Halogen-substituted pyrazole derivatives as pest-control agents

Patent metadata

Field	Value
Publication number	US-9487489-B2
Application number	US-201414762825-A
Country	US
Kind code	B2
Filing date	Feb 3, 2014
Priority date	Feb 6, 2013
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

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

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 (I) and possible intermediates for the preparation of these compounds. The compounds according to the invention are particularly suitable for controlling insects, arachnids and nematodes in agriculture and ectoparasites in veterinary medicine.

First claim

The invention claimed is:

1. Compound of formula (I),

in which
R 1 represents hydrogen, 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,
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, 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;
W represents oxygen or sulphur;
Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted groupings alkyl, alkyloxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl or represents a grouping N-alkylamino, N-alkylcarbonylamino, N,N-dialkylamino; or
Q represents an unsaturated 6-membered carbocycle which is optionally polysubstituted by V or an unsaturated 5- or 6-membered heterocyclic ring which is optionally polysubstituted by V, where
V represents halogen, cyano, nitro, 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-T7 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 -alkyloxy, 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 0-2;
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. Compound according to claim 1 in which
R 1 represents hydrogen, optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 2 -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,
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, optionally substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-alkoxyiminoalkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, 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;
W represents oxygen or sulphur;
Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted groupings C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 5 -heterocyclo alkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -alkyl-C 3 -C 6 -cycloalkyl, 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, N,N-di-C 1 -C 4 -alkylamino; or
Q represents an unsaturated 6-membered carbocycle which is optionally polysubstituted by V or an unsaturated 5- or 6-membered heterocyclic ring which is optionally polysubstituted by V, where
V independently of one another represent halogen, cyano, nitro, optionally substituted C 1 -C 6 -alkyl, C 1 -C 4 -alkenyl, C 1 -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-T7 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 -alkyloxy, 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;
Z 1 represents optionally substituted C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, or C 3 -C 6 -halocycloalkyl, and
Z 2 represents 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 alkyl, cycloalkyl, alkenyl, alkynyl, aryl or hetaryl.

3. Compound according to claim 1 in which
R 1 represents hydrogen or represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl, 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- or polysubstituted independently of one another by halogen, cyano, alkoxy or alkoxycarbonyl,
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, 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;
W represents oxygen or sulphur;
Q represents hydrogen, hydroxy, formyl or one of the groupings C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycl

Assignees

• Bayer Cropscience Ag
• Bretschneider Niklas Tim
• Bretschneider Uta Antje

Inventors

• Maue Michael
• Ilg Kerstin
• Decor Anne
• Bretschneider Thomas
• Hahn Julia Johanna
• Hallenbach Werner
• Fischer Reiner
• Schwarz Hans-Georg
• Goergens Ulrich
• Raming Klaus
• Koebberling Johannes
• Huebsch Walter
• Turberg Andreas
• Lindner Niels

Classifications

• A01N43/713

  having rings with four or more nitrogen atoms as the only ring hetero atoms · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D231/18

  One oxygen or sulfur atom · CPC title

• A01N43/56

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

• C07D231/12 Primary

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