Fungicidal N-cycloalkyl-N-{[ortho-(1-substituted-cycloalkyl)heteroaryl]methyl}(thio)carboxamides

Patent metadata

Field	Value
Publication number	US-10244756-B2
Application number	US-201615575292-A
Country	US
Kind code	B2
Filing date	May 19, 2016
Priority date	May 21, 2015
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

The invention relates to fungicidal N-cycloalkyl-N-{[ortho-(1-substituted-cycloalkyl)heteroaryl]methyl}carboxamides and their thiocarbonyl analogs of formula (I), their process of preparation, their use as fungicides, particularly in the form of fungicidal compositions, and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions. A represents a carbo-linked, unsaturated or partially saturated, optionally substituted 5-membered heterocyclyl group; T represents O or S; Z 1 represents an optionally substituted C 3 -C 7 -cycloalkyl; p represents 1-5; B 1 represents a carbo-linked, unsaturated, monocyclic or fused bicyclic 5-, 6-, 8-, 9-, 10-membered heterocyclyl ring, wherein the dotted line between the two adjacent carbons represents a single bond, a double bond or an aromatic bond.

First claim

The invention claimed is:

1. 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 that can be the same or different, provided that A is not a 3-(dihalogenomethyl)-5-halogeno-1-methyl-1H-pyrazol-4-yl group wherein the halogeno atoms are independently a fluoro or chloro atom;
T is O or S;
n is 0, 1, 2, 3 or 4;
m is 0, 1, 2, 3, 4, 5 or 6;
p is 1, 2, 3, 4 or 5;
Z 1 is a non-substituted C 3 -C 7 -cycloalkyl or a C 3 -C 7 -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, 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 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, 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 and di-C 1 -C 8 -alkylaminocarbonyl;
Z 2 and Z 3 are independently a hydrogen atom; substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; cyano; isonitrile; nitro; a halogen atom; substituted or non-substituted C 1 -C 8 -alkoxy; substituted or non-substituted C 2 -C 8 -alkenyloxy; substituted or non-substituted C 2 -C 8 -alkynyloxy; substituted or non-substituted C 3 -C 7 -cycloalkyl; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; amino; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; or substituted or non-substituted N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxy-carbamoyl; or
Z 2 and Z 3 together with the carbon atom to which they are linked can form a substituted or non-substituted C 3 -C 7 -cycloalkyl;
Z 4 is a halogen atom; hydroxy; cyano; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; formyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; carboxy; or substituted or non-substituted C 1 -C 8 -alkoxycarbonyl;
B 1 is a carbo-linked unsaturated, monocyclic or fused bicyclic 5-, 6-, 8-, 9-, 10-membered heterocyclyl ring comprising from 1 up to 4 heteroatoms selected in the list consisting of N, O, S; wherein the dotted line between the two adjacent carbons is a single bond, a double bond or an aromatic bond, with the proviso that B 1 is not a 1,3-benzodioxolyl group;
each W is independently a halogen atom; nitro; cyano; isonitrile; hydroxy; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; formyl; formyloxy; formylamino; substituted or non-substituted (hydroxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 3 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 9 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 7 -cycloalkenyl; C 4 -C 7 -halogenocycloalkenyl having 1 to 9 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkenyl; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkynyl; substituted or non-substituted bicyclo[2.2.1]heptanyl; substituted or non-substituted bicyclo[2.2.1]heptenyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonylamino C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkyloxycarbonyloxy C 1 -C 8 -halogenoalkoxycarbonyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted di-C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted N—(C 1 -C 8 -alkyl)hydroxy carbamoyl; substituted or non-substituted C 1 -C 8 -alkoxycarbamoyl; substituted or non-substituted N—(C 1 -C 8 -alkyl)-C 1 -C 8 -alkoxycarbamoyl; aryl that can be substituted by up to 6 groups Q which can be the same or different; C 1 -C 8 -arylalkyl that can be substituted by up to 6 groups Q which can be the same or different; C 2 -C 8 -arylalkenyl that can be substituted by up to 6 groups Q which can be the same or different; C 2 -C 8 -arylalkynyl that can be substituted by up to 6 groups Q which can be the same or different; aryloxy that can be substituted by up to 6 groups Q which can be the same or different; arylsulfanyl that can be substituted by up to 6 groups Q which can be the same or different; arylamino that can be substituted by up to 6 groups Q which can be the same or different; C 1 -C 8 -arylalkyloxy that can be substituted by up to 6 groups Q which can be the same or different; C 1 -C 8 -arylalkylsulfanyl that can be substituted by up to 6 groups Q which can be the same or different; C 1 -C 8 -arylalkylamino that can be substituted by up to 6 groups Q which can be the same or different; C 1 -C 8 -heteroarylalkyl that can be substituted by up to 6 groups Q which can be the same or different; heteroaryl which can be substituted by up to 4 groups Q; or heteroaryloxy which can be substituted by up to 4 groups Q;
each Y is indep

Assignees

• Bayer Cropscience Ag

Inventors

• Cristau Pierre
• Desbordes Philippe
• Geist Julie
• Nicolas Lionel
• Rinolfi Philippe
• Schmidt Jan Peter
• Tsuchiya Tomoki

Classifications

• A01N43/56 Primary

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

• C07D401/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title