Heteroarylpiperidine and piperazine derivatives as fungicides

Patent metadata

Field	Value
Publication number	US-9375009-B2
Application number	US-201214369007-A
Country	US
Kind code	B2
Filing date	Dec 21, 2012
Priority date	Dec 27, 2011
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

Heteroarylpiperidine and -piperazine derivatives of the formula (I)

in which the symbols R A1 , R A2 , X, Y, L 1 , L 2 , R B1 , R B2 , G, Q, p, R 1 , R 2 and R 10 are each as defined in the description, and salts, metal complexes and N-oxides of the compounds of the formula (I), and the use thereof for controlling phytopathogenic harmful fungi and processes for preparing compounds of the formula (I).

First claim

The invention claimed is:

1. A compound of formula (I)

in which the radicals are each defined as follows:
R A1 is hydrogen, halogen, cyano, amino, —CHO, —C(═O)OH, —C(═O)NH2, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, halocycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, alkylthio, haloalkylthio, cycloalkylthio, alkylamino, dialkylamino, haloalkylamino, halodialkylamino, cycloalkylamino, alkylcarbonylamino, haloalkylcarbonylamino, alkylsulphonylamino or haloalkylsulphonylamino,
R A2 is benzodioxyl,
R A6 is halogen, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy on the carbon ring members, and cyano, alkyl or alkoxy on the nitrogen ring members,
L 1 is oxygen, sulphur, —N(R L1 )—, —C(R L2 ) 2 —, —OC(R L2 ) 2 —, —SC(R L2 ) 2 —, —N(R L1 )—C(R L2 ) 2 —, where the bond pointing to the left is bonded to the nitrogen atom of formula I and the bond pointing to the right is bonded to the nitrogen atom of formula I,
R L1 is hydrogen, cyano, alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulphonyl or haloalkylsulphonyl, or the two R L1 and R A2 radicals together with the carbon atom to which they are bonded form a five- to seven-membered partially unsaturated ring optionally containing one, two or three heteroatoms from the group of oxygen, nitrogen and sulphur, where the ring may be unsubstituted or substituted, where the substituents are each independently selected from R A6 ,
R L2 is hydrogen, alkyl or haloalkyl,
R B1 is hydrogen, halogen, cyano, hydroxyl, formyl, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyloxy, haloalkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, or
R B1 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical, each of which may contain 0, 1, 2 or 3 substituents, where the substituents are each independently selected from the following list: hydrogen, halogen, alkyl, haloalkyl, cycloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,
R B2 is hydrogen, alkyl or haloalkyl,
or the two R B1 and R B2 radicals together with the carbon atom to which they are bonded form a three- to six-membered saturated ring,

Y is sulphur or oxygen,
X is carbon or nitrogen,
R 2 is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
R 10 is the same or different and is independently hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
p is 0, 1 or 2,
G is 5-membered heteroaryl which is substituted by Q and may otherwise be unsubstituted or substituted,
Q is saturated or partly or fully unsaturated 5-membered heterocyclyl which is substituted by L 2 -R 1 and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from R 5 ,
R 5 is the same or different and is independently:
bonded to carbon of the 5-membered heterocyclyl of Q:
oxo, thioxo, hydrogen, halogen, cyano, hydroxyl, nitro, amino, —CHO, —C(═O)OH, —C(═O)NH 2 , —NR 3 R 4 , alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl, hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl, alkylsulphonylamino, haloalkylsulphonylamino,

bonded to nitrogen of the 5-membered heterocyclyl of Q:
hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, —C(═O)H, alkoxycarbonyl or alkylcarbonyl,

R 3 is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl,
R 4 is alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl or -L 5 R 1 ,
L 5 is —O—, —C(═O)—, S(═O) m or CHR 20 ,
m is 0, 1 or 2,
L 2 is a direct bond, —O—, —C(═O)—, —S(═O) m —, —CHR 20 — or —NR 21 —,
R 20 is hydrogen, alkyl or haloalkyl,
R 21 is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl,
R 1 is phenyl which is substituted at least once by alkynyloxy and may otherwise be unsubstituted or substituted, where the substituents are each independently selected from Z 4 and optionally from Z 1 ,
Z 1 is
bonded to carbon of R 1 :
hydrogen, halogen, hydroxyl, amino, nitro, amino, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, alkoxyalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl, alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy, alkylamino, dialkylamino, cycloalkylalkyl, cycloalkylcycloalkyl, alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, trialkylsilyl, and cycloalkylamino, cycloalkenyl, halocycloalkenyl, cycloalkoxyalkyl, halocycloalkoxy, cycloalkylthio, cycloalkoxy, cycloalkylalkoxy, cycloalkylamino, halocycloalkylalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl, or -L 3 Z 3 ,

bonded to nitrogen of R 1 :
alkyl, alkylcarbonyl, alkoxycarbonyl or alkoxy,

L 3 is a direct bond, —C(═O)—, sulphur, oxygen, —NR 21 —, —C(═S)—, —S(═O) m —, —CHR 20 , —CHR 20 —CHR 20 —, —CR 20 ═CR 20 —, —OCHR 20 —, —CHR 20 O—,
Z 3 is a phenyl radical, naphthalenyl radical or a 5- or 6-membered heteroaryl radical, each of which may contain 0, 1, 2 or 3 substituents, where the substituents are each independently selected from the following list:
substituents on carbon: halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio, alkylsulphinyl, halo

Assignees

• Bayer Ip Gmbh

Inventors

• Tsuchiya Tomoki
• Wasnaire Pierre
• Hoffmann Sebastian
• Seitz Thomas
• Hillebrand Stefan
• Benting Juergen
• Schmidt Jan Peter
• Cristau Pierre

Classifications

• A61P31/04

  Antibacterial agents · CPC title

• C07D211/62 Primary

  attached in position 4 · CPC title

• A01N43/80 Primary

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D419/14

  containing three or more hetero rings · CPC title

• C07D417/14 Primary

  containing three or more hetero rings · CPC title