EP1965642A2 - Pyrazolylcarboxamides - Google Patents

Pyrazolylcarboxamides

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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
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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Withdrawn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
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German (de)
English (en)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Jörg Nico Greul
Herbert Gayer
Peter Dahmen
Arnd Voerste
Ulrike Wachendorff-Neumann
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Bayer CropScience AG
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Bayer CropScience AG
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Publication date
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Publication of EP1965642A2 publication Critical patent/EP1965642A2/fr
Withdrawn legal-status Critical Current

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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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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
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  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
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  • Plural Heterocyclic Compounds (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne de nouveaux pyrazolylcarboxamides de la formule (I) où R1, M, R9, R10, R11, R12 et m sont tels que définis dans la description, plusieurs procédés de production de ces matières et leur utilisation pour lutter contre les micro-organismes indésirables, ainsi que de nouveaux produits intermédiaires et leur production.
EP06829292A 2005-12-17 2006-12-05 Pyrazolylcarboxamides Withdrawn EP1965642A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005060464A DE102005060464A1 (de) 2005-12-17 2005-12-17 Pyrazolylcarboxamide
PCT/EP2006/011645 WO2007068370A2 (fr) 2005-12-17 2006-12-05 Pyrazolylcarboxamides

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EP1965642A2 true EP1965642A2 (fr) 2008-09-10

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US (1) US20090069398A1 (fr)
EP (1) EP1965642A2 (fr)
AR (1) AR058386A1 (fr)
DE (1) DE102005060464A1 (fr)
WO (1) WO2007068370A2 (fr)

Families Citing this family (7)

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Publication number Priority date Publication date Assignee Title
DE10347090A1 (de) 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE102005009458A1 (de) * 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
DE102005025989A1 (de) * 2005-06-07 2007-01-11 Bayer Cropscience Ag Carboxamide
DE102005035300A1 (de) 2005-07-28 2007-02-01 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
KR20100116675A (ko) * 2008-02-22 2010-11-01 바스프 에스이 ３'-브로민-２,３,４,６'-테트라메톡시-２',６-디메틸벤조페논을 포함하는 살진균성 조성물
US8987470B2 (en) 2010-10-27 2015-03-24 Solvay Sa Process for the preparation of pyrazole-4-carboxamides
DE102014014266B3 (de) * 2014-09-26 2015-08-27 Skw Stickstoffwerke Piesteritz Gmbh Verwendung von Pyrazol-Verbindungen als Mittel zur Verbesserung der Trockenstresstoleranz

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04316559A (ja) * 1990-11-28 1992-11-06 Nissan Chem Ind Ltd ピラゾールカルボキサニリド誘導体及び殺菌剤
US5093347A (en) * 1991-01-28 1992-03-03 Monsanto Company 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use
IL103614A (en) * 1991-11-22 1998-09-24 Basf Ag Carboxamides for controlling botrytis and certain novel such compounds
DE4231517A1 (de) * 1992-09-21 1994-03-24 Basf Ag Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen
ES2169773T3 (es) * 1995-04-11 2002-07-16 Mitsui Chemicals Inc Derivados de tiofeno sustituido y fungicidas agricolas y horticolas que contienen dichos derivados como ingrediente activo.
GB9510459D0 (en) * 1995-05-24 1995-07-19 Zeneca Ltd Bicyclic amines
DE19531813A1 (de) * 1995-08-30 1997-03-06 Basf Ag Bisphenylamide
JPH09132567A (ja) * 1995-11-08 1997-05-20 Mitsui Toatsu Chem Inc ピラゾールカルボン酸アニリド誘導体およびこれを有効成分とする農園芸用殺菌剤
HUP0000582A3 (en) * 1996-11-26 2001-10-29 Zeneca Ltd Insecticidal, acaricidal and nematocidal 8-azabicyclo[3.2.1]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- and 9-aza-3-thiabicyclo[3.3.1]nonane derivatives, preparation and use thereof
DE19735224A1 (de) * 1997-08-15 1999-02-18 Basf Ag Biphenylamide
DE19840322A1 (de) * 1998-09-04 2000-03-09 Bayer Ag Pyrazol-carboxanilide
KR20020058089A (ko) * 1999-12-09 2002-07-12 릴리 엠 씨즐러 스피허, 아네뜨 워너 살진균제로서의 피라졸카복스아미드 및 피라졸티오아미드
GB0101996D0 (en) * 2001-01-25 2001-03-14 Syngenta Participations Ag Organtic compounds
DE10215292A1 (de) * 2002-02-19 2003-08-28 Bayer Cropscience Ag Disubstitutierte Pyrazolylcarbocanilide
GB0230155D0 (en) * 2002-12-24 2003-02-05 Syngenta Participations Ag Chemical compounds
DE102005060462A1 (de) * 2005-12-17 2007-06-28 Bayer Cropscience Ag Biphenylcarboxamide
DE102005060467A1 (de) * 2005-12-17 2007-06-21 Bayer Cropscience Ag Carboxamide

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007068370A2 *

Also Published As

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WO2007068370A3 (fr) 2008-03-13
AR058386A1 (es) 2008-01-30
WO2007068370A2 (fr) 2007-06-21
US20090069398A1 (en) 2009-03-12
DE102005060464A1 (de) 2007-06-28

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