AU2001283841A1

AU2001283841A1 - N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives

Info

Publication number: AU2001283841A1
Application number: AU2001283841A
Authority: AU
Inventors: Martin Eberle; Christian Pillonel; Daniel Stierli; Hugo Ziegler
Original assignee: Syngenta Participations AG
Current assignee: Syngenta Participations AG
Priority date: 2000-06-08
Filing date: 2001-06-06
Publication date: 2002-03-07
Anticipated expiration: 2021-06-06

Claims

105What is claimed is

1. A process for protecting a plant against attack or infestation by a phytopathogenic organism, comprising applying at least one compound of the formula I,

wherein n is 0 or 1 ,

PM is halogen, alkoxy, haloalkyl, haloalkoxy or alkyl, R₂ is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, each of R₃, R₄ and R₅ is, independently of the others, hydrogen, lower alkyl or halogen, and R₆ is a) hydrazino, that is unsubstituted or one- to threefold substituted by optionally substituted alkyl and/or optionally substituted acyl, b) cyclohexylamino, tetrahydro-4H-pyranyl-4-amino, pyrrolidine-3-amino, 2- or 3-tetrahydro- furylamino, all optionally substitutedby amino. hydroxy, alkoxy, alkyl or alkoxyalkyl, c) piperazinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl, d) morpholinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl, e) oxazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, f) thiazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, g) imidazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, h) amino or mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more substitutents independently selected from the 106

group con- sisting of unsubstituted amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (= lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di- lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkyl-carbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl including formylpiperazinyl, optionally substituted heteroaryl and optionally substituted heteroaryloxy i) optionally substituted alkanoylamino, optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylamino- sulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino, j) N-(optionally substituted alkyl)-N-(optionally substituted lower alkanoyl)-amino, k) N-(optionally substituted alkyl)-N-(optionally substituted alkoxycarbonyl)-amino, I) N-(optionally substituted alkyl)-N-(N',N^'-mono- or di-[optionally substituted alkyl]- aminocarbonyl)-amino, or m) N=C(R₇,R₈) wherein R₇ is hydrogen, alkyl, amino, mono- or di-alkylamino and R₈ is amino, mono- or dialkylamino or wherein R₇ and R₈, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents; or a salt thereof; to one or more loci selected from the group consisting of a plant, a part of a plant, seeds and the site of a plant. 107

2. A process according to claim I, wherein the phytopathogenic organism is a fungal organism.

3. A process according to claim 1 , wherein the fungal organism is one or more selected from the group of classes consisting of Ascomycetes, Basidiomycetes, Oomycetes and Fungi imperfecti.

4. A process according to claim 1 wherein the phytopathogenic organism is a bacterium.

5. A process according to claim 1 wherein the phytopathogenic organism is a virus.

6. A process according to claim 1 wherein the phytopathogenic organism is a nematode.

7. A process according to any one of claims 1 to 6 wherein a compound of formula I is applied wherein n is 0 or 1 ,

Ri is halogen, haloalkyl or haloalkoxy,

R₂ is hydrogen or alkyl, each of R₃, R₄ and R₅ is, independently of the others, hydrogen, lower alkyl or halogen, and

R₆ is as defined in claim 1.

8. A process according to any one of claims 1 to 6 wherein a compound of formula I is applied wherein n is 0 or 1 ,

Ri is halogen, haloalkyl or haloalkoxy,

R₂ is hydrogen or alkyl, each of R₃, R₄ and R₅ is hydrogen, and

R₆ is as defined in claim 1.

9. A process according to any one of claims 1 to 6 wherein a compound of formula I is applied wherein 108

n is 0

R-i is chloro, trifluoromethyl, trifluoromethoxy or 1 ,1 ,2,2-tetrafluoroethoxy

R₂.R3, R and R₅ are hydrogen, and

R₆ is

(a) hydrazino, that is unsubstituted or one- to threefold substituted by optionally substituted alkyl and/or optionally substituted acyl, (e) amino or mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more substitutents independently selected from the group con- sisting of unsubstituted amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)- lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (= lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di- lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkyl-carbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl including formylpiperazinyl, optionally substituted heteroaryl and optionally substituted heteroaryloxy f) optionally substituted alkanoylamino, optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylamino- sulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino, g) N-(optionally substituted alkyl)-N-(optionally substituted lower alkanoyl)-amino, h) N-(optionally substituted alkyl)-N-(optionally substituted alkoxycarbonyl)-amino, i) N-(optionally substituted alkyl)-N-(N^',N^'-mono- or di-[optionally substituted alkyl]- aminocarbonyl)-amino, or 109

j) N=C(R₇,R₈) wherein R₇ is hydrogen, alkyl, amino, mono- or di-alkylamino and R₈ is amino, mono- or dialkylamino or wherein R₇ and R₈, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents; or a salt thereof.

10. A compound of the formula I, wherein n is1 ,

Ri is halogen, alkoxy, haloalkyl, haloalkoxy or alkyl,

R₂ is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, each of R₃, R₄ and R₅ is, independently of the others, hydrogen, lower alkyl or halogen, and

R₆ is a) hydrazino, that is unsubstituted or one- to threefold substituted by optionally substituted alkyl and/or optionally substituted acyl, b) cyclohexylamino, tetrahydro-4H-pyranyl-4-amino, pyrrolidine-3-amino, 2- or 3-tetrahydro- furylamino, all optionally substitutedby amino, hydroxy, alkoxy, alkyl or alkoxyalkyl, c) piperazinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl, d) morpholinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, alkoxy, alkyl or alkoxyalkyl, e) oxazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, f) thiazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, g) imidazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, h) amino or mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are unsubstituted or substituted by one or more substitutents independently selected from the group con- sisting of unsubstituted amino, N-mono- or N,N-di-(lower alkyl)-amino, (lower alkoxy)-lower alk-oxy, lower alkoxycarbonylamino, hydroxy-lower alkoxycarbonylamino, lower alkoxy-lower alkoxycarbonylamino, morpholinyl, hydroxy-lower alkylamino, cyano, halogen, oxo bound to a carbon that is not directly bound to a heteroatom, hydroximino, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, guanidyl, lower alkanoylamino, hydroxy-lower alkanoylamino, lower alkoxy-lower alkanoylamino, halo-lower 110

alkanoylamino, lower alkylaminocarbonylamino, hydroxy-lower alkylaminocarbonylamino, lower alkoxy-lower alkylaminocarbonylamino, amidino, di-lower-alkylamino-cyclohexyl, carboxy, lower alkoxycarbonyl, hydroxy-lower alkoxycarbonyl, lower alkoxy-lower alkoxycarbonyl, lower alkylcarbonyldioxy (= lower alkoxycarbonyloxy), hydroxy-lower alkoxycarbonyloxy, lower alkoxy-lower alkoxycarbonyloxy, lower alkanoyloxy, halo-lower alkanoyloxy, hydroxy-lower alkanoyloxy, lower alkoxy-lower alkanoyloxy, carbamoyl, N-mono- or N,N-di- lower alkylcarbamoyl, N-(hydroxy-lower alkyl)carbamoyl, N-lower alkyl-N-hydroxy-lower alkyl-carbamoyl, N,N-di-(hydroxy-lower alkyl)-carbamoyl, N-hydroxy-carbamoyl, hydroxy, lower alkoxy, lower alkenyloxy, lower alkinyloxy, lower haloalkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidinyl, 2- or 3-tetrahydrofuryl, 2- or 3-dihydrofuryl, piperazinyl, lower alkanoyl-piperazinyl including formylpiperazinyl, optionally substituted heteroaryl and optionally substituted heteroaryloxy i) optionally substituted alkanoylamino, optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylamino- sulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino, j) N-(optionally substituted alkyl)-N-(optionally substituted lower alkanoyl)-amino, k) N-(optionally substituted alkyl)-N-(optionally substituted alkoxycarbonyl)-amino, I) N-(optionally substituted alkyl)-N-(N',N'-mono- or di-[optionally substituted alkyl]- aminocarbonyl)-amino, or m) N=C(R₇,R₈) wherein R₇ is hydrogen, alkyl, amino, mono- or di-alkylamino and R₈ is amino, mono- or dialkylamino or wherein R₇ and R₈, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents; or a salt thereof.

11. A compound of the formula I wherein n is 0,

R_t is halogen, alkoxy, haloalkyl, haloalkoxy or alkyl,

R₂ is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, each of R₃, R₄ and R_s is, independently of the others, hydrogen, lower alkyl or halogen, and

R₆ is a) hydrazino, that is mono to threefold substituted by optionally substituted alkyl and/or 1 1 1

optionally substituted acyl, b) tetrahydro-4H-pyranyl-4-amino, pyrrolidine-3-amino, 2- or 3-tetrahydrofurylamino, all optionally substituted by amino, hydroxy, alkoxy, alkyl or alkoxyalkyl c) piperazinyl that is substituted by amino, hydroxy, alkoxy, alkyl, alkoxyalkyl, d) morpholinyl that is substitutedby amino, hydroxy, alkoxy, alkyl, e) oxazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, f) thiazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, g) imidazolidinyl that is optionally substituted by amino, amino-lower alkyl, hydroxy, hydroxy- lower alkyl, alkoxy, alkyl or alkoxyalkyl, h) mono- or di-(lower alkyl)amino wherein the lower alkyl moieties are substituted by one or more substitutents independently selected from the group consisting of (lower alkoxy)- lower alkoxy, lower halogenalkoxy, lower alkoxycarbonylamino, halogen, oxo, hydroximi- no, alkoximino, optionally substituted hydrazono, lower alkenyl, lower alkynyl, lower alkylcarbonyldioxy, lower alkanoyloxy, lower alkylcarbamoyl, alkenyloxy, alkynyloxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkoxysilyl, 4-tetrahydro-4H-pyranyl, 3-pyrrolidine, 2- or 3-tetra- hydrofuryl, 2- or 3-dihydrofuryl, substituted heteroaryl and optionally substituted heteroaryloxy, i) optionally substituted alkenoylamino, optionally substituted alkynoylamino, optionally substituted mono- or di-alkylaminocarbonylamino, optionally substituted alkoxycarbonylamino, optionally substituted mono- or di-alkylaminosulfonylamino, optionally substituted mono- or di-alkylaminosulfoxylamino, j) N=C(R₇,R₈) wherein R₇ is hydrogen, alkyl, amino, mono- or di-alkylamino and R₈ is amino, mono- or di-alkylamino or wherein R₇ and R_e, together with the binding carbon atom, form a saturated five- to seven-membered ring with 0, 1 or 2 ring nitrogen atoms that is optionally substituted by one or more substituents; or a salt thereof;

12. A compound of the formula I according to claim 11 selected from the group of N-(3-chloro-phenyl)-4-(ethylamino-4-pyridyl)-2-pyrimidine-amine,

N-(3-chloro-phenyl)-4-[2-{1-(2-methoxy-1-methyl)-ethylamino}-4-pyridyl]-2-pyrimidine-amine, N-(3-chloro-phenyl)-4-[2-(N", N'-dimethyl-acetamidino)-4-pyridyl]-2-pyrimidine-amine, 112

13. The use of a compound of the formula I, or a salt thereof, mentioned in any one of claim 1 to 11 for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant infested by a phytopathogenic organism, said use comprising the administration of a compound of the formula I or a salt thereof, or a composition comprising said compound or salt and a carrier material acceptable for agricultural purposes, to any one or more selected from the group consisting of a plant, a part of a plant, seeds and the locus of a plant.

14. A method of protecting a plant against attack by a phytopathogenic organism and/or the treatment of a plant infested by a phytopathogenic organism, said method comprising administering a compound of the formula I mentioned in any one of claims 1 to 11 or a salt thereof, or a composition comprising said compound or salt and a carrier material acceptable for agricultural purposes, to any one or more selected from the group consisting of a plant, a part of a plant, seeds and the locus of a plant, preferably if in need of such treatment.

15. A composition for protecting a plant against attack by a phytopathogenic organisms and/or the treatment of a plant infested by a phytopathogenic organism, said composition comprising a compound of the formula I as mentioned in any one of claims 1 to 11 or a salt thereof and a carrier material acceptable for agricultural purposes.