IP Library › Granted Patent US 8,283,349

Granted Patent B2

US 8,283,349 · App. 12/449,431 · Granted Oct 9, 2012

Fungicide N-(3-phenylpropyl) carboxamide derivatives

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Patent No.: US 8,283,349
App. No.: 12/449,431
Granted: Oct 9, 2012
Kind: B2

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Abstract

A compound of general formula (I): A process for preparing this compound. A fungicidal 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.

Claims (129)

1. A compound of formula (I)

wherein:

n is 1, 2, 3, 4 or 5;

T is selected from the group consisting of O, S, N—R a , N—OR b , N—NR a R b and N—CN;

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 -halogenoalkyl having 1 to 5 halogen atoms, 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 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 3 -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, 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 and a phenylamino;

R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, 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 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms and a C 1 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms;

R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, 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 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms or and a C 1 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms;

R 5 and R 6 are independently selected from the group consisting of a hydrogen atom, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, 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 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms and a C 1 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms;

R 7 is selected from the group consisting of a hydrogen atom, a C 1 -C 6 -alkyl and a C 3 -C 7 -cycloalkyl;

R a and R b are independently selected from the group consisting of a hydrogen atom; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C 3 -C 7 -cycloalkyl; C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl; C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different; phenyl that can be substituted by up to 5 groups Q; naphthyl that can be substituted by up to 6 groups Q; phenylmethylene that can be substituted by up to 5 groups Q; and phenylsulfonyl that can be substituted by up to 5 groups Q;

each Q is independently selected from the group consisting of a halogen atom; cyano; nitro; C 1 -C 8 -alkyl; C 1 -C 8 -alkoxy; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; tri(C 1 -C 8 )alkylsilyl and tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; C 1 -C 8 -alkoxyimino; and (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; and

Het is a 5-, 6- or 7-membered non-fused heterocycle with one, two or three heteroatoms which may be the same or different, Het being linked by a carbon atom and Het being substituted in ortho-position by at least one substituent linked by a carbon atom and optionally substituted in any other position by one or further more substituents independently selected from the group consisting of a halogen atom, a nitro group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkoxy-C 2 -C 8 -alkenyl, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, 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 -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 and a C 1 -C 8 -alkylsulfonamide;

as well as any salt, N-oxide, metallic complex, metalloidic complex, or optically active isomer thereof;

with the proviso that compound of formula (I) is different from:

4,6-dichloro-2-(methylthio)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,

4-chloro-2-(methylthio)-6-[(2-phenylethyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,

4-chloro-2-(methylthio)-6-[(2-phenylmethyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,

4-chloro-2-(methylthio)-6-(phenylamino)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,

4-chloro-2-(methylthio)-6-[(2-phenylpropyl)amino]-N-(3-phenylpropyl)-5-pyrimidinecarboxamide,

5-chloro-1-methyl-N-(3-phenylpropyl)-1H-pyrazole-4-carboxamide,

N-[3-(4-acetylphenyl)propyl]-5-chloro-3-methoxythiophene-2-carboxamide, and

4-(3-{[(5-chloro-3-methoxy-2-thienyl)carbonyl]amino}propyl)benzoic acid.

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 halogen atom, a (hydroxyimino)-C 1 -C 6 -alkyl group, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -alkyl, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -halogenoalkoxy 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 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.

4. The compound of claim 1 wherein R 1 and R 2 are independently selected from the group consisting of a hydrogen atom and a C 1 -C 8 -alkyl.

5. The compound of claim 1 wherein R 3 and R 4 are independently selected from the group consisting of a hydrogen atom and a C 1 -C 8 -alkyl.

6. The compound of claim 1 wherein R 5 and R 6 are independently selected from the group consisting of a hydrogen atom and a C 1 -C 8 -alkyl.

7. The compound of claim 1 wherein Het is selected from the group consisting of 2-furan, 3-furan, 4,5-dihydro-3-furan, 2-thiophene, 3-thiophene, 2-pyrrole, 3-pyrrole, 5-oxazole, 4-oxazole, 5-thiazole, 4-thiazole, 5-pyrazole, 4-pyrazole, 3-pyrazole, 4-isoxazole, 5-isoxazole, 4-isothiazole, 4-1,2,3-triazole, 4-thiadiazole, 5-1,2,3-thiadiazole, 4,5-dihydro-4-pyrazole, 2-pyridine, 3-pyridine, 4-pyridine, 1,4-oxathiine, 3,4-dihydro-5-pyran, 2,3-dihydro-1,4-oxathiine, and 2-pyrazine.

8. The compound of claim 1 wherein Het is substituted in ortho position by a moiety selected from the group consisting of a halogen atom, a C 1 -C 8 -alkyl and a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms.

9. The compound of claim 1 wherein Het is substituted in any position different from the ortho position by a moiety selected from the group consisting of a halogen atom, a C 1 -C 6 -alkyl, an amino group, a C 1 -C 8 -alkylamino and a di-C 1 -C 8 -alkylamino.

10. The compound of claim 1 wherein Het is a 5-membered heterocycle.

11. The compound of claim 1 wherein R 7 is hydrogen.

12. The compound of claim 1 wherein T is oxygen.

13. A process for the preparation of the compound of claim 1 comprising reacting a 3-phenylpropan-1-amine derivative of formula (II) or a salt thereof:

wherein:

n is 1, 2, 3, 4 or 5;

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 -halogenoalkyl having 1 to 5 halogen atoms 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 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 3 -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 and a phenylamino;

R 7 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 formula (III)

wherein:

Het is a 5-, 6- or 7-membered non-fused heterocycle with one, two or three heteroatoms which may be the same or different, Het being linked by a carbon atom and Het being substituted in ortho-position by at least one substituent linked by a carbon atom and optionally substituted in any other position by one or more substituents independently selected from the group consisting of a halogen atom, a nitro group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkoxy-C 2 -C 8 -alkenyl, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, 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 -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 and a C 1 -C 8 -alkylsulfonamide; and

L is a leaving group selected from the group consisting of a halogen atom, a hydroxyl group, —OR a , —OCOR a , R a being a C 1 -C 6 -alkyl, a C 1 -C 6 haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenyl or a group of formula

in the presence of a catalyst and, if L is a hydroxyl group, in the presence of a condensing agent.

14. The process of claim 13 wherein R 7 is a hydrogen atom, said process further comprising the step:

wherein:

Het is a 5-, 6- or 7-membered non-fused heterocycle with one, two or three heteroatoms which may be the same or different, Het being linked by a carbon atom and Het being substituted in ortho-position by at least one substituent linked by a carbon atom and optionally substituted in any other position by one or more substituents independently selected from the group consisting of a halogen atom, a nitro group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkoxy-C 2 -C 8 -alkenyl, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, 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 -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 and a C 1 -C 8 -alkylsulfonamide;

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 -halogenoalkyl having 1 to 5 halogen atoms a C 1 -C 8 -alkyl, a C 2 -C 3 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkylamino, 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 and a phenylamino;

n is 1, 2, 3, 4 or 5;

R 7a is selected from the group consisting of a hydrogen atom, a C 1 -C 6 -alkyl and a C 3 -C 7 -cycloalkyl; and

L 1 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 the compound of formula (I).

15. A fungicide composition comprising an effective amount of the compound of claim 1 and an agriculturally acceptable support.

16. A method for combating the phytopathogenic fungi of crops comprising applying an effective and non-phytotoxic amount of the composition of claim 15 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.

17. A method for combating the phytopathogenic fungi of crops comprising applying an effective and non-phytotoxic amount of the compound of claim 1 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.

18. A compound of formula (I)

wherein:

n is 1, 2, 3, 4 or 5;

T is selected from the group consisting of O, S, N—R a , N—OR b , N—NR a R b and N—CN;

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 -halogenoalkyl having 1 to 5 halogen atoms, 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 di-C 1 -C 8 -alkylamino, a C 1 -C 3 -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 and a phenylamino;

R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, 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 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms and a C 1 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms;

R 5 and R 6 independently selected from the group consisting of a hydrogen atom, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, 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 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 1 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms and a C 1 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms;

R 7 is selected from the group consisting of a hydrogen atom, a C 1 -C 6 -alkyl and a C 3 -C 7 -cycloalkyl;

each Q is independently selected from the group consisting of a halogen atom; cyano;

nitro; C 1 -C 8 -alkyl; C 1 -C 8 -alkoxy; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; tri(C 1 -C 8 )alkylsilyl and tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; C 1 -C 8 -alkoxyimino; and (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; and

Het is a 6-membered non-fused heterocycle with one, two or three heteroatoms which may be the same or different, Het being linked by a carbon atom and Het being substituted in ortho-position by at least one substituent linked by a carbon atom and optionally substituted in any other position by one or more substituents independently selected from the group consisting of a halogen atom, a nitro group, a pentafluoro-λ 6 -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a C 1 -C 8 -alkyl, a C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, a C 2 -C 8 -alkynyl, a C 1 -C 8 -alkoxy, a C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, a C 1 -C 8 -alkoxy-C 2 -C 8 -alkenyl, a C 1 -C 8 -alkylsulfanyl, a C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, 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 -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 and a C 1 -C 8 -alkylsulfonamide;

as well as any salt, N-oxide, metallic complek, metalloidic complex, or optically active isomer thereof;