Substituted (pyridyl)-azinylamine derivatives as fungicides

A substituted-pyridyl-azinylamino derivative of formula (I)

• wherein
• W represents phenyl or a saturated or unsaturated, aromatic or non-aromatic 4-, 5-, 6- or 7-membered heterocycle comprising up to four heteroatoms which may be the same or different
• A represents a carbon atom or a nitrogen atom provided that if A represents a carbon atom then W represents a saturated or unsaturated, aromatic or non-aromatic 4-, 5-, 6- or 7-membered heterocycle comprising up to four heteroatoms which may be the same or different
• Q1 independently represents a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulfanyl group, a pentafluoro-λ6-sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C1-C6-alkyl group, a C1-C8-alkyl, a tri(C1-C8-alkyl)silyl-C1-C8alkyl, C1-C8-cycloalkyl, tri(C1-C8-alkyl)silyl-C1-C8-cycloalkyl, a C1-C8-halogenoalkyl having 1 to 5 halogen atoms, a C1-C8-halogenocycloalkyl having 1 to 5 halogen atoms, a C2-C8-alkenyl, a C2-C8-alkynyl, a C2-C8alkenyloxy, a C2-C8alkynyloxy, a C1-C8alkylamino, a di-C1-C8alkylamino, a C1-C8-alkoxy, a C1-C8halogenoalkoxy having 1 to 5 halogen atoms, a C1-C8-alkylsulfanyl, a C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C2-C8-alkenyloxy, a C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, a C3-C8-alkynyloxy, a C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyl, a C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbamoyl, a di-C1-C8-alkylcarbamoyl, a N—C1-C8-alkyloxycarbamoyl, a C1-C8-alkoxycarbamoyl, a N—C1-C8-alkyl-C1-C8alkoxycarbamoyl, a C1-C8-alkoxycarbonyl, a C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyloxy, a C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C1-C8-alkylcarbonylamino, a C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C1-C8-alkylaminocarbonyloxy, a di-C1-C8-alkylaminocarbonyloxy, a C1-C8-alkyloxycarbonyloxy, a C1-C8-alkylsulphenyl, a C1-C8-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C1-C8alkylsulphinyl, a C1-C8-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphonyl, a C1-C8-halogenoalkylsulphonyl having 1 to 5 halogen atoms, a C1-C8alkylaminosulfamoyl, a di-C1-C8-alkylaminosulfamoyl, a (C1-C6-alkoxyimino)-C1-C6-alkyl, a (C1-C6-alkenyloxyimino)-C1-C6-alkyl, a (C1-C6-alkynyloxyimino)-C1-C6-alkyl, a 2-oxopyrrolidin-1-yl, (benzyloxyimino)-C1-C6-alkyl, C1-C8-alkoxyalkyl, C1-C8-halogenoalkoxyalkyl having 1 to 5 halogen atoms, benzyloxy, benzylsulfanyl, benzylamino, phenoxy, phenylsulfanyl, or phenylamino;
• it being possible for each of these groups or substituents to be substituted when chemically possible;
• p represents 0, 1, 2, 3, 4 or 5;
• Ra represents a hydrogen atom, a cyano group, a formyl group, a formyloxy group, a C1-Cs-alkoxycarbonyl, a C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyl, a C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphonyl, a C1-C8-halogenoalkylsulphonyl having 1 to 5 halogen atoms, a C1-C8-alkyl, a C1-C8-cycloalkyl, a C1-C8-halogenoalkyl having 1 to 5 halogen atoms, a C1-C8-halogenocycloalkyl having 1 to 5 halogen atoms, a C2-C8-alkenyl, a C2-C8-alkynyl, a C1-C8-alkoxyalkyl, or a C1-C8-halogenoalkoxyalkyl having 1 to 5 halogen atoms, a C1-C8-alkoxyalkylcarbonyl, a C1-C8-halogenoalkoxyalkycarbonyl having 1 to 5 halogen atoms, a C1-C8alkylthioalkylcarbonyl, a C1-C8-halogenoalkylthioalkylcarbonyl having 1 to 5 halogen atoms;
• it being possible for each of these groups or substituents to be substituted when chemically possible;
• Rb and Rc independently represent a hydrogen atom, a halogen atom, a cyano, a C1-C8-alkyl, a C1-C8-cycloalkyl, a C1-C8-halogenoalkyl having 1 to 5 halogen atoms, or a C1-C8-halogenocycloalkyl having 1 to 5 halogen atoms;
• it being possible for each of these groups or substituents to be substituted when chemically possible;
• L1 represents a substituted or non substituted pyridyl moiety;
• Y represents O, S, NRd, CReRf;
• L2 represents a direct bond, O, S, NRg, CRhRi;
• Q2 represents a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, (hydroxyimino)-C1-C6-alkyl group, C1-C8-alkyl, tri(C1-C8-alkyl)silyl-C1-C8 alkyl, C1-C8-cycloalkyl, tri(C1-C8alkyl)silyl-C1-C8-cycloalkyl, C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C1-C8-halogenocycloalkyl having 1 to 5 halogen atoms a C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkylsulfanyl, C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C2-C8-alkenyloxy, C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, C3-C8alkynyloxy, C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonyl, C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, N—C1-C8-alkyloxycarbamoyl, C1-C8-alkoxycarbamoyl, N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl, C1-C8alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8-alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8-alkylcarbonylamino, C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylaminocarbonyloxy, di-C1-C8-alkylaminocarbonyloxy, C1-C8-alkyloxycarbonyloxy, C1-C8-alkylsulphenyl, C1-C8-halogenoalkylsulphenyl having 1 to 5 halogen atoms, C1-C8-alkylsulphinyl, C1-C8-halogenoalkylsulphinyl having 1 to 5 halogen atoms, C1-C8-alkylsulphonyl, C1-C8-halogenoalkylsulphonyl having 1 to 5 halogen atoms, C1-C8alkylaminosulfamoyl, di-C1-C8alkylaminosulfamoyl, (C1-C6-alkoxyimino)-C1-C6-alkyl, (C1-C6-alkenyloxyimino)-C1-C6-alkyl, (C1-C6-alkynyloxyimino)-C1-C6-alkyl, (2-oxopyrrolidin-1-yl) C1-C8-alkyl, (2-oxopyrrolidin-1-yl) C1-C8-halogenoalkyl having 1 to 5 halogen atoms, (2-oxopiperidin-1-yl) C1-C8-alkyl, (2-oxopiperidin-1-yl) C1-C8-halogenoalkyl having 1 to 5 halogen atoms, (2-oxoazepan-1-yl) C1-C8-alkyl, (2-oxoazepan-1-yl) C1-C8-halogenoalkyl having 1 to 5 halogen atoms, (benzyloxyimino)-C1-C6-alkyl, C1-C8-alkoxyalkyl, C1-C8-halogenoalkoxyalkyl having 1 to 5 halogen atoms, benzyloxy, benzylsulfanyl, benzylamino, phenoxy, phenylsulfanyl, phenylamino, a or a 4-, 5-, 6- or 7-membered heterocycle comprising up to 4 heteroatoms selected in the list consisting of N, O, S, or a (4-, 5-, 6- or 7-membered heterocyclyl) C1-C6-alkyl comprising up to 4 heteroatoms selected in the list of consisting of N, O, S;
• it being possible for each of these groups or substituents to be substituted when chemically possible;
• Alternatively, L2 and Q2 can form together a substituted or non-substituted 4-, 5-, 6- or 7-membered heterocycle comprising up to 4 heteroatoms selected in the list consisting of N, O, S;
• Rd, Re, Rf, Rg, Rh and Ri independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, (hydroxyimino)-C1-C6-alkyl group, C1-C8-alkyl, tri(C1-C8-alkyl)silyl, tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C1-C8-cycloalkyl, tri(C1-C8-alkyl)silyl-C1-C8-cycloalkyl, C1-C8-halogenoalkyl having 1 to 5 halogen atoms, C1-C8-halogenocycloalkyl having 1 to 5 halogen atoms a C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-alkylamino, di-C1-C8-alkylamino, C1-C8-alkoxy, C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C1-C8-alkylsulfanyl, C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C2-C8-alkenyloxy, C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, C3-C8-alkynyloxy, C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, C1-C8alkylcarbonyl, C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C1-C8alkylcarbamoyl, di-C1-C8-alkylcarbamoyl, N—C1-C8-alkyloxycarbamoyl, C1-C8-alkoxycarbamoyl, N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl, C1-C8-alkoxycarbonyl, C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C1-C8alkylcarbonyloxy, C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C1-C8alkylcarbonylamino, C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C1-C8-alkylaminocarbonyloxy, di-C1-C8-alkylaminocarbonyloxy, C1-C8-alkyloxycarbonyloxy, C1-C8-alkylsulphenyl, C1-C8-halogenoalkylsulphenyl having 1 to 5 halogen atoms, C1-C8-alkylsulphinyl, C1-C8-halogenoalkylsulphinyl having 1 to 5 halogen atoms, C1-C8-alkylsulphonyl, C1-C8-halogenoalkylsulphonyl having 1 to 5 halogen atoms, C1-C8-alkylaminosulfamoyl, di-C1-C8-alkylaminosulfamoyl, (C1-C6-alkoxyimino)-C1-C6-alkyl, (C1-C6-alkenyloxyimino)-C1-C6-alkyl, (C1-C6-alkynyloxyimino)-C1-C6-alkyl, (2-oxopyrrolidin-1-yl) C1-C8-alkyl, (2-oxopyrrolidin-1-yl) C1-C8-halogenoalkyl having 1 to 5 halogen atoms, (2-oxopiperidin-1-yl) C1-C8-alkyl, (2-oxopiperidin-1-yl) C1-C8-halogenoalkyl having 1 to 5 halogen atoms, (2-oxoazepan-1-yl) C1-C8-alkyl, (2-oxoazepan-1-yl) C1-C8-halogenoalkyl having 1 to 5 halogen atoms, (benzyloxyimino)-C1-C6-alkyl, phenylamino, phenyl hetarylamino, or a 4-, 5-, 6- or 7-membered heterocycle comprising up to 4 heteroatoms selected in the list consisting of N, O, S;
• it being possible for each of these groups or substituents to be substituted when chemically possible;
• Unless indicated otherwise, a group or a substituent that is substituted is substituted by one or more of the following groups or atoms:
• a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulfanyl group, a pentafluoro-λ6-sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C1-C6-alkyl group, a C1-C8-alkyl, a tri(C1-C8-alkyl)silyl-C1-C8-alkyl, C1-C8-cycloalkyl, tri(C1-C8-alkyl)silyl-C1-C8-cycloalkyl, a C1-C8-halogenoalkyl having 1 to 5 halogen atoms, a C1-C8-halogenocycloalkyl having 1 to 5 halogen atoms, a C2-C8-alkenyl, a C2-C8-alkynyl, a C2-C8-alkenyloxy, a C2-C8-alkynyloxy, a C1-C8-alkylamino, a di-C1-C8-alkylamino, a C1-C8-alkoxy, a C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C8-alkylsulfanyl, a C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C2-C8-alkenyloxy, a C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, a C3-C8-alkynyloxy, a C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyl, a C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbamoyl, a di-C1-C8-alkylcarbamoyl, a N—C1-C8-alkyloxycarbamoyl, a C1-C8-alkoxycarbamoyl, a N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl, a C1-C8-alkoxycarbonyl, a C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyloxy, a C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C1-C8-alkylcarbonylamino, a C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C1-C8-alkylaminocarbonyloxy, a di-C1-C8-alkylaminocarbonyloxy, a C1-C8-alkyloxycarbonyloxy, a C1-C8-alkylsulphenyl, a C1-C8-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphinyl, a C1-C8-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphonyl, a C1-C8-halogenoalkylsulphonyl having 1 to 5 halogen atoms, a C1-C8alkylaminosulfamoyl, a di-C1-C8alkylaminosulfamoyl, a (C1-C6-alkoxyimino)-C1-C6-alkyl, a (C1-C6-alkenyloxyimino)-C1-C6-alkyl, a (C1-C6-alkynyloxyimino)-C1-C6-alkyl, a 2-oxopyrrolidin-1-yl, (benzyloxyimino)-C1-C6-alkyl, C1-C8-alkoxyalkyl, C1-C8-halogenoalkoxyalkyl having 1 to 5 halogen atoms, benzyloxy, benzylsulfanyl, benzylamino, phenoxy, phenylsulfanyl, or phenylamino;
• as well as salts, N-oxides, metallic complexes, metalloïdic complexes and optically active or geometric isomers thereof;
• provided that the following compounds are excluded:
• (3-{[4-(2-ethenylpyridin-4-yl)-1,3,5-triazin-2-yl]amino}phenyl)methanol;
• methyl 4-{4-[(3-{2-[(tert-butoxycarbonyl)amino]ethoxy}phenyl)amino]-1,3,5-triazin-2-yl}-pyridine-2-carboxylate;
• N-{3-[(4-{2-[(1Z)-3-amino-2-chloroprop-1-en-1-yl]pyridin-4-yl}-1,3,5-triazin-2-yl)amino]-benzyl}-N-methylglycine.