US 2010/0144785 A1 · FUNGICIDE N-6-MEMBERED FUSED (HETERO) ARYL-METHYLENE-N-CYCLOALKYL CARBOXAMIDE DERIVATIVES

Abstract

The present invention relates N-(aromatic, 6-membered, fused, (hetero)aryl-methylene)-N-cycloalkyl carboxamide derivatives, their thiocarboxamide or N-substituted carboximidamide analogues, all of formula (I) wherein A represents a carbo-linked 5-membered heterocyclyl group; T represents O, S, N—Rc, N—ORd, N—NRcRd or N—CN; Z1 to Z3 and B represents an aromatic, 6-membered, fused, (hetero)aryl; 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;
B represents
wherein
W1 to W5 independently represent N or CRb1;
Y1 to Y3 independently represent N, O, S, NRb2 or CRb3;
Y1 to Y3 together with the atoms Wn to which they are linked, form an aromatic 5- or 6-membered, fused heterocyclyl ring comprising up to four heteroatoms, or an aromatic 6-membered fused carbocyclyl ring;
p represents 1 or 2;
T represents O, S, N—R′, N—ORd, N—NRcRd or N—CN;
Z1 represents a non substituted C3-C7-cycloalkyl or a C3-C7 cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and that can be selected in the list 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;
di-(C1-C8-alkyl)aminocarbonyl;
Z2 and Z3 independently represent 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;
Ra independently represents 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-C7-cycloalkyl;
C3-C7-cycloalkyl-C1-C8-alkyl;
C1-C8-alkylsulphinyl;
C1-C8-alkylsulphonyl;
C1-C8alkoxyimino;
(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;
C1-C8-alkylaminocarbonyl;
di-(C1-C8-alkyl)aminocarbonyl;
Rc and Rd, that can be the same or different, represent 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-C3-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;
phenylsulphonyl that can be substituted by up to 5 groups Q;
Rb1 and Rb3 independently represent a hydrogen atom;
halogen atom;
nitro;
cyano;
hydroxyl;
sulphanyl;
amino;
pentafluoro-X6-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-C8-alkylsulphinyl, 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;
Rb2 represents 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;
phenylsulfonyl can be substituted by up to 5 groups Q;
benzyl that can be substituted by up to 5 groups Q;
Q, that can be the same or different, represents 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;
(C1-C8-alkoxyimino)-C1-C8-alkyl;
as well as salts, N-oxides, metallic complexes, metalloidic complexes and optically active or geometric isomers thereof provided that compound of formula (I) differs from N-cyclopropyl-N-((6,8-dimethyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl)-furane-2-carboxamide, N-cyclopropyl-N-((6-ethoxy-2-oxo-1,2-dihydroquinolin-3-yl)methyl)-furane-2-carboxamide, N-cyclopropyl-N-(6-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl)-furane-2-carboxamide, N-cyclopropyl-N-((7,8-difluoro-2-oxo-1,2-dihydroquinolin-4-yl)methyl)-4-methylthiazole-5-carboxamide and from N-cyclopropyl-N-(8-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)methyl)-4-methylthiazole-5-carboxamide.

191 more elements

Fungicide n-6-membered fused (hetero) aryl-methylene-n-cycloalkyl carboxamide derivatives

Life of this patent

Fungicide n-6-membered fused (hetero) aryl-methylene-n-cycloalkyl carboxamide derivatives

Life of this patent

Abstract

Claims13