US 8,026,195 B2Granted

Fungicidal N-cycloalkyl-carboxamide derivatives

AssigneeBayer CropScience AG

InventorsRalf Dunkel, Stéphanie Gary, Marie-Claire Grosjean-Cournoyer, Philippe Rinolfi, Arounarith Tuch

Life of this patent

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Abstract

The present invention relates to N-cycloalkyl-thiocarboxamide or N-cycloalkyl-N-substituted carboximidamide derivatives of formula (I) wherein A and B represent a 5-membered heterocyclyl groups, T represents an oxygen, sulphur or amino derivatives, Z1 represents a cycloalkyl group and Z2 and Z3 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.

Claims12

Dependent claims

A compound of formula (I)

wherein
R1 is C1-C8-alkyl;
R2 and R3 are independently selected from the group consisting of a hydrogen atom;
a halogen atom;
C1-C8-alkyl;
and C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
T is selected from the group consisting of O, S, N—Ra, N—ORa, N—NRaRb, and N—CN;
Ra and 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;
phenylsulfonyl that can be substituted by up to 5 groups Q;
B represents a carbo-linked, unsaturated, 5-membered heterocyclyl group that can be substituted by up to four groups X;
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 that can be the same or different and are selected from the group consisting of a halogen atom;
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-C8alkoxycarbonyl;
and C1-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different;
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-alkylamino;
C1-C8-alkoxycarbonyl;
C1-C8alkylcarbonyl;
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 which they are linked can form a substituted or non-substituted C3-C7-cycloalkyl;
each X is independently selected from the group consisting of a hydrogen atom;
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;
C1-C8-alkylsulfenyl;
C1-C8-halogenoalkylsulfenyl comprising up to 9 halogen atoms that can be the same or different, C1-C8-alkylsulfinyl;
C1-C8-halogenoalkylsulfinyl 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;
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;
N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl;
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-alkylaminocarbonyloxy;
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;
benzylsulfanyl 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;
phenylsulfanyl 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;
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;
tri(C1-C8)alkylsilyl-C1-C8-alkyl;
C1-C8-alkoxyimino;
and (C1-C8-alkoxyimino)-C1-C8-alkyl;
as well as salts, N-oxides, and optically active or geometric isomers thereof.

136 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/309,805Filed 30 Jul 2007
Priority: EP 0635609831 Jul 2006
Published: US 2009/0326016 A131 Dec 2009
Granted: 27 Sep 2011
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 413/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 403/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 409/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links

Family

US 2009/0326016 A1Pre-grant publication · published 31 Dec 2009
US 8,026,195 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of formula (I)

wherein
R1 is C1-C8-alkyl;
R2 and R3 are independently selected from the group consisting of a hydrogen atom;
a halogen atom;
C1-C8-alkyl;
and C1-C8-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
T is selected from the group consisting of O, S, N—Ra, N—ORa, N—NRaRb, and N—CN;
Ra and 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;
phenylsulfonyl that can be substituted by up to 5 groups Q;
B represents a carbo-linked, unsaturated, 5-membered heterocyclyl group that can be substituted by up to four groups X;
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 that can be the same or different and are selected from the group consisting of a halogen atom;
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-C8alkoxycarbonyl;
and C1-C8-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different;
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-alkylamino;
C1-C8-alkoxycarbonyl;
C1-C8alkylcarbonyl;
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 which they are linked can form a substituted or non-substituted C3-C7-cycloalkyl;
each X is independently selected from the group consisting of a hydrogen atom;
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;
C1-C8-alkylsulfenyl;
C1-C8-halogenoalkylsulfenyl comprising up to 9 halogen atoms that can be the same or different, C1-C8-alkylsulfinyl;
C1-C8-halogenoalkylsulfinyl 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;
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;
N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl;
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-alkylaminocarbonyloxy;
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;
benzylsulfanyl 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;
phenylsulfanyl 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;
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;
tri(C1-C8)alkylsilyl-C1-C8-alkyl;
C1-C8-alkoxyimino;
and (C1-C8-alkoxyimino)-C1-C8-alkyl;
as well as salts, N-oxides, and optically active or geometric isomers thereof.

136 more elements

Facts

Application

12/309,805Filed 30 Jul 2007

Priority

EP 0635609831 Jul 2006

Published

US 2009/0326016 A131 Dec 2009

Granted

27 Sep 2011

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07D 413/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 403/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 409/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07D 417/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links