EP2097412A2 - DÉRIVÉS FONGICIDES DE TYPE PYRIDINIQUE N-HÉTÉROARYL CONDENSÉ ET LEUR COMPOSITIONS FONGICIDES& xA; - Google Patents

DÉRIVÉS FONGICIDES DE TYPE PYRIDINIQUE N-HÉTÉROARYL CONDENSÉ ET LEUR COMPOSITIONS FONGICIDES& xA;

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Publication number
EP2097412A2
EP2097412A2 EP07821022A EP07821022A EP2097412A2 EP 2097412 A2 EP2097412 A2 EP 2097412A2 EP 07821022 A EP07821022 A EP 07821022A EP 07821022 A EP07821022 A EP 07821022A EP 2097412 A2 EP2097412 A2 EP 2097412A2
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EP
European Patent Office
Prior art keywords
alkyl
formula
compounds
methyl
compound
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EP07821022A
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German (de)
English (en)
Inventor
Bernd Müller
Jens Renner
Egon Haden
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BASF SE
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BASF SE
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Priority to EP07821022A priority Critical patent/EP2097412A2/fr
Publication of EP2097412A2 publication Critical patent/EP2097412A2/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to compounds of the formula I.
  • R 1 can carry one, two, three or four identical or different groups R a , where R a denotes:
  • R a is halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -
  • R a in which the aliphatic, alicyclic and aromatic groups in R a may in turn be partially or completely halogenated or may carry one, two or three groups R b , R b being
  • R b is halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, amino- carbonyl, aminothiocarbonyl, Ci-C 6 -alkyl, C 6 haloalkyl, C 2 -CS- alkenyl, C2 -Ce haloalkenyl , C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, Ci-C 6 alkylthio, Ci-C 6 alkyl amino, di-C 1 -C 6 -alkylamino, formyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylsulfoxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1
  • 5- or 6-membered heterocyclyl saturated or unsaturated 5- or 6-membered heterocyclyloxy, 5- or 6-membered heteroaryl, 5- or 6-membered heteroaryloxy, 5- or 6-membered heteroarylthio, 5- or 6-membered heteroarylthio , Phenyl, naphthyl, phenoxy, naphthoxy, phenylthio, naphthylthio, phenyl-C 1 -C 6 -alkoxy, phenyl-
  • C 1 -C 6 -alkyl where the cyclic systems may be partially or completely halogenated and / or substituted by alkyl and / or haloalkyl groups;
  • R 4 can carry one, two, three, four or five identical or different groups R c , where R c denotes:
  • R c is halogen, cyano, isocyano, hydroxy, cyanato (OCN), thiocyanato, cyanato Isothio-, mercapto, Ci-C 8 alkyl, Ci-C8-haloalkyl, Ci-C8-hydroxyalkyl, Ci-8 alkoxy C -C-C 8 alkyl, C 3 -C 6 cycloalkyl-Ci-C 8 alkyl, C 2 -Cio-alkenyl, C 2 - Cio-haloalkenyl, C 2 -Cio-alkynyl, C 2 -Cio-haloalkynyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 10 -alkenyloxy, C 2 -Cio -haloalkenyloxy, C 2 -CiO-
  • Alkylthio, Ci-C8-haloalkylthio, Ci-C8-alkylsulfinyl, Ci-C8-haloalkyl sulfinyl, carboxyl-C 1 -C 5 -alkyl, phenyl, naphthyl, five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group Oxygen, nitrogen and sulfur, NR A R B , NHCOR A , NHCON R A R B , CONR A R B , -OSO 2 R A , -COR A , -CSR A , -CR A NR B or
  • N CR A R B , where R A and R B are :
  • R A , R B are independently hydrogen, Ci-Cs-alkyl, Ci-Cs haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-Al kylthio, C3-C8-cycloalkyl, C 3 -C 8- halocycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 8 alkyl, phenyl or benzyl, wherein the phenyl and benzyl groups by one, two, three, four or five groups independently selected from halogen, Ci-Cs-alkyl and C 1 -C 8 alkoxy may be substituted; Phenoxy, benzyloxy, Benzoyloxy, five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group oxygen, nitrogen and Sulfur;
  • R c can carry one, two or three identical or different groups R cL , where R cL means:
  • R cL is halogen, cyano, nitro, hydroxy, amino, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 1 -C -alkoxy, C 1 -C 8 -synyl Haloalkoxy C 2 -C 8 -alkenyloxy, C 2 -C 8 -alkynyloxy, C 3 -C -cycloalkyl, C 3 -C -hydroxycycloalkyl, C 3 -C -cycloalkenyl, C 1 -C -cycloalkyloxy, C 3 -C -cycloalkenyloxy,
  • Ce-Al oxime C2-C8 alkenyloxyimino, C2-C8 alkynyloxyimino, Ci-Cs-alkoximino-Ci-Cs-alkyl, C2-C8 alkenyloximino-Ci-C8-alkyl, C2-C8-alkynyloximino-Ci-C8 alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, C 1 -C 6 -alkylamino, C 6 -C 8 -arylalkyl, C 1 -C 8 -alkyloximino, C 2 -C 10 -alkynyl, C 2 -C 10 -alkenyloxycarbonyl, C 2 -C 10 -
  • Ci-C 8 alkyl Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, halo-C 2 -C 8 alkenyl, C2-Cs-alkynyl, Cs-Cs haloalkynyl, Ci- Cs-alkoxy, Ci-Cs-haloalkoxy;
  • R 5 may carry one, two or three identical or different groups which are independently selected from cyano, nitro, C 1 -C 2 -alkoxy and C 1 -C 4 -cycloalkyl
  • a 1 B 1 D 1 E is in each case N or CR 6 , where at least one and at most three variables denote N, and those compounds in which A, B and D are simultaneously N and E is CR 6 and those compounds in which B, D and E are N and E is CR 6 , except; where R 6 means:
  • R 8 Al 6 alkyl, hydrogen, halogen, Ci -C, C 8 alkoxy, Ci-C8-haloalkyl, Ci-C8-haloalkoxy;
  • the invention relates to the use of these compounds as fungicides, agents containing them, methods for controlling harmful fungi using the compounds I, and methods and intermediates for their preparation.
  • the invention further relates to fungicidal compositions comprising as active components fungicidal compositions for controlling plant-pathogenic harmful fungi
  • R 1 is halogen, cyano, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C 2 -Cio-alkenyl, C 2 -C 0 -
  • C 1 -C 8 -alkylamino C 1 -C 8 -alkylamino, five- or six-membered heteroaryl containing one, two, three or four heteroatoms from the group O, N and S, five- or six-membered heteroaryl-d-Cs -alkyl, wherein the heteroaryl contains one, two, three or four heteroatoms from the group O, N and S;
  • R 3 is hydrogen, NR 7 R 8 or one of the groups mentioned in R 2 ; where R 7 and R 8 are :
  • alkyl, alkenyl, alkynyl and cycloalkyl groups in R 2 and / or R may bear one, two or three identical or different groups R d 3, wherein R d is:
  • R d is halogen, cyano, hydroxy, C -C -alkyl 8 -alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkoxy,
  • alkyl, alkenyl, alkynyl and cycloalkyl groups in R d can themselves carry one, two or three identical or different groups R dL , where R dL has the meanings given for R cL ; and wherein the aryl and heteroaryl groups in R 2 and / or R 3 may in turn carry one, two or three identical or different groups R e , where R e denotes:
  • R e is halogen, hydroxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro,
  • R 2 and R 3 may also together with the nitrogen atom to which they are attached form a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two or three further heteroatoms from the group consisting of O, N and S. may contain as ring members, wherein the heterocycle may carry one, two or three identical or different groups R f , wherein R f has the meanings given for R d ;
  • R 4 is halogen, Ci-C 8 -alkyl, C 8 haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C3-C 8 - haloalkynyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy, C3-C 8 - cycloalkyl, Cs-Cs-halocycloalkyl, C 3 -C 8 cycloalkyl-Ci-C 8 alkyl, Ci-C 8 alkyl - thio, C 6 -C 4 -aryl, C 6 -C 4 -aryloxy, C 6 -C 4 -arylthio, C 6 -C 4 -aryl-C 1 -C 8 -alkyl, C 6 -C 4 -aryl-ci C 8 -alkoxy, C 6 -C 4
  • R 4 may bear one, two, three, four or five identical or different groups R c , wherein R c is as defined in claim 1;
  • R 5 is halogen, cyano, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, halo-C 2 -C 8 alkenyl, C 2 -C 8 -alkyl kinyl, C3-C 8 haloalkynyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy or Ci-C 8 alkylthio;
  • R 5 may bear one, two or three identical or different groups independently selected from halogen, cyano, nitro, C 1 -C 2 alkoxy and C 1 -C 4 alkoxycarbonyl;
  • a 1 B 1 D 1 E are each N or CR 6 , wherein at least one and at most three variables are N and those compounds wherein A, B and D are N and E is CR 6 and those compounds wherein B, D and E is N and E is CR 6 , except; where R 6 means:
  • R 8 Al 6 alkyl, hydrogen, halogen, Ci -C, C 8 alkoxy, Ci-C8-haloalkyl, Ci-C8-haloalkoxy;
  • Azoles selected from bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole,
  • Metconazole myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridizole and hymexazole;
  • strobilurins selected from azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, (2-chloro-5- [1- (3-methyl-benzyloxyimino-ethyl ] -benzyl-carbamic acid methyl ester, (2-
  • C) carboxylic acid amides selected from carboxin, benalaxyl, benodanil,
  • Boscalid fenfuram, fenhexamide, flutolanil, furametpyr, mepronil, madoreryl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro-N- (2-cyanophenylisothiazole-5-carboxylic acid amide , Dimethomorph, flumorph, flumetover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet, mandipropamide, N-
  • fungicides selected from guanidine, dodin, iminoctadine, guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A,
  • Nitrophenyl derivatives binapacryl, dinocap, dinobutone, sulfur-containing heterocyclyl compounds: dithianone, isoprothiolane, organometallic compounds: fentin salts, organophosphorus compounds: edifenphos, Iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl, organochlorine compounds:
  • Chlorothalonil Dichlofluanid, Flusulfamide, Hexachlorobenzene, Phthalide, Pencycuron, Quintozen, Thiophanate-methyl, Tolylfluanid, Inorganic agents: Bordeaux broth, Copper acetate, Copper hydroxide, Copper oxychloride, Basic copper sulfate, Sulfur, Other: Cyflufenamid, Cymoxanil, Dimethirimol, Ethirimol , Furalaxyl, Metrafenone and Spiroxamine;
  • the invention relates to a method for controlling harmful fungi with a composition of at least one compound I and at least one of the active compounds II, the use of the compound (s) I with active ingredient (s) II for the preparation of such compositions and agents and seeds containing these compositions ,
  • the object of the present invention is to provide compounds with at least comparable action, preferably improved action and / or broad spectrum of action.
  • the present invention was also based on the object of providing possibilities whereby an improved action against harmful fungi, in particular for certain indications, can be achieved with a reduced total amount of active substances applied can.
  • compositions of the active compounds I and II were found. It has also been found that it is possible to combat harmful fungi more effectively in the simultaneous, joint or separate application of at least one compound I and of at least one of the active compounds II, or the compound (s) I and at least one of the active substances II with the individual compounds alone (synergistic compositions).
  • the compounds of the formula I used as component 1), their preparation and their action against harmful fungi are known in part from the literature (cf., for example, WO 2004/056824, WO2004 / 056825, WO 2004/056826, WO 2004/056829, WO 2005 / 123698, WO 2005/123733) or in the manner described therein.
  • the action of the compounds of formula I is not always sufficient, especially at low application rates.
  • the active compounds II mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are mostly commercially available.
  • al kyl also includes octyl, decyl, Tetradecyl and hexadecyl with a cis / trans ratio of 1: 1 [CAS RN
  • Dodemorph 4-cyclododecyl-2,6-dimethylmorpholine (DE-A 1198125); Fenpropimorph, (RS) -cis-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (DE-A 27 52 096);
  • Guazatine composition of the reaction products obtained from the amidation of technical lminodi (octamethylene) diamine containing various guanidines and polyamines [CAS RN 108173-90-6];
  • Spiroxamine (8-tert-butyl-1,4-dioxaspiro [4.5] dec-2-yl) diethylamine (EP-A 281 842);
  • Tridemorph 2,6-dimethyl-4-tridecylmorpholine (DE-A 1 164 152); Pyrimethanil, 4,6-dimethylpyrimidin-2-yl-phenylamine (DD-A 151 404);
  • Cycloheximide 4 - ⁇ (2R) -2 - [(1S, 3S, 5S) -3,5-dimethyl-2-oxocyclohexyl] -2-hydroxyethyl ⁇ piperidine-2,6-dione [CAS RN 66- 81-9]; Griseofulvin, 7-chloro-2 ', 4,6-trimethoxy-6'-methylspiro [benzofuran-2 (3H), 1'-cyclohex-2' -ene] -3,4'-dione [CAS RN 126-07 -8th];
  • Penconazole 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12.
  • Prothioconazole 2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro- [1,2,4] triazole-3-thione (WO 96/16048) ;
  • Triadimenol ⁇ - (4-chlorophenoxy) - ⁇ - (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (DE-A 23 24 010); Triflumizole, (4-chloro-2-trifluoromethylphenyl) - (2-propoxy-1 - [1, 2,4] triazole-1-yl-ethylidene) -amine (JP-A 79/1 19 462);
  • Triticonazole (5E) -5 - [(4-chlorophenyl) methylene] -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (FR 26 41 277); Iprodione, 3- (3,5-dichlorophenyl) -2,4-dioxo-imidazolidine-1-carboxylic acid isopropylamide (GB
  • Metiram zinc ammonium ethylenebis (dithiocarbamate) (US 3,248,400); Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
  • Carbendazim (1 H-benzimidazol-2-yl) -carbamic acid methyl ester (US 3,657,443); Carboxin, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (US 3,249,499);
  • Cyazofamide 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamid CAS RN 120116-88-3]; Dazomet, 3,5-dimethyl-1,3,5-thiadiazinan-2-thione (Bull Soc Soc. Chim. Fr. Vol. 15, p.891
  • Furametpyr 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88-3 ]; Isoprothiolane, diisopropyl-1,3-dithiolan-2-ylidene malonate (Proc. Insectic, Fungic, Conf.
  • Tricyclazole 5-methyl-1,2,4-triazolo [3,4-b] [1,3] benzothiazole [CAS RN 41814-78-2];
  • Copper oxychloride Cu 2 Cl (OH) 3 [CAS RN 1332-40-7]; Basic copper sulfate, CuSO 4 [CAS RN 1344-73-6];
  • Ethylhexyl and 1-propylpentyl is (US 2,526,660);
  • Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
  • Penthiopyrad (RS) -N- [2- (1, 3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10/130268);
  • Phthalide (DE-A 16 43 347); Toloclofos-methyl, O-2,6-dichloro-p-tolyl O, O-dimethyl phosphorothioate (GB 14 67 561);
  • Azoxystrobin 2- ⁇ 2- [6- (2-cyano-1-vinyl-penta-1,3-dienyloxy) -pyrimidin-4-yloxy] -phenyl ⁇ -
  • Trifloxystrobin (E) -methoxyimino- ⁇ (E) - ⁇ - [1- ( ⁇ , ⁇ , ⁇ -trifluoro-m-tolyl) -ethylideneaminooxy] -o-tolyl ⁇ -acetic acid methyl ester (EP-A 460 575);
  • the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention relates to both the pure enantiomers or diastereomers or rotamers and mixtures thereof or fungicidal compositions containing the same.
  • Suitable compounds of formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds according to the invention or the compounds I used in the compositions according to the invention can be present in various crystal modifications, such compositions also being the subject of the present invention.
  • 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 action of the compounds according to the invention.
  • the ions of the alkali metals preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (Ci-C4 ) -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) -alkylsulfonium and sulfoxonium ions, preferably tri (Ci -C4) -alkylsulfoxonium, into consideration.
  • the alkali metals preferably sodium or potassium
  • the alkaline earth metals preferably calcium, magnesium or barium
  • the transition metals preferably manganes
  • Anions of advantageously usable acid addition salts are, for example, 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. They can be obtained by reaction of the compounds of the formula I according to the invention with an acid of the corresponding anion, preferably
  • Hydrochloric acid hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Substituentenmaschine stand in composite groups.
  • the meaning (C n -Cm) gives the respective possible number of carbon atoms in the respective substituent or substituent part:
  • Halogen fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having preferably 1 to 4, 6, 8, 10 or 12 carbon atoms, for example 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-ethylbuty
  • Haloalkyl alkyl as mentioned above, where in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above: in particular C 1 -C 2 -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-chloroethyl 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having preferably 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 -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-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-
  • Haloalkenyl alkenyl as mentioned above, wherein in these groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • Alkynyl straight-chain or branched hydrocarbon groups having preferably 2 to 4, 2 to 6, 2 to 8 or 3 to 10 carbon atoms and one or two triple bonds in any position, e.g. 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-hexyn
  • Cycloalkyl mono- or bicyclic saturated hydrocarbon groups having preferably 3 to 6, 3 to 8 or 3 to 10 carbon ring members, e.g. Cs-Cs-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • heterocyclyl saturated or partially unsaturated heterocycle
  • ring members e.g. monocyclic saturated or partially unsaturated heterocycles containing, in addition to carbon ring members, one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, e.g.
  • Seven-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur as ring members e.g. mono- and bicyclic heterocycles having 7 ring members, containing, in addition to carbon ring members, one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro [1 H] azepine-1, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro [2H] azepine 2-, 3-, -A-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro [1 H] azepine-1 -,
  • hexahydrooxepinyl such as 2,3,4,5-tetrahydro [1 H] oxepin-2, -3, -4, -5, -6 or -7-yl, 2,3,4, 7-tetrahydro [1 H] oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1 H] oxepin 2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, -3- or -4-yl, tetra- and
  • Aryl aromatic hydrocarbon cycles, in particular having 6 to 14, preferably 6 to 10 carbon atoms. Phenyl (C 6 H 5 -) are preferred according to the rule and naphthyl (C 0 H 7 -).
  • the compounds of the formula I according to the invention can be prepared in various ways in analogy to prior art processes known per se, such as e.g. in analogy to the syntheses specified in WO 2004/056824, WO2004 / 056825, WO 2004/056826, WO 2004/056829, WO 2005/123698, WO 2005/123733.
  • the compounds according to the invention can be prepared by the syntheses shown below:
  • the reaction is carried out under transition metal catalysis, such as Ni or Pd catalysis.
  • transition metal catalysis such as Ni or Pd catalysis.
  • R 5 is halogen
  • corresponding compounds in which R 5 is cyano, C 1 -C 8 -alkoxy or C 1 -C 8 -haloalkoxy can be prepared.
  • compounds of the formula I in which R 5 is halogen, preferably chlorine, for this purpose can be reacted with compounds A a B b .
  • a a in the compounds A a B b is a cation
  • B b is cyanide, C 1 -C 8 alkoxylate or C 1 -C 8 haloalkoxylate.
  • the compounds A a B b are an inorganic cyanide (for example KCN, NH 4 CN) or a (halo) alkoxylate.
  • the cation A a has little significance and there are such different types into consideration. For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali metal or alkaline earth metal salts are usually preferred.
  • the reaction with A a B b is preferably carried out in an inert solvent.
  • suitable solvents include ethers such as dioxane, diethyl ether, methyl tert-butyl ether and preferably tetrahydrofuran, halogenated hydrocarbons such as dichloromethane or dichloroethane, aromatic hydrocarbons such as toluene, and mixtures thereof.
  • the reaction temperature is usually 0 to 120 ° C., preferably 10 to 40 ° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • R 5 is C 1 -C 8 -alkyl, C 1 -C 9 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -alkynyl or C 3 -C 8 -haloalkynyl
  • R 5 is halogen, in particular chlorine or bromine
  • MX a organometallic compound
  • M lithium, magnesium or zinc
  • X a is Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 -C 8 - alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, or C3-C8 haloalkynyl stands to be implemented.
  • the formula I may in this way by using the corresponding compounds MX a compounds are prepared wherein R 5 is Ci-C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkynyl.
  • the reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (l) halides and especially Cu (I) iodide.
  • the reaction is preferably carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic aliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • an inert organic solvent for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic aliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • the preferred temperatures for the reaction are in the range of -100 to +100 0 C, in particular in the range of -80 0 C to + 40 ° C. Methods for this are known, for. B. from the cited prior art (see, for example,
  • 5,7-Dihalogenderivate of formula II can be obtained, for example, by the corresponding 5,7-dihydroxy derivative of formula III
  • halogenating agents are preferably phosphorus oxyhalide or phosphorus (V) halide, for example phosphorus pentachloride, phosphorus oxybromide or phosphorus oxychloride or a mixture of phosphorus oxychloride and phosphorus pentachloride. It may be advantageous to add a hydrohalide of a tertiary amine, for example triethylamine hydrochloride, as a co-catalyst.
  • the halo- halogenating reaction of compounds of formula III to give compounds of the formula II is usually carried out at temperatures of 0 0 C to 150 0 C, preferably from 80 0 C to 125 ° C [see also EP-A 770 615].
  • the reaction can be carried out in bulk or in an inert solvent, for example a halogenated hydrocarbon, such as dichloromethane, dichloroethane or an aromatic hydrocarbon, for example toluene or o-, m-, p-xylene or in a mixture of the solvents mentioned.
  • R 5 is Ci -Ce-Al kyl, Ci-C 8 - haloalkyl, C 2 -C 8 -alkenyl -alkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, or C 3 -C 8 -
  • Haloalkynyl for example, can also be prepared by reacting a halogen derivative of the formula IIa
  • R 1 is introduced (see above), where Hal is halogen, R 5 is C 1 -C 8 -alkyl, Ci-C ⁇ -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -alkynyl or C 3 -C 8 - haloalkynyl and the remaining substituents and variables that for compounds of the formula I have meanings mentioned.
  • Halogenated derivatives of formula IIa can be obtained by the corresponding
  • Halogenation is analogous to that set forth above for the reaction of compounds of formula III with a halogenating agent.
  • Hydroxy derivatives of the formula IIIa can be prepared in analogy to the methods familiar to the person skilled in the art
  • the alkaline or acidic hydrolysis of the compounds V may be advantageous.
  • decarboxylation may be added to the compounds fertilize the formula I already done in whole or in part.
  • the decarboxylation is usually carried out at temperatures from 2O 0 C to 18O 0 C, preferably 5O 0 C to 12O 0 C.
  • the decarboxylation is carried out 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-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert. Butanol, and dimethyl sulfoxide, di
  • the reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products are z.T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature from volatile constituents. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • R 1 is C 3 -C 8 alkyl, halo-C 3 -C 8 alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 - Alkynyl, C 3 -C 8 -haloalkynyl, C 3 -C 6 -cycloalkyl (especially C 8 -C 6 -cycloalkyl), C 1 -C 6 -halocycloalkyl, C 6 -C 6 -cyclo-alkenyl or C 1 -C 6 -halocyclo-alkenyl, where R 1 can carry one, two, three or four identical or different groups R a .
  • R 1 is also C 1 -C 8 -alkyl or C 1 -C 8 -haloalkyl. Also preferably, R 1 is C 2 -C 10 alkenyl or C 2 -C 10 alkynyl. Each R 1 may be substituted by R a as defined herein.
  • R 1 is an unsubstituted or substituted by R a as defined herein, a five- or six-membered saturated carbon-bonded heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur.
  • R 1 is an unsubstituted or substituted by R a , as defined herein, a five- or six-membered partially unsaturated carbon-bonded heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur.
  • R 1 is an unsubstituted or substituted by R a , as defined herein, a five- or six-membered aromatic carbon-bonded heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur.
  • R 1 is C 3 -C 6 -cycloalkyl which may be substituted by R a as defined herein, and more particularly by C 1 -C 4 -alkyl.
  • R a is according to one embodiment are each independently halogen, cyano, -C 6 - alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkyl kinyl, Ci-C 6 alkoxy, Ci-C 6 alkoxycarbonyl, CrC 6 - alkoximino, C2-C6 -Alkenyloximino or C 2 -C 6 -alkyl kinyloximino.
  • R a is independently chlorine, fluorine or bromine, cyano, Ci-C4-alkyl, in particular methyl, ethyl, n-propyl and / or iso-propyl, or Ci-C 6 alkoxy, in particular Methoxy, ethoxy, n-propoxy and / or iso-propoxy.
  • R a may be substituted by R b .
  • R b in a preferred embodiment is in each case independently halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy.
  • R 4 is C 6 -C 4 aryl, preferably phenyl or naphthyl, each of which is unsubstituted or substituted by R c , as defined herein.
  • R 4 is phenyl which has at least one substituent R c .
  • R 4 is phenyl which has at least two substituents R c .
  • at least one substituent R c is in ortho position to the linking site of R 4 with the skeleton of the formula I.
  • R 4 is a substituted phenyl group P
  • # is the point of attachment to the skeleton of the formula I and L 1 is fluorine, chlorine, CH 3 or CF 3 ;
  • L 2 , L 4 are independently hydrogen, fluorine or methoxy;
  • L 3 is hydrogen, fluorine, chlorine, CN, CH 3 , OCH 3 , NH 2 , NHCH 3 , N (CH 2 ) 2 , C (O) NH 2 ,
  • L 5 is hydrogen, fluorine, chlorine or CH 3 .
  • R 4 is one of the following substituents: 2-fluoro-6-chlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro-6-methylphenyl, 2,4 , 6-trifluorophenyl, 2,6-difluoro-4-methoxyphenyl, 2-chloro-4-methoxyphenyl, pentafluorophenyl, 2-methyl-4-fluorophenyl, 2-trifluoromethylphenyl, 2-methoxy-6-fluorophenyl, 2-chlorophenyl , 2-fluorophenyl, 2,4-difluorophenyl, 2-fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2,3-difluorophenyl, 2,5-difluorophenyl, 2,3 , 4-Trifluorophenyl, 2-fluoro
  • R 4 is phenyl which is unsubstituted or substituted with one, two or three substituents R c independently selected from fluoro, chloro, bromo, cyano, nitro, formyl, methyl, ethyl, n -propyl, i -propyl , n-butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, methoxy, ethoxy, n-propoxy, i-propoxy, methylthio, ethylthio, n-propylthio, i-propylthio, methylsulfinyl, ethylsulfinyl , Methylsulfonyl, ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluo
  • R 4 is phenyl which contains one, two or three substituents in 2, 4 and / or 6-position which are independently selected from the R c mentioned herein as preferred, in particular independently selected from fluorine and chlorine.
  • R 4 is 2,4-, 2,5- or 2,6-disubstituted phenyl, 2-substituted phenyl or 2,4,6-trisubstituted phenyl, with substituents R c , which are independently selected are from the group fluorine, chlorine, bromine, cyano, nitro, OH, mercapto, methyl, ethyl, methoxy, methylthio, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and carboxymethyl.
  • R 4 is 2-trifluoromethylphenyl, 2-chloro-5-nitrophenyl or 2-chloro-4-methoxyphenyl.
  • R 4 is a five- or six-membered aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S.
  • R 4 is an unsubstituted or substituted 5- or 6-membered aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S.
  • the heteroaromatic can each (also in the following described embodiments) via a ring carbon atom or via a ring nitrogen atom to the skeleton of Be bound to formula I.
  • R c is independently selected from the meanings of R c given above unless otherwise specified.
  • R 4 contains at least one ring nitrogen atom. It may be preferred that the binding site of R 4 to the backbone of formula I is in the ortho-position to the at least one nitrogen atom.
  • R 4 is an unsubstituted or substituted 5-membered heteroaromatic radical containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur, wherein R 4 is unsubstituted or substituted by one, two , three or four identical or different substituents R c .
  • the five-membered heteroaromatic radical is nitrogen-containing.
  • the optionally substituted five-membered hetero- roaryl radical may be bonded to the skeleton of the formula I via a ring carbon atom or via a ring nitrogen atom.
  • the heteroaryl (R 4 ) has at least one substituent which is in the ortho position to the point of attachment to the skeleton of the formula I to which R 4 is attached. It may be particularly preferred for the ortho-R c to be fluorine, chlorine, ( C 1 -C 2) -alkyl, such as methyl or ethyl, C 1 -C 2 -fluoroalkyl, such as trifluoroalkyl or C 1 -C 2 -alkoxy, such as methoxy.
  • R c is bonded to a ring nitrogen of R 4 , it is particularly preferred that R c is each independently:
  • Ci-Cs-alkylcarbonyl Ci-Cs-alkylthiocarbonyl
  • d-Cs-alkyl Ci-C ⁇ -haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C3-C8-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halogenocycloalkyl, C3-Cs-cycloalkenyl, Cs-Cs-halocycloalkenyl, C 1 -Cs-alkoximinoalkyl, C 2 -C 8 -alkenyloximino- (C 1 -C 8) -alkyl or C 2 -C 8 -alkynyloximino-C 1 -C 8 -cycloalkyl alkyl.
  • R c is particularly preferably C 1 -C 6 -alkyl or C 1 -C 6 -halogenoalkyl, more preferably C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, in particular methyl or ethyl, particularly preferably methyl.
  • R c when it is bonded to a ring nitrogen of R 4 , in each case particularly preferably C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, -COO (C 1 -C 4 ), -CONH 2 or -CSNH 2 , in particular methyl, ethyl, isopropyl, cyclopropyl or -COOCH 3.
  • R c is bonded to a ring carbon of R 4 , R c is preferably each independently:
  • Ci-Cs-alkylcarbonyl Ci-Cs-alkylthiocarbonyl
  • Ci-C6-alkylamino di-Ci-C6-alkylamino
  • Ci-Cs-haloalkoxy Ci-Cs-alkenyloxy, d-Cs-haloalkenyloxy, d-Cs-alkynyloxy, d-Cs-haloalkynyloxy, Ci-Cs-cycloalkoxy, Ci-Cs-Halogencycloalkoxy; or
  • R 4 may contain one to four, one to three, or one or two identical or different substituents R c .
  • R 4 contains the same substituents R c .
  • Particularly preferably R 4 contains one or two substituents R c , particularly preferably one or two identical substituents R c .
  • R 4 preferably has two identical substituents R c .
  • R 4 is thiazolyl, imidazolyl, pyrazolyl, 1,2,4-triazolyl or 1,2,3-triazolyl and especially pyrazol-1-yl, where the abovementioned radicals are unsubstituted or 1 , 2 or 3 substituents R c .
  • R 4 is in particular one of the radicals Het-1 to Het-31 given below:
  • L 1 , L 2 , and L 3 independently of one another represent hydrogen or have one of the meanings mentioned for R c .
  • the radicals L 1 , L 2 and L 3 are independently selected from hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, especially C 1 -C 2 -fluoroalkyl, C 1 -C 4 -alkoxy and
  • L 1 , L 2 and L 3 are independently selected from hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-1 are 3,5-dimethylpyrazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropyl-pyrazol-1-yl, 3-isopropyl-5-methyl-pyrazole 1-yl, 3-ethyl-5-methyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-methyl-pyrazole-1 yl, 3-methyl-4-chloro-pyrazol-1-yl, 3-trifluoromethylpyrazol-1-yl, 3-trifluoromethyl-5-methoxypyrazol-1-yl, 3-trifluoromethyl-5-methyl-pyrazole 1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dichloro-4-methyl-pyrazol-1-yl, 3,5-dimethyl-4-chloro-pyrazol-1-yl, 3, 5-Ditrifluoromethyl-pyrazo
  • Het-3 are 1, 5-dimethylpyrazol-3-yl and 1-methyl-5-methoxypyrazol-3-yl.
  • Het-4 examples include 1, 3-dimethylpyrazol-4-yl, 1, 5-dimethylpyrazol-4-yl, 1, 3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl and 1-methyl-5-trifluoromethylpyrazol-4-yl.
  • Het-5 are 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl and 1-methyl-3,5- dichloropyrrole-2-yl.
  • Het-6 are 1, 4-dimethylpyrazol-3-yl and 1-methylpyrazol-3-yl.
  • Het-7 examples include thiazol-4-yl, 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl and 2,5-dichloro-thiazol-4-yl.
  • Het-8 is thiazol-2-yl.
  • Het-9 is thiazol-5-yl.
  • Het-10 examples include 3-methyl-isothiazol-4-yl and 3-methyl-5-chloro-isothiazol-4-yl.
  • Het-1 1 is isothiazol-3-yl.
  • het-12 is isothiazol-5-yl.
  • het-13 examples include isoxazol-4-yl, 3,5-dimethylisoxazol-4-yl, 3-methylisoxazole and 3-chloro-isoxazol-4-yl,
  • Het-14 is isoxazol-3-yl.
  • Het-15 is isoxazol-5-yl.
  • Het-16 examples include oxazol-4-yl, 2-methyl-oxazol-4-yl and 2,5-dimethyloxazol-4-yl,
  • Het-17 is oxazol-2-yl.
  • Het-18 is oxazol-5-yl.
  • Het-19 include 4,5-dichloro-imidazol-1-yl and 4,5-dimethyl-imidazol-1-yl.
  • Het-20 is 1-methyl-imidazol-4-yl.
  • Het-21 is 1-methylimidazol-2-yl.
  • Het-22 is 1-methylimidazol-5-yl.
  • Examples of het-23 include 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3-bromo-1, 2,4-triazole 1 -yl, 3-trifluoromethyl-1, 2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dichloro-1, 2,4- triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl and 3,5-ditrifluoromethyl-1, 2,4-triazol-1-yl.
  • Het-24 examples include 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1, 2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazol-1-yl, 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl, 5-methyl 1, 2,3-triazol-1-yl, 5-chloro-1, 2,3-triazol-1-yl, 5-fluoro-1, 2,3-triazol-1-yl, 5-bromo-1, 2,3-triazol-1-yl, 5-trifluoromethyl-1,2,3-triazol-1-yl.
  • Het-25 is 1,2,3-triazol-2-yl.
  • Het-26 is 1-methyl-1,2,4-triazol-5-yl.
  • Het-27 is 1-methyl-1,2,3-triazol-5-yl.
  • Het-28 is 2-methyl-1,2,3-triazol-4-yl.
  • Het-29 is 1-methyl-1,2,4-triazol-3-yl.
  • Het-30 is 1-methyl-1,2,3-triazol-4-yl.
  • Het-31 is 2-methyl-1,2,3-triazol-5-yl.
  • R 4 is thienyl which is unsubstituted or has 1, 2 or 3 substituents R c . Accordingly, R 4 is one of the following residues Het-32 or Het-33, wherein # denotes the attachment site and L 1 , L 2 , and L 3 independently of one another have the meanings previously given for the formulas Het-1 to Het-31.
  • Het-32 examples are 2-thienyl, 5-methylthiophene-2-yl, 5-chlorothiophene-2-yl, 5-bromothiophene-2-yl, 3,5-dichlorothiophene-2-yl, 3,4,5- Trichlorothiophen-2-yl and 5-bromothiophen-2-yl.
  • Het-33 examples are 3-thienyl, 2-methylthiophen-3-yl, 2,5-dichlorothiophene-3-yl, 2,4,5-trichloro-thiophen-3-yl and 2,5-dibromothiophene-3 yl.
  • a further embodiment of the invention relates to compounds of the formula I in which R 4 is 1,2,3-triazolyl or 1,2,4-triazolyl, where R 4 may have two identical or different substituents R c .
  • R 4 Preferred embodiments of these R 4 are 3,5-dimethyl-1, 2,4-triazol-1-yl, 3,5-dichloro-1, 2,4-triazol-1-yl, 3,5-dibromo-1 , 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl, 3,5-di- (trifluoromethyl) -1, 2,4-triazol-1-yl , 3-methyl-1, 2,4-triazol-1-yl, 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3 bromo-1, 2,4-triazol-1-yl, 3-trifluoromethyl-1,2,4-triazol-1-yl, 4,5-dimethyl-1,2,3-triazol-1-yl, 4 , 5-dichloro-1, 2,3-triazol-1-yl, 4,5-dibromo-1,2,3-
  • R 4 is a five-membered nitrogen-containing heteroaromatic ring selected from pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl and isothiazolyl, wherein R 4 is unsubstituted or substituted with one, two, three or four same or different substituents R c .
  • R 4 here is unsubstituted or substituted pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl or isothiazolyl.
  • R 4 is optionally substituted pyrrolyl, preferably via a ring carbon bonded to the skeleton of the formula I pyrrolyl, ie 2-, or 3-pyrrolyl, particularly preferably 2-pyrrolyl.
  • the pyrrolyl radical has one, two, three or four substituents R c .
  • R 4 is optionally substituted pyrazolyl, such as 1-, 3-, 4- or 5-pyrazolyl. More preferably, R 4 is 1-pyrazolyl or 4-pyrazolyl, more preferably 1-pyrazolyl.
  • the pyrazolyl radical has one, two or three substituents R c .
  • R 4 is optionally substituted imidazolyl, that is 1-, 2-, or 4-imidazolyl, more preferably 1- or 2-imidazolyl.
  • the imidazolyl radical has one, two or three substituents R c .
  • R 4 Preferred substitution patterns of R 4 are as indicated in the following Table A, wherein L 1 , L 2 and L 3 within a heteroaromatic R 4 are each identical or different R c , which are as defined above:
  • # means in each case the point of attachment of the respective R 4 with the skeleton of the compounds of the formula I or with the precursors thereof.
  • L 1 , L 2 , L 3 each independently have the meanings given herein for R c .
  • R 4 is pyrrolyl
  • a substitution pattern selected from A-1, A-2, A-3, A-4 and A-5, especially selected from A-2 and A-4 shown in Table A is particularly preferred.
  • R 4 is pyrazolyl
  • a substitution pattern is selected from A-7, A-8, A-10, A-1 1, A-13, A-14, A-15, A-16 and A-19.
  • R 4 is imidazolyl
  • a substitution pattern is selected from A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29 and A-30 in particular selected from A-22, A-23, A-24, A-25 and A-27, A-28, and A-29.
  • R 4 is oxazolyl
  • a substitution pattern selected from A-36 and A-37 is particularly preferred.
  • R 4 isoxazolyl
  • a substitution pattern selected from A-39, A-40 and A-41 is particularly preferable.
  • R 4 is thiazolyl
  • a substitution pattern selected from A-44 and A-45 is particularly preferred.
  • R 4 is isothiazolyl a substitution pattern selected from A-46 and A-47 is particularly preferable.
  • R 4 are: 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl, 1-methyl-3,5-dichloropyrrol-2-yl , 3-methyl-5-isopropylpyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 3-isopropyl-5-methylpyrazol-1-yl, 3-ethyl-5-methylpyrazol-1-yl, 3 -Methyl-5-methoxypyrazol-1-yl, 3,4,5-trimethylpyrazol-1-yl, 3,5-dimethyl-4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 3,4-dichloro -5-trichloromethylpyrazol-1-yl, 3-methylpyrazol-1-yl, 3,5-dichloro-4-methylpyrazol-1-yl, 3-methyl-4-chloropyrazol-1-yl, 1, 3-d
  • R 4 is a five-membered teroaryl group containing two nitrogen atoms as ring members, which is selected from 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,5-thiadiazolyl, 1, 2,4-oxadiazolyl, 1, 3,4-oxadiazolyl and 1, 2,5-oxadiazolyl, wherein R 4 may be unsubstituted or substituted with one or two R c , wherein R c is as above is defined, or preferably defined.
  • R 4 Specific meanings for such R 4 are: 1, 3,4-thiadiazol-2-yl, 5-methyl- [1, 3,4] thiadiazol-2-yl, 5-chloro [1, 3,4 ] -thiadiazol-2-yl, 5-bromo [1, 3,4] thiadiazol-2-yl, 1, 2,3-thiadiazol-4-yl, 5-methyl- [1, 2,3 ] -thiadiazol-4-yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1,2,3] thiadiazol-4-yl, 1,2,3 Thiadiazol-5-yl, 4-methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1,2,3] thiadiazol-5-yl, 4-bromo [1,2,5 , 3] -thiadiazol-5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl- [1, 2,4] thiadiazol-5-yl, 3-chloro [1, 2,4 ] -
  • R 4 is unsubstituted.
  • R 4 has one, two, three or four, preferably one or two, identical or different substituents R c .
  • An embodiment of this embodiment of the invention relates to compounds of the formula I in which R 4 is a 6-membered heteroaromatic radical which has 1, 2 or 3 nitrogen atoms as ring members and is unsubstituted or 1, 2, 3 or 4, preferably 1, 2 or 3 substituents R c carries.
  • R 4 is preferably pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, (1, 2,4-triazinyl or 1, 3,5-triazinyl), in particular pyridinyl, pyrimidinyl or pyrazinyl.
  • R 4 is selected from pyridinyl, pyridazinyl, pyrazinyl, 1, 2,4-triazinyl and 1, 3,5-triazinyl.
  • R 4 is pyrimidyl.
  • the R 4 are unsubstituted or carry 1, 2, 3 or 4 independently selected substituents R c .
  • R 4 is pyridinyl, optionally having 1, 2, 3 or 4 substituents R c .
  • R 4 is 2-pyridinyl which has 1 or 2 substituents R c .
  • those compounds are particularly preferred in which one of the substituents R c is located in the 5-position of the pyridinyl ring.
  • most preferred are compounds I wherein one of the substituents R c is located in the 3-position of the pyridinyl ring.
  • R c has in particular the meanings given as preferred.
  • Also preferred compounds of this embodiment are compounds of formula I wherein R 4 is 3-pyridinyl, optionally having 1 or 2 substituents R c .
  • R 4 is 3-pyridinyl, optionally having 1 or 2 substituents R c .
  • preference is given to those compounds which have a substituent R c in the 2-position and / or a substituent R c in the 4-position of the pyridine ring.
  • R 4 is 4-pyridinyl, which optionally has 1 or 2 substituents R c .
  • preference is given to those compounds which have a substituent R c in the 3-position and / or a substituent R c in the 5-position of the pyridine ring.
  • R 4 is pyrimidinyl and in particular 2- or 4-pyrimidinyl which optionally has 1, 2 or 3 substituents R c .
  • R 4 is 2-pyrimidinyl or 4-pyrimidinyl, which has 1 or 2 substituents R c .
  • R c has in particular those specified as preferred Meanings.
  • a further preferred embodiment of the invention relates to compounds of the formula I in which R 4 is 2-pyrazinyl which optionally has 1, 2 or 3 substituents R c .
  • a further preferred embodiment of the invention relates to compounds of the formula I in which R 4 is 3-pyridazinyl which optionally has 1, 2 or 3 substituents R c .
  • a further preferred embodiment of the invention relates to compounds of the formula I in which R 4 is 1,3,5-triazinyl which optionally has 1 or 2 substituents R c .
  • heterocyclic radicals R 4 of this embodiment are the radicals Het-34 to Het-39 given below:
  • L 1 , L 2 , L 3 and L 4 independently of one another are hydrogen or have one of the meanings mentioned for R c .
  • the radicals L 1 , L 2 , L 3 and L 4 are independently selected from among hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, especially C 1 -C 2 -fluoroalkyl, C 1 -C 4 -Aikoxy and C 1 -C 4 -alkoxycarbonyl.
  • L 1 , L 2 , L 3 and L 4 are independently selected from hydrogen, nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-34 examples are 2-pyridyl, 3-fluoropyridin-2-yl, 3-chloropyridin-2-yl, 3-bromo-2-pyridin-2-yl, 3-trifluoromethylpyridine-2-yl yl, 3-methylpyridin-2-yl, 3-ethyl-pyridin-2-yl 3,5-difluoropyridin-2-yl, 3,5-dichloro-pyridin-2-yl, 3,5-dibromo -pyridin-2-yl, 3-fluoro-5-trifluoromethylpyridin-2-yl, 3,5-dimethyl-pyridin-2-yl, 5-nitro-pyridin-2-yl, 5-cyano pyridin-2-yl, 5-methoxycarbonylpyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 5-methylpyridin-2-yl, 4-methylpyridin-2-yl, and 6-methyl pyridin-2-yl.
  • Het-35 examples are 3-pyridyl, 2-chloro-pyridin-3-yl, 2-bromo-pyridin-2-yl, 2-methyl-pyridin-3-yl, 2,4-dichloro-pyridine-3 yl, 2,4-dibromopyridin-3-yl, 2,4-dimethyl-pyridin-3-yl, 2,4,6-trichloropyridin-3-yl, 2,4,6-tribromopyridin-3-yl, 2,4,6-trimethylpyridin-3-yl and 2,4-dichloro-6-methylpyridin-3-yl.
  • Het-36 examples include 4-pyridyl, 3-chloro-pyridin-4-yl, 3-bromo-pyridin-4-yl, 3-methyl-pyridin-4-yl, 3,5-dichloro-pyridine-4 yl, 3,5-dibromo-pyridin-4-yl and 3,5-dimethyl-pyridin-4-yl
  • Het-37 examples include 5-chloropyrimidin-4-yl, 5-fluoropyrimidin-4-yl, 5-fluoro-6-chloropyrimidin-4-yl, 2-methyl-6-trifluoromethyl-pyrimidin-4-yl, 2, 5-Dimethyl-6-trifluoromethyl-pyrimidin-4-yl, 5-methyl-6-trifluoromethyl-pyrimidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl, 2-methyl-5-fluoro-pyrimidine-4 yl, 2-methyl-5-chloro-pyrimidin-4-yl, 5-chloro-6-methyl-pyrimidin-4-yl, 5-chloro-6-ethyl-pyrimidin-4-yl, 5-chloro-6 isopropyl-pyrimidin-4-yl, 5-bromo-6-methyl-pyrimidin-4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethyl-pyrimidin-4-y
  • het-38 examples include 4-methyl-pyrimidin-5-yl, 4,6-dimethyl-pyrimidin-5-yl, 2,4,6-trimethyl-pyrimidin-5-yl and 4-trifluoromethyl-6-methyl-pyrimidine 5-yl.
  • Het-39 examples include 4,6-dimethylpyrimidin-2-yl, 4,5,6-trimethylpyrimidin-2-yl, 4,6-ditrifluoromethyl-pyrimidin-2-yl and 4,6-dimethyl-5-chloro pyrimidin-2-yl.
  • R 5 is C 1 -C 4 -alkyl, in particular methyl, ethyl, isopropyl or n-propyl. In a specific embodiment, R 5 is methyl.
  • R 5 is C 1 -C 4 -haloalkyl, in particular halomethyl.
  • R 5 is halogen, in particular chlorine or fluorine.
  • compounds of the formula I are preferred in which E is N and A, B and D are as previously defined.
  • at least two of the variables A, B, D and E represent N.
  • two of the variables represent N.
  • three of the variables are N.
  • R 6 in the Verbindunden of formula I each independently is preferably hydrogen, halogen, Ci-C 4 -alkyl, -C 4 -alkoxy, Ci-C 4 haloalkyl, or -C 4 - haloalkoxy, in particular hydrogen, halo or Ci-C 4 - alkyl. According to a preferred embodiment, all R 6 are hydrogen.
  • linkages Id are preferred
  • all R 6 are each hydrogen, these compounds are also referred to herein as compounds of formula Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If.1.
  • the compounds of the formula I used as component 1), their preparation and their action against harmful fungi are, as stated above, partly known from the literature (cf., for example, WO 2004/056824, WO 2004/056826, WO 2004 / 056829, WO 2005/123698, WO 2005/123733) or in the manner described therein.
  • the active compounds II mentioned above as component 2), their preparation and their action against harmful fungi are generally known and largely commercially available (see above).
  • the compounds I can be used as synergists for a variety of different fungicidal agents.
  • the fungicidal activity is increased to a superadditive extent.
  • component 1) used is in particular compounds of the formula I in which the substituents have the meanings already described above for the compounds of the formula I according to the invention. Further embodiments of the compositions according to the invention are set forth below:
  • components 1) used are compounds of the formula I in which R 1 denotes NR 2 R 3 , where R 2 and R 3 are as previously defined.
  • R 2 represents Ci -Ce-Al kyl, Ci-C 8 - -alkenyl haloalkyl, C 2 -C 8 -alkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C 3 -C 8 -
  • R 3 is hydrogen, NR 7 R 8 or one of the groups mentioned in R 2 ; where R 7 and R 8 independently of one another represent hydrogen or one of the meanings mentioned for R 2 .
  • the alkyl, alkenyl, alkynyl and cycloalkyl groups in R 2 and / or R 3 can in turn carry one, two or three identical or different groups R d , where R d is each independently selected from halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl, C 1 -C 5 -haloalkoxy, ci C 1 -C 6 -alkylcarbonyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkylthio, tri-C 1 -C 6 -alkylsilyl, C 1 -C 8 -alkylamino and C 1 -C 8 -alkylamino.
  • R d is each independently selected from halogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl, C 1 -C 5 -haloalkoxy,
  • R 2 Ci-C 8 alkyl, C 8 - haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 haloalkenyl, C 3 -C 8 cycloalkyl, C 3 - C 8 - halocycloalkyl or C 3 -C 8 -cycloalkyl-Ci-C 8 -alkyl.
  • R 3 is hydrogen, or one of the groups mentioned in R 2 .
  • neither R 2 nor R 3 is hydrogen, wherein R 2 and R 3 are preferably independently selected from C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl , Cs-C ⁇ -cycloalkyl and Cs-C ⁇ -halogeno-cycloalkyl, in particular selected from Ci-C6-alkyl and Ci-C6-haloalkyl.
  • R 2 is as previously defined or preferably defined and R 3 is hydrogen.
  • R 2 and R 3 may each independently, one, two or three identical or different groups R d carry.
  • R d is as defined previously, and preferably in each case independently halogen, cyano, Ci-d-alkyl, dd-haloalkyl, C1-C4 alkoxy or haloalkoxy dd.
  • component 1) comprises compounds of the formula I in which R 2 is a group B:
  • Z 1 is hydrogen, fluorine or dd-fluoroalkyl
  • Z 2 is hydrogen or fluorine, or Z 1 and Z 2 together form a double bond
  • q is 0 or 1
  • R 9 is hydrogen or methyl. In a specific embodiment of this embodiment, R 3 is hydrogen.
  • R 3 in the compounds of the formula I is hydrogen and R 2 is Cs-C ⁇ -cycloalkyl which may be substituted by C 1-6 -alkyl.
  • R 2 and R 3 together with the nitrogen atom to which they are attached form a five- or six-membered saturated or partially unsaturated heterocycle containing one or two further heteroatoms from the group O, N and S may contain as ring members, which heterocycle may carry one, two or three identical or different groups R f as defined above.
  • R f is independently selected from halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy.
  • R f is preferably each independently selected from C 1 -C 6 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C -alkoxy and C 1 -C -haloalkoxy.
  • R 2 and R 3 together with the nitrogen atom to which they are attached form a piperidinyl, morpholinyl or thiomorpholinyl ring which is optionally substituted by one, two or three identical or different R f groups a piperidinyl ring.
  • the heterocycle formed is unsubstituted or substituted by one, two or three R f , wherein each R f is independently selected from halo, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.
  • R f is independently selected from halo, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.
  • R 2 and R 3 together with the nitrogen atom to which they are attached are a 4-methylpiperidine ring, a 4-trifluoromethylpiperidine ring, a morpholine ring or a 3,4-dimethylpiperidine ring and especially a 4-methylpiperidine ring or form a 3,4-dimethylpiperidine ring.
  • compositions of the invention are used in particular as component 1) compounds, wherein R 5 has the meanings given above.
  • R 5 in the compounds of the formula I is halogen, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl.
  • R 5 is C 1 -C 4 -alkyl, such as methyl, ethyl or n-propyl.
  • R 5 is C 1 -C 4 -haloalkyl, such as, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl.
  • a further embodiment relates to fungicidal compositions in which R 5 in the compounds of the formula I is halogen, in particular chlorine.
  • R 5 in the compounds of the formula I is C 1 -C 8 -alkoxy, preferably C 1 -C 4 -alkoxy, in particular methoxy or ethoxy. Furthermore, R 5 is preferably C 1 -C 8 -haloalkoxy, preferably C 1 -C 4 -haloalkoxy.
  • R 5 in the compounds of the formula I is cyano.
  • the components 1) used are compounds of the formula Ia, as illustrated above. According to one embodiment of this embodiment, compounds of the formula Ia.1 are used as component 1), as described above.
  • compositions according to the invention are used as component 1) compounds of formula Ib, as shown above.
  • compounds of the formula Ib.1 are used as component 1), as described above.
  • the components 1) used are compounds of the formula Ic, as illustrated above. According to one embodiment of this embodiment, compounds of the formula Ic.1 are used as component 1), as described above.
  • compositions according to the invention are used as component 1) compounds of the formula Id, as shown above.
  • compounds of formula Id.1 are used as component 1), as described above.
  • the components 1) used are compounds of the formula Ie, as illustrated above. According to one embodiment of this embodiment, compounds of the formula Ie.1 are used as component 1), as described above.
  • compositions according to the invention are used as component 1) compounds of the formula If, as shown above.
  • compounds of the formula lf.1 are used as component 1), as described above.
  • the substituents in the compounds used as component 1) in the compositions according to the invention Ia, Ib, Ic, Id, Ie, If or Ia.1, Ib.1, Ic.1, Id.1, Ie.1, If.1 in each case have the meanings as indicated elsewhere herein for the corresponding substituent according to the compounds according to the invention or for component 1) in the compositions according to the invention.
  • the component 1) corresponds to a compound of the formula Ia-1, in which R 6 is in each case hydrogen (compounds Ia.1-1).
  • component 1) corresponds to a compound of formula Ib-1:
  • the component 1) corresponds to a compound of the formula Ib-1, in which R 6 is in each case hydrogen (compounds Ib.1-1).
  • component 1) corresponds to a compound of formula Ic-1:
  • the component 1) corresponds to a compound of the formula Ic-1, in which R 6 is in each case hydrogen (compounds Ic.1-1).
  • the component 1) corresponds to a compound of the formula I-1:
  • the component 1) corresponds to a compound of the formula Id-1, in which R 6 is in each case hydrogen (compounds Id.1-1).
  • the component 1) corresponds to a compound of the formula le-1, wherein R 6 is in each case hydrogen (compounds Ie.1-1).
  • compound of the formula If-1 corresponds to:
  • the component 1) corresponds to a compound of the formula If-1, in which R 6 is in each case hydrogen (compounds 1 to 1).
  • the compounds I compiled in the following Tables 1 to 110 are preferably used in the compositions according to the invention. Regardless of the combination in which they are mentioned, the groups mentioned in the tables for a substituent also individually represent a particularly preferred embodiment of the substituent in question for a compound of the formula I. Those in these Tables 1 to 110 in combination with lines B-150 to B-157 and B-307 to B-314 of Table B individualized compounds further represent preferred compounds of the invention and are also the subject of the present invention.
  • Fluoropyrid-2-yl and the combination of R 1 and R 5 for each compound corresponds to one line of Table B corresponds to Table 23
  • Fluoropyrid-4-yl and the combination of R 1 and R 5 for each compound corresponds to one line of Table B corresponds to Table 25
  • Trifluoropyrid-3-yl and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Trifluoromethylpyrid-3-yl and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Table 44 Compounds of the formulas Ia.1, Ib.1, Ic.1, Id.1, Ie.1 and If. 1, in which R 4 is 2-fluoro-4-trifluoromethylpyrid-3-yl and the combination of R 1 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Fluorothien-2-yl and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Trifluorophenyl means and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Trifluorophenyl means and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Table 74 Compounds of the formulas Ia.1, Ib.1, Ic.1, Id.1, I.1 and If.1 in which R 4 is 2-chloro-4-fluorophenyl and the combination of R 1 and R 5 for a connection corresponds in each case to one row of Table B.
  • Dimethylphenyl means and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Dichlorophenyl means and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table B.
  • Table 104 Compounds of the formulas Ia.1, Ib.1, Ic.1, Id.1, Ie.1 and If.1 in which R 4 is 2-chloro-5-methoxyphenyl and the combination of R 1 and R 5 for a connection corresponds in each case to one row of Table B.
  • compositions of a compound of the formula I with at least one active substance selected from the group of A) azoles preference is given to compositions of a compound of the formula I with at least one active substance selected from the group of A) azoles.
  • the invention relates to compositions comprising one of the compounds of the formula I individualized in Tables 1 to 110 and at least one active compound selected from the group of A) azoles
  • compositions of a compound of the formula Ia with at least one active substance selected from the group of A) azoles are also preferred according to the present invention. Also preferred according to the present invention are compositions of a compound of the formula Ia.1 with at least one active substance selected from the group of A) azoles. Also preferred according to the present invention are compositions of a compound of the formula Ia-1 with at least one active substance selected from the group of A) azoles. Also preferred according to the present invention are compositions of a compound of the formula Ia.1-1 with at least one active substance selected from the group of A) azoles.
  • compositions of a compound of the formula Ib with at least one active substance selected from the group of A) azoles are also preferred according to the present invention. Also preferred according to the present invention are compositions of a compound of the formula Ib.1 with at least one active compound selected from the group of A) azoles. Also preferred according to the present invention are compositions of a compound of formula Ib-1 with at least one active ingredient selected from the group of A) azoles. Also preferred according to the present invention are compositions of a compound of formula Ib.1-1 with at least one active ingredient selected from the group of A) azoles.
  • compositions of a compound of the formula Ic with at least one active substance selected from the group of A) azoles are also preferred according to the present invention.
  • compositions of a compound of the formula Ic-1 with at least one active ingredient selected from the group of A) azoles are also preferred according to the present invention.
  • compositions of a compound of the formula Id with at least one active substance selected from the group of A) azoles are also preferred according to the present invention.
  • compositions of a compound of the formula Id-1 with at least one active ingredient selected from the group of A) azoles are also preferred according to the present invention.
  • compositions of a compound of the formula Ie with at least one active ingredient selected from the group of A) azoles are also preferred according to the present invention.
  • compositions of a compound of formula le-1 with at least one active ingredient selected from the group of A) azoles are also preferred according to the present invention.
  • compositions of a compound of the formula If with at least one active substance selected from the group of A) azoles are also preferred according to the present invention. Also preferred according to the present invention are compositions of a compound of the formula If.1 with at least one active substance selected from the group of A) azoles. Also preferred according to the present invention are compositions of a compound of the formula If-1 with at least one active ingredient selected from the group of A) azoles. Also preferred according to the present invention are compositions of a compound of formula If.1 -1 with at least one active ingredient selected from the group of A) azoles.
  • compositions of a compound of the formula I having at least one active ingredient selected from the group of B) strobilurins Preference is also given to compositions of a compound of the formula I having at least one active ingredient selected from the group of B) strobilurins.
  • the invention relates to compositions comprising one of the compounds of the formula I individualized in Tables 1 to 10 and at least one active compound selected from the group of B) strobilurins.
  • compositions of a compound of the formula Ia with at least one active compound selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Ia-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • Compositions of a compound of the formula Ia.1-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of formula Ib with at least one active ingredient selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Ib.1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • Compositions of a compound of the formula Ib.1-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Ic with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • Compositions of a compound of the formula Ic.1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • Also preferred according to the present invention are compositions of a compound of formula Ic-1 with at least one active ingredient selected from the group of B) strobilurins.
  • compositions of a compound of the formula Ic.1-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Id with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Id.1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • Compositions of a compound of the formula Id.1-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Ie with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Ie.1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula le-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula Ie.1-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula If.1 with at least one active ingredient selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of the formula If.1-1 with at least one active substance selected from the group of B) strobilurins are also preferred according to the present invention.
  • compositions of a compound of formula I with at least one active ingredient selected from the group of C) carboxylic acid amides are preferred.
  • the invention relates to compositions comprising one of the individualized in the tables 1 to 1 10 compounds of formula I and at least one active ingredient selected from the group of C) carboxylic acid amides.
  • compositions of a compound of the formula Ia.1 with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Ib with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Ib.1-1 with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Ic with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Ic.1 with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Ic.1-1 with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Id with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Id.1-1 with at least one active substance selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Id.1-1 with at least one active substance selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula Ie with at least one active substance selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula If with at least one active ingredient selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of the formula If.1 with at least one active compound selected from the group of C) carboxylic acid amides are also preferred according to the present invention.
  • compositions of a compound of formula I with at least one active ingredient selected from the group of D) heterocyclic compounds are also preferred.
  • the invention relates to compositions comprising one of the compounds of the formula I individualized in Tables 1 to 110 and at least one active compound selected from the group of the D) heterocyclic compounds.
  • compositions of a compound of the formula Ia.1 with at least one active compound selected from the group of D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula Ia-1 with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula Ib with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred.
  • compositions of a compound of the formula Ib-1 with at least one active substance selected from the group of the D) heterocyclic compounds are also preferred.
  • compositions of a compound of the formula Ib.1-1 with at least one active substance selected from the group of the D) heterocyclic compounds are also preferred.
  • compositions of a compound of the formula Ic with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula Id with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula Id.1 with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula Id.1-1 with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula Ie with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula If with at least one active substance selected from the group of D) Heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of the formula If.1 with at least one active compound selected from the group of the D) heterocyclic compounds are also preferred according to the present invention.
  • compositions of a compound of formula I with at least one active ingredient selected from the group of E) carbamates are also preferred.
  • the invention relates to compositions comprising one of the individualized in the tables 1 to 1 10 compounds of formula I and at least one active ingredient selected from the group of E) carbamates.
  • compositions of a compound of the formula Ia.1 with at least one active substance selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of formula Ia-1 with at least one active ingredient selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula Ia.1-1 with at least one active substance selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of formula Ia-1 with at least one active ingredient selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of formula Ia-1 with at least one active substance selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of formula Ia-1 with at least one active ingredient selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of formula Ib with at least one active ingredient selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula Ib.1 with at least one active compound selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula Ic with at least one active substance selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula Ic.1 with at least one active substance selected from the group of E) carbamates are also preferred according to the present invention.
  • substance selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula Id with at least one active compound selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula Id.1 with at least one active compound selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula Id.1-1 with at least one active compound selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of formula Ie with at least one active ingredient selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of the formula If with at least one active ingredient selected from the group of E) carbamates are also preferred according to the present invention.
  • compositions of a compound of formula I with at least one active ingredient selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula Ia.1 with at least one active compound selected from the group of F) Other fungicides are also preferred according to the present invention.
  • compositions of a compound of formula Ia-1 with at least one active ingredient selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of formula Ib with at least one active ingredient selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula Ib.1 with at least one active compound selected from the group of F) other fungicides are also preferred according to the present invention.
  • Compositions of a compound of the formula Ib.1-1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula Ic with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • Compositions of a compound of the formula Ic.1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • Compositions of a compound of the formula Ic-1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula Ic.1-1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula Id with at least one active compound selected from the group of F) Other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula I-1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound fertil the formula Id.1-1 with at least one active ingredient selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula Ie with at least one active substance selected from the group of F) Other fungicides are also preferred according to the present invention.
  • compositions of a compound of formula Ie.1 with at least one active ingredient selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula Ie.1-1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula If having at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • Compositions of a compound of the formula If.1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • Compositions of a compound of the formula III with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • Compositions of a compound of the formula If.1-1 with at least one active substance selected from the group of F) other fungicides are also preferred according to the present invention.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le .1-1 or If.1-1, with at least one active substance selected from the group of A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, Triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz,
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • azoles selected from cyazofamide, metconazole, fluquiconazole, triadimefon, triadimenol, penconazole, hexaconazole and thiabendazole, in particular selected from penconazole, hexaconazole and thiabendazole.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • azoles selected from epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If.1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le .1-1 or lf.1-1, with at least one active ingredient selected from the group of A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, propiconazole, prochloraz, prothioconazole and tebuconazole, in particular selected from cyproconazole, difenoconazole and propiconazole.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • strobilurins selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le .1-1 or lf.1-1, with at least one active ingredient selected from the group of B) strobilurins selected from kresoxim-methyl, orysastrobin and pyraclostrobin.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If.1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1- 1, le.1-1 or lf.1-1, with pyraclostrobin.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • strobilurins selected from azoxystrobin, fluoxastrobin, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin, in particular selected from azoxystrobin and picoxystrobin.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • carboxylic acid amides selected from fenhexamide, metalaxyl, mefenoxam, ofurace, dimethomorph, fluoromide, fluopicolide (picobenzamide), zoxamide, carpropamide and mandipropamide.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If.1, in particular - la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1 , le.1-1 or lf.1-1, with at least one active ingredient selected from the group of C) carboxylic acid amides selected from fenhexamide, metalaxyl, mefenoxam, ofurace, dimethomorph, zoxamide and carpropamide.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le .1-1 or lf.1-1, with at least one active ingredient selected from the group of C) carboxylic acid amides selected from fenhexamide and oxadixyl.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • heterocyclic compounds selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, Iprodione, vinclozolin, famoxadone, fenamidone, probenazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1, 5-a] pyrimidine, Proquinazid, Acbenzolar S-methyl, Captafol, Folpet, Fenoxanil and Quinoxyfen, especially Fluazi nampro, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenprop
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le .1-1 or If.1-1, with at least one active ingredient selected from the group of D) heterocyclic compounds selected from tridemorph, iprodione, pyrimethanil, fenpropimorph, fenpropidin, acibenzolar-S-methyl and pyrifenox, in particular selected from Fenpropimorph, fenpropidin, acibenzolar-S-methyl and pyrifenox.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If.1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le .1-1 or If.1-1, with at least one active compound selected from the group consisting of D) heterocyclic compounds selected from pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozoline, 5-chloro-7- (4- methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine and quinoxyfen, especially pyrimethanil, dodemorph,
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.
  • At least one active compound selected from the group consisting of D) heterocyclic compounds selected from fludioxonil, cyprodinil and 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1, 5-a] pyrimidine, in particular selected from fludioxonil and cyprodinil.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le. 1-1 or lf.1-1, with at least one active ingredient selected from the group consisting of E) carbamates, selected from Mancozeb, Metiram, Propineb, Thiram, Iprovalicarb, Flubenthiavalicarb and Propamocarb.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If.1, in particular - la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1 , le.1-1 or If.1-1, with at least one active ingredient selected from the group of E) carbamates selected from mancozeb and metiram.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If.1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le.1-1 or lf.1-1, with at least one active ingredient selected from the group of E) carbamates selected from iprovalicarb and metiram, preferably iprovalicarb.
  • compositions of a compound of formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le. 1-1 or lf.1-1, with at least one active ingredient selected from the group of F)
  • Other fungicides selected from chlorothalonil, fosetyl, fosetyl-aluminum, metrafenone and spiroxamine.
  • compositions of a compound of the formula I in particular Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or If1, in particular la-1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le .1-1 or lf.1-1, with at least one active substance selected from the group of F) other fungicides selected from phosphorous acid and its salts, chlorthalonil and metrafenone.
  • triple compositions of a compound of formula I especially Ia, Ib, Ic, Id, Ie or If, especially Ia.1, Ib.1, Ic.1, Id.1, Ie.1 or lf.1, in particular la -1, lb-1, lc-1, ld-1, le-1 or lf-1, especially la.1-1, lb.1-1, lc.1-1, Id.1-1, le. 1-1 or lf.1- 1, with two of the above mentioned or preferred as preferred active ingredients II.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is difenoconazole.
  • component 2) is difenoconazole.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is prochloraz.
  • Table M-5 Fungicidal compositions in which component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is prochloraz.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is epoxiconazole.
  • component 2) is epoxiconazole.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is azo-xystrobin.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is picoxystrobin.
  • component 2) is picoxystrobin.
  • Fungicidal compositions in which component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is fluorotastrobin.
  • Fungicidal compositions in which component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is trifloxystrobin.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is oryastrobin.
  • component 2) is oryastrobin.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is pyracoltrobin.
  • Table M-14 is pyracoltrobin.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is metaxaxyl.
  • component 2) is metaxaxyl.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is dipropamide.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is fluopidide.
  • component 1) is one of the compounds of formula I listed in Tables 1 to 11 and component 2) is bosca-
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is dimomorphic.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro 4-fluoro-biphenyl-2-yl) amide.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro 5-fluoro-biphenyl-2-yl) amide.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is 3-difluoromethyl-1-methyl-1H-pyrazole-1-carboxylic acid-1-bicyclopropyl-1-phenylphenoxyamide.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is cyprindinil.
  • component 1) is one of those listed in Tables 1 to 1 10 compounds of formula I and component 2) is Fludio xonil.
  • Table M-24 is
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 11 and component 2) 5
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is isopropavalentb.
  • Table M-26 isopropavalentb.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is chlorothalonil.
  • component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is Foseyl-Al.
  • component 2) is Foseyl-Al.
  • Fungicidal compositions in which component 1) is one of the compounds of the formula I mentioned in Tables 1 to 110 and component 2) is spiro-amine.
  • Fungicidal compositions in which component 1) is one of the compounds of the formula I mentioned in Tables 1 to 10 and component 2) is metaphfene.
  • fungicidal compositions described in the following Tables Z-1 to Z-29:
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is propiconazole.
  • component 2) is propiconazole.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is cyproconazole.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is difenoconazole.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is prochloraz.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is prothioconazole.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is tebuconazole.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is epoxiconazole.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is azoxystrobin.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is picoxystrobin.
  • component 2) is picoxystrobin.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is fluoxastrobin.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is trifloxystrobin.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is orysastrobin.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is pyraclostrobin.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is metalaxyl.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is mandipropamide.
  • component 2) is mandipropamide.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is fluopicolide.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is boscalid.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is dimethomorphic.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4' -dichloro 4-fluoro-biphenyl-2-yl) amide.
  • component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4' -dichloro 4-fluoro-biphenyl-2-yl) amide.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4' -dichloro 5-fluoro-biphenyl-2-yl) amide.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2) bicyclopropyl-2-yl-phenyl) amide.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is cyprodinil.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is fludioxonil.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is iprovalicarb.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is chlorothalonil.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is spiroxamine.
  • component 1) is one of the compounds C-1 to C-348 listed in Table C and component 2) is metrafenone.

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Abstract

L'invention concerne des composés de formule (I) et leur utilisation pour combattre des champignons phytopathogènes, ainsi que des mélanges fongicides contenant un composé de formule (I), les variables et substituants possédant les significations définies dans les revendications et la description.
EP07821022A 2006-10-06 2007-10-08 DÉRIVÉS FONGICIDES DE TYPE PYRIDINIQUE N-HÉTÉROARYL CONDENSÉ ET LEUR COMPOSITIONS FONGICIDES& xA; Withdrawn EP2097412A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07821022A EP2097412A2 (fr) 2006-10-06 2007-10-08 DÉRIVÉS FONGICIDES DE TYPE PYRIDINIQUE N-HÉTÉROARYL CONDENSÉ ET LEUR COMPOSITIONS FONGICIDES& xA;

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP06121914 2006-10-06
EP06122244 2006-10-13
EP07821022A EP2097412A2 (fr) 2006-10-06 2007-10-08 DÉRIVÉS FONGICIDES DE TYPE PYRIDINIQUE N-HÉTÉROARYL CONDENSÉ ET LEUR COMPOSITIONS FONGICIDES& xA;
PCT/EP2007/060649 WO2008040820A2 (fr) 2006-10-06 2007-10-08 Composés fongicides et compositions fongicides

Publications (1)

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EP2097412A2 true EP2097412A2 (fr) 2009-09-09

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EP07821022A Withdrawn EP2097412A2 (fr) 2006-10-06 2007-10-08 DÉRIVÉS FONGICIDES DE TYPE PYRIDINIQUE N-HÉTÉROARYL CONDENSÉ ET LEUR COMPOSITIONS FONGICIDES& xA;

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US (1) US20100093738A1 (fr)
EP (1) EP2097412A2 (fr)
JP (1) JP2010505799A (fr)
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WO (1) WO2008040820A2 (fr)

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WO2008040820A3 (fr) 2008-06-26
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WO2008040820A2 (fr) 2008-04-10

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