Tetrahydronaphthyl(thio) carboxamides

Patent metadata

Field	Value
Publication number	US-9630943-B2
Application number	US-201314652621-A
Country	US
Kind code	B2
Filing date	Dec 16, 2013
Priority date	Dec 19, 2012
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

The present invention relates to novel tetrahydronaphthyl(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. Tetrahydronaphthyl(thio) carboxamide of formula (I)

in which
Het represents a radical selected from the group Het1 or Het2;

X 1 represent 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 represents 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;

provided that when Het represents Het1, X 1 is not difluoro- or dichloromethyl and X 2 is not chlorine or fluorine;
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 -haloalkyl-sulfonyl, or halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine-atoms;
X represents fluorine, chlorine, methyl or trifluoromethyl;
m represents 0, 1 or 2;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen; cyano; C 1 -C 16 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 8 -cycloalkyl; (C 3 -C 8 -cycloalkyl)-C 1 -C 8 -alkyl; (C 3 -C 8 -cycloalkyl)-C 3 -C 8 -cycloalkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; C 2 -C 8 -alkenyl-C 1 -C 16 -alkyl; C 2 -C 8 -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 8 -alkenyloxy; C 3 -C 8 -alkynyloxy; 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 ; each of which is optionally substituted;
wherein one or more substituents of the group selected from R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 does not represent hydrogen;
or
R 1 and R 2 represent together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl; or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c ; or
R 3 and R 4 represent together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl; or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c ; or
R 5 and R 6 represent together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl; or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c ; or
R 7 and R 8 represent together with the carbon to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl; or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c or a group ═O; or
R 1 and R 3 represent together with the carbons to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl; or
R 3 and R 5 represent together with the carbons to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl; or
R 5 and R 7 represent together with the carbons to which they are attached an optionally substituted C 3 -C 8 -cycloalkyl; or
Y 1 and Y 2 independently of one another represent halogen, C 1 -C 12 -alkyl, C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms or form together with the carbon to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
R b represents halogen; nitro, cyano, C 1 -C 8 -alkyl; C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 4 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 4 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 4 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 8 -alkenyl; C 2 -C 8 -alkynyl; C 3 -C 6 -cycloalkyl; phenyl; tri(C 1 -C 6 )alkylsilyl; tri(C 1 -C 6 )alkylsilyl-C 1 -C 6 -alkyl;
R c represents C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 6 -cycloalkyl; (C 3 -C 6 -cycloalkyl)-C 1 -C 6 -alkyl; (C 3 -C 6 -cycloalkyl)-C 3 -C 6 -cycloalkyl; C 2 -C 6 -alkenyl-C 1 -C 12 -alkyl; C 2 -C 6 -alkynyl-C 1 -C 12 -alkyl; aryl-C 1 -C 6 -alkyl which is optionally substituted by up to 6 identical or different groups R b ; each of which is optionally substituted.

2. Tetrahydronaphthyl(thio) carboxamide of formula (I) according to claim 1 in which
Het represents Het1;
X 1 represents C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms selected from chlorine or fluorine;
X 2 represents hydrogen, fluorine, chlorine, bromine, iodine; C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 9 identical or different halogen atoms selected from chlorine or fluorine
provided that when Het represents Het1, X 1 is not difluoro- or dichloromethyl and X 2 is not chlorine or fluorine;
Q represents hydrogen, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- ortert-butyl sulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, tri-fluoromethylsulfonyl, trifluoromethoxymethyl
X represents fluorine, where fluorine is located in the 4-, 5- or 6-position of the tetra-hydronaphthyl radical;
m represents 0 or 1;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine; C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 3 -C 6 -cycloalkyl; (C 3 -C 6 -cycloalkyl)-C 1 -C 6 -alkyl ; (C 3 -C 6 -cycloalkyl) -C 3 -C 6 -cycloalkyl; C 1 -C 12 -alkoxy; C 3 -C 6 -cycloalkyloxy; (C 3 -C 6 -cycloalkyl) -C 1 -C 6 -alkyloxy; each of which is optionally substituted;
wherein one or more substituents of the group selected from R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 does not represent hydrogen;
R 1 and R 2 represent together with the carbon to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c ; or
R 3 and R 4 represent together with the carbon to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c ; or
R 5 and R 6 represent together with the carbon to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c ; or
R 7 and R 8 represent together with the carbon to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; or may form the group ═C(Y 1 )Y 2 or a group ═N—O—R c or a group ═O; or
R 1 and R 3 represents together with the carbons to which they are attached an optionally substituted cyclopropyl, cyclobutyl, cyclo

Assignees

• Bayer Cropscience Ag

Inventors

• Maechling Simon
• Coqueron Pierre-Yves
• Es-Sayed Mazen
• Sudau Alexander
• Wachendorff-Neumann Ulrike
• Carles Lionel
• Dubost Christophe
• Vors Jean-Pierre
• Brunet Stephane

Classifications

• A01N43/10

  with sulfur as the ring hetero atom · CPC title

• C07D333/38 Primary

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

• C07C211/60

  containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems · CPC title

• C07D277/32

  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

• C07D231/14 Primary

  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