US 8,410,157 B2 · Fungicidal N-cycloalkyl-benzyl-thiocarboxamides or N-cycloalkyl-benzyl-N′-substituted-amidine derivatives

Abstract

The present invention relates to N-cycloalkyl-benzyl-thiocarboxamide or N-cycloalkyl-benzyl-N-substituted-carboximidamide amide derivatives of formula (I) wherein A represents a carbo-linked, unsaturated or partially saturated, 5-membered heterocyclyl; T represents S, N—Ra, N—ORa, N—NRaRb or N—CN; Z1 represents a C3-C7-cycloalkyl and Z2; Z3, X and n represent various substituents; their process of preparation; their use as fungicide active agents, particularly in the form of fungicide compositions and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

A compound of formula (I)

wherein
A is a carbo-linked, unsaturated or partially saturated, 5-membered heterocyclyl group that can be substituted by up to four groups R;
T is selected from the group consisting of S, N—Ra, N—ORa, N—NRaRb and N—CN;
Z1 is selected from the group consisting of a non-substituted C3-C7-cycloalkyl and a C3-C7-cycloalkyl substituted by up to 10 atoms or groups independently selected in the group consisting of halogen atoms;
cyano;
C1-C8-alkyl;
C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8alkoxy;
C1-C8-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkoxycarbonyl;
C1-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylaminocarbonyl;
and di-C1-C8-alkylaminocarbonyl;
Z2 and Z3, are independently selected from the group consisting of a hydrogen atom;
C1-C8-alkyl;
C2-C8-alkenyl;
C2-C8-alkynyl;
cyano;
nitro;
a halogen atom;
C1-C8-alkoxy;
C2-C8-alkenyloxy;
C2-C8-alkynyloxy;
C3-C7-cycloalkyl;
C1-C8-alkylsulphenyl;
amino;
C1-C8-alkylamino;
di-C1-C8-alkylamino;
C1-C8-alkoxycarbonyl;
C1-C8-alkylcarbamoyl;
di-C1-C8-alkylcarbamoyl;
and N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl;
or
Z2 and Z3 together with the carbon atom to that they are linked can form a substituted or non substituted C3-C7-cycloalkyl;
each X, is independently selected from the group consisting of a halogen atom;
nitro;
cyano;
hydroxyl;
sulfanyl;
amino;
pentafluoro-λ6-sulfanyl;
C1-C8-alkyl;
C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylamino;
di-C1-C8-alkylamino;
C1-C8-alkoxy;
C1-C8-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkoxy-C1-C8-alkyl;
C1-C8-alkylsulfanyl;
C1-C8-halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkenyl;
C2-C8-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkynyl;
C2-C8-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different C2-C8-alkenyloxy;
C2-C8-halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkynyloxy;
C2-C8-halogenoalkynyloxy comprising up to 9 halogen atoms that can be the same or different;
C3-C7-cycloalkyl;
C3-C7-cycloalkyl-C1-C8-alkyl;
C3-C7-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different;
formyl;
formyloxy;
formylamino;
carboxy;
carbamoyl;
N-hydroxycarbamoyl;
carbamate;
(hydroxyimino)-C1-C8-alkyl;
C1-C8-alkylcarbonyl;
C1-C8-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylcarbamoyl;
di-C1-C8-alkylcarbamoyl;
N—C1-C8-alkyloxycarbamoyl;
C1-C8-alkoxycarbamoyl;
N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl;
C1-C8-alkoxycarbonyl;
C1-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8alkylaminocarbonyl;
di-C1-C8-alkylaminocarbonyl;
C1-C8-alkylcarbonyloxy;
C1-C8-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylcarbonylamino;
C1-C8-halogenoalkylcarbonylamino comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylaminocarbonyloxy;
di-C1-C8alkylaminocarbonyloxy;
C1-C8-alkyloxycarbonyloxy, C1-C8-alkylsulfenyl, C1-C8-halogenoalkylsulfenyl comprising up to 9 halogen atoms that can be the same or different, C1-C8-alkylsulfinyl, C1-C8halogenoalkylsulfinyl comprising up to 9 halogen atoms that can be the same or different, C1-C8-alkylsulfonyl, C1-C8-halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different, C1-C8-alkoxyimino, (C1-C8-alkoxyimino)-C1-C8-alkyl, (C1-C8alkenyloxyimino)-C1-C8-alkyl, (C1-C8-alkynyloxyimino)-C1-C8-alkyl, a (benzyloxyimino)-C1-C8-alkyl;
tri(C1-C8-alkyl)silyl;
tri(C1-C8-alkyl)silyl-C1-C8-alkyl;
benzyloxy that can be substituted by up to 5 groups Q;
benzylsulfanyl that can be substituted by up to 5 groups Q;
benzylamino that can be substituted by up to 5 groups Q;
naphthyl that can be substituted by up to 6 groups Q;
phenoxy that can be substituted by up to 5 groups Q;
phenylamino that can be substituted by up to 5 groups Q;
phenylsulfanyl that can be substituted by up to 5 groups Q;
phenylmethylene that can be substituted by up to 5 groups Q;
phenyl that can be substituted by up to 5 groups Q;
pyridinyl that can be substituted by up to four groups Q;
and pyridinyloxy that can be substituted by up to four groups Q;
two substituents X together with the consecutive carbon atoms to which they are linked can form a 5- or 6-membered, saturated, carbo- or hetero-cycle, that can be substituted by up to four groups Q that can be the same or different;
n is 1, 2, 3, 4 or 5;
each R is independently selected from the group consisting of a hydrogen atom;
halogen atom;
cyano;
nitro;
amino;
sulfanyl;
pentafluoro-λ-6-sulfanyl;
C1 -C8-alkylamino;
di-C1-C8-alkylamino;
tri(C1-C8-alkyl)silyl;
C1-C8-alkylsulfanyl;
C1-C8-halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkyl;
C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkenyl;
C2-C8-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkynyl;
C2-C8-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkoxy;
C1-C8-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkenyloxy;
C2-C8-alkynyloxy;
C3-C7-cycloalkyl;
C3-C7-cycloalkyl-C1-C8-alkyl;
C1-C8-alkylsulfinyl;
C1-C8-alkylsulfonyl;
C1-C8 alkoxyimino;
(C1-C8-alkoxyimino)-C1-C8-alkyl;
(benzyloxyimino)-C1-C8-alkyl;
phenoxy;
benzyloxy;
benzylsulfanyl;
benzylamino;
naphthyl;
halogenophenoxy comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylcarbonyl;
C1-C8-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkoxycarbonyl;
C1-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylaminocarbonyl;
di-C1-C8-alkylaminocarbonyl;
Raand Rb are independently selected from the group consisting of a hydrogen atom;
C1-C8-alkyl;
C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkoxy-C1-C8-alkyl;
C2-C8-alkenyl;
C2-C8-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkynyl;
C2-C8-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different;
C3-C7-cycloalkyl;
C3-C7-cycloalkyl-C1-C8-alkyl;
C3-C7-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different;
formyl;
C1-C8-alkylcarbonyl;
C1-C8-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylsulfonyl;
C1-C8-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;
C1-C8-alkyl;
C1-C8-alkoxy;
C1-C8-alkylsulfanyl;
C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
tri(C1-C8)alkylsilyl and tri(C1-C8)alkylsilyl-C1-C8-alkyl;
as well as any salt, N-oxide, or optically active or geometric isomer thereof.

169 more elements

Fungicidal N-cycloalkyl-benzyl-thiocarboxamides or N-cycloalkyl-benzyl-N′-substituted-amidine derivatives

Life of this patent

Fungicidal N-cycloalkyl-benzyl-thiocarboxamides or N-cycloalkyl-benzyl-N′-substituted-amidine derivatives

Life of this patent

Abstract

Claims12