Heterocyclylethylbenzamide derivatives
View Patent ↗A compound of general formula (I): A process for preparing this compound. A fungicide composition comprising a compound of general formula (I). A method for treating plants by applying a compound of general formula (I) or a composition comprising it.
1. A compound of general formula (I)
in which:
n is 1, 2, or 3;
p is 1, 2, 3 or 4;
A is a pyrimidine ring;
z is a carbon atom which can not be substituted by X;
each X is independently selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkylamino, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a di-C 1 -C 8 -alkylamino, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, C 1 -C 8 -alkylsulfenyl, a C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, a C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, a (benzyloxyimino)-C 1 -C 6 -alkyl, a benzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyl a phenyl, and a phenylamino;
R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a carboxy group, a carbamoyl group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl and a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms;
R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a carboxy group, a carbamoyl group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, and a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms;
R 5 is selected from the group consisting of a hydrogen atom, a C 1 -C 6 -alkyl, and a C 3 -C 7 -cycloalkyl;
each Y is independently selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulfenyl, a C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, a C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl and a (benzyloxyimino)-C 1 -C 6 -alkyl; and
Y a is selected from the group consisting of a halogen atom, a cyano group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulfenyl, a C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, a C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, and a (benzyloxyimino)-C 1 -C 6 -alkyl;
as well as its salts, N-oxides, and optically active isomers.
2. The compound of claim 1 , wherein n is 1 or 2.
3. The compound of claim 1 , wherein each X is independently selected from the group consisting of a hydrogen atom, a methyl group, a halogen atom, and a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms.
4. The compound of claim 1 wherein R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 3 -C 8 -cycloalkyl, a C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, and a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms.
5. The compound of claim 1 , wherein R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 3 -C 8 -cycloalkyl, a C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, and a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms.
6. The compound of claim 1 , wherein Y a is selected from the group consisting of a halogen atom, a pentafluoro-λ 6 -sulfanyl group, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, and a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms.
7. The compound of claim 1 wherein p is 1.
8. The compound of claim 1 , wherein each Y is independently selected from the group consisting of a hydrogen atom and a halogen atom.
9. The compound of claim 1 , wherein A is substituted in the 5-position.
10. A process for the preparation of the compound of claim 1 , which comprises reacting a heterocyclylethylamine derivative of general formula (II) or one of its salts:
in which
A is a pyrimidine ring,
each X is independently selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkylamino, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a di-C 1 -C 8 -alkylamino, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 2 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulfenyl, a C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, a C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, a (benzyloxyimino)-C 1 -C 6 -alkyl, a benzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyl a phenyl, and a phenylamino;
n is 1, 2, or 3;
z is a carbon atom which can not be substituted by X;
R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a carboxy group, a carbamoyl group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, and a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms;
R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a carboxy group, a carbamoyl group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, and a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen, atoms; and
R 5 is selected from the group consisting of a hydrogen atom, a C 1 -C 6 -alkyl, and a C 3 -C 7 -cycloalkyl;
with a carboxylic acid derivative of the general formula (III)
in which:
Y a is selected from the group consisting of a halogen atom, a cyano group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 1 -C 3 -alkenyl, a C 1 -C 8 -alkynyl, a C 1 -C 3 -alkoxy, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkynyloxy, a C 1 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulfenyl, C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, a (benzyloxyimino)-C 1 -C 6 -alkyl:
Y is the same or different and is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulphenyl, a C 1 -C 8 -halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulphinyl, a C 1 -C 8 -halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulphonyl, a C 1 -C 8 -halogenoalkylsulphonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, and a (benzyloxyimino)-C 1 -C 6 -alkyl; and
p is 1, 2, 3 or 4;
L 1 is a leaving group selected from the group consisting of a halogen atom, a hydroxyl group, —OR 23 , and —OCOR 23 ; wherein R 23 is selected from the group consisting of a C 1 -C 6 alkyl, a C 1 -C 6 haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenyl, and a group of formula:
in the presence of a catalyst and, if L 1 is a hydroxyl group, in the presence of a condensing agent.
11. The process of claim 10 , wherein R 5 is a hydrogen atom, and the process is completed by a further step according to the following reaction scheme:
in which:
A is a pyrimidine ring;
each X is selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkylamino, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a di-C 1 -C 8 -alkylamino, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulfenyl, a C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, a C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, a (benzyloxyimino)-C 1 -C 6 -alkyl, a benzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyl a phenyl, and a phenylamino;
n is 1, 2, or 3;
z is a carbon atom which can not be substituted by X:
R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a carboxy group, a carbamoyl group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, and a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms;
R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a cyano group, a formyl group, a carboxy group, a carbamoyl group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -cycloalkyl, a C 1 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, and a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms;
Y a is selected from the group consisting of a halogen atom, a cyano group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 1 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkylsulfenyl, a C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, a C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, a (benzyloxyimino)-C 1 -C 6 -alkyl;
each Y is independently selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyloxy, a C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -alkynyloxy, a C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyl, a C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbamoyl, a di-C 1 -C 8 -alkylcarbamoyl, a N—C 1 -C 8 -alkyloxycarbamoyl, a C 1 -C 8 -alkoxycarbamoyl, a N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, a C 1 -C 8 -alkoxycarbonyl, a C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonyloxy, a C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkylcarbonylamino, a C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C 1 -C 8 -alkylaminocarbonyloxy, a di-C 1 -C 8 -alkylaminocarbonyloxy, a C 1 -C 8 -alkyloxycarbonyloxy, a C 1 -C 8 -alkylsulfenyl, a C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfinyl, a C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkylsulfonyl, a C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, a C 1 -C 6 -alkoxyimino, a (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, a (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, and a (benzyloxyimino)-C 1 -C 6 -alkyl;
p is 1, 2, 3 or 4;
R 5a is selected from the group consisting of a C 1 -C 6 -alkyl, and a C 3 -C 7 -cycloalkyl; and
L 2 is a leaving group selected from the group consisting of a halogen atom, a 4-methyl phenylsulfonyloxy, and a methylsulfonyloxy;
comprising reacting a compound of formula (Ia) with a compound of formula (III) to provide a compound of formula (I).
12. A fungicide composition comprising an effective amount of the compound of claim 1 and an agriculturally acceptable support.
13. A method for combating the phytopathogenic fungi of crops comprising applying an effective and non-phytotoxic amount of the fungicide composition of claim 12 to the plant seeds or to the plant leaves and/or to the fruits of the plants or to the soil in which the plants are growing or in which it is desired to grow them.