US 7,803,821 B2 · Fungicide N-cycloalkyl-carboxamide, thiocarboxamide and N-substituted-carboximidamide derivatives

Abstract

The present invention relates to N-cycloalkyl-carboxamide, N-cycloalkyl-thiocarboxamide and N-cycloalkyl-N-substituted carboximidamide derivatives of formula (I) wherein A represents carbo-linked, 5-membered heterocyclyl groups, T represents O, S, NRc, N—ORd, N—NRcRd or N—CN, Z1 represents cycloalkyl groups and Z2 and Z3, W1 to W5 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 represents a carbo-linked unsaturated or partially saturated, 5-membered heterocyclyl group that can be substituted by up to four groups Ra;
T is selected from the group consisting of O, S, NRc, N—ORd, N—NRcRd, and N—CN;
Z1 represents a non substituted C3-C7-cycloalkyl or a C3-C7 cycloalkyl substituted by up to 10 atoms or groups independently selected from 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-C8-alkoxy;
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-alkyl)aminocarbonyl;
Z2 and Z3 are independently selected from the group consisting of a hydrogen atom;
a halogen atom;
C1-C8-alkyl;
C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkenyl;
C2-C8-alkynyl;
cyano;
nitro;
C1-C8-alkoxy;
C2-C8-alkenyloxy;
C2-C8-alkynyloxy;
C3-C7-cycloalkyl;
C1-C8-alkylsulphenyl;
amino;
C1-C8-alkylamino;
di-(C1-C8-alkyl)amino;
C1-C8-alkoxycarbonyl;
C1-C8-alkylcarbonyl;
C1-C8-alkylcarbamoyl;
di-(C1-C8-alkyl)carbamoyl;
N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl;
or
Z2 and Z3 together with the carbon atom to which they are linked can form a substituted or non substituted C3-C7 cycloalkyl;
W1 to W5 are independently represent selected from the group consisting of N and CRb, at least one of W1 to W5 representing N and at least three of W1 to W5 representing CRb;
each Ra is independently selected from the group consisting of a hydrogen atom;
halogen atom;
cyano;
nitro;
amino;
sulfanyl;
hydroxyl;
pentafluoro-λ-6-sulfanyl;
C1-C8-alkylamino;
di-(C1-C8-alkyl)amino;
tri(C1-C8-alkyl)silyl;
tri(C1-C8-alkyl)silyl-C1-C8-alkyl;
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-alkoxy-C1-C8-alkyl;
C1-C8-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
C2-C8-alkenyloxy;
C2-C8-alkynyloxy;
C3-C7cycloalkyl;
C3-C7-cycloalkyl-C1-C8-alkyl;
C1-C8-alkylsulphinyl;
C1-C8-alkylsulphonyl;
C1-C8 alkoxyimino;
(C1-C8-alkoxyimino)-C1-C8-alkyl;
(benzyloxyimino)-C1-C8-alkyl;
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;
and C1-C8-alkylaminocarbonyl;
di-(C1-C8-alkyl)aminocarbonyl;
each Rb is independently selected from the group consisting of a hydrogen atom;
halogen atom;
nitro;
cyano;
hydroxyl;
sulphanyl;
amino;
pentafluoro-λ6-sulphanyl;
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-alkyl)amino;
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-alkylsulphanyl;
C1-C8-halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylsulphenyl, C1-C8-halogenoalkylsulphenyl comprising up to 9 halogen atoms that can be the same or different, C1-C3alkylsulphinyl, C1-C8-halogenoalkylsulphinyl comprising up to 9 halogen atoms that can be the same or different, C1-C8-alkylsulphonyl, C1-C8-halogenoalkylsulphonyl 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-alkinyloxy;
C2-C8-halogenoalkinyloxy 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;
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-C8-alkylaminocarbonyl;
di-(C1-C8-alkyl)aminocarbonyl;
C1-C8-alkylcarbonyloxy;
C1-C8-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different;
C1-C8-alkylcarbonylamino;
C1-C8-alkylaminocarbonyloxy;
di-(C1-C8-alkyl)aminocarbonyloxy;
C1-C8-alkyloxycarbonyloxy;
C1-C8-alkoxyimino;
(C1-C8-alkoxyimino)-C1-C8-alkyl;
(C1-C8-alkenyloxyimino)-C1-C8-alkyl;
(C1-C8-alkynyloxyimino)-C1-C8-alkyl;
(benzyloxyimino)-C1-C8-alkyl;
tri(C1-C8-alkyl)silyl;
tri(C1-C8-alkyl)silyl-C1-C8-alkyl;
phenyl that can be substituted by up to 5 groups Q;
benzyloxy that can be substituted by up to 5 groups Q;
benzylsulphanyl that can be substituted by up to 5 groups Q;
benzylamino that can be substituted by up to 5 groups Q;
phenoxy that can be substituted by up to 5 groups Q;
phenylamino that can be substituted by up to 5 groups Q;
phenylsulphanyl that can be substituted by up to 5 groups Q;
benzyl 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;
Rc and Rd 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-alkylsulphonyl;
C1-C8-halogenoalkylsulphonyl 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 phenylsulphonyl 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;
C1-C8-alkoxyimino;
and (C1-C8-alkoxyimino)-C1-C8-alkyl;
as well as a salt, or an N-oxide, or a metallic complex, or a metalloidic complex, or an optically active isomer, or a geometric isomer thereof;
provided that, when W2 to W5 are all CRb, Rb within W2 to W5 does not represent a C1-C8-alkyl or a C1-C8-halogenoalkyl when W1 represents N and that, when W1 to W4 are all CRb, Rb within W1 to W4 does not represent a C1-C8-alkyl or a C1-C8-halogenoalkyl when W5 represents N.

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Fungicide N-cycloalkyl-carboxamide, thiocarboxamide and N-substituted-carboximidamide derivatives

Life of this patent

Fungicide N-cycloalkyl-carboxamide, thiocarboxamide and N-substituted-carboximidamide derivatives

Life of this patent

Abstract

Claims17