Pyridinylcarboxylic acid derivatives as fungicides

• US 8,604,040 B2
• Filed: 05/26/2011
• Issued: 12/10/2013
• Est. Priority Date: 05/27/2010
• Status: Active Grant

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer Cropscience AG (Bayer AG)
• Inventors: Cristau, Pierre, Hoffmann, Sebastian, Kluth, Joachim, Rahn, Nicola, Tsuchiya, Tomoki, Wasnaire, Pierre, Benting, Jrgen, Wachendorff-Neumann, Ulrike
• Primary Examiner(s): BERNHARDT, EMILY A
• Application Number:
  US13/117,041
• Publication Number:
  US 20120065197A1
• Time in Patent Office: 929 Days
• Field of Search: None
• US Class Current: 514/253.05
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/60 1,4-Diazines; Hydrogenated 1,4-diazines
• CPC Class Codes: A01N 43/84 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• CPC Class Codes: A61K 31/444 containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
• CPC Class Codes: C07D 213/06 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/14 containing three or more hetero rings

Abstract

Pyridinylcarboxylic acid derivatives of the formula (I)

in which the symbols A, X, Y¹, Y², Y³, L¹, L², R^G, and R¹ are each as defined in the description, and also salts, metal complexes and N-oxides of the compounds of the formula (I), and the use thereof for controlling phytopathogenic harmful fungi and processes for preparing compounds of the formula (I).

Claims

1. A compound of formula (I), a salt, or an N-oxide thereof,

2. The compound of the formula (I) according to claim 1, in which

L² is CH₂

Y¹ is oxygen,

and

R^G is hydrogen.

3. A method for controlling phytopathogenic harmful fungi, comprising applying at least one compound of formula (I), a salt, or an N-oxide thereof, according to claim 1 or 2, to the phytopathogenic harmful fungi, their habitat, or a combination thereof.

4. A composition, comprising at least one compound of formula (I), a salt, or an N-oxide thereof, according to claim 1 or 2, and an extender, a surfactant, or a combination thereof.

5. A method of controlling phytopathogenic harmful fungi, comprising applying the composition according to claim 4, to the phytopathogenic harmful fungi, their habitat, or a combination thereof.

6. A process for making a composition, comprising mixing at least one compound of formula (I), a salt, or an N-oxide thereof, according to claim 1 or 2, with an extender, a surfactant, or a combination thereof.

7. A method of treating a seed for controlling phytopathogenic harmful fungi, comprising applying at least one compound of formula (I), a salt, or an N-oxide thereof, according to claim 1 or 2, to the seed.

8. A method of treating a transgenic plant for controlling phytopathogenic harmful fungi, comprising applying at least one compound of formula (I), a salt, or an N-oxide thereof, according to claim 1 or 2, to the transgenic plant.

9. A method of treating a transgenic seed for controlling phytopathogenic harmful fungi, comprising applying at least one compound of formula (I), a salt, or an N-oxide thereof, according to claim 1 or 2, to the transgenic seed.

10. The compound of the formula (I) according to claim 1, in which A is 3,5-bis-(difluoromethyl)-1H-pyrazol-1-yl.

11. The compound of the formula (I) according to claim 1, in which Y² is oxygen.

12. The compound of the formula (I) according to claim 1, in which Y² is sulphur.

13. The compound of the formula (I) according to claim 1, in which

R¹ is hydrogen, 1,1-dimethylethyl, 3,3-dimethylbutyl, 2,2-dimethylpropyl, 1,2,2-trimethylpropyl, pentyl, 1-ethylpropyl, butyl, 2-methylpropyl, 1-methylethyl, ethyl, propyl, 4-methylpentyl, hexyl, trifluoromethyl, methoxymethyl, ethoxymethyl, ethenyl, prop-2-en-1-yl or but-3-en-1-yl, or

R¹ is cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, each of which optionally contains up to two substituents, where the substituents are each independently cyano, chlorine, fluorine, bromine, iodine, methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, ethenyl, 2-propenyl, 2-propynyloxy, phenyl, methoxy, ethoxy, propyloxy, trifluoromethoxy, ethynyl, methylthio, ethylthio or trifluoromethylthio, or

R¹ is cyclopentenyl, cyclohexenyl or cycloheptenyl, each of which optionally contains up to two substituents, where the substituents are each independently methyl, ethyl, methoxy, ethoxy, trifluoromethoxy, ethynyl, 2-propynyloxy, methylthio, ethylthio or trifluoromethylthio, or

R¹ is phenyl which optionally contains up to three substituents, where the substituents are each independently

fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, 1-methylethyl, butyl, 1,1-dimethylethyl, 1,2-dimethylethyl, ethenyl, ethynyl, trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, propoxy, 1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl, ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl, 2-propynyloxy, methylthio, ethylthio, methylsulphinyl or methylsulphonyl or -L³Q, or

R¹ is naphthalen-1-yl, naphthalen-2-yl, 1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl, 5,6,7,8-tetrahydronaphthalen-1-yl, 5,6,7,8-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl, dihydro-1H-inden-1-yl, 1H-inden-1-yl, 1H-inden-2-yl, 1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl, 1H-inden-7-yl, indan-1-yl, indan-2-yl, indan-3-yl, indan-4-yl or indan-5-yl, which optionally contain up to three substituents, where the substituents are each independently methyl, methoxy, cyano, fluorine, chlorine, bromine, or iodine,

L³ is a direct bond, —

O, —

C(═

O), —

S(O)_m, —

CHR^L31 or —

NR^L32,

m is 0, 1 or 2,

R^L31 is hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R^L32 is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkylcarbonyl, C₂-C₆-haloalkylcarbonyl, C₂-C₆-alkoxycarbonyl or C₂-C₆-haloalkoxycarbonyl,

and

Q is a phenyl.