EP1966149A1 - Biphenyl carboxamides for controlling micro-organisms - Google Patents

Biphenyl carboxamides for controlling micro-organisms

Info

Publication number
EP1966149A1
EP1966149A1 EP06829298A EP06829298A EP1966149A1 EP 1966149 A1 EP1966149 A1 EP 1966149A1 EP 06829298 A EP06829298 A EP 06829298A EP 06829298 A EP06829298 A EP 06829298A EP 1966149 A1 EP1966149 A1 EP 1966149A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
halogen
carbonyl
hydrogen
haloalkyl
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Withdrawn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
EP06829298A
Other languages
German (de)
French (fr)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Jörg Nico GREUL
Herbert Gayer
Arnd Voerste
Ulrike Wachendorff-Neumann
Peter Dahmen
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1966149A1 publication Critical patent/EP1966149A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to novel Biphenylcarboxanüde, several processes for their preparation and their use for controlling harmful microorganisms in crop protection and material protection.
  • R ' is hydrogen, C r C 8 alkyl, Ci-Ce-alkylsulfinyl, Ci-C6 alkylsulfonyl, Ci-C 4 -alkoxy-C 1 - C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C ⁇ haloalkyl, C r C 4 haloalkylthio, C r C 4 kylsulf ⁇ nyl -Halogenal-, 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-Ci- Cs-alkyl, (dQ-AlkyOcarbonyl-d-Ca-alkyl, (C 1 -C 3 alkoxy
  • R ' "A represents hydrogen, C, -C6 alkyl, C, -C 6 haloalkyl, C 2 -C ö alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 -
  • Cycloalkyl (C 1 -C 4 -alkoxy) carbonyl, (C 3 -C 6 -alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) -carbonyl or cyano
  • R 2 is hydrogen, C, -C 8 alkyl, C r C 8 alkoxy, C, -C 4 alkoxy-Ci-C 4 alkyl, C 3 -C 8 cycloalkyl; C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halogeno-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -HaJo gencycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms stands,
  • R 3 and R 4 are each independently hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; Ci-C8-haloalkyl, halo-Ci-C 4 alkyl C 1 -C 4 alkoxy, halo-C 3 -C 8 cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 3 and R 4 together with the nitrogen atom to which they are attached, form a saturated heterocycle having 5 to 8 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
  • R 5 and R 6 are each independently hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyl; Ci-C 8-halo, C 3 -C 8 alkyl -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 5 and R 6 furthermore together with the nitrogen atom to which they are attached form a optionally mono- or polysubstituted, identically or differently, by halogen or C 1 -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 7 , R 7 is hydrogen or C 1 -C 6 -alkyl,
  • R 8 is hydrogen or fluorine
  • R 10 is fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl
  • R 11 ö for Ci-C alkyl, or Ci-C is 6 haloalkyl having 1 to 13 halogen atoms, m is 1 or 2;
  • R 12 and R 13 together with the nitrogen atom to which they are attached additionally form a saturated heterocycle having 5 to 8 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
  • X is O (oxygen) or S (sulfur),
  • R 14 is hydrogen, C, -C 4 alkyl, C 1 -C 4 -alkoxy or -NR 16 R 17,
  • R 15 is hydrogen, C 1 -C 8 -alkyl, C, -C 8 alkoxy, QC QC-alkoxy-alkyl, C, -C 4 alkylthio C] -C 4 alkyl or d-C ⁇ -haloalkyl wherein the three radicals R 15 may each be identical or different,
  • 17 is hydrogen or C 1 -C 4 -alkyl
  • R 16 and R 17 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, the heterocycle being 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
  • A is one of the following radicals A1 to A19
  • R 18 represents hydrogen, cyano, halogen, nitro, Ci-C4-alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, C 3 - C ⁇ cycloalkyl, Ci-C 4 haloalkyl, Ci-C4- Haloalkoxy or Ci-C 4 -haloalkhyio each having 1 to 5 halogen atoms, aminocarbonyl or stands,
  • R 19 4 -alkoxy or C 1 -C 4 -AUCyWuO hydrogen, halogen, cyano, Ci-C 4 alkyl, C 1 -C
  • R 20 is hydrogen, C 1 -C 4 -alkyl, hydroxy-C r C 4 -a] kyl, QRC ⁇ alkenyl, C 3 -C 6 cycloalkyl, C 1 -C 4 - alkylthio-Ci-C 4 - alkyl, C 1 -C 4 -alkyl, each having 1 to 5 halogen atoms, or phenyl
  • R 21 and R 22 are independently hydrogen, halogen, C] -C 4 alkyl or C 4 halo-alkyl is having 1 to 5 halogen atoms
  • R 23 is halogen, cyano or Ci-C 4 alkyl, or C C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms
  • R 24 and R 25 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -a]
  • Halogenoalkyl having 1 to 5 halogen atoms, R 2 S, hydrogen, halogen, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
  • R 27 is hydrogen, halogen, hydroxy, cyano, Ci-C 6 alkyl, Ci-C 4 haloalkyl, C 1 -C 4 logenalkoxy -Ha- or Ci-C4-haloalkylthio having in each case 1 to 5 halogen atoms,
  • R 28 represents halogen, hydroxy, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -
  • Halogen atoms is,
  • R 2S hydrogen, halogen, cyano, Ci-C 4 alkyl, C r C 4 alkoxy, C, -C 4 alkylthio, Cj-C A- haloalkyl, Ci-C4-haloalkoxy having in each case 1 to 5 halogen atoms, , Ci-C 4 -
  • R 30 4 -alkyl or Ci-C 4 haloalkyl is Ci-C with 1 to 5 halogen atoms
  • R 31 is C, -C 4 -alkyl
  • Q 1 represents S (sulfur), SO, SO 2 or CH 2 p is 0, 1 or 2
  • R 22 is identical or different radicals, if p is 2,
  • R 32 4 haloalkyl is Ci-C 4 alkyl or C 1 to 5 halogen atoms
  • R 33 4 -alkyl or C is 4 -halogenoalkyl having 1 to 5 halogen atoms is C
  • R 34 and R 35 independently of one another represent hydrogen, halogen, amino, C 1 -C 4 -alkyl or C 1 -C 4 -
  • Haloalkyl having 1 to 5 halogen atoms R 3S is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 -haloalkyl having 1 to 5 halogen atoms, R 37 and R 38 independently of one another are hydrogen, halogen, amino, nitro , C 1 -C 4 -alkyl or
  • R 39 is hydrogen, halogen, C 1 -C 4 -AUCyI or C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
  • R 40 is hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) amino, cyano, C 1 -C 4 -
  • R 41 represents halogen, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms
  • R 42 is hydrogen, halogen, amino, Ci-C 4 alkylamino, di- (Ci -C 4 alkyl ) amino, cyano, Ci-C 4 - alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms
  • R 43 represents halogen, Ci-C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms
  • R 44 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms
  • R 45 is hydrogen or C 1 -C 4 -alkyl
  • R 46 is halogen or C 1 -C 4 -alkyl
  • R 47 is C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms
  • R 48 4 haloalkyl represents hydrogen, halogen, Ci-C 4 alkyl or C 1 to 5 halogen atoms
  • R 49 represents halogen, hydroxyl, Ci-C4-alkyl, Ci-C 4 alkoxy, Ci-C 4 -Alkyhhio, Ci-C 4 haloalkyl, Ci-C4-haloalkylthio or C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,
  • R 50 is 4 alkyl is C
  • R 51 represents hydrogen, cyano, C 1 -C 4 -alkyl, Ci-C 4 haloalkyl having 1 to 5 halogen atoms, C 1 -C 4 - alkoxy-Ci-C4- alkyl, hydroxy-d-Gralkyl, Ci-C 4 -Alkylsulfbnyl, DitQ-Q-alkytyalTrinosulfonyl, Ci-C f i-alkylcarbonyl or in each case optionally substituted phenylsulfonyl or benzoyl,
  • R 52 is hydrogen, halogen, Ci-C 4 -alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms
  • R 53 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl or C r C 4 -haloalkyl with 1 to 5 halogen atoms
  • R 54 is hydrogen, halogen, C 1 -C 4 -AllCyI or C r C 4 haloalkyl having 1 to 5 halogen atoms.
  • biphenylcarboxamides of the formula (I) are obtained by reacting (a) carboxylic acid halides of the formula (II)
  • X 1 is halogen or hydroxy, with amines of the formula (UI)
  • R 1 , R 8 , R 9 and R 10 have the meanings given above, if appropriate in the presence of a coupling reagent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
  • R 1 B is Ci-Cs-alkyl, d-Ce-alkylsulfinyl, Ci-C6 alkylsulfonyl, Ci-C4-alkoxy-Ci-C4 -AL- alkyl, C 3 -C 8 cycloalkyl; Q-C ⁇ -haloalkyl, dQ-haloalkylthio, Ci-C 4 -HaIo- genalkylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1
  • Hal is chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
  • novel biphenylcarboxamides 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 of the invention may optionally be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as. 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 claimed.
  • the biphenylthiazolecarboxamides according to the invention are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
  • R 1 preferably represents hydrogen, Ci-C 6 alkyl, Ci-C-alkylsulfinyl, Ci-C 4 alkylsulfonyl, C 1 - C 3 alkoxy-Ci-C 3 alkyl, C 3 -C 6 cycloalkyl; Ci-C 4 haloalkyl, C 4 haloalkylthio, C 1 - C 4 haloalkylsulfinyl, Ci-Q-haloalkylsulfonyl, halo-Ci-C 3 alkoxy-C] -C3 alkyl,
  • C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C, C 3 -alkyl, (C 1 -C 12 -alkylcarbonyl-C 1 -C 5 -alkyl, (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl; -C B -alkyl) carbonyl-C 3 -a] kyl, halo (Ci-C 3 alkoxy) carbonyl-C 1 -C 3 - alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms (Ci-C 6 alkyl) carbonyl, (Ci-C 4 alkoxy) carbonyl, (C r C 4 -alkylthio) carbonyl, (Ci-C 3 alkoxy
  • R 1 particularly preferably represents hydrogen, 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, Ethylsutfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, meth
  • R 1 very particularly preferably represents hydrogen, methyl, methoxymethyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, formyl, -
  • R 1 A is preferably hydrogen, Ci-C 4 alkyl, dC 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -
  • R 1 A is particularly preferably hydrogen, methyl or ethyl.
  • R 2 is preferably hydrogen, Q-C ⁇ -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -
  • Ce-cycloalkyl Ci-C 4 haloalkyl, Ci-C4-haloalkoxy, halo-d-Cs-alkoxy-Ci-Q-alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 2 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl,
  • R 3 and R 4 independently of one another preferably represent hydrogen, Ci-C 6 alkyl, Ci-C 3 alkoxy Ci-Cs-alkyl, C 3 -C 6 cycloalkyl; Ci-C 4 haloalkyl, halogen-Ci-C 3 -a-koxy-Ci-C 3 alkyl, C 3 - Ce-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 3 and R 4 also form, together with the nitrogen atom to which they are bonded, preferably a saturated heterocycle having 5 or 6 ring atoms which is optionally monosubstituted to disubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain.
  • R 3 and R 4 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 3 and R 4 also form, together with the nitrogen atom to which they are bonded, particularly preferably a saturated heterocycle which is optionally monosubstituted to monosubstituted, identically or differently by fluorine, chlorine, bromine or methyl, and belongs to the series morpholine,
  • Omomorpholine or piperazine wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
  • R 5 and R 6 are each independently preferably represents hydrogen, Ci-C 6 alkyl, C 3 -C 6 -Cycloal- alkyl; C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 5 and R 6 together with the nitrogen atom to which they are attached preferably also form an optionally mono- or polysubstituted by identical or different halogen or
  • R 5 and R 6 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
  • R 5 and R 6 together with the nitrogen atom to which they are attached moreover preferably form an optionally monosubstituted to tetravalent, identical or different, by fluorine,
  • Thiomorpholine or piperazine wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
  • R 7 is preferably hydrogen or C 1 -C 4 -alkyl.
  • R 7 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • R 8 is preferably hydrogen.
  • R 8 particularly preferably represents fluorine.
  • R 9 is preferably -SO m R ⁇ .
  • R 9 also preferably represents -SO 2 NR 12 R 13 .
  • R 9 is also preferably -Si (R 15 ) 3 .
  • R 9 also preferably represents -NR 12 R 13 .
  • R 9 also preferably represents -CH 2 -NR 12 R 13 .
  • R 10 is preferably fluorine. Chlorine or bromine.
  • R 10 also preferably represents methyl or trifluoromethyl.
  • R 10 particularly preferably represents fluorine.
  • R 10 is also more preferably chlorine.
  • R 10 is also more preferably methyl.
  • R 10 is also more preferably trifluoromethyl.
  • R 11 preferably represents Ci-C4 alkyl or Ci-C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or
  • R 11 particularly preferably represents methyl, ethyl, n-, iso-propyl, n-, i-, s-, t-butyl, trifluoromethyl, -CH 2 CF 3 , -C 2 F 5 or trichloromethyl.
  • R 11 is very particularly preferably methyl, trifluoromethyl, -CH 2 CF 3 or -C 2 F 5 .
  • n is preferably 1, m is also preferably 2, m is particularly preferably 2.
  • R 12 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-
  • R 12 most preferably represents hydrogen or methyl.
  • R 13 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-
  • R 13 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or
  • R 13 most preferably represents hydrogen or methyl.
  • R 12 and R 13 also together with the nitrogen atom to which they are attached preferably form a saturated heterocycle having 5 or 6 ring atoms, optionally mono- or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl the heterocycle may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 7 .
  • R 12 and R 13 also form, together with the nitrogen atom to which they are bonded, more preferably a saturated heterocycle optionally substituted once to four times, identically or differently by fluorine, chlorine, bromine or methyl, from the series
  • X is preferably O (oxygen). X is also preferably S (sulfur).
  • R 14 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, sec- or tert-butoxy or -NR 16 R 17 .
  • R 14 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy or -NR 16 R 17 .
  • R 14 very particularly preferably represents hydrogen, methyl, ethyl, methoxy, ethoxy or -NR 16 R 17 .
  • R 15 preferably represents Ci-C 6 alkyl, Ci-C 6 alkoxy, Ci-C 3 alkoxy-Ci-C 3 alkyl, or QC 3 - alkylthio-Ci-C 3 alkyl, where the three radicals R 15 may be the same or different.
  • R 15 particularly preferably represents methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or ethylthioethyl, where the three radicals R 15 may each be identical or different.
  • R 15 very particularly preferably represents methyl, methoxy, methoxymethyl or methylthio-methyl, where the three radicals R 15 may each be identical or different.
  • R 15 is particularly preferably methyl.
  • R 16 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • R 16 particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl.
  • R 16 very particularly preferably represents hydrogen or methyl.
  • R 17 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • R 17 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl.
  • R 17 most preferably represents hydrogen or methyl.
  • R 15 and R 17 together with the nitrogen atom to which they are attached furthermore preferably form a saturated heterocycle having 5 or 6 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 6 -alkyl, where the heterocycle is 1 or 2 further , non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain.
  • R 16 and R 17 also form, together with the nitrogen atom to which they are bonded, particularly preferably a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, optionally monosubstituted to trisubstituted, identically or differently by fluorine, chlorine, bromine or methyl the piperazine may be substituted on the second nitrogen atom by R 7 .
  • A is preferably one of the radicals Al, A2, A3, A4, A5, A6, A9, AlO, Al 1, A12, or A17.
  • A is particularly preferably one of the radicals
  • A is also very particularly preferably the radical A2.
  • A is also very particularly preferred for the rest of A4.
  • A is also most preferably the radical A5.
  • A is also most preferably the radical A6.
  • A is also most preferably the radical A9.
  • A is also very particularly preferably the radical Al 1.
  • A is also very particularly preferably the radical Al 6.
  • A is also very particularly preferably the radical Al 7.
  • R 18 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, Ci-C 2 haloalkyl, Ci-C genalkoxy 2 -HaIo- with in each case 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, di-fluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl.
  • R 18 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, Methylthio, ethylthio, trifluoromethylthio or difluoromethylthio.
  • R 18 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 18 particularly preferably represents methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl.
  • R 19 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
  • R 19 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or methyl.
  • R 19 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
  • R 20 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl , R 20 particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, di-fluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
  • R 20 very particularly preferably represents hydrogen, methyl, trifluoromethyl or phenyl.
  • R 20 particularly preferably represents methyl.
  • R 21 and R 22 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
  • R 21 and R 22 are particularly preferably each hydrogen.
  • R 23 is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, dC ⁇ -haloalkyl or Ci- C ⁇ -haloalkoxy each having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 23 particularly preferably represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl,
  • R 23 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or
  • R 23 is particularly preferably methyl or trifluoromethyl.
  • R 24 and R 25 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
  • R 24 and R 25 are particularly preferably each hydrogen.
  • R 26 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 26 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
  • R 26 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
  • R 27 is preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or C 1 -C 2 -haloalkylthio, each having 1 to 5 fluorine , Chlorine and / or bromine atoms.
  • R 27 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, Difhiormethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
  • R 27 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
  • R 27 is particularly preferably iodine, methyl, difluoromethyl or trifluoromethyl.
  • R 28 preferably represents fluorine, chlorine, bromine, iodine, hydroxy, cyano, C r C 4 alkyl, methoxy, ethoxy, methylthio, ethylthio, DifluormethyKhio, trifluoromethylthio, Ci-C 2 haloalkyl or Ci-C2 haloalkoxy with in each case 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 28 particularly preferably represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, Difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
  • R 28 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 29 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, Ci-C 4 alkyl, methoxy, ethoxy, methylthio, Ethyrthio, Ci-C 2 haloalkyl or Ci-C2 haloalkoxy, each with 1 to 5 Fluorine, chlorine and / or bromine atoms, C 1 -C 2 -alkylsulphinyl or C 1 -C 2 -alkylsulphonyl.
  • R 29 particularly preferably represents hydrogen ", fluorine, chlorine, bromine, iodine, cyano, n-propyl, iso-
  • Difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulfonyl Difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulfonyl.
  • R 29 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulphinyl or methylsulphonyl ,
  • R 29 particularly preferably represents hydrogen.
  • R 30 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 30 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 31 is preferably methyl or ethyl.
  • R 31 particularly preferably represents methyl
  • Q 1 is preferably S (sulfur), SO 2 or CH 2 .
  • Q 1 particularly preferably represents S (sulfur) or CH 2 .
  • Q 1 very particularly preferably represents S (sulfur).
  • p is preferably 0 or 1. p is particularly preferably 0.
  • R 32 is preferably methyl, ethyl or Ci-Qj-haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 32 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 32 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 33 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
  • R 33 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 33 is particularly anz g Favor g t represents methyl, trifluoromethyl, trichloromethyl or Difluo ⁇ nethyl.
  • R 34 and R 35 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 34 and R 35 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 34 and R 35 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 34 and R 35 are particularly preferably each hydrogen.
  • R 36 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C : -C 2 -
  • R 36 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 36 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 36 particularly preferably represents methyl.
  • R 37 and R 38 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 37 and R 38 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine,
  • R 37 and R 3S independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 37 and R 38 are particularly preferably each hydrogen.
  • R 39 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QC 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,
  • R 39 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 39 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 39 is particularly preferably methyl.
  • R 40 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 with 1 to 5 fluorine, Chlorine and / or bromine atoms.
  • R 40 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 40 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
  • R 40 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
  • R 41 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 41 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 41 is very particularly preferably fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 41 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
  • R 42 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-C 4 -Alkylarnino, di (Ci-C 4 - alkyl) amino, cyano, methyl, ethyl or Ci-C 2 haloalkyl having 1 to 5 fluorine , Chlorine and / or bromine atoms.
  • R 42 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 42 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
  • R 42 particularly preferably represents amino, methylamino, dimethylamino, methyl or
  • R 43 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl of 1 to 5
  • R 43 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
  • R 43 is very particularly preferably fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 43 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
  • R 44 is preferably fluorine, chlorine, bromine, methyl, ethyl or dC 2 -haloalkyl having 1 to 5
  • R 44 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
  • R 44 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl,
  • R 45 is preferably hydrogen, methyl or ethyl. R 45 is particularly preferably methyl.
  • R 46 is preferably fluorine, chlorine, bromine, methyl or ethyl.
  • R 46 particularly preferably represents fluorine, chlorine or methyl.
  • R 47 is preferably methyl, ethyl or dC 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 47 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 47 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 47 is particularly preferably methyl or trifluoromethyl.
  • R 48 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 48 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • R 49 is preferably fluorine, chlorine, bromine, iodine, hydroxy, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, each having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 49 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 49 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 50 is preferably methyl, ethyl, n-propyl or iso-propyl.
  • R 50 is particularly preferably methyl or ethyl.
  • R 51 preferably represents hydrogen, methyl, ethyl, Ci-C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, Ci-C 2 alkoxy-Ci-C 2 alkyl, hydroxymethyl, hydroxyethyl,
  • R 51 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl,
  • R 51 is very particularly preferably methyl or methoxymethyl.
  • R 52 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -
  • R 52 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl
  • R 52 is very particularly preferably hydrogen or methyl.
  • R 53 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 53 is particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 53 very particularly preferably represents hydrogen, methyl, difluoromethyl or trifluoromethyl.
  • R 54 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -
  • R 54 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
  • R 54 is very particularly preferably hydrogen.
  • R il 1 , R ⁇ > 8 ⁇ , R r> 9 9 , R ⁇ > 1 l 0 u and A have the meanings given above.
  • R 1 , R 8 , R 9 , R 1U and A have the meanings given above.
  • R 1 , R s , R 9 , R and IU have the meanings given above.
  • the carboxylic acid halides required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (H).
  • M of this formula (II) A is preferred, particularly preferred, very particularly preferred or particularly preferred for those meanings which have already been described in In connection with the description of the substances of the formula (I) according to the invention as preferred, particularly preferred, etc. were given for this radical.
  • X 1 is preferably fluorine, chlorine or hydroxyl, more preferably chlorine or hydroxy.
  • the carboxylic acid halides of the formula (II) are known and / or can be prepared by known processes (cf., for example, EP-A 0 545 099, JP-A 01-290662 and US 5,093,347).
  • R 1, R 8, R 9 and R 10 are preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have already in connection with the description of the substances according to the invention of the formula (I) as preferably, etc. are given for this radical.
  • Amines of the formulas (TII-I), (IH-2) and (III-3) can be prepared by known processes (see WO 01/53259 and WO 01/49664, see also the Preparation Examples).
  • Biphenylcarboxamides are generally defined by the formula (I-a). In this formula (I-a) have
  • R 8 , R 9 , R 10 and A are preferably, more preferably, very particularly preferably or particularly preferably those meanings which have already been mentioned in connection with the description of the invention.
  • compounds of the formula (I) as preferred, particularly preferred, etc. were given for these radicals.
  • the compounds of the formula (I-a) are compounds according to the invention and can be prepared by process (a).
  • halides which are furthermore required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (TV).
  • R 1 B preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have as preferred above for R 1, more preferred, etc., wherein R 1 B never for Hydrogen stands.
  • Hal is chlorine, bromine or iodine.
  • Halides of the formula (FV) are known.
  • Suitable diluents for carrying out process (a) 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-methylformaneate, N-methylpyrrolidone or hexamethylphosphoric triamide; their mixture
  • the process (a) according to the invention is 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, such as 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 tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylanine, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N -Methyknorphonium, N, N-dimethylaminopyr
  • the process (a) according to the invention is carried out in the presence of a suitable coupling reagent (if X 5 is hydroxyl).
  • a suitable coupling reagent if X 5 is hydroxyl.
  • all customary carbonyl actuators are suitable. These preferably include N- [3- (dimethylamino) propyl] -N'-ediylcarbodi ⁇ iide hydrochloride, N, N'-di-sec-butyl-carbodiirnide, N, N'-dicyclohexylcarbodiimide, N, N'-diisopropylcarbodi imide, 1 ⁇ 3 ⁇ imethylarnino) propyl) -3-ethyl-c ⁇ rbodiirnid ⁇ nethiodid, 2-Bromo-3-ethyl-4-methyl-thiazoh 'environmentally tetrafluoroborate, N, N-bis [2-oxo-3
  • reaction temperatures can be varied within a substantial range when carrying out process (a) 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.
  • Suitable diluents for carrying out process (b) 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 (b) 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 Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as 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 bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine , N-methylpiperidine, N-methylmorpholine, N,
  • reaction temperatures can be varied within a substantial range. 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 processes (a) and (b) 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.
  • the substances according to the invention have a strong microbicidal action 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 for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • pathogens of fungal and bacterial diseases which fall under the generic names enumerated above, are named: Diseases caused by powdery mildews such as e.g. Blumeria species, such as Blumeria graminis;
  • Podosphaera species such as Podosphaera leucotricha
  • Sphaerotheca species such as Sphaerotheca fiiliginea
  • Uncinula species such as Uncinula necator
  • Gymnosporangium species such as Gymnosporangium sabinae
  • Hemileia species such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as Puccinia recondita or Puccinia graminis
  • Uromyces species such as Uromyces appendiculatus
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Pythium species such as Pythium uhimum
  • Alternaria species such as Alternaria solani;
  • Cercospora species such as Cercospora beticola
  • Cladosporium species such as Cladosporium cucumerinum
  • Cochliobolus species such as Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium);
  • Colletotrichum species such as Colletotrichum lindemuthanium
  • Cycloconium species such as cycloconium oleaginum
  • Diaporthe species such as Diaporthe citri;
  • Elsinoe species such as Elsinoe fawcettii
  • Gloeosporium species such as, for example, Gloeosporium laeticolor
  • Glomerella species such as Glomerella cingulata
  • Guignardia species such as Guignardia bidwelli;
  • Leptosphaeria species such as Leptosphaeria maculans
  • Magnaporthe species such as Magnaporthe grisea
  • Mycosphaerella species such as Mycosphaerella graminicola and Mycosphaerella fijiensis
  • Mycosphaerella species such as Mycosphaerella graminicola and Mycosphaerella fijiensis
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Corticium species such as Corticium grarninearum
  • Fusarium species such as Fusarium oxysporum
  • Gaeumannomyces species such as Gaeumannomyces graminis
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis or Tapesia yallundae;
  • Thielaviopsis species such as Thielaviopsis basicola
  • Ear and panicle diseases caused by e.g.
  • Ahernaria species such as Alternaria spp .;
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium cladosporioides
  • Claviceps species such as Claviceps purpurea
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gibberella zeae
  • Monographella species such as Monographella nivalis
  • Sphacelotheca species such as Sphacelotheca reiliana
  • Tilletia species such as Tilletia caries
  • Urocystis species such as Urocystis occulta
  • Ustilago species such as Ustilago nuda
  • Aspergillus species such as Aspergillus flavus
  • Botrytis species such as Botrytis cinerea
  • Penicillium species such as Penicillium expansum and Penicillium purpurogenum
  • Sclerotinia species such as Sclerotinia sclerotiorum
  • Verticilium species such as Verticilium alboatrum; Seed and soil rots and wilts, and seedling diseases caused by, for example, Fusarium species such as Fusarium cubnorum; Phytophthora species, such as Phytophthora cactorum; Pythium species such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii;
  • Nectria species such as Nectria galligena
  • Esca species such as Phaeomoniella chlamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea; Flower and seed diseases caused by e.g. Botrytis species, such as Botrytis cinerea;
  • Rhizoctonia species such as Rhizoctonia solani
  • Hehninthosporium species such as Hehninthosporium solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as Erwinia amylovora
  • the following diseases of soybean beans can be controlled: fungal diseases on leaves, stems, pods and seeds caused by, for example, Alternaria leaf spot (Alternaria sp. Ater tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var.
  • Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • 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 attack by unwanted microorganisms.
  • 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 protect plants within a certain period of time after the treatment against the infestation by the said pathogens.
  • the period within which protection is induced generally extends from 1 to 28 days, preferably 1 to 14 days, more 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, 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.
  • 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 methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
  • the substances of the invention for the protection of technical Use materials against infestation and destruction by unwanted microorganisms.
  • technical material is meant herein non-living materials 201 that have been prepared for use in the art.
  • technical materials which are to be protected against microbial alteration or destruction by active compounds according to the invention may be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which attack or decompose microorganisms can be.
  • 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.
  • technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Examples include microorganisms of the following genera: Alternaria, such as Ahernaria tenuis,
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum
  • Coniophora like Coniophora puetana,
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum.
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma such as 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,
  • These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • organic solvents can also 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, eg 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
  • aliphatic hydrocarbons such
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example 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: eg broken 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-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and 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.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and 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.
  • 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, nematocides 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 1) inhibitors of nucleic acid synthesis: e.g. Benalaxyl, Benalaxyl M, Bupirimate, Clozylacon,
  • inhibitors of mitosis and cell division e.g. Benomyl, carbendazim, diethofencarb, ethaboxam,
  • inhibitors of complex I of the respiratory chain e.g. diflumetorim
  • inhibitors at the complex II of the respiratory chain e.g. Boscalid / nicobifen, carboxin, fenfuram, flutolanil, furametpyr, furmecyclox, mepronil, oxycarboxin, penthiopyrad, thifluzamide;
  • inhibitors at the complex Ell of the respiratory chain e.g. Amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metomino-strobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin;
  • decoupler e.g. Dinocap, fluazinam, meptyldinocap;
  • inhibitors of ATP production e.g. Fe ⁇ tin acetate, Fentin chloride, Fentin hydroxide, Silthiofam;
  • Inhibitors of amino acid and protein biosynthesis e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;
  • inhibitors of the signal transduction e.g. Fenpiclonil, fludioxonil, quinoxyfen;
  • inhibitors of lipid and membrane synthesis eg biphenyl, cholzoliiate, edifenphos, iodocarb, Iprobenfos, iprodione, isoprothiolanes, procymidones, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl, vinclozohn; 9)
  • Inhibitors of ergosterol biosynthesis eg aldimo ⁇ h, azaconazole, bitertanol, bromuconazoles, cyproconazole, diclobutrazoles, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamide, fenpropidin, fenpropimorph, fluquincon
  • resistance inducers e.g. Acibenzolar-S-methyl, Probenazoles, Tiadinil;
  • Pyrethroids eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, biotethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlorovaporthrin, cis-cypermethrin , Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (IR-isomer), esfenvalerate, etofenprox , Fenfluthrin, f
  • Oxadiazines e.g., Indoxacarb
  • Acetylcholine receptor agonists Z antagonists
  • chloronicotinyls / neonicotinoids for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, tenpyram, nithiazines, thiacloprid, thiamethoxam
  • Fiproles e.g., acetoprole, ethiprole, fipronil, vaniliprole
  • Fiproles e.g., acetoprole, ethiprole, fipronil, vaniliprole
  • Mectins for example, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milkmectin, milbemycin
  • diacylhydrazones e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides
  • Benzoylureas eg bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoron
  • Buprofezin eg bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoron
  • Inhibitors of oxidative phosphorylation, ATP disruptors 10.
  • Diafenthiuron 10.2
  • Organotin e.g., azocyclotin, cyhexatin, fenbutatin oxides
  • METI's 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 ethyl ester, CAS Reg.
  • Carboxamides e.g., flonicamid
  • Octopaminergic agonists e.g., amitraz
  • Inhibitors of magnesium-stimulated ATPase e.g., magnesium-stimulated ATPase
  • Fumigants for example aluminum phosphides, methyl bromides, sulphuryl fluorides
  • Selective feeding inhibitors for example cryolites, flonicamide, pymetrozines
  • 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 the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble
  • Powder, dusts and granules are applied.
  • the application happens in usual Example, by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc.
  • the active ingredients can be applied by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself in the soil. 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. In the treatment of parts of plants, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • 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 may also give rise to superadditive ("synergistic") effects, for example reduced application rates and / or extensions of the activity spectrum and / or a Strengthening of the effect of the substances and agents which can be used according to the invention, better plant growth, more developed root system, higher resistance of the plant species or plant variety, increased growth of the shoots, higher plant vigor, increased tolerance to high or low temperatures, increased tolerance to drought or to water or water Soil salt content, increased flowering power, easier harvesting, acceleration of ripeness, higher crop yields, larger Fruits, higher plant size, greener leaf color, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the fruits, higher storage capacity and / or workability of the harvest products possible, which go beyond the expected effects.
  • superadditive superadditive
  • the preferred plants or plant cultivars to be treated according to the invention 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 dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability 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 as well as an increased tolerance of the plants against certain herbicidal active substances.
  • microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses
  • 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 which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a) , CryIA (b), CryIA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof) in the plants (hereafter "Bt 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. ), the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosates or phosphinotricin (eg "PAT" gene), are particularly emphasized.
  • the genes conferring the desired properties (“traits”) can also be present in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YIELD GARD® (eg maize , Cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • YIELD GARD® eg maize , Cotton, soybean
  • 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 glyphosides).
  • Herbicide-resistant plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. 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.
  • reaction mixture is stirred for 2 hours at room temperature before a solution consisting of 210.6 mg (0.8 mmol) of methyl 2'-amino-3,5'-difluorobiphenyl-4-carboxylate and 0.16 ml (1.1 mmol) of triethylamine in 5 ml of dichloromethane is added dropwise , The reaction mixture is stirred for 16 hours at room temperature, added to 4 ml of water, the organic phase is dried over sodium sulfate and concentrated in vacuo.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluent; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration is 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.
  • dimethylacetamide emulsifier 1 part by weight of alkyl-aryl-polyglycol ether
  • active compound preparation 1 part by weight of active compound is mixed with the stated 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.
  • 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 alkylaiyl 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% to promote the development of rust pustules.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention relates to novel biphenyl carboxamides of formula (I), wherein R<SUP>1</SUP>, R<SUP>8</SUP>, R<SUP>9</SUP>, R<SUP>10</SUP> and A have the meanings cited in the description. The invention relates to several methods for producing said substances, to the use thereof for controlling undesired micro-organisms, to novel intermediate products and to the use thereof.

Description

BIPHENYLCARBOXAMIDE ZUR BEKÄMPFUNG VON MIKROORGANISMEN BIPHENYLCARBOXAMIDE FOR COMBATING MICROORGANISMS
Die vorliegende Erfindung betrifft neue Biphenylcarboxanüde, mehrere Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von schädlichen Mikroorganismen im Pflanzenschutz und Materialschutz.The present invention relates to novel Biphenylcarboxanüde, several processes for their preparation and their use for controlling harmful microorganisms in crop protection and material protection.
Es ist bereits bekannt geworden, dass bestimmte Biphenylcarboxamide fungizide Eigenschaften besitzen (vgl. z.B. WO 03/070705 und EP-A 0 545 099). Die Wirksamkeit der dort beschriebenen Stoffe ist gut, lässt aber in manchen Fallen zu wünschen übrig.It has already been disclosed that certain biphenylcarboxamides have fungicidal properties (cf., for example, WO 03/070705 and EP-A 0 545 099). The effectiveness of the substances described there is good, but leaves in some cases to be desired.
Es wurden nun neue Biphenylcarboxamide der Formel (I)There have now been new biphenylcarboxamides of the formula (I)
gefunden, in welcher found in which
R' für Wasserstoff, CrC8-Alkyl, Ci-Ce-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-C4-AIkOXy-C1- C4-alkyl, C3-C8-Cycloalkyl; Ci-Cδ-Halogenalkyl, CrC4-Halogenalkylthio, CrC4-Halogenal- kylsulfϊnyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-HaIo- gencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci- Cs-alkyl, (d-Q-AlkyOcarbonyl-d-Ca-alkyl, (C1-C3-Alkoxy)carbonyl-Ci-C3-alkyl; HaIo- gen-(Ci-C3-alkyl)carbonyl-Ci-C3-alkyl, Halogen-(Ci-C3-alkoxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen;R 'is hydrogen, C r C 8 alkyl, Ci-Ce-alkylsulfinyl, Ci-C6 alkylsulfonyl, Ci-C 4 -alkoxy-C 1 - C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C δ haloalkyl, C r C 4 haloalkylthio, C r C 4 kylsulfϊnyl -Halogenal-, 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-Ci- Cs-alkyl, (dQ-AlkyOcarbonyl-d-Ca-alkyl, (C 1 -C 3 alkoxy) carbonyl-Ci-C 3 alkyl; halo- gen- (Ci-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;
(Ci-Cs-Alkytycarbonyl, (d-C8-Alkoxy)carbonyl, (CrC8-Alkylthio)carbonyl, (C,-C4-Alkoxy- Ci-C4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)carbonyl, (C3-C8- Cycloalkyl)carbonyl; (Ci-Cβ-HalogenalkyOcarbonyl, (Ci-C6-Halogenalkoxy)carbonyl, (Ci- C6-Halogenalkylthio)carbonyl, (Halogen-Ci -C4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C6-HaIo- genalkenyloxy)carbonyl, (Cs-Cs-Halogenalkinyloxyjcarbonyl, (C3-C8-Halogencycloalkyl)- carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-CsC-R1^,(Ci-Cs-Alkytycarbonyl, (dC 8 alkoxy) carbonyl, (CrC 8 alkylthio) carbonyl, (C, -C 4 alkoxy Ci-C4 alkyl) carbonyl, (C 3 -C 6 alkenyloxy) carbonyl, (C 3 -C 6 alkynyloxy) carbonyl, (C 3 -C 8 - cycloalkyl) carbonyl; (Ci-Cβ-HalogenalkyOcarbonyl, (Ci-C 6 haloalkoxy) carbonyl, (Ci- C 6 haloalkylthio) carbonyl , (Halogeno-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C 6 -halogenoalkenyloxy) carbonyl, (C 5 -C 8 -haloalkynyloxyjcarbonyl, (C 3 -C 8 -halocycloalkyl) - carbonyl with in each case 1 to 9 fluorine, chlorine and / or bromine atoms, or -CH 2 -CsC-R 1 ^,
-CH2-CH=CH-R1^, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht,-CH 2 -CH = CH-R 1 ^, -CH = C = CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 stands,
R'"A für Wasserstoff, C,-C6-Alkyl, C,-C6-Halogenalkyl, C2-Cö-Alkenyl, C2-C6-Alkinyl, C3-C7-R '"A represents hydrogen, C, -C6 alkyl, C, -C 6 haloalkyl, C 2 -C ö alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 -
Cycloalkyl, (Ci-C4-Alkoxy)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)- carbonyl oder Cyano steht, R2 für Wasserstoff, C,-C8-Alkyl, CrC8-Alkoxy, C,-C4-Alkoxy-Ci-C4-alkyl, C3-C8-Cycloalkyl; d-Cβ-Halogenalkyl, Ci-C6-Halogenalkoxy, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-HaJo- gencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht,Cycloalkyl, (C 1 -C 4 -alkoxy) carbonyl, (C 3 -C 6 -alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) -carbonyl or cyano, R 2 is hydrogen, C, -C 8 alkyl, C r C 8 alkoxy, C, -C 4 alkoxy-Ci-C 4 alkyl, C 3 -C 8 cycloalkyl; C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halogeno-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -HaJo gencycloalkyl having in each case 1 to 9 fluorine, chlorine and / or or bromine atoms stands,
R3 und R4 unabhängig voneinander jeweils für Wasserstoff, Ci-Cs-Alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, C3-C8-Cycloalkyl; Ci-C8-Halogenalkyl, Halogen-Ci-C4-alkoxy-C1-C4-alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 3 and R 4 are each independently hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; Ci-C8-haloalkyl, halo-Ci-C 4 alkyl C 1 -C 4 alkoxy, halo-C 3 -C 8 cycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R3 und R4 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls 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 NR7 enthalten kann,R 3 and R 4 together with the nitrogen atom to which they are attached, form a saturated heterocycle having 5 to 8 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
R5 und R6 unabhängig voneinander für Wasserstoff, Ci-C8-Alkyl, C3-C8-Cycloalkyl; Ci-C8-Halogen- alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-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 NR7 enthalten kann, R7 für Wasserstoff oder C]-C6-Alkyl steht,R 5 and R 6 are each independently hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyl; Ci-C 8-halo, C 3 -C 8 alkyl -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 5 and R 6 furthermore together with the nitrogen atom to which they are attached form a optionally mono- or polysubstituted, identically or differently, by halogen or C 1 -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 7 , R 7 is hydrogen or C 1 -C 6 -alkyl,
R8 für Wasserstoff oder Fluor steht,R 8 is hydrogen or fluorine,
R9 für -SOmRn, -SO2NR12R13, -C(=X)R14, -Si(R15)3, -NR12R13, -CH2-NR12R13 steht,R 9 is -SO m R n , -SO 2 NR 12 R 13 , -C (= X) R 14 , -Si (R 15 ) 3 , -NR 12 R 13 , -CH 2 -NR 12 R 13 ,
R10 für Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl steht,R 10 is fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl,
R11 für Ci-Cö-Alkyl oder Ci-C6-Halogenalkyl mit 1 bis 13 Halogenatomen steht, m für 1 oder 2 steht,R 11 ö for Ci-C alkyl, or Ci-C is 6 haloalkyl having 1 to 13 halogen atoms, m is 1 or 2;
R12 für Wasserstoff, C,-C4-Alkyl oder -C(=X)R14 steht,R 12 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 14 ,
R13 für Wasserstoff, C,-C4-Alkyl oder -C(=X)R14 steht,R 13 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 14 ,
R12 und R13 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-C4-AUCyI 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 NR7 enthalten kann,R 12 and R 13 together with the nitrogen atom to which they are attached additionally form a saturated heterocycle having 5 to 8 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
X für O (Sauerstoff) oder S (Schwefel) steht,X is O (oxygen) or S (sulfur),
R14 für Wasserstoff, C,-C4-Alkyl, C1-C4-AIkOXy oder -NR16R17 steht, R 15 für Wasserstoff, C1-C8-AIlCyI, C,-C8-Alkoxy, Q-C-Alkoxy-Q-C-alkyl, C,-C4-Alkylthio- C]-C4-alkyl oder d-Cβ-Halogenalkyl steht, wobei die drei Reste R15 jeweils gleich oder verschieden sein können,R 14 is hydrogen, C, -C 4 alkyl, C 1 -C 4 -alkoxy or -NR 16 R 17, R 15 is hydrogen, C 1 -C 8 -alkyl, C, -C 8 alkoxy, QC QC-alkoxy-alkyl, C, -C 4 alkylthio C] -C 4 alkyl or d-Cβ-haloalkyl wherein the three radicals R 15 may each be identical or different,
16 Wasserstoff oder Ci-C4-Alkyl steht,16 is hydrogen or C 1 -C 4 -alkyl,
17 Wasserstoff oder Ci-C4-Alkyl steht,17 is hydrogen or C 1 -C 4 -alkyl,
R16 und R17 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-C4-AUCyI 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 NR7 enthalten kann,R 16 and R 17 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, the heterocycle being 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
A für einen der folgenden Reste Al bis A19 stehtA is one of the following radicals A1 to A19
A16 A17 A18 A19A16 A17 A18 A19
R 18 für Wasserstoff, Cyano, Halogen, Nitro, Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, C3- Cβ-Cycloalkyl, Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy oder Ci-C4-Halogenalkyhhio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder steht,R 18 represents hydrogen, cyano, halogen, nitro, Ci-C4-alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, C 3 - Cβ cycloalkyl, Ci-C 4 haloalkyl, Ci-C4- Haloalkoxy or Ci-C 4 -haloalkhyio each having 1 to 5 halogen atoms, aminocarbonyl or stands,
R19 für Wasserstoff, Halogen, Cyano, Ci-C4-Alkyl, C1-C4-AIkOXy oder C1-C4-AUCyWuO steht,R 19 4 -alkoxy or C 1 -C 4 -AUCyWuO hydrogen, halogen, cyano, Ci-C 4 alkyl, C 1 -C
R20 für Wasserstoff, C1-C4-AIkVl, Hydroxy-CrC4-a]kyl, QrCθ-Alkenyl, C3-C6-Cycloalkyl, C1-C4- Alkylthio-Ci-C4-alkyl, Ci-C4-alkyl, mit jeweils 1 bis 5 Halogenatomen, oder Phenyl steht, R21 und R22 unabhängig voneinander für Wasserstoff, Halogen, C]-C4-Alkyl oder d-C4-Halogen- alkyl mit 1 bis 5 Halogenatomen steht, R23 für Halogen, Cyano oder Ci-C4-Alkyl, oder Ci-C4-Halogenalkyl oder C]-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, R24 und R25 unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-R 20 is hydrogen, C 1 -C 4 -alkyl, hydroxy-C r C 4 -a] kyl, QRC θ alkenyl, C 3 -C 6 cycloalkyl, C 1 -C 4 - alkylthio-Ci-C 4 - alkyl, C 1 -C 4 -alkyl, each having 1 to 5 halogen atoms, or phenyl, R 21 and R 22 are independently hydrogen, halogen, C] -C 4 alkyl or C 4 halo-alkyl is having 1 to 5 halogen atoms, R 23 is halogen, cyano or Ci-C 4 alkyl, or C C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms, R 24 and R 25 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -
Halogenalkyl mit 1 bis 5 Halogenatomen steht, R2S für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,Halogenoalkyl having 1 to 5 halogen atoms, R 2 S, hydrogen, halogen, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R27 für Wasserstoff, Halogen, Hydroxy, Cyano, Ci-C6-Alkyl, Ci-C4-Halogenalkyl, C1-C4-Ha- logenalkoxy oder Ci-C4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht,R 27 is hydrogen, halogen, hydroxy, cyano, Ci-C 6 alkyl, Ci-C 4 haloalkyl, C 1 -C 4 logenalkoxy -Ha- or Ci-C4-haloalkylthio having in each case 1 to 5 halogen atoms,
R28 für Halogen, Hydroxy, Cyano, Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, Ci-C4-R 28 represents halogen, hydroxy, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -
Halogenalkyl, Ci-C4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5Haloalkyl, C 1 -C 4 -haloalkylthio or C 1 -C 4 -haloalkoxy each having 1 to 5
Halogenatomen steht,Halogen atoms is,
R2S für Wasserstoff, Halogen, Cyano, Ci-C4-Alkyl, CrC4-Alkoxy, C,-C4-Alkylthio, Cj-C A- Halogenalkyl, Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, Ci-C4-R 2S hydrogen, halogen, cyano, Ci-C 4 alkyl, C r C 4 alkoxy, C, -C 4 alkylthio, Cj-C A- haloalkyl, Ci-C4-haloalkoxy having in each case 1 to 5 halogen atoms, , Ci-C 4 -
Alkylsulphinyl oder Ci-C4-Alkylsulphonyl steht,Alkylsulphinyl or C 1 -C 4 -alkylsulphonyl,
R30 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R31 für C,-C4-Alkyl steht, Q1 für S (Schwefel), SO, SO2 oder CH2 steht, p für 0, 1 oder 2, wobei R22 für identische oder verschiedene Reste steht, wenn p für 2 steht,R 30 4 -alkyl or Ci-C 4 haloalkyl is Ci-C with 1 to 5 halogen atoms, R 31 is C, -C 4 -alkyl, Q 1 represents S (sulfur), SO, SO 2 or CH 2 p is 0, 1 or 2, where R 22 is identical or different radicals, if p is 2,
R32 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R33 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R34 und R35 unabhängig voneinander für Wasserstoff, Halogen, Amino, Ci-C4-Alkyl oder Ci-C4-R 32 4 haloalkyl is Ci-C 4 alkyl or C 1 to 5 halogen atoms, R 33 4 -alkyl or C is 4 -halogenoalkyl having 1 to 5 halogen atoms is C, R 34 and R 35 independently of one another represent hydrogen, halogen, amino, C 1 -C 4 -alkyl or C 1 -C 4 -
Halogenalkyl mit 1 bis 5 Halogenatomen stehen, R3S für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R37 und R38 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, C1-C4-AIlCyI oder Ci-Haloalkyl having 1 to 5 halogen atoms, R 3S is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 -haloalkyl having 1 to 5 halogen atoms, R 37 and R 38 independently of one another are hydrogen, halogen, amino, nitro , C 1 -C 4 -alkyl or
C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen,C 4 -haloalkyl having 1 to 5 halogen atoms,
R39 für Wasserstoff, Halogen, C1-C4-AUCyI oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 39 is hydrogen, halogen, C 1 -C 4 -AUCyI or C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R40 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)amino, Cyano, Ci-C4-R 40 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,Is alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R41 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R42 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci -C4-alkyl)amino, Cyano, Ci-C4- Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 41 represents halogen, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms, R 42 is hydrogen, halogen, amino, Ci-C 4 alkylamino, di- (Ci -C 4 alkyl ) amino, cyano, Ci-C 4 - alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms,
R43 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R44 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 43 represents halogen, Ci-C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms, R 44 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R45 für Wasserstoff oder Ci-C4-Alkyl steht,R 45 is hydrogen or C 1 -C 4 -alkyl,
R46 für Halogen oder d-C4-Alkyl steht,R 46 is halogen or C 1 -C 4 -alkyl,
R47 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R48 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 47 is C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms, R 48 4 haloalkyl represents hydrogen, halogen, Ci-C 4 alkyl or C 1 to 5 halogen atoms,
R49 für Halogen, Hydroxy, Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkyhhio, Ci-C4-Halogenalkyl, Ci-C4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht,R 49 represents halogen, hydroxyl, Ci-C4-alkyl, Ci-C 4 alkoxy, Ci-C 4 -Alkyhhio, Ci-C 4 haloalkyl, Ci-C4-haloalkylthio or C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,
R50 für Ci-C4-Alkyl steht, R51 für Wasserstoff, Cyano, C1-C4-AIlCyI, Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen, C1-C4- Alkoxy-Ci-C4-alkyl, Hydroxy-d-Gralkyl, Ci-C4-Alkylsulfbnyl, DitQ-Q-alkytyalTrinosulfonyl, Ci-Cfi-Alkylcarbonyl oder jeweils gegebenenfalls substituiertes Phenylsulfonyl oder Benzoyl steht,R 50 is 4 alkyl is C, R 51 represents hydrogen, cyano, C 1 -C 4 -alkyl, Ci-C 4 haloalkyl having 1 to 5 halogen atoms, C 1 -C 4 - alkoxy-Ci-C4- alkyl, hydroxy-d-Gralkyl, Ci-C 4 -Alkylsulfbnyl, DitQ-Q-alkytyalTrinosulfonyl, Ci-C f i-alkylcarbonyl or in each case optionally substituted phenylsulfonyl or benzoyl,
R52 für Wasserstoff, Halogen, Ci-C4-AIlCyI oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R53 für Wasserstoff, Halogen, Cyano, C1-C4-AIlCyI oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 52 is hydrogen, halogen, Ci-C 4 -alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms, R 53 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl or C r C 4 -haloalkyl with 1 to 5 halogen atoms,
R54 für Wasserstoff, Halogen, C1-C4-AIlCyI oder CrC4-Halogenalkyl mit 1 bis 5 Halogenatomen steht.R 54 is hydrogen, halogen, C 1 -C 4 -AllCyI or C r C 4 haloalkyl having 1 to 5 halogen atoms.
Weiterhin wurde gefunden, dass man Biphenylcarboxamide der Formel (I) erhält, indem man (a) Carbonsäurehalogenide der Formel (II)Furthermore, it has been found that biphenylcarboxamides of the formula (I) are obtained by reacting (a) carboxylic acid halides of the formula (II)
in welcher in which
A die oben angegebenen Bedeutungen hat, X1 für Halogen oder Hydroxy steht, mit Aminen der Formel (UI)A has the meanings given above, X 1 is halogen or hydroxy, with amines of the formula (UI)
in welcher R1, R8, R9 und R10 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Kupplungsreagenzes, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder in which R 1 , R 8 , R 9 and R 10 have the meanings given above, if appropriate in the presence of a coupling reagent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
(b) Biphenylcarboxaniide der Formel (I-a)(b) biphenylcarboxanides of the formula (I-a)
in welcher R8, R9, R10 und A die oben angegebenen Bedeutungen haben, mit Halogeniden der Formel (IV) in which R 8 , R 9 , R 10 and A have the meanings given above, with halides of the formula (IV)
R1^-HaI (IV) in welcherR 1 ^ -HaI (IV) in which
R1 B für Ci-Cs-Alkyl, d-Ce-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-C4-Alkoxy-Ci-C4-al- kyl, C3-C8-Cycloalkyl; Q-Cβ-Halogenalkyl, d-Q-Halogenalkylthio, Ci-C4-HaIo- genalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3-alkyl, (Ci-C3-Alkyl)carbonyl-Ci-C3-alkyl, (Ci-C3-Alkoxy)- carbonyl-Ci-C3-alkyl; Halogen-(Ci-C3-alkyl)carbonyl-Ci-C3-alkyl, Halogen-(Ci-C3— alkoxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oderR 1 B is Ci-Cs-alkyl, d-Ce-alkylsulfinyl, Ci-C6 alkylsulfonyl, Ci-C4-alkoxy-Ci-C4 -AL- alkyl, C 3 -C 8 cycloalkyl; Q-Cβ-haloalkyl, dQ-haloalkylthio, Ci-C 4 -HaIo- genalkylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy) -carbonyl-C 1 -C 3 -alkyl; Halogen (Ci-C 3 -alkyl) carbonyl-Ci-C 3 -alkyl, halogen- (Ci-C 3 - alkoxy) carbonyl-Ci-C 3 -alkyl with in each case 1 to 13 fluorine, chlorine and / or
Bromatomen;bromine atoms;
(Ci-C8-Alkyl)carbonyl, (Ci-C8-Alkoxy)carbonyl, (Ci-C3-Alkylthio)carbonyl, (C1-C4- Alkoxy-Ci -C4-alkyl)carbonyl, (C3-Cs-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)car- bonyl, (C3-C8-Cycloalkyl)carbonyl; (Ci-Cβ-HalogenalkyOcarbonyl, (Ci-C6-Halogen- alkoxy)carbonyl, (Ci-Cβ-Halogenalkyltbiojcarbonyl, (Halogen-Ci-C4-alkoxy-Ci-C4- alkyl)carbonyl, (C3-C6-Halogenalkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)car- bonyl, (C3-C8-Halogencycloa]kyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1 A, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht, R1 A, R2, R3, R4, R5 und R6 die oben angegebenen Bedeutungen haben,(Ci-C 8 -alkyl) carbonyl, (Ci-C 8 alkoxy) carbonyl, (Ci-C 3 alkylthio) carbonyl, (C 1 -C 4 - alkoxy-Ci-C4-alkyl) carbonyl, (C 3- Cs-alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) carbonyl, (C 3 -C 8 -cycloalkyl) carbonyl; (Ci-Cβ-HalogenalkyOcarbonyl, (Ci-C 6 halo-alkoxy) carbonyl, (Ci-Cβ-Halogenalkyltbiojcarbonyl, (halo-Ci-C4-alkoxy-Ci-C 4 - alkyl) carbonyl, (C 3 -C 6 -haloalkenyloxy) carbonyl, (C 3 -C 6 -haloalkynyloxy) carbonyl, (C 3 -C 8 -halocycloalkyl) carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, or -CH 2 -C≡CR 1 A , -CH 2 -CH = CH-R 1 A , -CH = C = CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 , R 1 A , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings given above,
HaI für Chlor, Brom oder Iod steht, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt.Hal is chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
Schließlich wurde gefunden, dass die neuen Biphenylcarboxamide 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 möglicher 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, beliebige Mischungen dieser Isomeren, sowie die möglichen tautomeren Formen beansprucht.Finally, it has been found that the novel biphenylcarboxamides 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 of the invention may optionally be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as. 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 claimed.
Die erfindungsgemäßen Biphenylthiazolcarboxamide sind durch die Formel (I) 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 Zwischenprodukte gleichermaßen.The biphenylthiazolecarboxamides according to the invention are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
R1 steht bevorzugt für Wasserstoff, Ci-C6-Alkyl, Ci-C-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, C1- C3-Alkoxy-Ci-C3-alkyl, C3-C6-Cycloalkyl; Ci-C4-Halogenalkyl, Ci-C4-Halogenalkylthio, C1- C4-Halogenalkylsulfinyl, Ci-Q-Halogenalkylsulfonyl, Halogen-Ci-C3-alkoxy-C]-C3-alkyl,R 1 preferably represents hydrogen, Ci-C 6 alkyl, Ci-C-alkylsulfinyl, Ci-C 4 alkylsulfonyl, C 1 - C 3 alkoxy-Ci-C 3 alkyl, C 3 -C 6 cycloalkyl; Ci-C 4 haloalkyl, C 4 haloalkylthio, C 1 - C 4 haloalkylsulfinyl, Ci-Q-haloalkylsulfonyl, halo-Ci-C 3 alkoxy-C] -C3 alkyl,
C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-C,-C3-alkyl, (Ci-Cj-Alky^carbonyl-d-Cs-alkyl, (C1-C3-Alkoxy)carbonyl-C1-C3- alkyl; Halogen-(Ci-CB-alkyl)carbonyl-Ci-C3-a]kyl, Halogen-(Ci-C3-alkoxy)carbonyl-C1-C3- alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Ci-C6-Alkyl)carbonyl, (Ci-C4-Alkoxy)carbonyl, (CrC4-Alkylthio)carbonyl, (Ci-C3-Alkoxy-C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C, C 3 -alkyl, (C 1 -C 12 -alkylcarbonyl-C 1 -C 5 -alkyl, (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl; -C B -alkyl) carbonyl-C 3 -a] kyl, halo (Ci-C 3 alkoxy) carbonyl-C 1 -C 3 - alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms (Ci-C 6 alkyl) carbonyl, (Ci-C 4 alkoxy) carbonyl, (C r C 4 -alkylthio) carbonyl, (Ci-C 3 alkoxy
Ci-C3-alkyl)carbonyl, (C3-C4-Alkenyloxy)carbonyl, (C3-C4-Alkinyloxy)carbonyl, (C3-C6- Cycloalkyl)carbonyl; (d-GrHalogenalkyOcarbonyl, (Ci-C4-Halogenalkoxy)carbonyl, (Ci- C4-Halogenalkyltbio)carbonyl, (Halogen-Ci-C3-alkoxy-Ci-C3-a]kyl)carbonyl, (C3-C4-HaIo- genalkenyloxy)carbonyl, (C3-C4-Halogenalkinyloxy)carbonyl, (C3-C6-Halogencycloalkyl)- carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-C=C-R1^,C 1 -C 3 -alkyl) carbonyl, (C 3 -C 4 -alkenyloxy) carbonyl, (C 3 -C 4 -alkynyloxy) carbonyl, (C 3 -C 6 -cycloalkyl) carbonyl; (d-GrHalogenalkyOcarbonyl, (Ci-C 4 haloalkoxy) carbonyl, (Ci- C 4 -Halogenalkyltbio) carbonyl, (halo-Ci-C 3 alkoxy-Ci-C 3 -a] kyl) carbonyl, (C 3 - C 4 -haloalkenyloxy) carbonyl, (C 3 -C 4 -haloalkynyloxy) carbonyl, (C 3 -C 6 -halocycloalkyl) -carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, or -CH 2 -C = CR 1 ^,
-CH2-CH=CH-R1 A, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6. R1 steht besonders bevorzugt für Wasserstoflζ Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pentyl oder Hexyl, Methylsulfinyl, Ethykulfinyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsulfinyl, Methylsulfonyl, Ethylsutfonyl, n- oder iso-Propylsulfonyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclo- propyl, Cyclopentyl, Cyclohexyl, Trifhioπnethyl, Trichlormethyl, Trifluorethyl, Difluormethyl- thio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethvlsuhmyl, Trifluormethylsutfonyl, Trifluormethoxymethyl; Formyl, -CH2-CHO, -(CHz)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)Z-CO-CH3, ^CHz)2-CO-CH2CH3, -(C^^O-CH^H^, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH,),, -(CH2^-CO2CH3,-CH 2 -CH = CH-R 1 A , -CH = C = CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 , R 1 particularly preferably represents hydrogen, 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, Ethylsutfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifhioπnethyl Trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfonyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; Formyl, -CH 2 -CHO, - (CH 2 ) 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 , - (CH 2) Z -CO-CH 3, ^ CHz) 2 -CO-CH 2 CH 3, - (C ^^ CH ^ H ^ O, -CH 2 -CO 2 CH 3, -CH 2 -CO 2 CH 2 CH 3 , -CH 2 -CO 2 CH (CH,) ,, - (CH 2 ^ -CO 2 CH 3 ,
-(CH2VCO2CH2CH3, -(CH^-COzO^CH^, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CHj)2-CO-CH2CF3, -(CH2VCO-CH2CCl3, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CH2)2-CO2CH2CF3, -(CH2VCO2CF2CF3, -(CH2VCO2CH2CCl33 -(CH2VCO2CCl2CCl3; Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butylcarbonyl, Methoxycaxbonyl, Ethoxycarbonyl, iso-Propoxycarbonyl, tert-Butoxycarbonyl, Methylthio- carbonyl, Ethylthiocarbonyl, iso-Propylthiocarbonyl, tert-Butylthiocarbonyl, Methoxymethylcarbonyl, Ethoxymethylcarbonyl, Cyclopropylcarbonyl; Trifluormethylcar- bonyl, Trifluormethoxycarbonyl, Trifluormethylthiocarbonyl, oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1 A, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6. R1 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Methoxymethyl, Methoxymethylcarbonyl, Ethoxymethylcarbonyl, Formyl, -CH2-C≡CH, -CH2-CH=CH2, -CH=C=CH2, -CH2-CHO, -(CH2VCHO3 -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CHs)2, -C(=O)CHO, -C(=0)C(=O)CH3, -C(=O)C(=O)CH2OCH3, -C(=O)CO2CH3,- (CH 2 VCO 2 CH 2 CH 3 , - (CH 2 -COzO ) CH 2 , -CH 2 -CO-CF 3 , -CH 2 -CO-CCl 3 , -CH 2 -CO-CH 2 CF 3 , -CH 2 -CO-CH 2 CCl 3 , - (CHj) 2 -CO-CH 2 CF 3 , - (CH 2 VCO-CH 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 2 VCO 2 CF 2 CF 3 , - (CH 2 VCO 2 CH 2 CCl 33 - (CH 2 VCO 2 CCl 2 CCl 3 ; methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tert. Butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, methylthio-carbonyl, ethylthiocarbonyl, isopropylmethylcarbonyl, tert-butylthiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, cyclopropylcarbonyl, trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, or -CH 2 -C≡CR 1 A , -CH 2 -CH = CH-R 1 A , -CH = C = CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6, R 1 very particularly preferably represents hydrogen, methyl, methoxymethyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, formyl, -CH 2 -C≡CH, -CH 2 -CH = CH 2 , -CH = C = CH 2 , -CH 2 -CHO, - (C H 2 VCHO 3 -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CHs) 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)CO2CH2CH3.-C (= O) CO 2 CH 2 CH 3 .
R1 A steht bevorzugt für Wasserstoff, Ci-C4-Alkyl, d-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-R 1 A is preferably hydrogen, Ci-C 4 alkyl, dC 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -
AMtiyl, C3-C6-Cycloalkyl, (Ci-C4-Alkoxy)carbonyl, oder Cyano. R1 A steht besonders bevorzugt für Wasserstoff, Methyl oder Ethyl.AMtiyl, C 3 -C 6 -cycloalkyl, (C 1 -C 4 -alkoxy) carbonyl, or cyano. R 1 A is particularly preferably hydrogen, methyl or ethyl.
R2 steht bevorzugt für Wasserstoff, Q-Cβ-Alkyl, Ci-C4-Alkoxy, Ci-C3-Alkoxy-Ci-C3-alkyl, C3-R 2 is preferably hydrogen, Q-Cβ-alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -
Ce-Cycloalkyl; Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy, Halogen-d-Cs-alkoxy-Ci-Q- alkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.Ce-cycloalkyl; Ci-C 4 haloalkyl, Ci-C4-haloalkoxy, halo-d-Cs-alkoxy-Ci-Q-alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
R2 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, tert-Butyl,R 2 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl,
Methoxy, Ethoxy, n- oder iso-Propoxy, tert-Butoxy, Methoxymethyl, Cyclopropyl; Trifluor- methyl, Trifluormethoxy.Methoxy, ethoxy, n- or iso -propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
R3 und R4 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-C6-Alkyl, Ci-C3-Alkoxy- Ci-Cs-alkyl, C3-C6-Cycloalkyl; Ci-C4-Halogenalkyl, Halogen-Ci-C3-a-koxy-Ci-C3-alkyl, C3- Ce-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R3 und R4 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann. R3 und R4 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.R 3 and R 4 independently of one another preferably represent hydrogen, Ci-C 6 alkyl, Ci-C 3 alkoxy Ci-Cs-alkyl, C 3 -C 6 cycloalkyl; Ci-C 4 haloalkyl, halogen-Ci-C 3 -a-koxy-Ci-C 3 alkyl, C 3 - Ce-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms. R 3 and R 4 also form, together with the nitrogen atom to which they are bonded, preferably a saturated heterocycle having 5 or 6 ring atoms which is optionally monosubstituted to disubstituted, identically or differently by halogen or C 1 -C 4 -alkyl, where the heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain. R 3 and R 4 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.
R3 und R4 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,R 3 and R 4 also form, together with the nitrogen atom to which they are bonded, particularly preferably a saturated heterocycle which is optionally monosubstituted to monosubstituted, identically or differently by fluorine, chlorine, bromine or methyl, and belongs to the series morpholine,
Ηύomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann.Omomorpholine or piperazine, wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
R5 und R6 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-C6-Alkyl, C3-C6-Cycloal- kyl; Ci-C4-Halogenalkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.R 5 and R 6 are each independently preferably represents hydrogen, Ci-C 6 alkyl, C 3 -C 6 -Cycloal- alkyl; C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
R5 und R6 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-R 5 and R 6 together with the nitrogen atom to which they are attached preferably also form an optionally mono- or polysubstituted by identical or different halogen or
C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff,C 4 alkyl-substituted saturated heterocycle having 5 or 6 ring atoms, wherein the heterocycle contains 1 or 2 further, non-adjacent heteroatoms from the series oxygen,
Schwefel oder NR7 enthalten kann.May contain sulfur or NR 7 .
R5 und R6 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.R 5 and R 6 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
R5 und R6 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor,R 5 and R 6 together with the nitrogen atom to which they are attached moreover preferably form an optionally monosubstituted to tetravalent, identical or different, by fluorine,
Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin,Chloro, bromo or methyl substituted saturated heterocycle from the series morpholine,
Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann.Thiomorpholine or piperazine, wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
R7 steht bevorzugt für Wasserstoff oder Ci-C4-Alkyl.R 7 is preferably hydrogen or C 1 -C 4 -alkyl.
R7 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl.R 7 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
R8 steht bevorzugt für Wasserstoff. R8 steht besonders bevorzugt für Fluor.R 8 is preferably hydrogen. R 8 particularly preferably represents fluorine.
R9 steht bevorzugt für -SOmRπ. R9 steht außerdem bevorzugt für -SO2NR12R13. R9 steht außerdem bevorzugt für -C(=X)R14. R9 steht außerdem bevorzugt für -Si(R15)3. R9 steht außerdem bevorzugt für -NR12R13. R9 steht außerdem bevorzugt für -CH2-NR12R13.R 9 is preferably -SO m R π . R 9 also preferably represents -SO 2 NR 12 R 13 . R 9 also preferably represents -C (= X) R 14 . R 9 is also preferably -Si (R 15 ) 3 . R 9 also preferably represents -NR 12 R 13 . R 9 also preferably represents -CH 2 -NR 12 R 13 .
R10 steht bevorzugt für Fluor. Chlor oder Brom.R 10 is preferably fluorine. Chlorine or bromine.
R10 steht außerdem bevorzugt für Methyl oder Trifluormethyl.R 10 also preferably represents methyl or trifluoromethyl.
R10 steht besonders bevorzugt für Fluor.R 10 particularly preferably represents fluorine.
R10 steht außerdem besonders bevorzugt für Chlor.R 10 is also more preferably chlorine.
R10 steht außerdem besonders bevorzugt für Methyl. R10 steht außerdem besonders bevorzugt für Trifluormethyl.R 10 is also more preferably methyl. R 10 is also more preferably trifluoromethyl.
R11 steht bevorzugt für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oderR 11 preferably represents Ci-C4 alkyl or Ci-C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or
Bromatomen.Bromine atoms.
R11 steht besonders bevorzugt für Methyl, Ethyl, n-, iso-Propyl, n-, i-, s-, t-Butyl, Trifluorme- thyl, -CH2CF3, -C2F5 oder Trichlormethyl.R 11 particularly preferably represents methyl, ethyl, n-, iso-propyl, n-, i-, s-, t-butyl, trifluoromethyl, -CH 2 CF 3 , -C 2 F 5 or trichloromethyl.
R11 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, -CH2CF3 oder -C2F5.R 11 is very particularly preferably methyl, trifluoromethyl, -CH 2 CF 3 or -C 2 F 5 .
m steht bevorzugt für 1. m steht auch bevorzugt für 2. m steht besonders bevorzugt für 2.m is preferably 1, m is also preferably 2, m is particularly preferably 2.
R12 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-R 12 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-
Butyl oder -C(=X)R14.Butyl or -C (= X) R 14 .
R12 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl oder -C(=X)R14 R 12 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl or -C (= X) R 14
R12 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.R 12 most preferably represents hydrogen or methyl.
R13 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-R 13 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-
Butyl oder -C(=X)R14. R13 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl oderButyl or -C (= X) R 14 . R 13 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or
-C(=X)R14. R13 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.-C (= X) R 14 . R 13 most preferably represents hydrogen or methyl.
R12 und R13 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevor- zugt einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann.R 12 and R 13 also together with the nitrogen atom to which they are attached preferably form a saturated heterocycle having 5 or 6 ring atoms, optionally mono- or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl the heterocycle may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 7 .
R12 und R13 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 ReiheR 12 and R 13 also form, together with the nitrogen atom to which they are bonded, more preferably a saturated heterocycle optionally substituted once to four times, identically or differently by fluorine, chlorine, bromine or methyl, from the series
Morpholin, Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann.Morpholine, thiomorpholine or piperazine, wherein the piperazine may be substituted on the second nitrogen atom by R 7 .
X steht bevorzugt für O (Sauerstoff). X steht auch bevorzugt für S (Schwefel).X is preferably O (oxygen). X is also preferably S (sulfur).
R14 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, n-, iso-, sec- oder tert-Butoxy oder -NR16R17.R 14 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, sec- or tert-butoxy or -NR 16 R 17 .
R14 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, Methoxy, Ethoxy, n- oder iso-Propoxy oder -NR16R17.R 14 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, methoxy, ethoxy, n- or iso-propoxy or -NR 16 R 17 .
R14 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Methoxy, Ethoxy oder -NR16R17.R 14 very particularly preferably represents hydrogen, methyl, ethyl, methoxy, ethoxy or -NR 16 R 17 .
R15 steht bevorzugt für Ci-C6-Alkyl, Ci-C6-Alkoxy, Ci-C3-Alkoxy-Ci-C3-alkyl oder Q-C3- Alkylthio-Ci-C3-alkyl, wobei die drei Reste R15 jeweils gleich oder verschieden sein können.R 15 preferably represents Ci-C 6 alkyl, Ci-C 6 alkoxy, Ci-C 3 alkoxy-Ci-C 3 alkyl, or QC 3 - alkylthio-Ci-C 3 alkyl, where the three radicals R 15 may be the same or different.
R15 steht besonders bevorzugt für Methyl, Ethyl, Methoxy, Ethoxy, Methoxymethyl, Ethoxyme- thyl, Methoxyethyl, Ethoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methyhhioethyl oder Ethylthioethyl, wobei die drei Reste R15 jeweils gleich oder verschieden sein können. R15 steht ganz besonders bevorzugt für Methyl, Methoxy, Methoxymethyl oder Methyhhio- methyl, wobei die drei Reste R15 jeweils gleich oder verschieden sein können.R 15 particularly preferably represents methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or ethylthioethyl, where the three radicals R 15 may each be identical or different. R 15 very particularly preferably represents methyl, methoxy, methoxymethyl or methylthio-methyl, where the three radicals R 15 may each be identical or different.
R15 steht insbesondere bevorzugt für Methyl.R 15 is particularly preferably methyl.
R16 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl. R16 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl. R16 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.R 16 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl. R 16 particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl. R 16 very particularly preferably represents hydrogen or methyl.
R17 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl.R 17 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
R17 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl.R 17 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl.
R17 steht ganz besonders bevorzugt für Wasserstoff oder Methyl. R15 und R17 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-CrAlkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann.R 17 most preferably represents hydrogen or methyl. R 15 and R 17 together with the nitrogen atom to which they are attached furthermore preferably form a saturated heterocycle having 5 or 6 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or C 1 -C 6 -alkyl, where the heterocycle is 1 or 2 further , non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain.
R16 und R17 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 R7 substituiert sein kann.R 16 and R 17 also form, together with the nitrogen atom to which they are bonded, particularly preferably a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, optionally monosubstituted to trisubstituted, identically or differently by fluorine, chlorine, bromine or methyl the piperazine may be substituted on the second nitrogen atom by R 7 .
A steht bevorzugt für einen der Reste Al, A2, A3, A4, A5, A6, A9, AlO, Al 1, A12, oder A17.A is preferably one of the radicals Al, A2, A3, A4, A5, A6, A9, AlO, Al 1, A12, or A17.
A steht besonders bevorzugt für einen der ResteA is particularly preferably one of the radicals
Al, A2, A4, A5, A6, A9, Al 1, A16, A17. A steht ganz besonders bevorzugt für den Rest Al .Al, A2, A4, A5, A6, A9, A1, A16, A17. A very particularly preferably represents the radical Al.
A steht außerdem ganz besonders bevorzugt für den Rest A2.A is also very particularly preferably the radical A2.
A steht außerdem ganz besonders bevorzugt für den Rest A4.A is also very particularly preferred for the rest of A4.
A steht außerdem ganz besonders bevorzugt für den Rest A5.A is also most preferably the radical A5.
A steht außerdem ganz besonders bevorzugt für den Rest A6. A steht außerdem ganz besonders bevorzugt für den Rest A9.A is also most preferably the radical A6. A is also most preferably the radical A9.
A steht außerdem ganz besonders bevorzugt für den Rest Al 1.A is also very particularly preferably the radical Al 1.
A steht außerdem ganz besonders bevorzugt für den Rest Al 6.A is also very particularly preferably the radical Al 6.
A steht außerdem ganz besonders bevorzugt für den Rest Al 7.A is also very particularly preferably the radical Al 7.
R18 steht bevorzugt für Wasserstoff, Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Cyclopropyl, Ci-C2-Halogenalkyl, Ci-C2-HaIo- genalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Trifluormethyfthio, Di- fluormethyhhio, Aminocarbonyl, Aminocarbonylmethyl oder Aminocarbonylethyl. R18 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, iso- Propyl, Monofluormethyl, Monofluorethyl, Difluormethyl, Trifluormethyl, Difluorchlor- methyl, Trichlormethyl, Dichlormethyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Trichlormethoxy, Methylthio, Ethylthio, Trifluormethylthio oder Difluormethylthio. R18 steht ganz besonders bevorzugt Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, iso-Propyl, Monofluormethyl, Monofluorethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlormethyl.R 18 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, Ci-C 2 haloalkyl, Ci-C genalkoxy 2 -HaIo- with in each case 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, di-fluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl. R 18 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, Methylthio, ethylthio, trifluoromethylthio or difluoromethylthio. R 18 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
R18 steht insbesondere bevorzugt für Methyl, Difluormethyl, Trifluormethyl oder 1-Fluorethyl. R19 steht bevorzugt fiir Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Methoxy, Ethoxy,R 18 particularly preferably represents methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl. R 19 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy,
Methylthio oder Ethylthio.Methylthio or ethylthio.
R19 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod oder Methyl. R19 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor oder Methyl.R 19 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or methyl. R 19 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
R20 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen, Hydroxymethyl, Hydroxyethyl, Cyclo- propyl, Cyclopentyl, Cyclohexyl oder Phenyl. R20 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, Trifluormethyl, Di- fluormethyl, Hydroxymethyl, Hydroxyethyl oder Phenyl.R 20 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl , R 20 particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, di-fluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
R20 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Trifluormethyl oder Phenyl.R 20 very particularly preferably represents hydrogen, methyl, trifluoromethyl or phenyl.
R20 steht insbesondere bevorzugt für Methyl.R 20 particularly preferably represents methyl.
R21 und R22 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl,R 21 and R 22 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R21 und R22 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlor- methyl. R21 und R22 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor,Ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 21 and R 22 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R 21 and R 22 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trichlormethyl. R21 und R22 stehen insbesondere bevorzugt jeweils für Wasserstoff.Bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 21 and R 22 are particularly preferably each hydrogen.
R23 steht bevorzugt für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, d-C∑-Halogenalkyl oder Ci- Cϊ-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 23 is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, dC Σ -haloalkyl or Ci- C ϊ -haloalkoxy each having 1 to 5 fluorine, chlorine and / or bromine atoms.
R23 steht besonders bevorzugt für Fluor, Chlor, Brom, Cyano, Methyl, Trifluormethyl,R 23 particularly preferably represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl,
Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Trichloπnethoxy. R23 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl oderTrifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R 23 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or
Trifluormethoxy. R23 steht insbesondere bevorzugt für Methyl oder Trifluormethyl.Trifluoromethoxy. R 23 is particularly preferably methyl or trifluoromethyl.
R24 und R25 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl,R 24 and R 25 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl,
Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R24 und R25 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlormethyl. R24 und R25 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor,Ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 24 and R 25 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R 24 and R 25 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trichlormethyl. R24 und R25 stehen insbesondere bevorzugt jeweils für Wasserstoff.Bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 24 and R 25 are particularly preferably each hydrogen.
R26 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder Ci-C2-HaIo- genalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R26 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oderR 26 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 26 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
Trifluormethyl.Trifluoromethyl.
R26 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl.R 26 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
R27 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, d-C4-Alkyl, Ci-C2-Halogenalkyl, Ci-C2-Halogenalkoxy oder Ci-C2-Halogenalkylthio mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 27 is preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or C 1 -C 2 -haloalkylthio, each having 1 to 5 fluorine , Chlorine and / or bromine atoms.
R27 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl, Trichlormethyl, Trifluormethoxy, Difhiormethoxy, Difluorchlor- methoxy, Trichlormethoxy, Trifluormethylthio, Difluormethylthio, Difluorchlormethylthio oder Trichlormethylthio.R 27 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, Difhiormethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
R27 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Difluor- methyl, Trifluormethyl oder Trichlormethyl.R 27 is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
R27 steht insbesondere bevorzugt für Iod, Methyl, Difluormethyl oder Trifluormethyl.R 27 is particularly preferably iodine, methyl, difluoromethyl or trifluoromethyl.
R28 steht bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, CrC4-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, DifluormethyKhio, Trifluormethylthio, Ci-C2-Halogenalkyl oder Ci-C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 28 preferably represents fluorine, chlorine, bromine, iodine, hydroxy, cyano, C r C 4 alkyl, methoxy, ethoxy, methylthio, ethylthio, DifluormethyKhio, trifluoromethylthio, Ci-C 2 haloalkyl or Ci-C2 haloalkoxy with in each case 1 to 5 fluorine, chlorine and / or bromine atoms.
R28 steht besonders bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Cyano, Methyl, Ethyl, n- Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl, Trichlormethyl, Methoxy, Ethoxy, Methyhhio, Ethylthio, Difluormethylthio, Trifluormethylthio, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Trichlormethoxy.R 28 particularly preferably represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, Difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
R28 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 28 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R29 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Ci-C4-Alkyl, Methoxy, Ethoxy, Methylthio, Ethyrthio, Ci-C2-Halogenalkyl oder Ci-C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Ci-C2-Alkylsulphinyl oder Ci-C2-Alkylsulphonyl. R29 steht besonders bevorzugt für Wasserstoff", Fluor, Chlor, Brom, Iod, Cyano, n-Propyl, iso-R 29 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, Ci-C 4 alkyl, methoxy, ethoxy, methylthio, Ethyrthio, Ci-C 2 haloalkyl or Ci-C2 haloalkoxy, each with 1 to 5 Fluorine, chlorine and / or bromine atoms, C 1 -C 2 -alkylsulphinyl or C 1 -C 2 -alkylsulphonyl. R 29 particularly preferably represents hydrogen ", fluorine, chlorine, bromine, iodine, cyano, n-propyl, iso-
Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluor- chlormethyl, Trichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Trifluormethoxy,Propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy,
Difluormethoxy, Difluorchlormethoxy, Trichlormethoxy, Methylsulphinyl oder Methyl- sulphonyl.Difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl or methylsulfonyl.
R29 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, n-Propyl, iso- Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Trichlormethyl, Methylsulphinyl oder Methylsulphonyl.R 29 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulphinyl or methylsulphonyl ,
R29 steht insbesondere bevorzugt für Wasserstoff.R 29 particularly preferably represents hydrogen.
R30 steht bevorzugt für Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 30 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R30 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluor- chlormethyl oder Trichlormethyl.R 30 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R31 steht bevorzugt für Methyl oder Ethyl.R 31 is preferably methyl or ethyl.
R31 steht besonders bevorzugt für Methyl.R 31 particularly preferably represents methyl.
Q1 steht bevorzugt für S (Schwefel), SO2 oder CH2. Q1 steht besonders bevorzugt für S (Schwefel) oder CH2. Q1 steht ganz besonders bevorzugt für S (Schwefel).Q 1 is preferably S (sulfur), SO 2 or CH 2 . Q 1 particularly preferably represents S (sulfur) or CH 2 . Q 1 very particularly preferably represents S (sulfur).
p steht bevorzugt für 0 oder 1. p steht besonders bevorzugt für 0.p is preferably 0 or 1. p is particularly preferably 0.
R32 steht bevorzugt für Methyl, Ethyl oder Ci-Qj-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 32 is preferably methyl, ethyl or Ci-Qj-haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen. R32 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlor- methyl oder Trichlormethyl. R32 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.Bromine atoms. R 32 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 32 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R33 steht bevorzugt für Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oderR 33 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or
Bromatomen. R33 steht besonders bevorzugt für .Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlor- methyl oder Trichlormethyl. R33 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluoπnethyl oder Trichlor- methyl.Bromine atoms. R 33 is particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 33 is particularly anz g Favor g t represents methyl, trifluoromethyl, trichloromethyl or Difluoπnethyl.
R34 und R35 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 34 and R 35 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R34 und R35 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlor- methyl.R 34 and R 35 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R34 und R35 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 34 and R 35 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R34 und R35 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 34 and R 35 are particularly preferably each hydrogen.
R36 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl oder C:-C2-R 36 is preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C : -C 2 -
Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R36 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, Trifluormethyl, Difluoπnethyl, Difluorchlormethyl oder Trichlormethyl.Haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 36 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R36 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 36 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R36 steht insbesondere bevorzugt für Methyl.R 36 particularly preferably represents methyl.
R37 und R38 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Nitro, Methyl, Ethyl oder Ci-C2-Halogenalkylmit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 37 and R 38 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R37 und R38 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom,R 37 and R 38 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine,
Nitro, Methyl, Ethyl, Trifhiormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R37 und R3S stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.Nitro, methyl, ethyl, trifhiormethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 37 and R 3S independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R37 und R38 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 37 and R 38 are particularly preferably each hydrogen.
R39 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-C2- Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen,R 39 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QC 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,
R39 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 39 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R39 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R39 steht insbesondere bevorzugt für Methyl. R40 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-C4-Alkylamino, Di(Ci-C4- alkyl)amino, Cyano, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 39 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 39 is particularly preferably methyl. R 40 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 with 1 to 5 fluorine, Chlorine and / or bromine atoms.
R40 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Cyano, Methyl, Ethyl, Trifluorrnethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R40 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino,R 40 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 40 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
Dimethylamino, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.Dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R40 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oder Trifluormethyl.R 40 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
R41 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 41 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R41 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 41 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R41 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 41 is very particularly preferably fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R41 steht insbesondere bevorzugt für Methyl, Trifluormethyl oder Difluormethyl.R 41 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
R42 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-C4-Alkylarnino, Di(Ci-C4- alkyl)amino, Cyano, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 42 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-C 4 -Alkylarnino, di (Ci-C 4 - alkyl) amino, cyano, methyl, ethyl or Ci-C 2 haloalkyl having 1 to 5 fluorine , Chlorine and / or bromine atoms.
R42 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 42 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R42 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino,R 42 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino,
Dimethylamino, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R42 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oderDimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 42 particularly preferably represents amino, methylamino, dimethylamino, methyl or
Trifluormethyl.Trifluoromethyl.
R43 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogenalkyl mit 1 bis 5R 43 is preferably fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl of 1 to 5
Fluor, Chlor und/oder Bromatomen. R43 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl,Fluorine, chlorine and / or bromine atoms. R 43 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R43 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R43 steht insbesondere bevorzugt für Methyl, Trifluormethyl oder Difluormethyl.Difluoromethyl, difluorochloromethyl or trichloromethyl. R 43 is very particularly preferably fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 43 is particularly preferably methyl, trifluoromethyl or difluoromethyl.
R44 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder d-C2-Halogenalkyl mit 1 bis 5R 44 is preferably fluorine, chlorine, bromine, methyl, ethyl or dC 2 -haloalkyl having 1 to 5
Fluor, Chlor und/oder Bromatomen. R44 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl,Fluorine, chlorine and / or bromine atoms. R 44 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,
Difluormethyl, Difluorchlormethyl oder Trichlortnethyl. R44 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl,Difluoromethyl, difluorochloromethyl or trichlorethylene. R 44 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl,
Difluormethyl oder Trichlormethyl.Difluoromethyl or trichloromethyl.
R45 steht bevorzugt für Wasserstoff, Methyl oder Ethyl. R45 steht besonders bevorzugt für Methyl.R 45 is preferably hydrogen, methyl or ethyl. R 45 is particularly preferably methyl.
R46 steht bevorzugt für Fluor, Chlor, Brom, Methyl oder Ethyl.R 46 is preferably fluorine, chlorine, bromine, methyl or ethyl.
R46 steht besonders bevorzugt für Fluor, Chlor oder Methyl.R 46 particularly preferably represents fluorine, chlorine or methyl.
R47 steht bevorzugt für Methyl, Ethyl oder d-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 47 is preferably methyl, ethyl or dC 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R47 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R47 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 47 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 47 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R47 steht insbesondere bevorzugt für Methyl oder Trifluormethyl.R 47 is particularly preferably methyl or trifluoromethyl.
R48 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-Halogen- alkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 48 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R48 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl oder Trifluormethyl.R 48 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
R49 steht bevorzugt für Fluor, Chlor, Brom, Iod, Hydroxy, Ci-C4-Alkyl, Methoxy, Ethoxy, Methyfthio, Ethyhhio, Difluormethylthio, Trifluormethylthio, Ci-C2-Halogenalkyl oder Ci- C2-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 49 is preferably fluorine, chlorine, bromine, iodine, hydroxy, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, each having 1 to 5 fluorine, chlorine and / or bromine atoms.
R49 steht besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 49 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R49 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Iod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R50 steht bevorzugt für Methyl, Ethyl, n-Propyl oder iso-Propyl. R50 steht besonders bevorzugt Methyl oder Ethyl.R 49 is very particularly preferably fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 50 is preferably methyl, ethyl, n-propyl or iso-propyl. R 50 is particularly preferably methyl or ethyl.
R51 steht bevorzugt für Wasserstoff, Methyl, Ethyl, Ci-C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen, Ci-C2-Alkoxy-Ci-C2-alkyl, Hydroxymethyl, Hydroxyethyl,R 51 preferably represents hydrogen, methyl, ethyl, Ci-C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, Ci-C 2 alkoxy-Ci-C 2 alkyl, hydroxymethyl, hydroxyethyl,
Methylsulfonyl oder Dimethylaπünosulfonyl. R51 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Trifluormethyl, Methoxymethyl,Methylsulfonyl or Dimethylaπünosulfonyl. R 51 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl,
Ethoxymethyl, Hydroxymethyl oder Hydroxyethyl. R51 steht ganz besonders bevorzugt für Methyl oder Methoxymethyl.Ethoxymethyl, hydroxymethyl or hydroxyethyl. R 51 is very particularly preferably methyl or methoxymethyl.
R52 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Ci-C2-R 52 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -
Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen. R52 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, EthylHaloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 52 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl
Trifluormethyl, Difluormethyl oder Trichlormethyl. R52 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.Trifluoromethyl, difluoromethyl or trichloromethyl. R 52 is very particularly preferably hydrogen or methyl.
R53 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, iso-Propyl oder Ci-C2-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen.R 53 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
R53 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, iso- Propyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 53 is particularly preferably hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, iso-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R53 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Difluormethyl oder Trifluormethyl.R 53 very particularly preferably represents hydrogen, methyl, difluoromethyl or trifluoromethyl.
R54 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder C1-C2-R 54 is preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -
Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R54 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oderHaloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms. R 54 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or
Trifluormethyl. R54 steht ganz besonders bevorzugt für Wasserstoff.Trifluoromethyl. R 54 is very particularly preferably hydrogen.
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.Particular preference is given to those compounds of the formula (I) in which all radicals each have the abovementioned particularly preferred meanings.
Bevorzugt sind außerdem Verbindungen der Formel (I-b) in welcher R1, R8, Ry, R1U und A die oben angegebenen Bedeutungen haben.Preference is furthermore given to compounds of the formula (Ib) in which R 1 , R 8 , R y , R 1U and A have the meanings given above.
Bevorzugt sind außerdem Verbindungen der Formel (I-c)Preference is furthermore given to compounds of the formula (I-c)
in welcher R i l1, R τ>8κ, R r>99, R τ> 1l0u und A die oben angegebenen Bedeutungen haben. in which R il 1 , R τ> 8 κ , R r> 9 9 , R τ> 1 l 0 u and A have the meanings given above.
Bevorzugt sind außerdem Verbindungen der Formel (I-d)Preference is furthermore given to compounds of the formula (I-d)
in welcher R1, R8, R9, R1U und A die oben angegebenen Bedeutungen haben. in which R 1 , R 8 , R 9 , R 1U and A have the meanings given above.
Bevorzugt sind außerdem Verbindungen der Formel (I-e)Preference is furthermore given to compounds of the formula (I-e)
in welcher R1, Rs, R9, RIU und A die oben angegebenen Bedeutungen haben. in which R 1 , R s , R 9 , R and IU have the meanings given above.
Bevorzugt sind außerdem Verbindungen der Formel (I-f) in welcher R , R , R , R und A die oben angegebenen Bedeutungen haben.Preference is furthermore given to compounds of the formula (If) in which R, R, R, R and A have the meanings given above.
Bevorzugt sind ebenfalls Verbindungen der Formeln (I) und (I-b) bis (I-f), in welchen R1 für Wasser- stoff steht.Preference is likewise given to compounds of the formulas (I) and (Ib) to (If) in which R 1 is hydrogen.
Bevorzugt sind ebenfalls Verbindungen der Formeln (I) und (I-b) bis (I-f), in welchen R8 für Wasserstoffsteht.Preference is likewise given to compounds of the formulas (I) and (Ib) to (If) in which R 8 is hydrogen.
Bevorzugt sind ebenfalls Verbindungen der Formeln (I) und (I-b) bis (I-f), in welchen R8 für Fluor steht.Preference is likewise given to compounds of the formulas (I) and (Ib) to (If) in which R 8 is fluorine.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen können jedoch auch untereinander, also zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechend.However, the general or preferred radical definitions or explanations given above can also be combined with one another as desired, ie between the respective ranges and preferred ranges. They apply accordingly to the end products as well as to the precursors and intermediates.
Verwendet man beispielsweise l-Methyl-3^τrifluorme1hyl)-lH-pyrazol-4-carbonylchlorid und Methyl-2'- airöno-3,5'-difkorbiphenyl-4-caiboxylat als Ausgangsstoffe sowie ein Base, so karm der Verlauf des erfindungsgemäßen Verfahrens (a) durch folgende Reaktionsgleichung veranschaulicht werden:If, for example, 1-methyl-3-yltrifluoromethyl) -1H-pyrazole-4-carbonyl chloride and methyl 2'-airone-3,5'-difarbiphenyl-4-carboxylate are used as starting materials and a base, then the course of the process according to the invention is poor (a) are illustrated by the following reaction equation:
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötigten Carbonsäurehalogenide sind durch die Formel (H) allgemein definiert, m dieser Formel (II) steht A bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere bevorzugt für diejenigen Bedeutungen, die bereits in Zusammenhang mit der Beschreibung der erfindungsgemäßen Stoffe der Formel (I) als bevorzugt, besonders bevorzugt usw. für diesen Rest angegeben wurden. X1 steht bevorzugt für Fluor, Chlor oder Hydroxy, besonders bevorzugt für Chlor oder Hydroxy. Die Carbonsäurehalogenide der Formel (II) sind bekannt und/oder lassen sich nach bekannten Verfahren herstellen (vgl. z.B. EP-A 0 545 099, JP-A 01-290662 und US 5,093,347).The carboxylic acid halides required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (H). M of this formula (II) A is preferred, particularly preferred, very particularly preferred or particularly preferred for those meanings which have already been described in In connection with the description of the substances of the formula (I) according to the invention as preferred, particularly preferred, etc. were given for this radical. X 1 is preferably fluorine, chlorine or hydroxyl, more preferably chlorine or hydroxy. The carboxylic acid halides of the formula (II) are known and / or can be prepared by known processes (cf., for example, EP-A 0 545 099, JP-A 01-290662 and US 5,093,347).
Die weiterhin zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötigten Amine sind durch die Formel (III) allgemein definiert. In dieser Formel (III) stehen R1, R8, R9 und R10 bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere bevorzugt für diejenigen Bedeutungen, die bereits in Zusammenhang mit der Beschreibung der erfindungsgemäßen Stoffe der Formel (I) als bevorzugt, besonders bevorzugt usw. für diesen Rest angegeben wurden.The amines furthermore required for carrying out the process (a) according to the invention as starting materials are generally defined by the formula (III). In this formula (III) R 1, R 8, R 9 and R 10 are preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have already in connection with the description of the substances according to the invention of the formula (I) as preferably, etc. are given for this radical.
Die Amine der Formeln (HI-I), (m-2) und (01-3) sind neu.The amines of formulas (HI-I), (m-2) and (01-3) are new.
Amine der Formeln (TII-I), (IH-2) und (III-3) lassen sich nach bekannten Verfahren herstellen (vgl. WO 01/53259 und WO 01/49664, siehe auch die Herstellungsbeispiele).Amines of the formulas (TII-I), (IH-2) and (III-3) can be prepared by known processes (see WO 01/53259 and WO 01/49664, see also the Preparation Examples).
Verwendet man Methyl-3 , 5 '-difluor-2'-( { [ 1 -methyl-3 -(trifluormethyl)- 1 H-pyrazol-4-yl]carbonyl} - amino)biphenyl-4-carboxylat und Acetylchlorid als Ausgangsstoffe, so kann der Verlauf des erßn- dungsgemäßen Verfahrens (b) durch das folgende Formelschema veranschaulicht werden:Using methyl-3, 5'-difluoro-2 '- ({[1-methyl-3 - (trifluoromethyl) -1H-pyrazol-4-yl] carbonyl} - amino) biphenyl-4-carboxylate and acetyl chloride as starting materials Thus, the course of the process (b) according to the invention can be illustrated by the following formula scheme:
Die zur Durchführung des erfuidungsgemäßen Verfahrens (b) als Ausgangsstoffe benötigtenThose required for carrying out the erfuidungsgemäßen method (b) as starting materials
Biphenylcarboxamide sind durch die Formel (I-a) allgemein definiert. In dieser Formel (I-a) habenBiphenylcarboxamides are generally defined by the formula (I-a). In this formula (I-a) have
R8, R9, R10 und A bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere be- vorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungs- gemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt usw. für diese Reste angegeben wurden.R 8 , R 9 , R 10 and A are preferably, more preferably, very particularly preferably or particularly preferably those meanings which have already been mentioned in connection with the description of the invention. compounds of the formula (I) as preferred, particularly preferred, etc. were given for these radicals.
Die Verbindungen der Formel (I-a) sind erfindungsgemäße Verbindungen und können nach Ver- fahren (a) hergestellt werden.The compounds of the formula (I-a) are compounds according to the invention and can be prepared by process (a).
Die zur Durchführung des erfindungsgemäßen Verfahrens (b) weiterhin als Ausgangsstoffe benötigten Halogenide sind durch die Formel (TV) allgemein definiert. In dieser Formel (IV) steht R1 B bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbesondere bevorzugt für diejenigen Bedeutungen, die bereits oben für den Rest R1 als bevorzugt, besonders bevorzugt usw. angegeben wurden, wobei R1 B niemals für Wasserstoff steht. HaI steht für Chlor, Brom oder Iod.The halides which are furthermore required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (TV). In this formula (IV) R 1 B preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have as preferred above for R 1, more preferred, etc., wherein R 1 B never for Hydrogen stands. Hal is chlorine, bromine or iodine.
Halogenide der Formel (FV) sind bekannt.Halides of the formula (FV) are known.
Als Verdünnungsmittel zur Durchfuhrung des erfindungsgemäßen Verfahrens (a) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicycli- sche 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- Methylformaniüd, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; deren Gemische mit Wasser oder reines Wasser.Suitable diluents for carrying out process (a) 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-methylformaneate, N-methylpyrrolidone or hexamethylphosphoric triamide; their mixtures with water or pure water.
Das erfindungsgemäße Verfahren (a) wird gegebenenfalls in Gegenwart eines geeigneten Säureakzeptors durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Basen infrage. Hierzu gehören vorzugsweise Erdalkalimetall- oder Alkalimetallhydride, -hydroxide, -amide, -alkoholate, -acetate, -carbonate oder -hydrogencarbonate, wie z.B. Natriumhydrid, Natriumamid, Lithiumdiisopropylamid, Natrium-methylat, Natrium-ethylat, Kalium-tert-butylat, Natriumhydroxid, Kaliumhydroxid, Natriumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogen- carbonat, Natriumhydrogencarbonat oder Ammoniumcarbonat, sowie tertiäre Amine, wie Trimethyl- amin, Triethylamin, Tributylamin, N,N-Dimethylanüin, N,N-Dimethyl-benzylamin, Pyridin, N- Methylpiperidin, N-Methyknorphoün, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU). Das erfindungsgemäße Verfahren (a) wird gegebenenfalls in Gegenwart eines geeigneten Kupplungsreagenzes durchgeführt (wenn X5 für Hydroxy steht). Als solche kommen alle üblichen Carbonyl- aktrvatoren infrage. Hierzu gehören vorzugsweise N-[3-(Dirnethylainino)propyl]-^N'-ediyl-carbodüπiide- hydrochlorid, N,N'-Di-sec-butyl-carbodiirnid, N^'-Dicyclohexylcarbodümid, N,N'-Diisopropylcarbodi- imid, 1^3^imethylarnino)propyl)-3-ethyl-c^rbodiirnid→nethiodid, 2-Bromo-3-ethyl-4-methyl-thiazoh'um- tetrafluoroborat, N,N-Bis[2-oxo-3κ)xazolidinyl]phosphorodiamidic Chloride, Chlor-tripyrrolidino- phosphonium-hexafluorphosphat, Brom-tripyrroudino-phosphonium-hexafluoφhosphat, O-(1H-Benzo- triazol- 1 -yloxy)tiis(dimethylarnino)phosphonium-hexafluoφhosphat, O-( 1 H-Benzotriazol- 1 -yl)-N,N, N^N'-tetramethyluromum-hexafluoφhosphat, 0-(lH-Beτizotriazol-l-yl)-N,N,N',N'-bis(tetrarnetliylen)- uronium-hexafluoφhosphat, O-(lH-Beri2»triazol-l-yl)-N,N,N\N'-bis(tetramediylen)urcmum-tetrafluor- borat, N,N,N',N'-Bis(tetramethylen)cWonιrcmium-tetrafluorborat, O-(7-Azabenzotriazol-l-yl)-N,N,N,N- tetramethyluronium hexafluoφhosphat und 1-Hydroxybenzotriazol. Diese Reagenzien können separat aber auch in Kombination eingesetzt werden.If appropriate, the process (a) according to the invention is 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, such as 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 tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylanine, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N -Methyknorphonium, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). If appropriate, the process (a) according to the invention is carried out in the presence of a suitable coupling reagent (if X 5 is hydroxyl). As such, all customary carbonyl actuators are suitable. These preferably include N- [3- (dimethylamino) propyl] -N'-ediylcarbodiπiide hydrochloride, N, N'-di-sec-butyl-carbodiirnide, N, N'-dicyclohexylcarbodiimide, N, N'-diisopropylcarbodi imide, 1 ^ 3 ^ imethylarnino) propyl) -3-ethyl-c ^ rbodiirnid → nethiodid, 2-Bromo-3-ethyl-4-methyl-thiazoh 'environmentally tetrafluoroborate, N, N-bis [2-oxo-3κ ) xazolidinyl] phosphorodiamidic chlorides, chloro-tripyrrolidinophosphonium hexafluorophosphate, bromo-tripyrroudino-phosphonium hexafluorophosphate, O- (1H-benzotriazol-1-oxy) tis (dimethylamino) phosphonium hexafluorophosphate, O- (1H-benzotriazole 1 -yl) -N, N, N, N'-tetramethyluromum hexafluorophosphate, 0- (1H-beotizotriazol-1-yl) -N, N, N ', N'-bis (tetrarnetliylene) uronium hexafluorophosphate, O- (1H-beriazolazol-1-yl) -N, N, N, N'-bis (tetramediylene) urcmum tetrafluoroborate, N, N, N ', N'-bis (tetramethylene) c-ammonium tetrafluoroborate , O- (7-Azabenzotriazol-1-yl) -N, N, N, N-tetramethyluronium hexafluorophosphate and 1-hydroxybenzotriazole. These reagents can be used separately or in combination.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (a) 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 process (a) 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 (a) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Carbonsäurehalogenids der Formel (IT) im Allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 2 Mol an Anilinderivat der Formel (III) ein. Die Aufarbeitung erfolgt nach üblichen Methoden.For carrying out the process (a) according to the invention for the preparation of the compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of aniline derivative of the formula (III) are employed per mole of the carboxylic acid halide of the formula (IT) ) one. The workup is carried out by conventional methods.
Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens (b) kommen alle inerten 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. Chlorbenzol, Dichlorbenzol, Dichlormethan, Chloroform, Tetrachlormethan, Dichlorethan oder Trichlor- ethan; 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-Methylpyrrolidon oder He- xamethylphosphorsäuretriamid.Suitable diluents for carrying out process (b) 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 (b) wird in Gegenwart einer Base durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Basen infrage. Hierzu gehören vorzugsweise Erdalkalimetall- oder Alkalimetallhydride, -hydroxide, -amide, -alkoholate, -acetate, -carbonate oder -hydrogencarbonate, wie z.B. Natriumhydrid, Natriumamid, Natrium-methylat, Natrium-ethylat, Kalium-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid, Natriumacetat, KaIi- umacetat, Calciumacetat, Ammoniumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogen- carbonat, Natriumhydrogencarbonat oder Caesiumcarbonat, sowie tertiäre Amine, wie Trimethyl- amin, Triethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N- Methylpiperidin, N-Methylmorpholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).The process (b) 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 Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as 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 bicarbonate, sodium bicarbonate or cesium 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 Reaktionstemperaturen können bei der Durchfuhrung des erfindungsgemäßen Verfahrens (b) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 00C bis 1500C, vorzugsweise bei Temperaturen von 200C bis 1100C.When carrying out process (b) according to the invention, the reaction temperatures can be varied within a substantial range. 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 (b) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Biphenylcarboxamids der Formel (I-a) im Allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 2 Mol an Halogenid der Formel (IV) ein.For carrying out the process (b) according to the invention for the preparation of 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 (IV) are employed per mole of the biphenylcarboxamide of the formula (Ia) ) one.
Die erfindungsgemäßen Verfahren (a) und (b) werden 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.The processes (a) and (b) 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 Pilzen und Bakterien, im Pflanzenschutz und im Materialschutz eingesetzt werden.The substances according to the invention have a strong microbicidal action 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, Enterobacteriaceae, Corynebacteriaceae und Streptomycetaceae einsetzen.Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Beispielhaft aber nicht begrenzend seien einige Erreger von pilzlichen und bakteriellen Erkrankungen, die unter die oben aufgezählten Oberbegriffe fallen, genannt: Erkrankungen, hervorgerufen durch Erreger des Echten Mehltaus wie z.B. Blumeria-Arten, wie beispielsweise Blumeria graminis;By way of example but not limitation, some pathogens of fungal and bacterial diseases, which fall under the generic names enumerated above, are named: Diseases caused by powdery mildews such as e.g. Blumeria species, such as Blumeria graminis;
Podosphaera-Arten, wie beispielsweise Podosphaera leucotricha; Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fiiliginea; Uncinula-Arten, wie beispielsweise Uncinula necator;Podosphaera species, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fiiliginea; Uncinula species, such as Uncinula necator;
Erkrankungen, hervorgerufen durch Erreger von Rostkrankheiten wie z.B. Gymnosporangium-Arten, wie beispielsweise Gymnosporangium sabinaeDiseases caused by causative agents of rust diseases, such as Gymnosporangium species, such as Gymnosporangium sabinae
Hemileia-Arten, wie beispielsweise Hemileia vastatrix;Hemileia species, such as Hemileia vastatrix;
Phakopsora-Arten, wie beispielsweise Phakopsora pachyrhizi und Phakopsora meibomiae;Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae;
Puccinia-Arten, wie beispielsweise Puccinia recondita oder Puccinia graminis;Puccinia species, such as Puccinia recondita or Puccinia graminis;
Uromyces-Arten, wie beispielsweise Uromyces appendiculatus;Uromyces species, such as Uromyces appendiculatus;
Erkrankungen, hervorgerufen durch Erreger der Gruppe der Oomyceten wie z.B.Diseases caused by pathogens of the group of Oomycetes, e.g.
Bremia-Arten, wie beispielsweise Bremia lactucae;Bremia species, such as Bremia lactucae;
Peronospora-Arten, wie beispielsweise Peronospora pisi oder P. brassicae;Peronospora species such as Peronospora pisi or P. brassicae;
Phytophthora-Arten, wie beispielsweise Phytophthora infestans; Plasmopara-Arten, wie beispielsweise Plasmopara viticola;Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmopara viticola;
Pseudoperonospora-Arten, wie beispielsweise Pseudoperonospora humuli oderPseudoperonospora species, such as Pseudoperonospora humuli or
Pseudoperonospora cubensis;Pseudoperonospora cubensis;
Pythium-Arten, wie beispielsweise Pythium uhimum;Pythium species such as Pythium uhimum;
Blattfleckenkrankheiten und Blattwelken, hervorgerufen durch z.B.Leaf spot diseases and leaf wilt caused by e.g.
Alternaria-Arten, wie beispielsweise Alternaria solani;Alternaria species, such as Alternaria solani;
Cercospora-Arten, wie beispielsweise Cercospora beticola;Cercospora species, such as Cercospora beticola;
Cladosporium-Arten, wie beispielsweise Cladosporium cucumerinum;Cladosporium species, such as Cladosporium cucumerinum;
Cochliobolus-Arten, wie beispielsweise Cochliobolus sativus (Konidienform: Drechslera, Syn: Helminthosporium);Cochliobolus species, such as Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium);
Colletotrichum-Arten, wie beispielsweise Colletotrichum lindemuthanium;Colletotrichum species, such as Colletotrichum lindemuthanium;
Cycloconium-Arten, wie beispielsweise Cycloconium oleaginum;Cycloconium species such as cycloconium oleaginum;
Diaporthe-Arten, wie beispielsweise Diaporthe citri;Diaporthe species, such as Diaporthe citri;
Elsinoe-Arten, wie beispielsweise Elsinoe fawcettii; Gloeosporium-Arten, wie beispielsweise Gloeosporium laeticolor;Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as, for example, Gloeosporium laeticolor;
Glomerella-Arten, wie beispielsweise Glomerella cingulata;Glomerella species, such as Glomerella cingulata;
Guignardia-Arten, wie beispielsweise Guignardia bidwelli;Guignardia species, such as Guignardia bidwelli;
Leptosphaeria-Arten, wie beispielsweise Leptosphaeria maculans;Leptosphaeria species, such as Leptosphaeria maculans;
Magnaporthe-Arten, wie beispielsweise Magnaporthe grisea; Mycosphaerella-Arten, wie beispielsweise Mycosphaerella graminicola und Mycosphaerella fijiensis;Magnaporthe species, such as Magnaporthe grisea; Mycosphaerella species, such as Mycosphaerella graminicola and Mycosphaerella fijiensis;
Phaeosphaeria-Arten, wie beispielsweise Phaeosphaeria nodorum; Pyrenophora-Arten, wie beispielsweise Pyrenophora teres; Ramularia-Arten, wie beispielsweise Ramularia collo-cygni; Rhynchosporium-Arten, wie beispielsweise Rhynchosporium secalis; Septoria-Arten, wie beispielsweise Septoria apii; Typhula-Arten, wie beispielsweise Typhula incarnata; Venturia-Arten, wie beispielsweise Venturia inaequalis;Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as, for example, Pyrenophora teres; Ramularia species, such as Ramularia collo-cygni; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis;
Wurzel- und Stengelkrankheiten, hervorgerufen durch z.B.Root and stem diseases caused by e.g.
Corticium-Arten, wie beispielsweise Corticium grarninearum; Fusarium-Arten, wie beispielsweise Fusarium oxysporum;Corticium species, such as Corticium grarninearum; Fusarium species such as Fusarium oxysporum;
Gaeumannomyces-Arten, wie beispielsweise Gaeumannomyces graminis;Gaeumannomyces species such as Gaeumannomyces graminis;
Rhizoctonia-Arten, wie beispielsweise Rhizoctonia solani;Rhizoctonia species, such as Rhizoctonia solani;
Tapesia-Arten, wie beispielsweise Tapesia acuformis oder Tapesia yallundae;Tapesia species such as Tapesia acuformis or Tapesia yallundae;
Thielaviopsis-Arten, wie beispielsweise Thielaviopsis basicola;Thielaviopsis species, such as Thielaviopsis basicola;
Ähren- und Rispenerkrankungen (inklusive Maiskolben), hervorgerufen durch z.B.Ear and panicle diseases (including corncob) caused by e.g.
Ahernaria-Arten, wie beispielsweise Alternaria spp.;Ahernaria species such as Alternaria spp .;
Aspergillus-Arten, wie beispielsweise Aspergillus flavus;Aspergillus species, such as Aspergillus flavus;
Cladosporium-Arten, wie beispielsweise Cladosporium cladosporioides; Claviceps-Arten, wie beispielsweise Claviceps purpurea;Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea;
Fusarium-Arten, wie beispielsweise Fusarium culmorum;Fusarium species such as Fusarium culmorum;
Gibberella-Arten, wie beispielsweise Gibberella zeae;Gibberella species, such as Gibberella zeae;
Monographella-Arten, wie beispielsweise Monographella nivalis;Monographella species, such as Monographella nivalis;
Erkrankungen, hervorgerufen durch Brandpilze wie z.B.Diseases caused by fire fungi, e.g.
Sphacelotheca-Arten, wie beispielsweise Sphacelotheca reiliana;Sphacelotheca species, such as Sphacelotheca reiliana;
Tilletia-Arten, wie beispielsweise Tilletia caries;Tilletia species, such as Tilletia caries;
Urocystis-Arten, wie beispielsweise Urocystis occulta;Urocystis species, such as Urocystis occulta;
Ustilago-Arten, wie beispielsweise Ustilago nuda;Ustilago species such as Ustilago nuda;
Fruchtfaule hervorgerufen durch z.B.Fruit rot caused by e.g.
Aspergillus-Arten, wie beispielsweise Aspergillus flavus;Aspergillus species, such as Aspergillus flavus;
Botrytis-Arten, wie beispielsweise Botrytis cinerea;Botrytis species, such as Botrytis cinerea;
Penicillium-Arten, wie beispielsweise Penicillium expansum und Penicillium purpurogenum; Sclerotinia-Arten, wie beispielsweise Sclerotinia sclerotiorum;Penicillium species such as Penicillium expansum and Penicillium purpurogenum; Sclerotinia species, such as Sclerotinia sclerotiorum;
Verticilium-Arten, wie beispielsweise Verticilium alboatrum; Samen- und bodenbürtige Fäulen und Welken, sowie Sämlingserkrankungen, hervorgerufen durch z.B. Fusarium-Arten, wie beispielsweise Fusarium cubnorum; Phytophthora Arten, wie beispielsweise Phytophthora cactorum; Pythium-Arten, wie beispielsweise Pythium ultimum; Rhizoctonia-Arten, wie beispielsweise Rhizoctonia solani; Sclerotium-Arten, wie beispielsweise Sclerotium rolfsii;Verticilium species such as Verticilium alboatrum; Seed and soil rots and wilts, and seedling diseases caused by, for example, Fusarium species such as Fusarium cubnorum; Phytophthora species, such as Phytophthora cactorum; Pythium species such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii;
Krebserkrankungen, Gallen und Hexenbesen, hervorgerufen durch z.B. Nectria-Arten, wie beispielsweise Nectria galligena;Cancers, galls and witches brooms caused by e.g. Nectria species, such as Nectria galligena;
Welkeerkrankungen hervorgerufen durch z.B. Monilinia-Arten, wie beispielsweise Monilinia laxa;Wilt diseases caused by e.g. Monilinia species, such as Monilinia laxa;
Deformationen von Blättern, Blüten und Früchten, hervorgerufen durch z.B. Taphrina-Arten, wie beispielsweise Taphrina deformans;Deformations of leaves, flowers and fruits caused by e.g. Taphrina species, such as Taphrina deformans;
Degenerationserkrankungen holziger pflanzen, hervorgerufen durch z.B.Degenerative diseases of woody plants, caused by e.g.
Esca-Arten, wie beispielsweise Phaeomoniella chlamydospora und Phaeoacremonium aleophilum und Fomitiporia mediterranea; Blüten- und Samenerkrankungen, hervorgerufen durch z.B. Botrytis-Arten, wie beispielsweise Botrytis cinerea;Esca species such as Phaeomoniella chlamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea; Flower and seed diseases caused by e.g. Botrytis species, such as Botrytis cinerea;
Erkrankungen von Pflanzenknollen, hervorgerufen durch z.B. Rhizoctonia-Arten, wie beispielsweise Rhizoctonia solani; Hehninthosporium-Arten, wie beispielsweise Hehninthosporium solani;Diseases of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani; Hehninthosporium species, such as Hehninthosporium solani;
Erkrankungen, hervorgerufen durch bakterielle Erreger wie z.B. Xanthomonas-Arten, wie beispielsweise Xanthomonas campestris pv. oryzae; Pseudomonas-Arten, wie beispielsweise Pseudomonas syringae pv. lachrymans; Erwinia-Arten, wie beispielsweise Erwinia amylovora;Diseases caused by bacterial agents such as e.g. Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora;
Bevorzugt können die folgenden Krankheiten von Soja-Bohnen bekämpft werden: Pilzkrankheiten an Blättern, Stängeln, Schoten und Samen verursacht durch z.B. Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf bhght (Choanephora rnfundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Pod and Stern Blight (Phomopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola)Preferably, the following diseases of soybean beans can be controlled: fungal diseases on leaves, stems, pods and seeds caused by, for example, Alternaria leaf spot (Alternaria sp. Ater tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines ), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf bhght (Choanephora rnfundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Pod and star blight (Phomopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola)
Pilzkrankheiten an Wurzeln und der Stängelbasis verursacht durch z.B. Black Root Rot (Calonectria crotalariae), Charcoal Rot (Macrophomina phaseolina), Fusarium Blight or WiIt, Root Rot, and Pod and Collar Rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stern Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var. caulivora), Phytophthora Rot (Phytophthora megasperma), Brown Stem Rot (Phialophora gregata), Pythium Rot (Pythium aphanidermatum, Pythium irreguläre, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Rot, Stem Decay, and Damping-Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot (Thielaviopsis basicola).Fungal diseases on roots and stem base caused by e.g. Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
Die erfindungsgemäßen Wirkstoffe weisen auch eine starke stärkende Wirkung in Pflanzen auf. Sie eignen sich daher zur Mobilisierung pflanzeneigener Abwehrkräfte gegen Befall durch unerwünschte Mikroorganismen.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 attack by unwanted microorganisms.
Unter pflanzenstärkenden (resistenzinduzierenden) Stoffen sind im vorliegenden Zusammenhang solche Substanzen zu verstehen, die in der Lage sind, das Abwehrsystem von Pflanzen so zu stimulieren, dass die behandelten Pflanzen bei nachfolgender Inokulation mit unerwünschten Mikroorganismen 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 28 Tage, vorzugsweise 1 bis 14 Tage, besonders bevorzugt 1 bis 7 Tage nach der Behandlung der Pflanzen mit den Wirkstoffen. 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.Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses. The substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens. The period within which protection is induced generally extends from 1 to 28 days, preferably 1 to 14 days, more 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.
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 Wildpflanzen 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, 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 Behandlungsmethoden, 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 methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
Im Materialschutz lassen sich die erfindungsgemäßen Stoffe zum Schutz von technischen Materialien gegen Befall und Zerstörung durch unerwünschte Mikroorganismen einsetzen. Unter technischen Materialien sind im vorliegenden Zusammenhang nichtlebende Materialien 201 verstehen, die für die Verwendung in der Technik zubereitet worden sind. Beispielsweise können technische Materialien, die durch erfindungsgemäße Wirkstoffe vor mikrobieller Veränderung oder Zerstörung ge- schützt werden sollen, Klebstoffe, Leime, Papier und Karton, Textilien, Leder, Holz, Anstrichmittel und Kunststoffartikel, Kühlschmierstoffe und andere Materiahen sein, die von Mikroorganismen 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, Anstrichmittel, Kühlschmiermittel und Wärmeübertragungsflüssigkeiten genannt, besonders bevorzugt Holz.In material protection, the substances of the invention for the protection of technical Use materials against infestation and destruction by unwanted microorganisms. By technical material is meant herein non-living materials 201 that have been prepared for use in the art. For example, technical materials which are to be protected against microbial alteration or destruction by active compounds according to the invention may be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which attack 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, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, 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. Vorzugsweise wirken die erfindungsgemäßen Wirkstoffe gegen Pilze, insbesondere Schimmelpilze, holzverfarbende 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. The active compounds according to the invention preferably 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: Alternaria, wie Ahernaria tenuis,Examples include microorganisms of the following genera: Alternaria, such as Ahernaria tenuis,
Aspergillus, wie Aspergillus niger,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, Penicillium, wie Penicillium glaucum.Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum.
Polyporus, wie Polyporus versicolor,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, Escherichia, wie Escherichia coli,Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli,
Pseudomonas, wie Pseudomonas aeruginosa,Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, wie Staphylococcus aureus.Staphylococcus, such as Staphylococcus aureus.
Die Wirkstoffe können in Abhängigkeit von ihren jeweiligen physikalischen und/ oder chemischen Eigenschaften in die üblichen Formulierungen überfuhrt werden, wie Lösungen, Emulsionen,Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions,
Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-KaIt- und Warmnebel-Formulierungen. 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 Benutzung 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 Kohlenwasserstoffe, 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 gemeint, 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, Sepio- lith, 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-Sulfitablaugen und Methylcellulose.Suspensions, powders, foams, pastes, granules, aerosols, microencapsulations in polymeric Substances and in encapsulants for seeds, as well as ULV-KaIt and warm mist formulations. These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as extender, for example, organic solvents can also 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, eg 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, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example 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: eg broken 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-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phosphoüpide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as 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.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and 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.
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, Nematoziden 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, nematocides 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: 1) Inhibitoren der Nukleinsäuresynthese: z.B. Benalaxyl, Benalaxyl-M, Bupirimate, Clozylacon,Fungicides: 1) inhibitors of nucleic acid synthesis: e.g. Benalaxyl, Benalaxyl M, Bupirimate, Clozylacon,
Dimethirimol, Ethirimol, Furalaxyl, Hymexazol, Mefenoxam, Metalaxyl, Metalaxyl-M, Ofurace,Dimethirimol, ethirimol, furalaxyl, hymexazole, mefenoxam, metalaxyl, metalaxyl-M, ofurace,
Oxadixyl, Oxolinic acid;Oxadixyl, oxolinic acid;
2) Inhibitoren von Mitose und Zellteilung: z.B. Benomyl, Carbendazim, Diethofencarb, Ethaboxam,2) inhibitors of mitosis and cell division: e.g. Benomyl, carbendazim, diethofencarb, ethaboxam,
Fuberidazole, Pencycuron, Thiabendazole, Thiophanate-methyl, Zoxamide; 3) Inhibitoren der Respiration (Atmungsketten-Inhibitoren):Fuberidazole, Pencycuron, Thiabendazole, Thiophanate-methyl, Zoxamide; 3) respiratory inhibitors (respiratory chain inhibitors):
3.1) Inhibitoren am Komplex I der Atmungskette: z.B. Diflumetorim;3.1) inhibitors of complex I of the respiratory chain: e.g. diflumetorim;
3.2) Inhibitoren am Komplex II der Atmungskette: z.B. Boscalid/Nicobifen, Carboxin, Fenfuram, Flutolanil, Furametpyr, Furmecyclox, Mepronil, Oxycarboxin, Penthiopyrad, Thifluzamide;3.2) inhibitors at the complex II of the respiratory chain: e.g. Boscalid / nicobifen, carboxin, fenfuram, flutolanil, furametpyr, furmecyclox, mepronil, oxycarboxin, penthiopyrad, thifluzamide;
3.3) Inhibitoren am Komplex Ell der Atmungskette: z.B. Amisulbrom, Azoxystrobin, Cyazofamid, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidone, Fluoxastrobin, Kresoxim-methyl, Metomino- strobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin;3.3) inhibitors at the complex Ell of the respiratory chain: e.g. Amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metomino-strobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin;
4) Entkoppler: z.B. Dinocap, Fluazinam, Meptyldinocap;4) decoupler: e.g. Dinocap, fluazinam, meptyldinocap;
5) hhibotoren der ATP Produktion: z.B. Feπtin acetate, Fentin chloride, Fentin hydroxide, Silthiofam;5) inhibitors of ATP production: e.g. Feπtin acetate, Fentin chloride, Fentin hydroxide, Silthiofam;
6) Inhibitoren der Aminosäure- und Protein-Biosynthese: z.B. Andoprim, Blasticidin-S, Cyprodinil, Kasugamycin, Kasugamycin hydrochloride hydrate, Mepanipyrim, Pyrimethanil;6) Inhibitors of amino acid and protein biosynthesis: e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;
7) Inhibitoren der Signahransduktion: z.B. Fenpiclonil, Fludioxonil, Quinoxyfen;7) inhibitors of the signal transduction: e.g. Fenpiclonil, fludioxonil, quinoxyfen;
8) Inhibitoren der Lipid- und Membran-Synthese: z.B. Biphenyl, Chlozolüiate, Edifenphos, Iodocarb, Iprobenfos, Iprodione, Isoprothiolane, Procymidone, Propamocarb, Propamocarb hydrochloride, Pyrazophos, Tolclofos-methyl, Vinclozohn; 9) Inhibitoren der Ergosterol-Biosynthese: z.B. Aldimoφh, Azaconazole, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazole, Difenoconazole, Diniconazole, Diniconazole-M, Dodemorph, Dodemorph acetate, Epoxiconazole, Etaconazole, Fenarimol, Fenbuconazole, Fenhexamid, Fenpropidin, Fenpropimorph, Fluquinconazole, Flurprimidol, Flusilazole, Flutriafol, Furconazole, Furconazole-cis, Hexaconazole, Lmazalil, Imazalil sulfate, Lnibenconazole, Ipconazole, Metconazole, Myclobutanil, Naftifine, Nuarimol, Oxpoconazole, Paclobutrazol, Pefurazoate, Penconazole, Prochloraz, Propiconazole, Prothioconazole, Pyributicarb, Pyrifenox, Simeconazole, Spiroxamine, Tebuconazole, Terbinafϊne, Tetraconazole, Triadimefon, Triadimenol, Tridemorph, Triflumizole, Triforine, Triticonazole, Uniconazole, Viniconazole, Voriconazole; 10) Inhibitoren der Zellwandsynthese: z.B. Benthiavalicarb, Ditnethomoφh, Flumorph, Iprovalicarb, Polyoxins, Polyoxorim, Validamycin A; 11) Inhibitoren der Melanin-Biosynthese: z.B. Carpropamid, Diclocymet, Fenoxanil, Phthalide, Pyroquilon, Tricyclazole;8) inhibitors of lipid and membrane synthesis: eg biphenyl, cholzoliiate, edifenphos, iodocarb, Iprobenfos, iprodione, isoprothiolanes, procymidones, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl, vinclozohn; 9) Inhibitors of ergosterol biosynthesis: eg aldimoφh, azaconazole, bitertanol, bromuconazoles, cyproconazole, diclobutrazoles, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamide, fenpropidin, fenpropimorph, fluquinconazole, Flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, lmazalil, imazalil sulfate, lnibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazole, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, simeconazole . Spiroxamine, tebuconazole, terbinafnene, tetraconazole, triadimefon, triadimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazole, viniconazole, voriconazole; 10) inhibitors of cell wall synthesis: eg Benthiavalicarb, Ditnethomoφh, Flumorph, Iprovalicarb, Polyoxins, Polyoxorim, Validamycin A; 11) inhibitors of melanin biosynthesis: eg carpropamide, diclocymet, fenoxanil, phthalides, pyroquilone, tricyclazoles;
12) Resistenzinduktoren: z.B. Acibenzolar-S-methyl, Probenazole, Tiadinil;12) resistance inducers: e.g. Acibenzolar-S-methyl, Probenazoles, Tiadinil;
13) Verbindungen mit MuMsite-Aktrvität: z.B. Bordeaux Mixture, Captafol, Captan, Chlorothalonil, Copper naphthenate, Copper oxide, Copper oxychloride, Kupferzubereitungen wie z.B. Kupferhy- droxid, Kupfersulfat, Dichlofluanid, Dithianon, Dodine, Dodine free base, Ferbam, Fluorofolpet, Folpet, Guazatine, Guazatine acetate, Iminoctadine, Iminoctadine albesilate, Iminoctadine triacetate, Mancopper, Mancozeb, Maneb, Metiram, Metiram Zinc, Oxine-Copper, Propineb, Sulphur und Schweferlzubereitungen wie z.B. Calcium polysulphide, Thiram, Tolylfluanid, Zineb, Ziram;13) Compounds with MuMsite activity: e.g. Bordeaux Mixture, Captafol, Captan, Chlorothalonil, Copper Naphthenate, Copper Oxide, Copper Oxychloride, Copper Preparations, e.g. Copper hydroxide, copper sulfate, dichlofluanid, dithianone, dodine, dodine free base, Ferbam, Fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, Propineb, Sulfur and Schweferlzubereitungen such as Calcium polysulphide, thiram, tolylfluanid, zineb, ziram;
14) eine Verbindung aus der folgenden Liste: (2E)-2-(2-{[6-(3-Chlor-2-methylphenoxy)-5-fluoφyrimi- din^-yl]oxy}phmyl)-2-(methoxyimino)-N-methylacetamid, (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-Fluor-2- phenylvinyl]oxy}phenyl)ethyHden]amino}oxy)me1hyl]ρhenyl}-2^methoxymiino)-N-me1hylace(2mid, 1- (4-Chlorphenyl)-2-(lH-l,2,4-triazol-l-yl)cycloheptanol, l-[(4-Methoxyphenoxy)methyl]-2,2-dime- thylpropyl- 1 H-imidazol- 1 -carboxylat, 2-(4-Chlorphenyl)-N- {2-[3 -methoxy-4-(prop-2-yn-l -yloxy)- phenyl]ethyl}-2-(prop-2-yn-l-yloxy)acetamid, 2,3,5,6-Tetrachlor-4-(methylsulfonyl)pyridin, 2- Butoxy-6-iod-3-propyl-4H-chromen-4-on, 2-Chlor-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl)nicotinamid, 2-Phenylphenol und Salze davon, 3,4;5-Trichloφyridin-2,6-dicarbonitril, 3,4- Dichlor-N-(2-cyanophenyl)isothiazol-5-carboxamid, 3-[5-(4-Chlθφhenyl)-2,3-dimethylisoxazolidin- 3-yl]pyridin, 5-Cmor-6-(2,4,6-trifluorophenyl)-N-[(lR)-l,2,2-trimethylpropyl][l,2,4]triazolo[l,5- a]pyrimidin-7-amin, 5-Chlor-7-(4-methylpiperidin-l-yl)-6-(2,4,6-trifluoφhenyl)[l,2,4]triazolo[l,5- a]pyrimidin, 5-Chlor-N-[(lR)-l,2-diπiethylpropyl]-6-(2,4,6-trifluoφhenyl)[l,2:,4]triazolo[l,5- a]pyrimidin-7-amin, 8-Hydroxyquinoünsulfat, Benthiazole, Bethoxazin, Capsimycin, Carvone, Chinomethionat, Cufraneb, Cyflufenamid, Cymoxanil, Dazomet, Debacarb, Dichlorophen, Diclomezine, Dicloran, Difenzoquat, Difenzoquat Methylsulphate, Diphenylamine, Ferimzone, Flumetover, Fluopicolide, Fluoroitnide, Flusulfamide, Fosetyl-Aluminium, Fosetyl-Calcium, Fosetyl- Sodium, Hexachlorobenzene, Irumamycin, Methasulfocarb, Methyl (2-chlor-5-{(lE)-N-[(6- meΛylpyridin-2-yl)medioxy]e1haniniidoyl}benzyl)carbamat, Methyl (2E)-2-{2-[({cyclopropyl[(4- methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylat, Methyl l-(2,2-dimethyl-2,3- dihydro-lH-inden-l-yl)-lH-imidazol-5-carboxylat, Methyl 3-(4-chloφhenyl)-3-{[N-14) a compound from the following list: (2E) -2- (2 - {[6- (3-chloro-2-methylphenoxy) -5-fluoro-pyrimidin-1-yl] oxy} phmyl) -2- (methoxyimino ) -N-methylacetamide, (2E) -2- {2 - [({[(LE) -l- (3 - {[(E) -l-fluoro-2-phenylvinyl] oxy} phenyl) ethylhyde] amino} oxy) methyl] phenyl} -2-methoxymiino) -N-methylthio (2mid, 1- (4-chlorophenyl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, 1 - [(4 -Methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-imidazole-1-carboxylate, 2- (4-chlorophenyl) -N- {2- [3-methoxy-4- (prop-2-yne- l -yloxy) phenyl] ethyl} -2- (prop-2-yn-1-yloxy) acetamide, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2-butoxy-6-iodo 3-propyl-4H-chromen-4-one, 2-chloro-N- (1, 1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) nicotinamide, 2-phenylphenol and salts thereof, 3,4; 5-Trichloφyridin-2,6-dicarbonitrile, 3,4-dichloro-N- (2-cyanophenyl) isothiazole-5-carboxamide, 3- [5- (4-Chlθφhenyl) -2,3-dimethylisoxazolidin- 3-yl] pyridine, 5-Cmor-6- (2,4,6-trifluorophenyl) -N - [(IR) -l, 2,2-trimethylpropyl] [1,2,4] triazolo [1,5] a] pyrimidin-7-amine, 5-chloro-7- (4-methy 1-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, 5-chloro-N - [(lR) -l, 2 diπiethylpropyl] -6- (2,4,6-trifluoφhenyl) [l, 2, 4] triazolo [l, 5- a] pyrimidin-7-amine, 8-Hydroxyquinoünsulfat, Benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, Cufraneb, Cyflufenamid, Cymoxanil, Dazomet, Debacarb, Dichlorophene, Diclomezine, Dicloran, Difenzoquat, Difenzoquat Methylsulphate, Diphenylamine, Ferimzone, Flumetover, Fluopicolide, Fluoroitnide, Flusulfamide, Fosetyl-Aluminum, Fosetyl-Calcium, Fosetyl-Sodium, Hexachlorobenzene, Irumamycin, Methasulfocarb , Methyl (2-chloro-5 - {(LE) -N - [(6-methylpyridin-2-yl) -medioxy] e1-haloiniyl} benzyl) carbamate, methyl (2E) -2- {2 - [({cyclopropyl [( 4-methoxyphenyl) imino] methyl} thio) methyl] phenyl} -3-methoxyacrylate, methyl 1- (2,2-dimethyl-2,3-dihydro-1H-inden-1-yl) -H-imidazole-5 carboxylate, methyl 3- (4-chlorophenyl) -3 - {[N-
(isopropoxycarbonyl)valyl]amino}propanoat, Methyl isothiocyanate, Metrafenone, Mildiomycin, N- (3^4'-DicWor-5-fluorbiphemyl-2-yl)0-(difluonnethyl)-l-methyl-lH-pyrazol-4-carboxamid, N-(3- EthylO,5,5-trmethylcyclohexyl)-3-(formylarnino)-2-hydroxybenzamid, N-(4-Chlor-2-nitrophenyl)- N-ethyl-4-methylbenzensxilfonamid, N-[(5-Brom-3^Mθφyridin-2-yl)methyl]-2,4-ΛcMoπiiccϊtinainid, N-[l-(5-Brom-3-cWoφyridin-2-yl)ethyl]-2,4-dichlormcσtinamid, N-[l-(5-Brom-3-chlorpyridin-2- yl)ethyl]-2-fluor-4-iodnicotinainid, N-[2-(4-{[3-(4-Chlorpheαyl)prop-2-yn-l-yl]oxy}-3- methoxyphenyl)ethyl]-N2-(melhylsulfonyl)valinaniid, N-{(Z)-[(Cyclopropylmethoxy)imino][6-(difluor- methoxy)-2,3-difluorphenyl]methyl} -2-phenylacetamid, N- {2-[3 -Chlor-5 -(trifluormethyl)pyridin-2- yl]ethyl}-2-(trifluoππethyl)benzamid, Natamycin, Nickel Dimethyldithiocarbamate, Nitrothal- isopropyl, O-{l-[(4-Methoxyphenoxy)methyl]-2,2-dimethylpropyl} lH-Irnidazol-1-carbothioat, Oc- thilinone, Oxamocarb, Oxyfenthiin, Pentachlorophenol und Salze, Phosphorsäure und ihre Salze, Piperalin, Propamocarb Fosetylate, Propanosine-Sodium, Proquinazid, Pyrrolnitrine, Quintozene, Tecloftalam, Tecnazene, Triazoxide, Trichlamide, Zarilamid.(isopropoxycarbonyl) valyl] amino} propanoate, methyl isothiocyanate, metrafenone, mildiomycin, N- (3 ^ 4'-dicor-5-fluorobiphemyl-2-yl) 0- (difluoro-ethyl) -l-methyl-1H-pyrazole-4 carboxamide, N- (3-ethyl-O, 5,5-trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide, N- (4-chloro-2-nitrophenyl) - N-ethyl-4-methylbenzenesulfonamide, N - [(5-bromo-3-methyl-pyridin-2-yl) -methyl] -2,4-c-amino-cinnamic acid, N- [1- (5-bromo-3-cyclohexyridin-2-yl ) ethyl] -2,4-dichlorometacamide, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodo-nicotinic acid, N- [2- (4 - {[3 - (4-chloro-phenyl) -prop-2-yn-1-yl] oxy} -3-methoxyphenyl) ethyl] -N 2 - (melysulfonyl) valinanide, N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, N- {2- [3-chloro-5 - (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, Natamycin, nickel dimethyldithiocarbamate, nitrothal isopropyl, O- {1- [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl} -1H-iridazole-1-carbothioate, octyninones, oxamocarb, oxyfenthiine, pentachlorophenol and salts, phosphoric acid and their salts, piperine, propamocarb fosetylate, propanosine sodium, proquinazide, pyrroline nitrine, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, zarilamide.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
1. Acetylcholinesterase (AChE) Inhibitoren1. Acetylcholinesterase (AChE) inhibitors
1.1 Carbamate (z.B. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbo- furan, Carbosulfan, Chloethocarb, Coumaphos, Cyanofenphos, Cyanophos, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Metbiocarb, 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, Chlorfenvin- phos, Chlormephos, Chlorpyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlor- fenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenhrothion, Fensulfothion, Fenthion, FIu- pyrazofos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Me- thamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyiy-ethyl), Pheπthoate, 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) 2. Natrium-Kanal-Modulatoren /Spannungsabhängige Natrium-Kanal-Blocker1.1 carbamates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carboofuran, carbosulfane, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, Fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, metbiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamates, trimethacarb, XMC, xylylcarb) 1.2 Organophosphates (eg, Acephate, Azamethiphos, Azinphos (-methyl , -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothione, chloroethoxyfos, chlorfenvinophos, chloroforms, chlorpyrifos (-methyl / -ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulfonot, EPN, ethione, ethoprophos, Etrimfos, Famphur, Fen amiphos, fenhrothione, fensulfothion, fenthion, fulpyrazofos, fonofos, formothion, fosmethilane, fosthiazate, heptenophos, iodofenofen, ipprobenfos, isazofos, isofenphos, isopropyl o-salicylates, isoxathione, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos , Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methylethyl), Pheπthoate, 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, thiometone, triazophos, triclorfone, vamidothion) 2. Sodium channel modulators / voltage-dependent sodium channel blockers
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, Empenthrin (lR-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fen- valerate, Flubrocythrinate, Flucythrinate, Fhifenprox, 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))2.1 Pyrethroids (eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, biotethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlorovaporthrin, cis-cypermethrin , Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (IR-isomer), esfenvalerate, etofenprox , Fenfluthrin, fenpropathrin, fenpyrithrin, fenvalate, flubrocythrinates, flucythrinates, fhifenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (lR- trans isomer), prallethrin, profuthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralomethyrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum))
2.2 Oxadiazine (z.B. Indoxacarb) 3. Acetylcholin-Rezeptor-AgonistenZ-Antagonisten2.2 Oxadiazines (e.g., Indoxacarb) 3. Acetylcholine receptor agonists 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, Cartap3.2 Nicotine, Bensultap, Cartap
4. Acetylcholin-Rezeptor-Modulatoren 4.1 Spinosyne (z.B. Spinosad)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, Methoxychlor5.1 Cyclodienes Organochlorines (e.g., camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
5.2 Fiprole (z.B. Acetoprole, Ethiprole, Fipronil, Vaniliprole) 6. Chlorid-Kanal-Aktivatoren5.2 Fiproles (e.g., acetoprole, ethiprole, fipronil, vaniliprole) 6. 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-Mimetika7. Juvenile hormone mimetics
(z.B. Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene)(e.g., diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene)
8. Ecdysonagonisten/disruptoren8. ecdysonagonists / disruptors
8.1 Diacylhydrazäne (z.B. Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide)8.1 diacylhydrazones (e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides)
9. Inhibitoren der Chitinbiosynthese9. Inhibitors of chitin biosynthesis
9.1 Benzoylhamstoffe (z.B. Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Tri- flumuron) 9.2 Buprofezin9.1 Benzoylureas (eg bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, trifluoron) 9.2 Buprofezin
9.3 Cyromazine9.3 Cyromazine
10. Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren 10.1 Diafenthiuron 10.2 Organotine (z.B. Azocyclotin, Cyhexatin, Fenbutatin-oxide)10. Inhibitors of oxidative phosphorylation, ATP disruptors 10.1 Diafenthiuron 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. Binapacyrl, Dinobuton, Dinocap, DNOC)11.2 Dinitrophenols (e.g., binapacyrl, dinobutone, dinocap, DNOC)
12. Site-I-Elektronentransportinhibitoren 12.1 METI's (z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)12. Site I Electron Transport Inhibitors 12.1 METI's (e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad)
12.2 Hydramethylnone12.2 Hydramethylnone
12.3 Dicofol12.3 Dicofol
13. Site-II-Elektronentransportinhibitoren 13.1 Rotenone13. Site II Electron Transport Inhibitors 13.1 Rotenone
14. Site-UI-Elektronentransportinhibitoren 14.1 Acequinocyl, Fluacrypyrim14. Site UI Electron Transport Inhibitors 14.1 Acequinocyl, Fluacrypyrim
15. Mikrobielle Disruptoren der Insektendarmmembran Bacillus thuringiensis-Stäπime 16. Inhibitoren der Fettsynthese15. 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 ethyl 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 ethyl 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 ATPase18. Octopaminergic agonists (e.g., amitraz) 19. Inhibitors of magnesium-stimulated ATPase
(z.B. Propargite)(e.g., propargite)
20. Agonisten des Ryanodin-Rezeptors,20. agonists of the ryanodine receptor,
20.1 Benzoesäuredicarboxamide [z.B. N2-[l,l-Dimethyl-2-(methylsulfonyl)ethyl]-3-iod-N1-[2- methyl-4-[l,2,2,2-te;trafluor-l-(trifluormethyl)ethyl]phenyl]-l,2-benzenedicarboxarnide (CAS-Reg.- No.: 272451-65-7), Flubendiamide] 20.2 Aπthranilamide (z.B. DPX E2Y45 = 3-Brom-N-{4-chlor-2-methyl-6-[(methylamino)carbonyl]- phenyl}-l-(3-chlθφyridin-2-yl)-lH-pyrazol-5-carboxamid)20.1 Benzoic acid dicarboxamides [eg N 2 - [l, l-dimethyl-2- (methylsulphonyl) ethyl] -3-iodo-N 1 - [2-methyl-4- [l, 2,2,2-tetrofluoro-1 - (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7), flubendiamide] 20.2 Aπthranilamides (eg DPX E2Y45 = 3-bromo-N- {4-chloro-2-methyl-6 - [(methylamino) carbonyl] -phenyl} -1- (3-chloro-pyridin-2-yl) -lH-pyrazole 5-carboxamide)
21. Nereistoxin-Analoge21. Nereistoxin Analogs
(z.B. Thiocyclam hydrogen Oxalate, Thiosultap-sodium) 22. Biologika, Hormone oder Pheromone(e.g., thiocyclam hydrogen oxalate, thiosultap-sodium) 22. Biologics, hormones or pheromones
(z.B. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizium spec, Paecilomyces speα, Thxiringiensin, Verticillium spec.)(e.g., Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhicon spec., Paecilomyces spec., Thxiringiensin, Verticillium spec.)
23. Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen 23.1 Begasungsmittel (z.B. Aluminium phosphide, Methyl bromide, Sulfuryl fluoride) 23.2 Selektive Fraßhemmer (z.B. Cryolite, Flonicamid, Pymetrozine)23. Active substances with unknown or nonspecific modes of action 23.1 Fumigants (for example aluminum phosphides, methyl bromides, sulphuryl fluorides) 23.2 Selective feeding inhibitors (for example cryolites, flonicamide, 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, Chinome- thionat, CMordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethyl- none, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, 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.23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, quinomethionate, CMordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flotenzin, Gossyplure, Hydramethylone, Japonilure, Metoxadiazone , Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, further the compound 3-methyl-phenyl-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 Isomers (CAS Reg. No. 185984-60-5) (see WO 96/37494, WO 98/25923), as well as preparations containing insecticide-effective 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.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.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Spritzpulver, Pasten, löslicheThe active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble
Pulver, Stäubemittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstäuben, Verschäumen, Bestreichen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low-Volume-Verfahren auszubringen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. Es kann auch das Saatgut der Pflanzen behandelt werden. Beim Einsatz der erfindungsgemäßen Wirkstoffe als Fungizide können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereiches variiert werden. Bei der Behandlung von Pflanzenteilen liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 10 und 1.000 g/ha. Bei der Saatgutbehandlung liegen die 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.Powder, dusts and granules are applied. The application happens in usual Example, by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself in the soil. It can also be the seed of the plants to be treated. When 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 parts of plants, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the seed treatment, the application rates of active ingredient are 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 Ausfuhrungsform werden wild vorkommende oder durch konventionelle biologischeAs already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild or by conventional biological
Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen undBreeding methods, such as crossing or protoplast fusion obtained plant species and plant varieties and their parts treated. In a further preferred embodiment, transgenic plants and
Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellenPlant varieties obtained by genetic engineering, optionally in combination with conventional
Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw. „Teile von Pflanzen" oder „Pflanzenteile" wurde oben erläutert.Methods were obtained (Genetically Modified Organisms) and their parts treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
Besonders bevorzugt werden erfindungsgemäß 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.It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. 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, 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, weiter entwickeltes Wurzelsystem, höhere Beständigkeit der Pflanzenart bzw. Pflanzensorte, gesteigertes Wachstum der Schösslinge, höhere Pflanzenvitahtät, 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, größere Früchte, höhere Pflanzengröße, grünere Blattfarbe, frühere Blüte, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Zuckerkonzentration in den Früchten, höhere Lagerfahigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen. 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 Eigenschaften („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, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfahigkeit 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 CryIA(a), CryIA(b), CryIA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im Folgenden „Bt 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 Wirkstoffen, z.B. Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"- Gen). Die jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für „Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen 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- säte 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 Clearfield® vertriebenen Sorten (z.B. Mais) erwähnt. Selbst- verständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften („Traits").Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention may also give rise to superadditive ("synergistic") effects, for example reduced application rates and / or extensions of the activity spectrum and / or a Strengthening of the effect of the substances and agents which can be used according to the invention, better plant growth, more developed root system, higher resistance of the plant species or plant variety, increased growth of the shoots, higher plant vigor, increased tolerance to high or low temperatures, increased tolerance to drought or to water or water Soil salt content, increased flowering power, easier harvesting, acceleration of ripeness, higher crop yields, larger Fruits, higher plant size, greener leaf color, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the fruits, higher storage capacity and / or workability of the harvest products possible, which go beyond the expected effects. The preferred plants or plant cultivars to be treated according to the invention 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 dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability 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 as well as an increased tolerance of the plants against certain herbicidal active substances. 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 which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a) , CryIA (b), CryIA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, and combinations thereof) in the plants (hereafter "Bt 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. ), the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosates or phosphinotricin (eg "PAT" gene), are particularly emphasized. The genes conferring the desired properties ("traits") can also be present in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YIELD GARD® (eg maize , Cotton, soybean), 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 glyphosides). corn, cotton, soybeans), 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 the varieties marketed under the name Clearfield® (eg corn) mentioned. 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 1example 1
Zu einer Suspension bestehend aus 155.3 mg (0.8 mmol) l-Methyl-3-(trifluormethyl)-lH-pyrazol-4- carbonsäure in 5 ml Dichlormethan und 30 μl Dimethylformamid werden 0.08 ml (0.88 mmol) Oxalsäuredichlorid gegeben. Die Reaktionsmischung wird für 2 Stunden bei Raumtemperatur gerührt bevor eine Lösung bestehend aus 210.6 mg (0.8 mmol) Methyl 2'-amino-3,5'- difluorbiphenyl-4-carboxylat und 0.16 ml (1.1 mmol) Triethylamin in 5 ml Dichlormethan zugetropft wird. Die Reaktionsmischung wird für 16 Stunden bei Raumtemperatur gerührt, auf 4 ml Wasser gegeben, die organische Phase wird über Natriumsulfat getrocknet und im Vakuum aufkonzentriert. Man erhält 308 mg (0.7 mmol, 87 % der Theorie) Methyl-3,5'-difluor-2'-({[l-methyl-3- (trifluormethyl)-lH-pyrazol-4-yl]carbonyl}amino)biphenyl-4-carboxylat (log P (pH 2.3) 2.64).To a suspension consisting of 155.3 mg (0.8 mmol) of 1-methyl-3- (trifluoromethyl) -1-H-pyrazole-4-carboxylic acid in 5 ml of dichloromethane and 30 ul of dimethylformamide 0.08 ml (0.88 mmol) of oxalic acid are added. The reaction mixture is stirred for 2 hours at room temperature before a solution consisting of 210.6 mg (0.8 mmol) of methyl 2'-amino-3,5'-difluorobiphenyl-4-carboxylate and 0.16 ml (1.1 mmol) of triethylamine in 5 ml of dichloromethane is added dropwise , The reaction mixture is stirred for 16 hours at room temperature, added to 4 ml of water, the organic phase is dried over sodium sulfate and concentrated in vacuo. This gives 308 mg (0.7 mmol, 87% of theory) of methyl 3,5'-difluoro-2 '- ({[l-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] carbonyl} amino) biphenyl-4-carboxylate (log P (pH 2.3) 2.64).
Analog Beispiel 1 sowie entsprechend den allgemeinen Beschreibungen der erfindungsgemäßen Verfahren können die in der folgenden Tabelle 1 genannten Verbindungen der Formel (I) erhalten werden.Analogously to Example 1 and according to the general descriptions of the process according to the invention, the compounds of the formula (I) mentioned in Table 1 below can be obtained.
Tabelle 1Table 1
Herstellung von Ausgangsstoffen der Formel (III)Preparation of starting materials of the formula (III)
Beispiel (111-1)Example (111-1)
Unter Inertgasatmosphäre (Argon) werden 4.5 ml einer gesättigten Natriumcarbonatlösung und 0.1 g (0.1 mmol) Tetrakis(triplienylphosphin)palladium(0) zu einer Suspension bestehend aus 0.9 g (4.8 mmol) 2- Brcan-4-fhκ>rani]in und 1.0 g (5.1 mmol) [3-Fluor-4-(methoxycarbonyl)phenyl]boronsäure in 5 ml Toluol und 0.5 ml Ethanol gegeben. Die Reaktionsmischung wird für 16 Stunden bei 80°C gerührt, anschließend auf 10 ml Wasser gegeben und mit 20 ml Toluol extrahiert. Die vereinigten organischen Phasen werden über Magnesiumsulfat getrocknet, filtriert und im Vakuum aufkonzentriert. Säulenchromatographie (Gradient Cyclohexan/Essigsäureethylester) liefert 0.5 g (1.76 mmol, 37 % der Theorie) an Metiiyl-2'- arnino-3,5'-<lifluorbψhenyl-4-carboxylat [log P (pH 2.3) 2.73].Under an inert gas atmosphere (argon), 4.5 ml of a saturated sodium carbonate solution and 0.1 g (0.1 mmol) of tetrakis (triplienylphosphine) palladium (0) are added to a suspension consisting of 0.9 g (4.8 mmol) of 2-brcan-4-fhκ> rani] in and 1.0 g (5.1 mmol) of [3-fluoro-4- (methoxycarbonyl) phenyl] boronic acid in 5 ml of toluene and 0.5 ml of ethanol. The reaction mixture is stirred for 16 hours at 80 ° C, then added to 10 ml of water and extracted with 20 ml of toluene. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography (gradient cyclohexane / ethyl acetate) gives 0.5 g (1.76 mmol, 37% of theory) of methyl 2'-arnino-3,5 '- <lifluorobenzyl-4-carboxylate [log P (pH 2.3) 2.73].
Analog Beispiel (HI-I) sowie entsprechend den allgemeinen Beschreibungen der erfindungsgemäßen Verfahren können die in der folgenden Tabelle 2 genannten Verbindungen der Formel (III) erhalten werden.Analogously to Example (HI-I) and according to the general descriptions of the process according to the invention, the compounds of the formula (III) mentioned in Table 2 below can be obtained.
Tabelle 2 Table 2
Die Bestimmung der in den voranstehenden Tabellen und Herstellungsbeispielen angegebenen logP- Werte erfolgt gemäß EEC-Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18). Temperatur: 43°C.The determination of the logP values indicated in the above tables and preparation examples is carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
Die Bestimmung erfolgt im sauren Bereich bei pH 2.3 mit 0,1 % wässriger Phosphorsäure und Acetonitril als Eluenten; linearer Gradient von 10 % Acetonitril bis 90 % Acetonitril.The determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluent; linear gradient from 10% acetonitrile to 90% acetonitrile.
Die Eichung erfolgt 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 is 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
Venturia - Test (Apfel) / protektiv Lösungsmittel: 24,5 Gewichtsteile AcetonVenturia - Test (Apple) / Protective Solvent: 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 Wirkstoflfzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable active compound preparation, 1 part by weight of active compound is mixed with the stated 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. Die Pflanzen werden dann im Gewächshaus bei ca. 21°C und einer relativen Luftfeuchtigkeit von ca. 90 % 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 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. 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.
Tabelle ATable A
Venturia - Test (Apfel) / protektivVenturia - test (apple) / protective
Beispiel B Example B
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.
Tabelle BTable B
Botrytis - Test (Bohne) / protektivBotrytis - test (bean) / protective
Beispiel C Example C
Uromyces - Test (Bohne) / protektivUromyces 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 die Pflanzen mit einer wässrigen Sporensuspension des Bohnenrosterregers Uromyces appendiculatus inokuliert und verbleiben dann 1 Tag bei ca. 200C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine. Die Pflanzen werden dann im Gewächshaus bei ca. 21°C und einer relativen Luftfeuchtigkeit von ca. 90 % 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 bean rust pathogen, Uromyces appendiculatus and then remain for 1 day at about 20 0 C and 100% relative humidity in an incubation cabinet. 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.
Tabelle CTable C
Uromyces - Test (Bohne) / protektivUromyces test (bean) / protective
Tabelle C Table C
Uromyces - Test (Bohne) / protektivUromyces test (bean) / protective
Beispiel DExample D
Puccinia - Test (Weizen) / protektivPuccinia - test (wheat) / protective
Lösungsmittel: 50 Gewichtsteile N,N-DimethylacetamidSolvent: 50 parts by weight of N, N-dimethylacetamide
Emulgator: 1 Gewichtsteil AlkylaiylpolyglykoletherEmulsifier: 1 part by weight of alkylaiyl 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 Wirkstofrzubereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer Konidiensuspension von Puccinia recondita 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 active compound preparation in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. 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, um die Entwicklung von Rostpusteln zu begünstigen.The plants are then placed in a greenhouse at a temperature of about 20 0 C and a relative humidity of 80% to promote the development of rust pustules.
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.
Tabelle DTable D
Puccinia - Test (Weizen) / protektivPuccinia - test (wheat) / protective
(1)(1)
Tabelle D Table D
Puccinia - Test (Weizen) / protektivPuccinia - test (wheat) / protective

Claims

Patentansprflche Patentansprflche
1. Biphenylcarboxamide der Formel (I)1. Biphenylcarboxamides of the formula (I)
in welcher in which
R1 für Wasserstoff, Ci-C8-Alkyl, Ci-C6-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Cj-C4- Alkoxy-Ci-C4-alkyl, C3-C8-Cycloalkyl; Ci-C6-Halogenalkyl, Ci-C4-Halogenalkyl- thio, Ci-GrHalogenalkylsulflnyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Ci-C4- alkoxy-Ci-C4-alkyl, C3-C8-Halogeiicycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3-alkyl, (Ci-C3-Alkyl)carbonyl-Ci-C3- alkyl, (Ci-C3-Alkoxy)carbonyl-Ci-C3-alkyl; Halogen-(Ci-C3-alkyl)carbonyl-Ci-C3- alkyl, Halogen-(Ci-C3-alkoxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Ci-Cg-Alkyljcarbonyl, (Ci-C8-Alkoxy)carbonyl, (Ci-C8-Alkylthio)carbonyl, (Ci-C4- Alkoxy-Ci-C4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)car- bonyl, (C3-C8-Cycloalkyl)carbonyl; (Ci-Cβ-Halogen- alkoxy)carbonyl, (Ci-C6-Halogenalkylthio)carbonyl, (Halogen-Ci-C4-alkoxy-Ci-C4- alkyl)carbonyl, (C3-C6-Halogenalkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)car- bonyl, (C3-C$-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/ oder Bromatomen; oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1^, -CH=C=CH-R1 A,R 1 represents hydrogen, Ci-C 8 alkyl, Ci-C 6 alkylsulfinyl, Ci-C6 alkylsulfonyl, Cj-C 4 - alkoxy-Ci-C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C 6 haloalkyl, Ci-C 4 haloalkyl thio, C GrHalogenalkylsulflnyl, Ci-C4-haloalkylsulfonyl, halo-Ci-C 4 - alkoxy-Ci-C 4 alkyl, C 3 -C 8 -Halogeiicycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 3 alkyl, (Ci-C 3 alkyl) carbonyl-Ci-C 3 - alkyl, (Ci-C 3 alkoxy) carbonyl-Ci-C 3 alkyl; Halogen (Ci-C 3 -alkyl) carbonyl-Ci-C 3 - alkyl, halogeno (Ci-C 3 -alkoxy) carbonyl-Ci-C 3 -alkyl with in each case 1 to 13 fluorine, chlorine and / or bromine atoms; (Ci-Cg-Alkyljcarbonyl, (Ci-C 8 alkoxy) carbonyl, (Ci-C 8 alkylthio) carbonyl, (Ci-C 4 - alkoxy-Ci-C4-alkyl) carbonyl, (C 3 -C 6 Alkenyloxy) carbonyl, (C 3 -C 6 alkynyloxy) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl; (Ci-Cβ-halo- alkoxy) carbonyl, (Ci-C 6 haloalkylthio) carbonyl, (halo-Ci-C4-alkoxy-Ci-C 4 - alkyl) carbonyl, (C 3 -C 6 haloalkenyloxy) carbonyl , (C 3 -C 6 -haloalkynyloxy) carbonyl, (C 3 -C 8 -halocycloalkyl) carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; or -CH 2 -C≡CR 1 A , -CH 2 -CH = CH-R 1 ^, -CH = C = CH-R 1 A ,
-C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht,-C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 ,
R1 A für Wasserstoff, Ci-C6-Alkyl, Ci-Cβ-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C7-Cycloalkyl, (Ci-C4-Alkoxy)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6- Alkinyloxy)carbonyl oder Cyano steht, R2 für Wasserstoff, C1-C8-AIlCyI, CrC8-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, C3-C8-R 1 A represents hydrogen, Ci-C 6 alkyl, Ci-Cβ-haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, (Ci-C 4 alkoxy ) carbonyl, (C 3 -C 6 alkenyloxy) carbonyl, (C 3 -C 6 - alkynyloxy) carbonyl or cyano, R 2 is hydrogen, C 1 -C 8 -alkyl, C r C 8 alkoxy, Ci- C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -
Cycloalkyl; Ci-C6-Halogenalkyl, Ci-C6-Halogenalkoxy, Halogen-Ci-C4-alkoxy-Ci-cycloalkyl; C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halogeno-C 1 -C 4 -alkoxy-ci-
C4-alkyl, C3-C8-Halogencycloa]kyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oderC 4 alkyl, C 3 -C 8 halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or
Bromatomen steht,Bromine atoms stands,
R3 und R4 unabhängig voneinander jeweils für Wasserstoff, Ci-Cg-Alkyl, Ci-C4-Alkoxy-Ci-C4- alkyi, C3-C8-Cycloalkyl; C,-C8-Halogenalkyl, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-R 3 and R 4 are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 8 -haloalkyl, halogeno-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -
Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R3 und R4 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q- 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 NR7 enthalten kann,Halogencycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 3 and R 4 together with the nitrogen atom to which they are attached, form a saturated heterocycle having 5 to 8 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or Q-C 4 -alkyl, where the heterocycle is 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain
R5 und R6 unabhängig voneinander für Wasserstoff, Ci-C8-Alkyl, C3-C8-Cycloalkyl; Q-C8- Halogenalkyl, Cs-Cs-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 5 and R 6 are each independently hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyl; QC 8 - are haloalkyl, Cs-Cs-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen ge- gebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q-R 5 and R 6 also together with the nitrogen atom to which they are bonded, optionally one or more times, identically or differently, by halogen or
C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus derC 4 alkyl substituted saturated heterocycle having 5 to 8 ring atoms form, wherein the heterocycle 1 or 2 further, non-adjacent heteroatoms of the
Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,May contain oxygen, sulfur or NR 7 ,
R7 für Wasserstoff oder Q-Cβ-Alkyl steht, R8 für Wasserstoff oder Fluor steht,R 7 is hydrogen or Q-Cβ-alkyl, R 8 is hydrogen or fluorine,
R9 für -SOmRπ, -SO2NR12R13, -C(=X)R14, -NR12R13, -CH2-NR12R13 steht,R 9 is -SO m R π , -SO 2 NR 12 R 13 , -C (= X) R 14 , -NR 12 R 13 , -CH 2 -NR 12 R 13 ,
R10 für Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl steht,R 10 is fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl,
R11 für Ci-Cβ-Alkyl oder Ci-C6-Halogenalkyl mit 1 bis 13 Halogenatomen steht, m für 1 oder 2 steht, R12 für Wasserstoff, C,-C4-Alkyl oder -C(=X)R14 steht,R 11 is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl having 1 to 13 halogen atoms, m is 1 or 2, R 12 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 14 stands,
R13 für Wasserstoff, Ci-C4-Alkyl oder -C(=X)R14 steht,R 13 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 14 ,
R12 und R13 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oderR 12 and R 13 also together with the nitrogen atom to which they are attached, optionally one or more times, identically or differently, by halogen or
Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus derCi-C 4 alkyl substituted saturated heterocycle having 5 to 8 ring atoms form, wherein the heterocycle 1 or 2 further, non-adjacent heteroatoms of the
Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,May contain oxygen, sulfur or NR 7 ,
X für O (Sauerstoff) oder S (Schwefel) steht,X is O (oxygen) or S (sulfur),
R14 für Wasserstoff, Ci-C4-Alkyl, Ci-C4-Alkoxy oder -NR16R17 steht,R 14 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or -NR 16 R 17 ,
R15 für Wasserstoff, Q-C8-Alkyl, Ci-C8-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Q-C4- Alkylthio-Q-C4-alkyl oder Q-Cβ-Halogenalkyl steht, wobei die drei Reste R15 jeweils gleich oder verschieden sein können,R 15 is hydrogen, QC 8 alkyl, Ci-C 8 alkoxy, Ci-C 4 alkoxy-Ci-C 4 alkyl, QC 4 - alkylthio-QC 4 alkyl or Q-Cβ-haloalkyl, wherein the each of three radicals R 15 may be the same or different,
R16 Wasserstoff oder Q-C4-Alkyl steht,R 16 is hydrogen or QC 4 -alkyl,
R17 Wasserstoff oder Q-C4-Alkyl steht,R 17 is hydrogen or QC 4 -alkyl,
R16 und R17 außerdem gemeinsam mit dem Stickstoflatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oderR 16 and R 17 also together with the nitrogen atom to which they are attached, optionally one or more times, identically or differently, by halogen or
Q-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 NR7 enthalten kann, A für einen der folgenden Reste Al bis Al 9 stehtForm QC 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 7 , A is one of the following radicals Al to Al 9
Al A2 A3 A4 A5Al A2 A3 A4 A5
All A12 A13 A14 A15All A12 A13 A14 A15
A16 A17 A18 A19A16 A17 A18 A19
R18 für Wasserstoff, Cyano, Halogen, Nitro, d-C4-Alkyl, Ci-C4-AIkOXy, Ci-C4-Alkyl- thio, C3-C6-Cycloalkyl, Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy oder Ci-C4-HaIo- genalkyhhio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder Aminocar- bonyl-Ci-C4-alkyl steht, R19 für Wasserstoff, Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Alkoxy oder Ci-C4-Alkylthio steht,R 18 represents hydrogen, cyano, halogen, nitro, dC 4 alkyl, Ci-C 4 -alkoxy, Ci-C 4 alkyl thio, C 3 -C 6 cycloalkyl, Ci-C 4 haloalkyl, Ci-C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C 1 -C 4 -alkyl, R 19 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkyl -C 4 alkoxy or Ci-C 4 alkylthio group,
R20 für Wasserstoff, C1-CVAIkJi-, Hydroxy-C-C.-alkyl, Cj-Cβ-Cycloalkyl, Ci-Q-AlkyliMo-Q-Q-alkyl, Ci-C4-Halogenalkyl, CrC4-R 20 is hydrogen, C 1 -C -alkenyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -cycloalkyl, C 1 -C 4 -alkyl-MoQQ-alkyl, C 1 -C 4 -haloalkyl, C r C 4 -
Halogenalkyltbio-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl mit jeweils 1 bis 5 Halogenalkyltbio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl having in each case 1 to 5
Halogenatomen, oder Phenyl steht,Halogen atoms, or phenyl,
R21 und R22 unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-R 21 and R 22 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -
Halogenalkyl mit 1 bis 5 Halogenatomen steht, R23 für Halogen, Cyano oder Ci-C4-Alkyl, oder Ci-C4-Halogenalkyl oder Ci-C4-HaIo- genalkoxy mit jeweils 1 bis 5 Halogenatomen steht,Halogenoalkyl having 1 to 5 halogen atoms, R 23 is halogen, cyano or Ci-C 4 alkyl, or Ci-C 4 haloalkyl or Ci-C 4 -HaIo- genalkoxy each having 1 to 5 halogen atoms,
R24 und R25 unabhängig voneinander für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4- Halogenalkyl mit 1 bis 5 Halogenatomen steht, R26 für Wasserstoff, Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 24 and R 25 are independently hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 - represents halogenoalkyl having 1 to 5 halogen atoms, R 26 is hydrogen, halogen, C r C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R27 für Wasserstoff, Halogen, Hydroxy, Cyano, Ci-C6-Alkyl, Ci-Q-Halogenalkyl, C1- C4-Halogenalkoxy oder Ci-C4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht,R 27 is hydrogen, halogen, hydroxyl, cyano, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio having in each case 1 to 5 halogen atoms,
R28 für Halogen, Hydroxy, Cyano, d-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, C1-C4- Halogenalkyl, Ci-C4-Halogenalkyhhio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht,R 28 is halogen, hydroxy, cyano, dC 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, C 1 -C 4 - haloalkyl, Ci-C4 -Halogenalkyhhio or Ci-C4-haloalkoxy with each 1 to 5 halogen atoms,
R29 für Wasserstoff, Halogen, Cyano, Ci-C4-Alkyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, C1- C4-Halogenalkyl, Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, C1-C4-R 29 is hydrogen, halogen, cyano, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, C 1 - C 4 haloalkyl, Ci-C4-halogenoalkoxy having in each case 1 to 5 halogen atoms, C 1 -C 4 -
Alkylsulphinyl oder Ci-C4-Alkylsulphonyl steht,Alkylsulphinyl or C 1 -C 4 -alkylsulphonyl,
R30 für CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 30 is C r C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms,
R31 für Ci-C4-Alkyl steht,R 31 is C 1 -C 4 -alkyl,
Q1 für S (Schwefel), SO, SO2 oder CH2 steht, p für O5 1 oder 2, wobei R22 für identische oder verschiedene Reste steht, wenn p für 2 steht,Q 1 is S (sulfur), SO, SO 2 or CH 2 , p is O 5 1 or 2, where R 22 is identical or different radicals when p is 2,
R32 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 32 is C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R33 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 33 4 -alkyl or Ci-C 4 haloalkyl having 1 stands for Ci-C to 5 halogen atoms,
R34 und R35 unabhängig voneinander für Wasserstoff, Halogen, Amino, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen,R 34 and R 35 are independently hydrogen, halogen, amino, Ci-C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 are halogen atoms,
R36 für Wasserstoff, Halogen, CrC4-Alkyl oder Q-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 36 is hydrogen, halogen, C r C 4 alkyl or QC is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R37 und R38 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen, R39 für Wasserstoff, Halogen, CrC4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5R 37 and R 38 are independently hydrogen, halogen, amino, Ci-C 4 alkyl or Ci-C4-haloalkyl nitro group having 1 to 5 halogen atoms, R 39 is hydrogen, halogen, C r C 4 alkyl or C C 4 haloalkyl having 1 to 5
Halogenatomen steht,Halogen atoms is,
R40 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)amino, Cyano, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 40 is hydrogen, halogen, amino, Ci-C 4 alkylamino, di- (Ci-C 4 alkyl) amino, cyano, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R41 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R42 für Wasserstoff, Halogen, Amino, Ci-C4-Alkylamino, Di-(Ci-C4-alkyl)amino,R 41 represents halogen, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms, R 42 is hydrogen, halogen, amino, Ci-C 4 alkylamino, di- (Ci-C4-alkyl) amino,
Cyano, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,Cyano, Ci-C 4 alkyl or Ci-C is 4 -halogenoalkyl having 1 to 5 halogen atoms,
R43 für Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 43 represents halogen, Ci-C 4 alkyl or Ci-C4-haloalkyl having 1 to 5 halogen atoms,
R44 für Halogen, Ci-C4-Alkyl oder C]-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 44 represents halogen, Ci-C 4 alkyl or C] -C 4 -halogenoalkyl having 1 to 5 halogen atoms,
R45 für Wasserstoff oder C1-C4-AIlCyI steht, R46 für Halogen oder C1-C4-AIlCyI steht,R 45 is hydrogen or C 1 -C 4 -alkyl, R 46 is halogen or C 1 -C 4 -alkyl,
R47 für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R48 für Wasserstoff, Halogen, C,-C4-Alkyl oder d-C-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 47 4 -alkyl or Ci-C 4 haloalkyl having 1 stands for Ci-C to 5 halogen atoms, R 48 is hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C -haloalkyl having 1 to 5 halogen atoms,
R49 für Halogen, Hydroxy, Ci-C4-A]kyl, Ci-C4-Alkoxy, Ci-C4-Alkylthio, CrC4-Halo- genalkyl, Ci-C4-Halogenalkylthio oder Ci-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht,R 49 represents halogen, hydroxyl, Ci-C 4 -A] -alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylthio, C r C 4 -Halo- genalkyl, Ci-C4-haloalkylthio or C 4 Haloalkoxy having in each case 1 to 5 halogen atoms,
R50 für CrC4-Alkyl steht,R 50 is C r C 4 -alkyl,
R51 für Wasserstoff, Cyano, Q-Q-Alkyl, Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen, d-Q-Alkoxy-d-C^alkyl, Hydroxy-d-C^alkyl, Q-Q-Alkylsulfonyl, Di(Ci-C4-alkyl)- aminosulfonyl, Ci-Cδ-Alkylcarbonyl oder jeweils gegebenenfalls substituiertes Phenylsulfonyl oder Benzoyl steht,R 51 is hydrogen, cyano, QQ-alkyl, QQ-haloalkyl having 1 to 5 halogen atoms, dQ-alkoxy-dC ^ alkyl, hydroxy-dC ^ alkyl, QQ-alkylsulfonyl, di (Ci-C 4 -alkyl) - aminosulfonyl, Ci-C δ alkylcarbonyl or in each case optionally substituted phenylsulfonyl or benzoyl,
R52 für Wasserstoff, Halogen, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht,R 52 is hydrogen, halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5 halogen atoms,
R53 für Wasserstoff, Halogen, Cyano, Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 5R 53 is hydrogen, halogen, cyano, Ci-C 4 alkyl or Ci-C 4 haloalkyl having 1 to 5
Halogenatomen steht, R54 für Wasserstoff, Halogen, C,-C4-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht.Halogen atoms, R 54 is hydrogen, halogen, C, -C 4 alkyl or QQ-haloalkyl having 1 to 5 halogen atoms.
2. Verfahren zum Herstellen von Biphenylcarboxamiden der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass man (a) Carbonsäurehalogenide der Formel (II)2. A process for preparing biphenylcarboxamides of the formula (I) according to claim 1, which comprises (a) carboxylic acid halides of the formula (II)
in welcher in which
A die in Anspruch 1 angegebenen Bedeutungen hat, X1 für Halogen oder Hydroxy steht, mit Aminen der Formel (IQ)A has the meanings given in claim 1, X 1 is halogen or hydroxy, with amines of the formula (IQ)
in welcher R1, R8, R9 und R10 die in Anspruch 1 angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Kupplungsreagenzes, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungs- mittels umsetzt, oder in which R 1 , R 8 , R 9 and R 10 have the meanings given in claim 1, if appropriate in the presence of a coupling reagent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
(b) Biphenylcarboxamide der Formel (I-a)(b) biphenylcarboxamides of the formula (I-a)
in welcher R8, R9, R10 und A die in Anspruch 1 angegebenen Bedeutungen haben, mit Halogeniden der Formel (IV) R1^-HaI (TV) in welcher in which R 8 , R 9 , R 10 and A have the meanings given in claim 1, with halides of the formula (IV) R 1 ^ -HaI (TV) in which
R1 B für Ci-Cs-Alkyl, d-Cβ-Allcylsulfinyl, Q-Cβ-Alkylsulfonyl, Ci-C4-Alkoxy- Ci-C4-alkyl, C3-C8-Cycloalkyl; Ci-C6-Halogenalkyl, CrC4-Halogenalkyl- thio, Ci-Q-Halogenalkylsulfinyl, Ci-C4-Halogenalkylsulfonyl, Halogen-Cr C4-alkoxy-Ci-C4-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3-alkyl, (Ci-C3-Alkyl)- carbonyl-Ci-Cs-alkyl, (Ci-C3-Alkoxy)carbonyl-Ci-C3-alkyl; Halogen-(Cr C3-alkyl)carbonyl-Ci-C3-alkyl, Halogen-(Ci-C3-alkoxy)carbonyl-Ci-C3- alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (d-C8-A]kyl)carbonyl, (d-Cs-AlkoxyJcarbonyl, (CrC8-Alkylthio)carbonyl, (Ci-C4-Alkoxy-C1-C4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6- Alkinyloxy)carbonyl, (C3-C8-Cycloalkyl)carbonyl; (Ci-C6-Halogenalkyl)- carbonyl, (Ci-C6-Halogenalkoxy)carbonyl, (Ci-C6-Halogenalkyhhio)car- bonyl, (Halogen-Ci-C4-alkoxy-Ci-C4-alkyl)carbonyL, (C3-C(rHalogen- alkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)carbonyl, (C3-C8-Halogen- cycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1^, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht,R 1 B is Ci-Cs-alkyl, d-Cβ-Allcylsulfinyl, Q-Cβ alkylsulfonyl, Ci-C4-alkoxy- Ci-C 4 alkyl, C 3 -C 8 cycloalkyl; Ci-C 6 haloalkyl, C r C 4 haloalkyl thio, Ci-Q-haloalkylsulfinyl, Ci-C4-haloalkylsulfonyl, halo-Cr C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 - Halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl) -carbonyl-C 1 -C 8 -alkyl, (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl; Halogen (C r C 3 alkyl) carbonyl-Ci-C 3 alkyl, halogeno (Ci-C 3 alkoxy) carbonyl-Ci-C 3 - alkyl with in each case 1 to 13 fluorine, chlorine and / or bromine atoms; (dC 8 -A] alkyl) carbonyl, (d-Cs-AlkoxyJcarbonyl, (CrC 8 alkylthio) carbonyl, (Ci-C 4 -alkoxy-C 1 -C 4 alkyl) carbonyl, (C 3 -C 6 - alkenyloxy) carbonyl, (C 3 -C 6 - alkynyloxy) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl, (Ci-C 6 -haloalkyl) - carbonyl, (Ci-C 6 haloalkoxy) carbonyl, (Ci- C 6 -haloalkylthio) carbonyl, (halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C (r -halogenoalkenyloxy) carbonyl, (C 3 -C 6 -haloalkynyloxy) carbonyl , (C 3 -C 8 -halogeno-cycloalkyl) carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, or -CH 2 -C≡CR 1 A , -CH 2 -CH = CH-R 1 ^ , -CH = C =CH-R 1 A , -C (= O) C (= O) R 2 , -CONR 3 R 4 or -CH 2 NR 5 R 6 ,
R1 A, R2, R3, R4, R5 und R6 die in Anspruch 1 angegebenen Bedeutungen haben,R 1 A , R 2 , R 3 , R 4 , R 5 and R 6 have the meanings given in claim 1,
HaI für Chlor, Brom oder Iod steht, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt. Hal is chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
3. Mittel zum Bekämpfen unerwünschter Mikroorganismen, gekennzeichnet durch einen Gehalt an mindestens einem Biphenylcarboxamid der Formel (I) gemäß Anspruch 1 neben Streckmitteln und/oder oberflächenaktiven Stoffen.3. A composition for controlling unwanted microorganisms, characterized by a content of at least one biphenylcarboxamide of the formula (I) according to claim 1 in addition to extenders and / or surface-active substances.
4. Verwendung von Biphenylcarboxamiden der Formel (I) gemäß Anspruch 1 zum Bekämpfen unerwünschter Mikroorganismen.4. Use of biphenylcarboxamides of the formula (I) according to claim 1 for controlling unwanted microorganisms.
5. Verfahren zum Bekämpfen unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Biphenylcarboxamide der Formel (I) gemäß Anspruch 1 auf die Mikroorganismen und/oder deren Lebensraum ausbringt.5. A method for controlling unwanted microorganisms, characterized in that Biphenylcarboxamide of formula (I) according to claim 1 on the microorganisms and / or their habitat applies.
6. Verfahren zum Herstellen von Mitteln zum Bekämpfen unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Biphenylcarboxamide der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt.6. A process for the preparation of agents for controlling unwanted microorganisms, characterized in that mixing biphenylcarboxamides of the formula (I) according to claim 1 with extenders and / or surface-active substances.
7. Verwendung von Biphenylcarboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von Saatgut.7. Use of biphenylcarboxamides of the formula (I) according to claim 1 for the treatment of seed.
8. Verwendung von Biphenylcarboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von transgenen Pflanzen.8. Use of biphenylcarboxamides of the formula (I) according to claim 1 for the treatment of transgenic plants.
9. Verwendung von Biphenylcarboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von Saatgut transgener Pflanzen.9. Use of biphenylcarboxamides of the formula (I) according to claim 1 for the treatment of seeds of transgenic plants.
10. Amine der Formeln (HI-I)5 (HI-2) und (m-3)10. Amines of Formulas (HI-I) 5 (HI-2) and (m-3)
(iπ-i) (m-2) (iπ-i) (m-2)
EP06829298A 2005-12-17 2006-12-05 Biphenyl carboxamides for controlling micro-organisms Withdrawn EP1966149A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005060462A DE102005060462A1 (en) 2005-12-17 2005-12-17 biphenylcarboxamides
PCT/EP2006/011652 WO2007068376A1 (en) 2005-12-17 2006-12-05 Biphenyl carboxamides for controlling micro-organisms

Publications (1)

Publication Number Publication Date
EP1966149A1 true EP1966149A1 (en) 2008-09-10

Family

ID=37808109

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06829298A Withdrawn EP1966149A1 (en) 2005-12-17 2006-12-05 Biphenyl carboxamides for controlling micro-organisms

Country Status (15)

Country Link
US (1) US7799739B2 (en)
EP (1) EP1966149A1 (en)
JP (1) JP2009519913A (en)
KR (1) KR20080085040A (en)
CN (1) CN101336234A (en)
AR (1) AR058387A1 (en)
AU (1) AU2006326336A1 (en)
BR (1) BRPI0620008A2 (en)
CA (1) CA2633190A1 (en)
CR (1) CR10075A (en)
DE (1) DE102005060462A1 (en)
EA (1) EA015496B9 (en)
IL (1) IL192244A0 (en)
UA (1) UA92625C2 (en)
WO (1) WO2007068376A1 (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10246959A1 (en) * 2002-10-09 2004-04-22 Bayer Cropscience Ag New N-biphenyl thiazole-5-carboxamide derivatives, useful as antimicrobials for the protection of plants and technical materials, e.g. wood, against bacteria, fungi and algae
DE10347090A1 (en) 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistic fungicidal drug combinations
DE10354607A1 (en) * 2003-11-21 2005-06-16 Bayer Cropscience Ag Siylated carboxamides
DE102004005786A1 (en) * 2004-02-06 2005-08-25 Bayer Cropscience Ag Haloalkylcarboxamide
DE102004005785A1 (en) * 2004-02-06 2005-08-25 Bayer Cropscience Ag 2-Halogenfuryl / thienyl-3-carboxamide
DE102004041530A1 (en) * 2004-08-27 2006-03-02 Bayer Cropscience Ag biphenyl thiazole carboxamides
DE102004041532A1 (en) * 2004-08-27 2006-03-02 Bayer Cropscience Ag biphenyl thiazole carboxamides
DE102005009458A1 (en) * 2005-03-02 2006-09-07 Bayer Cropscience Ag pyrazolylcarboxanilides
DE102005022147A1 (en) * 2005-04-28 2006-11-02 Bayer Cropscience Ag Active agent combination, useful to e.g. combat animal parasites and phytopathogenic fungus, comprises a carboxyamide compound and/or at least an active agent e.g. acetylcholine-receptor-agonist/antagonist
DE102005025989A1 (en) * 2005-06-07 2007-01-11 Bayer Cropscience Ag carboxamides
DE102005035300A1 (en) 2005-07-28 2007-02-01 Bayer Cropscience Ag Synergistic fungicidal composition containing a carboxamide, azole and optionally strobilurin, for control of e.g. Puccinia or Erysiphe by treatment of plants, seeds or soil
DE102005060464A1 (en) * 2005-12-17 2007-06-28 Bayer Cropscience Ag Pyrazolylcarboxamide
US8176828B2 (en) 2007-03-21 2012-05-15 Schott Corporation Glass-ceramic with laminates
US9091510B2 (en) 2007-03-21 2015-07-28 Schott Corporation Transparent armor system and method of manufacture
BR112013012082A2 (en) 2010-11-15 2016-07-19 Bayer Ip Gmbh 5-halopyrazole carboxamides
US8815772B2 (en) 2012-06-29 2014-08-26 E I Du Pont De Nemours And Company Fungicidal heterocyclic carboxamides
TWI670012B (en) * 2014-07-28 2019-09-01 美商陶氏農業科學公司 Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto
TWI677491B (en) * 2014-08-26 2019-11-21 美商陶氏農業科學公司 Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto
CN107592862B (en) * 2015-05-12 2021-06-15 Fmc公司 Aryl-substituted bicyclic compounds as herbicides
UY36887A (en) 2015-09-07 2017-03-31 Bayer Cropscience Ag HETEROCYCLIC CONDENSED DERIVATIVES REPLACED BY 2- (HET) ARILO AS PESTICIDES
BR112019019605B1 (en) 2017-03-21 2023-03-07 Fmc Corporation COMPOUNDS AND PROCESS FOR PREPARING A COMPOUND OF FORMULA II-A
CN106994725B (en) * 2017-05-27 2018-08-21 江苏农林职业技术学院 It is a kind of to be used to impregnate rosin furans preservative of poplar and its preparation method and application
CN113912534B (en) * 2021-11-10 2023-07-25 江苏科技大学 Biphenyl heterocyclic compound, synthesis method and application thereof

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0788362B2 (en) 1988-05-16 1995-09-27 三井東圧化学株式会社 Process for producing pyrazole carboxylic acid chlorides
US5093347A (en) * 1991-01-28 1992-03-03 Monsanto Company 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use
IL103614A (en) 1991-11-22 1998-09-24 Basf Ag Carboxamides for controlling botrytis and certain novel such compounds
GB9510459D0 (en) * 1995-05-24 1995-07-19 Zeneca Ltd Bicyclic amines
DE19531813A1 (en) * 1995-08-30 1997-03-06 Basf Ag Bisphenylamides
DE19629828A1 (en) * 1996-07-24 1998-01-29 Bayer Ag Carbanilides
HUP0000582A3 (en) * 1996-11-26 2001-10-29 Zeneca Ltd Insecticidal, acaricidal and nematocidal 8-azabicyclo[3.2.1]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- and 9-aza-3-thiabicyclo[3.3.1]nonane derivatives, preparation and use thereof
GB9624611D0 (en) 1996-11-26 1997-01-15 Zeneca Ltd Bicyclic amine compounds
DE19840322A1 (en) * 1998-09-04 2000-03-09 Bayer Ag Pyrazole carboxanilides
KR20020058089A (en) * 1999-12-09 2002-07-12 릴리 엠 씨즐러 스피허, 아네뜨 워너 Pyrazolecarboxamide and pyrazolethioamide as fungicide
GB9930750D0 (en) 1999-12-29 2000-02-16 Novartis Ag Organic compounds
GB0001447D0 (en) * 2000-01-21 2000-03-08 Novartis Ag Organic compounds
JP2001326542A (en) * 2000-05-16 2001-11-22 Texas Instr Japan Ltd Amplifier
DE10204391A1 (en) * 2002-02-04 2003-08-14 Bayer Cropscience Ag Difluormethylthiazolylcarboxanilide
DE10204390A1 (en) * 2002-02-04 2003-08-14 Bayer Cropscience Ag Disubstituted thiazolylcarboxanilides
DE10215292A1 (en) * 2002-02-19 2003-08-28 Bayer Cropscience Ag New N-biphenylyl-1-methyl-3-(di- or trifluoromethyl)-1H-pyrazole-4-carboxamides, useful as microbicides, especially fungicides and bactericides for protection of plants or materials such as wood
JP4426308B2 (en) * 2002-02-23 2010-03-03 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト Bactericides based on biphenylbenzamide derivatives
DE10218231A1 (en) * 2002-04-24 2003-11-06 Bayer Cropscience Ag methylthiophenecarboxanilides
EP1699763A1 (en) * 2003-12-23 2006-09-13 Basf Aktiengesellschaft 3-trifluoromethyl picolinic acid anilides, and use thereof as fungicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007068376A1 *

Also Published As

Publication number Publication date
DE102005060462A1 (en) 2007-06-28
BRPI0620008A2 (en) 2011-10-25
EA015496B9 (en) 2012-03-30
WO2007068376A1 (en) 2007-06-21
US20090076113A1 (en) 2009-03-19
CN101336234A (en) 2008-12-31
KR20080085040A (en) 2008-09-22
CA2633190A1 (en) 2007-06-21
CR10075A (en) 2008-10-08
IL192244A0 (en) 2008-12-29
US7799739B2 (en) 2010-09-21
AR058387A1 (en) 2008-01-30
UA92625C2 (en) 2010-11-25
EA200801560A1 (en) 2008-12-30
EA015496B1 (en) 2011-08-30
JP2009519913A (en) 2009-05-21
AU2006326336A1 (en) 2007-06-21

Similar Documents

Publication Publication Date Title
EP1856054B1 (en) Pyrazolylcarboxanilides
EP1966149A1 (en) Biphenyl carboxamides for controlling micro-organisms
EP1966161B1 (en) Carboxamides for controlling undesired micro-organisms in plant protection
EP1966147B1 (en) Carboxamides for controlling micro-organisms in plant and material protection
EP1966148A1 (en) Carboxamides
EP2216332B1 (en) Silicium containing 2-alkyl-cycloalk(en)yl-carboxamides and their use as fungizides
WO2006024387A2 (en) Biphenyl-thiazolo-carboxamides
EP1727816B1 (en) Microbicidal silylated carboxamides
EP1965642A2 (en) Pyrazolyl carboxamides
EP1965640A2 (en) Thienylpyridyl carboxamides
MX2008007856A (en) Biphenyl carboxamides for controlling micro-organisms

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20080717

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20100316

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20100928