N-cycloalkyl-N-{[2-(1-substitutedcycloalkyl)phenyl]methylene}-(thio)carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-10070645-B2
Application number	US-201415100966-A
Country	US
Kind code	B2
Filing date	Dec 4, 2014
Priority date	Dec 5, 2013
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention relates to fungicidal N-cycloalkyl-N-{[2-(1-substitutedcycloalkyl)phenyl]methylene} carboxamide derivatives and their thiocarbonyl derivatives, their process of preparation and intermediate compounds for their 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.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
X 1 and X 2 are independently a chlorine or a fluorine 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;
Z 1 is a non-substituted cyclopropyl or a cyclopropyl substituted by up to 10 atoms or groups that are independently selected from the group consisting of halogen, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that are the same or different, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that are the same or different, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that are 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 form a substituted or non-substituted C 3 -C 7 -cycloalkyl;
Z 4 is a halogen atom; hydroxy; cyano; non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms; non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms; non-substituted C 1 -C 8 -alkoxy; or C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms;
W independently is 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 is optionally substituted by up to 6 groups Q which are the same or different; C 1 -C 8 -arylalkyl that is optionally substituted by up to 6 groups Q which are the same or different; C 2 -C 8 -arylalkenyl that is optionally substituted by up to 6 groups Q which are the same or different; C 2 -C 8 -arylalkynyl that is optionally substituted by up to 6 groups Q which are the same or different; aryloxy that is optionally substituted by up to 6 groups Q which are the same or different; arylsulfanyl that is optionally substituted by up to 6 groups Q which can be the same or different; arylamino that is optionally substituted by up to 6 groups Q which are the same or different; C 1 -C 8 -arylalkyloxy that is optionally substituted by up to 6 groups Q which are the same or different; C 1 -C 8 -arylalkylsulfanyl that is optionally substituted by up to 6 groups Q which are the same or different; C 1 -C 8 -arylalkylamino that is optionally substituted by up to 6 groups Q which are the same or different; C 1 -C 8 -heteroarylalkyl that is optionally substituted by up to 6 groups Q which are the same or different; heteroaryl which is optionally substituted by up to 4 groups Q; or heteroaryloxy which is optionally substituted by up to 4 groups Q; or
Z 4 and its vicinal substituent W, together with the carbon atom to which they are linked, form a substituted or non-substituted C 4 -C 7 -cycloalkyl;
Y independently is a halogen atom; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl 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; or substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; and
Q independently is a halogen atom, cyano, nitro, substituted or non-substituted C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that are the same or different, substituted or non-substituted C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that are the same or different, substituted or non-substituted C 1 -C 8 -a

Assignees

• Bayer Cropscience Ag

Inventors

• Cristau Pierre
• Desbordes Philippe
• Geist Julie
• Nicolas Lionel
• Rinolfi Philippe
• Schmidt Jan-Peter
• Tsuchiya Tomoki
• Vors Jean-Pierre
• Wachendorff-Neumann Ulrike

Classifications

• C07D231/16 Primary

  Halogen atoms or nitro radicals · CPC title

• C07C47/546

  polycyclic · CPC title

• C07C2601/02

  with a three-membered ring · CPC title

• C07C47/575

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C47/55

  containing halogen · CPC title