
  • a further preferred embodiment relates to compounds I in which Z is C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl, in particular C 1 -C 4 -alkylcarbonyl or the like stands.
  • Another particularly preferred embodiment relates to compounds I in which Z is hydrogen.
  • the group Z is represented by one, two, three or four groups R b , such as halogen, or basic or acidic groups, such as NR A R B , guanidino (guaninyl), amidino (amidyl), hydroxy, carboxyl or sulfo (SO3H) substituted.
  • R b such as halogen, or basic or acidic groups, such as NR A R B , guanidino (guaninyl), amidino (amidyl), hydroxy, carboxyl or sulfo (SO3H) substituted.
  • a further embodiment relates to compounds I in which X is fluorine, chlorine or bromine, in particular chlorine.
  • a further embodiment relates to compounds I in which X is cyano, alkyl or alkoxy, in particular cyano, methyl or methoxy.
  • X is C 1 -C 3 -alkyl, in particular methyl, ethyl or n-propyl, especially methyl.
  • Het is a non-aromatic saturated or partially unsaturated 5- or 6-membered heterocyclyl containing one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, stands.
  • a further embodiment relates to compounds I in which Het is a 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom.
  • a further embodiment relates to compounds I in which Het is a 6-membered heteroaryl containing one to three or one to four nitrogen atoms.
  • a further embodiment relates to compounds I in which Het is pyridyl which is linked in the 2-, 3- or 4-position and may be monosubstituted, monosubstituted or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl , Ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl.
  • a further embodiment relates to compounds I in which Het is pyrimidyl which is linked in the 2- or 4-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, Methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl.
  • a further embodiment relates to compounds I in which Het is thienyl which is linked in the 2- or 3-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, Methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl.
  • a further embodiment relates to compounds I in which Het is thiazolyl which is linked in the 2-, 4- or 5-position and may be monosubstituted, disubstituted or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl , Ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl.
  • a further embodiment relates to compounds I in which Het is imidazolyl which is linked in the 4- or 5-position and may be monosubstituted or disubstituted by identical or different substituents by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, Methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl.
  • a further embodiment relates to compounds I in which Het is pyrazolyl which is linked in the 3-, 4- or 5-position and may be monosubstituted to trisubstituted, identically or differently substituted by fluorine, chlorine, bromine, cyano, nitro, methyl , Ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl.
  • a further embodiment relates to compounds I in which Het is oxazolyl which is linked in the 2-, 3- or 4-position and may be monosubstituted or disubstituted by identical, different or different substituents by fluorine, chlorine, bromine, cyano, nitro , Methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl.
  • at least one group L is ortho to the point of attachment to the pyrazolopyrimidine skeleton, in particular chlorine, fluorine or methyl.
  • L stands for halogen, hydroxy, cyanato (OCN), cyano, nitro, C -C -alkyl 8 -alkyl, Ci-C 8 - haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy, C2-Cio-alkenyloxy, C2-Cio-alkynyloxy, C3-C6-cycloalkyloxy, C 3 -C 6 -cycloalkenyloxy, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4) -alkylamino, C 1 -C 4 -alkylcarbonylamino
  • the index m is preferably from 1 to 4, where the groups L may be the same or different.
  • meanings for L come into question:
  • haloalkyl straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
  • alkylamino straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl.alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
  • the group Het substituted by L m is one of the following: 6-chloropyrid-2-yl, 6-fluoropyrid-2-yl, 6-methyl-pyrid-2-yl, 6-trifluoromethyl-pyridine 2-yl, 5-chloropyrimid-4-yl, 5-fluoropyrimid-4-yl, 5-methyl-pyrimid-4-yl, 5-trifluoromethyl-pyrimid-4-yl, thien-3-yl, 2-chlorothien-3-yl, 2-fluorothien-3-yl, 2-methylthien-3-yl, 2-trifluoromethylthien-3-yl, 2,5-dichlorothiene-3 yl, 2,5-difluoro-thien-3-yl, 2,5-dimethylthien-3-yl.
  • W 1 is hydrogen, fluorine, chlorine or bromine, in particular hydrogen.
  • W 2 is preferably cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine, chlorine and / or bromine atoms, alkyl having 1 to 4 carbon atoms , Cycloalkyl having 3 to 6 carbon atoms, thiocarbamoyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl part, hydroxyamidino, hydroximinoalkyl having 1 to 4 carbon atoms in the alkyl part or alkoxyiminoalkyl having 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl moiety.
  • W 2 is CR 10 R 11 OR 12 .
  • W 2 is hydrogen or cyano.
  • a further embodiment of the invention relates to compounds of the formula I.1A:
  • a further embodiment of the invention relates to compounds of the formula 1.1 B:
  • Another embodiment of the invention relates to compounds of the formula 1.1 C:
  • a further embodiment of the invention relates to compounds of the formula 1.1 D:
  • a further embodiment of the invention relates to compounds of the formula I.2A,
  • a further embodiment of the invention relates to compounds of the formula I.2C,
  • a further embodiment of the invention relates to compounds of the formula I.2D,
  • a further embodiment of the invention relates to compounds of the formula I.3A:
  • a further embodiment of the invention relates to compounds of the formula I.3B:
  • a further embodiment of the invention relates to compounds of the formula I.3C:
  • Another embodiment of the invention relates to compounds of the formula I.3D:
  • Table 5 Compounds of the formula 1.1B in which X is chlorine, L 1 is chlorine and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z is a compound in each case corresponds to one line of Table A.
  • Table 6 Compounds of the formula 1.1B in which X is chlorine, L 1 is fluorine and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z is a compound in each case corresponds to one line of Table A.
  • Table 7 Compounds of the formula IB in which X is chlorine, L 1 is methyl and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z is a compound in each case Line of Table A corresponds.
  • Table 8 Compounds of the formula 1.1B in which X is chlorine, L 1 is trifluoromethyl and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z is a compound in each case corresponds to one line of Table A.
  • Table 9 Compounds of the formula 1.1 C, in which X is chlorine, L 1 and L 2 are hydrogen and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z represents one compound corresponds in each case to one row of Table A.
  • Table 10 Compounds of the formula 1.1 C, in which X is chlorine, L 1 and L 2 are chlorine and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 1 Compounds of the formula I.1C, in which X is chlorine, L 1 is chlorine, L 2 is hydrogen and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 12 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are methyl and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 13 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are methyl and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 13 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are methyl and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 13 Compounds of the formula I.1
  • Table 22 Compounds of the formula 1.1 D in which X is chlorine, L 1 is fluorine, L 2 is hydrogen and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 23 Compounds of the formula 1.1 D, in which X is chlorine, L 1 is methyl, L 2 is hydrogen and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 24 Compounds of the formula 1.1 D, in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen and W 1 , W 2 , R 1 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 25 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are hydrogen and W 1 , W 2 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 28 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are methyl and W 1 , W 2 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 29 Compounds of the formula I.2D, in which X is chlorine, L 1 and L 2 are trifluoromethyl and W 1 , W 2 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 30 Compounds of the formula I.2D, in which X is chlorine, L 1 and L 2 are trifluoromethyl and W 1 , W 2 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 30 Compounds of the formula I.2D, in which X is chlorine, L 1 and L 2 are trifluoromethyl and W 1 , W 2 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R
  • Table 39 Compounds of the formula 1.1B in which X is chlorine, L 1 is methyl and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z is a compound corresponds to one row of Table A.
  • Table 40 Compounds of the formula 1.1B in which X is chlorine, L 1 is trifluoromethyl and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z is a compound corresponds to one row of Table A.
  • Table 41 Compounds of the formula 1.1 C, in which X is chlorine, L 1 and L 2 are hydrogen and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 42 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are chlorine and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 43 Compounds of the formula 1.1 C, in which X is chlorine, L 1 is chlorine, L 2 is hydrogen and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 44 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are methyl and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 45 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are trifluoromethyl and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 46 Compounds of the formula 1.1 C, in which X is chlorine, L 1 is fluorine, L 2 is hydrogen and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 47 Compounds of the formula 1.1 C, in which X is chlorine, L 1 is fluorine, L 2 is hydrogen and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 56 Compounds of the formula 1.1 D, in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen and R 1 is methyl, W 1 , W 2 , R 5 and R 6 are hydrogen and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 57 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are hydrogen and R 1 is methyl, W 1 , W 2 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 58 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are chlorine and R 1 is methyl, W 1 , W 2 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 60 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are methyl and R 1 is methyl, W 1 , W 2 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 63 Compounds of the formula I.2D, in which X is chlorine, L 1 is methyl, L 2 is hydrogen and R 1 is methyl, W 1 , W 2 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 64 Compounds of the formula I.2D, in which X is chlorine, L 1 is methyl, L 2 is hydrogen and R 1 is methyl, W 1 , W 2 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 64 Compounds of the formula I.2D, in which X is chlorine, L 1 is methyl, L 2 is hydrogen and R 1 is methyl, W 1 , W 2 , R 5 , R 6 , R 7 and R 8 are hydrogen and the combination of R
  • Table 73 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 74 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 75 Compounds of the formula 1.1 C in which X is chlorine, L 1 is chlorine, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 76 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 77 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are trifluoromethyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 78 Compounds of the formula I.1C, in which X is chlorine, L 1 is fluorine, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano, and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 79 Compounds of the formula I.1C, in which X is chlorine, L 1 is methyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano, and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 80 Compounds of the formula 1.1 C in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 81 Compounds of the formula 1.1 C in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 81 Compounds of the formula 1.1 C in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • R 1 , R 5 and R 6 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 90 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are chlorine, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 91 Compounds of the formula I.2D, in which X is chlorine, L 1 is chlorine, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 92 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 94 Compounds of the formula I.2D, in which X is chlorine, L 1 is fluorine, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 95 Compounds of the formula I.2D in which X is chlorine, L 1 is methyl, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 96 Compounds of the formula I.2D in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is cyano and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 97 Compounds of the formula I.1A in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 98 Compounds of the formula I.1A in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 98 Compounds of the formula I.1A in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 98 Compounds of the formula I.1A in which X
  • Table 107 Compounds of the formula I.1C in which X is chlorine, L 1 is chlorine, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 108 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 109 Compounds of the formula 1.1 C, in which X is chlorine, L 1 and L 2 are trifluoromethyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 1 12 Compounds of the formula 1.1 C, in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 1 13 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 1 14 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 1 15 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 1 15 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 1 15 Compounds of the formula 1.1 D in which X is
  • R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • R 7 and R 8 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 124 Compounds of the formula I.2D, in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 125 Compounds of the formula I.2D in which X is chlorine, L 1 and L 2 are trifluoromethyl, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 126 Compounds of the formula I.2D, in which X is chlorine, L 1 is fluorine, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is formyl, and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 127 Compounds of the formula I.2D in which X is chlorine, L 1 is methyl, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 128 Compounds of the formula I.2D, in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 129 Compounds of the formula I.1A in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is formyl and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 130 Compounds of the formula I.1A in which X is chlorine, L 1 is fluorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 131 Compounds of the formula I.1A in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 132 Compounds of the formula I.1A in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 132 Compounds of the formula I.1A in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 132 Compounds of the formula I.1A in which X is chlorine,
  • Table 141 Compounds of the formula I.1C in which X is chlorine, L 1 and L 2 are trifluoromethyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 142 Compounds of the formula I.1C in which X is chlorine, L 1 is fluorine, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 143 Compounds of the formula I.1C in which X is chlorine, L 1 is methyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 144 Compounds of the formula I.1C in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 145 Compounds of the formula 1.1 D, in which X is chlorine, L 1 and L 2 are hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 146 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 147 Compounds of the formula 1.1 D in which X is chlorine, L 1 is chlorine, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Table 148 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 149 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 149 Compounds of the formula 1.1 D in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 149 Compounds of the
  • R 1 , R 5 and R 6 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • R 7 and R 8 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and
  • R 6 , R 7 and R 8 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 158 Compounds of the formula I.2D, in which X is chlorine, L 1 is fluorine, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 159 Compounds of the formula I.2D, in which X is chlorine, L 1 is methyl, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is chlorine and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 160 Compounds of the formula I.2D, in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is chlorine, and the combination of R 3 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 161 Compounds of the formula I.1A in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 162 Compounds of the formula 1.1A, in which X is chlorine, L 1 is fluorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z is a compound corresponds to one row of Table A.
  • Table 163 Compounds of the formula I.1A in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 164 Compounds of the formula I.1A in which X is chlorine, L 1 is trifluoromethyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 165 Compounds of the formula 1.1B in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z is a compound corresponds to one row of Table A.
  • Table 166 Compounds of the formula 1.1B in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z is a compound corresponds to one row of Table A.
  • Table 166 Compounds of the formula 1.1B in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z is a compound corresponds to one row of Table A.
  • Table 166 Compounds of the formula 1.1B in which X is chlorine, L 1 is chlorine
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 175 Compounds of the formula 1.1 C, in which X is chlorine, L 1 is methyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 ,
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 176 Compounds of the formula 1.1 C, in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z for each compound corresponds to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 178 Compounds of the formula 1.1 D, in which X is chlorine, L 1 and L 2 are chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 180 Compounds of the formula 1.1 D, in which X is chlorine, L 1 and L 2 are methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 181 Compounds of the formula 1.1 D, in which X is chlorine, L 1 and L 2 are trifluoromethyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 ,
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 182 Compounds of the formula 1.1 D in which X is chlorine, L 1 is fluorine, L 2 is hydrogen, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 ,
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 192 Compounds of the formula I.2D in which X is chlorine, L 1 is trifluoromethyl, L 2 is hydrogen, W 1 , R 1 , R 5 , R 6 , R 7 and R 8 are hydrogen and W 2 is hydroxymethyl and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 193 Compounds of the formula 1.1A, in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 194 Compounds of the formula 1.1A, in which X is chlorine, L 1 is fluorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 195 Compounds of the formula I.1A in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 196 Compounds of the formula 1.1A in which X is chlorine, L 1 is trifluoromethyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 197 Compounds of the formula 1.1B in which X is chlorine, L 1 is chlorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 198 Compounds of the formula 1.1B in which X is chlorine, L 1 is fluorine, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 199 Compounds of the formula 1.1B in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 200 Compounds of the formula 1.1B in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • Table 200 Compounds of the formula 1.1B in which X is chlorine, L 1 is methyl, W 1 , R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z is one compound corresponds in each case to one row of Table A.
  • R 1 , R 5 and R 6 are hydrogen and W 2 is N-hydroxyamidino and the combination of R 3 , R 4 , Y and Z for a compound corresponds in each case to one row of Table A.
  • the compounds I are suitable as fungicides. They are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes, in particular from the class of the Oomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • Bipolaris and Drechslera species on maize, cereals, rice and turf eg D. teres on barley, D. tritici-repentis on wheat
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Bremia lactucae on lettuce - Cercospora species on maize, soybeans, rice and sugar beets (eg C. beticu- Ia on sugar beets),
  • Cochliobolus species on maize, cereals, rice eg Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice
  • Fusarium and Verticillium species eg V. dahliae
  • plants eg F. graminearum on wheat
  • Gaeumanomyces graminis on cereals
  • Helminthosporium species eg H. graminicola
  • Michrodochium nivale on cereals - Mycosphaerella species on cereals, bananas and peanuts (M. graminicola on wheat, M. fijiesis on banana),
  • Puccinia species on cereals, maize and asparagus P. triticina and P. striformis on wheat, P. asparagi on asparagus
  • Rhizoctonia species eg BR solani
  • Sclerotinia species eg S. sclerotiorum
  • oilseed rape e.g., sunflowers and other plants
  • Septoria tritici and Stagonospora nodorum on wheat e.g., S. sclerotiorum
  • Venturia species scab
  • pear eg V. inaequalis on apple
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleu- rotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the present invention relates to the pharmaceutical use of the compounds of the formula (I) according to the invention and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of tumors in mammals, such as in humans.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • novel active compounds are suitable for good plant tolerance and favorable toxicity to warm-blooded animals for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products and in the hygiene sector.
  • insects can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • the compounds of the formula I can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.
  • the compounds I can be converted into the customary formulations, for. As solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the Application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for. By stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • solvent mixtures can also be used
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • ketones eg cyclohexanone, gamma-butyrolactone
  • pyrrolidones NMP, NOP
  • acetates Glycol diacetate
  • Glycols dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • - Carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg highly disperse silicic acid, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg highly disperse silicic acid, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. As toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, eg. As dimethyl sulfoxide, N-methylpyrrolidone or water into consideration. Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules, for. B. coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are z.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such.
  • Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL, LS)
  • active compound 15 parts by weight are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has 15% by weight active ingredient content.
  • active compound 20 parts by weight of active compound are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of active compound are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • active compound 75 parts by weight of active compound are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • I dusts (DP, DS) 5 parts by weight of active compound are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.
  • 0.5 parts by weight of active compound are finely ground and combined with 99.5 parts by weight of carrier. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • K ULV solutions 10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for. B. XyIoI solved. This gives a product for direct application with 10 wt .-% active ingredient content.
  • water-soluble concentrates LS
  • suspensions FS
  • dusts DS
  • water-dispersible and water-soluble powders WS, SS
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for. B. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring are applied.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be effective substance wetting, adhesion, dispersing or emulsifying agents and possibly
  • Solvent or oil concentrates are prepared, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • organically modified polysiloxanes eg. B. Break Thru S 240®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B. Pluronic RPE 2035 ® and Genapol B ®
  • Alcohol ethoxylates eg. As Lutensol XP 80 ®
  • sodium dioctylsulfosuccinate e.g. B. Leophen RA ®.
  • compositions of the invention may also be present in the application form as fungicides together with other active ingredients, the z.
  • fungicides As with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • the compounds (I) or the agents containing them When mixing the compounds (I) or the agents containing them with one or more further active compounds, in particular fungicides, for example, in many cases, the activity spectrum can be broadened or development of resistance can be prevented. In many cases, synergistic effects are obtained.
  • Azoxystrobin dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate;
  • Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide (picobenzamide), zoxamide;
  • bitertanol bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetracona - zole, triadimenol, triadimefon, triticonazole;
  • - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; - Other: Ethaboxam, Etridiazole, Hymexazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • Dicarboximides iprodione, procymidone, vinclozolin;
  • acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- ( 4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6- iodo-3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;
  • Carbamates and Dithiocarbamates - Dithiocarbamates Ferbam, Mancozeb, Maneb, Metiram, Metam, Propineb, Thiram, Zineb, Ziram;
  • guanidines dodine, iminoctadine, guazatine
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, toluylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene;
  • Nitrophenyl derivatives binapacryl, dinocap, dinobuton;
  • the active substances were prepared as a stock solution with 25 mg of active ingredient, which was mixed with a mixture of acetone and / or dimethyl sulfoxide (DMSO) and the emulsifier Wettol® EM 31 (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume Ratio solvent emulsifier of 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Use Example 1 Curative activity against wheat brown rust caused by Puccinia recondita
  • test plants were incubated with an aqueous spore suspension of Pyrenophora [syn. Drechslera] teres, the causative agent of net blotch inoculation. Subsequently, the test plants were placed in the greenhouse at temperatures between 20 and 24 ° C and 95 to 100% relative humidity. After 6 days, the extent of disease development was determined visually as% of total leaf area.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des pyrazolopyrimidines substituées de formule (I) et leurs sels, formule dans laquelle les substituants ont les significations suivantes: R<SUP>1</SUP> désigne hydrogène, alkyle, halogène alkyle, alcényle, halogène alcényle, alkinyle, halogène alkinyle, cycloalkyle, halogène cycloalkyle, cycloalcényle, halogène cycloalcényle, alcoxy, halogène alcoxy, alcényloxy, alkinyloxy, cycloalcoxy, NH<SUB>2</SUB>, alkylamino, dialkylamino, phényle, naphtyle ou un hétérocycle saturé, partiellement saturé ou aromatique à cinq ou six membres, contenant un, deux, trois ou quatre hétéroatomes des groupes O, N et S; R<SUP>2 </SUP>signifie Z-Y-(CR<SUP>7</SUP>R<SUP>8</SUP>)<SUB>p</SUB>-(CR<SUP>5</SUP>R<SUP>6</SUP>)<SUB>q</SUB>-CR<SUP>3</SUP>R<SUP>4</SUP>-#, # étant le point de liaison avec l'atome d'azote; W<SUP>1</SUP>et W<SUP>2 </SUP>représentent indépendamment l'un de l'autre hydrogène, halogène, cyano, nitro, alkyle, alcényle, alkinyle, halogène alkyle, hydroxyalkyle, alcoxyalkyle, halogène alcényle, halogène alkinyle, cycloalkyle, halogène cycloalkyle, alcoxy, halogène alcoxy, alkylthio, alkylsulfinyle ou alkylsulfonyle, formyle, thiocarbamoyle, alkylcarbonyle, alcoxycarbonyle, alkylaminocarbonyle, alcoximinocarbonyle, hydroximinoalkyle, CR<SUP>10</SUP>R<SUP>11</SUP>OR<SUP>12</SUP>, C(R<SUP>13</SUP>)=NR<SUP>14</SUP>; X désigne halogène, cyano, alkyle, halogène alkyle, alcoxy ou halogène alcoxy; Het représente un hétérocycle saturé, partiellement saturé ou aromatique à cinq ou six membres, contenant un, deux, trois ou quatre hétéroatomes des groupes O, N et S, et pouvant être substitué selon la description. Les variables peuvent être substituées selon la description, et les autres variables ont les significations indiquées dans les revendications et la description. L'invention porte aussi sur des procédés et des produits intermédiaires pour réaliser ces composés, sur des agents les contenant et sur leur utilisation pour lutter contre les champignons phytopathogènes.
PCT/EP2007/052104 2006-03-07 2007-03-06 Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant WO2007101859A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP06110739 2006-03-07
EP06110739.7 2006-03-07
EP06111155 2006-03-15
EP06111155.5 2006-03-15

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008019723A1 (fr) * 2006-08-17 2008-02-21 Bayer Cropscience Ag Dérivés hétérocycliques insecticides d'acide carboxylique
WO2008046856A2 (fr) * 2006-10-18 2008-04-24 Basf Se Compositions fongicides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10223917A1 (de) * 2002-05-29 2003-12-11 Bayer Cropscience Ag Pyrazolopyrimidine
WO2005000851A1 (fr) * 2003-06-27 2005-01-06 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056558A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines utilisees comme agents fongicides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10223917A1 (de) * 2002-05-29 2003-12-11 Bayer Cropscience Ag Pyrazolopyrimidine
WO2005000851A1 (fr) * 2003-06-27 2005-01-06 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056558A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines utilisees comme agents fongicides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008019723A1 (fr) * 2006-08-17 2008-02-21 Bayer Cropscience Ag Dérivés hétérocycliques insecticides d'acide carboxylique
WO2008046856A2 (fr) * 2006-10-18 2008-04-24 Basf Se Compositions fongicides
WO2008046856A3 (fr) * 2006-10-18 2009-01-08 Basf Se Compositions fongicides

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