2-(4-pyrazolyloxy-pyrimidin-5-yl) acetic acid derivatives

• US 5,807,863 A
• Filed: 09/19/1996
• Issued: 09/15/1998
• Est. Priority Date: 09/28/1995
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Novartis Corporation (Novartis Ag)
• Inventors: Lamberth, Clemens, Eberle, Martin, Schaub, Fritz
• Primary Examiner(s): Ford, John M.
• Application Number:
  US08/715,980
• Time in Patent Office: 726 Days
• Field of Search: 544/300, 544/310, 544/316, 544/317, 544/319, 544/320, 544/321, 544/296, 544/238, 544/284, 514/269, 514/272, 514/274, 514/252, 514/259
• US Class Current: 514/269
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: C07D 231/08 with oxygen or sulfur atoms directly attached to ring carbon atoms
• CPC Class Codes: C07D 231/22 with aryl radicals attached to ring nitrogen atoms
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07D 413/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/14 containing three or more hetero rings

Abstract

This invention relates to novel 2-(4-pyrazolyloxy-pyrimidin-5-yl) acetic acid derivatives of formula I ##STR1## wherein R₁ is hydrogen, C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, C_3-6 cycloalkyl, or di-C_1-4 alkylamino,

R₂ is hydrogen, C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, or di-C_1-4 alkyl-amino,

R₃ is hydrogen or methyl,

R₄ is aryl, aryl-C_1-4 alkyl, heteroaryl, or heteroaryl-C_1-4 alkyl, wherein each of the aromatic rings may be optionally substituted; and

X is CH or nitrogen;

the use of such compounds for the control of phytopathogens, compositions for facilitating such use, and the preparation of the compounds of formula I.

Claims

1. A compound of formula I ##STR84## wherein R₁ is hydrogen, C_1-4 alkyl, C_1-4 alkoxy, C_3-6 cycloalkyl, C_1-4 alkylthio, or di- C_1-4 alkylamino,

R₂ is hydrogen, C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, or di- C_1-4 alkylamino,

R₃ is hydrogen or methyl,

R₄ is phenyl, naphthyl, benzyl, phenyethyl, phenylpropyl, 1-phenylethyl, or a heteroaryl selected from the group consisting of pyridyl, pyrimidinyl, thienyl, oxazolyl, oxadiazolyl, triazolyl, thiadiazolyl, furyl, isoxazolyl, thiazolyl, imidazolyl, pyridazinyl, quinolinyl, quinazolinyl, benzothienyl, benzofuryl, benzimidazolyl, pyrazolyl, benzothiazolyl, benzoxazolyl, and any one of said heteroaryl groups in combination with --CH₂, --CH₂ --CH₂ -- or --C(CH₃) and wherein each of the aromatic rings may be optionally substituted by one, two or three radicles selected from the group consisting of halogen, C_1-4 alkyl, C_1-4 alkoxy, C_1-4 haloalkyl, C_1-4 haloalkoxy, C_2-8 acyl, benzoyl, C_1-4 alkylthio, cyano, phenyl, phenoxy, nitro and --C(CH₃)═

N--O--C_1-4 alkyl; and

X is CH or nitrogen.

2. A compound according to claim 1 wherein the aromatic rings in R₄ are optionally substituted by one, two or three radicals selected from the group comprising halogen, C_1-4 alkyl, C_1-4 alkoxy, C_1-4 haloalkyl, C_1-4 haloalkoxy, C_1-4 alkylthio, cyano, phenyl, phenoxy, nitro, or a group --C(CH₃)═

N--O--C_1-4 alkyl.

3. A compound according to claim 1, wherein R₁ is methyl, ethyl, or cyclopropyl.

4. A compound according to claim 1, wherein R₂ is methyl, or methoxy.

5. A compound according to claim 1, wherein the pyrazole ring is linked to the oxygen bridge in the 3- or 4-position.

6. A compound according to claim 1, wherein R₄ is chlorophenyl, dichlorophenyl, fluorophenyl, methyl-chlorophenyl, trifluoromethylphenyl, trifluoromethyl-chlorophenyl, difluoromethoxyphenyl, trifluoromethoxyphenyl, methylphenyl, or dimethylphenyl.

7. A compound according to claim 1, wherein R₁ and R₂ are methyl, R₄ is chlorophenyl, dichlorophenyl, fluorophenyl, methyl-chlorophenyl, trifluoromethylphenyl, trifluoromethyl-chlorophenyl, difluoromethoxyphenyl, trifluoromethoxyphenyl, methylphenyl, or dimethylphenyl.

8. A compound according to claim 7, wherein X is CH.

9. A compound according to claim 1, selected from the group comprising

methyl 2- 2,4-dimethyl-6-(1-(3-trifluoromethylphenyl)-1H-pyrazol-3-yloxy)-pyrimidin-5-yl!-3-methoxyacrylate;

methyl 2- 2,4-dimethyl-6-(1-(3,5-dimethylphenyl)-1H-pyrazol-4-yloxy)-pyrimidin-5-yl!-3-methoxyacrylate;

methyl 2- 2,4-dimethyl-6-(1-(5-chloro-2-methylphenyl)-1H-pyrazol-3-yloxy)-pyrimidin-5-yl!-3-methoxyacrylate; and

methyl 2- 2-methyl-4-methoxy-6-(1-(5-chloro-2-methylphenyl)-1H-pyrazol-3-yloxy)-pyrimidin-5-yl!-3-methoxyacrylate.

10. Method of combatting phytopathogenic fungi comprising applying to the fungi or their habitat a fungicidally effective amount of a compound of formula I according to claim 1.

11. Fungicidal composition comprising a compound of formula I stated in claim 1 and a agriculturally acceptable diluent.

12. A compound of formula II ##STR85## wherein R₁ is hydrogen, C_1-4 alkyl, C_1-4 alkoxy, C_3-6 cycloalkyl, C_1-4 alkylthio, or di- C_1-4 alkylamino,

R₂ is hydrogen, C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, or di- C_1-4 alkylamino,

R₃ is hydrogen or methyl,

R₄ is phenyl, naphthyl, benzyl, phenyethyl, phenylpropyl, 1-phenylethyl, or a heteroaryl selected from the group consisting of pyridyl, pyrimidinyl, thienyl, oxazolyl, oxadiazolyl, triazolyl, thiadiazolyl, furyl, isoxazolyl, thiazolyl, imidazolyl, pyridazinyl, quinolinyl, quinazolinyl, benzothienyl, benzofuryl, benzimidazolyl, pyrazolyl, benzothiazolyl, benzoxazolyl, and any one of said heteroaryl groups in combination with --CH₂, --CH₂ --CH₂ -- or --C(CH₃) and wherein each of the aromatic rings may be optionally substituted by one, two or three radicles selected from the group consisting of halogen, C_1-4 alkyl, C_1-4 alkoxy, C_1-4 haloalkyl, C_1-4 haloalkoxy, C_2-8 acyl, benzoyl, C_1-4 alkylthio, cyano, phenyl, phenoxy, nitro and --C(CH₃)═

N--O--C_1-4 alkyl; and

X is CH or nitrogen.