US 2019/0053492 A1 · SUBSTITUTED PYRIDINE COMPOUNDS AS PESTICIDES

Abstract

The present invention relates to novel substituted pyridine compounds of the formula (I) in which R1, R2, R3, R4, R5, R6, V1, V2 and Q1 have the definitions given in the description, and to the use thereof as acaricides and insecticides for control of animal pests, particularly arthropods and especially insects and arachnids, and to processes and intermediates for preparation thereof.

Compound of formula (I) and/or salt thereof

in which
Q1 is in each case optionally singly or multiply, identically or differently substituted aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl or oxohetaryl,
where the substituents are selected from:
cyano, carboxyl, halogen, nitro, hydroxyl, amino, SCN, SF5, tri-(C1-C6)alkylsilyl, (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, hydroxycarbonyl-(C1-C6)-alkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)cyanoalkoxy, (C1-C6)alkoxycarbonyl-(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkoxy, (C3-C8)cycloalkyl, (C3-C9)halocycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, (C1-C6)haloalkyl-(C3-C8)cycloalkyl, (C1-C4)haloalkenoxy, (C1-C6)alkylhydroxyimino, (C1-C6)alkoxyimino, (C1-C6)alkyl-(C1-C6)alkoxyimino, (C1-C6)haloalkyl-(C1-C6)alkoxyimino, (C1-C6)alkylsulphanyl, (C1-C6)alkoxy-(C1-C6)alkylsulphanyl, (C1-C6)alkylsulphanyl-(C1-C6)alkyl, (C1-C6)alkylsulphinyl, (C1-C6)haloalkylsulphinyl, (C1-C6)alkoxy-(C1-C6)alkylsulphinyl, (C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkylsulphonyl, (C1-C6)haloalkylsulphonyl, (C1-C6)alkoxy-(C1-C6)alkylsulphonyl, (C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkylsulphonyloxy, (C1-C6)haloalkylsulphanyl, (C3-C6)cycloalkylsulphanyl, (C3-C6)halocycloalkylsulphanyl, (C3-C6)cycloalkylsulphonyl, (C3-C6)halocycloalkylsulphonyl, (C3-C6)cycloalkylsulphinyl, (C3-C6)halocycloalkylsulphinyl, (C1-C6)alkylcarbonyl, (C1-C6)haloalkylcarbonyl, (C1-C6)alkylcarbonyloxy, (C1-C6)alkoxycarbonyl, (C1-C6)haloalkoxycarbonyl, aminocarbonyl, (C1-C6)alkylaminocarbonyl, di-(C1-C6)alkylaminocarbonyl, (C2-C6)alkenylaminocarbonyl, di-(C2-C6)-alkenylaminocarbonyl, (C3-C8)cycloalkylaminocarbonyl, (C1-C6)alkylsulphonylamino, (C1-C6)alkylamino, di-(C1-C6)alkylamino, (C1-C6)haloalkylamino, bis-(C1-C6)haloalkylamino, aminosulphonyl, (C1-C6)alkylaminosulphonyl, di-(C1-C6)alkylaminosulphonyl, (C1-C6)alkylsulphoximino, aminothiocarbonyl, (C1-C6)alkylaminothiocarbonyl, di-(C1-C6)alkylaminothiocarbonyl, (C3-C8)cycloalkylamino,
R1 is (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)alkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, (C1-C6)haloalkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, cyano(C3-C8)cycloalkyl, (C2-C6)alkynyl-(C3-C8)cycloalkyl, (C1-C6)alkoxy-(C3-C8)cycloalkyl, (C1-C6)alkoxycarbonyl-(C3-C8)cycloalkyl, (C1-C6)alkylamino, di-(C1-C6)alkylamino, (C3-C8)cycloalkylamino, (C1-C6)alkylcarbonylamino, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)haloalkylthio-(C1-C6)alkyl, (C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)haloalkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)haloalkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkylcarbonyl-(C1-C6)alkyl, (C1-C6)haloalkylcarbonyl-(C1-C6)alkyl, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)haloalkoxycarbonyl-(C1-C6)alkyl, (C1-C6)alkylsulphonylamino, aminosulphonyl-(C1-C6)alkyl, (C1-C6)alkylaminosulphonyl-(C1-C6)alkyl, di-(C1-C6)alkylaminosulphonyl-(C1-C6)alkyl, (C1-C4)alkoxy, (C3-C6)cycloalkoxy, (C3-C6)cycloalkylcarbonyl or (C1-C4)alkylcarbonyl,
or in each case optionally singly or multiply, identically or differently aryl-, hetaryl-, oxohetaryl-, heterocyclyl- or oxoheterocyclyl-substituted (C1-C6)alkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, where aryl, hetaryl, oxohetaryl, heterocyclyl or oxoheterocyclyl may each optionally be mono- or polysubstituted identically or differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, aminosulphonyl, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulphinyl, (C1-C6)alkylsulphonyl, (C1-C6)alkylsulphimino, (C1-C6)alkylsulphimino-(C1-C6)alkyl, (C1-C6)alkylsulphimino-(C2-C6)alkylcarbonyl, (C1-C6)alkylsulphoximino, (C1-C6)alkylsulphoximino-(C1-C6)alkyl, (C1-C6)alkylsulphoximino-(C2-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylcarbonyl or (C3-C6)trialkylsilyl,
or in each case optionally singly or multiply, identically or differently substituted aryl, hetaryl, oxohetaryl, heterocyclyl or oxoheterocyclyl, where the substituents are selected from halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, (C1-C6)alkyl, (C3-C8)cycloalkyl, (C1-C6)-alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulphinyl, (C1-C6)alkylsulphonyl, (C1-C6)alkylsulphimino, (C1-C6)alkylsulphimino-(C1-C6)alkyl, (C1-C6)alkylsulphimino-(C2-C6)alkylcarbonyl, (C1-C6)alkylsulphoximino, (C1-C6)alkylsulphoximino-(C1-C6)alkyl, (C1-C6)alkylsulphoximino-(C2-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylcarbonyl, (C3-C6)trialkylsilyl,
R2 is hydrogen (C1-C6)alkyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C1-C6)alkylcarbonyl, (C3-C8)cycloalkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)alkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)haloalkylthio-(C1-C6)alkyl, (C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)haloalkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)haloalkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkylcarbonyl-(C1-C6)alkyl, (C1-C6)haloalkylcarbonyl-(C1-C6)alkyl, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)haloalkoxycarbonyl-(C1-C6)alkyl, aminocarbonyl-(C1-C6)alkyl, (C1-C6)alkylamino-(C1-C6)alkyl, di-(C1-C6)alkylamino-(C1-C6)alkyl or (C3-C8)cycloalkylamino-(C1-C6)alkyl,
R3 is hydrogen (C1-C6)alkyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C1-C6)alkylcarbonyl, (C3-C8)cycloalkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)alkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)haloalkylthio-(C1-C6)alkyl, (C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)haloalkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)haloalkyl sulphonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkylcarbonyl-(C1-C6)alkyl, (C1-C6)haloalkylcarbonyl-(C1-C6)alkyl, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)haloalkoxycarbonyl-(C1-C6)alkyl, aminocarbonyl-(C1-C6)alkyl, (C1-C6)alkylamino-(C1-C6)alkyl, di-(C1-C6)alkylamino-(C1-C6)alkyl or (C3-C8)cycloalkylamino-(C1-C6)alkyl,
R4 is (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)cyanoalkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)haloalkoxy-(C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyloxy-(C1-C6)alkyl, (C2-C6)haloalkenyl, (C2-C6)cyanoalkenyl, (C2-C6)alkynyl, (C2-C6)alkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyloxy-(C1-C6)alkyl, (C2-C6)haloalkynyl, (C2-C6)cyanoalkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(C1-C6)alkyl, cyano(C3-C8)cycloalkyl-(C1-C6)alkyl, halo(C3-C8)cycloalkyl-(C1-C6)alkyl, (C1-C4)haloalkyl-(C3-C8)cycloalkyl-(C1-C6)alkyl, (C3-C8)cycloalkyl-(C3-C8)cycloalkyl, (C1-C6)alkyl-(C3-C8)cycloalkyl, (C1-C6)haloalkyl-(C3-C8)cycloalkyl, halo(C3-C8)cycloalkyl, cyano(C3-C8)cycloalkyl, (C2-C6)alkynyl-(C3-C8)cycloalkyl, (C1-C6)alkoxy-(C3-C8)cycloalkyl, (C1-C6)alkoxycarbonyl-(C3-C8)cycloalkyl, carbamoyl-(C3-C8)cycloalkyl, thiocarbamoyl-(C3-C8)cycloalkyl, (C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)haloalkylthio-(C1-C6)alkyl, (C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)haloalkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)haloalkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylthio-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphinyl-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkylsulphonyl-(C1-C6)alkyl, (C1-C6)alkylcarbonyl-(C1-C6)alkyl, (C1-C6)haloalkylcarbonyl-(C1-C6)alkyl, (C1-C6)alkoxycarbonyl-(C1-C6)alkyl, (C1-C6)haloalkoxycarbonyl-(C1-C6)alkyl, (C1-C6)alkylsulphonylamino, aminosulphonyl-(C1-C6)alkyl, (C1-C6)alkylaminosulphonyl-(C1-C6)alkyl, di-(C1-C6)alkylaminosulphonyl-(C1-C6)alkyl, amino, (C1-C6)alkylamino, di-(C1-C6)alkylamino, (C3-C8)cycloalkylamino, N—(C1-C6)alkyl-(C3-C8)cycloalkylamino, benzylamino, cyanobenzylamino, nitrobenzylamino, halobenzylamino, N—(C1-C6)alkylbenzylamino, N—(C1-C6)alkylcyanobenzylamino, N—(C1-C6)alkylnitrobenzylamino, N—(C1-C6)alkylhalobenzylamino, (C1-C6)alkylcarbonylamino, (C3-C8)cycloalkylcarbonylamino, hydroxyl, (C1-C6)alkoxy, (C3-C8)cycloalkoxy, (C3-C8)cycloalkyl-(C1-C6)alkoxy, cyano(C1-C6)alkoxy, benzyloxy, cyanobenzyloxy, nitrobenzyloxy, halobenzyloxy, (C1-C6)alkylimino, (C3-C8)cycloalkylimino, benzylimino, cyanobenzylimino, nitrobenzylimino, halobenzylimino, (C1-C6)haloalkylbenzylimino, halo-[(C1-C6)haloalkyl]benzylimino, (C1-C6)alkylcarbonyl, (C1-C6)haloalkylcarbonyl, (C3-C8)cycloalkylcarbonyl or (C3-C8)cycloalkyl-(C1-C6)alkylcarbonyl,
or in each case optionally singly or multiply, identically or differently aryl-, 1,3-benzodioxolyl-, 2,3-dihydro-1,4-benzodioxinyl-, hetaryl-, oxohetaryl-, heterocyclyl- or oxoheterocyclyl-substituted (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, oxy, amino, N—(C1-C6)alkylamino, N—(C3-C8)cycloalkylamino or carbonyl, where aryl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, hetaryl, oxohetaryl, heterocyclyl or oxoheterocyclyl may each optionally be mono- or polysubstituted identically or differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, thiocarbamoyl, aminosulphonyl, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulphinyl, (C1-C6)alkylsulphonyl, (C1-C6)haloalkylsulphinyl, (C1-C6)haloalkylsulphonyl, (C1-C6)alkylsulphimino, (C1-C6)alkylsulphimino-(C1-C6)alkyl, (C1-C6)alkylsulphimino-(C2-C6)alkylcarbonyl, (C1-C6)alkylsulphoximino, (C1-C6)alkylsulphoximino-(C1-C6)alkyl, (C1-C6)alkylsulphoximino-(C2-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylcarbonyl, (C3-C6)trialkylsilyl or hetaryl, or
in each case optionally singly or multiply, identically or differently substituted aryl, 2,3-dihydro-1H-indenyl, 1,3-benzodioxolyl, hetaryl, oxohetaryl, heterocyclyl or oxoheterocyclyl, where the substituents are selected from halogen, cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, (C1-C6)alkyl, (C3-C8)cycloalkyl, (C1-C6)-alkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulphinyl, (C1-C6)alkylsulphonyl, (C1-C6)haloalkylsulphinyl, (C1-C6)haloalkylsulphonyl, (C1-C6)alkylsulphimino, (C1-C6)alkylsulphimino-(C1-C6)alkyl, (C1-C6)alkylsulphimino-(C2-C6)alkylcarbonyl, (C1-C6)alkylsulphoximino, (C1-C6)alkylsulphoximino-(C1-C6)alkyl, (C1-C6)alkylsulphoximino-(C2-C6)alkylcarbonyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylcarbonyl, (C3-C6)trialkylsilyl,
or R3 and R4 together are (C2-C6)-alkyl or (C2-C6)alkenyl, forming a 3-7-membered, optionally halogen-, cyano-, hydroxyl-, amino-, carboxyl-, carbamoyl-, (C1-C6)alkyl-, (C3-C8)cycloalkyl-, (C1-C6)-alkoxy-, (C1-C6)haloalkyl-, (C1-C6)haloalkoxy-, (C1-C6)alkylthio- or (C1-C6)haloalkylthio-substituted ring which may optionally contain one to two double bonds,
R5, R6 are independently hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino, (C1-C6)alkylamino, di-(C1-C6)alkylamino, (C3-C6)cycloalkyl, halo(C3-C6)cycloalkyl, (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)haloalkenyl, (C2-C6)alkynyl, (C2-C6)haloalkynyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulphinyl, (C1-C6)haloalkylsulphinyl, (C1-C6)alkylsulphonyl, (C1-C6)haloalkylsulphonyl,
V1 is oxygen or sulphur,
V2 is oxygen, sulphur or —NH.

13 more elements

Substituted pyridine compounds as pesticides

Life of this patent

Substituted pyridine compounds as pesticides

Life of this patent

Abstract

Claims11