Halogen-substituted compounds

Patent metadata

Field	Value
Publication number	US-10047076-B2
Application number	US-201515300057-A
Country	US
Kind code	B2
Filing date	Apr 1, 2015
Priority date	Apr 2, 2014
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

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

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

First claim

The invention claimed is:

1. A compound of formula (I)

in which
R 1 represents hydrogen, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl, arylalkyl, heteroarylalkyl,

the chemical moieties
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 moieties 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 alkyl, cycloalkyl, alkoxy, N-alkoxyiminoalkyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, N-alkylamino or N,N-dialkylamino;
if neither of the A 2 and A 3 moieties is nitrogen, R 3 and R 4 together with the carbon atom to which they are bonded may form a 5- or 6-membered ring containing 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or
if neither of the A 1 and A 2 moieties is nitrogen, R 2 and R 3 together with the carbon atom to which they are bonded may form a 6-membered ring containing 0, 1 or 2 nitrogen atoms;
W represents oxygen or sulphur;
Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted moieties alkyl, alkyloxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl or represents a moiety N-alkylamino, N-alkylcarbonylamino, N,N-dialkylamino; or
Q represents a mono- to polyunsaturated 5- to 6-membered carbocycle which may optionally be interrupted by heteroatoms and is optionally mono- to polysubstituted by V, where
V represents halogen, cyano, nitro, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, N-alkoxyiminoalkyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, N,N-dialkylamino;
T represents one of the 5-membered heteroaromatic systems T1-T35 shown below, where the bond to the pyrazolyl head group is indicated by an asterisk,

where
R 6 independently of one another represent halogen, cyano, nitro, amino or optionally substituted alkyl, alkyloxy, alkylcarbonyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, and
n represents the values 0-2;
R 7 represents hydrogen, or optionally substituted alkyl or cycloalkyl in which optionally one methylene group is substituted by a heteroatom;
Z 1 represents optionally substituted haloalkyl or halocycloalkyl, and
Z 2 represents hydrogen, halogen, cyano, nitro, amino or optionally substituted alkyl, alkylcarbonyl, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, and
Z 3 represents hydrogen or optionally substituted alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, where
if T is T23 or T24, one of the radicals Z 1 , Z 2 or Z 3 is substituted by at least 3 halogen atoms.

2. A compound according to claim 1 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 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, heteroaryl-(C 1 -C 3 )-alkyl,

the chemical moieties
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 moieties 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 -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, N,N-di-C 1 -C 6 -alkylamino, or
if neither of the A 2 and A 3 moieties is nitrogen, R 3 and R 4 together with the carbon atom to which they are bonded may form a 5- or 6-membered ring containing 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or
if neither of the A 1 and A 2 moieties is nitrogen, R 2 and R 3 together with the carbon atom to which they are bonded may form a 6-membered ring containing 0, 1 or 2 nitrogen atoms;
W represents oxygen or sulphur;
Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted moieties C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 5 -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 moiety N—C 1 -C 4 -alkylamino, N—C 1 -C 4 -alkylcarbonylamino, N,N-di-C 1 -C 4 -alkylamino; or
Q represents a mono- to triunsaturated 5- to 6-membered carbocycle which is optionally mono- or polysubstituted by V or a mono- to triunsaturated 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 -alkoxyimino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N,N-di-(C 1 -C 6 -alkyl)amino;
T represents one of the 5-membered heteroaromatic systems T1-T35 shown below, where the bond to the pyrazolyl head group is indicated by 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, C 1 -C 6 -alkylsulphonyl, and
n represents the values 0-1;
R 7 represents hydrogen, or optionally substituted C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl in which optionally one methylene group may be substituted by heteroatoms;
Z 1 represents optionally substituted C 1 -C 6 -haloalkyl, C 3 -C 6 -halocycloalkyl, and
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, 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 5 -heterocycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl,
where if T is T23 or T24, one of the radicals Z 1 , Z 2 or Z 3 is substituted by at least 3 halogen atoms.

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 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, heteroaryl-(C 1 -C 3 )-alkyl which are optionally mono- to pentasubstituted independently of one another by fluorine, chlorine, cyano, alkoxy and alkoxycarbonyl,

the chemical moieties
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 moieties A 1 to A 4 simultaneously represent nitrogen;
R 2 , R 3 , R 4 and R 5 independently of

Assignees

• Bayer Cropscience Ag
• Bretschneider Niklas Tim
• Bretschneider Uta

Inventors

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

Classifications

• A61P7/00

  Drugs for disorders of the blood or the extracellular fluid · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D417/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N43/82

  five-membered rings with three ring hetero atoms · CPC title