Fungicide N-cycloalkyl-N-biphenylmethyl-carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-9320277-B2
Application number	US-201414183965-A
Country	US
Kind code	B2
Filing date	Feb 19, 2014
Priority date	Aug 1, 2008
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

The present invention relates to N-cycloalkyl-N-biphenylmethyl-carboxamide derivatives of formula (I)

wherein A, Z 1 , Z 2 , Z 3 , X, n, Y and m represent various substituents, their process of preparation, preparation intermediate compounds, 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.

First claim

The invention claimed is:

1. A compound of formula (II)

wherein
Z 2 and Z 3 , that can be the same or different, represent a hydrogen atom; C 1 -C 8 -alkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; cyano; nitro; a halogen atom; C 1 -C 8 -alkoxy; C 2 C 8 -alkenyloxy; C 2 -C 8 -alkynyloxy; C 3 -C 7 -cycloalkyl; C 1 -C 8 -alkylsulphenyl; amino; C 1 -C 8 -alkylamino; di-C 1 -C 8 -alkylamino; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; or Z 2 and Z 3 together with the carbon atom to that they are linked can form a substituted or non substituted C 3 -C 7 -cycloalkyl;
X and Y independently represent a halogen atom; nitro; cyano; isonitrile; hydroxyl; sulfanyl; amino; pentafluoro-λ 6 -sulfanyl; 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 -alkylamino; di-C 1 -C 8 -alkylamino; C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; C 1 -C 8 -alkoxy-C 1 -C 8 -alkoxy; C 1 -C 8 -alkylsulphanyl; C 1 -C 8 -halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different; 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 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy 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 -cycloalkyl-C 2 -C 8 -alkenyl; C 3 -C 7 -cycloalkyl-C 2 -C 8 -alkynyl; C 3 -C 7 -halogenocycloalkyl 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 -cycloalkyl; C 6 -C 14 -bicycloalkyl; formyl; formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C 1 -C 8 -alkyl; 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 -alkylcarbamoyl; di-C 1 -C 8 -alkylcarbamoyl; N—C 1 -C 8 -alkyloxycarbamoyl; C 1 -C 8 -alkoxycarbamoyl; N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl; C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylaminocarbonyl; di-C 1 -C 8 -alkylaminocarbonyl; C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylaminocarbonyloxy; di-C 1 -C 8 -alkylaminocarbonyloxy; C 1 -C 8 -alkyloxycarbonyloxy, C 1 -C 8 -alkylsulphenyl; C 1 -C 8 -halogenoalkylsulphenyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulphinyl; C 1 -C 8 -halogenoalkylsulphinyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulphonyl; C 1 -C 8 -halogenoalkylsulphonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkoxyimino; (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; (C 2 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl; (C 2 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl; (benzyloxyimino)-C 1 -C 8 -alkyl; tri(C 1 -C 8 -alkyl)silyl; tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -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; aryl that can be substituted by up to 5 groups Q; aryloxy that can be substituted by up to 5 groups Q; arylamino that can be substituted by up to 5 groups Q; arylsulfanyl that can be substituted by up to 5 groups Q; aryl-C 1 -C 8 -alkyl that can be substituted by up to 5 groups Q; aryl-C 2 -C 8 -alkenyl that can be substituted by up to 5 groups Q; aryl-C 2 -C 8 -alkynyl that can be substituted by up to 5 groups Q; aryl-C 3 -C 7 -cycloalkyl that can be substituted by up to 5 groups Q; pyridinyl that can be substituted by up to 4 groups Q and pyridinyloxy that can be substituted by up to 4 groups Q; or
two substituents X together with the consecutive carbon atoms to that they are linked can form a 5- or 6-membered, saturated, carbo- or hetero-cycle comprising up to 3 heteroatoms fused with the phenyl ring to that the two substituent X are linked, that can be substituted by up to 4 groups Q that can be the same or different; or
two substituents Y together with the consecutive carbon atoms to that they are linked can form a 5- or 6-membered, saturated, carbo- or hetero-cycle comprising up to 3 heteroatoms fused with the phenyl ring to that the two substituent X are linked, that can be substituted by up to 4 groups Q that can be the same or different;
n represents 0, 1, 2, 3 or 4;
m represents 0, 1, 2, 3, 4 or 5;
Q independently represents a halogen atom; cyano; isonitrile; nitro; C 1 -C 8 -alkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; C 1 -C 8 -alkoxy; C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; C 1 -C 8 -alkoxy-C 1 -C 8 -alkoxy; C 1 -C 8 -alkylsulphanyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -halogenoalkynyl 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; C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl 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;

with the exclusion of N-(biphenyl-4-ylmethyl)cyclopropanamine and N-[1-(biphenyl-4-yl)ethyl]cyclopropanamine.

Assignees

• Desbordes Philippe
• Dunkel Ralf
• Gary Stephanie
• Grosjean-Cournoyer Marie-Claire
• Hartmann Benoit
• Rinolfi Philippe
• Vors Jean-Pierre
• Rama Rachel
• Bayer Ip Gmbh

Inventors

• Desbordes Philippe
• Dunkel Ralf
• Gary Stephanie
• Grosjean-Cournoyer Marie-Claire
• Hartmann Benoit
• Rinolfi Philippe
• Vors Jean-Pierre
• Rama Rachel

Classifications

• A01N43/78 Primary

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• C07D231/14

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07D277/56

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• C07D231/16 Primary

  Halogen atoms or nitro radicals · CPC title