Heterocyclic derivatives as pest control agents

Abstract

The present invention relates to novel compounds of formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Y, Z, n and m have the meanings indicated in the specification, and relate to their use as acaricides and / or insecticides for controlling animal pests, as well as to methods and intermediates for preparing them.

Description

[0001] The present invention relates to heterocyclic derivatives of formula (I), to their use as acaricides and / or insecticides for controlling animal pests, in particular arthropods and especially insects and arachnids, and to processes and intermediates for their preparation.

[0002] Heterocyclic derivatives having insecticidal properties are described, for example, in the following documents: WO 2010 / 125985, WO 2012 / 074135, WO 2012 / 086848, WO 2013 / 018928, WO 2013 / 180193, WO 2013 / 191113, WO 2014 / 142292, WO 2014 / 148451, WO 2015 / 000715, WO 2016 / 124563, WO 2016 / 124557, WO 2015 / 121136, WO 2015 / 133603, WO 2015 / 198859, WO 2015 / 002211, WO 2015 / 071180、WO2015 / 091945、WO 2016 / 005263、WO 2016 / 039441、WO 2015 / 198817、WO 2016 / 041819、WO2016 / 039441、WO 2016 / 039444、WO 2016 / 026848、WO 2016 / 023954、WO 2016 / 020286、WO2016 / 046071、WO 2016 / 058928、WO 2016 / 059145、WO 2016 / 071214、WO 2016 / 091731、WO2016 / 096584、WO 2016 / 107742、WO 2016 / 107831、WO 2016 / 113155、WO 2016 / 116338、WO2016 / 121997、WO 2016 / 125621、WO 2016 / 125622、WO 2016 / 129684、WO 2016 / 142326, WO2016 / 142327, WO 2016 / 169882, WO 2016 / 169886, WO 2018 / 130437, WO 2018 / 130443 and WO2020 / 002082.

[0003] Modern crop protection compositions have to meet numerous requirements, for example in relation to the extent, persistence and spectrum of their action and possible uses. Questions of toxicity, retention of beneficial species and pollinators, environmental properties, application rates, combinations with other active ingredients or formulation auxiliaries play a role, as do questions of the complexity involved in synthesizing the active ingredients, and resistance may also occur, to mention only some parameters. For all these reasons alone, the search for new crop protection compositions cannot be considered complete, and there is a constant need for new compounds which have improved properties at least in individual respects compared to the known compounds.

[0004] It is an object of the present invention to provide compounds which broaden the pesticide spectrum and / or improve its activity in different aspects.

[0005] Novel heterocyclic derivatives have now been found which have advantages over known compounds, examples of which include better biological or environmental properties, a wider range of application methods, better insecticidal or acaricidal action and good compatibility with useful plants. The heterocyclic derivatives can be used in combination with other compositions to improve the efficacy, in particular against difficult-to-control insects.

[0006] Therefore, the present invention provides novel compounds of formula (I)

[0007]

[0008] in

[0009] (Configuration 1-1)

[0010] R 1 Representative (C 1 -C 6 ) alkyl, (C 1 -C 6 ) cyanoalkyl, (C 1 -C 6 ) hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl or (C 3 -C 8 ) cycloalkyl,

[0011] R 2 represents hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) cyanoalkyl, (C 1 -C 6 ) hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkyl, (C 1 -C 6 )Haloalkoxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 )alkenyloxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 )Haloalkenyloxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 )alkynyloxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 )Haloalkynyloxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 ) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 ) cycloalkyl, halo(C 3 -C8 ) cycloalkyl, cyano (C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkylthio-(C 1 -C 6 ) alkyl, (C 1 -C 6 )Haloalkylthio-(C 1 -C 6 ) alkyl, (C 1 -C 6 )alkylsulfinyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )Haloalkylsulfinyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )Haloalkylsulfonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )Haloalkylcarbonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxycarbonyl-(C 1 -C 6 ) alkyl or (C 1 -C 6 )Haloalkoxycarbonyl-(C 1 -C 6 )alkyl,

[0012] R 3 Represents hydrogen, halogen, cyano, nitro, (C 1 -C 6 ) alkyl, (C 3 -C 8 ) cycloalkyl, cyano (C 3 -C 8 )cycloalkyl, (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) alkoxy, (C1 -C 6 ) haloalkoxy, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) halogenated alkylthio, (C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 ) haloalkylsulfinyl, (C 1 -C 6 ) alkylsulfonyl, (C 1 -C 6 ) alkyl sulfonyl halide, SCN, (C 1 -C 6 ) alkylcarbonyl, (C 1 -C 6 ) haloalkylcarbonyl, (C 1 -C 6 ) alkoxycarbonyl, (C 1 -C 6 ) halogenated alkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 ) haloalkylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 6 ) alkylaminothiocarbonyl, di(C 1 -C 6 ) alkylaminothiocarbonyl, (C 1 -C 6 ) haloalkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylaminothiocarbonyl, amino, (C 1 -C 6 ) alkylamino, (C 1 -C 6 ) haloalkylamino, di(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylamino, (C 1 -C 6 ) alkylsulfonylamino, (C 1 -C 6 )alkylcarbonylamino, (C 1 -C 6) haloalkylcarbonylamino, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylcarbonylamino, (C 3 -C 8 )cycloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )alkylthiocarbonylamino, (C 1 -C 6 ) haloalkylthiocarbonylamino, (C 1 -C 6 )alkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylthiocarbonylamino, (C 3 -C 8 )cycloalkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 3 -C 8 )cycloalkyl-(C 2 ) alkenyl, (C 2 -C 6 ) alkynyl or (C 2 -C 6 ) haloalkynyl, (C 3 -C 8 )cycloalkyl-(C 2 ) alkynyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 ) alkyl, (C 1 -C 6)alkylaminocarbonylamino, di(C 1 -C 6 )alkylaminocarbonylamino, (C 3 -C 8 )cycloalkylaminocarbonylamino, (C 1 -C 6 ) haloalkylaminocarbonylamino, (C 1 -C 6 )alkylaminocarbonyl-(C 1 -C 6 ) alkylamino, di(C 1 -C 6 )alkylaminocarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylaminocarbonyl-(C 1 -C 6 ) alkylamino or (C 1 -C 6 )haloalkylaminocarbonyl-(C 1 -C 6 )alkylamino, or, represents a saturated, partially saturated or heteroaromatic ring which is optionally mono- or polysubstituted by identical or different substituents and in which at least one carbon atom is substituted by a heteroatom, or represents a saturated or partially saturated carbocyclic ring which is mono- or polysubstituted by identical or different substituents, or represents an aromatic ring in which at least one carbonyl group may optionally be present in each case and / or in which the possible substituents in each case are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, SF 5 , three (C 1 -C 6 ) alkylsilyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )Haloalkyl-(C 3 -C 8 ) cycloalkyl, halo(C 3 -C 8 ) cycloalkyl, cyano (C 3 -C 8 )cycloalkyl, (C 1 -C 6) alkyl, (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) cyanoalkyl, (C 1 -C 6 ) cyanohaloalkyl, (C 1 -C 6 ) hydroxyalkyl, hydroxycarbonyl-(C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkoxycarbonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 3 -C 8 )cycloalkyl-(C 2 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy, (C 1 -C 6 ) cyanoalkoxy, (C 1 -C 6 ) alkoxycarbonyl-(C 1 -C 6 ) alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkoxyimino, (C 1 -C 6 ) haloalkoxyimino, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) halogenated alkylthio, (C1 -C 6 )alkoxy-(C 1 -C 6 ) alkylthio, (C 1 -C 6 )alkylthio-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 ) haloalkylsulfinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 )alkylsulfinyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfonyl, (C 1 -C 6 ) halogenated alkylsulfonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkylsulfonyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfonyloxy, (C 1 -C 6 ) haloalkylsulfonyloxy, (C 1 -C 6 ) alkylcarbonyl, (C 1 -C 6 ) haloalkylcarbonyl, (C 1 -C 6 ) alkylcarbonyloxy, (C 1 -C 6 ) alkoxycarbonyl, (C 1 -C 6 ) halogenated alkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 ) haloalkylaminocarbonyl, (C 2 -C 6)alkenylaminocarbonyl, di(C 2 -C 6 )alkenylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, (C 1 -C 6 ) alkylsulfonylamino, (C 1 -C 6 ) alkylamino, di(C 1 -C 6 ) alkylamino, (C 1 -C 6 ) haloalkylamino, (C 3 -C 8 ) cycloalkylamino, aminosulfonyl, (C 1 -C 6 ) alkylaminosulfonyl, di(C 1 -C 6 ) alkylaminosulfonyl, (C 1 -C 6 ) alkylsulfoximino, aminothiocarbonyl, (C 1 -C 6 ) alkylaminothiocarbonyl, di(C 1 -C 6 ) alkylaminothiocarbonyl, (C 1 -C 6 ) haloalkylaminothiocarbonyl, (C 3 -C 8 ) cycloalkylaminothiocarbonyl, (C 1 -C 6 )alkylcarbonylamino, (C 1 -C 6 ) haloalkylcarbonylamino, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylcarbonylamino, (C 3 -C 8 )cycloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )alkylthiocarbonylamino, (C 1 -C 6 ) haloalkylthiocarbonylamino, (C 1 -C6 )alkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylthiocarbonylamino, (C 3 -C 8 )cycloalkylthiocarbonyl-(C 1 -C 6 )alkylamino, heteroaryl, oxaaryl, halogenated heteroaryl, halogenated oxaaryl, cyanoheteroaryl, cyanooxaaryl, (C 1 -C 6 ) haloalkylheteroaryl or (C 1 -C 6 ) haloalkyloxaaryl,

[0013] R 4 , R 5 , R 6 , R 7 independently represent hydrogen, cyano, halogen, (C 1 -C 3 ) alkyl or (C 1 -C 3 ) haloalkyl,

[0014] Y represents oxygen, =NH or =N-CN,

[0015] Z stands for -NR 8 , oxygen or sulfur, of which

[0016] R 8 represents hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) cyanoalkyl, (C 1 -C 6 ) hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkyl, (C 1 -C 6 )Haloalkoxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C6 )alkenyloxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 )Haloalkenyloxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl or (C 3 -C 8 ) cycloalkyl,

[0017] m represents 0 or 1,

[0018] n represents 0 or 1.

[0019] Furthermore, it has been found that the compounds of the formula (I) have very good efficacy as pesticides, preferably as insecticides and / or acaricides, and generally also have very good plant compatibility, in particular with respect to crop plants.

[0020] The compounds of the invention are defined in general terms by formula (I). Preferred substituents or ranges of the radicals given in the formulae mentioned above and below are explained below:

[0021] Configuration 2-1

[0022] R 1 Preferably represents (C 1 -C 4 ) alkyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl or (C 3 -C 6 ) cycloalkyl,

[0023] R2 Preferably represents hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 ) hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 ) alkyl, (C 1 -C 4 )Haloalkoxy-(C 1 -C 4 ) alkyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 ) cycloalkyl, halo(C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkylthio-(C 1 -C 4 ) alkyl, (C 1 -C 4 )Haloalkylthio-(C 1 -C 4 ) alkyl, (C 1 -C 4 )alkylsulfinyl-(C 1 -C 4 ) alkyl, (C 1 -C 4 )Haloalkylsulfinyl-(C 1 -C 4 ) alkyl, (C 1 -C 4 )alkylsulfonyl-(C 1 -C 4 ) alkyl or (C 1 -C 4 )Haloalkylsulfonyl-(C 1 -C 4 )alkyl,

[0024] R 3 Preferably represents hydrogen, halogen, cyano, nitro, (C 1 -C 6 ) alkyl, (C 3 -C 8 ) cycloalkyl, cyano (C 3 -C 8 )cycloalkyl, (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) halogenated alkylthio, (C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 ) haloalkylsulfinyl, (C 1 -C 6 ) alkylsulfonyl, (C 1 -C 6 ) alkyl sulfonyl halide, SCN, (C 1 -C 6 ) alkylcarbonyl, (C 1 -C 6 ) haloalkylcarbonyl, (C 1 -C 6 ) alkoxycarbonyl, (C 1 -C 6 ) halogenated alkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 ) haloalkylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 6 ) alkylaminothiocarbonyl, di(C 1 -C 6 ) alkylaminothiocarbonyl, (C 1 -C 6 ) haloalkylaminothiocarbonyl, (C 3 -C 8 )cycloalkylaminothiocarbonyl, amino, (C 1 -C 6) alkylamino, (C 1 -C 6 ) haloalkylamino, di(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylamino, (C 1 -C 6 ) alkylsulfonylamino, (C 1 -C 6 )alkylcarbonylamino, (C 1 -C 6 ) haloalkylcarbonylamino, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylcarbonylamino, (C 3 -C 8 )cycloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )alkylthiocarbonylamino, (C 1 -C 6 ) haloalkylthiocarbonylamino, (C 1 -C 6 )alkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylthiocarbonylamino, (C 3 -C 8 )cycloalkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 3 -C 8 )cycloalkyl-(C 2 ) alkenyl, (C2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 8 )cycloalkyl-(C 2 ) alkynyl, (C 3 -C 8 )cycloalkyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )alkylaminocarbonylamino, di(C 1 -C 6 )alkylaminocarbonylamino, (C 3 -C 8 )cycloalkylaminocarbonylamino, (C 1 -C 6 ) haloalkylaminocarbonylamino, (C 1 -C 6 )alkylaminocarbonyl-(C 1 -C 6 ) alkylamino, di(C 1 -C 6 )alkylaminocarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylaminocarbonyl-(C 1 -C 6 ) alkylamino or (C 1 -C 6 )haloalkylaminocarbonyl-(C 1 -C 6 )alkylamino, or, represents aryl, heteroaryl, cyclopentenyl or cyclohexenyl, each of which is optionally mono- or polysubstituted by identical or different substituents, wherein (in the case of heteroaryl) at least one carbonyl group may optionally be present, and the possible substituents in each case are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, SF 5 , three (C 1 -C 6 ) alkylsilyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkyl-(C 3 -C 8 )cycloalkyl, (C 1 -C 6 )alkyl-(C 3 -C 8 )cycloalkyl, (C1 -C 6 )Haloalkyl-(C 3 -C 8 ) cycloalkyl, halo(C 3 -C 8 ) cycloalkyl, cyano (C 3 -C 8 )cycloalkyl, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) cyanoalkyl, (C 1 -C 6 ) cyanohaloalkyl, (C 1 -C 6 ) hydroxyalkyl, hydroxycarbonyl-(C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkoxycarbonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 )cyanoalkenyl, (C 3 -C 8 )cycloalkyl-(C 2 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl, (C 2 -C 6 ) cyanoalkynyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) haloalkoxy, (C 1 -C 6 ) cyanoalkoxy, (C 1 -C 6 ) alkoxycarbonyl-(C 1 -C 6 ) alkoxy, (C 1 -C 6 )alkoxy-(C 1 -C6 ) alkoxy, (C 1 -C 6 ) alkoxyimino, (C 1 -C 6 ) haloalkoxyimino, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) halogenated alkylthio, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkylthio, (C 1 -C 6 )alkylthio-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 ) haloalkylsulfinyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkylsulfinyl, (C 1 -C 6 )alkylsulfinyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfonyl, (C 1 -C 6 ) halogenated alkylsulfonyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 ) alkylsulfonyl, (C 1 -C 6 )alkylsulfonyl-(C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkylsulfonyloxy, (C 1 -C 6 ) haloalkylsulfonyloxy, (C 1 -C 6 ) alkylcarbonyl, (C 1 -C 6 ) haloalkylcarbonyl, (C 1 -C 6 ) alkylcarbonyloxy, (C 1 -C 6 ) alkoxycarbonyl, (C 1 -C6 ) halogenated alkoxycarbonyl, aminocarbonyl, (C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, (C 1 -C 6 ) haloalkylaminocarbonyl, (C 2 -C 6 )alkenylaminocarbonyl, di(C 2 -C 6 )alkenylaminocarbonyl, (C 3 -C 8 )cycloalkylaminocarbonyl, (C 1 -C 6 ) alkylsulfonylamino, (C 1 -C 6 ) alkylamino, di(C 1 -C 6 ) alkylamino, (C 1 -C 6 ) haloalkylamino, (C 3 -C 8 ) cycloalkylamino, aminosulfonyl, (C 1 -C 6 ) alkylaminosulfonyl, di(C 1 -C 6 ) alkylaminosulfonyl, (C 1 -C 6 ) alkylsulfoximino, aminothiocarbonyl, (C 1 -C 6 ) alkylaminothiocarbonyl, di(C 1 -C 6 ) alkylaminothiocarbonyl, (C 1 -C 6 ) haloalkylaminothiocarbonyl, (C 3 -C 8 ) cycloalkylaminothiocarbonyl, (C 1 -C 6 )alkylcarbonylamino, (C 1 -C 6 ) haloalkylcarbonylamino, (C 1 -C 6 )alkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylcarbonylamino, (C3 -C 8 )cycloalkylcarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )alkylthiocarbonylamino, (C 1 -C 6 ) haloalkylthiocarbonylamino, (C 1 -C 6 )alkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 1 -C 6 )Haloalkylthiocarbonyl-(C 1 -C 6 ) alkylamino, (C 3 -C 8 )cycloalkylthiocarbonylamino, (C 3 -C 8 )cycloalkylthiocarbonyl-(C 1 -C 6 )alkylamino, heteroaryl, oxaaryl, halogenated heteroaryl, halogenated oxaaryl, cyanoheteroaryl, cyanooxaaryl, (C 1 -C 6 ) haloalkylheteroaryl or (C 1 -C 6 ) haloalkyloxaaryl,

[0025] R 4 , R 5 , R 6 , R 7 Preferably independently of one another represent hydrogen, cyano, halogen, (C 1 -C 3 ) alkyl or (C 1 -C 3 ) haloalkyl,

[0026] Y preferably represents oxygen, =NH or =N-CN,

[0027] Z preferably represents -NR 8 , oxygen or sulfur, of which

[0028] R 8 Preferably represents hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 ) hydroxyalkyl, (C 1-C 4 )alkoxy-(C 1 -C 4 ) alkyl, (C 1 -C 4 )Haloalkoxy-(C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 )alkenyloxy-(C 1 -C 4 ) alkyl, (C 2 -C 4 )Haloalkenyloxy-(C 1 -C 4 ) alkyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl or (C 3 -C 6 ) cycloalkyl,

[0029] m preferably represents 0 or 1,

[0030] n preferably represents 0 or 1.

[0031] Configuration 3-1

[0032] R 1 Particularly preferably represents (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 )haloalkenyl or (C 3 -C 6 ) cycloalkyl,

[0033] R 2 Particularly preferably represents hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 3 -C 6 )cycloalkyl or halogenated (C 3 -C 6 ) cycloalkyl,

[0034] R 3 Particularly preferably represents hydrogen, halogen, cyano, (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, amino, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) haloalkylamino, di(C 1 -C 4 ) alkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 ) alkylsulfonylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 ) haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )Haloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 2 -C 4 ) alkenyl, (C 2-C 4 ) haloalkenyl, (C 2 -C 4 )cyanoalkenyl or (C 3 -C 6 )cycloalkyl-(C 2 )alkenyl or, particularly preferably, represents phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, furyl, pyrazolyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents, wherein (in the case of heteroaryl) at least one carbonyl group may optionally be present, and possible substituents in each case are as follows: cyano, halogen, nitro, acetyl, hydroxy, amino, SF 5 , (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )Haloalkyl-(C 3 -C 6 ) cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) alkyl, cyano (C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 ) cyanohaloalkyl, (C 1 -C 4 ) hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 3 -C 6 )cycloalkyl-(C 2 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C2 -C 4 ) cyanoalkynyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) cyanoalkoxy, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkoxy, (C 1 -C 4 ) alkoxyimino, (C 1 -C 4 ) haloalkoxyimino, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) halogenated alkylthio, (C 1 -C 4 )alkylthio-(C 1 -C 2 ) alkyl, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C 4 ) haloalkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (C 1 -C 4 ) halogenated alkylsulfonyl, (C 1 -C 4 ) alkylsulfonyloxy, (C 1 -C 4 ) haloalkylsulfonyloxy, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 4 ) alkylaminothiocarbonyl, di(C 1 -C 4 ) alkylaminothiocarbonyl, (C 1 -C4 ) haloalkylaminothiocarbonyl, (C 3 -C 6 ) cycloalkylaminothiocarbonyl, (C 1 -C 4 ) alkylsulfonylamino, (C 1 -C 4 ) alkylamino, di(C 1 -C 4 ) alkylamino, (C 1 -C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, aminosulfonyl, (C 1 -C 4 ) alkylaminosulfonyl, di(C 1 -C 4 ) alkylaminosulfonyl, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 ) haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 2 )Haloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )alkylthiocarbonylamino, (C 1 -C 4 ) haloalkylthiocarbonylamino, (C 1 -C 4 )alkylthiocarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )Haloalkylthiocarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylthiocarbonylamino or (C 3 -C 6 )cycloalkylthiocarbonyl-(C 1 -C2 ) alkylamino,

[0035] R 4 , R 5 , R 6 , R 7 are particularly preferably identical and represent hydrogen or fluorine,

[0036] Y particularly preferably represents oxygen or =NH,

[0037] Z particularly preferably represents -NR 8 or oxygen, where

[0038] R 8 Particularly preferably represents hydrogen or (C 1 -C 4 )alkyl,

[0039] m particularly preferably represents 0 or 1,

[0040] n particularly preferably represents 0 or 1.

[0041] Configuration 3-2

[0042] R 1 Particularly preferably represents (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 )haloalkenyl or (C 3 -C 6 ) cycloalkyl,

[0043] R 2 Particularly preferably represents hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 3 -C 6 )cycloalkyl or halogenated (C 3 -C 6 ) cycloalkyl,

[0044] R 3 Particularly preferably represents hydrogen, halogen, cyano, (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, cyano (C 3 -C 6 )cycloalkyl, (C 1 -C4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, amino, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) haloalkylamino, di(C 1 -C 4 ) alkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 ) alkylsulfonylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 ) haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )Haloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 )cyanoalkenyl or (C 3 -C 6 )cycloalkyl-(C 2)alkenyl or, particularly preferably, represents phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, furyl, pyrazolyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents, wherein (in the case of heteroaryl) at least one carbonyl group may optionally be present, and possible substituents in each case are as follows: cyano, halogen, nitro, acetyl, hydroxy, amino, SF 5 , (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )Haloalkyl-(C 3 -C 6 ) cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) alkyl, cyano (C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 ) cyanohaloalkyl, (C 1 -C 4 ) hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 )cyanoalkenyl, (C 3 -C 6 )cycloalkyl-(C 2 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 2 -C 4 ) cyanoalkynyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C1 -C 4 ) cyanoalkoxy, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkoxy, (C 1 -C 4 ) alkoxyimino, (C 1 -C 4 ) haloalkoxyimino, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) halogenated alkylthio, (C 1 -C 4 )alkylthio-(C 1 -C 2 ) alkyl, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C 4 ) haloalkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (C 1 -C 4 ) halogenated alkylsulfonyl, (C 1 -C 4 ) alkylsulfonyloxy, (C 1 -C 4 ) haloalkylsulfonyloxy, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, aminothiocarbonyl, (C 1 -C 4 ) alkylaminothiocarbonyl, di(C 1 -C 4 ) alkylaminothiocarbonyl, (C 1 -C 4 ) haloalkylaminothiocarbonyl, (C 3 -C 6 ) cycloalkylaminothiocarbonyl, (C 1 -C 4 ) alkylsulfonylamino, (C1 -C 4 ) alkylamino, di(C 1 -C 4 ) alkylamino, (C 1 -C 4 ) haloalkylamino, (C 3 -C 6 ) cycloalkylamino, aminosulfonyl, (C 1 -C 4 ) alkylaminosulfonyl, di(C 1 -C 4 ) alkylaminosulfonyl, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 ) haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 2 )Haloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )alkylthiocarbonylamino, (C 1 -C 4 ) haloalkylthiocarbonylamino, (C 1 -C 4 )alkylthiocarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )Haloalkylthiocarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylthiocarbonylamino, (C 3 -C 6 )cycloalkylthiocarbonyl-(C 1 -C 2 ) alkylamino or pyridyl optionally substituted by halogen,

[0045] R 4 , R 5 , R 6 , R7 are particularly preferably identical and represent hydrogen or fluorine,

[0046] Y particularly preferably represents oxygen or =NH,

[0047] Z particularly preferably represents -NR 8 or oxygen, where

[0048] R 8 Particularly preferably represents hydrogen or (C 1 -C 4 )alkyl,

[0049] m particularly preferably represents 0 or 1,

[0050] n particularly preferably represents 0 or 1.

[0051] Configuration 4-1

[0052] R 1 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,

[0053] R 2 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,

[0054] R 3 Very particularly preferably represents hydrogen, halogen, (C 1 -C 4 ) alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 )cyanoalkenyl or (C 3 -C 6 )cycloalkyl-(C 2 ) alkenyl,

[0055] Alternatively, very particularly preferably represents phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, nitro, acetyl, hydroxyl, amino, SF 5 , (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )Haloalkyl-(C 3 -C 6 ) cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) alkyl, cyano (C 3 -C 8 )cycloalkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 ) hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkoxy, (C 1 -C 4 ) alkoxyimino, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) halogenated alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C 4 ) haloalkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (C 1 -C 4) halogenated alkylsulfonyl, (C 1 -C 4 ) alkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, (C 1 -C 4 ) alkylsulfonylamino, (C 1 -C 4 ) alkylamino, di(C 1 -C 4 ) alkylamino, (C 1 -C 4 ) haloalkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 ) haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )Haloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino or (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 ) alkylamino,

[0056] Alternatively, very particularly preferably represents pyrazolyl, triazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a nitrogen atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, nitro, hydroxyl, amino, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C1 -C 4 ) a haloalkoxy group or an aminocarbonyl group,

[0057] R 4 , R 5 , R 6 , R 7 are very particularly preferably identical and represent hydrogen or fluorine,

[0058] Y very particularly preferably represents oxygen or ═NH,

[0059] Z very particularly preferably represents -NR 8 or oxygen, where

[0060] R 8 Very particularly preferably represents hydrogen or methyl,

[0061] m very particularly preferably represents 0 or 1,

[0062] n very particularly preferably represents 0 or 1.

[0063] Configuration 4-2

[0064] R 1 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,

[0065] R 2 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,

[0066] R 3 Very particularly preferably represents hydrogen, halogen, (C 1 -C 4 ) alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 )cyanoalkenyl or (C 3 -C 6 )cycloalkyl-(C 2 ) alkenyl,

[0067] Alternatively, very particularly preferably represents phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, nitro, acetyl, hydroxyl, amino, SF 5 , (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )alkyl-(C 3 -C 6 )cycloalkyl, (C 1 -C 4 )Haloalkyl-(C 3 -C 6 ) cycloalkyl, halo(C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) alkyl, cyano (C 3 -C 8 )cycloalkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 ) hydroxyalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 )alkoxy-(C 1 -C 2 ) alkoxy, (C 1 -C 4 ) alkoxyimino, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) halogenated alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C 4 ) haloalkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (C 1 -C 4) halogenated alkylsulfonyl, (C 1 -C 4 ) alkylcarbonyl, aminocarbonyl, (C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, (C 3 -C 6 )cycloalkylaminocarbonyl, (C 1 -C 4 ) alkylsulfonylamino, (C 1 -C 4 ) alkylamino, di(C 1 -C 4 ) alkylamino, (C 1 -C 4 ) haloalkylamino, (C 3 -C 6 )cycloalkylamino, (C 1 -C 4 )alkylcarbonylamino, (C 1 -C 4 ) haloalkylcarbonylamino, (C 1 -C 4 )alkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 1 -C 4 )Haloalkylcarbonyl-(C 1 -C 2 ) alkylamino, (C 3 -C 6 )cycloalkylcarbonylamino, (C 3 -C 6 )cycloalkylcarbonyl-(C 1 -C 2 ) alkylamino or pyridyl optionally monosubstituted by chlorine or bromine,

[0068] Alternatively, very particularly preferably represents pyrazolyl, triazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a nitrogen atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, nitro, hydroxyl, amino, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C4 ) alkoxy, (C 1 -C 4 ) a haloalkoxy group or an aminocarbonyl group,

[0069] R 4 , R 5 , R 6 , R 7 are very particularly preferably identical and represent hydrogen or fluorine,

[0070] Y very particularly preferably represents oxygen or ═NH,

[0071] Z very particularly preferably represents -NR 8 or oxygen, where

[0072] R 8 Very particularly preferably represents hydrogen or methyl,

[0073] m very particularly preferably represents 0 or 1,

[0074] n very particularly preferably represents 0 or 1.

[0075] Configuration 5-1

[0076] R 1 In particular, ethyl,

[0077] R 2 In particular, it represents a methyl group,

[0078] R 3 In particular, bromo, cyclopropyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl,

[0079] Alternatively, represents phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, SF 5 , 2-cyano-2-propyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1-fluoro-1-cyclopropyl or 1-trifluoromethyl-1-cyclopropyl,

[0080] Alternatively, represents an optionally monosubstituted triazolyl group which is bridged to the remainder of the molecule via a nitrogen atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, trifluoromethyl or cyclopropyl,

[0081] R 4 , R 5 , R 6 , R 7 In particular, fluorine

[0082] Y represents in particular oxygen or =NH,

[0083] Z specifically stands for -NR 8 ,in

[0084] R 8 represents in particular hydrogen or methyl,

[0085] m specifically represents 0 or 1,

[0086] n specifically represents 0 or 1.

[0087] Configuration 5-2

[0088] R 1 In particular, ethyl,

[0089] R 2 In particular, it represents a methyl group,

[0090] R 3 represents in particular hydrogen, bromine, cyclopropyl, trifluoromethyl, tetrafluoroethyl, pentafluoroethyl,

[0091] Alternatively, represents phenyl, pyridyl, pyrimidinyl, pyridazinyl, thienyl, thiazolyl, oxazolyl or imidazolyl, each of which is optionally mono- or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, SF 5 , 2-cyano-2-propyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1-fluoro-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or pyridinyl which is optionally monosubstituted by chlorine or bromine,

[0092] Alternatively, represents an optionally monosubstituted triazolyl group which is bridged to the remainder of the molecule via a nitrogen atom, where the following substituents are possible in each case: cyano, fluorine, chlorine, bromine, trifluoromethyl or cyclopropyl,

[0093] R 4 , R 5 , R 6 , R 7 In particular, fluorine

[0094] Y represents in particular oxygen or =NH,

[0095] Z specifically stands for -NR 8 ,in

[0096] R 8 represents in particular hydrogen or methyl,

[0097] m specifically represents 0 or 1,

[0098] n specifically represents 0 or 1.

[0099] Configuration 6-1a

[0100] R 1 Especially represents ethyl,

[0101] R 2 Especially represents methyl,

[0102] R 3 In particular, bromine, cyclopropyl,

[0103] or, phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluoro-1-cyclopropyl, or, represents an optionally monosubstituted triazolyl group which is bridged to the remainder of the molecule via a nitrogen atom, where in each case the possible substituents are as follows: cyano, chlorine, bromine, cyclopropyl or 1-cyano-1-cyclopropyl,

[0104] Alternatively, represents thienyl or thiazolyl, each of which is optionally monosubstituted and bridged to the remainder of the molecule via a carbon atom, where the possible substituents in each case are as follows: chlorine or 1-cyano-1-cyclopropyl,

[0105] Alternatively, represents an optionally monosubstituted triazolyl radical which is bridged to the remainder of the molecule via a nitrogen atom, where the possible substituents in each case are as follows: cyclopropyl,

[0106] R 4 , R 5 , R 6 , R 7 Especially represents fluorine,

[0107] In particular, Y represents oxygen,

[0108] Z especially stands for -NR 8 ,in

[0109] R 8 represents in particular hydrogen or methyl,

[0110] In particular, m and n represent 0, or

[0111] In particular, m and n represent 1.

[0112] Configuration 6-1b

[0113] R 1 Especially represents ethyl,

[0114] R 2 Especially represents methyl,

[0115] R 3In particular, bromine, cyclopropyl,

[0116] or phenyl optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluoro-1-cyclopropyl,

[0117] R 4 , R 5 , R 6 , R 7 Especially represents fluorine,

[0118] In particular, Y represents oxygen,

[0119] Z especially stands for -NR 8 ,in

[0120] R 8 represents in particular hydrogen or methyl,

[0121] In particular, m and n represent 0, or

[0122] In particular, m and n represent 1.

[0123] Configuration 6-2

[0124] R 1 Especially represents ethyl,

[0125] R 2 Especially represents methyl,

[0126] R 3 In particular, it represents hydrogen, bromine, cyclopropyl,

[0127] or phenyl optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluoro-1-cyclopropyl, or phenyl optionally disubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano,

[0128] or represents an optionally monosubstituted pyridinyl group which is bridged to the remainder of the molecule via a carbon atom, where the possible substituents are in each case the following: cyano, chlorine, bromine, cyclopropyl, 1-cyano-1-cyclopropyl or a pyridinyl group which is monosubstituted by chlorine or bromine and where the pyridinyl group is bridged to the remainder of the molecule via a carbon atom,

[0129] Alternatively, represents thienyl or thiazolyl, each of which is optionally monosubstituted and bridged to the remainder of the molecule via a carbon atom, where the possible substituents in each case are as follows: chlorine,

[0130] Alternatively, represents an optionally monosubstituted triazolyl radical which is bridged to the remainder of the molecule via a nitrogen atom, where the possible substituents in each case are as follows: cyclopropyl,

[0131] R 4 , R 5 , R 6 , R 7 Especially represents fluorine,

[0132] Y represents in particular oxygen or =NH,

[0133] Z especially stands for -NR 8 ,in

[0134] R 8 represents in particular hydrogen or methyl,

[0135] In particular, m and n represent 0, or

[0136] In particular, m and n represent 1.

[0137] In a preferred embodiment, the invention relates to compounds of formula (I) in which Y represents oxygen, m=1, n=1, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and Z has the definition specified in Configuration (1-1) or Configuration (2-1) or Configuration (3-1) or Configuration (3-2) or Configuration (4-1) or Configuration (4-2) or Configuration (5-1) or Configuration (5-2) or Configuration (6-1a) or Configuration (6-1b) or Configuration (6-2).

[0138] In a preferred embodiment, the present invention relates to compounds of formula (I), wherein R 4 , R 5 , R 6 , R 7 represents fluorine, and R 1 , R 2 , R 3 , R 8 , Y, Z, n and m have the definitions specified in Configuration (1-1) or Configuration (2-1) or Configuration (3-1) or Configuration (3-2) or Configuration (4-1) or Configuration (4-2) or Configuration (5-1) or Configuration (5-2) or Configuration (6-1a) or Configuration (6-1b) or Configuration (6-2).

[0139] In a preferred embodiment, the present invention relates to compounds of formula (I), wherein R 1 Represents ethyl, R 2 Represents methyl, R 4 , R 5 , R6 , R 7 represents fluorine, Z represents N-methyl, and R 3 , Y, n and m have the definitions specified in Configuration (1-1) or Configuration (2-1) or Configuration (3-1) or Configuration (3-2) or Configuration (4-1) or Configuration (4-2) or Configuration (5-1) or Configuration (5-2) or Configuration (6-1a) or Configuration (6-1b) or Configuration (6-2).

[0140] In the general or preferred definitions, unless otherwise stated, halogen is selected from fluorine, chlorine, bromine and iodine, preferably selected in that order from fluorine, chlorine and bromine.

[0141] Aryl (including as part of a larger unit, such as aralkyl), unless defined differently, is selected from the following series: phenyl, naphthyl, anthracenyl, phenanthrenyl, preferably phenyl.

[0142] In the context of the present invention, unless defined differently, the term "alkyl" - by itself or in combination with other terms such as haloalkyl - is understood to mean a radical having 1 to 12 carbon atoms and which may be branched or unbranched, saturated aliphatic hydrocarbon radical. 1 -C 12 Examples of -alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Among these alkyl groups, C 1 -C 6 -alkyl. C 1 -C 4 -alkyl.

[0143] According to the present invention, unless defined differently, the term "alkenyl" - by itself or in combination with other terms - is understood to mean a straight-chain or branched C-alkyl group having at least one double bond. 2 -C 12 -alkenyl, for example, vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1,4-hexadienyl. Among these groups, C 2 -C 6 -alkenyl, and particularly preferably C 2 -C 4 -alkenyl.

[0144] According to the present invention, unless defined differently, the term "alkynyl" - by itself or in combination with other terms - is to be understood as meaning a straight-chain or branched C alkyl radical having at least one triple bond. 2 -C 12 -alkynyl, such as ethynyl, 1-propynyl and propargyl. Among these groups, C 3 -C 6 -alkynyl, and particularly preferably C 3 -C 4 -Alkynyl. The alkynyl group may also contain at least one double bond.

[0145] According to the present invention, unless otherwise defined, the term "cycloalkyl" - by itself or in combination with other terms - is to be understood as meaning C 3 -C 8 - cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Among these groups, C 3 -C 6 -cycloalkyl.

[0146] The term "alkoxy" - by itself or in combination with other terms such as haloalkoxy - is to be understood as meaning in the context of the present invention O-alkyl, wherein the term "alkyl" is as defined above.

[0147] Halogen-substituted groups (e.g. haloalkyl) are monohalogenated or polyhalogenated, up to the maximum number of possible substituents. In the case of polyhalogenation, the halogen atoms may be identical or different. In the case of the present invention, halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.

[0148] Unless otherwise stated, optionally substituted radicals may be mono- or polysubstituted, where the substituents in the case of polysubstitution may be identical or different.

[0149] The radical definitions or illustrations given above in general terms or listed in the preferred ranges apply correspondingly to the end products, and to the starting materials and intermediates. These radical definitions can be combined with one another as desired, i.e. including combinations between the respective preferred ranges.

[0150] According to the invention, preference is given to using compounds of the formula (I) which comprise a combination of the definitions listed above as being preferred.

[0151] According to the invention, particular preference is given to using compounds of the formula (I) which comprise a combination of the definitions listed above as being particularly preferred.

[0152] According to the invention, very particular preference is given to using compounds of the formula (I) which comprise a combination of the definitions listed above as very particularly preferred.

[0153] According to the invention, use is made in particular of compounds of the formula (I) which comprise a combination of the definitions listed above as particular definitions.

[0154] According to the invention, use is made in particular of compounds of the formula (I) which comprise a combination of the definitions listed above as particular definitions.

[0155] Depending on the nature of the substituents, the compounds of formula (I) may be in the form of geometrical isomers and / or optically active isomers or corresponding isomer mixtures of different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometrical isomers. Therefore, the present invention includes the pure stereoisomers and any desired mixtures of these isomers.

[0156] The compounds of formula (I) according to the present invention can be obtained by the process shown in the following scheme:

[0157] Method A

[0158]

[0159] Group R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings given above. 1 and X 2 Represents halogen. 9 Represents a straight chain or branched (C 1 -C 4 )alkyl or benzyl.

[0160] Step a)

[0161] Compounds of formula (III) can be prepared from imidazole derivatives of formula (II), for example by reaction with a halogenating agent (e.g., such as N-bromosuccinimide (NBS)) in a solvent (e.g., such as tetrahydrofuran), or by reaction of compounds of formula (II) with NBS in combination with azobis(isobutyronitrile) (AIBN) in tetrachloromethane or chloroform (e.g., similar to the methods described in WO 2013 / 149997, WO 2014 / 115077 or WO 2011 / 123609).

[0162] Imidazole derivatives of the formula (II) are commercially available or can be prepared by known methods, for example analogously to the methods described in WO 2014 / 191894, US 2003 / 229079 or WO 2013 / 156608.

[0163] Step b)

[0164] Where X 1 Compounds of formula (III) which preferably represent halogens from the group consisting of chlorine and bromine can be converted into compounds of formula (IV), for example, by transition metal-mediated cross-coupling reactions [see Chem. Rev. 1995, 95, 2457-2483; Tetrahedron 2002, 58, 9633-9695; Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), 2nd edition, Wiley-VCH, Weinheim, 2004] or by nucleophilic aromatic substitution reactions (see the methods described in Bioorganic and Medicinal Chemistry Letters 2007, 17, 5825-5830 or US 4125726).

[0165] For example, where X 1 The compound of formula (III) which preferably represents chlorine or bromine can be reacted according to known methods (see WO 2012 / 143599, US 2014 / 094474, US 2014 / 243316, US 2015 / 284358 or Journal of Organic Chemistry 2004, 69, 8829-8835) with a suitable boronic acid [R 3 -B(OH) 2 ] or borate ester reaction to obtain a compound of formula (IV). Examples of preferred coupling catalysts include palladium catalysts, such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(triphenylphosphine)dichloropalladium(II) or tetrakis(triphenylphosphine)palladium. Suitable alkaline reaction aids for carrying out these methods are preferably sodium, potassium or cesium carbonates. Some desired boronic acid derivatives [R 3 -B(OH) 2 ] or boric acid ester derivatives are known and / or commercially available, or they can be prepared by generally known methods (see Boronic Acids (eds.: DG Hall), second edition, Wiley-VCH, Weinheim, 2011). In this case, the above reaction is preferably carried out in a mixture of water and an organic solvent, the organic solvent being selected from conventional solvents that are inert under the prevailing reaction conditions. Ethers are often used, such as, for example, tetrahydrofuran, dioxane or 1,2-dimethoxyethane.

[0166] In addition, stannane derivatives [R 3-Sn(n-Bu) 3 ] as a coupling partner (see US 2013 / 281433, WO 2004 / 099177 or WO 2016 / 071214). Some desired stannane derivatives [R 3 -Sn(n-Bu) 3 ] are known and / or commercially available, or they can be prepared by generally known methods (see WO 2016 / 071214 or WO 2007 / 148093).

[0167] Compounds of formula (IV) can be obtained by coupling a halogenated imidazole derivative of formula (III) with an NH-containing heteroaromatic hydrocarbon (e.g., such as imidazoles or pyrazoles (which are optionally substituted as described above)) under basic conditions (e.g., with sodium hydride in dimethylformamide, see, e.g., WO 2005 / 058898). Alternatively, the reaction can be carried out under an inert gas atmosphere by catalysis with a copper (I) salt (e.g., cuprous iodide), in the presence of a suitable ligand (e.g., trans-N,N'-dimethylcyclohexane-1,2-diamine or R-(+)-proline) and a suitable base (e.g., potassium carbonate or potassium phosphate), in a suitable solvent (e.g., such as 1,4-dioxane or toluene) (see, e.g., WO 2016 / 109559).

[0168] Step c)

[0169] Where X 2 Imidazole derivatives of formula (V) which preferably represent halogen from bromine and iodine can be prepared using standard methods by reacting compounds of formula (IV) with, for example, bromine or N-bromosuccinimide (NBS) (see WO 2009 / 115572 or WO 2010 / 091411) or N-iodosuccinimide (NIS), optionally in the presence of acetic acid or trifluoroacetic acid (see WO 2008 / 063287, WO 2007 / 087548 or WO 2009 / 152025).

[0170] Step d)

[0171] Where X 2 Compounds of formula (V) which preferably represent halogens from the group consisting of bromine and iodine can be prepared, for example, by reacting with thiol derivatives (R 1 -SH) and a copper (I) salt reaction (see EP257918 or WO 2009 / 152025) or through a nucleophilic aromatic substitution reaction (see Australian Journal of Chemistry 1987, 40, 1415-1425) to convert into a compound of formula (VI).

[0172] In addition, X 2 Preferably, the compound of formula (V) represents a halogen from the group consisting of bromine and iodine and a thiol derivative (R 1 -SH) can be reacted over a palladium catalyst (e.g., tris(dibenzylideneacetone)dipalladium [Pd 2 (dba) 3 ]). In this case, amine bases (for example, triethylamine or N, N-diisopropylethylamine (DIPEA)) are often used, as well as phosphine ligands (for example, such as Xantphos) (see WO 2013 / 025958, WO 2013 / 066869, US 2009 / 027039, WO 2011 / 058149, WO 2011 / 143466 or Bioorganic and Medicinal Chemistry Letters 2016, 26, 2984-2987). In this case, the reaction is preferably carried out in a solvent, the solvent being selected from conventional solvents that are inert under the reaction conditions at the time. Preferably, ethers, such as dioxane or 1,2-dimethoxyethane.

[0173] Thiol derivatives such as methyl mercaptan, ethyl mercaptan or isopropyl mercaptan are commercially available or can be prepared by known methods such as analogously to methods described in US 2006 / 025633, US 2006 / 111591, US 2820062, Chemical Communications 2000, 13, 1163-1164 or Journal of the American Chemical Society 1922, 44, 1323-1333.

[0174] Step e)

[0175] Esters of formula (VI) can be converted into carboxylic acids of formula (VII) using standard methods (see, for example, WO 2014 / 191894, US 2006 / 194779, WO2014 / 086663 or European Journal of Organic Chemistry 2009, 213-222), for example by reaction with an alkali metal hydroxide as base (e.g. sodium hydroxide or lithium hydroxide) in an alcohol (e.g. methanol or ethanol) or an ether (e.g. THF) as solvent, preferably in the presence of water.

[0176] Step f)

[0177] The compound of formula (I, m=0, n=0) can be prepared by reacting the compound of formula (VII) with the compound of formula (VIII) in the presence of a condensing agent.

[0178] Compounds of formula (VIII) are commercially available or can be prepared by known methods (for example analogously to the methods described in Chemistry-A European Journal 2017, 23, 13607-13611 or EP0234449 A2).

[0179] The conversion to the compound of formula (I, m=0, n=0) can be carried out in the absence of a solvent or in a solvent, preferably in a solvent, the solvent being selected from conventional solvents that are inert under the reaction conditions at the time. Preferred are ethers, such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols, such as methanol, ethanol or isopropanol; nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons, such as toluene or xylene; aprotic polar solvents, such as N,N-dimethylformamide or N-methylpyrrolidone, or nitrogen-containing compounds, such as pyridine.

[0180] Examples of suitable condensing agents are carbodiimides, such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; acid anhydrides, such as acetic anhydride, trifluoroacetic anhydride; mixtures of triphenylphosphine, a base and carbon tetrachloride, or mixtures of triphenylphosphine and an azodiester (e.g. diethylazodicarboxylic acid).

[0181] The reaction can be carried out in the presence of a suitable catalyst such as 1-hydroxybenzotriazole.

[0182] The reaction can be carried out in the presence of an acid or a base.

[0183] Examples of acids that can be used in the reaction are sulfonic acids, such as methanesulfonic acid or p-toluenesulfonic acid; carboxylic acids, such as acetic acid, or polyphosphoric acid.

[0184] Examples of suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such as triethylamine and N,N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.

[0185] Step g)

[0186] The compound of formula (I, m=1, n=0 or 1) can be prepared by oxidizing the compound of formula (I, m=0, n=0), for example, similar to the method described in WO 2016 / 169882 or WO 2016 / 124557. The oxidation reaction is usually carried out in a solvent. Preferred are halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols, such as methanol or ethanol; formic acid, acetic acid, propionic acid or water.

[0187] Examples of suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.

[0188] Method B

[0189]

[0190] Group R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings given above. 1 Represents halogen. 9 Represents a straight chain or branched (C 1 -C 4 )alkyl or benzyl.

[0191] Step a)

[0192] Compounds of formula (III) can be prepared from imidazole derivatives of formula (II), for example by reaction with a halogenating agent (e.g., such as N-bromosuccinimide (NBS)) in a solvent (e.g., such as tetrahydrofuran), or by reaction of compounds of formula (II) with NBS in combination with azobisisobutyronitrile (AIBN) in tetrachloromethane or chloroform (e.g., similar to the methods described in WO 2013 / 149997, WO2014 / 115077 or WO 2011 / 123609).

[0193] Imidazole derivatives of the formula (II) are commercially available or can be prepared by known methods, for example analogously to the methods described in WO 2014 / 191894, US 2003 / 229079 or WO 2013 / 156608.

[0194] Step b)

[0195] The imidazole derivatives of formula (IX) can be reacted with the compounds of formula (III) by standard methods via reaction with disulfide (R 1 -SSR 1 ) with, for example, a strong base (preferably lithium diisopropylamide (LDA)) in tetrahydrofuran (see Bioorganic and Medicinal Chemistry Letters 2010, 20, 1084-1089), or, for example, hydrogen peroxide and iodine in ethanol (see Synthesis 2015, 47, 659-671) for preparation.

[0196] Step c)

[0197] The compound of formula (IX) is converted in analogy to method A, step e) into the compound of formula (X).

[0198] Step d)

[0199] The compound of formula (X) is reacted with the compound of formula (VIII) in a manner similar to step f) of method A to give a compound of formula (I, m=0, n=0, R 3 =X 1 ) compounds.

[0200] Steps e, h)

[0201] Formula (I, m = 0, n = 0, R 3 =X 1 ) to a compound of formula (I, m=1, n=0 or 1, R 3 =X 1 ) and the conversion of the compound of formula (I, m=0, n=0) to the compound of formula (I, m=1, n=0 or 1) is carried out in a manner similar to step g) of method A.

[0202] Step f, g)

[0203] Formula (I, m = 0, n = 0, R 3 =X 1 ) to a compound of formula (I, m=0, n=0), and a compound of formula (I, m=1, n=0 or 1, R 3 =X 1 The conversion of the compound of formula (I, m=1, n=0 or 1) is carried out in a manner similar to step b) of method A.

[0204] Method C

[0205]

[0206] Group R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the above-mentioned meanings. Y represents NH, m and n represent 0 or m and n represent 1.

[0207] Step a)

[0208] The compound of formula (I, m = 1, n = 1, Y = NH) can be prepared, for example, by reacting a suitable nitrogen source with a suitable oxidant in a suitable solvent or diluent using a suitable nitrogen source. The corresponding conversion is recorded in the literature, for example, in Chem. Commun. 2017, 53, 348-351. An example of a suitable oxidant is (diacetoxy iodine) benzene. Examples of suitable nitrogen sources include ammonium carbamate, ammonium acetate or ammonia in methanol. Suitable solvents are inert under selected reaction conditions. Examples of suitable solvents include methanol, acetonitrile or toluene. For example, a compound of formula (I, m = 0, n = 0) can be converted to a compound of formula (I, m = 1, n = 1, Y = NH) by treating with (diacetoxy iodine) benzene and ammonium carbamate in methanol at room temperature.

[0209] Method D

[0210]

[0211] Group R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and Z have the meanings given above. 1 represents halogen, and Y represents NH.

[0212] Steps a, d)

[0213] Formula (I, m = 0, n = 0, R 3 =X 1 ) to the compound of formula (I, m=1, n=1, R 3 =X 1 ) and the conversion of the compound of formula (I, m=0, n=0) to the compound of formula (I, m=1, n=1) is carried out in a manner similar to step a) of method C.

[0214] Step b, c)

[0215] Formula (I, m = 0, n = 0, R 3 =X 1 ) to a compound of formula (I, m=0, n=0), and a compound of formula (I, m=1, n=1, R 3 =X 1 The conversion of the compound of formula (I, m=1, n=1) into the compound of formula (I, m=1, n=1) is carried out in a manner analogous to step b) of method A.

[0216] Method E

[0217]

[0218] Group R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and Y have the above-mentioned meanings, m represents halogen 0 or 1, and n represents 0 or 1.

[0219] Step a)

[0220] Formula (I, R 8 ≠H) can be, for example, a compound of formula (I, R 8 =H) is prepared in the presence of a suitable alkylating agent and a suitable base in a suitable solvent or diluent. Suitable alkylating agents are alkyl halides, preferably alkyl bromides or alkyl iodides, and alkyl sulfonates, for example alkyl methyl sulfonates, alkyl toluene sulfonates or alkyl trifluoromethyl sulfonates. Suitable auxiliary bases are sodium, potassium or cesium carbonates, sterically hindered and non-nucleophilic amine bases, for example N,N-diisopropylethylamine or hydride bases, for example sodium hydride. Suitable solvents are inert under the respectively selected reaction conditions. Depending on the base used, the following are suitable: ethers, such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons, such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons, such as toluene or xylene; or aprotic polar solvents, such as acetone, N,N-dimethylformamide or N-methylpyrrolidone. Preferably, the reaction is carried out using a carbonate base in acetone or N,N-dimethylformamide.

[0221] For example, formula (I, R 8 =H) can be converted to the compound of formula (I, R 8 =Me).

[0222] Method F

[0223]

[0224] Group R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 Has the meaning given above. X 1and X 2 Represents halogen.

[0225] Step a)

[0226] The compound of formula (XII) can be prepared from the diphenylamine of formula (XI) by reaction with formic acid, a formate ester or an orthoformate, in the presence or absence of a solvent which is inert under the reaction conditions prevailing. If necessary, the reaction can be carried out by adding Acid or Lewis acid catalysis.

[0227] Compounds of formula (XI) are commercially available or can be prepared by known methods (for example, analogously to the methods described in Chemistry-A European Journal 2017, 23, 13607-13611 or EP0234449 A2).

[0228] Step b)

[0229] The compound of formula (XII) is converted in analogy to process E, step a) into the compound of formula (XIII).

[0230] Step c)

[0231] Formula (I, m = 0, n = 0, R 3 =H) can be prepared by reacting a compound of formula (XIII) with a compound of formula (XIV). For this purpose, the compound of formula (XIII) is first treated with a strong base (e.g., such as tetramethylpiperidinyl zinc chloride lithium chloride complex) and then reacted with a compound of formula (XIV) in the presence of a palladium catalyst (e.g., such as tetrakis(triphenylphosphine)palladium(0)). In this case, the reaction is preferably carried out in a solvent selected from conventional solvents that are inert under the reaction conditions at the time. Preferably, ethers, such as dioxane or tetrahydrofuran.

[0232] The compound of formula (XIV) can be prepared by known methods (for example analogously to the method described in WO2020074558 A1).

[0233] Step d)

[0234] The compound of formula (I, m=0, n=0) can be prepared by 3 =H) are prepared. For this purpose, the formula (I, m=0, n=0, R 3=H) is first treated with a strong base (e.g., tetramethylpiperidinyl zinc chloride lithium chloride complex) and then reacted with an aryl halide or heteroaryl halide (preferably a bromide or iodide) in the presence of a palladium catalyst (e.g., tetrakis(triphenylphosphine)palladium(0)). In this case, the reaction is preferably carried out in a solvent selected from conventional solvents that are inert under the reaction conditions prevailing. Preferably, ethers, such as dioxane or tetrahydrofuran, are used.

[0235] Step e)

[0236] The compound of formula (I, m=0, n=0) is converted analogously to method A, step g) into the compound of formula (I, m=1, n=0 or 1).

[0237] Methods and uses

[0238] The invention also relates to methods for controlling animal pests, wherein the compounds of formula (I) are acted on animal pests and / or their habitat. The control of animal pests is preferably carried out in agriculture and forestry and in material protection. This preferably excludes methods for surgical or therapeutic treatment of the human or animal body and diagnostic methods performed on the human or animal body.

[0239] The invention also relates to the use of the compounds of formula (I) as pesticides, in particular crop protection agents.

[0240] In the context of the present application, the term "pesticide" always also includes the term "crop protection composition" in each case.

[0241] Due to good plant tolerance, favorable homeothermic animal toxicity and good environmental compatibility, the compounds of the formula (I) are suitable for protecting plants and plant organs against biotic and abiotic stress factors, increasing the harvest yield, improving the quality of the harvested material, and for controlling animal pests encountered in agriculture, horticulture, animal husbandry, aquaculture, forestry, gardening and leisure facilities, in the protection of stored products and materials, and in the hygiene sector, in particular insects, arachnids, helminths, in particular nematodes and molluscs.

[0242] In the context of the present patent application, the term "sanitation" should be understood to mean any and all measures, regulations and methods intended to prevent disease (particularly infectious diseases) and to protect the health of humans and animals and / or to protect the environment and / or to keep clean. According to the present invention, this particularly includes measures for cleaning, disinfecting and sterilizing such as textiles or hard surfaces (particularly surfaces made of glass, wood, cement, porcelain, ceramics, plastics or other metals) to ensure that they are free from sanitary pests and / or their secretions. In this regard, the scope of protection of the present invention preferably excludes methods for surgical operations or therapeutic treatments applied to the human or animal body and diagnostic methods implemented on the human or animal body.

[0243] The term "sanitation sector" therefore covers all areas, technical fields and industrial applications in which these hygiene measures, regulations and methods are important, for example hygiene in kitchens, bakeries, airports, baths, swimming pools, department stores, hotels, hospitals, livestock pens, animal husbandry, etc.

[0244] The term "hygiene pest" is therefore understood to mean one or more animal pests, the presence of which in the sanitary sector is problematic, in particular for health reasons. The main aim is therefore to avoid the presence of hygiene pests and / or to limit exposure to these pests in the sanitary sector, or to limit them to a minimum. This can be achieved in particular by using pesticides that can be used to prevent infection and overcome existing infections. Formulations that prevent or reduce exposure to pests can also be used. For example, hygiene pests include the organisms mentioned below.

[0245] The term "sanitation protection" therefore covers all actions to maintain and / or improve these sanitation measures, regulations and methods.

[0246] The compounds of formula (I) can preferably be used as pesticides. They are active against normally sensitive and resistant species and against all or specific stages of development. The above-mentioned pests include:

[0247] Pests from the phylum Arthropoda, in particular from the class Arachnida, for example Acarus spp. (e.g. Acarus siro), Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp. (e.g. Aculus fockeui, Aculus schlechtendali), Amblyomma sp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp. (e.g. Brevipalpus phoenicis), Bryobia graminum), Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp. (e.g., Eotetranychus hicoriae), Epitrimerus pyri, Eutetranychus spp. (e.g., Eutetranychus banksi), Eriophyes spp. (e.g., Eriophyes pyri), Glycyphagus domesticus), Halotydeus destructor, Hemitarsonemus spp. (e.g. Hemitarsonemus latus (= Polyphagotarsonemus latus)), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp.), Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp. (e.g. Oligonychus coffeae, Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus syothersi), Ornithodorus spp., Ornithonyssus spp., Panonychus spp. (e.g. Panonychus citri (=Metatetranychus citri)), Panonychus spp. ulmi (= Metatetranychus ulmi)), citrus rust mite (Phyllocoptruta oleivora), Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpiomaurus, Stenotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp. (e.g. Tarsonemus confusus, Tarsonemus pallidus), Tetranychus spp. (e.g. Tetranychus canadensis), canadensis), Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;

[0248] Pests of the class Chilopoda, for example, Geophilus spp., Scutigera spp.;

[0249] Pests of the order Collembola or class Collembola, for example, Onychiurus armatus; Sminthurus viridis;

[0250] Pests of the class Diplopoda, for example, millipede (Blaniulus guttulatus);

[0251] Pests of the class Insecta, for example, of the order Blattodea, such as Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaeamaderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp. (for example, Periplaneta americana, Periplaneta australasiae), Pycnoscelus surinamensis, Supella longipalpa;

[0252] Pests of the order Coleoptera, for example, Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasta alni, Agrilus spp. (for example, Agrilus planipennis, Agrilus coxalis, Agrilus bilineatus, Agrilus anxius), Agriotes spp. (for example, Agriotes linneatus, Agriotes mancus, Agriotes obscurus), Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anomala dubia, Anoplophora spp. (e.g. Anoplophora glabripennis), Anthonomus spp. (e.g. Anthonomus grundis), Anthrenus spp., Apion spp., Apogonia spp., Athous haemorrhoidales, Atomaria spp. (e.g. Atomaria linearis), Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp. (e.g. Bruchus pisorum, Bruchus rufimanus), Cassida spp., Cerotoma trifurcata), Ceutorrhynchus spp. (e.g. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae), Chaetocnema spp.) (e.g., sweet potato leaf beetle (Chaetocnema confinis), American tooth flea beetle (Chaetocnema denticulata), millet concave shank flea beetle (Chaetocnema ectypa)), Cleonus mendicus, broad-breasted click beetle (Conorus spp.), root neck weevil (Cosmopolites spp.) (e.g., banana weevil (Cosmopolites sordidus)), brown New Zealand ribbed gill beetle (Costelytra zealundica), click beetle (Ctenicera spp.), weevil (Curculio spp.) (e.g., American walnut weevil (Curculio caryae), large chestnut weevil (Curculio caryatrypes), American hazelnut weevil (Curculio obtusus), small chestnut weevil (Curculio sayi)), rusty red flat grain beetle (Cryptolestes ferrugineus), long-horned flat grain beetle (Cryptolestes pusillus), poplar stem hidden beak weevil (Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dendroctonus spp. (e.g. Dendroctonus ponderosae), Dermestes spp., Diabrotica spp. (e.g. Diabrotica balteata, Diabrotica barberi), Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera), Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloborus spp., Epicaerus spp., Epilachna spp.) (e.g. Epilachna borealis, Epilachna varivestis), Epitrix spp. (e.g. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis), Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychusarator, Heteronyx spp., Hoplia argentea, Hylamorpha elegans, Hylotrupes bajulus), Hypera postica, Hypothenemus spp., Hypothenemus spp. (e.g., Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens), Lachnosterna consanguinea, Lasiorma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa ​​decemlineata, Leucoptera spp. (e.g., Leucoptera coffeella), Limonius ectypus, Lissorhoptrus oryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthora, Lyctus spp., Megacyllene spp. (e.g. Megacyllenerobiniae), Megascelis spp.), Melanotus spp. (e.g. Melanotus longulus oregonensis), Meligethes aeneus, Melolontha spp. (e.g. Melolontha melolontha), Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp. (e.g. Otiorhynchus cribricollis, Otiorhynchus cribricollis), ligustici), Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus), Oulema spp. (e.g. Oulema melanopus, Oulema oryzae), Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp. (e.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta serrata, Phyllotreta serrata striolata), Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp.) (e.g., potato flea beetle (Psylliodes affinis), rape flea beetle (Psylliodes chrysocephala), hop flea beetle (Psylliodes punctulata)), spider beetle (Ptinus spp.), dusky lady beetle (Rhizobius ventralis), grain borer (Rhizopertha dominica), cryptophorus weevil (Rhynchophorus spp.), red palm weevil (Rhynchophorus ferrugineus), palm weevil (Rhynchophorus palmarum), Scolytus spp. (e.g., European elm borer (Scolytus multistriatus)), Sinoxylon perforans, grain weevil (Sitophilus spp.) (e.g., grain weevil (Sitophilus granarius), tamarind weevil (Sitophilus linearis), rice weevil (Sitophilus oryzae), corn weevil (Sitophilus zeamais), Sphenophorus spp., Stegobium paniceum, Sternechus spp. (e.g. Sternechus paludatus), Symphyletes spp., Tanymecus spp. (e.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus), Tenebrio molitor, Tenebrio mauretanicus, Tribolium spp. (e.g. Tribolium audax, Tribolium castaneum, Tribolium confusum), Trogorma spp., Tychius spp.), Xylotrechus spp., Zabrus spp. (e.g., Zabrus tenebrioides);

[0253] Pests of the order Dermaptera, for example, Anisolabis maritime, Forficula auricularia, Labidura riparia;

[0254] Pests of the order Diptera, for example, Aedes spp. (e.g. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans), Agromyza spp. (e.g. Agromyza frontella, Agromyza parvicornis), Anastrepha spp., Anopheles spp. (e.g. Anopheles quadrimaculatus, Anopheles gambiae), Asphondylia spp., Bactrocera spp. (e.g. Bactrocera cucurbitae, Bactrocera orientalis), dorsalis, Bactrocera oleae), Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp. (e.g. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghum sorghicola), Contarinia tritici), Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp. (e.g. Culex pipiens, Culex quinquefasciatus), Culicoides spp., Culiseta spp.), Cuterebra spp., Dacus oleae, Dasineura spp. (e.g. Dasineura brassicae), Delia spp. (e.g. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum), Dermatobia hominis, Drosophila spp. (e.g. Drosphila melanogaster, Drosophila suzukii), Echinocnemus spp., Euleia heraclei, Fannia spp., Gastrophilus spp., Glossina spp.), Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hyporma spp., Liriomyza spp. (e.g. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae), Lucilia spp. (e.g. Lucilia cuprina), Lutzomyia spp., Mansonia spp., Musca spp. (e.g. Musca domestica, Musca domestica vicina), Oestrus spp.), Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyia spp.) (e.g., Pegomya betae, Pegomya hyoscyami, Pegomya rubivora), Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platyparea poeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp. (e.g., Rhagoletis cingulata, Rhagoletis completea, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella), Sarcophaga spp. spp.), Simulium spp. (e.g. Simulium meridionale), Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp. (e.g. Tipula paludosa, Tipula simplex), Toxotrypana curvicauda;

[0255] Pests of the order Hemiptera, for example Acizzia acaciaebaileyanae, Acizziadodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp. (for example Acyrthosiphon pisum), Acrogonia spp., Aeneolamia spp., Agonascena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp. (for example Amrasca bigutulla, Amrasca devastans), Anuraphis cardui, Aonidiella spp. (e.g. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata), Aphanostigma piri, Aphis spp. (e.g. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis sillinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis apple aphid (Aphis nerii), Aphis spp. pomi), leaf rollers (Aphis spiraecola), Aphis viburniphila), grape sawflies (Arboridia apicalis), Arytainilla spp., Aspidiella spp., Aspidiotus spp.) (e.g. Aspidiotus nerii), Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreoglycaspis melaleucae, Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp. (e.g. Cacopsylla pyricola), Calligypona marginata, Capulinia spp., Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp.), Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulinambila, Coccomytilus halli, Coccus spp. (e.g. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis), Cryptomyzus ribis, Cryptonossa spp., Ctenarytaina spp. spp.), Dalbulus spp., Dialeurodes chittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp., Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp.) (e.g., Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae), Dysmicoccus spp., Empoasca spp. (e.g., Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca solana, Empoasca stevensi), Eriosoma spp. (e.g., Eriosoma americanum, Eriosomalanigerum, Eriosoma pyricola), Erythroneura spp., Eucalyptolyma spp., Euphyllura spp.), Euscelis bilobatus, Ferrisia spp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp. (e.g. Icerya purchasi), Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp. (e.g. Lecanium corni) (= Parthenolecanium corni), Lepidosaphes spp. (e.g. Lepidosaphes ulmi), Lipaphis erysimi, Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp.) (e.g., Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae), Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp. (e.g., Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus tobacco aphid, Myzus nicotianae), Nasonovia ribis nigri, Neomaskellia spp., Nephotettix spp. (e.g. Nephotettix cincticeps, Nephotettix nigropictus), Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp. (e.g. Paratrioza cockerelli), Parlatoria spp., Pemphigus spp. (e.g. Pemphigus spp. bursarius), Pemphigus populivenae), Peregrinus maidis, Perkinsiella spp., Phenacoccus spp. (e.g. Phenacoccus madeirensis), Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp.) (e.g. Phylloxera devastatrix, Phylloxera notabilis), Pinnaspis aspidistrae, Planococcus spp. (e.g. Planococcus citri), Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp. (e.g. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus fusca, Pseudococcus spp. viburni), Psyllopsis, Psylla spp. (e.g., Psylla buxi, Psylla mali, Psylla pyri), Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp. (e.g., Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus), Quesada gigas, Rastrococcus spp., Rhopalosiphum spp. (e.g., Rhopalosiphum maidis, Rhopalosiphum oxyacanthae), rice and wheat aphids (Rhopalosiphum padi), red-bellied constriction aphids (Rhopalosiphum rufiabdominale), black-helmeted scale (Saissetia spp.) (e.g., Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetiaoleae), Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp.) (e.g., Toxoptera aurantii, Toxoptera citricidus), Trialeurodes vaporariorum, Trioza spp. (e.g., Trioza diospyri), Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

[0256] Pests of the suborder Heteroptera, for example, Aelia spp., Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp. (e.g. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus), Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp. (e.g. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius), Eurydemas spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis), Leptoglossus phyllopus, Lygocoris spp. (e.g. Lygocoris pabulinus), Lygus spp. (e.g. Lygus elisus, Lygus hesperus, Lygus lineolaris), Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp.) (e.g. Nezaraviridula), Nysius spp., Oebalus spp., Pentomidae, Piesmaquadrata, Piezodorus spp. (e.g. Piezodorus guildinii), Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.;

[0257] Pests of the order Hymenoptera, for example, Acromyrmex spp., Athalia spp. (e.g. Athalia rosae), Atta spp., Camponotus spp., Dolichovespula spp., Diprion spp. (e.g. Diprion similis), Hoplocampa spp. (e.g. Hoplocampa cookei, Hoplocampa testudinea), Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp.) (e.g. Sirex noctilio), Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp. (e.g. Vespa crabro), Wasmannia auropunctata, Xeris spp.;

[0258] Pests of the order Isopoda, for example, Armadillidium vulgare, Oniscusasellus, Porcellio scaber;

[0259] Pests of the order Isoptera, for example, Coptotermes spp. (e.g. Coptotermes formosanus), Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermes spp., Reticulitermes spp. (e.g. Reticulitermes flavipes, Reticulitermes hesperus);

[0260] Pests of the order Lepidoptera, for example, Achroia grisella, Acronicta major, Adoxophyes spp. (e.g. Adoxophyesorana), Aedia leucomelas, Agrotis spp. (e.g. Agrotissegetum, Agrotis ipsilon), Alabama spp. (e.g. Alabama argillacea), Amyelois transitella, Anarsia spp., Anticarsia spp. (e.g. Anticarsia gemmatalis), Argyroploce spp., Autographa spp.), Cabbage armyworm (Barathrabrassicae), Apple marrow moth (Blastodacna atra), Indica skipper (Borbo cinnara), Cotton miner (Bucculatrix thurberiella), Pine looper (Bupalus piniarius), Brown armyworm (Busseola spp.), Leaf roller (Cacoecia spp.), Tea moth (Caloptilia theivora), Tobacco roller (Capuareticulana), Apple roller (Carpocapsa pomonella), Peach fruit moth (Carposina niponensis), Winter moth (Cheimatobia brumata), Grass moth (Chilo spp.) (e.g., Chilo plejadellus, Chilo suppressalis), Choreutis pariana, Choristoneura spp., Chrysodeixis chalcites, Grape fruit moth (Clysia ambiguella), Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp.) (e.g., Cydia nigricana, Cydia pomonella), Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp. (e.g., Dioryctriazimmermani), Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp. (e.g., Ephestia elutella, Ephestia kuehniella), Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp., Eupocilia ambiguella, Euproctis spp. (e.g., Euproctis chrysorrhoea), Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp. (e.g., Grapholita molesta, Grapholita prunivora), Hedylepta spp., Helicoverpa spp.) (e.g., Helicoverpa armigera, Helicoverpa zea), Heliothis spp. (e.g., Heliothis virescens), Hepialus spp. (e.g., Hepialus humuli), Hofmannophila pseudospretella, Homoeosoma spp., Homona spp.), apple nest moth (Hyponomeuta padella), persimmon moth (Kakivoriaflavofasciata), Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp. (e.g., coffee leafminer (Leucoptera coffeella)), Lithocolletis spp. (e.g., apple leafminer (Lithocolletis blancardella)), green fruit armyworm (Lithophaneantennata), Lobesia spp. (e.g., grape leafminer (Lobesia botrana)), bean rootworm (Loxagrotis albicosta), Lymantria spp.) (e.g. Lymantriadispar), Lyonetia spp. (e.g. Lyonetia clerkella), Malacosoma neustria, Maruca testulalis, Mamstrabrassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp. (e.g. Ostrinia nubilalis), Panolis flammea, Parnara spp., Pectinophora spp. (e.g. Pectinophora gossypiella), Perileucoptera spp., Phthorimaea spp.) (e.g. Phthorimaea operculella), Phyllocnistis citrella, Phyllonorycter spp. (e.g. Phyllonorycter blancardella, Phyllonorycter crataegella), Pieris spp. (e.g. Pieris rapae), Platynota stultana, Plodia interpunctella, Plusia spp., Plutella axylostella (= Plutella maculipennis), Podesia spp. (e.g. Podesia syringae), Prays spp., Prodenia spp., Protoparce spp.), Pseudaletia spp. (e.g., Pseudaletia unipuncta), Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp. (e.g., Schoenobius bipunctifer), Scirpophaga spp. (e.g., Scirpophaga innotata), Scotia segetum, Sesamia spp. (e.g., Sesamia inferens), Sparganothis spp., Spodoptera spp. (e.g., Spodoptera aeradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera spp. frugiperda), Spodoptera praefica), Stathmopoda spp., Stenoma spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thaumetopoea spp.), soybean armyworm (Thermesiagemmatalis), cork moth (Tinea cloacella), bag moth (Tinea pellionella), curtain moth (Tineola bisselliella), Tortrix spp., felt moth (Trichophaga tapetzella), powder moth (Trichoplusia spp.) (such as Trichoplusia ni), yellow stem borer (Tryporyza incertulas), tomato leafminer (Tuta absoluta), and blue butterfly (Virachola spp.);

[0261] Pests of the order Orthoptera or Saltatoria, for example, Acheta domesticus, Dichroplus spp., Gryllotalpa spp. (for example Gryllotalpa gryllotalpa), Hieroglyphus spp., Locusta spp. (for example Locusta migratoria), Melanoplus spp. (for example Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria);

[0262] Pests from the order of the Phthiraptera, for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Ptirus pubis, Trichodectes spp.;

[0263] Pests of the order Psocoptera, for example, Lepinatus spp., Liposcelis spp.;

[0264] Pests of the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp. (for example Ctenocephalides canis, Ctenocephalides felis), Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

[0265] Pests from the order of the Thysanoptera, for example, Anaphothrips obscurus, Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp. (for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi), Haplothrips spp., Heliothrips spp. spp.), Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp. (e.g. Thrips palmi, Thrips tabaci);

[0266] Pests of the order Zygentoma (=suborder Thysanura), for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

[0267] Pests of the class Symphyla, for example, Scutigerella spp. (for example Scutigerella immaculata);

[0268] Pests of the phylum Mollusca, for example, pests of the class Bivalvia, such as Dreissena spp.,

[0269] and pests of the class Gastropoda, for example, Arion spp. (e.g. Arion ater rufus), Biomphalaria spp., Bulinus spp., Deroceras spp. (e.g. Deroceras laeve), Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.;

[0270] Plant pests of the class Nematoda, i.e. plant parasitic nematodes, in particular Aglenchus spp. (e.g. Aglenchus agricola), Anguinas spp. (e.g. Anguina tritici), Aphelenchoides spp. (e.g. Aphelenchoides arachidis, Aphelenchoides fragariae), Belonolaimus spp. (e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni), Bursaphelenchus spp. (e.g. Bursaphelenchus spp. cocophilus), Bursaphelenchus eremus, Bursaphelenchus xylophilus), Cacopaurus spp. (e.g. Cacopaurus pestis), Criconemella spp. (e.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax)), Criconemoides spp. (e.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum), Ditylenchusapp. (e.g., Ditylenchus dipsaci), Dolichodorus spp., Globora spp.) (e.g. Globora pallida, Globora rostochiensis), Helicotylenchus spp. (e.g. Helicotylenchus dihystera), Hemicriconemoides spp., Hemicycliophora spp., Heterora spp. (e.g. Heterora avenae, Heterora glycines, Heterora schachtii), Hirschmaniella spp., Hoplolaimus spp., Longidorus spp. (e.g. Longidorus africanus), Meloidogyne spp.) (e.g., Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita), Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp. (e.g., Paratrichodorus minor), Paratylenchus spp., Pratylenchus spp. (e.g., Pratylenchus penetrans penetrans), Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp. (e.g. Radopholus citrophilus, Radopholus similis), Rotylenchulus spp.), Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp. (e.g. Trichodorus obtusus, Trichodorus primitivus), Tylenchorhynchus spp. (e.g. Tylenchorhynchus annulatus), Tylenchulus spp. (e.g. Tylenchulus semipenetrans), Xiphinema spp. (e.g. Xiphinema index). .

[0271] The compounds of formula (I) can be used as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antifungals, bactericides, viricides (including agents against viroids) or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms) at certain concentrations or application rates, as appropriate. They can also be used as intermediates or precursors for the synthesis of other active ingredients.

[0272] Formulation / use form

[0273] The invention further relates to a formulation, in particular a formulation for controlling unwanted animal pests. The formulation can be applied to the animal pests and / or their habitat.

[0274] The formulations of the invention can be provided to the end user as a ready-to-use "use form", i.e., the formulation can be applied directly to plants or seeds using suitable equipment (such as a sprayer or duster). Alternatively, the formulation can be provided to the end user in the form of a concentrate, which is diluted before use, preferably with water. Unless otherwise indicated, the term "formulation" refers to the above-mentioned concentrate, while the term "use form" refers to a solution that can be used by the end user, i.e., usually the above-mentioned diluted formulation.

[0275] The formulations of the invention may be prepared in conventional manner, for example by mixing a compound of the invention with one or more suitable adjuvants (eg, those disclosed herein).

[0276] The formulations comprise at least one compound according to the invention and at least one agriculturally useful adjuvant, such as a carrier and / or a surfactant.

[0277] The carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally allows the compound to be better applied to, for example, plants, plant parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, especially ammonium sulfate, ammonium phosphate and ammonium nitrate; natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth; silica gel and synthetic rock powders such as finely divided silica, alumina and silicates. Examples of typical suitable solid carriers for preparing granules include, but are not limited to, crushed and graded natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic particles of inorganic and organic grains, and particles of organic materials such as paper, sawdust, coconut shells, corn cobs and tobacco straw. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, such as aromatic and nonaromatic hydrocarbons (e.g. cyclohexane, alkanes, alkylbenzenes, xylene, toluene, tetralin, alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or methylene chloride), alcohols and polyols (which may optionally be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted The carrier may also be a liquefied gas extender, i.e. a liquid which is gaseous at standard temperature and standard pressure, for example an aerosol propellant such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.

[0278] Preferred solid carriers are selected from clay, talc and silica.

[0279] Preferred liquid carriers are selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams, lactones, carbonates, ketones and (poly)ethers.

[0280] The amount of the carrier is generally 1 to 99.99% by weight, preferably 5 to 99.9% by weight, particularly preferably 10 to 99.5% by weight, most preferably 20 to 99% by weight, based on the weight of the preparation.

[0281] The liquid carrier is typically present in 20 to 90 wt %, such as 30 to 80 wt %, based on the weight of the formulation.

[0282] The solid carrier is generally present at 0 to 50 wt%, preferably 5 to 45 wt%, such as 10 to 30 wt%, based on the weight of the formulation.

[0283] If the formulation contains two or more carriers, the above ranges refer to the total amount of the carriers.

[0284] The surfactant may be an ionic (cationic or anionic), amphoteric or nonionic surfactant, such as an ionic or nonionic emulsifier, foaming agent, dispersant, wetting agent, penetration enhancer, and any mixture of these surfactants. Examples of suitable surfactants include, but are not limited to, polyacrylates, ethoxylated poly(α-substituted)acrylate derivatives, lignin sulfonates (e.g., sodium lignin sulfonate), phenol sulfonates or naphthalene sulfonates, polycondensates of ethylene oxide and / or propylene oxide with or without alcohols, fatty acids or fatty amines (e.g., polyoxyethylene fatty acid esters, such as castor oil ethoxylate; polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), phosphate esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols (e.g., fatty acid esters of glycerol, sorbitol or sucrose), sulfates (e.g., alkyl sulfates and alkyl ether sulfates), sulfonates (e.g., alkyl sulfonates, aryl sulfonates and alkylbenzene sulfonates), naphthalene / formaldehyde sulfonated polymers, phosphate esters, protein hydrolysates, lignin sulfate waste liquor, and methylcellulose. If salts are mentioned in this paragraph, the salts preferably refer to the relevant alkali metal salts, alkaline earth metal salts and ammonium salts.

[0285] Preferred surfactants are selected from ethoxylated poly(α-substituted) acrylate derivatives, polycondensates of ethylene oxide and / or propylene oxide with alcohols, polyoxyethylene fatty acid esters, alkylbenzene sulfonates, naphthalene / formaldehyde sulfonated polymers, polyoxyethylene fatty acid esters such as castor oil ethoxylates, sodium lignin sulfonate and aromatic phenol ethoxylates.

[0286] The amount of surfactant is generally 5 to 40% by weight, such as 10 to 20% by weight, based on the weight of the formulation.

[0287] Other examples of suitable auxiliaries include water repellents, desiccants, binders (adhesives, tackifiers, fixatives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latexes (e.g. gum arabic, polyvinyl alcohol and polyvinyl acetate), natural phospholipids (e.g. cephalin and lecithin) and synthetic phospholipids, polyvinylpyrrolidone and sodium tylose acetate), thickeners and secondary thickeners (e.g. cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, for example the products available under the name Bentone, and finely divided silica), stabilizers (e.g. cold stabilizers, preservatives (e.g. dichlorobenzene, benzyl alcohol hemiformal, 1,2-benzisothiazole The invention also includes but is not limited to: organic pigments, such as 2-methyl-2-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-methyl-2-isothiazolin-3-one, antioxidants, light stabilizers (especially UV stabilizers) or other agents that can improve chemical and / or physical stability), dyes or pigments (for example inorganic pigments, such as iron oxide, titanium oxide and Prussian blue; organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes), defoamers (for example silicone defoamers and magnesium stearate), antifreeze agents, adhesives, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including trace nutrients, such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts), protective colloids, thixotropic substances, penetrants, chelating agents and complex formers.

[0288] The selection of auxiliary agent is related to the expected mode of administration of the compound of the present invention and / or the physical properties of the compound. In addition, auxiliary agent can be selected to give the preparation or the use form prepared therefrom with specific properties (technical, physical and / or biological properties). By suitable auxiliary agent selection, the preparation can be adapted to specific needs.

[0289] The formulation comprises an insecticidal / miticidal / nematicidal effective amount of the compound of the present invention. The term "effective amount" refers to an amount sufficient to prevent and treat harmful insects / mites / nematodes or protective materials on cultivated plants, and will not cause substantial damage to the treated plants. Such an amount can vary over a wide range and depends on various factors, such as the species of insects / mites / nematodes to be prevented and treated, the cultivated plants or materials to be treated, climatic conditions and the compound of the present invention used in each case. Typically, the formulation of the present invention comprises 0.01 to 99% by weight, preferably 0.05 to 98% by weight, more preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight, and most preferably 1 to 80% by weight of the compound of the present invention. The formulation may comprise two or more compounds of the present invention. In this case, the above range refers to the total amount of the compound of the present invention.

[0290] The formulation of the present invention can be in the form of any conventional formulation type, such as solutions (e.g., aqueous solutions), emulsions, water-based and oil-based suspensions, powders (e.g., wettable powders, soluble powders), dusts, pastes, granules (e.g., soluble granules, granules for broadcasting), suspension emulsion concentrates, natural or synthetic products impregnated with the compound of the present invention, fertilizers, and microcapsules in polymeric substances. The compound of the present invention can be present in a suspended, emulsified, or dissolved form. Examples of particularly suitable formulation types are solutions, water-soluble concentrates (such as SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (such as SC, OD, OF, FS), emulsifiable concentrates (such as EC), emulsions (such as EW, EO, ES, ME, SE), capsules (such as CS, ZC), pastes, lozenges, wettable powders or dusts (such as WP, SP, WS, DP, DS), compressed tablets (such as BR, TB, DT), granules (such as WG, SG, GR, FG, GG, MG), insecticides (such as LN) and gel formulations (such as GW, GF) for treating plant propagation materials such as seeds. These and other formulation types are defined by the Food and Agriculture Organization of the United Nations (FAO). The overview given is provided in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th edition May 2008, Croplife International.

[0291] Preferably, the preparation of the present invention is in the form of one of the following types: EC, SC, FS, SE, OD, WG, WP, CS, particularly preferred are EC, SC, OD, WG, CS.

[0292] Further details about the types of formulations and examples of their preparation are given below. If there are two or more compounds of the invention, the defined amount of the compounds of the invention refers to the total amount of the compounds of the invention. Conversely, if there are two or more such components (e.g., wetting agents or adhesives), this also applies to any other components in the formulation.

[0293] i) Water-soluble concentrates (SL, LS)

[0294] 10-60% by weight of at least one compound of the present invention and 5-15% by weight of a surfactant (e.g., a polycondensate of ethylene oxide and / or propylene oxide with alcohols) are dissolved in a corresponding amount of water and / or a water-soluble solvent (e.g., alcohols such as propylene glycol, and carbonates such as propylene carbonate) to obtain a total amount of 100% by weight. Before application, the concentrate is diluted with water.

[0295] ii) Dispersible Concentrate (DC)

[0296] 5-25 wt% of at least one compound of the present invention and 1-10 wt% of a surfactant and / or binder (eg polyvinyl pyrrolidone) are dissolved in a corresponding amount of an organic solvent (eg cyclohexanone) to give a total amount of 100 wt%. The dispersion is diluted with water.

[0297] iii) Emulsifiable Concentrate (EC)

[0298] 15-70% by weight of at least one compound of the present invention and 5-10% by weight of a surfactant (e.g. a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a corresponding amount of a water-insoluble organic solvent (e.g. an aromatic hydrocarbon or a fatty acid amide), and if necessary, a water-soluble solvent is added to give a total amount of 100% by weight. The emulsion is obtained by diluting with water.

[0299] iv) Emulsions (EW, EO, ES)

[0300] 5-40% by weight of at least one compound of the present invention and 1-10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate, a polycondensate of ethylene oxide and / or propylene oxide with or without alcohols) are dissolved in 20-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbons). The mixture is added to a corresponding amount of water using an emulsifier to obtain a total amount of 100% by weight. The resulting preparation is a uniform emulsion. Prior to application, the emulsion may be further diluted with water.

[0301] v) Suspension concentrates and suspension concentrates

[0302] v-1) Water-based (SC, FS)

[0303] In a suitable mill (e.g. a ball mill), 20-60% by weight of at least one compound of the invention is crushed with 2-10% by weight of a surfactant (e.g. sodium lignin sulfonate and polyoxyethylene fatty alcohol ether) added, 0.1-2% by weight of a thickener (e.g. xanthan gum) and water to obtain a fine active ingredient suspension. Water is added in a corresponding amount to give a total amount of 100% by weight. Dilution with water gives a stable suspension of the active ingredient. For FS-type preparations, up to 40% by weight of a binder (e.g. polyvinyl alcohol) is added.

[0304] v-2) Oil-based (OD, OF)

[0305] In a suitable mill (e.g. a ball mill), 20-60% by weight of at least one compound of the invention is pulverized with 2-10% by weight of a surfactant (e.g. sodium lignin sulfonate and polyoxyethylene fatty alcohol ether) added, 0.1-2% by weight of a thickener (e.g. modified clay, in particular bentone or silica) and an organic carrier to obtain a fine active ingredient / oil suspension. The organic carrier is added in a corresponding amount to give a total amount of 100% by weight. Dilution with water gives a stable dispersion of the active ingredient.

[0306] vi) Water dispersible granules and water soluble granules (WG, SG)

[0307] 1-90% by weight, preferably 20-80% by weight, most preferably 50-80% by weight of at least one compound according to the invention is finely ground with added surfactants (e.g. sodium lignin sulfonate and sodium alkylnaphthalene sulfonate) and optionally carrier materials and converted into water-dispersible or water-soluble granules by typical industrial methods (e.g. extrusion, spray drying, fluidized bed granulation). Surfactants and carrier materials are used in corresponding amounts to give a total amount of 100% by weight. Dilution with water gives a stable dispersion or solution of the active ingredient.

[0308] vii) Water dispersible powders and water soluble powders (WP, SP, WS)

[0309] In a rotor / stator mill, 50-80% by weight of at least one compound of the invention is ground with 1-20% by weight of a surfactant (e.g. sodium lignin sulfonate, sodium alkylnaphthalene sulfonate) added and a corresponding amount of a solid carrier (e.g. silica gel) to give a total amount of 100% by weight. Dilution with water gives a stable dispersion or solution of the active ingredient.

[0310] viii) Gel (GW, GF)

[0311] In a ball mill, 5-25% by weight of at least one compound according to the invention are comminuted with 3-10% by weight of a surfactant (e.g. sodium lignin sulfonate) added, 1-5% by weight of a binder (e.g. carboxymethylcellulose) and the corresponding amount of water to give a total amount of 100% by weight. This gives a fine suspension of the active ingredient. Dilution with water gives a stable suspension of the active ingredient.

[0312] ix) Microemulsion (ME)

[0313] 5-20% by weight of at least one compound of the present invention is added to 5-30% by weight of an organic solvent mixture (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant mixture (e.g., polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and a corresponding amount of water to give a total amount of 100% by weight. The mixture is stirred for 1 hour to give a spontaneously generated thermodynamically stable microemulsion.

[0314] x) Microcapsules (CS)

[0315] An oil phase comprising 5-50% by weight of at least one compound according to the invention, 0-40% by weight of a water-insoluble organic solvent (e.g. aromatic hydrocarbons), 2-15% by weight of acrylic monomers (e.g. methyl methacrylate, methacrylic acid and diacrylates or triacrylates) is dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator leads to the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of at least one compound according to the invention, 0-40% by weight of a water-insoluble organic solvent (e.g. aromatic hydrocarbons) and isocyanate monomers (e.g. diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol), which leads to the formation of polyurea microcapsules. If appropriate, polyamines (e.g. hexamethylenediamine) can also be added to induce the formation of polyurea microcapsules. The amount of monomers is 1-10% by weight, based on the weight of the total CS formulation.

[0316] xi) Powders (DP, DS)

[0317] 1 to 10% by weight of at least one compound according to the invention are ground finely and intimately mixed with a corresponding amount of solid carrier (eg finely divided kaolin) to give a total amount of 100% by weight.

[0318] xii) Granules (GR, FG)

[0319] 0.5 to 30% by weight of at least one compound according to the invention are ground finely and combined with a corresponding amount of a solid carrier (eg silicate) to give a total amount of 100% by weight.

[0320] xiii) Ultra Low Volume Liquid (UL)

[0321] 1 to 50% by weight of at least one compound according to the invention is dissolved in a corresponding amount of an organic solvent (eg an aromatic hydrocarbon) to give a total amount of 100% by weight.

[0322] Formulation types i) to xiii) may comprise further auxiliaries, for example 0.1 to 1% by weight of preservatives, 0.1 to 1% by weight of antifoams, 0.1 to 1% by weight of dyes and / or pigments and 5 to 10% by weight of antifreeze agents.

[0323] mixture

[0324] The compounds of formula (I) can also be used with a mixture of one or more suitable following substances: fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microorganisms, beneficial organisms, herbicides, fertilizers, bird repellents, phytotoxins (phytotonic), sterilizers, safeners, chemical semiochemicals and / or plant growth regulators, thereby, for example, widening the spectrum of action, prolonging the duration of action, increasing the rate of action, preventing repulsion or preventing the development of resistance. In addition, such active ingredient combinations can improve plant growth and / or tolerance to abiotic factors, such as tolerance to high or low temperatures, to drought or to high water content or soil salinity. It is also possible to improve flowering and fruiting performance, optimize germination ability and root development, promote harvesting and increase yield, affect ripening, improve the quality and / or nutritional value of harvested products, prolong storage period and / or improve the processability of harvested products.

[0325] In addition, the compounds of formula (I) may be mixed with other active ingredients or semiochemicals such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Similarly, the compounds of formula (I) can be used to improve plant performance such as growth, yield and quality of harvested material.

[0326] In a particular embodiment of the invention, the compounds of the formula (I) are present in a mixture with other compounds, preferably those mentioned below, in the formulations or in the use forms prepared from these formulations.

[0327] If one of the compounds mentioned below can exist in different tautomeric forms, these are also included, even if not explicitly mentioned in the individual case. If appropriate, all the mixing components mentioned can also form salts with suitable bases or acids if they are capable of forming salts based on their functional groups.

[0328] Insecticides / Acaricides / Nematicides

[0329] The active ingredients referred to herein by their common names are known and are described, for example, in "The Pesticide Manual", 16th edition, British Crop Protection Council 2012, or can be retrieved on the Internet (e.g. http: / / www.alanwood.net / pesticides). The classification is based on the IRAC mode of action classification scheme applicable at the time of filing this patent application.

[0330] (1) an acetylcholinesterase (AChE) inhibitor, preferably a carbamate selected from the following group: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furath iocarb), isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or an organophosphate selected from the group consisting of acephate, azamethiphos , azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chloropyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos ophos), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, methyl pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

[0331] (2) GABA-gated chloride channel blockers, preferably cyclopentadienyl organochlorines selected from chlordane and endosulfan; or phenylpyrazoles (fiproles) selected from ethiprole and fipronil.

[0332] (3) Sodium channel modulators, preferably selected from the following pyrethroids: acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, isomer), bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer] isomers]), deltamethrin, empenthrin [(EZ)-(1R) isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans]isomer]), prallethrin, pyrethrine (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomers], tralomethrin and transfluthrin; or DDT; or methoxychlor.

[0333] (4) A competitive modulator of nicotinic acetylcholine receptor (nAChR), preferably selected from the following neonicotinoids: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or nicotine; or sulfoximines selected from sulfoxaflor; or butenolides selected from flupyradifurone; or mesoionics selected from triflumezopyrim.

[0334] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, preferably spinosyns selected from spinetoram and spinosad.

[0335] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, preferably selected from the following avermectins / milbemycins: abamectin, emamectin benzoate, lepimectin and milbemectin.

[0336] (7) Juvenile hormone mimetics, preferably selected from the following juvenile hormone analogs: hydroprene, kinoprene and methoprene; or fenoxycarb; or pyriproxyfen.

[0337] (8) Other non-specific (multi-site) inhibitors, preferably alkyl halides selected from the following: methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic; or methyl isocyanate generators selected from diazomet or metam.

[0338] (9) TRPV channel modulators of the chordotonal organ, preferably pyridyl azomethanes selected from pymetrozine and pyrifluquinazon, or pyropenes selected from afidopyropen.

[0339] (10) A mite growth inhibitor related to CHS1 selected from clofentezine, hexythiazox, diflovidazin and etoxazole.

[0340] (11) A microbial disruptor of the insect midgut membrane, which is selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and a Bt plant protein selected from the following: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1.

[0341] (12) Inhibitors of mitochondrial ATP synthase, preferably selected from the following ATP disruptors: diafenthiuron, or an organotin compound selected from azoxatin, cyclohexidine and fenbutatin oxide, or propargite or tetradifon.

[0342] (13) An uncoupler of oxidative phosphorylation by blocking the proton gradient, selected from chlorfenapyr, dinitrocresol (DNOC) and sulphluramid.

[0343] (14) A nicotinic acetylcholine receptor channel blocker selected from the group consisting of bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0344] (15) A chitin biosynthesis inhibitor related to CHS1, preferably a benzyl urea selected from bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0345] (16) Chitin biosynthesis inhibitors, type 1, selected from buprofezin.

[0346] (17) Molting disruptors (especially for Diptera) selected from cyromazine.

[0347] (18) An ecdysone receptor agonist, preferably a diacylhydrazine selected from the group consisting of chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0348] (19) An octopamine receptor agonist selected from amitraz.

[0349] (20) A mitochondrial complex III electron transport inhibitor selected from the group consisting of hydramethylnone, acequinocyl, fluacrypyrim and bifenazate.

[0350] (21) Mitochondrial complex I electron transport inhibitors, preferably METI miticides and insecticides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or rotenone (Derris).

[0351] (22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone.

[0352] (23) Inhibitors of acetyl CoA carboxylase, preferably tetronic acid and tetramic acid derivatives selected from spirodiclofen, spiromesifen, spiropidion and spirotetramat.

[0353] (24) Mitochondrial complex IV electron transport inhibitors, preferably selected from the following phosphines: aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or selected from the following cyanides: calcium cyanide, potassium cyanide and sodium cyanide.

[0354] (25) Mitochondrial complex II electron transport inhibitors, preferably β-ketonitrile derivatives selected from the group consisting of cyenopyrafen and cyflumetofen, or carboxanilides selected from the group consisting of pyflubumide.

[0355] (28) nicotinic acid receptor modulators, preferably diamides selected from the group consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide and tetraniliprole;

[0356] (29) A chord organ modulator (with an undefined target structure) selected from flonicamid.

[0357] (30) An allosteric modulator of a GABA-gated chloride channel, preferably an isoxazole selected from the group consisting of broflanilide and fluxametamide.

[0358] (31) Baculoviruses, preferably granuloviruses (GVs) selected from the group consisting of Cydiapomonella GV and Thaumatotibia leucotreta GV; or nuclear polyhedrosis viruses (NPVs) selected from the group consisting of Anticarsia gemmatalis MNPV and Helicoverpa armigera NPV.

[0359] (32) An allosteric modulator of the nicotinic acetylcholine receptor (site II) selected from the group consisting of GS-omega / kappa-HXTX-Hv1a peptides.

[0360] (33) Other active ingredients selected from the group consisting of acynonapyr, afoxolaner, azadirachtin, benclothiaz, benzoximat, benzpyrimoxan, bromopropylate, chinomethionat, chloroprallethrin, cryolite, cyclobutrifluram, cycloxaprid, cyetpyrafen, cyhalodiamide, cyproflanilide (CAS 2375110-88-4), dicloromezotiaz, dicofol, dimpropyridaz, epsilon-metofluthrin, epsilon-momfluthrin, flometoquin, fluazaindolizine, flucypyriprol (CAS 1771741-86-6), fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, flupyrimin, fluralaner, fufenozide, flupentiofenox, guadipyr, heptafluthrin, imidaclothiz, iprodione, isocycloseram, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, nicofluprole (CAS1771741-86-6), oxazosulfyl, paichongding, pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner, spidoxamat, spirobudiclofen, tetramethylfluthrin, tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, tyclopyrazoflor, iodomethane; and Bacillus firmus-based firmus) (I-1582, Votivo) and azadirachtin (BioNeem), and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (known from EP 2647626) (CAS-1440516-42-6), PF1364 (known from JP2010 / 018586) (CAS 1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one (known from WO2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide (known from WO 2013 / 050317 A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US 2014 / 0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN103109816 A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012 / 034403 A1) (CAS1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylic acid 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-pyranose (known from US 2014 / 0275503 A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (known from WO2007040280 A1, WO 2007040282 A1) (CAS934001-66-8), N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from CN103265527 A) (CAS 1452877-50-7), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO 2014 / 187846 A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylcarboxylic acid ethyl ester (known from WO 2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-(2,6-difluorophenyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014 / 053450 A1) (CAS 1594624-87-9), N-[2-(2,6-difluorophenyl)-2H-1,2,3-triazol-4-yl]-2-(trifluoromethyl)benzamide (known from WO 2014 / 053450 A1) (CAS 1594637-65-6), N-[1-(3,5-difluoro-2-pyridyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014 / 053450 A1) (CAS 1594626-19-3), (3R)-3-(2-chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium internal salt (known from WO 2018 / 177970 A1) (CAS 2246757-58-2); 3-(2-chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium internal salt (known from WO 2018 / 177970 A1) (CAS 2246757-56-0); N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)propionamide (known from WO 2019 / 236274 A1) (CAS 2396747-83-2), N-[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzoyl)amino]benzamide (known from WO2019059412 A1) (CAS 1207977-87-4).

[0361] Fungicides

[0362] The active ingredients referred to herein by their common names are known and are described, for example, in the “Pesticide Handbook” (16th edition, British Crop Protection Council) or can be retrieved on the Internet (eg: www.alanwood.net / pesticides).

[0363] All the mixing partners mentioned in classes (1) to (15) can optionally form salts with suitable bases or acids if they are capable of forming salts based on their functional groups. All the fungicidal mixing partners mentioned in classes (1) to (15) can optionally include tautomeric forms.

[0364] 1) Inhibitors of ergosterol biosynthesis, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamin, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate sulfate), (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyraclostrobin pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.02 7) (1S, 2R, 5R) -5- (4-chlorobenzyl) -2- (chloromethyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol, (1.028) (2R) -2- (1-chlorocyclopropyl) -4- [(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.029) (2R) -2- (1-chlorocyclopropyl) -4- [(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazol-1-yl) butan-2-ol, (1.030) (2R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1 H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro- 2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione 4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) mefenthrin ifluconazole), (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3 -thioketone, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylthio)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylthio)-1-{[rel(2R,3S)-3-(2 -chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)thio]phenoxy}phenyl)-N-ethyl N-(4-{[3-(difluoromethoxy)phenyl]thio}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, (1.073) N'-(4-{3-[(difluoromethyl)thio]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyliminocarboxamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3 -yl}-N-ethyl-N-methyliminocarboxamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.081) ipfentrifluconazole, (1.082) 1-(1.084) 1-(1.086) 1-(1.087) 1-(1.088) 1-(1.090) 1-(1.091) 1-(1.093) 1-(1.094) 1-(1.095) 1-(1.096) 1-(1.097) 1-(1.098) 1-(1.099) 1-(1.091 ...9) 1-(1.091) 1-(1.093) 1-(1.094) 1-(1.095) 1-(1.096) 1-(1.097) 1-(1.098)082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and (1.086) 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzenecarbonitrile. .

[0365] 2) Respiratory chain inhibitors acting on complex I or II, such as (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) isofetamid, (2.010) pyrimidine Isopyrazam (trans epimeric enantiomers 1R, 4S, 9S), (2.011) isopyrazam (trans epimeric enantiomers 1S, 4R, 9R), (2.012) isopyrazam (trans epimeric racemates 1RS, 4SR, 9SR), (2.013) isopyrazam (mixture of cis epimeric racemates 1RS, 4SR, 9RS and trans epimeric racemates 1RS, 4SR, 9SR), (2.014) isopyrazam (cis epimeric enantiomers 1R, 4S, 9R), (2.015) isopyrazam (cis epimeric enantiomers 1S, 4R, 9S), (2.016) isopyrazam (cis-diameric racemates 1RS, 4SR, 9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4 -yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) inpyrfluxam, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H -pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)- 1,2,3,4-tetrahydro-1,4-naphthyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxyprop-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide (Difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-thiocarboxamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide 1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide Amide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) pyrapropoyn. .

[0366] 3) Inhibitors of respiratory complex III, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxazole adon), (3.010) fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin strobin), (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[( 2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029)029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole, (3.031) florylpicoxamid. .

[0367] 4) Mitosis and cell division inhibitors, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl -5-phenylpyridazine, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H- Pyrazole-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine. .

[0368] 5) Compounds that can show multi-site effects, such as (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, oxychloride), (5.009) copper sulfate (2+), (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017) copper quinoline oxine), (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0369] 6) Compounds that can induce host defense responses, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, and (6.004) tiadinil.

[0370] 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[0371] 8) ATP production inhibitors, for example (8.001) silthiofam.

[0372] 9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0373] 10) Inhibitors of lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[0374] 11) Melanin biosynthesis inhibitors, for example, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

[0375] 12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl, (12.002) kiralaxyl, (12.003) metalaxyl, (12.004) mefenoxam.

[0376] 13) Signal transduction inhibitors, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

[0377] 14) Compounds that can act as uncouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.

[0378] 15) Other fungicides selected from (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) 009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate isothiocyanate), (15.016) metrafenon, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its salts, (15.025) Phosphoric acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032)032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) dipymetitrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone 1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, )-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) ipflufenoquin, (15.042 )2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043)fluoxapiprolin, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.044)fluoxapiprolin, (15.045)2-phenylphenol and its salts, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047)047) quinofumelin, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene 2-sulfonylhydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro -2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) {6-[({[(1-methyl -1H-tetrazolyl-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamic acid tert-butyl ester, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) aminopyrifen, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidocarboxamide), (15.065) (N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimidocarboxamide), (15.066) (2-{2-[(7,8-dihydrophenoxy)-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one fluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067) (5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068) (3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline), (15.069) (1-(4,5-dimethyl-1H-benzoimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15.070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.071) 8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.072) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.073) (N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide), (15.074) (methyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate), (15.075) (N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide amine), (15.076) N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.077) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.078) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.079) N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, (15.080) N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, (15.081) 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.082) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.083) N-[(E)-N-methoxy-C-methylcarboimido]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-methoxy-C-methylcarboimido]-4-[5-(trifluoromethyl)-1,2 ,4-oxadiazol-3-yl]benzamide, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropionamide, (15.090) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091) 1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.093) N-methoxy-N-[[4-[5- 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2 ,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, ( 15.102) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.104) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one, (15.106)106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.108) (1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one 4-oxadiazol-3-yl]benzyl}-1H-pyrazol-4-yl)ethyl acetate, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine and (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide.

[0379] Biopesticides as components of mixtures

[0380] The compounds of formula (I) may be combined with biopesticides.

[0381] Biopesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.

[0382] Biopesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that function as bioinsecticides, fungicides, or nematicides.

[0383] Examples of such bacteria which are or can be used as biopesticides are:

[0384] Bacillus amyloliquefaciens, strain FZB42 (DSM231179); or Bacillus cereus, in particular Bacillus cereus strain CNCM I-1562; or Bacillus firmus, strain I-1582 (accession number CNCM I-1582); or Bacillus pumilus, in particular strain GB34 (accession number ATCC 700814) and strain QST2808 (accession number NRRLB-30087); or Bacillus subtilis, in particular strain GB03 (accession number ATCC SD-1397); or Bacillus subtilis strain QST713 (accession number NRRL B-21661) or Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421); Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276); or Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372); or Bacillus thuringiensis subsp. kurstaki strain HD-1; or Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428); Pasteuria penetrans; Pasteuria spp. spp.) (Rotylenchulus reniformis nematode)-PR3 (Accession No. ATCC SD-5834); Streptomyces microflavus strain AQ6121 (=QRD31.013, NRRL B-50550); Streptomyces galbus strain AQ 6047 (Accession No. NRRL 30232).

[0385] Examples of fungi and yeasts that are or can be used as biopesticides are:

[0386] Beauveria bassiana, in particular strain ATCC 74040; Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM-9660); Lecanicillium spp., in particular strain HRO LEC12; Lecanicillium lecanii, (formerly Verticillium lecanii), in particular strain KV01; Metarhizium anisopliae, in particular strain F52 (DSM 3884 / ATCC 90448); Metschnikowia fructicola, in particular strain NRRL Y-30752; Paecilomyces fumosoroseus (now known as Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (accession number ATCC 20874); Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89 / 030550); Talaromyces flavus, in particular strain V117b; Trichoderma atroviride, in particular strain SC1 (accession number CBS 122089); Trichoderma harzianum, in particular T. harzianum rifai T39 (accession number CNCM I-952).

[0387] Examples of viruses that are or can be used as biopesticides are:

[0388] Adoxophyes orana (summer fruit tortrix) granulovirus (GV), Cydia pomonella (codling moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm)) mNPV, Spodoptera littoralis (African cotton leafworm)) NPV.

[0389] Also included are bacteria and fungi that are added to plants or plant parts or plant organs as "inoculants" which, through their specific properties, promote plant growth and plant health.

[0390] Examples include:

[0391] Agrobacterium spp.; Azorhizobium caulinodans; Azospirillum spp.; Azotobacter spp.; Bradyrhizobium spp.; Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia); Gigaspora spp.; or Gigaspora monosporum; Glomus spp.; Laccaria spp.; Lactobacillus buchneri; Paraglomus spp.; Pisolithus tinctorus; Pseudomonas spp.; Rhizobium spp., in particular Rhizobium trifolii; Rhizopogon spp.; Scleroderma spp.; Suillus spp.; Streptomyces spp.

[0392] Examples of plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that are or can be used as biopesticides are:

[0393] Garlic (Allium sativum); Wormwood (Artemisia absinthium); Azadirachtin; Biokeeper WP; Cassia nigricans; Celastrus angulatus; Chenopodium anhelminticum; Chitin; Armour-Zen; Dryopteris filix-mas; Equisetum arvense; Fortune Aza; Fungastop; Heads Up (Chenopodium quinoa saponin extract); Pyrethrum / pyrethrins; Quassia amara; Quercus; Quillaja; Regalia; "RequiemTM "insecticides"; rotenone; ryanodine / ryanodine; Symphytum officinale; Tanacetum vulgare; thymol; Triact 70; TriCon; Tropaeulum majus; Urtica dioica; Veratrin; Viscumalbum; extracts of the Brassicaceae family, in particular rapeseed powder or mustard powder; and biological insecticidal / acaricidal active ingredients obtained from olive oil, in particular with C 16 -C 20 Unsaturated fatty acids / carboxylic acids with carbon chain lengths are used as active ingredients, for example in products sold under the trade name products.

[0394] Safener as a component of a mixture

[0395] The compounds of formula (I) may be combined with safeners such as benoxacor, cloquintocet(-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole(-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen(-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-{4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

[0396] Plants and plant parts

[0397] All plants and plant parts can be processed according to the present invention. Plants are understood to mean all plants and plant populations in this article, such as expected and undesirable wild plants or crop plants (including naturally occurring crop plants), such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybean, potato, sugar beet, sugar cane, tomato, sweet pepper, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (such as cabbage) and other vegetable varieties, cotton, tobacco, rapeseed, and fruit plants (fruit is apple, pear, citrus fruit and grape). Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnology methods and genetic engineering methods or the combination of these methods, including transgenic plants and plant cultivars that can or may not be protected by plant breeders' rights. Plants are understood to mean all developmental stages, such as seeds, seedlings, early (immature) plants until and including mature plants. Plant parts are understood to mean all parts and organs of the plant above and below the ground, such as buds, leaves, flowers and roots, examples being leaves, needles, stems, branches, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. Plant parts also include harvested plants or harvested plant parts and material for asexual and sexual propagation, such as cuttings, tubers, rhizomes, slips and seeds.

[0398] The treatment of plants and plant parts with the compounds of formula (I) according to the invention is carried out directly by conventional treatment methods or by allowing the compounds to act on their environment, habitat or storage space, for example by dipping, spraying, evaporation, atomization, broadcasting, painting, injection and, in the case of propagation materials (especially seeds), also by applying one or more coatings.

[0399] As described above, all plants and their parts can be treated according to the present invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods (such as hybridization or protoplast fusion) and their parts are treated. In another preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate, in combination with conventional methods (genetically modified organisms), and their parts are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above. It is particularly preferred to treat plants of each commercially available conventional plant cultivar or those plants that are being used according to the present invention. Plant cultivars are understood to mean plants with new properties ("traits") and obtained by conventional breeding, by mutagenesis or by recombinant DNA technology. They can be cultivars, variants, biotypes or genotypes.

[0400] Transgenic plants, seed treatments and integration events

[0401] According to the present invention, the compound of formula (I) can be advantageously used to treat transgenic plants, plant cultivars or plant parts that have received genetic material, which respectively impart favorable and / or useful properties (traits) to these plants, plant cultivars or plant parts. Therefore, one option is to combine the present invention with one or more recombinant traits or transgenic strains (transgenic event) or a combination thereof. For the purpose of this application, transgenic strains are produced by inserting specific recombinant DNA molecules into specific locations (sites) of plant genome chromosomes. The insertion creates a new DNA sequence called a "strain", which is characterized in that the inserted recombinant DNA molecules and a certain amount of genomic DNA are directly adjacent to the two ends of the inserted DNA / side by the two ends of the inserted DNA. This trait or transgenic strain includes, but is not limited to, resistance to pests and diseases, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production and herbicide tolerance, wherein the trait is determined relative to plants lacking this trait or transgenic strain. Specific examples of such advantageous and / or useful properties (traits) are better plant growth, vigor, stress tolerance, stability, lodging resistance, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated ripening, higher yield, higher quality and / or higher nutritional value of the harvested product, better storage life and / or processability of the harvested product, and increased resistance to animal or microbial pests (for example against insects, arachnids, nematodes, mites, slugs and snails).

[0402] Among the DNA sequences encoding proteins which confer tolerance or resistance traits on these animal or microbial pests, in particular insects, mention will be made in particular of the genetic material consisting of Bacillus thuringiensis encoding the Bt protein, which is well described in the literature and is well known to those skilled in the art. Mention will also be made of proteins extracted from bacteria, such as Photorhabdus (WO 97 / 17432 and WO 98 / 08932). In particular, mention will be made of the genetic material consisting of Bacillus thuringiensis encoding the Bt protein, which is well described in the literature and is well known to those skilled in the art. Mention will also be made of proteins extracted from bacteria, such as Photorhabdus (WO 97 / 17432 and WO 98 / 08932). Cry or VIP proteins including Cry1A, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof, and hybrids or combinations thereof, in particular Cry1F protein or hybrids derived from Cry1F protein (such as hybrid Cry1A-Cry1F protein or toxic fragments thereof), Cry1A-type protein or toxic fragments thereof, preferably Cry1Ac protein or hybrids derived from Cry1Ac protein (such as hybrid Cry1Ab-Cry1Ac protein) or Cry1Ab or Bt2 protein or toxic fragments thereof, Cry2Ae, Cry2Af or Cry2Ag protein or toxic fragments thereof, Cry1A.105 protein or toxic fragments thereof, VIP3Aa19 protein, VIP3Aa20 protein, VIP3A protein produced in COT202 or COT203 cotton strains, as described in Estruch et al. (1996), Proc Natl Acad Sci US A.28; 93 (11): 5389-94 or a toxic fragment thereof, a Cry protein described in WO2001 / 47952, an insecticidal protein from Xenorhabdus (such as described in WO98 / 50427), Serratia (especially from S. entomophila) or a Photorhabdus species strain, such as the Tc protein from Photorhabdus described in WO98 / 08932. In addition, the present invention also includes all variants or mutants of any of the above proteins that differ from any of the above-listed sequences (especially the sequences of their toxic fragments) in some amino acids (1-10, preferably 1-5), or any variant or mutant of the above proteins fused with a transit peptide (such as a plastid transit peptide) or another protein or peptide.

[0403] Another and particularly emphasized example of such a property is the conferring of tolerance to one or more herbicides, such as imidazolinones, sulfonylureas, glyphosate or glufosinate. Among the DNA sequences encoding proteins that confer tolerance to certain herbicides on transformed plant cells and plants, the bar or PAT genes or the Streptomyces coelicolor genes described in WO 2009 / 152359 that confer tolerance to glufosinate herbicides, suitable EPSPS (5-enolpyruvylshikimate-3-phosphate-synthase) genes encoding tolerance to herbicides targeting EPSPS, in particular to herbicides such as glyphosate and its salts, genes encoding glyphosate N-acetyltransferase, or genes encoding glyphosate oxidoreductase, will be mentioned in particular. Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., WO2007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g., U.S. Pat. No. 6,855,533), a gene encoding a 2,4-D-monooxygenase conferring tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), a gene encoding a dicamba monooxygenase conferring tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).

[0404] Further and particularly emphasized examples of such traits are increased resistance to bacteria and / or viruses due to, for example, systemic acquired resistance (SAR), systemin, phytoalexins, inducers and resistance genes and correspondingly expressed proteins and toxins.

[0405] Particularly useful transgenic lines among the transgenic plants or plant cultivars that can be preferentially treated according to the present invention include line 531 / PV-GHBK04 (cotton, insect control, described in WO2002 / 040677), line 1143-14A (cotton, insect control, not deposited, described in WO2006 / 128569); line 1143-51B (cotton, insect control, not deposited, described in WO2006 / 128570); line 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO2002 / 034946); Line 17053 (rice, herbicide tolerant, deposited as PTA-9843, described in WO2010 / 117737); Line 17314 (rice, herbicide tolerant, deposited as PTA-9844, described in WO2010 / 117735); Line 281-24-236 (cotton, insect control-herbicide tolerant, deposited as PTA-6233, described in WO2005 / 103266 or US-A2005-216969); Line 3006-210-23 (cotton, insect control-herbicide tolerant, deposited as PTA-6233, described in US-A 2007-143876 or WO2005 / 103266); Line 3272 (maize, quality traits, deposited as PTA-9972, described in WO2006 / 098952 or US-A 2006-230473); Line 33391 (wheat, herbicide tolerance, deposited as PTA-2347, described in WO2002 / 027004), Line 40416 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-11508, described in WO 11 / 075593); Line 43A47 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-11509 deposited and described in WO2011 / 075595); Line 5307 (corn, insect control, deposited as ATCC PTA-9561, described in WO2010 / 077816); Line ASR-368 (bent grass, herbicide tolerant, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO2004 / 053062); Line B16 (corn, herbicide tolerant, not deposited, described in US-A 2003-126634); line BPS-CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No. 41603, described in WO2010 / 080829); line BLR1 (rapeseed, restored male sterility, deposited as NCIMB No. 41193, described in WO2005 / 074671), line CE43-67B (cotton,insect control, deposited as DSMACC2724, described in US-A 2009-217423 or WO2006 / 128573); strain CE44-69D (cotton, insect control, not deposited, described in US-A 2010-0024077); strain CE44-69D (cotton, insect control, not deposited, described in WO2006 / 128571); strain CE46-02A (cotton, insect control, not deposited, described in WO2006 / 128572); strain COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004 / 039986); strain COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005 / 054479); line COT203 (cotton, insect control, not deposited, described in WO2005 / 054480); line DAS21606-3 / 1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO2012 / 033794), line DAS40278 (corn, herbicide tolerance, deposited as ATCC PTA-10244 deposited, described in WO2011 / 022469); line DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, deposited as PTA-11336, described in WO2012 / 075426), line DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide tolerance, deposited as PTA-11335, described in WO2012 / 075429), line DAS-59122-7 (corn, insect control-herbicide tolerance, deposited as ATCC PTA 11384, described in US-A 2006-070139); line DAS-59132 (corn, insect control-herbicide tolerance, not deposited, described in WO2009 / 100188); line DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO2011 / 066384 or WO2011 / 066360); line DP-098140-6 (corn, herbicide tolerance, deposited as ATCC PTA-8296, described in US-A 2009-137395 or WO 08 / 112019); line DP-305423-1 (soybean, quality traits, not deposited, described in US-A 2008-312082 or WO2008 / 054747); strain DP-32138-1 (maize, hybrid system, deposited as ATCC PTA-9158,09-0210970 or WO2009 / 103049); line DP-356043-5 (soybean, herbicide tolerant, deposited as ATCC PTA-8287, described in US-A 2010-0184079 or WO2008 / 002872); line EE-I (eggplant, insect control, not deposited, described in WO 07 / 091277); line Fil17 (maize, herbicide tolerant, deposited as ATCC 209031, described in US-A 2006-059581 or WO 98 / 044140); line FG72 (soybean, herbicide tolerant, deposited as PTA-11041, described in WO2011 / 063413), line GA21 (maize, herbicide tolerant, deposited as ATCC 209033, described in US-A 2005-086719 or WO 98 / 044140); line GG25 (maize, herbicide tolerant, deposited as ATCC 209032, described in US-A 2005-188434 or WO 98 / 044140); line GHB119 (cotton, insect control-herbicide tolerant, deposited as ATCC PTA-8398, described in WO2008 / 151780); line GHB614 (cotton, herbicide tolerant, deposited as ATCC PTA-6878 deposited, described in US-A 2010-050282 or WO 2007 / 017186); line GJ11 (maize, herbicide tolerant, deposited as ATCC 209030, described in US-A 2005-188434 or WO 98 / 044140); line GM RZ13 (sugar beet, virus resistant, deposited as NCIMB-41601, described in WO 2010 / 076212); line H7-1 (sugar beet, herbicide tolerant, deposited as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004 / 074492); line JOPLIN1 (wheat, disease resistant, not deposited, described in US-A 2008-064032); line LL27 (soybean, herbicide tolerant, deposited as NCIMB 41658, described in WO 2006 / 108674 or US-A 2008-320616); line LL55 (soybean, herbicide tolerant, deposited as NCIMB 41660, described in WO 2006 / 108675 or US-A 2008-196127); line LLcotton25 (cotton, herbicide tolerant, deposited as ATCC PTA-3343, described in2003 / 013224 or US A2003-097687); line LLRICE06 (rice, herbicide tolerance, deposited as ATCC 203353, described in US 6,468,747 or WO2000 / 026345); line LLRICE62 (rice, herbicide tolerance, deposited as ATCC 203352, described in WO2000 / 026345), line LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A2008-2289060 or WO2000 / 026356); line LY038 (maize, quality traits, deposited as ATCC PTA-5623, described in US-A 2007-028322 or WO2005 / 061720); line MIR162 (corn, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO2007 / 142840); line MIR604 (corn, insect control, not deposited, described in US-A 2008-167456 or WO2005 / 103301); line MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US-A 2004-250317 or WO2002 / 100163); line MON810 (corn, insect control, not deposited, described in US-A 2002-102582); line MON863 (maize, insect control, deposited as ATCC PTA-2605, described in WO2004 / 011601 or US-A 2006-095986); line MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in WO2011 / 062904); line MON87460 (maize, stress resistance, deposited as ATCC PTA-8910, described in WO2009 / 111263 or US-A 2011-0138504); line MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A 2009-130071 or WO2009 / 064652); line MON87705 (soybean, quality trait - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A 2010-0080887 or WO2010 / 037016); line MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011 / 034704); line MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012 / 051199),Strain MON87754 (soybean, quality traits, deposited as ATCC PTA-9385, described in WO2010 / 024976); Strain MON87769 (soybean, quality traits, deposited as ATCC PTA-8911, described in US-A 2011-0067141 or WO2009 / 102873); Strain MON88017 (corn, insect control-herbicide tolerance, deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO2005 / 059103); Strain MON88913 (cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in WO2004 / 072235 or US-A 2006-059590); line MON88302 (rapeseed, herbicide tolerant, deposited as PTA-10955, described in WO2011 / 153186), line MON88701 (cotton, herbicide tolerant, deposited as PTA-11754, described in WO2012 / 134808), line MON89034 (corn, insect control, deposited as ATCC PTA-7455, described in WO 07 / 140256 or US-A 2008-260932); line MON89788 (soybean, herbicide tolerant, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO2006 / 130436); line MS1 1 (canola, pollination control-herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO2001 / 031042); line MS8 (canola, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); line NK603 (maize, herbicide tolerance, deposited as ATCC PTA-2478, described in US-A 2007-292854); line PE-7 (rice, insect control, not deposited, described in WO2008 / 114282); line RF3 (canola, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO2001 / 041558 or US-A 2003-188347); line RT73 (rapeseed, herbicide tolerant, not deposited, described in WO2002 / 036831 or US-A 2008-070260); line SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerant, deposited as PTA-11226, described in WO2012 / 082548), line T227-1 (sugar beet, herbicide tolerant, not deposited,2002 / 44407 or US-A 2009-265817); line T25 (corn, herbicide tolerance, not deposited, described in US-A 2001-029014 or WO2001 / 051654); line T304-40 (cotton, insect control-herbicide tolerance, deposited as ATCC PTA-8171, described in US-A 2010-077501 or WO2008 / 122406); line T342-142 (cotton, insect control, not deposited, described in WO2006 / 128568); line TC1507 (corn, insect control-herbicide tolerance, not deposited, described in US-A 2005-039226 or WO2004 / 099447); line VIP1034 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-3925, described in WO2003 / 052073), line 32316 (maize, insect control-herbicide tolerance, deposited as PTA-11507, described in WO2011 / 084632), line 4114 (maize, insect control-herbicide tolerance, deposited as PTA-11506, described in WO2011 / 084621), optionally with line EE-GM1 / LL27 or line EE-GM2 / LL55 (WO2011 / 063413A2) stacked strain EE-GM3 / FG72 (soybean, herbicide tolerance, ATCC accession number PTA-11041), strain DAS-68416-4 (soybean, herbicide tolerance, ATCC accession number PTA-10442, WO2011 / 066360A1), strain DAS-68416-4 (soybean, herbicide tolerance, ATCC accession number PTA-10442, WO2011 / 066384 A1), line DP-040416-8 (corn, insect control, ATCC accession number PTA-11508, WO2011 / 075593A1), line DP-043A47-3 (corn, insect control, ATCC accession number PTA-11509, WO2011 / 075595A1), line DP-004114-3 (corn, insect control, ATCC accession number PTA-11506, WO2011 / 084621A1) , strain DP-032316-8 (corn, insect control, ATCC accession number PTA-11507, WO2011 / 084632A1), strain MON-88302-9 (rapeseed, herbicide tolerance, ATCC accession number PTA-10955, WO2011 / 153186A1), strain DAS-21606-3 (soybean, herbicide tolerance, ATCC accession number PTA-11028, WO2012 / 033794A2),Line MON-87712-4 (soybean, quality traits, ATCC Accession No. PTA-10296, WO2012 / 051199A2), Line DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11336, WO2012 / 075426A1), Line DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11335, WO2012 / 075429 A1), line SYN-000H2-5 (soybean, herbicide tolerance, ATCC accession number PTA-11226, WO2012 / 082548A2), line DP-061061-7 (rapeseed, herbicide tolerance, no available deposit number, WO2012071039A1), line DP-073496-4 (rapeseed, herbicide tolerance, no available deposit number, US2012131692), line 8264.44.06.1 (soybean, superimposed herbicide herbicide tolerance, registration number PTA-11336, WO2012075426A2), line 8291.45.36.2 (soybean, stacked herbicide tolerance, registration number PTA-11335, WO2012075429A2), line SYHT0H2 (soybean, ATCC registration number PTA-11226, WO2012 / 082548A2), line MON88701 (cotton, ATCC registration number PTA-11754, WO2012075429A2). 12 / 134808A1), strain KK179-2 (alfalfa, ATCC accession number PTA-11833, WO2013 / 003558A1), strain pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC accession number PTA-11993, WO2013 / 010094A1), strain MZDT09Y (corn, ATCC accession number PTA-13025, WO2013 / 012775A1). ,

[0406] In addition, the United States Department of Agriculture (USDA) Animal and Plant Health Inspection Service (APHIS) provides a list of such transgenic lines which can be found on the Internet at their website aphis.usda.gov. For the purposes of this application, this list is relevant as of the filing date of this application.

[0407] In transgenic plants, genes / lines conferring the desired traits may also be present in combination with one another. Examples of transgenic plants that may be mentioned include important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetable species, cotton, tobacco, rapeseed and fruit plants (fruits are apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed. Traits that should be particularly emphasized are increased resistance of the plants to insects, arachnids, nematodes and slugs and snails, and increased resistance of the plants to one or more herbicides.

[0408] Commercially available examples of such plants, plant parts or plant seeds which can preferably be treated according to the invention include RIB ROUNDUP VT DOUBLE VT TRIPLE BOLLGARD ROUNDUP READY 2 ROUNDUP 2XTEN DTM 、INTACTA RR2 VISTIVE and / or XTENDFLEX TM A commercially available product, such as plant seeds, sold or distributed under a trade name.

[0409] Crop protection – types of treatments

[0410] Plants and plant parts are treated with the compounds of formula (I) directly or by acting on their environment, habitat or storage space using customary treatment methods, such as dipping, spraying, atomizing, irrigation, evaporation, dusting, misting, broadcasting, foaming, smearing, spreading, injection, watering (irrigation), drip irrigation, and in the case of propagation materials (especially seeds), also by dry seed treatment, wet seed treatment, slurry treatment, crusting, by coating with one or more coatings, etc. It is also possible to apply the compounds of formula (I) by the ultra-low volume method or to inject the use forms or the compounds of formula (I) themselves into the soil.

[0411] A preferred direct treatment of plants is foliar application, ie application of the compounds of formula (I) to the leaves, in which case the frequency of treatment and the application rate should be adjusted to the level of infestation of the pest in question.

[0412] In the case of systemically active ingredients, the compounds of formula (I) also enter the plant via the root system. The plant is then treated by applying the compound of formula (I) to the plant's habitat. This can be done in the following ways: for example, by watering; or by mixing into the soil or nutrient solution, which means that the plant's growing place (e.g., soil or hydroponic system) is impregnated with the compound of formula (I) in liquid form; or by soil application, which means that the compound of formula (I) of the present invention is introduced into the plant's growing place in solid form (e.g., in the form of granules); or by drip irrigation application (often also referred to as "chemical irrigation"), which means that the compound of formula (I) of the present invention is introduced into a specified position near the plant through a ground or underground drip irrigation pipe over a certain period of time together with different amounts of water. In the case of rice crops, this can also be done by metering the compound of formula (I) into the rice field in a solid application form (e.g., as granules).

[0413] Digital Technology

[0414] The compositions of the invention can be used in combination with models, such as those embedded in computer programs, for site-specific crop plant management, satellite agriculture, precision farming or precision agriculture. These models support site-specific management of agricultural sites using data from a variety of sources, such as soil, weather, crop plants (e.g., species, growth stage, plant health), weeds (e.g., species, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., with the goal of optimizing profitability, sustainability, and environmental protection. In particular, such models can help optimize agronomic decisions, control the accuracy of pesticide application, and monitor the operations performed.

[0415] For example, if the model modulates the occurrence of pests and calculates that a threshold has been reached that recommends application of a compound of the invention to a crop plant, the compound of the invention can be applied to the crop plant according to an appropriate use regimen.

[0416] Commercially available systems including agronomic models are, for example, FieldScripts from The Climate Corporation. TM , Xarvio from BASF TM AGLogic from John Deere TM wait.

[0417] In addition, the compounds of the present invention can also be used in combination with intelligent sprayers, for example, devices for selective spraying or precision spraying attached to or contained in agricultural vehicles (such as tractors, robots, helicopters, airplanes, unmanned aerial vehicles (UAVs) such as unmanned aircraft, etc.). Such equipment generally includes an input sensor (such as a camera) and a processing unit, and the processing unit is configured to analyze the input data and is configured to provide a decision based on the analysis of the input data, and the compounds of the present invention are applied to crop plants (or weeds) in a specific and accurate manner. Using such intelligent sprayers generally requires a positioning system (such as a GPS receiver) to locate the resulting data and guide or control agricultural vehicles, a geographic information system (GIS) to represent information on understandable maps, and appropriate agricultural vehicles to perform desired agricultural actions, such as spraying.

[0418] In one example, pests can be detected from an image captured by a camera. In one example, pests can be identified and / or classified based on the image. Such identification and / or classification can utilize image processing algorithms. Such image processing algorithms can utilize machine learning algorithms, such as artificial neural networks, decision trees, and artificial intelligence algorithms. In this way, compounds described herein can only be used when needed.

[0419] Seed treatment

[0420] It has long been known that animal pests are prevented and treated by processing plant seeds and this is a constantly improving theme. However, seed treatment relates to a series of problems that can not always be solved in a satisfactory manner. Therefore, it is necessary to develop a method for protecting seeds and germinating plants, which method does not need or at least significantly reduces the additional application of agricultural chemicals during storage, after sowing or after plant emergence. In addition, it is also necessary to optimize the amount of the active component used, so that best protection is provided for seeds and germinating plants to be protected from the infringement of animal pests, and the active component used will not damage the plant itself. Especially, the method for processing seeds should also take into account the inherent insecticide or nematicide characteristics of pest resistance or pest tolerance transgenic plants, so that the best protection of seeds and germinating plants is realized with a minimum amount of agricultural chemicals.

[0421] Therefore, in particular, the present invention also relates to a method for protecting seeds and germinating plants from pests by treating seeds with one of the compounds of formula (I). The method of the present invention for protecting seeds and germinating plants from pests also includes a method for treating seeds using a compound of formula (I) and a mixed component simultaneously or sequentially in one operation. It also includes a method for treating seeds using a compound of formula (I) and a mixed component at different times.

[0422] The invention also relates to the use of the compounds of the formula (I) for treating seed for protecting the seed and the resulting plant from attack by animal pests.

[0423] The present invention also relates to seeds treated with compounds of formula (I) of the present invention to protect them from animal pests. The present invention also relates to seeds treated with compounds of formula (I) and mixed components simultaneously. The present invention also relates to seeds treated with compounds of formula (I) and mixed components at different times. In the case of seeds treated with compounds of formula (I) and mixed components at different times, each substance may be present on the seeds in different layers. In this case, the layers comprising compounds of formula (I) and mixed components may optionally be separated by intermediate layers. The present invention also relates to seeds to which compounds of formula (I) and mixed components are applied as part of a coating or as another layer or layers in addition to a coating.

[0424] The present invention also relates to seeds which, after treatment with the compound of formula (I), are subjected to a film coating process to protect the seeds from dust abrasion.

[0425] When the compounds of formula (I) act systemically, one of the advantages that results is that the treatment of the seed protects not only the seed itself but also the resulting plant from it from attack by animal pests after emergence. In this way, it is not necessary to treat the crop immediately at sowing or shortly thereafter.

[0426] Another advantage is that treatment of seeds with a compound of formula (I) may promote germination and emergence of the treated seeds.

[0427] It is likewise considered to be advantageous that the compounds of the formula (I) can also be used, in particular, in transgenic seeds.

[0428] Furthermore, the compounds of formula (I) can also be used in combination with compositions or compounds for signaling technology, leading to better colonization of symbionts (eg rhizobia, mycorrhizae and / or endophytic bacteria or fungi), and / or optimized nitrogen fixation.

[0429] The compound of formula (I) is suitable for protecting the seed of any plant variety used in agriculture, greenhouse, forestry or gardening. More specifically, it is the seed of following plant: cereal (such as wheat, barley, rye, millet and oat), corn, cotton, soybean, rice, potato, sunflower, coffee, tobacco, canola, rape, beet (such as sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, kidney bean, cruciferous vegetables, onion and lettuce), fruit plant, lawn plant and ornamental plant. It is particularly important to process the seed of cereal (such as wheat, barley, rye and oat), corn, soybean, cotton, canola, rape, vegetables and rice.

[0430] As mentioned above, it is also particularly important to treat transgenic seeds with compounds of formula (I). This includes seeds of plants that generally contain at least one heterologous gene that controls the expression of a polypeptide that has, in particular, insecticidal and / or nematicidal properties. The heterologous gene in the transgenic seed may be derived from a microorganism such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for treating transgenic seeds that contain at least one heterologous gene derived from Bacillus. The heterologous gene is more preferably derived from Bacillus thuringiensis.

[0431] In the context of the present invention, the compound of formula (I) is applied to the seed. It is preferred to treat the seed in such a state that it is sufficiently stable so that no damage occurs during the treatment process. Usually, the seed can be treated at any time between harvesting and sowing. Usually, the seed separated from the plant and the cob, shell, stem, pod (coat), hair or pulp is removed. For example, the seed that has been harvested, cleaned and dried to a moisture content that allows storage can be used. Alternatively, the seed that is treated with water and then dried (for example, pre-treated (priming)) after drying can also be used. In the case of rice seeds, it is also possible to use seeds that have been, for example, soaked in water until it reaches a certain stage of the rice embryo ("endosperm (pigeon breast) stage"), which leads to stimulation of germination and more uniform germination.

[0432] When treating seed, it is generally necessary to ensure that the amount of compound of formula (I) and / or other additives applied to the seed is selected so that the germination of the seed is not adversely affected or the resulting plant is not damaged. This must be ensured in particular for active ingredients that may exhibit phytotoxic effects at certain application rates.

[0433] Typically, the compounds of formula (I) are applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.

[0434] The compounds of formula (I) can be converted into conventional seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.

[0435] These preparations are prepared in a known manner by mixing the compounds of formula (I) with conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.

[0436] Dyes that may be present in the seed dressing formulations to be used according to the invention are all dyes customary for such purposes. Pigments that are sparingly soluble in water or dyes that are soluble in water can be used. Examples include the dyes known by the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.

[0437] Useful wetting agents that may be present in the seed dressing formulations to be used according to the invention are all substances which promote wetting and are customarily used for formulating agrochemical active ingredients. Preference is given to using alkyl naphthalenesulfonates, such as diisopropyl naphthalenesulfonate or diisobutyl naphthalenesulfonate.

[0438] Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations to be used according to the invention are all nonionic, anionic and cationic dispersants which are customary for the formulation of agrochemical active ingredients. It is preferred to use nonionic or anionic dispersants, or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include in particular ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and phosphated or sulfated derivatives thereof. Suitable anionic dispersants are in particular lignin sulfonates, polyacrylates and arylsulfonate-formaldehyde condensates.

[0439] Antifoams which may be present in the seed dressing formulations to be used according to the invention are all foam-inhibiting substances which are customary for formulating agrochemical active ingredients. Silicone antifoams and magnesium stearate may preferably be used.

[0440] Preservatives which may be present in the seed dressing formulations to be used according to the invention are all substances which can be employed for such purposes in agrochemical compositions. Examples include dichlorophenol and benzyl alcohol hemiformal.

[0441] Secondary thickeners which may be present in the seed dressing formulations to be used according to the invention are all substances which can be employed for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silica.

[0442] Useful adhesives that may be present in the seed dressing formulations to be used according to the invention are all customary binders which can be used for seed dressing products. Preferred examples include polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0443] The gibberellins which may be present in the seed dressing formulations to be used according to the invention are preferably the gibberellins A1, A3 (=gibberellic acid), A4 and A7; particular preference is given to using gibberellic acid. The gibberellins are known (cf. R. Wegler "Chemie der Pflanzenschutz-und Volume 2, Springer Verlag, 1970, pp. 401-412).

[0444] The seed dressing formulations which can be used according to the invention can be used directly or after prior dilution with water to treat a wide variety of different types of seeds. For example, the concentrates or the preparations obtainable therefrom by dilution with water can be used for seed dressing of cereals, such as wheat, barley, rye, oats and triticale, as well as of corn, rice, rape, peas, beans, cotton, sunflower, soybeans and beets, or of various vegetable seeds. The seed dressing formulations which can be used according to the invention or their diluted use forms can also be used for seed dressing of transgenic plant seeds.

[0445] For treating the seed with the seed dressing formulations which can be used according to the invention or with the use forms prepared therefrom by adding water, all mixing apparatus customary for seed dressing are suitable. In particular, the seed dressing process consists in placing the seed in a batchwise or continuously operated mixer, adding the specifically desired amount of the seed dressing formulation (as such or after prior dilution with water), and mixing until the formulation is evenly distributed on the seed. If appropriate, this is followed by a drying operation.

[0446] The application rate of the seed dressing formulations that can be used according to the invention can vary within a wide range. This is determined by the specific content of the compound of formula (I) in the formulation and the seeds. The application rate of the compound of formula (I) is generally 0.001 to 50 g / kg seed, preferably 0.01 to 15 g / kg seed.

[0447] Animal Health

[0448] In the field of animal health, i.e. veterinary medicine, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term "endoparasites" particularly includes helminths and protozoa, such as coccidia. Ectoparasites are usually and preferably arthropods, in particular insects or mites.

[0449] In the field of veterinary medicine, the compounds of formula (I) with favorable homeothermic toxicity are suitable for controlling parasites that occur in animal breeding and animal husbandry in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are active against all or specific developmental stages of parasites.

[0450] Agricultural livestock include, for example, mammals, such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, deer, in particular cattle and pigs; or poultry, such as turkeys, ducks, geese, in particular chickens; or fish or crustaceans, such as in aquaculture; or optionally, insects such as bees.

[0451] Domestic animals include, for example, mammals, such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, in particular dogs, cats, cage birds; reptiles, amphibians or ornamental fish.

[0452] In a specific embodiment, a compound of formula (I) is administered to a mammal.

[0453] In other specific embodiments, the compounds of formula (I) are administered to avians, ie caged birds or in particular poultry.

[0454] The use of compounds of formula (I) for controlling animal parasites is intended to reduce or prevent disease, mortality and performance decline (in the case of meat, milk, wool, hide, eggs, honey, etc.), thereby making animal husbandry more economical and simpler and achieving better animal health.

[0455] In the context of this article, with respect to the field of animal health, the term "control" or "controlling" means that the compounds of formula (I) are effective in reducing the incidence of specific parasites in animals infected by the above-mentioned parasites to harmless levels. More specifically, in the context of this article, "control" means that the compounds of formula (I) kill various parasites, inhibit their growth or inhibit their proliferation.

[0456] Arthropods include, but are not limited to:

[0457] From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.;

[0458] From the order of the Mallophagida, and the suborders Amblycerina and Ischnocerina, for example, Bovicola spp., Damalina spp., Felicola spp., Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp.;

[0459] From the order Diptera and the suborder Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culex spp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematobia spp., Haematopota spp. spp.), Hippobosca spp., Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Lucilia spp., Lutzomyia spp., Melophagus spp., Morellia spp., Muscas spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp.), Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

[0460] From the order of the Siphonapterida, for example, Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsyllas spp.;

[0461] From the order of the Heteropterida, for example, Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp.; and nuisance and hygiene pests from the order of the Blattarida.

[0462] Furthermore, in the case of arthropods, mention may be made of, for example but not limited to, the following Acari:

[0463] Subclass Acari (order Acarina) and order Metastigmata, for example Argasidae such as Argas spp., Ornithodorus spp., Otobius spp., Ixodidae such as Amblyomma spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genus of multi-host ticks); Order Mesostigmata such as Dermanyssus spp. spp.), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Sternostoma spp., Tropilelaps spp., Varroa spp.; from the order of the Actinedida (order Prostigmata), for example, Acarapis spp., Cheyletiella spp., Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp., Ornithocheyletia spp., Psorergates spp., Trombicula spp.); and from the order of the Acaridida (order Astigmata), for example, Acarus spp., Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp., Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp., Psoroptes spp., Pterolichus spp.), Sarcoptes spp., Trixacarus spp., Tyrophagus spp.

[0464] Examples of parasitic protozoa include, but are not limited to:

[0465] Mastigophora (Flagellata), for example:

[0466] Metamonada: Order Diplomonadida, e.g., Giardia spp., Spironucleus spp.

[0467] Parabasala: From the order of the Trichomonadida, for example, Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.

[0468] Euglenozoa: Trypanosomatida, e.g., Leishmania spp., Trypanosoma spp.

[0469] Subdivision Sarcomastigophora (subdivision Rhizopoda), for example, Entamoebidae, for example, Entamoeba spp., Centramoebidae, for example, Acanthamoeba sp., Euamoebidae, for example, Harmanella sp.

[0470] Alveolata, for example Apicomplexa (Sporozoa): for example Cryptosporidium spp.; Eimeriida, for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp.; Adeleida, for example Hepatozoon spp., Klossiella spp. spp.); Haemosporida, for example, Leucocytozoon spp., Plasmodium spp.; Piroplasmida, for example, Babesia spp., Ciliophora spp., Echinozoon spp., Theileria spp.; Vesibuliferida, for example, Balantidium spp., Buxtonella spp.

[0471] Microspora, for example, Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., and for example, Myxozoa spp.

[0472] Helminths pathogenic to humans or animals include, for example, Acanthocephala, Nematodes, Pentastoma, and Platyhelminthes (eg, Monogenea, Cestodes, and trematodes).

[0473] Exemplary worms include, but are not limited to:

[0474] Monogenea: for example, Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystoma spp., Troglecephalus spp.

[0475] Taenia: Pseudophyllidea, for example, Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.;

[0476] From the order of the Cyclophyllidea, for example: Andyra spp., Anoplocephala spp., Avitellina spp., Bertiella spp., Cittataenia spp., Davainea spp., Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp., Echinocotyle spp., Echinolepis spp., Hydatigera spp.), Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezias spp., Paranoplocehala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosomsa spp.;

[0477] Trematodes: from the class Digenea, for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp., Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp. spp.), Eurytemas spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp., Gigantobilharzia spp., Gigantoctyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp.), Opisthorchis spp., Ornithobilharzia spp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp., Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp., Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.;

[0478] Nematodes: order Trichinellida, for example: Capillaria spp., Eucoleus, Paracapillaria, Trichinella spp., Trichomosoides, Trichuris spp.;

[0479] From the order of the Tylenchida, for example: Micronema spp., Parastrangyloides spp., Strongyloides spp.;

[0480] From the order of the Rhabditina, for example: Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonema spp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp., Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomum spp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp.), Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp., Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp.), Nippostrongylus spp., Obeliscoides spp., Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp., Ornithostrongylus spp., Oslerus spp., Ostertagiaspp., Paracooperia spp.), Paracrenosoma, Parafilaroides spp., Parelaphostrongylus spp., Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp., Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylus spp., Syngamus spp., Teledorsagia spp., Trichoonema spp., Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp., Uncinaria spp.);.

[0481] From the order of the Spirurida, for example: Acanthocheilonema spp., Anisakis spp., Ascaridia spp., Ascaris spp., Ascarops spp., Aspiculuris spp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp., Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp., Draschia spp., Enterobius spp., Filaria spp.), Gnathostoma spp., Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loa spp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp., Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp., Pseudofilaria spp., Setaria spp.), Skjrabinema spp., Spirocerca spp., Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Wuchereria spp.;

[0482] Acanthocephala: Oligacanthorhynchida, e.g. Macracanthorhynchus spp., Prosthenorchis spp.; Moniliformida, e.g. Moniliformis spp.;

[0483] From the order of the Polymorphida, for example, Filicollis spp.; from the order of the Echinorhynchida, for example, Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.;

[0484] Phylum Pentastoma: Order Porocephalida, e.g. Linguatula spp.

[0485] In the veterinary field and in animal husbandry, the compounds of formula (I) are administered in the form of suitable formulations by methods generally known in the art, for example enteral, parenteral, dermal or nasal routes. Administration may be prophylactic, metaphylactic or therapeutic.

[0486] Therefore, one embodiment of the present invention relates to compounds of formula (I) for use as medicaments.

[0487] Another aspect relates to compounds of formula (I) for use as anti-endoparasitic agents.

[0488] Another specific aspect relates to compounds of formula (I) for use as antihelminthic agents, in particular as nematicides, platyhelminthicides, acanthocephalicides or linguicidalides.

[0489] Another specific aspect relates to compounds of formula (I) for use as antiprotozoal agents.

[0490] A further aspect relates to compounds of the formula (I) for use as anti-ectoparasitic agents, in particular arthropodicides, very particularly insecticides or acaricides.

[0491] Another aspect of the present invention is a veterinary preparation comprising an effective amount of at least one compound of formula (I) and at least one of the following substances: a pharmaceutically acceptable excipient (e.g. a solid or liquid diluent), a pharmaceutically acceptable adjuvant (e.g. a surfactant), in particular a pharmaceutically acceptable excipient conventionally used in veterinary preparations and / or a pharmaceutically acceptable adjuvant conventionally used in veterinary preparations.

[0492] A related aspect of the invention is a method for preparing a veterinary formulation as described herein, comprising the steps of mixing at least one compound of formula (I) with pharmaceutically acceptable excipients and / or auxiliaries, in particular with pharmaceutically acceptable excipients conventionally used in veterinary formulations and / or auxiliaries conventionally used in veterinary formulations.

[0493] Another particular aspect of the invention is a veterinary preparation selected from ectoparasiticidal preparations and endoparasiticidal preparations, in particular selected from anthelmintic, antiprotozoan and arthropodicidal preparations according to the mentioned aspects, very particularly selected from nematocidal, platyhelmintic, acanthocephalicidal, linguicidal, insecticidal and acaricidal preparations, and a process for their preparation.

[0494] Another aspect relates to a method for treating parasitic infections, in particular infections caused by parasites selected from the ectoparasites and endoparasites mentioned herein, by using an effective amount of a compound of formula (I) in an animal in need thereof, in particular a non-human animal.

[0495] Another aspect relates to a method for treating parasitic infections, in particular infections caused by parasites selected from the ectoparasites and endoparasites mentioned herein, by using a veterinary formulation as defined herein in an animal, in particular a non-human animal, in need thereof.

[0496] Another aspect relates to the use of a compound of formula (I) for treating parasitic infections in animals, especially non-human animals, especially infections caused by parasites selected from the ectoparasites and endoparasites mentioned herein.

[0497] In the animal health or veterinary context of the present invention, the term "treatment" includes prophylactic, remedial or therapeutic treatment.

[0498] In a specific embodiment, in this way, mixtures of at least one compound of the formula (I) with other active ingredients, in particular with endoparasiticides and ectoparasiticides, are provided for use in the veterinary field.

[0499] In the field of animal health, "mixture" refers not only to two (or more) different active ingredients formulated in a conventional formulation and used together accordingly, but also to products containing separate formulations for each active ingredient. Therefore, when more than two active ingredients are used, all active ingredients can be formulated in a conventional formulation or all active ingredients can be formulated in separate formulations; it can also be in a mixed form, in which some active ingredients are formulated together and some active ingredients are formulated separately. The separate formulations can apply the active ingredients separately or sequentially.

[0500] The active ingredients referred to herein by their common names are known and are described, for example, in the “Pesticide Manual” (see above) or can be retrieved on the Internet (eg: http: / / www.alanwood.net / pesticides).

[0501] Exemplary active ingredients of the ectoparasiticides as admixtures include (but are not intended to be limited to) the insecticides and acaricides listed in detail above. Other active ingredients that can be used are listed below according to the above classification based on the current IRAC mode of action classification scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodium channel modulators; (4) nicotinic acetylcholine receptor (nAChR) competitive modulators; (5) nicotinic acetylcholine receptor (nAChR) allosteric modulators; (6) glutamate-gated chloride channel (GluCl) allosteric modulators; (7) juvenile hormone mimetics; (8) other non-specific (multi-site) inhibitors; (9) chord organ modulators; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) Uncouplers of oxidative phosphorylation that interrupt the proton gradient; (14) Nicotinic acetylcholine receptor channel blockers; (15) Chitin biosynthesis inhibitors, type 0; (16) Chitin biosynthesis inhibitors, type 1; (17) Molting disruptors (especially for Diptera); (18) Ecdysone receptor agonists; (19) Octopamine receptor agonists; (21) Mitochondrial complex I electron transport inhibitors; (25) Mitochondrial complex II electron transport inhibitors; (20) Mitochondrial complex III electron transport inhibitors; (22) Voltage-dependent sodium channel blockers; (23) Inhibitors of acetyl CoA carboxylase; (28) Nicotinic receptor modulators; (30) Allosteric modulators of GABA-gated chloride channels.

[0502] Active ingredients with unknown or non-specific mechanisms of action, such as fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionat, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flutenzine, brompropylate, cryolite;

[0503] Other types of compounds, such as butacarb, dimetilan, cloethocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl), methacrifos, isopropylo-salicylate, trichlorfon, tigolaner, sulprofos, propaphos, sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methyl sulfone), isazofos, cyanofenphos, dialifos, carbophenothion, autathiofos, aromfenvinfos(-methyl), azinphos(-ethyl), chlorpyrifos(-ethyl), fosmethilan, iodofenphos, dioxabenzofos, formothion, fonofos, flupyrazofos, fensulfothion, etrimfos;

[0504] Organic chlorides, such as camphechlor, lindane, heptachlor; or phenylpyrazoles, such as acetoprole, pyrafluprole, pyriprole, vaniliprole, sisapronil; or isoxazolines, such as sarolaner, afoxolaner, lotilaner, fluralaner;

[0505] Pyrethroids, such as (cis-, trans-)metofluthrin, profluthrin, flufenprox, flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin, RU15525, terallethrin, cis-resmethrin cis-resmethrin), heptafluthrin, bioethanomethrin, biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin, clocythrin, cyhalothrin (lambda-), chlovaporthrin, or a halogenated hydrocarbon compound (HCH),

[0506] Neonicotinoids, such as nithiazine;

[0507] dicloromezotiaz, triflumezopyrim;

[0508] Macrolides, such as nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin oxime;

[0509] Triprene, epofenonane, and diofenolan;

[0510] Biological agents, hormones or pheromones, for example natural products such as thuringiensin, codlemone or neem components;

[0511] Dinitrophenols, such as dinocap, dinobuton, and binapacryl;

[0512] Benzoyl ureas, such as fluazuron and penfluron;

[0513] Amidine derivatives, for example chlormebuform, cymiazole, demiditraz;

[0514] Beehive varroa acaricide, for example an organic acid, such as formic acid, oxalic acid.

[0515] Exemplary active compounds of the endoparasiticides as admixtures include, but are not limited to, active anthelmintic ingredients and active antiprotozoal ingredients.

[0516] Active anthelmintic compounds include, but are not limited to, the following active nematicidal, trematicidal and / or cestocidal ingredients:

[0517] Macrolides, for example, eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, ivermectin, emamectin, and milbemycin;

[0518] Benzimidazoles and probenzimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimin, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flubendazole;

[0519] Depsipeptides, preferably cyclic depsipeptides, especially 24-membered cyclic depsipeptides, for example: emodepside, PF 1022A;

[0520] Tetrahydropyrimidines, such as morantel, pyrantel, and oxantel;

[0521] Imidazolothiazoles, for example, butamisole, levamisole, tetramisole;

[0522] Aminophenylamidines, such as amidantel, deacylated amidantel (dAMD), and tribendimidine;

[0523] Aminoacetonitriles, such as monepantel;

[0524] paraherquamides, for example paraherquamide, derquantel;

[0525] Salicylanilides, such as tribromsalan, bromoxanide, brotianide, clioxanide, closantel, niclosamide, oxyclozanide, and rafoxanide;

[0526] Substituted phenols, for example, nitroxynil, bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;

[0527] Organophosphates, such as trichlorfon, naphthalofos, dichlorvos (DDVP), crufomate, coumaphos, haloxon;

[0528] Piperazinones / quinolines, such as praziquantel and epsiprantel;

[0529] Piperazines, for example, piperazine, hydroxyzine;

[0530] Tetracyclines, such as tetracycline, chlorotetracycline, doxycycline, oxytetracycline, and rolitetracycline;

[0531] Various others, for example: bunamidine, niridazole, resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquin, mirasan, miracil, lucanthon, hycanthon, hetolin, emetin, diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium, amoscanate, clorsulon.

[0532] Active antiprotozoal ingredients include, but are not limited to, the following active ingredients:

[0533] Triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril;

[0534] Polyether ionophores, for example, monensin, salinomycin, maduramicin, narasin;

[0535] Macrolides, such as milbemycin and erythromycin;

[0536] Quinolones, such as enrofloxacin and pradofloxacin;

[0537] Quinines, such as chloroquine;

[0538] Pyrimidines, such as pyrimethamine;

[0539] Sulfonamides, such as sulfaquinoxaline, trimethoprim, and sulfaclozin;

[0540] Thiamines, such as amprolium;

[0541] Lincosamides, such as clindamycin;

[0542] Carbanilides, such as imidocarb;

[0543] Nitrofurans, such as nifurtimox;

[0544] Quinazolinone alkaloids, such as halofuginone;

[0545] Various other types, such as oxamniquine, paromomycin;

[0546] Vaccines or antigens from microorganisms, such as Babesia canisrossi, Eimeria tenella, Eimeria praecox, Eimeria necatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeria acervulina, Babesia canis vogeli, Leishmania infantum, Babesia canis canis, Dictyocaulus viviparus.

[0547] If appropriate, all of the mixing components mentioned can also form salts with suitable bases or acids if they are capable of forming salts based on their functional groups.

[0548] Vector Control

[0549] The compounds of formula (I) can also be used for vector control. In the context of the present invention, vectors are arthropods, particularly insects or arachnids, which are capable of transmitting pathogens such as viruses, worms, unicellular organisms and bacteria from reservoirs (plants, animals, humans, etc.) to hosts. Pathogens can be transmitted to hosts mechanically (e.g., by non-stinging flies to spread trachoma), or can be transmitted to hosts after injection (e.g., by mosquitoes to spread Plasmodium).

[0550] Examples of vectors and the diseases or pathogens they transmit are:

[0551] 1)Mosquito

[0552] - Anopheles: malaria, filariasis;

[0553] - Culex spp.: Japanese encephalitis, other viral diseases, filariasis, other helminthic diseases;

[0554] - Aedes: yellow fever, dengue fever, other viral diseases, filariasis;

[0555] - Simulidae: worm-borne, especially Onchocerca volvulus;

[0556] - Trichodinae: transmission of leishmaniasis;

[0557] 2) Lice: skin infection, epidemic typhus;

[0558] 3) Fleas: plague, typhus, tapeworms;

[0559] 4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterial diseases;

[0560] 5) Mites: tick disease, epidemic typhus, rickettsial pox, tularemia, Saint Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo haemorrhagic fever, borreliosis;

[0561] 6) Ticks: borrelioses, such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), babesioses (Babesia canis canis), ehrlichiosis.

[0562] In the context of the present invention, examples of disease vectors are insects, such as aphids, flies, leafhoppers or thrips, which can transmit plant viruses to plants. Other disease vectors capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.

[0563] Further examples of disease vectors in the context of the present invention are insects and arachnids, such as mosquitoes, in particular Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, Ceratidae, such as Phlebotomus, Lophatherium, lice, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.

[0564] Vector control is also possible if the compounds of the formula (I) are resistance-breaking.

[0565] The compounds of formula (I) are suitable for preventing diseases and / or pathogens transmitted by vectors. Therefore, another aspect of the invention is the use of the compounds of formula (I) for vector control in, for example, agriculture, horticulture, gardening and leisure equipment, and in the protection of materials and stored products.

[0566] Protection of industrial materials

[0567] The compounds of the formula (I) are suitable for protecting industrial materials from attack or destruction by insects, for example from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Euptera and Zygentoma.

[0568] In the context of the present invention, industrial materials are understood to mean inanimate materials, such as, preferably, plastics, adhesives, sizes, paper and card, leather, wood, processed wood products and coating compositions. Particular preference is given to the use according to the invention for protecting wood.

[0569] In another embodiment, the compounds of formula (I) are used together with at least one other insecticide and / or at least one fungicide.

[0570] In another embodiment, the compound of formula (I) is in the form of a ready-to-use pesticide, meaning that it can be applied to the material in question without further modification. Useful further insecticides or fungicides include in particular those mentioned above.

[0571] Surprisingly, it has also been found that the compounds of formula (I) can be used for protecting objects which come into contact with salt water or brackish water from fouling, in particular hulls, bulkheads, nets, buildings, moorings and signalling systems. The compounds of formula (I) can likewise be used as antifouling agents, either alone or in combination with other active compounds.

[0572] Control of animal pests in the health sector

[0573] The compounds of formula (I) are suitable for controlling animal pests in the sanitary field. More specifically, the present invention can be used in the field of indoor protection, the field of sanitary protection and the protection of stored products, in particular for controlling insects, arachnids, ticks and mites encountered in confined spaces, such as residences, factory halls, offices, vehicle cabins and animal breeding facilities. In order to control animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or adjuvants. It is preferably used in indoor insecticide products. The compounds of formula (I) are effective against sensitive species and resistant species, and against all their developmental stages.

[0574] These pests include, for example, the following: Arachnida; Scorpiones, Araneae and Opiliones; Chilopoda and Diplopoda; Insecta, Blattodea; Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phycoptera, Pseudostellaria, Saltatoria or Orthoptera, Siphonaptera and Silverfish; Malacrusta, Isopoda.

[0575] For example, in aerosols, non-pressure sprayer products (such as pump sprayers and atomizing sprayers); automatic atomizing systems, atomizers, foams, gels; evaporator products with evaporator sheets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propeller-driven evaporators; energy-free or passive evaporation systems, moth papers, moth bags and moth glues, as granules or powders, for application to baits or bait stations for broadcasting.

[0576] Analytical determination

[0577] The procedures for the analytical assays described below apply to all cases throughout the document unless the respective analytical assay procedures are described separately in the relevant paragraphs herein.

[0578] Mass spectrometry

[0579] [M+H] was determined by LC-MS under acidic chromatographic conditions + or M - , 1 ml formic acid / L acetonitrile and 0.9 ml formic acid / L Millipore water were used as mobile phases. Zorbax Eclipse Plus C18 column, 50 mm*2.1 mm, was used at a column oven temperature of 55°C.

[0580] instrument:

[0581] LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManager sample changer. Linear gradient 10% acetonitrile to 95% acetonitrile from 0.0 to 1.70 minutes, constant at 95% acetonitrile from 1.70 to 2.40 minutes, flow rate 0.85 ml / min.

[0582] LC-MS6 and LC-MS7: Agilent 1290LC, Agilent MSD, HTS PAL sample changer. Linear gradient from 10% acetonitrile to 95% acetonitrile from 0.0 to 1.80 minutes, constant at 95% acetonitrile from 1.80 to 2.50 minutes, flow rate 1.0 ml / min.

[0583] Determination of [M+H] by LC-MS under neutral chromatographic conditions + , using acetonitrile and Millipore water with 79 mg / l ammonium carbonate as mobile phase.

[0584] instrument:

[0585] LC-MS4: Waters IClass Acquity with QDA mass spectrometer and FTN sample changer (column WatersAcquity 1.7μm 50mm*2.1mm, column oven temperature 45°C). Linear gradient from 10% acetonitrile to 95% acetonitrile from 0.0 to 2.10 minutes, constant at 95% acetonitrile from 2.10 to 3.00 minutes, flow rate 0.7 ml / min.

[0586] LC-MS5: Agilent 1100 LC system with MSD mass spectrometer and HTS PAL sample changer (column: ZorbaxXDB C18 1.8 μm 50 mm*4.6 mm, column oven temperature 55°C). Linear gradient from 10% acetonitrile to 95% acetonitrile from 0.0 to 4.25 minutes, constant at 95% acetonitrile from 4.25 to 5.80 minutes, flow rate 2.0 ml / min.

[0587] In all cases, retention time indices were determined for the homologous series of linear alkan-2-ones having from 3 to 16 carbon atoms, with the index for the first alkanone set to 300, the index for the last alkanone set to 1600 and linear interpolation between consecutive alkanone values.

[0588] 1 H NMR spectra were measured using a Bruker Avance III 400 MHz spectrometer equipped with a 1.7 mm TCI sampling head using tetramethylsilane as the standard (0.00 ppm). Measurements were typically recorded on a solvent CD. 3 CN、CDCl 3 or 6 -solution in DMSO. Alternatively, the measurements were performed using a Bruker Avance III 600MHz spectrometer equipped with a 5mm CPNMP sampling head or a Bruker Avance NEO 600MHz spectrometer equipped with a 5mm TCI sampling head. Typically, the measurements were performed at a sampling head temperature of 298K. If other measurement temperatures are used, this should be specifically mentioned.

[0589] NMR peak list method

[0590] Selected Embodiments 1 H-NMR data 1 H-NMR peaks are shown in the form of a table. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. The δ value / signal intensity pairs are separated by semicolons.

[0591] Thus, the peak list for an instance takes the following form:

[0592] δ 1 (strength 1 );δ 2 (strength 2 );........;δ i (strength i );........;δ n (strength n )

[0593] The intensity of a sharp signal is related to the height of the signal shown in a printout of the NMR spectrum in centimeters and shows the true scale of the signal strength. In the case of a broad signal, multiple peaks or the middle of the signal can be shown along with their relative intensities compared to the strongest signal in the spectrum.

[0594] If the sample does not contain any tetramethylsilane, then the calibration 1The chemical shifts of the H NMR spectra were performed using the chemical shifts of tetramethylsilane and / or the solvent used. Thus, in some cases, 1 The H NMR peak list may include the tetramethylsilane peak.

[0595] 1 H NMR peak lists are equivalent to conventional 1 H NMR shows that, therefore, it usually contains the same conventional 1 H NMR analysis of all peaks listed.

[0596] In addition, as usual 1 H-NMR indicates that it may show a solvent signal, a signal of a stereoisomer of the subject compound of the present invention, and / or a signal of an impurity peak.

[0597] Since the solvent 1 The reported intensity values ​​for the H NMR solvent, tetramethylsilane, and water signals can be very high and therefore they were excluded from the calibration of relative intensities.

[0598] The peaks of stereoisomers of the compounds of the invention and / or the peaks of impurities are usually less intense than the peaks of the compounds of the invention (eg, at a purity of >90%).

[0599] Such stereoisomers and / or impurities may be typical for a particular preparation process. Therefore, in this case, their peaks may help identify the reproducibility of the preparation process according to the "by-product fingerprint".

[0600] Experts who calculate the peaks of target compounds by known methods (MestreC, ACD simulation, and using empirically estimated expected values) can optionally identify the peaks of target compounds using additional intensity filters as needed. This identification is equivalent to conventional 1 H-NMR analysis related peak list.

[0601] The utilized solvent can be read from the JCAMP file in the parameter "Solvent", the measurement frequency of the spectrometer from "Observation frequency" and the spectrometer model from "Spectrometer / Data System".

[0602] 13 C NMR data and 1 H NMR data are similar, using broadband-decoupled 13 C NMR spectra are reported as peak lists. 13 CNMR solvent signals and tetramethylsilane can have very high intensity values, so these signals were excluded from the calibration of relative intensities.

[0603] Further details of NMR data interpretation using peak lists can be found in: "Citation of NMR Peaklist Data within Patent Applications" in Research Disclosure Database No. 564025.

[0604] logP value

[0605] The logP value was determined according to EEC Directive 79 / 831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a reverse phase column (C18) using the following method:

[0606] [a] The logP values ​​were determined by LC-UV measurement in the acidic range using 0.9 ml / l aqueous formic acid and 1.0 ml / l formic acid in acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0607] [b] The logP values ​​were determined by LC-UV measurement in the neutral range using 0.001 molar aqueous ammonium acetate solution and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0608] The calibration was performed using linear alkan-2-ones (having 3 to 16 carbon atoms) with known logP values. The above values ​​between consecutive alkanes were determined by linear regression.

[0609] List of abbreviations

[0610] DIPEA Diisopropylethylamine

[0611] DMF N,N-Dimethylformamide

[0612] DMSO Dimethyl sulfoxide

[0613] dppf 1,1'-Bis(diphenylphosphino)ferrocene

[0614] EDCI 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

[0615] h hour

[0616] HATU O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

[0617] HPLC High Performance Liquid Chromatography

[0618] min

[0619] MTBE 2-methoxy-2-methylpropane (methyl tert-butyl ether)

[0620] RT Room temperature

[0621] THF Tetrahydrofuran

[0622] Preparation Example

[0623] Intermediates

[0624] Intermediate 1A

[0625] 2-Bromo-1-methyl-1H-imidazole-4-carboxylic acid ethyl ester

[0626]

[0627] 30.0 g (195 mmol) of ethyl 1-methyl-1H-imidazole-4-carboxylate was dissolved in 1.0 l of tetrahydrofuran and cooled to 0° C. 34.5 g (195 mmol) of N-bromosuccinimide were added portionwise to the solution, and the reaction mixture was stirred at room temperature overnight. The mixture was stirred overnight by adding saturated sodium thiosulfate solution (Na 2 S 2 O 3 ) to terminate the reaction and add 800 ml of ethyl acetate. Separate each phase and extract three times with 800 ml of ethyl acetate each time. Combine the organic phases, dry over sodium sulfate and filter. Distill out the solvent under reduced pressure and purify the residue by column chromatography using a petroleum ether / ethyl acetate gradient (3:1) as the mobile phase.

[0628] 1 H-NMR (300MHz, d 6 -DMSO)δppm:1,26(t,3H),3,64(s,3H),4,22(q,2H),8,07(s,1H).

[0629] Intermediate 2A

[0630] 2-Bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-carboxylic acid

[0631]

[0632] 31.0 g (134 mmol) of ethyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate and 24.4 g (200 mmol) of diethyl disulfide were dissolved in 620 ml of tetrahydrofuran and cooled to 78 ° C. 100 ml (2M in THF, 200 mmol) of lithium diisopropylamine (LDA) was added dropwise to the solution and the reaction mixture was stirred at 78 ° C for 30 minutes. The reaction was terminated by adding a saturated ammonium chloride solution. The phases were separated and the aqueous phase was extracted three times with 300 ml of ethyl acetate each time. The organic phases were combined, dried over magnesium sulfate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography using a petroleum ether / ethyl acetate gradient as the mobile phase. 28.5 g (97.3 mmol) of ethyl 2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-carboxylate was obtained. It was dissolved in 300 ml of methanol and the solution was cooled to 0 ° C. Then add 300ml sodium hydroxide (2N aqueous solution, 600mmol), and stir the mixture at room temperature for 1 hour. The mixture is concentrated on a rotary evaporator and neutralized by adding 1N HCl. The mixture is then extracted with ethyl acetate. The solvent is distilled off under reduced pressure to obtain the target compound.

[0633] 1 H-NMR (300MHz, d 6 -DMSO)δppm:1,09(t,3H),2,86(q,2H),3,64(s,3H),12,60(s,1H).

[0634] Intermediate 3A

[0635] N-(7-amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxan-6-yl)-2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-carboxamide

[0636]

[0637] To an initial charge of 2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-carboxylic acid (557 mg, 2.10 mmol) in DMF (40.0 ml) was added HATU (957 mg, 2.52 mmol) at room temperature and the mixture was stirred for 30 minutes. The mixture was then cooled to -10°C and a solution of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxane-6,7-diamine (500 mg, 2.10 mmol) in DMF (10.0 ml) was slowly added dropwise. After the addition was complete, the mixture was stirred at -10°C for 1 hour. The mixture was then poured into water and extracted with dichloromethane. The combined organic phases were washed twice with 1.0 M hydrochloric acid, once with saturated aqueous sodium chloride solution and dried over sodium sulfate. The solution was concentrated to dryness to give the title compound (1.34 g, 73% purity, 96% of theory). The title compound obtained was reacted further without further purification.

[0638] ESI mass [m / z]: 484.9 / 486.9 [M+H] +

[0639] Intermediate 4A

[0640] 4,4,5,5-Tetramethyl-2-{4-[1-(trifluoromethyl)cyclopropyl]phenyl}-1,3,2-dioxaborolane

[0641]

[0642] 1-Bromo-4-[1-(trifluoromethyl)cyclopropyl]benzene (250 mg, 943 μmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (287 mg, 1132 μmol), Pd(dppf)Cl 2 *CH 2 Cl 2 A mixture of 4-(4-(2-nitro-1-yl)-2-nitropropene (34.65 mg, 47 μmol) and potassium acetate (278 mg, 2.83 mmol) in acetonitrile (4.0 ml) was heated to 150 ° C in a microwave reactor for 15 minutes. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by column chromatography on silica gel to give the title compound (281 mg, 81% purity, 77% of theoretical value).

[0643] ESI mass [m / z]: 313.1 [M+H] +

[0644] 1 H-NMR (400 MHz, DMSO-d 6): δ[ppm]=7.68(d,2H),7.47(d,2H),1.37-1.32(m,2H),1.29(s,12H),1.15-1.09(m,2H).

[0645] Intermediate 5A

[0646] 2-Cyclopropyl-1-methyl-1H-imidazole-4-carboxylic acid tert-butyl ester

[0647]

[0648] To a solution of tert-butyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate (10.0 g, 38.3 mmol) in THF (300 ml) was added a solution of potassium phosphate (16.0 g, 116 mmol) in water (60 ml). The mixture was stirred for 10 minutes under an inert atmosphere and then X-Phos Pd G2 (CAS: 1310584-14-5, 2.00 g, 2.54 mmol) was added. The mixture was heated to boiling and then a solution of cyclopropylboronic acid (10.0 g, 116 mmol) in THF (100 ml) was added dropwise over 8 hours. After the addition was complete, the mixture was further refluxed overnight and then more potassium phosphate (16.0 g, 116 mmol) was added and then a solution of cyclopropylboronic acid (10.0 g, 116 mmol) in THF (100 ml) was added. After the addition was complete, the reaction mixture was refluxed for another 16 hours. After cooling to room temperature, the mixture was diluted with water (1000 ml) and extracted with ethyl acetate (2×500 ml). The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered through a thin layer of silica gel and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (4.0 g, 49% of theoretical value).

[0649] Intermediate 6A

[0650] tert-Butyl 5-bromo-2-cyclopropyl-1-methyl-1H-imidazole-4-carboxylate

[0651]

[0652] To a solution of tert-butyl 2-cyclopropyl-1-methyl-1H-imidazole-4-carboxylate (6.00 g, 27.0 mmol) in dichloromethane (100 ml) was added a solution of sodium bicarbonate (2.88 g, 34.3 mmol) in water (12 ml). A solution of bromine (1.73 ml, 33.8 mmol) in dichloromethane (20.0 ml) was added dropwise while cooling with an ice bath. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The solution was then diluted with dichloromethane (200 ml) and washed successively with saturated aqueous sodium bicarbonate solution (150 ml), saturated aqueous sodium thiosulfate solution (150 ml) and saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (7.00 g, 23.2 mmol, 86% of theoretical value).

[0653] Intermediate 7A

[0654] tert-Butyl 2-cyclopropyl-5-(ethylthio)-1-methyl-1H-imidazole-4-carboxylate

[0655]

[0656] n-Butyl lithium (2.5 M hexane fraction solution, 23.0 ml, 57.5 mmol) was added dropwise to a solution of tert-butyl 5-bromo-2-cyclopropyl-1-methyl-1H-imidazole-4-carboxylate (13.0 g, 43.0 mmol) in THF (200 ml) at -80°C. After the addition was complete, the mixture was stirred at -80°C for another hour, and then diethyl disulfide (30.0 g, 250 mmol) was added dropwise. After the addition was complete, the mixture was stirred at 50°C overnight. After cooling to room temperature, saturated aqueous ammonium chloride solution (200 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (3×300 ml). The combined organic phases were washed with water, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (7.20 g, 25.5 mmol, 78% of theoretical value).

[0657] Intermediate 8A

[0658] tert-Butyl 2-cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-carboxylate

[0659]

[0660] Meta-chloroperbenzoic acid (13.5 g, 78.0 mmol) was added to a solution of tert-butyl 2-cyclopropyl-5-(ethylthio)-1-methyl-1H-imidazole-4-carboxylate (7.20 g, 25.5 mmol) in dichloromethane (100 ml) at 0°C, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was then cooled to 0°C, saturated aqueous sodium bicarbonate solution (150 ml) and saturated aqueous sodium thiosulfate solution (50 ml) were added thereto and the mixture was filtered. The phases were separated, the organic phase was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (7.80 g, 24.8 mmol, 90% of theory).

[0661] Intermediate 9A

[0662] 2-Cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-carboxylic acid

[0663]

[0664] Trifluoroacetic acid (10 ml) was added to a solution of tert-butyl 2-cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-carboxylate (7.80 g, 24.8 mmol) in dichloromethane (100 ml) at 0°C. After the addition was complete, the mixture was stirred at room temperature for 4 days. The mixture was then concentrated and the residue was stirred in a mixture of MTBE and hexane (1:1). The solid was filtered off. The crude product thus obtained was recrystallized from diethyl ether to give the title compound (6.00 g, 23.2 mmol, 93% of theoretical value).

[0665] Intermediate 10A

[0666] N-(7-amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxan-6-yl)-2-cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-carboxamide

[0667]

[0668] To an initial charge of 2-cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-carboxylic acid (163 mg, 0.63 mmol) in DMF was added HATU (287.1 mg, 0.76 mmol) and DIPEA (274 μmol, 1.58 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled to -10°C. At this temperature, a DMF solution of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxane-6,7-diamine (150 mg, 0.63 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at -10°C for another hour. Then, HATU (287.1 mg, 0.76 mmol) and DIPEA (274 μmol, 1.58 mmol) were added and the mixture was stirred at room temperature for 1 hour. Water was added and the reaction mixture was extracted with dichloromethane. The combined organic phases were washed twice with 1.0 M hydrochloric acid, once with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (163 mg, 54% of theory).

[0669] ESI mass [m / z]: 479.4 [M+H] +

[0670] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=9.65(s,1H),7.38(s,1H),6.71(s,1H),5.26(s,2H),3.91(s,3H),3.61(q,2H),2.21-2.10(m,1H),1.21(t,3H),1.08-0.99(m,4H).

[0671] Intermediate 11A

[0672] 2-[4-(1-Fluorocyclopropyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0673]

[0674] 1-Bromo-4-(1-fluorocyclopropyl)benzene (200 mg, 930 μmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (283 mg, 1116 μmol), Pd(dppf)Cl 2 *CH 2 Cl 2A mixture of 4-( ...

[0675] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.68(d,2H),7.26(d,2H),1.57-1.42(m,2H),1.29(s,12H),1.25-1.13(m,2H).

[0676] Intermediate 12A

[0677] 4,4,5,5-Tetramethyl-2-{3-[1-(trifluoromethyl)cyclopropyl]phenyl}-1,3,2-dioxaborolane

[0678]

[0679] 1-Bromo-3-[1-(trifluoromethyl)cyclopropyl]benzene (200 mg, 755 μmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (229 mg, 905 μmol), Pd(dppf)Cl 2 A mixture of 4-(2-nitropropene)-2-nitropropene (25.1 mg, 34 μmol) and potassium acetate (222 mg, 2.26 mmol) in acetonitrile (8.0 ml) was heated to 150 ° C in a microwave reactor for 15 minutes. After cooling to room temperature, the reaction mixture was filtered through Celite, washed with acetonitrile and the filtrate was concentrated. The residue was first subjected to repeated column chromatography on silica gel and then the title compound (152 mg, 77% purity, 50% of theoretical value) was obtained by preparative HPLC.

[0680] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.74(s,1H),7.68-7.64(m,1H),7.61-7.57(m,1H),7.45-7.39(m,1H),1.36-1.32(m,2H),1.30(s,12H),1.15-1.09(m,2H).

[0681] Intermediate 13A

[0682] 2-[3-(1-Fluorocyclopropyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

[0683]

[0684] 1-Bromo-3-(1-fluorocyclopropyl)benzene (200 mg, 930 μmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (283 mg, 1116 μmol), Pd(dppf)Cl 2 A mixture of 4-(4-(4-(4-(4-piperidin-2-yl)-1-yl)-2-nitropropene (31.0 mg, 42 μmol) and potassium acetate (274 mg, 2.79 mmol) in acetonitrile (8.0 ml) was heated to 150 ° C in a microwave reactor for 15 minutes. After cooling to room temperature, the reaction mixture was filtered through Celite, washed with acetonitrile and the filtrate was concentrated. The residue was first subjected to repeated column chromatography on silica gel and then to preparative HPLC to give the title compound (50.4 mg, 72% purity, 15% of theoretical value).

[0685] ESI mass [m / z]: 263.2 [M+H] +

[0686] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.64-7.57(m,2H),7.44-7.35(m,2H),1.53-1.38(m,2H),1.34-1.27(m,12H),1.18-1.11(m,2H).

[0687] Intermediate 14A

[0688] 6,6,7,7-Tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0689]

[0690] A mixture of 2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxane-6,7-diamine (1.00 g, 4.19 mmol) and formic acid (5.0 ml) was heated to 150 ° C in a microwave reactor for 30 minutes. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by column chromatography on silica gel to give the title compound (588 mg, 56% of theoretical value).

[0691] ESI mass [m / z]: 249.1 [M+H] +

[0692] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=12.77(br s,1H),8.36(s,1H),7.70(br s,2H).

[0693] Intermediate 15A

[0694] 6,6,7,7-Tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0695]

[0696] 6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (644mg, 2.59mmol) was divided into four reaction vessels (161mg, 0.65mmol each). Iodomethane (101μl, 1.62mmol), potassium carbonate (314mg, 2.27mmol) and acetone (1.5ml) were added to each vessel. The container was sealed and heated to 60°C for 3 hours. After cooling to room temperature, the four reaction mixtures were combined and distributed between 1.0M hydrochloric acid and dichloromethane. The aqueous phase was neutralized with 1.0M sodium hydroxide aqueous solution and thoroughly extracted with ethyl acetate. All organic phases were combined, washed with saturated sodium chloride aqueous solution, dried with sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel to obtain the title compound (345mg, 51% of theoretical value).

[0697] ESI mass [m / z]: 263.3 [M+H] +

[0698] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.34(s,1H),7.81(s,1H),7.77(s,1H),3.84(s,3H).

[0699] Working Example

[0700] Example I-1

[0701] 2-[2-Bromo-5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0702]

[0703] A mixture of N-(7-amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxane-6-yl)-2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-carboxamide (1.02 g, 73% purity, 1.53 mmol) and toluene-4-sulfonic acid monohydrate (878 mg, 4.59 mmol) in toluene (40 ml) was heated to boiling for 2 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated, the organic phase was washed with water until a neutral reaction was achieved, dried and concentrated. The residue was purified by preparative HPLC. This provided two fractions of the title compound. Fraction 1: 207 mg (98% purity, 28% of theoretical value); Fraction 2: 144 mg (88% purity, 18% of theoretical value).

[0704] ESI mass [m / z]: 467.0 / 469.0 [M+H] +

[0705] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.70-7.48(m,2H),3.72(s,3H),3.03(q,2H),1.11(t,3H).

[0706] Example I-2

[0707] 2-[2-Bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0708]

[0709] At room temperature, formic acid (0.325ml, 8.61mmol) and hydrogen peroxide (35% aqueous solution, 1.04ml, 12.0mmol) were added sequentially to a solution of 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (805mg, 1.72mmol) in dichloromethane (5.0ml). The reaction mixture was stirred at room temperature overnight. Water and saturated aqueous sodium bisulfite solution were then added to the mixture while cooling with ice, and the mixture was stirred at room temperature for another night. The mixture was diluted with water (50ml) and dichloromethane (100ml). The phases were separated, and the organic phase was washed with water, then with saturated aqueous sodium bicarbonate solution, dried with sodium sulfate and concentrated. Acetonitrile (4.0ml) was added to the residue, and the mixture was stirred at room temperature. The solid was filtered off and dried to give an initial amount of the target compound (485 mg, 92% purity, 41% of theory). The mother liquor was concentrated and the residue was purified by silica gel column chromatography to isolate further title compound (114 mg, 93% purity, 12% of theory).

[0710] ESI mass [m / z]: 498.9 / 500.9 [M+H] +

[0711] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=13.37(s,1H),7.81(br s,1H),7.53(br s,1H),4.03(q,2H),3.91(s,3H),1.28(t,3H).

[0712] Example I-3

[0713] 2-[2-Bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0714]

[0715] To the initial charge 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (495 mg, 0.99 mmol) in acetone was added potassium carbonate (480 mg, 3.47 mmol) and iodomethane (154 μl, 2.47 mmol). The mixture was heated to boiling for 2 hours. After cooling to room temperature, the reaction mixture was concentrated to dryness. The residue was dissolved in dichloromethane and washed with 1.0 M hydrochloric acid. The organic phase was washed with saturated sodium chloride aqueous solution and dried with sodium sulfate. The resulting solution was concentrated to dryness to give the title compound (469 mg, 90% purity, 83% of theoretical value).

[0716] ESI mass [m / z]: 513.0 / 515.0 [M+H] +

[0717] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.83(s,1H),3.91(s,3H),3.77(s,3H),3.73(q,2H),1.26(t,3H).

[0718] Example I-4

[0719] 2-[2-(4-chlorophenyl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0720]

[0721] A mixture of dioxane (2.6 ml) and 1.0 M aqueous sodium carbonate solution (3.1 ml) was degassed in an argon stream for 30 minutes. 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (100 mg, 195 μmol), (4-chlorophenyl)boronic acid (30.5 mg, 195 μmol) and tetrakis(triphenylphosphine)palladium(0) (11.2 mg, 10 μmol) were then added and the mixture was heated at 92° C. overnight. After cooling to room temperature, the reaction mixture was concentrated to dryness and the residue was dissolved in water and dichloromethane. The phases were separated and the organic phase was washed twice with water, then dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (49.3 mg, 88% purity, 52% of theory).

[0722] ESI mass [m / z]: 545.0 [M+H] +

[0723] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.87-7.79(m,3H),7.67(d,2H),3.95(s,3H),3.84-3.76(m,5H),1.31(t,3H).

[0724] Example I-5

[0725] 2-[5-(Ethylsulfonyl)-2-(4-fluorophenyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0726]

[0727] A mixture of dioxane (1.0 ml) and 1.0 M aqueous sodium carbonate solution (1.1 ml) was degassed in an argon stream for 30 minutes. 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (35.0 mg, 68 μmol), (4-fluorophenyl)boric acid (9.5 mg, 68 μmol) and tetrakis(triphenylphosphine)palladium(0) (3.9 mg, 3 μmol) were then added and the mixture was heated to 92° C. for 4 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, the organic phase was washed with saturated aqueous ammonium chloride solution, dried and concentrated. The residue was dissolved in dioxane (1.0 ml), 1.0 M aqueous sodium carbonate solution (1.1 ml), (4-fluorophenyl) boronic acid (9.5 mg, 68 μmol) and tetrakis (triphenylphosphine) palladium (0) (3.9 mg, 3 μmol) were added thereto, and the mixture was heated to 92 ° C again for 7 hours. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by preparative HPLC to give the title compound (12.7 mg, 35% of theoretical value).

[0728] ESI mass [m / z]: 529.0 [M+H] +

[0729] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.90-7.84(m,3H),7.83(s,1H),7.50-7.41(m,2H),3.93(s,3H),3.85-3.75(m,5H),2.55-2.52(m,2H),2.08(s,1H),1.31(t,3H).

[0730] Example I-6

[0731] 1-{4-[5-(ethylsulfonyl)-1-methyl-4-(6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazol-2-yl)-1H-imidazol-2-yl]phenyl}cyclopropylcarbonitrile

[0732]

[0733] A mixture of dioxane (1.0 ml) and 1.0 M aqueous sodium carbonate solution (1.1 ml) was degassed in an argon stream for 30 minutes. 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (35.0 mg, 68 μmol), 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropylcarbonitrile (36.7 mg, 136 μmol) and tetrakis(triphenylphosphine)palladium(0) (7.8 mg, 7 μmol) were then added and the mixture was heated at 92° C. overnight. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the organic phase was washed with water, 1.0 M hydrochloric acid and saturated aqueous sodium chloride. The organic phase was then dried and concentrated. The residue was purified by preparative HPLC to give the title compound (48.7 mg, 85% purity, 53% of theory).

[0734] ESI mass [m / z]: 576.3 [M+H] +

[0735] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.88(s,1H),7.86-7.81(m,3H),7.54(d,2H),3.94(s,3H),3.84-3.77(m,5H),1.89-1.82(m,2H),1.67-1.60(m,2H),1.31(t,3H).

[0736] Example I-7

[0737] 2-[5-(Ethylsulfonyl)-1-methyl-2-{4-[1-(trifluoromethyl)cyclopropyl]phenyl}-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0738]

[0739] A mixture of dioxane (2.6 ml) and 1.0 M aqueous sodium carbonate solution (3.1 ml) was degassed in an argon stream for 30 minutes. 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (82.1 mg, 160 μmol), 4,4,5,5-tetramethyl-2-{4-[1-(trifluoromethyl)cyclopropyl]phenyl}-1,3,2-dioxaborolane (50.0 mg, 160 μmol) and tetrakis(triphenylphosphine)palladium(0) (9.2 mg, 8 μmol) were then added and the mixture was heated at 92° C. overnight. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the organic phase was washed with water, 1.0 M hydrochloric acid and saturated aqueous sodium chloride solution. The organic phase was then dried and concentrated. The residue was purified by preparative HPLC to give the title compound (65.0 mg, 66% of theory).

[0740] ESI mass [m / z]: 619.1 [M+H] +

[0741] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.86-7.81(m,3H),7.68(d,2H),3.95(s,3H),3.89-3.75(m,5H),1.45-1.37(m,2H),1.31(t,3H),1.26-1.19(m,2H).

[0742] Example I-8

[0743] 2-[2-Cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0744]

[0745] A mixture of N-(7-amino-2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxane-6-yl)-2-cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-carboxamide (163 mg, 341 μmol) and toluene-4-sulfonic acid monohydrate (195 mg, 1022 μmol) in toluene (3.4 ml) was heated to boiling for 6 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated, and the organic phase was washed with water until a neutral reaction was reached, dried and concentrated to obtain the title compound (149 mg, 93% purity, 88% of theoretical value).

[0746] ESI mass [m / z]: 461.3 [M+H] +

[0747] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=12.98(s,1H),7.76(s,1H),7.52(s,1H),3.96(s,3H),3.96-3.92(m,2H),2.25-2.13(m,1H),1.25(t,3H),1.11-1.01(m,4H).

[0748] Example I-9

[0749] 2-[2-Cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0750]

[0751] To the initial charge 2-[2-cyclopropyl-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (135 mg, 293 μmol) in acetone (2.0 ml) was added potassium carbonate (142 mg, 1026 μmol) and iodomethane (46 μl, 733 μmol). The mixture was heated to boiling for 3 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue was distributed between dichloromethane and 1.0 M hydrochloric acid. The organic phase was washed with water, dried and concentrated. The residue was purified by preparative HPLC to give the title compound (74.0 mg, 93% purity, 49% of theoretical value).

[0752] ESI mass [m / z]: 475.4 [M+H] +

[0753] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.84(s,1H),7.78(s,1H),3.96(s,3H),3.73(s,3H),3.67(q,2H),2.25-2.17(m,1H),1.24(t,3H),1.12-0.97(m,4H).

[0754] Example I-10

[0755] 2-[2-(4-bromophenyl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0756]

[0757] In a microwave vessel, to an initial charge of 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (40.0 mg, 0.078 mmol) and 4-bromophenylboronic acid (31.3 mg, 0.156 mmol) in dioxane (3.0 ml) was added 2.0 M aqueous sodium carbonate (195 μl, 0.390 mmol) and dichlorobis(tricyclohexylphosphine)palladium(II) (5.8 mg, 8.0 μmol). The mixture was degassed in a stream of argon for 5 minutes, then the vessel was sealed and heated to 120° C. in a microwave reactor for 12 minutes. After cooling, tetrakis(triphenylphosphine)palladium(0) (9.0 mg, 8.0 μmol) was added and the mixture was heated to 120° C. again for 24 minutes. After cooling, tetrakis(triphenylphosphine)palladium(0) (9.0 mg, 8.0 μmol) was added again and the mixture was heated to 120° C. again for 1 hour. Water and dichloromethane were added to the cooled reaction mixture, the phases were separated, the organic phase was washed twice with water, then dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (9.1 mg, 20% of theoretical value).

[0758] ESI mass [m / z]: 589.1 / 591.1 [M+H] +

[0759] 1 H-NMR (400 MHz, DMSO-d 6): δ[ppm]=7.89(s,1H),7.83(s,1H),7.83-7.75(m,4H),3.94(s,3H),3.82(s,3H),3.79(q,2H),1.31(t,3H).

[0760] Example I-11

[0761] 2-{5-(ethylsulfonyl)-2-[4-(1-fluorocyclopropyl)phenyl]-1-methyl-1H-imidazol-4-yl}-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0762]

[0763] First, 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (45.0 mg, 88.0 μmol), 2-[4-(1-fluorocyclopropyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (46.0 mg, 175 μmol) and tetrakis(triphenylphosphine)palladium(0) (20.3 mg, 18.0 μmol) were loaded into a microwave container and dissolved in a degassed mixture of dioxane (3.0 ml) and 1.0 M sodium carbonate aqueous solution (438 μl, 438 μmol). The reaction mixture was heated to 120° C. in a microwave reactor for 30 minutes. After cooling to room temperature, water was added to the mixture, and the mixture was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (30.0 mg, 60% of theory).

[0764] ESI mass [m / z]: 569.0 [M+H] +

[0765] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.85-7.81(m,3H),7.47(d,2H),3.96(s,3H),3.83(s,3H),3.80(q,2H),1.62-1.49(m,2H),1.36-1.24(m,5H).

[0766] Example I-12

[0767] 2-[2-(3-bromophenyl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0768]

[0769] First, 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (45.0mg, 88.0μmol), 4-bromophenylboric acid (35.2mg, 156μmol) and tetrakis(triphenylphosphine)palladium(0) (20.3mg, 18.0μmol) were loaded into a microwave container and dissolved in a degassed mixture of dioxane (3.0ml) and 1.0M sodium carbonate aqueous solution (438μl, 438μmol). The reaction mixture was heated to 120°C in a microwave reactor for 30 minutes. After cooling to room temperature, water was added to the mixture, and the mixture was extracted with dichloromethane. The combined organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (9.3 mg, 18% of theory).

[0770] ESI mass [m / z]: 589.0 / 591.0 [M+H] +

[0771] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.03-8.01(m,1H),7.89(s,1H),7.84-7.80(m,3H),7.61-7.54(m,1H),3.95(s,3H),3.84-3.76(m,5H),1.31(t,3H).

[0772] Example I-13

[0773] 2-[2-(3-chlorophenyl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0774]

[0775] First, 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (45.0mg, 88.0μmol), 3-chlorophenylboronic acid (27.4mg, 175μmol) and tetrakis(triphenylphosphine)palladium(0) (20.3mg, 18.0μmol) were loaded into a microwave container and dissolved in a degassed mixture of dioxane (3.0ml) and 1.0M sodium carbonate aqueous solution (438μl, 438μmol). The reaction mixture was heated to 120°C in a microwave reactor for 30 minutes. After cooling to room temperature, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (26.2 mg, 99% purity, 54% of theory).

[0776] ESI mass [m / z]: 545.0 [M+H] +

[0777] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.90-7.88(m,2H),7.83(s,1H),7.80-7.77(m,1H),7.70-7.60(m,2H),3.95(s,3H),3.83(s,3H),3.79(q,2H),1.31(t,3H).

[0778] Example I-14

[0779] 2-[5-(Ethylsulfonyl)-2-(3-fluorophenyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0780]

[0781] First, 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (45.0mg, 88.0μmol), 3-fluorophenylboric acid (24.5mg, 175μmol) and tetrakis(triphenylphosphine)palladium(0) (20.3mg, 18.0μmol) were loaded into a microwave container and dissolved in a degassed mixture of dioxane (3.0ml) and 1.0M sodium carbonate aqueous solution (438μl, 438μmol). The reaction mixture was heated to 120°C in a microwave reactor for 30 minutes. After cooling to room temperature, water was added to the mixture, and the mixture was extracted with dichloromethane. The combined organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (22.5 mg, 49% of theory).

[0782] ESI mass [m / z]: 529.2 [M+H] +

[0783] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.83(s,1H),7.71-7.62(m,3H),7.49-7.43(m,1H),3.96(s,3H),3.83(s,3H),3.80(q,2H),1.31(t,3H).

[0784] Example I-15

[0785] 2-{5-(ethylsulfonyl)-1-methyl-2-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl}-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0786]

[0787] First, 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (45.0mg, 88.0μmol), [4-(trifluoromethyl)phenyl]boric acid (33.3mg, 175μmol) and tetrakis(triphenylphosphine)palladium(0) (20.3mg, 18.0μmol) were loaded into a microwave container and dissolved in a degassed mixture of dioxane (3.0ml) and 1.0M sodium carbonate aqueous solution (438μl, 438μmol). The reaction mixture was heated to 120°C in a microwave reactor for 30 minutes. After cooling to room temperature, water was added to the mixture and the mixture was extracted with dichloromethane. The combined organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (33.0 mg, 98% purity, 64% of theory).

[0788] ESI mass [m / z]: 579.0 [M+H] +

[0789] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.06(d,2H),7.97(d,2H),7.89(s,1H),7.84(s,1H),3.98(s,3H),3.84(s,3H),3.81(q,2H),1.36-1.28m,3H).

[0790] Example I-16

[0791] 2-[5-(Ethylsulfonyl)-1-methyl-2-phenyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0792]

[0793] First, 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (45.0mg, 88.0μmol), phenylboronic acid (21.4mg, 175μmol) and tetrakis(triphenylphosphine)palladium(0) (20.2mg, 18.0μmol) were loaded into a microwave container and dissolved in a degassed mixture of dioxane (3.0ml) and 1.0M sodium carbonate aqueous solution (438μl, 438μmol). The reaction mixture was heated to 120°C in a microwave reactor for 30 minutes. After cooling to room temperature, water was added to the mixture, and the mixture was extracted with dichloromethane. The combined organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (30.0 mg, 99% purity, 66% of theory).

[0794] ESI mass [m / z]: 511.3 [M+H] +

[0795] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.83(s,1H),7.83-7.79(m,2H),7.63-7.58(m,3H),3.95(s,3H),3.83(s,3H),3.80(q,2H),1.35-1.29(m,3H).

[0796] Example I-17

[0797] 2-[5-(ethylsulfonyl)-1-methyl-2-{3-[1-(trifluoromethyl)cyclopropyl]phenyl}-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0798]

[0799] A mixture of dioxane (3.0 ml) and 1.0 M sodium carbonate aqueous solution (0.4 ml) was degassed in an argon stream for 30 minutes. Then 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (41.0 mg, 80 μmol), 4,4,5,5-tetramethyl-2-{3-[1-(trifluoromethyl)cyclopropyl]phenyl}-1,3,2-dioxaborolane (64.8 mg, 160 μmol) and tetrakis(triphenylphosphine)palladium(0) (18.5 mg, 16 μmol) were added and the mixture was heated to 120 ° C in a microwave reactor for 30 minutes. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (33.5 mg, 68% of theory).

[0800] ESI mass [m / z]: 619.2 [M+H] +

[0801] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.90-7.87(m,2H),7.84(s,1H),7.81(d,1H),7.69(d,1H),7.65-7.60(m,1H),3 .94(s,3H),3.82(s,3H),3.78(q,2H),1.42-1.38(m,2H),1.31(t,3H),1.25-1.21(m,2H).

[0802] Example I-18

[0803] 2-[2-(6-cyclopropylpyridin-3-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0804]

[0805] A mixture of dioxane (3.0 ml) and 1.0 M aqueous sodium carbonate solution (0.4 ml) was degassed in an argon stream for 30 minutes. 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (41.0 mg, 80 μmol), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (39.2 mg, 160 μmol) and tetrakis(triphenylphosphine)palladium(0) (18.5 mg, 16 μmol) were then added and the mixture was heated to 120 ° C in a microwave reactor for 30 minutes. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (28.2 mg, 64% of theory).

[0806] ESI mass [m / z]: 552.3 [M+H] +

[0807] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.80(d,1H),8.07(dd,1H),7.89(s,1H),7.83(s,1H),7.52(d,1H),3.95( s,3H),3.83(s,3H),3.80(q,2H),2.26-2.20(m,1H),1.31(t,3H),1.08-1.00(m,4H).

[0808] Example I-19

[0809] 2-[2-(5-chloro-2-thienyl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0810]

[0811] A mixture of dioxane (3.0 ml) and 1.0 M aqueous sodium carbonate solution (0.4 ml) was degassed in an argon stream for 30 minutes. 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (41.0 mg, 80 μmol), 2-(5-chloro-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (39.1 mg, 160 μmol) and tetrakis(triphenylphosphine)palladium(0) (18.4 mg, 16 μmol) were then added and the mixture was heated to 120 ° C in a microwave reactor for 30 minutes. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (16.9 mg, 38% of theory).

[0812] ESI mass [m / z]: 551.1 / 553.0 [M+H] +

[0813] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.83(s,1H),7.65(d,1H),7.34(d,1H),4.08(s,3H),3.79(s,3H),3.73(q,2H),1.28(t,3H).

[0814] Example I-20

[0815] 2-{5-(ethylsulfonyl)-2-[3-(1-fluorocyclopropyl)phenyl]-1-methyl-1H-imidazol-4-yl}-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0816]

[0817] A mixture of dioxane (3.0 ml) and 1.0 M aqueous sodium carbonate solution (0.4 ml) was degassed in an argon stream for 30 minutes. Then 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (41.0 mg, 80 μmol), 2-[3-(1-fluorocyclopropyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (50.4 mg, 192 μmol) and tetrakis(triphenylphosphine)palladium(0) (18.5 mg, 16 μmol) were added and the mixture was heated to 120 ° C in a microwave reactor for 30 minutes. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (29.3 mg, 97% purity, 60% of theory).

[0818] ESI mass [m / z]: 569.0 [M+H] +

[0819] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.89(s,1H),7.83(s,1H),7.77-7.69(m,1H),7.67-7.59(m,2H),7.50(d,1H),3 .94(s,3H),3.82(s,3H),3.78(q,2H),1.59-1.45(m,2H),1.31(t,3H),1.29-1.23(m,2H).

[0820] Example I-21

[0821] 2-[2-(6-chloropyridin-2-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0822]

[0823] A mixture of 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (70.0 mg, 136 μmol), 2-chloro-6-(tributylstannyl)pyridine (71.3 mg, 177 μmol), lithium chloride (15.0 mg, 355 μmol), copper (I) iodide (2.6 mg, 14 μmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 μmol) in degassed dioxane (3.0 ml) was heated to 150° C. in a microwave reactor for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a silica gel layer and washed with a mixture of dichloromethane and triethylamine (95:5 volume %), and the filtrate was concentrated. The residue was purified by preparative HPLC followed by repeated chromatography on silica gel to give the title compound (16.0 mg, 98% purity, 21% of theory).

[0824] ESI mass [m / z]: 546.3 / 538.1 [M+H] +

[0825] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.17(m,1H),8.07-8.12(m,1H),7.90(s,1H),7.84(s,1H),7.72 (m,1H),5.75(s,1H),4.30(s,3H),3.81(s,3H),3.76(m,2H),1.29(m,3H).

[0826] Example I-22

[0827] 2-[2-(6'-chloro[2,2'-bipyridyl]-6-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0828]

[0829] A mixture of 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (70.0 mg, 136 μmol), 2-chloro-6-(tributylstannyl)pyridine (71.3 mg, 177 μmol), lithium chloride (15.0 mg, 355 μmol), copper (I) iodide (2.6 mg, 14 μmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 μmol) in degassed dioxane (3.0 ml) was heated to 150° C. in a microwave reactor for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a silica gel layer and washed with a mixture of dichloromethane and triethylamine (95:5 volume %), and the filtrate was concentrated. The residue was purified by preparative HPLC followed by repeated chromatography on silica gel to give the title compound (4.3 mg, 98% purity, 5% of theory).

[0830] ESI mass [m / z]: 623.3 [M+H] +

[0831] 1 H-NMR (600 MHz, DMF-d 7 ): δ[ppm]=8.59(d,1H),8.52(d,1H),8.37(d,1H),8.28(m,1H),8.14-8.19(m,1H),7.92 (s,1H),7.82(s,1H),7.70(d,1H),4.62(s,3H),4.01(s,3H),3.93(m,2H),1.43(m,3H).

[0832] Example I-23

[0833] 2-[2-(3-cyclopropyl-1H-1,2,4-triazol-1-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0834]

[0835] 2-[2-Bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (40.0 mg, 78 μmol), 3-cyclopropyl-1H-1 ， 24-Triazole (8.5 mg ，78μmol) and potassium carbonate (10.7mg ， A mixture of 4-(2-(4-(2-cyclopropyl-1H-1-yl)-2-nitropropene (76 μmol)) in DMF was heated at 96 ° C overnight. Subsequently, 3-cyclopropyl-1H-1,2,4-triazole (8.5 mg, 78 μmol) and potassium carbonate (10.7 mg, 78 μmol) were added again, and the mixture was stirred at 96 ° C for another 5 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and water. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (23.0 mg, 98% purity, 53% of theoretical value).

[0836] ESI mass [m / z]: 542.2 [M+H] +

[0837] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=9.04(s,1H),7.90(s,1H),7.85(s,1H),3.94(s,3H),3.80-3.8 5(m,5H),2.12-2.19(m,1H),1.31(m,3H),0.99-1.09(m,2H),0.94(m,2H).

[0838] Example I-24

[0839] 2-[2-(5-bromopyridin-2-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0840]

[0841] A mixture of 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (70.0 mg, 136 μmol), 5-bromo-2-(tributylstannyl)pyridine (79.3 mg, 177 μmol), lithium chloride (15.0 mg, 355 μmol), copper (I) iodide (2.6 mg, 14 μmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 μmol) in degassed dioxane (3.0 ml) was heated to 150° C. in a microwave reactor for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a silica gel layer and washed with a mixture of dichloromethane and triethylamine (95:5 volume %), and the filtrate was concentrated. The residue was purified first by preparative HPLC and then by repeated chromatography on silica gel to give the title compound (4.5 mg, 6% of theory).

[0842] ESI mass [m / z]: 589.9 / 591.9 [M+H] +

[0843] 1 H-NMR (400 MHz, acetonitrile-d 3 ): δ[ppm]=8.81-8.83(m,1H),8.08-8.12(m,2H),7.59(s,1H),7.47(s,1H),4.34(s,3H),3.81(s,3H),3.66(m,2H),1.34(m,3H).

[0844] Example I-25

[0845] 2-[2-(5-bromo[2,3'-bipyridyl]-6'-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0846]

[0847] A mixture of 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (70.0 mg, 136 μmol), 5-bromo-2-(tributylstannyl)pyridine (79.3 mg, 177 μmol), lithium chloride (15.0 mg, 355 μmol), copper (I) iodide (2.6 mg, 14 μmol) and tetrakis (triphenylphosphine) palladium (0) (31.5 mg, 27 μmol) in degassed dioxane (3.0 ml) was heated to 150° C. in a microwave reactor for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a silica gel layer and washed with a mixture of dichloromethane and triethylamine (95:5 volume %), and the filtrate was concentrated. The residue was purified by preparative HPLC and then by repeated chromatography on silica gel to give the title compound (2.7 mg, 3% of theory).

[0848] ESI mass [m / z]: 666.9 / 668.9 [M+H] +

[0849] 1 H-NMR (400 MHz, acetonitrile-d 3 ): δ[ppm]=9.33-9.36(m,1H),8.81-8.83(m,1H),8.53(m,1H),8.28(m,1H),8.09(m,1H),7 .93(d,1H),7.60(s,1H),7.48(s,1H),4.43(s,3H),3.84(s,3H),3.68(m,2H),1.36(m,3H).

[0850] Example I-26

[0851] 2-[5-(Ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0852]

[0853] 2,2,6,6-tetramethylpiperidinyl zinc chloride lithium chloride complex (1.3M solution in THF, 1.20 ml, 1.58 mmol) was added to a solution of 6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (345 mg, 1.32 mmol) in anhydrous dioxane (15.0 ml) over 5 minutes, and the mixture was stirred at room temperature for 20 minutes. Subsequently, a solution of tetrakis(triphenylphosphine)palladium(0) (152 mg, 132 μmol) in dioxane (5.0 ml) and a solution of 5-(ethylthio)-4-iodo-1-methyl-1H-imidazole (353 mg, 1.32 mmol) in dioxane (5.0 ml) were added, and the mixture was stirred at 115° C. (oil bath temperature) for 2 hours. After cooling to room temperature, the reaction mixture was introduced into a half-saturated aqueous ammonium chloride solution (40 ml) and diluted with ethyl acetate (40 mL). During this process, a portion of the target compound precipitated out. The solid was filtered and dried to obtain the first fraction of the title compound (158 mg, 30% of theoretical value).

[0854] From the filtrate, the title compound was obtained as a second fraction. For this purpose, the phases were separated and the aqueous phase was extracted with ethyl acetate (2×40 ml). The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound as a second fraction (166 mg, 31% of theory).

[0855] ESI mass [m / z]: 403.5 [M+H] +

[0856] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.10(s,1H),7.81(s,1H),7.77(s,1H),3.99(s,3H),3.75(s,3H),2.96(m,2H),1.07(m,3H).

[0857] Example I-27

[0858] 1-{6-[5-(ethylthio)-1-methyl-4-(6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazol-2-yl)-1H-imidazol-2-yl]pyridin-2-yl}cyclopropylcarbonitrile

[0859]

[0860] To a solution of 2-[5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (82.5 mg, 205 μmol) in anhydrous dioxane (15.0 ml) was added 2,2,6,6-tetramethylpiperidinylzinc chloride lithium chloride complex (1.3 M solution in THF, 186 μl, 246 μmol) over 5 minutes, and the mixture was stirred at room temperature for 20 minutes. Subsequently, tetrakis(triphenylphosphine)palladium(0) (23.7 mg, 21 μmol) in dioxane (5.0 ml) and 1-(6-bromopyridin-2-yl)cyclopropylnitrile (45.7 mg, 205 μmol) in dioxane (5.0 ml) were added, and the mixture was stirred at 115° C. (oil bath temperature) for 2 hours. After cooling to room temperature, the reaction mixture was introduced into a half-saturated aqueous ammonium chloride solution (40 ml) and diluted with ethyl acetate (40 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (2×40 ml). The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (19 mg, 40% purity, 7% of theoretical value).

[0861] ESI mass [m / z]: 545.2 [M+H] +

[0862] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.14(d,1H),7.99-8.04(m,1H),7.86(s,1H),7.81(s,1H),7.59(br m,1H),4.18(s,3H),4.05(s,3H),2.96-3.03(m,2H),1.82-1.94(m,4H),1.11(m,3H).

[0863] Example I-28

[0864] 1-{6-[5-(ethylsulfonyl)-1-methyl-4-(6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazol-2-yl)-1H-imidazol-2-yl]pyridin-2-yl}cyclopropylcarbonitrile

[0865]

[0866] To the initial charge 1-{6-[5-(ethylthio)-1-methyl-4-(6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazol-2-yl)-1H-imidazol-2-yl]pyridin-2-yl}cyclopropylnitrile (17.0 mg, 31.0 μmol) in dichloromethane (20.0 ml) was added formic acid (12 μl, 312 μmol) and hydrogen peroxide (35% aqueous solution, 27 μl, 312 μmol). The mixture was stirred at room temperature overnight. Subsequently, water (50.0 ml) and saturated aqueous sodium bisulfite solution (15.0 ml) were added to the reaction mixture, and the mixture was then stirred for 1 hour. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (7.5 mg, 42% of theory).

[0867] ESI mass [m / z]: 577.0 [M+H] +

[0868] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.03-8.11(m,2H),7.90(s,1H),7.84(s,1H),7.67(m,1H),4.30(s,3H ),3.80(s,3H),3.76(m,2H),1.91-1.95(m,2H),1.82-1.86(m,2H),1.29(m,3H).

[0869] Example I-29

[0870] 2-[2-(6-bromopyridin-2-yl)-5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0871]

[0872] To a solution of 2-[5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (82.5 mg, 205 μmol) in anhydrous dioxane (15.0 ml) was added 2,2,6,6-tetramethylpiperidinyl zinc chloride lithium chloride complex (1.3 M solution in THF, 186 μl, 246 μmol) over 5 minutes, and the mixture was stirred at room temperature for 20 minutes. Subsequently, a solution of tetrakis(triphenylphosphine)palladium(0) (23.7 mg, 21 μmol) in dioxane (5.0 ml) and a solution of 2,6-dibromopyridine (48.6 mg, 205 μmol) in dioxane (5.0 ml) were added, and the mixture was stirred at 115° C. (oil bath temperature) for 2 hours. After cooling to room temperature, the reaction mixture was introduced into a half-saturated aqueous ammonium chloride solution (40 ml) and diluted with ethyl acetate (40 mL). Filtered to filter out insoluble components. Separated phases, the aqueous phase was extracted with ethyl acetate (2 × 40 ml). The combined organic phases were dried over sodium sulfate and concentrated. The residue was combined with the previously filtered solid. The crude product thus obtained was purified by preparative HPLC to obtain the title compound (28.2 mg, 90% purity, 22% theoretical value).

[0873] ESI mass [m / z]: 558.0 / 560.0 [M+H] +

[0874] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.23(m,1H),7.91-7.97(m,1H),7.86(s,1H),7.82(s,1H),7.75(m,1H),4.17(s,3H),4.05(s,3H),3.01(m,2H),1.11(m,3H).

[0875] Example I-30

[0876] 2-[2-(6-bromopyridin-2-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0877]

[0878] To the initial charge 2-[2-(6-bromopyridin-2-yl)-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (25.0 mg, 45.0 μmol) in dichloromethane (20.0 ml) was added formic acid (17 μl, 448 μmol) and hydrogen peroxide (35% aqueous solution, 39 μl, 448 μmol). The mixture was stirred at room temperature overnight. Subsequently, water (50.0 ml) and saturated aqueous sodium bisulfite solution (15.0 ml) were added to the reaction mixture, and the mixture was stirred for 1 hour. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound (13.7 mg, 52% of theory).

[0879] ESI mass [m / z]: 590.0 / 592.0 [M+H] +

[0880] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.85(d,1H),8.15-8.21(m,2H),7.90(s,1H),7.84(s,1H),4.31(s,3H),3.82(s,3H),3.77(m,2H),1.29(m,3H).

[0881] Example I-31

[0882] 2-[2-(5-chloropyridin-2-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0883]

[0884] A mixture of 2-[2-bromo-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (90.0 mg, 175 μmol), 5-bromo-2-(tributylstannyl)pyridine (91.7 mg, 228 μmol), lithium chloride (19.3 mg, 456 μmol), copper (I) iodide (3.3 mg, 18 μmol) and tetrakis (triphenylphosphine) palladium (0) (40.5 mg, 35 μmol) in degassed dioxane (3.0 ml) was heated to 150° C. in a microwave reactor for 1 hour. After cooling to room temperature, the reaction mixture was filtered through a silica gel layer and washed with a mixture of dichloromethane and triethylamine (95:5 volume %), and the filtrate was concentrated. The residue was chromatographed by preparative HPLC to give the title compound (57.8 mg, 98% purity, 59% of theory).

[0885] ESI mass [m / z]: 546.0 / 548.0 [M+H] +

[0886] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=8.85(d,1H),8.15-8.21(m,2H),7.90(s,1H),7.84(s,1H),4.31(s,3H),3.82(s,3H),3.77(q,2H),1.29(m,3H).

[0887] Example I-32

[0888] 6-[5-(Ethylsulfonyl)-1-methyl-4-(6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazol-2-yl)-1H-imidazol-2-yl]nicotinonitrile

[0889]

[0890] 2-[2-(5-chloropyridin-2-yl)-5-(ethylsulfonyl)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (37.0 mg, 68 μmol), allylpalladium chloride dimer (7.9 mg, 22 μmol), potassium hexacyanoferrate trihydrate (57.3 mg, 136 μmol) and 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (Xphos, 13.9 mg, 28 μmol) were added to a degassed mixture of water (170 μl) and cyclopentyl methyl ether (430 μl), and the reaction mixture was heated at 100°C overnight. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The crude product thus obtained was purified by preparative HPLC to give the title compound (18.7 mg, 51% of theory).

[0891] ESI mass [m / z]: 537.4 [M+H] +

[0892] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=9.23(d,1H),8.52(m,1H),8.35(d,1H),7.91(s,1H),7.85(s,1H),4.35(s,3H),3.82(s,3H),3.75-3.81(m,2H),1.29(m,3H).

[0893] Example I-33

[0894] 2-[2-(4-chlorophenyl)-5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0895]

[0896] A mixture of dioxane (3.0 ml) and 1.0 M sodium carbonate aqueous solution (0.5 ml) was degassed in an argon stream for 30 minutes. Then 2-[2-bromo-5-(ethylthio)-1-methyl-1H-imidazole-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (50.0 mg, 104 μmol), 4-chlorophenylboronic acid (32.5 mg, 208 μmol) and tetrakis(triphenylphosphine)palladium(0) (24.0 mg, 21 μmol) were added and the mixture was heated to 120 ° C in a microwave reactor for 30 minutes. After cooling to room temperature, the reaction mixture was concentrated to dryness and then dissolved in dichloromethane and water. Separate each phase and extract the aqueous phase with dichloromethane. The combined organic phase was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (30.3 mg, 89% purity, 51% of theory).

[0897] ESI mass [m / z]: 513.0 / 515.0 [M+H] +

[0898] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.85-7.88(m,2H),7.83(s,1H),7.80(s,1H),7.60-7.66(m,2H),4.03(s,3H),3.86(s,3H),3.00(m,2H),1.13(m,3H).

[0899] Example I-34

[0900] rac-2-[2-(4-chlorophenyl)-5-(ethylsulfoximino)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole

[0901]

[0902] To a solution of 2-[2-(4-chlorophenyl)-5-(ethylthio)-1-methyl-1H-imidazol-4-yl]-6,6,7,7-tetrafluoro-1-methyl-6,7-dihydro-1H-[1,4]dioxino[2,3-f]benzimidazole (30.0 mg, 94% purity, 55 μmol) in dichloromethane and methanol was added ammonium carbamate (8.6 mg, 110 μmol) and (diacetoxyiodo)benzene (45.2 mg, 137 μmol), and the suspension was stirred at room temperature in a closed reaction vessel for 1 hour. Subsequently, the reaction mixture was concentrated. The residue was purified by column chromatography on silica gel to give the title compound (16.4 mg, 95% purity, 52% of theoretical value).

[0903] ESI mass [m / z]: 544.4 / 546.2 [M+H] +

[0904] 1 H-NMR (400 MHz, DMSO-d 6 ): δ[ppm]=7.87(s,1H),7.79-7.83(m,3H),7.63-7.68(m,2H),4.76(s,1H),3.98(s,3H),3.76(s,3H),3.42-3.58(m,2H),1.23(m,3H).

[0905] Similar to the embodiment, according to the above preparation method, the compound of the following formula (I) can be obtained:

[0906]

[0907]

[0908]

[0909]

[0910]

[0911]

[0912]

[0913] Application Examples

[0914] Cucumber beetle - spray test

[0915] Solvent: 78 parts by weight of acetone

[0916] 1.5 parts by weight of dimethylformamide

[0917] Emulsifier: Alkyl aryl polyglycol ether

[0918] Suitable active ingredient preparations are prepared by using the above-mentioned weight parts of solvent to dissolve 1 weight part of active ingredient, and supplementing water containing 1000 ppm of emulsifier to make the solution reach the desired concentration. Other test concentrations are prepared by diluting the preparation with water containing emulsifier.

[0919] Pre-swollen wheat grains (Triticum aestivum) are incubated for one day in a multiwell plate filled with agar and a small amount of water (5 seeds per well). The germinated wheat grains are sprayed with the active ingredient preparation of the desired concentration. Subsequently, each well is infested with 10-20 beetle larvae of the spotted cucumber leaf beetle.

[0920] After 7 days, the efficacy is determined in %. 100% means that all wheat plants grow like the untreated, uninfected control; 0% means that no wheat plants grow.

[0921] In this test, for example, the following compounds of the preparation examples showed an efficacy of 100% at an application rate of 100 g / ha (= 32 μg / well): I-2, I-5, I-6, I-7, I-8, I-9, I-10, I-11, I-12, I-13, I-14, I-15, I-16, I-18, I-20, I-21, I-24, I-30, I-32, I-34, I-36, I-38.

[0922] In this test, for example, the following compounds of the preparation examples showed an efficacy of 80% at an application rate of 100 g / ha (=32 μg / well): I-4, I-23, I-37.

[0923] Southern root-knot nematode test

[0924] Solvent: 125.0 parts by weight of acetone

[0925] Suitable active ingredient preparations are prepared by mixing 1 part by weight of the active ingredient with the above-mentioned amount of solvent and diluting the concentrate with water to the desired concentration.

[0926] Containers were filled with sand, active ingredient solution, egg / larvae suspension of southern root-knot nematode (Meloidogyne incognita) and lettuce seeds. Lettuce seeds germinated and plants developed. Galls developed on the roots.

[0927] After 14 days, the nematicidal efficacy is determined in % based on the formation of galls. 100% means that no galls are found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.

[0928] In this test, for example, the following compounds of the preparation examples showed an efficacy of 100% at an application rate of 20 ppm: I-6, I-38.

[0929] In this test, for example, the following compounds of the preparation examples showed an efficacy of 90% at an application rate of 20 ppm: I-4, I-8, I-34, I-37.

[0930] Myzus persicae - oral test

[0931] Solvent: 100 parts by weight of acetone

[0932] A suitable active ingredient preparation is prepared by using the above-mentioned parts by weight of the solvent to dissolve 1 part by weight of the active ingredient, and supplementing with water to make the solution reach the desired concentration.

[0933] 50 μl of the active ingredient preparation was transferred to a microtiter plate and supplemented with 150 μl of IPL41 insect medium (33% + 15% sugar) to a final volume of 200 μl. Subsequently, the plate was sealed using parafilm and a mixed population of peach aphids (Myzus persicae) in a second microtiter plate was able to pierce and absorb the solution.

[0934] After 5 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that none of the aphids have been killed.

[0935] In this test, for example, the following compound of the preparation example showed an efficacy of 100% at an application rate of 20 ppm: I-8.

[0936] Green peach aphid - spray test

[0937] Solvent...

Claims

1. Compounds of formula (I) in R 1 represents ethyl, R 2 Represents methyl, R 3 represents bromine, cyclopropyl, Alternatively, represents phenyl, pyridyl, thienyl, each of which is optionally mono- or polysubstituted by identical or different substituents and bridged to the remainder of the molecule via a carbon atom, wherein the substituents mentioned in each case are as follows: cyano, fluorine, chlorine, bromine, trifluoromethyl, cyclopropyl, 1-cyano-1-cyclopropyl, 1-fluoro-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or pyridyl which is optionally monosubstituted by chlorine or bromine, Alternatively, represents a triazolyl group which is optionally monosubstituted and bridged to the remainder of the molecule via a nitrogen atom, wherein the substituents are as follows: cyclopropyl, R 4 , R 5 , R 6 , R 7 Represents fluorine, Y represents oxygen or =NH, Z stands for -NR 8 ,in R 8 represents hydrogen or methyl, m represents 1, n represents 1.

2. The compound of formula (I) according to claim 1, wherein R 1 represents ethyl, R 2 Represents methyl, R 3 represents bromine, cyclopropyl, or, phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluoro-1-cyclopropyl, or, represents an optionally monosubstituted pyridyl radical which is bridged to the remainder of the molecule via a carbon atom, wherein the substituents mentioned in each case are as follows: cyano, chlorine, bromine, cyclopropyl or 1-cyano-1-cyclopropyl, or, represents a thienyl group which is optionally monosubstituted and bridged to the remainder of the molecule via a carbon atom, wherein the substituents stated in each case are as follows: chlorine, or, represents a triazolyl group which is optionally monosubstituted and bridged to the remainder of the molecule via a nitrogen atom, wherein the substituents stated in each case are as follows: cyclopropyl, R 4 , R 5 , R 6 , R 7 Represents fluorine, Y represents oxygen, Z stands for -NR 8 ,in R 8 represents hydrogen or methyl, m and n represent 1.

3. The compound of formula (I) according to claim 1, wherein R 1 represents ethyl, R 2 Represents methyl, R 3 represents bromine, cyclopropyl, or phenyl optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, 1-cyano-1-cyclopropyl, 1-trifluoromethyl-1-cyclopropyl or 1-fluoro-1-cyclopropyl, or phenyl optionally disubstituted by the same or different substituents: fluorine, chlorine, bromine, cyano, or represents an optionally monosubstituted pyridinyl group which is bridged to the remainder of the molecule via a carbon atom, wherein the substituents mentioned in each case are as follows: cyano, chlorine, bromine, cyclopropyl or 1-cyano-1-cyclopropyl or a pyridinyl group which is monosubstituted by chlorine or bromine, wherein the pyridinyl group is bridged to the remainder of the molecule via a carbon atom, or, represents a thienyl group which is optionally monosubstituted and bridged to the remainder of the molecule via a carbon atom, wherein the substituents mentioned in each case are as follows: chlorine, or, represents a triazolyl group which is optionally monosubstituted and bridged to the remainder of the molecule via a nitrogen atom, wherein the substituents mentioned are as follows: cyclopropyl, R 4 , R 5 , R 6 , R 7 Represents fluorine, Y represents oxygen or =NH, Z stands for -NR 8 ,in R 8 represents hydrogen or methyl, m and n represent 1.

4. The compound of formula (I) according to claim 1, wherein the compound has the following structure:

5. An agrochemical formulation comprising a compound of formula (I) according to claim 1 and an extender and / or a surfactant.

6. The agricultural chemical formulation according to claim 5, further comprising other agricultural chemical active ingredients.

7. A method for controlling animal pests, characterized in that: The compound of formula (I) according to claim 1 or the agricultural chemical preparation according to claim 5 or 6 is allowed to act on animal pests and / or their habitat.

8. Use of the compound of formula (I) according to claim 1 or the agricultural chemical preparation according to claim 5 or 6 for controlling animal pests.

Images