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EP1965642A2 - Pyrazolyl carboxamides - Google Patents

Pyrazolyl carboxamides

Info

Publication number
EP1965642A2
EP1965642A2 EP06829292A EP06829292A EP1965642A2 EP 1965642 A2 EP1965642 A2 EP 1965642A2 EP 06829292 A EP06829292 A EP 06829292A EP 06829292 A EP06829292 A EP 06829292A EP 1965642 A2 EP1965642 A2 EP 1965642A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
carbonyl
alkoxy
hydrogen
formula
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Withdrawn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
EP06829292A
Other languages
German (de)
French (fr)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Jörg Nico Greul
Herbert Gayer
Peter Dahmen
Arnd Voerste
Ulrike Wachendorff-Neumann
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 EP1965642A2 publication Critical patent/EP1965642A2/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • 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
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to novel pyrazolylcarboxamides, to a plurality of processes for their preparation and to their use for controlling harmful microorganisms in crop protection and material protection.
  • the compounds N- (4'-fluorobiphenyl-2-yl) -1-methyl-3- (pentafluoroethyl) -1H-pyrazole-4-carboxamide (from WO 01/42223) and N-acetyl-N- ( 4'-fluorobiphenyl-2-yl) -1- (methoxymethyl) -3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (from WO 02/059086).
  • the effectiveness of the compounds described in the prior art is good, but leaves at low application rates in some cases to be desired.
  • R 1 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -cralkyl, C 3 -C 8 -cycloalkyl; Ci-C 6 haloalkyl, dC ⁇ haloalkylthio, C r C 4 -Halogenal- kylsulfinyl, C 1 -C 4 -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; Phenyl, formyl-Q-C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -
  • R ' A fiii hydrogen, C, -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C
  • Cycloalkyl (C 1 -C 4 -alkoxy) carbonyl, (C 3 -C 6 -alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) carboyl or cyano,
  • R 2 Fuei hydrogen, C 1 -C 8 -alkyl, Ci-C 8 alkoxy, Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 cycloalkyl;
  • Ci-C ⁇ -haloalkyl Ci-C5 haloalkoxy, halogen-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -HaIo- geicycloalkyl each having 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; Q-Cs-haloalkyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -halo-cydoalkyl 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 heterocyclic group > clus may contain 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulfur or NR 7 , R 5 and R 6 independently of one another represent hydrogen, Q-Cg-alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 8 -haloalkyl,
  • C j-Cg-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 5 and R (also together with the nitrogen atom to which they are attached, optionally one or more times, the same or different form a halogenated or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, where the heterocycle may contain 1 or 2 further, nonadjacent heteroatoms from the series oxygen, sulfur or NR,
  • R 7 is hydrogen or C 1 -C 6 -alkyl
  • M is a phenyl ring which is monosubstituted by R 8 or a thiophene ring which is monosubstituted by R 8'A ,
  • R 8 is fluorine, chlorine, methyl, iso-propyl, methylthio or trifluoromethyl
  • R 8 A f is hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl
  • R 9 is hydrogen, fluorine or chlorine a)
  • R 10 is Ci-C 6 alkyl or Ci-C is 6 haloalkyl having 1 to 13 halogen atoms, and
  • R 11 represents hydrogen, C 2 -C 6 -alkyl, hydroxy-GKValkyl, Ca-C ⁇ cycloalkyl, C r C 4 alkylthio
  • R 10 is C 2 -C 6 -alkyl or C 2 -C 6 haloalkyl having 1 to 13 halogen atoms, and
  • R 1 ' is hydrogen; C r C 6 -A] kyl, hydroxy-QQ-alkyl, Cs-Ce-cycloalkyl, C r C 4 alkylthio -C 4 alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 haloalkyl, Ci-C 4 -haloalkylthio Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl having in each case 1 to 9 halogen atoms, (d- C8-alkyl) carbonyl, (Ci- C 8 alkoxy) carbonyl, (Ci-C 8 alkylthio) carbonyl, (C r C4 alkoxy Ci-C4 alkyl) carbonyl; (C 1 -C 6 -haloalkyl) carbonyl, (C 1 -C 6 -haloalkoxy) carbonyl,
  • R 12 represents halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, Thiocarb- ar ⁇ oyl, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C r C 4 Alkoxy, C, -C 4 alkylthio, C, -
  • R 14 and R 15 together with the nitrogen atom to which they are attached additionally form an optionally mono- or polysubstituted by identical or different halogen or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, where the hetero cyclus may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 7 ,
  • X is O (oxygen) or S (sulfur)
  • R 16 is hydrogen, C 1 -C 4 -alkyl, Ci-C 4 -alkoxy or -NR 18 R * is'
  • R ⁇ represents hydrogen, Ci-C 8 alkyl, C r C 8 alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 alkylthio C r C 4 alkyl or C 6 -haloalkyl, where the three radicals R 17 may each be the same or different, R 18 is ether or C 1 -C 4 -alkyl,
  • R 19 is hydrogen or C 1 -C 4 -alkyl
  • R 18 and R 19 also together with the nitrogen atom to which they are attached form a given ifalls monosubstituted or polysubstituted by identical or different halogen or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, where the hetero cyolus may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 7 .
  • R ' ', R 10 and R 11 have the meanings given above,
  • X 1 is halogen or hydroxy, with amines of the formula (III)
  • R 1 B is QQ-alkyl, CQ-alkylsulfinyl, Ci-Q-alkylsulfonyl, dC-alkoxy-C ⁇ -alkyl, C 3 -C 8 -cycloalkyl; CrC ⁇ haloalkyl, dC 4 haloalkylthio, C r C 4 -Halo- 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 3 alkyl, (Ci-C 3 alkyl) carbonyl-Ci-C 3 alkyl, (C r C 3 alkoxy) - carbonyl-Ci-C 3 alkyl;
  • 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 are as indicated above H, d is chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
  • novel pyrazolylcarboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials.
  • the compounds according to the invention can be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, B. E- and Z-, threo- and erythro-, as well as 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.
  • stereoisomers such as, for example, B. E- and Z-, threo- and erythro-, as well as optical isomers, but optionally also of tautomers.
  • the pyrazolylcarboxamides according to the invention are generally defined by the formula (I).
  • Preferred radical definitions of the above and below mentioned formers 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, C r C 4 alkylsulfinyl, Ci-C 4 -Alkylsu] fonyl, C 1 - Cs-Ci-Cs-.Ukoxy-alkyl, C 3 -C 6 - cycloalkyl; Ci-C 4 haloalkyl, C r C 4 haloalkylthio, C 1 - C 4 haloalkylsulfinyl, Ci-Q-haloalkylsulfonyl, halo-C) -C 3 alkoxy-C] -C 3 alkyl, C 3 -C 8- halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, Ci-Cs-Fortnyl-alkyl, (Ci-C 3 alkyl) carbonyl-C r C 3 alkyl, (Ci-C
  • -CH 2 -CH CH-R 1 ⁇
  • R 1 is particularly preferably 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-butylsurfinyl, methylsubfonyl, ethylsulphonyl, n- or iso-propylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifluoromethyl, trichloroethyl, trifluoroethyl,
  • R stand 1 A preferably represents hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -
  • R ' "A is particularly preferably hydrogen, methyl or ethyl.
  • R 2 is preferably hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; Ci-C 4 haloalkyl, Ci-C4 haloalkoxy, halogen-Ci-C 3 alkoxy-Ci-C 3 - alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 2 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, meihoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
  • R 3 and R 4 independently of one another preferably represent hydrogen, Ci-C ⁇ alkyl, Ci-C 3 alkoxy Ci-C 3 alkyl, C 3 -C 6 cycloalkyl; C 1 -C 4 -haloalkyl, halogeno-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -
  • C ⁇ -halogenocycloalkyl 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 one to four times, identically or differently, by halogen or
  • 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, ethyl-oxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
  • R 3 and R 4 together with the nitrogen atom to which they are attached, moreover preferably form an optionally monosubstituted to quadruple, identical or different, by fluorine,
  • R 5 and R 6 independently of one another preferably represent hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, or bromine atoms.
  • R 5 and R 6 together with the nitrogen atom to which they are attached preferably also 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 4 -alkyl, where the hetcarocycle is 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain.
  • R 5 and R 6 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,
  • 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,
  • 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.
  • M is particularly preferably a cycle selected from MI, M-2 and M-4.
  • M is most preferably for the cycle M-1.
  • M is also very particularly preferably the heterocycle M-2.
  • R 8 is preferably fluorine, with fluorine being particularly preferably in the A, S or 6 position, very particularly preferably in the 4- or 6-position, in particular in the 4-position of the anilide radical.
  • R 8 furthermore preferably represents chlorine, chlorine being particularly preferably in the 5-position of
  • R 8 is preferably methyl, with methyl being particularly preferably in the 3-position of the anilide radical.
  • R 8 furthermore preferably represents trifluoromethyl, trifluoromethyl being particularly preferably in the 4- or 5-position of the anilide radical.
  • R 8 A stands. preferred for hydrogen.
  • R 8 A is furthermore preferably chlorine, with chlorine being more preferably in the 5 position (M-2,
  • R 8 A is furthermore preferably methyl, with methyl being particularly preferably in the 5-position (M-)
  • R 9 is preferably hydrogen.
  • R 9 is also preferably fluorine.
  • R 9 is also preferably chlorine.
  • R 10 and R 11 are depending on one another preferably represent the following combinations: a) R 10 preferably represents dC 4 alkyl or C ⁇ -C 4 -haloalkyl having 1 to 9 fluorine, chlorine or bromine atoms, and
  • R 11 is preferably hydrogen, C 2 -C 4 -alkyl, hydroxy-C 2 -C 4 -alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, Ci-C 3 -AIkOXy- Ci-Cs-alkyl, C 2 -C 4 haloalkyl, C, -C 3 haloalkylthio--C 3 alkyl, C 1 -C 3 -
  • R u is preferably hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, C 1 -C 3 -alkylthio-C 1 -C 3 -alkyl, C 1 -C 3 - alkoxy
  • Haloalkoxy-C 1 -C 3 -alkyl having in each case 1 to 9 fluorine, chlorine or bromine atoms,
  • R 10 particularly preferably represents methyl, ethyl, n-, isopropyl, n-, i-, s-, t-butyl,
  • R 11 particularly preferably represents hydrogen, ethyl, n-, isopropyl, n-, i-, s-, t-butyl,
  • R 10 particularly preferably represents ethyl, n-, isopropyl, n-, i-, s-, t-butyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3
  • R 11 particularly preferably represents hydrogen, methyl, ethyl, n-, iso-propyl, n-, i-, s-, t-butyl, -CH 2 CH 2 OH, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylthiomethyl, methylthioethyl , Ethylthiomethyl, ethylthioethyl, methoxymethyl, methoxyethyl, Ethoxymethyl, ethoxyethyl, trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, difluorochlonvethyl, fluorodichloromethyl, pectafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 3 , -CF (CFj) 2 , -CH (CF 3
  • R 10 very particularly preferably represents methyl, trifluoromethyl or difluoromethyl
  • R 11 is very particularly preferably hydrogen, ethyl, n-propyl, n-butyl, -CH 2 CH 2 OH, cyclopropyl, methylthiomethyl, methoxymethyl, ethoxymethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -CH (CF 3 ) 2 , trifluoromethylthiomethyl,
  • R 10 very particularly preferably represents n-propyl, n-, t-butyl, pentafluoroethyl, -CH 2 CF 3 ,
  • anz is particularly preferably hydrogen, methyl, ethyl, n-propyl, n-butyl,
  • -CH 2 CH 2 OH cyclopropyl, methylthiomethyl, methoxymethyl, ethoxymethyl, trifluoromethyl, difluoromethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 J 2 , -CH (CF 3 ) 2 , trifluoromethylthiomethyl, -CH 2 SCH 2 CF 3 , -CH 2 SCF 2 CF 3 , trifluoromethoxymethyl, -CH 2 OCH 2 CF 3 , -CH 2 OCF 2 CF 3 , methylcarbonyl, n-propylcarbonyl , Methoxycarbonyl, methylthiocarbonyl, methoxymethylcarbonyl,
  • Ethoxymethylcarbonyl Trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, particularly preferably methyl, ethyl, methylthiomethyl, methoxymethyl, trifluoromethoxymethyl, methylcarbonyl.
  • m is preferably 1, where R 12 is then particularly preferably in the 4'-position.
  • m is preferably 2, where the radicals R 12 are particularly preferably in the 3 ', 4'- 5 2', 4 'or 3', 5 'position.
  • m is preferably 3, where the radicals R 12 are particularly preferably in 2 ', 4', 6 '
  • R 12 is preferably fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, n- or i-propylthio, cyclopropyl,
  • Trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio or trifluoromethylthio, -CH 2 Si (CH 3 ) 3 or -Si (CH 3 ) 3 , or for -C (Q.sub.1) ) NQ 2 , in which
  • Q 1 is hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl and Q 2 is hydroxy, methoxy, ethoxy, propoxy or isopropoxy.
  • R 13 preferably represents Ci-C4 alkyl or Ci-C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or Broinatomen.
  • R 13 is particularly preferably methyl, ethyl, n-, iso-propyl, n-, i-, s-, t-butyl, trifluoromethyl-CH 2 CF 3 , -C 2 F 5 or trichloromethyl.
  • R 13 very particularly preferably represents methyl, trifluoromethyl, -CH 2 CF 3 or -C 2 F 5 .
  • n is preferably 1. n is also preferably 2. n is particularly preferably 2.
  • R 14 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or
  • R 14 is very particularly preferably hydrogen or methyl.
  • R 15 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or
  • QR 16 R 15 is very particularly preferably hydrogen or methyl.
  • R 14 and R 15 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 mono- 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 14 and R 15 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 .
  • X is preferably O (oxygen). X is also preferably S (sulfur).
  • R 16 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 18 R 19 .
  • R l ⁇ is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, methoxy,
  • R 16 stehl very particularly preferably for hydrogen, methyl, ethyl, methoxy, ethoxy or
  • R 17 is preferably C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C -alkoxy-C 1 -C 6 -alkyl or QC 3 -
  • R 17 stands. particularly preferred for methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxy-methy l methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or Ethyltbioethyl, where the three radicals R 17 may be the same or different.
  • R 17 radicals are very particularly preferably methyl, methoxy, methoxymethyl or methylthiomethyl, where the three radicals R 17 may each be identical or different.
  • R 17 is particularly preferably methyl.
  • R 18 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • R 18 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl.
  • R 18 is very particularly preferably hydrogen or methyl.
  • R 19 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
  • R 19 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl.
  • R 19 is very particularly preferably hydrogen or methyl.
  • R 18 and R 19 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 or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl Heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen,
  • R 18 and R 19 also together with the nitrogen atom to which they are attached form bg; sondsrs preferably prefers one to four times, identically or differently
  • K 1 , M 3 R 8 A , R 9 , R 10 , R ⁇ , R 12 and m have the meanings given above.
  • R 8'A is then preferably chlorine or methyl.
  • R 8'A is then preferably chlorine or methyl.
  • R 8'A is then preferably chlorine or methyl.
  • compounds of the formula (Ic) in which m is 1 and R 12 is in 4'-position.
  • R 8'A is then preferably chlorine or methyl.
  • R 8 A is then preferably chlorine or methyl.
  • R 8 A is particularly preferred are compounds of the formula (Ie) in which m is 1 and R 12 is in the 4'-position.
  • Preference is likewise given to compounds of the formula (I) in which R 1 is hydrogen. Preference is furthermore given to compounds of the formula (I) in which m is 1 and R 12 is in the 4'-position.
  • R ⁇ is ethyl, n-propyl, n-eutyl, -CH 2 CH 2 OH, cyclopropyl, methylthiomethyl, methoxymethyl, ethoxymethyl, CH 2 CF 3 , CH 2 CF 2 CF 3 , trifluoromethylthiomethyl, -CH 2 SCH 2 CF 3 , -CH 2 SCF 2 CF 3 , trifluoromethoxymethyl, -CH 2 OCH 2 CF 3 , -CH 2 OCF 2 CF 3 , Methylcarbonyl, n-propylcarbonyl, methoxycarbonyl, methylthiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, trifluoromethylcarbcnyl, trifluoromethoxycarbonyl or trifluoromethylthiocarbonyl.
  • R ⁇ is ethyl, cyclopropyl, methylthiomethyl, methoxymethyl, trifluoromethoxymethyl or methylcarbonyl.
  • R 10 is ethyl, n-, isopropyl, n-, i-, s-, t-butyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 or -CH (CFs) 2 .
  • R 10 is n-propyl, n-, t-butyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 or -CH (CFB) 2 is absent.
  • the carboxylic acid halogierides required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (II).
  • R 9, R 10 and R 11 are preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have already as preferred in connection with the description of the substances according to the invention of the formula (I), especially preferred, etc. were given for these radicals.
  • 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 1-290662 and US 5,093,347).
  • the triedh n for carrying out the process (a) required as starting materials amines are generally defined by the formula (III).
  • R 1, M, R and m are 12 preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have already as preferred in connection with the description of the substances of formula (I) according to the invention, particularly preferably, etc., are given for these radicals or this index.
  • the amines of the formula (III) are known and / or can be prepared by known processes (cf., for example, EP-A 0 545 099, WO 03/070705).
  • the pyrazolylcarboxamides required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (Ia).
  • M, R 9 , R 10 , R 11 , R 12 and m have preferably, more preferably, very particularly preferably or in particular preferably those meanings which have already been mentioned in connection with the description of the compounds according to the invention of the formula (I) as preferred, particularly preferred, etc. for these radicals or this index.
  • the compounds of the formula (I-a) are compounds according to the invention and can be prepared by process (a) h.
  • R 1 B is preferably, more preferably, very particularly preferably or in particular preferred for those meanings which have already been indicated above for the radical R 1 as being preferred, particularly preferred etc., where R 1 "3 never is hydrogen, Hal is chlorine, bromine or iodine.
  • 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-methylfo ⁇ anilide, N-methylpyrrolidone or hexamethylphosphoric triamide;
  • H erzu preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholate, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide , Sodium hydroxide, KEdiurnhydroxid, sodium acetate, Natriumcarbo ⁇ at, Kaliumcarbo ⁇ at, potassium bicarbonate, Nalriumhydrogencarbonat or ammonium carbonate, and tertiary amines, such as trimethylamine, triethylamine, Tributylartiin, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine , N-methylmorpholine
  • the process (a) according to the invention is optionally carried out in the presence of a suitable coupling reagent (when X 5 is hydroxy).
  • a suitable coupling reagent when X 5 is hydroxy.
  • all common carbonyl activators come into question. These preferably include N- [3- (dimethylamino) propyl] -N'-ethyl-carbodiirnide hydrochloride, N, N'-di-sec-butyl-carbodiimide, N, N'-dicyclohexylcarbodiimide, N, N'-diisopropylcarbodiimide , 1- (3- (p) methylammo) propyl) -3-ethyl-aryldiimide methiodide, 2-bromo-3-ethyl-4-methylthiazolorum tetrafhioroborate, N, N-bis [2-oxo-3 -oxazolidinyl] phosphorodia
  • reaction temperatures can be varied in carrying out the process (a) according to the invention in a wider 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.
  • Suitable diluents for carrying out process (b) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylcl or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorothan or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethy oxyethane, 1,2-diethoxyethane or anisole or amides, such as N
  • the process (b) according to the invention is carried out in the presence of a base.
  • a base any customary inorganic or organic bases are suitable. These include, preferably, alkaline earth metal dl or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, e.g.
  • DABCO diazabicyclooctane
  • DBN diazabicyclcnone
  • DBU Diaz
  • the Reaktioristemperaturen can be varied in carrying out the process (b) according to the invention in a large range.
  • 0 C preferably at temperatures from O to 150 0 C at temperatures of from 2O 0 C and 11O 0 C.
  • the erfinduigsdorfen substances have a strong microbicidal activity and can be used for controlling unwanted microorganisms such as fungi and bacteria in crop protection and in the protection of materials.
  • Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomvcetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • diseases caused by pathogens of powdery mildew such as Blumeria species, such as Blumeria graminis
  • Podosphaera species such as Podosphaera leucotricha
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Uncinula ars such as Uncinula necator
  • Gymnosporangium species such as Gymnosporangium sabinae
  • Hemileia Arcen such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia arlen 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;
  • Phytophthori species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Pythium arlen such as Pythium ultimum
  • Alternaria species such as Alternaria solani;
  • Cercospora species such as Cercospora beticola
  • Cladosporiutn species such as Cladosporium cucumerinum
  • Cochliobolus species such as Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium);
  • Colletotrichiim 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; Leptosphaieri species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea;
  • Mycosphaerdla 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; Rhynchospoiium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii; Typhula artiai, such as Typhila incamata; Venturia Arts, such as Venturia inaequalis;
  • Corticium species such as Corticium graminearum; Fusarium Aiten, such as Fusarium oxysporum;
  • Gaeumannoriyces species such as Gaeumannomyces graminis
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis or Tapesia yallundae;
  • Thielaviopsi species such as Thielaviopsis basicola;
  • Ears and itispens caused by e.g.
  • Alternaria species such as Alternaria spp .
  • Aspergillus such as Aspergillus flavus
  • Cladosporiuin species such as Cladosporium cladosporioides
  • Claviceps species such as Claviceps pu ⁇ urea
  • Fusarium Aiten such as Fusarium culmorum
  • Gibberella species such as Gibberella zeae
  • Monographella species such as Monographella nivalis
  • Sphacel ⁇ theoa species such as Sphacelotheca reiliana
  • Tilletia species such as Tilletia caries
  • Urocystis species such as Urocystis occulta
  • Ustilago arlen such as Ustilago nuda
  • Fruit rot animal caused by eg Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea;
  • Penicilli species such as Penicillium expansum and Penicillium purpurogenum
  • Sclerotinia species such as Sclerotinia sclerotioram
  • Verticilium species such as Verticilium alboatrum
  • 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; Hehninthos]
  • Helminthosporiurn solani a species of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani; Hehninthos]
  • Helminthosporiurn solani a species of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani; Hehninthos]
  • Helminthosporiurn solani Helminthosporiurn 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 are known to be controlled by soy beans: fungal diseases on leaves, stems, pods and seeds caused, for example, by Alternaria leaf spot (Alternaria spec. Atrans temiissima), Anthracnose (Colletotrichum gloeosporoidus dematium var.
  • Fungus diseases on roots and stalk bases 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 vasinfeeta), Pod and Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var.
  • Phytophthora Red (Phytophthora megasperma), Brown Star Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, rythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Star Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Star Decay (Sclerotinia sclerotiorurr), 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 more suitable for mobilizing plant-own defenses against infestation by unwanted microorganisms.
  • peat-enhancing substances are substances which are capable of stimulating the defense system of plants in such a way that the treated plants, upon subsequent inoculation with unwanted microorganisms, exhibit extensive resistance to these microorganisms.
  • Unwanted microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to plants within a certain period of time after treatment to protect against infestation by said pathogens.
  • the period within which protection is 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 compatibility of the active ingredients in the concentrations necessary for the control of plant diseases allows a 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 combating cereal cranial diseases, such as, for example, against Puccinia species and diseases in the wine, fruit and vegetable growing, such. against B ⁇ trytis, 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 can 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 employed as intermediates and precursors for the synthesis of further active ingredients.
  • 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 means of bio-detec- tological and genetic engineering methods or combinations of these methods, including transgenic plants and including plant varieties that can be protected or not protected by plant variety rights.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies *, fruits and seeds, and roots, tubers and rhizomes ,
  • the plant parts also include emmentals as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the erfinduigsdorfe treatment of plants and parts of plants with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual For example, by immersion, spraying, evaporation, nebulization, scattering, brushing and Verniehrungsmaterial, especially in seeds, by one or more layers wrapping.
  • the substances according to the invention can be used for the protection of industrial materials against infestation and destruction by undesired microorganisms.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • technical materials which are to be protected from 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 may be attacked or decomposed by microorganisms .
  • 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.
  • adhesives, glues, papers and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids are preferably mentioned, with particular preference wood.
  • microorganisms which can cause degradation or alteration of the technical materials, mention may be made, for example, of bacteria, fungi, yeasts, algae and slime organisms.
  • 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.
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum
  • Coniophora like Coniophora puetana,
  • 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, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV -KaIt- and Wa ⁇ nnebel formulations.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders that is to say liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-forming agents.
  • water e.g. also organic solvents can be used as Hüfsuccin.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenec; or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenec
  • methylene chloride aliphatic hydrocarbons
  • liquefied gaseous diluents or carriers liquids which are gaseous at normal temperature and under normal pressure, i. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: e.g. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: e.g.
  • Emulgicr and / or foam-forming agents are suitable: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylarylpolyglycolether, alkyl sulfonates, alkyl sulfates, Arylsulf ⁇ nate and protein hydrolysates.
  • Suitable dispersants are: e.g. Lignin Sulfii leach and MethylceUulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids may be used in the formulations.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments such as 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 can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance.
  • synergistic effects i. E. the effectiveness of the mixture isl greater than the effectiveness of the individual components.
  • Fungicides are suitable as mixed partners: Fungicides:
  • inhibitor of nucleic acid synthesis e.g. Benalaxyl, Benalaxyl-M, Bupirimate, Clozylacone, Dimethirimcl, Ethirimol, Furalaxyl, Hymexazole, Mefenoxam, Metalaxyl, Metalaxyl-M, Ofurace, Oxadixyl, Oxolinic acid;
  • inhibitors of mitosis and cell division e.g. Benomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole ;, pencycuron, thiabendazole, thiophanate-methyl, zoxamide;
  • 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; 3.3) inhibitors on the complex in the respiratory chain: e.g.
  • decoupler e.g. Dinocap, fluazinam, meptyldinocap;
  • Inhibitor of ATP production e.g. Fentin acetate, Fe ⁇ tin chloride, Fe ⁇ tin hydroxide, Silthiofäm; 6) Inhibitors of amino acid and protein biosynthesis: e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;
  • Signal transduction inhibitor e.g. Fenpiclonil, fhidioxonil, quinoxyfen;
  • inhibitors of lipid and membrane synthesis eg biphenyl, chlozolinates, edifenphos, iodocarb, Iprobenfos, iprodione, isoprothiolanes, procymidones, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl, vinclozolin; 9)
  • Inhibitors of ergosterol biosynthesis eg aldimoiph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexarnide, fenpropidin, fenpropimorph, fluqui
  • Inhibitors of melanin biosynthesis e.g. Carpropamide, diclocymet, fenoxanil, phthalides, pyroquilon, tricyclazole;
  • Resist2inductors e.g. Acibenzolar-S-methyl, Probenazoles, Tiadinil
  • Compounds with MuMsite activity e.g. Bordeaux Mixture, Captafol, Captan, Chlorothalonil, Copper naphthenate, Copper oxide, Copper oxycoboride, Copper Preparations such as e.g.
  • Carbanates eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carboofuran, carbosulfen, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, Fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamates, trimethacarb, XMC, xylylcarb) 1.2 Organophosphat
  • Pyrethroids eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, biotethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, cbJovaporthrin, cis-cypermethrin , Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthriB (lR-isomer), esfenvalerate, etofenprox , Fenfluth
  • Oxadiazines e.g., indoxacarb
  • Acetylcholine receptor agonists / antagonists 3.1 Chloroacotinyls / neonicotinoids (e.g., aceta ⁇ ripride, clolhianidine, dinotefuran, imidacloprid, nitropyiamine, nithiazines, tbiacloprid, thiamethoxam) 3.2 Nicotine, Bensultap, Cartap
  • Organochlorines e.g., calcium chloride, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
  • Fiprol e.g., acetoprole, etbiprole, fipronil, vaniliprole
  • Mectins e.g., abamectin, avermectin, emamectin, emamectin-beta-azate, ivermectin, milbemectin, milbemycin
  • diacylhydrazines eg chromafenozides, halofenozides, methoxyfenozides, tebufenozides
  • inhibitors of chitin biosynthesis eg chromafenozides, halofenozides, methoxyfenozides, tebufenozides
  • Benzoylureas for example, bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
  • Buprofezin 9.3 Cyiomarins 10. Inhibitors of oxidative phosphorylation, ATP disruptors
  • MEll's e.g., Fenazaquin, Fenpyroximate, Pyrimidifeo, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Inhibitors of Fat Synthesis 16.1 Tetroic 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-eri-4-yl ethylcarbinate (aka: Carbonic acid, 3- (2,5-dimethylphiyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl, ethyl ester, CAS Reg.
  • Octopaminergic agonists e.g., Amitraz
  • mite growth inhibitors eg clofentezine, etoxazole, hexythiazox
  • amidcflumet benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, clordordimeform, chlorobenzenate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimines, Flufenerim, Flutenzin, Gossyplure, Hydramethylone, Japoidlure, Metoxadiaz ⁇ ne, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, the compound 3-Meih
  • the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad antiinykotiscb.es 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 active substances 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 powders, dusts and granules.
  • the application is carried out in a customary manner, for example by casting, spraying, spraying, scattering, dusting, foaming, spreading, etc. It is also possible to apply the active ingredients according to the ultra-low volume method or the active ingredient preparation or the active ingredient inject yourself into the ground. It can also treat the seeds of the plants.
  • the application rates can be varied within a relatively wide range, depending on the application.
  • Plant parts are the application rates of active ingredient generally between 0.1 and 0.1
  • Effluent to active ingredient 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.
  • plants and their parts can be treated.
  • wild or by conventional biological Bregenzmethc iden such as crossing or protoplast fusion obtained plant species and plant varieties and their parts are treated.
  • transgenic plants and plant species which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above
  • 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 Enhancement of the effect of the substances and agents which can be used according to the invention, better plant growth, further developed Root system, higher resistance of the plant species or plant variety, increased growth of the shoots, higher plant vitality, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity, increased Bliih educa, easier harvesting, acceleration of maturity, 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 shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.
  • superadditive superadditive
  • the preferred transgenic (genetically engineered) plants or plant species 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 ( 5 "traits”.) Examples of such properties are better plant growth. increased to 1 tolerance is to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and / or a higher nutritional value of the harvested products, better storage stability and / or Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or Vir and increased tolerance of the plants to certain herbicidal active substances.
  • transgenic plants are the important crops, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apple, pear, citrus and grapes) mentioned, with corn, soybean, potato , Cotton, tobacco and oilseed rape.
  • cereals wheat, rice
  • corn, soybeans, potatoes cotton
  • tobacco, rapeseed and fruit plants with the fruits apple, pear, citrus and grapes mentioned
  • 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 (cf.
  • Bt plants are produced in the plants (hereinafter "Bt plants”. Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic activated resistance (SAR), systemin, phytoalexins, elicitors, and resistance genes and correspondingly expressed proteins and toxins. ) are further particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (eg "PAT" gene).
  • SAR systemic activated resistance
  • PAT phosphinothricin
  • genes conferring the desired properties can also occur in combination with one another in the transgenic plants, examples being "Bt plants” Maize varieties, cotton varieties, soybean varieties and potato varieties mentioned under the trade names YIELD GARD® (eg maize, cotton, soy), KnockOut® (eg maize), StarLink® (eg maize), BoIl gard® (cotton), Nucoton® (cotton ) and NewLeaf® (potato).
  • YIELD GARD® eg maize, cotton, soy
  • KnockOut® eg maize
  • StarLink® eg maize
  • BoIl gard® cotton
  • Nucoton® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, eg rapeseed), IMI® ( Tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinothricin, eg rapeseed
  • IMI® Tolerance to imidazolinone
  • STS® tolerance to sulfonylureas eg corn.
  • Clearfield® marketed varieties eg corn
  • the plants listed can be treated particularly advantageously erf ⁇ ndungshack with the compounds of the general formula (I) or the drug 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 adding a solution consisting of 384.2 mg (1.5 mmol) of 3 ', 4'-dichloro-5-fluorobiphenyl-2-amine and 0.27 ml (1.95 mmol) of triethylamine in 9 ml of dichloromethane , After stirring for 16 hours at room temperature, the reaction mixture is poured onto 10 ml of water, the organic phase 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 2 between two consecutive alkanones).
  • the lambla-max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chroniatographic signals. Applications do not apply
  • Emulsifier 1 part by weight of alkylaiyl polyglycol ether
  • 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.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the Graphai are then placed in a greenhouse at a temperature of about 20 0 C and relative humidity of about 80%.
  • Emulsifier 1 part by weight of alkylaiyl polyglycol ether
  • active compound 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.
  • Botrytis test (cucumber) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

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Abstract

The invention relates to novel pyrazolyl carboxamides of formula (I), wherein R<SUP>1</SUP>, M, R<SUP>9</SUP>, R<SUP>10</SUP>, R<SUP>11</SUP>, R<SUP>12</SUP> and m have the meanings cited in the description. The invention also relates to several methods for producing said substances and to the use thereof for controlling unwanted micro-organisms, and to novel intermediate products and to the production thereof.

Description

Pyrazolylc arboxamidePyrazolylc arboxamide
Die vorliegende Erfindung betrifft neue Pyrazolylcarboxamide, mehrere Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von schädlichen Mikroorganismen im Pflanzenschutz und Materialschutz.The present invention relates to novel pyrazolylcarboxamides, to a plurality of processes for their preparation and to their use for controlling harmful microorganisms in crop protection and material protection.
Es ist bereits bekannt geworden, dass zahlreiche Pyrazolylcarboxamide fungizide Eigenschaften besitzen (vgl. z.B. WO 03/070705, WO 02/059086, WO 01/42223, EP-A 0 737 682, EP-A 0 589 301, EP-A 0 545 099 und JP-A 4-316559). So sind beispielsweise die Verbindungen N-(4'- Fluorbiphenyl-2-yl)-l-methyl-3-(pentafluorethyl)-lH-pyrazol-4-carboxamid (aus WO 01/42223) und N-Acetyl-N-(4'-fluorbiphenyl-2-yl)-l-(methoxymethyl)-3-(trifluormethyl)-lH-pyrazol-4- carboxamid (aus WO 02/059086) bekannt geworden. Die Wirksamkeit der im Stand der Technik beschriebenen Verbindungen ist gut, lässt aber bei niedrigen Aufwandmengen in manchen Fällen zu wünschen übrig.It has already been disclosed that numerous pyrazolylcarboxamides have fungicidal properties (cf., for example, WO 03/070705, WO 02/059086, WO 01/42223, EP-A 0 737 682, EP-A 0 589 301, EP-A 0 545 099 and JP-A 4-316559). Thus, for example, the compounds N- (4'-fluorobiphenyl-2-yl) -1-methyl-3- (pentafluoroethyl) -1H-pyrazole-4-carboxamide (from WO 01/42223) and N-acetyl-N- ( 4'-fluorobiphenyl-2-yl) -1- (methoxymethyl) -3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (from WO 02/059086). The effectiveness of the compounds described in the prior art is good, but leaves at low application rates in some cases to be desired.
Es wurden nun neue Pyrazolylcarboxamide der Formel (I)There have now been new pyrazolylcarboxamides of the formula (I)
gefunden, in welcher found in which
R1 flr Wasserstoff, Ci-Cg-Alkyl, Ci-C6-Alkylsulfinyl, Ci-Ce-Alkylsulfonyl, C1-C4-AIkOXy-C1- Cralkyl, C3-C8-Cycloalkyl; Ci-C6-Halogenalkyl, d-C^Halogenalkylthio, CrC4-Halogenal- kylsulfinyl, C1-C4-Halogenalkylsulfonyl, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-HaIo- gcncycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Foπnyl, Formyl-Q- C3-alkyl, (Ci-C3-Alkyl)carbonyl-Ci-C3-alkyl, (CrCs-AlkoxyJcarbonyl-Q-Gralkyl; HaIo- gιai-(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 1 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -cralkyl, C 3 -C 8 -cycloalkyl; Ci-C 6 haloalkyl, dC ^ haloalkylthio, C r C 4 -Halogenal- kylsulfinyl, C 1 -C 4 -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; Phenyl, formyl-Q-C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (C 1 -C 5 -alkoxy-carbonyl-Q-gralkyl; haloalkyl- (C 1 -C 3 -alkyl) carbonyl -C 1 -C 3 -alkyl, halogeno (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms;
(Ci-C8-Alkyl)carbonyl, (CrC8-Alkoxy)carbonyl, (C1-C4-AIkOXy- C i-C4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)carbonyl, (C3-C8- Cycloalkyl)carbonyl; (Ci-Ce-Halogenalkyljcarbonyl, (C!-C6-Halogenalkoxy)carbonyl, (C1- C!6-Halogenalkylthio)carbonyl, (Halogen-Ci-C4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C6-HaIo- genalkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)carbonyl, (C3-C8-Halogencycloalkyl)- caibonyl 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,(Ci-C 8 -alkyl) carbonyl, (C r C 8 alkoxy) carbonyl, (C 1 -C 4 -AIkOXy- C iC 4 alkyl) carbonyl, (C 3 -C 6 alkenyloxy) carbonyl, (C 3 -C 6 alkynyloxy) carbonyl, (C 3 -C 8 - cycloalkyl) carbonyl; (Ci-Ce Halogenalkyljcarbonyl, (C-C6 haloalkoxy) carbonyl, (C 1 -! C 6 haloalkylthio) carbonyl, (halo-Ci-C4-alkoxy-Ci-C4-alkyl) carbonyl, (C 3 -C 6 -haloalkenyloxy) carbonyl, (C 3 -C 6 -haloalkynyloxy) carbonyl, (C 3 -C 8 -halocycloalkyl) - caibonyl 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 ,
R' A fiii Wasserstoff, C,-C6-Alkyl, d-Cβ-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-CR ' A fiii hydrogen, C, -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C
Cycloalkyl, (Ci-C4-Alkoxy)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)car- bo iyl oder Cyano steht,Cycloalkyl, (C 1 -C 4 -alkoxy) carbonyl, (C 3 -C 6 -alkenyloxy) carbonyl, (C 3 -C 6 -alkynyloxy) carboyl or cyano,
R2 füi Wasserstoff, C1-C8-AIlCyI, Ci-C8-Alkoxy, Ci-C4-Alkoxy-CrC4-alkyl, C3-C8-Cycloalkyl;R 2 Fuei hydrogen, C 1 -C 8 -alkyl, Ci-C 8 alkoxy, Ci-C 4 -alkoxy-C r C 4 alkyl, C 3 -C 8 cycloalkyl;
Ci-Cβ-Halogenalkyl, Ci-C5-Halogenalkoxy, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-HaIo- geicycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht,Ci-Cβ-haloalkyl, Ci-C5 haloalkoxy, halogen-Ci-C4-alkoxy-Ci-C 4 alkyl, C 3 -C 8 -HaIo- geicycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms stands,
R3 und R4 unabhängig voneinander jeweils für Wasserstoff, Ci-Cs-Alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, C3-C8-Cycloalkyl; Q-Cs-Halogenalkyl, Halogen-Ci-C4-alkoxy-Ci-C4-alkyl, C3-C8-Halogen- cydoalkyl 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; Q-Cs-haloalkyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -halo-cydoalkyl 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- c>clus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann, R5 und R6 unabhängig voneinander für Wasserstoff, Q-Cg-Alkyl, C3-C8-Cycloalkyl; Ci-C8-Halogenalkyl,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 heterocyclic group > clus may contain 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulfur or NR 7 , R 5 and R 6 independently of one another represent hydrogen, Q-Cg-alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 8 -haloalkyl,
C j-Cg-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R5 und R( außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenen- falls 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 NR enthalten kann,C j-Cg-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms, R 5 and R ( also together with the nitrogen atom to which they are attached, optionally one or more times, the same or different form a halogenated or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, where the heterocycle may contain 1 or 2 further, nonadjacent heteroatoms from the series oxygen, sulfur or NR,
R7 für Wasserstoff oder Ci-C6-Alkyl steht, M für einen einfach durch R8 substituierten Phenyl-Ring oder einen einfach durch R8'A substituierten Thiophen-Ring steht,R 7 is hydrogen or C 1 -C 6 -alkyl, M is a phenyl ring which is monosubstituted by R 8 or a thiophene ring which is monosubstituted by R 8'A ,
R8 für Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluormethyl steht, R8 A f ir Wasserstoff, Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluormethyl steht, R9 f ir Wasserstoff, Fluor oder Chlor steht, a) R10 für Ci-C6-Alkyl oder Ci-C6-Halogenalkyl mit 1 bis 13 Halogenatomen steht, undR 8 is fluorine, chlorine, methyl, iso-propyl, methylthio or trifluoromethyl, R 8 A f is hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl, R 9 is hydrogen, fluorine or chlorine a) R 10 is Ci-C 6 alkyl or Ci-C is 6 haloalkyl having 1 to 13 halogen atoms, and
R11 für Wasserstoff, C2-C6-AIlCyI, Hydroxy-GKValkyl, Ca-Cβ-Cycloalkyl, CrC4-Alkylthio-R 11 represents hydrogen, C 2 -C 6 -alkyl, hydroxy-GKValkyl, Ca-Cβ cycloalkyl, C r C 4 alkylthio
Ci-C4-alkyl, CrC4-Alkoxy-Ci-C4-alkyl, Q-C4-Halogenalkyl, Ci-C4-Halogenalkyllhio-Ci-C 4 alkyl, C r C 4 alkoxy-Ci-C4-alkyl, QC 4 haloalkyl, Ci-C4 -Halogenalkyllhio-
Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl mit jeweils 1 bis 9 Halogenatomen, (Cr Cs-Alkyl)carbonyl, (Ci-Cs-Alkoxy)carbonyl, (CrC8-Alkylthio)carbonyl, (Ci-C4-Alkoxy- Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl having in each case 1 to 9 halogen atoms, (Cr Cs-alkyl) carbonyl, (Ci-Cs alkoxy) carbonyl, (C r C 8 - Alkylthio) carbonyl, (C 1 -C 4 -alkoxy)
CrC4-alkyl)carbonyl; (Ci-Q-Halogena1kyl)carbonyl, (Ci-Cβ-Halogenalkoxy)carbonyl, (Ci-C6-Halogenalkylthio)carbonyl, (Halogen-Ci-C4-alkoxy-Ci-C4-alkyl)carbonyl mit jeweils 1 bis 9 Halogenatomen steht, od;r b) R10 für C2-C6-Alkyl oder C2-C6-Halogena]kyl mit 1 bis 13 Halogenatomen steht, undC 1 -C 4 -alkyl) carbonyl; (Ci-Q-Halogena1kyl) carbonyl, (Ci-C β haloalkoxy) carbonyl, (Ci-C6-haloalkylthio) carbonyl, (halo-Ci-C 4 alkoxy-Ci-C 4 -alkyl) carbonyl having in each case 1 to 9 halogen atoms, or; rb) R 10 is C 2 -C 6 -alkyl or C 2 -C 6 haloalkyl having 1 to 13 halogen atoms, and
R1 ' für Wasserstoff; CrC6-A]kyl, Hydroxy-Q-Q-alkyl, Cs-Ce-Cycloalkyl, CrC4-Alkylthio- CrC4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Halogenalkyl, Ci-C4-Halogenalkylthio- Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl mit jeweils 1 bis 9 Halogenatomen, (d- C8-Alkyl)carbonyl, (Ci-C8-Alkoxy)carbonyl, (Ci-C8-Alkylthio)carbonyl, (CrC4-Alkoxy- Ci-C4-alkyl)carbonyl; (Ci-C6-Halogenalkyl)carbonyl, (Ci-C6-Halogenalkoxy)carbonyl,R 1 'is hydrogen; C r C 6 -A] kyl, hydroxy-QQ-alkyl, Cs-Ce-cycloalkyl, C r C 4 alkylthio -C 4 alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 haloalkyl, Ci-C 4 -haloalkylthio Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl having in each case 1 to 9 halogen atoms, (d- C8-alkyl) carbonyl, (Ci- C 8 alkoxy) carbonyl, (Ci-C 8 alkylthio) carbonyl, (C r C4 alkoxy Ci-C4 alkyl) carbonyl; (C 1 -C 6 -haloalkyl) carbonyl, (C 1 -C 6 -haloalkoxy) carbonyl,
(Ci-C6-Halogenalkylthio)carbonyl, (Halogen-Ci-C4-alkoxy-C]-C4-alkyl)carbonyl mit jeweils 1 bis 9 Halogenatomen steht, m für 1, 2, 3, 4 oder 5 steht,(C 1 -C 6 -haloalkylthio) carbonyl, (halogeno-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl having in each case 1 to 9 halogen atoms, m is 1, 2, 3, 4 or 5,
R12 für Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxy, Carbamoyl, Thiocarb- arαoyl, Ci-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, CrC4-Alkoxy, C,-C4-Alkylthio, C,-R 12 represents halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, Thiocarb- arαoyl, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C r C 4 Alkoxy, C, -C 4 alkylthio, C, -
C rAlkylsulfinyl, CrC4-Alkylsulfonyl, C3-C6-Cycloalkyl, oder für Ci-C4-Halogenalkyl, C,-C rAlkylsulfinyl, C r C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl, or Ci-C 4 haloalkyl, C, -
C t-Halogenalkoxy, Ci-C4-Halogenalkylthio, Ci-C4-HalogenalkylsιJrlnyl oder Ci-C4-HaIo- gemalkylsulfonyl mit jeweils 1 bis 5 Halogenatomen, -(CH2)Si(CH3)3 oder -Si(CH3)3 steht, oder für -C(Q!)=N-Q2 steht, worin Q1 für Wasserstoff, Hydroxy, Ci-C4-Alkyl, Ci-C4-Halogenalkyl 1 bis 9 Halogenatomen oder C3-C6-Cycloalkyl steht,C t haloalkoxy, Ci-C4-haloalkylthio, Ci-C4 or Ci-C4 -HalogenalkylsιJrlnyl -HaIo- gemalkylsulfonyl each having 1 to 5 halogen atoms, - (CH 2) Si (CH 3) 3 or -Si (CH 3) 3; or) = NQ 2 is -C (Q, wherein Q 1 is hydrogen, hydroxy, Ci-C4-alkyl, Ci-C4-haloalkyl 1 to 9 halogen atoms, or C 3 -C 6! - Is cycloalkyl,
C32 für Hydroxy, Amino, Methylamino, Phenyl, Benzyl oder für jeweils gegebenenfalls durch Halogen, Cyano, Hydroxy, Ci-C4-Alkoxy, Ci-C4-Alkylthio, CrC4-Alkyl- amino, Di(Ci-C4-alkyl)amino oder Phenyl substituiertes Ci-C4-Alkyl oder Ci-C4- Alkoxy, oder für C2-C4-Alkenyloxy oder C2-C4-Alkinyloxy steht, oder für -SOnR13, -SO2NR14R15, -C(=X)R16, -Si(R17)3, -NR14R15, -CH2-NR14R15 steht, R13 für Ci-Cβ-Alkyl oder Ci-C6-Halogenalkyl mit 1 bis 13 Halogenatomen steht, n f ir 1 oder 2 steht,C3 2 is hydroxy, amino, methylamino, phenyl, benzyl or represents in each case optionally halogen-, cyano, hydroxy, Ci-C 4 alkoxy, Ci-C 4 alkylthio, C r C 4 alkyl amino, di (Ci- C 4 alkyl) amino or phenyl-substituted Ci-C 4 alkyl or Ci-C 4 - alkoxy, or C 2 -C 4 alkenyloxy or C 2 -C 4 alkynyloxy, or -SO n R 13, -SO 2 NR 14 R 15 , -C (= X) R 16 , -Si (R 17 ) 3 , -NR 14 R 15 , -CH 2 -NR 14 R 15 , R 13 is C 1 -C 6 -alkyl or Ci-C 6 haloalkyl having 1 to 13 halogen atoms, nf ir is 1 or 2,
R14 f ir Wasserstoff, Ci-C4-Alkyl oder -C(=X)R16 steht, R15 f ir Wasserstoff, Ci-C4-Alkyl oder -C(=X)R16 steht,R 14 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 16 , R 15 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 16 ,
R14 und R15 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebe- renfalls 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 14 and R 15 together with the nitrogen atom to which they are attached additionally form an optionally mono- or polysubstituted by identical or different halogen or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, where the hetero cyclus may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 7 ,
X lür O (Sauerstoff) oder S (Schwefel) steht, R16 für Wasserstoff, C1-C4-AIlCyI, Ci-C4-AIkOXy oder -NR18R'* steht,X is O (oxygen) or S (sulfur), R 16 is hydrogen, C 1 -C 4 -alkyl, Ci-C 4 -alkoxy or -NR 18 R * is'
Rπ für Wasserstoff, Ci-C8-Alkyl, CrC8-Alkoxy, Ci-C4-Alkoxy-Ci-C4-alkyl, Ci-C4-Alkylthio- Cr C4-alkyl oder Ci-C6-Halogenalkyl steht, wobei die drei Reste R17 jeweils gleich oder vei schieden sein können, R18 Wiisserstoffoder C-CrAlkyl steht,R π represents hydrogen, Ci-C 8 alkyl, C r C 8 alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 alkylthio C r C 4 alkyl or C 6 -haloalkyl, where the three radicals R 17 may each be the same or different, R 18 is ether or C 1 -C 4 -alkyl,
R19 W;ιsserstoff oder d-C4-Alkyl steht,R 19 is hydrogen or C 1 -C 4 -alkyl,
R18 und R19 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebene) ifalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen bilden, wobei der Hetero- cyolus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel od≥r NR7 enthalten kann.R 18 and R 19 also together with the nitrogen atom to which they are attached form a given ifalls monosubstituted or polysubstituted by identical or different halogen or C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, where the hetero cyolus may contain 1 or 2 further non-adjacent heteroatoms selected from oxygen, sulfur or NR 7 .
Weiterhin wurde gefunden, dass man Pyrazolylcarboxamide der Formel (I) erhält, indem man (a) Qixbonsäurehalogenide der Formel (II)Furthermore, it has been found that pyrazolylcarboxamides of the formula (I) are obtained by reacting (a) quixonic acid halides of the formula (II)
in welcher in which
R'', R10 und R11 die oben angegebenen Bedeutungen haben,R ' ', R 10 and R 11 have the meanings given above,
X1 für Halogen oder Hydroxy steht, mit Aminen der Formel (III)X 1 is halogen or hydroxy, with amines of the formula (III)
in. welcher R1, M, R12 und m die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Kupplungsreagenzes, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder (b) Pyrazolylcarboxamide der Formel (I-a) in welcher M, R9, R10, R11, R12 und m die oben angegebenen Bedeutungen haben, mit Halogeniden der Formel (FV) in which R 1 , M, R 12 and m 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) pyrazolylcarboxamides of the formula (Ia) in which M, R 9 , R 10 , R 11 , R 12 and m have the meanings given above, with halides of the formula (IV)
R1-8— HaI (IV) in welcherR 1 - 8 - Hal (IV) in which
R1 B für Q-Q-Alkyl, C-Q-Alkylsulfinyl, Ci-Q-Alkylsulfonyl, d-C-Alkoxy-C^-al- kyl, C3-C8-Cycloalkyl; CrCβ-Halogenalkyl, d-C4-Halogenalkylthio, CrC4-Halo- 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, (CrC3-Alkoxy)- carbonyl-Ci-C3-alkyl; Halogen-(Ci-C3-alkyl)carbonyl-Ci-C3-aUcyl, Halogen-(CrC3- alkoxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen;R 1 B is QQ-alkyl, CQ-alkylsulfinyl, Ci-Q-alkylsulfonyl, dC-alkoxy-C ^ -alkyl, C 3 -C 8 -cycloalkyl; CrCβ haloalkyl, dC 4 haloalkylthio, C r C 4 -Halo- 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 3 alkyl, (Ci-C 3 alkyl) carbonyl-Ci-C 3 alkyl, (C r C 3 alkoxy) - carbonyl-Ci-C 3 alkyl; Halogen (Ci-C 3 -alkyl) carbonyl-Ci-C 3 -aUcyl, halogen (C r C 3 - alkoxy) carbonyl-Ci-C 3 -alkyl with in each case 1 to 13 fluorine, chlorine and / or bromine atoms;
(C,-C8-A]kyl)carbonyl, (C1-C8-Alkoxy)caτbonyl, (Ci-C8-Alkylthio)carbonyl5 (Ci-C4- Alkoxy-Ci-C4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-C6-Alkinyloxy)car- bonyl, (C3-C8-Cycloalkyl)carbonyl; (d-Cö-HalogenalkyOcarbonyl, (Ci-Q-Halogen- alkoxy)carbonyl, (Ci-C6-Halogenalkyhhio)carbonyl, (Halogen-Ci-C4-alkoxy-Ci-C4- alkyl)carbonyl, (C3-C6-Halogenalkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)car- bonyl, (C3-C8-Halogencycloalkyl)carbonyl mit jeweils I bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -CH2-C≡C-R1 A, -CH2-CH=CH-R1^, -CH=C=CH-R1 A,(C, -C 8 -A] alkyl) carbonyl, (C 1 -C 8 alkoxy) caτbonyl, (Ci-C 8 alkylthio) carbonyl 5 (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; (dC ö -HalogenalkyOcarbonyl, (Ci-Q-halo- alkoxy) carbonyl, (Ci-C 6 -Halogenalkyhhio) 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, R1 A, R2, R3, R4, R5 und R6 die oben angegebenen Bedeutungen haben, H;d für Chlor, Brom oder Iod steht, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt.-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 are as indicated above H, d is chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
Schließlich wurde gefunden, dass die neuen Pyrazolylcarboxamide der Formel (I) sehr gute mikrobizide Eigenschaften besitzen und zur Bekämpfung unerwünschter Mikroorganismen sowohl im Pflanzenschutz als auch im Materialschutz verwendbar sind.Finally, it has been found that the novel pyrazolylcarboxamides 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.
Die erfϊncungsgemäßen 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.If appropriate, the compounds according to the invention can be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, B. E- and Z-, threo- and erythro-, as well as 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 Pyrazolylcarboxamide sind durch die Formel (I) allgemein definiert. Bevorzugte Restedefinitionen der vorstehenden und nachfolgend genannten Formern sind im Folgenden angegeben. Diese Definitionen gelten für die Endprodukte der Formel (I) wie für alle Zwischenprodukte gleichermaßen.The pyrazolylcarboxamides according to the invention are generally defined by the formula (I). Preferred radical definitions of the above and below mentioned formers 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, CrC4-Alkylsulfinyl, Ci-C4-Alkylsu]fonyl, C1- Cs-.Ukoxy-Ci-Cs-alkyl, C3-C6-Cycloalkyl; Ci-C4-Halogenalkyl, CrC4-Halogenalkylthio, C1- C4-Halogenalkylsulfinyl, Ci-Q-Halogenalkylsulfonyl, Halogen-C)-C3-alkoxy-C]-C3-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Fortnyl-Ci-Cs-alkyl, (Ci-C3-Alkyl)carbonyl-CrC3-alkyl, (Ci-C3-Alkoxy)carbonyl-Ci-C3-al- kyl; Halogen^Ci-Cs-alkyOcarbonyl-CrCs-alkyl, Halogen-(CrC3-alkoxy)carbonyl-Ci-C3-al- kyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen;R 1 preferably represents hydrogen, Ci-C 6 alkyl, C r C 4 alkylsulfinyl, Ci-C 4 -Alkylsu] fonyl, C 1 - Cs-Ci-Cs-.Ukoxy-alkyl, C 3 -C 6 - cycloalkyl; Ci-C 4 haloalkyl, C r C 4 haloalkylthio, C 1 - C 4 haloalkylsulfinyl, Ci-Q-haloalkylsulfonyl, halo-C) -C 3 alkoxy-C] -C 3 alkyl, C 3 -C 8- halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, Ci-Cs-Fortnyl-alkyl, (Ci-C 3 alkyl) carbonyl-C r C 3 alkyl, (Ci-C 3 alkoxy) carbonyl-Ci-C 3 alkyl -AL-; Halogen ^ Ci-Cs-alkyOcarbonyl CRCS alkyl, halo (C r C 3 alkoxy) carbonyl-Ci-C3-alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms;
(Cr C6-A]kyl)carbonyl, (d-C4-Alkoxy)carbonyl, (Ci-C4-Alkylthio)carbonyl, (Ci-C3-Alkoxy- Ci-C3-alkyl)carbonyl, (C3-C4-Alkenyloxy)carbonyl, (C3-C4-Alkinyloxy)carbonyl, (C3-Ce- Cydoalkyl)carbonyl; (d-C4-Halogenalkyl)carbonyl, (Ci-C4-Halogenalkoxy)carbonyl, (C1- C4- rIalogenalkylthio)carbonyl, (Halogen-Ci-C3-alkoxy-Ci-C3-alkyl)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 A,(Cr C 6 -A] alkyl) carbonyl, (dC 4 alkoxy) carbonyl, (Ci-C 4 alkylthio) carbonyl, (Ci-C 3 alkoxy Ci-C 3 alkyl) carbonyl, (C 3 - C 4 alkenyloxy) carbonyl, (C 3 -C 4 alkynyloxy) carbonyl, (C 3 -CE cycloalkyl) carbonyl; (dC 4 -haloalkyl) carbonyl, (Ci-C 4 haloalkoxy) carbonyl, (C 1 - C 4 - rIalogenalkylthio) carbonyl, (halo-Ci-C 3 alkoxy-Ci-C 3 alkyl) carbonyl, (C 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 A ,
-CH2-CH=CH-R1^, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6.-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 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert -Butyl, Pentyl oder Hexyl, Methylsulfinyl, Ethyisulfinyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsurfinyl, Methylsubfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclo- prqjyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Trichloπnethyl, Trifluorethyl, Difluormethyl- thic, Difluorchlormethylthio, Trifluormethylthio, Trifluormethylsulfinyl, Trifluormethylsulfonyl, Triluormethoxymethyl; Formyl, -CH2-CHO, -(CH2VCHO, -CH2-CO-CH3, -CH2-CO-CH2CH3,R 1 is particularly preferably 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-butylsurfinyl, methylsubfonyl, ethylsulphonyl, n- or iso-propylsulphonyl, n-, iso-, sec- or tert-butylsulphonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifluoromethyl, trichloroethyl, trifluoroethyl, difluoromethylthic, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, triluoromethoxymethyl; Formyl, -CH 2 -CHO, - (CH 2 VCHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 ,
-CH2-CO-CH(CHa)2, -(CHz)2-CO-CH3, -(CH2J2-CO-CH2CH3, -(CH^-CO-CH^H^, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CHrCOzCH^H,),, -(CH2^-CO2CH3,-CH 2 -CO-CH (CHa) 2 , - (CH 2 ) 2 -CO-CH 3 , - (CH 2 J 2 -CO-CH 2 CH 3 , - (CH 2 -CO-CH 2 H 3 , - CH 2 -CO 2 CH 3 , -CH 2 -CO 2 CH 2 CH 3 , -CHrCOzCH ^ H,) ,, - (CH 2 ^ -CO 2 CH 3 ,
-(C Hz)2-CO2CH2CH3, -OCH2)I-CO2CH(CHi)2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CHj)2-CO-CH2CF33 -(CHj)2-CO-CH2CCl3, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3,- (C Hz) 2 -CO 2 CH 2 CH 3 , -OCH 2 ) I -CO 2 CH (CHi) 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 33 - (CHj) 2 -CO-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 ,
-(CHz)2-CO2CH2CF3, -(CH2VCO2CF2CF3, ^CH2VCO2CH2CCl3, -(CH2)Z-CO2CCl2Ca3; Metliylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcaxbonyl, tert-Butylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, iso-Propoxycarbonyl, tert-Butoxycarbonyl, Methylthio- carbonyl, Ethylthiocarbonyl, iso-Propylthiocarbonyl, tert-Butylthiocarbonyl, Metltoxymethylcarbonyl, Ethoxymethylcarbonyl, Cyclopropylcarbonyl; Trifluormethylcar- bonjl, Trifluoπnethoxycarbonyl, Trifmormethylthiocarbonyl, oder -CH2-CsC-R1"^- (CH 2 ) 2 -CO 2 CH 2 CF 3 , - (CH 2 VCO 2 CF 2 CF 3 , CH 2 VCO 2 CH 2 CCl 3 , - (CH 2 ) Z -CO 2 CCl 2 Ca 3 ; Metylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso -propylcaxbonyl, tert -butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, methylthio-carbonyl, ethylthiocarbonyl, isopropylphenylthiocarbonyl, tert-butylthiocarbonyl, metltoxymethylcarbonyl, ethoxymethylcarbonyl, cyclopropylcarbonyl; Trifluoromethylcarbonyl, trifluoromethoxycarbonyl, triformomethylthiocarbonyl, or -CH 2 -CsC-R 1 "
-CHrCH=CH-R1 A, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6. R1 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Cyclopropyl, Methoxymethyl, Methoxymethylcarbonyl, Ethoxymethylcarbonyl, Formyl, -CH2-OCH, -CH2-CH=CH2, -CH=C=CH2, -CH2-CHO, -(CH2^-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CHj-CO-CH(CH3K -C(=O)CHO, -C(=0)C(=0)CH3, -C(=O)C(=O)CH2OCH3,-CHRCH = 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, cyclopropyl, methoxymethyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, formyl, -CH 2 -OCH, -CH 2 -CH = CH 2 , -CH = C =CH 2 , -CH 2 -CHO, - (CH 2 ^ -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CHj-CO-CH (CH 3 K -C (= O) CHO, -C (= 0) C (= O) CH 3 , -C (= O) C (= O) CH 2 OCH 3 ,
-C(= O)CO2CH3, -C(O)CO2CH2CH3.-C (= O) CO 2 CH 3 , -C (O) CO 2 CH 2 CH 3 .
R1 A steh: bevorzugt für Wasserstoff, Ci-C4-Alkyl, Ci-C4-Halogenalkyl, C2-C4-Alkenyl, C2-C4-R stand 1 A: preferably represents hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -
Alfanyl, C3-C6-Cycloalkyl, (Ci-C4-Alkoxy)carbonyl, oder Cyano. R'"A steht besonders bevorzugt für Wasserstoff, Methyl oder Ethyl.Alfanyl, C 3 -C 6 -cycloalkyl, (C 1 -C 4 -alkoxy) carbonyl, or cyano. R '"A is particularly preferably hydrogen, methyl or ethyl.
R2 steht bevorzugt für Wasserstoff, Ci-C6-Alkyl, Ci-C4-Alkoxy, Ci-C3-Alkoxy-Ci-C3-alkyl, C3- C6-Cycloalkyl; Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy, Halogen-Ci-C3-alkoxy-Ci-C3- alkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R2 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, tert-Butyl, Meihoxy, Ethoxy, n- oder iso-Propoxy, tert-Butoxy, Methoxymethyl, Cyclopropyl; Trifluor- metdyl, Trifluormethoxy.R 2 is preferably hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; Ci-C 4 haloalkyl, Ci-C4 haloalkoxy, halogen-Ci-C 3 alkoxy-Ci-C 3 - alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms. R 2 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, meihoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
R3 und R4 stehen unabhängig voneinander bevorzugt für Wasserstoff, Ci-Cβ-Alkyl, Ci-C3-Alkoxy- Ci-C3-alkyl, C3-C6-Cycloalkyl; Ci-C4-Halogenalkyl, Halogen-Ci-C3-alkoxy-C,-C3-alkyl, C3-R 3 and R 4 independently of one another preferably represent hydrogen, Ci-Cβ alkyl, Ci-C 3 alkoxy Ci-C 3 alkyl, C 3 -C 6 cycloalkyl; C 1 -C 4 -haloalkyl, halogeno-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -
Cβ-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.Cβ-halogenocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
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 oderR 3 and R 4 also form, together with the nitrogen atom to which they are bonded, preferably one to four times, identically or differently, by halogen or
Ci-C4-Alkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Helerocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff,C 1 -C 4 -alkyl-substituted saturated heterocycle having 5 or 6 ring atoms, where the helerocycle contains 1 or 2 further non-adjacent heteroatoms from the series oxygen,
Schwefel oder NR7 enthalten kann.May contain sulfur or NR 7 .
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, Ett oxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifiuormethyl, Trichlormethyl, Trifluorethyl, Trifluormethoxymethyl. 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,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, ethyl-oxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R 3 and R 4 , together with the nitrogen atom to which they are attached, moreover preferably form an optionally monosubstituted to quadruple, 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,
Thiomoφholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann.Thiomoφholin 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-Q-Alkyl, C3-Cβ-Cycloal- kyl; Ci-C4-Halogenalkyl, C3-C6-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- unάVoder Bromatomen. 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- C4-Λlkyl substituierten gesättigten Heterocyclus mit 5 oder 6 Ringatomen, wobei der Hetcarocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR7 enthalten kann. 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,R 5 and R 6 independently of one another preferably represent hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, or bromine atoms. R 5 and R 6 together with the nitrogen atom to which they are attached preferably also 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 4 -alkyl, where the hetcarocycle is 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 may contain. R 5 and R 6 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; Trifluormethyl, Trichlormethyl,Ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; Trifluoromethyl, trichloromethyl,
Trif luorethyl, Trifluormethoxymethyl.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, Thiamorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann.Chloro, bromo or methyl substituted saturated heterocycle from the series morpholine, thiamorpholine or piperazine, wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
R7 steht bevorzugt für Wasserstoff oder Ci-C4-AUCyI.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.
M ste] it bevorzugt für einen der folgenden CyclenM it is preferable for one of the following cycles
M-I M-2 M-3 M-4 wobei die mit „*" markierte Bindung mit dem Amid, die mit „#" markierte Bindung mit dem Phaiylrest verknüpft ist. M steht besonders bevorzugt für einen Cyclus ausgewählt aus M-I, M-2 und M-4. MI M-2 M-3 M-4 wherein the bond marked with "*" is linked to the amide, the bond marked "#" to the phaiyl radical. M is particularly preferably a cycle selected from MI, M-2 and M-4.
M steht ganz besonders bevorzugt für den Cyclus M- 1.M is most preferably for the cycle M-1.
M steht außerdem ganz besonders bevorzugt für den Heterocyclus M-2.M is also very particularly preferably the heterocycle M-2.
R8 steht bevorzugt für Fluor, wobei Fluor besonders bevorzugt in A-, S- oder 6-Position, ganz besonders bevorzugt in 4- oder 6-Position, insbesondere in 4-Position des Anilidrestes steht. R8 steht außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 5 -Position desR 8 is preferably fluorine, with fluorine being particularly preferably in the A, S or 6 position, very particularly preferably in the 4- or 6-position, in particular in the 4-position of the anilide radical. R 8 furthermore preferably represents chlorine, chlorine being particularly preferably in the 5-position of
Anil xlrestes steht.Anil xlrestes stands.
R8 stehl außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3-Position des Anilidrestes steht.In addition, R 8 is preferably methyl, with methyl being particularly preferably in the 3-position of the anilide radical.
R8 steht außerdem bevorzugt für Trifluormethyl, wobei Trifluormethyl besonders bevorzugt in 4- oder 5-Position des Anilidrestes steht.R 8 furthermore preferably represents trifluoromethyl, trifluoromethyl being particularly preferably in the 4- or 5-position of the anilide radical.
R8 A stehi. bevorzugt für Wasserstoff. R8 A steh: außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 5 -Position (M-2,R 8 A stands. preferred for hydrogen. R 8 A is furthermore preferably chlorine, with chlorine being more preferably in the 5 position (M-2,
M-3) oder in 3-Position (M-4) steht. R8 A steht außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 5-Position (M-M-3) or in the 3-position (M-4). R 8 A is furthermore preferably methyl, with methyl being particularly preferably in the 5-position (M-)
2, M-3) oder in 3-Position (M-4) steht.2, M-3) or in the 3-position (M-4).
R9 steht bevorzugt für Wasserstoff.R 9 is preferably hydrogen.
R9 steh t außerdem bevorzugt für Fluor. R9 steht außerdem bevorzugt für Chlor.R 9 is also preferably fluorine. R 9 is also preferably chlorine.
R10 und R11 stehen in Abhängigkeit voneinander bevorzugt für folgende Kombinationen: a) R10 steht bevorzugt für d-C4-Alkyl oder Cα-C4-Halogenalkyl mit 1 bis 9 Fluor-, Chloroder Bromatomen, undR 10 and R 11 are depending on one another preferably represent the following combinations: a) R 10 preferably represents dC 4 alkyl or C α -C 4 -haloalkyl having 1 to 9 fluorine, chlorine or bromine atoms, and
R11 steht bevorzugt für Wasserstoff, C2-C4-AIlCyI, Hydroxy-C2-C4-alkyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Ci-C3-AIkOXy- Ci-Cs-alkyl, C2-C4-Halogenalkyl, C,-C3-Halogenalkylthio-CrC3-alkyl, C1-C3-R 11 is preferably hydrogen, C 2 -C 4 -alkyl, hydroxy-C 2 -C 4 -alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, Ci-C 3 -AIkOXy- Ci-Cs-alkyl, C 2 -C 4 haloalkyl, C, -C 3 haloalkylthio--C 3 alkyl, C 1 -C 3 -
Halogenalkoxy-Ci-C3-alkyl mit jeweils 1 bis 9 Fluor-, Chlor- oder Bromatomen, (Ci-C6-Alkyl)carbonyl, (Ci-C4-Alkoxy)carbonyl, (Ci-C4-Alkylthio)carbonyl, (Ci-C3- Alkoxy-Ci-C3-alkyl)carbonyl; (Ci-C4-Halogenalkyl)carbonyl, (Ci-C4-Halogen- alkoxy)carbonyl, (Ci-C4-Halogenalkylthio)carbonyl, (Halogen-Ci-C3-alkoxy-Ci-C3- alkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- oder Bromatomen; oder b) R10 steht bevorzugt für C2-C4-Alkyl oder C2-C4-Halogenalkyl mit 1 bis 9 Fluor-, Chloroder Bromatomen, undHaloalkoxy-C 1 -C 3 -alkyl having in each case 1 to 9 fluorine, chlorine or bromine atoms, (C 1 -C 6 -alkyl) carbonyl, (C 1 -C 4 -alkoxy) carbonyl, (C 1 -C 4 -alkylthio) carbonyl , (Ci-C 3 - alkoxy-Ci-C 3 alkyl) carbonyl; (Ci-C 4 haloalkyl) carbonyl, (Ci-C4-halo-alkoxy) carbonyl, (Ci-C 4 haloalkylthio) carbonyl, (halo-Ci-C 3 alkoxy-Ci-C 3 - alkyl) carbonyl each having 1 to 9 fluorine, chlorine or bromine atoms; or b) R 10 is preferably C 2 -C 4 -alkyl or C 2 -C 4 -haloalkyl having 1 to 9 fluorine, chlorine or bromine atoms, and
Ru steht bevorzugt für Wasserstoff, Ci-C4-Alkyl, Hydroxy-Ci-C4-alkyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Ci-C3-Alkylthio-Ci-C3-alkyl, Ci-C3-Alkoxy-R u is preferably hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, C 1 -C 3 -alkylthio-C 1 -C 3 -alkyl, C 1 -C 3 - alkoxy
Ci-C3-alkyl, d-C4-Halogenalkyl, Ci-C3-Hdogenalkylthio-Ci-C3-alkyl, Q-C3-Ci-C 3 -alkyl, dC 4 -haloalkyl, Ci-C 3 -Hdogenalkylthio-Ci-C 3 -alkyl, QC 3 -
Halogenalkoxy-Ci-C3-alkyl mit jeweils 1 bis 9 Fluor-, Chlor- oder Bromatomen,Haloalkoxy-C 1 -C 3 -alkyl having in each case 1 to 9 fluorine, chlorine or bromine atoms,
(Ci-C6-Alkyl)carbonyl, (Q-C4-Alkoxy)carbonyl, (Ci-C4-Alkyhhio)carbonyl, (C1-C3-(Ci-C 6 alkyl) carbonyl, (QC 4 alkoxy) carbonyl, (Ci-C 4 -Alkyhhio) carbonyl, (C 1 -C 3 -
Alkoxy-Ci-C3-alkyl)carbonyl; (Ci-C4-Halogenalkyl)carbonyl, (Ci-C4-Halogen- alkoxy)carbonyl, (Ci-C4-Halogenalkylthio)carbonyl, (Halogen-Ci-C3-alkoxy-Ci-C3- alkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- oder Bromatomen.Alkoxy-C 1 -C 3 -alkyl) carbonyl; (Ci-C 4 haloalkyl) carbonyl, (Ci-C4-halo-alkoxy) carbonyl, (Ci-C 4 haloalkylthio) carbonyl, (halo-Ci-C 3 alkoxy-Ci-C 3 - alkyl) carbonyl with 1 to 9 fluorine, chlorine or bromine atoms.
a) R10 steht besonders bevorzugt für Methyl, Ethyl, n-, iso-Propyl, n-, i-, s-, t-Butyl,a) R 10 particularly preferably represents methyl, ethyl, n-, isopropyl, n-, i-, s-, t-butyl,
Trifluormethyl, Difluormethyl, Trichlormethyl, Dichlormethyl, Difluorchlormethyl, Fluordichlormethyl, Pentafluorethyl, -CH2CF3, -CH2CF2CF3, -CH2CF2CF2CF3,Trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, difluorochloromethyl, fluorodichloromethyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 ,
-CF(CF3), oder -CH(CF3)2, und-CF (CF 3 ), or -CH (CF 3 ) 2 , and
R11 steht besonders bevorzugt für Wasserstoff, Ethyl, n-, iso-Propyl, n-, i-, s-, t-Butyl,R 11 particularly preferably represents hydrogen, ethyl, n-, isopropyl, n-, i-, s-, t-butyl,
-CH2CH2OH, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Methylthiomethyl, Methylthioethyl, Ethylthiomethyl, Ethylthioethyl, Methoxymethyl, Methoxyethyl,-CH 2 CH 2 OH, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, methoxymethyl, methoxyethyl,
Ethoxymethyl, Ethoxyethyl, Pentafluorethyl, -CH2CF3, -CH2CF2CF3, -CH2CF2CF2CF3,Ethoxymethyl, ethoxyethyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 ,
-CF(CFa)2, -CH(CFj)2, Trifluormethylthiomethyl, -CH2SCH2CF3, -CH2SCF2CF3, Tri- fluormethoxymethyl, -CH2OCH2CF3, -CH2OCF2CF3, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butylcarbonyl, Methoxycarbonyl, Ethoxycar- bonyl, iso-Propoxycarbonyl, tert-Butoxycarbonyl, Methyltiiiocarbonyl, EthyKbiocarbo- nyl, iso-Propyhhiocarbonyl, tert-Butylthiocarbonyl, Methoxyrnethylcarbonyl, Ethoxy- methylcarbonyl; Trifluormethylcarbonyl, Trifluormethoxycarbonyl, Trifluorme- thylthiocarbonyl; oder b) R10 steht besonders bevorzugt für Ethyl, n-, iso-Propyl, n-, i-, s-, t-Butyl, Pentafluorethyl, -CH2CF3, -CH2CF2CF3, -CH2CF2CF2CF3, -CF(CF3)2 oder - CH(CF3)2, und-CF (CFa) 2 , -CH (CFj) 2 , trifluoromethylthiomethyl, -CH 2 SCH 2 CF 3 , -CH 2 SCF 2 CF 3 , trifluoromethoxymethyl, -CH 2 OCH 2 CF 3 , -CH 2 OCF 2 CF. 3 , methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylpolyyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, methyltiiiocarbonyl, ethyKbiocarbonyl, isopropylmuthyl, tert-butylthiocarbonyl, methoxyrnethylcarbonyl, ethoxy- methylcarbonyl; Trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl; or b) R 10 particularly preferably represents ethyl, n-, isopropyl, n-, i-, s-, t-butyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 or - CH (CF 3 ) 2 , and
R11 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-, iso-Propyl, n-, i-, s-, t- Butyl, -CH2CH2OH, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Methylthiomethyl, Methylthioethyl, Ethylthiomethyl, Ethylthioethyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Trifluormethyl, Difluoπnethyl, Trichlormethyl, Dichlor- methyl, Difluorchlonτvethyl, Fluordichlonnethyl, Peπtafluorethyl, -CH2CF3, -CH2CF2CF3, -CH2CF2CF2CF3, -CF(CFj)2, -CH(CF3),, Trifluormethylilüomethyl, -CH2SCH2CF3, -CH2SCF2CF3, -CH2OCH2CF3, -CH2OCF2CF3, Tnfluormethoxyme- thyl, Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butyl- carbonyl, Methoxycarbonyl, Ethoxycarbonyl, iso-Propoxycarbonyl, tert-Butoxycarbonyl, Methylthiocarbonyl, Ethyllhiocarbonyl, iso-Propylthiocarbonyl, tert-Butyhhiocarbonyl, Methoxymethylcarbonyl, Ethoxymethylcarbonyl; Trifluormethylcarbonyl, Triftuorme- thoxycarbonyl, Trifluoπnethylthiocarbonyl.R 11 particularly preferably represents hydrogen, methyl, ethyl, n-, iso-propyl, n-, i-, s-, t-butyl, -CH 2 CH 2 OH, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylthiomethyl, methylthioethyl , Ethylthiomethyl, ethylthioethyl, methoxymethyl, methoxyethyl, Ethoxymethyl, ethoxyethyl, trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, difluorochlonvethyl, fluorodichloromethyl, pectafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CFj) 2 , -CH (CF 3 ) ,, Trifluoromethylilomethyl, -CH 2 SCH 2 CF 3 , -CH 2 SCF 2 CF 3 , -CH 2 OCH 2 CF 3 , -CH 2 OCF 2 CF 3 , Tnfluoromethoxy- methyl, methylcarbonyl, ethylcarbonyl , n-propylcarbonyl, iso -propylcarbonyl, tert -butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, methylthiocarbonyl, ethyllithiocarbonyl, iso-propylthiocarbonyl, tert-butylhiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl; Trifluoromethylcarbonyl, Triftuormethoxycarbonyl, Trifluoπnethylthiocarbonyl.
a) R10 steht ganz besonders bevorzugt für Methyl, Trifluoπnethyl oder Difluormethyl, unda) R 10 very particularly preferably represents methyl, trifluoromethyl or difluoromethyl, and
R11 steht ganz besonders bevorzugt für Wasserstoff, Ethyl, n-Propyl, n-Butyl, -CH2CH2OH, Cyclopropyl, Methylthiomethyl, Methoxymethyl, Ethoxymethyl, -CH2CF3, -CH2CF2CF3, -CF(CF3)2, -CH(CF3)2, Trifluormethylthiomethyl,R 11 is very particularly preferably hydrogen, ethyl, n-propyl, n-butyl, -CH 2 CH 2 OH, cyclopropyl, methylthiomethyl, methoxymethyl, ethoxymethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CF (CF 3 ) 2 , -CH (CF 3 ) 2 , trifluoromethylthiomethyl,
-CH2SCH2CF3, -CH2SCF2CF3, Trifluormethoxymethyl, -CH2OCH2CF3,-CH 2 SCH 2 CF 3 , -CH 2 SCF 2 CF 3 , trifluoromethoxymethyl, -CH 2 OCH 2 CF 3 ,
-CH2OCF2CF3, Methylcarbonyl, n-Propylcarbonyl, Methoxycarbonyl, Methylthiocarbonyl, Methoxymethylcarbonyl, Ethoxymethylcarbonyl; Trifluormethylcarbonyl, Trifluormethoxycarbonyl, Trifluoπnethylthiocarbonyl, insbesondere bevorzugt für Ethyl, Methylthiomethyl, Methoxymethyl, Trifluormethoxymethyl, Methylcarbonyl; oder b) R10 steht ganz besonders bevorzugt für n-Propyl, n-, t-Butyl, Pentafluorethyl, -CH2CF3,-CH 2 OCF 2 CF 3 , methylcarbonyl, n -propylcarbonyl, methoxycarbonyl, methylthiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl; Trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, particularly preferably ethyl, methylthiomethyl, methoxymethyl, trifluoromethoxymethyl, methylcarbonyl; or b) R 10 very particularly preferably represents n-propyl, n-, t-butyl, pentafluoroethyl, -CH 2 CF 3 ,
-CH2CF2CF3, -CH2CF2CF2CF3, -CF(CF3), oder -CH(CF3)2, und R" steht ρ;anz besonders bevorzugt füi Wasserstoff, Methyl, Ethyl, n-Propyl, n-Butyl,-CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 ), or -CH (CF 3 ) 2 , and R "is ρ; anz is particularly preferably hydrogen, methyl, ethyl, n-propyl, n-butyl,
-CH2CH2OH, Cyclopropyl, Methylthiomethyl, Methoxymethyl, Ethoxymethyl, Trifluormethyl, Difluormethyl, -CH2CF3, -CH2CF2CF3, -CH2CF2CF2CF3, -CF(CF3J2, -CH(CF3)2, Trifluormethylthiomethyl, -CH2SCH2CF3, -CH2SCF2CF3, Trifluormethoxymethyl, -CH2OCH2CF3, -CH2OCF2CF3, Methylcarbonyl, n- Propylcarbonyl, Methoxycarbonyl, Methylthiocarbonyl, Methoxymethylcarbonyl,-CH 2 CH 2 OH, cyclopropyl, methylthiomethyl, methoxymethyl, ethoxymethyl, trifluoromethyl, difluoromethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 J 2 , -CH (CF 3 ) 2 , trifluoromethylthiomethyl, -CH 2 SCH 2 CF 3 , -CH 2 SCF 2 CF 3 , trifluoromethoxymethyl, -CH 2 OCH 2 CF 3 , -CH 2 OCF 2 CF 3 , methylcarbonyl, n-propylcarbonyl , Methoxycarbonyl, methylthiocarbonyl, methoxymethylcarbonyl,
Ethoxymethylcarbonyl; Trifluormethylcarbonyl, Trifluormethoxycarbonyl, Trifluor- methylthiocarbonyl, insbesondere bevorzugt für Methyl, Ethyl, Methylthiomethyl, Methoxymethyl, Trifluormethoxymethyl, Methylcarbonyl.Ethoxymethylcarbonyl; Trifluoromethylcarbonyl, trifluoromethoxycarbonyl, trifluoromethylthiocarbonyl, particularly preferably methyl, ethyl, methylthiomethyl, methoxymethyl, trifluoromethoxymethyl, methylcarbonyl.
m steht bevorzugt für 1, wobei R12 dann besonders bevorzugt in 4'-Position steht. m steht außerdem bevorzugt für 2, wobei die Reste R12 dann besonders bevorzugt in 3',4'-5 2',4'- oder 3',5'-Position stehen. m steht außerdem bevorzugt für 3, wobei die Reste R12 dann besonders bevorzugt in 2',4',6'-m is preferably 1, where R 12 is then particularly preferably in the 4'-position. In addition, m is preferably 2, where the radicals R 12 are particularly preferably in the 3 ', 4'- 5 2', 4 'or 3', 5 'position. In addition, m is preferably 3, where the radicals R 12 are particularly preferably in 2 ', 4', 6 '
Position stehenStanding position
R12 steht bevorzugt für Fluor, Chlor, Brom, Cyano, Nitro, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Cyclopropyl,R 12 is preferably fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, ethylthio, n- or i-propylthio, cyclopropyl,
Trifluormethyl, Trichlormethyl, Trifluorethyl, Difluormethoxy, Trifluormethoxy, Difluor- chloi methoxy, Trifluorethoxy, Difluormethylthio, Difluorchlormethylthio oder Trifluorme- thylttiio, -CH2Si(CH3)3 oder -Si(CH3)3, oder für -C(Q^)=N-Q2, worinTrifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio or trifluoromethylthio, -CH 2 Si (CH 3 ) 3 or -Si (CH 3 ) 3 , or for -C (Q.sub.1) ) = NQ 2 , in which
Q1 für Wasserstoff, Methyl, Ethyl, Trifluormethyl oder Cyclopropyl steht und Q2 für Hydroxy, Methoxy, Ethoxy, Propoxy oder Isopropoxy steht.Q 1 is hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl and Q 2 is hydroxy, methoxy, ethoxy, propoxy or isopropoxy.
R12 stehl besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethoxy, Trifluormethoxy, -C(CH3)=N-OCH3, -C(CH3)=N-O(i-C3H7) oder -C(Cyclopropyl)=N- OCH3.R 12 is particularly preferably fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, -C (CH 3 ) = N-OCH 3 , -C (CH 3 ) = NO (iC 3 H 7 ) or -C ( Cyclopropyl) = N-OCH 3 .
R12 stehl außerdem besonders bevorzugt für -SOnR13, -SO2NR14R15, -C(=X)R16, -Si(R17)3, -NR14R15 oder -CH2-NR14R15.R 12 is also particularly preferred for -SO n R 13 , -SO 2 NR 14 R 15 , -C (= X) R 16 , -Si (R 17 ) 3 , -NR 14 R 15 or -CH 2 -NR 14 R 15 .
R13 steht bevorzugt für Ci-C4-Alkyl oder Ci-C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Broinatomen.R 13 preferably represents Ci-C4 alkyl or Ci-C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or Broinatomen.
R13 steh: besonders bevorzugt für Methyl, Ethyl, n-, iso-Propyl, n-, i-, s-, t-Butyl, Trifluormethyl -CH2CF3, -C2F5 oder Trichlormethyl. R13 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, -CH2CF3 oder -C2F5.R 13 is particularly preferably methyl, ethyl, n-, iso-propyl, n-, i-, s-, t-butyl, trifluoromethyl-CH 2 CF 3 , -C 2 F 5 or trichloromethyl. R 13 very particularly preferably represents methyl, trifluoromethyl, -CH 2 CF 3 or -C 2 F 5 .
n steht bevorzugt für 1. n steht auch bevorzugt für 2. n steht besonders bevorzugt für 2.n is preferably 1. n is also preferably 2. n is particularly preferably 2.
R14 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Butyl oder -C(=X)Rlδ.R 14 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl or -C (= X) R lδ .
R14 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl oderR 14 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or
-C(==X)R16. R14 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.-C (= X) R 16 . R 14 is very particularly preferably hydrogen or methyl.
R15 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Butyl oder -C(=X)R16. R15 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl oderR 15 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl or -C (= X) R 16 . R 15 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl or
-C(= *QR16. R15 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.-C (= * QR 16 R 15 is very particularly preferably hydrogen or methyl.
R14 und R15 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt 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. R14 und R15 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 14 and R 15 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 mono- 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 14 and R 15 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 .
X steht bevorzugt für O (Sauerstoff). X steht auch bevorzugt für S (Schwefel).X is preferably O (oxygen). X is also preferably S (sulfur).
R16 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Butjl, Methoxy, Ethoxy, n- oder iso-Propoxy, n-, iso-, sec- oder tert-Butoxy oder -NR18R19.R 16 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 18 R 19 .
Rlδ steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, Methoxy,R lδ is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, methoxy,
Ethcxy, n- oder iso-Propoxy oder -NR18R19. R16 stehl ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Methoxy, Ethoxy oderEthoxy, n- or iso-propoxy or -NR 18 R 19 . R 16 stehl very particularly preferably for hydrogen, methyl, ethyl, methoxy, ethoxy or
-NR18R19.-NR 18 R 19 .
R17 steht bevorzugt für Ci-C6-Alkyl, CrC6-Alkoxy, Q-Cj-Alkoxy-C-Cs-alkyl oder Q-C3-R 17 is preferably C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C -alkoxy-C 1 -C 6 -alkyl or QC 3 -
Alkylthio-Ci-C3-alkyl, wobei die drei Reste R17 jeweils gleich oder verschieden sein können. R17 stehi. besonders bevorzugt für Methyl, Ethyl, Methoxy, Ethoxy, Methoxymethyl, Ethoxyme- thyL Methoxyethyl, Ethoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methylthioethyl oder Ethyltbioethyl, wobei die drei Reste R17 jeweils gleich oder verschieden sein können.Alkylthio-Ci-C 3 -alkyl, wherein the three radicals R 17 may be the same or different. R 17 stands. particularly preferred for methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxy-methy l methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl or Ethyltbioethyl, where the three radicals R 17 may be the same or different.
R17 steh: ganz besonders bevorzugt für Methyl, Methoxy, Methoxymethyl oder Methylthiomethyl, wobei die drei Reste R17 jeweils gleich oder verschieden sein können. R17 steht insbesondere bevorzugt für Methyl.R 17 radicals are very particularly preferably methyl, methoxy, methoxymethyl or methylthiomethyl, where the three radicals R 17 may each be identical or different. R 17 is particularly preferably methyl.
R18 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Butyl. R18 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl. R18 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.R 18 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl. R 18 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl. R 18 is very particularly preferably hydrogen or methyl.
R19 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert- Buty .R 19 is preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
R19 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl.R 19 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl.
R19 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.R 19 is very particularly preferably hydrogen or methyl.
R18 und R19 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,R 18 and R 19 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 or polysubstituted, identically or differently by halogen or C 1 -C 4 -alkyl Heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen,
Schwefel oder NR7 enthalten kann.May contain sulfur or NR 7 .
R18 und R19 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bg; sondsrs bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durchR 18 and R 19 also together with the nitrogen atom to which they are attached form bg; sondsrs preferably prefers one to four times, identically or differently
Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der ReiheFluorine, chlorine, bromine or methyl substituted saturated heterocycle from the series
Moroholin, Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R7 substituiert sein kann.Moroholin, thiomorpholine or piperazine, wherein the piperazine on the second nitrogen atom may be substituted by R 7 .
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)Preference is furthermore given to compounds of the formula (I-b)
in welcher FL1, M, R8, R9, R10, R11, R12 und m die oben angegebenen Bedeutungen haben. in which FL 1 , M, R 8 , R 9 , R 10 , R 11 , R 12 and m have the meanings given above.
Besonders bevorzugt sind Verbindungen der Formel (I-b), in welcher R1 für Wasserstoff steht. Außerdem besonders bevorzugt sind Verbindungen der Formel (I-b), in welcher die Reste R8 in 4- Posrtion stellt. Außerdem besonders bevorzugt sind Verbindungen der Formel (I-b), in welcher R8 für Fluor steht. Außerdem b ;sonders bevorzugt sind Verbindungen der Formel (I-b), in welcher R8 für Fluor steht, wobei R8 in 4-Position steht.Particular preference is given to compounds of the formula (Ib) in which R 1 is hydrogen. In addition, particular preference is given to compounds of the formula (Ib) in which the radicals R 8 are in position 4. In addition, particular preference is given to compounds of the formula (Ib) in which R 8 is fluorine. Also particularly preferred are compounds of the formula (Ib) in which R 8 is fluorine, where R 8 is in the 4-position.
Außerdem besonders bevorzugt sind Verbindungen der Formel 0-b), in welcher m für 1 steht und R12 in 4'-Pos ition steht.Particular preference is furthermore given to compounds of the formula 0-b) in which m is 1 and R 12 is in the 4'-position.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-b), in welcher m für 2 steht und R12 in 3',4'-, 2',4'- oder 3 ',5 '-Position, ganz besonders bevorzugt in 3',4'-Position steht. Außerdem besonders bevorzugt sind Verbindungen der Formel (I-b), in welcher R12 für Fluor oder Chlor steht.Particular preference is furthermore given to compounds of the formula (Ib) in which m is 2 and R 12 is in the 3 ', 4', 2 ', 4' or 3 ', 5' position, very particularly preferably in 3 ', 4'-position is. In addition, particular preference is given to compounds of the formula (Ib) in which R 12 is fluorine or chlorine.
Bevorzugt sind außerdem Verbindungen der Formel (I-c)Preference is furthermore given to compounds of the formula (I-c)
in welcher K1, M3 R8 A, R9, R10, Rπ, R12 und m die oben angegebenen Bedeutungen haben. in which K 1 , M 3 R 8 A , R 9 , R 10 , R π , R 12 and m have the meanings given above.
Besonders b evorzugt sind Verbindungen der Formel (I-c), in welcher R1 für Wasserstoff steht.Particular preference is given to compounds of the formula (Ic) in which R 1 is hydrogen.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-c), in welcher die Reste R8 A fürIn addition, particular preference is given to compounds of the formula (Ic) in which the radicals R 8 A are
Wasserstoff' steht.Hydrogen ' stands.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-c), in welcher die Reste R8 A in 5-Particular preference is furthermore given to compounds of the formula (Ic) in which the radicals R 8 A in 5
Position stellt, wobei R8'A dann bevorzugt für Chlor oder Methyl steht. Außerdem besonders bevorzugt sind Verbindungen der Formel (I-c), in welcher m für 1 steht und R12 in 4'-Positicn steht.Position wherein R 8'A is then preferably chlorine or methyl. In addition, particular preference is given to compounds of the formula (Ic) in which m is 1 and R 12 is in 4'-position.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-c), in welcher m für 2 steht und R12 in 3',4'-, 2',4'- oder 3',5'-Position, ganz besonders bevorzugt in 3',4'-Position steht.Particular preference is furthermore given to compounds of the formula (Ic) in which m is 2 and R 12 is in the 3 ', 4', 2 ', 4' or 3 ', 5' position, very particularly preferably in 3 ', 4'-position stands.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-c), in welcher R12 für Fluor oder Chlor steht.In addition, particular preference is given to compounds of the formula (Ic) in which R 12 is fluorine or chlorine.
Bevorzugt s:ind außerdem Verbindungen der Formel (I-d) in welcher R1, M, R8 A, R9, R10, R11, R12 und m die oben angegebenen Bedeutungen haben.Preferably, furthermore, compounds of the formula (Id) in which R 1 , M, R 8 A , R 9 , R 10 , R 11 , R 12 and m have the meanings given above.
Besonders bevorzugt sind Verbindungen der Formel (I-d), in welcher R1 für Wasserstoff steht. Außerdem besonders bevorzugt sind Verbindungen der Formel (I-d), in welcher die Reste R8 A fürParticular preference is given to compounds of the formula (Id) in which R 1 is hydrogen. In addition, particular preference is given to compounds of the formula (Id) in which the radicals R 8 A are
Wasserstoff steht.Hydrogen stands.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-d), in welcher die Reste R8 A in 5-Particular preference is furthermore given to compounds of the formula (Id) in which the radicals R 8 A in 5
Position steht, wobei R8'A dann bevorzugt für Chlor oder Methyl steht.Position, wherein R 8'A is then preferably chlorine or methyl.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-d), in welcher m für 1 steht und R12 in 4'-Position steht.In addition, particular preference is given to compounds of the formula (Id) in which m is 1 and R 12 is in the 4'-position.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-d), in welcher m für 2 steht und R12 in 3',4'-, 2',4'- oder 3',5'-Position, ganz besonders bevorzugt in 3',4'-Position steht.Particular preference is furthermore given to compounds of the formula (Id) in which m is 2 and R 12 is in the 3 ', 4', 2 ', 4' or 3 ', 5' position, very particularly preferably in 3 ', 4'-position stands.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-d), in welcher R12 für Fluor oderParticular preference is furthermore given to compounds of the formula (Id) in which R 12 is fluorine or
Chlor steht.Chlorine stands.
Bevorzugt sind außerdem Verbindungen der Formel (I-e)Preference is furthermore given to compounds of the formula (I-e)
in welcher P1, M, R8^, Rs, R1U, R11, R12 und m die oben angegebenen Bedeutungen haben. in which P 1 , M, R 8 ^, R s , R 1U , R 11 , R 12 and m have the meanings given above.
Besonders bevorzugt sind Verbindungen der Formel (I-e), in welcher R1 für Wasserstoff steht.Particular preference is given to compounds of the formula (Ie) in which R 1 is hydrogen.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-e), in welcher die Reste R8 A fürIn addition, particular preference is given to compounds of the formula (Ie) in which the radicals R 8 A are
Wasserstoff steht.Hydrogen stands.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-e), in welcher die Reste R8A in 3-Particular preference is furthermore given to compounds of the formula (Ie) in which the radicals R 8A in 3
Position stellt, wobei R8 A dann bevorzugt für Chlor oder Methyl steht. Außerdem t esonders bevorzugt sind Verbindungen der Formel (I-e), in welcher m für 1 steht und R12 in 4'-Position steht.Position wherein R 8 A is then preferably chlorine or methyl. In addition, particularly preferred are compounds of the formula (Ie) in which m is 1 and R 12 is in the 4'-position.
Außerdem besonders bevorzugt sind Verbindungen der Formel (I-e), in welcher m für 2 steht und R12 in 3',4'-, 2'/,'- oder 3',5'-Position, ganz besonders bevorzugt in 3',4'-Position steht. Außerdem besonders bevorzugt sind Verbindungen der Formel (I-e), in welcher R12 für Fluor oder Chlor steht.Particular preference is furthermore given to compounds of the formula (Ie) in which m is 2 and R 12 is in the 3 ', 4', 2 '/,' or 3 ', 5' position, very particularly preferably in 3 ', 4'-position stands. Particular preference is furthermore given to compounds of the formula (Ie) in which R 12 is fluorine or chlorine.
Bevorzugt sind ebenfalls Verbindungen der Formel (I), in welcher R1 für Wasserstoff steht. Außerdem bevorzugt sind Verbindungen der Formel (I), in welcher m für 1 steht und R12 in 4'- Position steht.Preference is likewise given to compounds of the formula (I) in which R 1 is hydrogen. Preference is furthermore given to compounds of the formula (I) in which m is 1 and R 12 is in the 4'-position.
Außerdem bevorzugt sind Verbindungen der Formel (I), in welcher m für 2 steht und R12 in 3',4'-, 2',4'- oder 3' ,5'-Position, ganz besonders bevorzugt in 3',4'-Position steht. Außerdem besonders bevorzugt sind Verbindungen der Formel (I), in welcher R12 für Fluor oder Chlor steht.Preference is furthermore given to compounds of the formula (I) in which m is 2 and R 12 is in the 3 ', 4', 2 ', 4' or 3 ', 5' position, very particularly preferably in 3 ', 4 'Position stands. In addition, particular preference is given to compounds of the formula (I) in which R 12 is fluorine or chlorine.
Weiter bevorzugt sind Verbindungen der Formeln (I) und (I-b) bis (I-e), in welchen, Rπ für Ethyl, n- Propyl, n-Eutyl, -CH2CH2OH, Cyclopropyl, Methylthiomethyl, Methoxymethyl, Ethoxymethyl, -CH2CF3, CH2CF2CF3, Trifluormethylthiomethyl, -CH2SCH2CF3, -CH2SCF2CF3, Trifluor- methoxymethyl, -CH2OCH2CF3, -CH2OCF2CF3, Methylcarbonyl, n-Propylcarbonyl, Methoxycarbonyl, Methylthiocarbonyl, Methoxymethylcarbonyl, Ethoxymethylcarbonyl, Trifluor- methylcarbcnyl, Trifluormethoxycarbonyl oder Trifluormethylthiocarbonyl steht. Weiter besonders bevorzugt sind Verbindungen der Formeln (I) und (I-b) bis (I-e), in welchen, Rπ für Ethyl, Cyclopropyl, Methylthiomethyl, Methoxymethyl, Trifluormethoxymethyl oder Methylcarbonyl steht. Weiter bevorzugt sind Verbindungen der Formeln (I) und (I-b) bis (I-e), in welchen R10 für Ethyl, n-, iso-Propyl, n-, i-, s-, t-Butyl, Pentafluorethyl, -CH2CF3, -CH2CF2CF3, -CH2CF2CF2CF3, -CF(CF3)2 oder -CH(CFs)2 steht.Further preferred are compounds of the formulas (I) and (Ib) to (Ie) in which R π is ethyl, n-propyl, n-eutyl, -CH 2 CH 2 OH, cyclopropyl, methylthiomethyl, methoxymethyl, ethoxymethyl, CH 2 CF 3 , CH 2 CF 2 CF 3 , trifluoromethylthiomethyl, -CH 2 SCH 2 CF 3 , -CH 2 SCF 2 CF 3 , trifluoromethoxymethyl, -CH 2 OCH 2 CF 3 , -CH 2 OCF 2 CF 3 , Methylcarbonyl, n-propylcarbonyl, methoxycarbonyl, methylthiocarbonyl, methoxymethylcarbonyl, ethoxymethylcarbonyl, trifluoromethylcarbcnyl, trifluoromethoxycarbonyl or trifluoromethylthiocarbonyl. Further particularly preferred are compounds of the formulas (I) and (Ib) to (Ie) in which R π is ethyl, cyclopropyl, methylthiomethyl, methoxymethyl, trifluoromethoxymethyl or methylcarbonyl. Further preferred are compounds of the formulas (I) and (Ib) to (Ie) in which R 10 is ethyl, n-, isopropyl, n-, i-, s-, t-butyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 or -CH (CFs) 2 .
Weiter besonders bevorzugt sind Verbindungen der Formeln (I) und (I-b) bis (I-e), in welchen R10 für n-Propyl, n-, t-Butyl, Pentafluorethyl, -CH2CF3, -CH2CF2CF3, -CH2CF2CF2CF3, -CF(CF3)2 oder -CH(CFB)2 irteht.Further particularly preferred are compounds of the formulas (I) and (Ib) to (Ie) in which R 10 is n-propyl, n-, t-butyl, pentafluoroethyl, -CH 2 CF 3 , -CH 2 CF 2 CF 3 , -CH 2 CF 2 CF 2 CF 3 , -CF (CF 3 ) 2 or -CH (CFB) 2 is absent.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen können jedoch auch untereinander, also zwischen den jeweiligen Bereichen und Vorzugsbeieichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenpiodukte 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 areas and preferred areas. They apply accordingly to the end products as well as to the pre- and intermediate-periodients.
Verwendet man beispielsweise 3-(Difluormethyl)-l-ethyl-lH-pyrazol-4-carbonylchlorid und 3',4'-Di- chlor-5-fluorbiphenyl-2-amin als Ausgangsstoffe sowie ein Base, so kann der Verlauf des erfindungsgemäßen Verfahrens (a) durch folgende Reaktionsgleichung veranschaulicht werden: If, for example, 3- (difluoromethyl) -1-ethyl-1H-pyrazole-4-carbonyl chloride and 3 ', 4'-dichloro-5-fluorobiphenyl-2-amine are used as starting materials and a base, the course of the process according to the invention can be used Process (a) are illustrated by the following reaction equation:
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötigten Carbon- säurehalogeriide sind durch die Formel (II) allgemein definiert. In dieser Formel (II) stehen R9, R10 und R11 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 diese Reste angegeben wurden. X1 steht bevorzjgt für Fluor, Chlor oder Hydroxy, besonders bevorzugt für Chlor oder Hydroxy.The carboxylic acid halogeriides required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (II). In this formula (II) R 9, R 10 and R 11 are preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have already as preferred in connection with the description of the substances according to the invention of the formula (I), especially preferred, etc. were given for these radicals. X 1 is preferably fluorine, chlorine or hydroxyl, more preferably chlorine or hydroxy.
Die Carbon säurehalogenide der Formel (II) sind bekannt und/oder lassen sich nach bekannten Verfahren herstellen (vgl. z.B. EP-A 0 545 099, JP-A 1-290662 und US 5,093,347).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 1-290662 and US 5,093,347).
Die weiterh n zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötigten Amine sind durch die Formel (III) allgemein definiert. In dieser Formel (III) stehen R1, M, R12 und m 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 diese Reste bzw. diesen Index angegeben ivurden.The weiterh n for carrying out the process (a) required as starting materials amines are generally defined by the formula (III). In this formula (III) R 1, M, R and m are 12 preferred, particularly preferred, very particularly preferred or especially preferred for those meanings which have already as preferred in connection with the description of the substances of formula (I) according to the invention, particularly preferably, etc., are given for these radicals or this index.
Die Amine der Formel (III) sind bekannt und/oder lassen sich nach bekannten Verfahren herstellen (vgl. z.B. EP-A 0 545 099, WO 03/070705).The amines of the formula (III) are known and / or can be prepared by known processes (cf., for example, EP-A 0 545 099, WO 03/070705).
Verwendet man N-(3 ',4'-Dichlor-5 -fluorbiphenyl-2-yl)-3 -(difluormethyl)- 1 -ethyl- lH-pyrazol-4-carb- oxamid und Acetylchlorid als Ausgangsstoffe, so kann der Verlauf des erfindungsgemäßen Verfahrens (b) durch das folgende Formelschema veranschaulicht werden:If N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3- (difluoromethyl) -1-ethyl-1H-pyrazole-4-carboxamide and acetyl chloride are used as starting materials, the course of the process (b) according to the invention are illustrated by the following equation:
Die zur Durchführung des erfindungsgemäßen Verfahrens (b) als Ausgangsstoffe benötigten Pyrazolylcarboxamide sind durch die Formel (I-a) allgemein definiert. In dieser Formel (I-a) haben M, R9, R10, R11, R12 und m bevorzugt, besonders bevorzugt, ganz besonders bevorzugt bzw. insbe- sondere bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsg anäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt usw. für diese Reste bzw. diesen Index angegeben wurden. The pyrazolylcarboxamides required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (Ia). In this formula (Ia), M, R 9 , R 10 , R 11 , R 12 and m have preferably, more preferably, very particularly preferably or in particular preferably those meanings which have already been mentioned in connection with the description of the compounds according to the invention of the formula (I) as preferred, particularly preferred, etc. for these radicals or this index.
Die Verbindungen der Formel (I-a) sind erfindungsgemäße Verbindungen und können nach Ver- fahren (a) h ergestellt werden.The compounds of the formula (I-a) are compounds according to the invention and can be prepared by process (a) h.
Die zur Durchführung des erfindungsgemäßen Verfahrens (b) weiterhin als Ausgangsstoffe benötigten Halogenide sind durch die Formel (IV) allgemein definiert. In dieser Formel (TV) 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"3 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 (IV). In this formula (TV), R 1 B is preferably, more preferably, very particularly preferably or in particular preferred for those meanings which have already been indicated above for the radical R 1 as being preferred, particularly preferred etc., where R 1 "3 never is hydrogen, Hal is chlorine, bromine or iodine.
Halogenide der Formel (IV) sind bekannt.Halides of the formula (IV) are known.
Als Verdünnungsmittel zur Durchführung 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- Butyronitnl oder Benzonitril; Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N- Methylfoπαanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; deren Gemische mit Wasser odar 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-methylfoπαanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; their mixtures with water or pure water.
Das erfinctungsgemäße Verfahren (a) wird gegebenenfalls in Gegenwart eines geeigneten Säureakzeptors durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Basen infrage. H erzu gehören vorzugsweise Erdalkalimetall- oder Alkalimetallhydride, -hydroxide, -amide, -alkoholat:, -acetate, -carbonate oder -hydrogencarbonate, wie z.B. Natriumhydrid, Natriumamid, Lithiumdiisopropylamid, Natrium-methylat, Natrium-ethylat, Kalium-tert.-butylat, Natrium- hydroxid, KEdiurnhydroxid, Natriumacetat, Natriumcarboπat, Kaliumcarboπat, Kaliumhydrogen- carbonat, Nalriumhydrogencarbonat oder Ammoniumcarbonat, sowie tertiäre Amine, wie Trimethyl- amin, Triethylamin, Tributylartiin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N- Methylpiperidin, N-Methylmoφholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).If appropriate, the 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. H erzu preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholate, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide , Sodium hydroxide, KEdiurnhydroxid, sodium acetate, Natriumcarboπat, Kaliumcarboπat, potassium bicarbonate, Nalriumhydrogencarbonat or ammonium carbonate, and tertiary amines, such as trimethylamine, triethylamine, Tributylartiin, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine , N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
Das erfindunjjsgernäße Verfahren (a) wird gegebenenfalls in Gegenwart eines geeigneten Kupplungsreagenzes durchgeführt (wenn X5 für Hydroxy steht). Als solche kommen alle üblichen Carbonyl- aktivatoren in frage. Hierzu gehören vorzugsweise N-[3-(Dimethylamino)prcφyl]-N'-ethyl-carbodiirnide- hydrochlorid, N,N'-Di-sec-butyl-carbodiimid, N^'-Dicyclohexylcarbodümid, N,N'-Diisopropylcarbodi- imid, l-(3-(p]methylammo)propyl)-3-ethyl-<arbcdiiniid-methiodid, 2-Bromo-3-ethyl-4-methyl-thiazolrum- tetrafhioroborat, N,N-Bis[2-oxo-3-oxazolidinyl]phosphorodiamidic Chloride, Chlor-tripyrrolidino-phos- phonium-hex∑fluoφhosphat, 0-(lH-Berizotriazol-l-yloxy)tris(d^e1hylarnino)phosphonium-hexafluor- phosphat, Brom-tripyrrolidino-phosphonium-hexafluorphosphat, O-(lH-Benzotriazol-l-yl)-N,N,N',N'- tetramethyluronium-hexafluorphosphat, 0-(lH-Benzc^azol-l-yl)-N,N,N\N'-bis(lB-ramelhylen)uromum- hexafluoφhoϊ phat, O-(lH-Benzotriazol-l-yl)-N,N,N',N'-bis(tetramethylen)urc)rdum-tetrafluorborat, N,N,N\N'-Bis(tetramemylen)cMorurcmium-tetrafluorborat, O-(7-A2abenzotriazol-l-yl)-N,N,N,N- tetramethyluronium hexafluoφhosphat und 1-Hydroxybenzotriazol. Diese Reagenzien können separat aber auch in Kombination eingesetzt werden.The process (a) according to the invention is optionally carried out in the presence of a suitable coupling reagent (when X 5 is hydroxy). As such, all common carbonyl activators come into question. These preferably include N- [3- (dimethylamino) propyl] -N'-ethyl-carbodiirnide hydrochloride, N, N'-di-sec-butyl-carbodiimide, N, N'-dicyclohexylcarbodiimide, N, N'-diisopropylcarbodiimide , 1- (3- (p) methylammo) propyl) -3-ethyl-aryldiimide methiodide, 2-bromo-3-ethyl-4-methylthiazolorum tetrafhioroborate, N, N-bis [2-oxo-3 -oxazolidinyl] phosphorodiamidic chlorides, chloro-tripyrrolidinophosphonium hexafluorophosphate, O- (1H-berizotriazol-1-yloxy) tris (d 1 -ethylamino) phosphonium hexafluorophosphate, bromo-tripyrrolidino-phosphonium hexafluorophosphate, O - (1H-benzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, 0- (1H-benzo-azol-1-yl) -N, N, N \ N'-bis ( lB-ramelhylene) uromum-hexafluorophosphate, O- (1H-benzotriazol-1-yl) -N, N, N ', N'-bis (tetramethylene) urc) tetrafluoroborate, N, N, N \ N'- Bis (tetramethylene) c Morurium tetrafluoroborate, O- (7-aza-benzotriazol-1-yl) -N, N, N, N-tetramethyluronium hexafluorophosphate and 1-hydroxybenzotriazole. These reagents can be used separately or in combination.
Die Reaktion stemperaturen 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 in carrying out the process (a) according to the invention in a wider 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 Durchfuhrung des erfindungsgemäßen Verfahrens (a) zur Herstellung der Verbindungen der Formel (I) s<rtzt man pro Mol des Carbonsäurehalogenids der Formel (B) im Allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 2 Mol an Amin der Formel (ED) ein. Die Aufarbeitung erfolgt nach üblichen Methoden.For carrying out the process (a) according to the invention for preparing the compounds of the formula (I), in general from 0.2 to 5 mol, preferably from 0.5 to 2 mol, of amine of the formula are obtained per mole of the carboxylic acid halide of the formula (B) (ED). The workup is carried out by conventional methods.
Als Verdürmiingsmittel 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, Methylcyclohexan, Benzol, Toluol, Xylcl oder Decalin; halogenierte Kohlenwasserstoffe, wie z.B. Chlorbenzol, DichlorbenzoL Dichlormethaα, Chloroform, Tetrachlormethan, Dichlorcthan oder Trichlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-tert-butylether, Methyl-tert-Amylether, Dioxan, Tetrahydrofuran, 1,2- Dimeth- oxyethan, 1,2-Diethoxyethan oder Anisol oder Amide, wie N,N-Dimethylformamid, N,N-Dimethyl- acetamid, N-Methylfortnanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid.Suitable diluents for carrying out process (b) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylcl or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorothan or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethy oxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylfortanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
Das erflnduiigsgemäße Verfahren (b) wird in Gegenwart einer Base durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Basen infrage. Hierzu gehören vorzugsweise Erdalkalimet dl- 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, Trietiylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N- Methylpiperidin, N-Methylmorpholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclcnonen (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 include, preferably, alkaline earth metal dl or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, e.g. Sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, kai- umacetat, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclcnone (DBN) or Diazabicycloundecene (DBU).
Die Reaktioristemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (b) in einem größeien Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen von O0C bis 1500C, vorzugsweise bei Temperaturen von 2O0C bis 11O0C.The Reaktioristemperaturen can be varied in carrying out the process (b) according to the invention in a large range. In general, 0 C, preferably at temperatures from O to 150 0 C at temperatures of from 2O 0 C and 11O 0 C.
Zur Durchftthrang des erfindungsgemäßen Verfahrens (b) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Pyrazolylcarboxamids der Formel (I-a) im Allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 2 Mol an Halogenid der Formel (IV) ein.To Durchftthrang the process (b) for preparing the compounds of formula (I) is used per mole of Pyrazolylcarboxamids of formula (Ia) is generally 0.2 to 5 moles, preferably 0.5 to 2 moles of halide of the formula (IV ) one.
Die erfindurgsgemäßen Verfahren (a) und (b) werden im Allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, unter erhöhtem oder vermindertem Druck - im Allgemeinen zwischen 0, I 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, I bar and 10 bar.
Die erfinduiigsgemäßen 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 erfinduigsgemäßen substances have a strong microbicidal activity and can be used for controlling unwanted microorganisms such as fungi and bacteria in crop protection and in the protection of materials.
Fungizide lassen sich im Pflanzenschutz zur Bekämpfung von Plasmodiophoromycetes, Oomycetes, Chytridiomvcetes, Zygomycetes, Ascomycetes, Basidiomycetes und Deuteromycetes einsetzen.Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomvcetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bakterizide lassen sich im Pflanzenschutz zur Bekämpfung von Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae und Streptomycetaceae einsetzen. 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; Podosphaera -Arten, wie beispielsweise Podosphaera leucotricha; Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fuliginea; Uncinula-Ar ;en, wie beispielsweise Uncinula necator;Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae. By way of example but not limitation, some pathogens of fungal and bacterial diseases, which fall under the above-mentioned generic terms, called: diseases caused by pathogens of powdery mildew such as Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula ars, 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-Arcen, wie beispielsweise Hemileia vastatrix;Hemileia Arcen, such as Hemileia vastatrix;
Phakopsora- Arten, wie beispielsweise Phakopsora pachyrhizi und Phakopsora meibomiae;Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae;
Puccinia-Arlen, wie beispielsweise Puccinia recondita oder Puccinia graminis;Puccinia arlen 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;
Phytophthori-Arten, wie beispielsweise Phytophthora infestans; Plasmopara- Arten, wie beispielsweise Plasmopara viticola;Phytophthori 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-Arlen, wie beispielsweise Pythium ultimum;Pythium arlen such as Pythium ultimum;
Blattfleckenlcrankheiten 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;
Cladosporiutn-Arten, wie beispielsweise Cladosporium cucumerinum;Cladosporiutn 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);
Colletotrichiim-Arten, wie beispielsweise Colletotrichum lindemuthanium;Colletotrichiim 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-Artcn, wie beispielsweise Elsinoe fawcettii; Gloeosporiυm-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; Guignardia-Arten, wie beispielsweise Guignardia bidwelli; Leptosphaerii-Arten, wie beispielsweise Leptosphaeria maculans; Magnaporthe -Arten, wie beispielsweise Magnaporthe grisea;Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaerii species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea;
Mycosphaerdla-Arten, wie beispielsweise Mycosphaerella graminicola und Mycosphaerella fijiensis; Phaeosphaeria-Arten, wie beispielsweise Phaeosphaeria nodorum; Pyrenophora Arten, wie beispielsweise Pyrenophora teres; Ramularia-Arten, wie beispielsweise Ramularia collo-cygni; Rhynchospoiium-Arten, wie beispielsweise Rhynchosporium secalis; Septoria-Artcn, wie beispielsweise Septoria apii; Typhula-Artiai, wie beispielsweise Typhυla incamata; Venturia-Artsn, wie beispielsweise Venturia inaequalis;Mycosphaerdla 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; Rhynchospoiium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii; Typhula artiai, such as Typhila incamata; Venturia Arts, such as Venturia inaequalis;
Wurzel- und Stengelkrankheiten, hervorgerufen durch z.B.Root and stem diseases caused by e.g.
Corticium-Arten, wie beispielsweise Corticium graminearum; Fusarium-Aiten, wie beispielsweise Fusarium oxysporum;Corticium species, such as Corticium graminearum; Fusarium Aiten, such as Fusarium oxysporum;
Gaeumannoriyces-Arten, wie beispielsweise Gaeumannomyces graminis;Gaeumannoriyces 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;
Thielaviopsi;-Arten, wie beispielsweise Thielaviopsis basicola;Thielaviopsi; species such as Thielaviopsis basicola;
Ähren- und Itispenerkrankungen (inklusive Maiskolben), hervorgerufen durch z.B.Ears and itispens (including corncob) caused by e.g.
Alternaria-Arten, wie beispielsweise Alternaria spp.;Alternaria species, such as Alternaria spp .;
Aspergillus-, \rten, wie beispielsweise Aspergillus flavus;Aspergillus, such as Aspergillus flavus;
Cladosporiuin-Arten, wie beispielsweise Cladosporium cladosporioides; Claviceps-Arten, wie beispielsweise Claviceps puφurea;Cladosporiuin species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps puφurea;
Fusarium-Aiten, wie beispielsweise Fusarium culmorum;Fusarium Aiten, 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;
Erkrankungfn, hervorgerufen durch Brandpilze wie z.B.Diseases caused by fire fungi, e.g.
Sphacelσtheoa-Arten, wie beispielsweise Sphacelotheca reiliana;Sphacelσtheoa species, such as Sphacelotheca reiliana;
Tilletia-Arteα, wie beispielsweise Tilletia caries;Tilletia species, such as Tilletia caries;
Urocystis-Arten, wie beispielsweise Urocystis occulta;Urocystis species, such as Urocystis occulta;
Ustilago-Arlen, wie beispielsweise Ustilago nuda;Ustilago arlen, such as Ustilago nuda;
Fruchtfäule tiervorgerufen durch z.B. Aspergillus-Arten, wie beispielsweise Aspergillus flavus; Botrytis-Arten, wie beispielsweise Botrytis cinerea;Fruit rot animal caused by eg Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea;
Penicilliurn-Arten, wie beispielsweise Penicillium expansum und Penicillium purpurogenum; Sclerotinia-Arten, wie beispielsweise Sclerotinia sclerotioram; Verticilium-Arten, wie beispielsweise Verticilium alboatrum;Penicilli species such as Penicillium expansum and Penicillium purpurogenum; Sclerotinia species such as Sclerotinia sclerotioram; Verticilium species such as Verticilium alboatrum;
Samen- und bodenbürtige Fäulen und Welken, sowie SämlingserkrankungeiL, hervorgerufen durch z.B. Fusarium-Arten, wie beispielsweise Fusarium culmorum; Phytophthora Arten, wie beispielsweise Phytophthora cactorum; Pythium-Artun, wie beispielsweise Pythium ultimum;Seed and soil rots and wilts, as well as seedling diseases caused by e.g. Fusarium species such as Fusarium culmorum; Phytophthora species, such as Phytophthora cactorum; Pythium artun, such as Pythium ultimum;
Rhizoctonia- Arten, wie beispielsweise Rhizoctonia solani; Sclerotium-Arten, wie beispielsweise Sclerotium rolfsii;Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii;
Krebserkranlαmgen, Gallen und Hexenbesen, hervorgerufen durch z.B. Nectria-Arten, wie beispielsweise Nectria galligena;Krebserkranlαmgen, galls and witches broom, caused by e.g. Nectria species, such as Nectria galligena;
Welkeerkrankungen hervorgerufen durch z.B. Monilinia-Aften, wie beispielsweise Monilinia laxa; Deformationen von Blättern, Blüten und Früchten, hervorgerufen durch z.B. Taphrina-Aiten, wie beispielsweise Taphrina deformans;Wilt diseases caused by e.g. Monilinia afts such as Monilinia laxa; Deformations of leaves, flowers and fruits caused by e.g. Taphrina Aiten, such as Taphrina deformans;
Degeneratioiiserkrankungen 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; Hehninthos])orium-Arten, wie beispielsweise Helminthosporiurn solani;Diseases of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani; Hehninthos]) orium species, such as Helminthosporiurn 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-Ar:en, wie beispielsweise Erwinia amylovora; Bevorzugt kennen 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 temiissima), Anthracnose (Colletotrichum gloeosporoidus dematium var. truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophoia leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera llight (Drechslera glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulüia Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Pod and Stern Blight (Phoinopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeia glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora paehyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphylium botryosum), Target Spot (Corynespora cassiicola)Diseases caused by bacterial pathogens such as Xanthomonas species, such as Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora; Preferably, the following diseases are known to be controlled by soy beans: fungal diseases on leaves, stems, pods and seeds caused, for example, by Alternaria leaf spot (Alternaria spec. Atrans temiissima), Anthracnose (Colletotrichum gloeosporoidus dematium var. Truncatum), Brown spot (Septoria glycines ), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophoia leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera llight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulüia Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Pod and Star Blight (Phoinopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeia glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora paehyrhizi), Scab (Sphaceloma glycines), Stemphylium Leaf Blight (Stemphyl ium botryosum), Target Spot (Corynespora cassiicola)
Pilzkrankhei:en an Wurzehi 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 vasinfeeta), Pod and Stern Blight (Diaporthe phaseolorum), Stern Canker (Diaporthe phaseolorum var. caulivora), Phytophthora Rot (Phytophthora megasperma), Brown Stern Rot (Phialophora gregata), Pythium Rot (Pythium aphanidermatum, Pythium irreguläre, rythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Rot, Stern Decay, and Damping-Off (Rhizoctonia solani), Sclerotinia Stern Decay (Sclerotinia sclerotiorurr), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot (Thielaviopsis basicola).Fungus diseases on roots and stalk bases 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 vasinfeeta), Pod and Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var. Caulivora), Phytophthora Red (Phytophthora megasperma), Brown Star Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, rythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Star Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Star Decay (Sclerotinia sclerotiorurr), 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 iaher zur Mobilisierung pflanzeneigener Abwehrkräfte gegen Befall durch unerwünschte Mikroorgan ismen.The active compounds according to the invention also have a strong tonic effect in plants. They are more suitable for mobilizing plant-own defenses against infestation by unwanted microorganisms.
Unter pflaEzenstärkenden (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, peat-enhancing substances (resistance-inducing substances) are substances which are capable of stimulating the defense system of plants in such a way that the treated plants, upon subsequent inoculation with unwanted microorganisms, exhibit extensive resistance to these microorganisms.
Unter unerwünschten Mikroorganismen sind im vorliegenden Fall phytopathogene Pilze, Bakterien und Viren j:u 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 Allgemeiren von 1 bis 28 Tage, vorzugsweise 1 bis 14 Tage, besonders bevorzugt 1 bis 7 Tage nach der Behandlung der Pflanzen mit den Wirkstoffen.Unwanted microorganisms in the present case are phytopathogenic fungi, bacteria and viruses. The substances according to the invention can therefore be used to plants within a certain period of time after treatment to protect against infestation by said pathogens. The period within which protection is 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.
Die gute Pflϊnzenverträglichkeit der Wirkstoffe in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behandlung von oberirdischen Pflanzenteilen, von Pflanz- und Saatgut, und des Bodens.The good plant compatibility of the active ingredients in the concentrations necessary for the control of plant diseases allows a 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 GetreidekranlJieiten, wie z.B. gegen Puccinia-Arten und von Krankheiten im Wein-, Obst- und Gemüseanbau, wie z.B. gegen Bσtrytis-, Venturia- oder Alternaria-Arten, einsetzen.In this case, the active compounds according to the invention can be used with particularly good success for combating cereal cranial diseases, such as, for example, against Puccinia species and diseases in the wine, fruit and vegetable growing, such. against Bσtrytis, 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 erfinduEgsgemäßen 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.If appropriate, the active compounds according to the invention can 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 employed as intermediates and precursors for the synthesis of further active ingredients.
Erfindungsgsmäß können alle Pflanzen und Pflanzenteüe 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 biotedinologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten wei den 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, Fruchtkörpe*, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilsn gehört auch Emtegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.Erfindungsgsmäß all plants and Pflanzenteüe 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 means of bio-detec- tological and genetic engineering methods or combinations of these methods, including transgenic plants and including plant varieties that can be protected or not protected by plant variety rights. Plant parts are understood to mean all aboveground and subterranean parts and organs of plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies *, fruits and seeds, and roots, tubers and rhizomes , The plant parts also include emmentals as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfinduiigsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Be- handlungsmeihoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen und bei Verniehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.The erfinduigsgemäße treatment of plants and parts of plants with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual For example, by immersion, spraying, evaporation, nebulization, scattering, brushing and Verniehrungsmaterial, especially in seeds, by one or more layers wrapping.
Im Material: ϊchutz lassen sich die erfindungsgemäßen Stoffe zum Schutz von technischen Materialien gϊgen Befall und Zerstörung durch unerwünschte Mikroorganismen einsetzen.In the material: protection, the substances according to the invention can be used for the protection of industrial materials against infestation and destruction by undesired microorganisms.
Unter technischen Materialien sind im vorliegenden Zusammenhang nichtlebende Materialien zu verstehen, die für die Verwendung in der Technik zubereitet worden sind. Beispielsweise können technische Materialien, cie durch erfindungsgemäße Wirkstoffe vor mikrobieller Veränderung oder Zerstörung geschützt werden sollen, Klebstoffe, Leime, Papier und Karton, Textilien, Leder, Holz, Anstrichmittel und Kunststoffartikel, Kühlschmierstoffe und andere 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 Materiahen vorzugsweise Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Anstrichmittel, Kühlschmierrnittel und Wärmeübertragungsflüssigkeiten genannt, besonders bevorzugt Holz.Technical materials as used herein mean non-living materials that have been prepared for use in the art. For example, technical materials which are to be protected from 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 may be attacked or decomposed by microorganisms , 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, as technical materials adhesives, glues, papers and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids are preferably mentioned, with particular preference wood.
Als Mikroorganismen, die einen Abbau oder eine Veränderung der technischen Materialien bewirken kön- nen, seien beispielsweise Bakterien, Pilze, Hefen, Algen und Schleimorganismen genannt. Vorzugsweise wirken die erBndungsgemäßen Wirkstoffe gegen Pilze, insbesondere Schimmelpilze, holzverfärbende und holzzerstöreraie Pilze (Basidiomyceten) sowie gegen Schleimorganismen und Algen.As microorganisms which can cause degradation or alteration of the technical materials, mention may be made, for example, of bacteria, fungi, yeasts, algae and slime organisms. 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 Alternaria tenuis,There may be mentioned, for example, microorganisms of the following genera: Alternaria, such as Alternaria 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, wiu Lentinus tigrinus, Penicillium, wie Penicillium glaueum,Lentinus, wiu Lentinus tigrinus, Penicillium, like Penicillium glaueum,
Polyporus, vtie Polyporus versicolor,Polyporus, v. Polyporus versicolor,
Aureobasidiiim, wie Aureobasidium pullulans,Aureobasidium, such as Aureobasidium pullulans,
Sclerophom∑i, 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, Staphylococcus, wie Staphylococcus aureus.Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.
Die WirkstoiFe können in Abhängigkeit von ihren jeweiligen physikalischen und/ oder chemischen Eigenschaften in die üblichen Formulierungen überfuhrt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-KaIt- und Waπnnebel-Formulierungen.Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV -KaIt- and Waπnnebel formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/ oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Ln Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hüfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im Wesentlichen infrage: Aromaten, wie Xylol, Toluol oder Alkyl- naphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylenc; oder Methylenchlorid, aliphatische Kohlenwasserstoffe, 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 Dimethyl- formamid uni Dimethylsulfoxid, sowie Wasser. Mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasför- mig sind, z.H. 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 bochdisperse Kieselsäure, Aluminiumoxid und Silikate. Als feste Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Bims, Marmor, Sepio- üth, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnussschalen, Maiskolben und Tabakstängel. Als Emulgicr und/oder schaumerzeugende Mittel kommen infrage: z.B. nichtionogene und aniαnische Emulgatoren, wie Polyoxyethylen-Fettsäureester, Polyoxyethylen-Fettalkoholether, z.B. Alkylarylpolyglycolether, Alkyl- sulfonate, Alkylsulfate, Arylsulfαnate sowie Eiweißhydrolysate. Als Dispergiermittel kommen infrage: z.B. Lignin-Sulfii ablaugen und MethylceUulose.These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as extender, e.g. also organic solvents can be used as Hüfslösungsmittel. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenec; or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and water. By liquefied gaseous diluents or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, i. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: e.g. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, pumice, marble, sepia, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems. Emulgicr and / or foam-forming agents are suitable: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylarylpolyglycolether, alkyl sulfonates, alkyl sulfates, Arylsulfαnate and protein hydrolysates. Suitable dispersants are: e.g. Lignin Sulfii leach and MethylceUulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvϊrige, körnige oder latexfbrmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein. 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.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids may be used in the formulations. Other additives may be mineral and vegetable oils. Dyes such as inorganic pigments such as 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 can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise: zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formulierungen auch in Mischung mit bekannten Fungiziden, Bakteriziden, Akariziden, Nematiziden oder Insektiziden verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern oder Resistenzentwicklungen vorzubeugen. In vielen Fällen erhält man dabei synergistische Effekte, d.h. die Wirksamkeit der Mischung isl größer als die Wirksamkeit der Einzelkomponenten.The active compounds according to the invention, as such or in their formulations, can also be used in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance. In many cases synergistic effects, i. E. the effectiveness of the mixture isl greater than the effectiveness of the individual components.
Als Mischpartner kommen zum Beispiel folgende Verbindungen infrage: Fungizide:For example, the following compounds are suitable as mixed partners: Fungicides:
1) Inhibitoriai der Nukleinsäuresynthese: z.B. Benalaxyl, Benalaxyl-M, Bupirimate, Clozylacon, Dimethirimcl, Ethirimol, Furalaxyl, Hymexazol, Mefenoxam, Metalaxyl, Metalaxyl-M, Ofurace, Oxadixyl, Oxolinic acid;1) inhibitor of nucleic acid synthesis: e.g. Benalaxyl, Benalaxyl-M, Bupirimate, Clozylacone, Dimethirimcl, Ethirimol, Furalaxyl, Hymexazole, Mefenoxam, Metalaxyl, Metalaxyl-M, Ofurace, Oxadixyl, Oxolinic acid;
2) Inhibitoren von Mitose und Zellteilung: z.B. Benomyl, Carbendazim, Diethofencarb, Ethaboxam, Fuberidazol;, Pencycuron, Thiabendazole, Thiophanate-methyl, Zoxamide;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):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; 3.3) Inhibitoren am Komplex in der Atmungskette: z.B. Amisulbrom, Azoxystrobin, Cyazofamid, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidone, Fluoxastrobin, Kresoxim-methyl, Metomino- strobin, Or) sastrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin;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) inhibitors on the complex in the respiratory chain: e.g. Amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metomino-strobin, orsastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin;
4) Entkoppler: z.B. Dinocap, Fluazinam, Meptyldinocap;4) decoupler: e.g. Dinocap, fluazinam, meptyldinocap;
5) Inhibotorm der ATP Produktion: z.B. Fentin acetate, Feπtin chloride, Feπtin hydroxide, Silthiofäm; 6) Inhibitoren der Aminosäure- und Protein-Biosynthese: z.B. Andoprim, Blasticidin-S, Cyprodinil, Kasugamycin, Kasugamycin hydrochloride hydrate, Mepanipyrim, Pyrimethanil;5) Inhibitor of ATP production: e.g. Fentin acetate, Feπtin chloride, Feπtin hydroxide, Silthiofäm; 6) Inhibitors of amino acid and protein biosynthesis: e.g. Andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil;
7) Inhibitorai der Signaltransduktion: z.B. Fenpiclonil, Fhidioxonil, Quinoxyfen;7) Signal transduction inhibitor: e.g. Fenpiclonil, fhidioxonil, quinoxyfen;
8) Inhibitcren der Lipid- und Membran-Synthese: z.B. Biphenyl, Chlozolinate, Edifenphos, Iodocarb, Iprobenfos, Iprodione, Isoprothiolane, Procymidone, Propamocarb, Propamocarb hydrochloride, Pyrazophos, Tolclofos-methyl, Vinclozolin; 9) Inhibitoren der Ergosterol-Biosynthese: z.B. Aldimoiph, Azaconazole, BitertanoL, Bromuconazole, Cyproconazole, Diclobutrazole, Difenoconazole, Diniconazole, Diniconazole-M, Dodemorph, Dodemorph acetate, Epoxiconazole, Etaconazole, Fenarimol, Fenbuconazole, Fenhexarnid, Fenpropidin, Fenpropimorph, Fluquinconazole, Flurprimidol, Flusilazole, Flutriafol, Furconazole, Furconazole-cis, Hexaconazole, hnazalil, Imazalil sulfate, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Naftifine, Nuarimol, Oxpoconazole, Paclobutrazol, Pefurazoate, Penconazole, Prochloraz, Propiconazole, Prothioconazole, Pyributicarb, Pyrifenox, Simeconazole, Spiroxatnine, Tebuconazole, Terbinafine, Tetraconazole, Triadimefon, Triadimenol, Tridemorph, Triflumizole, Triforine, Triticonazole, Uniconazole, Viniconazole, Voriconazole; 10) Inhibitoren der Zellwandsynthese: z.B. Benthiavalicarb, Dimethomorph, Flumorph, Iprovalicarb, Polyoxins, Pcilyoxorim, Validarnycin A;8) inhibitors of lipid and membrane synthesis: eg biphenyl, chlozolinates, edifenphos, iodocarb, Iprobenfos, iprodione, isoprothiolanes, procymidones, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl, vinclozolin; 9) Inhibitors of ergosterol biosynthesis: eg aldimoiph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexarnide, fenpropidin, fenpropimorph, fluquinconazole, Flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, hnazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazole, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, simeconazole , Spiroxatnine, Tebuconazole, Terbinafine, Tetraconazole, Triadimefon, Triadimenol, Tridemorph, Triflumizole, Triforine, Triticonazole, Uniconazole, Viniconazole, Voriconazole; 10) inhibitors of cell wall synthesis: eg Benthiavalicarb, Dimethomorph, Flumorph, Iprovalicarb, Polyoxins, Pcilyoxorim, Validarnycin A;
11) Inhibitoien der Melanin-Biosynthese: z.B. Carpropamid, Diclocymet, Fenoxanil, Phthalide, Pyroquilon, Tricyclazole;11) Inhibitors of melanin biosynthesis: e.g. Carpropamide, diclocymet, fenoxanil, phthalides, pyroquilon, tricyclazole;
12) Resisten2induktoren: z.B. Acibenzolar-S-methyl, Probenazole, Tiadinil; 13) Verbindungen mit MuMsite-Aktivität: z.B. Bordeaux Mixture, Captafol, Captan, Chlorothalonil, Copper naphthenate, Copper oxide, Copper oxycbJoride, Kupferzubereitungen wie z.B. Kupferhydroxid, Kupiersulfat, Dichlofluanid, Dithianon, Dodine, Dodine free base, Ferbam, Fluorofolpet, Folpet, Guazatine, Guazatine acetate, Iminoctadine, Iminoctadine albesilate, [minoctadine triacetate, Mancopper, Mancozeb, Maneb, Metiram, Metiram Zinc, Oxine-Copper, Propineb, Sulphur und Schweferlzubereitungen wie z.B. Calcium polysulphide, Thiram, Tolylfluanid, Zineb, Ziram;12) Resist2inductors: e.g. Acibenzolar-S-methyl, Probenazoles, Tiadinil; 13) Compounds with MuMsite activity: e.g. Bordeaux Mixture, Captafol, Captan, Chlorothalonil, Copper naphthenate, Copper oxide, Copper oxycoboride, Copper Preparations such as e.g. Copper hydroxide, cupric sulfate, dichlofluanid, dithianone, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, [minoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, propineb , Sulfur and Schweferlzubereitungen such as Calcium polysulphide, thiram, tolylfluanid, zineb, ziram;
14) eine Vertindung aus der folgenden Liste: (2E)-2-(2-{[6-(3-CWor-2-methylpheacocy)-5-fluoφyrirnidin- 4-yl]oxy}phaiyl)-2-(methoxyimino)-N^ethyla∞tamid, (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-Fluor-2-phe- nylvmyl]oxy}phenyl)eihyüden]anibo}oxy)me1hyl]phenyl}-2-(methoxyiniino)-N-^^ l-(4-14) is a compound from the following list: (2E) -2- (2 - {[6- (3-C-or-2-methylphacyc) -5-fluoropyridinyl-4-yl] oxy} -phaiyl) -2- (methoxyimino) -N'-ethyl-α-tamide, (2E) -2- {2 - [({[(LE) -l- (3 - {[(E) -l-fluoro-2-phenyl-nylmethyl) oxy} -phenyl) ] anibo} oxy) methyl] phenyl} -2- (methoxyiniino) -N - ^^ 1- (4-
Chlorpheayl) -2-(lH-l,2,4-triazol-l-yl)cycloheptanol, 2-(4-Chlorphenyl)-N-{2-[3-methoxy-4-(prop-2-yn- l-yloxy)phm^]ethyl}-2-<prop-2-yn-l-yloxy)acetarπid, l-[(4-Methoxyphenoxy)methyl]-2,2-dimethyl- prcρyl-lH-irradazol-l-carboxylat,2,3,5,6-TetracMoM-(methylsiitfonyl)ρyrid^ 2-Butoxy-6-iod-3-propyl- 4H-chromen-4-on, 2-CMor-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)rü∞tirjarnid, 2-Phenylphenol und Salze davon, 3,4,5-TricWorpyridin-2,6-dicarbonitril, 3,4-DicUor-N-(2-cyanophenyl)isothiazol-5- carboxamid, 3-[5-(4-CWoφhmyl)-2,3^1imethylisoxazolidin-3-yl]pyridin, 5-CMor-6-(2,4J6-triflu- orophenyl)-N -[(lR^l^^-trime^lprφylJtl^^ltiiazololljS-alpyrMdJn-T-anΗn, 5-Chlor-7-(4-methyl- piperidin^-l-yl)-6-(2,4,6-trifluorphenyl)[l,2,4]triazolo[l,5-a]pyrimidin, 5-Chlor-N-[(lR)-l,2-dime- thylpropyl]-6^2,4,6-trMuorphenyl)[l,2,4]triazolo[l,5-a]pyrinήdm-7-arnin, Benthiazole, 8-Hfydroxyquino- hnsulfet, Bethoxazin, Capsimycin, Carvone, Chinomethionat, Cufraneb, Cyflufenamid, Cymoxanil, Da- zomet, Deb∑icarb, Dichlorophen, Diclomezine, Dicloran, Difenzoquat, Difenzoquat Methylsulphate, Diphenylamiae, Ferimzone, Flumetover, Fhiopicolide, Fhioroπrride, Fiusulfamide, Fosetyl-Aluminium, Fosetyl-Calcωm, Fosetyl-Sodium, Hexachlorobenzene, Irumamycin, Methasulfocarb, Methyl (2-chlor-5- {(lE)-N-[(6-methylpyridin-2-yl)methoxy]ethaiiimidoyl}benzyl)caibain^ Methyl (2E)-2-{2-[({cyclopro- pyl[(4-methoxyphenyl)imino]methyl}iMo)methyl]phenyl}-3-methoxyaciylat, Methyl l-(2,2-dimethyl-2,3- dihydro-lH-iiiden-l-yl)-lH-imida2θl-5-carboxylat, Methyl 3-(4-chlorphenyl)-3-{[N-(isopropoxy- carbonyl)val>l]amino}propanoat, Methyl isothiocyanate, Metrafenone, Mildiomycin, N-(3',4'-Dichlor-5- fluort)iphenyl-2-yl)-3-(difluoπnethyl)-l-mdhyl-lH-pyrazol-4-carboxatnid, N-(3-Ethyl-3,5,5-trime- thylcyclohex5rl)-3-(foπnylamino)-2-hydroxybenzamid, N-(4-Chlor-2-nitrophenyl)-N-ethyl-4-methylben- zensulfonamid, N-[(5-Brom-3-cUoφyridin-2-yl)tneΛyl]-2,4^cMornicotinairiid, N-[l-(5-Brom-3-chlor- pyridin-2-yl)£!thyl]-2,4-dichlomicotmamid, N-[l-(5-Brom-3-chloφyridin-2-yl)ethyl]-2-fluor-4-iod- nicotinamid, N-[2-(4-{[3-(4-CMoφhenyl)prφ-2-yn-l-yl]o^}-3-mefthoxyphemyl)ethyl]-N2-(methylsulfo- nyl)valinamicl, N-{(Z)-[(Cyclcφropylmemoxy)imko][6-(difl^^ phenylacetaniid, N-{2-[3-CUor-5-(trifluormethyl)pyiidin-2-yl]ethyl}-2-(trifluormethyl)ben2ainid, Nata- mycin, Niels el Dimethyldithiocarbamate, Nitrothal-isopropyl, O-{l-[(4-Methoxyphenoxy)methyl]-2,2- dimethylpropyl} lH-Imidazol-l-caibothioat, Octhflinone, Oxamocarb, Oxyfenthiin, Peπtachlorphenol und Salze, Phosphorsäure und ihre Salze, Piperalin, Propamocarb Fosetylate, Propanosine-Sodium, Proquinazid, Pyrrolnitrine, Quiπtozene, Tecloftalatn, Tecnazene, Triazoxide, Trichlamide, Zaπlamid.Chloropheayl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, 2- (4-chlorophenyl) -N- {2- [3-methoxy-4- (prop-2-yn-1H) -yloxy) phm ^] ethyl} -2- <prop-2-yn-1-yloxy) acetylamide, 1- [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-1H-irradazole-1-carboxylate , 2,3,5,6-TetracMoM- (methylsulfonyl) pyrid ^ 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2-CMor-N- (1,1,3-trimethyl -2,3-dihydro-1H-inden-4-yl), rü∞tirjarnide, 2-phenylphenol and salts thereof, 3,4,5-tric-wormyridine-2,6-dicarbonitrile, 3,4-dicor-N- (2 cyano-phenyl) -isothiazole-5-carboxamide, 3- [5- (4-cyclohexa) -2,3,3-dimethylisoxazolidin-3-yl] pyridine, 5-CMor-6- (2,4- J- 6-trifluorophenyl) - N - [(lR ^ l ^^ - trime ^ lprφylJtl ^^ ltiiazololl j S-alpyrMdJn-T-anΗn, 5-chloro-7- (4-methylpiperidin ^ -l-yl) -6- (2,4 , 6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine, 5-chloro-N - [(lR) -l, 2-dimethylpropyl] -6 ^ 2,4,6- tri-fluorophenyl) [l, 2,4] triazolo [l, 5-a] pyridine-7-arnine, benthiazoles, 8-hydroxyquinoline sulfite, bethoxazine, capsimycin, carvone, quinomethionate, Cufraneb, cyflufenamid, cymoxanil, dazomet , Debialcarb, dichlorophen, diclomethine, diclorane, difenzoquat, difenzoquat methylsulphate, diphenylamiae, ferimzone, flumetover, fhiopicolide, fluorouripride, fiusulfamide, fosetyl-aluminum, fosetyl-calcωm, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methyl (2 chloro-5- {(IE) -N - [(6-methylpyridin-2-yl) methoxy] ethaneimidoyl} benzyl) caibain ^ methyl (2E) -2- {2 - [({cyclopropyl] (4-methoxyphenyl) imino] methyl iMo) methyl] phenyl} -3-methoxyaciylate, methyl 1- (2,2-dimethyl-2,3-dihydro-1H-iiidene-1-yl) -1H-imida2θl-5-carboxylate, methyl 3- (4 -chlorophenyl) -3 - {[N- (isopropoxycarbonyl) val> 1] amino} propanoate, methyl isothiocyanate, metrafenone, mildiomycin, N- (3 ', 4'-dichloro-5-fluoro) iphenyl-2-yl ) -3- (difluoπnethyl) -l-mdhyl-lH-pyrazol-4-carboxatnid, N- (3-ethyl-3,5,5-trimethyl- thylcyclohex5 r l) -3- (foπnylamino) -2-hydroxybenzamide, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methylbenzenesulfonamide, N - [(5-bromo-3-cocoo-2-pyridin-2-yl) -thyl] -2,4-c-mornicotinic acid, N- [ 1- (5-bromo-3-chloro-pyridin-2-yl) ethyl] -2,4-dichloromotomamide, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2 fluoro-4-iodo-nicotinamide, N- [2- (4 - {[3- (4-CMo-phenyl) -prφ-2-yn-1-yl] o ^} - 3-mehthoxyphemyl) ethyl] -N 2 - (methylsulfonyl) valinamicl, N - {(Z) - [(cyclopropylmemoxy) imo] [6- (diflxy) phenylacetamide, N- {2- [3-Cuor-5- (trifluoromethyl ) pyiidin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, natamycin, Niels dimethyldithiocarbamate, nitrothal isopropyl, O- {1- [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl} -1H Imidazole-1-caibothioate, octhflinones, oxamocarb, oxyfenthiine, pentachlorophenol and salts, phosphoric acid and its salts, piperaline, propamocarbosubstylate, propanosine-sodium, proquinazide, pyrrolonitrines, quinitecene, teclotalatn, tecnazenes, triazoxides, trichlamides, azamidamide.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarboiisäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboic 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 Carbaniate (z.B. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb. Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbo- furan, Carbosulfen, Chloethocarb, Coumaphos, Cyanofenphos, Cyanophos, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb) 1.2 Organophosphate (z.B. Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvirfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chlorethoxyfos, Chlorfenvin- phos, Chlo-mephos, Chlorpyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlor- fenvinphos. Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofeπthion, Dichlorvo&ODVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Etlioprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, FIu- pyrazofos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, lodofenphos, Iprobenfos, Isazofos, Is afenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Me- thamidophoä, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyV-ethyl), Pheothoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxirn, Piiimiphos (-methylAethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion)1.1 Carbanates (eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carboofuran, carbosulfen, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, Fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamates, trimethacarb, XMC, xylylcarb) 1.2 Organophosphates (eg, acephates, azamethiphos, azinphos (-methyl , -ethyl), bromophos-ethyl, Bromfenvirfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chlorethoxyfos, Chlorfenvin- phos, Chlo-mephos, Chlorpyrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos. Demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinon, dichlorofeπthione, dichloro & ODVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulphoton, EPN, ethion, etlioprophos, Etrimfos, Famphur, F enamiphos, fenitrothion, fensulfothion, fenthion, flurpyrazofos, fonofos, formothion, fosmethilane, fosthiazate, heptenophos, iodofenphos, ipamplesfos, Isazofos, Isaphos, Isopropyl O-salicylates, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophoä, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyV-ethyl), Pheothoates, Phorates, Phosalones, Phosmet, phosphamidon, phosphocarb, phoxirn, piiimiphos (-methylethyl), profenofos, propaphos, propetamphos, prothiofos, prothoates, pyraclofos, pyridaphenthione, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, Triclorfone, vamidothione)
2. Natrium- Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker2. 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, CbJo- vaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cycloprothrin, Cyflu- thrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, DDT, Deltamethriπ, EmpenthriB (lR-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrilhrin, Feα- valerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flmnethrin, Fluvalinate, Fubfenprox, Gamma- Cyhalothriii, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Peπnethrin (eis-, trans-), Phenothrin (lR-trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethriπ, Resmethrin, RU 15525, Sil.ifluofen, 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, cbJovaporthrin, cis-cypermethrin , Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthriB (lR-isomer), esfenvalerate, etofenprox , Fenfluthrin, fenpropathrin, fenpyrilhrin, faα valerates, flubrocythrinates, flucythrinates, flufenprox, flmnethrin, fluvalinates, fubfenprox, gamma-cyhalothriii, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, penidin (cis-, trans-), phenothrin (lR- trans isomer), prallethrin, profuthrin, protrifenbutene, pyresmethriπ, resmethrin, RU 15525, silylfluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralomethyrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum))
2.2 Oxadiazine (z.B. Indoxacarb)2.2 Oxadiazines (e.g., indoxacarb)
3. Acetylch olin-Rezeptor-Agonisten/-Antagonisten 3.1 Chloroαicotinyle/Neonicotinoide (z.B. Acetaαriprid, Clolhianidin, Dinotefuran, Imidacloprid, Ni- tenpyiam, Nithiazine, Tbiacloprid, Thiamethoxam) 3.2 Nicotine, Bensultap, Cartap3. Acetylcholine receptor agonists / antagonists 3.1 Chloroacotinyls / neonicotinoids (e.g., acetaαripride, clolhianidine, dinotefuran, imidacloprid, nitropyiamine, nithiazines, tbiacloprid, thiamethoxam) 3.2 Nicotine, Bensultap, Cartap
4. Acetylcliolin-Rezeptor-Modulatoren 4.1 Spinouyne (z.B. Spinosad) 5. GABA-gesteuerte Chlorid-Kanal-Antagonisten4. Acetylcliolin receptor modulators 4.1 Spinouyne (e.g., spinosad) 5. GABA-driven chloride channel antagonists
5.1 Cycloijiene Organochlorine (z.B. Caπφhechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor5.1 Cycloiodienes Organochlorines (e.g., calcium chloride, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
5.2 Fiprol; (z.B. Acetoprole, Etbiprole, Fipronil, Vaniliprole)5.2 Fiprol; (e.g., acetoprole, etbiprole, fipronil, vaniliprole)
6. Chloria-Kanal-Aktivatoren 6.1 Mectine (z.B. Abamectin, Avermectin, Emamectin, Emamectin-beαzoate, Ivermectin, Milbe- mectin, Milbemycin)6. Chloria Channel Activators 6.1 Mectins (e.g., abamectin, avermectin, emamectin, emamectin-beta-azate, ivermectin, milbemectin, milbemycin)
7. Juvenilhormon-Mimetika7. Juvenile hormone mimetics
(z.B. Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene) & Ecdysonagonisten/disruptoren(e.g., diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprenes) & ecdysone agonists / disruptors
8.1 Diacylhydrazine (z.B. Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide) P. Inhibitoren der Chitinbiosynthese8.1 diacylhydrazines (eg chromafenozides, halofenozides, methoxyfenozides, tebufenozides) P. inhibitors of chitin biosynthesis
9.1 Benzoylharnstoffe (z.B. Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, Tri- flumuron) 9.2 Buprofezin 9.3 Cyiomarine 10. Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren9.1 Benzoylureas (for example, bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron) 9.2 Buprofezin 9.3 Cyiomarins 10. Inhibitors of oxidative phosphorylation, ATP disruptors
10.1 Diafenthiυron10.1 Slide Door
10.2 Organ« rtine (z.B. Azocyclotin, Cyhexatin, Fenbutatin-oxide) 11. Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten10.2 Organotin (for example, azocyclotin, cyhexatin, fenbutatin oxides) 11. Decoupling of oxidative phosphorylation by interruption of the H proton gradient
11.1 Pyrroli; (z.B. Chlorfenapyr)11.1 Pyrroli; (e.g., chlorfenapyr)
11.2 Dinitrophenole (z.B. Binapacryl, Dinobuton, Dinocap, DNOC)11.2 Dinitrophenols (e.g., binapacryl, dinobutone, dinocap, DNOC)
12. Site-I-Elektronentransportinhibitoren12. Site I electron transport inhibitors
12.1 MEll's (z.B. Fenazaquin, Fenpyroximate, Pyrimidifeö, Pyridaben, Tebufenpyrad, Tolfenpyrad)12.1 MEll's (e.g., Fenazaquin, Fenpyroximate, Pyrimidifeo, Pyridaben, Tebufenpyrad, Tolfenpyrad)
12.2 Hydra methylnone12.2 Hydra methylnone
12.3 Dicofol12.3 Dicofol
13. Site-II-Elektronentransportinhibitoren 13.1 Rotenone 14. Site-III Elektronentransportinhibitoren13. Site II Electron Transport Inhibitors 13.1 Rotenone 14. Site III Electron Transport Inhibitors
14.1 Acequrnocyl, Fluacrypyrim14.1 Acecurnocyl, Fluacrypyrim
15. Mikrobielle Disruptoren der Insektendarmmembran Bacillus thuringiensis-Stämme15. Insect intestinal membrane microbial disruptors Bacillus thuringiensis strains
16. Inhibitoren der Fettsynthese 16.1 Tetroiisäuren. (z.B. Spirodiclofen, Spiromesifen)16. Inhibitors of Fat Synthesis 16.1 Tetroic Acids. (e.g., spirodiclofen, spiromesifen)
16.2 Tetramsäuren [z.B. 3-(2,5-Dimethylpheiιyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-eri-4-yl ethyl carbcinate (alias: Carbonic acid, 3-(2,5-dimethylphαiyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec- 3-en-4-yl eüiyl ester, CAS-Reg.-No.: 382608-10-8) and Carbonic acid, ris-3-(2,5-dirreÜiylpb.enyl)- 8-methoxy -2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl estαr (CAS -Reg. -No.: 203313-25-1)] 17. Carborximide (z.B. Flonicamid)16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-eri-4-yl ethylcarbinate (aka: Carbonic acid, 3- (2,5-dimethylphiyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl, ethyl ester, CAS Reg. No .: 382608-10-8) and carbonic acid, ris-3 ( 2,5-dirreilylphenyl) - 8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg. No .: 203313-25-1)] 17. Carborximides (eg flonicamide)
18. Oktopaminerge Agonisten (z.B. Amitraz)18. Octopaminergic agonists (e.g., Amitraz)
19. Inhibitoren der Magnesium-stimulierten ATPase (z.B. Propjigite)19. Inhibitors of Magnesium Stimulated ATPase (e.g., Propjigites)
20. Agonii ten des Ryanodin-Rezeptors, 20.1 Benzoesäuredicarboxamide [z.B. N2-[l,l-Dimethyl-2-(methylsulfonyl)ethyl]-3-iod-N1-[2- methyl-4-[l,2,2,2-tetrafluor-l-(trifluormethyl)ethyl]pheayl]-l,2-benzenedicarboxamide (CAS-Reg.- No.: 272451-65-7), Flubendiamide]20. agonists of the ryanodine receptor, 20.1 Benzoic dicarboxamides [eg N 2 - [l, l-dimethyl-2- (methylsulphonyl) ethyl] -3-iodo-N 1 - [2-methyl-4- [l, 2,2,2-tetrafluoro-l- ( trifluoromethyl) ethyl] pheayl] -1,2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7), flubendiamide]
20.2 Anthraoilamide (z.B. DPX E2Y45 = 3-Brom-N-{4-chlor-2-methyl-6-[(mdhylamino)carboii>'l]- phenyl}-l-(3 cblorpyridin-2-yl)-lH-pyrazol-5-carboxamid)20.2 Anthraoilamides (eg DPX E2Y45 = 3-bromo-N- {4-chloro-2-methyl-6 - [(methylamino) carboii] 1] -phenyl} -1- (3-cpyrorpyridin-2-yl) -H- pyrazole-5-carboxamide)
21. Nereistoxin-Analoge21. Nereistoxin Analogs
(z.B. Thiocyclam hydrogen Oxalate, Thiosultap-sodium)(e.g., thiocyclam hydrogen oxalate, thiosultap-sodium)
22. Biologika, Hormone oder Pheromone22. Biologics, hormones or pheromones
(z.B. Azadή achtin, Bacillus spec, Beauveria spec., Codlemone, Metarrhizium spec., Paecilomyces spec, Thuriigiensin, Verticillium spec.)(e.g., Azadή eightin, Bacillus spec, Beauveria spp., Codlemone, Metarrhicon spec., Paecilomyces sp., Thuriigiensin, Verticillium spec.)
23. Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen23. Active substances with unknown or non-specific mechanisms of action
23.1 (z.B. Aluminium phosphide, Methyl bromide, Sulfuryl fluoride)23.1 (eg aluminum phosphides, methyl bromides, sulfuryl fluorides)
23.2 Selektive Fraßhemmer (z.B. Cryolite, Flonicamid, Pymetrozine)23.2 Selective feeding inhibitors (e.g., cryolites, flonicamid, pymetrozines)
23.3 Milben Wachstumsinhibitoren (z.B. Clofentezine, Etoxazole, Hexythiazox) 23.4 Amidcflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chinome- thionat, Clύordimeform, Chlor ob enzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Hydramethyl- none, Japoidlure, Metoxadiazσne, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, femer die Verbindung 3-Meihyl-rAenyl-propylcarbamat (Tsumacide Z), die Verbindung 3-(5-Chlor-3-pyridinyl)-8-(2,2,2- trifluorethyrι-8-azabicyclo[3.2.1]octan-3-carborjitril (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 PQanzenextrakte, Nematoden, Pilze oder Viren enthalten.23.3 mite growth inhibitors (eg clofentezine, etoxazole, hexythiazox) 23.4 amidcflumet, benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, clordordimeform, chlorobenzenate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimines, Flufenerim, Flutenzin, Gossyplure, Hydramethylone, Japoidlure, Metoxadiazσne, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin, the compound 3-Meihyl-rAenyl-propylcarbamat (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoro-ethyl-8-azabicyclo [3.2.1] octane-3-carboronitrile (CAS Reg. No. 185982 -80-3) and the corresponding 3-endo-isomer (CAS Reg. No. 185984-60-5) (see WO 96/37494, WO 98/25923), as well as preparations which insecticidally effective PQanzenextrakte, nematodes , Fungi or viruses included.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstums regulatoren, Safener bzw. Semiochemicals ist möglich.A mixture with other known active ingredients, 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 antimykotiϊiche Wirkungen auf. Sie besitzen ein sehr breites antiinykotiscb.es Wirkungsspektrum, insbesondere gegen Dermatophyten und Sprosspilze, Schimmel und diphasische Pilze (z.B. gegen Candida-Spezies wie Candida albicans, Candida glabrata) sowie Epidermophyton floccosum, Aspergillus -Spezies wie Aspergillus niger und Aspergillus fumigatus, Trichophyton-Spezies wie Trichophyton mentagrophytes, Microsporon-Spezies wie Microsporon canis und audouinii. Die Aufzählung dieser Pilze stellt keinesfalls eine Beschränkung des erfassbaren mykotischen Spektrums dar, sondern hat nur erläuternden Charakter. Die Wirkst äffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Spritzpulver, Pasten, lösliche Pulver, Stäubemittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstäuben, Verschäumen, Bestrei- chen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low-Volume-V erfahren auszubringen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. Es kann auch das Sa atgut der Pflanzen behandelt werden.In addition, the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad antiinykotiscb.es spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character. The active substances 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 powders, dusts and granules. The application is carried out in a customary manner, for example by casting, spraying, spraying, scattering, dusting, foaming, spreading, etc. It is also possible to apply the active ingredients according to the ultra-low volume method or the active ingredient preparation or the active ingredient inject yourself into the ground. It can also treat the seeds of the plants.
Beim Einsatz der erfindungsgemäßen Wirkstoffe als Fungizide können die Aufwandmengen je nach Applikation sart innerhalb eines größeren Bereiches variiert werden. Bei der Behandlung vonWhen using the active compounds according to the invention as fungicides, the application rates can be varied within a relatively wide range, depending on the application. In the treatment of
Pflanzenteilen liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 undPlant parts are the application rates of active ingredient generally between 0.1 and
10.000 g/hfi, vorzugsweise zwischen 10 und 1.000 g/ha. Bei der Saatgutbehandlung liegen die10,000 g / hfi, preferably between 10 and 1,000 g / ha. In the seed treatment are the
Aufwandmiäigen 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.Effluent to active ingredient generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethc iden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensαten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff „Teile" bzw. „Teile von Pflanzen" oder „Pflanzenteile" wurde oben erläutertAs already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild or by conventional biological Bregenzmethc iden, such as crossing or protoplast fusion obtained plant species and plant varieties and their parts are treated. In a further preferred embodiment, transgenic plants and plant species which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above
Besonders bevorzugt werden 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 Wurzelsystεm, höhere Beständigkeit der Pflanzenart bzw. Pflanzensorte, gesteigertes Wachstum der Schösslinge, höhere Pflanzenvitalität, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Bliihleistung, 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 Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.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 Enhancement of the effect of the substances and agents which can be used according to the invention, better plant growth, further developed Root system, higher resistance of the plant species or plant variety, increased growth of the shoots, higher plant vitality, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity, increased Bliihleistung, easier harvesting, acceleration of maturity, 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 shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.
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 (5 Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte To1 eranz 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 Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. AIJ Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Baumwolle, Tabak, Raps sowie Obstpflanzen (mit den Früchten Apfel, 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 Schn≥cken 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 Akqurrierte 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 Phosphinothricin (z.B. "PAT"- Gen). Di^ jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kom- binationαi miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für „Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die tinter den Handelsbezeichnungen YIELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), BoIl gard® (Baumwolle), Nucoton® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glypho- sate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinothricin, 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 tue 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").The preferred transgenic (genetically engineered) plants or plant species 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 ( 5 "traits".) Examples of such properties are better plant growth. increased to 1 tolerance is to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and / or a higher nutritional value of the harvested products, better storage stability and / or Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or Vir and increased tolerance of the plants to certain herbicidal active substances. AIJ Examples of transgenic plants are the important crops, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apple, pear, citrus and grapes) mentioned, 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 (cf. a), CryIA (b), CryIA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (hereinafter "Bt plants"). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic activated resistance (SAR), systemin, phytoalexins, elicitors, and resistance genes and correspondingly expressed proteins and toxins. ) are further particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (eg "PAT" gene). The genes conferring the desired properties ("traits") can also occur in combination with one another in the transgenic plants, examples being "Bt plants" Maize varieties, cotton varieties, soybean varieties and potato varieties mentioned under the trade names YIELD GARD® (eg maize, cotton, soy), KnockOut® (eg maize), StarLink® (eg maize), BoIl gard® (cotton), Nucoton® (cotton ) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, eg rapeseed), IMI® ( Tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn). As herbicide-resistant (conventionally grown on herbicide tolerance) plants are also tue under the name Clearfield® marketed varieties (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 erfϊndungsgemäß mit den Verbindungen der allgemeinen Formel (I) bzw. den erfindungsgemäßen Wirkstofrmischungen 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 plants listed can be treated particularly advantageously erfϊndungsgemäß with the compounds of the general formula (I) or the drug 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.
HerstelluiH'sbeisnieleHerstelluiH'sbeisniele
Beispiel 1example 1
Bei Raumtemperatur werden 0.14 ml (1.65 mmol) Oxalsäuredichlorid zu einer Suspension von 285.2 mg (1.5 mmol) 3-(Difluormethyl)-l-ethyl-lH-pyrazol-4-carbonsäure in 9 ml Dichlormethan und 30 μl Dimethylformamid getropft. Die Reaktionsmischung wird für 2 Stunden bei Raumtemperatur gerührt, bevor eine Lösung bestehend aus 384.2 mg (1.5 mmol) 3',4'-Dichloro-5- fluorobiρhenyl-2-amin und 0.27 ml (1.95 mmol) Triethylamin in 9 ml Dichlormethan zugegeben werden. Nach 16 Stunden Rühren bei Raumtemperatur wird die Reaktionsmischung auf 10 ml Wasser gogeben, die organische Phase über Natriumsulfat getrocknet und im Vakuum aufkonzentriert. Man erhält nach Säulenchromatographie (Petrolether/Aceton 4:1) 640.2 mg (99 % der Theorie) N-(3^4'-DicWor-5-fluorbiphmyl-2-yl)-3-(difluormemyl)-l-ethyl-lH-pyrazol-4- carboxamicl [logP (pH 2.3) = 3.61].At room temperature, 0.14 ml (1.65 mmol) of oxalic acid dichloride are added dropwise to a suspension of 285.2 mg (1.5 mmol) of 3- (difluoromethyl) -1-ethyl-1H-pyrazole-4-carboxylic acid in 9 ml of dichloromethane and 30 μl of dimethylformamide. The reaction mixture is stirred for 2 hours at room temperature before adding a solution consisting of 384.2 mg (1.5 mmol) of 3 ', 4'-dichloro-5-fluorobiphenyl-2-amine and 0.27 ml (1.95 mmol) of triethylamine in 9 ml of dichloromethane , After stirring for 16 hours at room temperature, the reaction mixture is poured onto 10 ml of water, the organic phase dried over sodium sulfate and concentrated in vacuo. After column chromatography (petroleum ether / acetone 4: 1) 640.2 mg (99% of theory) of N- (3 ^ 4'-dicor-5-fluorobiphmyl-2-yl) -3- (difluoromethyl) -l-ethyl-lH pyrazole-4-carboxamicl [logP (pH 2.3) = 3.61].
Beispiel 2Example 2
Bei Raumtemperatur werden 0.14 ml (1.65 mmol) Oxalsäuredichlorid zu einer Suspension von 285.2 mg (1.5 mmol) 3-(DifluormeÜiyl)-l-ethyl-lH-pyrazol-4-carbonsäure in 9 ml Dichlormethan und 30 μl Dimethylformamid getropft. Die Reaktionsmischung wird für 2 Stunden bei Raumtempe- ratur gerülut, bevor eine Lösung bestehend aus 359.5 mg (1.5 mmol) 4'-Chlor-3',5-difiuorbiphenyl- 2-amin und 0.27 ml (1.95 mmol) Triethylamin in 9 ml Dichlormethan zugegeben werden. Nach 16 Stunden Rühren bei Raumtemperatur wird die Reaktionsmischung auf 10 ml Wasser gegeben, die organische Phase über Natriumsulfat getrocknet und im Vakuum aufkonzentriert. Man erhält nach Säulenchromatographie (Petrolether/Aceton 4:1) 477.0 mg (76 % der Theorie) N-(4'-Chlor-3',5-di- fluorbipheiyl-2-yl)-3-(difluoπnethyl)-l-ethyl-lH-pyrazol-4-carboxamid [logP (pH 2.3) = 3.34]. Analog den Beispielen 1 und 2 sowie entsprechend den allgemeinen Beschreibungen der erfindungsgemäßen Verfahren können die in der folgenden Tabelle 1 genannten Verbindungen der Formel (I) erhalten werden.At room temperature, 0.14 ml (1.65 mmol) of oxalic acid dichloride are added dropwise to a suspension of 285.2 mg (1.5 mmol) of 3- (difluoromethyl) -1-ethyl-1H-pyrazole-4-carboxylic acid in 9 ml of dichloromethane and 30 μl of dimethylformamide. The reaction mixture is stirred for 2 hours at room temperature before adding a solution consisting of 359.5 mg (1.5 mmol) of 4'-chloro-3 ', 5-difluorobiphenyl-2-amine and 0.27 ml (1.95 mmol) of triethylamine in 9 ml of dichloromethane be added. After stirring for 16 hours at room temperature, the reaction mixture is added to 10 ml of water, the organic phase dried over sodium sulfate and concentrated in vacuo. After column chromatography (petroleum ether / acetone 4: 1) 477.0 mg (76% of theory) of N- (4'-chloro-3 ', 5-di-fluorobipheiyl-2-yl) -3- (difluoπnethyl) -l- ethyl-1H-pyrazole-4-carboxamide [logP (pH 2.3) = 3.34]. Analogously to Examples 1 and 2 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
Die Bestirimυng der in den voranstehenden Tabellen und Herstellungsbeispielen angegebenen logP- Werte erfolgt gemäß EEC-Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromato.graphy) an einer Phasenumkehrsäule (C 18). Temperatur: 43°C.The determination of the log P values given 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 2 wischen 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 2 between two consecutive alkanones).
Die lambla-max-Werte wurden an Hand der UV-Spektren von 200 nm bis 400 mn in den Maxima der chroniatographischen Signale ermittelt. Anwendune s beis nieleThe lambla-max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chroniatographic signals. Applications do not apply
Beispiel AExample A
Puccinia - Test (Weizen) / protektiv Lösungsmitlei: 50 Gewichtsteile N,N-DimethylacetamidPuccinia - test (wheat) / protective Solvent: 50 parts by weight N, N-dimethylacetamide
Emulgator: 1 Gewichtsteil AlkylaiylpolyglykoletherEmulsifier: 1 part by weight of alkylaiyl polyglycol ether
Zur Herstel [ung 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.For the manufacture [ung a suitable preparation of active compound 1 part by weight active ingredient are 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 Konidiensuspension von Puccinia recondita besprüht. Die Pflanzen verbleiben 48 Stunden bei 20°C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain for 48 hours at 20 ° 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 nich der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigerj der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird.The evaluation takes place 10 days after inoculation. 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
Puccinia - Test (Weizen) / protektivPuccinia - test (wheat) / protective
Beispiel B Example B
Pyrenophora teres - Test (Gerste) / protektivPyrenophora teres - test (barley) / protective
Lösungsmittel: 50 Gewichtsteile N.N-DimetbylacetamidSolvent: 50 parts by weight N.N-dimetbylacetamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der Wirkstoffzubereitung in der angegeben Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer Konidiensuspension von Pyrenophora teres besprüht. Die Pflanzen verbleiben 48 Stunden bei 200C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine.To test for protective activity, young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain 48 hours at 20 0 C and 100% relative humidity in an incubation cabin.
Die Pflanzai werden dann in einem Gewächshaus bei einer Temperatur von ca. 200C und relativen Luftfeuchtigkeit von ca. 80 % aufgestellt.The Pflanzai are then placed in a greenhouse at a temperature of about 20 0 C and relative humidity of about 80%.
8 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.8 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 ItTable It
Pyrenophora teres - Test (Gerste) / protektivPyrenophora teres - test (barley) / protective
(1)(1)
Betspiel C Bet game C
Botrytis -1 est (Gurke) / protektivBotrytis -1 est (cucumber) / protective
Lösungsmittel: 49 Gewichtsteile N,N-DimethylfoππainidSolvent: 49 parts by weight of N, N-Dimethylfoππainid
Emulgator: 1 Gewichtsteil AlkylaiylpolyglykoletherEmulsifier: 1 part by weight of alkylaiyl polyglycol ether
Zur Herstellimg 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 produce a suitable preparation of active compound, 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 bespritzt man junge Gurkenpflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge. 1 Tag nach der Behandlung werden die Pflanzen mit einer Sporensuspension von Botrytis cinerea inokuliert und stehen dann 48h bei 100 % relativer Feuchte uni 200C. Anschließend stehen die Pflanzen bei 96 % relativer Luftfeuchtigkeit und einer Temperatur von 13°C.To test for protective activity, young cucumber plants are sprayed with the preparation of active compound in the stated application rate. 1 day after the treatment, the plants are inoculated with a spore suspension of Botrytis cinerea and are then 48 h at 100% relative humidity and 20 0 C. Then the plants are at 96% relative humidity and a temperature of 13 ° C.
5-6 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 i vir d.5-6 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 i vir d.
Tabelle CTable C
Botrytis - Test (Gurke) / protektivBotrytis test (cucumber) / protective
Wirkstoff Aufwandmenge Wirkungsgrad Erfindung .sgemäß an Wirkstoff in ppm in %Active substance Application rate Efficiency Invention According to active substance in ppm in%
Beispiel DExample D
Alternaria -Test (Tomate) / protektivAlternaria test (tomato) / protective
Lösungsmittel: 49 Gewichtsteile N,N-DimethylformamidSolvent: 49 parts by weight of N, N-dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit bespritzt man junge Tomatenpflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge. 1 Tag nach der Behandlung werden die Pflanzen mit einer Sporensuspension von Alternaria solani inokuliert und stehen dann 24h bei 100 % relativer Feuchte und 200C. Anschließend stehen die Pflanzen bei 96 % relativer Luftfeuchtigkeit und einer Temperatur von 200C.To test for protective activity, young tomato plants are sprayed with the preparation of active compound in the stated application rate. One day after the treatment, the plants are inoculated with a spore suspension of Alternaria solani and then stand for 24 h at 100% relative humidity and 20 0 C. Then the plants are at 96% relative humidity and a temperature of 20 0 C.
7 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird.7 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
Tabelle E'Table E '
Alternaria -Test (Tomate) / protektivAlternaria test (tomato) / protective

Claims

Patentansn ruche Patentansn ruche
1. Pyrazolylcarboxamide der Formel (T)1. pyrazolylcarboxamides of the formula (T)
in welcher in which
R' für Wasserstoff, d-Cg-Alkyl, d-Cβ-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Ci-C4-AIk- oxy-Ci-C4-alkyl, C3-C3-Cycloalkyl; d-Cβ-Halogenalkyl, C1-C4-Halogenalkylthio, Ci-C4-Halogenalkylsulfinyl, C)-C4-HalogenalkylsulfOnyl, Halogen-Ci-C4-alkoxy-Ci- C4-alkyl, d-Cs-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-d-alkyl, (d-Cs-Alkytycarbonyl-Ci-d-alkyl, (Ci-R 'is hydrogen, d-Cg-alkyl, d-Cβ-alkylsulfinyl, Ci-C6 alkylsulfonyl, Ci-C 4 -AIk- oxy-Ci-C 4 alkyl, C 3 -C 3 cycloalkyl; d-Cβ-haloalkyl, C 1 -C 4 haloalkylthio, Ci-C4-haloalkylsulfinyl, C) -C 4 -haloalkylsulfonyl, halo-Ci-C4-alkoxy-Ci- C4-alkyl, d-Cs-halocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 1 -d-alkyl, (C 1 -C 5 -alkytycarbonyl-C 1 -d-alkyl,
C3-Alkoxy)carbonyl-Ci-C3-alkyl; Halogen-(C1-C3-alkyl)carbonyl-Ci-C3-allQ'l> C 3 alkoxy) carbonyl-C 1 -C 3 -alkyl; Halogen- (C 1 -C 3 -alkyl) carbonyl-Ci-C 3 -allQ'l >
Halogen-(Ci-C3-alkoxy)carbonyl-Ci-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Ci-C8-Alkyl)carbonyl, (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-Halogenalkyl1hio)carbonyl, (Halogen-Ci-C4-alkoxy-Ci-C4- alkyl)carbonyl, (C3-C6-Halogenalkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)car- bonyl, (C3-Cg-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/ oder Bromatomen; oder -CH2-CsC-R1 A, -CH2-CH=CH-R1^, -CH=C=CH-R1^5 Halogeno (C 1 -C 3 -alkoxy) carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 8 -alkyl) carbonyl, (C 1 -C 8 -alkoxy) carbonyl, (C 1 -C 8 -alkylthio) carbonyl, (C 1 -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-Cβ-halo- alkoxy) carbonyl, (Ci-C 6 -Halogenalkyl1hio) 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 9 -halocycloalkyl) carbonyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; or -CH 2 -CsC-R 1 A , -CH 2 -CH = CH-R 1 ^, -CH = C = CH-R 1 ^ 5
-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 ,
Rl A für Wasserstoff, d-Cβ-Alkyl, Ci-C6-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C7-Cydoalkyl, (Ci-C4-Alkoxy)carbonyl, (C3-C6-Alkeαyloxy)carbonyl, (C3-C6- Alkinyloxy)carbonyl oder Cyano steht, R2 fiir Wasserstoff, Ci-Cg-Alkyl, Ci-C8-Alkoxy, C3-C8-Cy- doalkyl; Ci-C6-Halogenalkyl, Ci-Cβ-Halogenalkoxy, Halogen-Ci-C4-alkoxy-Ci-C4- alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom- atomen steht,R l A represents hydrogen, d-Cβ-alkyl, Ci-C 6 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 6 -alkyl, C 1 -C 8 -alkoxy, C 3 -C 8 -cycloalkyl; Ci-C 6 haloalkyl, Ci-Cβ-haloalkoxy, 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 stands,
R3 und R4 unabhängig voneinander jeweils fiir Wasserstoff, Ci-C8-Alkyl, Ci-C4-Alkoxy-C]- C4-alkyl, C3-C8-Cycloalkyl; Ci-C8-Halogenalkyl, Halogen-Ci-C4-alkoxy-Ci-C4- alkyl, Cs-Cs-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 3 and R 4 each independently represents hydrogen, Ci-C 8 alkyl, Ci-C 4 -alkoxy-C] - C 4 alkyl, C 3 -C 8 cycloalkyl; C 1 -C 8 -haloalkyl, halogeno-C 1 -C 4 -alkoxy-C 1 -C 4 - alkyl, Cs-Cs-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R3 lind 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 Heterocyclus 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 mono- or polysubstituted, identically or differently by halogen or C 1 -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-Cs-Alkyl, C3-C8-Cycloalkyl; Ci-C8- Halogenalkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 5 and R 6 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl; Ci-C 8 - haloalkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
R5 ijnd 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,R 5 and R 6 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
R7 für Wasserstoff oder Ci-Cβ-Alkyl steht,R 7 is hydrogen or C 1 -C 6 -alkyl,
M für einen einfach durch R8 substituierten Phenyl-Ring oder einen einfach durch R8"A substituierten Tbiophen-Ring steht,M represents a phenyl ring simply substituted by R 8 or a tbiophen ring which is monosubstituted by R 8 "A ,
R8 für Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluoπnethyl steht, R8 '* für Wasserstoff, Fluor, Chlor, Methyl, iso-Propyl, Methylthio oder Trifluoπnethyl steht,R 8 is fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl, R 8 ' * is hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,
R9 für Wasserstoff, Fluor oder Chlor steht, a) R10 für Ci-Cβ-Alkyl oder Ci-C6-Halogenalkyl mit 1 bis 13 Halogenatomen steht, uni R1 1 für Wasserstoff, C2-C6-Alkyl, Hydroxy-C2-C4-alkyl, C3-C6-Cycloalkyl> Ci-C4-Alkyl- thio-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, C2-C4-Halogenalkyl, Ci-C4-Halogenal- kylthio-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl mit jeweils 1 bis 9 Halogenatomen, (Ci-C8-Alkyl)caτbonyl, (Ci-C8-Alkoxy)carbonyl, (Ci-C8- Alkylthio)carbonyl, (Ci-C4-AIkOXy-C1 -C4-alkyl)carbonyl; (Ci-C6-Halogenalkyl)car- bonyl, (Ci-C6-Halogenalkoxy)carbonyl, (Ci-Cg-Halogenalkylthio^arbonyl, (Ha- logen-Ci-C4-alkoxy-Ci-C4-alkyi)carbonyl mit jeweils 1 bis 9 Halogenatomen steht, oder b) R10 für Cj-Cβ-Alkyl oder C2-C6-Halogenalkyl mit 1 bis 13 Halogenatomen steht, und R 1 für Wasserstoff, Ci-C6-Alkyl, Hydroxy-CrC4-alkyl, C3-C6-Cycloalkyl, Ci-C4-Alkyl- ihio-Ci-C4-alkyl, Ci -C4-AIkOXy-C1 -C4-alkyl, C1-C4-HaIOgCiIaIlCyI, Cj-C-Halogenal- kylthio-Ci-C4-alkyl, Ci-C4-Halogenalkoxy-Ci-C4-alkyl mit jeweils 1 bis 9 Halogenatomen, (Ci-C8-Alkyl)carbonyl, (Ci-C8-Alkoxy)carbonyl, (Ci-C8- Alkylthio)carbonyl, (C i-C4-Alkoxy-C i -C4-alkyl)carbonyl; (C2 -C6-HaI ogenalkyl)car- bonyl, (Ci-C6-Halogenalkoxy)carbonyl, (C1-C6-Halogenalkyltbio)carbonyl, (Ha- logen-Ci-C4-alkoxy-Ci-C4-alkyl)carbonyl mit jeweils 1 bis 9 Halogenatomen steht, m für 1, 2, 3, 4 oder 5 steht,R 9 represents hydrogen, fluorine or chlorine, a) R 10 is Ci-Cβ-alkyl, or Ci-C 6 haloalkyl having 1 to 13 halogen atoms, uni R 1 1 represents hydrogen, C 2 -C 6 alkyl, hydroxy C 2 -C 4 alkyl, C 3 -C 6 -cycloalkyl> Ci-C 4 alkyl thio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C 4 alkyl, C 2 - C 4 haloalkyl, Ci-C4 -Halogenal- alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl having in each case 1 to 9 halogen atoms, (Ci-C 8 -alkyl) caτbonyl , (Ci-C 8 alkoxy) carbonyl, (Ci-C 8 - alkylthio) carbonyl, (Ci-C 4 -alkoxy-C 1 -C 4 alkyl) carbonyl; (Ci-C 6 haloalkyl) carbonyl, (Ci-C 6 haloalkoxy) carbonyl, (Ci-Cg haloalkylthio ^ arbonyl, (halogen-Ci-C 4 -alkoxy-Ci-C 4 -alkyi) carbonyl having in each case 1 to 9 halogen atoms, or b) R 10 is C 1 -C 6 -alkyl or C 2 -C 6 -haloalkyl having 1 to 13 halogen atoms, and R 1 is hydrogen, C 1 -C 6 -alkyl, hydroxyl -C 4 alkyl, C 3 -C 6 cycloalkyl, Ci-C 4 alkyl ihio-Ci-C4-alkyl, Ci -C 4 -alkoxy-C 1 -C 4 alkyl, C 1 -C 4 - HaloCliAlCyI, Cj-C-haloal alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl having in each case 1 to 9 halogen atoms, (Ci-C 8 -alkyl) carbonyl, (Ci-C 8 alkoxy) carbonyl, (C -C 8 -alkylthio) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl; (C 2 -C 6 -Hal ogenalkyl) carbonyl, (Ci-C 6 haloalkoxy) carbonyl, (C 1 -C 6 -Halogenalkyltbio) carbonyl, (halogen-Ci-C4-alkoxy-Ci-C4- alkyl) carbonyl having in each case 1 to 9 halogen atoms, m is 1, 2, 3, 4 or 5,
R12 für Halogen, Cyano, Nitro, Amino, Hydroxy, Formyl, Carboxy, Carbamoyl, Tbio- carbamoyl, C,-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, Ci-C4-Alkoxy, C1-C4- Alkylthio, C,-C4-Alkylsulfinyl, Ci-C4-Alkylsulfonyl, C3-C6-Cycloalkyl, oder für Ci-C4-Halogenalkyl, Ci-C4-Halogenalkoxy, Ci-C-Halogenalkylthio, Ci-C4-HaIo- genalkylsulfinyl oder Ci-C4-Halogenalkylsulfonyl mit jeweils 1 bis 5 Halogenatomen, -(CH2)Si(CHs)3 oder -Si(CH3)3 steht, oder für -C(Q')=N-Q2 steht, worinR 12 represents halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, Tbio- carbamoyl, C, -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 4 alkoxy, C 1 -C 4 - alkylthio, C, -C 4 alkylsulfinyl, Ci-C 4 alkylsulfonyl, C 3 -C 6 cycloalkyl, or Ci-C 4 haloalkyl, Ci-C4-haloalkoxy , C-haloalkylthio, Ci-C 4 -HaIo- 4 haloalkylsulfonyl having in each case 1 to 5 halogen atoms, genalkylsulfinyl or C - (CH 2) Si (CHs) 3 or -Si (CH 3) 3; or is -C (Q ') = NQ 2 wherein
Q1 für Wasserstoff, Hydroxy, Ci -C4- Alkyl, Ci-C4-Halogenalkyl mit 1 bis 9Q 1 is hydrogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl having 1 to 9
Halogenatomen oder C3-C6-Cycloalkyl steht, Q2 für Hydroxy, Amino, Methylamino, Phenyl, Benzyl oder für jeweils gegebenenfalls durch Halogen, Cyano, Hydroxy, C]-C4-Alkoxy, Ci-C4-Alkylthio, d-C4-Alkyl- amino, Di(Ci-C4-alkyl)amino oder Phenyl substituiertes Ci-C4-Alkyl oder Ci-C4- Alkoxy, oder für C2-C4-Alkenyloxy oder C2-C4- Alkinyloxy steht, od a- für -SOnR13, -SO2NR14R13, -C(=X)R16, -Si(R17)3, -NR14R15, -CH2-NR14R15 steht, R1 J für Ci-C6- Alkyl oder Ci-C6-Halogenalkyl mit 1 bis 13 Halogenatomen steht, n für 1 oder 2 steht,Halogen atoms or C 3 -C 6 -cycloalkyl, Q 2 is hydroxy, amino, methylamino, phenyl, benzyl or in each case optionally by halogen, cyano, hydroxy, C] -C 4 alkoxy, Ci-C 4 alkylthio, dC 4- alkylamino, di (Ci-C 4 -alkyl) amino or phenyl-substituted Ci-C 4 alkyl or Ci-C 4 - alkoxy, or for C 2 -C 4 alkenyloxy or C 2 -C 4 - alkynyloxy or a- represents -SO n R 13 , -SO 2 NR 14 R 13 , -C (= X) R 16 , -Si (R 17 ) 3 , -NR 14 R 15 , -CH 2 -NR 14 R 15, R 1 J is C 6 -, alkyl or C 6 haloalkyl having 1 to 13 halogen atoms, n is 1 or 2;
R14 für Wasserstoff, Ci-C4-Alkyl oder -C(=X)R16 steht,R 14 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 16 ,
R15 für Wasserstoff, Ci-C4-Alkyl oder -C(=X)R16 steht,R 15 is hydrogen, C 1 -C 4 -alkyl or -C (= X) R 16 ,
R14 vmd R15 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oderR 14 vmd R 15 together with the nitrogen atom to which they are attached, one optionally mono- or polysubstituted by identical or different halogen or
C]-C4-Alkyl substituierten gesättigten Heterocydus mit 5 bis 8 Ringatomen bilden, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus derC] -C 4 -alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, wherein the heterocycle 1 or 2 further, non-adjacent heteroatoms of the
Reihe Sauerstoff, Schwefel oder NR7 enthalten kann,May contain oxygen, sulfur or NR 7 ,
X für O (Sauerstoff) oder S (Schwefel) steht, R16 für Wasserstoff, Ci-C4-Alkyl, C1-C4-AIkOXy oder -NR18R19 steht,X is O (oxygen) or S (sulfur), R 16 represents hydrogen, Ci-C 4 -alkoxy or -NR 18 R 19 is 4 alkyl, C 1 -C
R17 für Wasserstoff, Ci-C8-Alkyl, Ci-Cg-Alkoxy, C1-C4- Alkylthio-d-C^alkyl oder Ci-Cβ-Halogenalkyl steht, wobei die drei Reste R17 jeweils gleich oder verschieden sein können,R 17 is hydrogen, C 1 -C 8 -alkyl, C 1 -C -alkoxy, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl, where the three radicals R 17 may each be identical or different,
R 18 Wasserstoff oder Ci-C4- Alkyl steht, R19 Wasserstoff oder Ci-C4- Alkyl steht, R18 und R19 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oderR 18 is hydrogen or C 1 -C 4 -alkyl, R 19 is hydrogen or C 1 -C 4 -alkyl, R 18 and R 19 also together with the nitrogen atom to which they are attached, optionally one or more times, identically or differently, by halogen or
Ci-C4-AIkVl 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.Ci-C 4 -AlkVl substituted saturated heterocycle having 5 to 8 ring atoms form, wherein the heterocycle may contain 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 7 .
2. Vei fahren zum Herstellen von Pyrazolylcarboxamiden der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass man (a) Carbonsäurehalogenide der Formel (II)2. Vei go for the production of pyrazolylcarboxamides of the formula (I) according to claim 1, characterized in that (a) carboxylic acid halides of the formula (II)
in welcher in which
R9, R10 und Rn die in Anspruch 1 angegebenen Bedeutungen haben,R 9 , R 10 and R n have the meanings given in claim 1,
X1 für Halogen oder Hydroxy steht, mit Aminen der Formel (III)X 1 is halogen or hydroxy, with amines of the formula (III)
in welcher R1, M, R12 und m die in Anspruch 1 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 , M, R 12 and m 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) Pyrazolylcarboxamide der Formel (I-a)(b) pyrazolylcarboxamides of the formula (I-a)
in welcher in which
M, R9, R10, R11, R12 und m die in Anspruch 1 angegebenen Bedeutungen haben, mit Halogeniden der Formel (IV) R1 — HaI (IV) in welcherM, R 9 , R 10 , R 11 , R 12 and m have the meanings given in claim 1, with halides of the formula (IV) R 1 - Hal (IV) in which
R1 B für C1-C8-AIkVl, C,-C6-Alkylsulfmyl, Ci-Q-Alkylsulfonyl, Ci-C4-Alkoxy- Ci-C-alkyl, C3-C8-Cycloalkyl; C3-C6-Halogenalkyl, C,-C4-Halogenalkyl- thio, Ci-C-rHalogenalkylsulfinyl, Ci-GrHalogenalkylsulfonyl, Halogen-d- C4-alkoxy-C,-C4-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Ci-C3-alkyl, (CrC3-Alkyl)- carbonyl-Ci-C3-alkyl, (CrC3-Alkoxy)carbonyl-Ci-C3-alkyl; Halogen-(Cr C3-alkyl)carbonyl-d-C3-alkyl, Halogen-(Ci-C3-alkoxy)carbonyl-Ci-C3- alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Ci-C8-Alkyl)carbonyl, (Ci-Cg-Alkoxy)carbonyl, (C1-C3-Alkyltbio)carbonyl, (Ci-C4-Alkoxy-Ci-C4-alkyl)carbonyl, (C3-C6-Alkenyloxy)carbonyl, (C3-CO- Alkinyloxy)carbonyl, (C3-C8-Cycloalkyl)carbonyl; (Ci-Cβ-Halogenalkyl)- carbonyl, (Ci-C6-Halogenalkoxy)carbonyl, (Ci-C6-Halogenalkyltbio)car- bonyl, (Halogen-Ci-C4-alkoxy-Ci-C4-alkyl)carbonyl, (C3-C6-HaIOgBn- alkenyloxy)carbonyl, (C3-C6-Halogenalkinyloxy)carbonyl, (C3-C8-Halogen- cycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Brom- atomen; oder -CH2-CsC-R1 A, -CH2-CH=CH-R1 A, -CH=C=CH-R1 A, -C(=O)C(=O)R2, -CONR3R4 oder -CH2NR5R6 steht,R 1 B is C 1 -C 8 -alkyl, C 1 -C 6 -alkylsulfmyl, C 1 -C -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C -alkyl, C 3 -C 8 -cycloalkyl; C 3 -C 6 haloalkyl, C, -C 4 haloalkyl thio, C-rHalogenalkylsulfinyl, Ci-GrHalogenalkylsulfonyl, halo-d- C4-alkoxy-C, -C 4 alkyl, C 3 -C 8 Halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C 3 alkyl, (C r C 3 alkyl) - carbonyl-Ci-C 3 alkyl, (C r C 3 -alkoxy) carbonyl-Ci-C 3 alkyl; Halo (C r C 3 alkyl) carbonyl-dC 3 alkyl, halo (Ci-C 3 alkoxy) carbonyl-Ci-C 3 - alkyl having in each case 1 to 13 fluorine, chlorine and / or bromine atoms; (C 1 -C 8 -alkyl) carbonyl, (C 1 -C 6 -alkoxy) carbonyl, (C 1 -C 3 -alkyltbio) carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) carbonyl, (C 3 -C 4 -alkyl) carbonyl, C 6 alkenyloxy) carbonyl, (C 3 -C 10 alkynyloxy) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl; (Ci-Cβ-haloalkyl) - carbonyl, (Ci-C6 haloalkoxy) carbonyl, (Ci-C6-Halogenalkyltbio) carbonyl, (halo-Ci-C4-alkoxy-Ci-C4-alkyl) carbonyl, ( C 3 -C 6 -HaiogBn-alkenyloxy) 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 -CsC-R 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 ,
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 Pyrazolylcarboxamid 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 Pyrazolylcarboxamid of formula (I) according to claim 1 in addition to extenders and / or surface-active substances.
4. Viϊrwendung von Pyrazolylcarboxamiden der Formel (I) gemäß Anspruch 1 zum Bekämpfen unerwünschter Mikroorganismen.4. Viϊrwendung of Pyrazolylcarboxamiden of formula (I) according to claim 1 for controlling unwanted microorganisms.
5. Varfahren zum Bekämpfen unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Pyrazolylcarboxamide der Formel (I) gemäß Anspruch ] auf die Mikroorganismen und/oder deren Lebensraum ausbringt. 5. Varfahren for controlling unwanted microorganisms, characterized in that pyrazolylcarboxamides of the formula (I) according to claim] on the microorganisms and / or their habitat ausbringt.
6. Verfahren zum Herstellen von Mitteln zum Bekämpfen unerwünschter Mikroorganismen, dacurch gekennzeichnet, dass man Pyrazolylcarboxamide der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt.6. A process for preparing means for controlling unwanted microorganisms, characterized in that mixing pyrazolylcarboxamides of the formula (I) according to claim 1 with extenders and / or surface-active substances.
7. Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von7. Use of carboxamides of the formula (I) according to claim 1 for the treatment of
Saatgut.Seed.
8. Verwendung von Carboxamiden der Formel (I) gemäß Anspruch 1 zur Behandlung von transgenen Pflanzen.8. Use of carboxamides of the formula (I) according to claim 1 for the treatment of transgenic plants.
9. Verwendung von Carboxamiden der Formel (T) gemäß Anspruch 1 zur Behandlung von Saatgut transgener Pflanzen 9. Use of carboxamides of the formula (T) according to claim 1 for the treatment of seed transgenic plants
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