Thiazolyl substituted aminopyrimidines as plant protection agents

• US 7,105,517 B2
• Filed: 09/19/2002
• Issued: 09/12/2006
• Est. Priority Date: 10/01/2001
• Status: Expired due to Fees

• Current Assignee: Syngenta Crop Protection Incorporated (China National Chemical Corporation)
• Original Assignee: Syngenta Crop Protection Incorporated (China National Chemical Corporation)
• Inventors: Stanetty, Peter, Eberle, Martin, Mueller, Urs, Lutz, William, Pillonel, Christian
• Primary Examiner(s): RAO, DEEPAK R
• Application Number:
  US10/491,231
• Publication Number:
  US 20050038059A1
• Time in Patent Office: 1,454 Days
• Field of Search: 544/122, 544/331, 514/235.8, 514/275
• US Class Current: 514/235.8
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/14 containing three or more hetero rings

Abstract

Compounds of formula (I), or a salt thereof, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, and R₈ are specified organic redicals; and compositions containing them, processes for making them and their use as fungicides.

Claims

1. A compound of formula IA

3. A method according to claim 1, wherein R₃, R₆ and R₈ are all hydrogen.

4. A method according to claim 1, wherein R₁ is hydrogen, C₁–

C₄alkyl, or is a group —

CO—

R₉; and

R₂ is hydrogen or C₁–

C₄alkyl;

or R₁ and R₂ together form the group —

N═

CR₉—

NR₁₀R₁₁;

R₃ is hydrogen or methyl; and

R₄ is hydrogen, hydroxy, amino, C₁–

C₄alkyl, C₁–

C₄haloalkyl, C₁–

C₄cyanoalkyl, C₁–

C₆alkylamino, di(C₁–

C₄alkyl)-amino, C₁–

C₆aminoalkyl, halogen, mercapto, cyano, C₁–

C₆alkoxy, C₂–

C₆alkenyloxy, C₂–

C₆alkynyloxy, C₁–

C₆alkylthio, C₁–

C₆alkylsulfinyl, C₁–

C₆alkylsulfonyl, C₁–

C₆hydroxyalkyl, C₁–

C₄alkoxy-C₁–

C₆alkyl, C₁–

C₄alkyl-C₁–

C₆aminoalkyl, di(C₁–

C₄alkyl)-C₁–

C₆aminoalkyl, C₁–

C₄alkoxycarbonyl;

—

CO—

R₉, or —

NH—

CO—

R₉; and

R₅ is hydrogen, hydroxy, or methoxy; and

R₆ is hydrogen; and

R₇ is 4-pyridyl or optionally substituted aryl carrying one to three substituents independently selected from the group comprising halogen, C₁–

C₄alkyl, C₁–

C₄alkoxy, C₁–

C₄haloalkyl and C₁–

C₄haloalkoxy; and

R₈ is hydrogen, C₁–

C₄alkanoyl, C₁–

C₄haloalkanoyl or C₁–

C₄alkyl.

5. A method according to claim 1, wherein;

R₁ is hydrogen, methyl, trifluoroacetyl, pentafluoropropionyl or heptafluorobutyryl; and

R₂ is hydrogen or C₁–

C₄alkyl;

or R₁ and R₂ are both hydrogen, or R₁ and R₂ together form the groups —

N═

CH—

N(CH₃)₂ or —

N═

C(CH₃)—

N(CH₃)₂; and

R₃ is hydrogen or methyl; and

R₄ is hydrogen, hydroxy, C₁–

C₄alkyl, C₁–

C₄alkoxy, C₁–

C₄haloalkoxy, C₁–

C₄haloalkyl, C₁–

C₄cyanoalkyl, C₁–

C₄alkanoyloxy, C₁–

C₄hydroxyalkyl, C₁–

C₄haloalkanoyloxy, C₁–

C₄alkanoyl-C₁–

C₆aminoalkyl, C₁–

C₄alkanoyloxy-C₁–

C₄alkyl, C₁–

C₄alkanoyl, C₁–

C₄alkylthio or C₁–

C₄alkoxycarbonyl; and

R₅ is hydrogen or hydroxy; and

R₆ is hydrogen; and

R₇ is phenyl or halophenyl; and

R₈ is hydrogen or C₁–

C₄fluoroalkanoyl.

6. A method according to claim 1, wherein;

R₁ is acetyl; and

R₂ is hydrogen or methyl;

or R₁ and R₂ together form the groups —

N═

CH—

N(CH₃)₂ or —

N═

C(CH₃)—

N(CH₃)₂; and

R₃ is hydrogen; and

R₄ is hydrogen, hydroxy, cyano, fluorine, chlorine, bromine, methyl, tert. butyl, methylthio, trifluoromethyl, hydroxymethyl, cyanomethyl, 2-cyanoethyl, 1-hydroxyethyl, 2-hydroxyisopropyl, acetyl, acetoxymethyl, methoxycarbonyl, methoxy, ethoxy or trifluoromethoxy; and

R₅ and R₆ are hydrogen; and

R₇ is phenyl, 4-fluorophenyl or 4-chlorophenyl; and

R₈ is hydrogen or C₁–

C₄fluoroalkanoyl.

7. A method according to claim 1, wherein R₁, R₂, R₃, R₅, R₆ and R₈ are all hydrogen and R₄ is hydrogen, hydroxy, cyano, fluorine, chlorine, bromine, methyl, tert.butyl, methylthio, trifluoromethyl, cyanomethyl, 2-cyanoethyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyisopropyl, acetyl, acetoxymethyl, and R₇ is phenyl, 4-fluorophenyl or 4-chlorophenyl.

8. A method according to claim 1, wherein the compound of formula I is a compound of subformula IA

9. A method according to claim 1, wherein the compound of formula I is a compound of subformula IB

10. A method according to claim 1, wherein the compound of formula I is selected from the group consisting of:

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-phenyl-amine,

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-phenyl-amine;

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(1-hydroxyethyl)-phenyl]-amine;

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-[3-(1-hydroxyethyl)-phenyl]-amine;

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(1-hydroxy-1-methylethyl)-phenyl]-amine;

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-[3-(1-hydroxy-1-methylethyl)-phenyl]-amine;

N-[4-(2-amino-4-phenyl, thiazol-5-yl)-pyrimidin-2-yl]-N-(3-acetyl-phenyl)-amine;

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-acetyl-phenyl)-amine;

N-[4-(2-amino-4-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyano-phenyl)-amine;

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-(3-cyano-phenyl)-amine;

{4-[2-acetylamino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-acetoxymethyl-phenyl)-amine;

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-methoxy-phenyl)-amine;

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-methoxy-phenyl)-amine;

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyano-phenyl)-amine;

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(4-fluoro-phenyl)-amine;

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-cyano-phenyl)-amine;

N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-cyanomethyl-phenyl)-amine; and

N-{4-[2-amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-pyrimidin-2-yl}-N-(3-cyanomethyl-phenyl)-amine.

11. A method according to claim 1, wherein the phytopathogenic microorganisms are fungal organisms.

2. A method of controlling and preventing an infestation of crop plants by phytopathogenic microorganisms, which comprises the application of a compound of formula I