EP1786795A2 - Biphenyl thiazol carboxamides - Google Patents

Biphenyl thiazol 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Withdrawn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)
English (en)
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/fr
Withdrawn legal-status Critical Current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.

Abstract

L'invention concerne de nouveaux biphényl thiazol carboxamides de formule (I) dans laquelle R<SUP>1</SUP>, R<SUP>2</SUP>, R<SUP>3</SUP>, R<SUP>4</SUP>, m et R<SUP>5</SUP> ont les significations indiquées dans la description. La présente invention porte également sur plusieurs procédés pour produire ces substances et sur leur utilisation pour lutter contre des micro-organismes indésirables, ainsi que sur de nouveaux produits intermédiaires et leur réalisation.
EP05771671A 2004-08-27 2005-08-13 Biphenyl thiazol carboxamides Withdrawn EP1786795A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004041532A DE102004041532A1 (de) 2004-08-27 2004-08-27 Biphenylthiazolcarboxamide
PCT/EP2005/008839 WO2006024389A2 (fr) 2004-08-27 2005-08-13 Biphenyl thiazol carboxamides

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EP1786795A2 true EP1786795A2 (fr) 2007-05-23

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US (1) US20090105316A1 (fr)
EP (1) EP1786795A2 (fr)
JP (1) JP2008510746A (fr)
KR (1) KR20070050958A (fr)
CN (1) CN101044128B (fr)
AR (1) AR050516A1 (fr)
BR (1) BRPI0514439A (fr)
CA (1) CA2577997A1 (fr)
CR (1) CR8879A (fr)
DE (1) DE102004041532A1 (fr)
MX (1) MX2007002243A (fr)
WO (1) WO2006024389A2 (fr)

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DE102004005786A1 (de) * 2004-02-06 2005-08-25 Bayer Cropscience Ag Haloalkylcarboxamide
DE102004041530A1 (de) * 2004-08-27 2006-03-02 Bayer Cropscience Ag Biphenylthiazolcarboxamide
DE102005022147A1 (de) * 2005-04-28 2006-11-02 Bayer Cropscience Ag Wirkstoffkombinationen
BRPI0710774A2 (pt) * 2006-05-03 2011-06-21 Basf Se método para proteger plantas após germinação contra o ataque de fungos fitopatogênicos foliares, formulação para tratamento de semente, semente, e, uso de pelo menos um composto
JO3598B1 (ar) 2006-10-10 2020-07-05 Infinity Discovery Inc الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني
CN102046179B (zh) 2008-04-09 2015-01-14 英菲尼提制药公司 脂肪酸酰胺水解酶抑制剂
AR074623A1 (es) * 2008-05-02 2011-02-02 Basf Se Procedimiento para la preparacion de esteres de acido 2-(aminometiliden)-3-oxobutirico, sustituidos por halogeno
WO2009133178A1 (fr) 2008-05-02 2009-11-05 Basf Se Procédé de fabrication d’esters de l’acide 2-(aminométhylidène)-4,4-difluoro-3-oxobutyrique
CN102015654B (zh) 2008-05-05 2014-03-12 巴斯夫欧洲公司 制备1，3，4-取代的吡唑化合物的方法
EP2307384B1 (fr) * 2008-07-21 2012-04-25 Basf Se Procédé de préparation d esters de pyrazolecarboxylique disubstitués en 1,3
JP2012523425A (ja) 2009-04-07 2012-10-04 インフイニトイ プハルマセウトイカルス インコーポレイテッド 脂肪酸アミドヒドロラーゼの阻害薬
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JP2013510111A (ja) 2009-11-05 2013-03-21 ビーエーエスエフ ソシエタス・ヨーロピア １，３−二置換ピラゾール化合物の調製方法
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CN101044128A (zh) 2007-09-26
KR20070050958A (ko) 2007-05-16
WO2006024389A2 (fr) 2006-03-09
WO2006024389A3 (fr) 2006-05-18
AR050516A1 (es) 2006-11-01
US20090105316A1 (en) 2009-04-23
CR8879A (es) 2007-08-28
CA2577997A1 (fr) 2006-03-09
DE102004041532A1 (de) 2006-03-02
MX2007002243A (es) 2007-04-20
JP2008510746A (ja) 2008-04-10
CN101044128B (zh) 2012-04-18
BRPI0514439A (pt) 2008-06-10

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