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US 6,617,330 B2Granted
Pyrimidin-4-enamine as fungicide
AssigneeSyngenta Participations AG
InventorHarald Walter
Life of this patent
Estimating the term…
Abstract
Novel pyrimidine derivatives of formula I as well as possible isomers and mixtures of isomers thereof. The novel compounds have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms and insecticidal attack.
Claims15
A compound of formula I
- wherein
- A is a 5- or 6-membered ring which may be saturated or unsaturated, aromatic or non-aromatic and which may contain no hetero atoms or 1-3 hetero atoms O, S and/or N, each in the free form or in salt form;
- with the exception of the imidazol ring;
- R1, R2 and R3 are each independently of the other hydrogen;
- halogen;
- C1-C8alkyl, C2-C8alkenyl or C2-C8alkinyl which are unsubstituted or mono- to tri-substituted by C3-C6cycloalkyl, halogen, C1-C6alkoxy, C1-C6alkylthio or C1-C6haloalkoxy;
- O—C1-C6alkyl, C2-C6alkenyl, O—C2-C6alkynyl, S—C1-C6alkyl, S—C2-C6alkenyl or S—C2-C6alkynyl, which are unsubstituted or mono- to tri-substituted by C3-C6cycloalkyl, halogen, C1-C6alkoxy or C1-C6haloalkoxy;
- cyano;
- nitro;
- or trimethylsilyl;
- provided that R1, R2 and R3 are not hydrogen at the same time;
- R4 is C1-C8alkyl, C2-C8alkenyl or C2-C8alkinyl which are unsubstituted or mono- to tri-substituted by C3-C6cycloalkyl, halogen, cyano, nitro, CO—C1-C4alkyl, COO—C1-C4alkyl, CO-aryl, COO-aryl, C1-C6alkoxy, C1-C6alkylthio or C1-C6haloalkoxy;
- C3-C6cycloalkyl which is unsubstituted or mono- to tri-substituted by C1-C8alkyl, C1-C6haloalkyl, halogen, cyano, C1-C6alkoxy or C1-C6haloalkoxy;
- phenyl or benzyl, in which the phenyl group is unsubstituted or mono- to pentasubstituted by halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkinyl, C1-C6alkoxy, C1-C6haloalkoxy or C1-C8haloalkyl;
- NHR7;
- SR7;
- or CR7;
- R5 is C1-C8alkyl, C2-C8alkenyl or C2-C8alkinyl which are unsubstituted or mono- to tri-substituted by C3-C6cycloalkyl, halogen, cyano, nitro, CO—C1-C4alkyl, COO—C1-C4alkyl, CO-aryl, COO-aryl, C1-C6alkoxy, C1-C6alkylthio or C1-C6haloalkoxy;
- C3-C6cycloalkyl which is unsubstituted or mono- to tri-substituted by C1-C6alkyl, halogen, cyano, C1-C6alkoxy, C1-C6haloalkyl or C1-C6haloalkoxy;
- R6 is hydrogen;
- C1-C8alkyl, C2-C8alkenyl or C2-C8alkinyl which are unsubstituted or mono- to tri substituted by C3-C6cycloalkyl, halogen, cyano, nitro, CO—C1-C4alkyl, COO—C1-C4alkyl, CO-aryl, COO-aryl, C1-C6alkoxy, C1-C6alkylthio or C1-C6haloalkoxy;
- C3-C6cycloalkyl which is unsubstituted or mono- to tri-substituted by C1-C6alkyl, halogen, cyano, C1-C6alkoxy, C1-C6haloalkyl or C1-C6haloalkoxy;
- O—C1-C6alkyl, O—C2-C6alkenyl, O—C2-C6alkynyl, S—C1-C6alkyl, S—C2-C6alkenyl or S—C2-C6alkynyl, which are unsubstituted or mono- to tri-substituted by C3-C6cycloalkyl, halogen, cyano, C1-C6alkoxy or C1-C6haloalkoxy;
- aryl or heteroaryl which are unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- CO-heteroaryl;
- CO—C1-C6alkyl;
- CO—C1-C6alkyl-O—C1-C6alkyl;
- CO—C1-C6haloalkyl;
- SO2—C1-C6alkyl;
- SO2-aryl;
- CO-phenyl or CO—C1-C6alkyl-O-phenyl in which phenyl is unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- COOR8 wherein R8 is C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C4cycloalkyl or phenyl which is unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;
- cyano;
- nitro;
- or halogen;
- and
- R7 is C1-C8alkyl, C2-C8alkenyl or C2-C8alkinyl which are unsubstituted or mono- to tri-substituted by C3-C6cycloalkyl, halogen, cyano, nitro, CO—C1-C4alkyl, COO—C1-C4alkyl, CO-aryl, COO-aryl, C1-C6alkoxy, C1-C6alkylthio or C1-C6haloalkoxy;
- C3-C6cycloalkyl which is unsubstituted or mono- to tri-substituted by C1-C6alkyl, C1-C6haloalkyl, halogen, cyano, C1-C6alkoxy or C1-C6haloalkoxy;
- phenyl or benzyl, in which the phenyl group is unsubstituted or mono- to pentasubstituted by halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkinyl, C1-C6alkoxy, C1-C6haloalkoxy or C1-C8haloalkyl.
36 more elements
Dependencies are inferred from the claim text.