Halogen-substituted compounds

Patent metadata

Field	Value
Publication number	US-9706775-B2
Application number	US-201414772471-A
Country	US
Kind code	B2
Filing date	Feb 27, 2014
Priority date	Mar 4, 2013
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

The invention relates inter alia to halogen-substituted compounds of the general formula (II)

in which the radicals A 1 -A 4 , T, n, W, Q, R 1 and Z 1 -Z 3 have the meanings given in the description. Also described are processes for preparing the compounds of the formula (II). The compounds according to the invention are particularly suitable for controlling insects, arachnids and nematodes in agriculture and ectoparasites in veterinary medicine.

First claim

We claim:

1. A compound of the general formula (II)

in which
R 1 represents hydrogen, or optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, or heteroaryl-(C 1 -C 3 )-alkyl,
M 1 and M 2 each independently of one another represent hydrogen, cyano or represent optionally mono- or polysubstituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, or C 1 -C 6 -alkoxycarbonyl, or
M 1 and M 2 with the carbon atom to which they are attached form an optionally substituted 3-, 4-, 5- or 6-membered ring which optionally contains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulphur atoms,
the chemical groupings
A 1 represents CR 2 or nitrogen,
A 2 represents CR 3 or nitrogen,
A 3 represents CR 4 or nitrogen and
A 4 represents CR 5 or nitrogen,
but where not more than three of the chemical groupings A 1 to A 4 simultaneously represent nitrogen;
R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, nitro, or optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxy-imino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino or N,N-di-C 1 -C 6 -alkylamino;
if none of the groupings A 2 and A 3 represents nitrogen, R 3 and R 4 together with the carbon atom to which they are attached may form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or
if none of the groupings A 1 and A 2 represents nitrogen, R 2 and R 3 together with the carbon atom to which they are attached may form a 6-membered ring which contains 0, 1 or 2 nitrogen atoms;
Q represents hydrogen, hydroxy, amino or one of the optionally substituted groupings alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl or represents a grouping N-alkylamino, N-alkylcarbonylamino, or N,N-dialkylamino; or
Q represents an unsaturated 6-membered carbocycle which is optionally mono- or polysubstituted by V or an unsaturated 5- or 6-membered heterocyclic ring which is optionally mono- or polysubstituted by V, where
V independently of one another represent halogen, cyano, nitro, or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, N-alkoxyiminoalkyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, or N,N-dialkylamino,
T represents one of the 5-membered heteroaromatics T1-T8 listed below, where the bond to the pyrazole head group is marked with an asterisk,

where
R 6 independently of one another represent halogen, cyano, nitro, amino or optionally substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, or C 1 -C 6 -alkylsulphonyl, and
n represents the values 0, 1, or 2;
Z 1 represents optionally substituted alkyl or cycloalkyl, and
Z 2 represents hydrogen, halogen, cyano, nitro, amino or optionally substituted alkyl, alkylcarbonyl, alkylsulphanyl, alkylsulphinyl, or alkylsulphonyl,
and
Z 3 represents hydrogen or optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl or hetaryl.

2. A compound according to claim 1 in which
R 1 represents hydrogen, or optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, or heteroaryl-(C 1 -C 3 )-alkyl,
M 1 and M 2 each independently of one another represent hydrogen, cyano or represent optionally mono- or polysubstituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, or C 1 -C 6 -alkoxycarbonyl, or
M 1 and M 2 with the carbon atom to which they are attached form an optionally substituted 3-, 4-, 5- or 6-membered ring which optionally contains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulphur atoms,
the chemical groupings
A 1 represents CR 2 or nitrogen,
A 2 represents CR 3 or nitrogen,
A 3 represents CR 4 or nitrogen and
A 4 represents CR 5 or nitrogen,
but where not more than three of the chemical groupings A 1 to A 4 simultaneously represent nitrogen;
R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, halogen, cyano, nitro, or optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxyimino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino or N,N-di-C 1 -C 6 -alkylamino;
if none of the groupings A 2 and A 3 represents nitrogen, R 3 and R 4 together with the carbon atom to which they are attached may form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or
if none of the groupings A 1 and A 2 represents nitrogen, R 2 and R 3 together with the carbon atom to which they are attached may form a 6-membered ring which contains 0, 1 or 2 nitrogen atoms;
Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted groupings C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 2 -C 7 -heterocycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, aryl-(C 1 -C 3 )-alkyl, heteroaryl-(C 1 -C 3 )-alkyl or represents a grouping N—C 1 -C 4 -alkylamino, N—C 1 -C 4 -alkylcarbonylamino, or N,N-di-C 1 -C 4 -alkylamino; or
Q represents an unsaturated 6-membered carbocycle which is optionally mono- or polysubstituted by V or an unsaturated 5- or 6-membered heterocyclic ring which is optionally mono- or polysubstituted by V, where
V independently of one another represent halogen, cyano, nitro, or optionally substituted C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxy-imino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, or N,N-di-(C 1 -C 6 -alkyl)amino;
T represents one of the 5-membered heteroaromatics T1-T8 listed below, where the bond to the pyrazole head group is marked with an asterisk,

where
R 6 independently of one another represent halogen, cyano, nitro, amino or optionally halogen-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, or C 1 -C 6 -alkylsulphonyl, and
n represents the values 0 or 1;
Z 1 represents optionally substituted C 1 -C 6 -haloalkyl, or C 3 -C 6 -halocycloalkyl,
Z 2 represents hydrogen, halogen, cyano, nitro, amino or optionally substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, or C 1 -C 6 -alkylsulphonyl, and
Z 3 represents hydrogen or optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, aryl or hetaryl.

3. A compound according to claim 1 in which
R 1 represents hydrogen or represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, aryl-(C 1 -C 3 )-alkyl, or heteroaryl-(C 1 -C 3 )-alkyl which are optionally mono- to heptasubstituted independently of one anot

Assignees

• Bayer Animal Health Gmbh

Inventors

• Maue Michael
• Decor Anne
• Bretschneider Thomas
• Hahn Julia Johanna
• Hallenbach Werner
• Fischer Reiner
• Schwarz Hans-Georg
• Görgens Ulrich
• Ilg Kerstin
• Raming Klaus
• Köbberling Johannes
• Hübsch Walter
• Turberg Andreas

Classifications

• A61P33/00 Primary

  Antiparasitic agents · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A01N43/647

  Triazoles; Hydrogenated triazoles · CPC title

• C07D403/14

  containing three or more hetero rings · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title