EP1786795A2 - Biphenyl thiazole carboxamides - Google Patents

Biphenyl thiazole carboxamides

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Publication number
EP1786795A2
EP1786795A2 EP05771671A EP05771671A EP1786795A2 EP 1786795 A2 EP1786795 A2 EP 1786795A2 EP 05771671 A EP05771671 A EP 05771671A EP 05771671 A EP05771671 A EP 05771671A EP 1786795 A2 EP1786795 A2 EP 1786795A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
carbonyl
alkoxy
formula
chlorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05771671A
Other languages
German (de)
French (fr)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Jörg Nico GREUL
Benoit Hartmann
Herbert Gayer
Thomas Seitz
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1786795A2 publication Critical patent/EP1786795A2/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the present invention relates to novel Biphenylthiazolcarboxamide, several processes for their preparation and their use for controlling unwanted microorganisms.
  • the effectiveness of these substances is good, but in some cases, eg to be desired at low application rates.
  • R 1 is hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) amino, cyano, C 1 -C 4 -
  • R 2 represents halogen
  • C] -C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 3 is hydrogen, C 1 -C 8 -AIkV-, C r C 6 alkylsulfinyl, C, -C 6 alkylsulfonyl, Ci-C 4 -alkoxy-C r C 4 - alkyl, C 3 -C 8 cycloalkyl ; C r C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4 haloalkyl sulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -halogeno-cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C] -C 3 - alkyl, (CRCS AlkyOcarbonyl-C-Cj-alkyl, (C, -C 3
  • R 4 is halogen, C r C 4 alkyl, C r C 4 alkoxy, C r is C 4 -alkylthio or C r C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, m represents 1 or 2, where R 4 may be the same or different when m is 2,
  • R 5 represents halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, C r C 8 alkyl, C 2 -C 6 alkenyl, C, -C 8 alkoxy, C 2 -C 6 - Alkenyloxy, C, -C 8 alkylthio, C 1 -C 8 -
  • R 7 and R 8 are each independently hydrogen, C r C 8 alkyl, Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 cycloalkyl; , Halo-C r C 4 are C r C 8 haloalkyl alkoxy-Ci-C4-alkyl, halo-C 3 -C 8 cycloalkyl with in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 7 and R 8 together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms, which is optionally mono- or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl Heterocycle may contain 1 or 2 further, nonadjacent heteroatoms from the series oxygen, sulfur or NR 11 ,
  • R 9 and R 10 are independently hydrogen, Ci-Cg-alkyl, C 3 -Cs-cycloalkyl; Ci-Q-haloalkyl, C 3 -C 8 -halogencycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 9 and R 10 together with the nitrogen atom to which they are attached additionally form a saturated heterocycle having 5 to 8 ring atoms, which is optionally mono- or polysubstituted, identically or differently, by halogen or C 1 -C 4 -alkyl, where the hetero ⁇ cyclus can contain 1 or 2 further non-adjacent heteroatoms from the series oxygen, sulfur or NR 11 ,
  • R 1 ' is hydrogen or QQ-alkyl, with the exception of compounds of the formula (I) in which R 1 is hydrogen or methyl,
  • R 2 is chlorine, methyl, difluoromethyl or trifluoromethyl
  • C r C 4 alkoxy or C r C 4 alkylthio is, when R 3 is hydrogen and R 4 m is 1 and represents fluorine.
  • biphenylthiazolecarboxamides of the formula (1) are obtained by reacting (a) carboxylic acid derivatives of the formula (II)
  • R 1 and R 2 have the meanings given above and X 1 is halogen or hydroxy, with biphenylamines of the formula (HI)
  • R 3 , R 4 , m and R 5 have the abovementioned meanings, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
  • R 1 , R 2 , R 3 , R 4 and m have the meanings given above, X 2 is bromine, iodine or trifluoromethylsulfonate, with boronic acid derivatives of the formula (V)
  • G 1 and G 2 are each hydrogen or together are tetramethylethylene, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or (c) boronic acid derivatives of the formula (VT)
  • R 1 , R 2 , R 3 , R 4 and m have the meanings given above, G 3 and G 4 are each hydrogen or together are tetramethylethylene, with phenyl derivatives of the formula (VII)
  • R 5 has the abovementioned meanings and X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or (d) halocarboxamides of the formula (TV)
  • X 2 is bromine, iodine or trifluoromethylsulfonate, with phenyl derivatives of the formula (VII)
  • R 5 has the abovementioned meanings and X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate, in the presence of a palladium or nickel catalyst and in the presence of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-l, 3,2-dioxaborolane, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or (e) biphenylthiazolecarboxamides of the formula (Ia)
  • R 1 , R 2 , R 4 , m and R 5 have the meanings given above, with halides of the formula (VHI)
  • R 3A represents C r C 8 alkyl, C r C 6 alkylsulfinyl, C, -C 6 alkylsulfonyl, C r C 4 alkoxy-C, -C 4 -AL- alkyl, C 3 -C 8 cycloalkyl; C r C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4-halo-alkylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 -
  • Halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-Ci-Cs-alkyl, (Ci-C 3 alkyl) carbonyl-Ci-C 3 alkyl, (C, -C 3 -alkoxy) carbonyl-Ci- C3 alkyl; Halo (Ci-C 3 alkyl) carbonyl-Ci-C 3 alkyl, halo (Ci-C 3 alkoxy) carbonyl-C] -C 3 alkyl each having 1 to 13 fluorine, chlorine and / or bromine atoms; (CRCG-alkyl) carbonyl, (C r C 8 alkoxy) carbonyl, (Ci-C 4 alkoxy-C, -C 4 alkyl) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl; (Ci-C ⁇ -HalogenalkyOcarbonyl, (C
  • X 4 is chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
  • the novel biphenylthiazolecarboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials.
  • the compounds according to the invention can be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms are claimed.
  • the Biphenylthiazolcarboxamide invention are generally defined by the formula (T). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of the formula (I) as well as to all intermediate products.
  • R 1 preferably represents hydrogen, fluorine, chlorine, bromine, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, cyano, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 Fluorine, chlorine and / or bromine atoms.
  • R 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
  • R 1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
  • R 1 particularly preferably represents amino, methylamino, dimethylamino, chlorine, methyl or
  • R 2 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5
  • R 2 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, 1-fluoroethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 2 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 2 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
  • R 3 preferably represents hydrogen, C r C 6 alkyl, C, -C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C, -C 3 - alkoxy-Ci-Cs-alkyl, C 3 -C 6 cycloalkyl , C, -C 4 haloalkyl, C r C 4 haloalkylthio, C r C 4 -Ha- logenalkylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C 3 alkoxy-Ci-C 3 alkyl, C 3 - C 8 - halogenocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl C r C 3 alkyl, (C, -C 3 -alkyl) carbonyl-C, -C r alkyl,
  • R 3 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfmyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, Trichloromethyl, trifluoroethyl,
  • R 4 is preferably fluorine, with fluorine being particularly preferably in the 3- or 5-position, very particularly preferably in the 5-position of the respective compound [cf. eg formula (I)].
  • R 4 is preferably chlorine, with chlorine being particularly preferably in the 4- or 5-position, very particularly preferably in the 4-position, moreover very particularly preferably in the 5-position of the respective compound.
  • R 4 furthermore preferably represents trifluoromethyl, trifluoromethyl being particularly preferably in
  • R 4 furthermore preferably represents methoxy or methylthio, with methoxy or methylthio being particularly preferably in the 3- or 5-position, very particularly preferably in the 5-position of the respective compound.
  • R 4 furthermore preferably represents methyl, where methyl is particularly preferably in the 4- or 5-position, very particularly preferably in the 4-position of the respective compound.
  • R 4 is also preferably isopropyl, with isopropyl being particularly preferred in 4- or 5-
  • n is preferably 1. m is furthermore preferably 2, where the radicals R 4 may be identical or different.
  • R 5 is preferably fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, vinyl, allyl, methoxy , Ethoxy, n- or iso-propoxy, vinyloxy, allyloxy, methylthio, ethylthio, n- or iso-propylthio, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, methoxymethyl , Methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethyl
  • R 5 is particularly preferably fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, methylthio, ethylthio , n- or iso-Propylthio, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, methoxymethyl, methylthiomethyl, methylamino, ethylamino, iso-propylamino, dimethylamino, diethylamino, diisopropylamino, methylcarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylcarbonylamino, cyclopropyl, trifluoromethyl Trifluoroethyl, difluoromethoxy
  • R 5 most preferably represents fluoro, chloro, bromo, methyl, iso-propyl, tert-butyl, methoxy, iso-propoxy, methylthio, iso-propylthio, methoxymethyl, methylthiomethyl, methylamino, dimethylamino, methylaminocarbonyl, methylcarbonylamino, cyclopropyl, trifluoromethyl , Trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio or
  • R 5 particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy.
  • R 6 preferably represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; Alkyl C r C 4 haloalkyl, C r C 4 haloalkoxy, halo-Ci-Cs-alkoxy-Ci-Cs, Cs-C ⁇ -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 6 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
  • R 7 and R 8 independently of one another preferably represent hydrogen, C 1 -C 6 -alkyl, C 1 -C 3 -alkoxy-C r C 3 -alkyl, C 3 -C 6 -cycloalkyl; C r C 4 -haloalkyl, haloC r C 3 -alkoxy-C, C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 7 and R 8 also form, together with the nitrogen atom to which they are bonded, preferably a saturated heterocycle having 5 or 6 ring atoms optionally monosubstituted to monosubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the hetero cyclus may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 11 .
  • R 7 and R 8 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl,
  • R 7 and R 8 also together with the nitrogen atom to which they are attached, more preferably form an optionally mono- to di-quadratic, identical or different, by fluorine,
  • R 9 and R 10 independently of one another preferably represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl; CpGi-haloalkyl, C 3 -C 6 -halo cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 9 and R 10 together with the nitrogen atom to which they are attached preferably also form an optionally monosubstituted to quadruple, identical or different, by halogen or
  • Heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the series oxygen, sulfur or NR 11 .
  • R 9 and R 10 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
  • R 9 and R 10 also together with the nitrogen atom to which they are attached, more preferably form an optionally monosubstituted to quadruple, identical or different, by fluorine, Chloro, bromo or methyl substituted saturated heterocycle from the series morpholine, thiomorpholine or piperazine, wherein the piperazine may be substituted on the second nitrogen atom by R 11 .
  • R 11 is preferably hydrogen or C r C 4 alkyl.
  • R 11 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • R 2 is chlorine, methyl, difluoromethyl or trifluoromethyl
  • R 5 is fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, iso-propoxy or methylthio, when R 3 is hydrogen and R 4 is fluorine and m is 1.
  • R 1 , R 2 , R 4 , m and R 5 have the meanings given above.
  • Group 2 biphenylthiazolecarboxamides of the formula (Ib) in which R 1 , R 2 , R 3A , R 4 , m and R 5 have the meanings given above.
  • R 3A is preferably C r C 6 alkyl, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, Ci-C 3 alkoxy-C r C 3 alkyl, C 3 -C 6 cycloalkyl; C r C 4 haloalkyl, Ci-C4-haloalkylthio, C, -C 4 -Halogenal- kylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C 3 alkoxy-Ci-C 3 alkyl, C 3 - C 8 -halo-cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 3 - alkyl, (C r C 3 alkyl) carbonyl-Ci-C 3 alkyl, (C r C 3 alkoxy) carbonyl-C
  • R 3A particularly preferably represents methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso- , sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, Trichloromethyl, trifluoroethyl
  • R 1 , R 2 , R 3 , R 4 , m and R 5 have the meanings given above.
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above.
  • R 1 , R 2 , R 3 and R 5 have the meanings given above and R 4A and R 4B independently of one another have the meanings of R 4 .
  • R 4 is chlorine, bromine, C r C 4 alkyl, C 1 -C 4 alkoxy, C, -C 4 alkylthio or C r C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • dialkylamino also includes an unsymmetrically alkyl-substituted amino group, such as e.g. Methyl ethylamino.
  • Halogen substituted radicals e.g. Haloalkyl
  • Halogen substituted radicals are halogenated singly or multiply.
  • the halogen atoms may be the same or different.
  • Halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • process (a) according to the invention can be replaced by the following Formula Scheme to be illustrated:
  • the carboxylic acid derivatives required for carrying out the process (a) according to the invention as starting materials are generally defined by the formula (II).
  • R 1 and R 2 are preferred, particularly preferred and very particularly preferred meanings, the formula already mentioned in connection with the description of the inventive compounds (I) as being preferred, particularly preferred and very particularly preferably these residues were indicated.
  • X 1 is preferably chlorine, bromine or hydroxyl.
  • the carboxylic acid derivatives of the formula (II) are known and / or can be prepared by known processes (cf., WO 03/066609, WO 03/066610, EP-A 0 545 099, EP-A 0 589 301, EP-A A 0 589 313 and US 3,547,917).
  • the biphenylamines which are furthermore required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (III).
  • R 3, R 4, m and R 5 are preferred, particularly preferred and very particularly preferably have those meanings already mentioned in connection with the description of the compounds of formula (I) according to the invention for these radicals or this Index as preferred, particularly preferred or very particularly preferred.
  • the biphenylamines of the formula (HI) are known in some cases or can be obtained by known processes (cf., for example, WO 03/070705, WO 99/09013, WO 97/08148, JP 2001-302605).
  • halo-carboxamides required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (IV).
  • R 1, R 2, R 3, R 4 and m have preferred, particularly preferred and very particularly preferably those Bedeutun ⁇ gene corresponding to the formula already mentioned in connection with the description of the inventive compounds (I) as preferred, particularly preferred or very particularly preferred for these radicals or this index.
  • X 2 is bromine or iodine.
  • Halogencarboxamide of formula (FV) are not yet known. They are also the subject of the present application as novel chemical compounds. They are obtained by reacting (f) carboxylic acid derivatives of the formula (IT)
  • R 3 , R 4 , m and X 2 have the meanings given above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
  • haloanilines which are furthermore required as starting materials for carrying out the process (f) according to the invention are generally defined by the formula (DC).
  • R 3, R 4, m and X 2 being preferred, particularly preferred and very particularly preferably have those meanings Be ⁇ , the gene already in connection with the description of the inventive Verbindun ⁇ of formula (I) or the precursors of the formula (IV) have been indicated as being preferred, particularly preferred or very particularly preferred for these radicals or this index.
  • haloanilines of the formula (IX) are commercially available synthetic chemicals or can be obtained by known methods.
  • the boronic acid derivatives which are furthermore required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (V).
  • R 5 has preferably, more preferably or very particularly preferably those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) as being preferred, particularly preferred or very particularly preferred for this radical were.
  • G 1 and G 2 are each hydrogen or together are tetramethylethylene.
  • the boronic acid derivatives of the formula (V) are known and / or can be prepared by known processes (cf., for example, WO 01/90084, JP-A 2001-302605 and US Pat. No. 5,633,218).
  • Boron ⁇ acid derivatives are generally defined by the formula (VT).
  • R 1, R 2, R 3, R 4 and m have preferred, particularly preferred and very particularly preferably have those meanings already mentioned in connection with the description of the compounds of formula (I) as being preferred according to the invention, particularly preferred or very particularly preferred for these radicals or this index.
  • G 3 and G 4 are each hydrogen or together are tetra methylethylene.
  • the boronic acid derivatives of the formula (VI) are not yet known. They are new chemical compounds and are also the subject of the present application. They are obtained by reacting (g) a carboxylic acid derivative of the formula (IT)
  • R 3 , R 4 , m, G 3 and G 4 have the meanings given above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
  • the anilinboronic acid derivatives furthermore required for carrying out the process (g) according to the invention as starting materials are generally defined by the formula (X).
  • R 3, R 4 and m have preferred, particularly preferred and very particularly preferably have those meanings Be ⁇ , the gene already in connection with the description of Verbindun ⁇ invention of the formula (I) as being preferred, particularly preferably or very particularly preferably for these radicals or this index.
  • G 3 and G 4 are each hydrogen or together are tetramethylethylene.
  • aniline boronic acid derivatives of the formula (X) are known synthetic chemicals or can be obtained by known methods.
  • R 5 vorzugt be ⁇ particularly preferred and very particularly preferably have those meanings which have undergone working in connection with the description of erfuidungswashen compounds of formula (I) as Preferably, particularly preferred or very particularly preferred for this remainder.
  • X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate.
  • the phenyl derivatives of the formula (VII) are known synthetic chemicals.
  • the 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-l, 3,2-dioxaborolane furthermore required for carrying out the process (d) according to the invention is a commercially available one chemical for synthesis.
  • the biphenyl-thiazolecarboxamides required as starting materials for carrying out the process (e) according to the invention are generally defined by the formula (Ia).
  • R 1, R 2, R 4, R 5 and n are preferred, particularly preferred and very particularly preferred are those loading meanings which have already been stated in connection with the description of the compounds according to the invention of the formula (I) as being preferred, particularly preferred or very particularly preferred for these radicals or this index.
  • the compounds of the formula (I-a) are compounds according to the invention and can be prepared by the processes (a) to (d).
  • halides which are furthermore required as starting materials for carrying out the process (e) according to the invention are generally defined by the formula (VHT).
  • R 3A is preferred, particularly preferably or very particularly preferably for those meanings which have already been indicated above for the compounds of the formula (Ib) as being preferred, particularly preferred or very particularly preferred for this radical
  • X 4 is chlorine, bromine or iodine.
  • Suitable diluents for carrying out the processes (a), (f) and (g) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as e.g. Petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g.
  • Chlorobenzene dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole
  • Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; their mixture
  • the processes (a), (f) and (g) according to the invention are carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor all customary inorganic or organic bases are suitable.
  • These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, for example sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide , Sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, Pyridine, N-methylpiperidine, N-methylmorpholine, N, N-
  • the processes (a), (f) and (g) according to the invention are carried out in the presence of a catalyst.
  • a catalyst examples which may be mentioned are 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.
  • reaction temperatures can be varied within a substantial range when carrying out the processes (a), (f) and (g) according to the invention. In general, one works at temperatures of 0 0 C to 150 0 C, preferably at temperatures of 0 0 C to 80 0 C.
  • Suitable diluents for carrying out the processes (b), (c) and (d) according to the invention are all inert organic solvents. These include preferably aliphatic, alicyclic see or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N 5 N-dimethylformamide, N, N-dimethylacetamide,
  • reaction temperatures can be varied within a substantial range when carrying out the processes (b), (c) and (d) according to the invention. In general, one works at temperatures of 0 0 C to 180 0 C, preferably at temperatures of 20 0 C to 150 0 C.
  • the processes (b), (c) and (d) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor As such, all customary inorganic or organic bases are suitable. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, fluorides, phosphates, carbonates or hydrogencarbonates, such as, for example, Sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium phosphate, potassium phosphate, potassium fluoride, cesium fluoride, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline,
  • a catalyst e.g. a palladium salt or complex.
  • a catalyst e.g. a palladium salt or complex.
  • a catalyst e.g. a palladium salt or complex.
  • a catalyst e.g. a palladium salt or complex.
  • a catalyst e.g. a palladium salt or complex.
  • a palladium complex can also be produced in the reaction mixture if a palladium salt and a complex ligand, such as, for example, triethylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, 2- (dicyclohexylphosphine) -biphenyl, 2- (di-tert-butylphosphane) -biphenyl, 2- (dicyclohexylphosphine) -2 '- (N, N-dimethylamino) biphenyl, triphenylphosphine, tris (o-tolyl) phosphane, sodium 3- (diphenylphosphino) benzenesulfonate, tris-2- ( Methoxyphenyl) phosphane, 2,2'-bis (diphenyl) nylphosphane) - 1, 1'-binaphthyl, 1, 4-bis (
  • process (d) for preparing the compounds of the formula (I), in general from 0.8 to 15 mol, preferably from 0.8 to 8 mol, of phenyl derivative of the formula are employed per mole of the halocarboxamide of the formula (IV) (VE) and 0.8 to 15 mol, preferably 0.8 to 8 mol of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis- l, 3,2-dioxaborolane.
  • Suitable diluents for carrying out the process (e) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, e.g. Petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g.
  • Chlorobenzene dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N- Dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
  • Ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethan
  • the process (e) according to the invention is carried out in the presence of a base.
  • a base As such, all customary inorganic or organic bases are suitable. These are preferably
  • hydrogencarbonates e.g. Sodium hydride, sodium amide, sodium methoxide, sodium ethoxide,
  • Potassium tert-butoxide sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines, such as trimethylamine,
  • DABCO diazabicyclooctane
  • DBN diazabicyclo- nonene
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out the process (e) according to the invention. In general, one works at temperatures of 0 0 C to 150 0 C, preferably at temperatures of 20 0 C to 110 0 C.
  • the substances according to the invention have a strong microbicidal activity and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae,
  • Xanthomonas species e.g. Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species e.g. Pseudomonas syringae pv. Lachrymans; Erwinia species, e.g. Erwinia amylovora;
  • Pythium species e.g. Pythium ultimum
  • Phytophthora species e.g. Phytophthora infestans
  • Pseudoperonospora species such as e.g. Pseudoperonospora humuli or
  • Plasmopara species e.g. Plasmopara viticola
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Erysiphe species e.g. Erysiphe graminis
  • Sphaerotheca species e.g. Sphaerotheca fuliginea
  • Podosphaera species e.g. Podosphaera leucotricha
  • Venturia species e.g. Venturia inaequalis
  • Pyrenophora species e.g. Pyrenophora teres or P. graminea
  • Cochliobolus species e.g. Cochliobolus sativus
  • Drechslera Syn: Helminthosporium
  • Uromyces species e.g. Uromyces appendiculatus
  • Puccinia species e.g. Puccinia recondita
  • Sclerotinia species e.g. Sclerotinia sclerotiorum
  • Tilletia species e.g. Tilletia caries
  • Ustilago species e.g. Ustilago nuda or Ustilago avenae
  • Pellicularia species e.g. Pellicularia sasaku
  • Pyricularia species e.g. Pyricularia oryzae
  • Fusarium species e.g. Fusarium culmorum
  • Botrytis species e.g. Botrytis cinerea
  • Septoria species e.g. Septoria nodorum
  • Leptosphaeria species e.g. Leptosphaeria nodorum
  • Leptosphaeria nodorum e.g. Leptosphaeria nodorum
  • Cercospora species e.g. Cercospora canescens
  • Alternaria species such as e.g. Alternaria brassicae;
  • Pseudocercosporella species e.g. Pseudocercosporella herpotrichoides
  • Rhizoctonia species e.g. Rhizoctonia solani.
  • the active compounds according to the invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against infestation by unwanted
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
  • Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to plants within a certain period of time after treatment to protect against infestation by said pathogens.
  • the period within which protection is provided generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
  • the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
  • the active compounds according to the invention can be used with particularly good success for controlling cereal diseases, such as, for example, against Puccinia species and diseases in the wine, fruit and vegetable growing, such. against Botrytis, Venturia or Alternaria species.
  • the active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the active compounds according to the invention may optionally also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant variety rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment.
  • treatment methods eg by dipping, spraying, vaporizing, atomizing, spreading, brushing and in the case of propagation material, in particular in the case of seeds, furthermore by single-layer or multi-layer coating.
  • the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • technical materials which are to be protected against microbial change or destruction by active compounds according to the invention are adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which infest or decompose microorganisms can be.
  • materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms.
  • technical materials which may be mentioned are preferably adhesives, glues, paper and cardboard, leather, wood, paint, cooling lubricants and heat transfer liquids, particularly preferably wood.
  • the active compounds according to the invention act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera There may be mentioned, for example, microorganisms of the following genera:
  • Alternaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
  • Chaetomium such as Chaetomium globosum
  • Coniophora like Coniophora puetana,
  • Lentinus like Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in seed coating compositions, as well as ULV -KaIt- and warm mist formulations.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents.
  • water e.g. also organic solvents can be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: e.g. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: e.g.
  • Suitable emulsifiers and / or foam-forming agents are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates.
  • Suitable dispersants are: e.g. Lignin-Sulf ⁇ tablaugen and methylcellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • dyes such as inorganic pigments, such as iron oxide, titanium oxide, and Ferrocyanblau organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance.
  • synergistic effects i. E. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Fungicides 2-phenylphenol; 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Amphropolys; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benalaxyl M; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos;
  • binapacryl binapacryl; biphenyl; bitertanol; Blasticidin-S; boscalid; bromuconazole; Bupirimate; Buthiobate;
  • Dagger G debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; Diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; Diniconazoles; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolone; edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone;
  • fluoromides fluoxastrobin; fluquinconazole; Flu ⁇ rimidol; flusilazole; flusulfamide; flutolanil;
  • Iminoctadine triacetate Iminoctadine tris (albesilate); lodocarb; ipconazole; iprobenfos; iprodione;
  • iprovalicarb Irumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb;
  • Bactericides bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • Insecticides / acaricides / nematicides 1. Acetylcholinesterase (AChE) inhibitors
  • carbamates eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, Formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, Triazamate, trimethacarb, XMC, xylylcarb)
  • organophosphates eg acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chlormephos, chlo ⁇ yrifos (-methyl / -ethyl), Coumophos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fe
  • Sodium channel modulators / voltage-dependent sodium channel blockers 2.1 pyrethroids (for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl-isomer , Bioethanomethrin, biopermethrin, bioresmethrin, chlorovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, em-
  • Penthrine (lR-isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalate, flubrocythrinates, flucythrinates, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin ( cis-, trans-), phenothrin (IR trans isomer), prallethrin, profuthrin, protrifenbutene, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralome
  • chloronicotinyls / neonicotinoids for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, tenpyram, nithiazines, thiacloprid, thiamethoxam
  • Mectins for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milkmectin, milbemycin
  • Juvenile hormone mimetics eg, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene
  • diacylhydrazines e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides
  • Benzoylureas e.g., bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoronon
  • bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoronon e.g., bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron
  • Organotin e.g., azocyclotin, cyhexatin, fenbutatin oxides
  • METTs e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Tetronic acids e.g., spirodiclofen, spiromesifen
  • 16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ester, CAS Reg. No .: 382608-10-8) and carbonic acid, cis-3 - (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg. No .: 203313-25-1)]
  • Carboxamides e.g., flonicamid
  • Octopaminergic agonists eg, Amitraz
  • Inhibitors of magnesium-stimulated ATPase eg, propargite
  • Nereistoxin analogs e.g., thiocyclam hydrogen oxalate, thiosultap-sodium
  • Fumigants for example aluminum phosphides, methyl bromides, sulfuryl fluorides
  • mite growth inhibitors e.g., clofentezine, etoxazole, hexythiazox
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is by no means
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • the application is carried out in a customary manner, for example by casting, spraying, spraying, scattering, dusting, foaming, spreading, etc.
  • the active ingredients by the ultra-low-volume method pointedbrin ⁇ or the preparation of active compound or the To inject active substance into the soil itself. It can also be the seed of the plants to be treated.
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • Plant parts are the application rates of active ingredient generally between 0.1 and 0.1
  • Application rates of active ingredient generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above.
  • plants of the respective commercially available or used plant cultivars are particularly preferably treated.
  • Plant varieties are understood to be plants having new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.
  • the treatment according to the invention can also give rise to superadditive ("synergistic") effects, for example, reduced application rates and / or enhancements of the activity spectrum and / or an increase in the effect of Substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering efficiency, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value Harvest products, higher storage capacity and / or workability of the harvested products possible, which go beyond the expected effects actually.
  • superadditive superadditive
  • the preferred plants or plant varieties to be treated according to the invention which are to be treated include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") Examples of such properties are better Plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering, easier harvesting, acceleration of maturity, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or Viruses and increased tolerance of plants against certain herbicidal active ingredients.
  • microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or Viruses and increased tolerance of plants against certain herbicidal active ingredients.
  • transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, potato , Cotton, tobacco and oilseed rape.
  • Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylHA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof) in the plants (hereinafter "JBt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylHA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof
  • genes conferring the desired properties can also occur in combinations with one another in the transgenic plants Examples of maize varieties, cotton varieties, soybean varieties and potato varieties which may be mentioned under the trade names YIELD GARD ® (eg corn, cotton, soy), KnockOut® (eg corn), StarLink® (eg Corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • YIELD GARD ® eg corn, cotton, soy
  • KnockOut® eg corn
  • StarLink® eg Corn
  • Bollgard® cotton
  • Nucoton® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® ( Tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rapeseed
  • IMI® Tolerance to imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Herbicide-resistant plants are also mentioned under the name Clearf ⁇ eld® varieties (eg corn). Of course, these statements also apply to plant varieties developed or to be marketed in the future with these or future developed genetic traits.
  • the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • the specified logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (C 18). Temperature: 43 ° C.
  • Eluents for determination in the acidic range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose LogP values are known (determination of the LogP values by means of the retention times by linear interpolation between two consecutive alkanones).
  • the lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • dimethylacetamide emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at about 21 ° C and a relative humidity of about 90%.
  • dimethylacetamide emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at a temperature of about 20 0 C and a relative humidity of 80%.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

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Abstract

Disclosed are novel biphenyl thiazole carboxamides of formula (I), wherein R1, R2, R3, R4, m, and R5 have the meanings indicated in the description, several methods for producing said substances, the use thereof for controlling undesired microorganisms, and novel intermediate products as well as the production thereof.

Description

Biphenylthiazolcarboxamidebiphenyl thiazole carboxamides
Die vorliegende Erfindung betrifft neue Biphenylthiazolcarboxamide, mehrere Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von unerwünschten Mikroorganismen.The present invention relates to novel Biphenylthiazolcarboxamide, several processes for their preparation and their use for controlling unwanted microorganisms.
Es ist bereits bekannt, dass zahlreiche Carboxamide fungizide Eigenschaften besitzen (vgl. z.B. WO 03/070705, WO 97/08148 und JP-A 2001-302605). So sind bereits zahlreiche Biphenylcarboxamide be¬ kannt geworden, die im Biphenylteil substituiert sein können, wie z.B. N-{3',4'-Dichlor-3-fluor-l,r-bi- phenyl-2-yl>l-methyl-3-(trifluormethyl)-lH-pyrazol-4-carboxamid aus WO 03/070705, N-(5-Fluor-4'- methylbiphenyl-2-yl)-2-methyl-4-(trifluorme%l>-l,3-thiazol-5-carboxamid aus WO 97/08148 und N-(4'-Methoxy-6-methylbiphenyl-2-yI)-2-methyM-(trifluormethyl)- 1 ,3-thiazol-5-carb-oxamid aus JP 2001-302605. Die Wirksamkeit dieser Stoffe ist gut, lässt aber in manchen Fällen, z.B. bei niedrigen Aufwandmengen zu wünschen übrig.It is already known that numerous carboxamides have fungicidal properties (see, for example, WO 03/070705, WO 97/08148 and JP-A 2001-302605). Thus, numerous biphenylcarboxamides have already been known, which may be substituted in the biphenyl moiety, such as e.g. N- {3 ', 4'-dichloro-3-fluoro-1, r-biphenyl-2-yl> 1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide from WO 03/070705, N- (5-fluoro-4'-methylbiphenyl-2-yl) -2-methyl-4- (trifluoromethyl) -1,3-thiazole-5-carboxamide from WO 97/08148 and N- (4'- Methoxy-6-methylbiphenyl-2-yl) -2-methyl- (trifluoromethyl) -1,3-thiazole-5-carboxamide from JP 2001-302605 The effectiveness of these substances is good, but in some cases, eg to be desired at low application rates.
Es wurden nun neue Biphenylthiazolcarboxamide der Formel (I)There have now been new Biphenylthiazolcarboxamide of formula (I)
in welcher in which
R1 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)amino, Cyano, Ci-C4-R 1 is hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) amino, cyano, C 1 -C 4 -
Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R2 für Halogen, C]-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,Alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 2 represents halogen, C] -C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R3 für Wasserstoff, C1-C8-AIkV-, CrC6-Alkylsulfinyl, C,-C6-Alkylsulfonyl, Ci-C4-Alkoxy-CrC4- alkyl, C3-C8-Cycloalkyl; CrC6-Halogenalkyl, CrC4-Halogenalkylthio, CrC4-Halogenalkyl- sulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-C]-C3- alkyl, (CrCs-AlkyOcarbonyl-C-Cj-alkyl, (C,-C3-Alkoxy)carbonyl-CrC3-alkyl; Halogen-(Ci-R 3 is hydrogen, C 1 -C 8 -AIkV-, C r C 6 alkylsulfinyl, C, -C 6 alkylsulfonyl, Ci-C 4 -alkoxy-C r C 4 - alkyl, C 3 -C 8 cycloalkyl ; C r C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4 haloalkyl sulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -halogeno-cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C] -C 3 - alkyl, (CRCS AlkyOcarbonyl-C-Cj-alkyl, (C, -C 3 -alkoxy) carbonyl-C r C 3 alkyl; halo (Ci-
C3-alkyl)carbonyl-C]-C3-alkyl, Halogen-(Ci-C3-alkoxy)carbonyl-C]-C3-alkyl mit jeweils 1 bisC 3 -alkyl) carbonyl-C] -C3 alkyl, halo (Ci-C 3 alkoxy) carbonyl-C] -C 3 alkyl each having 1 to
13 Fluor-, Chlor- und/oder Bromatomen;13 fluorine, chlorine and / or bromine atoms;
(Cj-Cg-AlkyOcarbonyl, (C,-C8-Alkoxy)carbonyl, (C,-C4-Alkoxy-Ci-C4-alkyl)carbonyl, (C3-(C 1 -C 6 -alkyloxycarbonyl, (C 1 -C 8 -alkoxy) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -
C8-Cycloalkyl)carbonyl; (CrC6-Halogenalkoxy)carbonyl, (Halogen-CrC4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C8-Halogencycloalkyl)carbonyl mit jeweilsC 8 cycloalkyl) carbonyl; (C r C 6 haloalkoxy) carbonyl, (halo-C r C 4 alkoxy-Ci-C4-alkyl) carbonyl, (C 3 -C 8 halocycloalkyl) carbonyl having in each case
1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R6, -CONR7R8 oder1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 6 , -CONR 7 R 8 or
-CH2NR9R10 steht, R4 für Halogen, CrC4-Alkyl, CrC4-Alkoxy, CrC4-Alkylthio oder CrC4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht, m für 1 oder 2 steht, wobei die Reste R4 gleich oder verschieden sein können, wenn m für 2 steht,-CH 2 NR 9 R 10 , R 4 is halogen, C r C 4 alkyl, C r C 4 alkoxy, C r is C 4 -alkylthio or C r C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, m represents 1 or 2, where R 4 may be the same or different when m is 2,
R5 für Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxy, Carbamoyl, Thiocarbamoyl, CrC8-Alkyl, C2-C6-Alkenyl, C,-C8-Alkoxy, C2-C6-Alkenyloxy, C,-C8-Alkylthio, C1-C8-R 5 represents halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, C r C 8 alkyl, C 2 -C 6 alkenyl, C, -C 8 alkoxy, C 2 -C 6 - Alkenyloxy, C, -C 8 alkylthio, C 1 -C 8 -
Alkylsulfinyl, C,-C8-Alkylsulfonyl, C,-C8-Hydroxyalkyl, CrC8-Oxoalkyl, C,-C8-Alkoxyal- kyl, Ci-C8-Alkylthioalkyl, C,-C8-Dialkoxyalkyl, C,-C6-Alkylamino, Di(Ci-C6-alkyl)amino, (CrC6-Alkyl)carbonyl, (CrC6-Alkyl)carbonyloxy, (C,-C6-Alkoxy)carbonyl, (C,-C6-Alkyl)- aminocarbonyl, Di(Ci-C6-alkyi)aminocarbonyl, (CrC6-Alkyl)carbonylamino, (Ci-C6-Alkyl)- carbonyl(Ci-C6-alkyl)amino, (C2-C6-Alkenyl)carbonyl, (C2-C6- Alkinyl)carbonyl, C3-C6-Alkylsulfinyl, C, -C 8 alkylsulfonyl, C, -C 8 hydroxyalkyl, C r C 8 -oxoalkyl, C, -C 8 alkyl -Alkoxyal-, Ci-C 8 alkylthioalkyl, C, -C 8 -Dialkoxyalkyl, C, -C 6 alkylamino, di (Ci-C 6 alkyl) amino, (C r C 6 alkyl) carbonyl, (C r C 6 alkyl) carbonyloxy, (C, -C 6 alkoxy) carbonyl, (C, -C 6 alkyl) - aminocarbonyl, di (Ci-C 6 -alkyi) aminocarbonyl, (C r C 6 alkyl) carbonylamino, (Ci-C 6 alkyl) - carbonyl (Ci-C 6 alkyl ) amino, (C 2 -C 6 -alkenyl) carbonyl, (C 2 -C 6 -alkynyl) carbonyl, C 3 -C 6 -
Cycloalkyl, C3-C6-Cycloalkyloxy, oder für Ci-C6-Halogenalkyl, CrC6-Halogenalkoxy, C]-C6- Halogenalkylthio, CrC6-Halogenalkylsulfinyl oder Ci-C6-Halogenalkylsulfonyl mit jeweils 1 bis 13 Halogenatomen, C2-C6-Halogenalkenyl, C2-C6-Halogenalkenyloxy mit jeweils 1 bis 11 gleichen oder verschiedenen Halogenatomen steht, R6 für Wasserstoff, CrC8-Alkyl, C,-C8-Alkoxy, C,-C4-Alkoxy-CrC4-alkyl, C3-C8-Cycloalkyl; Ci-C6-Halogenalkyl, Ci-C6-Halogenalkoxy, Halogen-Ci-C4-alkoxy-CrC4-alkyl, C3-C8-HaIo- gencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht,Cycloalkyl, C 3 -C 6 cycloalkyloxy, or for Ci-C 6 haloalkyl, C r C 6 haloalkoxy, C] -C6 - haloalkylthio, C r C 6 haloalkylsulfinyl or C 6 haloalkylsulfonyl, each with 1 to 13 halogen atoms, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkenyloxy same, each having 1 to 11 or different halogen atoms, R 6 is hydrogen, C r C 8 alkyl, C, -C 8 alkoxy, C 1 -C 4 alkoxyC r C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C 6 haloalkyl, Ci-C 6 haloalkoxy, halogen-Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 -HaIo- gencycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms stands,
R7 und R8 unabhängig voneinander jeweils für Wasserstoff, CrC8-Alkyl, Ci-C4-Alkoxy-CrC4-alkyl, C3-C8-Cycloalkyl; CrC8-Halogenalkyl, Halogen-CrC4-alkoxy-Ci-C4-alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 7 and R 8 are each independently hydrogen, C r C 8 alkyl, Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 cycloalkyl; , Halo-C r C 4 are C r C 8 haloalkyl alkoxy-Ci-C4-alkyl, halo-C 3 -C 8 cycloalkyl with in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R7 und R8 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenen¬ falls einfach oder mehrfach, gleich oder verschieden durch Halogen oder C]-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Hetero- cyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR11 enthalten kann,R 7 and R 8 together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms, which is optionally mono- or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl Heterocycle may contain 1 or 2 further, nonadjacent heteroatoms from the series oxygen, sulfur or NR 11 ,
R9 und R10 unabhängig voneinander für Wasserstoff, Ci-Cg-Alkyl, C3-Cs-Cycloalkyl; Ci-Q-Halogen- alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 9 and R 10 are independently hydrogen, Ci-Cg-alkyl, C 3 -Cs-cycloalkyl; Ci-Q-haloalkyl, C 3 -C 8 -halogencycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R9 und R10 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebe¬ nenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Hetero¬ cyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR11 enthalten kann,R 9 and R 10 together with the nitrogen atom to which they are attached additionally form a saturated heterocycle having 5 to 8 ring atoms, which is optionally mono- or polysubstituted, identically or differently, by halogen or C 1 -C 4 -alkyl, where the hetero ¬ cyclus can contain 1 or 2 further non-adjacent heteroatoms from the series oxygen, sulfur or NR 11 ,
R1 ' für Wasserstoff oder Q-Q-Alkyl steht, gefunden, wobei Verbindungen der Formel (I) ausgenommen sind, in welcher R1 für Wasserstoff oder Methyl steht,R 1 'is hydrogen or QQ-alkyl, with the exception of compounds of the formula (I) in which R 1 is hydrogen or methyl,
R2 für Chlor, Methyl, Difluormethyl oder Trifluormethyl steht, R5 fiir Halogen, CrC4-Alkyl, Trifluormethyl, CrC4-Alkoxy oder CrC4-Alkylthio steht, wenn R3 für Wasserstoff und R4 für Fluor und m für 1 steht.R 2 is chlorine, methyl, difluoromethyl or trifluoromethyl, R 5 fiir halogen, C r C 4 alkyl, trifluoromethyl, C r C 4 alkoxy or C r C 4 alkylthio is, when R 3 is hydrogen and R 4 m is 1 and represents fluorine.
Weiterhin wurde gefunden, dass man Biphenylthiazolcarboxamide der Formel (1) erhält, indem man (a) Carbonsäure-Derivate der Formel (II)Furthermore, it has been found that biphenylthiazolecarboxamides of the formula (1) are obtained by reacting (a) carboxylic acid derivatives of the formula (II)
in welcher in which
R1 und R2 die oben angegebenen Bedeutungen haben und X1 für Halogen oder Hydroxy steht, mit Biphenylaminen der Formel (HI)R 1 and R 2 have the meanings given above and X 1 is halogen or hydroxy, with biphenylamines of the formula (HI)
in welcher R3, R4, m und R5 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Konden¬ sationsmittels, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder in which R 3 , R 4 , m and R 5 have the abovementioned meanings, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
(b) Halogencarboxamide der Formel (TV)(b) Halo carboxamides of the formula (TV)
in welcher in which
R1, R2, R3, R4 und m die oben angegebenen Bedeutungen haben, X2 für Brom, Iod oder Trifluormethylsulfonat steht, mit Boronsäure-Derivaten der Formel (V)R 1 , R 2 , R 3 , R 4 and m have the meanings given above, X 2 is bromine, iodine or trifluoromethylsulfonate, with boronic acid derivatives of the formula (V)
in welcher R5 die oben angegebenen Bedeutungen hat und in which R 5 has the meanings given above and
G1 und G2 jeweils für Wasserstoff oder zusammen für Tetramethylethylen stehen, in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder (c) Boronsäure-Derivate der Formel (VT)G 1 and G 2 are each hydrogen or together are tetramethylethylene, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or (c) boronic acid derivatives of the formula (VT)
in welcher in which
R1, R2, R3, R4 und m die oben angegebenen Bedeutungen haben, G3 und G4 jeweils für Wasserstoff oder zusammen für Tetramethylethylen stehen, mit Phenyl-Derivaten der Formel (VII)R 1 , R 2 , R 3 , R 4 and m have the meanings given above, G 3 and G 4 are each hydrogen or together are tetramethylethylene, with phenyl derivatives of the formula (VII)
in welcher in which
R5 die oben angegebenen Bedeutungen hat und X3 für Chlor, Brom, Iod oder Trifluormethylsulfonat steht, in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder (d) Halogencarboxamide der Formel (TV)R 5 has the abovementioned meanings and X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or (d) halocarboxamides of the formula (TV)
in welcher R1, R2, R3, R4 und m die oben angegebenen Bedeutungen haben, in which R 1 , R 2 , R 3 , R 4 and m have the meanings given above,
X2 für Brom, Iod oder Trifluormethylsulfonat steht, mit Phenyl-Derivaten der Formel (VII)X 2 is bromine, iodine or trifluoromethylsulfonate, with phenyl derivatives of the formula (VII)
in welcher R5 die oben angegebenen Bedeutungen hat und X3 für Chlor, Brom, Iod oder Trifluormethylsulfonat steht, in Gegenwart eines Palladium- oder Nickel-Katalysators und in Gegenwart von 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis-l,3,2-dioxaborolan, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder (e) Biphenylthiazolcarboxamide der Formel (I-a) in which R 5 has the abovementioned meanings and X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate, in the presence of a palladium or nickel catalyst and in the presence of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-l, 3,2-dioxaborolane, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or (e) biphenylthiazolecarboxamides of the formula (Ia)
in welcher in which
R1, R2, R4, m und R5 die oben angegebenen Bedeutungen haben, mit Halogeniden der Formel (VHl)R 1 , R 2 , R 4 , m and R 5 have the meanings given above, with halides of the formula (VHI)
R^-X4 (Vm) in welcherR ^ -X 4 (Vm) in which
R3A für CrC8-Alkyl, CrC6-Alkylsulfinyl, C,-C6-Alkylsulfonyl, CrC4-Alkoxy-C,-C4-al- kyl, C3-C8-Cycloalkyl; CrC6-Halogenalkyl, CrC4-Halogenalkylthio, CrC4-Halogen- alkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-CrC4-alkyl, C3-C8-R 3A represents C r C 8 alkyl, C r C 6 alkylsulfinyl, C, -C 6 alkylsulfonyl, C r C 4 alkoxy-C, -C 4 -AL- alkyl, C 3 -C 8 cycloalkyl; C r C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4-halo-alkylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 -
Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-Cs-alkyl, (Ci-C3-Alkyl)carbonyl-Ci-C3-alkyl, (C,-C3-Alkoxy)carbonyl-Ci- C3-alkyl; Halogen-(Ci-C3-alkyl)carbonyl-Ci-C3-alkyl, Halogen-(Ci-C3-alkoxy)carbo- nyl-C]-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (CrCg-Alkyl)carbonyl, (CrC8-Alkoxy)carbonyl, (Ci-C4-Alkoxy-C,-C4-alkyl)carbo- nyl, (C3-C8-Cycloalkyl)carbonyl; (Ci-Cβ-HalogenalkyOcarbonyl, (Ci-C6-Halogenalk- oxy)carbonyl, (Halogen-CrC4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C8-Halogencyclo- alkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R6, -CONR7R8 oder -CH2NR9R10 steht, R6, R7, R8, R9 und R10 die oben angegebenen Bedeutungen haben,Halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-Ci-Cs-alkyl, (Ci-C 3 alkyl) carbonyl-Ci-C 3 alkyl, (C, -C 3 -alkoxy) carbonyl-Ci- C3 alkyl; Halo (Ci-C 3 alkyl) carbonyl-Ci-C 3 alkyl, halo (Ci-C 3 alkoxy) carbonyl-C] -C 3 alkyl each having 1 to 13 fluorine, chlorine and / or bromine atoms; (CRCG-alkyl) carbonyl, (C r C 8 alkoxy) carbonyl, (Ci-C 4 alkoxy-C, -C 4 alkyl) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl; (Ci-Cβ-HalogenalkyOcarbonyl, (Ci-C 6 -Halogenalk- oxy) carbonyl, (halo-C r C 4 alkoxy-Ci-C4-alkyl) carbonyl, (C 3 -C 8 -Halogencyclo- alkyl) carbonyl with 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10 , R 6 , R 7 , R 8 , R 9 and R 10 have the meanings given above,
X4 fiir Chlor, Brom oder Iod steht, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt.X 4 is chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
Schließlich wurde gefunden, dass die neuen Biphenylthiazolcarboxamide der Formel (I) sehr gute mikrobizide Eigenschaften besitzen und zur Bekämpfung unerwünschter Mikroorganismen sowohl im Pflanzenschutz als auch im Materialschutz verwendbar sind. Die erfindungsgemäßen Verbindungen können gegebenenfalls als Mischungen verschiedener mög¬ licher isomerer Formen, insbesondere von Stereoisomeren, wie z. B. E- und Z-, threo- und erythro-, sowie optischen Isomeren, gegebenenfalls aber auch von Tautomeren vorliegen. Es werden sowohl die E- als auch die Z-Isomeren, wie auch die threo- und erythro-, sowie die optischen Isomeren, be- liebige Mischungen dieser Isomeren, sowie die möglichen tautomeren Formen beansprucht.Finally, it has been found that the novel biphenylthiazolecarboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials. If appropriate, the compounds according to the invention can be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms are claimed.
Die erfindungsgemäßen Biphenylthiazolcarboxamide sind durch die Formel (T) allgemein definiert. Bevorzugte Restedefinitionen der vorstehenden und nachfolgend genannten Formeln sind im Folgen¬ den angegeben. Diese Definitionen gelten für die Endprodukte der Formel (I) wie für alle Zwischen- produkte gleichermaßen.The Biphenylthiazolcarboxamide invention are generally defined by the formula (T). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of the formula (I) as well as to all intermediate products.
R1 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-C4-Alkylamino, Di(C]-C4- alkyl)amino, Cyano, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R1 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino,R 1 preferably represents hydrogen, fluorine, chlorine, bromine, amino, C 1 -C 4 -alkylamino, di (C 1 -C 4 -alkyl) amino, cyano, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 Fluorine, chlorine and / or bromine atoms. R 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
Dimethylamino, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R1 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino,Dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
Dimethylamino, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R1 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Chlor, Methyl oderDimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 1 particularly preferably represents amino, methylamino, dimethylamino, chlorine, methyl or
Trifluormethyl.Trifluoromethyl.
R2 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5R 2 is preferably fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5
Fluor, Chlor und/oder Bromatomen. R2 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, 1-Fluorethyl, Trifluorme¬ thyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.Fluorine, chlorine and / or bromine atoms. R 2 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, 1-fluoroethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R2 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluor¬ methyl oder Trichlormethyl.R 2 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R2 steht insbesondere bevorzugt für Methyl, Trifluormethyl oder Difluormethyl.R 2 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
R3 steht bevorzugt für Wasserstoff, CrC6-Alkyl, C,-C4-Alkylsulfinyl, CrC4-Alkylsulfonyl, C,-C3- Alkoxy-Ci-Cs-alkyl, C3-C6-Cycloalkyl; C,-C4-Halogenalkyl, CrC4-Halogenalkylthio, CrC4-Ha- logenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C3-alkoxy-Ci-C3-alkyl, C3-C8- Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl- CrC3-alkyl, (C,-C3-Alkyl)carbonyl-C,-Cralkyl, (Ci-C3-A]koxy)carbonyl-C]-C3-alkyl; Halogen-R 3 preferably represents hydrogen, C r C 6 alkyl, C, -C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C, -C 3 - alkoxy-Ci-Cs-alkyl, C 3 -C 6 cycloalkyl , C, -C 4 haloalkyl, C r C 4 haloalkylthio, C r C 4 -Ha- logenalkylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C 3 alkoxy-Ci-C 3 alkyl, C 3 - C 8 - halogenocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl C r C 3 alkyl, (C, -C 3 -alkyl) carbonyl-C, -C r alkyl, (Ci-C 3 -A] -alkoxy) carbonyl-C] -C3 alkyl; Halogen-
(Ci-C3-alkyl)carbonyl-Ci-C3-alkyl, Halogen-(CrC3-alkoxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen;(Ci-C 3 alkyl) carbonyl-Ci-C 3 alkyl, halo (C r C 3 alkoxy) carbonyl-Ci-C 3 alkyl each having 1 to 13 fluorine, chlorine and / or bromine atoms;
(CrC6-Alkyl)carbonyl, (CrC4-Alkoxy)carbonyl, (Ci-C3-Alkoxy-CrC3-alkyl)carbonyl, (C3-C6- Cycloalkyl)carbonyl; (Q-C^Halogenalkyl^arbonyl, (CrC4-Halogenalkoxy)carbonyl, (HaIo- gen-Ci-C3-alkoxy-Ci-C3-alkyl)carbonyl, (C3-C6-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R6, -CONR7R8 oder -CH2NR9R10.(-C 6 alkyl) carbonyl, (C r C 4 alkoxy) carbonyl, (Ci-C 3 alkoxy-C r C 3 alkyl) carbonyl, (C 3 -C 6 - cycloalkyl) carbonyl; (QC ^ haloalkyl ^ arbonyl, (C r C 4 haloalkoxy) carbonyl, (halogeno-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl) carbonyl, (C 3 -C 6 -halocycloalkyl) carbonyl each having 1) to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10 .
R3 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pentyl oder Hexyl, Methylsulfinyl, Ethylsulfmyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Trichlormethyl, Trifluorethyl, Difluor- methylthio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethylsulfinyl, Trifluormethyl- sulfonyl, Trifluormethoxymethyl; Formyl, -CH2-CHO, -(CH2VCHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CHz)2-CO-CH3, -(CH2)Z-CO-CH2CH3, -(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)Z, -(CH2VCO2CH3, -(CHz)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CH2-CO-CCl3,R 3 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfmyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, Trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; Formyl, -CH 2 -CHO, - (CH 2 VCHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 , - (CHz ) 2 -CO-CH 3 , - (CH 2 ) Z -CO-CH 2 CH 3 , - (CH 2 ) 2 -CO-CH (CH 3 ) 2 , -CH 2 -CO 2 CH 3 , -CH 2 -CO 2 CH 2 CH 3 , -CH 2 -CO 2 CH (CH 3 ) Z , - (CH 2 VCO 2 CH 3 , - (CH 2 ) 2 -CO 2 CH 2 CH 3 , - (CH 2 ) 2 - CO 2 CH (CH 3 ) 2 , -CH 2 -CO-CF 3 , -CH 2 -CO-CCl 3 ,
-CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CH2VCaCH2CF3, -(CH2VCaCH2CCl3, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CHz)2-CO2CH2CF3, -(CHZ)2-COZCF2CF3, -(CH2VCO2CH2CCl3, -(CH2VCO2CCl2CCl3; Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, tert-Butoxycarbonyl, Cyclopropylcarbonyl; Trifluorme- thylcarbonyl, Trifluormethoxycarbonyl, oder -C(=O)C(=O)R6, -CONR7R8 oder -CH2NR9R10. R3 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Methoxymethyl, Formyl, -CH2-CHO, -(CH2VCHO, -CH2-CO-CH3, -CH2-CaCH2CH3, -CH2-CO-CH(CH3)Z, -C(=O)CHO, -C(=O)C(=O)CH3, -C(=O)C(=O)CH2OCH3, -Q=O)CO2CH3, -C(O)CO2CH2CH3.-CH 2 -CO-CH 2 CF 3 , -CH 2 -CO-CH 2 CCl 3 , - (CH 2 VCaCH 2 CF 3 , - (CH 2 VCaCH 2 CCl 3 , -CH 2 -CO 2 CH 2 CF 3 , -CH 2 -CO 2 CF 2 CF 3 , -CH 2 -CO 2 CH 2 CCl 3 , -CH 2 -CO 2 CCl 2 CCl 3 , - (CH 2 ) 2 -CO 2 CH 2 CF 3 , - (CH Z) 2 -CO Z CF 2 CF 3, - (CH 2 VCO 2 CH 2 CCl 3, - (CH 2 VCO 2 CCl 2 CCl 3; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tert-butylcarbonyl, methoxycarbonyl , Ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl, trifluoromethylcarbonyl, trifluoromethoxycarbonyl, or -C (= O) C (= O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10. R 3 is very particularly preferred for hydrogen, methyl, methoxymethyl, formyl, -CH 2 -CHO, - (CH 2 VCHO, -CH 2 -CO-CH 3 , -CH 2 -CaCH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) Z, -C (= O) CHO, -C (= O) C (= O) CH 3 , -C (= O) C (= O) CH 2 OCH 3 , -Q = O) CO 2 CH 3 , -C (O) CO 2 CH 2 CH 3 .
R4 steht bevorzugt für Fluor, wobei Fluor besonders bevorzugt in 3- oder 5- Position, ganz besonders bevorzugt in 5-Position der jeweiligen Verbindung steht [vgl. z.B. Formel (I)]. R4 steht bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 4- oder 5- Position, ganz besonders bevorzugt in 4-Position, außerdem ganz besonders bevorzugt in 5-Position der jeweiligen Verbindung steht.R 4 is preferably fluorine, with fluorine being particularly preferably in the 3- or 5-position, very particularly preferably in the 5-position of the respective compound [cf. eg formula (I)]. R 4 is preferably chlorine, with chlorine being particularly preferably in the 4- or 5-position, very particularly preferably in the 4-position, moreover very particularly preferably in the 5-position of the respective compound.
R4 steht außerdem bevorzugt für Trifluormethyl, wobei Trifluormethyl besonders bevorzugt inR 4 furthermore preferably represents trifluoromethyl, trifluoromethyl being particularly preferably in
4- oder 5-Position der jeweiligen Verbindung steht.4- or 5-position of the respective connection stands.
R4 steht außerdem bevorzugt für Methoxy oder Methylthio, wobei Methoxy oder Methylthio besonders bevorzugt in 3- oder 5- Position, ganz besonders bevorzugt in 5-Position der jeweiligen Verbindung stehen. R4 steht außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 4- oder 5- Position, ganz besonders bevorzugt in 4-Position der jeweiligen Verbindung steht.R 4 furthermore preferably represents methoxy or methylthio, with methoxy or methylthio being particularly preferably in the 3- or 5-position, very particularly preferably in the 5-position of the respective compound. R 4 furthermore preferably represents methyl, where methyl is particularly preferably in the 4- or 5-position, very particularly preferably in the 4-position of the respective compound.
R4 steht außerdem bevorzugt für iso-Propyl, wobei iso-Propyl besonders bevorzugt in 4- oder 5-R 4 is also preferably isopropyl, with isopropyl being particularly preferred in 4- or 5-
Position, ganz besonders bevorzugt in 5-Position der jeweiligen Verbindung steht.Position, most preferably in the 5-position of the respective compound.
m steht bevorzugt für 1. m steht außerdem bevorzugt für 2, wobei die Reste R4 gleich oder verschieden sein können.In addition, m is preferably 1. m is furthermore preferably 2, where the radicals R 4 may be identical or different.
R5 steht bevorzugt für Fluor, Chlor, Brom, Cyano, Nitro, Amino, Hydroxy, Formyl, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Vinyl, Allyl, Methoxy, Ethoxy, n- oder iso-Propoxy, Vinyloxy, Allyloxy, Methylthio, Ethylthio, n- oder iso-Propylthio, Methyl- sulfinyl, Ethylsulfinyl, n- oder iso-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso- Propylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Methyl- thiomethyl, Methylthioethyl, Ethylthiomethyl, Ethylthioethyl, Methylamino, Ethylamino, iso- Propylamino, Dimethylamino, Diethylamino, Dipropylamino, Diisopropylamino, Methyl- carbonyl, Ethylcarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, Methylcarbonyl- amino, Methylcarbonylmethylamino, Cyclopropyl, Cyclopropyloxy, Trifluormethyl, Tri- chlormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluorchlormethoxy, Tri- fluorethoxy, Difluormethylthio, Difluorchlormethylthio oder Trifluormethylthio. R5 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, Methylthio, Ethylthio, n- oder iso-Propylthio, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, Methoxymethyl, Methylthiomethyl, Methylamino, Ethylamino, iso-Propylamino, Dimethylamino, Diethyl¬ amino, Diisopropylamino, Methylcarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, Methylcarbonylamino, Cyclopropyl, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluor¬ methoxy, Difluormethylthio oder Trifluormethylthio.R 5 is preferably fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, vinyl, allyl, methoxy , Ethoxy, n- or iso-propoxy, vinyloxy, allyloxy, methylthio, ethylthio, n- or iso-propylthio, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, methoxymethyl , Methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, methylamino, ethylamino, iso-propylamino, dimethylamino, diethylamino, dipropylamino, diisopropylamino, methylcarbonyl, ethylcarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylcarbonylamino, methylcarbonylmethylamino, cyclopropyl , Cyclopropyloxy, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio or trifluoromethylthio. R 5 is particularly preferably fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, methylthio, ethylthio , n- or iso-Propylthio, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, methoxymethyl, methylthiomethyl, methylamino, ethylamino, iso-propylamino, dimethylamino, diethylamino, diisopropylamino, methylcarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylcarbonylamino, cyclopropyl, trifluoromethyl Trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio or trifluoromethylthio.
R5 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, iso-Propyl, tert-Butyl, Methoxy, iso-Propoxy, Methylthio, iso-Propylthio, Methoxymethyl, Methylthiomethyl, Methylamino, Dimethylamino, Methylaminocarbonyl, Methylcarbonylamino, Cyclopropyl, Trifluormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluormethylthio oderR 5 most preferably represents fluoro, chloro, bromo, methyl, iso-propyl, tert-butyl, methoxy, iso-propoxy, methylthio, iso-propylthio, methoxymethyl, methylthiomethyl, methylamino, dimethylamino, methylaminocarbonyl, methylcarbonylamino, cyclopropyl, trifluoromethyl , Trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio or
Trifluormethylthio.Trifluoromethylthio.
R5 steht insbesondere bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluor¬ methoxy oder Trifluormethoxy. R6 steht bevorzugt für Wasserstoff, C,-C6-Alkyl, C,-C4-Alkoxy, C,-C3-Alkoxy-C|-C3-alkyl, C3- C6-Cycloalkyl; CrC4-Halogenalkyl, CrC4-Halogenalkoxy, Halogen-Ci-Cs-alkoxy-Ci-Cs- alkyl, Cs-Cβ-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R6 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, tert-Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, tert-Butoxy, Methoxymethyl, Cyclopropyl; Trifluor- methyl, Trifluormethoxy.R 5 particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy. R 6 preferably represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; Alkyl C r C 4 haloalkyl, C r C 4 haloalkoxy, halo-Ci-Cs-alkoxy-Ci-Cs, Cs-Cβ-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms. R 6 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
R7 und R8 stehen unabhängig voneinander bevorzugt für Wasserstoff, C1-C6-AUCyI, Ci-C3-Alkoxy-Cr C3-aIkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, Halogen-CrC3-alkoxy-C,-C3-alkyl, C3-C6- Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.R 7 and R 8 independently of one another preferably represent hydrogen, C 1 -C 6 -alkyl, C 1 -C 3 -alkoxy-C r C 3 -alkyl, C 3 -C 6 -cycloalkyl; C r C 4 -haloalkyl, haloC r C 3 -alkoxy-C, C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
R7 und R8 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder C]- C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Hetero- cyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR11 enthalten kann.R 7 and R 8 also form, together with the nitrogen atom to which they are bonded, preferably a saturated heterocycle having 5 or 6 ring atoms optionally monosubstituted to monosubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the hetero cyclus may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 11 .
R7 und R8 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifluormethyl, Trichlormethyl,R 7 and R 8 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl,
Trifluorethyl, Trifluormethoxymethyl.Trifluoroethyl, trifluoromethoxymethyl.
R7 und R8 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 7 and R 8 also together with the nitrogen atom to which they are attached, more preferably form an optionally mono- to di-quadratic, identical or different, by fluorine,
Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R11 substituiert sein kann.Chloro, bromo or methyl substituted saturated heterocycle from the series morpholine, thiomorpholine or piperazine, wherein the piperazine may be substituted on the second nitrogen atom by R 11 .
R9 und R10 stehen unabhängig voneinander bevorzugt für Wasserstoff, C]-C6-Alkyl, C3-C6-Cycloal- kyl; CpGi-Halogenalkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.R 9 and R 10 independently of one another preferably represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl; CpGi-haloalkyl, C 3 -C 6 -halo cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
R9 und R10 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder Q-R 9 and R 10 together with the nitrogen atom to which they are attached preferably also form an optionally monosubstituted to quadruple, identical or different, by halogen or
C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei derC 4 alkyl substituted saturated heterocycle having 5 or 6 ring atoms, wherein the
Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR11 enthalten kann.Heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the series oxygen, sulfur or NR 11 .
R9 und R10 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifluormethyl, Trichlormethyl, Trifluorethyl, Trifluormethoxymethyl. R9 und R10 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R11 substituiert sein kann.R 9 and R 10 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R 9 and R 10 also together with the nitrogen atom to which they are attached, more preferably form an optionally monosubstituted to quadruple, identical or different, by fluorine, Chloro, bromo or methyl substituted saturated heterocycle from the series morpholine, thiomorpholine or piperazine, wherein the piperazine may be substituted on the second nitrogen atom by R 11 .
R11 steht bevorzugt für Wasserstoff oder CrC4-Alkyl.R 11 is preferably hydrogen or C r C 4 alkyl.
R11 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl.R 11 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
Ausgenommen sind insbesondere jeweils Verbindungen der Formel (I), in welcher R1 für Wasserstoff oder Methyl steht,Particular exceptions are in each case compounds of the formula (I) in which R 1 is hydrogen or methyl,
R2 für Chlor, Methyl, Difluormethyl oder Trifluormethyl steht,R 2 is chlorine, methyl, difluoromethyl or trifluoromethyl,
R5 für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Methoxy, iso-Propoxy oder Methylthio steht, wenn R3 für Wasserstoff und R4 für Fluor und m für 1 steht.R 5 is fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, iso-propoxy or methylthio, when R 3 is hydrogen and R 4 is fluorine and m is 1.
Bevorzugt sind solche Verbindungen der Formel (I), in welcher alle Reste jeweils die oben genannten bevorzugten Bedeutungen haben.Preference is given to those compounds of the formula (I) in which all radicals each have the abovementioned preferred meanings.
Besonders bevorzugt sind solche Verbindungen der Formel (I), in welcher alle Reste jeweils die oben genannten besonders bevorzugten Bedeutungen haben. Ganz besonders bevorzugt sind solche Verbindungen der Formel (I), in welcher alle Reste jeweils die oben genannten ganz besonders bevorzugten Bedeutungen haben.Particular preference is given to those compounds of the formula (I) in which all radicals each have the abovementioned particularly preferred meanings. Very particular preference is given to those compounds of the formula (I) in which all the radicals in each case have the above-mentioned very particularly preferred meanings.
Bevorzugt und jeweils als Teilmenge der oben genannten Verbindungen der Formel (I) zu verstehen sind folgende Gruppen von neuen Carboxamiden: Gruppe 1 : Biphenylthiazolcarboxamide der Formel (I-a)The following groups of new carboxamides are to be understood as being preferred and in each case as a subset of the abovementioned compounds of the formula (I): Group 1: biphenylthiazolecarboxamides of the formula (I-a)
in welcher R1, R2, R4, m und R5 die oben angegebenen Bedeutungen haben. in which R 1 , R 2 , R 4 , m and R 5 have the meanings given above.
Gruppe 2: Biphenylthiazolcarboxamide der Formel (I-b) in welcher R1, R2, R3A, R4, m und R5 die oben angegebenen Bedeutungen haben.Group 2: biphenylthiazolecarboxamides of the formula (Ib) in which R 1 , R 2 , R 3A , R 4 , m and R 5 have the meanings given above.
R3A steht bevorzugt für CrC6-Alkyl, CrC4-Alkylsulfinyl, CrC4-Alkylsulfonyl, Ci-C3-Alkoxy-Cr C3-alkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, Ci-C4-Halogenalkylthio, C,-C4-Halogenal- kylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C3-alkoxy-Ci-C3-alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3- alkyl, (CrC3-Alkyl)carbonyl-Ci-C3-alkyl, (CrC3-Alkoxy)carbonyl-CrC3-alkyl; Halogen-(Ci- C3-alkyl)carbonyl-Ci-C3-alkyl, Halogen-(Ci-C3-alkoxy)carbonyl-CrC3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen;R 3A is preferably C r C 6 alkyl, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, Ci-C 3 alkoxy-C r C 3 alkyl, C 3 -C 6 cycloalkyl; C r C 4 haloalkyl, Ci-C4-haloalkylthio, C, -C 4 -Halogenal- kylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C 3 alkoxy-Ci-C 3 alkyl, C 3 - C 8 -halo-cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 3 - alkyl, (C r C 3 alkyl) carbonyl-Ci-C 3 alkyl, (C r C 3 alkoxy) carbonyl-C r C 3 alkyl; Halogeno (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogeno (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms;
(C,-C6-Alkyl)carbonyl, (CrC4-Alkoxy)carbonyl, (CrC3-Alkoxy-Ci-C3-alkyl)carbonyl, (C3-C6- Cycloalkyl)carbonyl; (CrC4-Halogenalkyl)carbonyl, (CrC4-Halogenalkoxy)carbonyl, (Ha- logen-C]-C3-alkoxy-Ci-C3-alkyl)carbonyl, (C3-C6-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R6, -CONR7R8 oder -CH2NR9R10. R3A steht besonders bevorzugt für Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pentyl oder Hexyl, Methylsulfinyl, Ethylsulfinyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cy- clopropyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Trichlormethyl, Trifluorethyl, Difluor- methylthio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethylsulfinyl, Trifluorme- thylsulfonyl, Trifluormethoxymethyl; Formyl, -CH2-CHO, -(CH2VCHO, -CH2-CO-CH3, -CH2-CaCH2CH3, -CH2-CO-CH(CH3)z, -(CH2^-CO-CH3, -(CHz)2-CO-CH2CH3, -(CH2VCO-CH(CH3V -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CH2VCO2CH3, -(CH2)Z-CO2CH2CH3, -(CH2VCO2CH(CH3V -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CH2VCO-CH2CF3, -(CHz)2-CO-CH2CCl3,(C, -C 6 alkyl) carbonyl, (C r C 4 alkoxy) carbonyl, (C r C 3 alkoxy-Ci-C 3 alkyl) carbonyl, (C 3 -C 6 - cycloalkyl) carbonyl; (C r C 4 haloalkyl) carbonyl, (C r C 4 haloalkoxy) carbonyl, (halogen-C] -C3 -alkoxy-Ci-C 3 alkyl) carbonyl, (C 3 -C 6 halocycloalkyl ) carbonyl each having 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10 . R 3A particularly preferably represents methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso- , sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, Trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; Formyl, -CH 2 -CHO, - (CH 2 VCHO, -CH 2 -CO-CH 3 , -CH 2 -CaCH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) z, - (CH 2 ^ -CO-CH 3 , - (CH 2 ) 2 -CO-CH 2 CH 3 , - (CH 2 VCO-CH (CH 3 V -CH 2 -CO 2 CH 3 , -CH 2 -CO 2 CH 2 CH 3 , -CH 2 -CO 2 CH (CH 3 ) 2 , - (CH 2 VCO 2 CH 3 , - (CH 2 ) Z -CO 2 CH 2 CH 3 , - (CH 2 VCO 2 CH (CH 3 V -CH 2 -CO-CF 3 , -CH 2 -CO-CCl 3 , -CH 2 -CO-CH 2 CF 3 , -CH 2 -CO-CH 2 CCl 3 , - (CH 2 VCO-CH 2 CF 3 , - ( CHz) 2 -CO-CH 2 CCl 3 ,
-CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCIZCCI3, -(CH2VCOZCHZCF3, -(CH2VCO2CF2CF3, -(CHz)2-CO2CH2CCl3, -(CH2VCO2CCl2CCl3; Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, tert-Butoxycarbonyl, Cyclopropylcarbonyl; Trifluorme- thylcarbonyl, Trifluormethoxycarbonyl, oder -C(=O)C(=O)R6, -CONR7R8 oder -CH2NR9R10. R steht ganz besonders bevorzugt für Methyl, Methoxymethyl, Formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CHrCO-CH^Ha^ -C(=O)CHO, -C(=O)C(=O)CH3, -C(O)C(O)CH2OCH3, -C(O)CO2CH3, -C(=O)CO2CH2CH3.-CH 2 -CO 2 CH 2 CF 3 , -CH 2 -CO 2 CF 2 CF 3 , -CH 2 -CO 2 CH 2 CCl 3 , -CH 2 -CO 2 CCI Z CCI 3 , - (CH 2 VCO Z CH Z CF 3, - (CH 2 VCO 2 CF 2 CF 3, - (CHz) 2 -CO 2 CH 2 CCl 3, - (CH 2 VCO 2 CCl 2 CCl 3; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso- Propylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl, trifluoromethylcarbonyl, trifluoromethoxycarbonyl, or -C (= O) C (= O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10 , R very particularly preferably represents methyl, methoxymethyl, formyl, -CH 2 -CHO, - (CH 2 ) 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CHrCO- CH 2 Ha 2 -C (= O) CHO, -C (= O) C (= O) CH 3 , -C (O) C (O) CH 2 OCH 3 , -C (O) CO 2 CH 3 , -C (= O) CO 2 CH 2 CH 3 .
Gruppe 3: Biphenylthiazolcarboxamide der Formel (I-c)Group 3: biphenylthiazolecarboxamides of the formula (I-c)
in welcher R1, R2, R3, R4, m und R5 die oben angegebenen Bedeutungen haben. in which R 1 , R 2 , R 3 , R 4 , m and R 5 have the meanings given above.
Gruppe 4: Biphenylthiazolcarboxamide der Formel (I-d)Group 4: biphenylthiazolecarboxamides of the formula (I-d)
in welcher R > 1 , τ R>2 , Ώ R3 , R , m . , u.n„dJ r R>5 die oben angegebenen Bedeutungen haben. in which R> 1, τ R> 2, Ώ R 3 , R, m. , and "R"> 5 have the meanings given above.
Gruppe 5: Biphenylthiazolcarboxamide der Formel (I-e)Group 5: biphenylthiazolecarboxamides of the formula (I-e)
in welcher R > 1 , τ R>2 , τ R>3 , - RΓJ4 , m und R die oben angegebenen Bedeutungen haben. in which R> 1, τ R> 2, τ R> 3, RΓJ 4, m and R have the meanings given above.
Gruppe 6: Biphenylthiazolcarboxamide der Formel (I-f)Group 6: biphenylthiazolecarboxamides of the formula (I-f)
in welcher R , R , R , R und R die oben angegebenen Bedeutungen haben. Gruppe 7: Biphenylthiazolcarboxamide der Formel (I-g) in which R, R, R, R and R have the meanings given above. Group 7: Biphenylthiazolecarboxamides of the formula (Ig)
in welcher R , R , R , R und R die oben angegebenen Bedeutungen haben. in which R, R, R, R and R have the meanings given above.
Gruppe 9: Biphenylthiazolcarboxamide der Formel (I-h)Group 9: biphenylthiazolecarboxamides of the formula (I-h)
in welcher R1, R2, R3, R4 und R5 die oben angegebenen Bedeutungen haben. in which R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above.
Gruppe 9: Biphenylthiazolcarboxamide der Formel (I-i)Group 9: Biphenylthiazolecarboxamides of the formula (I-i)
in welcher R1, R2, R3 und R5 die oben angegebenen Bedeutungen haben und R4A und R4B unabhängig voneinander die Bedeutungen von R4 haben. in which R 1 , R 2 , R 3 and R 5 have the meanings given above and R 4A and R 4B independently of one another have the meanings of R 4 .
Hervorgehoben sind Verbindungen der Formel (I) (und ebenso der Gruppen 1 bis 9), in welcher R1 für Methyl steht.Emphasis is given to compounds of the formula (I) (and also groups 1 to 9) in which R 1 is methyl.
Hervorgehoben sind Verbindungen der Formel (I) (und ebenso der Gruppen 1 bis 9), in welcher R2 für Difluormethyl oder Trifluormethyl steht.Emphasis is given to compounds of the formula (I) (and also groups 1 to 9) in which R 2 is difluoromethyl or trifluoromethyl.
Hervorgehoben sind Verbindungen der Formel (I) (und ebenso der Gruppen 1 bis 9), in welcher R4 für Chlor, Brom, CrC4-Alkyl, C1-C4-AIkOXy, C,-C4-Alkylthio oder CrC4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht.Emphasis is given to compounds of the formula (I) (and also groups 1 to 9) in which R 4 is chlorine, bromine, C r C 4 alkyl, C 1 -C 4 alkoxy, C, -C 4 alkylthio or C r C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms.
Hervorgehoben sind Verbindungen der Formel (I) (und ebenso der Gruppen 1 bis 9), in welcher R4 für Chlor, Methyl, Trifluormethyl, Methoxy oder Methylthio, insbesondere für Chlor, steht. Hervorgehoben sind Verbindungen der Formel (I) (und ebenso der Gruppen 1 bis 9), in welcher R3 für Formyl steht.Emphasis is given to compounds of the formula (I) (and also groups 1 to 9) in which R 4 is chlorine, methyl, trifluoromethyl, methoxy or methylthio, in particular chlorine. Emphasis is given to compounds of the formula (I) (and also groups 1 to 9) in which R 3 is formyl.
Hervorgehoben sind außerdem Verbindungen der Formel (I) (und ebenso der Gruppen 1 bis 9), in welcher R3 für -C(=O)C(=O)R6 steht, wobei R6 die oben angegebenen Bedeutungen hat.Also highlighted are compounds of formula (I) (and also groups 1 to 9) in which R 3 is -C (= O) C (= O) R 6 , wherein R 6 has the meanings given above.
Gesättigte oder ungesättigte Kohlenwasserstoffreste wie Alkyl oder Alkenyl können, auch in Verbin¬ dung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein.Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. So schließt die Definition Dialkylamino auch eine unsymmetrisch durch Alkyl substituierte Aminogruppe wie z.B. Methyl-ethylamino ein.Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different. Thus, the definition of dialkylamino also includes an unsymmetrically alkyl-substituted amino group, such as e.g. Methyl ethylamino.
Durch Halogen substituierte Reste, wie z.B. Halogenalkyl, sind einfach oder mehrfach halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom und Iod, insbesondere für Fluor, Chlor und Brom.Halogen substituted radicals, e.g. Haloalkyl, are halogenated singly or multiply. For multiple halogenation, the halogen atoms may be the same or different. Halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen können zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechend. Insbesondere können die in den Gruppen 1 bis 6 genannten Verbindungen sowohl mit den allgemei¬ nen wie auch mit bevorzugten, besonders bevorzugten usw. Bedeutungen kombiniert werden, wobei auch hier jeweils alle Kombinationen zwischen den Vorzugsbereichen möglich sind.The general or preferred radical definitions or explanations given above can be combined as desired between the respective ranges and preferred ranges. They apply accordingly to the end products as well as to the precursors and intermediates. In particular, the compounds mentioned in groups 1 to 6 can be combined with the general as well as with preferred, particularly preferred meanings, whereby all combinations between the preferred ranges are also possible here.
Beschreibung der crfindungsgemäßen Verfahren zum Herstellen der Biphenylthiazolcarbox- amide der Formel (I) sowie der ZwischenprodukteDescription of the process according to the invention for preparing the biphenylthiazolecarboxamides of the formula (I) and the intermediates
Verfahren (a)Method (a)
Verwendet man 2-Methyl-4-(trifluormefhyl)-l,3-thiazol-5-carbonylchloride und 4-Chlor-4'-fluorbi- phenyl-2-amin als Ausgangsstoffe, so kann das erfindungsgemäße Verfahren (a) durch das folgende Formelschema veranschaulicht werden: If 2-methyl-4- (trifluoromethyl) -1,3-thiazole-5-carbonyl chloride and 4-chloro-4'-fluorobiphenyl-2-amine are used as starting materials, process (a) according to the invention can be replaced by the following Formula Scheme to be illustrated:
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötigten Carbon¬ säure-Derivate sind durch die Formel (II) allgemein definiert. In dieser Formel (Q) stehen R1 und R2 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden. X1 steht bevorzugt für Chlor, Brom oder Hydroxy.The carboxylic acid derivatives required for carrying out the process (a) according to the invention as starting materials are generally defined by the formula (II). In this formula (Q) R 1 and R 2 are preferred, particularly preferred and very particularly preferred meanings, the formula already mentioned in connection with the description of the inventive compounds (I) as being preferred, particularly preferred and very particularly preferably these residues were indicated. X 1 is preferably chlorine, bromine or hydroxyl.
Die Carbonsäure-Derivate der Formel (II) sind bekannt und/oder lassen sich nach bekannten Verfah- ren herstellen (vgl. WO 03/066609, WO 03/066610, EP-A 0 545 099, EP-A 0 589301, EP-A 0 589 313 und US 3,547,917).The carboxylic acid derivatives of the formula (II) are known and / or can be prepared by known processes (cf., WO 03/066609, WO 03/066610, EP-A 0 545 099, EP-A 0 589 301, EP-A A 0 589 313 and US 3,547,917).
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe weiterhin benötig¬ ten Biphenylamine sind durch die Formel (III) allgemein definiert. In dieser Formel (IH) haben R3, R4, m und R5 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) für diese Reste bzw. diesen Index als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt angegeben wurden.The biphenylamines which are furthermore required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (III). In this formula (III) R 3, R 4, m and R 5 are preferred, particularly preferred and very particularly preferably have those meanings already mentioned in connection with the description of the compounds of formula (I) according to the invention for these radicals or this Index as preferred, particularly preferred or very particularly preferred.
Die Biphenylamine der Formel (HI) sind teilweise bekannt oder können nach bekannten Verfahren erhalten werden (vgl. z.B. WO 03/070705, WO 99/09013, WO 97/08148, JP 2001-302605).The biphenylamines of the formula (HI) are known in some cases or can be obtained by known processes (cf., for example, WO 03/070705, WO 99/09013, WO 97/08148, JP 2001-302605).
Es ist auch möglich, zunächst Biphenylamine der Formel (HI-a)It is also possible to first of all biphenylamines of the formula (HI-a)
in welcher R3Λ, R4, m und R5 die oben angegebenen Bedeutungen haben, herzustellen und diese gege¬ benenfalls anschließend mit Halogeniden der Formel (VIlI) R^-X4 (VEI) in welcher R3A und X4 die oben angegebenen Bedeutungen haben, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umzusetzen. [Die Reaktionsbedingungen des erfindungsge¬ mäßen (e) gelten entsprechend.] in which R 3Λ , R 4 , m and R 5 have the abovementioned meanings, and these are then optionally reacted with halides of the formula (VIlI) R ^ -X 4 (VEI) in which R 3A and X 4 have the meanings given above, in the presence of a base and in the presence of a diluent. [The reaction conditions of erfindungsge¬ Maäßen (e) apply accordingly.]
Verfahren (b)Method (b)
Verwendet man N-(2-Brom-5-chloφhenyl)-2-methyl-4-(trifluormethyl)-l,3-thiazol-5-carboxamid und (4-Methylphenyl)boronsäure als Ausgangsstoffe sowie einen Katalysator, so kann der Verlauf des erfindungsgemäßen Verfahrens (b) durch das folgende Formelschema veranschaulicht werden:If N- (2-bromo-5-chloro-phenyl) -2-methyl-4- (trifluoromethyl) -l, 3-thiazole-5-carboxamide and (4-methylphenyl) boronic acid are used as starting materials and a catalyst, the course of the reaction can be determined of the process (b) according to the invention are illustrated by the following equation:
Die zur Durchführung des erfindungsgemäßen Verfahrens (b) als Ausgangsstoffe benötigten HaIo- gencarboxamide sind durch die Formel (IV) allgemein definiert. In dieser Formel (TV) haben R1, R2, R3, R4 und m bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutun¬ gen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste bzw. diesen Index angegeben wurden. X2 steht für Brom oder Iod.The halo-carboxamides required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (IV). In this formula (IV) R 1, R 2, R 3, R 4 and m have preferred, particularly preferred and very particularly preferably those Bedeutun¬ gene corresponding to the formula already mentioned in connection with the description of the inventive compounds (I) as preferred, particularly preferred or very particularly preferred for these radicals or this index. X 2 is bromine or iodine.
Die Halogencarboxamide der Formel (FV) sind noch nicht bekannt. Sie sind als neue chemische Verbindungen ebenfalls Gegenstand der vorliegenden Anmeldung. Sie werden erhalten, indem man (f) Carbonsäure-Derivate der Formel (IT)The Halogencarboxamide of formula (FV) are not yet known. They are also the subject of the present application as novel chemical compounds. They are obtained by reacting (f) carboxylic acid derivatives of the formula (IT)
in welcher R1, HaI und X1 die oben angegebenen Bedeutungen haben, mit Halogenanilinen der Formel (FX), in which R 1 , Hal and X 1 have the meanings given above, with haloanilines of the formula (FX),
in welcher R3, R4, m und X2 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Konden¬ sationsmittels, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels, umsetzt. in which R 3 , R 4 , m and X 2 have the meanings given above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Die zur Durchführung des erfindungsgemäßen Verfahrens (f) als Ausgangsstoffe benötigten Carbonsäure-Derivate der Formel (II) sind bereits im Zusammenhang mit dem erfindungsgemäßen Verfahren (a) beschrieben worden.The carboxylic acid derivatives of the formula (II) required as starting materials for carrying out the process (f) according to the invention have already been described in connection with the process (a) according to the invention.
Die zur Durchführung des erfindungsgemäßen Verfahrens (f) weiterhin als Ausgangsstoffe benötig- ten Halogenaniline sind durch die Formel (DC) allgemein definiert. In dieser Formel (Dt) haben R3, R4, m und X2 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Be¬ deutungen, die bereits im Zusammenhang mit der Beschreibung der erfϊndungsgemäßen Verbindun¬ gen der Formel (I) bzw. der Vorprodukte der Formel (IV) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste bzw. diesen Index angegeben wurden.The haloanilines which are furthermore required as starting materials for carrying out the process (f) according to the invention are generally defined by the formula (DC). In this formula (Dt) R 3, R 4, m and X 2 being preferred, particularly preferred and very particularly preferably have those meanings Be¬, the gene already in connection with the description of the inventive Verbindun¬ of formula (I) or the precursors of the formula (IV) have been indicated as being preferred, particularly preferred or very particularly preferred for these radicals or this index.
Die Halogenaniline der Formel (IX) sind handelsübliche Synthesechemikalien oder können nach bekannten Verfahren erhalten werden.The haloanilines of the formula (IX) are commercially available synthetic chemicals or can be obtained by known methods.
Es ist auch möglich, zunächst Halogenaniline der Formel (IX-a)It is also possible first to use haloanilines of the formula (IX-a)
in welcher R4 und X2 die oben angegebenen Bedeutungen haben, herzustellen und diese gegebenen¬ falls anschließend mit Halogeniden der Formel (VUI) R3*— X4 (VHI) in welcher R3A und X4 die oben angegebenen Bedeutungen haben, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umzusetzen. [Die Reaktionsbedingungen des erfϊndungsge¬ mäßen (i) gelten entsprechend.] in which R 4 and X 2 have the meanings given above, and if appropriate subsequently with halides of the formula (VUI) R 3 * - X 4 (VHI) in which R 3A and X 4 have the meanings given above, in Present a base and react in the presence of a diluent. [The reaction conditions of the erfϊndungsge¬ maäßen (i) apply accordingly.]
Die zur Durchführung des erfindungsgemäßen Verfahrens (b) weiterhin als Ausgangsstoffe benötig¬ ten Boronsäure-Derivate sind durch die Formel (V) allgemein definiert. In dieser Formel (V) hat R5 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben wurden. G1 und G2 stehen jeweils für Wasserstoff oder zusammen für Tetramethylethylen. Die Boronsäure-Derivate der Formel (V) sind bekannt und/oder lassen sich nach bekannten Ver¬ fahren herstellen (vgl. z.B. WO 01/90084, JP-A 2001-302605 und US 5,633,218).The boronic acid derivatives which are furthermore required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (V). In this formula (V), R 5 has preferably, more preferably or very particularly preferably those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) as being preferred, particularly preferred or very particularly preferred for this radical were. G 1 and G 2 are each hydrogen or together are tetramethylethylene. The boronic acid derivatives of the formula (V) are known and / or can be prepared by known processes (cf., for example, WO 01/90084, JP-A 2001-302605 and US Pat. No. 5,633,218).
Verfahren (c)Method (c)
Verwendet man [5-Methoxy-2-({[2-methyl-4-(trifluormethyl)-l ,3-thiazol-5-yl]carbonyl}amino)phe- nyl]boronsäure und l-Brom-4-chlorbenzol als Ausgangsstoffe sowie einen Katalysator, so kann der Verlauf des erfindungsgemäßen Verfahrens (c) durch das folgende Formelschema veranschaulicht werden.Using [5-methoxy-2 - ({[2-methyl-4- (trifluoromethyl) -l, 3-thiazol-5-yl] carbonyl} amino) phenyl] boronic acid and 1-bromo-4-chlorobenzene as Starting materials and a catalyst, the course of the process (c) according to the invention can be illustrated by the following equation.
Katalysatorcatalyst
Die zur Durchführung des erfindungsgemäßen Verfahrens (c) als Ausgangsstoffe benötigten Boron¬ säure-Derivate sind durch die Formel (VT) allgemein definiert. In dieser Formel (VI) haben R1, R2, R3, R4 und m bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste bzw. diesen Index angegeben wurden. G3 und G4 stehen jeweils für Wasserstoff oder zusammen für Tetra- methylethylen. For carrying out the process (c) required as starting materials Boron¬ acid derivatives are generally defined by the formula (VT). In this formula (VI) R 1, R 2, R 3, R 4 and m have preferred, particularly preferred and very particularly preferably have those meanings already mentioned in connection with the description of the compounds of formula (I) as being preferred according to the invention, particularly preferred or very particularly preferred for these radicals or this index. G 3 and G 4 are each hydrogen or together are tetra methylethylene.
Die Boronsäure-Derivate der Formel (VI) sind noch nicht bekannt. Sie sind neue chemische Verbin¬ dungen und ebenfalls Gegenstand der vorliegenden Anmeldung. Sie werden erhalten, indem man (g) ein Carbonsäure-Derivat der Formel (IT)The boronic acid derivatives of the formula (VI) are not yet known. They are new chemical compounds and are also the subject of the present application. They are obtained by reacting (g) a carboxylic acid derivative of the formula (IT)
in welcher R1, R2 und X1 die oben angegebenen Bedeutungen haben, mit einem Anilinboronsäure-Derivat der Formel (X) in which R 1 , R 2 and X 1 have the meanings given above, with an anilinboronic acid derivative of the formula (X)
in welcher R3, R4, m, G3 und G4 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Konden¬ sationsmittels, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels, umsetzt. in which R 3 , R 4 , m, G 3 and G 4 have the meanings given above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Die zur Durchführung des erfϊndungsgemäßen Verfahrens (g) als Ausgangsstoffe benötigten Carbon¬ säure-Derivate der Formel (II) sind bereits im Zusammenhang mit dem erfindungsgemäßen Verfahren (a) beschrieben worden.The carboxylic acid derivatives of the formula (II) required as starting materials for carrying out the process (g) according to the invention have already been described in connection with the process (a) according to the invention.
Die weiterhin zur Durchführung des erfindungsgemäßen Verfahrens (g) als Ausgangsstoffe benötig- ten Anilinboronsäure-Derivate sind durch die Formel (X) allgemein definiert. In dieser Formel (X) haben R3, R4 und m bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Be¬ deutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindun¬ gen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste bzw. diesen Index angegeben wurden. G3 und G4 stehen jeweils für Wasserstoff oder gemeinsam für Tetramethylethylen.The anilinboronic acid derivatives furthermore required for carrying out the process (g) according to the invention as starting materials are generally defined by the formula (X). In this formula (X) R 3, R 4 and m have preferred, particularly preferred and very particularly preferably have those meanings Be¬, the gene already in connection with the description of Verbindun¬ invention of the formula (I) as being preferred, particularly preferably or very particularly preferably for these radicals or this index. G 3 and G 4 are each hydrogen or together are tetramethylethylene.
Die Anilinboronsäure-Derivate der Formel (X) sind bekannte Synthesechemikalien oder können nach bekannten Verfahren erhalten werden.The aniline boronic acid derivatives of the formula (X) are known synthetic chemicals or can be obtained by known methods.
Es ist auch möglich, zunächst Anilinboronsäure-Derivate der Formel (X-a)It is also possible to first prepare anilinboronic acid derivatives of the formula (X-a)
in welcher R4, m, G3 und G4 die oben angegebenen Bedeutungen haben, herzustellen und diese gege¬ benenfalls anschließend mit Halogeniden der Formel (VlII) in welcher R3A und X4 die oben angegebenen Bedeutungen haben, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umzusetzen. [Die Reaktionsbedingungen des erfindungsge¬ mäßen (i) gelten entsprechend.] in which R 4 , m, G 3 and G 4 have the abovementioned meanings, and these are then subsequently reacted with halides of the formula (VIII) in which R 3A and X 4 have the abovementioned meanings, in the presence of a base and in the presence of a diluent. [The reaction conditions of erfindungsge¬ maäßen (i) apply accordingly.]
Die zur Durchführung des erfindungsgemäßen Verfahrens (c) weiterhin als Ausgangsstoffe benötig- ten Phenyl-Derivate sind durch die Formel (VT!) allgemein definiert. In dieser Formel (VII) hat R5 be¬ vorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfuidungsgemäßen Verbindungen der Formel (I) als be- vorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben wurden. X3 steht für Chlor, Brom, Iod oder Trifluormethylsulfonat.The phenyl derivatives which are furthermore required as starting materials for carrying out the process (c) according to the invention are generally defined by the formula (IV!). In this formula (VII) R 5 vorzugt be¬, particularly preferred and very particularly preferably have those meanings which have undergone working in connection with the description of erfuidungsgemäßen compounds of formula (I) as Preferably, particularly preferred or very particularly preferred for this remainder. X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate.
Die Phenyl-Derivate der Formel (VII) sind bekannte Synthesechemikalien.The phenyl derivatives of the formula (VII) are known synthetic chemicals.
Verfahren (d)Method (d)
Verwendet man N-(2-Brom-4-methoxyphenyl)-2-methyl-4-(trif!uormethyl)-l,3-thiazol-5-carboxamid und l-Brom-4-chlorbenzol als Ausgangsstoffe sowie einen Katalysator und 4,4,4',4',5,5,5',5'-Octa- methyl-2,2'-bis-l,3,2-dioxaborolan, so kann der Verlauf des erfindungsgemäßen Verfahrens (d) durch das folgende Formelschema veranschaulicht werden.Using N- (2-bromo-4-methoxyphenyl) -2-methyl-4- (trifluoromethyl) -l, 3-thiazole-5-carboxamide and 1-bromo-4-chlorobenzene as starting materials and a catalyst and 4 , 4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-l, 3,2-dioxaborolan, the course of the process (d) according to the invention by the the following formula schema are shown.
Die zur Durchführung des erfϊndungsgemäßen Verfahrens (d) als Ausgangsstoffe benötigten HaIo- gencarboxamide der Formel (IV), sowie die Phenyl-Derivate der Formel (VII) sind bereits im Zusammenhang mit den erfindungsgemäßen Verfahren (b) und (c) beschrieben worden.The halo-carboxamides of the formula (IV) required as starting materials for carrying out the process (d) according to the invention and the phenyl derivatives of the formula (VII) have already been described in connection with the processes (b) and (c) according to the invention.
Das weiterhin zur Durchführung des erfϊndungsgemäßen Verfahrens (d) benötigte 4,4,4',4',5,5,5',5'- Octamethyl-2,2'-bis-l,3,2-dioxaborolan ist eine handelsübliche Synthesechemikalie.The 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-l, 3,2-dioxaborolane furthermore required for carrying out the process (d) according to the invention is a commercially available one chemical for synthesis.
Verfahren (e)Method (s)
Verwendet man N-(4-Chloro-4'-fluorbiphenyl-2-yl)-2-methyl-4-(trifluormethyl)- 1 ,3-thiazol-5-carbox- amid und Acetylchlorid als Ausgangsstoffe, so kann der Verlauf des erfindungsgemäßen Verfahrens (e) durch das folgende Formelschema veranschaulicht werden:If N- (4-chloro-4'-fluorobiphenyl-2-yl) -2-methyl-4- (trifluoromethyl) -1,3-thiazole-5-carboxamide and acetyl chloride are used as starting materials, the course of the process (e) according to the invention are illustrated by the following formula scheme:
Die zur Durchführung des erfindungsgemäßen Verfahrens (e) als Ausgangsstoffe benötigten Biphe- nylthiazolcarboxamide sind durch die Formel (I-a) allgemein definiert. In dieser Formel (I-a) haben R1, R2, R4, R5 und n bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Be- deutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindun¬ gen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste bzw. diesen Index angegeben wurden.The biphenyl-thiazolecarboxamides required as starting materials for carrying out the process (e) according to the invention are generally defined by the formula (Ia). In this formula (Ia) R 1, R 2, R 4, R 5 and n are preferred, particularly preferred and very particularly preferred are those loading meanings which have already been stated in connection with the description of the compounds according to the invention of the formula (I) as being preferred, particularly preferred or very particularly preferred for these radicals or this index.
Die Verbindungen der Formel (I-a) sind erfindungsgemäße Verbindungen und können nach den Verfahren (a) bis (d) hergestellt werden.The compounds of the formula (I-a) are compounds according to the invention and can be prepared by the processes (a) to (d).
Die zur Durchfuhrung des erfindungsgemäßen Verfahrens (e) weiterhin als Ausgangsstoffe benötig¬ ten Halogenide sind durch die Formel (VHT) allgemein definiert. In dieser Formel (VDDT) steht R3A be- vorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diejenigen Bedeutungen, die bereits oben für die Verbindungen der Formel (I-b) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben wurden. X4 steht für Chlor, Brom oder Iod.The halides which are furthermore required as starting materials for carrying out the process (e) according to the invention are generally defined by the formula (VHT). In this formula (VDDT), R 3A is preferred, particularly preferably or very particularly preferably for those meanings which have already been indicated above for the compounds of the formula (Ib) as being preferred, particularly preferred or very particularly preferred for this radical , X 4 is chlorine, bromine or iodine.
Halogenide der Formel (VIQ) sind bekannt.Halides of the formula (VIQ) are known.
Reaktionsbedingungenreaction conditions
Als Verdünnungsmittel zur Durchführung der erfϊndungsgemäßen Verfahren (a), (f) und (g) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicy- clische oder aromatische Kohlenwasserstoffe, wie z.B. Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan, Benzol, Toluol, Xylol oder Decalin; halogenierte Kohlenwasserstoffe, wie z.B. Chlorbenzol, Dichlorbenzol, Dichlormethan, Chloroform, Tetrachlormethan, Dichlorethan oder Tri- chlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-Amylether, Di- oxan, Tetrahydrofuran, 1,2- Dimethoxyethan, 1,2-Diethoxyethan oder Anisol; Ketone, wie Aceton, Butanon, Methyl-isobutylketon oder Cyclohexanon; Nitrile, wie Acetonitril, Propionitril, n- oder i- Butyronitril oder Benzonitril; Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N- Methylformanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; deren Gemische mit Wasser oder reines Wasser.Suitable diluents for carrying out the processes (a), (f) and (g) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as e.g. Petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g. Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; their mixtures with water or pure water.
Die erfindungsgemäßen Verfahren (a), (f) und (g) werden gegebenenfalls in Gegenwart eines geeig- neten Säureakzeptors durchgeführt. Als solche kommen alle üblichen anorganischen oder organi¬ schen Basen infrage. Hierzu gehören vorzugsweise Erdalkalimetall- oder Alkalimetallhydride, -hy- droxide, -amide, -alkoholate, -acetate, -carbonate oder -hydrogencarbonate, wie z.B. Natriumhydrid, Natriumamid, Lithiumdiisopropylamid, Natrium-methylat, Natrium-ethylat, Kalium-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Natriumacetat, Natriumcarbonat, Kaliumcarbonat, Kalium- hydrogencarbonat, Natriumhydrogencarbonat oder Ammoniumcarbonat, sowie tertiäre Amine, wie Trimethylamin, Triethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N-Methylpiperidin, N-Methylmoφholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).If appropriate, the processes (a), (f) and (g) according to the invention are carried out in the presence of a suitable acid acceptor. As such, all customary inorganic or organic bases are suitable. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, for example sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide , Sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, Pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
Die erfindungsgemäßen Verfahren (a), (f) und (g) werden gegebenenfalls in Gegenwart eines geeig- neten Kondensationsmittels durchgeführt. Als solche kommen alle üblicherweise für derartige Ami- dierungsreaktionen verwendbaren Kondensationsmittel infrage. Beispielhaft genannt seien Säure- halogenidbildner wie Phosgen, Phosphortribromid, Phosphortrichlorid, Phosphorpentachlorid, Phosphoroxychlorid oder Thionylchlorid; Anhydridbildner wie Chlorameisensäureethylester, Chlor¬ ameisensäuremethylester, Chlorameisensäureisopropylester, Chlorameisensäureisobutylester oder Methansulfonylchlorid; Carbodiimide, wie NjN'-Dicyclohexylcarbodiimid (DCC) oder andere übliche Kondensationsmittel, wie Phosphorpentoxid, Polyphosphorsäure, N,N'-Carbonyldiimidazol, 2-Ethoxy-N-ethoxycarbonyl-l ,2-dihydrochinolin (EEDQ), Triphenylphosphin/Tetrachlorkohlenstoff oder Brom-tripyrrolidinophosphonium-hexafluorophosphat.The processes (a), (f) and (g) according to the invention are optionally carried out in the presence of a suitable condensing agent. As such, all conventionally suitable for such Ami- dierungsreaktionen condensing agent come into question. Examples which may be mentioned are acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydridbildner such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; Carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride or bromine tripyrrolidinophosphonium hexafluorophosphate.
Die erfindungsgemäßen Verfahren (a), (f) und (g) werden gegebenenfalls in Gegenwart eines Kataly¬ sators durchgeführt. Beispielsweise genannt seien 4-Dimethylaminopyridin, 1-Hydroxy-benzotriazol oder Dimethylformamid.If appropriate, the processes (a), (f) and (g) according to the invention are carried out in the presence of a catalyst. Examples which may be mentioned are 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.
Die Reaktionstemperaturen können bei der Durchführung der erfindungsgemäßen Verfahren (a), (f) und (g) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 00C bis 1500C, vorzugsweise bei Temperaturen von 00C bis 800C.The reaction temperatures can be varied within a substantial range when carrying out the processes (a), (f) and (g) according to the invention. In general, one works at temperatures of 0 0 C to 150 0 C, preferably at temperatures of 0 0 C to 80 0 C.
Zur Durchführung des erfindungsgemäßen Verfahrens (a) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Carbonsäure-Derivates der Formel (II) im Allgemeinen 0,8 bis 15 Mol, vorzugsweise 0,8 bis 8 Mol an Anilin-Derivat der Formel (TS) ein.For carrying out the process (a) according to the invention for the preparation of the compounds of the formula (I), in general 0.8 to 15 mol, preferably 0.8 to 8 mol, of aniline derivative are employed per mole of the carboxylic acid derivative of the formula (II) of the formula (TS).
Zur Durchführung des erfindungsgemäßen Verfahrens (f) zur Herstellung der Verbindungen der Formel (TV) setzt man pro Mol des Carbonsäure-Derivates der Formel (II) im Allgemeinen 0,8 bis 15 Mol, vorzugsweise 0,8 bis 8 Mol an Halogenaniline der Formel (TX) ein.For carrying out the process (f) according to the invention for the preparation of the compounds of the formula (TV), in general from 0.8 to 15 mol, preferably from 0.8 to 8 mol, of haloanilines of the formula are employed per mole of the carboxylic acid derivative of the formula (II) (TX).
Zur Durchführung des erfindungsgemäßen Verfahrens (g) zur Herstellung der Verbindungen der Formel (VI) setzt man pro Mol des Carbonsäure-Derivates der Formel (II) im Allgemeinen 0,8 bis 15 Mol, vorzugsweise 0,8 bis 8 Mol an Anilinboronsäure-Derivat der Formel (X) ein.For carrying out the process (g) according to the invention for preparing the compounds of the formula (VI), in general 0.8 to 15 mol, preferably 0.8 to 8 mol, of anilinboronic acid derivative are employed per mole of the carboxylic acid derivative of the formula (II) of the formula (X).
Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren (b), (c) und (d) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicycli- sehe oder aromatische Kohlenwasserstoffe, wie z.B. Petrolether, Hexan, Heptan, Cyclohexan, Methyl- cyclohexan, Benzol, Toluol, Xylol oder Decalin; Ether, wie Diethylether, Diisopropylether, Methyl-t- butylether, Methyl-t-Amylether, Dioxan, Tetrahydrofliran, 1,2-Dimethoxyethan, 1,2-Diethoxyethan oder Anisol; Nitrile, wie Acetonitril, Propionitril, n- oder i-Butyronitril oder Benzonitril; Amide, wie N5N-Di- methylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methylpyrrolidon oder Hexamethyl- phosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester; Sulfoxide, wie Dimethylsulfoxid; Sulfone, wie Sulfolan; Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, n-, i-, sec- oder tert-Butanol, Ethandiol, Propan-l,2-diol, Ethoxyethanol, Methoxyethanol, Diethylenglykolmo- nomethylether, Diethylenglykolmonoethylether, deren Gemische mit Wasser oder reines Wasser.Suitable diluents for carrying out the processes (b), (c) and (d) according to the invention are all inert organic solvents. These include preferably aliphatic, alicyclic see or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N 5 N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethyl phosphoric acid triamide; Esters, such as methyl acetate or ethyl acetate; Sulfoxides, such as dimethylsulfoxide; Sulfones, such as sulfolane; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-l, 2-diol, ethoxyethanol, methoxyethanol, diethylene glycol, 2,2'-diethylenglykolmonoethylether whose mixtures with Water or pure water.
Die Reaktionstemperaturen können bei der Durchführung der erfindungsgemäßen Verfahren (b), (c) und (d) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 00C bis 1800C, vorzugsweise bei Temperaturen von 200C bis 1500C.The reaction temperatures can be varied within a substantial range when carrying out the processes (b), (c) and (d) according to the invention. In general, one works at temperatures of 0 0 C to 180 0 C, preferably at temperatures of 20 0 C to 150 0 C.
Die der erfindungsgemäßen Verfahren (b), (c) und (d) werden gegebenenfalls in Gegenwart eines ge¬ eigneten Säureakzeptors durchgeführt. Als solche kommen alle üblichen anorganischen oder organi¬ schen Basen infrage. Hierzu gehören vorzugsweise Erdalkalimetall- oder Alkalimetallhydride, -hy- droxide, -amide, -alkoholate, -acetate, fluoride, phosphate, -carbonate oder -hydrogencarbonate, wie z.B. Natriumhydrid, Natriumamid, Lithiumdiisopropylamid, Natrium-methylat, Natrium-ethylat, Kalium-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Natriumacetat, Natriumphosphat, Kalium¬ phosphat, Kaliumfluorid, Cäsiumfluorid, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencarbo- nat, Natriumhydrogencarbonat oder Cäsiumcarbonat, sowie tertiäre Amine, wie Trimethylamin, Tri- ethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N-Methylpiperi- din, N-Methylmoφholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclo- nonen (DBN) oder Diazabicycloundecen (DBU).The processes (b), (c) and (d) according to the invention are optionally carried out in the presence of a suitable acid acceptor. As such, all customary inorganic or organic bases are suitable. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, fluorides, phosphates, carbonates or hydrogencarbonates, such as, for example, Sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, sodium phosphate, potassium phosphate, potassium fluoride, cesium fluoride, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclo - nonene (DBN) or diazabicycloundecene (DBU).
Die der erfindungsgemäßen Verfahren (b), (c) und (d) werden in Gegenwart eines Katalysators, wie z.B. eines Palladiumsalzes oder -komplexes, durchgeführt. Hierzu kommen vorzugsweise Palladiumchlorid, Palladiumacetat, Tetrakis-(triphenylphosphin)-Palladium, Bis-(triphenylphosphin)- Palladiumdichlorid oder (l,r-Bis(diphenylphosphino)ferrocenpalladium(II)chlorid) infrage.The processes (b), (c) and (d) according to the invention are carried out in the presence of a catalyst, e.g. a palladium salt or complex. For this purpose, preferably palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) - palladium dichloride or (l, r-bis (diphenylphosphino) ferrocenpalladium (II) chloride) come into question.
Es kann auch ein Palladiumkomplex in der Reaktionsmischung erzeugt werden, wenn man ein Palladiumsalz und ein Komplexligand, wie z.B. Triethylphosphan, Tri-tert-butylphosphan, Tricyclo- hexylphosphan, 2-(Dicyclohexylphosphan)-biphenyl, 2-(Di-tert-butylphosphan)-biphenyl, 2-(Dicy- clohexylphosphan)-2'-(N,N-dimethylamino)-biphenyl, Triphenylphosphan, Tris-(o-tolyl)-phosphan, Natrium-3-(diphenylphosphino)benzolsulfonat, Tris-2-(Methoxyphenyl)-phosphan, 2,2'-Bis-(diphe- nylphosphan)- 1 , 1 '-binaphthyl, 1 ,4-Bis-(diphenylphosphan)-butan, 1 ,2-Bis-(diphenylphosphan)-ethan, 1 ,4-Bis-(dicyclohexylphosphan)-butan, 1 ,2-Bis-(dicyclohexylphosphan)-ethan, 2-(Dicyclohexylphos- phan)-2'-(N,N-dimethylamino)-biphenyl, Bis(diphenylphosphino)ferrocen oder Tris-(2,4-tert-butyl- phenyl)-phosphit getrennt zur Reaktion zugibt.A palladium complex can also be produced in the reaction mixture if a palladium salt and a complex ligand, such as, for example, triethylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, 2- (dicyclohexylphosphine) -biphenyl, 2- (di-tert-butylphosphane) -biphenyl, 2- (dicyclohexylphosphine) -2 '- (N, N-dimethylamino) biphenyl, triphenylphosphine, tris (o-tolyl) phosphane, sodium 3- (diphenylphosphino) benzenesulfonate, tris-2- ( Methoxyphenyl) phosphane, 2,2'-bis (diphenyl) nylphosphane) - 1, 1'-binaphthyl, 1, 4-bis (diphenylphosphine) -butane, 1, 2-bis (diphenylphosphane) -ethane, 1, 4-bis (dicyclohexylphosphane) -butane, 1, 2 Bis (dicyclohexylphosphane) ethane, 2- (dicyclohexylphosphine) -2 '- (N, N-dimethylamino) biphenyl, bis (diphenylphosphino) ferrocene or tris (2,4-tert-butylphenyl) phosphite added separately to the reaction.
Zur Durchführung des erfindungsgemäßen Verfahrens (b) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Halogencarboxamids der Formel (TV) im Allgemeinen 1 bis 15 Mol, vorzugsweise 2 bis 8 Mol an Boronsäure-Derivaten der Formel (V) ein.For carrying out the process (b) according to the invention for the preparation of the compounds of the formula (I), in general from 1 to 15 mol, preferably from 2 to 8 mol, of boronic acid derivatives of the formula (V) are employed per mole of the halocarboxamide of the formula (TV) ,
Zur Durchführung des erfindungsgemäßen Verfahrens (c) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Boronsäure-Derivates der Formel (VI) im Allgemeinen 0,8 bis 15 Mol, vorzugsweise 0,8 bis 8 Mol an Phenyl-Derivat der Formel (VJT) ein.For carrying out the process (c) according to the invention for preparing the compounds of the formula (I), in general from 0.8 to 15 mol, preferably from 0.8 to 8 mol, of phenyl derivative are employed per mole of the boronic acid derivative of the formula (VI) the formula (VJT).
Zur Durchführung des erfindungsgemäßen Verfahrens (d) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Halogencarboxamides der Formel (IV) im Allgemeinen 0,8 bis 15 Mol, vorzugsweise 0,8 bis 8 Mol an Phenyl-Derivat der Formel (VE) und 0,8 bis 15 Mol, vorzugs¬ weise 0,8 bis 8 Mol an 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis-l,3,2-dioxaborolan ein.To carry out process (d) according to the invention for preparing the compounds of the formula (I), in general from 0.8 to 15 mol, preferably from 0.8 to 8 mol, of phenyl derivative of the formula are employed per mole of the halocarboxamide of the formula (IV) (VE) and 0.8 to 15 mol, preferably 0.8 to 8 mol of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis- l, 3,2-dioxaborolane.
Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens (e) kommen alle in- erten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicyclische oder aromatische Kohlenwasserstoffe, wie z.B. Petrolether, Hexan, Heptan, Cyclohexan, Methyl- cyclohexan, Benzol, Toluol, Xylol oder Decalin; halogenierte Kohlenwasserstoffe, wie z.B. Chlor¬ benzol, Dichlorbenzol, Dichlormethan, Chloroform, Tetrachlormethan, Dichlorethan oder Trichlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-tert-butylether, Methyl-tert- Amylether, Dioxan, Tetrahydrofuran, 1,2- Dimethoxyethan, 1,2-Diethoxyethan oder Anisol oder Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methyl- pyrrolidon oder Hexamethylphosphorsäuretriamid.Suitable diluents for carrying out the process (e) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, e.g. Petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, e.g. Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N- Dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
Das erfindungsgemäße Verfahren (e) wird in Gegenwart einer Base durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Basen infrage. Hierzu gehören vorzugsweiseThe process (e) according to the invention is carried out in the presence of a base. As such, all customary inorganic or organic bases are suitable. These are preferably
Erdalkalimetall- oder Alkalimetallhydride, -hydroxide, -amide, -alkoholate, -acetate, -carbonate oderAlkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or
-hydrogencarbonate, wie z.B. Natriumhydrid, Natriumamid, Natrium-methylat, Natrium-ethylat,hydrogencarbonates, e.g. Sodium hydride, sodium amide, sodium methoxide, sodium ethoxide,
Kalium-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid, Natriumacetat, KaIi- umacetat, Calciumacetat, Ammoniumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencar- bonat, Natriumhydrogencarbonat oder Caesiumcarbonat, sowie tertiäre Amine, wie Trimethylamin,Potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines, such as trimethylamine,
Triethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N-Methylpipe- ridin, N-Methylmorpholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclo- nonen (DBN) oder Diazabicycloundecen (DBU).Triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpipe ridin, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclo- nonene (DBN) or diazabicycloundecene (DBU).
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (e) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 00C bis 1500C, vorzugsweise bei Temperaturen von 200C bis 1100C.The reaction temperatures can be varied within a substantial range when carrying out the process (e) according to the invention. In general, one works at temperatures of 0 0 C to 150 0 C, preferably at temperatures of 20 0 C to 110 0 C.
Zur Durchführung des erfindungsgemäßen Verfahrens (e) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Biphenylthiazolcarboxamide der Formel (I-a) im Allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 2 Mol an Halogenid der Formel (VIII) ein.For carrying out the process (e) according to the invention for preparing the compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of halide of the formula (VIII) are employed per mole of the biphenylthiazolecarboxamide of the formula (Ia) ) one.
Wenn nicht anders angegeben, werden alle erfindungsgemäßen Verfahren im Allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, unter erhöhtem oder vermindertem Druck — im Allgemeinen zwischen 0,1 bar und 10 bar - zu arbeiten.Unless stated otherwise, all processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under elevated or reduced pressure, generally between 0.1 bar and 10 bar.
Die erfindungsgemäßen Stoffe weisen eine starke mikrobizide Wirkung auf und können zur Bekämpfung von unerwünschten Mikroorganismen, wie Fungi und Bakterien, im Pflanzenschutz und im Materialschutz eingesetzt werden.The substances according to the invention have a strong microbicidal activity and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
Fungizide lassen sich Pflanzenschutz zur Bekämpfung von Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes und Deuteromycetes einsetzen.Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bakterizide lassen sich im Pflanzenschutz zur Bekämpfung von Pseudomonadaceae, Rhizobiaceae,Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae,
Enterobacteriaceae, Corynebacteriaceae und Streptomycetaceae einsetzen.Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Beispielhaft aber nicht begrenzend seien einige Erreger von pilzlichen und bakteriellenExemplary but not limiting are some pathogens of fungal and bacterial
Erkrankungen, die unter die oben aufgezählten Oberbegriffe fallen, genannt:Diseases that fall under the above-mentioned generic terms, called:
Xanthomonas-Arten, wie z.B. Xanthomonas campestris pv. oryzae;Xanthomonas species, e.g. Xanthomonas campestris pv. Oryzae;
Pseudomonas-Arten, wie z.B. Pseudomonas syringae pv. lachrymans; Erwinia-Arten, wie z.B. Erwinia amylovora;Pseudomonas species, e.g. Pseudomonas syringae pv. Lachrymans; Erwinia species, e.g. Erwinia amylovora;
Pythium-Arten, wie z.B. Pythium ultimum;Pythium species, e.g. Pythium ultimum;
Phytophthora-Arten, wie z.B. Phytophthora infestans;Phytophthora species, e.g. Phytophthora infestans;
Pseudoperonospora-Arten, wie z.B. Pseudoperonospora humuli oderPseudoperonospora species, such as e.g. Pseudoperonospora humuli or
Pseudoperonospora cubensis; Plasmopara-Arten, wie z.B. Plasmopara viticola;Pseudoperonospora cubensis; Plasmopara species, e.g. Plasmopara viticola;
Bremia-Arten, wie z.B. Bremia lactucae; Peronospora-Arten, wie z.B. Peronospora pisi oder P. brassicae;Bremia species, such as Bremia lactucae; Peronospora species such as Peronospora pisi or P. brassicae;
Erysiphe- Arten, wie z.B. Erysiphe graminis;Erysiphe species, e.g. Erysiphe graminis;
Sphaerotheca-Arten, wie z.B. Sphaerotheca fuliginea;Sphaerotheca species, e.g. Sphaerotheca fuliginea;
Podosphaera-Arten, wie z.B. Podosphaera leucotricha; Venturia-Arten, wie z.B. Venturia inaequalis;Podosphaera species, e.g. Podosphaera leucotricha; Venturia species, e.g. Venturia inaequalis;
Pyrenophora-Arten, wie z.B. Pyrenophora teres oder P. gramineaPyrenophora species, e.g. Pyrenophora teres or P. graminea
(Konidienform: Drechslera, Syn: Hebninthosporium);(Conidia form: Drechslera, Syn: Hebninthosporium);
Cochliobolus- Arten, wie z.B. Cochliobolus sativusCochliobolus species, e.g. Cochliobolus sativus
(Konidienform: Drechslera, Syn: Helminthosporium); Uromyces-Arten, wie z.B. Uromyces appendiculatus;(Conidia form: Drechslera, Syn: Helminthosporium); Uromyces species, e.g. Uromyces appendiculatus;
Puccinia-Arten, wie z.B. Puccinia recondita;Puccinia species, e.g. Puccinia recondita;
Sclerotinia-Arten, wie z.B. Sclerotinia sclerotiorum;Sclerotinia species, e.g. Sclerotinia sclerotiorum;
Tilletia-Arten, wie z.B. Tilletia caries;Tilletia species, e.g. Tilletia caries;
Ustilago- Arten, wie z.B. Ustilago nuda oder Ustilago avenae; Pellicularia-Arten, wie z.B. Pellicularia sasakü;Ustilago species, e.g. Ustilago nuda or Ustilago avenae; Pellicularia species, e.g. Pellicularia sasaku;
Pyricularia-Arten, wie z.B. Pyricularia oryzae;Pyricularia species, e.g. Pyricularia oryzae;
Fusarium-Arten, wie z.B. Fusarium culmorum;Fusarium species, e.g. Fusarium culmorum;
Botrytis-Arten, wie z.B. Botrytis cinerea;Botrytis species, e.g. Botrytis cinerea;
Septoria-Arten, wie z.B. Septoria nodorum; Leptosphaeria-Arten, wie z.B. Leptosphaeria nodorum;Septoria species, e.g. Septoria nodorum; Leptosphaeria species, e.g. Leptosphaeria nodorum;
Cercospora- Arten, wie z.B. Cercospora canescens;Cercospora species, e.g. Cercospora canescens;
Alternaria- Arten, wie z.B. Alternaria brassicae;Alternaria species, such as e.g. Alternaria brassicae;
Pseudocercosporella-Arten, wie z.B. Pseudocercosporella herpotrichoides;Pseudocercosporella species, e.g. Pseudocercosporella herpotrichoides;
Rhizoctonia-Arten, wie z.B. Rhizoctonia solani.Rhizoctonia species, e.g. Rhizoctonia solani.
Die erfindungsgemäßen Wirkstoffe weisen auch eine starke stärkende Wirkung in Pflanzen auf. Sie eignen sich daher zur Mobilisierung pflanzeneigener Abwehrkräfte gegen Befall durch unerwünschteThe active compounds according to the invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against infestation by unwanted
Mikroorganismen.Microorganisms.
Unter pflanzenstärkenden (resistenzinduzierenden) Stoffen sind im vorliegenden Zusammenhang solche Substanzen zu verstehen, die in der Lage sind, das Abwehrsystem von Pflanzen so zu stimulie¬ ren, dass die behandelten Pflanzen bei nachfolgender Inokulation mit unerwünschten Mikro¬ organismen weitgehende Resistenz gegen diese Mikroorganismen entfalten.In the present context, plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
Unter unerwünschten Mikroorganismen sind im vorliegenden Fall phytopathogene Pilze, Bakterien und Viren zu verstehen. Die erfindungsgemäßen Stoffe können also eingesetzt werden, um Pflanzen innerhalb eines gewissen Zeitraumes nach der Behandlung gegen den Befall durch die genannten Schaderreger zu schützen. Der Zeitraum, innerhalb dessen Schutz herbeigeführt wird, erstreckt sich im Allgemeinen von 1 bis 10 Tage, vorzugsweise 1 bis 7 Tage nach der Behandlung der Pflanzen mit den Wirkstoffen.Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses. The substances according to the invention can therefore be used to plants within a certain period of time after treatment to protect against infestation by said pathogens. The period within which protection is provided generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
Die gute Pflanzenverträglichkeit der Wirkstoffe in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behandlung von oberirdischen Pflanzenteilen, von Pflanz- und Saatgut, und des Bodens.The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
Dabei lassen sich die erfindungsgemäßen Wirkstoffe mit besonders gutem Erfolg zur Bekämpfung von Getreidekrankheiten, wie z.B. gegen Puccinia-Arten und von Krankheiten im Wein-, Obst- und Gemüseanbau, wie z.B. gegen Botrytis-, Venturia- oder Alternaria-Arten, einsetzen.In this case, the active compounds according to the invention can be used with particularly good success for controlling cereal diseases, such as, for example, against Puccinia species and diseases in the wine, fruit and vegetable growing, such. against Botrytis, Venturia or Alternaria species.
Die erfindungsgemäßen Wirkstoffe eignen sich auch zur Steigerung des Ernteertrages. Sie sind außerdem mindertoxisch und weisen eine gute Pflanzenverträglichkeit auf.The active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
Die erfindungsgemäßen Wirkstoffe können gegebenenfalls in bestimmten Konzentrationen und Aufwandmengen auch als Herbizide, zur Beeinflussung des Pflanzenwachstums, sowie zur Bekämpfung von tierischen Schädlingen verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- und Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.The active compounds according to the invention may optionally also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wild¬ pflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen). Kulturpflan- zen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sorten- schutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant variety rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behand- lungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.The treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment. treatment methods, eg by dipping, spraying, vaporizing, atomizing, spreading, brushing and in the case of propagation material, in particular in the case of seeds, furthermore by single-layer or multi-layer coating.
Im Materialschutz lassen sich die erfindungsgemäßen Stoffe zum Schutz von technischen Materialien gegen Befall und Zerstörung durch unerwünschte Mikroorganismen einsetzen.In the protection of materials, the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
Unter technischen Materialien sind im vorliegenden Zusammenhang nichtlebende Materialien zu verstehen, die für die Verwendung in der Technik zubereitet worden sind. Beispielsweise können technische Materialien, die durch erfindungsgemäße Wirkstoffe vor mikrobieller Veränderung oder Zerstörung geschützt werden sollen, Klebstoffe, Leime, Papier und Karton, Textilien, Leder, Holz, Anstrichmittel und Kunststoffartikel, Kühlschmierstoffe und andere Materialien sein, die von Mikroor¬ ganismen befallen oder zersetzt werden können. Im Rahmen der zu schützenden Materialien seien auch Teile von Produktionsanlagen, beispielsweise Kühlwasserkreisläufe, genannt, die durch Vermehrung von Mikroorganismen beeinträchtigt werden können. Im Rahmen der vorliegenden Erfindung seien als technische Materialien vorzugsweise Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Anstrich¬ mittel, Kühlschmiermittel und Wärmeübertragungsflüssigkeiten genannt, besonders bevorzugt Holz.Technical materials as used herein mean non-living materials that have been prepared for use in the art. For example, technical materials which are to be protected against microbial change or destruction by active compounds according to the invention are adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which infest or decompose microorganisms can be. In the context of the materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms. In the context of the present invention, technical materials which may be mentioned are preferably adhesives, glues, paper and cardboard, leather, wood, paint, cooling lubricants and heat transfer liquids, particularly preferably wood.
Als Mikroorganismen, die einen Abbau oder eine Veränderung der technischen Materialien bewirken können, seien beispielsweise Bakterien, Pilze, Hefen, Algen und Schleimorganismen genannt. Vorzugs- weise wirken die erfindungsgemäßen Wirkstoffe gegen Pilze, insbesondere Schimmelpilze, holz¬ verfärbende und holzzerstörende Pilze (Basidiomyceten) sowie gegen Schleimorganismen und Algen.As microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned. Preferably, the active compounds according to the invention act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
Es seien beispielsweise Mikroorganismen der folgenden Gattungen genannt:There may be mentioned, for example, microorganisms of the following genera:
Alternaria, wie Alternaria tenuis, Aspergillus, wie Aspergillus niger,Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
Chaetomium, wie Chaetomium globosum,Chaetomium, such as Chaetomium globosum,
Coniophora, wie Coniophora puetana,Coniophora, like Coniophora puetana,
Lentinus, wie Lentinus tigrinus,Lentinus, like Lentinus tigrinus,
Penicillium, wie Penicillium glaucum, Polyporus, wie Polyporus versicolor,Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor,
Aureobasidium, wie Aureobasidium pullulans,Aureobasidium, such as Aureobasidium pullulans,
Sclerophoma, wie Sclerophoma pityophila,Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, wie Trichoderma viride,Trichoderma, like Trichoderma viride,
Escherichia, wie Escherichia coli, Pseudomonas, wie Pseudomonas aeruginosa,Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, wie Staphylococcus aureus. Die Wirkstoffe können in Abhängigkeit von ihren jeweiligen physikalischen und/ oder chemischen Eigenschaften in die üblichen Formulierungen überfuhrt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-KaIt- und Warmnebel-Formulierungen.Staphylococcus, such as Staphylococcus aureus. Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in seed coating compositions, as well as ULV -KaIt- and warm mist formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/ oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Be- nutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungs- mittel verwendet werden. Als flüssige Lösungsmittel kommen im Wesentlichen infrage: Aromaten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlen¬ wasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasser¬ stoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser. Mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten ge¬ meint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol- Treibgase, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Als feste Trägerstoffe kommen infrage: z.B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate. Als feste Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Bims, Marmor, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnussschalen, Maiskolben und Tabakstängel. Als Emulgier und/oder schaumerzeugende Mittel kommen infrage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäureester, Polyoxyethylen-Fettalkoholether, z.B. Alkylaryl- polyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate. Als Disper¬ giermittel kommen infrage: z.B. Lignin-Sulfϊtablaugen und Methylcellulose.These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents. In the case of the use of water as extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water. By liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: e.g. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems. Suitable emulsifiers and / or foam-forming agents are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates. Suitable dispersants are: e.g. Lignin-Sulfϊtablaugen and methylcellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthe¬ tische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Other additives may be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe, wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.It can dyes such as inorganic pigments, such as iron oxide, titanium oxide, and Ferrocyanblau organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
Die Formulierungen enthalten im Allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formulierungen auch in Mischung mit bekannten Fungiziden, Bakteriziden, Akariziden, Nematiziden oder Insektiziden verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern oder Resistenzentwicklungen vorzubeugen. In vielen Fällen erhält man dabei synergistische Effekte, d.h. die Wirksamkeit der Mischung ist größer als die Wirksamkeit der Einzelkomponenten.The active compounds according to the invention, as such or in their formulations, can also be used in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance. In many cases synergistic effects, i. E. the effectiveness of the mixture is greater than the effectiveness of the individual components.
Als Mischpartner kommen zum Beispiel folgende Verbindungen infrage:As mixing partners, for example, the following compounds are suitable:
Fungizide: 2-Phenylphenol; 8-Hydroxyquinoline sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampro- pylfos; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Benala- xyl-M; Benodanil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; Bilanafos;Fungicides: 2-phenylphenol; 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Amphropolys; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benalaxyl M; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos;
Binapacryl; Biphenyl; Bitertanol; Blasticidin-S; Boscalid; Bromuconazole; Bupirimate; Buthiobate;binapacryl; biphenyl; bitertanol; Blasticidin-S; boscalid; bromuconazole; Bupirimate; Buthiobate;
Butylamine; Calcium polysulfϊde; Capsimycin; Captafol; Captan; Carbendazim; Carboxin; Carprop- amid; Carvone; Chinomethionat; Chlobenthiazone; Chlorfenazole; Chloroneb; Chlorothalonil; Chlozoli- nate; Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil; Cyproconazole; Cyprodinil; Cyprofuram;butylamine; Calcium polysulfϊde; capsimycin; captafol; captan; carbendazim; carboxin; Carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; Chlozolinates; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram;
Dagger G; Debacarb; Dichlofluanid; Dichlone; Dichlorophen; Diclocymet; Diclomezine; Dicloran; Di- ethofencarb; Difenoconazole; Diflumetorim; Dimethirimol; Dimethomorph; Dimoxystrobin; Dinicon- azole; Diniconazole-M; Dinocap; Diphenylamine; Dipyrithione; Ditalimfos; Dithianon; Dodine; Dra- zoxolon; Edifenphos; Epoxiconazole; Ethaboxam; Ethirimol; Etridiazole; Famoxadone; Fenamidone;Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; Diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; Diniconazoles; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolone; edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone;
Fenapanil; Fenarimol; Fenbuconazole; Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil;Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil;
Fenpropidin; Fenpropimorph; Ferbam; Fluazinam; Flubenzimine; Fludioxonil; Flumetover, Flumoφh;fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; Flumetov, Flumoφh;
Fluoromide; Fluoxastrobin; Fluquinconazole; Fluφrimidol; Flusilazole; Flusulfamide; Flutolanil;fluoromides; fluoxastrobin; fluquinconazole; Fluφrimidol; flusilazole; flusulfamide; flutolanil;
Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium; Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil; Furmecyclox; Guazatine; Hexachlorobenzene; Hexaconazole; Hymexazol; Imazalil; Imibenconazole;flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; imazalil; Imibenconazole;
Iminoctadine triacetate; Iminoctadine tris(albesilate); lodocarb; Ipconazole; Iprobenfos; Iprodione;Iminoctadine triacetate; Iminoctadine tris (albesilate); lodocarb; ipconazole; iprobenfos; iprodione;
Iprovalicarb; Irumamycin; Isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl; Mancozeb;iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb;
Maneb; Meferimzone; Mepanipyrim; Mepronil; Metalaxyl; Metalaxyl-M; Metconazole; Metha- sulfocarb; Methfuroxam; Metiram; Metominostrobin; Metsulfovax; Mildiomycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen; Nitrothal-isopropyl; Noviflumuron; Nuarimol; Ofurace; Orysa- strobin; Oxadixyl; Oxolinic acid; Oxpoconazole; Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefura- zoate; Penconazole; Pencycuron; Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins; PoIy- oxorim; Probenazole; Prochloraz; Procymidone; Propamocarb; Propanosine-sodium; Propiconazole; Propineb; Proquinazid; Prothioconazole; Pyraclostrobin; Pyrazophos; Pyrifenox; Pyrimethanil; Pyro- quilon; Pyroxyfur, Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene; Simeconazole; Spiroxamine; Sulfiir; Tebuconazole; Tecloftalam; Tecnazene; Tetcyclacis; Tetraconazole; Thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; Thiram; Tioxymid; Tolclofos-methyl; Tolylfluanid; Triadimefon; Triadimenol; Triazbutil; Triazoxide; Tricyclamide; Tricyclazole; Tridemorph; Trifloxystrobin; Trifiu- mizole; Triforine; Triticonazole; Uniconazole; Validamycin A; Vinclozolin; Zineb; Ziram; Zoxamide; (2S)-N-[2-[4-[[3-(4-Chloφhenyl>2φropnyl]oxy]-3-me1hoxyphenyl]ethyl]-3-methyl-2-[(methylsulfo- nyl)amino]-butanamid; l-(l-Naphthalinyl)-lH-pyrrol-2,5-dion; 2,3,5,6-Tetrachlor-4-(methylsulfonyl)- pyridin; 2-Amino-4-methyl-N-phenyl-5-thiazolcarboxamid; 2-Chlor-N-(2,3-dihydro-l,l,3-trimethyl-lH- inden-4-yl)-3-pyridincarboxamid; 3,4,5-Trichlor-2,6-pyridindicarbonitril; Actinovate; cis-l-(4-Chlor- phenyl>2-(lH-l,2,4-triazol-l-yl)-cycloheptanol; Methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl> lH-imidazol-5-carboxylat; Monokaliumcarbonat; N^ό-Methoxy-S-pyridinylJ-cyclopropancarboxamid; N-Butyl-8-(l,l-dimethylethyl)-l-oxaspiro[4.5]decan-3-aπiin; Natriumtetracarbonat; sowie Kupfersalze und -Zubereitungen, wie Bordeaux mixture; Copper hydroxide; Copper naphthe- nate; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxide; Mancopper; Oxine-copper.maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; Methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; Orysazrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefura- Zoate; penconazole; pencycuron; phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorime; Probenazole; prochloraz; procymidone; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; Pyroquilon; Pyroxyfur, pyrroline nitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; Triflicizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-chlorophenyl) 2-propynyl] oxy] -3-me1hoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamide; 1- (1-naphthalenyl) -1 H -pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl-5-dione; thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-1- (4-chlorophenyl> 2- (1H-l, 2,4-triazol-1-yl) -cycloheptanol; methyl 1- (2,3-dihydro-2,2-dimethyl-1H -inden-1-yl>1H-imidazole-5-carboxylate; monopotassium carbonate; N, ό-methoxy-S-pyridinyl-1-cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decane 3-aπiin; sodium tetracarbonate; and copper salts and preparations such as Bordeaux mixture; Copper Hydroxide; Copper Naphthenate; Copper Oxychloride; Copper Sulfate; Cufraneb; Cuprous Oxide; Mancopper; Oxine-copper.
Bakterizide: Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bactericides: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
Insektizide / Akarizide / Nematizide: 1. Acetylcholinesterase (AChE) InhibitorenInsecticides / acaricides / nematicides: 1. Acetylcholinesterase (AChE) inhibitors
1.1 Carbamate (z.B. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Chloethocarb, Coumaphos, Cyanofenphos, Cyanophos, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb)1.1 carbamates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, Formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, Triazamate, trimethacarb, XMC, xylylcarb)
1.2 Organophosphate (z.B. Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chlorethoxyfos, Chlorfen- vinphos, Chlormephos, Chloφyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupy- razofos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Metha- midophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Para- thion (-methyl/-ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl/-ethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion)1.2 organophosphates (eg acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chlormephos, chloφyrifos (-methyl / -ethyl), Coumophos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylates, Isoxathion, Malathion, Mecarbam, Methacrifos , Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidone, Phosphocarb, Phoxim, Pirimiphos (-methyl) ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoates, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion)
2. Natrium-Kanal-Modulatoren /Spannungsabhängige Natrium-Kanal-Blocker 2.1 Pyrethroide (z.B. Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifenthrin, Bio- allethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, ChIo- vaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyflu- thrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Deltamethrin, Em-2. Sodium channel modulators / voltage-dependent sodium channel blockers 2.1 pyrethroids (for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl-isomer , Bioethanomethrin, biopermethrin, bioresmethrin, chlorovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, em-
• penthrin (lR-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fen- valerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma- Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (eis-, trans-), Phenothrin (lR-trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (lR-isomer), Tralome- thrin, Transfluthrin, ZXI 8901, Pyrethrins (pyrethrum)) 2.2 Oxadiazine (z.B. Indoxacarb)Penthrine (lR-isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalate, flubrocythrinates, flucythrinates, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin ( cis-, trans-), phenothrin (IR trans isomer), prallethrin, profuthrin, protrifenbutene, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralomethine, transfluthrin , ZXI 8901, pyrethrins (pyrethrum)) 2.2 Oxadiazines (eg indoxacarb)
3. Acetylcholin-Rezeptor-AgonistenZ-Antagonisten3. Acetylcholine receptor agonist Z antagonists
3.1 Chloronicotinyle/Neonicotinoide (z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Ni- tenpyram, Nithiazine, Thiacloprid, Thiamethoxam)3.1 chloronicotinyls / neonicotinoids (for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, tenpyram, nithiazines, thiacloprid, thiamethoxam)
3.2 Nicotine, Bensultap, Cartap 4. Acetylcholin-Rezeptor-Modulatoren 4.1 Spinosyne (z.B. Spinosad)3.2 Nicotine, Bensultap, Cartap 4. Acetylcholine Receptor Modulators 4.1 Spinosyns (e.g., Spinosad)
5. GABA-gesteuerte Chlorid-Kanal-Antagonisten5. GABA-driven chloride channel antagonists
5.1 Cyclodiene Organochlorine (z.B. Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor 5.2 Fiprole (z.B. Acetoprole, Ethiprole, Fipronil, Vaniliprole)5.1 Cyclodienes Organochlorines (e.g., camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor 5.2 Fiproles (e.g., acetoprole, ethiprole, fipronil, vaniliprole)
6. Chlorid-Kanal-Aktivatoren6. Chloride Channel Activators
6.1 Mectine (z.B. Abamectin, Avermectin, Emamectin, Emamectin-benzoate, Ivermectin, Milbe- mectin, Milbemycin)6.1 Mectins (for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milkmectin, milbemycin)
7. Juvenilhormon-Mimetika (z.B. Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene) 8. Ecdysonagonisten/disruptoren7. Juvenile hormone mimetics (eg, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene) 8. ecdysonagonists / disruptors
8.1 Diacylhydrazine (z.B. Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide)8.1 diacylhydrazines (e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides)
9. Inhibitoren der Chitinbiosynthese9. Inhibitors of chitin biosynthesis
9.1 Benzoylharnstoffe (z.B. Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Tri- flumuron)9.1 Benzoylureas (e.g., bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoronon)
9.2 Buprofezin9.2 Buprofezin
9.3 Cyromazine9.3 Cyromazine
10. Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren lO.l Diafenthiuron10. Inhibitors of oxidative phosphorylation, ATP disruptors IO.l diafenthiuron
10.2 Organotine (z.B. Azocyclotin, Cyhexatin, Fenbutatin-oxide)10.2 Organotin (e.g., azocyclotin, cyhexatin, fenbutatin oxides)
11. Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten11. Decoupling of oxidative phosphorylation by interruption of the H proton gradient
11.1 Pyrrole (z.B. Chlorfenapyr)11.1 Pyrroles (e.g., chlorfenapyr)
11.2 Dinitrophenole (z.B. Binapacryl, Dinobuton, Dinocap, DNOC) 12. Seite-I-Elektronentransportinhibitoren11.2 Dinitrophenols (e.g., binapacryl, dinobutone, dinocap, DNOC) 12. Side-I electron transport inhibitors
12.1 METTs (z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)12.1 METTs (e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)
12.2 Hydramethylnone12.2 Hydramethylnone
12.3 Dicofol12.3 Dicofol
13. Seite-II-Elektronentransportinhibitoren 13.1 Rotenone13. Side II Electron Transport Inhibitors 13.1 Rotenones
14. Seite-III-Elektronentramportinhibitoren 14.1 Acequinocyl, Fluacrypyrim14. Side III Electron Centrifugation Inhibitors 14.1 Acequinocyl, Fluacrypyrim
75. Mikrobielle Disruptoren der Insektendarmmembran Bacillus thuringiensis-Stämme 16. Inhibitoren der Fettsynthese75. Microbial disruptors of insect intestinal membrane Bacillus thuringiensis strains 16. Inhibitors of fat synthesis
16.1 Tetronsäuren (z.B. Spirodiclofen, Spiromesifen)16.1 Tetronic acids (e.g., spirodiclofen, spiromesifen)
16.2 Tetramsäuren [z.B. 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4- yl e%l ester, CAS-Reg.-No.: 382608-10-8) and Carbonic acid, cis-3-(2,5-dimethylphenyl)-8- methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl ester (CAS-Reg.-No.: 203313-25-1)]16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ester, CAS Reg. No .: 382608-10-8) and carbonic acid, cis-3 - (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg. No .: 203313-25-1)]
17. Carboxamide (z.B. Flonicamid)17. Carboxamides (e.g., flonicamid)
18. Oktopaminerge Agonisten (z.B. Amitraz) 19. Inhibitoren der Magnesium-stimulierten ATPase (z.B. Propargite) 20. Phthalamide18. Octopaminergic agonists (eg, Amitraz) 19. Inhibitors of magnesium-stimulated ATPase (eg, propargite) 20. phthalamides
(z.B. N^f l.l-Dimethyl^-CmethylsulfonyOethyη-S-iod-N'-p-methyM-tl^^^-tetrafluor-Htrifluor- methyl)ethyl]phenyl]-l,2-benzenedicarboxamide (CAS-Reg.-No.: 272451-65-7), Flubendiamide)(For example, N, F-dimethyl-methylsulfonyoethyi-S-iodo-N'-p-methyl-tl-1-yl-tetrafluoro-trifluoromethyl) ethyl, phenyl, -l, 2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7), Flubendiamide)
21. Nereistoxin-Analoge (z.B. Thiocyclam hydrogen Oxalate, Thiosultap-sodium)21. Nereistoxin analogs (e.g., thiocyclam hydrogen oxalate, thiosultap-sodium)
22. Biologika, Hormone oder Pheromone22. Biologics, hormones or pheromones
(z.B. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizium spec, Paecilomyces spec, Thuringiensin, Verticillium spec.)(e.g., Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhicon spec, Paecilomyces spec, Thuringiensin, Verticillium spec.)
23. Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen 23.1 Begasungsmittel (z.B. Aluminium phosphide, Methyl bromide, Sulfuryl fluoride)23. Active substances with unknown or nonspecific modes of action 23.1 Fumigants (for example aluminum phosphides, methyl bromides, sulfuryl fluorides)
23.2 Selektive Fraßhemmer (z.B. Cryolite, Flonicamid, Pymetrozine)23.2 Selective feeding inhibitors (e.g., cryolites, flonicamid, pymetrozines)
23.3 Milbenwachstumsinhibitoren (z.B. Clofentezine, Etoxazole, Hexythiazox)23.3 mite growth inhibitors (e.g., clofentezine, etoxazole, hexythiazox)
23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chinomethi- onat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Di- cyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethyl- none, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin,23.4 Amidoflumet, benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flotenzin, gossyplasty, hydramethylnone, japonilure , Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramide, Tetradifon, Tetrasul, Triarathene, Verbutin,
ferner die Verbindung 3-Methyl-phenyl-propylcarbamat (Tsumacide Z), die Verbindung 3-(5-Chlor-3- pyridinyl>8-(2,2,2-trifluorethyl>8-azabicyclo[3.2.1]octan-3-carbonitril (CAS-Reg.-Nr. 185982-80-3) und das entsprechende 3-endo-Isomere (CAS-Reg.-Nr. 185984-60-5) (vgl. WO 96/37494, WO 98/25923), sowie Präparate, welche insektizid wirksame Pflanzenextrakte, Nematoden, Pilze oder Viren enthalten.the compound 3-methylphenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl> 8- (2,2,2-trifluoroethyl> 8-azabicyclo [3.2.1] octane-3) carbonitrile (CAS Reg. No. 185982-80-3) and the corresponding 3-endo isomer (CAS Reg. No. 185984-60-5) (see WO 96/37494, WO 98/25923 ), as well as preparations containing insecticidal plant extracts, nematodes, fungi or viruses.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren, Safener bzw. Semiochemicals ist möglich.A mixture with other known active substances, such as herbicides or with fertilizers and growth regulators, safeners or semiochemicals is possible.
Darüber hinaus weisen die erfindungsgemäßen Verbindungen der Formel (I) auch sehr gute antimykotische Wirkungen auf. Sie besitzen ein sehr breites antimykotisches Wirkungsspektrum, insbesondere gegen Dermatophyten und Sprosspilze, Schimmel und diphasische Pilze (z.B. gegen Candida-Spezies wie Candida albicans, Candida glabrata) sowie Epidermophyton floccosum, Aspergillus-Spezies wie Aspergillus niger und Aspergillus fumigatus, Trichophyton-Spezies wie Trichophyton mentagrophytes, Microsporon-Spezies wie Microsporon canis und audouinii. Die Aufzählung dieser Pilze stellt keinesfalls eine Beschränkung des erfassbaren mykotischen Spektrums dar, sondern hat nur erläuternden Charakter. Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver, Stäubemittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstäuben, Verschäumen, Bestrei- chen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low-Volume- Verfahren auszubrin¬ gen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. Es kann auch das Saatgut der Pflanzen behandelt werden.In addition, the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character. The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. The application is carried out in a customary manner, for example by casting, spraying, spraying, scattering, dusting, foaming, spreading, etc. It is also possible to use the active ingredients by the ultra-low-volume method auszubrin¬ or the preparation of active compound or the To inject active substance into the soil itself. It can also be the seed of the plants to be treated.
Beim Einsatz der erfindungsgemäßen Wirkstoffe als Fungizide können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereiches variiert werden. Bei der Behandlung vonWhen using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the mode of administration. In the treatment of
Pflanzenteilen liegen die Aufwandmengen an Wirkstoff im Allgemeinen zwischen 0,1 undPlant parts are the application rates of active ingredient generally between 0.1 and
10.000 g/ha, vorzugsweise zwischen 10 und 1.000 g/ha. Bei der Saatgutbehandlung liegen die10,000 g / ha, preferably between 10 and 1,000 g / ha. In the seed treatment are the
Aufwandmengen an Wirkstoff im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 10 g pro Kilogramm Saatgut. Bei der Behandlung des Bodens liegen die Aufwandmengen an Wirkstoff im Allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 1 und 5.000 g/ha.Application rates of active ingredient generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modifϊed Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw. „Teile von Pflanzen" oder „Pflanzenteile" wurde oben erläutert.As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
Besonders bevorzugt werden erfϊndungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein.According to the invention, plants of the respective commercially available or used plant cultivars are particularly preferably treated. Plant varieties are understood to be plants having new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden,Depending on the plant species or plant cultivars, their location and growth conditions (soils,
Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive („synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfindungsgemäß verwendbaren Stoffe und Mittel, besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfahigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.Climate, vegetation period, nutrition), the treatment according to the invention can also give rise to superadditive ("synergistic") effects, for example, reduced application rates and / or enhancements of the activity spectrum and / or an increase in the effect of Substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering efficiency, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value Harvest products, higher storage capacity and / or workability of the harvested products possible, which go beyond the expected effects actually.
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigen¬ schaften („Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Be¬ schleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Baumwolle, Tabak, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften („Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CryΙA(a), CryΙA(b), CryΙA(c), CryllA, CrylHA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im Folgenden ,JBt Pflanzen"). Als Eigenschaften („Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften („Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirk¬ stoffen, z.B. Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"- Gen). Die jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kom¬ binationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für ,3t Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeich¬ nungen YIELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucoton® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glypho- sate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z.B. Raps), IMI® (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfϊeld® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständ¬ lich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kom¬ mende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften („Traits").The preferred plants or plant varieties to be treated according to the invention which are to be treated include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") Examples of such properties are better Plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering, easier harvesting, acceleration of maturity, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or Viruses and increased tolerance of plants against certain herbicidal active ingredients. Examples of transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, potato , Cotton, tobacco and oilseed rape. Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryΙA (b), CryΙA (c), CryllA, CrylHA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof) in the plants (hereinafter "JBt plants"). Traits also highlight the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. ) are further particularly emphasized the increased tolerance of the plants to certain herbicidal Wirk¬ substances, eg imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes conferring the desired properties ("traits") can also occur in combinations with one another in the transgenic plants Examples of maize varieties, cotton varieties, soybean varieties and potato varieties which may be mentioned under the trade names YIELD GARD ® (eg corn, cotton, soy), KnockOut® (eg corn), StarLink® (eg Corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® ( Tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also mentioned under the name Clearfϊeld® varieties (eg corn). Of course, these statements also apply to plant varieties developed or to be marketed in the future with these or future developed genetic traits.
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit den Verbindungen der allgemeinen Formel (I) bzw. den erfindungsgemäßen Wirkstoffmischungen behandelt werden. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen.The listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active substance mixtures according to the invention. The preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe geht aus den folgenden Beispielen hervor. The preparation and the use of the active compounds according to the invention are evident from the following examples.
HerstellungsbeispielePreparation Examples
Beispiel 1 (Verbindung 1.15*)Example 1 (compound 1.15 * )
Zu einer Lösung bestehend aus 230 mg (2,3 mmol) Triethylamin und 600 mg (2,3 mmol) 4'-Methyl- 5-trifluormethyl-biphenyl-2-amin in 10 ml Toluol werden 500 mg (2,3 mmol) 2-Methyl-4-(trifluor- methyl)-l,3-thiazol-5-carbonylchlorid in 2,5 ml Toluol bei Raumtemperatur zugetropft. Die Reak¬ tionsmischung wird für 2 Stunden bei 500C gerührt, auf Raumtemperatur abgekühlt und anschließend mit 10 ml Wasser gewaschen. Die organische Phase wird über Natriumsulfat getrocknet und im Vakuum aufkonzentriert. Das Rohprodukt wird mit n-Hexan/Essigsäureethylester (2:1) an Kieselgel chromatographiert.To a solution consisting of 230 mg (2.3 mmol) of triethylamine and 600 mg (2.3 mmol) of 4'-methyl-5-trifluoromethyl-biphenyl-2-amine in 10 ml of toluene are added 500 mg (2.3 mmol) 2-methyl-4- (trifluoromethyl) -1,3-thiazole-5-carbonyl chloride in 2.5 ml of toluene was added dropwise at room temperature. The Reak¬ tion mixture is stirred for 2 hours at 50 0 C, cooled to room temperature and then washed with 10 ml of water. The organic phase is dried over sodium sulfate and concentrated in vacuo. The crude product is chromatographed on silica gel with n-hexane / ethyl acetate (2: 1).
Man erhält 650 mg (89%ig, 66 % der Theorie) 2-Methyl-N-[4'-methyl-5-(trifluormethyl)biphenyl-2- yl]-4-(trifluormethyl)-l,3-thiazol-5-carboxamid [logP (pH 2,3) = 4,48].This gives 650 mg (89%, 66% of theory) of 2-methyl-N- [4'-methyl-5- (trifluoromethyl) biphenyl-2-yl] -4- (trifluoromethyl) -1,3-thiazole 5-carboxamide [logP (pH 2.3) = 4.48].
Herstellung von Ausgangsstoffen der Formel (111)Preparation of starting materials of the formula (111)
4'-Methyl-5-(trifluormethyl)biphenyl-2-amin4'-methyl-5- (trifluoromethyl) biphenyl-2-amine
5,2 g (0,037 mol) 4-Methylphenylboronsäure, 5,0 g (0,020 mol) 2-Brom-4-trifiuormethylanilin und 9,7 g (0,092 mol) Natriumcarbonat werden unter Ausschluss von Sauerstoff in einer Mischung aus 45 ml 1,2-Dimethoxyethan und 45 ml Wasser unter Argon suspendiert. Die Reaktionsmischung wird mit 0,85 g Tetrakis(triphenylphosphin)palladium(0) versetzt und 12 Stunden bei 800C gerührt. Die organische Phase wird abgetrennt und die wässrige Phase mit Essigsäureethylester extrahiert. Die vereinigten organischen Phasen werden über Natriumsulfat getrocknet und im Vakuum eingeengt. Der Rückstand wird mit n-Hexan/Methyl-tert-butylether (3:1) an Kieselgel chromatographiert. Man erhält 3,3 g (96,3%ig, 62,5 % d. Th.) an 4'-Methyl-5-(trifluormethyl)biphenyl-2-amin [logP (pH2,3) = 3,98].5.2 g (0.037 mol) of 4-methylphenylboronic acid, 5.0 g (0.020 mol) of 2-bromo-4-trifluoromethylaniline and 9.7 g (0.092 mol) of sodium carbonate are added in the absence of oxygen in a mixture of 45 ml 1, Suspended 2-dimethoxyethane and 45 ml of water under argon. The reaction mixture is mixed with 0.85 g of tetrakis (triphenylphosphine) palladium (0) and stirred at 80 0 C for 12 hours. The organic phase is separated and the aqueous phase extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel with n-hexane / methyl tert-butyl ether (3: 1). 3.3 g (96.3%, 62.5% of theory) of 4'-methyl-5- (trifluoromethyl) biphenyl-2-amine [logP (pH 2.3) = 3.98] are obtained. ,
Analog obigem Beispiel und entsprechend den allgemeinen Verfahrensbeschreibungen können die in der nachfolgenden Tabelle 1 genannten Verbindungen erhalten werden.Analogously to the above example and according to the general process descriptions, the compounds mentioned in Table 1 below can be obtained.
Tabelle 1Table 1
Nr. R1 R2 R3 R4 R5 Log P / Fp. (0C)No. R 1 R 2 R 3 R 4 R 5 Log P / Fp. ( 0 C)
1.01 CH3 CF3 H 4-Cl 4'-F 3,901.01 CH 3 CF 3 H 4-Cl 4'-F 3.90
1.02 CH3 CF3 H 4-Cl 4'-CH3 4,301.02 CH 3 CF 3 H 4 Cl 4'-CH 3 4.30
1.03 CH3 CF3 H 4-Cl 4'-SCH3 4,301.03 CH 3 CF 3 H 4-Cl 4'-SCH 3 4.30
1.04 CH3 CF3 H 4-Cl 3'-CF3 4,301.04 CH 3 CF 3 H 4-Cl 3'-CF 3 4.30
1.05 CH3 CF3 H 4-Cl 3'-NHC(O)CH3 2,901.05 CH 3 CF 3 H 4-Cl 3'-NHC (O) CH 3 2.90
1.06 CH3 CF3 H 4-Cl 2'-CF3 4,301.06 CH 3 CF 3 H 4-Cl 2'-CF 3 4.30
1.07 CH3 CF3 H 4-Cl 4'-CF3 4,301.07 CH 3 CF 3 H 4-Cl 4'-CF 3 4.30
1.08 CH3 CF3 H 4-Cl 3'-OCH3 3,901.08 CH 3 CF 3 H 4-Cl 3'-OCH 3 3.90
1.09 CH3 CF3 H 4-Cl 3'-OC2H5 4,301.09 CH 3 CF 3 H 4-Cl 3'-OC 2 H 5 4.30
1.10 CH3 CF3 H 5-OCH3 3'-NHC(O)CH3 2,301.10 CH 3 CF 3 H 5-OCH 3 3'-NHC (O) CH 3 2.30
1.11 CH3 CF3 H 5-F 4'-OCF3 4,441.11 CH 3 CF 3 H 5-F 4'-OCF 3 4.44
1.12 CH3 CF3 H 5-OCH3 2'-CH3 2,301.12 CH 3 CF 3 H 5-OCH 3 2'-CH 3 2.30
1.13 CH3 CF3 H 5-CH3 4'-CH3 3,92 / 95-96°C1.13 CH 3 CF 3 H 5 -CH 3 4'-CH 3 3.92 / 95-96 ° C
1.14 CH3 CF3 H 5-CH(CHs)2 4'-CH3 4,591.14 CH 3 CF 3 H 5-CH (CHs) 2 4'-CH 3 4.59
1.15 CH3 CF3 H 5-CF3 4'-CH3 4,481.15 CH 3 CF 3 H 5-CF 3 4'-CH 3 4.48
1.16 CH3 CF3 H 5-OCH3 2'-OCH3 3,201.16 CH 3 CF 3 H 5 OCH 3 2'-OCH 3 3.20
1.17 CH3 CF3 H 5-OCH3 2'-CF3 3,101.17 CH 3 CF 3 H 5-OCH 3 2'-CF 3 3,10
1.18 CH3 CF3 H 5-OCH3 3'-OC2H5 3,101.18 CH 3 CF 3 H 5-OCH 3 3'-OC 2 H 5 3.10
1.19 CH3 CF3 H 5-OCH3 3'-C(O)CH3 3,101.19 CH 3 CF 3 H 5-OCH 3 3'-C (O) CH 3 3.10
1.20 CH3 CF3 H 5-OCH3 2'-Cl 3,201.20 CH 3 CF 3 H 5-OCH 3 2'-Cl 3.20
1.21 CH3 CF3 H 5-OCH3 3'-NO2 3,501.21 CH 3 CF 3 H 5 -OCH 3 3'-NO 2 3.50
1.22 CH3 CF3 H 5-OCH3 4'-Br 3,50 Nr. R1 R2 R3 R4 R5 Log P / Fp. (0C)1.22 CH 3 CF 3 H 5-OCH 3 4'-Br 3.50 No. R 1 R 2 R 3 R 4 R 5 Log P / Fp. ( 0 C)
1.23 CH3 CF3 H 5-OCH3 4'-Cl 3,501.23 CH 3 CF 3 H 5-OCH 3 4'-Cl 3.50
1.24 CH3 CF3 H 5-OCH3 4'-CH3 3,501.24 CH 3 CF 3 H 5-OCH 3 4'-CH 3 3.50
1.25 CH3 CF3 H 5-OCH3 3'-CH3 3,601.25 CH 3 CF 3 H 5-OCH 3 3'-CH 3 3.60
Die Bestimmung der angegebenen logP- Werte erfolgte gemäß EEC-Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18). Temperatur: 43°C.The specified logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (C 18). Temperature: 43 ° C.
Eluenten für die Bestimmung im sauren Bereich (pH 2,3): 0,1 % wässrige Phosphorsäure, Aceto- nitril; linearer Gradient von 10 % Acetonitril bis 90 % Acetonitril.Eluents for determination in the acidic range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
Die Eichung erfolgte mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren LogP- Werte bekannt sind (Bestimmung der LogP-Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinanderfolgenden Alkanonen).The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose LogP values are known (determination of the LogP values by means of the retention times by linear interpolation between two consecutive alkanones).
Die lambda-max- Werte wurden an Hand der UV-Spektren von 200 nm bis 400 nm in den Maxima der chromatographischen Signale ermittelt. The lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
Anwendungsbeispieleapplications
Beispiel AExample A
Podosphaera - Test (Apfel) / protektivPodosphaera - test (apple) / protective
Lösungsmittel: 24,5 Gewichtsteile AcetonSolvent: 24.5 parts by weight of acetone
24,5 Gewichtsteile Dimethylacetamid24.5 parts by weight of dimethylacetamide
Emulgator: 1 Gewichtsteil Alkyl-Aryl-PolyglykoletherEmulsifier: 1 part by weight of alkyl-aryl-polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer wässrigen Sporensuspension von Podosphaera leucotricha inokuliert. Die Pflanzen werden dann im Gewächshaus bei ca. 230C und einer relativen Luftfeuchtigkeit von ca. 70 % aufgestellt.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Podosphaera leucotricha. The plants are then placed in the greenhouse at about 23 0 C and a relative humidity of about 70%.
10 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird. 10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
Beispiel BExample B
Venturia - Test (Apfel) / protektivVenturia - test (apple) / protective
Lösungsmittel: 24,5 Gewichtsteile AcetonSolvent: 24.5 parts by weight of acetone
24,5 Gewichtsteile Dimethylacetamid Emulgator: 1 Gewichtsteil Alkyl-Aryl-Polyglykolether24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer wässrigen Konidiensuspension des Apfelschorferregers Venturia inaequalis inokuliert und verbleiben dann 1 Tag bei ca. 200C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain in an incubation cabin for 1 day at about 20 ° C. and 100% relative atmospheric humidity.
Die Pflanzen werden dann im Gewächshaus bei ca. 21°C und einer relativen Luftfeuchtigkeit von ca. 90 % aufgestellt.The plants are then placed in the greenhouse at about 21 ° C and a relative humidity of about 90%.
10 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird. 10 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
Beispiel CExample C
Botrytis - Test (Bohne) / protektivBotrytis - test (bean) / protective
Lösungsmittel: 24,5 Gewichtsteile AcetonSolvent: 24.5 parts by weight of acetone
24,5 Gewichtsteile Dimethylacetamid Emulgator: 1 Gewichtsteil Alkyl-Aryl-Polyglykolether24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl-aryl-polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden auf jedes Blatt 2 kleine mit Botrytis cinerea bewachsene Agarstückchen aufgelegt. Die inokulierten Pflanzen werden in einer abgedunkelten Kammer bei ca. 200C und 100 % relativer Luftfeuchtigkeit aufgestellt.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried, 2 small pieces of agar covered with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at about 20 0 C and 100% relative humidity.
2 Tage nach der Inokulation wird die Größe der Befallsflecken auf den Blättern ausgewertet. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird. 2 days after the inoculation, the size of the infestation spots on the leaves is evaluated. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
Beispiel DExample D
Pyrenophora teres - Test (Gerste) / protektivPyrenophora teres - test (barley) / protective
Lösungsmittel: 50 Gewichtsteile N,N-DimethylacetamidSolvent: 50 parts by weight of N, N-dimethylacetamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer Konidiensuspension von Pyrenophora teres besprüht. Die Pflanzen verbleiben 48 Stunden bei 200C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain 48 hours at 20 0 C and 100% relative humidity in an incubation cabin.
Die Pflanzen werden dann in einem Gewächshaus bei einer Temperatur von ca. 200C und einer relativen Luftfeuchtigkeit von 80 % aufgestellt.The plants are then placed in a greenhouse at a temperature of about 20 0 C and a relative humidity of 80%.
7 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird. 7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
Beispiel EExample E
Alternaria - Test (Tomate) / protektivAlternaria - Test (Tomato) / Protective
Lösungsmittel: 49 Gewichtsteile N, N-DimethylformamidSolvent: 49 parts by weight of N, N-dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit bespritzt man junge Tomatenpflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge. 1 Tag nach der Behandlung werden die Pflanzen mit einer Sporensuspension von Alternaria solani inokuliert und stehen dann 24 h bei 100 % rel. Feuchte und 200C. Anschließend stehen die Pflanzen bei 96 % rel. Luftfeuchtigkeit und einer Temperatur von 200C.To test for protective activity, young tomato plants are sprayed with the preparation of active compound in the stated application rate. One day after the treatment, the plants are inoculated with a spore suspension of Alternaria solani and then stand for 24 h at 100% rel. Humidity and 20 0 C. Subsequently, the plants are at 96% rel. Humidity and a temperature of 20 0 C.
7 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird. 7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.

Claims

Patentansprüche claims
1. Biphenylthiazolcarboxamide der Formel (!)1. Biphenylthiazolecarboxamides of the formula (I)
in welcher in which
R1 für Wasserstoff, Halogen, Amino, CrC4-Alkylamino, Di-(Ci-C4-alkyl)amino, Cyano,R 1 represents hydrogen, halogen, amino, C r C 4 alkylamino, di- (Ci-C 4 alkyl) amino, cyano,
CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R2 für Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R3 für Wasserstoff, C-Cg-Alkyl, C,-C6-Alkylsulfinyl, d-Q-Alkylsulfonyl, CrC4-Alkoxy- CrC4-alkyl, C3-C8-Cycloalkyl; C,-C6-Halogenalkyl, CrC4-Halogenalkylthio, C]-C4-Ha- logenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-CrC4-alkyl, C3- Cg-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-CrC3-alkyl, (Ci-C3-Alkyl)carbonyl-CrC3-alkyl, (C1-C3-AIkOXy)CaTbO- nyl-Ci-C3-alkyl; Halogen-(Ci-C3-alkyl)carbonyl-C,-C3-alkyl, Halogen-(Ci-C3-alkoxy> carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen;C r C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms, R 2 is halogen, C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 3 represents hydrogen, C-Cg-alkyl, C, -C6 alkylsulfinyl, dQ alkylsulfonyl, C r C 4 alkoxy C r C 4 alkyl, C 3 -C 8 cycloalkyl; R C, -C 6 haloalkyl, C C 4 haloalkylthio, C] -C 4 logenalkylsulfinyl -Ha-, Ci-C4-haloalkylsulfonyl, halo-Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 - Cg-Halogencycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl--C 3 alkyl, (Ci-C 3 alkyl) carbonyl-C r C 3 alkyl, (C 1 -C 3 -alkoxy) CaTbO- nyl-Ci-C 3 alkyl; Halogeno (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, halogeno (C 1 -C 3 -alkoxy ) -carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and / or or bromine atoms;
(CrCg-Alkyl)carbonyl, (CrC8-Alkoxy)carbonyl, (C,-C4-Alkoxy-CrC4-alkyl)carbonyl, (C3-Cg-Cycloalkyl)carbonyl; (Ci-C6-Halogenalkyl)carbonyl, (Ci-C6-Halogenalkoxy)car- bonyl, (Halogen-CrC4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C8-Halogencycloalkyl)carbo- nyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R6, -CONR7R8 oder -CH2NR9R10 steht,(C r Cg-alkyl) carbonyl, (C r C 8 alkoxy) carbonyl, (C, -C 4 alkoxy-C r C 4 alkyl) carbonyl, (C3 -CG-cycloalkyl) carbonyl; (Ci-C 6 haloalkyl) carbonyl, (Ci-C 6 haloalkoxy) carbonyl, (halo-C r C 4 alkoxy-Ci-C4-alkyl) carbonyl, (C 3 -C 8 halocycloalkyl) carbo- nyl with in each case 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10 ,
R4 für Halogen, CrC4-Alkyl, CrC4-Alkoxy, CrC4-Alkylthio oder CrC4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht, m für 1 oder 2 steht, wobei die Reste R4 gleich oder verschieden sein können, wenn m für 2 steht, R5 für Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxy, Carbamoyl, Thio- carbamoyl, Ci-Cg-Alkyl, C2-C6-Alkenyl, CrC8-Alkoxy, C2-C6-Alkenyloxy, Ci-C8-Al- kylthio, CrC8-Alkylsulfmyl, Ci-C8-Alkylsulfonyl, CrCg-Hydroxyalkyl, CrC8-Oxo- alkyl, CrC8-Alkoxyalkyl, d-Cg-Alkylthioalkyl, CrC8-Dialkoxyalkyl, C,-C6-Alkyl- amino, Di(Ci-C6-alkyl)amino, (Ci-C6-Alkyl)aminocarbonyl, Di(C]-C6-alkyl)aminocarbo- nyl, (Ci-C6-Alkyl)carbonylamino, (Ci-C6-Alkyl)carbonyl(Ci-C6-alkyl)amino, (C2-C6- Alkenyl)carbonyl, (C2-C6-AIkinyl)carbonyl, C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, oder für CrC6-Halogenalkyl, Ci-Cβ-Halogenalkoxy, Ci-C6-Halogenalkylthio, Ci-C6- Halogenalkylsulfinyl oder Ci-C6-Halogenalkylsulfonyl mit jeweils 1 bis 13 Halogen¬ atomen, C2-C6-Halogenalkenyl, C2-C6-Halogenalkenyloxy mit jeweils 1 bis 11 gleichen oder verschiedenen Halogenatomen steht, R6 für Wasserstoff, C,-C8-Alkyl, CrC8-Alkoxy, C,-C4-Alkoxy-C,-C4-alkyl, C3-C8-Cy- cloalkyl; Ci-C6-Halogenalkyl, CrC6-Halogenalkoxy, Halogen-CrC4-alkoxy-CrC4- alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom¬ atomen steht,R 4 is halogen, C r C 4 alkyl, C r C 4 alkoxy, C r is C 4 -alkylthio or C r C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, m represents 1 or 2, where R 4 may be the same or different when m is 2, R 5 is halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, Ci-Cg-alkyl, C 2 -C 6 alkenyl, C r C 8 alkoxy, C 2 -C 6 alkenyloxy, Ci-C 8 alkylthio -Al-, C r C 8 -Alkylsulfmyl, Ci-C 8 alkylsulfonyl, C r Cg hydroxyalkyl, C r C 8 alkyl oxo, C r C 8 alkoxyalkyl, d-Cg alkylthioalkyl, C r C 8 -Dialkoxyalkyl, C, -C 6 alkyl amino, di (Ci-C 6 alkyl) amino, (C 1 -C 6 -alkyl) aminocarbonyl, di (C 1 -C 6 -alkyl) aminocarbonyl, (C 1 -C 6 -alkyl) carbonylamino, (C 1 -C 6 -alkyl) carbonyl (C 1 -C 6 -alkyl) amino, (C 2 -C 6 -alkenyl) carbonyl, (C 2 -C 6 -alkynyl) carbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, Ci-C atoms haloalkylsulfinyl or haloalkylsulfonyl having in each case 6 1 to 13 halogenoalkyl, C 2 -C 6 - or C r C 6 haloalkyl, Ci-Cβ-haloalkoxy, Ci-C6 haloalkylthio, Ci-C 6 - haloalkenyl, C 2 -C 6 haloalkenyloxy same, each having 1 to 11 or different halogen atoms, R 6 represents hydrogen, C, -C 8 alkyl, C r C 8 alkoxy, C, -C 4 alkoxy-C -C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C 6 haloalkyl, C r C 6 haloalkoxy, halogen-CrC 4 -alkoxy-C r C 4 - alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or hydrogen bromide atoms,
R7 und R8 unabhängig voneinander jeweils für Wasserstoff, CrC8-Alkyl, Ci-C4-Alkoxy-CrC4- alkyl, C3-C8-Cycloalkyl; CrC8-Halogenalkyl, Halogen-C,-C4-alkoxy-Ci-C4-alkyl, C3-R 7 and R 8 are each independently hydrogen, C r C 8 alkyl, Ci-C 4 -alkoxy-C r C 4 - alkyl, C 3 -C 8 cycloalkyl; C r C 8 -haloalkyl, halo-C, -C 4 -alkoxy-Ci-C 4 alkyl, C 3 -
Cs-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R7 und R8 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen ge¬ gebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Cp C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, . wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus derCs-halogenocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 7 and R 8 together with the nitrogen atom to which they are attached are optionally mono- or polysubstituted, identically or differently, by halogen or Cp C 4 alkyl substituted saturated heterocycle having 5 to 8 ring atoms,. wherein the heterocycle 1 or 2 further, non-adjacent heteroatoms of the
Reihe Sauerstoff, Schwefel oder NR11 enthalten kann,May contain oxygen, sulfur or NR 11 ,
R9 und R10 unabhängig voneinander für Wasserstoff, CrC8-Alkyl, C3-C8-Cycloalkyl; CrC8- Halogenalkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R9 und R10 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen ge¬ gebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Cp C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR11 enthalten kann, R11 für Wasserstoff oder Ci-C6-Alkyl steht, wobei Verbindungen der Formel (I) ausgenommen sind, in welcher R1 für Wasserstoff oder Methyl steht,R 9 and R 10 are independently hydrogen, C r C 8 alkyl, C 3 -C 8 cycloalkyl; C r C 8 - haloalkyl, C 3 -C 8 halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 9 and R 10 also together with the nitrogen atom to which they are attached, a ge optionally mono- or polysubstituted, identically or differently, by halogen or Cp C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, wherein the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the series oxygen, sulfur or NR 11 , R 11 is hydrogen or C 1 -C 6 -alkyl, compounds of the formula (I) being excluded in which R 1 is hydrogen or methyl,
R2 für Chlor, Methyl, Difluormethyl oder Trifluormethyl steht,R 2 is chlorine, methyl, difluoromethyl or trifluoromethyl,
R5 für Halogen, CrC4-Alkyl, Trifluormethyl, CrC4-Alkoxy oder CrC4-Alkylthio steht, wenn R3 für Wasserstoff und R4 für Fluor und m für 1 steht.R 5 is halogen, C r C 4 alkyl, trifluoromethyl, C r C 4 alkoxy or C r C 4 alkylthio, when R 3 is hydrogen and R 4 is fluorine and m is 1.
2. Biphenylthiazolcarboxamide der Formel (I) gemäß Anspruch 1, in welcher2. Biphenylthiazolcarboxamide of the formula (I) according to claim 1, in which
R1 für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-C4-Alkylamino, Di(Ci-C4- alkyl)amino, Cyano, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, R2 für Fluor, Chlor, Brom, Methyl, Ethyl oder CrC2-Halogenalkyl mit 1 bis 5 Fluor,R 1 represents hydrogen, fluorine, chlorine, bromine, amino, Ci-C 4 alkylamino, di (Ci-C 4 - alkyl) amino, cyano, methyl, ethyl or C r C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R 2 represents fluorine, chlorine, bromine, methyl, ethyl or C r C 2 -haloalkyl having 1 to 5 fluorine,
Chlor und/oder Bromatomen steht,Chlorine and / or bromine atoms is,
R3 für Wasserstoff, C1-C6-AlM, CrC4-Alkylsulfinyl, CrC4-Alkylsulfonyl, CrC3-Alkoxy- CrC3-alkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, CrC4-Halogenalkylthio, CrC4- Halogenalkylsulfinyl, CrC4-Halogenalkylsulfonyl, Halogen-CrC3-alkoxy-Ci-C3-alkyl,R 3 is hydrogen, C 1 -C 6 -Alm, C r C 4 alkylsulfinyl, C r C 4 alkylsulfonyl, C r C 3 alkoxy C r C 3 alkyl, C 3 -C 6 cycloalkyl; C r C 4 haloalkyl, C r C 4 haloalkylthio, C r C 4 - haloalkylsulfinyl, C r C 4 -haloalkylsulfonyl, halo-C r C 3 alkyl alkoxy-Ci-C 3,
C3-Cg-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-CrC3-alkyl, (CrC3-Alkyl)carbonyl-Ci-C3-alkyl, (CrC3-Alkoxy)car- bonyl-Ci-C3-alkyl; Halogen^d-Cs-alky^carbonyl-Cj-Cralkyl, Halogen-(Ci-C3-alk- oxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (C,-C6-Alkyl)carbonyl, (CrC4-Alkoxy)carbonyl, (CrC3-Alkoxy-CrC3-alkyl)carbo- nyl, (C3-C6-Cycloalkyl)carbonyl; (CrC4-Halogenalkyl)carbonyI, (CrC4-Halogenalk- oxy)carbonyl, (Halogen-Ci-C3-alkoxy-Ci-C3-alkyl)carbonyl, (C3-C6-Halogencyclo- alkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R6, -CONR7R8 oder -CH2NR9R10 steht, R4 für Fluor, Chlor, Methyl, iso-Propyl, Methoxy, Methylthio oder Trifluormethyl steht, m für 1 oder 2 steht, wobei die Reste R4 gleich oder verschieden sein können, wenn m für 2 steht,C 3 -Cg-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C r C 3 alkyl, (C r C 3 alkyl) carbonyl-Ci-C 3 alkyl, (C r C 3 alkoxy) carbonyl-Ci-C 3 alkyl; Halogeno-C 1 -C 6 -alkyl-carbonyl-C 1 -C 4 -alkyl, halogeno (C 1 -C 3 -alkoxy) -carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms; (C, -C 6 alkyl) carbonyl, (C r C 4 alkoxy) carbonyl, (C r C 3 alkoxy-C r C 3 alkyl) carbonyl, (C 3 -C 6 cycloalkyl) carbonyl ; (C r C 4 haloalkyl) carbonyl, (C r C 4 -Halogenalk- oxy) carbonyl, (halo-Ci-C 3 alkoxy-Ci-C 3 alkyl) carbonyl, (C 3 -C 6 -Halogencyclo- alkyl) carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10 , R 4 represents fluorine, chlorine, methyl, isopropyl, methoxy, methylthio or trifluoromethyl, m is 1 or 2, where the radicals R 4 may be the same or different, when m is 2,
R5 für Fluor, Chlor, Brom, Cyano, Nitro, Amino, Hydroxy, Formyl, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Vinyl, Allyl, Methoxy, Ethoxy, n- oder iso- Propoxy, Vinyloxy, Allyloxy, Methylthio, Ethylthio, n- oder iso-Propylthio, Methyl- sulfinyl, Ethylsulfinyl, n- oder iso-Propylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Methylthiomethyl, Methylthioethyl, Ethylthiomethyl, Ethylthioethyl, Methylamino, Ethylamino, iso-Propylamino, Dimethylamino, Diethylamino, Dipropylamino, Diiso- propylamino, Methylcarbonyl, Ethylcarbonyl, Methylaminocarbonyl, Dimethylamino- carbonyl, Methylcarbonylamino, Methylcarbonylmethylamino, Cyclopropyl, Cyclopro- pyloxy, Trifluormethyl, Trichlormethyl, Trifluorethyl, Difluormethoxy, Trifluormeth- oxy, Difluorchlormethoxy, Trifluorethoxy, Difluormethylthio, Difluorchlormethylthio oder Trifluormethylthio steht, R6 für Wasserstoff, Q-Q-Alkyl, CrC4-Alkoxy, Ci-C3-Alkoxy-C,-C3-alkyl, C3-C6-R 5 is fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, vinyl, allyl, methoxy, ethoxy , n- or isopropoxy, vinyloxy, allyloxy, methylthio, ethylthio, n- or iso-propylthio, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, methoxymethyl, methoxyethyl , Ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, methylamino, ethylamino, isopropylamino, dimethylamino, diethylamino, dipropylamino, diisopropylamino, methylcarbonyl, ethylcarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methylcarbonylamino, methylcarbonylmethylamino, cyclopropyl, cyclopropyloxy , trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, Trifluormeth- oxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio or trifluoromethylthio, R 6 is hydrogen, QQ-alkyl, C r C 4 alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -
Cycloalkyl; Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy, Halogen-Ci-C3-alkoxy-Ci- C3-alkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom¬ atomen steht, R7 und R8 unabhängig voneinander jeweils für Wasserstoff, Ci-C6-Alkyl, Ci-C3-AIkOXy-Ci-C3- alkyl, C3-C6-Cycloalkyl; CrC4-Halogenalkyl, Halogen-CrC3-alkoxy-CrC3-alkyl, C3-cycloalkyl; Ci-C 4 haloalkyl, Ci-C4 haloalkoxy, halogen-Ci-C 3 alkoxy-Ci- C 3 alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or hydrobromic stands atoms, R 7 and R 8 are each independently hydrogen, Ci-C 6 -alkyl, C 3 -alkoxy-Ci-C 3 - alkyl, C 3 -C 6 cycloalkyl; C r C 4 -haloalkyl, haloCrC 3 -alkoxy-C r C 3 -alkyl, C 3 -
C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R7 und R8 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen ge¬ gebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder Ci-C4- Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR11 enthalten kann,C 6 -halo cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 7 and R 8 furthermore together with the nitrogen atom to which they are attached form a ge is optionally mono- to tetrasubstituted by identical or different halogen or Ci-C 4 - alkyl substituted saturated heterocycle having 5 or 6 ring atoms, where the heterocycle May contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 11 ,
R9 und R10 unabhängig voneinander für Wasserstoff, C,-C6-Alkyl, C3-C6-Cycloalkyl; CrC4- Halogenalkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 9 and R 10 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl; C r C 4 - haloalkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R9 und R10 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen ge- gebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder Ci-C4-R 9 and R 10 together with the nitrogen atom to which they are attached are optionally monosubstituted to quadruple, identical or different, by halogen or C 1 -C 4 -
Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oderNRπ enthalten kann, R11 für Wasserstoff oder CrC4-Alkyl steht, wobei Verbindungen der Formel (I) ausgenommen sind, in welcherForm alkyl-substituted saturated heterocycle having 5 or 6 ring atoms, wherein the heterocycle may contain 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR π , R 11 is hydrogen or C r C 4 alkyl, wherein compounds of the formula (I) are excluded, in which
R1 für Wasserstoff oder Methyl steht,R 1 is hydrogen or methyl,
R2 für Chlor, Methyl, Difluormethyl oder Trifluormethyl steht,R 2 is chlorine, methyl, difluoromethyl or trifluoromethyl,
R5 für Halogen, CrC4-Alkyl, Trifluormethyl, CrC4-Alkoxy oder CrC4-Alkylthio steht, wenn R3 für Wasserstoff und R4 für Fluor und m für 1 steht.R 5 is halogen, C r C 4 alkyl, trifluoromethyl, C r C 4 alkoxy or C r C 4 alkylthio, when R 3 is hydrogen and R 4 is fluorine and m is 1.
3. Verfahren zum Herstellen der Biphenylthiazolcarboxamide der Formel (I) gemäß An¬ spruch 1, dadurch gekennzeichnet, dass man (a) Carbonsäure-Derivate der Formel (H)3. A process for preparing the Biphenylthiazolcarboxamide of formula (I) according to An¬ claim 1, characterized in that (a) carboxylic acid derivatives of the formula (H)
in welcher in which
R1 und R2 die in Anspruch 1 angegebenen Bedeutungen haben und X1 für Halogen oder Hydroxy steht, mit Biphenylaminen der Formel (DI)R 1 and R 2 have the meanings given in claim 1 and X 1 is halogen or hydroxy, with biphenylamines of the formula (DI)
(in) in welcher R3, R4, m und R5 die in Anspruch 1 angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Kondensationsmittels, gegebenenfalls in Gegenwart eines Säurebindemittels und ge¬ gebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder(in) in which R 3 , R 4 , m and R 5 have the meanings given in claim 1, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
(b) Halogencarboxamide der Formel (TV)(b) Halo carboxamides of the formula (TV)
in welcher in which
R1, R2, R3, R4 und m die in Anspruch 1 angegebenen Bedeutungen haben, X2 für Brom, Iod oder Trifluormethylsulfonat steht, mit Boronsäure-Derivaten der Formel (V)R 1 , R 2 , R 3 , R 4 and m have the meanings given in claim 1, X 2 is bromine, iodine or trifluoromethylsulfonate, with boronic acid derivatives of the formula (V)
in welcher in which
R5 die in Anspruch 1 angegebenen Bedeutungen hat und G1 und G2 jeweils für Wasserstoff oder zusammen für Tetramethylethylen stehen, in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebindemit¬ tels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oderR 5 has the meanings given in claim 1 and G 1 and G 2 are each hydrogen or together are tetramethylethylene, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
(c) Boronsäure-Derivate der Formel (VT)(c) boronic acid derivatives of the formula (VT)
in welcher in which
R1, R2, R3, R4 und m die in Anspruch 1 angegebenen Bedeutungen haben,R 1 , R 2 , R 3 , R 4 and m have the meanings given in claim 1,
G3 und G4 jeweils für Wasserstoff oder zusammen für Tetramethylethylen stehen, mit Phenyl-Derivaten der Formel (VH) in welcherG 3 and G 4 are each hydrogen or together are tetramethylethylene, with phenyl derivatives of the formula (VH) in which
R5 die in Anspruch 1 angegebenen Bedeutungen hat und X3 für Chlor, Brom, Iod oder Trifluormethylsulfonat steht, in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Säurebinde¬ mittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oderR 5 has the meanings given in claim 1 and X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
(d) Halogencarboxamide der Formel (FV)(d) Halo carboxamides of the formula (IV)
in welcher in which
R1, R2, R3, R4 und m die in Anspruch 1 angegebenen Bedeutungen haben,R 1 , R 2 , R 3 , R 4 and m have the meanings given in claim 1,
X2 für Brom, Iod oder Trifluormethylsulfonat steht, mit Phenyl-Derivaten der Formel (VIT)X 2 is bromine, iodine or trifluoromethylsulfonate, with phenyl derivatives of the formula (VIT)
in welcher in which
R5 die in Anspruch 1 angegebenen Bedeutungen hat und X3 für Chlor, Brom, Iod oder Trifluormethylsulfonat steht, in Gegenwart eines Palladium- oder Nickel-Katalysators und in Gegenwart von 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis-l,3,2-dioxaborolan, gegebenenfalls in Gegen¬ wart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungs¬ mittels umsetzt, oderR 5 has the meanings given in claim 1 and X 3 is chlorine, bromine, iodine or trifluoromethylsulfonate, in the presence of a palladium or nickel catalyst and in the presence of 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-l, 3,2-dioxaborolane, optionally in the presence of an acid-binding agent and if appropriate in the presence of a diluent, or
(e) Biphenylthiazolcarboxamide der Formel (I-a)(e) Biphenylthiazolecarboxamides of the formula (I-a)
in welcher in which
R1, R2, R4, m und R5 die in Anspruch 1 angegebenen Bedeutungen haben, mit Halogeniden der Formel (VH1)R 1 , R 2 , R 4 , m and R 5 have the meanings given in claim 1, with halides of the formula (VH1)
R^-X4 (VIII) in welcherR ^ -X 4 (VIII) in which
R3A für Ci-C8-Alkyl, C,-C6-Alkylsulfinyl, C,-C6-Alkylsulfonyl, C1-C4-AIk0Xy-C1- C4-alkyl, C3-C8-Cycloalkyl; Ci-Ce-Halogenalkyl, C1-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, Ci-Q-Halogenalkylsulfonyl, Halogen-Ci-C4- alkoxy-CrC4-alkyl, C3-Cg-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3-alkyl, (C]-C3-Alkyl)- carbonyl-CrC3-alkyl, (CrC3-Alkoxy)carbonyl-Ci-C3-alkyl; Halogen-(Ci-C3- alkyl)carbonyl-Ci-C3-alkyl, Halogen-(CrC3-alkoxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (C,-C8-Alkyl)carbonyl, (C,-C8-Alkoxy)carbonyl, (C,-C4-Alkoxy-Ci-C4-alkyl> carbonyl, (C3-C8-Cycloalkyl)carbonyl; (Ci-C6-Halogenalkyl)carbonyl, (CrC6-R 3A represents C 8 alkyl, C, -C6 alkylsulfinyl, C, -C 6 alkylsulfonyl, C 1 -C 4 -AIk 0 Xy-C 1 - C 4 alkyl, C 3 -C 8 - cycloalkyl; Ci-Ce haloalkyl, C 1 -C 4 haloalkylthio, Ci-C4-haloalkylsulfinyl, Ci-Q-haloalkylsulfonyl, halo-Ci-C 4 - alkoxy-C r C 4 alkyl, C 3 -CG-halocycloalkyl with in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 3 alkyl, (C] -C3 alkyl) - carbonyl-C r C 3 alkyl, (C r C 3 alkoxy) carbonyl-Ci-C 3 alkyl; Halogen (Ci-C 3 - alkyl) carbonyl-Ci-C 3 -alkyl, halogen- (C r C 3 -alkoxy) carbonyl-Ci-C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 8 -alkyl) carbonyl, (C 1 -C 8 -alkoxy) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C 8 -cycloalkyl) carbonyl (C 1 -C 6 -haloalkyl) carbonyl, (C r C 6 -
Halogenalkoxy)carbonyl, (Halogen-CrC4-alkoxy-CrC4-alkyl)carbonyl, (C3- C8-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(O)C(O)R6, -CONR7R8 oder -CH2NR9R10 steht, R6, R7, R8, R9 und R10 die in Anspruch 1 angegebenen Bedeutungen haben, X4 für Chlor, Brom oder Iod steht, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt.Haloalkoxy) carbonyl, (halo-C r C 4 -alkoxy-C r C 4 alkyl) carbonyl, (C 3 - C 8 halocycloalkyl) carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (O) C (O) R 6 , -CONR 7 R 8 or -CH 2 NR 9 R 10 , R 6 , R 7 , R 8 , R 9 and R 10 have the meanings given in claim 1, X 4 represents chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
4. Mittel zur Bekämpfung unerwünschter Mikroorganismen, gekennzeichnet durch einen Gehalt an mindestens einem Biphenylthiazolcarboxamid der Formel (I) gemäß Anspruch 1 neben4. A composition for controlling unwanted microorganisms, characterized by a content of at least one Biphenylthiazolcarboxamid of the formula (I) according to claim 1 in addition
Streckmitteln und/oder oberflächenaktiven Stoffen.Extenders and / or surfactants.
5. Verwendung von Biphenylthiazolcarboxamiden der Formel (I) gemäß Anspruch 1 zur Be¬ kämpfung unerwünschter Mikroorganismen.5. Use of biphenylthiazolecarboxamides of the formula (I) according to Claim 1 for controlling unwanted microorganisms.
6. Verfahren zur Bekämpfung unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Biphenylthiazolcarboxamide der Formel (I) gemäß Anspruch 1 auf die Mikro¬ organismen und/oder deren Lebensraum ausbringt. 6. A method for controlling unwanted microorganisms, characterized in that biphenylthiazolcarboxamides of the formula (I) according to claim 1 on the microorganisms and / or their habitat ausbringt.
7. Verfahren zur Herstellung von Mitteln zur Bekämpfung unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Biphenylthiazolcarboxamide der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt.7. A process for the preparation of agents for controlling unwanted microorganisms, characterized in that mixed Biphenylthiazolcarboxamide of formula (I) according to claim 1 with extenders and / or surface-active substances.
8. Halogencarboxamide der Formel (IV)8. Halo carboxamides of the formula (IV)
in welcher in which
R1, R2, R3, R4 und m die in Anspruch 1 angegebenen Bedeutungen haben, X2 für Brom, Iod oder Trifluormethylsulfonat steht.R 1 , R 2 , R 3 , R 4 and m have the meanings given in claim 1, X 2 is bromine, iodine or trifluoromethylsulfonate.
9. Boronsäure-Derivate der Formel (VT)9. Boronic acid derivatives of the formula (VT)
in welcher in which
R1, R2, R3, R4 und m die in Anspruch 1 angegebenen Bedeutungen haben, G3 und G4 jeweils für Wasserstoff oder zusammen für Tetramethylethylen stehen. R 1 , R 2 , R 3 , R 4 and m have the meanings given in claim 1, G 3 and G 4 are each hydrogen or together are tetramethylethylene.
EP05771671A 2004-08-27 2005-08-13 Biphenyl thiazole carboxamides Withdrawn EP1786795A2 (en)

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DE102004041532A DE102004041532A1 (en) 2004-08-27 2004-08-27 biphenyl thiazole carboxamides
PCT/EP2005/008839 WO2006024389A2 (en) 2004-08-27 2005-08-13 Biphenyl thiazole carboxamides

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JP2008510746A (en) 2008-04-10
MX2007002243A (en) 2007-04-20
BRPI0514439A (en) 2008-06-10
WO2006024389A2 (en) 2006-03-09
KR20070050958A (en) 2007-05-16
CN101044128A (en) 2007-09-26
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CR8879A (en) 2007-08-28
AR050516A1 (en) 2006-11-01

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