Benzocyclobutane(thio) carboxamides

Patent metadata

Field	Value
Publication number	US-9878985-B2
Application number	US-201415031456-A
Country	US
Kind code	B2
Filing date	Oct 28, 2014
Priority date	Oct 30, 2013
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

The present invention relates to novel benzocyclobutane(thio) carboxamides, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials.

First claim

The invention claimed is:

1. Benzocyclobutane(thio) carboxamide of formula (I)

in which
Ar represents a radical selected from the group Ar1 to Ar15:

X 1 , X 2 , X 3 , X 4 and X 5 independently represent hydrogen; halogen; cyano; nitro, hydroxyl; C 1 -C 16 -alkyl, C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; or C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms;
T represents an oxygen or sulfur atom;
Q represents hydrogen, C 1 -C 6 -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkylsulfonyl, or halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
X represents halogen, nitro, cyano, C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 6 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfinyl; C 1 -C 6 -haloalkylsulfinyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 12 -alkenyl; C 2 -C 12 -alkynyl; C 3 -C 7 -cycloalkyl; phenyl; or tri(C 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;
m represents 0, 1, 2 or 3;
R 1 , R 2 , R 3 and R 4 independently one to another represent hydrogen; halogen; C 1 -C 16 -alkyl; C 2 -C 16 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 8 -cycloalkyl; C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyl; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl; C 2 -C 16 -alkenyl; C 2 -C 16 -alkynyl; C 2 -C 16 -alkenyl-C 1 -C 16 -alkyl; C 2 -C 16 -alkynyl-C 1 -C 16 -alkyl; C 1 -C 16 -alkoxy; C 3 -C 8 -cycloalkyloxy; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyloxy; C 1 -C 8 -alkylsulfanyl; C 3 -C 8 -cycloalkylsulfanyl; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkylsulfanyl; C 2 -C 16 -alkenyloxy; C 3 -C 8 -alkynyloxy; aryl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkyloxy which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkylsulfanyl which is optionally substituted by up to 6 identical or different groups R b ; aryloxy which is optionally substituted by up to 6 identical or different groups R b ; arylsulfanyl which is optionally substituted by up to 6 identical or different groups R b ; (C 3 -C 8 -cycloalkyl)-C 2 -C 8 -alkenyl; (C 3 -C 8 -cycloalkyl)-C 2 -C 8 -alkynyl; tri(C 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; aryl-C 1 -C 8 -alkyl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 2 -C 8 -alkenyl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 2 -C 8 -alkynyl which is optionally substituted by up to 6 identical or different groups R b ;
provided that R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen or

R 1 and R 2 represent together with the carbon to which they are attached a C 3 -C 8 -cycloalkyl; C 3 -C 8 -cycloalkenyl, each of which is optionally substituted or
R 1 and R 2 represent a group ═C(Y 1 )Y 2 or
R 1 and R 2 represent a 5 or 6 membered ring containing 1 or 2 heteroatoms or
R 3 and R 4 represent together with the carbon to which they are attached a C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl each of which is optionally substituted or
R 3 and R 4 represent a group ═C(Y 1 )Y 2 or
R 3 and R 4 represent a 5 or 6 membered ring containing 1 or 2 heteroatoms or
R 1 and R 3 represent with the carbons to which they are attached a C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl each of which is optionally substituted;
R b represents halogen; nitro, cyano, C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 6 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 12 -alkenyl; C 2 -C 12 -alkynyl; C 3 -C 7 -cycloalkyl; phenyl; tri(C 1 -C 8 )alkylsilyl; or tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl;
Y 1 and Y 2 independently of one another represent hydrogen, halogen, C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 8 -alkylsulfanyl; phenyl; each of which is optionally substituted or Y 1 and Y 2 can form together with the carbon to which they are attached a C 3 -C 8 -cycloalkyl or a C 3 -C 8 -cycloalkenyl or a saturated 5, 6 or 7 membered heterocycle; each of which is optionally substituted.

2. Benzocyclobutane(thio) carboxamide of formula (I) according to claim 1
in which
Ar represents a radical selected from the group Ar1, Ar2, Ar4, Ar7, Ar8, Ar10 and Ar13;
X 1 represents halogen; C 1 -C 16 -alkyl, C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 7 -cycloalkyl, or C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms;
X 2 , X 3 , X 4 and X 5 independently from each other represent hydrogen, halogen, C 1 -C 16 -alkyl, C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 7 -cycloalkyl, or C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms;
T represents an oxygen atom;
Q represents hydrogen, C 1 -C 4 -alkylsulfonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl having in each case 1 to 9 fluorine, chlorine or bromine atoms;
X represents fluorine, chlorine, methyl or trifluoromethyl;
m represents 0, 1 or 2;
R 1 , R 2 , R 3 and R 4 independently of one another represent hydrogen; halogen; C 1 -C 16 -alkyl; C 2 -C 16 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 8 -cycloalkyl; C 3 -C 7 -halocycloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyl; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl; C 1 -C 16 -alkoxy; C 3 -C 8 -cycloalkyloxy; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyloxy; aryl which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkyloxy which is optionally substituted by up to 6 identical or different groups R b ; aryl-C 1 -C 8 -alkyl which is optionally substituted by up to 6 identical or different groups R b ;
provided that R 1 , R 2 , R 3 and R 4 do not simultaneously represent hydrogen or
R 1 and R 2 represents together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl where the substituents can be chosen from halogen and C 1 -C 6 -alkyl or
R 3 and R 4 represents together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl where the substituents can be chosen from halogen and C 1 -C 6 -alkyl or
R 1 and R 3 represents together with the carbons to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl where the substituents can be chosen from halogen and C 1 -C 6 -alkyl;
R b represen

Assignees

• Bayer Cropscience Ag

Inventors

• Dubost Christophe
• Wachendorff-Neumann Ulrike
• Winter Philipp
• Brunet Stephane
• Vors Jean-Pierre
• Montagne Cyril

Classifications

• A01N43/56

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

• C07C17/275

  of hydrocarbons and halogenated hydrocarbons · CPC title

• C07D213/82

  in position 3 · CPC title

• C07C211/61

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C07C209/62

  by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds (C07C209/24 takes precedence) · CPC title